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  3. (1S,3R,8S,9S,10R,11R,13S,14S,17R)-3-acetyloxy-1,11-dihydroxy-10-methyl-17-[(1R)-1-[(1S,2R)-2-methyl-2-[(2R)-3-methylbutan-2-yl]cyclopropyl]ethyl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-13-carboxylic acid

SCS-C003183

(1S,3R,8S,9S,10R,11R,13S,14S,17R)-3-acetyloxy-1,11-dihydroxy-10-methyl-17-[(1R)-1-[(1S,2R)-2-methyl-2-[(2R)-3-methylbutan-2-yl]cyclopropyl]ethyl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-13-carboxylic acid

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

Structure of (1S,3R,8S,9S,10R,11R,13S,14S,17R)-3-acetyloxy-1,11-dihydroxy-10-methyl-17-[(1R)-1-[(1S,2R)-2-methyl-2-[(2R)-3-methylbutan-2-yl]cyclopropyl]ethyl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-13-carboxylic 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.
Download: SDF SMILES

Source Information

Sinularia dissecta (NA)
Kingdom Metazoa Phylum Cnidaria Class Anthozoa Order Malacalcyonacea Family Sinulariidae Genus Sinularia Species Sinularia dissecta
Hainan Island
DOI: 10.1016/j.steroids.2005.01.001  · Steroids

Drug-likeness (Lipinski Ro5)

Molecular Weight
530.7 Da
Threshold ≤ 500
ALogP
5.46
Threshold ≤ 5
H-Bond Donors
3
Threshold ≤ 5
H-Bond Acceptors
5
Threshold ≤ 10
2 violations (MW, ALogP) — not drug-like by Ro5

Chemical Properties

Molecular Formula:
C32H50O6
Molecular Weight:
530.7460 Da
SMILES:
CC(=O)O[C@@H]1CC2=CC[C@@H]3[C@H]([C@H](O)C[C@]4(C(=O)O)[C@@H]([C@H](C)[C@@H]5C[C@]5(C)[C@H](C)C(C)C)CC[C@@H]34)[C@@]2(C)[C@@H](O)C1
InChIKey:
DZXQTTROFDWABI-WNJZUXGUSA-N
InChI:
InChI=1S/C32H50O6/c1-16(2)18(4)30(6)14-25(30)17(3)23-10-11-24-22-9-8-20-12-21(38-19(5)33)13-27(35)31(20,7)28(22)26(34)15-32(23,24)29(36)37/h8,16-18,21-28,34-35H,9-15H2,1-7H3,(H,36,37)/t17-,18+,21+,22-,23+,24-,25-,26+,27-,28+,30+,31+,32-/m0/s1
Calculated Properties
ALogP:
5.458 lipophilicity
TPSA:
104.06 Ų polar surface area
H-Bond Donors:
3
H-Bond Acceptors:
5
Rotatable Bonds:
6
Ring Count:
5 (0 aromatic)
Chiral Centers:
13
Fsp³:
0.8750 fraction sp³ carbon

Database Information

Compound ID:
SCS-C003183
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: CMNPD15419

Biological Activity Data

No bioactivity data available for this compound.

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Structure enlarged