[(2R,3R,4R,5R,6S)-2-[[(1S,4aR,5S,7aS)-7-(hydroxymethyl)-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-5-yl]oxy]-4,5-dihydroxy-6-methyloxan-3-yl] (E)-3-(4-hydroxyphenyl)prop-2-enoate

Details

• Internal ID: fdb41c18-285e-42b2-b8b0-66f79da04812
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Iridoid O-glycosides
• IUPAC Name: [(2R,3R,4R,5R,6S)-2-[[(1S,4aR,5S,7aS)-7-(hydroxymethyl)-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-5-yl]oxy]-4,5-dihydroxy-6-methyloxan-3-yl] (E)-3-(4-hydroxyphenyl)prop-2-enoate
• SMILES (Canonical): CC1C(C(C(C(O1)OC2C=C(C3C2C=COC3OC4C(C(C(C(O4)CO)O)O)O)CO)OC(=O)C=CC5=CC=C(C=C5)O)O)O
• SMILES (Isomeric): C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)O[C@@H]2C=C([C@@H]3[C@H]2C=CO[C@H]3O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)CO)OC(=O)/C=C/C5=CC=C(C=C5)O)O)O
• InChI: InChI=1S/C30H38O15/c1-13-22(35)25(38)27(44-20(34)7-4-14-2-5-16(33)6-3-14)30(41-13)42-18-10-15(11-31)21-17(18)8-9-40-28(21)45-29-26(39)24(37)23(36)19(12-32)43-29/h2-10,13,17-19,21-33,35-39H,11-12H2,1H3/b7-4+/t13-,17-,18+,19+,21+,22-,23+,24-,25+,26+,27+,28-,29-,30-/m0/s1
• InChI Key: YYHNQOISCKVABM-MBIIODOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₀H₃₈O₁₅
• Molecular Weight: 638.60 g/mol
• Exact Mass: 638.22107050 g/mol
• Topological Polar Surface Area (TPSA): 234.00 Ų
• XlogP: -1.80
• Atomic LogP (AlogP): -1.98
• H-Bond Acceptor: 15
• H-Bond Donor: 8
• Rotatable Bonds: 9

Synonyms

• ACon1_001414
• NCGC00180530-01

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6608	66.08%
Caco-2	-	0.8913	89.13%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	-	0.8571	85.71%
Subcellular localzation	Mitochondria	0.6881	68.81%
OATP2B1 inhibitior	-	0.8583	85.83%
OATP1B1 inhibitior	+	0.8052	80.52%
OATP1B3 inhibitior	+	0.9687	96.87%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	+	0.5695	56.95%
P-glycoprotein inhibitior	-	0.5139	51.39%
P-glycoprotein substrate	+	0.5000	50.00%
CYP3A4 substrate	+	0.6774	67.74%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8776	87.76%
CYP3A4 inhibition	-	0.9356	93.56%
CYP2C9 inhibition	-	0.8553	85.53%
CYP2C19 inhibition	-	0.7471	74.71%
CYP2D6 inhibition	-	0.8744	87.44%
CYP1A2 inhibition	-	0.8189	81.89%
CYP2C8 inhibition	+	0.6957	69.57%
CYP inhibitory promiscuity	+	0.5280	52.80%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6168	61.68%
Eye corrosion	-	0.9903	99.03%
Eye irritation	-	0.9175	91.75%
Skin irritation	-	0.7910	79.10%
Skin corrosion	-	0.9563	95.63%
Ames mutagenesis	-	0.5691	56.91%
Human Ether-a-go-go-Related Gene inhibition	-	0.3843	38.43%
Micronuclear	-	0.5567	55.67%
Hepatotoxicity	-	0.8375	83.75%
skin sensitisation	-	0.8267	82.67%
Respiratory toxicity	-	0.5778	57.78%
Reproductive toxicity	+	0.8000	80.00%
Mitochondrial toxicity	+	0.6000	60.00%
Nephrotoxicity	-	0.8354	83.54%
Acute Oral Toxicity (c)	III	0.5473	54.73%
Estrogen receptor binding	+	0.7724	77.24%
Androgen receptor binding	+	0.5683	56.83%
Thyroid receptor binding	-	0.5000	50.00%
Glucocorticoid receptor binding	+	0.5935	59.35%
Aromatase binding	-	0.5333	53.33%
PPAR gamma	+	0.6437	64.37%
Honey bee toxicity	-	0.6968	69.68%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.5755	57.55%
Fish aquatic toxicity	+	0.8225	82.25%

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	98.67%	91.11%
CHEMBL1293249	Q13887	Kruppel-like factor 5	95.18%	86.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	94.22%	89.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.97%	96.09%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	92.09%	96.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.05%	95.56%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	89.51%	91.71%
CHEMBL3714130	P46095	G-protein coupled receptor 6	89.37%	97.36%
CHEMBL3401	O75469	Pregnane X receptor	88.00%	94.73%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.72%	97.09%
CHEMBL3060	Q9Y345	Glycine transporter 2	85.48%	99.17%
CHEMBL2581	P07339	Cathepsin D	84.43%	98.95%
CHEMBL3194	P02766	Transthyretin	83.58%	90.71%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	83.35%	95.89%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	83.14%	86.92%
CHEMBL2107	P61073	C-X-C chemokine receptor type 4	82.51%	93.10%
CHEMBL2563	Q9UQL6	Histone deacetylase 5	82.10%	89.67%
CHEMBL1951	P21397	Monoamine oxidase A	81.82%	91.49%
CHEMBL226	P30542	Adenosine A1 receptor	80.47%	95.93%

Plants that contains it

• Verbascum nigrum
• Verbascum undulatum

Cross-Links

• PubChem: 23928106
• LOTUS: LTS0024113
• wikiData: Q105368651