Pheophorbide a

Details

Physical and Chemical Properties

Synonyms

2D Structure

3D Structure

ADMET Properties

Targets (proven and/or predicted)

Plants that contains it

Cross-Links

Details

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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

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Molecular Formula	C₃₅H₃₆N₄O₅
Molecular Weight	592.70 g/mol
Exact Mass	592.26857026 g/mol
Topological Polar Surface Area (TPSA)	133.00 Å²
XlogP	2.70
Atomic LogP (AlogP)	6.11
H-Bond Acceptor	8
H-Bond Donor	3
Rotatable Bonds	6

Synonyms

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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

There are more than 10 synonyms. If you wish to see them all click here.

2D Structure

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3D Structure

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ADMET Properties (via admetSAR 2)

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Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9438	94.38%
Caco-2	-	0.8235	82.35%
Blood Brain Barrier	+	0.7250	72.50%
Human oral bioavailability	-	0.5143	51.43%
Subcellular localzation	Mitochondria	0.6855	68.55%
OATP2B1 inhibitior	-	0.5699	56.99%
OATP1B1 inhibitior	+	0.7950	79.50%
OATP1B3 inhibitior	+	0.9207	92.07%
MATE1 inhibitior	-	0.8400	84.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	+	0.9572	95.72%
P-glycoprotein inhibitior	+	0.7721	77.21%
P-glycoprotein substrate	+	0.6798	67.98%
CYP3A4 substrate	+	0.7048	70.48%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8601	86.01%
CYP3A4 inhibition	-	0.7834	78.34%
CYP2C9 inhibition	-	0.5819	58.19%
CYP2C19 inhibition	-	0.7693	76.93%
CYP2D6 inhibition	-	0.8460	84.60%
CYP1A2 inhibition	-	0.5000	50.00%
CYP2C8 inhibition	+	0.7181	71.81%
CYP inhibitory promiscuity	-	0.7299	72.99%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9025	90.25%
Carcinogenicity (trinary)	Non-required	0.4707	47.07%
Eye corrosion	-	0.9818	98.18%
Eye irritation	-	0.9161	91.61%
Skin irritation	-	0.7414	74.14%
Skin corrosion	-	0.9097	90.97%
Ames mutagenesis	-	0.6608	66.08%
Human Ether-a-go-go-Related Gene inhibition	-	0.5149	51.49%
Micronuclear	+	0.6800	68.00%
Hepatotoxicity	+	0.5898	58.98%
skin sensitisation	-	0.8306	83.06%
Respiratory toxicity	+	0.7556	75.56%
Reproductive toxicity	+	0.8000	80.00%
Mitochondrial toxicity	+	0.8250	82.50%
Nephrotoxicity	-	0.8450	84.50%
Acute Oral Toxicity (c)	III	0.5223	52.23%
Estrogen receptor binding	+	0.8299	82.99%
Androgen receptor binding	+	0.7998	79.98%
Thyroid receptor binding	+	0.6161	61.61%
Glucocorticoid receptor binding	+	0.7167	71.67%
Aromatase binding	+	0.7069	70.69%
PPAR gamma	+	0.6767	67.67%
Honey bee toxicity	-	0.7450	74.50%
Biodegradation	-	0.9500	95.00%
Crustacea aquatic toxicity	-	0.6800	68.00%
Fish aquatic toxicity	+	0.7960	79.60%

Targets

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Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
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

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Below are displayed all the plants proven (via scientific papers) to contain this compound!
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Solanum pseudocapsicum

Stratiotes aloides