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Record Information
Version2.0
Created at2022-04-28 06:45:17 UTC
Updated at2022-04-28 06:45:17 UTC
NP-MRD IDNP0062079
Secondary Accession NumbersNone
Natural Product Identification
Common NameEndocrocin
DescriptionEndocrocin belongs to the class of organic compounds known as anthracenecarboxylic acids. These are organic compounds containing a carboxylic acid group attached to an anthracene ring system. Endocrocin is an extremely weak basic (essentially neutral) compound (based on its pKa). Endocrocin is found in Aspergillus amstelodami, Aspergillus fumigatus, Claviceps purpurea, Cortinarius cardinalis, Cortinarius cinnabarinus, Cortinarius sanguineus, Flavocetraria cucullata, Penicillium oxalicum, Planococcus kraunhiae, Pyrenochaeta terrestris, Rumex dentatus , Rumex nepalensis, Rumex vesicarius , Setophoma terrestris and Talaromyces islandicus. Endocrocin was first documented in 1979 (PMID: 541252). A trihydroxyanthraquinone that is 9,10-anthraquinone which is substituted by a carboxy group at position 2, a methyl group at position 3, and hydroxy groups at positions 1, 6, and 8 (PMID: 21512234) (PMID: 22492455).
Structure
Thumb
Synonyms
ValueSource
9,10-Dihydro-1,6,8-trihydroxy-3-methyl-9,10-dioxo-2-anthracenecarboxylic acidChEBI
9,10-Dihydro-1,6,8-trihydroxy-3-methyl-9,10-dioxo-2-anthracenecarboxylateGenerator
Chemical FormulaC16H10O7
Average Mass314.2490 Da
Monoisotopic Mass314.04265 Da
IUPAC Name1,6,8-trihydroxy-3-methyl-9,10-dioxo-9,10-dihydroanthracene-2-carboxylic acid
Traditional Name1,6,8-trihydroxy-3-methyl-9,10-dioxoanthracene-2-carboxylic acid
CAS Registry NumberNot Available
SMILES
CC1=CC2=C(C(O)=C1C(O)=O)C(=O)C1=C(O)C=C(O)C=C1C2=O
InChI Identifier
InChI=1S/C16H10O7/c1-5-2-7-12(14(20)10(5)16(22)23)15(21)11-8(13(7)19)3-6(17)4-9(11)18/h2-4,17-18,20H,1H3,(H,22,23)
InChI KeyUZOHDKGTYVTYDZ-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Aspergillus amstelodamiLOTUS Database
Aspergillus fumigatusFungi
Claviceps purpureaLOTUS Database
Cortinarius cardinalisLOTUS Database
Cortinarius cinnabarinusLOTUS Database
Cortinarius sanguineusLOTUS Database
Flavocetraria cucullataLOTUS Database
Penicillium oxalicumLOTUS Database
Planococcus kraunhiaeLOTUS Database
Pyrenochaeta terrestrisFungi
Rumex dentatusPlant
Rumex nepalensisLOTUS Database
Rumex vesicariusPlant
Setophoma terrestrisLOTUS Database
Talaromyces islandicusLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as anthracenecarboxylic acids. These are organic compounds containing a carboxylic acid group attached to an anthracene ring system.
KingdomOrganic compounds
Super ClassBenzenoids
ClassAnthracenes
Sub ClassAnthracenecarboxylic acids and derivatives
Direct ParentAnthracenecarboxylic acids
Alternative Parents
Substituents
  • Anthracene carboxylic acid
  • 9,10-anthraquinone
  • Anthraquinone
  • Hydroxyanthraquinone
  • 2-naphthalenecarboxylic acid
  • 2-naphthalenecarboxylic acid or derivatives
  • Salicylic acid or derivatives
  • Hydroxybenzoic acid
  • Aryl ketone
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Vinylogous acid
  • Ketone
  • Monocarboxylic acid or derivatives
  • Polyol
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organooxygen compound
  • Aromatic homopolycyclic compound
Molecular FrameworkAromatic homopolycyclic 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
logP2.11ALOGPS
logP4.13ChemAxon
logS-3ALOGPS
pKa (Strongest Acidic)2.22ChemAxon
pKa (Strongest Basic)-5.4ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area132.13 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity79.39 m³·mol⁻¹ChemAxon
Polarizability29.75 ųChemAxon
Number of Rings3ChemAxon
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 IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound160483
PDB IDNot Available
ChEBI ID64450
Good Scents IDNot Available
References
General References
  1. Kikuchi N, Teshiba M, Tsutsumi T, Fudou R, Nagasawa H, Sakuda S: Endocrocin and its derivatives from the Japanese mealybug Planococcus kraunhiae. Biosci Biotechnol Biochem. 2011;75(4):764-7. doi: 10.1271/bbb.100742. Epub 2011 Apr 22. [PubMed:21512234 ]
  2. Lim FY, Hou Y, Chen Y, Oh JH, Lee I, Bugni TS, Keller NP: Genome-based cluster deletion reveals an endocrocin biosynthetic pathway in Aspergillus fumigatus. Appl Environ Microbiol. 2012 Jun;78(12):4117-25. doi: 10.1128/AEM.07710-11. Epub 2012 Apr 6. [PubMed:22492455 ]
  3. Kurobane I, Vining LC, McInnes AG: Biosynthetic relationships among the secalonic acids. Isolation of emodin, endocrocin and secalonic acids from Pyrenochaeta terrestris and Aspergillus aculeatus. J Antibiot (Tokyo). 1979 Dec;32(12):1256-66. doi: 10.7164/antibiotics.32.1256. [PubMed:541252 ]