5,10,15,20-tetrakis(m-hydroxyphenyl)chlorin

ID: ALA500576

Max Phase: Preclinical

Molecular Formula: C44H32N4O4

Molecular Weight: 680.76

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Oc1cccc(-c2c3nc(c(-c4cccc(O)c4)c4ccc([nH]4)c(-c4cccc(O)c4)c4nc(c(-c5cccc(O)c5)c5ccc2[nH]5)CC4)C=C3)c1

Standard InChI:  InChI=1S/C44H32N4O4/c49-29-9-1-5-25(21-29)41-33-13-15-35(45-33)42(26-6-2-10-30(50)22-26)37-17-19-39(47-37)44(28-8-4-12-32(52)24-28)40-20-18-38(48-40)43(36-16-14-34(41)46-36)27-7-3-11-31(51)23-27/h1-17,19,21-24,46-47,49-52H,18,20H2/b41-33-,41-34-,42-35-,42-37-,43-36-,43-38-,44-39-,44-40-

Standard InChI Key:  LYPFDBRUNKHDGX-LWQDQPMZSA-N

Molfile:  

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M  END

Alternative Forms

1. Parent:

   

   ALA500576

   ---

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: 680.76

Molecular Weight (Monoisotopic): 680.2424

AlogP: 9.76

#Rotatable Bonds: 4

Polar Surface Area: 138.28

Molecular Species: NEUTRAL

HBA: 6

HBD: 6

#RO5 Violations: 3

HBA (Lipinski): 8

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 9.12

CX Basic pKa: 5.79

CX LogP: 9.21

CX LogD: 9.20

Aromatic Rings: 7

Heavy Atoms: 52

QED Weighted: 0.11

Np Likeness Score: 0.15

References

1. Hirohara S, Oka C, Totani M, Obata M, Yuasa J, Ito H, Tamura M, Matsui H, Kakiuchi K, Kawai T, Kawaichi M, Tanihara M..  (2015)  Synthesis, Photophysical Properties, and Biological Evaluation of trans-Bisthioglycosylated Tetrakis(fluorophenyl)chlorin for Photodynamic Therapy.,  58  (21): [PMID:26457363] [10.1021/acs.jmedchem.5b01262]

2. Marydasan B, Madhuri B, Cherukommu S, Jose J, Viji M, Karunakaran SC, Chandrashekar TK, Rao KS, Rao CM, Ramaiah D..  (2018)  In Vitro and In Vivo Demonstration of Human-Ovarian-Cancer Necrosis through a Water-Soluble and Near-Infrared-Absorbing Chlorin.,  61  (11): [PMID:29767974] [10.1021/acs.jmedchem.8b00460]

3. Bernhard Ellinger, Denisa Bojkova, Andrea Zaliani, Jindrich Cinatl, Carsten Claussen, Sandra Westhaus, Jeanette Reinshagen, Maria Kuzikov, Markus Wolf, Gerd Geisslinger, Philip Gribbon, Sandra Ciesek.  (2020)  Identification of inhibitors of SARS-CoV-2 in-vitro cellular toxicity in human (Caco-2) cells using a large scale drug repurposing collection,  [10.21203/rs.3.rs-23951/v1]

4. Sobotta L, Skupin-Mrugalska P, Piskorz J, Mielcarek J..  (2019)  Porphyrinoid photosensitizers mediated photodynamic inactivation against bacteria.,  175  [PMID:31096157] [10.1016/j.ejmech.2019.04.057]

5. Gao YH, Lovreković V, Kussayeva A, Chen DY, Margetić D, Chen ZL..  (2019)  The photodynamic activities of dimethyl 13¹-[2-(guanidinyl)ethylamino] chlorin e₆ photosensitizers in A549 tumor.,  177  [PMID:31132530] [10.1016/j.ejmech.2019.05.050]

6. Maria Kuzikov, Elisa Costanzi, Jeanette Reinshagen, Francesca Esposito, Laura Vangeel, Markus Wolf, Bernhard Ellinger, Carsten Claussen, Gerd Geisslinger, Angela Corona, Daniela Iaconis, Carmine Talarico, Candida Manelfi, Rolando Cannalire, Giulia Rossetti, Jonas Gossen, Simone Albani, Francesco Musiani, Katja Herzog, Yang Ye, Barbara Giabbai, Nicola Demitri, Dirk Jochmans, Steven De Jonghe, Jasper Rymenants, Vincenzo Summa, Enzo Tramontano, Andrea R. Beccari, Pieter Leyssen, Paola Storici, Johan Neyts, Philip Gribbon, and Andrea Zaliani.  (2020)  Identification of inhibitors of SARS-Cov2 M-Pro enzymatic activity using a small molecule repurposing screen,  [10.6019/CHEMBL4495564]

7. Andrea Zaliani, Laura Vangeel, Jeanette Reinshagen, Daniela Iaconis, Maria Kuzikov, Oliver Keminer, Markus Wolf, Bernhard Ellinger, Francesca Esposito, Angela Corona, Enzo Tramontano, Candida Manelfi, Katja Herzog, Dirk Jochmans, Steven De Jonghe, Winston Chiu, Thibault Francken, Joost Schepers, Caroline Collard, Kayvan Abbasi, Carsten Claussen , Vincenzo Summa, Andrea R. Beccari, Johan Neyts, Philip Gribbon and Pieter Leyssen.  (2020)  Cytopathic SARS-Cov2 screening on VERO-E6 cells in a large repurposing effort,  [10.6019/CHEMBL4495565]

8. Gao YH,Li MY,Sajjad F,Wang JH,Meharban F,Gadoora MA,Yan YJ,Nyokong T,Chen ZL.  (2020)  Synthesis and pharmacological evaluation of chlorin derivatives for photodynamic therapy of cholangiocarcinoma.,  189  [PMID:31945666] [10.1016/j.ejmech.2020.112049]

9. Sun YM,Jiang X,Liu ZY,Liu LG,Liao YH,Zeng L,Ye Y,Liu HY.  (2020)  Hydroxy-corrole and its gallium(III) complex as new photosensitizer for photodynamic therapy against breast carcinoma.,  208  [PMID:32916313] [10.1016/j.ejmech.2020.112794]

10. Bernhard Ellinger, Justus Dick, Vanessa Lage-Rupprecht, Bruce Schultz, Andrea Zaliani, Marcin Namysl, Stephan Gebel, Ole Pless, Jeanette Reinshagen, Christian Ebeling, Alexander Esser, Marc Jacobs, Carsten Claussen, and Martin Hofmann-Apitius.  (2021)  HDAC6 screening dataset using tau-based substrate in an enzymatic assay yields selective inhibitors and activators,  [10.6019/CHEMBL4808148]

11. Janas K, Boniewska-Bernacka E, Dyrda G, Słota R..  (2021)  Porphyrin and phthalocyanine photosensitizers designed for targeted photodynamic therapy of colorectal cancer.,  30  [PMID:33341498] [10.1016/j.bmc.2020.115926]

12. Voss S, Nitsche C..  (2021)  Targeting the protease of West Nile virus.,  12  (8.0): [PMID:34458734] [10.1039/D1MD00080B]

Source

Source(3):

• Scientific Literature
• SARS-CoV-2 Screening Data 2020-21
• Fraunhofer HDAC6