SCS-C007503
pentactaside B
Pathway: Terpenoids
Superclass: Triterpenoids
Class: Lanostane, Tirucallane and Euphane triterpenoids
Glycoside
Chemical Structure
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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.
Source Information
Colochirus quadrangularis
(NA)
Original source name: Pentacta quadrangularis
Kingdom
Metazoa
Phylum
Echinodermata
Class
Holothuroidea
Order
Dendrochirotida
Family
Cucumariidae
Genus
Colochirus
Species
Colochirus quadrangularis
South China Sea
DOI:
10.1002/cbdv.200800324
· Chemistry & Biodiversity
Drug-likeness (Lipinski Ro5)
Molecular Weight
1303.4 Da
Threshold ≤ 500
ALogP
-6.23
Threshold ≤ 5
H-Bond Donors
7
Threshold ≤ 5
H-Bond Acceptors
28
Threshold ≤ 10
3 violations (MW, HBD, HBA) — not drug-like by Ro5
Chemical Properties
Molecular Formula:
C55H84Na2O28S2
Molecular Weight:
1303.3630 Da
SMILES:
COC1C(O)[C@H](OC2C(O)[C@H](O[C@@H]3C(C)O[C@@H](OC4C(O)[C@H](OS(=O)(=O)[O-])CO[C@H]4O[C@H]4CC[C@]5(C)[C@@H]6CC[C@]78C(=O)O[C@@](C)(CCC=C(C)C)[C@H]7[C@@H](OC(C)=O)C[C@@]8(C)C6=CC[C@H]5C4(C)C)C(OS(=O)(=O)[O-])C3O)OC[C@H]2O)OC(CO)[C@H]1O.[Na+].[Na+]
InChIKey:
GEUZVICMXONVRK-PBTVESTBSA-L
InChI:
InChI=1S/C55H86O28S2.2Na/c1-24(2)12-11-17-54(9)45-30(75-26(4)57)20-53(8)28-13-14-33-51(5,6)34(16-18-52(33,7)27(28)15-19-55(45,53)50(64)81-54)77-48-43(36(60)32(23-73-48)82-84(65,66)67)80-49-44(83-85(68,69)70)37(61)40(25(3)74-49)78-46-38(62)41(29(58)22-72-46)79-47-39(63)42(71-10)35(59)31(21-56)76-47;;/h12-13,25,27,29-49,56,58-63H,11,14-23H2,1-10H3,(H,65,66,67)(H,68,69,70);;/q;2*+1/p-2/t25?,27-,29-,30+,31?,32-,33+,34+,35-,36?,37?,38?,39?,40-,41?,42?,43?,44?,45-,46+,47+,48+,49+,52-,53+,54+,55-;;/m1../s1
Calculated Properties
ALogP:
-6.230 lipophilicity
TPSA:
410.14 Ų polar surface area
H-Bond Donors:
7
H-Bond Acceptors:
28
Rotatable Bonds:
18
Ring Count:
9
(0 aromatic)
Chiral Centers:
27
Fsp³:
0.8909 fraction sp³ carbon
Database Information
Compound ID:
SCS-C007503
NPClassifier Pathway:
Terpenoids
NPClassifier Superclass:
Triterpenoids
NPClassifier Class:
Lanostane, Tirucallane and Euphane triterpenoids
Glycoside:
Yes
NPClassifier Status:
Classified
External Links:
General chemistry
Natural product databases
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 | HCT-116 human colon cancer cells | 0.09 μM | 10.1002/cbdv.200800324 Chemistry & Biodiversity |
| Antitumor | IC50 | P-388 leukemic cells | 2.3 μM | 10.1002/cbdv.200800324 Chemistry & Biodiversity |
| Antitumor | IC50 | A-549 human lung cancer cells | 0.77 μM | 10.1002/cbdv.200800324 Chemistry & Biodiversity |
| Antitumor | IC50 | MCF-7 human breast cancer cells | 1.76 μM | 10.1002/cbdv.200800324 Chemistry & Biodiversity |
| Antitumor | IC50 | MKN-28 human gastric cancer cells | 1.59 μM | 10.1002/cbdv.200800324 Chemistry & Biodiversity |