Pheophorbide a

Details

• Internal ID: c3a9ce14-1a34-4254-a981-9c27f028d3c6
• Taxonomy: Organoheterocyclic compounds > Tetrapyrroles and derivatives
• IUPAC Name: 3-[(3R,21S,22S)-16-ethenyl-11-ethyl-4-hydroxy-3-methoxycarbonyl-12,17,21,26-tetramethyl-7,23,24,25-tetrazahexacyclo[18.2.1.15,8.110,13.115,18.02,6]hexacosa-1,4,6,8(26),9,11,13(25),14,16,18(24),19-undecaen-22-yl]propanoic acid
• SMILES (Canonical): CCC1=C(C2=NC1=CC3=C(C4=C(C(C(=C5C(C(C(=CC6=NC(=C2)C(=C6C)C=C)N5)C)CCC(=O)O)C4=N3)C(=O)OC)O)C)C
• SMILES (Isomeric): CCC1=C(C2=NC1=CC3=C(C4=C([C@@H](C(=C5[C@H]([C@@H](C(=CC6=NC(=C2)C(=C6C)C=C)N5)C)CCC(=O)O)C4=N3)C(=O)OC)O)C)C
• InChI: InChI=1S/C35H36N4O5/c1-8-19-15(3)22-12-24-17(5)21(10-11-28(40)41)32(38-24)30-31(35(43)44-7)34(42)29-18(6)25(39-33(29)30)14-27-20(9-2)16(4)23(37-27)13-26(19)36-22/h8,12-14,17,21,31,38,42H,1,9-11H2,2-7H3,(H,40,41)/t17-,21-,31+/m0/s1
• InChI Key: RKEBXTALJSALNU-LDCXZXNSSA-N
• Popularity: 300 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₅H₃₆N₄O₅
• Molecular Weight: 592.70 g/mol
• Exact Mass: 592.26857026 g/mol
• Topological Polar Surface Area (TPSA): 133.00 Ų
• XlogP: 2.70

Synonyms

• 15664-29-6
• Phaeophorbid a
• Phaeophorbid-a
• IA2WNI2HO2
• 3-Phorbinepropanoic acid, 9-ethenyl-14-ethyl-21-(methoxycarbonyl)-4,8,13,18-tetramethyl-20-oxo-, (3S,4S,21R)-
• CHEBI:38257
• 3-[(3R,21S,22S)-16-ethenyl-11-ethyl-4-hydroxy-3-methoxycarbonyl-12,17,21,26-tetramethyl-7,23,24,25-tetrazahexacyclo[18.2.1.15,8.110,13.115,18.02,6]hexacosa-1,4,6,8(26),9,11,13(25),14,16,18(24),19-undecaen-22-yl]propanoic acid
• Phaeophorbide A
• (2(2)R,17S,18S)-7-ethyl-2(1),2(2),17,18-tetrahydro-2(2)-(methoxycarbonyl)-3,8,13,17-tetramethyl-2(1)-oxo-12-ethenylcyclopenta[at]porphyrin-18-propanoic acid
• (3S,4S,21R)-9-ethenyl-14-ethyl-21-(methoxycarbonyl)-4,8,13,18-tetramethyl-20-oxo-3-phorbinepropanoic acid
• 3-[(3S,4S,21R)-14-ethyl-21-(methoxycarbonyl)-4,8,13,18-tetramethyl-20-oxo-9-vinylphorbin-3-yl]propanoic acid
• EINECS 239-738-5
• UNII-IA2WNI2HO2
• phaeophorbide
• PhaeophorbideA
• CCRIS 8091
• Pheophorbide a'
• 13-epi-Phaeophorbide a
• pheophorbide a, AldrichCPR
• SCHEMBL56439
• SCHEMBL579034
• CHEMBL510103
• CHEMBL2006244
• DTXSID10884550
• NSFSLUUZQIAOOX-LDCXZXNSSA-N
• Pheophorbide-a, >=90% (HPLC)
• NSC-75783
• (3S-(3alpha,4beta,21beta))-14-Ethyl-21-(methoxycarbonyl)-4,8,13,18-tetramethyl-20-oxo-9-vinylphorbine-3-propionic acid
• NCI60_041663
• HY-125665
• CS-0092948
• C18021
• Q63370
• Pheophorbide A (>80%) (mixture of diastereomers)
• (3S,4S)-9-Ethenyl-14-ethyl-21-(methoxycarbonyl)-4,8,13,18-tetramethyl-20-oxo-3-phorbinepropanoic acid
• 3-[(3R,8Z,13Z,19Z,21S,22S)-11-Ethyl-3-(methoxycarbonyl)-12,17,21,26-tetramethyl-4-oxo-16-vinyl-7,23,24,25-tetraazahexacyclo[18.2.1.1~5,8~.1~10,13~.1~15,18~.0~2,6~]hexacosa-1(23),2(6),5(26),8,10(25),11,13,15,17,19-decaen-22-yl]propanoic acid

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
No predicted properties yet!

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.86%	96.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	98.21%	85.14%
CHEMBL2581	P07339	Cathepsin D	96.56%	98.95%
CHEMBL221	P23219	Cyclooxygenase-1	96.51%	90.17%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	94.18%	94.45%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	92.85%	91.11%
CHEMBL230	P35354	Cyclooxygenase-2	87.60%	89.63%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	87.48%	96.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	87.47%	99.17%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	86.72%	96.90%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	82.50%	93.03%
CHEMBL202	P00374	Dihydrofolate reductase	82.15%	89.92%
CHEMBL255	P29275	Adenosine A2b receptor	81.73%	98.59%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	80.73%	99.23%

Plants that contains it

• Artemisia capillaris
• Berberis fendleri
• Berberis fremontii
• Camellia sinensis
• Ginkgo biloba
• Isatis tinctoria
• Palicourea acuminata
• Saussurea medusa
• Solanum pseudocapsicum
• Stratiotes aloides

Cross-Links

• PubChem: 253193
• LOTUS: LTS0159450
• wikiData: Q104253072