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  3. [(3S,5aS,5bR,7aS,8S,11aS,11bR,13S,13aS)-8-ethyl-3-hydroxy-3,5b,8,11a,13a-pentamethyl-1-oxo-5a,6,7,7a,9,10,11,11b,12,13-decahydrophenanthro[2,1-e][2]benzofuran-13-yl] 3-hydroxypentanoate

SCS-C002799

[(3S,5aS,5bR,7aS,8S,11aS,11bR,13S,13aS)-8-ethyl-3-hydroxy-3,5b,8,11a,13a-pentamethyl-1-oxo-5a,6,7,7a,9,10,11,11b,12,13-decahydrophenanthro[2,1-e][2]benzofuran-13-yl] 3-hydroxypentanoate

Pathway: Terpenoids Superclass: Sesterterpenoids Class: Scalarane sesterterpenoids Glycoside
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Chemical Structure

Structure of [(3S,5aS,5bR,7aS,8S,11aS,11bR,13S,13aS)-8-ethyl-3-hydroxy-3,5b,8,11a,13a-pentamethyl-1-oxo-5a,6,7,7a,9,10,11,11b,12,13-decahydrophenanthro[2,1-e][2]benzofuran-13-yl] 3-hydroxypentanoate
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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

Phyllospongia papyracea (NA)
Kingdom Metazoa Phylum Porifera Class Demospongiae Order Dictyoceratida Family Thorectidae Genus Phyllospongia Species Phyllospongia papyracea
Hainan Island
DOI: 10.1039/b805113p  · Natural Product Reports

Drug-likeness (Lipinski Ro5)

Molecular Weight
528.7 Da
Threshold ≤ 500
ALogP
5.86
Threshold ≤ 5
H-Bond Donors
2
Threshold ≤ 5
H-Bond Acceptors
6
Threshold ≤ 10
2 violations (MW, ALogP) — not drug-like by Ro5

Chemical Properties

Molecular Formula:
C32H48O6
Molecular Weight:
528.7300 Da
SMILES:
CCC(O)CC(=O)O[C@H]1C[C@@H]2[C@@]3(C)CCC[C@](C)(CC)[C@@H]3CC[C@@]2(C)[C@@H]2C=CC3=C(C(=O)O[C@]3(C)O)[C@@]12C
InChIKey:
VFNCNKUOQSBSAZ-MQVPXQDFSA-N
InChI:
InChI=1S/C32H48O6/c1-8-19(33)17-25(34)37-24-18-23-29(4)15-10-14-28(3,9-2)21(29)13-16-30(23,5)22-12-11-20-26(31(22,24)6)27(35)38-32(20,7)36/h11-12,19,21-24,33,36H,8-10,13-18H2,1-7H3/t19?,21-,22-,23+,24-,28-,29-,30-,31+,32-/m0/s1
Calculated Properties
ALogP:
5.856 lipophilicity
TPSA:
93.06 Ų polar surface area
H-Bond Donors:
2
H-Bond Acceptors:
6
Rotatable Bonds:
5
Ring Count:
5 (0 aromatic)
Chiral Centers:
10
Fsp³:
0.8125 fraction sp³ carbon

Database Information

Compound ID:
SCS-C002799
NPClassifier Pathway:
Terpenoids
NPClassifier Superclass:
Sesterterpenoids
NPClassifier Class:
Scalarane sesterterpenoids
Glycoside:
Yes
NPClassifier Status:
Classified
External Links:
General chemistry
PubChem ChemSpider ChEMBL
Natural product databases
COCONUT NP Atlas CMNPD: CMNPD17066

Biological Activity Data

No bioactivity data available for this compound.

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Structure enlarged