CHEBI:145105 - asperphenamate

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ChEBI Name asperphenamate
ChEBI ID CHEBI:145105
Definition A carboxylic ester resulting from the formal condensation of the carboxy group of N-benzoyl-L-phenylalanine with the hydroxy group of N-benzoyl-L-phenylalaninol. A metabolite found in several Pencillium and Aspergillus species, as well as in plants as a product of endophytic fungi.
Stars This entity has been manually annotated by the ChEBI Team.
Submitter Kristian Axelsen
Supplier Information
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Formula C32H30N2O4
Net Charge 0
Average Mass 506.602
Monoisotopic Mass 506.22056
InChI InChI=1S/C32H30N2O4/c35-30(26-17-9-3-10-18-26)33-28(21-24-13-5-1-6-14-24)23-38-32(37)29(22-25-15-7-2-8-16-25)34-31(36)27-19-11-4-12-20-27/h1-20,28-29H,21-23H2,(H,33,35)(H,34,36)/t28-,29-/m0/s1
InChIKey CVULDJMCSSACEO-VMPREFPWSA-N
SMILES C=1C(=CC=CC1)C(=O)N[C@H](COC([C@H](CC=2C=CC=CC2)NC(C=3C=CC=CC3)=O)=O)CC=4C=CC=CC4
Metabolite of Species Details
Penicillium sp.thulatum (NCBI:txid1263194) of strain B35 See: PubMed
Ficus mucuso (NCBI:txid309328) Found in bark (BTO:0001301). Isolated from stem bark. See: PubMed
Piptadenia gonoacantha (NCBI:txid397634) Found in branches and leaves. See: PubMed
Aspergillus flavipes (NCBI:txid41900) Found in cell suspension culture (BTO:0000221). of strain ATCC 11013 See: PubMed
Penicillium brevicompactum (NCBI:txid5074) See: PubMed
Roles Classification
Application(s): antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
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ChEBI Ontology
Outgoing asperphenamate (CHEBI:145105) has functional parent N-benzoyl-L-phenylalanine (CHEBI:90412)
asperphenamate (CHEBI:145105) has functional parent N-benzoyl-L-phenylalaninol (CHEBI:145107)
asperphenamate (CHEBI:145105) has role antineoplastic agent (CHEBI:35610)
asperphenamate (CHEBI:145105) is a L-phenylalanine derivative (CHEBI:84144)
asperphenamate (CHEBI:145105) is a benzamides (CHEBI:22702)
asperphenamate (CHEBI:145105) is a carboxylic ester (CHEBI:33308)
IUPAC Name
(2S)-2-benzamido-3-phenylpropyl N-benzoyl-L-phenylalaninate
Synonyms Sources
(2S)-2-benzamido-3-phenylpropyl (2S)-2-benzamido-3-phenylpropanoate IUPAC
anabellamide ChEBI
asjanin ChEBI
asperphenamate UniProt
auranamide ChEBI
N-benzoyl-L-phenylalanine,2S-(benzoylamino)-3-phenylpropyl ester ChEBI
Manual Xref Database
C00041362 KNApSAcK
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Registry Number Type Source
63631-36-7 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
16345939 PubMed citation Europe PMC
16835084 PubMed citation Europe PMC
21139276 PubMed citation Europe PMC
21562684 PubMed citation Europe PMC
22668848 PubMed citation Europe PMC
23173673 PubMed citation Europe PMC
27399232 PubMed citation Europe PMC
29719714 PubMed citation SUBMITTER
875642 PubMed citation Europe PMC
Last Modified
17 October 2019