CHEBI:29655 - neocarzinostatin chromophore

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ChEBI Name neocarzinostatin chromophore
ChEBI ID CHEBI:29655
Definition A naphthoate ester obtained by formal condensation of the carboxy group of 2-hydroxy-7-methoxy-5-methyl-1-naphthoic acid with the 5-hydroxy group of (1aS,5R,6R,6aE,9aR)-5-hydroxy-1a-[(4R)-2-oxo-1,3-dioxolan-4-yl]-2,3,8,9-tetradehydro-1a,5,6,9a-tetrahydrocyclopenta[5,6]cyclonona[1,2-b]oxiren-6-yl 2,6-dideoxy-2-(methylamino)-α-D-galactopyranoside. The chromophoric part of neocarzinostatin, it is tightly and non-covelently bound to a 113-membered apoprotein, which serves to protect it and release it to the target DNA.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:41563
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Formula C35H33NO12
Net Charge 0
Average Mass 659.63600
Monoisotopic Mass 659.20028
InChI InChI=1S/C35H33NO12/c1-16-12-19(42-4)14-22-20(16)8-9-23(37)27(22)32(40)45-24-13-18-10-11-35(26-15-43-34(41)46-26)25(48-35)7-5-6-21(18)31(24)47-33-28(36-3)30(39)29(38)17(2)44-33/h6,8-9,12-14,17,24-26,28-31,33,36-39H,15H2,1-4H3/b21-6+/t17-,24-,25-,26-,28-,29+,30-,31-,33-,35+/m1/s1
InChIKey QZGIWPZCWHMVQL-UIYAJPBUSA-N
SMILES CN[C@@H]1[C@@H](O)[C@@H](O)[C@@H](C)O[C@@H]1O[C@H]1[C@H](OC(=O)c2c(O)ccc3c(C)cc(OC)cc23)C=C2C#C[C@@]3(O[C@@H]3C#C/C=C1\2)[C@H]1COC(=O)O1
Roles Classification
Application(s): antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing neocarzinostatin chromophore (CHEBI:29655) has role antineoplastic agent (CHEBI:35610)
neocarzinostatin chromophore (CHEBI:29655) is a D-galactosaminide (CHEBI:20954)
neocarzinostatin chromophore (CHEBI:29655) is a cyclopentacyclononaoxirene (CHEBI:46830)
neocarzinostatin chromophore (CHEBI:29655) is a dioxolane (CHEBI:39430)
neocarzinostatin chromophore (CHEBI:29655) is a monosaccharide derivative (CHEBI:63367)
neocarzinostatin chromophore (CHEBI:29655) is a naphthoate ester (CHEBI:46831)
IUPAC Name
(1aS,5R,6R,6aE,9aR)-6-{[2,6-dideoxy-2-(methylamino)-α-D-galactopyranosyl]oxy}-1a-[(4R)-2-oxo-1,3-dioxolan-4-yl]-2,3,8,9-tetradehydro-1a,5,6,9a-tetrahydrocyclopenta[5,6]cyclonona[1,2-b]oxiren-5-yl 2-hydroxy-7-methoxy-5-methyl-1-naphthoate
Synonyms Sources
Ncs-chrom ChemIDplus
Neocarzinostatin chromophore KEGG COMPOUND
Manual Xrefs Databases
4108 DrugCentral
C12049 KEGG COMPOUND
CHR PDBeChem
Neocarzinostatin Wikipedia
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Registry Numbers Types Sources
4224827 Reaxys Registry Number Reaxys
81604-85-5 CAS Registry Number KEGG COMPOUND
81604-85-5 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
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Last Modified
22 February 2017