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  3. (1R,5aS,5bR,7aS,8S,11aS,11bR,13S,13aS)-8-ethyl-1,13-dihydroxy-5b,8,11a,13a-tetramethyl-1,2,4,5,5a,6,7,7a,9,10,11,11b,12,13-tetradecahydrocyclopenta[a]chrysen-3-one

SCS-C000139

(1R,5aS,5bR,7aS,8S,11aS,11bR,13S,13aS)-8-ethyl-1,13-dihydroxy-5b,8,11a,13a-tetramethyl-1,2,4,5,5a,6,7,7a,9,10,11,11b,12,13-tetradecahydrocyclopenta[a]chrysen-3-one

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

Structure of (1R,5aS,5bR,7aS,8S,11aS,11bR,13S,13aS)-8-ethyl-1,13-dihydroxy-5b,8,11a,13a-tetramethyl-1,2,4,5,5a,6,7,7a,9,10,11,11b,12,13-tetradecahydrocyclopenta[a]chrysen-3-one
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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.
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Source Information

Dysidea granulosa (NA)
Kingdom Metazoa Phylum Porifera Class Demospongiae Order Dictyoceratida Family Dysideidae Genus Dysidea Species Dysidea granulosa
Xisha Islands
DOI: 10.1021/acs.jnatprod.9b01202  · Journal of Natural Products

Drug-likeness (Lipinski Ro5)

Molecular Weight
414.3 Da
Threshold ≤ 500
ALogP
5.44
Threshold ≤ 5
H-Bond Donors
2
Threshold ≤ 5
H-Bond Acceptors
3
Threshold ≤ 10
1 violation (ALogP) — borderline drug-like

Chemical Properties

Molecular Formula:
C27H42O3
Molecular Weight:
414.3139 Da
SMILES:
CC[C@@]1(C)CCC[C@]2(C)[C@H]3C[C@H](O)[C@]4(C)C5=C(CC[C@H]4[C@]3(C)CC[C@@H]12)C(=O)C[C@H]5O
InChIKey:
TVDIFPWLPHKASG-VMFLZRSCSA-N
InChI:
InChI=1S/C27H42O3/c1-6-24(2)11-7-12-25(3)19(24)10-13-26(4)20-9-8-16-17(28)14-18(29)23(16)27(20,5)22(30)15-21(25)26/h18-22,29-30H,6-15H2,1-5H3/t18-,19+,20+,21-,22+,24+,25+,26+,27-/m1/s1
Calculated Properties
ALogP:
5.437 lipophilicity
TPSA:
57.53 Ų polar surface area
H-Bond Donors:
2
H-Bond Acceptors:
3
Rotatable Bonds:
1
Ring Count:
5 (0 aromatic)
Chiral Centers:
9
Fsp³:
0.8889 fraction sp³ carbon

Database Information

Compound ID:
SCS-C000139
NPClassifier Pathway:
Terpenoids
NPClassifier Superclass:
Sesterterpenoids
NPClassifier Class:
Scalarane sesterterpenoids
Glycoside:
No
NPClassifier Status:
Classified
External Links:
General chemistry
PubChem ChemSpider ChEMBL
Natural product databases
COCONUT NP Atlas

Biological Activity Data

Activity values are displayed only when a quantitative or clearly reported result is available. Tested organisms, cell lines and molecular targets are shown under Target / model.
Activity Assay Target / model Result Reference
Antitumor — HCT116,A549,BEL-7402,Jurkat,K562 > 30.0 μM 10.1021/acs.jnatprod.9b01202 Journal of Natural Products
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Structure enlarged