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SCS-C001805

19-hydroxycytochalasin B

Pathway: Alkaloids Superclass: Pseudoalkaloids Class: Cytochalasan alkaloids
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Chemical Structure

Structure of 19-hydroxycytochalasin B
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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.
Download: SDF SMILES

Source Information

Curvularia verruculosa (deep-sea endozoic fungus)
Kingdom Fungi Phylum Ascomycota Class Dothideomycetes Order Pleosporales Family Pleosporaceae Genus Curvularia Species Curvularia verruculosa
South China Sea
DOI: 10.1021/acs.jnatprod.1c00907  · Journal of Natural Products

Drug-likeness (Lipinski Ro5)

Molecular Weight
481.6 Da
Threshold ≤ 500
ALogP
2.07
Threshold ≤ 5
H-Bond Donors
4
Threshold ≤ 5
H-Bond Acceptors
6
Threshold ≤ 10
Passes Lipinski Rule of Five — drug-like candidate

Chemical Properties

Molecular Formula:
C28H35NO6
Molecular Weight:
481.5890 Da
SMILES:
C=C1[C@@H](C)[C@H]2[C@H](Cc3ccccc3)NC(=O)[C@]23OC(=O)/C=C/[C@H](O)[C@H](O)CC[C@@H](C)/C=C/[C@H]3[C@@H]1O
InChIKey:
QUFRGKQJQKJUMF-SOFYIBFKSA-N
InChI:
InChI=1S/C28H35NO6/c1-16-9-11-20-26(33)18(3)17(2)25-21(15-19-7-5-4-6-8-19)29-27(34)28(20,25)35-24(32)14-13-23(31)22(30)12-10-16/h4-9,11,13-14,16-17,20-23,25-26,30-31,33H,3,10,12,15H2,1-2H3,(H,29,34)/b11-9+,14-13+/t16-,17+,20-,21-,22+,23-,25-,26+,28+/m0/s1
Calculated Properties
ALogP:
2.073 lipophilicity
TPSA:
116.09 Ų polar surface area
H-Bond Donors:
4
H-Bond Acceptors:
6
Rotatable Bonds:
2
Ring Count:
4 (1 aromatic)
Chiral Centers:
9
Fsp³:
0.5000 fraction sp³ carbon

Database Information

Compound ID:
SCS-C001805
NPClassifier Pathway:
Alkaloids
NPClassifier Superclass:
Pseudoalkaloids
NPClassifier Class:
Cytochalasan alkaloids
Glycoside:
No
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
Antibacterial MIC Edwardisella ictarda 8.0 μg/mL 10.1021/acs.jnatprod.1c00907 Journal of Natural Products
Antitumor IC50 HCT-116, HepG-2, MCF-7 9.5 ± 1.9 μM 10.1021/acs.jnatprod.1c00907 Journal of Natural Products
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Structure enlarged