[(1S,4aR,7S,7aS)-7-hydroxy-7-methyl-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] (Z)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate

Details

• Internal ID: 06d12041-a9fe-47bf-aa02-42c66fe08ac3
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Iridoid O-glycosides
• IUPAC Name: [(1S,4aR,7S,7aS)-7-hydroxy-7-methyl-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] (Z)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate
• SMILES (Canonical): CC1(CC(C2C1C(OC=C2)OC3C(C(C(C(O3)CO)O)O)O)OC(=O)C=CC4=CC(=C(C=C4)O)OC)O
• SMILES (Isomeric): C[C@@]1(CC([C@H]2[C@@H]1[C@@H](OC=C2)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)OC(=O)/C=C\C4=CC(=C(C=C4)O)OC)O
• InChI: InChI=1S/C25H32O12/c1-25(32)10-16(35-18(28)6-4-12-3-5-14(27)15(9-12)33-2)13-7-8-34-23(19(13)25)37-24-22(31)21(30)20(29)17(11-26)36-24/h3-9,13,16-17,19-24,26-27,29-32H,10-11H2,1-2H3/b6-4-/t13-,16?,17+,19+,20+,21-,22+,23-,24-,25-/m0/s1
• InChI Key: LOCASNZLOPRAJY-ULTVMYMVSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₅H₃₂O₁₂
• Molecular Weight: 524.50 g/mol
• Exact Mass: 524.18937645 g/mol
• Topological Polar Surface Area (TPSA): 185.00 Ų
• XlogP: 0.10
• Atomic LogP (AlogP): -0.60
• H-Bond Acceptor: 12
• H-Bond Donor: 6
• Rotatable Bonds: 7

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7567	75.67%
Caco-2	-	0.8951	89.51%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	-	0.8429	84.29%
Subcellular localzation	Mitochondria	0.5174	51.74%
OATP2B1 inhibitior	-	0.8601	86.01%
OATP1B1 inhibitior	+	0.8549	85.49%
OATP1B3 inhibitior	+	0.9544	95.44%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	-	0.5000	50.00%
P-glycoprotein inhibitior	-	0.6161	61.61%
P-glycoprotein substrate	-	0.5923	59.23%
CYP3A4 substrate	+	0.6854	68.54%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8689	86.89%
CYP3A4 inhibition	-	0.7980	79.80%
CYP2C9 inhibition	-	0.9250	92.50%
CYP2C19 inhibition	-	0.8799	87.99%
CYP2D6 inhibition	-	0.8572	85.72%
CYP1A2 inhibition	-	0.8165	81.65%
CYP2C8 inhibition	+	0.7134	71.34%
CYP inhibitory promiscuity	-	0.8378	83.78%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.5976	59.76%
Eye corrosion	-	0.9907	99.07%
Eye irritation	-	0.9571	95.71%
Skin irritation	-	0.7681	76.81%
Skin corrosion	-	0.9398	93.98%
Ames mutagenesis	-	0.6200	62.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6739	67.39%
Micronuclear	-	0.5226	52.26%
Hepatotoxicity	-	0.8069	80.69%
skin sensitisation	-	0.8298	82.98%
Respiratory toxicity	-	0.5000	50.00%
Reproductive toxicity	+	0.9111	91.11%
Mitochondrial toxicity	+	0.6250	62.50%
Nephrotoxicity	-	0.9077	90.77%
Acute Oral Toxicity (c)	III	0.5478	54.78%
Estrogen receptor binding	+	0.7615	76.15%
Androgen receptor binding	-	0.5000	50.00%
Thyroid receptor binding	+	0.5810	58.10%
Glucocorticoid receptor binding	+	0.6297	62.97%
Aromatase binding	+	0.5241	52.41%
PPAR gamma	+	0.6784	67.84%
Honey bee toxicity	-	0.7485	74.85%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.5955	59.55%
Fish aquatic toxicity	+	0.8121	81.21%

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	99.86%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.27%	96.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	97.42%	86.33%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	95.89%	96.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	95.24%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	93.70%	89.00%
CHEMBL241	Q14432	Phosphodiesterase 3A	92.13%	92.94%
CHEMBL3137262	O60341	LSD1/CoREST complex	89.88%	97.09%
CHEMBL4208	P20618	Proteasome component C5	89.11%	90.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	87.81%	99.17%
CHEMBL3194	P02766	Transthyretin	87.40%	90.71%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	86.55%	94.45%
CHEMBL5608	Q16288	NT-3 growth factor receptor	84.17%	95.89%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	83.73%	96.21%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	83.72%	92.62%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	83.59%	89.62%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	83.23%	95.50%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	83.08%	96.95%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	80.43%	97.14%

Plants that contains it

• Actaea cimicifuga
• Actaea dahurica
• Allium cepa
• Angelica sinensis
• Beta vulgaris
• Capparis spinosa
• Catalpa ovata
• Chamaemelum nobile
• Citrus limon
• Conioselinum anthriscoides
• Coptis chinensis
• Corydalis decumbens
• Equisetum hyemale
• Foeniculum vulgare
• Hansenia weberbaueriana
• Huperzia selago
• Lycopodium japonicum
• Neopicrorhiza scrophulariiflora
• Oryza sativa
• Plantago major
• Raphanus raphanistrum subsp. sativus
• Rehmannia glutinosa
• Taraxacum officinale
• Tsuga heterophylla
• Urtica dioica

Cross-Links

• PubChem: 6325178
• NPASS: NPC3780