[(6S)-6,7-dihydroxy-7-methyl-1-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4a,5,6,7a-tetrahydro-1H-cyclopenta[c]pyran-4-yl]methyl 3-methylbutanoate

Details

• Internal ID: 569f06d6-10e5-4bd9-9d00-344b17a56809
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Iridoid O-glycosides
• IUPAC Name: [(6S)-6,7-dihydroxy-7-methyl-1-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4a,5,6,7a-tetrahydro-1H-cyclopenta[c]pyran-4-yl]methyl 3-methylbutanoate
• SMILES (Canonical): CC(C)CC(=O)OCC1=COC(C2C1CC(C2(C)O)O)OC3C(C(C(C(O3)CO)O)O)O
• SMILES (Isomeric): CC(C)CC(=O)OCC1=COC(C2C1C[C@@H](C2(C)O)O)O[C@@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O
• InChI: InChI=1S/C21H34O11/c1-9(2)4-14(24)29-7-10-8-30-19(15-11(10)5-13(23)21(15,3)28)32-20-18(27)17(26)16(25)12(6-22)31-20/h8-9,11-13,15-20,22-23,25-28H,4-7H2,1-3H3/t11?,12-,13+,15?,16-,17+,18-,19?,20-,21?/m1/s1
• InChI Key: RWQUPFFXRZRCHW-UMFOEYFWSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₃₄O₁₁
• Molecular Weight: 462.50 g/mol
• Exact Mass: 462.21011190 g/mol
• Topological Polar Surface Area (TPSA): 175.00 Ų
• XlogP: -1.70
• Atomic LogP (AlogP): -1.62
• 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	+	0.7764	77.64%
Caco-2	-	0.8641	86.41%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.8571	85.71%
Subcellular localzation	Mitochondria	0.7213	72.13%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8146	81.46%
OATP1B3 inhibitior	+	0.8806	88.06%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.9040	90.40%
P-glycoprotein inhibitior	-	0.7247	72.47%
P-glycoprotein substrate	-	0.7044	70.44%
CYP3A4 substrate	+	0.6680	66.80%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8847	88.47%
CYP3A4 inhibition	-	0.9301	93.01%
CYP2C9 inhibition	-	0.8804	88.04%
CYP2C19 inhibition	-	0.8967	89.67%
CYP2D6 inhibition	-	0.9319	93.19%
CYP1A2 inhibition	-	0.8854	88.54%
CYP2C8 inhibition	-	0.6287	62.87%
CYP inhibitory promiscuity	-	0.9133	91.33%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6299	62.99%
Eye corrosion	-	0.9905	99.05%
Eye irritation	-	0.9610	96.10%
Skin irritation	-	0.6432	64.32%
Skin corrosion	-	0.9425	94.25%
Ames mutagenesis	-	0.5400	54.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3700	37.00%
Micronuclear	-	0.8300	83.00%
Hepatotoxicity	-	0.6875	68.75%
skin sensitisation	-	0.8643	86.43%
Respiratory toxicity	+	0.6222	62.22%
Reproductive toxicity	+	0.8889	88.89%
Mitochondrial toxicity	+	0.5125	51.25%
Nephrotoxicity	-	0.7163	71.63%
Acute Oral Toxicity (c)	III	0.5897	58.97%
Estrogen receptor binding	+	0.6437	64.37%
Androgen receptor binding	+	0.6143	61.43%
Thyroid receptor binding	-	0.6286	62.86%
Glucocorticoid receptor binding	+	0.6126	61.26%
Aromatase binding	+	0.6459	64.59%
PPAR gamma	-	0.5113	51.13%
Honey bee toxicity	-	0.7808	78.08%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.6555	65.55%
Fish aquatic toxicity	+	0.9282	92.82%

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	98.58%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	95.62%	97.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.37%	91.11%
CHEMBL226	P30542	Adenosine A1 receptor	95.30%	95.93%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	92.05%	97.21%
CHEMBL1806	P11388	DNA topoisomerase II alpha	91.68%	89.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	90.70%	94.45%
CHEMBL4040	P28482	MAP kinase ERK2	90.41%	83.82%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	89.75%	96.95%
CHEMBL2581	P07339	Cathepsin D	89.00%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.38%	86.33%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	86.11%	95.89%
CHEMBL2996	Q05655	Protein kinase C delta	86.08%	97.79%
CHEMBL3060	Q9Y345	Glycine transporter 2	85.54%	99.17%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	83.55%	95.56%
CHEMBL1994	P08235	Mineralocorticoid receptor	82.20%	100.00%
CHEMBL253	P34972	Cannabinoid CB2 receptor	81.92%	97.25%
CHEMBL1293316	Q9HBX9	Relaxin receptor 1	80.72%	82.50%
CHEMBL5255	O00206	Toll-like receptor 4	80.71%	92.50%

Plants that contains it

• Angelica sinensis
• Valeriana officinalis

Cross-Links

• PubChem: 24893667
• NPASS: NPC114046