[(1R,2S,4R,5S,6S,10S,11R,12R,14R,15R)-5,6,11,14-tetrahydroxy-4-(hydroxymethyl)-8,12-dimethyl-7-oxo-14-prop-1-en-2-yl-3-oxatetracyclo[9.4.0.02,4.06,10]pentadec-8-en-15-yl] (2E,4E)-pentadeca-2,4-dienoate

Details

• Internal ID: 8d29c6ef-3579-458a-a010-a787e537b326
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids > Rhamnofolane and daphnane diterpenoids
• IUPAC Name: [(1R,2S,4R,5S,6S,10S,11R,12R,14R,15R)-5,6,11,14-tetrahydroxy-4-(hydroxymethyl)-8,12-dimethyl-7-oxo-14-prop-1-en-2-yl-3-oxatetracyclo[9.4.0.02,4.06,10]pentadec-8-en-15-yl] (2E,4E)-pentadeca-2,4-dienoate
• SMILES (Canonical): CCCCCCCCCCC=CC=CC(=O)OC1C2C3C(O3)(C(C4(C(C2(C(CC1(C(=C)C)O)C)O)C=C(C4=O)C)O)O)CO
• SMILES (Isomeric): CCCCCCCCCC/C=C/C=C/C(=O)O[C@@H]1[C@H]2[C@H]3[C@](O3)([C@H]([C@]4([C@H]([C@]2([C@@H](C[C@]1(C(=C)C)O)C)O)C=C(C4=O)C)O)O)CO
• InChI: InChI=1S/C35H52O9/c1-6-7-8-9-10-11-12-13-14-15-16-17-18-26(37)43-29-27-30-33(21-36,44-30)31(39)35(42)25(19-23(4)28(35)38)34(27,41)24(5)20-32(29,40)22(2)3/h15-19,24-25,27,29-31,36,39-42H,2,6-14,20-21H2,1,3-5H3/b16-15+,18-17+/t24-,25+,27+,29-,30+,31-,32-,33+,34+,35-/m1/s1
• InChI Key: RRXYNHPLKDIRDY-BWPZUKLGSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₅H₅₂O₉
• Molecular Weight: 616.80 g/mol
• Exact Mass: 616.36113323 g/mol
• Topological Polar Surface Area (TPSA): 157.00 Ų
• XlogP: 5.60
• Atomic LogP (AlogP): 3.62
• H-Bond Acceptor: 9
• H-Bond Donor: 5
• Rotatable Bonds: 14

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9188	91.88%
Caco-2	-	0.8315	83.15%
Blood Brain Barrier	+	0.5500	55.00%
Human oral bioavailability	-	0.8286	82.86%
Subcellular localzation	Mitochondria	0.6639	66.39%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8210	82.10%
OATP1B3 inhibitior	+	0.9439	94.39%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.5818	58.18%
BSEP inhibitior	+	0.8304	83.04%
P-glycoprotein inhibitior	+	0.7148	71.48%
P-glycoprotein substrate	+	0.6465	64.65%
CYP3A4 substrate	+	0.7092	70.92%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8963	89.63%
CYP3A4 inhibition	+	0.5909	59.09%
CYP2C9 inhibition	+	0.5765	57.65%
CYP2C19 inhibition	-	0.7843	78.43%
CYP2D6 inhibition	-	0.9254	92.54%
CYP1A2 inhibition	-	0.7812	78.12%
CYP2C8 inhibition	+	0.6920	69.20%
CYP inhibitory promiscuity	-	0.9108	91.08%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.7017	70.17%
Eye corrosion	-	0.9878	98.78%
Eye irritation	-	0.9130	91.30%
Skin irritation	-	0.5284	52.84%
Skin corrosion	-	0.9360	93.60%
Ames mutagenesis	-	0.6800	68.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7826	78.26%
Micronuclear	-	0.7000	70.00%
Hepatotoxicity	-	0.5347	53.47%
skin sensitisation	-	0.8878	88.78%
Respiratory toxicity	+	0.6000	60.00%
Reproductive toxicity	+	0.8000	80.00%
Mitochondrial toxicity	+	0.8500	85.00%
Nephrotoxicity	+	0.4875	48.75%
Acute Oral Toxicity (c)	III	0.4638	46.38%
Estrogen receptor binding	+	0.7281	72.81%
Androgen receptor binding	+	0.7048	70.48%
Thyroid receptor binding	-	0.4949	49.49%
Glucocorticoid receptor binding	+	0.6195	61.95%
Aromatase binding	+	0.5914	59.14%
PPAR gamma	+	0.5794	57.94%
Honey bee toxicity	-	0.8101	81.01%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	+	0.6639	66.39%
Fish aquatic toxicity	+	0.9879	98.79%

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	97.56%	91.11%
CHEMBL2581	P07339	Cathepsin D	96.06%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.62%	96.09%
CHEMBL230	P35354	Cyclooxygenase-2	95.29%	89.63%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	94.98%	94.45%
CHEMBL1293249	Q13887	Kruppel-like factor 5	94.86%	86.33%
CHEMBL3060	Q9Y345	Glycine transporter 2	92.97%	99.17%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	92.84%	96.95%
CHEMBL2996	Q05655	Protein kinase C delta	91.39%	97.79%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.88%	95.56%
CHEMBL299	P17252	Protein kinase C alpha	90.21%	98.03%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	90.08%	94.80%
CHEMBL3401	O75469	Pregnane X receptor	90.08%	94.73%
CHEMBL2072	P35499	Sodium channel protein type IV alpha subunit	89.71%	92.32%
CHEMBL221	P23219	Cyclooxygenase-1	89.14%	90.17%
CHEMBL4769	O95749	Geranylgeranyl pyrophosphate synthetase	87.33%	92.08%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.63%	97.09%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	86.62%	96.90%
CHEMBL340	P08684	Cytochrome P450 3A4	86.05%	91.19%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.77%	89.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	84.73%	95.89%
CHEMBL3359	P21462	Formyl peptide receptor 1	84.42%	93.56%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	83.91%	89.34%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	83.90%	95.50%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	83.70%	100.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	82.96%	100.00%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	81.19%	96.47%
CHEMBL3267	P48736	PI3-kinase p110-gamma subunit	80.76%	95.71%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	80.60%	93.00%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	80.26%	91.24%
CHEMBL5103	Q969S8	Histone deacetylase 10	80.16%	90.08%

Plants that contains it

• Wikstroemia retusa

Cross-Links

• PubChem: 162884723
• LOTUS: LTS0258664
• wikiData: Q105244429