Dammar-23-en-16-one, 3-[[2-O-(6-deoxy-alpha-L-mannopyranosyl)-alpha-L-arabinopyranosyl]oxy]-20,25-dihydroxy-30-[(6-O-beta-D-xylopyranosyl-beta-D-glucopyranosyl)oxy]-, (3beta,23E)-

Details

• Internal ID: 66eefd24-f1b7-4f5f-88af-11ea5e099d8b
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Triterpene glycosides > Triterpene saponins
• IUPAC Name: (3S,5R,8R,9R,10R,13R,14S,17S)-17-[(E,2S)-2,6-dihydroxy-6-methylhept-4-en-2-yl]-3-[(2S,3R,4S,5S)-4,5-dihydroxy-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-4,4,8,10-tetramethyl-14-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxymethyl]oxan-2-yl]oxymethyl]-1,2,3,5,6,7,9,11,12,13,15,17-dodecahydrocyclopenta[a]phenanthren-16-one
• SMILES (Canonical): CC1C(C(C(C(O1)OC2C(C(COC2OC3CCC4(C5CCC6C(C(=O)CC6(C5(CCC4C3(C)C)C)COC7C(C(C(C(O7)COC8C(C(C(CO8)O)O)O)O)O)O)C(C)(CC=CC(C)(C)O)O)C)O)O)O)O)O
• SMILES (Isomeric): C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)O[C@@H]2[C@H]([C@H](CO[C@H]2O[C@H]3CC[C@@]4([C@H]5CC[C@@H]6[C@H](C(=O)C[C@]6([C@@]5(CC[C@H]4C3(C)C)C)CO[C@H]7[C@@H]([C@H]([C@@H]([C@H](O7)CO[C@H]8[C@@H]([C@H]([C@@H](CO8)O)O)O)O)O)O)[C@](C)(C/C=C/C(C)(C)O)O)C)O)O)O)O)O
• InChI: InChI=1S/C52H86O22/c1-23-33(56)37(60)41(64)45(71-23)74-42-35(58)27(55)20-68-46(42)73-31-13-16-49(6)29(48(31,4)5)12-17-50(7)30(49)11-10-24-32(51(8,66)15-9-14-47(2,3)65)25(53)18-52(24,50)22-70-44-40(63)38(61)36(59)28(72-44)21-69-43-39(62)34(57)26(54)19-67-43/h9,14,23-24,26-46,54-66H,10-13,15-22H2,1-8H3/b14-9+/t23-,24+,26+,27-,28+,29-,30+,31-,32+,33-,34-,35-,36+,37+,38-,39+,40+,41+,42+,43-,44+,45-,46-,49-,50+,51-,52-/m0/s1
• InChI Key: APVZJAWOWWMSMG-ZXXALAAYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₅₂H₈₆O₂₂
• Molecular Weight: 1063.20 g/mol
• Exact Mass: 1062.56107437 g/mol
• Topological Polar Surface Area (TPSA): 354.00 Ų
• XlogP: -1.50
• Atomic LogP (AlogP): -1.75
• H-Bond Acceptor: 22
• H-Bond Donor: 13
• Rotatable Bonds: 14

Synonyms

• 154971-13-8
• Dammar-23-en-16-one, 3-[[2-O-(6-deoxy-alpha-L-mannopyranosyl)-alpha-L-arabinopyranosyl]oxy]-20,25-dihydroxy-30-[(6-O-beta-D-xylopyranosyl-beta-D-glucopyranosyl)oxy]-, (3beta,23E)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7227	72.27%
Caco-2	-	0.8881	88.81%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.7286	72.86%
Subcellular localzation	Mitochondria	0.8006	80.06%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8226	82.26%
OATP1B3 inhibitior	+	0.8421	84.21%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.7750	77.50%
BSEP inhibitior	+	0.8518	85.18%
P-glycoprotein inhibitior	+	0.7497	74.97%
P-glycoprotein substrate	+	0.5839	58.39%
CYP3A4 substrate	+	0.7569	75.69%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8682	86.82%
CYP3A4 inhibition	-	0.9505	95.05%
CYP2C9 inhibition	-	0.9064	90.64%
CYP2C19 inhibition	-	0.8982	89.82%
CYP2D6 inhibition	-	0.9578	95.78%
CYP1A2 inhibition	-	0.9281	92.81%
CYP2C8 inhibition	+	0.7357	73.57%
CYP inhibitory promiscuity	-	0.9666	96.66%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6596	65.96%
Eye corrosion	-	0.9917	99.17%
Eye irritation	-	0.9020	90.20%
Skin irritation	-	0.6103	61.03%
Skin corrosion	-	0.9490	94.90%
Ames mutagenesis	-	0.5700	57.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7384	73.84%
Micronuclear	-	0.8800	88.00%
Hepatotoxicity	-	0.5756	57.56%
skin sensitisation	-	0.9123	91.23%
Respiratory toxicity	+	0.7222	72.22%
Reproductive toxicity	+	0.7778	77.78%
Mitochondrial toxicity	+	0.5250	52.50%
Nephrotoxicity	-	0.9307	93.07%
Acute Oral Toxicity (c)	I	0.5931	59.31%
Estrogen receptor binding	+	0.7962	79.62%
Androgen receptor binding	+	0.7402	74.02%
Thyroid receptor binding	+	0.5475	54.75%
Glucocorticoid receptor binding	+	0.7826	78.26%
Aromatase binding	+	0.6115	61.15%
PPAR gamma	+	0.8088	80.88%
Honey bee toxicity	-	0.6130	61.30%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	+	0.5500	55.00%
Fish aquatic toxicity	+	0.9549	95.49%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL253	P34972	Cannabinoid CB2 receptor	98.16%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.03%	91.11%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	95.54%	96.77%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.31%	96.09%
CHEMBL226	P30542	Adenosine A1 receptor	93.07%	95.93%
CHEMBL1937	Q92769	Histone deacetylase 2	92.64%	94.75%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.19%	86.33%
CHEMBL3714130	P46095	G-protein coupled receptor 6	92.17%	97.36%
CHEMBL241	Q14432	Phosphodiesterase 3A	91.38%	92.94%
CHEMBL1806	P11388	DNA topoisomerase II alpha	89.80%	89.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.40%	95.56%
CHEMBL1902	P62942	FK506-binding protein 1A	88.78%	97.05%
CHEMBL1871	P10275	Androgen Receptor	88.62%	96.43%
CHEMBL325	Q13547	Histone deacetylase 1	88.35%	95.92%
CHEMBL1907605	P24864	Cyclin-dependent kinase 2/cyclin E1	87.13%	92.88%
CHEMBL5608	Q16288	NT-3 growth factor receptor	86.82%	95.89%
CHEMBL2581	P07339	Cathepsin D	86.68%	98.95%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.44%	97.09%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	86.36%	100.00%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	85.55%	97.14%
CHEMBL5957	P21589	5'-nucleotidase	84.41%	97.78%
CHEMBL4829	O00763	Acetyl-CoA carboxylase 2	84.18%	98.00%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	83.08%	95.71%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	83.07%	91.07%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	82.91%	96.38%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	82.24%	92.62%
CHEMBL2179	P04062	Beta-glucocerebrosidase	82.13%	85.31%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	81.91%	95.89%
CHEMBL5028	O14672	ADAM10	81.81%	97.50%
CHEMBL3713062	P10646	Tissue factor pathway inhibitor	81.48%	97.33%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	81.01%	94.00%
CHEMBL3401	O75469	Pregnane X receptor	80.73%	94.73%
CHEMBL218	P21554	Cannabinoid CB1 receptor	80.23%	96.61%
CHEMBL2085	P14174	Macrophage migration inhibitory factor	80.19%	80.78%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	80.06%	93.04%

Plants that contains it

• Hovenia dulcis

Cross-Links

• PubChem: 162940517
• LOTUS: LTS0111631
• wikiData: Q104916579