Phaeophytin A

Details

• Internal ID: 0b6c5579-972e-4dec-81f1-fdd6e99d39c0
• Taxonomy: Organoheterocyclic compounds > Tetrapyrroles and derivatives
• IUPAC Name: methyl 16-ethenyl-11-ethyl-4-hydroxy-12,17,21,26-tetramethyl-22-[3-oxo-3-[(E)-3,7,11,15-tetramethylhexadec-2-enoxy]propyl]-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-undecaene-3-carboxylate
• 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)OCC=C(C)CCCC(C)CCCC(C)CCCC(C)C)C4=N3)C(=O)OC)O)C)C
• SMILES (Isomeric): CCC1=C(C2=NC1=CC3=C(C4=C(C(C(=C5C(C(C(=CC6=NC(=C2)C(=C6C)C=C)N5)C)CCC(=O)OC/C=C(\C)/CCCC(C)CCCC(C)CCCC(C)C)C4=N3)C(=O)OC)O)C)C
• InChI: InChI=1S/C55H74N4O5/c1-13-39-35(8)42-28-44-37(10)41(24-25-48(60)64-27-26-34(7)23-17-22-33(6)21-16-20-32(5)19-15-18-31(3)4)52(58-44)50-51(55(62)63-12)54(61)49-38(11)45(59-53(49)50)30-47-40(14-2)36(9)43(57-47)29-46(39)56-42/h13,26,28-33,37,41,51,58,61H,1,14-25,27H2,2-12H3/b34-26+,44-28?,46-29?,47-30?,52-50?
• InChI Key: FDHFJXKRMIVNCQ-RRNMINROSA-N
• Popularity: 98 references in papers

Physical and Chemical Properties

• Molecular Formula: C₅₅H₇₄N₄O₅
• Molecular Weight: 871.20 g/mol
• Exact Mass: 870.56592147 g/mol
• Topological Polar Surface Area (TPSA): 122.00 Ų
• XlogP: 11.70
• Atomic LogP (AlogP): 12.95
• H-Bond Acceptor: 9
• H-Bond Donor: 2
• Rotatable Bonds: 20

Synonyms

• NSC26686
• Phaeophytin A
• Phaeophytin-a
• SCHEMBL578506
• SCHEMBL14999658
• NSC-26686
• methyl ethyl-tetramethyl-oxo-[3-oxo-3-[(E)-3,7,11,15-tetramethylhexadec-2-enoxy]propyl]-vinyl-[?]carboxylate

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9592	95.92%
Caco-2	-	0.8487	84.87%
Blood Brain Barrier	+	0.6500	65.00%
Human oral bioavailability	-	0.5429	54.29%
Subcellular localzation	Mitochondria	0.8086	80.86%
OATP2B1 inhibitior	-	0.8594	85.94%
OATP1B1 inhibitior	+	0.8126	81.26%
OATP1B3 inhibitior	+	0.9217	92.17%
MATE1 inhibitior	-	0.7200	72.00%
OCT2 inhibitior	-	0.7000	70.00%
BSEP inhibitior	+	0.9928	99.28%
P-glycoprotein inhibitior	+	0.7637	76.37%
P-glycoprotein substrate	+	0.8121	81.21%
CYP3A4 substrate	+	0.7409	74.09%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8492	84.92%
CYP3A4 inhibition	-	0.7442	74.42%
CYP2C9 inhibition	-	0.6523	65.23%
CYP2C19 inhibition	-	0.7566	75.66%
CYP2D6 inhibition	-	0.8787	87.87%
CYP1A2 inhibition	-	0.5596	55.96%
CYP2C8 inhibition	+	0.7651	76.51%
CYP inhibitory promiscuity	-	0.7777	77.77%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.8600	86.00%
Carcinogenicity (trinary)	Non-required	0.5230	52.30%
Eye corrosion	-	0.9817	98.17%
Eye irritation	-	0.9039	90.39%
Skin irritation	-	0.7394	73.94%
Skin corrosion	-	0.9202	92.02%
Ames mutagenesis	-	0.6532	65.32%
Human Ether-a-go-go-Related Gene inhibition	+	0.6743	67.43%
Micronuclear	+	0.6200	62.00%
Hepatotoxicity	+	0.5398	53.98%
skin sensitisation	-	0.8323	83.23%
Respiratory toxicity	+	0.7444	74.44%
Reproductive toxicity	+	0.7222	72.22%
Mitochondrial toxicity	+	0.7750	77.50%
Nephrotoxicity	-	0.8555	85.55%
Acute Oral Toxicity (c)	III	0.5592	55.92%
Estrogen receptor binding	+	0.8268	82.68%
Androgen receptor binding	+	0.7856	78.56%
Thyroid receptor binding	+	0.6301	63.01%
Glucocorticoid receptor binding	+	0.7882	78.82%
Aromatase binding	+	0.6478	64.78%
PPAR gamma	+	0.7659	76.59%
Honey bee toxicity	-	0.6942	69.42%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.6000	60.00%
Fish aquatic toxicity	+	0.9858	98.58%

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	98.96%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	98.53%	94.45%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	98.41%	85.14%
CHEMBL2581	P07339	Cathepsin D	97.14%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.41%	91.11%
CHEMBL202	P00374	Dihydrofolate reductase	94.24%	89.92%
CHEMBL3267	P48736	PI3-kinase p110-gamma subunit	93.40%	95.71%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	93.17%	90.71%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	92.25%	96.90%
CHEMBL5979	P05186	Alkaline phosphatase, tissue-nonspecific isozyme	90.34%	85.40%
CHEMBL3060	Q9Y345	Glycine transporter 2	89.87%	99.17%
CHEMBL4227	P25090	Lipoxin A4 receptor	89.86%	100.00%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	89.83%	96.00%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	89.82%	91.24%
CHEMBL221	P23219	Cyclooxygenase-1	89.78%	90.17%
CHEMBL4224	P49759	Dual specificty protein kinase CLK1	89.70%	85.30%
CHEMBL3401	O75469	Pregnane X receptor	88.63%	94.73%
CHEMBL230	P35354	Cyclooxygenase-2	86.85%	89.63%
CHEMBL255	P29275	Adenosine A2b receptor	86.06%	98.59%
CHEMBL3359	P21462	Formyl peptide receptor 1	85.03%	93.56%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	83.77%	93.03%
CHEMBL2094135	Q96BI3	Gamma-secretase	82.50%	98.05%
CHEMBL1937	Q92769	Histone deacetylase 2	82.33%	94.75%
CHEMBL1907605	P24864	Cyclin-dependent kinase 2/cyclin E1	82.03%	92.88%
CHEMBL213	P08588	Beta-1 adrenergic receptor	80.87%	95.56%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	80.60%	96.47%
CHEMBL2563	Q9UQL6	Histone deacetylase 5	80.40%	89.67%

Plants that contains it

• Megaceros flagellaris
• Ophiorrhiza pumila
• Richardia grandiflora
• Tapura fischeri

Cross-Links

• PubChem: 135421897
• LOTUS: LTS0133102
• wikiData: Q104253070