(1S,4aR,7S,7aR)-7-(hydroxymethyl)-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-4-carboxylic acid

Details

• Internal ID: 90f11bb0-1234-4873-a887-d5a063ac8c48
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Iridoid O-glycosides
• IUPAC Name: (1S,4aR,7S,7aR)-7-(hydroxymethyl)-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-4-carboxylic acid
• SMILES (Canonical): C1CC2C(C1CO)C(OC=C2C(=O)O)OC3C(C(C(C(O3)CO)O)O)O
• SMILES (Isomeric): C1C[C@@H]2[C@H]([C@H]1CO)[C@@H](OC=C2C(=O)O)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O
• InChI: InChI=1S/C16H24O10/c17-3-6-1-2-7-8(14(22)23)5-24-15(10(6)7)26-16-13(21)12(20)11(19)9(4-18)25-16/h5-7,9-13,15-21H,1-4H2,(H,22,23)/t6-,7+,9-,10+,11-,12+,13-,15+,16+/m1/s1
• InChI Key: XJOPDXRZTFGTIW-CLTNYIICSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₆H₂₄O₁₀
• Molecular Weight: 376.36 g/mol
• Exact Mass: 376.13694696 g/mol
• Topological Polar Surface Area (TPSA): 166.00 Ų
• XlogP: -1.80
• Atomic LogP (AlogP): -2.24
• H-Bond Acceptor: 9
• H-Bond Donor: 6
• Rotatable Bonds: 5

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5459	54.59%
Caco-2	-	0.8935	89.35%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	-	0.7714	77.14%
Subcellular localzation	Mitochondria	0.8096	80.96%
OATP2B1 inhibitior	-	0.8596	85.96%
OATP1B1 inhibitior	+	0.6985	69.85%
OATP1B3 inhibitior	+	0.9450	94.50%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.7750	77.50%
BSEP inhibitior	-	0.9468	94.68%
P-glycoprotein inhibitior	-	0.9186	91.86%
P-glycoprotein substrate	-	0.9393	93.93%
CYP3A4 substrate	-	0.5000	50.00%
CYP2C9 substrate	-	0.8078	80.78%
CYP2D6 substrate	-	0.8715	87.15%
CYP3A4 inhibition	-	0.9636	96.36%
CYP2C9 inhibition	-	0.9264	92.64%
CYP2C19 inhibition	-	0.8394	83.94%
CYP2D6 inhibition	-	0.8775	87.75%
CYP1A2 inhibition	-	0.8221	82.21%
CYP2C8 inhibition	-	0.7741	77.41%
CYP inhibitory promiscuity	-	0.8738	87.38%
UGT catelyzed	-	0.7000	70.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.7117	71.17%
Eye corrosion	-	0.9847	98.47%
Eye irritation	-	0.9523	95.23%
Skin irritation	-	0.8045	80.45%
Skin corrosion	-	0.9624	96.24%
Ames mutagenesis	-	0.5870	58.70%
Human Ether-a-go-go-Related Gene inhibition	-	0.6208	62.08%
Micronuclear	-	0.8800	88.00%
Hepatotoxicity	-	0.8714	87.14%
skin sensitisation	-	0.8818	88.18%
Respiratory toxicity	+	0.5889	58.89%
Reproductive toxicity	+	0.7222	72.22%
Mitochondrial toxicity	-	0.5000	50.00%
Nephrotoxicity	-	0.5703	57.03%
Acute Oral Toxicity (c)	III	0.4168	41.68%
Estrogen receptor binding	-	0.5129	51.29%
Androgen receptor binding	-	0.4920	49.20%
Thyroid receptor binding	-	0.5084	50.84%
Glucocorticoid receptor binding	-	0.7124	71.24%
Aromatase binding	+	0.5495	54.95%
PPAR gamma	+	0.5910	59.10%
Honey bee toxicity	-	0.9044	90.44%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.7750	77.50%
Fish aquatic toxicity	+	0.7533	75.33%

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	94.56%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.22%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.76%	97.09%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	87.45%	86.92%
CHEMBL5255	O00206	Toll-like receptor 4	86.14%	92.50%
CHEMBL3060	Q9Y345	Glycine transporter 2	84.69%	99.17%
CHEMBL216	P11229	Muscarinic acetylcholine receptor M1	83.36%	94.23%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.72%	89.00%
CHEMBL218	P21554	Cannabinoid CB1 receptor	82.12%	96.61%

Plants that contains it

• Cordylanthus kingii

Cross-Links

• PubChem: 21591680
• LOTUS: LTS0175962
• wikiData: Q105329100