SCS-C005919

(1R,4S,9S,10S,11R,14S)-4,11-dihydroxy-1,10,14,18,18-pentamethyl-7-oxapentacyclo[11.8.0.0^{14,19}.0^{2,10}.0^{5,9}]henicosan-8-one

Pathway: Terpenoids Superclass: Sesterterpenoids Class: Scalarane sesterterpenoids

Chemical Structure

$Structure of (1R,4S,9S,10S,11R,14S)-4,11-dihydroxy-1,10,14,18,18-pentamethyl-7-oxapentacyclo[11.8.0.0^{14,19}.0^{2,10}.0^{5,9}]henicosan-8-one$

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Source Information

Hyrtios sp. (NA)

Kingdom Metazoa Phylum Porifera Class Demospongiae Order Dictyoceratida Family Thorectidae Genus Hyrtios Species NA

South China Sea

DOI: 10.1177/1934578x1400900608 · Natural Product Communications

Drug-likeness (Lipinski Ro5)

Molecular Weight

404.6 Da

Threshold ≤ 500

ALogP

4.18

Threshold ≤ 5

H-Bond Donors

Threshold ≤ 5

H-Bond Acceptors

Threshold ≤ 10

Passes Lipinski Rule of Five — drug-like candidate

Chemical Properties

Molecular Formula:

C25H40O4

Molecular Weight:

404.5910 Da

SMILES:

CC1(C)CCC[C@@]2(C)C1CC[C@]1(C)C2C[C@@H](O)[C@@]2(C)C1C[C@H](O)C1COC(=O)[C@@H]12

InChIKey:

                        OOZOSXWXRPGQQY-ROVPGTEOSA-N
                        
                    

InChI:

InChI=1S/C25H40O4/c1-22(2)8-6-9-23(3)16(22)7-10-24(4)17(23)12-19(27)25(5)18(24)11-15(26)14-13-29-21(28)20(14)25/h14-20,26-27H,6-13H2,1-5H3/t14?,15-,16?,17?,18?,19+,20+,23-,24+,25+/m0/s1

Calculated Properties

ALogP:

4.176 lipophilicity

TPSA:

66.76 Å² polar surface area

H-Bond Donors:

H-Bond Acceptors:

Rotatable Bonds:

Ring Count:

5 (0 aromatic)

Chiral Centers:

Fsp³:

0.9600 fraction sp³ carbon

Database Information

Compound ID:

SCS-C005919

NPClassifier Pathway:

Terpenoids

NPClassifier Superclass:

Sesterterpenoids

NPClassifier Class:

Scalarane sesterterpenoids

Glycoside:

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	IC50	human cancer cell line HCT-116	12.7 μg/mL	10.1177/1934578x1400900608 Natural Product Communications

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