JAZL/ChemGist-CHON huggingface dataset:
Compound: Cathinone
SMILES: O=C(c1ccccc1)[C@@H](N)C
InChIKey: PUAQLLVFLMYYJJ-ZETCQYMHSA-N
Synonyms: Cathinone, Norephedrone, d-Cathinone, 71031-15-7, (2S)-2-amino-1-phenylpropan-1-one, Catinona, Cathinonum, alpha-Aminopropiophenone, S-(-)-cathinone, 1-Propanone, 2-amino-1-phenyl-, (2S)-, (-)-alpha-Aminopropiophenone, J18.754B, C08301, 540EI4406J, Cathinine, CHEBI:4110, RefChem:574903, 1-propanone, 2-amino-1-phenyl, 1-Propanone, 2-amino-1-phenyl-, 2-Amino-1-phenyl-1-propanone, CX1Z9618HE, (-)-Cathinone, l-Cathinone, Cathinone [INN], (S)-2-Aminopropiophenone, (S)-(-)-Cathinone, 1-Propanone, 2-amino-1-phenyl-, (S)-, (-)-.alpha.-Aminopropiophenone, Cathinone (incb:green list), CATHINONE [INCB:GREEN LIST], Cathinonum [INN-Latin], Catinona [INN-Spanish], NCGC00168262-01, NCGC00168262-02, (2S)-2-Amino-1-phenyl-1-propanone, BRN 5247015, CCRIS 9310, DEA No. 1235, UNII-540EI4406J, S(-)-Cathinone, CATHINONE [MI], CATHINONE [MART.], CATHINONE [WHO-DD], S(-)-Cathinone (NIST), SCHEMBL34513, SCHEMBL6016818, SCHEMBL7301230, CATHINONE [USP IMPURITY], CHEMBL2104047, DTXSID0050427, SCHEMBL27262005, 2-Amino-1-phenyl-1-propanone #, PDSP1_001350, PDSP2_001334, DB01560, (2S)-2-amino-1-phenyl-propan-1-one, NS00001122, Q414242, AMFETAMINE SULFATE IMPURITY C [EP IMPURITY]
Theoretical properties:
molecular_formula: C9H11NO
molecular_weight: 149.19 g/mol
exact_mass: 149.084063974 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 1
hydrogen_bond_acceptor_count: 2
rotatable_bond_count: 2
heavy_atom_count: 11
topological_polar_surface_area: 43.1 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
physical_state: Pale yellow leaf from petroleum ether
color: Pale yellow leaf from petroleum ether
boiling_point: BP: 93 °C at 0.8 mm Hg
melting_point: 46.5 °C
solubility: Very soluble in ether, ethanol
Descriptions:
pubchem: Cathinone is the S stereoisomer of 2-aminopropiophenone. It has a role as a central nervous system stimulant and a psychotropic drug. It is a 2-aminopropiophenone and a monoamine alkaloid.
chebi: The <em>S</em> stereoisomer of 2-aminopropiophenone.
chembl: CATHINONE is a small molecule listed in the ChEMBL database and has reached clinical trial phase 2.0.
wikipedia: Cathinone (; also known as β-ketoamphetamine) is a monoamine alkaloid found in the shrub Catha edulis (khat) and is chemically similar to ephedrine, cathine, methcathinone and other amphetamines. It is probably the main contributor to the stimulant effect of Catha edulis. Cathinone differs from many other amphetamines in that it has a ketone functional group. Other phenethylamines that share this structure include the stimulants methcathinone, MDPV, mephedrone and the antidepressant bupropion.
SMILES: O=C(/C(=C/C=C/C(=C/C=C/C=C(/C=C/C=C(/C=C=C1C(O)(CC(OC(=O)C)CC1(C)C)C)\C)\C)/C)/C)CC23OC2(CC(CC3(C)C)O)C
InChIKey: SJWWTRQNNRNTPU-BWRPRJLXSA-N
Theoretical properties:
Physical properties:
Descriptions:
chebi: An epoxycarotenol that is found in brown seaweed and which exhibits anti-cancer, anti-diabetic, anti-oxidative and neuroprotective properties.
Compound: Fenobucarb
SMILES: O=C(Oc1c(cccc1)C(CC)C)NC
InChIKey: DIRFUJHNVNOBMY-UHFFFAOYSA-N
Synonyms: Fenobucarb, 3766-81-2, BPMC, Baycarb, Bassa, Barizon, 2-sec-Butylphenyl N-methylcarbamate, Fenobcarb, Carvil, 2-sec-Butylphenyl methylcarbamate, 2-(1-Methylpropyl)phenyl methylcarbamate, Geocarb 50EC, Methylcarbamic acid o-sec-butylphenyl ester, Phenol, 2-(1-methylpropyl)-, methylcarbamate, BAY 41637, o-sec-Butylphenyl methylcarbamate, Carbamic acid, methyl-, o-sec-butylphenyl ester, 2-(butan-2-yl)phenyl methylcarbamate, 5MS2P7M0CF, 2-Butylphenyl methylcarbamate, DTXSID4058077, o-sec-butylphenyl n-methylcarbamate, BAY-41637, 2-(butan-2-yl)phenyl N-methylcarbamate, Phenol, 2-(1-methylpropyl)-, 1-(N-methylcarbamate), CHEBI:34304, RefChem:598885, DTXCID0031845, 223-188-8, Hopcin, Osbac, 2-(Sec-butyl)phenyl methylcarbamate, (2-butan-2-ylphenyl) N-methylcarbamate, Bayer 41367C, Bayer 41637, MFCD00053081, 2-sek.Butylfenylester kyseliny methylkarbaminove, 2-sec-Butylphenyl-N-methylcarbamate, Fenobucarb 10 microg/mL in Cyclohexane, Fenobucarb [BSI:ISO], EINECS 223-188-8, UNII-5MS2P7M0CF, BRN 2052332, AI3-27212, baycarb (tm), 2-sek.Butylfenylester kyseliny methylkarbaminove [Czech], Fenobucarb (Standard), Methylcarbamic acid 2-sec-butylphenyl ester, FENOBUCARB [ISO], (+/-)-FENOBUCARB, SCHEMBL73674, 3766-81-2(solution), CHEMBL226650, orb1694046, SCHEMBL29368514, DIRFUJHNVNOBMY-UHFFFAOYSA-, FENOBUCARB, (+/-)-, HY-B0835R, 2-sec butylphenyl N-methylcarbamate, HY-B0835, MSK20257, 2-Sec-butylphenyl methylcarbamate #, 2-Sec. butylphenyl N-methylcarbamate, (2-sec-butylphenyl) n-methylcarbamate, AKOS015960925, AS-76198, SY110156, DB-049163, CS-0012849, NS00009809, Fenobucarb, PESTANAL(R), analytical standard, Q3268119, InChI=1/C12H17NO2/c1-4-9(2)10-7-5-6-8-11(10)15-12(14)13-3/h5-9H,4H2,1-3H3,(H,13,14)
Theoretical properties:
molecular_formula: C12H17NO2
molecular_weight: 207.27 g/mol
exact_mass: 207.125928785 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 1
hydrogen_bond_acceptor_count: 2
rotatable_bond_count: 4
heavy_atom_count: 15
topological_polar_surface_area: 38.3 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
Descriptions:
pubchem: Fenobucarb is a carbamate ester obtained by the formal condensation of 2-sec-butylphenol with methylcarbamic acid. It has a role as a herbicide, an insecticide, an agrochemical, an EC 3.1.1.7 (acetylcholinesterase) inhibitor and an environmental contaminant. It is functionally related to a 2-sec-butylphenol and a methylcarbamic acid.
chebi: A carbamate ester obtained by the formal condensation of 2-<em>sec</em>-butylphenol with methylcarbamic acid.
chembl: FENOBUCARB is a small molecule listed in the ChEMBL database but has not progressed to an approved clinical phase.
wikipedia: Fenobucarb is a carbamate insecticide, also widely known as BPMC. A pale yellow or pale red liquid, insoluble in water; used as an agricultural insecticide, especially for control of Hemipteran pests, on rice and cotton and moderately toxic for humans.
Compound: 108333-82-0
SMILES: O=C(O)C(NC(=O)CCN)Cc1nc[nH]c1
InChIKey: CQOVPNPJLQNMDC-UHFFFAOYSA-N
Synonyms: 108333-82-0, beta-Alanylhistidine, DTXSID50861860, RefChem:1079608, DTXCID90204277, Ribonuclease A, 9001-99-4, RIBONUCLEASE, ribonuclease A from bovine pancreas, 2-(3-aminopropanoylamino)-3-(1H-imidazol-5-yl)propanoic acid, DL-(3-aminopropanoyl)histidine, 2-(3-aminopropanamido)-3-(1H-imidazol-5-yl)propanoic acid, B-Ala-his-oh, Nuclease, ribo-, L-Histidine, N-.beta.-alanyl-, 2-(3-aminopropanoylamino)-3-(3H-imidazol-4-yl)propanoic acid, RNase A,bovine pancreas, L-histidine, N-beta-alanyl, SCHEMBL33768, 7683-28-5, CHEMBL18545, L-Histidine, .beta.-alanyl-, SCHEMBL1160796, CQOVPNPJLQNMDC-UHFFFAOYSA-N, ss-Alanyl-L-Histidine [Carnosine], OAH-3085, MFCD00131791, NSC524045, AKOS015905612, AKOS030238597, DA-56585, DA-57439, NCI60_004277, SY078156, NS00014799, Ribonuclease A from bovine pancreas(Purified), EN300-717716, BRD-A96051074-001-02-2, 2-(3-aminopropanamido)-3-(1H-imidazol-4-yl)propanoic acid, 2-(3-amino-propanoylamino)-3-(1H-imidazol-4-yl)-propionic acid, L-Carnosin, L-Carnosine, Beta-Alanyl-L-histidine, Beta-Ala-His-OH
Theoretical properties:
molecular_formula: C9H14N4O3
molecular_weight: 226.23 g/mol
exact_mass: 226.10659032 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 4
hydrogen_bond_acceptor_count: 5
rotatable_bond_count: 6
heavy_atom_count: 16
topological_polar_surface_area: 121 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
Descriptions:
chebi: A dipeptide that is the <em>N</em>-(β-alanyl) derivative of <small>L</small>-histidine.
chembl: Unnamed Compound is a small molecule listed in the ChEMBL database but has not progressed to an approved clinical phase.
wikipedia: This is a list of the National Register of Historic Places listings in Oconee County, South Carolina.
This is intended to be a complete list of the properties and districts on the National Register of Historic Places in Oconee County, South Carolina, United States.  The locations of National Register properties and districts for which the latitude and longitude coordinates are included below, may be seen on a map.
There are 24 properties and districts listed on the National Register in the county.  Another 2 properties were once listed but have been removed.
          This National Park Service list is complete through NPS recent listings posted April 10, 2026.
SMILES: O=C(O)/C=C(/C=C/C=C(/C=C/C1=C(CCCC1(C)C)C)\C)\C
InChIKey: SHGAZHPCJJPHSC-YCNIQYBTSA-N
Theoretical properties:
Physical properties:
Descriptions:
chebi: A retinoic acid in which all four exocyclic double bonds have <i>E</i>- (<i>trans</i>-) geometry.
chembl: TRETINOIN is a small molecule listed in the ChEMBL database and has reached clinical trial phase 4.0.
SMILES: Oc1cc2c([C@@H]3[C@H]([C@H]4[C@]([C@@H](O)[C@@H](C4)O)(C)CC3)CC2)cc1
InChIKey: PROQIPRRNZUXQM-ZXXIGWHRSA-N
Theoretical properties:
Physical properties:
Descriptions:
chebi: A 3-hydroxy steroid that is estra-1,3,5(10)-trien-3-ol substituted by additional hydroxy groups at positions 16 and 17 (16α,17β-stereoisomer).
chembl: ESTRIOL is a small molecule listed in the ChEMBL database and has reached clinical trial phase 4.0.
Compound: CORONENE
SMILES: c12c3c4c5c6ccc4ccc3ccc1ccc7c2c5c(cc7)cc6
InChIKey: VPUGDVKSAQVFFS-UHFFFAOYSA-N
Synonyms: CORONENE, 191-07-1, Hexabenzobenzene, superbenzene, Dibenzo(ghi,pqr)perylene, Dibenzo[ghi,pqr]perylene, 7YY0X5XT1W, DTXSID5047740, NSC-90725, CHEBI:29863, RefChem:579250, DTXCID5027724, 205-881-7, C24H12, MFCD00004134, 1,12:4,5:8,9-Triethenotriphenylene,Dibenzo(ghi,pqr)perylene, Coronene; Circumbenzene; NSC 90725, CCRIS 908, EINECS 205-881-7, NSC 90725, UNII-7YY0X5XT1W, Coronene, 97%, CORONENE (purity), CORONENE [IARC], CORONENE [MI], SCHEMBL26856, SCHEMBL510787, orb3023631, SCHEMBL1815373, SCHEMBL29363009, SCHEMBL29563511, MSK4361, NSC90725, Coronene 10 microg/mL in Cyclohexane, AKOS015840942, Coronene 10 microg/mL in Acetonitrile, CS-W012132, FC62148, Coronene, purified by sublimation, 99%, AS-56034, SY051583, DB-002675, C1961, NS00004856, ST45022219, C19375, Coronene, BCR(R) certified Reference Material, F448567, Q420614, InChI=1/C24H12/c1-2-14-5-6-16-9-11-18-12-10-17-8-7-15-4-3-13(1)19-20(14)22(16)24(18)23(17)21(15)19/h1-12
Theoretical properties:
molecular_formula: C24H12
molecular_weight: 300.4 g/mol
exact_mass: 300.093900383 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 0
hydrogen_bond_acceptor_count: 0
rotatable_bond_count: 0
heavy_atom_count: 24
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
Descriptions:
pubchem: Coronene is a ortho- and peri-fused polycyclic arene that consists of six peri-fused benzene rings.
chebi: A <em>ortho</em>- and <em>peri</em>-fused polycyclic arene that consists of six <em>peri</em>-fused benzene rings.
wikipedia: Coronene (also known as superbenzene and cyclobenzene) is a polycyclic aromatic hydrocarbon (PAH) comprising seven peri-fused benzene rings. Its chemical formula is C24H12. It is a yellow material that dissolves in common solvents including benzene, toluene, and dichloromethane. Its solutions emit blue light fluorescence under UV light. It has been used as a solvent probe, similar to pyrene.
The compound is of theoretical interest to organic chemists because of its aromaticity. It can be described by 20 resonance structures or by a set of three mobile Clar sextets. In the Clar sextet case,  most stable structure for coronene has only  three isolated outer sextets as fully aromatic although superaromaticity would still be possible when these sextets are able to migrate into next ring.
Compound: N,N-Diethylhydroxylamine
SMILES: ON(CC)CC
InChIKey: FVCOIAYSJZGECG-UHFFFAOYSA-N
Synonyms: N,N-Diethylhydroxylamine, 3710-84-7, DIETHYLHYDROXYLAMINE, Ethanamine, N-ethyl-N-hydroxy-, 314I05EDVH, DTXSID2027543, DTXCID107543, RefChem:161197, 223-055-4, N-Hydroxydiethylamine, N,N-Diethylhydroxyamine, Hydroxylamine, N,N-diethyl-, N-ethyl-N-hydroxyethanamine, MFCD00002126, hydroxydiethylamine, CCRIS 964, EINECS 223-055-4, BRN 1731349, UNII-314I05EDVH, AI3-28026, HSDB 6819, Pennstop 1866, n,n-diethyl-hydroxylamine, EC 223-055-4, SCHEMBL57247, 4-04-00-03304 (Beilstein Handbook Reference), SCHEMBL243598, (C2H5)2NOH, SCHEMBL2442627, SCHEMBL3669514, CHEMBL3184786, FVCOIAYSJZGECG-UHFFFAOYSA-, N,N-Diethylhydroxylamine solution, 1-[Ethyl(hydroxy)amino]ethane #, N,N-Diethylhydroxylamine, >=98%, Tox21_200264, AKOS015903887, CS-W013744, N,N-DIETHYLHYDROXYLAMINE [HSDB], NCGC00248584-01, NCGC00257818-01, CAS-3710-84-7, D1178, D1339, NS00009592, E83007, EN300-136085, F129600, Q3334148, InChI=1/C4H11NO/c1-3-5(6)4-2/h6H,3-4H2,1-2H3, N,N-Diethylhydroxylamine (ca. 85% in Water, ca. 8.6mol/L)
Theoretical properties:
molecular_formula: C4H11NO
molecular_weight: 89.14 g/mol
exact_mass: 89.084063974 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 1
hydrogen_bond_acceptor_count: 2
rotatable_bond_count: 2
heavy_atom_count: 6
topological_polar_surface_area: 23.5 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
physical_state: Liquid
color: Liquid
boiling_point: 130 °C
melting_point: 10 °C
density: 0.8669 at 20 °C
flash_point: 113 °F
vapor_pressure: 0.02 [mmHg]
Descriptions:
chembl: Unnamed Compound is a small molecule listed in the ChEMBL database but has not progressed to an approved clinical phase.
wikipedia: Diethylhydroxylamine (DEHA) is an organic compound with the formula (C2H5)2NOH. Strictly, this is N,N-diethylhydroxylamine. It has an isomer, N,O-diethylhydroxylamine with the formula EtNHOEt. Pure N,N-diethylhydroxylamine is a colorless liquid, although it is usually encountered as a colourless-to-yellow solution in water with an amine-like odor. 
DEHA can be synthesised from a reaction between triethylamine and a peroxide.
SMILES: O=C(O)CCCCCCC/C=C\CCCCCCCC
InChIKey: ZQPPMHVWECSIRJ-KTKRTIGZSA-N
Theoretical properties:
Physical properties:
Descriptions:
chebi: An octadec-9-enoic acid in which the double bond at C-9 has <i>Z</i> (<i>cis</i>) stereochemistry.
chembl: OLEIC ACID is a small molecule listed in the ChEMBL database and has reached clinical trial phase 2.0.
Compound: DIAZOMETHANE
SMILES: [N+](#N)[C-]
InChIKey: QDZARNQKIZUXDK-UHFFFAOYSA-N
Synonyms: DIAZOMETHANE, Azimethylene, 334-88-3, Acomethylene, Methane, diazo-, Diazonium methylide, 60A625P70P, DTXSID0024008, CHEBI:73716, azomethylene, RefChem:388924, DTXCID604008, 206-382-7, EINECS 206-382-7, METHANE,DIAZO, CCRIS 205, HSDB 1628, BRN 0102415, diazomethan, diazo methane, diazo-methane, CNN radical, UNII-60A625P70P, CNN, DIAZOMETHYL GROUP, DIAZOMETHANE [MI], SCHEMBL258, DIAZOMETHANE [HSDB], DIAZOMETHANE [IARC], 4-01-00-03056 (Beilstein Handbook Reference), SCHEMBL1038531, SCHEMBL4835369, SCHEMBL8351385, AKOS015901056, 186581-53-3, DB-264755, NS00029498, C19387, Q413683
Theoretical properties:
molecular_formula: CH2N2
molecular_weight: 42.040 g/mol
exact_mass: 42.021798072 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: 2 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
physical_state: Yellow gas [Note: Shipped as a liquefied compressed gas]
color: Yellow gas [Note: Shipped as a liquefied compressed gas]
odor: Musty odor
boiling_point: -9 °F at 760 mmHg (NIOSH, 2024)
melting_point: -229 °F (NIOSH, 2024)
density: 1.45
solubility: Reacts with water (NIOSH, 2024)
flash_point: Flammable gas
vapor_pressure: greater than 1 atm (NIOSH, 2024)
Descriptions:
pubchem: Diazomethane is the simplest diazo compound, in which a diazo group is attached to a methylene group. It has a role as an alkylating agent, an antineoplastic agent, a carcinogenic agent and a poison.
wikipedia: Diazomethane is an organic chemical compound with the formula CH2N2, discovered by German chemist Hans von Pechmann in 1894. It is the simplest diazo compound. In the pure form at room temperature, it is an extremely sensitive explosive yellow gas; thus, it is almost universally used as a solution in diethyl ether.  The compound is a popular methylating agent in the laboratory, but it is too hazardous to be employed on an industrial scale without special precautions. Use of diazomethane has been significantly reduced by the introduction of the safer and equivalent reagent trimethylsilyldiazomethane.
SMILES: O=C1C=C([C@](O)(/C=C/C(=C/C(=O)O)/C)C(C1)(C)C)C
InChIKey: JLIDBLDQVAYHNE-IBPUIESWSA-N
Theoretical properties:
Physical properties:
Descriptions:
chebi: A 2-<i>trans</i>-abscisic acid with (<i>S</i>)-configuration at the chiral centre.
Compound: azulene
SMILES: c12-c(ccccc1)ccc2
InChIKey: CUFNKYGDVFVPHO-UHFFFAOYSA-N
Synonyms: azulene, 275-51-4, Cyclopentacycloheptene, Azunamic, Bicyclo[5.3.0]decapentaene, azulen, Bicyclo(5.3.0)decapentaene, 82R6M9MGLP, Bicyclo(5.3.0)-1,3,5,7,9-decapentaene, Bicyclo(5.3.0)-deca-2,4,6,8,10-pentaene, NSC-89248, DTXSID2059770, CHEBI:31249, RefChem:116159, DTXCID7037686, 205-993-6, MFCD00003810, Azulene (JAN), AZULENE [JAN], EINECS 205-993-6, NSC 89248, UNII-82R6M9MGLP, Azulene (Standard), Azulene, 99%, AZULENE [MI], AZULENE [MART.], AZULENE [WHO-DD], SCHEMBL8463, Azulene, analytical standard, SCHEMBL26516, SCHEMBL183516, SCHEMBL195477, SCHEMBL348614, Azusalen [as sodium sulfonate], orb1299207, SCHEMBL1510123, SCHEMBL1968724, SCHEMBL5586324, SCHEMBL7190249, SCHEMBL9381015, CHEMBL3272628, SCHEMBL23805068, HY-B0055R, HY-B0055, NSC89248, SBB056611, AKOS015840881, EBC-616622, FC66428, CS-15638, SY049872, Bicyclo[5.3.0]-1,5,7,9-decapentaene, DB-047243, A0634, Bicyclo(0.3.5)deca-1,3,5,7,9-pentaene, CS-0006517, NS00013373, ST50411971, Azulene, standard for GC, >=99.0% (GC), bicyclo[5.3.0]deca-2,4,6,8,10-pentaene, C13408, D09768, Q144362, SR-01000944574, SR-01000944574-1, BICYCLO-(0.3.5)-DECA-1,3,5,7,9-PENTAENE, BICYCLO-(5.3.0)-DECA-2,4,6,8,10-PENTAENE, InChI=1/C10H8/c1-2-5-9-7-4-8-10(9)6-3-1/h1-8, 82451-56-7
Theoretical properties:
molecular_formula: C10H8
molecular_weight: 128.17 g/mol
exact_mass: 128.062600255 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 0
hydrogen_bond_acceptor_count: 0
rotatable_bond_count: 0
heavy_atom_count: 10
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
Descriptions:
pubchem: Azulene is a mancude carbobicyclic parent consisting of a cycloheptatriene and cyclopentadiene rings. It has a role as a volatile oil component and a plant metabolite. It is an ortho-fused bicyclic arene, a member of azulenes and a mancude carbobicyclic parent.
chebi: A mancude carbobicyclic parent consisting of a cycloheptatriene and cyclopentadiene rings.
chembl: Unnamed Compound is a small molecule listed in the ChEMBL database but has not progressed to an approved clinical phase.
wikipedia: Azulene is an aromatic organic compound and an isomer of naphthalene. Naphthalene is colourless, whereas azulene is dark blue. The compound is named after its colour, as "azul" is Spanish for blue. Two terpenoids, vetivazulene (4,8-dimethyl-2-isopropylazulene) and guaiazulene (1,4-dimethyl-7-isopropylazulene), that feature the azulene skeleton are found in nature as constituents of pigments in mushrooms, guaiac wood oil, and some marine invertebrates.
Azulene has a long history, dating back to the 15th century as the azure-blue chromophore obtained by steam distillation of German chamomile. The chromophore was discovered in yarrow and wormwood and named in 1863 by Septimus Piesse. Its structure was first reported by Lavoslav Ružička, followed by its organic synthesis in 1937 by Placidus Plattner.
Compound: norgestrel
SMILES: O=C1C=C2[C@@H]([C@@H]3[C@H]([C@H]4[C@](C(O)(C#C)CC4)(CC)CC3)CC2)CC1
InChIKey: WWYNJERNGUHSAO-CULCCENASA-N
Synonyms: norgestrel, FH-122A, SH-850, NSC-757251, SH-70850, SCHEMBL37118, CHEMBL2107797, WWYNJERNGUHSAO-CULCCENASA-N, Q7051185, (8R,9S,10R,13S,14S)-13-ethyl-17-ethynyl-17-hydroxy-1,2,6,7,8,9,10,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-3-one
Theoretical properties:
molecular_formula: C21H28O2
molecular_weight: 312.4 g/mol
exact_mass: 312.208930132 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 1
hydrogen_bond_acceptor_count: 2
rotatable_bond_count: 2
heavy_atom_count: 23
topological_polar_surface_area: 37.3 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
physical_state: Crystals from methanol
color: Crystals from methanol
melting_point: 205-207 °C
solubility: In water, 1.73 mg/L, temp not stated.
Descriptions:
pubchem: Norgestrel can cause developmental toxicity according to state or federal government labeling requirements.
chebi: A 3-oxo-Δ<small><sup>4</small></sup> steroid that is gon-4-en-3-one that carries ethyl, hydroxy, and ethynyl groups at positions 13, 17 and 17, respectively.
chembl: NORGESTREL is a small molecule listed in the ChEMBL database and has reached clinical trial phase 4.0.
wikipedia: Norgestrel, sold under the brand name Opill among others, is a progestin which is used in birth control pills. It is often combined with the estrogen ethinylestradiol, marketed as Ovral. It is also used in menopausal hormone therapy. It is taken by mouth.
Side effects of norgestrel include menstrual irregularities, headaches, nausea, and breast tenderness. The most common side effects of the norgestrel include irregular bleeding, headaches, dizziness, nausea, increased appetite, abdominal pain, cramps, or bloating. Norgestrel is a progestin, or a synthetic progestogen, and hence is an agonist of the progesterone receptor, the biological target of progestogens like progesterone. It has weak androgenic activity and no other important hormonal activity.
Norgestrel was patented in 1961 and came into medical use, specifically in birth control pills, in 1966. It was subsequently introduced for use in menopausal hormone therapy as well. Norgestrel is sometimes referred to as a "second-generation" progestin. It is marketed widely throughout the world. Norgestrel is available as a generic medication. In 2022, the version with ethinylestradiol was the 264th most commonly prescribed medication in the United States, with more than 1 million prescriptions. In July 2023, the US Food and Drug Administration (FDA) approved norgestrel for over-the-counter sale.