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Showing metabocard for Triethylenephosphoramide (HMDB0258822)

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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2021-09-11 20:34:38 UTC
Update Date2021-09-26 23:16:00 UTC
HMDB IDHMDB0258822
Secondary Accession NumbersNone
Metabolite Identification
Common NameTriethylenephosphoramide
Description1-[bis(aziridin-1-yl)phosphoroso]aziridine, also known as TEPA or APO, belongs to the class of organic compounds known as organic phosphoramides. These are organic compounds containing the phosphoric acid amide functional group. Based on a literature review very few articles have been published on 1-[bis(aziridin-1-yl)phosphoroso]aziridine. This compound has been identified in human blood as reported by (PMID: 31557052 ). Triethylenephosphoramide is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Triethylenephosphoramide 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 HMDB0258822 (Triethylenephosphoramide)

  Mrv1572004201615502D          

 11 13  0  0  0  0            999 V2000
   -1.9520    0.6507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1270    0.6507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1270    3.7296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9520    3.7296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    1.7776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    2.6026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5395    1.3651    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5395    3.0151    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.1901    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3645    2.1901    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5395    2.1901    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  4  3  1  0  0  0  0
  6  5  1  0  0  0  0
  7  1  1  0  0  0  0
  7  2  1  0  0  0  0
  8  3  1  0  0  0  0
  8  4  1  0  0  0  0
  9  5  1  0  0  0  0
  9  6  1  0  0  0  0
 11  7  1  0  0  0  0
 11  8  1  0  0  0  0
 11  9  1  0  0  0  0
 11 10  2  0  0  0  0
M  END
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3D MOL for HMDB0258822 (Triethylenephosphoramide)

HMDB0258822
     RDKit          3D
Triethylenephosphoramide
 23 25  0  0  0  0  0  0  0  0999 V2000
    0.3027    0.1520    1.4411 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0210    0.0417   -0.0603 P   0  0  0  0  0  5  0  0  0  0  0  0
    0.1154    1.6857   -0.6843 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4984    2.6857    0.1840 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0693    2.3422   -1.1259 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3744   -0.8174   -0.7526 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6356   -0.0676   -0.6298 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3931   -1.3612    0.0880 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4858   -0.6970   -0.2853 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6919   -2.0697   -0.5583 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9252   -1.5969    0.8461 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0549    2.3228    1.0759 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1631    3.5560    0.3521 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0284    1.8203   -1.1762 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8933    3.0785   -1.9561 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2973   -0.0245   -1.5135 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6753    0.8138    0.0036 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2854   -1.3788    1.1747 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9796   -2.2152   -0.3334 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6280   -2.2838   -1.1526 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8910   -2.7845   -0.7317 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9327   -1.3357    1.1990 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1440   -1.8662    1.5690 H   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  1  0
  2  6  1  0
  6  7  1  0
  7  8  1  0
  2  9  1  0
  9 10  1  0
 10 11  1  0
  5  3  1  0
  8  6  1  0
 11  9  1  0
  4 12  1  0
  4 13  1  0
  5 14  1  0
  5 15  1  0
  7 16  1  0
  7 17  1  0
  8 18  1  0
  8 19  1  0
 10 20  1  0
 10 21  1  0
 11 22  1  0
 11 23  1  0
M  END
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3D SDF for HMDB0258822 (Triethylenephosphoramide)

  Mrv1572004201615502D          

 11 13  0  0  0  0            999 V2000
   -1.9520    0.6507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1270    0.6507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1270    3.7296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9520    3.7296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    1.7776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    2.6026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5395    1.3651    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5395    3.0151    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.1901    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3645    2.1901    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5395    2.1901    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  4  3  1  0  0  0  0
  6  5  1  0  0  0  0
  7  1  1  0  0  0  0
  7  2  1  0  0  0  0
  8  3  1  0  0  0  0
  8  4  1  0  0  0  0
  9  5  1  0  0  0  0
  9  6  1  0  0  0  0
 11  7  1  0  0  0  0
 11  8  1  0  0  0  0
 11  9  1  0  0  0  0
 11 10  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0258822

> <DATABASE_NAME>
hmdb

> <SMILES>
O=P(N1CC1)(N1CC1)N1CC1

> <INCHI_IDENTIFIER>
InChI=1S/C6H12N3OP/c10-11(7-1-2-7,8-3-4-8)9-5-6-9/h1-6H2

> <INCHI_KEY>
FYAMXEPQQLNQDM-UHFFFAOYSA-N

> <FORMULA>
C6H12N3OP

> <MOLECULAR_WEIGHT>
173.156

> <EXACT_MASS>
173.071799016

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
23

> <JCHEM_AVERAGE_POLARIZABILITY>
16.33213997537745

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1-[bis(aziridin-1-yl)phosphoroso]aziridine

> <ALOGPS_LOGP>
-0.56

> <JCHEM_LOGP>
-1.917250099666667

> <ALOGPS_LOGS>
-0.31

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
0.670249274567347

> <JCHEM_POLAR_SURFACE_AREA>
26.33

> <JCHEM_REFRACTIVITY>
42.731300000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.50e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
TEPA

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for HMDB0258822 (Triethylenephosphoramide)

HMDB0258822
     RDKit          3D
Triethylenephosphoramide
 23 25  0  0  0  0  0  0  0  0999 V2000
    0.3027    0.1520    1.4411 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0210    0.0417   -0.0603 P   0  0  0  0  0  5  0  0  0  0  0  0
    0.1154    1.6857   -0.6843 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4984    2.6857    0.1840 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0693    2.3422   -1.1259 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3744   -0.8174   -0.7526 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6356   -0.0676   -0.6298 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3931   -1.3612    0.0880 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4858   -0.6970   -0.2853 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6919   -2.0697   -0.5583 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9252   -1.5969    0.8461 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0549    2.3228    1.0759 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1631    3.5560    0.3521 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0284    1.8203   -1.1762 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8933    3.0785   -1.9561 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2973   -0.0245   -1.5135 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6753    0.8138    0.0036 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2854   -1.3788    1.1747 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9796   -2.2152   -0.3334 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6280   -2.2838   -1.1526 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8910   -2.7845   -0.7317 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9327   -1.3357    1.1990 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1440   -1.8662    1.5690 H   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  1  0
  2  6  1  0
  6  7  1  0
  7  8  1  0
  2  9  1  0
  9 10  1  0
 10 11  1  0
  5  3  1  0
  8  6  1  0
 11  9  1  0
  4 12  1  0
  4 13  1  0
  5 14  1  0
  5 15  1  0
  7 16  1  0
  7 17  1  0
  8 18  1  0
  8 19  1  0
 10 20  1  0
 10 21  1  0
 11 22  1  0
 11 23  1  0
M  END
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PDB for HMDB0258822 (Triethylenephosphoramide)

HEADER    PROTEIN                                 20-APR-16   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-APR-16         0                                  
HETATM    1  C   UNK     0      -3.644   1.215   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.104   1.215   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.104   6.962   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -3.644   6.962   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.000   3.318   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.000   4.858   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0      -2.874   2.548   0.000  0.00  0.00           N+0
HETATM    8  N   UNK     0      -2.874   5.628   0.000  0.00  0.00           N+0
HETATM    9  N   UNK     0      -1.334   4.088   0.000  0.00  0.00           N+0
HETATM   10  O   UNK     0      -4.414   4.088   0.000  0.00  0.00           O+0
HETATM   11  P   UNK     0      -2.874   4.088   0.000  0.00  0.00           P+0
CONECT    1    2    7                                                       
CONECT    2    1    7                                                       
CONECT    3    4    8                                                       
CONECT    4    3    8                                                       
CONECT    5    6    9                                                       
CONECT    6    5    9                                                       
CONECT    7    1    2   11                                                  
CONECT    8    3    4   11                                                  
CONECT    9    5    6   11                                                  
CONECT   10   11                                                            
CONECT   11    7    8    9   10                                             
MASTER        0    0    0    0    0    0    0    0   11    0   26    0
END
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3D PDB for HMDB0258822 (Triethylenephosphoramide)

COMPND    HMDB0258822
HETATM    1  O1  UNL     1       0.303   0.152   1.441  1.00  0.00           O  
HETATM    2  P1  UNL     1       0.021   0.042  -0.060  1.00  0.00           P  
HETATM    3  N1  UNL     1       0.115   1.686  -0.684  1.00  0.00           N  
HETATM    4  C1  UNL     1      -0.498   2.686   0.184  1.00  0.00           C  
HETATM    5  C2  UNL     1      -1.069   2.342  -1.126  1.00  0.00           C  
HETATM    6  N2  UNL     1       1.374  -0.817  -0.753  1.00  0.00           N  
HETATM    7  C3  UNL     1       2.636  -0.068  -0.630  1.00  0.00           C  
HETATM    8  C4  UNL     1       2.393  -1.361   0.088  1.00  0.00           C  
HETATM    9  N3  UNL     1      -1.486  -0.697  -0.285  1.00  0.00           N  
HETATM   10  C5  UNL     1      -1.692  -2.070  -0.558  1.00  0.00           C  
HETATM   11  C6  UNL     1      -1.925  -1.597   0.846  1.00  0.00           C  
HETATM   12  H1  UNL     1      -1.055   2.323   1.076  1.00  0.00           H  
HETATM   13  H2  UNL     1       0.163   3.556   0.352  1.00  0.00           H  
HETATM   14  H3  UNL     1      -2.028   1.820  -1.176  1.00  0.00           H  
HETATM   15  H4  UNL     1      -0.893   3.078  -1.956  1.00  0.00           H  
HETATM   16  H5  UNL     1       3.297  -0.024  -1.513  1.00  0.00           H  
HETATM   17  H6  UNL     1       2.675   0.814   0.004  1.00  0.00           H  
HETATM   18  H7  UNL     1       2.285  -1.379   1.175  1.00  0.00           H  
HETATM   19  H8  UNL     1       2.980  -2.215  -0.333  1.00  0.00           H  
HETATM   20  H9  UNL     1      -2.628  -2.284  -1.153  1.00  0.00           H  
HETATM   21  H10 UNL     1      -0.891  -2.785  -0.732  1.00  0.00           H  
HETATM   22  H11 UNL     1      -2.933  -1.336   1.199  1.00  0.00           H  
HETATM   23  H12 UNL     1      -1.144  -1.866   1.569  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    6    9
CONECT    3    4    5
CONECT    4    5   12   13
CONECT    5   14   15
CONECT    6    7    8
CONECT    7    8   16   17
CONECT    8   18   19
CONECT    9   10   11
CONECT   10   11   20   21
CONECT   11   22   23
END
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SMILES for HMDB0258822 (Triethylenephosphoramide)

O=P(N1CC1)(N1CC1)N1CC1
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INCHI for HMDB0258822 (Triethylenephosphoramide)

InChI=1S/C6H12N3OP/c10-11(7-1-2-7,8-3-4-8)9-5-6-9/h1-6H2
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View in JSmolView Stereo Labels
Synonyms
ValueSource
TEPAKegg
APOKegg
TriethylenephosphoramideMeSH
Chemical FormulaC6H12N3OP
Average Molecular Weight173.156
Monoisotopic Molecular Weight173.071799016
IUPAC Name1-[bis(aziridin-1-yl)phosphoroso]aziridine
Traditional NameTEPA
CAS Registry NumberNot Available
SMILES
O=P(N1CC1)(N1CC1)N1CC1
InChI Identifier
InChI=1S/C6H12N3OP/c10-11(7-1-2-7,8-3-4-8)9-5-6-9/h1-6H2
InChI KeyFYAMXEPQQLNQDM-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as organic phosphoramides. These are organic compounds containing the phosphoric acid amide functional group.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassOrganic phosphoric acids and derivatives
Sub ClassOrganic phosphoramides
Direct ParentOrganic phosphoramides
Alternative Parents
Substituents
  • Organic phosphoric acid amide
  • Azacycle
  • Organoheterocyclic compound
  • Aziridine
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic 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
Predicted Chromatographic Properties
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 ID10550
KEGG Compound IDC19543
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 ]