7-Hydroxy-7-methyl-1-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4a,5,6,7a-tetrahydro-1H-cyclopenta[c]pyran-4-carboxylic acid

Details

Physical and Chemical Properties

Synonyms

2D Structure

3D Structure

ADMET Properties

Targets (proven and/or predicted)

Plants that contains it

Cross-Links

Details

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Internal ID	3db68c05-cc89-40af-884b-1db2a513d297
Taxonomy	Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Iridoid O-glycosides
IUPAC Name	7-hydroxy-7-methyl-1-[3,4,5-trihydroxy-6-(hydroxymethyl)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)CO)O)O)O)O
SMILES (Isomeric)	CC1(CCC2C1C(OC=C2C(=O)O)OC3C(C(C(C(O3)CO)O)O)O)O
InChI	InChI=1S/C16H24O10/c1-16(23)3-2-6-7(13(21)22)5-24-14(9(6)16)26-15-12(20)11(19)10(18)8(4-17)25-15/h5-6,8-12,14-15,17-20,23H,2-4H2,1H3,(H,21,22)
InChI Key	VLCHQFXSBHIBRV-UHFFFAOYSA-N
Popularity	0 references in papers

Physical and Chemical Properties

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Molecular Formula	C₁₆H₂₄O₁₀
Molecular Weight	376.36 g/mol
Exact Mass	376.13694696 g/mol
Topological Polar Surface Area (TPSA)	166.00 Å²
XlogP	-2.00
Atomic LogP (AlogP)	-2.10
H-Bond Acceptor	9
H-Bond Donor	6
Rotatable Bonds	4

Synonyms

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7-Hydroxy-7-methyl-1-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4a,5,6,7a-tetrahydro-1H-cyclopenta[c]pyran-4-carboxylic acid

2D Structure

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3D Structure

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ADMET Properties (via admetSAR 2)

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Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7659	76.59%
Caco-2	-	0.8657	86.57%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	-	0.7857	78.57%
Subcellular localzation	Mitochondria	0.7195	71.95%
OATP2B1 inhibitior	-	0.8601	86.01%
OATP1B1 inhibitior	-	0.3229	32.29%
OATP1B3 inhibitior	+	0.9184	91.84%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.7879	78.79%
BSEP inhibitior	-	0.9339	93.39%
P-glycoprotein inhibitior	-	0.8961	89.61%
P-glycoprotein substrate	-	0.9076	90.76%
CYP3A4 substrate	+	0.6090	60.90%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8863	88.63%
CYP3A4 inhibition	-	0.9341	93.41%
CYP2C9 inhibition	-	0.8851	88.51%
CYP2C19 inhibition	-	0.9071	90.71%
CYP2D6 inhibition	-	0.9191	91.91%
CYP1A2 inhibition	-	0.8644	86.44%
CYP2C8 inhibition	-	0.6473	64.73%
CYP inhibitory promiscuity	-	0.8847	88.47%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6368	63.68%
Eye corrosion	-	0.9912	99.12%
Eye irritation	-	0.9714	97.14%
Skin irritation	-	0.5643	56.43%
Skin corrosion	-	0.9285	92.85%
Ames mutagenesis	-	0.6640	66.40%
Human Ether-a-go-go-Related Gene inhibition	-	0.6077	60.77%
Micronuclear	-	0.8600	86.00%
Hepatotoxicity	-	0.8690	86.90%
skin sensitisation	-	0.8894	88.94%
Respiratory toxicity	+	0.5778	57.78%
Reproductive toxicity	+	0.8556	85.56%
Mitochondrial toxicity	+	0.6125	61.25%
Nephrotoxicity	+	0.5573	55.73%
Acute Oral Toxicity (c)	III	0.4596	45.96%
Estrogen receptor binding	+	0.6141	61.41%
Androgen receptor binding	-	0.5000	50.00%
Thyroid receptor binding	+	0.5214	52.14%
Glucocorticoid receptor binding	+	0.5395	53.95%
Aromatase binding	+	0.5706	57.06%
PPAR gamma	+	0.5649	56.49%
Honey bee toxicity	-	0.8929	89.29%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.7550	75.50%
Fish aquatic toxicity	+	0.7290	72.90%

Targets

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Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
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	97.50%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	93.70%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.24%	97.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	85.34%	86.33%
CHEMBL5255	O00206	Toll-like receptor 4	85.30%	92.50%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.57%	95.56%
CHEMBL253	P34972	Cannabinoid CB2 receptor	84.52%	97.25%
CHEMBL4208	P20618	Proteasome component C5	83.20%	90.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	83.01%	100.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.80%	95.89%
CHEMBL2581	P07339	Cathepsin D	82.45%	98.95%
CHEMBL4227	P25090	Lipoxin A4 receptor	82.33%	100.00%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	82.27%	94.62%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.83%	89.00%
CHEMBL216	P11229	Muscarinic acetylcholine receptor M1	80.45%	94.23%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	80.16%	95.89%
CHEMBL218	P21554	Cannabinoid CB1 receptor	80.02%	96.61%

Plants that contains it

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Below are displayed all the plants proven (via scientific papers) to contain this compound!
To see more specific details click the taxa you are interested in.