7,8-Didehydropenstemoside

Details

• Internal ID: a0198ed5-47fe-456d-bd66-e94025bc8036
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Iridoid O-glycosides
• IUPAC Name: methyl (1S,4aR,5R,7aR)-4a,5-dihydroxy-7-methyl-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-5,7a-dihydro-1H-cyclopenta[c]pyran-4-carboxylate
• SMILES (Canonical): CC1=CC(C2(C1C(OC=C2C(=O)OC)OC3C(C(C(C(O3)CO)O)O)O)O)O
• SMILES (Isomeric): CC1=C[C@H]([C@]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)O
• InChI: InChI=1S/C17H24O11/c1-6-3-9(19)17(24)7(14(23)25-2)5-26-15(10(6)17)28-16-13(22)12(21)11(20)8(4-18)27-16/h3,5,8-13,15-16,18-22,24H,4H2,1-2H3/t8-,9-,10+,11-,12+,13-,15+,16+,17-/m1/s1
• InChI Key: WUZGENDUAYSYJW-BKDJBYHXSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₇H₂₄O₁₁
• Molecular Weight: 404.40 g/mol
• Exact Mass: 404.13186158 g/mol
• Topological Polar Surface Area (TPSA): 175.00 Ų
• XlogP: -2.70
• Atomic LogP (AlogP): -3.12
• H-Bond Acceptor: 11
• H-Bond Donor: 6
• Rotatable Bonds: 4

Synonyms

• 7,8-Didehydropenstemoside
• CHEMBL2048532

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6019	60.19%
Caco-2	-	0.8601	86.01%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.8429	84.29%
Subcellular localzation	Mitochondria	0.7140	71.40%
OATP2B1 inhibitior	-	0.8564	85.64%
OATP1B1 inhibitior	+	0.7753	77.53%
OATP1B3 inhibitior	+	0.9477	94.77%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.8313	83.13%
P-glycoprotein inhibitior	-	0.8672	86.72%
P-glycoprotein substrate	-	0.7864	78.64%
CYP3A4 substrate	+	0.6451	64.51%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8781	87.81%
CYP3A4 inhibition	-	0.9274	92.74%
CYP2C9 inhibition	-	0.9205	92.05%
CYP2C19 inhibition	-	0.8751	87.51%
CYP2D6 inhibition	-	0.9106	91.06%
CYP1A2 inhibition	-	0.9005	90.05%
CYP2C8 inhibition	-	0.6199	61.99%
CYP inhibitory promiscuity	-	0.7532	75.32%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6718	67.18%
Eye corrosion	-	0.9877	98.77%
Eye irritation	-	0.9547	95.47%
Skin irritation	-	0.7532	75.32%
Skin corrosion	-	0.9503	95.03%
Ames mutagenesis	-	0.5200	52.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6147	61.47%
Micronuclear	-	0.6641	66.41%
Hepatotoxicity	-	0.8625	86.25%
skin sensitisation	-	0.8530	85.30%
Respiratory toxicity	+	0.5222	52.22%
Reproductive toxicity	+	0.8667	86.67%
Mitochondrial toxicity	+	0.5375	53.75%
Nephrotoxicity	-	0.5584	55.84%
Acute Oral Toxicity (c)	III	0.4425	44.25%
Estrogen receptor binding	-	0.5707	57.07%
Androgen receptor binding	+	0.5683	56.83%
Thyroid receptor binding	-	0.5236	52.36%
Glucocorticoid receptor binding	-	0.5151	51.51%
Aromatase binding	+	0.5892	58.92%
PPAR gamma	-	0.5342	53.42%
Honey bee toxicity	-	0.8126	81.26%
Biodegradation	-	0.6000	60.00%
Crustacea aquatic toxicity	-	0.7100	71.00%
Fish aquatic toxicity	-	0.5319	53.19%

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	96.56%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.61%	91.11%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	88.31%	86.92%
CHEMBL3401	O75469	Pregnane X receptor	88.28%	94.73%
CHEMBL2581	P07339	Cathepsin D	86.35%	98.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	83.53%	94.45%
CHEMBL4208	P20618	Proteasome component C5	82.83%	90.00%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	81.31%	94.00%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	81.24%	94.33%
CHEMBL3060	Q9Y345	Glycine transporter 2	80.33%	99.17%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	80.14%	91.24%

Plants that contains it

• Phlomoides rotata

Cross-Links

• PubChem: 70684135
• NPASS: NPC272827
• LOTUS: LTS0225991
• wikiData: Q105313398