Compound: Betulin
SMILES: O[C@@H]1C([C@H]2[C@]([C@@H]3[C@@]([C@]4([C@@H]([C@@H]5[C@@](CC[C@H]5C(=C)C)(CO)CC4)CC3)C)(C)CC2)(C)CC1)(C)C
InChIKey: FVWJYYTZTCVBKE-ROUWMTJPSA-N
Synonyms: Betulin, 473-98-3, Betulinol, Trochol, Betuline, Betulol, Betulinic alcohol, (+)-betulin, Lup-20(30)-ene-3beta,28-diol, NSC-4644, 6W70HN7X7O, ORISTRACT BTL, CP BETULIN, Lup-20(29)-ene-3,28-diol, (3beta)-, lup-20(29)-ene-3 beta,28-diol, CHEBI:3086, DTXSID101019934, (1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-3a-(hydroxymethyl)-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]chrysen-9-ol, (1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-3a-(hydroxymethyl)-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)chrysen-9-ol, RefChem:568020, DTXCID801477793, lup-20(29)-ene-3,28-diol, 3,28-diacetate, (3 beta)-, 207-475-5, Lup-20(29)-ene-3b,28-diol, MFCD00016802, (1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-3a-(Hydroxymethyl)-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)icosahydro-1H-cyclopenta[a]chrysen-9-ol, NSC 4644, (3beta)-lup-20(29)-ene-3,28-diol, Lup-20(29)-ene-3,28-diol, (3.beta.)-, (1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-3a-(hydroxymethyl)-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]chrysen-9-ol, (1R,2R,5S,8R,9R,10R,13R,14R,17S,19R)-5-(hydroxymethyl)-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}]henicosan-17-ol, SR-05000002167, EINECS 207-475-5, NSC4644, UNII-6W70HN7X7O, Botulin, AI3-62999, NSC692218, Lup-20(29)-ene-3.beta.,28-diol, Lup-20(30)-ene-3.beta.,28-diol, Betulin (Standard), Betulinol (obsol.), Betulin, 23, Betulin, >=98%, BETULIN [MI], Prestwick3_000990, Betulin, analytical standard, BSPBio_001059, CHEMBL23236, SCHEMBL131739, BPBio1_001165, MEGxp0_001726, orb1304514, orb3139432, ACon1_000091, BDBM23207, HY-N0083R, WLZ4627, HMS2098E21, 7372-31-8, EX-A3354, HY-N0083, MSK000520, s4754, SBB080743, Lup-20(29)-ene-3 ,28-diol, AKOS005267212, Lup-20(29)-ene-3beta ,28-diol, Lup-20(30)-ene-3beta ,28-diol, CCG-208619, CS-6156, EBC-615459, FB29605, GS-3254, LMPR0106140005, NSC-692218, NCGC00168803-01, NCGC00168803-02, NCGC00168803-04, (1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-3a-(hydroxymethyl)-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)-icosahydro-1H-cyclopenta[a]chrysen-9-ol, SY038977, AB00513988, B0803, NS00018049, (3.beta.)-Lup-20(29)-ene-3,28-diol, C08618, Lup-20(29)-ene-3,28-diol, (3beta )-, F547257, Q419726, SR-05000002167-2, SR-05000002167-3, BRD-K64874225-001-01-3, BRD-K64874225-001-04-7, (1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-3 a-(hydroxymethyl)-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)icosahydro-1H-cyclopenta[a]chrysen-9-ol, (1R,3AS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-3a-(Hydroxymethyl)-5a,5b,8,8,1 1a-pentamethyl-1-(prop-1-en-2-y  l)icosahydro-1H-cyclopenta[a]chrysen-9-ol, (5S,17S,1R,2R,8R,9R,10R,13R,14R,19R)-5-(hydroxymethyl)-1,2,14,18,18-pentamethy l-8-(1-methylvinyl)pentacyclo[11.8.0.0<2,10>.0<5,9>.0<14,19>]henicosan-17-ol
Theoretical properties:
molecular_formula: C30H50O2
molecular_weight: 442.7 g/mol
exact_mass: 442.381080833 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 2
hydrogen_bond_acceptor_count: 2
rotatable_bond_count: 2
heavy_atom_count: 32
topological_polar_surface_area: 40.5 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
boiling_point: 284.00 to 288.00 °C. @ 743.00 mm Hg
melting_point: 251 - 252 °C
Descriptions:
pubchem: Betulin is a pentacyclic triterpenoid that is lupane having a double bond at position 20(29) as well as 3beta-hydroxy and 28-hydroxymethyl substituents. It has a role as an antiviral agent, a metabolite, an analgesic, an antineoplastic agent and an anti-inflammatory agent. It is a diol and a pentacyclic triterpenoid. 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-hydroxymethyl substituents.
chembl: BETULIN is a small molecule listed in the ChEMBL database but has not progressed to an approved clinical phase.
wikipedia: Betulin is an abundant, naturally occurring triterpene. It is commonly isolated from the bark of birch trees, hence its name, from betula. It forms up to 30% of the dry weight of silver birch bark. It is also found in birch sap. Inonotus obliquus contains betulin.
The compound in the bark gives the tree its white color which appears to protect the tree from mid-winter overheating by the sun. As a result, birches are some of the northernmost occurring deciduous trees.