13-O-p-Coumaroylplumieride

Details

• Internal ID: f53e4956-4046-46a9-ac24-6e6012000f02
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Iridoid O-glycosides
• IUPAC Name: methyl (1S,4aS,7R,7aS)-4'-[(1S)-1-[(E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxyethyl]-5'-oxo-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyspiro[4a,7a-dihydro-1H-cyclopenta[c]pyran-7,2'-furan]-4-carboxylate
• SMILES (Canonical): CC(C1=CC2(C=CC3C2C(OC=C3C(=O)OC)OC4C(C(C(C(O4)CO)O)O)O)OC1=O)OC(=O)C=CC5=CC=C(C=C5)O
• SMILES (Isomeric): C[C@@H](C1=C[C@@]2(C=C[C@H]3[C@@H]2[C@@H](OC=C3C(=O)OC)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)OC1=O)OC(=O)/C=C/C5=CC=C(C=C5)O
• InChI: InChI=1S/C30H32O14/c1-14(41-21(33)8-5-15-3-6-16(32)7-4-15)18-11-30(44-27(18)38)10-9-17-19(26(37)39-2)13-40-28(22(17)30)43-29-25(36)24(35)23(34)20(12-31)42-29/h3-11,13-14,17,20,22-25,28-29,31-32,34-36H,12H2,1-2H3/b8-5+/t14-,17+,20+,22+,23+,24-,25+,28-,29-,30+/m0/s1
• InChI Key: WBCMGDNFDRNGGZ-DEYYTONKSA-N
• Popularity: 3 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₀H₃₂O₁₄
• Molecular Weight: 616.60 g/mol
• Exact Mass: 616.17920569 g/mol
• Topological Polar Surface Area (TPSA): 208.00 Ų
• XlogP: 0.50
• Atomic LogP (AlogP): -0.41
• H-Bond Acceptor: 14
• H-Bond Donor: 5
• Rotatable Bonds: 8

Synonyms

• CHEMBL499977
• 80416-52-0
• Plumeride p-coumarate
• 13-O-p-coumaroylplumeride
• methyl (1S,4aS,7aS)-4'-[(1S)-1-[(E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxyethyl]-5'-oxo-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyspiro[4a,7a-dihydro-1H-cyclopenta[c]pyran-7,2'-furan]-4-carboxylate
• BDBM50480282
• AKOS040760939
• FS-9046
• Plumeride p-coumarate, >=90% (LC/MS-ELSD)

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7435	74.35%
Caco-2	-	0.8796	87.96%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.8714	87.14%
Subcellular localzation	Mitochondria	0.6948	69.48%
OATP2B1 inhibitior	-	0.7147	71.47%
OATP1B1 inhibitior	+	0.7497	74.97%
OATP1B3 inhibitior	+	0.9478	94.78%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	+	0.8990	89.90%
P-glycoprotein inhibitior	+	0.6294	62.94%
P-glycoprotein substrate	+	0.5998	59.98%
CYP3A4 substrate	+	0.7084	70.84%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8769	87.69%
CYP3A4 inhibition	-	0.8093	80.93%
CYP2C9 inhibition	-	0.8087	80.87%
CYP2C19 inhibition	-	0.7972	79.72%
CYP2D6 inhibition	-	0.8993	89.93%
CYP1A2 inhibition	-	0.8781	87.81%
CYP2C8 inhibition	+	0.7751	77.51%
CYP inhibitory promiscuity	-	0.6147	61.47%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.5387	53.87%
Eye corrosion	-	0.9880	98.80%
Eye irritation	-	0.9168	91.68%
Skin irritation	-	0.7597	75.97%
Skin corrosion	-	0.9390	93.90%
Ames mutagenesis	-	0.5900	59.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3613	36.13%
Micronuclear	+	0.5633	56.33%
Hepatotoxicity	-	0.6832	68.32%
skin sensitisation	-	0.8075	80.75%
Respiratory toxicity	+	0.6556	65.56%
Reproductive toxicity	+	0.8889	88.89%
Mitochondrial toxicity	+	0.7375	73.75%
Nephrotoxicity	+	0.8064	80.64%
Acute Oral Toxicity (c)	III	0.5002	50.02%
Estrogen receptor binding	+	0.7719	77.19%
Androgen receptor binding	+	0.6915	69.15%
Thyroid receptor binding	+	0.5933	59.33%
Glucocorticoid receptor binding	+	0.7711	77.11%
Aromatase binding	+	0.5196	51.96%
PPAR gamma	+	0.6714	67.14%
Honey bee toxicity	-	0.6821	68.21%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	-	0.6100	61.00%
Fish aquatic toxicity	+	0.8590	85.90%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.16%	91.11%
CHEMBL2581	P07339	Cathepsin D	96.85%	98.95%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	95.24%	96.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	94.99%	89.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	94.86%	86.33%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	94.56%	85.14%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.20%	96.09%
CHEMBL2563	Q9UQL6	Histone deacetylase 5	92.84%	89.67%
CHEMBL3401	O75469	Pregnane X receptor	91.85%	94.73%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.61%	95.56%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	87.78%	94.45%
CHEMBL3060	Q9Y345	Glycine transporter 2	86.14%	99.17%
CHEMBL4208	P20618	Proteasome component C5	85.37%	90.00%
CHEMBL2996	Q05655	Protein kinase C delta	83.88%	97.79%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	83.53%	91.07%
CHEMBL1951	P21397	Monoamine oxidase A	82.82%	91.49%
CHEMBL3137262	O60341	LSD1/CoREST complex	82.44%	97.09%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.42%	95.89%
CHEMBL5966	P55899	IgG receptor FcRn large subunit p51	80.55%	90.93%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	80.43%	95.83%

Plants that contains it

• Allamanda cathartica
• Plumeria rubra

Cross-Links

• PubChem: 44593497
• LOTUS: LTS0224769
• wikiData: Q105300646