ID: ALA170101

Max Phase: Preclinical

Molecular Formula: C21H25N5O6

Molecular Weight: 443.46

Molecule Type: Small molecule

Representations

Canonical SMILES:  Nc1nc(O)c2c(n1)NCC(CCc1ccc(C(=O)NC(CCC(=O)O)C(=O)O)cc1)C2

Standard InChI:  InChI=1S/C21H25N5O6/c22-21-25-17-14(19(30)26-21)9-12(10-23-17)2-1-11-3-5-13(6-4-11)18(29)24-15(20(31)32)7-8-16(27)28/h3-6,12,15H,1-2,7-10H2,(H,24,29)(H,27,28)(H,31,32)(H4,22,23,25,26,30)

Standard InChI Key:  ZUQBAQVRAURMCL-UHFFFAOYSA-N

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Properties

Molecular Weight: 443.46

Molecular Weight (Monoisotopic): 443.1805

AlogP: 1.03

#Rotatable Bonds: 9

Polar Surface Area: 187.76

Molecular Species: ACID

HBA: 8

HBD: 6

#RO5 Violations: 1

HBA (Lipinski): 11

HBD (Lipinski): 7

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 3.34

CX Basic pKa: 3.83

CX LogP: 1.40

CX LogD: -4.63

Aromatic Rings: 2

Heavy Atoms: 32

QED Weighted: 0.33

Np Likeness Score: 0.24

References

1. Bigham EC, Hodson SJ, Mallory WR, Wilson D, Duch DS, Smith GK, Ferone R..  (1992)  Synthesis and biological activity of open-chain analogues of 5,6,7,8-tetrahydrofolic acid--potential antitumor agents.,  35  (8): [PMID:1573633] [10.1021/jm00086a008]

2. Borrell JI, Teixidó J, Matallana JL, Martínez-Teipel B, Colominas C, Costa M, Balcells M, Schuler E, Castillo MJ..  (2001)  Synthesis and biological activity of 7-oxo substituted analogues of 5-deaza-5,6,7,8-tetrahydrofolic acid (5-DATHF) and 5,10-dideaza-5,6,7,8-tetrahydrofolic acid (DDATHF).,  44  (14): [PMID:11428931] [10.1021/jm990411u]

3. Taylor EC, Kuhnt D, Shih C, Rinzel SM, Grindey GB, Barredo J, Jannatipour M, Moran RG..  (1992)  A dideazatetrahydrofolate analogue lacking a chiral center at C-6, N-[4-[2-(2-amino-3,4-dihydro-4-oxo-7H-pyrrolo[2,3-d]pyrimidin-5- yl)ethyl]benzoyl]-L-glutamic acid, is an inhibitor of thymidylate synthase.,  35  (23): [PMID:1447744] [10.1021/jm00101a023]

4. Taylor EC, Dowling JE.  (1997)  Synthesis of a pyrimido[4,5-b]azepine analog of 5,10-dideaza-5,6,7,8-tetrahydrofolic acid (DDATHF),  7  (4): [10.1016/S0960-894X(97)00041-3]

5. Singh SK, Dev IK, Duch DS, Ferone R, Smith GK, Freisheim JH, Hynes JB..  (1991)  Synthesis and biological evaluation of 5-deazaisofolic acid, 5-deaza-5,6,7,8-tetrahydroisofolic acid, and their N9-substituted analogues.,  34  (2): [PMID:1995883] [10.1021/jm00106a021]

6. Gossett LS, Habeck LL, Shackelford KA, Mendelsohn LG, Gates SB, Worzalla JF, Self TD, Theobald KS, Andis SL, Schultz RM, Shih C..  (1999)  The synthesis and biological activity of a series of 2,4-diaminopyrido[2,3-d]pyrimidine based antifolates as antineoplastic and antiarthritic agents.,  9  (1): [PMID:9990460] [10.1016/s0960-894x(98)00683-0]

7. Taylor EC, Harrington PJ, Fletcher SR, Beardsley GP, Moran RG..  (1985)  Synthesis of the antileukemic agents 5,10-dideazaaminopterin and 5,10-dideaza-5,6,7,8-tetrahydroaminopterin.,  28  (7): [PMID:4009615] [10.1021/jm00145a012]

Source

Source(1):

• Scientific Literature