SCS-C007285

aspergillamide B

Pathway: Amino acids and Peptides Superclass: Small peptides Class: Dipeptides

Chemical Structure

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Source Information

Aspergillus terreus (mangrove endophytic fungus)

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

South China Sea

DOI: 10.1016/s1875-5364(19)30017-2 · Chinese Journal of Natural Medicines

Drug-likeness (Lipinski Ro5)

Molecular Weight

474.6 Da

Threshold ≤ 500

ALogP

3.88

Threshold ≤ 5

H-Bond Donors

Threshold ≤ 5

H-Bond Acceptors

Threshold ≤ 10

Passes Lipinski Rule of Five — drug-like candidate

Chemical Properties

Molecular Formula:

C28H34N4O3

Molecular Weight:

474.6050 Da

SMILES:

CC(=O)N[C@@H](CC(C)C)C(=O)N(C)[C@@H](Cc1ccccc1)C(=O)N/C=C/c1c[nH]c2ccccc12

InChIKey:

                        UTJKZLHQWWNPPP-VGKVPDMSSA-N
                        
                    

InChI:

InChI=1S/C28H34N4O3/c1-19(2)16-25(31-20(3)33)28(35)32(4)26(17-21-10-6-5-7-11-21)27(34)29-15-14-22-18-30-24-13-9-8-12-23(22)24/h5-15,18-19,25-26,30H,16-17H2,1-4H3,(H,29,34)(H,31,33)/b15-14+/t25-,26-/m0/s1

Calculated Properties

ALogP:

3.875 lipophilicity

TPSA:

94.30 Å² polar surface area

H-Bond Donors:

H-Bond Acceptors:

Rotatable Bonds:

Ring Count:

3 (3 aromatic)

Chiral Centers:

Fsp³:

0.3214 fraction sp³ carbon

Database Information

Compound ID:

SCS-C007285

NPClassifier Pathway:

Amino acids and Peptides

NPClassifier Superclass:

Small peptides

NPClassifier Class:

Dipeptides

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
Antimycobacterial	inhibition rate	Mycobacterium tuberculosis protein tyrosine phosphatase B (MptpB)	< 60.0 %	10.1016/s1875-5364(19)30017-2 Chinese Journal of Natural Medicines
Antitumor	activity level	human glioma U87 cells	all these compounds (1?17) exhibited weak or no cytotoxic activities towards human glioma U87 cells at a concentration of 10 μmol·L?1	10.1016/s1875-5364(19)30017-2 Chinese Journal of Natural Medicines
Neuroprotective / Neuromodulatory	activity level	glutamate-induced toxicity in HT22 cells	— Structured numeric value is not available in this record; see the primary reference.	10.1016/s1875-5364(19)30017-2 Chinese Journal of Natural Medicines

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