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  3. (1S,4S,10R,12R)-12-[3-[[(3S,8aR)-1,4-dioxo-2,3,6,7,8,8a-hexahydropyrrolo[1,2-a]pyrazin-3-yl]methyl]-1H-indol-5-yl]-2,8,19-triazapentacyclo[10.7.0.02,10.04,8.013,18]nonadeca-13,15,17-triene-3,9-dione

SCS-C005022

(1S,4S,10R,12R)-12-[3-[[(3S,8aR)-1,4-dioxo-2,3,6,7,8,8a-hexahydropyrrolo[1,2-a]pyrazin-3-yl]methyl]-1H-indol-5-yl]-2,8,19-triazapentacyclo[10.7.0.02,10.04,8.013,18]nonadeca-13,15,17-triene-3,9-dione

Pathway: Amino acids and Peptides Superclass: Oligopeptides Class: Cyclic peptides
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Chemical Structure

Structure of (1S,4S,10R,12R)-12-[3-[[(3S,8aR)-1,4-dioxo-2,3,6,7,8,8a-hexahydropyrrolo[1,2-a]pyrazin-3-yl]methyl]-1H-indol-5-yl]-2,8,19-triazapentacyclo[10.7.0.02,10.04,8.013,18]nonadeca-13,15,17-triene-3,9-dione
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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

Streptomyces sp. (bacterium)
Kingdom Bacillati Phylum Actinomycetota Class Actinomycetes Order Kitasatosporales Family Streptomycetaceae Genus Streptomyces Species NA
South China Sea
DOI: 10.1021/acs.orglett.6b02620  · Organic Letters

Drug-likeness (Lipinski Ro5)

Molecular Weight
564.6 Da
Threshold ≤ 500
ALogP
1.84
Threshold ≤ 5
H-Bond Donors
3
Threshold ≤ 5
H-Bond Acceptors
5
Threshold ≤ 10
1 violation (MW) — borderline drug-like

Chemical Properties

Molecular Formula:
C32H32N6O4
Molecular Weight:
564.6460 Da
SMILES:
O=C1N[C@@H](Cc2c[nH]c3ccc([C@@]45C[C@@H]6C(=O)N7CCC[C@H]7C(=O)N6[C@@H]4Nc4ccccc45)cc23)C(=O)N2CCC[C@H]12
InChIKey:
LQDCHAOARKZZQM-CEQPYWFKSA-N
InChI:
InChI=1S/C32H32N6O4/c39-27-24-7-3-11-36(24)28(40)23(34-27)13-17-16-33-21-10-9-18(14-19(17)21)32-15-26-29(41)37-12-4-8-25(37)30(42)38(26)31(32)35-22-6-2-1-5-20(22)32/h1-2,5-6,9-10,14,16,23-26,31,33,35H,3-4,7-8,11-13,15H2,(H,34,39)/t23-,24+,25-,26+,31-,32+/m0/s1
Calculated Properties
ALogP:
1.843 lipophilicity
TPSA:
117.85 Ų polar surface area
H-Bond Donors:
3
H-Bond Acceptors:
5
Rotatable Bonds:
3
Ring Count:
9 (3 aromatic)
Chiral Centers:
6
Fsp³:
0.4375 fraction sp³ carbon

Database Information

Compound ID:
SCS-C005022
NPClassifier Pathway:
Amino acids and Peptides
NPClassifier Superclass:
Oligopeptides
NPClassifier Class:
Cyclic peptides
Glycoside:
No
NPClassifier Status:
Classified
External Links:
General chemistry
PubChem ChemSpider ChEMBL
Natural product databases
COCONUT NP Atlas CMNPD: CMNPD27216

Biological Activity Data

No bioactivity data available for this compound.

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Structure enlarged