CAS 113857-87-7 | Benzoic acid, 2-[[[(4S)-4-carboxy-4-[[4-[[(2,4-diamino-6-pteridinyl)methyl]amino]benzoyl]amino]butyl]amino]carbonyl]- | CAS Number 113857-87-7

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113857-87-7 | Benzoic acid, 2-[[[(4S)-4-carboxy-4-[[4-[[(2,4-diamino-6-pteridinyl)methyl]amino]benzoyl]amino]butyl]amino]carbonyl]-

CAS No: 113857-87-7 Catalog No: AG0009YK MDL No:

Product Description

Catalog Number:

AG0009YK

Chemical Name:

Benzoic acid, 2-[[[(4S)-4-carboxy-4-[[4-[[(2,4-diamino-6-pteridinyl)methyl]amino]benzoyl]amino]butyl]amino]carbonyl]-

CAS Number:

113857-87-7

Molecular Formula:

C27H27N9O6

Molecular Weight:

573.5600

IUPAC Name:

2-[[(4S)-4-carboxy-4-[[4-[(2,4-diaminopteridin-6-yl)methylamino]benzoyl]amino]butyl]carbamoyl]benzoic acid

InChI:

InChI=1S/C27H27N9O6/c28-21-20-22(36-27(29)35-21)32-13-16(33-20)12-31-15-9-7-14(8-10-15)23(37)34-19(26(41)42)6-3-11-30-24(38)17-4-1-2-5-18(17)25(39)40/h1-2,4-5,7-10,13,19,31H,3,6,11-12H2,(H,30,38)(H,34,37)(H,39,40)(H,41,42)(H4,28,29,32,35,36)/t19-/m0/s1

InChI Key:

NYQPLPNEESYGNO-IBGZPJMESA-N

SMILES:

OC(=O)[C@@H](NC(=O)c1ccc(cc1)NCc1cnc2c(n1)c(N)nc(n2)N)CCCNC(=O)c1ccccc1C(=O)O

UNII:

A8E516A20K

Properties

Complexity:

949

Compound Is Canonicalized:

Yes

Covalently-Bonded Unit Count:

Defined Atom Stereocenter Count:

Defined Bond Stereocenter Count:

Exact Mass:

573.208g/mol

Formal Charge:

Heavy Atom Count:

Hydrogen Bond Acceptor Count:

Hydrogen Bond Donor Count:

Isotope Atom Count:

Molecular Weight:

573.57g/mol

Monoisotopic Mass:

573.208g/mol

Rotatable Bond Count:

Topological Polar Surface Area:

248A^2

Undefined Atom Stereocenter Count:

Undefined Bond Stereocenter Count:

XLogP3:

-0.6

Literature

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Synthesis, biological, and antitumor activity of a highly potent 6-substituted pyrrolo[2,3-d]pyrimidine thienoyl antifolate inhibitor with proton-coupled folate transporter and folate receptor selectivity over the reduced folate carrier that inhibits β-glycinamide ribonucleotide formyltransferase.	Journal of medicinal chemistry 20111027
Investigational approaches for mesothelioma.	Frontiers in oncology 20110101
In silico structure-based design of a novel class of potent and selective small peptide inhibitor of Mycobacterium tuberculosis Dihydrofolate reductase, a potential target for anti-TB drug discovery.	Molecular diversity 20100801
Clinical potency of methotrexate, aminopterin, talotrexin and pemetrexed in childhood leukemias.	Cancer chemotherapy and pharmacology 20100501
Synthesis and antitumor activity of a novel series of 6-substituted pyrrolo[2,3-d]pyrimidine thienoyl antifolate inhibitors of purine biosynthesis with selectivity for high affinity folate receptors and the proton-coupled folate transporter over the reduced folate carrier for cellular entry.	Journal of medicinal chemistry 20100211
Cancer chemotherapy: targeting folic acid synthesis.	Cancer management and research 20100101
Emerging therapeutic options for Philadelphia-positive acute lymphocytic leukemia.	Expert opinion on emerging drugs 20070301
Treatment of acute lymphoblastic leukaemia : a new era.	Drugs 20070101
Coexistence of multiple mechanisms of PT523 resistance in human leukemia cells harboring 3 reduced folate carrier alleles: transcriptional silencing, inactivating mutations, and allele loss.	Blood 20060415
The inverse relationship between reduced folate carrier function and pemetrexed activity in a human colon cancer cell line.	Molecular cancer therapeutics 20060201
AACR-NCI-EORTC--17th symposium: Molecular targets and cancer therapeutics. 14-18th November 2005, Philadelphia, PA, USA.	IDrugs : the investigational drugs journal 20060101
Selective preservation of pemetrexed pharmacological activity in HeLa cells lacking the reduced folate carrier: association with the presence of a secondary transport pathway.	Cancer research 20040501
Further studies on the interaction of nonpolyglutamatable aminopterin analogs with dihydrofolate reductase and the reduced folate carrier as determinants of in vitro antitumor activity.	Biochemical pharmacology 20030501
Synthesis and in vitro antitumor activity of new deaza analogues of the nonpolyglutamatable antifolate N(alpha)-(4-amino-4-deoxypteroyl)-N(delta)-hemiphthaloyl-L-ornithine (PT523).	Journal of medicinal chemistry 20020411
Multiple mechanisms of resistance to methotrexate and novel antifolates in human CCRF-CEM leukemia cells and their implications for folate homeostasis.	Biochemical pharmacology 20020115