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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:49 UTC
Update Date2022-03-07 02:51:41 UTC
HMDB IDHMDB0014631
Secondary Accession Numbers
  • HMDB14631
Metabolite Identification
Common NameAltretamine
DescriptionAltretamine is only found in individuals that have used or taken this drug. It is an alkylating agent proposed as an antineoplastic. It also acts as a chemosterilant for male houseflies and other insects. [PubChem]The precise mechanism by which altretamine exerts its cytotoxic effect is unknown although it is classified as an alkylating anti-neoplastic agent. Through this mechanism, the drug is metabolized into alkylating agents by N-demethylation. These alkylating species consequently damage tumor cells.
Structure
Data?1582753201
Synonyms
ValueSource
2,4,6-Tris(dimethylamino)-1,3,5-triazineChEBI
2,4,6-Tris(dimethylamino)-S-triazineChEBI
AltretaminaChEBI
AltretaminumChEBI
HexalenChEBI
HexastatChEBI
HMMChEBI
HEXAMETHYLMELAMINEHMDB
HTMHMDB
HXMHMDB
Bellon brand OF altretamineHMDB
Chiesi brand OF altretamineHMDB
MGI pharma brand OF altretamineHMDB
Rhône poulenc rorer brand OF altretamineHMDB
Altretamine bellon brandHMDB
Altretamine chiesi brandHMDB
HexinawasHMDB
Wassermann brand OF altretamineHMDB
HemelHMDB
Altretamine wassermann brandHMDB
Rhône-poulenc rorer brand OF altretamineHMDB
AltretamineChEBI
Chemical FormulaC9H18N6
Average Molecular Weight210.2794
Monoisotopic Molecular Weight210.159294606
IUPAC NameN2,N2,N4,N4,N6,N6-hexamethyl-1,3,5-triazine-2,4,6-triamine
Traditional Namealtretamine
CAS Registry Number645-05-6
SMILES
CN(C)C1=NC(=NC(=N1)N(C)C)N(C)C
InChI Identifier
InChI=1S/C9H18N6/c1-13(2)7-10-8(14(3)4)12-9(11-7)15(5)6/h1-6H3
InChI KeyUUVWYPNAQBNQJQ-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as dialkylarylamines. These are aliphatic aromatic amines in which the amino group is linked to two aliphatic chains and one aromatic group.
KingdomOrganic compounds
Super ClassOrganic nitrogen compounds
ClassOrganonitrogen compounds
Sub ClassAmines
Direct ParentDialkylarylamines
Alternative Parents
Substituents
  • Dialkylarylamine
  • N-aliphatic s-triazine
  • Aminotriazine
  • Amino-1,3,5-triazine
  • 1,3,5-triazine
  • Triazine
  • Heteroaromatic compound
  • Azacycle
  • Organoheterocyclic compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point172 - 174 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility3.1 g/LNot Available
LogP1.7Not Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M+H]+Not Available145.612http://allccs.zhulab.cn/database/detail?ID=AllCCS00000713
Predicted Molecular Properties
PropertyValueSource
Water Solubility3.1 g/LALOGPS
logP2.43ALOGPS
logP2.22ChemAxon
logS-1.8ALOGPS
pKa (Strongest Basic)7.75ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area48.39 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity65.65 m³·mol⁻¹ChemAxon
Polarizability23.7 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+149.9231661259
DarkChem[M-H]-149.18331661259
DeepCCS[M+H]+152.85230932474
DeepCCS[M-H]-150.45730932474
DeepCCS[M-2H]-183.71930932474
DeepCCS[M+Na]+158.88430932474
AllCCS[M+H]+149.132859911
AllCCS[M+H-H2O]+145.632859911
AllCCS[M+NH4]+152.432859911
AllCCS[M+Na]+153.332859911
AllCCS[M-H]-149.832859911
AllCCS[M+Na-2H]-150.832859911
AllCCS[M+HCOO]-152.032859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
AltretamineCN(C)C1=NC(=NC(=N1)N(C)C)N(C)C1929.9Standard polar33892256
AltretamineCN(C)C1=NC(=NC(=N1)N(C)C)N(C)C1695.2Standard non polar33892256
AltretamineCN(C)C1=NC(=NC(=N1)N(C)C)N(C)C1663.0Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Altretamine GC-MS (Non-derivatized) - 70eV, Positivesplash10-01ox-7790000000-e6026ce486911f4322312017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Altretamine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Altretamine LC-ESI-qTof , Positive-QTOFsplash10-03dj-9781100000-4553bbbe9a30a0391bb42017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Altretamine , positive-QTOFsplash10-03di-3490000000-4af5631898604d2cec102017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Altretamine , positive-QTOFsplash10-03dj-9781100000-4553bbbe9a30a0391bb42017-09-14HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Altretamine 10V, Positive-QTOFsplash10-03di-0090000000-d69cd870b4294e5bc1702016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Altretamine 20V, Positive-QTOFsplash10-03di-0090000000-eab4cf11b3d7c71c506a2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Altretamine 40V, Positive-QTOFsplash10-03di-1890000000-772056487934c472a76f2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Altretamine 10V, Negative-QTOFsplash10-0a4i-0090000000-72599b7d9a667dc243392016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Altretamine 20V, Negative-QTOFsplash10-0a4i-0190000000-18a5954520aa78e7f71a2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Altretamine 40V, Negative-QTOFsplash10-0a4l-0940000000-1d4df681882fc50a12022016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Altretamine 10V, Negative-QTOFsplash10-0a4i-0090000000-a14cd1e86a35ad0351f12021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Altretamine 20V, Negative-QTOFsplash10-0a4i-0090000000-517d269b99785ef1fe2a2021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Altretamine 40V, Negative-QTOFsplash10-0udl-3900000000-7516b289587ed30b86d12021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Altretamine 10V, Positive-QTOFsplash10-03di-0090000000-0434331ef81b820cb7f02021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Altretamine 20V, Positive-QTOFsplash10-03di-0090000000-0434331ef81b820cb7f02021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Altretamine 40V, Positive-QTOFsplash10-01ba-9100000000-f88e708bc1bf0a456d922021-09-25Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00488 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00488 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00488
Phenol Explorer Compound IDNot Available
FooDB IDFDB001629
KNApSAcK IDC00008231
Chemspider ID2038
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkAltretamine
METLIN IDNot Available
PubChem Compound2123
PDB IDNot Available
ChEBI ID24564
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. Damia G, D'Incalci M: Clinical pharmacokinetics of altretamine. Clin Pharmacokinet. 1995 Jun;28(6):439-48. [PubMed:7656502 ]
  2. Malik IA: Altretamine is an effective palliative therapy of patients with recurrent epithelial ovarian cancer. Jpn J Clin Oncol. 2001 Feb;31(2):69-73. [PubMed:11302345 ]
  3. Keldsen N, Havsteen H, Vergote I, Bertelsen K, Jakobsen A: Altretamine (hexamethylmelamine) in the treatment of platinum-resistant ovarian cancer: a phase II study. Gynecol Oncol. 2003 Feb;88(2):118-22. [PubMed:12586589 ]
  4. Chan JK, Loizzi V, Manetta A, Berman ML: Oral altretamine used as salvage therapy in recurrent ovarian cancer. Gynecol Oncol. 2004 Jan;92(1):368-71. [PubMed:14751188 ]