(1S,4aS,7S,7aS)-7-hydroxy-7-methyl-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxymethyl]oxan-2-yl]oxy-4a,5,6,7a-tetrahydro-1H-cyclopenta[c]pyran-4-carboxylic acid

Details

• Internal ID: 12e1ffa6-0fe1-43c2-b914-d394e7e288f2
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Iridoid O-glycosides
• IUPAC Name: (1S,4aS,7S,7aS)-7-hydroxy-7-methyl-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxymethyl]oxan-2-yl]oxy-4a,5,6,7a-tetrahydro-1H-cyclopenta[c]pyran-4-carboxylic acid
• SMILES (Canonical): CC1(CCC2C1C(OC=C2C(=O)O)OC3C(C(C(C(O3)COC(=O)C=CC4=CC=C(C=C4)O)O)O)O)O
• SMILES (Isomeric): C[C@@]1(CC[C@H]2[C@@H]1[C@@H](OC=C2C(=O)O)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)COC(=O)/C=C/C4=CC=C(C=C4)O)O)O)O)O
• InChI: InChI=1S/C25H30O12/c1-25(33)9-8-14-15(22(31)32)10-35-23(18(14)25)37-24-21(30)20(29)19(28)16(36-24)11-34-17(27)7-4-12-2-5-13(26)6-3-12/h2-7,10,14,16,18-21,23-24,26,28-30,33H,8-9,11H2,1H3,(H,31,32)/b7-4+/t14-,16-,18-,19-,20+,21-,23+,24+,25+/m1/s1
• InChI Key: BZOWSEVETQYSBF-WYQBJTCVSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₅H₃₀O₁₂
• Molecular Weight: 522.50 g/mol
• Exact Mass: 522.17372639 g/mol
• Topological Polar Surface Area (TPSA): 192.00 Ų
• XlogP: -0.20
• Atomic LogP (AlogP): -0.13
• H-Bond Acceptor: 11
• H-Bond Donor: 6
• Rotatable Bonds: 7

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8525	85.25%
Caco-2	-	0.9047	90.47%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	-	0.8429	84.29%
Subcellular localzation	Mitochondria	0.7597	75.97%
OATP2B1 inhibitior	-	0.8562	85.62%
OATP1B1 inhibitior	+	0.7516	75.16%
OATP1B3 inhibitior	+	0.9248	92.48%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.7867	78.67%
BSEP inhibitior	-	0.6898	68.98%
P-glycoprotein inhibitior	-	0.6209	62.09%
P-glycoprotein substrate	-	0.7095	70.95%
CYP3A4 substrate	+	0.6779	67.79%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8803	88.03%
CYP3A4 inhibition	-	0.8787	87.87%
CYP2C9 inhibition	-	0.7952	79.52%
CYP2C19 inhibition	-	0.8243	82.43%
CYP2D6 inhibition	-	0.8937	89.37%
CYP1A2 inhibition	-	0.7746	77.46%
CYP2C8 inhibition	+	0.7787	77.87%
CYP inhibitory promiscuity	-	0.8366	83.66%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.5555	55.55%
Eye corrosion	-	0.9914	99.14%
Eye irritation	-	0.9299	92.99%
Skin irritation	-	0.6166	61.66%
Skin corrosion	-	0.9218	92.18%
Ames mutagenesis	-	0.6770	67.70%
Human Ether-a-go-go-Related Gene inhibition	-	0.4666	46.66%
Micronuclear	-	0.7400	74.00%
Hepatotoxicity	-	0.7601	76.01%
skin sensitisation	-	0.8583	85.83%
Respiratory toxicity	+	0.5889	58.89%
Reproductive toxicity	+	0.9111	91.11%
Mitochondrial toxicity	+	0.8000	80.00%
Nephrotoxicity	-	0.6771	67.71%
Acute Oral Toxicity (c)	I	0.5007	50.07%
Estrogen receptor binding	+	0.7759	77.59%
Androgen receptor binding	+	0.6514	65.14%
Thyroid receptor binding	+	0.5194	51.94%
Glucocorticoid receptor binding	+	0.6938	69.38%
Aromatase binding	+	0.5368	53.68%
PPAR gamma	+	0.6689	66.89%
Honey bee toxicity	-	0.8296	82.96%
Biodegradation	-	0.6500	65.00%
Crustacea aquatic toxicity	-	0.5900	59.00%
Fish aquatic toxicity	+	0.9633	96.33%

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	96.88%	91.11%
CHEMBL1293249	Q13887	Kruppel-like factor 5	96.85%	86.33%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.81%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	94.31%	97.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	92.27%	89.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.07%	95.56%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	89.52%	96.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	87.28%	95.89%
CHEMBL4208	P20618	Proteasome component C5	87.23%	90.00%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	86.66%	94.62%
CHEMBL4227	P25090	Lipoxin A4 receptor	86.64%	100.00%
CHEMBL5255	O00206	Toll-like receptor 4	85.91%	92.50%
CHEMBL206	P03372	Estrogen receptor alpha	85.59%	97.64%
CHEMBL221	P23219	Cyclooxygenase-1	84.46%	90.17%
CHEMBL1994	P08235	Mineralocorticoid receptor	84.28%	100.00%
CHEMBL3194	P02766	Transthyretin	84.26%	90.71%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	82.64%	95.89%
CHEMBL226	P30542	Adenosine A1 receptor	82.57%	95.93%
CHEMBL2581	P07339	Cathepsin D	81.16%	98.95%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	80.04%	93.00%

Plants that contains it

• Scutellaria albida

Cross-Links

• PubChem: 163190893
• LOTUS: LTS0263812
• wikiData: Q104950610