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Showing metabocard for Trifluoroacetic anhydride (HMDB0259203)

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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2021-09-11 21:41:27 UTC
Update Date2022-11-23 22:29:20 UTC
HMDB IDHMDB0259203
Secondary Accession NumbersNone
Metabolite Identification
Common NameTrifluoroacetic anhydride
DescriptionTrifluoroacetic anhydride belongs to the class of organic compounds known as dicarboxylic acids and derivatives. These are organic compounds containing exactly two carboxylic acid groups. Based on a literature review a significant number of articles have been published on Trifluoroacetic anhydride. This compound has been identified in human blood as reported by (PMID: 31557052 ). Trifluoroacetic anhydride is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Trifluoroacetic anhydride 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 HMDB0259203 (Trifluoroacetic anhydride)


  Mrv1652309112123412D          

 13 12  0  0  0  0            999 V2000
    0.1105   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6039   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3184   -2.8875    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1914   -3.1895    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0164   -1.7605    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    0.1105   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.8250    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -0.0000    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  3  6  1  0  0  0  0
  1  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 10 13  1  0  0  0  0
M  END
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3D MOL for HMDB0259203 (Trifluoroacetic anhydride)

HMDB0259203
     RDKit          3D
TRIFLUOROACETIC ANHYDRIDE
 13 12  0  0  0  0  0  0  0  0999 V2000
   -1.1405   -1.2527    1.1734 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1973   -0.4010    0.2487 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0146    0.1416   -0.2103 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2329   -0.1746    0.2637 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3074   -1.0248    1.1887 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4857    0.4489   -0.2751 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4654    1.8202   -0.1085 F   0  0  0  0  0  0  0  0  0  0  0  0
    3.5675   -0.0240    0.4409 F   0  0  0  0  0  0  0  0  0  0  0  0
    2.6850    0.1194   -1.6001 F   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5203    0.0005   -0.3255 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7374    1.3618   -0.1592 F   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6106   -0.3179   -1.6638 F   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5231   -0.6974    0.3181 F   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  0
  6  8  1  0
  6  9  1  0
  2 10  1  0
 10 11  1  0
 10 12  1  0
 10 13  1  0
M  END
Download

3D SDF for HMDB0259203 (Trifluoroacetic anhydride)


  Mrv1652309112123412D          

 13 12  0  0  0  0            999 V2000
    0.1105   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6039   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3184   -2.8875    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1914   -3.1895    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0164   -1.7605    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    0.1105   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.8250    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -0.0000    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  3  6  1  0  0  0  0
  1  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 10 13  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0259203

> <DATABASE_NAME>
hmdb

> <SMILES>
FC(F)(F)C(=O)OC(=O)C(F)(F)F

> <INCHI_IDENTIFIER>
InChI=1S/C4F6O3/c5-3(6,7)1(11)13-2(12)4(8,9)10

> <INCHI_KEY>
QAEDZJGFFMLHHQ-UHFFFAOYSA-N

> <FORMULA>
C4F6O3

> <MOLECULAR_WEIGHT>
210.031

> <EXACT_MASS>
209.975162838

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
13

> <JCHEM_AVERAGE_POLARIZABILITY>
9.992630990572898

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2,2,2-trifluoroacetyl 2,2,2-trifluoroacetate

> <ALOGPS_LOGP>
1.69

> <JCHEM_LOGP>
1.9521378583333333

> <ALOGPS_LOGS>
-4.59

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-8.291901065928272

> <JCHEM_POLAR_SURFACE_AREA>
43.370000000000005

> <JCHEM_REFRACTIVITY>
24.102399999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.36e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2,2,2-trifluoroacetyl trifluoroacetate

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for HMDB0259203 (Trifluoroacetic anhydride)

HMDB0259203
     RDKit          3D
TRIFLUOROACETIC ANHYDRIDE
 13 12  0  0  0  0  0  0  0  0999 V2000
   -1.1405   -1.2527    1.1734 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1973   -0.4010    0.2487 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0146    0.1416   -0.2103 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2329   -0.1746    0.2637 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3074   -1.0248    1.1887 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4857    0.4489   -0.2751 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4654    1.8202   -0.1085 F   0  0  0  0  0  0  0  0  0  0  0  0
    3.5675   -0.0240    0.4409 F   0  0  0  0  0  0  0  0  0  0  0  0
    2.6850    0.1194   -1.6001 F   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5203    0.0005   -0.3255 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7374    1.3618   -0.1592 F   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6106   -0.3179   -1.6638 F   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5231   -0.6974    0.3181 F   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  0
  6  8  1  0
  6  9  1  0
  2 10  1  0
 10 11  1  0
 10 12  1  0
 10 13  1  0
M  END
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PDB for HMDB0259203 (Trifluoroacetic anhydride)

HEADER    PROTEIN                                 11-SEP-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-21         0                                  
HETATM    1  C   UNK     0       0.206  -3.850   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       1.540  -4.620   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -1.127  -4.620   0.000  0.00  0.00           C+0
HETATM    4  F   UNK     0      -2.461  -5.390   0.000  0.00  0.00           F+0
HETATM    5  F   UNK     0      -0.357  -5.954   0.000  0.00  0.00           F+0
HETATM    6  F   UNK     0      -1.897  -3.286   0.000  0.00  0.00           F+0
HETATM    7  O   UNK     0       0.206  -2.310   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       1.540  -1.540   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       2.874  -2.310   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       1.540   0.000   0.000  0.00  0.00           C+0
HETATM   11  F   UNK     0       1.540   1.540   0.000  0.00  0.00           F+0
HETATM   12  F   UNK     0       3.080  -0.000   0.000  0.00  0.00           F+0
HETATM   13  F   UNK     0       0.000   0.000   0.000  0.00  0.00           F+0
CONECT    1    2    3    7                                                  
CONECT    2    1                                                            
CONECT    3    1    4    5    6                                             
CONECT    4    3                                                            
CONECT    5    3                                                            
CONECT    6    3                                                            
CONECT    7    1    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   12   13                                             
CONECT   11   10                                                            
CONECT   12   10                                                            
CONECT   13   10                                                            
MASTER        0    0    0    0    0    0    0    0   13    0   24    0
END
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3D PDB for HMDB0259203 (Trifluoroacetic anhydride)

COMPND    HMDB0259203
HETATM    1  O1  UNL     1      -1.140  -1.253   1.173  1.00  0.00           O  
HETATM    2  C1  UNL     1      -1.197  -0.401   0.249  1.00  0.00           C  
HETATM    3  O2  UNL     1      -0.015   0.142  -0.210  1.00  0.00           O  
HETATM    4  C2  UNL     1       1.233  -0.175   0.264  1.00  0.00           C  
HETATM    5  O3  UNL     1       1.307  -1.025   1.189  1.00  0.00           O  
HETATM    6  C3  UNL     1       2.486   0.449  -0.275  1.00  0.00           C  
HETATM    7  F1  UNL     1       2.465   1.820  -0.109  1.00  0.00           F  
HETATM    8  F2  UNL     1       3.567  -0.024   0.441  1.00  0.00           F  
HETATM    9  F3  UNL     1       2.685   0.119  -1.600  1.00  0.00           F  
HETATM   10  C4  UNL     1      -2.520   0.001  -0.326  1.00  0.00           C  
HETATM   11  F4  UNL     1      -2.737   1.362  -0.159  1.00  0.00           F  
HETATM   12  F5  UNL     1      -2.611  -0.318  -1.664  1.00  0.00           F  
HETATM   13  F6  UNL     1      -3.523  -0.697   0.318  1.00  0.00           F  
CONECT    1    2    2
CONECT    2    3   10
CONECT    3    4
CONECT    4    5    5    6
CONECT    6    7    8    9
CONECT   10   11   12   13
END
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SMILES for HMDB0259203 (Trifluoroacetic anhydride)

FC(F)(F)C(=O)OC(=O)C(F)(F)F
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INCHI for HMDB0259203 (Trifluoroacetic anhydride)

InChI=1S/C4F6O3/c5-3(6,7)1(11)13-2(12)4(8,9)10
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View in JSmolView Stereo Labels
Synonyms
ValueSource
2,2,2-Trifluoroacetyl 2,2,2-trifluoroacetic acidHMDB
Chemical FormulaC4F6O3
Average Molecular Weight210.031
Monoisotopic Molecular Weight209.975162838
IUPAC Name2,2,2-trifluoroacetyl 2,2,2-trifluoroacetate
Traditional Name2,2,2-trifluoroacetyl trifluoroacetate
CAS Registry NumberNot Available
SMILES
FC(F)(F)C(=O)OC(=O)C(F)(F)F
InChI Identifier
InChI=1S/C4F6O3/c5-3(6,7)1(11)13-2(12)4(8,9)10
InChI KeyQAEDZJGFFMLHHQ-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as dicarboxylic acids and derivatives. These are organic compounds containing exactly two carboxylic acid groups.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassDicarboxylic acids and derivatives
Direct ParentDicarboxylic acids and derivatives
Alternative Parents
Substituents
  • Dicarboxylic acid or derivatives
  • Carboxylic acid anhydride
  • Alpha-halocarboxylic acid or derivatives
  • Alpha-halocarboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organofluoride
  • Organohalogen compound
  • Carbonyl group
  • Alkyl halide
  • Alkyl fluoride
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
Biological locationSource
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
logP1.69ALOGPS
logP1.95ChemAxon
logS-4.6ALOGPS
pKa (Strongest Basic)-8.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area43.37 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity24.1 m³·mol⁻¹ChemAxon
Polarizability9.99 ųChemAxon
Number of Rings0ChemAxon
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]+139.7230932474
DeepCCS[M-H]-137.32430932474
DeepCCS[M-2H]-171.9130932474
DeepCCS[M+Na]+146.26230932474
AllCCS[M+H]+141.332859911
AllCCS[M+H-H2O]+137.732859911
AllCCS[M+NH4]+144.832859911
AllCCS[M+Na]+145.732859911
AllCCS[M-H]-127.232859911
AllCCS[M+Na-2H]-128.132859911
AllCCS[M+HCOO]-129.232859911

Predicted Retention Times

Underivatized

Chromatographic MethodRetention TimeReference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.4.24 minutes32390414
Predicted by Siyang on May 30, 202213.9182 minutes33406817
Predicted by Siyang using ReTip algorithm on June 8, 20221.55 minutes32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid1728.0 seconds40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid539.2 seconds40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid193.1 seconds40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid392.2 seconds40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid236.4 seconds40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid539.3 seconds40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid636.5 seconds40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)527.7 seconds40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid1079.3 seconds40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid380.3 seconds40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid1043.2 seconds40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid409.6 seconds40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid396.9 seconds40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate660.0 seconds40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA496.5 seconds40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water196.7 seconds40023050

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
TRIFLUOROACETIC ANHYDRIDEFC(F)(F)C(=O)OC(=O)C(F)(F)F778.7Standard polar33892256
TRIFLUOROACETIC ANHYDRIDEFC(F)(F)C(=O)OC(=O)C(F)(F)F472.6Standard non polar33892256
TRIFLUOROACETIC ANHYDRIDEFC(F)(F)C(=O)OC(=O)C(F)(F)F411.1Semi standard non polar33892256
Spectra
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 ID21106178
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkTrifluoroacetic anhydride
METLIN IDNot Available
PubChem Compound9845
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 ]