Hmdb loader

Showing metabocard for Thiotepa (HMDB0015576)

Jump To Section:
IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesenzymes (2) Show 2 proteinsXML
enzymes (2) Show 2 proteins
Show more...Show more...Show more...
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:52 UTC
Update Date2023-02-21 17:18:32 UTC
HMDB IDHMDB0015576
Secondary Accession Numbers
  • HMDB15576
Metabolite Identification
Common NameThiotepa
DescriptionThiotepa, also known as thioplex or tepadina, belongs to the class of organic compounds known as organic thiophosphoric acids and derivatives. These are organic compounds containing the thiophosphoric acid functional group or a derivative thereof, with the general structure RP(R')(R'')=S, where R,R',R'' = O,N, halogen residue. It is a stable derivative of N,N',N''- triethylenephosphoramide (TEPA). Thiotepa is an extremely weak basic (essentially neutral) compound (based on its pKa). Thiotepa is formally rated as a carcinogen (by IARC 1) and is also a potentially toxic compound. These drugs act nonspecifically. They stop tumor growth by crosslinking guanine nucleobases in DNA double-helix strands, directly attacking DNA.
Structure
Thumb
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0015576 (Thiotepa)

  Mrv0541 02241205512D          

 11 13  0  0  0  0            999 V2000
    0.7145    3.0151    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395    3.0151    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395    2.1901    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520    1.4757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270    1.4757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395    3.8401    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270    4.5546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520    4.5546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    3.0151    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0789    3.4276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0789    2.6026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  3  5  1  0  0  0  0
  2  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  6  8  1  0  0  0  0
  2  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
  9 11  1  0  0  0  0
M  END
Download

3D MOL for HMDB0015576 (Thiotepa)

HMDB0015576
     RDKit          3D
Thiotepa
 23 25  0  0  0  0  0  0  0  0999 V2000
    0.5847   -0.1386   -1.9096 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.0504    0.0640   -0.2887 P   0  0  0  0  0  5  0  0  0  0  0  0
    1.1269   -0.7980    0.8006 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5137   -0.4221    0.6460 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0656   -1.7404    0.2557 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1759    1.7645    0.1124 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9897    2.5906    0.0074 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1474    2.6775   -0.9992 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5819   -0.4758   -0.1460 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9865   -1.2417    1.0120 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8380   -1.8778   -0.3597 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0157   -0.1992    1.6084 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8048    0.2916   -0.1548 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9190   -1.9326   -0.8314 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3435   -2.6449    0.8622 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0575    3.4770    0.6789 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9333    2.1017   -0.2962 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1260    2.2664   -2.0007 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8055    3.5816   -0.9685 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2325   -1.4977    1.7879 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0062   -1.0352    1.3992 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0062   -2.5987   -0.4311 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7952   -2.2122   -0.7850 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
Download

3D SDF for HMDB0015576 (Thiotepa)

  Mrv0541 02241205512D          

 11 13  0  0  0  0            999 V2000
    0.7145    3.0151    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395    3.0151    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395    2.1901    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520    1.4757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270    1.4757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395    3.8401    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270    4.5546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520    4.5546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    3.0151    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0789    3.4276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0789    2.6026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  3  5  1  0  0  0  0
  2  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  6  8  1  0  0  0  0
  2  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
  9 11  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0015576

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C6H12N3PS/c11-10(7-1-2-7,8-3-4-8)9-5-6-9/h1-6H2

> <INCHI_KEY>
FOCVUCIESVLUNU-UHFFFAOYSA-N

> <FORMULA>
C6H12N3PS

> <MOLECULAR_WEIGHT>
189.218

> <EXACT_MASS>
189.048954601

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
18.228092043834042

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
tris(aziridin-1-yl)-λ⁵-phosphanethione

> <ALOGPS_LOGP>
0.17

> <JCHEM_LOGP>
-1.0273805153333337

> <ALOGPS_LOGS>
-1.31

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-0.29921290491100205

> <JCHEM_POLAR_SURFACE_AREA>
9.03

> <JCHEM_REFRACTIVITY>
50.72220000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.27e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
thiophosphamide

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for HMDB0015576 (Thiotepa)

HMDB0015576
     RDKit          3D
Thiotepa
 23 25  0  0  0  0  0  0  0  0999 V2000
    0.5847   -0.1386   -1.9096 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.0504    0.0640   -0.2887 P   0  0  0  0  0  5  0  0  0  0  0  0
    1.1269   -0.7980    0.8006 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5137   -0.4221    0.6460 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0656   -1.7404    0.2557 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1759    1.7645    0.1124 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9897    2.5906    0.0074 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1474    2.6775   -0.9992 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5819   -0.4758   -0.1460 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9865   -1.2417    1.0120 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8380   -1.8778   -0.3597 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0157   -0.1992    1.6084 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8048    0.2916   -0.1548 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9190   -1.9326   -0.8314 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3435   -2.6449    0.8622 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0575    3.4770    0.6789 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9333    2.1017   -0.2962 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1260    2.2664   -2.0007 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8055    3.5816   -0.9685 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2325   -1.4977    1.7879 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0062   -1.0352    1.3992 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0062   -2.5987   -0.4311 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7952   -2.2122   -0.7850 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
Download

PDB for HMDB0015576 (Thiotepa)

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  S   UNK     0       1.334   5.628   0.000  0.00  0.00           S+0
HETATM    2  P   UNK     0       2.874   5.628   0.000  0.00  0.00           P+0
HETATM    3  N   UNK     0       2.874   4.088   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0       3.644   2.755   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.104   2.755   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0       2.874   7.168   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0       2.104   8.502   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.644   8.502   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0       4.414   5.628   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0       5.747   6.398   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.747   4.858   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    6    9                                             
CONECT    3    2    4    5                                                  
CONECT    4    3    5                                                       
CONECT    5    4    3                                                       
CONECT    6    2    7    8                                                  
CONECT    7    6    8                                                       
CONECT    8    7    6                                                       
CONECT    9    2   10   11                                                  
CONECT   10    9   11                                                       
CONECT   11   10    9                                                       
MASTER        0    0    0    0    0    0    0    0   11    0   26    0
END
Download

3D PDB for HMDB0015576 (Thiotepa)

COMPND    HMDB0015576
HETATM    1  S1  UNL     1       0.585  -0.139  -1.910  1.00  0.00           S  
HETATM    2  P1  UNL     1       0.050   0.064  -0.289  1.00  0.00           P  
HETATM    3  N1  UNL     1       1.127  -0.798   0.801  1.00  0.00           N  
HETATM    4  C1  UNL     1       2.514  -0.422   0.646  1.00  0.00           C  
HETATM    5  C2  UNL     1       2.066  -1.740   0.256  1.00  0.00           C  
HETATM    6  N2  UNL     1       0.176   1.764   0.112  1.00  0.00           N  
HETATM    7  C3  UNL     1      -0.990   2.591   0.007  1.00  0.00           C  
HETATM    8  C4  UNL     1       0.147   2.677  -0.999  1.00  0.00           C  
HETATM    9  N3  UNL     1      -1.582  -0.476  -0.146  1.00  0.00           N  
HETATM   10  C5  UNL     1      -1.987  -1.242   1.012  1.00  0.00           C  
HETATM   11  C6  UNL     1      -1.838  -1.878  -0.360  1.00  0.00           C  
HETATM   12  H1  UNL     1       3.016  -0.199   1.608  1.00  0.00           H  
HETATM   13  H2  UNL     1       2.805   0.292  -0.155  1.00  0.00           H  
HETATM   14  H3  UNL     1       1.919  -1.933  -0.831  1.00  0.00           H  
HETATM   15  H4  UNL     1       2.343  -2.645   0.862  1.00  0.00           H  
HETATM   16  H5  UNL     1      -1.057   3.477   0.679  1.00  0.00           H  
HETATM   17  H6  UNL     1      -1.933   2.102  -0.296  1.00  0.00           H  
HETATM   18  H7  UNL     1      -0.126   2.266  -2.001  1.00  0.00           H  
HETATM   19  H8  UNL     1       0.806   3.582  -0.969  1.00  0.00           H  
HETATM   20  H9  UNL     1      -1.233  -1.498   1.788  1.00  0.00           H  
HETATM   21  H10 UNL     1      -3.006  -1.035   1.399  1.00  0.00           H  
HETATM   22  H11 UNL     1      -1.006  -2.599  -0.431  1.00  0.00           H  
HETATM   23  H12 UNL     1      -2.795  -2.212  -0.785  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
Download

SMILES for HMDB0015576 (Thiotepa)

S=P(N1CC1)(N1CC1)N1CC1
Download

INCHI for HMDB0015576 (Thiotepa)

InChI=1S/C6H12N3PS/c11-10(7-1-2-7,8-3-4-8)9-5-6-9/h1-6H2
Download
View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
ValueSource
ThioplexKegg
TepadinaKegg
RethioKegg
GirostanHMDB
TespaHMDB
TespaminHMDB
Thio-tepaHMDB
Thio tepaHMDB
TriethylenethiophosphoramideHMDB
Tris(1-aziridinyl)phosphine sulfideHMDB
ThiophosphamideHMDB
Chemical FormulaC6H12N3PS
Average Molecular Weight189.218
Monoisotopic Molecular Weight189.048954601
IUPAC Nametris(aziridin-1-yl)-λ⁵-phosphanethione
Traditional Namethiophosphamide
CAS Registry Number52-24-4
SMILES
S=P(N1CC1)(N1CC1)N1CC1
InChI Identifier
InChI=1S/C6H12N3PS/c11-10(7-1-2-7,8-3-4-8)9-5-6-9/h1-6H2
InChI KeyFOCVUCIESVLUNU-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as organic thiophosphoric acids and derivatives. These are organic compounds containing the thiophosphoric acid functional group or a derivative thereof, with the general structure RP(R')(R'')=S, where R,R',R'' = O,N, halogen residue.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassOrganic thiophosphoric acids and derivatives
Sub ClassNot Available
Direct ParentOrganic thiophosphoric acids and derivatives
Alternative Parents
Substituents
  • Organic thiophosphoric acid or derivatives
  • Azacycle
  • Organoheterocyclic compound
  • Aziridine
  • Organic nitrogen compound
  • Organopnictogen compound
  • 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
StateSolid
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 Locations
  • Cytoplasm
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB04572 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB04572 details
Abnormal Concentrations
Not Available
Predicted Concentrations
BiospecimenValueOriginal ageOriginal sexOriginal conditionComments
Blood0.000 uMAdult (>18 years old)BothNormalPredicted based on drug qualities
Blood0.000 umol/mmol creatinineAdult (>18 years old)BothNormalPredicted based on drug qualities
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB04572
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID5254
KEGG Compound IDC07641
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkThioTEPA
METLIN IDNot Available
PubChem Compound5453
PDB IDNot Available
ChEBI ID128310
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. Maanen MJ, Smeets CJ, Beijnen JH: Chemistry, pharmacology and pharmacokinetics of N,N',N" -triethylenethiophosphoramide (ThioTEPA). Cancer Treat Rev. 2000 Aug;26(4):257-68. [PubMed:10913381 ]

Enzymes

Enzyme Details
1. Cytochrome P450 3A4
General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
Gene Name:
CYP3A4
Uniprot ID:
P08684
Molecular weight:
57255.585
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
Enzyme Details
2. Cytochrome P450 2B6
General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,4-cineole 2-exo-monooxygenase.
Gene Name:
CYP2B6
Uniprot ID:
P20813
Molecular weight:
56277.81
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]