7,8-Dehydropenstemonoside

Details

• Internal ID: 649c5085-6883-4d58-8769-007b4b387396
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Iridoid O-glycosides
• IUPAC Name: methyl (1S,4aS,5R,7aS)-5-hydroxy-7-methyl-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-4-carboxylate
• SMILES (Canonical): CC1=CC(C2C1C(OC=C2C(=O)OC)OC3C(C(C(C(O3)CO)O)O)O)O
• SMILES (Isomeric): CC1=C[C@H]([C@H]2[C@@H]1[C@@H](OC=C2C(=O)OC)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)O
• InChI: InChI=1S/C17H24O10/c1-6-3-8(19)11-7(15(23)24-2)5-25-16(10(6)11)27-17-14(22)13(21)12(20)9(4-18)26-17/h3,5,8-14,16-22H,4H2,1-2H3/t8-,9-,10-,11+,12-,13+,14-,16+,17+/m1/s1
• InChI Key: ZDZSVXGUBMNYJD-LPGRTNKPSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₇H₂₄O₁₀
• Molecular Weight: 388.40 g/mol
• Exact Mass: 388.13694696 g/mol
• Topological Polar Surface Area (TPSA): 155.00 Ų
• XlogP: -2.20
• Atomic LogP (AlogP): -2.23
• H-Bond Acceptor: 10
• H-Bond Donor: 5
• Rotatable Bonds: 4

Synonyms

• CHEMBL2048635

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.5789	57.89%
Caco-2	-	0.8508	85.08%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	-	0.7571	75.71%
Subcellular localzation	Mitochondria	0.6858	68.58%
OATP2B1 inhibitior	-	0.8593	85.93%
OATP1B1 inhibitior	+	0.7692	76.92%
OATP1B3 inhibitior	+	0.9601	96.01%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	-	0.8833	88.33%
P-glycoprotein inhibitior	-	0.8779	87.79%
P-glycoprotein substrate	-	0.8652	86.52%
CYP3A4 substrate	+	0.5807	58.07%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8748	87.48%
CYP3A4 inhibition	-	0.8900	89.00%
CYP2C9 inhibition	-	0.9190	91.90%
CYP2C19 inhibition	-	0.8705	87.05%
CYP2D6 inhibition	-	0.8892	88.92%
CYP1A2 inhibition	-	0.8992	89.92%
CYP2C8 inhibition	-	0.6872	68.72%
CYP inhibitory promiscuity	-	0.6928	69.28%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.7134	71.34%
Eye corrosion	-	0.9867	98.67%
Eye irritation	-	0.9552	95.52%
Skin irritation	-	0.7853	78.53%
Skin corrosion	-	0.9598	95.98%
Ames mutagenesis	-	0.5637	56.37%
Human Ether-a-go-go-Related Gene inhibition	-	0.5089	50.89%
Micronuclear	-	0.6641	66.41%
Hepatotoxicity	-	0.8000	80.00%
skin sensitisation	-	0.8808	88.08%
Respiratory toxicity	-	0.6000	60.00%
Reproductive toxicity	+	0.8444	84.44%
Mitochondrial toxicity	-	0.5125	51.25%
Nephrotoxicity	+	0.7418	74.18%
Acute Oral Toxicity (c)	III	0.4966	49.66%
Estrogen receptor binding	-	0.5601	56.01%
Androgen receptor binding	-	0.5591	55.91%
Thyroid receptor binding	-	0.6030	60.30%
Glucocorticoid receptor binding	-	0.6524	65.24%
Aromatase binding	-	0.5863	58.63%
PPAR gamma	-	0.6166	61.66%
Honey bee toxicity	-	0.8274	82.74%
Biodegradation	-	0.6500	65.00%
Crustacea aquatic toxicity	-	0.8100	81.00%
Fish aquatic toxicity	-	0.5356	53.56%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3401	O75469	Pregnane X receptor	94.41%	94.73%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.87%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	89.98%	91.11%
CHEMBL3060	Q9Y345	Glycine transporter 2	87.38%	99.17%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	86.99%	86.92%
CHEMBL3714130	P46095	G-protein coupled receptor 6	86.11%	97.36%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	83.06%	96.95%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	81.50%	96.00%

Plants that contains it

• Phlomoides rotata

Cross-Links

• PubChem: 70690437
• NPASS: NPC287262