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

Details

• Internal ID: 333410bd-0e62-472c-b005-11b5ede83dcd
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Iridoid O-glycosides
• IUPAC Name: [(1S,4aR,5S,6R,7S,7aS)-6,7-dihydroxy-7-(hydroxymethyl)-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4a,5,6,7a-tetrahydro-1H-cyclopenta[c]pyran-5-yl] (E)-3-(4-hydroxyphenyl)prop-2-enoate
• SMILES (Canonical): C1=COC(C2C1C(C(C2(CO)O)O)OC(=O)C=CC3=CC=C(C=C3)O)OC4C(C(C(C(O4)CO)O)O)O
• SMILES (Isomeric): C1=CO[C@H]([C@H]2[C@@H]1[C@@H]([C@H]([C@]2(CO)O)O)OC(=O)/C=C/C3=CC=C(C=C3)O)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O
• InChI: InChI=1S/C24H30O13/c25-9-14-17(29)18(30)19(31)23(35-14)37-22-16-13(7-8-34-22)20(21(32)24(16,33)10-26)36-15(28)6-3-11-1-4-12(27)5-2-11/h1-8,13-14,16-23,25-27,29-33H,9-10H2/b6-3+/t13-,14-,16-,17-,18+,19-,20+,21-,22+,23+,24-/m1/s1
• InChI Key: CISPZGJMMIWQCY-WVSQEAJASA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₄H₃₀O₁₃
• Molecular Weight: 526.50 g/mol
• Exact Mass: 526.16864101 g/mol
• Topological Polar Surface Area (TPSA): 216.00 Ų
• XlogP: -1.40
• Atomic LogP (AlogP): -2.67
• H-Bond Acceptor: 13
• H-Bond Donor: 8
• Rotatable Bonds: 7

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.5822	58.22%
Caco-2	-	0.9230	92.30%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	-	0.8714	87.14%
Subcellular localzation	Mitochondria	0.5469	54.69%
OATP2B1 inhibitior	-	0.8504	85.04%
OATP1B1 inhibitior	+	0.8225	82.25%
OATP1B3 inhibitior	+	0.9580	95.80%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	-	0.5715	57.15%
P-glycoprotein inhibitior	-	0.6630	66.30%
P-glycoprotein substrate	-	0.7120	71.20%
CYP3A4 substrate	+	0.6463	64.63%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8713	87.13%
CYP3A4 inhibition	-	0.9197	91.97%
CYP2C9 inhibition	-	0.9482	94.82%
CYP2C19 inhibition	-	0.8346	83.46%
CYP2D6 inhibition	-	0.8656	86.56%
CYP1A2 inhibition	-	0.9075	90.75%
CYP2C8 inhibition	+	0.6870	68.70%
CYP inhibitory promiscuity	-	0.8525	85.25%
UGT catelyzed	-	0.6638	66.38%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.5510	55.10%
Eye corrosion	-	0.9923	99.23%
Eye irritation	-	0.9403	94.03%
Skin irritation	-	0.7825	78.25%
Skin corrosion	-	0.9525	95.25%
Ames mutagenesis	-	0.5800	58.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4108	41.08%
Micronuclear	-	0.5467	54.67%
Hepatotoxicity	-	0.8750	87.50%
skin sensitisation	-	0.8181	81.81%
Respiratory toxicity	-	0.5222	52.22%
Reproductive toxicity	+	0.8444	84.44%
Mitochondrial toxicity	+	0.5750	57.50%
Nephrotoxicity	-	0.6318	63.18%
Acute Oral Toxicity (c)	III	0.5135	51.35%
Estrogen receptor binding	+	0.6997	69.97%
Androgen receptor binding	+	0.5428	54.28%
Thyroid receptor binding	+	0.5512	55.12%
Glucocorticoid receptor binding	-	0.5181	51.81%
Aromatase binding	+	0.6149	61.49%
PPAR gamma	+	0.7477	74.77%
Honey bee toxicity	-	0.6957	69.57%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.6300	63.00%
Fish aquatic toxicity	+	0.6642	66.42%

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	98.79%	91.11%
CHEMBL4040	P28482	MAP kinase ERK2	95.10%	83.82%
CHEMBL1293249	Q13887	Kruppel-like factor 5	93.23%	86.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	91.29%	89.00%
CHEMBL2563	Q9UQL6	Histone deacetylase 5	91.16%	89.67%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	90.58%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.49%	95.56%
CHEMBL3194	P02766	Transthyretin	90.38%	90.71%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	89.71%	96.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	88.55%	97.09%
CHEMBL211	P08172	Muscarinic acetylcholine receptor M2	85.68%	94.97%
CHEMBL3060	Q9Y345	Glycine transporter 2	85.16%	99.17%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	85.02%	94.45%
CHEMBL216	P11229	Muscarinic acetylcholine receptor M1	85.00%	94.23%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	84.89%	86.92%
CHEMBL4208	P20618	Proteasome component C5	84.70%	90.00%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	80.17%	95.89%

Plants that contains it

• Stereospermum cylindricum

Cross-Links

• PubChem: 101397352
• LOTUS: LTS0004513
• wikiData: Q104960207