4-{3-[4-amino(imino)methylphenoxy]propoxy}phenyl-iminomethanamine

ID: ALA23013

Chembl Id: CHEMBL23013

Cas Number: 104-32-5

PubChem CID: 64949

Max Phase: Phase

Molecular Formula: C17H20N4O2

Molecular Weight: 312.37

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Propamidine | M&B 782 [AS ISETHIONATE] | Propamidine|104-32-5|Propamidinum|Propamidina|4,4'-(Trimethylenedioxy)dibenzamidine|Benzenecarboximidamide, 4,4'-[1,3-propanediylbis(oxy)]bis-|1,3-BIS(AMIDINOPHENOXY)PROPANE|Propamide dihydrochloride|4,4'-(1,3-Propanediylbis(oxy))bis-benzenecarboximidamide|4-[3-(4-carbamimidoylphenoxy)propoxy]benzenecarboximidamide|DTXSID6048674|CHEBI:87462|GNF-PF-3839|4,4'-(propane-1,3-diylbis(oxy))dibenzimidamide|Propamidine (INN)|M&B 782 [AS ISETHIONATE]|G20G12V769|NCGShow More⌵

Canonical SMILES:  N=C(N)c1ccc(OCCCOc2ccc(C(=N)N)cc2)cc1

Standard InChI:  InChI=1S/C17H20N4O2/c18-16(19)12-2-6-14(7-3-12)22-10-1-11-23-15-8-4-13(5-9-15)17(20)21/h2-9H,1,10-11H2,(H3,18,19)(H3,20,21)

Standard InChI Key:  WTFXJFJYEJZMFO-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA23013

   PROPAMIDINE

2. Alternative Forms:

   

   ALA23013

   Benzamidine, 4,4'-(trimethylenedioxy)di-, dihydrochloride

Molecule Features

Natural Product: Yes

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: Yes

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 312.37

Molecular Weight (Monoisotopic): 312.1586

AlogP: 2.10

#Rotatable Bonds: 8

Polar Surface Area: 118.20

Molecular Species: BASE

HBA: 4

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 12.13

CX LogP: 1.36

CX LogD: -3.46

Aromatic Rings: 2

Heavy Atoms: 23

QED Weighted: 0.34

Np Likeness Score: -0.20

References

1. Johnson HA, Thomas NR..  (2002)  Polyhydroxylated azepanes as new motifs for DNA minor groove binding agents.,  12  (2): [PMID:11755363] [10.1016/s0960-894x(01)00719-3]

2. So SS, Karplus M..  (1997)  Three-dimensional quantitative structure-activity relationships from molecular similarity matrices and genetic neural networks. 2. Applications.,  40  (26): [PMID:9435905] [10.1021/jm970488n]

3. Cory M, Tidwell RR, Fairley TA..  (1992)  Structure and DNA binding activity of analogues of 1,5-bis(4-amidinophenoxy)pentane (pentamidine),  35  (3): [PMID:1738139] [10.1021/jm00081a003]

4. Queener SF..  (1995)  New drug developments for opportunistic infections in immunosuppressed patients: Pneumocystis carinii.,  38  (24): [PMID:7490723] [10.1021/jm00024a001]

5. Acharya BN, Saraswat D, Kaushik MP..  (2008)  Pharmacophore based discovery of potential antimalarial agent targeting haem detoxification pathway.,  43  (12): [PMID:18395298] [10.1016/j.ejmech.2008.02.005]

6. Prado-Prado FJ, García-Mera X, González-Díaz H..  (2010)  Multi-target spectral moment QSAR versus ANN for antiparasitic drugs against different parasite species.,  18  (6): [PMID:20185316] [10.1016/j.bmc.2010.01.068]

7. USP Dictionary of USAN and International Names (2010 edition) and USAN registrations 2007-date, 

8. PubChem BioAssay data set, 

9. Parrish RF, Straus JW, Paulson JD, Polakoski KL, Tidwell RR, Geratz JD, Stevens FM..  (1978)  Structure-activity relationships for the inhibition of acrosin by benzamidine derivatives.,  21  (11): [PMID:722718] [10.1021/jm00209a008]

10. Berger ML, Maciejewska D, Vanden Eynde JJ, Mottamal M, Żabiński J, Kaźmierczak P, Rezler M, Jarak I, Piantanida I, Karminski-Zamola G, Mayence A, Rebernik P, Kumar A, Ismail MA, Boykin DW, Huang TL..  (2015)  Pentamidine analogs as inhibitors of [(3)H]MK-801 and [(3)H]ifenprodil binding to rat brain NMDA receptors.,  23  (15): [PMID:26117647] [10.1016/j.bmc.2015.06.012]

11. WHO Anatomical Therapeutic Chemical Classification, 

12. Zhang J, Qian K, Yan C, He M, Jassim BA, Ivanov I, Zheng YG..  (2017)  Discovery of Decamidine as a New and Potent PRMT1 Inhibitor.,  8  (2): [PMID:28649316] [10.1039/C6MD00573J]

13. Unpublished dataset, 

14. Peiffer AL, Garlick JM, Wu Y, Wotring JW, Arora S, Harmata AS, Bochar DA, Stephenson CJ, Soellner MB, Sexton JZ, Brooks CL, Mapp AK..  (2023)  TMPRSS2 Inhibitor Discovery Facilitated through an In Silico and Biochemical Screening Platform.,  14  (6): [PMID:37284689] [10.1021/acsmedchemlett.3c00035]

Source

Source(5):

• Scientific Literature
• PubChem BioAssays
• Clinical Candidates
• USP Dictionary of USAN and International Drug Names
• WHO Anatomical Therapeutic Chemical Classification