SCS-C006773

cyclotryprostatin B

Pathway: Alkaloids | Amino acids and Peptides Superclass: Peptide alkaloids Class: Indole diketopiperazine alkaloids (L-Trp, L-Pro)

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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.

Download: SDF SMILES

Source Information

Aspergillus sydowii (coral-derived fungus)

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

South China Sea

DOI: 10.1177/1934578x1300800313 · Natural Product Communications

Drug-likeness (Lipinski Ro5)

Molecular Weight

395.5 Da

Threshold ≤ 500

ALogP

2.40

Threshold ≤ 5

H-Bond Donors

Threshold ≤ 5

H-Bond Acceptors

Threshold ≤ 10

Passes Lipinski Rule of Five — drug-like candidate

Chemical Properties

Molecular Formula:

C22H25N3O4

Molecular Weight:

395.4590 Da

SMILES:

CO[C@@H]1c2c([nH]c3ccccc23)[C@H](C=C(C)C)N2C(=O)[C@@H]3CCCN3C(=O)[C@@]12O

InChIKey:

                        QTOVUUPWQCFFQD-RZJBWQBDSA-N
                        
                    

InChI:

InChI=1S/C22H25N3O4/c1-12(2)11-16-18-17(13-7-4-5-8-14(13)23-18)19(29-3)22(28)21(27)24-10-6-9-15(24)20(26)25(16)22/h4-5,7-8,11,15-16,19,23,28H,6,9-10H2,1-3H3/t15-,16-,19+,22-/m0/s1

Calculated Properties

ALogP:

2.398 lipophilicity

TPSA:

85.87 Å² polar surface area

H-Bond Donors:

H-Bond Acceptors:

Rotatable Bonds:

Ring Count:

5 (2 aromatic)

Chiral Centers:

Fsp³:

0.4545 fraction sp³ carbon

Database Information

Compound ID:

SCS-C006773

NPClassifier Pathway:

Alkaloids Amino acids and Peptides

NPClassifier Superclass:

Peptide alkaloids

NPClassifier Class:

Indole diketopiperazine alkaloids (L-Trp, L-Pro)

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
Antifouling	settlement inhibition	Bugula neritina larvae	— Structured numeric value is not available in this record; see the primary reference.	10.1177/1934578x1300800313 Natural Product Communications

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