(2R,3R,4S,5S,6R)-2-[[(1S,4aS,10aR)-5-hydroxy-7-[(2S)-1-hydroxypropan-2-yl]-1,4a-dimethyl-6-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2,3,4,9,10,10a-hexahydrophenanthren-1-yl]methoxy]-6-(hydroxymethyl)oxane-3,4,5-triol

Details

• Internal ID: 94336e80-a352-4728-986a-cedd19e16a06
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Diterpene glycosides
• IUPAC Name: (2R,3R,4S,5S,6R)-2-[[(1S,4aS,10aR)-5-hydroxy-7-[(2S)-1-hydroxypropan-2-yl]-1,4a-dimethyl-6-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2,3,4,9,10,10a-hexahydrophenanthren-1-yl]methoxy]-6-(hydroxymethyl)oxane-3,4,5-triol
• SMILES (Canonical): CC(CO)C1=C(C(=C2C(=C1)CCC3C2(CCCC3(C)COC4C(C(C(C(O4)CO)O)O)O)C)O)OC5C(C(C(C(O5)CO)O)O)O
• SMILES (Isomeric): C[C@H](CO)C1=C(C(=C2C(=C1)CC[C@@H]3[C@@]2(CCC[C@]3(C)CO[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)C)O)O[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)CO)O)O)O
• InChI: InChI=1S/C32H50O14/c1-14(10-33)16-9-15-5-6-19-31(2,13-43-29-26(41)24(39)21(36)17(11-34)44-29)7-4-8-32(19,3)20(15)23(38)28(16)46-30-27(42)25(40)22(37)18(12-35)45-30/h9,14,17-19,21-22,24-27,29-30,33-42H,4-8,10-13H2,1-3H3/t14-,17-,18-,19+,21-,22-,24+,25+,26-,27-,29-,30+,31-,32+/m1/s1
• InChI Key: AKJKBBDQAFRAJQ-KKAOFZDASA-N
• Popularity: 3 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₂H₅₀O₁₄
• Molecular Weight: 658.70 g/mol
• Exact Mass: 658.32005626 g/mol
• Topological Polar Surface Area (TPSA): 239.00 Ų
• XlogP: 0.30
• Atomic LogP (AlogP): -1.51
• H-Bond Acceptor: 14
• H-Bond Donor: 10
• Rotatable Bonds: 9

Synonyms

• (15S)-12,19-Bis(beta-D-glucopyranosyloxy)abieta-8,11,13-triene-11,16-diol

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.4707	47.07%
Caco-2	-	0.8647	86.47%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.7000	70.00%
Subcellular localzation	Mitochondria	0.7343	73.43%
OATP2B1 inhibitior	-	0.8638	86.38%
OATP1B1 inhibitior	+	0.8141	81.41%
OATP1B3 inhibitior	+	0.8397	83.97%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.5000	50.00%
BSEP inhibitior	-	0.5353	53.53%
P-glycoprotein inhibitior	+	0.5930	59.30%
P-glycoprotein substrate	-	0.6429	64.29%
CYP3A4 substrate	+	0.6714	67.14%
CYP2C9 substrate	-	0.7779	77.79%
CYP2D6 substrate	-	0.7893	78.93%
CYP3A4 inhibition	-	0.9557	95.57%
CYP2C9 inhibition	-	0.9034	90.34%
CYP2C19 inhibition	-	0.8392	83.92%
CYP2D6 inhibition	-	0.9578	95.78%
CYP1A2 inhibition	-	0.7527	75.27%
CYP2C8 inhibition	+	0.6312	63.12%
CYP inhibitory promiscuity	-	0.9329	93.29%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9400	94.00%
Carcinogenicity (trinary)	Non-required	0.6790	67.90%
Eye corrosion	-	0.9919	99.19%
Eye irritation	-	0.9223	92.23%
Skin irritation	-	0.7829	78.29%
Skin corrosion	-	0.9612	96.12%
Ames mutagenesis	-	0.6900	69.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6891	68.91%
Micronuclear	-	0.8700	87.00%
Hepatotoxicity	-	0.7625	76.25%
skin sensitisation	-	0.9437	94.37%
Respiratory toxicity	+	0.5667	56.67%
Reproductive toxicity	+	0.7222	72.22%
Mitochondrial toxicity	-	0.6875	68.75%
Nephrotoxicity	-	0.9503	95.03%
Acute Oral Toxicity (c)	III	0.4890	48.90%
Estrogen receptor binding	+	0.7392	73.92%
Androgen receptor binding	+	0.6366	63.66%
Thyroid receptor binding	-	0.5603	56.03%
Glucocorticoid receptor binding	+	0.5465	54.65%
Aromatase binding	+	0.6382	63.82%
PPAR gamma	+	0.6626	66.26%
Honey bee toxicity	-	0.8017	80.17%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.6800	68.00%
Fish aquatic toxicity	+	0.9422	94.22%

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	99.50%	91.11%
CHEMBL2581	P07339	Cathepsin D	96.71%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.20%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	95.09%	94.45%
CHEMBL3137262	O60341	LSD1/CoREST complex	94.00%	97.09%
CHEMBL5608	Q16288	NT-3 growth factor receptor	93.92%	95.89%
CHEMBL253	P34972	Cannabinoid CB2 receptor	93.55%	97.25%
CHEMBL226	P30542	Adenosine A1 receptor	92.64%	95.93%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.74%	89.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	87.12%	100.00%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	86.63%	96.21%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.23%	95.56%
CHEMBL3286	P00749	Urokinase-type plasminogen activator	86.20%	97.88%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	86.07%	94.00%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	85.19%	92.62%
CHEMBL3359	P21462	Formyl peptide receptor 1	85.18%	93.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	84.99%	86.33%
CHEMBL4681	P42330	Aldo-keto-reductase family 1 member C3	84.22%	89.05%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	84.10%	95.50%
CHEMBL3401	O75469	Pregnane X receptor	83.59%	94.73%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	83.54%	90.71%
CHEMBL259	P32245	Melanocortin receptor 4	82.69%	95.38%
CHEMBL241	Q14432	Phosphodiesterase 3A	82.13%	92.94%
CHEMBL5203	P33316	dUTP pyrophosphatase	81.82%	99.18%
CHEMBL237	P41145	Kappa opioid receptor	81.37%	98.10%
CHEMBL1937	Q92769	Histone deacetylase 2	80.52%	94.75%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	80.32%	95.83%
CHEMBL1873	P00750	Tissue-type plasminogen activator	80.22%	93.33%

Plants that contains it

• Ajuga decumbens
• Ajuga reptans
• Clerodendrum bungei

Cross-Links

• PubChem: 44577025
• NPASS: NPC200645
• LOTUS: LTS0019504
• wikiData: Q104913673