SCS-C005988

variegatuside F

Pathway: Terpenoids Superclass: Triterpenoids Class: Lanostane, Tirucallane and Euphane triterpenoids Glycoside

Chemical Structure

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Source Information

Stichopus variegates Semper (sea cucumber)

Kingdom Metazoa Phylum Echinodermata Class Holothuroidea Order Aspidochirotida Family Stichopodidae Genus Stichopus Species Stichopus horrens

South China Sea

DOI: 10.3390/md12042004 · Marine Drugs

Drug-likeness (Lipinski Ro5)

Molecular Weight

1413.6 Da

Threshold ≤ 500

ALogP

-4.42

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:

C66H108O32

Molecular Weight:

1413.5580 Da

SMILES:

CO[C@@H]1[C@@H](O)[C@H](O[C@@H]2[C@@H](O)[C@H](O[C@@H]3CO[C@@H](O[C@H]4CC[C@]5(C)[C@@H]6CC[C@]78C(=O)O[C@@](C)(C[C@H](O)CC(C)C)[C@H]7CC[C@@]8(C)C6=CC[C@H]5C4(C)C)[C@H](O[C@@H]4O[C@H](CO)[C@@H](O)[C@H](O[C@@H]5OC[C@@H](O)[C@H](O[C@@H]6O[C@H](CO)[C@@H](O)[C@H](OC)[C@H]6O)[C@H]5O)[C@H]4O)[C@H]3O)O[C@H](CO)[C@H]2O)O[C@H](CO)[C@H]1O

InChIKey:

                        MFVRKJASTHTUAM-BSPWTDKFSA-N
                        
                    

InChI:

InChI=1S/C66H108O32/c1-26(2)18-27(71)19-65(7)37-13-16-64(6)29-10-11-36-62(3,4)38(14-15-63(36,5)28(29)12-17-66(37,64)61(83)98-65)93-60-54(43(77)35(25-87-60)92-56-47(81)53(42(76)33(22-69)88-56)96-58-46(80)51(85-9)40(74)32(21-68)90-58)97-59-48(82)52(41(75)34(23-70)91-59)95-55-44(78)49(30(72)24-86-55)94-57-45(79)50(84-8)39(73)31(20-67)89-57/h10,26-28,30-60,67-82H,11-25H2,1-9H3/t27-,28-,30-,31-,32-,33-,34-,35-,36+,37-,38+,39-,40-,41-,42-,43+,44-,45-,46-,47-,48-,49+,50+,51+,52+,53+,54-,55+,56+,57+,58+,59+,60+,63-,64+,65+,66-/m1/s1

Calculated Properties

ALogP:

-4.423 lipophilicity

TPSA:

479.20 Å² polar surface area

H-Bond Donors:

H-Bond Acceptors:

Rotatable Bonds:

Ring Count:

11 (0 aromatic)

Chiral Centers:

Fsp³:

0.9545 fraction sp³ carbon

Database Information

Compound ID:

SCS-C005988

NPClassifier Pathway:

Terpenoids

NPClassifier Superclass:

Triterpenoids

NPClassifier Class:

Lanostane, Tirucallane and Euphane triterpenoids

Glycoside:

Yes

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
Antifungal	MC80	in vitro assay against six fungal strains	— Structured numeric value is not available in this record; see the primary reference.	10.3390/md12042004 Marine Drugs

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