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150399-23-8 molecular structure
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disodium (2R)-2-{[4-(2-{2-amino-4-oxo-1H,4H,7H-pyrrolo[2,3-d]pyrimidin-5-yl}ethyl)phenyl]formamido}pentanedioate

ChemBase ID: 176254
Molecular Formular: C20H19N5Na2O6
Molecular Mass: 471.3743
Monoisotopic Mass: 471.11307192
SMILES and InChIs

SMILES:
c1(nc(=O)c2c([nH]1)[nH]cc2CCc1ccc(cc1)C(=O)N[C@H](CCC(=O)[O-])C(=O)[O-])N.[Na+].[Na+]
Canonical SMILES:
[O-]C(=O)CC[C@H](C(=O)[O-])NC(=O)c1ccc(cc1)CCc1c[nH]c2c1c(=O)nc([nH]2)N.[Na+].[Na+]
InChI:
InChI=1S/C20H21N5O6.2Na/c21-20-24-16-15(18(29)25-20)12(9-22-16)6-3-10-1-4-11(5-2-10)17(28)23-13(19(30)31)7-8-14(26)27;;/h1-2,4-5,9,13H,3,6-8H2,(H,23,28)(H,26,27)(H,30,31)(H4,21,22,24,25,29);;/q;2*+1/p-2/t13-;;/m1../s1
InChIKey:
NYDXNILOWQXUOF-FFXKMJQXSA-L

Cite this record

CBID:176254 http://www.chembase.cn/molecule-176254.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
disodium (2R)-2-{[4-(2-{2-amino-4-oxo-1H,4H,7H-pyrrolo[2,3-d]pyrimidin-5-yl}ethyl)phenyl]formamido}pentanedioate
IUPAC Traditional name
disodium (2R)-2-{[4-(2-{2-amino-4-oxo-1H,7H-pyrrolo[2,3-d]pyrimidin-5-yl}ethyl)phenyl]formamido}pentanedioate
Synonyms
N-[4-[2-(2-Amino-4,7-dihydro-4-oxo-3H-pyrrolo[2,3-d]pyrimidin-5-yl)ethyl]benzoyl]-L-glutamic Acid Sodium Salt
N-[4-[(2-Amino-4,7-dihydro-4-oxo-1H-pyrrolo[2,3-d]pyrimidin-5-yl)ethyl]benzoyl]-L-glutamic Acid Disodium
Alimta
LY 231514
LY 231514 Disodium
Pemetrexed Sodium
Rolazar
Tifolar
Pemetrexed Disodium
D-Pemetrexed Hydrate
N-[4-[2-(2-Amino-4,7-dihydro-4-oxo-3H-pyrrolo[2,3-d]pyrimidin-5-yl)ethyl]benzoyl]-D-glutamic Acid Hydrate
CAS Number
150399-23-8
PubChem SID
164232164
PubChem CID
125891

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources
Data Source Data ID
PubChem 125891 external link

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem
Acid pKa 3.3411286  H Acceptors
H Donor LogD (pH = 5.5) -2.0354757 
LogD (pH = 7.4) -5.0479527  Log P 1.4881234 
Molar Refractivity 131.1238 cm3 Polarizability 40.18901 Å3
Polar Surface Area 192.63 Å2 Rotatable Bonds
Lipinski's Rule of Five true 

PROPERTIES

PROPERTIES

Physical Property Safety Information Product Information Bioassay(PubChem)
Solubility
DMSO expand Show data source
Methanol expand Show data source
Water expand Show data source
Apperance
Off-White Solid expand Show data source
Melting Point
176-178°C (dec.) expand Show data source
254-258°C (dec.) expand Show data source
Storage Condition
-20°C Freezer expand Show data source
MSDS Link
Download expand Show data source
Certificate of Analysis
Download expand Show data source

DETAILS

DETAILS

TRC TRC
Toronto Research Chemicals - P219490 external link
Pemetrexed (P219500) isomer impurity.
Toronto Research Chemicals - P219500 external link
Multitargeted antifolate; inhibits thymidylate synthase as well as other folate dependent enzymes. Antineoplastic.

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • McDonald, A.C., et al.: Clin. Cancer Res., 4, 605 (1998)
  • • John, W., et al.: Cancer, 88, 1807 (1998)
  • • Miller, K.D., et al.: Ann. Oncol., 11, 101 (1998)
  • • McDonald, A.C., et al.: Clin. Cancer Res., 4, 605 (1998)
  • • John, W., et al.: Cancer, 88, 1807 (1998)
  • • Miller, K.D., et al.: Ann. Oncol., 11, 101 (1998)
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PATENTS

PATENTS

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INTERNET

INTERNET

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