SCS-C003199

3-[(3S,6R,9S,12R,15S,18R,22S)-3-[(2S)-butan-2-yl]-22-[(2R)-decan-2-yl]-18-[(1R)-1-hydroxyethyl]-6-[(4-hydroxyphenyl)methyl]-12,15-dimethyl-2,5,8,11,14,17,20-heptaoxo-1-oxa-4,7,10,13,16,19-hexazacyclodocos-9-yl]propanamide

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,12R,15S,18R,22S)-3-[(2S)-butan-2-yl]-22-[(2R)-decan-2-yl]-18-[(1R)-1-hydroxyethyl]-6-[(4-hydroxyphenyl)methyl]-12,15-dimethyl-2,5,8,11,14,17,20-heptaoxo-1-oxa-4,7,10,13,16,19-hexazacyclodocos-9-yl]propanamide

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Source Information

Fusarium sp. (marine fungus #2489)

Kingdom Fungi Phylum Ascomycota Class Sordariomycetes Order Hypocreales Family Nectriaceae Genus Fusarium Species NA

Hainan Island

DOI: 10.1039/c6np00124f · Natural Product Reports

Drug-likeness (Lipinski Ro5)

Molecular Weight

860.1 Da

Threshold ≤ 500

ALogP

1.28

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:

C43H69N7O11

Molecular Weight:

860.0630 Da

SMILES:

CCCCCCCC[C@@H](C)[C@@H]1CC(=O)N[C@H]([C@@H](C)O)C(=O)N[C@@H](C)C(=O)N[C@H](C)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@H](Cc2ccc(O)cc2)C(=O)N[C@@H]([C@@H](C)CC)C(=O)O1

InChIKey:

                        ZORNNKGAQUDOAY-DWDBLGDQSA-N
                        
                    

InChI:

InChI=1S/C43H69N7O11/c1-8-10-11-12-13-14-15-25(4)33-23-35(54)49-37(28(7)51)42(59)46-26(5)38(55)45-27(6)39(56)47-31(20-21-34(44)53)40(57)48-32(22-29-16-18-30(52)19-17-29)41(58)50-36(24(3)9-2)43(60)61-33/h16-19,24-28,31-33,36-37,51-52H,8-15,20-23H2,1-7H3,(H2,44,53)(H,45,55)(H,46,59)(H,47,56)(H,48,57)(H,49,54)(H,50,58)/t24-,25+,26-,27+,28+,31-,32+,33-,36-,37+/m0/s1

Calculated Properties

ALogP:

1.278 lipophilicity

TPSA:

284.45 Å² polar surface area

H-Bond Donors:

H-Bond Acceptors:

Rotatable Bonds:

Ring Count:

2 (1 aromatic)

Chiral Centers:

Fsp³:

0.6744 fraction sp³ carbon

Database Information

Compound ID:

SCS-C003199

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 CMNPD: CMNPD26307

Biological Activity Data

No bioactivity data available for this compound.

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