Page last updated: 2024-11-08

neocarzinostatin chromophore

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth

Description

neocarzinostatin chromophore: nonprotein chromophore of neocarzinostatin; antibiotic activity of Neocarzinostatin depends on wholy on chromophore interaction with DNA; Chrom A & Chrom B are separated by HPLC; Chrom C is derived from Chrom A; Chrom D is inactive minor component [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

neocarzinostatin chromophore : 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)-alpha-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. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Cross-References

ID SourceID
PubMed CID447545
CHEBI ID29655
MeSH IDM0101081

Synonyms (21)

Synonym
neocarzinostatin-chromophore
81604-85-5
neocarzinostatin chromophore
DB04408
1O5P
ncs-chromophore
CHEBI:29655
ncs-chrom
(1as,5r,6r,6ae,9ar)-6-{[2,6-dideoxy-2-(methylamino)-alpha-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
(+)-neocarzinostatin chromophore
neocarzinostatin chrom i
1-naphthalenecarboxylic acid, 2-hydroxy-7-methoxy-5-methyl-, (1as,5r,6r,6ae,9ar)-2,3,8,9-tetradehydro-6-((2,6-dideoxy-2-(methylamino)-.alpha.-d-galactopyranosyl)oxy)-1a,5,6,9a-tetrahydro-1a-((4r)-2-oxo-1,3-dioxolan-4-yl)cyclopenta(5,6)cyclonon(1,2-b)oxire
neocarzinostatin chromophore a
neocarzinostatin chromophore i
2SJ8J82D90 ,
79633-18-4
unii-2sj8j82d90
(1as,5r,6r,6ae,9ar)-6-{[2,6-dideoxy-2-(methylamino)-alpha-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-methylnaphthalene-1-carboxylate
Q26847067
[(4s,6r,9e,11r,12r)-11-[(2r,3r,4r,5r,6r)-4,5-dihydroxy-6-methyl-3-(methylamino)oxan-2-yl]oxy-4-[(4r)-2-oxo-1,3-dioxolan-4-yl]-5-oxatricyclo[8.3.0.04,6]trideca-1(13),9-dien-2,7-diyn-12-yl] 2-hydroxy-7-methoxy-5-methylnaphthalene-1-carboxylate
DTXSID70868619

Research Excerpts

Effects

ExcerptReferenceRelevance
"Neocarzinostatin chromophore (NCS-chrom) has been found previously to induce thiol-dependent abasic site formation and cleavage on the RNA strand of RNA-DNA hybrids. "( Characterization of a novel covalent monoadduct on the RNA overhang of an RNA-DNA hybrid induced by antitumor antibiotic neocarzinostatin.
Goldberg, IH; Liu, CL; Smith, RD; Xi, Z; Zheng, P, 1998
)
1.74
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (1)

RoleDescription
antineoplastic agentA substance that inhibits or prevents the proliferation of neoplasms.
[role information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Drug Classes (5)

ClassDescription
cyclopentacyclononaoxirene
D-galactosaminide
dioxolane
naphthoate ester
monosaccharide derivativeA carbohydrate derivative that is formally obtained from a monosaccharide.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Protein Targets (1)

Activation Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Chain A, NeocarzinostatinStreptomyces carzinostaticusKd0.00010.00010.00010.0001AID977611
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (2)

Assay IDTitleYearJournalArticle
AID977611Experimentally measured binding affinity data (Kd) for protein-ligand complexes derived from PDB2005The Journal of biological chemistry, Mar-25, Volume: 280, Issue:12
Solution NMR structure investigation for releasing mechanism of neocarzinostatin chromophore from the holoprotein.
AID1811Experimentally measured binding affinity data derived from PDB2005The Journal of biological chemistry, Mar-25, Volume: 280, Issue:12
Solution NMR structure investigation for releasing mechanism of neocarzinostatin chromophore from the holoprotein.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (63)

TimeframeStudies, This Drug (%)All Drugs %
pre-199016 (25.40)18.7374
1990's22 (34.92)18.2507
2000's20 (31.75)29.6817
2010's4 (6.35)24.3611
2020's1 (1.59)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews2 (3.17%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other61 (96.83%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]