4-[2-(8-Hydroxy-7,8-dihydro-6H-imidazo[4,5-d][1,3]diazepin-3-yl)-ethyl]-5,6,7,8-tetrahydro-naphthalene-2-carboxylic acid benzyl ester

Names and Identifiers

Canonical SMILES: O=C(OCc1ccccc1)c1cc2c(c(CCn3cnc4c3NC=NCC4O)c1)CCCC2

Standard InChI: InChI=1S/C26H28N4O3/c31-23-14-27-16-28-25-24(23)29-17-30(25)11-10-20-13-21(12-19-8-4-5-9-22(19)20)26(32)33-15-18-6-2-1-3-7-18/h1-3,6-7,12-13,16-17,23,31H,4-5,8-11,14-15H2,(H,27,28)

Standard InChI Key: XFACVNHRKQEKLU-UHFFFAOYSA-N

Molfile:

     RDKit          2D

 33 37  0  0  0  0  0  0  0  0999 V2000
    2.3167   -2.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7542   -2.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5667   -1.6917    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2875   -2.3375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7167   -3.2417    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1625   -1.7542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8917   -2.6667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4250   -2.3667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8542   -2.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3750   -3.5667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8542   -3.2667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7292   -2.3375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8917   -3.2667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3792   -2.3542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2292   -3.5792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -3.4042    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8125   -2.6542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9500   -2.6792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3292   -2.3500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4417   -1.7667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9417   -3.2792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3875   -1.8292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4375   -2.8542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4667   -3.5792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3667   -4.1667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3292   -3.5667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4625   -4.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9792   -3.2792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8417   -4.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3292   -4.1625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5000   -3.5792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9792   -4.4917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5000   -4.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  1  1  0
  4  2  1  0
  5  2  1  0
  6  3  2  0
  7 14  2  0
  8  7  1  0
  9 19  1  0
 10 11  1  0
 11  9  2  0
 12  1  1  0
 13  7  1  0
 14  9  1  0
 15  5  1  0
 16 23  1  0
 17  4  1  0
 18  8  1  0
 19 17  1  0
 20  8  2  0
 21 18  1  0
 22 12  1  0
 23 12  1  0
 24 21  1  0
 25 10  1  0
 26 11  1  0
 27 24  2  0
 28 24  1  0
 29 30  1  0
 30 26  1  0
 31 28  2  0
 32 27  1  0
 33 31  1  0
  6  4  1  0
 15 16  2  0
 13 10  2  0
 25 29  1  0
 33 32  2  0
M  END

Alternative Forms

Parent:

ALA157723
4-[2-(8-Hydroxy-7,8-dihydro-6H-imidazo[4,5-d][1,3]diazepin-3-yl)-ethyl]-5,6,7,8-tetrahydro-naphthalene-2-carboxylic acid benzyl ester

Associated Targets(Human)

AMPD3 Tchem AMP deaminase 3 (49 Activities)

Discover Target: AMPD3

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

Associated Targets(non-human)

ADA Adenosine deaminase (739 Activities)

Discover Target: ADA

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: Small molecule	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

Biocomponents

Calculated Properties

Molecular Weight: 444.54	Molecular Weight (Monoisotopic): 444.2161	AlogP: 3.85	#Rotatable Bonds: 6
Polar Surface Area: 88.74	Molecular Species: NEUTRAL	HBA: 7	HBD: 2
#RO5 Violations: ┄	HBA (Lipinski): 7	HBD (Lipinski): 2	#RO5 Violations (Lipinski): ┄
CX Acidic pKa: 13.06	CX Basic pKa: 6.50	CX LogP: 4.14	CX LogD: 4.09
Aromatic Rings: 3	Heavy Atoms: 33	QED Weighted: 0.56	Np Likeness Score: -0.07

References

1. Kasibhatla SR, Bookser BC, Xiao W, Erion MD.. (2001) AMP deaminase inhibitors. 5. Design, synthesis, and SAR of a highly potent inhibitor series., 44 (4): [PMID:11170651] [10.1021/jm000355t]

Source

Source(1):

Scientific Literature