Deoxyaminopteroic Acid
Basic information
- CAS
19741-14-1- Standard SMILES
CN(Cc1cnc2nc(N)nc(N)c2n1)c1ccc(C(=O)O)cc1- InChIKey
LWCXZSDKANNOAR-UHFFFAOYSA-N- Molecular formula
- C15H15N7O2
- Average molar mass
- 325.33 g/mol
- Monoisotopic mass
- 325.12872275
Overview
Deoxyaminopteroic Acid is a metabolite resulting from the carboxypeptidase-mediated cleavage of methotrexate. Deoxyaminopteroic acid can be used a marker for methotrexate exposure.
Names & identifiers
- Preferred name
- Deoxyaminopteroic Acid
- IUPAC
- 4-[(2,4-diaminopteridin-6-yl)methyl-methylamino]benzoic acid
- English name
- 4-[N-(2,4-DIAMINO-6-PTERIDINYLMETHYL)-N-METHYLAMINO] BENZOIC ACID
- Molecular formula
- C15H15N7O2
- Molecular weight
- 325.33
Names & synonyms
19741-14-1DAMPADeoxyaminopteroic acid4-(((2,4-Diaminopteridin-6-yl)methyl)(methyl)amino)benzoic acid4-{[(2,4-diaminopteridin-6-yl)methyl](methyl)amino}benzoic acid2,4-ApaP7OVP484DX2,4-Diamino-N(10)-methylpteroic acid4-Deoxy-4-amino-N(10)-methylpteroic acidDTXSID201734272,4-diamino-N10-methylpteroic acid4-(((2,4-Diamino-6-pteridinyl)methyl)methylamino)benzoic acid
Show more names
NSC 133723Nsc 131463NSC 131463 (DAMPA)DAMPA hydrochloride hydrateMethotrexate Impurity 5(EP-E)4-(((2,4-Diaminopteridin-6-yl)
4-[[(2,4-diamino-6-pteridinyl)methyl]methylamino]benzoic acid4-[[(2,4-Diaminopteridin-6-yl)methyl](methyl)amino]benzoic Acid4-Amino-4-deoxy-N-10-methylpteroic acidRefChem:516469DTXCID00959184-amino-4-deoxy-N 10-methylpteroic acidMethotrexate metaboliteMethotrexate EP Impurity E
Database identifiers
- CAS
19741-14-1
Properties
Computed structural properties
- XLogP
- -1.1
- Topological polar surface area
- 144 Ų
- Hydrogen bond donors
- 3
- Hydrogen bond acceptors
- 9
- Rotatable bonds
- 4
- Heavy atoms
- 24
- Formal charge
- 0
- Complexity
- 444
Physicochemical properties
- Melting point
- 255 °C · 255 °C (dec.)(lit.)
- Boiling point
- 689.3 · 689.3±65.0 °C(Predicted)
- Density
- 1.532 · 1.532
- storage temp.
- 2 · 2-8°C(protect from light)
- solubility
- Aqueous Base, DMSO
- pka
- 4.63 · 4.63±0.10(Predicted)
- form
- Solid
- color
- Dark Yellow to Very Dark Brown
- Stability
- Hygroscopic
- Major Application
- pharmaceutical (small molecule)
- InChI
- 1S/C15H15N7O2/c1-22(10-4-2-8(3-5-10)14(23)24)7-9-6-18-13-11(19-9)12(16)20-15(17)21-13/h2-6H,7H2,1H3,(H,23,24)(H4,16,17,18,20,21)
- InChIKey
- LWCXZSDKANNOAR-UHFFFAOYSA-N
- SMILES
- N(Cc2nc3c(nc(nc3N)N)nc2)(C)c1ccc(cc1)C(=O)O
- CAS DataBase Reference
- 19741 · 19741-14-1
- FDA UNII
- 7 OVP484DX · P7OVP484DX
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Danger
H301 (95%): Toxic if swallowed [Danger Acute toxicity, oral]
P203, P261, P264, P264+P265, P270, P271, P280, P301+P316, P302+P352, P304+P340, P305+P351+P338, P318, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 20 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Hazard Classes and CategoriesAcute Tox. 3 (95%)
Safety data
- wgk
- 3
- risk_code
- 43-52/53
- Signal word
- Danger
- Symbol(GHS)
- GHS06,GHS08
- hazard_code
- Xi
- safety_code
- 36/37
- Storage Class
- 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
- Hazard statements
- H301-H315-H319-H341-H360D
- Hazard Classifications
- Acute Tox. 3 OralEye Irrit. 2Muta. 2Repr. 1BSkin Irrit. 2
- Precautionary statements
- P202-P264-P270-P301+P310-P302+P352-P305+P351+P338
Chemistry & industry
Applications
UsesDAMPA is a Methotrexate (M260675) analog (1). DAMPA is an antitumor agent (2).
Upstream & downstream products
Downstream products
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Related reactions
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Compound notes
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