3-[(1Z,4Z,9Z,15Z)-18-(2-Carboxy-ethyl)-3,7,12,17-tetramethyl-8,13-divinyl-porphyrin-2-yl]-propionic acid

ID: ALA267548

Chembl Id: CHEMBL267548

Max Phase: Preclinical

Molecular Formula: C34H34N4O4

Molecular Weight: 562.67

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C=CC1=C(C)c2cc3nc(cc4[nH]c(cc5[nH]c(cc1n2)c(C)c5C=C)c(C)c4CCC(=O)O)C(CCC(=O)O)=C3C

Standard InChI:  InChI=1S/C34H34N4O4/c1-7-21-17(3)25-13-26-19(5)23(9-11-33(39)40)31(37-26)16-32-24(10-12-34(41)42)20(6)28(38-32)15-30-22(8-2)18(4)27(36-30)14-29(21)35-25/h7-8,13-16,36,38H,1-2,9-12H2,3-6H3,(H,39,40)(H,41,42)/b25-13-,26-13-,27-14-,28-15-,29-14-,30-15-,31-16-,32-16-

Standard InChI Key:  OXTIQTUKEUGAPP-UJJXFSCMSA-N

Alternative Forms

1. Parent:

   

   ALA267548

   PROTOPORPHYRIN

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

Calculated Properties

Molecular Weight: 562.67

Molecular Weight (Monoisotopic): 562.2580

AlogP: 7.50

#Rotatable Bonds: 8

Polar Surface Area: 131.96

Molecular Species: ACID

HBA: 4

HBD: 4

#RO5 Violations: 2

HBA (Lipinski): 8

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 3.62

CX Basic pKa: 5.03

CX LogP: 6.88

CX LogD: 2.33

Aromatic Rings: 3

Heavy Atoms: 42

QED Weighted: 0.22

Np Likeness Score: 0.64

References

1. Debnath AK, Jiang S, Strick N, Lin K, Haberfield P, Neurath AR..  (1994)  Three-dimensional structure-activity analysis of a series of porphyrin derivatives with anti-HIV-1 activity targeted to the V3 loop of the gp120 envelope glycoprotein of the human immunodeficiency virus type 1.,  37  (8): [PMID:8164251] [10.1021/jm00034a007]

2. DeCamp DL, Babé LM, Salto R, Lucich JL, Koo MS, Kahl SB, Craik CS..  (1992)  Specific inhibition of HIV-1 protease by boronated porphyrins.,  35  (18): [PMID:1527792] [10.1021/jm00096a020]

3. PubChem BioAssay data set, 

4. PubChem BioAssay data set, 

5. PubChem BioAssay data set, 

6. PubChem BioAssay data set, 

7. PubChem BioAssay data set, 

8. PubChem BioAssay data set, 

9. PubChem BioAssay data set, 

10. PubChem BioAssay data set, 

11. De Bruyn T, van Westen GJ, Ijzerman AP, Stieger B, de Witte P, Augustijns PF, Annaert PP..  (2013)  Structure-based identification of OATP1B1/3 inhibitors.,  83  (6): [PMID:23571415] [10.1124/mol.112.084152]

12. Mölzer C, Huber H, Steyrer A, Ziesel GV, Wallner M, Hong HT, Blanchfield JT, Bulmer AC, Wagner KH..  (2013)  Bilirubin and related tetrapyrroles inhibit food-borne mutagenesis: a mechanism for antigenotoxic action against a model epoxide.,  76  (10): [PMID:24156291] [10.1021/np4005807]

13. McEwan C, Nesbitt H, Nicholas D, Kavanagh ON, McKenna K, Loan P, Jack IG, McHale AP, Callan JF..  (2016)  Comparing the efficacy of photodynamic and sonodynamic therapy in non-melanoma and melanoma skin cancer.,  24  (13): [PMID:27234890] [10.1016/j.bmc.2016.05.015]

Source

Source(2):

• Scientific Literature
• PubChem BioAssays