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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:30:50 UTC
Update Date2022-03-07 02:52:11 UTC
HMDB IDHMDB0029508
Secondary Accession Numbers
  • HMDB29508
Metabolite Identification
Common NameLaccaic acid D
DescriptionLaccaic acid D, also known as flavokermesate or laccaate D, 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. Laccaic acid D is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review a small amount of articles have been published on Laccaic acid D.
Structure
Data?1582753428
Synonyms
ValueSource
9,10-Dihydro-3,6,8-trihydroxy-1-methyl-9,10-dioxo-2-anthracenecarboxylic acidChEBI
Flavokermesic acidChEBI
Xanthokermesic acidChEBI
9,10-Dihydro-3,6,8-trihydroxy-1-methyl-9,10-dioxo-2-anthracenecarboxylateGenerator
FlavokermesateGenerator
XanthokermesateGenerator
Laccaate DGenerator
9,10-Dihydro-3,6,8-trihydroxy-1-methyl-9,10-dioxo-2-anthracenecarboxylic acid, 9ciHMDB
Chemical FormulaC16H10O7
Average Molecular Weight314.2464
Monoisotopic Molecular Weight314.042652674
IUPAC Name3,6,8-trihydroxy-1-methyl-9,10-dioxo-9,10-dihydroanthracene-2-carboxylic acid
Traditional Name3,6,8-trihydroxy-1-methyl-9,10-dioxoanthracene-2-carboxylic acid
CAS Registry Number18499-84-8
SMILES
CC1=C(C(O)=O)C(O)=CC2=C1C(=O)C1=C(C=C(O)C=C1O)C2=O
InChI Identifier
InChI=1S/C16H10O7/c1-5-11-8(4-10(19)12(5)16(22)23)14(20)7-2-6(17)3-9(18)13(7)15(11)21/h2-4,17-19H,1H3,(H,22,23)
InChI KeyDDTNCHWMNZLWKO-UHFFFAOYSA-N
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 DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility5.5 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.25 g/LALOGPS
logP2.08ALOGPS
logP3.48ChemAxon
logS-3.1ALOGPS
pKa (Strongest Acidic)2.23ChemAxon
pKa (Strongest Basic)-4.2ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area132.13 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity79.39 m³·mol⁻¹ChemAxon
Polarizability29.65 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+171.52131661259
DarkChem[M-H]-171.58631661259
DeepCCS[M+H]+169.21230932474
DeepCCS[M-H]-166.85430932474
DeepCCS[M-2H]-200.90930932474
DeepCCS[M+Na]+176.13630932474
AllCCS[M+H]+169.432859911
AllCCS[M+H-H2O]+166.032859911
AllCCS[M+NH4]+172.632859911
AllCCS[M+Na]+173.532859911
AllCCS[M-H]-170.132859911
AllCCS[M+Na-2H]-169.332859911
AllCCS[M+HCOO]-168.732859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Laccaic acid DCC1=C(C(O)=O)C(O)=CC2=C1C(=O)C1=C(C=C(O)C=C1O)C2=O4387.3Standard polar33892256
Laccaic acid DCC1=C(C(O)=O)C(O)=CC2=C1C(=O)C1=C(C=C(O)C=C1O)C2=O2090.2Standard non polar33892256
Laccaic acid DCC1=C(C(O)=O)C(O)=CC2=C1C(=O)C1=C(C=C(O)C=C1O)C2=O3103.7Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Laccaic acid D,1TMS,isomer #1CC1=C(C(=O)O[Si](C)(C)C)C(O)=CC2=C1C(=O)C1=C(O)C=C(O)C=C1C2=O2968.2Semi standard non polar33892256
Laccaic acid D,1TMS,isomer #2CC1=C(C(=O)O)C(O[Si](C)(C)C)=CC2=C1C(=O)C1=C(O)C=C(O)C=C1C2=O2922.7Semi standard non polar33892256
Laccaic acid D,1TMS,isomer #3CC1=C(C(=O)O)C(O)=CC2=C1C(=O)C1=C(O)C=C(O[Si](C)(C)C)C=C1C2=O2996.9Semi standard non polar33892256
Laccaic acid D,1TMS,isomer #4CC1=C(C(=O)O)C(O)=CC2=C1C(=O)C1=C(O[Si](C)(C)C)C=C(O)C=C1C2=O2911.7Semi standard non polar33892256
Laccaic acid D,2TMS,isomer #1CC1=C(C(=O)O[Si](C)(C)C)C(O[Si](C)(C)C)=CC2=C1C(=O)C1=C(O)C=C(O)C=C1C2=O2918.8Semi standard non polar33892256
Laccaic acid D,2TMS,isomer #2CC1=C(C(=O)O[Si](C)(C)C)C(O)=CC2=C1C(=O)C1=C(O[Si](C)(C)C)C=C(O)C=C1C2=O2905.7Semi standard non polar33892256
Laccaic acid D,2TMS,isomer #3CC1=C(C(=O)O[Si](C)(C)C)C(O)=CC2=C1C(=O)C1=C(O)C=C(O[Si](C)(C)C)C=C1C2=O3017.5Semi standard non polar33892256
Laccaic acid D,2TMS,isomer #4CC1=C(C(=O)O)C(O[Si](C)(C)C)=CC2=C1C(=O)C1=C(O[Si](C)(C)C)C=C(O)C=C1C2=O2877.3Semi standard non polar33892256
Laccaic acid D,2TMS,isomer #5CC1=C(C(=O)O)C(O[Si](C)(C)C)=CC2=C1C(=O)C1=C(O)C=C(O[Si](C)(C)C)C=C1C2=O2925.8Semi standard non polar33892256
Laccaic acid D,2TMS,isomer #6CC1=C(C(=O)O)C(O)=CC2=C1C(=O)C1=C(O[Si](C)(C)C)C=C(O[Si](C)(C)C)C=C1C2=O2933.4Semi standard non polar33892256
Laccaic acid D,3TMS,isomer #1CC1=C(C(=O)O[Si](C)(C)C)C(O[Si](C)(C)C)=CC2=C1C(=O)C1=C(O[Si](C)(C)C)C=C(O)C=C1C2=O2906.1Semi standard non polar33892256
Laccaic acid D,3TMS,isomer #2CC1=C(C(=O)O[Si](C)(C)C)C(O[Si](C)(C)C)=CC2=C1C(=O)C1=C(O)C=C(O[Si](C)(C)C)C=C1C2=O2956.1Semi standard non polar33892256
Laccaic acid D,3TMS,isomer #3CC1=C(C(=O)O[Si](C)(C)C)C(O)=CC2=C1C(=O)C1=C(O[Si](C)(C)C)C=C(O[Si](C)(C)C)C=C1C2=O2957.0Semi standard non polar33892256
Laccaic acid D,3TMS,isomer #4CC1=C(C(=O)O)C(O[Si](C)(C)C)=CC2=C1C(=O)C1=C(O[Si](C)(C)C)C=C(O[Si](C)(C)C)C=C1C2=O2940.0Semi standard non polar33892256
Laccaic acid D,4TMS,isomer #1CC1=C(C(=O)O[Si](C)(C)C)C(O[Si](C)(C)C)=CC2=C1C(=O)C1=C(O[Si](C)(C)C)C=C(O[Si](C)(C)C)C=C1C2=O2981.6Semi standard non polar33892256
Laccaic acid D,1TBDMS,isomer #1CC1=C(C(=O)O[Si](C)(C)C(C)(C)C)C(O)=CC2=C1C(=O)C1=C(O)C=C(O)C=C1C2=O3203.1Semi standard non polar33892256
Laccaic acid D,1TBDMS,isomer #2CC1=C(C(=O)O)C(O[Si](C)(C)C(C)(C)C)=CC2=C1C(=O)C1=C(O)C=C(O)C=C1C2=O3164.5Semi standard non polar33892256
Laccaic acid D,1TBDMS,isomer #3CC1=C(C(=O)O)C(O)=CC2=C1C(=O)C1=C(O)C=C(O[Si](C)(C)C(C)(C)C)C=C1C2=O3233.4Semi standard non polar33892256
Laccaic acid D,1TBDMS,isomer #4CC1=C(C(=O)O)C(O)=CC2=C1C(=O)C1=C(O[Si](C)(C)C(C)(C)C)C=C(O)C=C1C2=O3166.0Semi standard non polar33892256
Laccaic acid D,2TBDMS,isomer #1CC1=C(C(=O)O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=CC2=C1C(=O)C1=C(O)C=C(O)C=C1C2=O3367.4Semi standard non polar33892256
Laccaic acid D,2TBDMS,isomer #2CC1=C(C(=O)O[Si](C)(C)C(C)(C)C)C(O)=CC2=C1C(=O)C1=C(O[Si](C)(C)C(C)(C)C)C=C(O)C=C1C2=O3367.4Semi standard non polar33892256
Laccaic acid D,2TBDMS,isomer #3CC1=C(C(=O)O[Si](C)(C)C(C)(C)C)C(O)=CC2=C1C(=O)C1=C(O)C=C(O[Si](C)(C)C(C)(C)C)C=C1C2=O3444.6Semi standard non polar33892256
Laccaic acid D,2TBDMS,isomer #4CC1=C(C(=O)O)C(O[Si](C)(C)C(C)(C)C)=CC2=C1C(=O)C1=C(O[Si](C)(C)C(C)(C)C)C=C(O)C=C1C2=O3363.6Semi standard non polar33892256
Laccaic acid D,2TBDMS,isomer #5CC1=C(C(=O)O)C(O[Si](C)(C)C(C)(C)C)=CC2=C1C(=O)C1=C(O)C=C(O[Si](C)(C)C(C)(C)C)C=C1C2=O3417.5Semi standard non polar33892256
Laccaic acid D,2TBDMS,isomer #6CC1=C(C(=O)O)C(O)=CC2=C1C(=O)C1=C(O[Si](C)(C)C(C)(C)C)C=C(O[Si](C)(C)C(C)(C)C)C=C1C2=O3429.3Semi standard non polar33892256
Laccaic acid D,3TBDMS,isomer #1CC1=C(C(=O)O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=CC2=C1C(=O)C1=C(O[Si](C)(C)C(C)(C)C)C=C(O)C=C1C2=O3529.2Semi standard non polar33892256
Laccaic acid D,3TBDMS,isomer #2CC1=C(C(=O)O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=CC2=C1C(=O)C1=C(O)C=C(O[Si](C)(C)C(C)(C)C)C=C1C2=O3609.5Semi standard non polar33892256
Laccaic acid D,3TBDMS,isomer #3CC1=C(C(=O)O[Si](C)(C)C(C)(C)C)C(O)=CC2=C1C(=O)C1=C(O[Si](C)(C)C(C)(C)C)C=C(O[Si](C)(C)C(C)(C)C)C=C1C2=O3617.0Semi standard non polar33892256
Laccaic acid D,3TBDMS,isomer #4CC1=C(C(=O)O)C(O[Si](C)(C)C(C)(C)C)=CC2=C1C(=O)C1=C(O[Si](C)(C)C(C)(C)C)C=C(O[Si](C)(C)C(C)(C)C)C=C1C2=O3597.4Semi standard non polar33892256
Laccaic acid D,4TBDMS,isomer #1CC1=C(C(=O)O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=CC2=C1C(=O)C1=C(O[Si](C)(C)C(C)(C)C)C=C(O[Si](C)(C)C(C)(C)C)C=C1C2=O3775.7Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Laccaic acid D GC-MS (Non-derivatized) - 70eV, Positivesplash10-02ds-0491000000-1358b194a0c9351ccb982017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Laccaic acid D GC-MS (4 TMS) - 70eV, Positivesplash10-05tr-2202190000-65c1b7258bee80c66ba92017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Laccaic acid D GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Laccaic acid D GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Laccaic acid D 10V, Positive-QTOFsplash10-014i-0049000000-ffd6441f57a0b87b09222016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Laccaic acid D 20V, Positive-QTOFsplash10-00kb-0094000000-b793451cac47f1a576762016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Laccaic acid D 40V, Positive-QTOFsplash10-0a4i-2590000000-cdace83113f5c43ec5dd2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Laccaic acid D 10V, Negative-QTOFsplash10-03xr-0069000000-d71f14e1a742275501af2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Laccaic acid D 20V, Negative-QTOFsplash10-014i-0091000000-c72b244aa19ca6d9de132016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Laccaic acid D 40V, Negative-QTOFsplash10-016r-0290000000-fcfd0ee63ab61408da2e2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Laccaic acid D 10V, Negative-QTOFsplash10-03xr-0098000000-65fbab827b8177985dbf2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Laccaic acid D 20V, Negative-QTOFsplash10-014i-0091000000-e73d5be536d73183f9182021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Laccaic acid D 40V, Negative-QTOFsplash10-00or-0090000000-f99d06f1f8a3e9b7d4b42021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Laccaic acid D 10V, Positive-QTOFsplash10-00kb-0095000000-9e34f0b963f3809e8c162021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Laccaic acid D 20V, Positive-QTOFsplash10-0002-0090000000-e32a154b20754d0f29842021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Laccaic acid D 40V, Positive-QTOFsplash10-004i-0290000000-75ccc2ef75c2baf210112021-09-22Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB000643
KNApSAcK IDC00051186
Chemspider ID8058979
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound9883304
PDB IDNot Available
ChEBI ID90194
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1810061
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .