[(1R,2R,6S,7S,8R,10S,11S,12R,16S,17R,18R)-6,7-dihydroxy-8-(hydroxymethyl)-16-isopropenyl-4,18-dimethyl-14-[(1E,3E)-nona-1,3-dienyl]-5-oxo-9,13,15,19-tetraoxahexacyclo[12.4.1.01,11.02,6.08,10.012,16]nonadec-3-en-17-yl] propanoate

Details

• Internal ID: c03df41f-e9cb-4052-a1fe-5cbe42ee4723
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids > Rhamnofolane and daphnane diterpenoids
• IUPAC Name: [(1R,2R,6S,7S,8R,10S,11S,12R,16S,17R,18R)-6,7-dihydroxy-8-(hydroxymethyl)-4,18-dimethyl-14-[(1E,3E)-nona-1,3-dienyl]-5-oxo-16-prop-1-en-2-yl-9,13,15,19-tetraoxahexacyclo[12.4.1.01,11.02,6.08,10.012,16]nonadec-3-en-17-yl] propanoate
• SMILES (Canonical): CCCCCC=CC=CC12OC3C4C5C(O5)(C(C6(C(C4(O1)C(C(C3(O2)C(=C)C)OC(=O)CC)C)C=C(C6=O)C)O)O)CO
• SMILES (Isomeric): CCCCC/C=C/C=C/C12O[C@@H]3[C@@H]4[C@H]5[C@](O5)([C@H]([C@]6([C@H]([C@@]4(O1)[C@@H]([C@H]([C@@]3(O2)C(=C)C)OC(=O)CC)C)C=C(C6=O)C)O)O)CO
• InChI: InChI=1S/C33H44O10/c1-7-9-10-11-12-13-14-15-30-41-27-23-26-29(17-34,40-26)28(37)31(38)21(16-19(5)24(31)36)33(23,43-30)20(6)25(39-22(35)8-2)32(27,42-30)18(3)4/h12-16,20-21,23,25-28,34,37-38H,3,7-11,17H2,1-2,4-6H3/b13-12+,15-14+/t20-,21-,23+,25-,26+,27-,28-,29+,30?,31-,32+,33+/m1/s1
• InChI Key: PVCYGTPNUOIKHH-SQADMDDHSA-N
• Popularity: 3 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₃H₄₄O₁₀
• Molecular Weight: 600.70 g/mol
• Exact Mass: 600.29344760 g/mol
• Topological Polar Surface Area (TPSA): 144.00 Ų
• XlogP: 3.60
• Atomic LogP (AlogP): 2.80
• H-Bond Acceptor: 10
• H-Bond Donor: 3
• Rotatable Bonds: 10

Synonyms

• [(1R,2R,6S,7S,8R,10S,11S,12R,16S,17R,18R)-6,7-dihydroxy-8-(hydroxymethyl)-16-isopropenyl-4,18-dimethyl-14-[(1E,3E)-nona-1,3-dienyl]-5-oxo-9,13,15,19-tetraoxahexacyclo[12.4.1.01,11.02,6.08,10.012,16]nonadec-3-en-17-yl] propanoate

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8797	87.97%
Caco-2	-	0.8000	80.00%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	-	0.6857	68.57%
Subcellular localzation	Mitochondria	0.7178	71.78%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.7857	78.57%
OATP1B3 inhibitior	+	0.9319	93.19%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.7750	77.50%
BSEP inhibitior	+	0.8593	85.93%
P-glycoprotein inhibitior	+	0.7444	74.44%
P-glycoprotein substrate	+	0.6461	64.61%
CYP3A4 substrate	+	0.7128	71.28%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8862	88.62%
CYP3A4 inhibition	+	0.5131	51.31%
CYP2C9 inhibition	-	0.6929	69.29%
CYP2C19 inhibition	-	0.7760	77.60%
CYP2D6 inhibition	-	0.9119	91.19%
CYP1A2 inhibition	-	0.7777	77.77%
CYP2C8 inhibition	+	0.7338	73.38%
CYP inhibitory promiscuity	-	0.7597	75.97%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.5936	59.36%
Eye corrosion	-	0.9837	98.37%
Eye irritation	-	0.9163	91.63%
Skin irritation	-	0.6041	60.41%
Skin corrosion	-	0.9175	91.75%
Ames mutagenesis	-	0.6900	69.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3697	36.97%
Micronuclear	-	0.7100	71.00%
Hepatotoxicity	-	0.5500	55.00%
skin sensitisation	-	0.8650	86.50%
Respiratory toxicity	+	0.6889	68.89%
Reproductive toxicity	+	0.8667	86.67%
Mitochondrial toxicity	+	0.7000	70.00%
Nephrotoxicity	+	0.6130	61.30%
Acute Oral Toxicity (c)	III	0.5736	57.36%
Estrogen receptor binding	+	0.7017	70.17%
Androgen receptor binding	+	0.7350	73.50%
Thyroid receptor binding	+	0.5623	56.23%
Glucocorticoid receptor binding	+	0.6722	67.22%
Aromatase binding	+	0.6810	68.10%
PPAR gamma	+	0.6530	65.30%
Honey bee toxicity	-	0.7883	78.83%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	+	0.5202	52.02%
Fish aquatic toxicity	+	0.9887	98.87%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4040	P28482	MAP kinase ERK2	98.04%	83.82%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.66%	91.11%
CHEMBL3060	Q9Y345	Glycine transporter 2	95.13%	99.17%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.96%	96.09%
CHEMBL2996	Q05655	Protein kinase C delta	93.77%	97.79%
CHEMBL2581	P07339	Cathepsin D	93.48%	98.95%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	90.46%	96.90%
CHEMBL2072	P35499	Sodium channel protein type IV alpha subunit	89.79%	92.32%
CHEMBL299	P17252	Protein kinase C alpha	89.32%	98.03%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	89.18%	91.24%
CHEMBL1806	P11388	DNA topoisomerase II alpha	87.88%	89.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.31%	86.33%
CHEMBL5103	Q969S8	Histone deacetylase 10	86.19%	90.08%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	85.89%	94.80%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	85.78%	96.95%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	82.74%	96.47%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	82.26%	95.56%
CHEMBL3359	P21462	Formyl peptide receptor 1	81.91%	93.56%
CHEMBL2265	P23141	Acyl coenzyme A:cholesterol acyltransferase	81.74%	85.94%
CHEMBL5255	O00206	Toll-like receptor 4	81.34%	92.50%
CHEMBL2001	Q9H244	Purinergic receptor P2Y12	81.11%	96.00%

Plants that contains it

• Daphne genkwa

Cross-Links

• PubChem: 46191238
• NPASS: NPC471137
• ChEMBL: CHEMBL2376817
• LOTUS: LTS0265606
• wikiData: Q105215395