SCS-C007937

prelapatin B

Pathway: Alkaloids Superclass: Anthranilic acid alkaloids Class: Quinazoline alkaloids

Chemical Structure

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Source Information

Aspergillus clavatonanicus (sponge-associated fungus)

Kingdom Fungi Phylum Ascomycota Class Eurotiomycetes Order Eurotiales Family Aspergillaceae Genus Aspergillus Species Aspergillus clavatonanicus

South China Sea

DOI: 10.1021/acs.jnatprod.5c01575 · Journal of Natural Products

Drug-likeness (Lipinski Ro5)

Molecular Weight

356.4 Da

Threshold ≤ 500

ALogP

2.37

Threshold ≤ 5

H-Bond Donors

Threshold ≤ 5

H-Bond Acceptors

Threshold ≤ 10

Passes Lipinski Rule of Five — drug-like candidate

Chemical Properties

Molecular Formula:

C21H16N4O2

Molecular Weight:

356.3850 Da

SMILES:

C[C@]12NC(=O)[C@@H](Cc3c1[nH]c1ccccc31)n1c2nc2ccccc2c1=O

InChIKey:

                        JLBVVGKVADHTHK-IERDGZPVSA-N
                        
                    

InChI:

InChI=1S/C21H16N4O2/c1-21-17-13(11-6-2-4-8-14(11)22-17)10-16(18(26)24-21)25-19(27)12-7-3-5-9-15(12)23-20(21)25/h2-9,16,22H,10H2,1H3,(H,24,26)/t16-,21+/m1/s1

Calculated Properties

ALogP:

2.368 lipophilicity

TPSA:

79.78 Å² polar surface area

H-Bond Donors:

H-Bond Acceptors:

Rotatable Bonds:

Ring Count:

7 (4 aromatic)

Chiral Centers:

Fsp³:

0.1905 fraction sp³ carbon

Database Information

Compound ID:

SCS-C007937

NPClassifier Pathway:

Alkaloids

NPClassifier Superclass:

Anthranilic acid alkaloids

NPClassifier Class:

Quinazoline alkaloids

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
Antifibrotic / Organ protection	inhibition	FN, α-SMA	10.0 μM	10.1021/acs.jnatprod.5c01575 Journal of Natural Products

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