(2S)-2-{[4-({[(6S)-2-amino-4-oxo-4,4a,5,6,7,8-hexahydropteridin-6-yl]methyl}amino)phenyl]formamido}pentanedioic acid

• ChemBase ID: 178349
• Molecular Formular: C19H23N7O6
• Molecular Mass: 445.42922
• Monoisotopic Mass: 445.17098149
• SMILES: N1=C(N=C2C(C1=O)N[C@H](CN2)CNc1ccc(cc1)C(=O)N[C@@H](CCC(=O)O)C(=O)O)N
• Canonical SMILES: OC(=O)CC[C@@H](C(=O)O)NC(=O)c1ccc(cc1)NC[C@H]1CNC2=NC(=NC(=O)C2N1)N
• InChI: InChI=1S/C19H23N7O6/c20-19-25-15-14(17(30)26-19)23-11(8-22-15)7-21-10-3-1-9(2-4-10)16(29)24-12(18(31)32)5-6-13(27)28/h1-4,11-12,14,21,23H,5-8H2,(H,24,29)(H,27,28)(H,31,32)(H3,20,22,25,26,30)/t11-,12-,14?/m0/s1
• InChIKey: GTHBYNYDVOUIBB-VHBIQUBJSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-{[4-({[(6S)-2-amino-4-oxo-4,4a,5,6,7,8-hexahydropteridin-6-yl]methyl}amino)phenyl]formamido}pentanedioic acid
• IUPAC Traditional name: (2S)-2-{[4-({[(6S)-2-amino-4-oxo-5,6,7,8-tetrahydro-4aH-pteridin-6-yl]methyl}amino)phenyl]formamido}pentanedioic acid
• Synonyms: (S)-N-[4-[[(2-Amino-1,4,5,6,7,8-hexahydro-4-oxo-6-pteridinyl)methyl]amino]benzoyl]-L-glutamic Acid; (6S)-Tetrahydrofolic Acid

Database IDs

• CAS Number: 71963-69-4
• PubChem SID: 164234259
• PubChem CID: 71752454

CALCULATED PROPERTIES

• Acid pKa: 3.1318212
• H Acceptors: 12
• H Donor: 7
• LogD (pH = 5.5): -6.851179
• LogD (pH = 7.4): -10.537097
• Log P: -4.0540705
• Molar Refractivity: 110.0061 cm^3
• Polarizability: 41.545555 Å^3
• Polar Surface Area: 207.6 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Dimethyl Sulfoxide
• Apperance: Yellow Solid

Safety Information

• Storage Condition: Refrigerator, under inert atmosphere

DETAILS

Toronto Research Chemicals - T293585

Folic Acid (F680300) derivative. Has been shown to increase methotrexalate metabolism in humans.

REFERENCES

• Jolivet, J. et al.; Biochem. Phamacol. 36, 3310 (1987).