CHEBI:74351 - aclacinomycin T

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ChEBI Name aclacinomycin T
ChEBI ID CHEBI:74351
Definition An anthracycline that is aklavinone having an α-L-rhodosaminyl residue attached at position 4 via a glycosidic linkage.
Stars This entity has been manually annotated by the ChEBI Team.
Submitter KAX
Secondary ChEBI IDs CHEBI:74734
Supplier Information ZINC000003977735
Download Molfile XML SDF
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Formula C30H35NO10
Net Charge 0
Average Mass 569.607
Monoisotopic Mass 569.22610
InChI InChI=1S/C30H35NO10/c1-6-30(38)12-19(41-20-11-17(31(3)4)25(33)13(2)40-20)22-15(24(30)29(37)39-5)10-16-23(28(22)36)27(35)21-14(26(16)34)8-7-9-18(21)32/h7-10,13,17,19-20,24-25,32-33,36,38H,6,11-12H2,1-5H3/t13-,17-,19-,20-,24-,25+,30+/m0/s1
InChIKey LJZPVWKMAYDYAS-QKKPTTNWSA-N
SMILES C1=CC=C(C2=C1C(C=3C=C4[C@H]([C@](C[C@@H](C4=C(C3C2=O)O)O[C@H]5C[C@@H]([C@@H]([C@@H](O5)C)O)N(C)C)(CC)O)C(=O)OC)=O)O
Roles Classification
Biological Role(s): antimicrobial agent
A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.
metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
(via anthracycline )
Application(s): antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing aclacinomycin T (CHEBI:74351) has functional parent aklavinone (CHEBI:31181)
aclacinomycin T (CHEBI:74351) has role antimicrobial agent (CHEBI:33281)
aclacinomycin T (CHEBI:74351) has role antineoplastic agent (CHEBI:35610)
aclacinomycin T (CHEBI:74351) has role metabolite (CHEBI:25212)
aclacinomycin T (CHEBI:74351) is a aminoglycoside (CHEBI:47779)
aclacinomycin T (CHEBI:74351) is a anthracycline (CHEBI:48120)
aclacinomycin T (CHEBI:74351) is a deoxy hexoside (CHEBI:35315)
aclacinomycin T (CHEBI:74351) is a methyl ester (CHEBI:25248)
aclacinomycin T (CHEBI:74351) is a monosaccharide derivative (CHEBI:63367)
aclacinomycin T (CHEBI:74351) is a phenols (CHEBI:33853)
aclacinomycin T (CHEBI:74351) is a polyketide (CHEBI:26188)
aclacinomycin T (CHEBI:74351) is a tertiary alcohol (CHEBI:26878)
aclacinomycin T (CHEBI:74351) is a tetracenequinones (CHEBI:51286)
aclacinomycin T (CHEBI:74351) is conjugate base of aclacinomycin T(1+) (CHEBI:74755)
aclacinomycin T (CHEBI:74351) is tautomer of aclacinomycin T zwitterion (CHEBI:77979)
Incoming aclacinomycin T(1+) (CHEBI:74755) is conjugate acid of aclacinomycin T (CHEBI:74351)
aclacinomycin T zwitterion (CHEBI:77979) is tautomer of aclacinomycin T (CHEBI:74351)
IUPAC Name
methyl (1R,2R,4S)-2-ethyl-2,5,7-trihydroxy-6,11-dioxo-4-{[2,3,6-trideoxy-3-(dimethylamino)-α-L-lyxo-hexopyranosyl]oxy}-1,2,3,4,6,11-hexahydrotetracene-1-carboxylate
Synonyms Sources
1-deoxypyrromycin ChemIDplus
aclacinomycin T ChemIDplus
aklavin ChemIDplus
aklavine ChEBI
antibiotic MA 144T1 ChemIDplus
doxypyrromycin ChemIDplus
MA 144T1 ChemIDplus
methyl (1R,2R,4S)-4-{[(2R,4S,5S,6S)-4-(dimethylamino)-5-hydroxy-6-methyltetrahydro-2H-pyran-2-yl]oxy}-2-ethyl-2,5,7-trihydroxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracene-1-carboxylate IUPAC
NSC 100290 ChemIDplus
Rhodosaminyl-aklavinone KEGG COMPOUND
Manual Xrefs Databases
3VL PDBeChem
C18634 KEGG COMPOUND
US2009149545 Patent
US7544712 Patent
View more database links
Registry Numbers Types Sources
4898215 Reaxys Registry Number Reaxys
60504-57-6 CAS Registry Number KEGG COMPOUND
60504-57-6 CAS Registry Number ChemIDplus
Citations
Grocholski T, Dinis P, Niiranen L, Niemi J, Metsä-Ketelä M (2015)
Divergent evolution of an atypical S-adenosyl-l-methionine-dependent monooxygenase involved in anthracycline biosynthesis.
Proceedings of the National Academy of Sciences of the United States of America 112, 9866-9871 [PubMed:26216966]
[show Abstract]
Jansson A, Niemi J, Mäntsälä P, Schneider G (2003)
Crystal structure of aclacinomycin methylesterase with bound product analogues: implications for anthracycline recognition and mechanism.
The Journal of biological chemistry 278, 39006-39013 (Source: SUBMITTER) [PubMed:12878604]
[show Abstract]
Wang Y, Niemi J, Mäntsälä P (2002)
Modification of aklavinone and aclacinomycins in vitro and in vivo by rhodomycin biosynthesis gene products.
FEMS microbiology letters 208, 117-122 [PubMed:11934504]
[show Abstract]
Räty K, Hautala A, Torkkell S, Kantola J, Mäntsälä P, Hakala J, Ylihonko K (2002)
Characterization of mutations in aclacinomycin A-non-producing Streptomyces galilaeus strains with altered glycosylation patterns.
Microbiology (Reading, England) 148, 3375-3384 [PubMed:12427929]
[show Abstract]
Wang Y, Niemi J, Airas K, Ylihonko K, Hakala J, Mäntsälä P (2000)
Modifications of aclacinomycin T by aclacinomycin methyl esterase (RdmC) and aclacinomycin-10-hydroxylase (RdmB) from Streptomyces purpurascens.
Biochimica et biophysica acta 1480, 191-200 (Source: SUBMITTER) [PubMed:11004563]
[show Abstract]
Umezawa K, Sawamura M, Matsushima T, Sugimura T (1978)
Mutagenicity of aclacinomycin A and daunomycin derivatives.
Cancer research 38, 1782-1784 [PubMed:348304]
[show Abstract]
Kumar V, Remers WA, Grulich R (1977)
The structure of aklavin.
The Journal of antibiotics 30, 881-882 [PubMed:591449]
Kumar V, Remers WA, Grulich R (1977)
The structure of aklavin.
The Journal of antibiotics 30, 881-882 [PubMed:591449]
STRELITZ F, FLON H, WEISS U, ASHESHOV IN (1956)
Aklavin, an antibiotic substance with antiphage activity.
Journal of bacteriology 72, 90-94 [PubMed:13345780]
STRELITZ F, FLON H, WEISS U, ASHESHOV IN (1956)
Aklavin, an antibiotic substance with antiphage activity.
Journal of bacteriology 72, 90-94 [PubMed:13345780]
Last Modified
25 November 2019