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  3. [(3R,4S,5S,6S)-4,5-dihydroxy-6-[[(3S,8S,9S,10S,13R,14S,17R)-10-(hydroxymethyl)-13-methyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl]oxy]oxan-3-yl] acetate

SCS-C004682

[(3R,4S,5S,6S)-4,5-dihydroxy-6-[[(3S,8S,9S,10S,13R,14S,17R)-10-(hydroxymethyl)-13-methyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl]oxy]oxan-3-yl] acetate

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

Structure of [(3R,4S,5S,6S)-4,5-dihydroxy-6-[[(3S,8S,9S,10S,13R,14S,17R)-10-(hydroxymethyl)-13-methyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl]oxy]oxan-3-yl] acetate
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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

Junceella juncea (gorgonian coral)
Kingdom Metazoa Phylum Cnidaria Class Anthozoa Order Scleralcyonacea Family Ellisellidae Genus Junceella Species Junceella juncea
South China Sea
DOI: 10.1248/cpb.52.1476  · Chemical and Pharmaceutical Bulletin

Drug-likeness (Lipinski Ro5)

Molecular Weight
576.8 Da
Threshold ≤ 500
ALogP
5.40
Threshold ≤ 5
H-Bond Donors
3
Threshold ≤ 5
H-Bond Acceptors
7
Threshold ≤ 10
2 violations (MW, ALogP) — not drug-like by Ro5

Chemical Properties

Molecular Formula:
C34H56O7
Molecular Weight:
576.8150 Da
SMILES:
CC(=O)O[C@@H]1CO[C@@H](O[C@H]2CC[C@@]3(CO)C(=CC[C@@H]4[C@@H]3CC[C@]3(C)[C@@H]([C@H](C)CCCC(C)C)CC[C@@H]43)C2)[C@@H](O)[C@@H]1O
InChIKey:
VECOUZYKNOVLDX-BRWLXSOXSA-N
InChI:
InChI=1S/C34H56O7/c1-20(2)7-6-8-21(3)26-11-12-27-25-10-9-23-17-24(13-16-34(23,19-35)28(25)14-15-33(26,27)5)41-32-31(38)30(37)29(18-39-32)40-22(4)36/h9,20-21,24-32,35,37-38H,6-8,10-19H2,1-5H3/t21-,24+,25+,26-,27+,28+,29-,30-,31+,32+,33-,34-/m1/s1
Calculated Properties
ALogP:
5.395 lipophilicity
TPSA:
105.45 Ų polar surface area
H-Bond Donors:
3
H-Bond Acceptors:
7
Rotatable Bonds:
9
Ring Count:
5 (0 aromatic)
Chiral Centers:
12
Fsp³:
0.9118 fraction sp³ carbon

Database Information

Compound ID:
SCS-C004682
NPClassifier Pathway:
Terpenoids
NPClassifier Superclass:
Steroids
NPClassifier Class:
Cholestane steroids
Glycoside:
Yes
NPClassifier Status:
Classified
External Links:
General chemistry
PubChem ChemSpider ChEMBL
Natural product databases
COCONUT NP Atlas CMNPD: CMNPD14549

Biological Activity Data

No bioactivity data available for this compound.

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Structure enlarged