SCS-C006476

benthol A

Pathway: Polyketides Superclass: Linear polyketides Class: Open-chain polyketides

Chemical Structure

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Source Information

unclassified Dinophyceae (benthic dinoflagellate) (NA)

Original source name: benthic dinoflagellate

Kingdom NA Phylum Alveolata Class Dinophyceae Order NA Family NA Genus NA Species NA

South China Sea

DOI: 10.1039/d1sc02810c · Chemical Science

Drug-likeness (Lipinski Ro5)

Molecular Weight

1507.8 Da

Threshold ≤ 500

ALogP

-2.01

Threshold ≤ 5

H-Bond Donors

Threshold ≤ 5

H-Bond Acceptors

Threshold ≤ 10

3 violations (MW, HBD, HBA) — not drug-like by Ro5

Chemical Properties

Molecular Formula:

C75H126O30

Molecular Weight:

1507.8030 Da

SMILES:

C=C1C[C@@H](C[C@@H](O)C/C=C/[C@@H](O)CC[C@H]2O[C@@H](CCCC[C@H]3O[C@@H](C[C@H](O)[C@@H]4C[C@@H](O)[C@H](O)[C@@H]([C@H](O)[C@@H](O)CC/C(C)=C/[C@H](O)C[C@@H](O)[C@H]5O[C@@H](C[C@H]6O[C@@H](C/C(C)=C/[C@H](O)C/C=C/[C@@H](O)C[C@H]7OCC[C@H](O)[C@@H]7O)C[C@H](O)[C@@H]6O)C[C@H]5O)O4)C[C@H]3O)C[C@H]2O)O[C@]2(C1)C[C@@H](O)[C@H](O)[C@@H](C[C@H](O)CO)O2

InChIKey:

                        KLCGSXXYINBJGR-UEXDJNTBSA-N
                        
                    

InChI:

InChI=1S/C75H126O30/c1-38(20-45(81)25-59(90)73-60(91)32-50(102-73)33-66-69(94)57(88)31-48(101-66)22-39(2)21-42(78)9-7-11-44(80)26-65-68(93)53(84)18-19-98-65)14-16-52(83)71(96)74-72(97)58(89)34-64(103-74)56(87)30-49-29-55(86)62(100-49)13-5-4-12-47-28-54(85)63(99-47)17-15-41(77)8-6-10-43(79)24-51-23-40(3)35-75(104-51)36-61(92)70(95)67(105-75)27-46(82)37-76/h6-8,11,20-21,41-74,76-97H,3-5,9-10,12-19,22-37H2,1-2H3/b8-6+,11-7+,38-20+,39-21+/t41-,42-,43+,44-,45+,46+,47+,48+,49-,50-,51+,52+,53+,54-,55-,56+,57+,58-,59-,60-,61-,62-,63-,64+,65-,66-,67-,68+,69+,70+,71-,72+,73-,74-,75+/m1/s1

Calculated Properties

ALogP:

-2.009 lipophilicity

TPSA:

518.90 Å² polar surface area

H-Bond Donors:

H-Bond Acceptors:

Rotatable Bonds:

Ring Count:

8 (0 aromatic)

Chiral Centers:

Fsp³:

0.8667 fraction sp³ carbon

Database Information

Compound ID:

SCS-C006476

NPClassifier Pathway:

Polyketides

NPClassifier Superclass:

Linear polyketides

NPClassifier Class:

Open-chain polyketides

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
Antiparasitic	EC50	Plasmodium falciparum	60.8 nM	10.1039/d1sc02810c Chemical Science
Antiviral	inhibition rate	HIV-1	57.1 %	10.1039/d1sc02810c Chemical Science
Antiviral	inhibition rate	HIV-1	16.5 %	10.1039/d1sc02810c Chemical Science

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