calcium (2S)-2-[(4-{[(2-amino-5-formyl-4-oxo-1,4,5,6,7,8-hexahydropteridin-6-yl)methyl]amino}phenyl)formamido]pentanedioate pentahydrate

• ChemBase ID: 72586
• Molecular Formular: C20H31CaN7O12
• Molecular Mass: 601.57784
• Monoisotopic Mass: 601.16566045
• SMILES: n1c([nH]c2c(c1=O)N(C(CN2)CNc1ccc(cc1)C(=O)N[C@@H](CCC(=O)[O-])C(=O)[O-])C=O)N.[Ca+2].O.O.O.O.O
• Canonical SMILES: O=CN1C(CNc2ccc(cc2)C(=O)N[C@H](C(=O)[O-])CCC(=O)[O-])CNc2c1c(=O)nc([nH]2)N.O.O.O.O.O.[Ca+2]
• InChI: InChI=1S/C20H23N7O7.Ca.5H2O/c21-20-25-16-15(18(32)26-20)27(9-28)12(8-23-16)7-22-11-3-1-10(2-4-11)17(31)24-13(19(33)34)5-6-14(29)30;;;;;;/h1-4,9,12-13,22H,5-8H2,(H,24,31)(H,29,30)(H,33,34)(H4,21,23,25,26,32);;5*1H2/q;+2;;;;;/p-2/t12?,13-;;;;;;/m0....../s1
• InChIKey: NPPBLUASYYNAIG-ZIGBGYJWSA-L

NAMES AND DATABASE IDS

Names

• IUPAC name: calcium (2S)-2-[(4-{[(2-amino-5-formyl-4-oxo-1,4,5,6,7,8-hexahydropteridin-6-yl)methyl]amino}phenyl)formamido]pentanedioate pentahydrate
• IUPAC Traditional name: calcium (2S)-2-[(4-{[(2-amino-5-formyl-4-oxo-1,6,7,8-tetrahydropteridin-6-yl)methyl]amino}phenyl)formamido]pentanedioate pentahydrate; calcium(2+) (2S)-2-[(4-{[(2-amino-5-formyl-4-oxo-1,6,7,8-tetrahydropteridin-6-yl)methyl]amino}phenyl)formamido]pentanedioate pentahydrate
• Synonyms: N-[4-[[(2-Amino-5-formyl-1,4,5,6,7,8-hexahydro-4-oxo-6-pteridinyl)methyl]amino]benzoyl]-L-glutamic Acid Calcium Salt Pentahydrate; Folaren; Foliben; Folidan; Folinic Acid Calcium Salt Pentahydrate; Lederfolat; Lederfolin; Leucovorin Calcium Salt Pentahydrate; Sodium Folinate; Calcium Folinate; Leucovorin Calcium

Database IDs

• CAS Number: 6035-45-6
• PubChem SID: 162037511
• PubChem CID: 20835958

CALCULATED PROPERTIES

• Acid pKa: 3.2672794
• H Acceptors: 12
• H Donor: 5
• LogD (pH = 5.5): -6.2633014
• LogD (pH = 7.4): -8.90289
• Log P: -2.846294
• Molar Refractivity: 148.1362 cm^3
• Polarizability: 43.079628 Å^3
• Polar Surface Area: 221.21 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Water
• Apperance: Off-White to Pale Yellow Solid
• Melting Point: >260°C (dec.)

Safety Information

• Storage Condition: -20°C; -20°C Freezer

Product Information

• Salt Data: Calcium salt

DETAILS

Selleck Chemicals - S1236

Research Area: Cancer, Metabolic Disease , Endocrinology
Biological Activity:
Human lymphoid cell lines were studied for leucovorin requirements to protect from methotrexate (MTX)-induced growth suppression. Over a 72h continuous exposure leucovorin provided better protection to the cell lines LAZ-007 and RAJI than to the cell lines CCRF-CEM and MOLT-4. [1]Leucovorin is a compound similar to folic acid, which is a necessary vitamin.  It has been around and in use for many decades. Leucovorin is a medication frequently used in combination with the chemotherapy drugs fluoruracil and methotrexate.  Leucovorin is a chemoprotectant, not a chemotherapy drug, however,  it is used in addition to these chemotherapy drugs to enhance anti cancer effects (with fluorouracil) or to help prevent or lessen side effects (with methotrexate). [2]

Toronto Research Chemicals - L330400

An intermediate product of the metabolism of Folic Acid. This compound is a mixture of diastereomers.

REFERENCES

• Pont, L.O., et al.: Anal. Profiles Drug Subs., 8, 315 (1979)
• Yale, R.J.D, et al.: J. Biol. Med., 61, 23 (1979)