4-(4-((2-amino-4-oxo-4,7-dihydro-3H-pyrrolo[2,3-d]pyrimidin-5-yl)methyl)benzamido)benzoic acid

Names and Identifiers

Canonical SMILES: Nc1nc2[nH]cc(Cc3ccc(C(=O)Nc4ccc(C(=O)O)cc4)cc3)c2c(=O)[nH]1

Standard InChI: InChI=1S/C21H17N5O4/c22-21-25-17-16(19(28)26-21)14(10-23-17)9-11-1-3-12(4-2-11)18(27)24-15-7-5-13(6-8-15)20(29)30/h1-8,10H,9H2,(H,24,27)(H,29,30)(H4,22,23,25,26,28)

Standard InChI Key: DCQTYKQXUDEDCB-UHFFFAOYSA-N

Molfile:

 
     RDKit          2D

 30 33  0  0  0  0  0  0  0  0999 V2000
    3.2688  -20.2936    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2688  -21.1108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9740  -21.5152    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9740  -19.8809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6793  -20.2936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6838  -21.1072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4590  -21.3545    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.9337  -20.6935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4518  -20.0380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9740  -19.0637    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5617  -21.5204    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.7000  -19.2594    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4984  -19.0851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0451  -19.6929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8428  -19.5191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0918  -18.7398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5368  -18.1342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7412  -18.3111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8899  -18.5644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4409  -19.1680    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.1371  -17.7855    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.9353  -17.6102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4818  -18.2145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2793  -18.0397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5272  -17.2601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9715  -16.6552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1761  -16.8332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3260  -17.0837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8778  -17.6865    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.5722  -16.3044    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  4  1  0
  2  3  2  0
  3  6  1  0
  5  4  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9  5  1  0
  4 10  2  0
  2 11  1  0
  9 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 13  1  0
 16 19  1  0
 19 20  2  0
 19 21  1  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 22  1  0
 28 29  1  0
 28 30  2  0
 25 28  1  0
M  END

Alternative Forms

Parent:

ALA4544605
---

Associated Targets(Human)

TYMS Tclin Thymidylate synthase (1651 Activities)

Discover Target: TYMS

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Associated Targets(non-human)

Bifunctional dihydrofolate reductase-thymidylate synthase (81 Activities)

Explore this target

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Molecule Features

Natural Product: No	Oral: No	Chemical Probe: No	Parenteral: No
Molecule Type: Unknown	Topical: No	First In Class: No	Black Box: No
Chirality: No	Availability: No	Prodrug: No

Drug Indications

MESH ID	MESH Heading	EFO IDs	EFO Terms	Max Phase for Indication	References

Mechanisms of Action

Mechanism of Action	Action Type	target ID	Target Name	Target Type	Target Organism	Binding Site Name	References

Calculated Properties

Molecular Weight: 403.40	Molecular Weight (Monoisotopic): 403.1281	AlogP: 2.37	#Rotatable Bonds: 5
Polar Surface Area: 153.96	Molecular Species: ACID	HBA: 5	HBD: 5
#RO5 Violations: ┄	HBA (Lipinski): 9	HBD (Lipinski): 6	#RO5 Violations (Lipinski): 1
CX Acidic pKa: 4.16	CX Basic pKa: 2.52	CX LogP: 2.36	CX LogD: -0.56
Aromatic Rings: 4	Heavy Atoms: 30	QED Weighted: 0.34	Np Likeness Score: -0.53

References

1. Czyzyk DJ, Valhondo M, Deiana L, Tirado-Rives J, Jorgensen WL, Anderson KS.. (2019) Structure activity relationship towards design of cryptosporidium specific thymidylate synthase inhibitors., 183 [PMID:31536894] [10.1016/j.ejmech.2019.111673]

Source

Source(1):

Scientific Literature