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Showing metabocard for SARIN (HMDB0257497)

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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2021-09-11 18:30:03 UTC
Update Date2021-09-26 23:13:55 UTC
HMDB IDHMDB0257497
Secondary Accession NumbersNone
Metabolite Identification
Common NameSARIN
Descriptionisopropyl methylphosphonofluoridate belongs to the class of organic compounds known as phosphonic acid esters. These are organic compounds containing phosphonic acid ester functional group, with the general structure ROP(=O)OH (R = organyl group). Based on a literature review very few articles have been published on isopropyl methylphosphonofluoridate. This compound has been identified in human blood as reported by (PMID: 31557052 ). Sarin is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically SARIN 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 HMDB0257497 (SARIN)


  Mrv1572004191601122D          

  8  7  0  0  0  0            999 V2000
    2.0625   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250   -1.4289    0.0000 C   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
    1.2375   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
  4  1  1  0  0  0  0
  4  2  1  0  0  0  0
  7  4  1  0  0  0  0
  8  3  1  0  0  0  0
  8  5  1  0  0  0  0
  8  6  2  0  0  0  0
  8  7  1  0  0  0  0
M  END
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3D MOL for HMDB0257497 (SARIN)

HMDB0257497
     RDKit          3D
SARIN
 18 17  0  0  0  0  0  0  0  0999 V2000
   -1.5390   -1.2611   -0.0956 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9961    0.1530   -0.0454 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9860    1.1178    0.5669 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2300    0.1675    0.5487 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5031    0.6320   -0.4120 P   0  0  0  0  0  5  0  0  0  0  0  0
    2.8528   -0.5602   -0.1648 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0364    1.9939   -0.1299 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9890    0.6079   -2.0155 F   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9370   -1.6116    0.8541 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2898   -1.3594   -0.9298 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6902   -1.9194   -0.3739 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8684    0.4736   -1.1029 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9701    1.0929    1.6730 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7379    2.1234    0.1691 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0200    0.8545    0.2620 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3862   -0.7702   -1.1211 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4526   -1.5353    0.2298 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5845   -0.1993    0.5648 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  5  7  2  0
  5  8  1  0
  1  9  1  0
  1 10  1  0
  1 11  1  0
  2 12  1  0
  3 13  1  0
  3 14  1  0
  3 15  1  0
  6 16  1  0
  6 17  1  0
  6 18  1  0
M  END
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3D SDF for HMDB0257497 (SARIN)


  Mrv1572004191601122D          

  8  7  0  0  0  0            999 V2000
    2.0625   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250   -1.4289    0.0000 C   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
    1.2375   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
  4  1  1  0  0  0  0
  4  2  1  0  0  0  0
  7  4  1  0  0  0  0
  8  3  1  0  0  0  0
  8  5  1  0  0  0  0
  8  6  2  0  0  0  0
  8  7  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0257497

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(C)OP(C)(F)=O

> <INCHI_IDENTIFIER>
InChI=1S/C4H10FO2P/c1-4(2)7-8(3,5)6/h4H,1-3H3

> <INCHI_KEY>
DYAHQFWOVKZOOW-UHFFFAOYSA-N

> <FORMULA>
C4H10FO2P

> <MOLECULAR_WEIGHT>
140.094

> <EXACT_MASS>
140.040244723

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
18

> <JCHEM_AVERAGE_POLARIZABILITY>
12.13834799065111

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl(propan-2-yloxy)phosphinoyl fluoride

> <ALOGPS_LOGP>
0.54

> <JCHEM_LOGP>
0.7672783086666662

> <ALOGPS_LOGS>
-1.21

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-8.501154004723805

> <JCHEM_POLAR_SURFACE_AREA>
26.3

> <JCHEM_REFRACTIVITY>
29.764400000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.57e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
isopropoxy(methyl)phosphinoyl fluoride

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for HMDB0257497 (SARIN)

HMDB0257497
     RDKit          3D
SARIN
 18 17  0  0  0  0  0  0  0  0999 V2000
   -1.5390   -1.2611   -0.0956 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9961    0.1530   -0.0454 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9860    1.1178    0.5669 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2300    0.1675    0.5487 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5031    0.6320   -0.4120 P   0  0  0  0  0  5  0  0  0  0  0  0
    2.8528   -0.5602   -0.1648 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0364    1.9939   -0.1299 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9890    0.6079   -2.0155 F   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9370   -1.6116    0.8541 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2898   -1.3594   -0.9298 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6902   -1.9194   -0.3739 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8684    0.4736   -1.1029 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9701    1.0929    1.6730 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7379    2.1234    0.1691 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0200    0.8545    0.2620 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3862   -0.7702   -1.1211 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4526   -1.5353    0.2298 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5845   -0.1993    0.5648 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  5  7  2  0
  5  8  1  0
  1  9  1  0
  1 10  1  0
  1 11  1  0
  2 12  1  0
  3 13  1  0
  3 14  1  0
  3 15  1  0
  6 16  1  0
  6 17  1  0
  6 18  1  0
M  END
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PDB for HMDB0257497 (SARIN)

HEADER    PROTEIN                                 19-APR-16   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-APR-16         0                                  
HETATM    1  C   UNK     0       3.850  -1.334   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.540  -2.667   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.540   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.310  -1.334   0.000  0.00  0.00           C+0
HETATM    5  F   UNK     0       0.000   1.540   0.000  0.00  0.00           F+0
HETATM    6  O   UNK     0       0.000  -1.540   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0       1.540   0.000   0.000  0.00  0.00           O+0
HETATM    8  P   UNK     0       0.000   0.000   0.000  0.00  0.00           P+0
CONECT    1    4                                                            
CONECT    2    4                                                            
CONECT    3    8                                                            
CONECT    4    1    2    7                                                  
CONECT    5    8                                                            
CONECT    6    8                                                            
CONECT    7    4    8                                                       
CONECT    8    3    5    6    7                                             
MASTER        0    0    0    0    0    0    0    0    8    0   14    0
END
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3D PDB for HMDB0257497 (SARIN)

COMPND    HMDB0257497
HETATM    1  C1  UNL     1      -1.539  -1.261  -0.096  1.00  0.00           C  
HETATM    2  C2  UNL     1      -0.996   0.153  -0.045  1.00  0.00           C  
HETATM    3  C3  UNL     1      -1.986   1.118   0.567  1.00  0.00           C  
HETATM    4  O1  UNL     1       0.230   0.167   0.549  1.00  0.00           O  
HETATM    5  P1  UNL     1       1.503   0.632  -0.412  1.00  0.00           P  
HETATM    6  C4  UNL     1       2.853  -0.560  -0.165  1.00  0.00           C  
HETATM    7  O2  UNL     1       2.036   1.994  -0.130  1.00  0.00           O  
HETATM    8  F1  UNL     1       0.989   0.608  -2.016  1.00  0.00           F  
HETATM    9  H1  UNL     1      -1.937  -1.612   0.854  1.00  0.00           H  
HETATM   10  H2  UNL     1      -2.290  -1.359  -0.930  1.00  0.00           H  
HETATM   11  H3  UNL     1      -0.690  -1.919  -0.374  1.00  0.00           H  
HETATM   12  H4  UNL     1      -0.868   0.474  -1.103  1.00  0.00           H  
HETATM   13  H5  UNL     1      -1.970   1.093   1.673  1.00  0.00           H  
HETATM   14  H6  UNL     1      -1.738   2.123   0.169  1.00  0.00           H  
HETATM   15  H7  UNL     1      -3.020   0.855   0.262  1.00  0.00           H  
HETATM   16  H8  UNL     1       3.386  -0.770  -1.121  1.00  0.00           H  
HETATM   17  H9  UNL     1       2.453  -1.535   0.230  1.00  0.00           H  
HETATM   18  H10 UNL     1       3.584  -0.199   0.565  1.00  0.00           H  
CONECT    1    2    9   10   11
CONECT    2    3    4   12
CONECT    3   13   14   15
CONECT    4    5
CONECT    5    6    7    7    8
CONECT    6   16   17   18
END
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SMILES for HMDB0257497 (SARIN)

CC(C)OP(C)(F)=O
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INCHI for HMDB0257497 (SARIN)

InChI=1S/C4H10FO2P/c1-4(2)7-8(3,5)6/h4H,1-3H3
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View in JSmolView Stereo Labels
Synonyms
ValueSource
Isopropyl methylphosphonofluoridic acidGenerator
Gas, sarinMeSH
Phosphonofluoridate, ortho-isopropylmethylMeSH
O-Isopropylmethyl phosphonofluoridateMeSH
O Isopropylmethyl phosphonofluoridateMeSH
Sarin gasMeSH
Phosphonofluoridate, O-isopropylmethylMeSH
SarinMeSH
ortho-Isopropylmethyl phosphonofluoridateMeSH
ortho Isopropylmethyl phosphonofluoridateMeSH
Chemical FormulaC4H10FO2P
Average Molecular Weight140.094
Monoisotopic Molecular Weight140.040244723
IUPAC Namemethyl(propan-2-yloxy)phosphinoyl fluoride
Traditional Nameisopropoxy(methyl)phosphinoyl fluoride
CAS Registry NumberNot Available
SMILES
CC(C)OP(C)(F)=O
InChI Identifier
InChI=1S/C4H10FO2P/c1-4(2)7-8(3,5)6/h4H,1-3H3
InChI KeyDYAHQFWOVKZOOW-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as phosphonic acid esters. These are organic compounds containing phosphonic acid ester functional group, with the general structure ROP(=O)OH (R = organyl group).
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassOrganic phosphonic acids and derivatives
Sub ClassPhosphonic acid esters
Direct ParentPhosphonic acid esters
Alternative Parents
Substituents
  • Phosphonic acid ester
  • Alkylphosphonofluoridic acid or ester derivatives
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organophosphorus compound
  • Organooxygen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
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
logP0.54ALOGPS
logP0.77ChemAxon
logS-1.2ALOGPS
pKa (Strongest Basic)-8.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity29.76 m³·mol⁻¹ChemAxon
Polarizability12.14 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+130.49730932474
DeepCCS[M-H]-128.0630932474
DeepCCS[M-2H]-164.3930932474
DeepCCS[M+Na]+138.83230932474
AllCCS[M+H]+132.632859911
AllCCS[M+H-H2O]+128.632859911
AllCCS[M+NH4]+136.432859911
AllCCS[M+Na]+137.532859911
AllCCS[M-H]-130.932859911
AllCCS[M+Na-2H]-134.432859911
AllCCS[M+HCOO]-138.232859911

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, 2022.4.45 minutes32390414
Predicted by Siyang on May 30, 202211.6855 minutes33406817
Predicted by Siyang using ReTip algorithm on June 8, 20223.23 minutes32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid1263.9 seconds40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid343.3 seconds40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid122.7 seconds40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid212.9 seconds40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid76.1 seconds40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid305.3 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 Acid398.9 seconds40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)104.1 seconds40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid768.3 seconds40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid265.4 seconds40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid964.7 seconds40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid260.9 seconds40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid263.0 seconds40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate455.5 seconds40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA308.9 seconds40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water85.2 seconds40023050

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
SARINCC(C)OP(C)(F)=O1255.7Standard polar33892256
SARINCC(C)OP(C)(F)=O762.9Standard non polar33892256
SARINCC(C)OP(C)(F)=O810.6Semi 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 ID7583
KEGG Compound IDC11764
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI ID75873
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 ]