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Record Information
Version2.0
Created at2022-09-12 03:10:00 UTC
Updated at2022-09-12 03:10:00 UTC
NP-MRD IDNP0323621
Secondary Accession NumbersNone
Natural Product Identification
Common Name4,6,8-trihydroxy-3-methyltetraphene-1,2,7,12-tetrone
DescriptionOviedomycin belongs to the class of organic compounds known as phenanthrols. Phenanthrols are compounds containing a phenanthrene (or its hydrogenated derivative) to which a hydroxyl group is attached. 4,6,8-trihydroxy-3-methyltetraphene-1,2,7,12-tetrone is found in Streptomyces ansochromogenes. 4,6,8-trihydroxy-3-methyltetraphene-1,2,7,12-tetrone was first documented in 2014 (PMID: 25303210). Based on a literature review a small amount of articles have been published on Oviedomycin (PMID: 28972184) (PMID: 35439610) (PMID: 34572679) (PMID: 28562006).
Structure
Thumb
SynonymsNot Available
Chemical FormulaC19H10O7
Average Mass350.2820 Da
Monoisotopic Mass350.04265 Da
IUPAC Name4,6,8-trihydroxy-3-methyl-1,2,7,12-tetrahydrotetraphene-1,2,7,12-tetrone
Traditional Name4,6,8-trihydroxy-3-methyltetraphene-1,2,7,12-tetrone
CAS Registry NumberNot Available
SMILES
CC1=C(O)C2=CC(O)=C3C(=O)C4=C(O)C=CC=C4C(=O)C3=C2C(=O)C1=O
InChI Identifier
InChI=1S/C19H10O7/c1-6-15(22)8-5-10(21)13-14(12(8)19(26)16(6)23)17(24)7-3-2-4-9(20)11(7)18(13)25/h2-5,20-22H,1H3
InChI KeySKUDQXAQMMVQKR-UHFFFAOYSA-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 ansochromogenesLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as phenanthrols. Phenanthrols are compounds containing a phenanthrene (or its hydrogenated derivative) to which a hydroxyl group is attached.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPhenanthrenes and derivatives
Sub ClassPhenanthrols
Direct ParentPhenanthrols
Alternative Parents
Substituents
  • Phenanthrol
  • Anthracene
  • 1-naphthol
  • 2-naphthol
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Vinylogous acid
  • Cyclic ketone
  • Polyol
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic homopolycyclic compound
Molecular FrameworkAromatic homopolycyclic compounds
External DescriptorsNot Available
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
logP0.39ChemAxon
pKa (Strongest Acidic)2.18ChemAxon
pKa (Strongest Basic)5.95ChemAxon
Physiological Charge-3ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area128.97 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity91.47 m³·mol⁻¹ChemAxon
Polarizability33.54 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDC00046255
Chemspider ID4481084
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5323531
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Rico S, Yepes A, Rodriguez H, Santamaria J, Antoraz S, Krause EM, Diaz M, Santamaria RI: Regulation of the AbrA1/A2 two-component system in Streptomyces coelicolor and the potential of its deletion strain as a heterologous host for antibiotic production. PLoS One. 2014 Oct 10;9(10):e109844. doi: 10.1371/journal.pone.0109844. eCollection 2014. [PubMed:25303210 ]
  2. Xu J, Zhang J, Zhuo J, Li Y, Tian Y, Tan H: Activation and mechanism of a cryptic oviedomycin gene cluster via the disruption of a global regulatory gene, adpA, in Streptomyces ansochromogenes. J Biol Chem. 2017 Dec 1;292(48):19708-19720. doi: 10.1074/jbc.M117.809145. Epub 2017 Sep 25. [PubMed:28972184 ]
  3. Li J, Wang W, Liu X, Tian Y, Tan H, Zhang J: A butenolide signaling system synergized with biosynthetic gene modules led to effective activation and enhancement of silent oviedomycin production in Streptomyces. Metab Eng. 2022 Jul;72:289-296. doi: 10.1016/j.ymben.2022.04.002. Epub 2022 Apr 18. [PubMed:35439610 ]
  4. Li Y, Yu H, Guan H, Li J, Zhang J, Xiang H, Li J, Tan H: Activation of Cryptic Antibiotic Biosynthetic Gene Clusters Guided by RNA-seq Data from Both Streptomyces ansochromogenes and DeltawblA. Antibiotics (Basel). 2021 Sep 10;10(9):1097. doi: 10.3390/antibiotics10091097. [PubMed:34572679 ]
  5. Zhang B, Tian W, Wang S, Yan X, Jia X, Pierens GK, Chen W, Ma H, Deng Z, Qu X: Activation of Natural Products Biosynthetic Pathways via a Protein Modification Level Regulation. ACS Chem Biol. 2017 Jul 21;12(7):1732-1736. doi: 10.1021/acschembio.7b00225. Epub 2017 Jun 2. [PubMed:28562006 ]
  6. LOTUS database [Link]