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  3. ethyl (2S,3aR,3bS,5aR,6R,8aS,8bS,9R)-2,9-dihydroxy-3a,5a-dimethyl-6-[(E,2R)-6-methylhept-3-en-2-yl]-1-oxo-3,3b,4,5,6,7,8,8a,8b,9-decahydroindeno[5,4-e]indene-2-carboxylate

SCS-C003180

ethyl (2S,3aR,3bS,5aR,6R,8aS,8bS,9R)-2,9-dihydroxy-3a,5a-dimethyl-6-[(E,2R)-6-methylhept-3-en-2-yl]-1-oxo-3,3b,4,5,6,7,8,8a,8b,9-decahydroindeno[5,4-e]indene-2-carboxylate

Pathway: Terpenoids Superclass: Steroids Class: Cholestane steroids
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Chemical Structure

Structure of ethyl (2S,3aR,3bS,5aR,6R,8aS,8bS,9R)-2,9-dihydroxy-3a,5a-dimethyl-6-[(E,2R)-6-methylhept-3-en-2-yl]-1-oxo-3,3b,4,5,6,7,8,8a,8b,9-decahydroindeno[5,4-e]indene-2-carboxylate
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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.
Download: SDF SMILES

Source Information

Haliclona oculata (NA)
Original source name: Haliclona (Haliclona) oculata
Kingdom Metazoa Phylum Porifera Class Demospongiae Order Haplosclerida Family Chalinidae Genus Haliclona Species Haliclona oculata
Hainan Island
DOI: 10.1021/np0600494  · Journal of Natural Products

Drug-likeness (Lipinski Ro5)

Molecular Weight
472.7 Da
Threshold ≤ 500
ALogP
4.86
Threshold ≤ 5
H-Bond Donors
2
Threshold ≤ 5
H-Bond Acceptors
5
Threshold ≤ 10
Passes Lipinski Rule of Five — drug-like candidate

Chemical Properties

Molecular Formula:
C29H44O5
Molecular Weight:
472.6660 Da
SMILES:
CCOC(=O)[C@]1(O)C[C@@]2(C)C(=C[C@H](O)[C@H]3[C@@H]4CC[C@H]([C@H](C)/C=C/CC(C)C)[C@@]4(C)CC[C@@H]32)C1=O
InChIKey:
WLOSXWARCGDQKV-KIKXXBTMSA-N
InChI:
InChI=1S/C29H44O5/c1-7-34-26(32)29(33)16-28(6)21-13-14-27(5)19(18(4)10-8-9-17(2)3)11-12-20(27)24(21)23(30)15-22(28)25(29)31/h8,10,15,17-21,23-24,30,33H,7,9,11-14,16H2,1-6H3/b10-8+/t18-,19-,20+,21+,23+,24+,27-,28-,29+/m1/s1
Calculated Properties
ALogP:
4.858 lipophilicity
TPSA:
83.83 Ų polar surface area
H-Bond Donors:
2
H-Bond Acceptors:
5
Rotatable Bonds:
6
Ring Count:
4 (0 aromatic)
Chiral Centers:
9
Fsp³:
0.7931 fraction sp³ carbon

Database Information

Compound ID:
SCS-C003180
NPClassifier Pathway:
Terpenoids
NPClassifier Superclass:
Steroids
NPClassifier Class:
Cholestane steroids
Glycoside:
No
NPClassifier Status:
Classified
External Links:
General chemistry
PubChem ChemSpider ChEMBL
Natural product databases
COCONUT NP Atlas CMNPD: CMNPD16081

Biological Activity Data

No bioactivity data available for this compound.

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Structure enlarged