JAZL/ChemGist-CHON huggingface dataset:
Compound: Isocyanomethane
SMILES: [N+](#[C-])C
InChIKey: ZRKSVHFXTRFQFL-UHFFFAOYSA-N
Synonyms: Isocyanomethane, METHYL ISOCYANIDE, 593-75-9, Methyl isonitrile, Methylisonitrile, Methane, isocyano-, B5B6DXM7GG, CNMe, MeNC, CH3-NC, DTXSID3075040, CHEBI:44177, RefChem:149233, DTXCID9042598, 209-806-9, isoacetonitrile, MFCD05864413, Isoacetonitrile; Methyl Isonitrile, methylisocyanide, EINECS 209-806-9, UNII-B5B6DXM7GG, SCHEMBL90230, SCHEMBL1160215, SCHEMBL1985952, SCHEMBL31010575, AKOS015959046, InChI=1/C2H3N/c1-3-2/h1H, AT35255, DB04337, GS-0345, SY262092, NS00043663, EN300-313295, Q2435355
Theoretical properties:
molecular_formula: C2H3N
molecular_weight: 41.05 g/mol
exact_mass: 41.026549100 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 0
hydrogen_bond_acceptor_count: 1
rotatable_bond_count: 0
heavy_atom_count: 3
topological_polar_surface_area: 4.4 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
Descriptions:
pubchem: Isocyanomethane is an isocyanide.
wikipedia: Methyl isocyanide or isocyanomethane is an organic compound and a member of the isocyanide family. This colorless liquid is isomeric and isoelectronic to methyl cyanide (acetonitrile), but its reactivity is very different. In contrast to the faintly sweet, ethereal odor of acetonitrile, the smell of methyl isocyanide, like that of other simple volatile isocyanides, is distinctly penetrating and vile. Methyl isocyanide is mainly used for making 5-membered heterocyclic rings.  The C-N distance in methyl isocyanide is very short, 1.158 Å as is characteristic of isocyanides.
Compound: 2420-87-3
SMILES: O=C1OC(=O)c2c1cc(-c3cc4C(=O)OC(c4cc3)=O)cc2
InChIKey: WKDNYTOXBCRNPV-UHFFFAOYSA-N
Synonyms: 2420-87-3, 3,3',4,4'-Biphenyltetracarboxylic dianhydride, [5,5'-Biisobenzofuran]-1,1',3,3'-tetrone, 4,4'-Biphthalic dianhydride, 5,5'-bi-2-benzofuran-1,1',3,3'-tetrone, SN5KO2N6PC, DTXSID8044886, EINECS 219-342-9, J28.182D, 3,3',4,4'-biphenyltetracarboxylic anhydride, DTXCID6024886, (5,5'-Biisobenzofuran)-1,1',3,3'-tetrone, 1,1'-Biphenyl-3,3',4,4'-tetracarboxylic acid dianhydride, 3,3',4,4'-Biphenyltetracarboxylic 3,4:3',4'-dianhydride, RefChem:527640, 219-342-9, 4,4'-Biphthalic anhydride, [5,5'-Biisobenzofuran]-1,1',3,3'-tetraone, 3,3,4,4-Biphenyltetracarboxylic Dianhydride, BPDA, MFCD00039140, 5-(1,3-dioxo-2-benzofuran-5-yl)-2-benzofuran-1,3-dione, 3,3',4,4'-Biphenyltetracarboxylic acid dianhydride, 3,3',4,4'-Biphenyltetracarboxylic dianhydride (BPDA), 5-(1,3-dioxoisobenzofuran-5-yl)isobenzofuran-1,3-dione, 5,5'-biisobenzofuran-1,1',3,3'-tetraone, Diphenyl-3,3',4,4'-tetracarboxylic Dianhydride, UNII-SN5KO2N6PC, SCHEMBL169305, 3,4,3',4'-biphenyltetracarboxylic acid dianhydride, orb2939805, CHEMBL3185102, SCHEMBL29359977, SCHEMBL29423347, WZG0044, Tox21_301695, STK366517, AKOS003242023, CS-W009437, FB62603, HY-W008721, 5-(1,3-dioxo-1,3-dihydro-2-benzofuran-5-yl)-1,3-dihydro-2-benzofuran-1,3-dione, NCGC00256278-01, AC-14433, AS-14497, SY009581, CAS-2420-87-3, 4,4a(2)-Biphenyltetracarboxylic dianhydride, B1326, B4262, NS00027589, ST50907563, 3,3`,4,4`-Biphenyltetracarboxylic dianhydride, H11254, [5,5'-Bi-2-benzofuran]-1,1',3,3'-tetrone, 3,3',4,4'-biphenyltetracarboxylic acid anhydride, 3,3\',4,4\'-Biphenyltetracarboxylic dianhydride, F078864, 3,3',4,4'-Biphenyltetracarboxylic dianhydrideBPDA, 4,4'-Biphthalic Anhydride (purified by sublimation), Q4836253, 3,3',4,4'-Biphenyltetracarboxylic dianhydride, 97%, 1,1'-Biphenyl-3,3',4,4'-tetracarboxylic dianhydride, [1,1'-Biphenyl]-3,3',4,4'-tetracarboxylic 3,4:3',4'-dianhydride, 3,3 inverted exclamation mark ,4,4 inverted exclamation mark -Biphenyltetracarboxylic Dianhydride, 3,3 inverted exclamation marka,4,4 inverted exclamation marka-Biphenyltetracarboxylic dianhydride
Theoretical properties:
molecular_formula: C16H6O6
molecular_weight: 294.21 g/mol
exact_mass: 294.01643791 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 0
hydrogen_bond_acceptor_count: 6
rotatable_bond_count: 1
heavy_atom_count: 22
topological_polar_surface_area: 86.7 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
Descriptions:
chembl: Unnamed Compound is a small molecule listed in the ChEMBL database but has not progressed to an approved clinical phase.
wikipedia: BPDA or biphenyl-tetracarboxylic acid dianhydride is a monomer used in the production of some polyimides.
Compound: CP-22185
SMILES: N([C@H]1c2c(cccc2)[C@@H](c3ccccc3)CC1)C
InChIKey: NVXPZMLRGBVYQV-RHSMWYFYSA-N
Synonyms: CP-22185, (1RS,4RS)-N-Methyl-4-phenyl-1,2,3,4-tetrahydronaphthalen-1-amine, UNII-X4CR040L3W, 52758-03-9, X4CR040L3W, (1R,4R)-N-methyl-4-phenyl-1,2,3,4-tetrahydronaphthalen-1-amine, Sertraline hydrochloride specified impurity B [EP], 1-Naphthalenamine, 1,2,3,4-tetrahydro-N-methyl-4-phenyl-, cis-(+/-)-, 1-Naphthalenamine, 1,2,3,4-tetrahydro-N-methyl-4-phenyl-, (1R,4R)-rel-, Tametraline, cis-, CP22185, Sertraline Impurity 34, SCHEMBL4619208, SCHEMBL30592536, Q27293547, SERTRALINE HYDROCHLORIDE IMPURITY B [EP IMPURITY]
Theoretical properties:
molecular_formula: C17H19N
molecular_weight: 237.34 g/mol
exact_mass: 237.151749610 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 1
hydrogen_bond_acceptor_count: 1
rotatable_bond_count: 2
heavy_atom_count: 18
topological_polar_surface_area: 12 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
Descriptions:
wikipedia: Ras association domain-containing protein 2 is a protein that in humans is encoded by the RASSF2 gene.
This gene encodes a protein that contains a Ras association domain. Similar to its cattle and sheep counterparts, this gene is located near the prion gene. Two alternatively spliced transcripts encoding the same isoform have been reported.
Compound: 40817-08-1
SMILES: N#Cc1ccc(-c2ccc(CCCCC)cc2)cc1
InChIKey: HHPCNRKYVYWYAU-UHFFFAOYSA-N
Synonyms: 40817-08-1, 4-Cyano-4'-pentylbiphenyl, [1,1'-Biphenyl]-4-carbonitrile, 4'-pentyl-, p-Cyano-p'-pentylbiphenyl, 4-n-pentyl-4'-cyanobiphenyl, 2R6RYG3ZGM, 4'-Pentyl[1,1'-biphenyl]-4-carbonitrile, (1,1'-Biphenyl)-4-carbonitrile, 4'-pentyl-, DTXSID3068255, 4'-Pentyl(1,1'-biphenyl)-4-carbonitrile, RefChem:98646, DTXCID4039817, 255-093-2, 4'-Pentyl-[1,1'-biphenyl]-4-carbonitrile, 4-Cyano-4'-n-pentylbiphenyl, 4-(4-pentylphenyl)benzonitrile, 4'-Pentyl-4-biphenylcarbonitrile, 4-Pentyl-4'-cyanobiphenyl, MFCD00036350, 4'-pentylbiphenyl-4-carbonitrile, 4-Cyano-4-pentylbiphenyl, 4'-pentyl-4-cyanobiphenyl, 5CB, 4-(4-pentylphenyl)benzenecarbonitrile, 4'-Amyl-4-biphenylcarbonitrile, pentyl cyanobiphenyl, EINECS 255-093-2, UNII-2R6RYG3ZGM, 4,4'-n-Pentylcyanobiphenyl, SCHEMBL263560, 4?-Pentyl-biphenyl-4-carbonitrile, 4\'-Heptyl-4-biphenylcarbonitrile, 4'-n-Pentyl-4-biphenylcarbonitrile, SBB008542, AKOS015839649, CS-W012656, AS-17503, SY036398, DB-009037, 4-Pentyl-[1,1'-biphenyl]-4'-carbonitrile, NS00030851, ST50825933, 4'-Pentyl[1,1'-biphenyl]-4-carbonitrile #, F049366, Q1490706, 4-Cyano-4 inverted exclamation mark -n-Pentylbiphenyl, 4 inverted exclamation mark -Pentylbiphenyl-4-carbonitrile, 4 inverted exclamation marka-Pentyl-4-biphenylcarbonitrile, 4'-Pentyl-4-biphenylcarbonitrile, liquid crystal (nematic), 98%, 4-(4'-Pentylphenyl)benzonitrile; 4'-Pentyl[1,1'-biphenyl]-4-carbonitrile, InChI=1/C18H19N/c1-2-3-4-5-15-6-10-17(11-7-15)18-12-8-16(14-19)9-13-18/h6-13H,2-5H2,1H
Theoretical properties:
molecular_formula: C18H19N
molecular_weight: 249.3 g/mol
exact_mass: 249.151749610 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 0
hydrogen_bond_acceptor_count: 1
rotatable_bond_count: 5
heavy_atom_count: 19
topological_polar_surface_area: 23.8 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
Descriptions:
wikipedia: 4-Cyano-4'-pentylbiphenyl is a commonly used nematic liquid crystal with the chemical formula C18H19N. It frequently goes by the common name 5CB. 5CB was first synthesized by George William Gray, Ken Harrison, and J.A. Nash at the University of Hull in 1972 and at the time it was the first member of the cyanobiphenyls. The liquid crystal was discovered after Gray's group received a grant from the UK Ministry of Defence to find a liquid crystal that had liquid crystal phases near room temperature with the specific intention of using them in liquid crystal displays. The molecule is about 20 Å long. The liquid crystal 5CB undergoes a phase transition from a crystalline state to a nematic state at 22.5 °C and it goes from a nematic to an isotropic state at 35.0 °C.
Compound: 3,4-Dihydroxyphenylacetaldehyde
SMILES: O=CCc1cc(O)c(O)cc1
InChIKey: IADQVXRMSNIUEL-UHFFFAOYSA-N
Synonyms: 3,4-Dihydroxyphenylacetaldehyde, 2-(3,4-dihydroxyphenyl)acetaldehyde, 5707-55-1, Protocatechuatealdehyde, (3,4-dihydroxyphenyl)acetaldehyde, DTXSID10205680, Benzeneacetaldehyde, 3,4-dihydroxy-, CHEBI:27978, DHPAA aldehyde, RefChem:486239, DTXCID40128171, Dopal, Dopal (>80%), MFCD19707262, F2E9Q24TSL, 3,4-Dihydroxybenzeneacetaldehyde, Benzeneacetaldehyde,3,4-dihydroxy-, Dopal (purity>80%), UNII-F2E9Q24TSL, SCHEMBL891837, GTPL6632, orb1692810, SCHEMBL3217327, SCHEMBL29929036, 2-(3,4-dihydroxyphenyl)ethanal, 3,4-dihydroxy-Benzeneacetaldehyde, GLXC-03720, EX-A14301, AKOS022634762, HY-121252A, SY237352, DB-226533, HY-121252, 2-(3,4-BIS(OXIDANYL)PHENYL)ETHANAL, C04043, EN300-732949, Q4634065
Theoretical properties:
molecular_formula: C8H8O3
molecular_weight: 152.15 g/mol
exact_mass: 152.047344113 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 2
hydrogen_bond_acceptor_count: 3
rotatable_bond_count: 2
heavy_atom_count: 11
topological_polar_surface_area: 57.5 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
Descriptions:
pubchem: 3,4-dihydroxyphenylacetaldehyde is a phenylacetaldehyde in which the 3 and 4 positions of the phenyl group are substituted by hydroxy groups. It has a role as a mouse metabolite, an Escherichia coli metabolite and a human metabolite. It is a member of phenylacetaldehydes, a member of catechols and an alpha-CH2-containing aldehyde.
chebi: A phenylacetaldehyde in which the 3 and 4 positions of the phenyl group are substituted by hydroxy groups.
wikipedia: 3,4-Dihydroxyphenylacetaldehyde (DOPAL), also known as dopamine aldehyde, is a metabolite of the monoamine neurotransmitter dopamine formed by monoamine oxidase (MAO).
Other metabolic pathways of dopamine metabolism include methylation by catechol O-methyltransferase (COMT) into 3-methoxytyramine and β-hydroxylation by dopamine β-hydroxylase (DBH) into norepinephrine. There is also spontaneous oxidation of dopamine into dopamine quinones and reactive oxygen species.
Compound: Homovanillyl alcohol
SMILES: O(c1c(O)ccc(c1)CCO)C
InChIKey: XHUBSJRBOQIZNI-UHFFFAOYSA-N
Synonyms: Homovanillyl alcohol, 2380-78-1, 4-(2-Hydroxyethyl)-2-methoxyphenol, 3-METHOXY-4-HYDROXYPHENYLETHANOL, Benzeneethanol, 4-hydroxy-3-methoxy-, MOPET, 9A7EE8MS6A, DTXSID40178494, MHPE, RefChem:788469, Hydroxymethoxyphenethyl Alcohol, Alcohol, Hydroxymethoxyphenethyl, 3 Methoxy 4 hydroxyphenylethanol, DTXCID70100985, 219-175-1, Methoxyhydroxyphenylethanol, 4-Hydroxy-3-methoxyphenethanol, Vanillylmethanol, Guaiacyl ethanol, 4-(2-Hydroxyethyl)guaiacol, 4-Hydroxy-3-methoxyphenethyl alcohol, 4-Hydroxy-3-methoxyphenylethyl alcohol, (4-Hydroxy-3-methoxyphenyl)ethanol, 2-(4-Guaiacyl)-ethanol, 2-(4-Hydroxy-3-methoxyphenyl)-ethanol, Homovanillin alcohol, 4-(2-hydroxyethyl)-2-methoxy-phenol, UNII-9A7EE8MS6A, 4-Hydroxy-3-methoxybenzeneethanol, EINECS 219-175-1, Homovanilline alcohol, MFCD00002903, Homovanillyl alcohol, 99%, SCHEMBL43681, orb1297337, CHEMBL3747068, SCHEMBL30045575, XHUBSJRBOQIZNI-UHFFFAOYSA-, 3-methoxy-4-hydroxy phenylethanol, CHEBI:173769, 4-Hydroxy-3-methoxy-Benzeneethanol, HY-N7513, MFCD0002903, AKOS003382015, CCG-356420, EBC-616274, FH66260, FS-3438, 4-(2-Hydroxyethyl)-2-methoxyphenol #, ST088597, DB-046251, CS-0131118, NS00027490, D95086, EN300-1250800, Q5891855, InChI=1/C9H12O3/c1-12-9-6-7(4-5-10)2-3-8(9)11/h2-3,6,10-11H,4-5H2,1H3, VTL
Theoretical properties:
molecular_formula: C9H12O3
molecular_weight: 168.19 g/mol
exact_mass: 168.078644241 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 2
hydrogen_bond_acceptor_count: 3
rotatable_bond_count: 3
heavy_atom_count: 12
topological_polar_surface_area: 49.7 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
melting_point: 40 - 42 °C
Descriptions:
pubchem: (4-Hydroxy-3-methoxyphenyl)ethanol is a member of phenols and a member of methoxybenzenes.
chembl: Unnamed Compound is a small molecule listed in the ChEMBL database but has not progressed to an approved clinical phase.
wikipedia: Homovanillyl alcohol is a metabolite of hydroxytyrosol, which in turn is a metabolite of the neurotransmitter dopamine.
Compound: 1,2-Dioxetane-3,4-dione
SMILES: O=C1OOC1=O
InChIKey: WYNZXNXFHYJUTE-UHFFFAOYSA-N
Synonyms: 1,2-Dioxetane-3,4-dione, 26974-08-3, DTXSID80564519, RefChem:1052309, DTXCID50515295, 1,2-Dioxetanedione, SCHEMBL345920, Q161485
Theoretical properties:
molecular_formula: C2O4
molecular_weight: 88.02 g/mol
exact_mass: 87.97965848 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 0
hydrogen_bond_acceptor_count: 4
rotatable_bond_count: 0
heavy_atom_count: 6
topological_polar_surface_area: 52.6 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
Descriptions:
wikipedia: The chemical compound 1,2-dioxetanedione, or 1,2-dioxacyclobutane-3,4-dione, often called peroxyacid ester, is an unstable oxide of carbon (an oxocarbon) with formula C2O4. It can be viewed as a double ketone of 1,2-dioxetane (1,2-dioxacyclobutane), or a cyclic dimer of carbon dioxide.
In ordinary conditions, it quickly decomposes to carbon dioxide (CO2) even at 180 K (−93.1 °C), but can be detected by mass spectrometry and other techniques.
1,2-Dioxetanedione is an intermediate in the chemoluminescent reactions used in glowsticks. The decomposition proceeds via a paramagnetic oxalate biradical intermediate.
It is an intermediate in a reaction (between oxalyl chloride and hydrogen peroxide in ethyl acetate, accumulating in solution at room temperature  up to a few micromoles, provided that the activating dye and all traces of metals and other reducing agents are removed from the system, and the reactions are carried out in an inert atmosphere.
Compound: 5-Hydroxymethylcytosine
SMILES: O=c1ncc(CO)c([nH]1)N
InChIKey: RYVNIFSIEDRLSJ-UHFFFAOYSA-N
Synonyms: 5-Hydroxymethylcytosine, 1123-95-1, 5-(hydroxymethyl)cytosine, 4-Amino-5-(hydroxymethyl)-2(1H)-pyrimidinone, 6CD2RLN1NK, 2(1H)-Pyrimidinone, 4-amino-5-(hydroxymethyl)-, DTXSID70149990, NSC-27368, CHEBI:76792, 5-hydroxylmethylcytosine, RefChem:102910, DTXCID0072481, 4-amino-5-(hydroxymethyl)pyrimidin-2-ol, 6-amino-5-(hydroxymethyl)-1H-pyrimidin-2-one, 4-amino-5-(hydroxymethyl)pyrimidin-2(1H)-one, MFCD00047369, 5-pyrimidinemethanol, 4-amino-2-hydroxy-, HM-cytosine, 5-Oxymethylcytosin, MFCD18432304, NSC 27368, DEMETHYLBACIMETHRIN, UNII-6CD2RLN1NK, SCHEMBL26506, SCHEMBL30092, 5-(OXYMETHYL)CYTOSINE, SCHEMBL546483, SCHEMBL546484, orb1694648, SCHEMBL2493947, ALBB-023625, NSC27368, SBB071695, STK803144, AKOS005266249, AKOS006229006, AKOS015854852, CYTOSINE, 5-(HYDROXYMETHYL)-, CS-W019110, ES-2013, FH35238, HY-W018324, SB57403, s10224, PD158492, ST095765, DB-007057, 2-Hydroxy-5-hydroxymethyl-6-amino-pyrimidin, 4-AMINO-2-HYDROXY-5-PYRIMIDINEMETHANOL, 6-Amino-5-(hydroxymethyl)pyrimidin-2(1H)-one, pyrimidin-2(1H)-one, 4-amino-5-hydroxymethyl-, Q238535, 6-AMINO-5-(HYDROXYMETHYL)-2(1H)-PYRIMIDINONE, 2(1H)-PYRIMIDINONE, 6-AMINO-5-(HYDROXYMETHYL)-
Theoretical properties:
molecular_formula: C5H7N3O2
molecular_weight: 141.13 g/mol
exact_mass: 141.053826475 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 3
hydrogen_bond_acceptor_count: 3
rotatable_bond_count: 1
heavy_atom_count: 10
topological_polar_surface_area: 87.7 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
Descriptions:
pubchem: 5-(hydroxymethyl)cytosine is a nucleobase analogue that is cytosine in which the hydrogen at position 5 is replaced by a hydroxymethyl group. It has a role as a mouse metabolite and a human metabolite. It is an aromatic primary alcohol, a pyrimidone, an aminopyrimidine and a nucleobase analogue. It is functionally related to a cytosine.
chebi: A nucleobase analogue that is cytosine in which the hydrogen at position 5 is replaced by a hydroxymethyl group.
wikipedia: 5-Hydroxymethylcytosine (5hmC) is a DNA pyrimidine nitrogen base derived from cytosine. It is potentially important in epigenetics, because the hydroxymethyl group on the cytosine can possibly switch a gene on and off. It was first seen in bacteriophages in 1952. However, in 2009 it was found to be abundant in human and mouse brains, as well as in embryonic stem cells. In mammals, it can be generated by oxidation of 5-methylcytosine, a reaction mediated by TET enzymes.
Compound: Cupanone
SMILES: O=C1C2=CC(C(C)C3C2C4(Oc5cc6OCOc6cc35)OCOC4=C1)C
InChIKey: WTXORUUTAZJKSN-UHFFFAOYSA-N
Synonyms: Cupanone, SCHEMBL30898580, NSC156298, Q5045601, 7,8-Dimethyl-7,8,8a,14b-tetrahydro-2H,5H,11H-benzo[kl]bis[1,3]dioxolo[4,5-b:4',5'-g]xanthen-5-one
Theoretical properties:
molecular_formula: C20H18O6
molecular_weight: 354.4 g/mol
exact_mass: 354.11033829 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 0
hydrogen_bond_acceptor_count: 6
rotatable_bond_count: 0
heavy_atom_count: 26
topological_polar_surface_area: 63.2 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
Descriptions:
{"pubchem": null, "chebi": null, "chembl": null, "wikipedia": "Carpanone is a naturally occurring lignan-type natural product most widely known for the remarkably complex way nature prepares it, and the similarly remarkable success that an early chemistry group, that of Orville L. Chapman, had at mimicking nature's pathway. Carpanone is an organic compound first isolated from the carpano trees (Cinnamomum sp.) of Bougainville Island by Brophy and coworkers, trees from which the natural product derives its name. The hexacyclic lignan is one of a class of related diastereomers isolated from carpano bark as mixtures of equal proportion of the \"handedness\" of its components (i.e., racemic mixtures), and is notable in its stereochemical complexity, because it contains five contiguous stereogenic centers. The route by which this complex structure is achieved through biosynthesis involves a series of reactions that, almost instantly, take a molecule with little three-dimensionality to the complex final structure. Notably, Brophy and coworkers isolated the simpler carpacin, a phenylpropanoid with a 9-carbon framework, recognized its substructure as being dimerized within the complex carpanone structure, and proposed a hypothesis of how carpacin was converted to carpanone in plant cells:\n\ncarpacin underwent loss of a methyl (-CH3) group from the ring methoxy (-OCH3) group to provide the phenol, desmethylcarpacin,\nthis phenol intermediate then underwent a phenolic coupling to generate a dimeric intermediate, which was\nfollowed immediately by a Diels-Alder (4+2) cycloaddition reaction to create 2 new rings, to give the final carpanone product.\nRemarkably, within two years, Chapman and coworkers were able to chemically design a route to mimic this proposed biosynthetic route, and achieved the synthesis of carpanone from carpacin in a single \"pot\", in about 50% yield.\nCarpanone itself is limited in its pharmacologic and biologic activities, but related analogs arrived at by variations of the Brophy-Chapman approach have shown activities as tool compounds relevant to mammalian exocytosis and vesicular traffic, and provided therapeutic \"hits\" in antiinfective, antihypertensive, and hepatoprotective areas.\nThe original Chapman design and synthesis is considered a classic in total synthesis, and one that highlights the power of biomimetic synthesis."}
SMILES: O=C(NC[C@H](O)CC/C=C\C/C=C\CC)CCC[N+](C)(C)C
InChIKey: QYFDYRHORFAECH-SVCKQPKZSA-O
Theoretical properties:
Physical properties:
Descriptions:
chembl: Unnamed Compound is a small molecule listed in the ChEMBL database but has not progressed to an approved clinical phase.
Compound: INDOLIZINE
SMILES: n12c(cccc1)ccc2
InChIKey: HOBCFUWDNJPFHB-UHFFFAOYSA-N
Synonyms: INDOLIZINE, 274-40-8, Pyrrocoline, Pyrrolo[1,2-a]pyridine, Pyrrolo(1,2-a)pyridine, B48FMH8YFQ, CHEBI:35583, DTXSID50181818, RefChem:148211, DTXCID90104309, 691-518-1, Indolizin, MFCD00030189, 4-Azaindene, CHEMBL3622747, Pyrrocolin, 4H-indolizine, UNII-B48FMH8YFQ, SCHEMBL7913, SCHEMBL107542, SCHEMBL107848, SCHEMBL129192, SCHEMBL129701, SCHEMBL133333, SCHEMBL133817, SCHEMBL136008, SCHEMBL453998, SCHEMBL1607479, SCHEMBL15062451, SCHEMBL15062613, BDBM50123663, AKOS005254677, AB01491, AS-77407, SY056632, DB-047222, CS-0155664, P1943, D94752, EN300-209020, F230857, Q910641, InChI=1/C8H7N/c1-2-6-9-7-3-5-8(9)4-1/h1-7
Theoretical properties:
molecular_formula: C8H7N
molecular_weight: 117.15 g/mol
exact_mass: 117.057849228 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 0
hydrogen_bond_acceptor_count: 0
rotatable_bond_count: 0
heavy_atom_count: 9
topological_polar_surface_area: 4.4 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
Descriptions:
pubchem: Indolizine is a mancude organic heterobicyclic parent and a member of indolizines.
chembl: Unnamed Compound is a small molecule listed in the ChEMBL database but has not progressed to an approved clinical phase.
wikipedia: Indolizine is an heterocyclic compound with the formula C8H7N). It is an uncommon isomer of indole with the nitrogen located at a ring fusion position. The saturated analog is indolizidine, which is the core of a variety of alkaloids such as swainsonine. 
Examples of some simple fully synthetic substituted indolizines include 2ZEDMA, 1ZP2MA, and 1Z2MAP1O.
Compound: (-)-alpha-isocomene
SMILES: C1(=C[C@@]2(CCC[C@@]32[C@]1(CC[C@H]3C)C)C)C
InChIKey: SAOJPWFHRMUCFN-UQOMUDLDSA-N
Synonyms: (-)-alpha-isocomene, CHEBI:68666, (1R,3aS,5aS,8aR)-1,3a,4,5a-tetramethyl-1,2,3,3a,5a,6,7,8-octahydrocyclopenta[c]pentalene, (1R,2R,5S,8S)-2,5,6,8-tetramethyltricyclo[6.3.0.01,5]undec-6-ene, (1R,2R,5S,8S)-2,5,6,8-tetramethyltricyclo(6.3.0.01,5)undec-6-ene, (1R,3aS,5aS,8aR)-1,3a,4,5a-Tetramethyl-1,2,3,3a,5a,6,7,8-octahydrocyclopenta(c)pentalene, RefChem:67691, Berkheyaradulene, 65372-78-3, Cyclopenta(a)pentalene, 1,2,3,3a,5a,6,7,8-octahydro-1,3a,4,5a-tetramethyl-, (S-(1alpha,3aalpha,5abeta,8aR*))-, Isocomene, (+/-)-, UF2Y987D5F, (+/-)-Isocomene, SCHEMBL29496466, C20477, Q27137092, CYCLOPENTA(C)PENTALENE, 1,2,3,3A,5A,6,7,8-OCTAHYDRO-1,3A,4,5A-TETRAMETHYL-, (1.ALPHA.,3A.ALPHA.,5A.BETA.,8AR*)-, CYCLOPENTA(C)PENTALENE, 1,2,3,3A,5A,6,7,8-OCTAHYDRO-1,3A,4,5A-TETRAMETHYL-, (1.ALPHA.,3A.ALPHA.,5A.BETA.,8AR*)-(+/-)-, REL-(1R,3AS,5AS,8AR)-1,2,3,3A,5A,6,7,8-OCTAHYDRO-1,3A,4,5A-TETRAMETHYLCYCLOPENTA(C)PENTALENE
Theoretical properties:
molecular_formula: C15H24
molecular_weight: 204.35 g/mol
exact_mass: 204.187800766 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 0
hydrogen_bond_acceptor_count: 0
rotatable_bond_count: 0
heavy_atom_count: 15
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
Descriptions:
pubchem: (-)-alpha-isocomene is a tricyclic sesquiterpene that is 1,2,3,3a,5a,6,7,8-octahydrocyclopenta[c]pentalene bearing four methyl substituents at positions 1, 3a, 4 and 5a. It has a role as a volatile oil component and a plant metabolite. It is a sesquiterpene and a carbotricyclic compound.
chebi: A tricyclic sesquiterpene that is 1,2,3,3a,5a,6,7,8-octahydrocyclopenta[<em>c</em>]pentalene bearing four methyl substituents at positions 1, 3a, 4 and 5a.
wikipedia: α-Isocomene synthase (EC 4.2.3.136, MrTPS2) is an enzyme with systematic name (2E,6E)-farnesyl-diphosphate diphosphate-lyase (cyclizing, (–)-α-isocomene-forming). This enzyme catalyses the following chemical reaction

(2E,6E)-farnesyl diphosphate 
  
    
      
        ⇌
      
    
    {\displaystyle \rightleftharpoons }
  
 (–)-α-isocomene + diphosphate
This enzyme is isolated from the roots of the plant Matricaria chamomilla var. recutita (chamomile).