SCS-C001866

cembrene-C

Pathway: Terpenoids Superclass: Diterpenoids Class: Cembrane diterpenoids

Chemical Structure

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Source Information

Sarcophyton ehrenbergi (soft coral)

Kingdom Metazoa Phylum Cnidaria Class Anthozoa Order Malacalcyonacea Family Alcyoniidae Genus Sarcophyton Species Sarcophyton ehrenbergi

Weizhou Island · -10 m

DOI: 10.1016/j.bioorg.2020.103993 · Bioorganic Chemistry

Sarcophyton trocheliophorum (NA)

Original source name: Sarcophyton trocheliophorum Marenzeller

Kingdom Metazoa Phylum Cnidaria Class Anthozoa Order Malacalcyonacea Family Alcyoniidae Genus Sarcophyton Species Sarcophyton trocheliophorum

South China Sea · -20 m

DOI: 10.1016/j.bmc.2013.06.043 · Bioorganic & Medicinal Chemistry

Drug-likeness (Lipinski Ro5)

Molecular Weight

272.5 Da

Threshold ≤ 500

ALogP

6.91

Threshold ≤ 5

H-Bond Donors

Threshold ≤ 5

H-Bond Acceptors

Threshold ≤ 10

1 violation (ALogP) — borderline drug-like

Chemical Properties

Molecular Formula:

C20H32

Molecular Weight:

272.5000 Da

SMILES:

CC(C)=C1C/C=C(\C)CC/C=C(\C)CC/C=C(\C)CC1

InChIKey:

                        SHVZFTWRFOQOFU-GDVLXBNMSA-N
                        
                    

InChI:

InChI=1S/C20H32/c1-16(2)20-14-12-18(4)10-6-8-17(3)9-7-11-19(5)13-15-20/h8,11-12H,6-7,9-10,13-15H2,1-5H3/b17-8+,18-12+,19-11+

Calculated Properties

ALogP:

6.906 lipophilicity

TPSA:

0.00 Å² polar surface area

H-Bond Donors:

H-Bond Acceptors:

Rotatable Bonds:

Ring Count:

1 (0 aromatic)

Chiral Centers:

Fsp³:

0.6000 fraction sp³ carbon

Database Information

Compound ID:

SCS-C001866

NPClassifier Pathway:

Terpenoids

NPClassifier Superclass:

Diterpenoids

NPClassifier Class:

Cembrane diterpenoids

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
Anti-inflammatory	IC50	TNF-α	29.5 μM	10.1016/j.bioorg.2020.103993 Bioorganic Chemistry
Enzyme inhibition	IC50	human protein tyrosine phosphatase 1B (PTP1B)	>= 20.0 μg/mL	10.1016/j.bmc.2013.06.043 Bioorganic & Medicinal Chemistry
Antitumor	—	human A-549 and HL-60 cell lines	None of the tested compounds exhibited cytotoxicity toward two human cell lines, A-549 and HL-60.	10.1016/j.bmc.2013.06.043 Bioorganic & Medicinal Chemistry

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