SCS-C006777

cyclotryprostatin E

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: 10.1038/ja.2011.117 · The Journal of Antibiotics

Drug-likeness (Lipinski Ro5)

Molecular Weight

443.5 Da

Threshold ≤ 500

ALogP

1.60

Threshold ≤ 5

H-Bond Donors

Threshold ≤ 5

H-Bond Acceptors

Threshold ≤ 10

Passes Lipinski Rule of Five — drug-like candidate

Chemical Properties

Molecular Formula:

C23H29N3O6

Molecular Weight:

443.5000 Da

SMILES:

COc1ccc2c3c([nH]c2c1)[C@H](CC(C)(C)O)N1C(=O)[C@@H]2CCCN2C(=O)[C@@]1(O)[C@H]3OC

InChIKey:

                        IQQGHQDLZFLSGU-YZQOHXRLSA-N
                        
                    

InChI:

InChI=1S/C23H29N3O6/c1-22(2,29)11-16-18-17(13-8-7-12(31-3)10-14(13)24-18)19(32-4)23(30)21(28)25-9-5-6-15(25)20(27)26(16)23/h7-8,10,15-16,19,24,29-30H,5-6,9,11H2,1-4H3/t15-,16-,19-,23-/m0/s1

Calculated Properties

ALogP:

1.601 lipophilicity

TPSA:

115.33 Å² polar surface area

H-Bond Donors:

H-Bond Acceptors:

Rotatable Bonds:

Ring Count:

5 (2 aromatic)

Chiral Centers:

Fsp³:

0.5652 fraction sp³ carbon

Database Information

Compound ID:

SCS-C006777

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
Antitumor	—	A375 (human melanoma); HeLa (human cervical carcinoma) cell lines	Compound (1) had no obvious cytotoxicity towards the above mentioned three cell lines.	10.1038/ja.2011.117 The Journal of Antibiotics

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