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

Details

• Internal ID: f4163227-41c4-492b-8468-32805fab4fa8
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Iridoid O-glycosides
• IUPAC Name: (1S,4aR,7S,7aS)-7-(hydroxymethyl)-1-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4a,5,7,7a-tetrahydro-1H-cyclopenta[c]pyran-6-one
• InChI: InChI=1S/C15H22O9/c16-4-7-8(18)3-6-1-2-22-14(10(6)7)24-15-13(21)12(20)11(19)9(5-17)23-15/h1-2,6-7,9-17,19-21H,3-5H2/t6-,7-,9+,10-,11+,12-,13+,14-,15+/m0/s1
• InChI Key: ZJCJWENRZLVNQE-ZAPPMGNXSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₂O₉
• Molecular Weight: 346.33 g/mol
• Exact Mass: 346.12638228 g/mol
• Topological Polar Surface Area (TPSA): 146.00 Ų
• XlogP: -1.90
• Atomic LogP (AlogP): -2.51
• H-Bond Acceptor: 9
• H-Bond Donor: 5
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.6415	64.15%
Caco-2	-	0.8841	88.41%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	-	0.8000	80.00%
Subcellular localzation	Mitochondria	0.7040	70.40%
OATP2B1 inhibitior	-	0.8593	85.93%
OATP1B1 inhibitior	+	0.8680	86.80%
OATP1B3 inhibitior	+	0.9600	96.00%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	-	0.9305	93.05%
P-glycoprotein inhibitior	-	0.9055	90.55%
P-glycoprotein substrate	-	0.9167	91.67%
CYP3A4 substrate	+	0.5452	54.52%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8409	84.09%
CYP3A4 inhibition	-	0.9330	93.30%
CYP2C9 inhibition	-	0.9568	95.68%
CYP2C19 inhibition	-	0.8463	84.63%
CYP2D6 inhibition	-	0.9069	90.69%
CYP1A2 inhibition	-	0.9175	91.75%
CYP2C8 inhibition	-	0.8721	87.21%
CYP inhibitory promiscuity	-	0.8858	88.58%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.7135	71.35%
Eye corrosion	-	0.9890	98.90%
Eye irritation	-	0.9497	94.97%
Skin irritation	-	0.8455	84.55%
Skin corrosion	-	0.9643	96.43%
Ames mutagenesis	+	0.5400	54.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5657	56.57%
Micronuclear	-	0.8000	80.00%
Hepatotoxicity	-	0.7696	76.96%
skin sensitisation	-	0.9030	90.30%
Respiratory toxicity	+	0.6333	63.33%
Reproductive toxicity	+	0.5889	58.89%
Mitochondrial toxicity	-	0.5250	52.50%
Nephrotoxicity	+	0.5859	58.59%
Acute Oral Toxicity (c)	IV	0.4205	42.05%
Estrogen receptor binding	-	0.6490	64.90%
Androgen receptor binding	-	0.4917	49.17%
Thyroid receptor binding	-	0.7002	70.02%
Glucocorticoid receptor binding	-	0.7602	76.02%
Aromatase binding	-	0.5460	54.60%
PPAR gamma	+	0.5188	51.88%
Honey bee toxicity	-	0.7826	78.26%
Biodegradation	-	0.5750	57.50%
Crustacea aquatic toxicity	-	0.6050	60.50%
Fish aquatic toxicity	+	0.7603	76.03%

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	98.17%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	88.67%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	88.46%	97.09%
CHEMBL2581	P07339	Cathepsin D	87.59%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.61%	95.56%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	85.00%	86.92%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	84.09%	94.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	80.79%	99.17%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.17%	95.89%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	80.05%	96.21%

Plants that contains it

• Pedicularis procera

Cross-Links

• PubChem: 162909417
• LOTUS: LTS0245499
• wikiData: Q105377775