Compound: betulinic acid
SMILES: O=C(O)[C@]12[C@@H]([C@@H]3[C@@]([C@]4([C@@H]([C@@]5([C@H](C([C@@H](O)CC5)(C)C)CC4)C)CC3)C)(C)CC1)[C@H](C(=C)C)CC2
InChIKey: QGJZLNKBHJESQX-FZFNOLFKSA-N
Synonyms: betulinic acid, 472-15-1, Mairin, Betulic acid, Lupatic Acid, als-357, 3-Hydroxylup-20(29)-en-28-oic acid, beta-betulinic acid, NSC-113090, NSC-677578, 3beta-Hydroxy-lup-20(29)-en-28-oic acid, 4G6A18707N, CHEBI:3087, DTXSID80861974, (1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-9-hydroxy-5a,5b,8,8,11a-pentamethyl-1-prop-1-en-2-yl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysene-3a-carboxylic acid, NSC113090, (1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-9-hydroxy-5a,5b,8,8,11a-pentamethyl-1-prop-1-en-2-yl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta(a)chrysene-3a-carboxylic acid, 3 Epi betulinic Acid, RefChem:5606, DTXCID301506361, 3-Hydroxy-lup-20(29)-en-28-oic Acid, (3beta)-3-Hydroxy-lup-20(29)-en-28-oic Acid, 207-448-8, Betulinicacid, MFCD00009619, 3beta-Hydroxy-20(29)-lupaene-28-oic acid, .beta.-betulinic acid, Lupatic acid;Betulic acid, NSC677578, (3beta)-3-hydroxylup-20(29)-en-28-oic acid, 3beta-hydroxylup-20(29)-en-28-oic acid, CHEMBL269277, (1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-9-hydroxy-1-isopropenyl-5a,5b,8,8,11a-pentamethyl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysene-3a-carboxylic acid, (1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-9-hydroxy-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)icosahydro-1H-cyclopenta[a]chrysene-3a-carboxylic acid, SMR000445624, NSC 113090, CCRIS 6748, EINECS 207-448-8, NSC 677578, betulinic-acid, Betulinic acid?, UNII-4G6A18707N, Prestwick_95, Betulinic Acid, 24, Lup-20(29)-en-28-oic acid, 3-hydroxy-, (3beta)-, Prestwick0_000417, Prestwick1_000417, Prestwick2_000417, Prestwick3_000417, Betulinic acid (Standard), BETULINIC ACID [MI], Lup-20(29)-en-28-oic acid, 3-hydroxy-, (3.beta.)-, SCHEMBL61767, BSPBio_000374, BSPBio_001587, cid_64971, MLS000728510, MLS006011257, SPBio_002313, BPBio1_000412, GTPL3945, orb1304966, orb3139434, BDBM23208, GLXC-06559, HMS1569C16, HMS1791P09, HMS1989P09, HMS2096C16, HMS2232K03, HMS3402P09, HMS6018J07, Betulinic acid, analytical standard, Betulinic acid, >=98% (HPLC), MSK40138, HB3799, HY-10529R, s3603, STL570261, AKOS015920276, Betulinic acid, technical grade, 90%, CCG-208159, CS-1216, DB12480, EBC-445041, FB16425, LMPR0106140004, RL9-080, SMP2_000205, NCGC00163409-02, NCGC00163409-03, NCGC00163409-09, NCGC00163409-12, (1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-9-hydroxy-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)-icosahydro-1H-cyclopenta[a]chrysene-3a-carboxylic acid, (1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-9-hydroxy-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)icosahydro-3aH-cyclopenta[a]chrysene-3a-carboxylic acid, BP-25391, DS-15257, HY-10529, SY058034, 3b-Hydroxy-20(29)-lupaene-28-oic acid, NS00042781, C08619, M01408, Lup-20(29)-en-28-oic acid, 3beta -hydroxy-, (3|_)-3-Hydroxylup-20(29)-en-28-oic acid, 3-Hydroxy-(3beta)-Lup-20(29)-en-28-oic acid, Q384111, SR-01000779609, SR-01000779609-3, BRD-K45401373-001-05-0, BRD-K45401373-001-20-9, BRD-K45401373-001-22-5, (3.BETA.)-3-HYDROXYLUP-20(29)-EN-28-OIC ACID, (1R,2R,5S,8R,9R,10R,13R,14R,17S,19R)-17-hydroxy-1,2,14,18,18-pentamethyl-8-(prop-1-en-2-yl)pentacyclo[11.8.0.0^{2,10}.0^{5,9}.0^{14,19}]henicosane-5-carboxylic acid, (1R,3 aS,5aR,5bR,7aR,9S,11aR,11bR,13 aR,13bR)-9-hydroxy-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)icosahydro-1H-cyclopenta[a]chrysene-3a-carboxylic acid, (1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-9-Hydroxy-1-isopropenyl-5a,5b,8,8,11a-pentamethyl-eicosahydro-cyclopenta[a]chrysene-3a-carboxylic acid, (1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-9-hydroxy-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)icosahydro-1H-cyclopenta[a]chrysene-3a-carboxylicacid, (1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-9-hydroxy-5a,5b,8,8,11a-pentamethyl-1-prop-1-en-2-yl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysene-3a-carboxylicacid, 06L
Theoretical properties:
molecular_formula: C30H48O3
molecular_weight: 456.7 g/mol
exact_mass: 456.36034539 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 2
hydrogen_bond_acceptor_count: 3
rotatable_bond_count: 2
heavy_atom_count: 33
topological_polar_surface_area: 57.5 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
melting_point: 316 - 318 °C
Descriptions:
pubchem: Betulinic acid is a pentacyclic triterpenoid that is lupane having a double bond at position 20(29) as well as 3beta-hydroxy and 28-carboxy substituents. It is found in the bark and other plant parts of several species of plants including Syzygium claviflorum. It exhibits anti-HIV, antimalarial, antineoplastic and anti-inflammatory properties. It has a role as an antineoplastic agent, an antimalarial, an EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor, an anti-HIV agent, an anti-inflammatory agent and a plant metabolite. It is a pentacyclic triterpenoid and a hydroxy monocarboxylic acid. It derives from a hydride of a lupane.
chebi: A pentacyclic triterpenoid that is lupane having a double bond at position 20(29) as well as 3β-hydroxy and 28-carboxy substituents. It is found in the bark and other plant parts of several species of plants including <em>Syzygium claviflorum</em>. It exhibits anti-HIV, antimalarial, antineoplastic and anti-inflammatory properties.
chembl: BETULINIC ACID is a small molecule listed in the ChEMBL database and has reached clinical trial phase 1.0.
wikipedia: Betulinic acid is a naturally occurring pentacyclic triterpenoid which has antiretroviral, antimalarial, and anti-inflammatory properties, as well as a more recently discovered potential as an anticancer agent, by inhibition of topoisomerase. It is found in the bark of several species of plants, principally the white birch (Betula pubescens) from which it gets its name, same as the bracket fungus Fomitopsis betulina, but also the ber tree (Ziziphus mauritiana), selfheal (Prunella vulgaris), the tropical carnivorous plants Triphyophyllum peltatum and Ancistrocladus heyneanus, Diospyros leucomelas, a member of the persimmon family, Tetracera boiviniana, the jambul (Syzygium formosanum), flowering quince (Pseudocydonia sinensis, former Chaenomeles sinensis KOEHNE), 
rosemary,
and Pulsatilla chinensis.