protoporphyrin IX

Details

• Internal ID: 7a8bf2df-4aed-4704-9ea8-d5cbfaa4a344
• Taxonomy: Organoheterocyclic compounds > Tetrapyrroles and derivatives > Porphyrins
• IUPAC Name: 3-[18-(2-carboxyethyl)-8,13-bis(ethenyl)-3,7,12,17-tetramethyl-22,23-dihydroporphyrin-2-yl]propanoic acid
• 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)
• InChI Key: ZCFFYALKHPIRKJ-UHFFFAOYSA-N
• Popularity: 9,647 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₄H₃₄N₄O₄
• Molecular Weight: 562.70 g/mol
• Exact Mass: 562.25800558 g/mol
• Topological Polar Surface Area (TPSA): 132.00 Ų
• XlogP: 4.60
• Atomic LogP (AlogP): 7.42
• H-Bond Acceptor: 4
• H-Bond Donor: 4
• Rotatable Bonds: 8

Synonyms

• protoporphyrin
• 553-12-8
• Ooporphyrin
• Protoporpyrin IX
• Porphyrinogen IX
• Protoporphyrin IX disodium
• Kammerer's prophyrin
• ppIX
• H2ppIX
• Kammerer's porphyrin
• MLS001074731
• 3-[18-(2-carboxyethyl)-8,13-bis(ethenyl)-3,7,12,17-tetramethyl-22,23-dihydroporphyrin-2-yl]propanoic acid
• CHEBI:15430
• NSC2632
• NSC-2632
• 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
• 3,3'-(3,7,12,17-Tetramethyl-8,13-divinylporphine-2,18-diyl)di(propionic acid)
• protoporphyrin ix containing fe
• C2K325S808
• 2,18-Porphinedipropionic acid, 3,8,13,17-tetramethyl-7,12-divinyl-
• 21H,23H-Porphine-2,18-dipropanoic acid,7,12-diethenyl-3,8,13,17-tetramethyl-
• 3,3'-(3,7,12,17-tetramethyl-8,13-divinyl-21H,23H-porphine-2,18-diyl)-bis-propionic acid
• ProtoporphyrinIX
• 3,7,12,17-tetramethyl-8,13-divinylporphyrin-2,18-dipropanoic acid
• 7,12-diethenyl-3,8,13,17-tetramethylporphyrin-2,18-dipropanoic acid
• 3,3'-(3,8,13,17-tetramethyl-7,12-divinylporphyrin-2,18-diyl)dipropionic acid
• SR-01000076084
• NSC 2632
• EINECS 209-033-7
• Protoporphyrin-9
• UNII-C2K325S808
• protoporphyrin-"IX"
• Spectrum_001300
• Spectrum2_001016
• Spectrum3_001440
• Spectrum4_000419
• Spectrum5_001303
• cid_4971
• Lopac0_000973
• SCHEMBL25719
• BSPBio_003180
• KBioGR_000718
• KBioSS_001780
• Protoporphyrin IX, >=95%
• DivK1c_000074
• SCHEMBL805850
• SPECTRUM1501111
• SPBio_001171
• PROTOPORPHYRIN IX [MI]
• SCHEMBL3287054
• PROTOPORPHYRIN [WHO-DD]
• CHEMBL1325592
• CHEMBL1618319
• CHEMBL1907972
• CHEMBL1907974
• CHEMBL4463327
• DTXSID4048353
• SCHEMBL14552654
• BDBM51757
• HMS500D16
• KBio1_000074
• KBio2_001780
• KBio2_004348
• KBio2_006916
• KBio3_002400
• FEDYMSUPMFCVOD-UHFFFAOYSA-N
• KSFOVUSSGSKXFI-UHFFFAOYSA-N
• NINDS_000074
• OXTIQTUKEUGAPP-UJJXFSCMSA-N
• HMS1921F05
• HMS2271B12
• HMS3263C07
• Pharmakon1600-01501111
• HY-B1247
• Tox21_500973
• BDBM50523755
• CCG-39673
• NSC757839
• AKOS027320494
• CS-4849
• DB02285
• LP00973
• NSC-757839
• SDCCGMLS-0066712.P001
• SDCCGSBI-0050946.P004
• IDI1_000074
• NCGC00015844-01
• NCGC00015844-02
• NCGC00015844-03
• NCGC00015844-04
• NCGC00015844-05
• NCGC00015844-07
• NCGC00015844-08
• NCGC00015844-12
• NCGC00094273-01
• NCGC00094273-02
• NCGC00094273-03
• NCGC00162303-01
• NCGC00185010-01
• NCGC00261658-01
• AS-17461
• SBI-0050946.P003
• EU-0100973
• FT-0696783
• protoporphyrin IX [MeSH: protoporphyrin IX]
• 2, 3,8,13,17-tetramethyl-7,12-divinyl-
• C02191
• C75594
• P 8293
• AB00052204_02
• A870226
• Q619815
• SR-01000763747
• SR-01000076084-1
• SR-01000076084-4
• SR-01000076084-5
• SR-01000763747-3
• BRD-K26813314-001-04-4
• 1,3,5,8-TETRAMETHYL-2,4-DIVINYLPORPHINE-6,7-DIPROPIONATE
• 21H,18-dipropanoic acid, 7,12-diethenyl-3,8,13,17-tetramethyl-
• 3,3'-(3,7,12,17-tetramethyl-8,13-divinylporphine-2,18-diyl)di
• 2,18-Porphinedipropionic acid, 3,8,13,17-tetramethyl-7,12-divinyl- (8CI)
• 3,3'-(3,7,12,17-tetramethyl-8,13-divinyl-21H,23H-porphine-2,18-diyl)-bis-propionate
• 3,3'-(7,12-diethenyl-3,8,13,17-tetramethylporphyrin-2,18-diyl)dipropanoic acid
• 3-[(1Z,4Z,9Z,15Z)-18-(2-Carboxy-ethyl)-3,7,12,17-tetramethyl-8,13-divinyl-porphyrin-2-yl]-propionic acid
• 3-[(1Z,4Z,9Z,15Z)-18-(2-carboxyethyl)-3,7,12,17-tetramethyl-8,13-divinyl-21,23-dihydroporphyrin-2-yl]propanoic acid
• 3-[18-(2-carboxyethyl)-3,7,12,17-tetramethyl-8,13-divinyl-22,23-dihydroporphin-2-yl]propionic acid
• 3-[18-(2-carboxyethyl)-3,8,13,17-tetramethyl-7,12-divinyl-21,23-dihydroporphyrin-2-yl]propanoic acid
• 3-[8,13-bis(ethenyl)-18-(3-hydroxy-3-oxopropyl)-3,7,12,17-tetramethyl-22,23-dihydroporphyrin-2-yl]propanoic acid

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9095	90.95%
Caco-2	-	0.8399	83.99%
Blood Brain Barrier	+	0.6250	62.50%
Human oral bioavailability	-	0.5286	52.86%
Subcellular localzation	Mitochondria	0.6909	69.09%
OATP2B1 inhibitior	-	0.7125	71.25%
OATP1B1 inhibitior	-	0.6293	62.93%
OATP1B3 inhibitior	+	0.9447	94.47%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	+	0.9037	90.37%
P-glycoprotein inhibitior	+	0.7504	75.04%
P-glycoprotein substrate	-	0.7935	79.35%
CYP3A4 substrate	-	0.5335	53.35%
CYP2C9 substrate	-	0.8071	80.71%
CYP2D6 substrate	-	0.8933	89.33%
CYP3A4 inhibition	-	0.8758	87.58%
CYP2C9 inhibition	+	0.7852	78.52%
CYP2C19 inhibition	-	0.9026	90.26%
CYP2D6 inhibition	-	0.7023	70.23%
CYP1A2 inhibition	+	0.9107	91.07%
CYP2C8 inhibition	+	0.5128	51.28%
CYP inhibitory promiscuity	-	0.8589	85.89%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.8600	86.00%
Carcinogenicity (trinary)	Non-required	0.5907	59.07%
Eye corrosion	-	0.9866	98.66%
Eye irritation	-	0.8617	86.17%
Skin irritation	-	0.7609	76.09%
Skin corrosion	-	0.9190	91.90%
Ames mutagenesis	-	0.6000	60.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7429	74.29%
Micronuclear	+	0.5200	52.00%
Hepatotoxicity	+	0.7750	77.50%
skin sensitisation	-	0.8475	84.75%
Respiratory toxicity	+	0.7778	77.78%
Reproductive toxicity	+	0.7778	77.78%
Mitochondrial toxicity	+	0.7875	78.75%
Nephrotoxicity	-	0.9376	93.76%
Acute Oral Toxicity (c)	III	0.5890	58.90%
Estrogen receptor binding	+	0.8907	89.07%
Androgen receptor binding	+	0.6738	67.38%
Thyroid receptor binding	+	0.6169	61.69%
Glucocorticoid receptor binding	+	0.6793	67.93%
Aromatase binding	+	0.6392	63.92%
PPAR gamma	+	0.6623	66.23%
Honey bee toxicity	-	0.9541	95.41%
Biodegradation	-	0.9250	92.50%
Crustacea aquatic toxicity	-	0.8100	81.00%
Fish aquatic toxicity	+	0.9351	93.51%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	97.11%	98.95%
CHEMBL4040	P28482	MAP kinase ERK2	94.16%	83.82%
CHEMBL1781	P11387	DNA topoisomerase I	91.06%	97.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	90.11%	99.17%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	89.45%	96.09%
CHEMBL3401	O75469	Pregnane X receptor	88.11%	94.73%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.69%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.42%	95.56%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	82.92%	99.23%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	82.51%	90.71%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	81.90%	96.95%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	81.17%	96.90%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	80.89%	96.00%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	80.25%	93.03%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 4971
• LOTUS: LTS0089084
• wikiData: Q619815