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  3. 3-[(1R,2R,4R,4aR,4bR,5S,6aR,7S,10aR,12aR)-2-[(2R)-1,2-dihydroxypropan-2-yl]-4,5,7-trihydroxy-1,4a,4b,6a,9,9-hexamethyl-3,4,5,6,7,8,10,10a,10b,12a-decahydro-2H-chrysen-1-yl]propanoic acid

SCS-C002601

3-[(1R,2R,4R,4aR,4bR,5S,6aR,7S,10aR,12aR)-2-[(2R)-1,2-dihydroxypropan-2-yl]-4,5,7-trihydroxy-1,4a,4b,6a,9,9-hexamethyl-3,4,5,6,7,8,10,10a,10b,12a-decahydro-2H-chrysen-1-yl]propanoic acid

Pathway: Terpenoids Superclass: Triterpenoids Class: Oleanane triterpenoids
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Chemical Structure

Structure of 3-[(1R,2R,4R,4aR,4bR,5S,6aR,7S,10aR,12aR)-2-[(2R)-1,2-dihydroxypropan-2-yl]-4,5,7-trihydroxy-1,4a,4b,6a,9,9-hexamethyl-3,4,5,6,7,8,10,10a,10b,12a-decahydro-2H-chrysen-1-yl]propanoic acid
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3D conformers are computationally generated from SMILES by RDKit for visualization and download; they are not experimental crystal or NMR structures.
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Source Information

Phomopsis sp. (fungus)
Kingdom Fungi Phylum Ascomycota Class Sordariomycetes Order Diaporthales Family Diaporthaceae Genus Phomopsis Species NA
Dongzhaigang
DOI: 10.1016/j.phytochem.2007.08.010  · Phytochemistry

Drug-likeness (Lipinski Ro5)

Molecular Weight
522.7 Da
Threshold ≤ 500
ALogP
3.36
Threshold ≤ 5
H-Bond Donors
6
Threshold ≤ 5
H-Bond Acceptors
6
Threshold ≤ 10
2 violations (MW, HBD) — not drug-like by Ro5

Chemical Properties

Molecular Formula:
C30H50O7
Molecular Weight:
522.7230 Da
SMILES:
CC1(C)C[C@@H]2C3C=C[C@@H]4[C@@](C)(CCC(=O)O)[C@H]([C@@](C)(O)CO)C[C@@H](O)[C@@]4(C)[C@]3(C)[C@@H](O)C[C@@]2(C)[C@@H](O)C1
InChIKey:
UDEQLICEDFYIBR-XVVUDCCVSA-N
InChI:
InChI=1S/C30H50O7/c1-25(2)13-18-17-8-9-19-26(3,11-10-24(35)36)20(28(5,37)16-31)12-21(32)30(19,7)29(17,6)23(34)15-27(18,4)22(33)14-25/h8-9,17-23,31-34,37H,10-16H2,1-7H3,(H,35,36)/t17?,18-,19-,20-,21-,22+,23+,26-,27-,28+,29+,30+/m1/s1
Calculated Properties
ALogP:
3.364 lipophilicity
TPSA:
138.45 Ų polar surface area
H-Bond Donors:
6
H-Bond Acceptors:
6
Rotatable Bonds:
5
Ring Count:
4 (0 aromatic)
Chiral Centers:
12
Fsp³:
0.9000 fraction sp³ carbon

Database Information

Compound ID:
SCS-C002601
NPClassifier Pathway:
Terpenoids
NPClassifier Superclass:
Triterpenoids
NPClassifier Class:
Oleanane triterpenoids
Glycoside:
No
NPClassifier Status:
Classified
External Links:
General chemistry
PubChem ChemSpider ChEMBL
Natural product databases
COCONUT NP Atlas CMNPD: CMNPD18585

Biological Activity Data

No bioactivity data available for this compound.

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Structure enlarged