1-O-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] 16-O-[[(1S,2S,3S,4R,5S)-2,3,4-trihydroxy-5-(1,3,6,7-tetrahydroxy-9-oxoxanthen-2-yl)cyclohexyl]methyl] (2E,4E,6E,8Z,10E,12E,14E)-2,6,11,15-tetramethylhexadeca-2,4,6,8,10,12,14-heptaenedioate

Details

• Internal ID: 53810a48-cbcb-433e-bc30-2273d5800280
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids
• IUPAC Name: 1-O-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] 16-O-[[(1S,2S,3S,4R,5S)-2,3,4-trihydroxy-5-(1,3,6,7-tetrahydroxy-9-oxoxanthen-2-yl)cyclohexyl]methyl] (2E,4E,6E,8Z,10E,12E,14E)-2,6,11,15-tetramethylhexadeca-2,4,6,8,10,12,14-heptaenedioate
• SMILES (Canonical): CC(=CC=CC=C(C)C=CC=C(C)C(=O)OC1C(C(C(C(O1)CO)O)O)O)C=CC=C(C)C(=O)OCC2CC(C(C(C2O)O)O)C3=C(C4=C(C=C3O)OC5=CC(=C(C=C5C4=O)O)O)O
• SMILES (Isomeric): C/C(=C\C=C/C=C(\C)/C=C/C=C(\C)/C(=O)O[C@H]1[C@@H]([C@H]([C@@H]([C@H](O1)CO)O)O)O)/C=C/C=C(\C)/C(=O)OC[C@@H]2C[C@H]([C@H]([C@@H]([C@H]2O)O)O)C3=C(C4=C(C=C3O)OC5=CC(=C(C=C5C4=O)O)O)O
• InChI: InChI=1S/C46H52O18/c1-21(9-5-6-10-22(2)12-8-14-24(4)45(60)64-46-43(58)42(57)39(54)33(19-47)63-46)11-7-13-23(3)44(59)61-20-25-15-27(38(53)41(56)36(25)51)34-30(50)18-32-35(40(34)55)37(52)26-16-28(48)29(49)17-31(26)62-32/h5-14,16-18,25,27,33,36,38-39,41-43,46-51,53-58H,15,19-20H2,1-4H3/b6-5-,11-7+,12-8+,21-9+,22-10+,23-13+,24-14+/t25-,27-,33+,36-,38+,39+,41+,42-,43+,46-/m0/s1
• InChI Key: NCWGUSGGDZUCES-BMPAEULOSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₆H₅₂O₁₈
• Molecular Weight: 892.90 g/mol
• Exact Mass: 892.31536481 g/mol
• Topological Polar Surface Area (TPSA): 311.00 Ų
• XlogP: 4.40
• Atomic LogP (AlogP): 2.29
• H-Bond Acceptor: 18
• H-Bond Donor: 11
• Rotatable Bonds: 13

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.5763	57.63%
Caco-2	-	0.8630	86.30%
Blood Brain Barrier	-	0.6750	67.50%
Human oral bioavailability	-	0.6429	64.29%
Subcellular localzation	Mitochondria	0.6362	63.62%
OATP2B1 inhibitior	-	0.5702	57.02%
OATP1B1 inhibitior	+	0.8378	83.78%
OATP1B3 inhibitior	+	0.9480	94.80%
MATE1 inhibitior	-	0.8400	84.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	+	0.9658	96.58%
P-glycoprotein inhibitior	+	0.7488	74.88%
P-glycoprotein substrate	+	0.6177	61.77%
CYP3A4 substrate	+	0.7024	70.24%
CYP2C9 substrate	+	0.5915	59.15%
CYP2D6 substrate	-	0.8600	86.00%
CYP3A4 inhibition	-	0.9221	92.21%
CYP2C9 inhibition	-	0.7219	72.19%
CYP2C19 inhibition	-	0.8258	82.58%
CYP2D6 inhibition	-	0.9418	94.18%
CYP1A2 inhibition	-	0.8311	83.11%
CYP2C8 inhibition	+	0.6689	66.89%
CYP inhibitory promiscuity	-	0.6330	63.30%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.6733	67.33%
Eye corrosion	-	0.9906	99.06%
Eye irritation	-	0.9037	90.37%
Skin irritation	-	0.8180	81.80%
Skin corrosion	-	0.9517	95.17%
Ames mutagenesis	+	0.5163	51.63%
Human Ether-a-go-go-Related Gene inhibition	+	0.8239	82.39%
Micronuclear	+	0.5300	53.00%
Hepatotoxicity	-	0.6426	64.26%
skin sensitisation	-	0.8530	85.30%
Respiratory toxicity	+	0.7333	73.33%
Reproductive toxicity	+	0.8667	86.67%
Mitochondrial toxicity	+	0.6625	66.25%
Nephrotoxicity	-	0.9735	97.35%
Acute Oral Toxicity (c)	III	0.5378	53.78%
Estrogen receptor binding	+	0.8007	80.07%
Androgen receptor binding	+	0.7453	74.53%
Thyroid receptor binding	+	0.6105	61.05%
Glucocorticoid receptor binding	+	0.7045	70.45%
Aromatase binding	+	0.6331	63.31%
PPAR gamma	+	0.7782	77.82%
Honey bee toxicity	-	0.6930	69.30%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.6400	64.00%
Fish aquatic toxicity	+	0.9640	96.40%

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	99.84%	91.11%
CHEMBL1806	P11388	DNA topoisomerase II alpha	98.53%	89.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	96.00%	94.45%
CHEMBL3137262	O60341	LSD1/CoREST complex	95.80%	97.09%
CHEMBL241	Q14432	Phosphodiesterase 3A	94.49%	92.94%
CHEMBL2581	P07339	Cathepsin D	93.94%	98.95%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	93.63%	96.21%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.27%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.04%	95.56%
CHEMBL3401	O75469	Pregnane X receptor	91.88%	94.73%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	91.70%	94.00%
CHEMBL1937	Q92769	Histone deacetylase 2	91.12%	94.75%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	89.98%	99.23%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	89.24%	94.80%
CHEMBL5852	Q96P65	Pyroglutamylated RFamide peptide receptor	86.71%	85.00%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	86.57%	86.92%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	85.43%	95.50%
CHEMBL1994	P08235	Mineralocorticoid receptor	85.23%	100.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	84.10%	86.33%
CHEMBL5255	O00206	Toll-like receptor 4	82.92%	92.50%
CHEMBL3060	Q9Y345	Glycine transporter 2	81.69%	99.17%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	80.88%	89.62%
CHEMBL5103	Q969S8	Histone deacetylase 10	80.79%	90.08%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	80.52%	90.71%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.13%	95.89%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	80.04%	95.64%

Plants that contains it

• Crocus sativus
• Prunus armeniaca

Cross-Links

• PubChem: 11972403
• NPASS: NPC181314