SCS-C007111

3-((3S,6R,9S,12S,15R,18S,21S,25R)-18-((2S)-butan-2-yl)-9-(2-hydroxy-2-oxoethyl)-25-(8-methylnonyl)-3,6,15-tris(2-methylpropyl)-2,5,8,11,14,17,20,23-octaoxo-12-(propan-2-yl)-1-oxa-4,7,10,13,16,19,22-heptaazacyclopentacosan-21-yl)propanoic acid

Pathway: Amino acids and Peptides | Polyketides Superclass: Oligopeptides Class: Cyclic peptides | Depsipeptides | Lipopeptides

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Chemical Structure

Structure of 3-((3S,6R,9S,12S,15R,18S,21S,25R)-18-((2S)-butan-2-yl)-9-(2-hydroxy-2-oxoethyl)-25-(8-methylnonyl)-3,6,15-tris(2-methylpropyl)-2,5,8,11,14,17,20,23-octaoxo-12-(propan-2-yl)-1-oxa-4,7,10,13,16,19,22-heptaazacyclopentacosan-21-yl)propanoic acid

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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.

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Source Information

Limimaricola sp. SCSIO 53532 (NA)

Kingdom Pseudomonadati Phylum Pseudomonadota Class Alphaproteobacteria Order Rhodobacterales Family Paracoccaceae Genus Limimaricola Species Limimaricola sp.

South China Sea · 2437 m

DOI: 10.1016/j.bioorg.2021.105589 · Bioorganic Chemistry

Drug-likeness (Lipinski Ro5)

Molecular Weight

1008.3 Da

Threshold ≤ 500

ALogP

4.26

Threshold ≤ 5

H-Bond Donors

Threshold ≤ 5

H-Bond Acceptors

Threshold ≤ 10

3 violations (MW, HBD, HBA) — not drug-like by Ro5

Chemical Properties

Molecular Formula:

C51H89N7O13

Molecular Weight:

1008.3090 Da

SMILES:

CC[C@H](C)[C@@H]1NC(=O)[C@H](CCC(=O)O)NC(=O)C[C@@H](CCCCCCCC(C)C)OC(=O)[C@H](CC(C)C)NC(=O)[C@@H](CC(C)C)NC(=O)[C@H](CC(=O)O)NC(=O)[C@H](C(C)C)NC(=O)[C@@H](CC(C)C)NC1=O

InChIKey:

                        GHHISGYZABZYST-GGQWIZSMSA-N
                        
                    

InChI:

InChI=1S/C51H89N7O13/c1-13-33(12)44-50(69)54-37(24-30(6)7)48(67)57-43(32(10)11)49(68)55-38(27-42(62)63)47(66)53-36(23-29(4)5)46(65)56-39(25-31(8)9)51(70)71-34(20-18-16-14-15-17-19-28(2)3)26-40(59)52-35(45(64)58-44)21-22-41(60)61/h28-39,43-44H,13-27H2,1-12H3,(H,52,59)(H,53,66)(H,54,69)(H,55,68)(H,56,65)(H,57,67)(H,58,64)(H,60,61)(H,62,63)/t33-,34+,35-,36+,37+,38-,39-,43-,44-/m0/s1

Calculated Properties

ALogP:

4.262 lipophilicity

TPSA:

304.60 Å² polar surface area

H-Bond Donors:

H-Bond Acceptors:

Rotatable Bonds:

Ring Count:

1 (0 aromatic)

Chiral Centers:

Fsp³:

0.8039 fraction sp³ carbon

Database Information

Compound ID:

SCS-C007111

NPClassifier Pathway:

Amino acids and Peptides Polyketides

NPClassifier Superclass:

Oligopeptides

NPClassifier Class:

Cyclic peptides Depsipeptides Lipopeptides

Glycoside:

NPClassifier Status:

Classified

External Links:

General chemistry

PubChem ChemSpider ChEMBL

Natural product databases

COCONUT NP Atlas

Biological Activity Data

No bioactivity data available for this compound.

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