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Showing metabocard for Terreic acid (HMDB0258836)

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IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesenzymes (6) Show 6 proteinsXML
enzymes (6) Show 6 proteins
Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2021-09-11 20:36:58 UTC
Update Date2021-10-01 23:19:57 UTC
HMDB IDHMDB0258836
Secondary Accession NumbersNone
Metabolite Identification
Common NameTerreic acid
Description3-hydroxy-4-methyl-7-oxabicyclo[4.1.0]hept-3-ene-2,5-dione belongs to the class of organic compounds known as cyclohexenones. Cyclohexenones are compounds containing a cylohexenone moiety, which is a six-membered aliphatic ring that carries a ketone and has one endocyclic double bond. Based on a literature review very few articles have been published on 3-hydroxy-4-methyl-7-oxabicyclo[4.1.0]hept-3-ene-2,5-dione. This compound has been identified in human blood as reported by (PMID: 31557052 ). Terreic acid is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Terreic acid is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0258836 (Terreic acid)


  Mrv1533004161519502D          

 11 12  0  0  0  0            999 V2000
    3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
  2 10  1  0  0  0  0
 10 11  2  0  0  0  0
M  END
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3D MOL for HMDB0258836 (Terreic acid)

HMDB0258836
     RDKit          3D
Terreic acid
 17 18  0  0  0  0  0  0  0  0999 V2000
   -2.0478   -0.8365   -0.0633 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6202   -0.3570   -0.0441 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3169    0.9295   -0.2881 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3508    1.8277   -0.5606 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0911    1.3248   -0.2563 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4042    2.5072   -0.0715 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0408    0.2621   -0.4509 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8874   -0.4197    0.2881 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6890   -0.6687    0.7489 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4750   -1.2857    0.2517 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2473   -2.5012    0.0455 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1930   -1.6478    0.6923 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3316   -1.1302   -1.0730 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7272   -0.0035    0.2632 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6983    2.3490    0.2569 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9328   -0.2065   -1.4816 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5182   -0.1434    1.7429 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  3  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 10  2  1  0
  9  7  1  0
  1 12  1  0
  1 13  1  0
  1 14  1  0
  4 15  1  0
  7 16  1  0
  9 17  1  0
M  END
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3D SDF for HMDB0258836 (Terreic acid)


  Mrv1533004161519502D          

 11 12  0  0  0  0            999 V2000
    3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
  2 10  1  0  0  0  0
 10 11  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0258836

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1=C(O)C(=O)C2OC2C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C7H6O4/c1-2-3(8)5(10)7-6(11-7)4(2)9/h6-8H,1H3

> <INCHI_KEY>
ATFNSNUJZOYXFC-UHFFFAOYSA-N

> <FORMULA>
C7H6O4

> <MOLECULAR_WEIGHT>
154.121

> <EXACT_MASS>
154.026608673

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
17

> <JCHEM_AVERAGE_POLARIZABILITY>
13.408421921609726

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-hydroxy-4-methyl-7-oxabicyclo[4.1.0]hept-3-ene-2,5-dione

> <ALOGPS_LOGP>
-0.19

> <JCHEM_LOGP>
0.2748246343333334

> <ALOGPS_LOGS>
0.48

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
19.94808234332145

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.478417529922911

> <JCHEM_PKA_STRONGEST_BASIC>
-4.320529302381678

> <JCHEM_POLAR_SURFACE_AREA>
66.9

> <JCHEM_REFRACTIVITY>
35.449600000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.71e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
terreic acid

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for HMDB0258836 (Terreic acid)

HMDB0258836
     RDKit          3D
Terreic acid
 17 18  0  0  0  0  0  0  0  0999 V2000
   -2.0478   -0.8365   -0.0633 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6202   -0.3570   -0.0441 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3169    0.9295   -0.2881 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3508    1.8277   -0.5606 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0911    1.3248   -0.2563 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4042    2.5072   -0.0715 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0408    0.2621   -0.4509 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8874   -0.4197    0.2881 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6890   -0.6687    0.7489 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4750   -1.2857    0.2517 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2473   -2.5012    0.0455 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1930   -1.6478    0.6923 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3316   -1.1302   -1.0730 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7272   -0.0035    0.2632 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6983    2.3490    0.2569 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9328   -0.2065   -1.4816 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5182   -0.1434    1.7429 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  3  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 10  2  1  0
  9  7  1  0
  1 12  1  0
  1 13  1  0
  1 14  1  0
  4 15  1  0
  7 16  1  0
  9 17  1  0
M  END
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PDB for HMDB0258836 (Terreic acid)

HEADER    PROTEIN                                 16-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   16-APR-15         0                                  
HETATM    1  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.335   3.080   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       6.668   0.770   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       4.001   0.770   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       4.001  -0.770   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       1.334   2.310   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       2.667   3.080   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       4.001   5.390   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   10                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8    9                                                  
CONECT    8    7    9                                                       
CONECT    9    8    7   10                                                  
CONECT   10    9    2   11                                                  
CONECT   11   10                                                            
MASTER        0    0    0    0    0    0    0    0   11    0   24    0
END
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3D PDB for HMDB0258836 (Terreic acid)

COMPND    HMDB0258836
HETATM    1  C1  UNL     1      -2.048  -0.837  -0.063  1.00  0.00           C  
HETATM    2  C2  UNL     1      -0.620  -0.357  -0.044  1.00  0.00           C  
HETATM    3  C3  UNL     1      -0.317   0.930  -0.288  1.00  0.00           C  
HETATM    4  O1  UNL     1      -1.351   1.828  -0.561  1.00  0.00           O  
HETATM    5  C4  UNL     1       1.091   1.325  -0.256  1.00  0.00           C  
HETATM    6  O2  UNL     1       1.404   2.507  -0.072  1.00  0.00           O  
HETATM    7  C5  UNL     1       2.041   0.262  -0.451  1.00  0.00           C  
HETATM    8  O3  UNL     1       2.887  -0.420   0.288  1.00  0.00           O  
HETATM    9  C6  UNL     1       1.689  -0.669   0.749  1.00  0.00           C  
HETATM   10  C7  UNL     1       0.475  -1.286   0.252  1.00  0.00           C  
HETATM   11  O4  UNL     1       0.247  -2.501   0.045  1.00  0.00           O  
HETATM   12  H1  UNL     1      -2.193  -1.648   0.692  1.00  0.00           H  
HETATM   13  H2  UNL     1      -2.332  -1.130  -1.073  1.00  0.00           H  
HETATM   14  H3  UNL     1      -2.727  -0.003   0.263  1.00  0.00           H  
HETATM   15  H4  UNL     1      -1.698   2.349   0.257  1.00  0.00           H  
HETATM   16  H5  UNL     1       1.933  -0.207  -1.482  1.00  0.00           H  
HETATM   17  H6  UNL     1       1.518  -0.143   1.743  1.00  0.00           H  
CONECT    1    2   12   13   14
CONECT    2    3    3   10
CONECT    3    4    5
CONECT    4   15
CONECT    5    6    6    7
CONECT    7    8    9   16
CONECT    8    9
CONECT    9   10   17
CONECT   10   11   11
END
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SMILES for HMDB0258836 (Terreic acid)

CC1=C(O)C(=O)C2OC2C1=O
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INCHI for HMDB0258836 (Terreic acid)

InChI=1S/C7H6O4/c1-2-3(8)5(10)7-6(11-7)4(2)9/h6-8H,1H3
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View in JSmolView Stereo Labels
SynonymsNot Available
Chemical FormulaC7H6O4
Average Molecular Weight154.121
Monoisotopic Molecular Weight154.026608673
IUPAC Name3-hydroxy-4-methyl-7-oxabicyclo[4.1.0]hept-3-ene-2,5-dione
Traditional Nameterreic acid
CAS Registry NumberNot Available
SMILES
CC1=C(O)C(=O)C2OC2C1=O
InChI Identifier
InChI=1S/C7H6O4/c1-2-3(8)5(10)7-6(11-7)4(2)9/h6-8H,1H3
InChI KeyATFNSNUJZOYXFC-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as cyclohexenones. Cyclohexenones are compounds containing a cylohexenone moiety, which is a six-membered aliphatic ring that carries a ketone and has one endocyclic double bond.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbonyl compounds
Direct ParentCyclohexenones
Alternative Parents
Substituents
  • Cyclohexenone
  • Vinylogous acid
  • Oxacycle
  • Organoheterocyclic compound
  • Ether
  • Oxirane
  • Enol
  • Dialkyl ether
  • Organic oxide
  • Hydrocarbon derivative
  • Aldehyde
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
Biological location
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
logP-0.19ALOGPS
logP0.27ChemAxon
logS0.48ALOGPS
pKa (Strongest Acidic)4.48ChemAxon
pKa (Strongest Basic)-4.3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area66.9 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity35.45 m³·mol⁻¹ChemAxon
Polarizability13.41 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+129.31530932474
DeepCCS[M-H]-125.54330932474
DeepCCS[M-2H]-163.03630932474
DeepCCS[M+Na]+138.45530932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Terreic acidCC1=C(O)C(=O)C2OC2C1=O2306.2Standard polar33892256
Terreic acidCC1=C(O)C(=O)C2OC2C1=O1169.6Standard non polar33892256
Terreic acidCC1=C(O)C(=O)C2OC2C1=O1288.3Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Terreic acid,2TMS,isomer #1CC1=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C2OC2C1=O1545.6Semi standard non polar33892256
Terreic acid,2TMS,isomer #1CC1=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C2OC2C1=O1522.5Standard non polar33892256
Terreic acid,2TMS,isomer #1CC1=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C2OC2C1=O1825.0Standard polar33892256
Terreic acid,2TMS,isomer #2CC1=C(O[Si](C)(C)C)C(=O)C2OC2=C1O[Si](C)(C)C1518.9Semi standard non polar33892256
Terreic acid,2TMS,isomer #2CC1=C(O[Si](C)(C)C)C(=O)C2OC2=C1O[Si](C)(C)C1491.5Standard non polar33892256
Terreic acid,2TMS,isomer #2CC1=C(O[Si](C)(C)C)C(=O)C2OC2=C1O[Si](C)(C)C1800.1Standard polar33892256
Terreic acid,2TMS,isomer #3CC1=C(O)C(O[Si](C)(C)C)=C2OC2=C1O[Si](C)(C)C1652.7Semi standard non polar33892256
Terreic acid,2TMS,isomer #3CC1=C(O)C(O[Si](C)(C)C)=C2OC2=C1O[Si](C)(C)C1637.5Standard non polar33892256
Terreic acid,2TMS,isomer #3CC1=C(O)C(O[Si](C)(C)C)=C2OC2=C1O[Si](C)(C)C1889.3Standard polar33892256
Terreic acid,3TMS,isomer #1CC1=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C2OC2=C1O[Si](C)(C)C1711.6Semi standard non polar33892256
Terreic acid,3TMS,isomer #1CC1=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C2OC2=C1O[Si](C)(C)C1744.4Standard non polar33892256
Terreic acid,3TMS,isomer #1CC1=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C2OC2=C1O[Si](C)(C)C1655.4Standard polar33892256
Terreic acid,3TMS,isomer #2CC1=C(O[Si](C)(C)C)C2=C(O2)C(O[Si](C)(C)C)=C1O[Si](C)(C)C1711.6Semi standard non polar33892256
Terreic acid,3TMS,isomer #2CC1=C(O[Si](C)(C)C)C2=C(O2)C(O[Si](C)(C)C)=C1O[Si](C)(C)C1744.4Standard non polar33892256
Terreic acid,3TMS,isomer #2CC1=C(O[Si](C)(C)C)C2=C(O2)C(O[Si](C)(C)C)=C1O[Si](C)(C)C1655.4Standard polar33892256
Terreic acid,2TBDMS,isomer #1CC1=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C2OC2C1=O2052.7Semi standard non polar33892256
Terreic acid,2TBDMS,isomer #1CC1=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C2OC2C1=O1981.5Standard non polar33892256
Terreic acid,2TBDMS,isomer #1CC1=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C2OC2C1=O2065.5Standard polar33892256
Terreic acid,2TBDMS,isomer #2CC1=C(O[Si](C)(C)C(C)(C)C)C(=O)C2OC2=C1O[Si](C)(C)C(C)(C)C2039.7Semi standard non polar33892256
Terreic acid,2TBDMS,isomer #2CC1=C(O[Si](C)(C)C(C)(C)C)C(=O)C2OC2=C1O[Si](C)(C)C(C)(C)C1943.2Standard non polar33892256
Terreic acid,2TBDMS,isomer #2CC1=C(O[Si](C)(C)C(C)(C)C)C(=O)C2OC2=C1O[Si](C)(C)C(C)(C)C2043.5Standard polar33892256
Terreic acid,2TBDMS,isomer #3CC1=C(O)C(O[Si](C)(C)C(C)(C)C)=C2OC2=C1O[Si](C)(C)C(C)(C)C2139.4Semi standard non polar33892256
Terreic acid,2TBDMS,isomer #3CC1=C(O)C(O[Si](C)(C)C(C)(C)C)=C2OC2=C1O[Si](C)(C)C(C)(C)C2092.5Standard non polar33892256
Terreic acid,2TBDMS,isomer #3CC1=C(O)C(O[Si](C)(C)C(C)(C)C)=C2OC2=C1O[Si](C)(C)C(C)(C)C2158.0Standard polar33892256
Terreic acid,3TBDMS,isomer #1CC1=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C2OC2=C1O[Si](C)(C)C(C)(C)C2398.8Semi standard non polar33892256
Terreic acid,3TBDMS,isomer #1CC1=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C2OC2=C1O[Si](C)(C)C(C)(C)C2374.4Standard non polar33892256
Terreic acid,3TBDMS,isomer #1CC1=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C2OC2=C1O[Si](C)(C)C(C)(C)C2163.5Standard polar33892256
Terreic acid,3TBDMS,isomer #2CC1=C(O[Si](C)(C)C(C)(C)C)C2=C(O2)C(O[Si](C)(C)C(C)(C)C)=C1O[Si](C)(C)C(C)(C)C2398.8Semi standard non polar33892256
Terreic acid,3TBDMS,isomer #2CC1=C(O[Si](C)(C)C(C)(C)C)C2=C(O2)C(O[Si](C)(C)C(C)(C)C)=C1O[Si](C)(C)C(C)(C)C2374.4Standard non polar33892256
Terreic acid,3TBDMS,isomer #2CC1=C(O[Si](C)(C)C(C)(C)C)C2=C(O2)C(O[Si](C)(C)C(C)(C)C)=C1O[Si](C)(C)C(C)(C)C2163.5Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Terreic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a6r-9200000000-d7f7a39188745049e3182021-09-23Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Terreic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Terreic acid GC-MS (TMS_1_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Terreic acid GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Terreic acid GC-MS (TMS_1_3) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Terreic acid GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Terreic acid GC-MS (TBDMS_1_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Terreic acid GC-MS (TBDMS_1_3) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID3755306
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Enzymes

Enzyme Details
1. Terreic acid biosynthesis cluster protein D
General function:
Not Available
Specific function:
part of the gene cluster that mediates the biosynthesis of terreic acid, a quinone epoxide inhibitor of Bruton's tyrosine kinase (PubMed:24534845, PubMed:25265334). The first step of the pathway is the synthesis of 6-methylsalicylic acid (6-MSA) by the 6-methylsalicylic acid synthase atX (PubMed:9003280, PubMed:9438344, PubMed:25265334). In the biosynthesis of 6-MSA, atX utilizes one acetyl-CoA and three malonyl-CoAs as its substrates and catalyzes a series of programmed reactions including Claisen condensation, dehydration, reduction, and cyclization to yield 6-MSA (PubMed:9003280, PubMed:9438344, PubMed:25265334). The 6-methylsalicylic acid decarboxylase atA then catalyzes the decarboxylative hydroxylation of 6-MSA to 3-methylcatechol (PubMed:25265334). The next step is the conversion of 3-methylcatechol to terremutin via several oxidation steps involving the cytochrome P450 monooxygenase atE and probably also the cytochrome P450 monooxygenase atG (PubMed:25265334). Lastly, atC is required for the oxidation of terremutin to terreic acid (PubMed:25265334). No function could be assigned to atD yet, although it is involved in the biosynthesis of terreic acid (PubMed:25265334).
Gene Name:
ATD
Uniprot ID:
Q0CJ58
Molecular weight:
40885.965
Enzyme Details
2. Cytochrome P450 monooxygenase atE
General function:
Not Available
Specific function:
Cytochrome P450 monooxygenase; part of the gene cluster that mediates the biosynthesis of terreic acid, a quinone epoxide inhibitor of Bruton's tyrosine kinase (PubMed:24534845, PubMed:25265334). The first step of the pathway is the synthesis of 6-methylsalicylic acid (6-MSA) by the 6-methylsalicylic acid synthase atX (PubMed:9003280, PubMed:9438344, PubMed:25265334). In the biosynthesis of 6-MSA, atX utilizes one acetyl-CoA and three malonyl-CoAs as its substrates and catalyzes a series of programmed reactions including Claisen condensation, dehydration, reduction, and cyclization to yield 6-MSA (PubMed:9003280, PubMed:9438344, PubMed:25265334). The 6-methylsalicylic acid decarboxylase atA then catalyzes the decarboxylative hydroxylation of 6-MSA to 3-methylcatechol (PubMed:25265334). The next step is the conversion of 3-methylcatechol to terremutin via several oxidation steps involving the cytochrome P450 monooxygenase atE and probably also the cytochrome P450 monooxygenase atG (PubMed:25265334). Lastly, atC is required for the oxidation of terremutin to terreic acid (PubMed:25265334). No function could be assigned to atD yet, although it is involved in the biosynthesis of terreic acid (PubMed:25265334).
Gene Name:
ATE
Uniprot ID:
Q0CJ57
Molecular weight:
53876.42
Enzyme Details
3. Cytochrome P450 monooxygenase atG
General function:
Not Available
Specific function:
Cytochrome P450 monooxygenase; part of the gene cluster that mediates the biosynthesis of terreic acid, a quinone epoxide inhibitor of Bruton's tyrosine kinase (BTK) (PubMed:24534845, PubMed:25265334). The first step of the pathway is the synthesis of 6-methylsalicylic acid (6-MSA) by the 6-methylsalicylic acid synthase atX (PubMed:9003280, PubMed:9438344, PubMed:25265334). In the biosynthesis of 6-MSA, atX utilizes one acetyl-CoA and three malonyl-CoAs as its substrates and catalyzes a series of programmed reactions including Claisen condensation, dehydration, reduction, and cyclization to yield 6-MSA (PubMed:9003280, PubMed:9438344, PubMed:25265334). The 6-methylsalicylic acid decarboxylase atA then catalyzes the decarboxylative hydroxylation of 6-MSA to 3-methylcatechol (PubMed:25265334). The next step is the conversion of 3-methylcatechol to terremutin via several oxidation steps involving the cytochrome P450 monooxygenase atE and probably also the cytochrome P450 monooxygenase atG (PubMed:25265334). Lastly, atC is required for the oxidation of terremutin to terreic acid (PubMed:25265334). No function could be assigned to atD yet, although it is involved in the biosynthesis of terreic acid (PubMed:25265334).
Gene Name:
ATG
Uniprot ID:
Q0CJ54
Molecular weight:
14740.8
Enzyme Details
4. 6-methylsalicylic acid synthase
General function:
Not Available
Specific function:
6-methylsalicylic acid synthase; part of the gene cluster that mediates the biosynthesis of terreic acid, a quinone epoxide inhibitor of Bruton's tyrosine kinase (PubMed:24534845, PubMed:25265334). The first step of the pathway is the synthesis of 6-methylsalicylic acid (6-MSA) by the 6-methylsalicylic acid synthase atX (PubMed:9003280, PubMed:9438344, PubMed:25265334). In the biosynthesis of 6-MSA, atX utilizes one acetyl-CoA and three malonyl-CoAs as its substrates and catalyzes a series of programmed reactions including Claisen condensation, dehydration, reduction, and cyclization to yield 6-MSA (PubMed:9003280, PubMed:9438344, PubMed:25265334). The 6-methylsalicylic acid decarboxylase atA then catalyzes the decarboxylative hydroxylation of 6-MSA to 3-methylcatechol (PubMed:25265334). The next step is the conversion of 3-methylcatechol to terremutin via several oxidation steps involving the cytochrome P450 monooxygenase atE and probably also the cytochrome P450 monooxygenase atG (PubMed:25265334). Lastly, atC is required for the oxidation of terremutin to terreic acid (PubMed:25265334). No function could be assigned to atD yet, although it is involved in the biosynthesis of terreic acid (PubMed:25265334).
Gene Name:
ATX
Uniprot ID:
Q0CJ59
Molecular weight:
193792.24
Enzyme Details
5. 6-methylsalicylic acid decarboxylase atA
General function:
Not Available
Specific function:
6-methylsalicylic acid decarboxylase; part of the gene cluster that mediates the biosynthesis of terreic acid, a quinone epoxide inhibitor of Bruton's tyrosine kinase (PubMed:24534845, PubMed:25265334). The first step of the pathway is the synthesis of 6-methylsalicylic acid (6-MSA) by the 6-methylsalicylic acid synthase atX (PubMed:9003280, PubMed:9438344, PubMed:25265334). In the biosynthesis of 6-MSA, atX utilizes one acetyl-CoA and three malonyl-CoAs as its substrates and catalyzes a series of programmed reactions including Claisen condensation, dehydration, reduction, and cyclization to yield 6-MSA (PubMed:9003280, PubMed:9438344, PubMed:25265334). The 6-methylsalicylic acid decarboxylase atA then catalyzes the decarboxylative hydroxylation of 6-MSA to 3-methylcatechol (PubMed:25265334). The next step is the conversion of 3-methylcatechol to terremutin via several oxidation steps involving the cytochrome P450 monooxygenase atE and probably also the cytochrome P450 monooxygenase atG (PubMed:25265334). Lastly, atC is required for the oxidation of terremutin to terreic acid (PubMed:25265334). No function could be assigned to atD yet, although it is involved in the biosynthesis of terreic acid (PubMed:25265334).
Gene Name:
ATA
Uniprot ID:
Q0CJ62
Molecular weight:
48455.485
Enzyme Details
6. Cyclase atC
General function:
Not Available
Specific function:
Cyclase; part of the gene cluster that mediates the biosynthesis of terreic acid, a quinone epoxide inhibitor of Bruton's tyrosine kinase (PubMed:24534845, PubMed:25265334). The first step of the pathway is the synthesis of 6-methylsalicylic acid (6-MSA) by the 6-methylsalicylic acid synthase atX (PubMed:9003280, PubMed:9438344, PubMed:25265334). In the biosynthesis of 6-MSA, atX utilizes one acetyl-CoA and three malonyl-CoAs as its substrates and catalyzes a series of programmed reactions including Claisen condensation, dehydration, reduction, and cyclization to yield 6-MSA (PubMed:9003280, PubMed:9438344, PubMed:25265334). The 6-methylsalicylic acid decarboxylase atA then catalyzes the decarboxylative hydroxylation of 6-MSA to 3-methylcatechol (PubMed:25265334). The next step is the conversion of 3-methylcatechol to terremutin via several oxidation steps involving the cytochrome P450 monooxygenase atE and probably also the cytochrome P450 monooxygenase atG (PubMed:25265334). Lastly, atC is required for the oxidation of terremutin to terreic acid (PubMed:25265334). No function could be assigned to atD yet, although it is involved in the biosynthesis of terreic acid (PubMed:25265334).
Gene Name:
ATC
Uniprot ID:
Q0CJ60
Molecular weight:
63450.735