Details of the Drug

General Information of Drug (ID: DMWYE7A)

Drug Name

Protoporphyrin IX

Synonyms

protoporphyrin IX; protoporphyrin; 553-12-8; Ooporphyrin; Protoporpyrin IX; Porphyrinogen IX; Protoporphyrin IX disodium; Kammerer's prophyrin; ppIX; Protoporphyrin IX (VAN); H2ppIX; Kammerer's porphyrin; MLS001074731; UNII-C2K325S808; NSC2632; NSC 2632; EINECS 209-033-7; 3,7,12,17-Tetramethyl-8,13-divinyl-2,18-porphinedipropionic acid; SMR000127405; 21H,23H-Porphine-2,18-dipropanoic acid, 7,12-diethenyl-3,8,13,17-tetramethyl-; CHEMBL267548; CHEBI:15430; C34H34N4O4

Indication

Disease Entry	ICD 11	Status	REF
Discovery agent	N.A.	Investigative	[1]
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Drug Type

Small molecular drug

Structure

3D MOL

2D MOL

#Ro5 Violations (Lipinski): 1

Molecular Weight (mw)

562.7

Logarithm of the Partition Coefficient (xlogp)

4.6

Rotatable Bond Count (rotbonds)

8

Hydrogen Bond Donor Count (hbonddonor)

4

Hydrogen Bond Acceptor Count (hbondacc)

6

Chemical Identifiers

Formula: C34H34N4O4
IUPAC Name: 3-[18-(2-carboxyethyl)-8,13-bis(ethenyl)-3,7,12,17-tetramethyl-22,23-dihydroporphyrin-2-yl]propanoic acid
Canonical SMILES: CC1=C(C2=CC3=NC(=CC4=NC(=CC5=C(C(=C(N5)C=C1N2)C=C)C)C(=C4CCC(=O)O)C)C(=C3C)CCC(=O)O)C=C
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/h7-8,13-16,35-36H,1-2,9-12H2,3-6H3,(H,39,40)(H,41,42)
InChIKey: ZCFFYALKHPIRKJ-UHFFFAOYSA-N

Cross-matching ID

PubChem CID: 4971
ChEBI ID: CHEBI:15430
CAS Number: 553-12-8
DrugBank ID: DB02285
TTD ID: D0AF3A
VARIDT ID: DR01454

Molecular Interaction Atlas of This Drug

Drug Therapeutic Target (DTT)

DTT Name	DTT ID	UniProt ID	MOA	REF
Glutathione-dependent PGD synthase (HPGDS)	TTCYE56	HPGDS_HUMAN	Inhibitor	[1]

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Drug Transporter (DTP)

DTP Name	DTP ID	UniProt ID	MOA	REF
Breast cancer resistance protein (ABCG2)	DTI7UX6	ABCG2_HUMAN	Substrate	[2]

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Drug Off-Target (DOT)

DOT Name	DOT ID	UniProt ID	Interaction	REF
5-aminolevulinate synthase, erythroid-specific, mitochondrial (ALAS2)	OTJXOUCL	HEM0_HUMAN	Gene/Protein Processing	[3]
72 kDa type IV collagenase (MMP2)	OT5NIWA2	MMP2_HUMAN	Gene/Protein Processing	[4]
Albumin (ALB)	OTVMM513	ALBU_HUMAN	Protein Interaction/Cellular Processes	[5]
Apoptosis regulator BAX (BAX)	OTAW0V4V	BAX_HUMAN	Gene/Protein Processing	[6]
Apoptosis regulator Bcl-2 (BCL2)	OT9DVHC0	BCL2_HUMAN	Gene/Protein Processing	[6]
Baculoviral IAP repeat-containing protein 2 (BIRC2)	OTFXFREP	BIRC2_HUMAN	Gene/Protein Processing	[7]
Caspase-3 (CASP3)	OTIJRBE7	CASP3_HUMAN	Protein Interaction/Cellular Processes	[6]
Caspase-8 (CASP8)	OTA8TVI8	CASP8_HUMAN	Gene/Protein Processing	[8]
Copper-transporting ATPase 2 (ATP7B)	OTPWLNCO	ATP7B_HUMAN	Biotransformations	[9]
Corticoliberin (CRH)	OT2MOC4T	CRF_HUMAN	Protein Interaction/Cellular Processes	[10]

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Molecular Interaction Atlas (MIA)

MIA Detail

Jump to Detail Molecular Interaction Atlas of This Drug

Molecular Expression Atlas of This Drug

The Studied Disease

Discovery agent

ICD Disease Classification

N.A.

Molecule Name	Molecule Type	Gene Name	p-value	Fold-Change	Z-score
Glutathione-dependent PGD synthase (HPGDS)	DTT	HPGDS	1.63E-05	0.34	0.71
Breast cancer resistance protein (ABCG2)	DTP	BCRP	9.45E-01	-5.34E-02	-9.01E-02

Molecular Expression Atlas (MEA)

MEA Detail

Jump to Detail Molecular Expression Atlas of This Drug

References

1	Inhibition of glutathione-S-transferase from Plasmodium yoelii by protoporphyrin IX, cibacron blue and menadione: implications and therapeutic bene... Parasitol Res. 2008 Mar;102(4):805-7.
2	Pharmacogenomic importance of ABCG2. Pharmacogenomics. 2008 Aug;9(8):1005-9.
3	Changes in DNA methylation of erythroid-specific genes in K562 cells exposed to phenol and hydroquinone. Toxicology. 2013 Oct 4;312:108-14. doi: 10.1016/j.tox.2013.08.007. Epub 2013 Aug 20.
4	Structural requirements within protoporphyrin IX in the inhibition of heat shock protein 90. Chem Biol Interact. 2013 Jun 25;204(1):49-57. doi: 10.1016/j.cbi.2013.04.006. Epub 2013 Apr 24.
5	The three recombinant domains of human serum albumin. Structural characterization and ligand binding properties. J Biol Chem. 1999 Oct 8;274(41):29303-10. doi: 10.1074/jbc.274.41.29303.
6	Induction of heme oxygenase-1 with hemin alleviates cisplatin-induced reproductive toxicity in male rats and enhances its cytotoxicity in prostate cancer cell line. Toxicol Lett. 2016 Dec 15;264:38-50. doi: 10.1016/j.toxlet.2016.10.019. Epub 2016 Nov 1.
7	Upregulation of heme oxygenase-1 and p21 confers resistance to apoptosis in human gastric cancer cells. Oncogene. 2004 Jan 15;23(2):503-13. doi: 10.1038/sj.onc.1207173.
8	Metalloporphyrins inactivate caspase-3 and -8. FASEB J. 2005 Aug;19(10):1272-9. doi: 10.1096/fj.04-3259com.
9	Regulation of heme synthesis and proteasomal activity by copper: possible implications for Wilson's disease. J Environ Pathol Toxicol Oncol. 2009;28(3):209-21.
10	Evidence for a functional link between the heme oxygenase-carbon monoxide pathway and corticotropin-releasing hormone release from primary cultures of human trophoblast cells. J Clin Endocrinol Metab. 2001 Jan;86(1):317-23. doi: 10.1210/jcem.86.1.7091.