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Record Information
Version2.0
Created at2022-09-12 07:42:22 UTC
Updated at2022-09-12 07:42:23 UTC
NP-MRD IDNP0326284
Secondary Accession NumbersNone
Natural Product Identification
Common Nameaclacinomycin t
DescriptionAclacinomycin T, also known as aklavin or 1-deoxypyrromycin, belongs to the class of organic compounds known as anthracyclines. These are polyketides containing a tetracenequinone ring structure with a sugar attached by glycosidic linkage. Aclacinomycin T is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. aclacinomycin t is found in Streptomyces galilaeus. aclacinomycin t was first documented in 2002 (PMID: 12427929). Based on a literature review a small amount of articles have been published on aclacinomycin T (PMID: 26216966) (PMID: 12925797).
Structure
Thumb
Synonyms
ValueSource
1-DeoxypyrromycinChEBI
AklavinChEBI
AklavineChEBI
Antibiotic ma 144T1ChEBI
DoxypyrromycinChEBI
MA 144T1ChEBI
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-carboxylateChEBI
NSC 100290ChEBI
Rhodosaminyl-aklavinoneChEBI
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-carboxylic acidGenerator
MA 144 S1MeSH
Aclacinomycin hydrochlorideMeSH
Aclacinomycin mMeSH
Aclacinomycin bMeSH
Aclacinomycin SMeSH
Aclacinomycin XMeSH
Aclacinomycin yMeSH
AclacinomycinsMeSH
SiwenmycinMeSH
AclacinomycinMeSH
MA 144 N1MeSH
Aclacinomycin NMeSH
Chemical FormulaC30H35NO10
Average Mass569.6070 Da
Monoisotopic Mass569.22610 Da
IUPAC Namemethyl (1R,2R,4S)-4-{[(2R,4S,5S,6S)-4-(dimethylamino)-5-hydroxy-6-methyloxan-2-yl]oxy}-2-ethyl-2,5,7-trihydroxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracene-1-carboxylate
Traditional Namemethyl (1R,2R,4S)-4-{[(2R,4S,5S,6S)-4-(dimethylamino)-5-hydroxy-6-methyloxan-2-yl]oxy}-2-ethyl-2,5,7-trihydroxy-6,11-dioxo-3,4-dihydro-1H-tetracene-1-carboxylate
CAS Registry NumberNot Available
SMILES
CC[C@@]1(O)C[C@H](O[C@H]2C[C@@H]([C@H](O)[C@H](C)O2)N(C)C)C2=C(C=C3C(=O)C4=CC=CC(O)=C4C(=O)C3=C2O)[C@H]1C(=O)OC
InChI Identifier
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
InChI KeyLJZPVWKMAYDYAS-QKKPTTNWSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Streptomyces galilaeusLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as anthracyclines. These are polyketides containing a tetracenequinone ring structure with a sugar attached by glycosidic linkage.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassAnthracyclines
Sub ClassNot Available
Direct ParentAnthracyclines
Alternative Parents
Substituents
  • Anthracyclinone-skeleton
  • Anthracycline
  • Aminoglycoside core
  • Tetracenequinone
  • Anthracene carboxylic acid
  • Anthracene carboxylic acid or derivatives
  • 1,4-anthraquinone
  • 9,10-anthraquinone
  • Anthracene
  • 1-naphthalenecarboxylic acid or derivatives
  • Hexose monosaccharide
  • O-glycosyl compound
  • Glycosyl compound
  • Tetralin
  • Aryl ketone
  • 1-hydroxy-4-unsubstituted benzenoid
  • Amino saccharide
  • 1-hydroxy-2-unsubstituted benzenoid
  • Benzenoid
  • Monosaccharide
  • Oxane
  • Tertiary alcohol
  • Methyl ester
  • Vinylogous acid
  • Secondary alcohol
  • Tertiary amine
  • Tertiary aliphatic amine
  • Ketone
  • 1,2-aminoalcohol
  • Carboxylic acid ester
  • Amino acid or derivatives
  • Polyol
  • Acetal
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Oxacycle
  • Organoheterocyclic compound
  • Alcohol
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Carbonyl group
  • Amine
  • Organonitrogen compound
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP2.48ChemAxon
pKa (Strongest Acidic)7.48ChemAxon
pKa (Strongest Basic)8.67ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area163.06 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity146.84 m³·mol⁻¹ChemAxon
Polarizability59.48 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID131997
KEGG Compound IDC18634
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound149755
PDB IDNot Available
ChEBI ID74351
Good Scents IDNot Available
References
General References
  1. Grocholski T, Dinis P, Niiranen L, Niemi J, Metsa-Ketela M: Divergent evolution of an atypical S-adenosyl-l-methionine-dependent monooxygenase involved in anthracycline biosynthesis. Proc Natl Acad Sci U S A. 2015 Aug 11;112(32):9866-71. doi: 10.1073/pnas.1501765112. Epub 2015 Jul 27. [PubMed:26216966 ]
  2. Jansson A, Niemi J, Mantsala P, Schneider G: Crystallization and preliminary X-ray diffraction studies of aclacinomycin-10-methyl esterase and aclacinomycin-10-hydroxylase from Streptomyces purpurascens. Acta Crystallogr D Biol Crystallogr. 2003 Sep;59(Pt 9):1637-9. doi: 10.1107/s0907444903014100. Epub 2003 Aug 19. [PubMed:12925797 ]
  3. Raty K, Hautala A, Torkkell S, Kantola J, Mantsala P, Hakala J, Ylihonko K: Characterization of mutations in aclacinomycin A-non-producing Streptomyces galilaeus strains with altered glycosylation patterns. Microbiology (Reading). 2002 Nov;148(Pt 11):3375-3384. doi: 10.1099/00221287-148-11-3375. [PubMed:12427929 ]
  4. LOTUS database [Link]