SCS-C006328
cytochalasin H
Pathway: Alkaloids
Superclass: Pseudoalkaloids
Class: Cytochalasan alkaloids
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
Diaporthe liquidambaris
(NA)
Original source name: Phomopsis liquidambari
Kingdom
Fungi
Phylum
Ascomycota
Class
Sordariomycetes
Order
Diaporthales
Family
Diaporthaceae
Genus
Diaporthe
Species
Diaporthe liquidambaris
South China Sea
DOI:
10.3892/or.2018.6347
· Oncology Reports
Drug-likeness (Lipinski Ro5)
Molecular Weight
493.6 Da
Threshold ≤ 500
ALogP
3.74
Threshold ≤ 5
H-Bond Donors
3
Threshold ≤ 5
H-Bond Acceptors
5
Threshold ≤ 10
Passes Lipinski Rule of Five — drug-like candidate
Chemical Properties
Molecular Formula:
C30H39NO5
Molecular Weight:
493.6440 Da
SMILES:
C=C1[C@@H](C)[C@H]2[C@H](Cc3ccccc3)NC(=O)[C@]23[C@H](OC(C)=O)/C=C/[C@](C)(O)C[C@@H](C)C/C=C/[C@H]3[C@@H]1O
InChIKey:
NAEWXXDGBKTIMN-OWTACEMYSA-N
InChI:
InChI=1S/C30H39NO5/c1-18-10-9-13-23-27(33)20(3)19(2)26-24(16-22-11-7-6-8-12-22)31-28(34)30(23,26)25(36-21(4)32)14-15-29(5,35)17-18/h6-9,11-15,18-19,23-27,33,35H,3,10,16-17H2,1-2,4-5H3,(H,31,34)/b13-9+,15-14+/t18-,19+,23-,24-,25+,26-,27+,29-,30+/m0/s1
Calculated Properties
ALogP:
3.738 lipophilicity
TPSA:
95.86 Ų polar surface area
H-Bond Donors:
3
H-Bond Acceptors:
5
Rotatable Bonds:
3
Ring Count:
4
(1 aromatic)
Chiral Centers:
9
Fsp³:
0.5333 fraction sp³ carbon
Database Information
Compound ID:
SCS-C006328
NPClassifier Pathway:
Alkaloids
NPClassifier Superclass:
Pseudoalkaloids
NPClassifier Class:
Cytochalasan alkaloids
Glycoside:
No
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 | A549 cell viability/growth | 158.452–160.548 μM | 10.3892/or.2018.6347 Oncology Reports |
| Cellular modulation | cell cycle phase arrest | G2/M phase cell cycle arrest | The treatment of CyH arrested A549 cells at the G2/M phase. Furthermore, sub?G1 peaks and fragmented DNA ladders were observed | 10.3892/or.2018.6347 Oncology Reports |
| Cellular modulation | apoptosis induction | altered apoptosis-related protein expression | — Structured numeric value is not available in this record; see the primary reference. | 10.3892/or.2018.6347 Oncology Reports |
| Antitumor | migration inhibition | A549 cell migration ability | — Structured numeric value is not available in this record; see the primary reference. | 10.3892/or.2018.6347 Oncology Reports |