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  3. [(3R,4S,5S,6S)-4,5-dihydroxy-6-[[(3S,8S,9S,10S,13R,14S,17R)-10-(hydroxymethyl)-17-[(2R)-6-hydroxy-6-methylheptan-2-yl]-13-methyl-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-C004454

[(3R,4S,5S,6S)-4,5-dihydroxy-6-[[(3S,8S,9S,10S,13R,14S,17R)-10-(hydroxymethyl)-17-[(2R)-6-hydroxy-6-methylheptan-2-yl]-13-methyl-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)-17-[(2R)-6-hydroxy-6-methylheptan-2-yl]-13-methyl-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: 10.1002/mrc.1530  · Magnetic Resonance in Chemistry

Drug-likeness (Lipinski Ro5)

Molecular Weight
592.8 Da
Threshold ≤ 500
ALogP
4.51
Threshold ≤ 5
H-Bond Donors
4
Threshold ≤ 5
H-Bond Acceptors
8
Threshold ≤ 10
1 violation (MW) — borderline drug-like

Chemical Properties

Molecular Formula:
C34H56O8
Molecular Weight:
592.8140 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)O)CC[C@@H]43)C2)[C@@H](O)[C@@H]1O
InChIKey:
AGJIAJMCPCZGCE-QBVSUKJSSA-N
InChI:
InChI=1S/C34H56O8/c1-20(7-6-14-32(3,4)39)25-10-11-26-24-9-8-22-17-23(12-16-34(22,19-35)27(24)13-15-33(25,26)5)42-31-30(38)29(37)28(18-40-31)41-21(2)36/h8,20,23-31,35,37-39H,6-7,9-19H2,1-5H3/t20-,23+,24+,25-,26+,27+,28-,29-,30+,31+,33-,34-/m1/s1
Calculated Properties
ALogP:
4.510 lipophilicity
TPSA:
125.68 Ų polar surface area
H-Bond Donors:
4
H-Bond Acceptors:
8
Rotatable Bonds:
9
Ring Count:
5 (0 aromatic)
Chiral Centers:
12
Fsp³:
0.9118 fraction sp³ carbon

Database Information

Compound ID:
SCS-C004454
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: CMNPD15451

Biological Activity Data

No bioactivity data available for this compound.

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Structure enlarged