Ajugol

Details

• Internal ID: 8aceb74d-de43-409b-99a1-1bde80149d74
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Iridoid O-glycosides
• IUPAC Name: (2S,3R,4S,5S,6R)-2-[[(1S,4aR,5R,7S,7aS)-5,7-dihydroxy-7-methyl-4a,5,6,7a-tetrahydro-1H-cyclopenta[c]pyran-1-yl]oxy]-6-(hydroxymethyl)oxane-3,4,5-triol
• SMILES (Canonical): CC1(CC(C2C1C(OC=C2)OC3C(C(C(C(O3)CO)O)O)O)O)O
• SMILES (Isomeric): C[C@@]1(C[C@H]([C@H]2[C@@H]1[C@@H](OC=C2)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)O)O
• InChI: InChI=1S/C15H24O9/c1-15(21)4-7(17)6-2-3-22-13(9(6)15)24-14-12(20)11(19)10(18)8(5-16)23-14/h2-3,6-14,16-21H,4-5H2,1H3/t6-,7+,8+,9+,10+,11-,12+,13-,14-,15-/m0/s1
• InChI Key: VELYAQRXBJLJAK-XKKWFBPMSA-N
• Popularity: 51 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₄O₉
• Molecular Weight: 348.34 g/mol
• Exact Mass: 348.14203234 g/mol
• Topological Polar Surface Area (TPSA): 149.00 Ų
• XlogP: -2.20
• Atomic LogP (AlogP): -2.58
• H-Bond Acceptor: 9
• H-Bond Donor: 6
• Rotatable Bonds: 3

Synonyms

• 52949-83-4
• Leonuride
• Ajugol; Leonuride
• SCHEMBL4604126
• CHEMBL3810218
• HY-N0914
• MFCD28902296
• s9119
• AKOS030526836
• CCG-268007
• CS-4174
• AC-35048
• MS-25360
• (1S,4AR,5R,7S,7AS)-1,4A,5,6,7,7A-HEXAHYDRO-5,7-DIHYDROXY-7-METHYLCYCLOPENTA(C)PYRAN-1-YL .BETA.-D-GLUCOPYRANOSIDE
• (2S,3S,4R,5R,6S)-6-(((1R,4AS,7S,7AR)-7-HYDROXY-7-METHYL-1,4A,5,6,7,7A-HEXAHYDROCYCLOPENTA(C)PYRAN-1-YL)OXY)-2-(HYDROXYMETHYL)TETRAHYDRO-2H-PYRAN-2,3,4,5-TETRAOL
• .BETA.-D-GLUCOPYRANOSIDE, (1S,4AR,5R,7S,7AS)-1,4A,5,6,7,7A-HEXAHYDRO-5,7-DIHYDROXY-7-METHYLCYCLOPENTA(C)PYRAN-1-YL
• .BETA.-D-GLUCOPYRANOSIDE, 1,4A,5,6,7,7A-HEXAHYDRO-5,7-DIHYDROXY-7-METHYLCYCLOPENTA(C)PYRAN-1-YL, (1S-(1.ALPHA.,4A.ALPHA.,5.ALPHA.,7.ALPHA.,7A.ALPHA.))-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5539	55.39%
Caco-2	-	0.8728	87.28%
Blood Brain Barrier	+	0.5500	55.00%
Human oral bioavailability	-	0.8000	80.00%
Subcellular localzation	Mitochondria	0.5003	50.03%
OATP2B1 inhibitior	-	0.8581	85.81%
OATP1B1 inhibitior	+	0.8657	86.57%
OATP1B3 inhibitior	+	0.9576	95.76%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	-	0.9752	97.52%
P-glycoprotein inhibitior	-	0.8977	89.77%
P-glycoprotein substrate	-	0.8933	89.33%
CYP3A4 substrate	+	0.5991	59.91%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8372	83.72%
CYP3A4 inhibition	-	0.9212	92.12%
CYP2C9 inhibition	-	0.9430	94.30%
CYP2C19 inhibition	-	0.8888	88.88%
CYP2D6 inhibition	-	0.9291	92.91%
CYP1A2 inhibition	-	0.9110	91.10%
CYP2C8 inhibition	-	0.8257	82.57%
CYP inhibitory promiscuity	-	0.8853	88.53%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.5847	58.47%
Eye corrosion	-	0.9918	99.18%
Eye irritation	-	0.9896	98.96%
Skin irritation	-	0.7876	78.76%
Skin corrosion	-	0.9491	94.91%
Ames mutagenesis	-	0.6400	64.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5854	58.54%
Micronuclear	-	0.7500	75.00%
Hepatotoxicity	-	0.8552	85.52%
skin sensitisation	-	0.8931	89.31%
Respiratory toxicity	-	0.5667	56.67%
Reproductive toxicity	+	0.6444	64.44%
Mitochondrial toxicity	-	0.5250	52.50%
Nephrotoxicity	-	0.6562	65.62%
Acute Oral Toxicity (c)	III	0.4625	46.25%
Estrogen receptor binding	-	0.7161	71.61%
Androgen receptor binding	-	0.6578	65.78%
Thyroid receptor binding	+	0.5515	55.15%
Glucocorticoid receptor binding	-	0.6367	63.67%
Aromatase binding	+	0.5720	57.20%
PPAR gamma	+	0.6312	63.12%
Honey bee toxicity	-	0.7758	77.58%
Biodegradation	-	0.6500	65.00%
Crustacea aquatic toxicity	-	0.7500	75.00%
Fish aquatic toxicity	-	0.5335	53.35%

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	96.95%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.86%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.42%	97.09%
CHEMBL226	P30542	Adenosine A1 receptor	90.34%	95.93%
CHEMBL253	P34972	Cannabinoid CB2 receptor	87.39%	97.25%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	87.17%	96.21%
CHEMBL2996	Q05655	Protein kinase C delta	83.73%	97.79%
CHEMBL218	P21554	Cannabinoid CB1 receptor	83.01%	96.61%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	82.98%	95.83%
CHEMBL1293249	Q13887	Kruppel-like factor 5	82.93%	86.33%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	82.28%	85.14%
CHEMBL4208	P20618	Proteasome component C5	81.56%	90.00%
CHEMBL241	Q14432	Phosphodiesterase 3A	80.94%	92.94%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.73%	95.89%

Plants that contains it

• Ajuga genevensis
• Ajuga salicifolia
• Angelonia integerrima
• Asystasia gangetica
• Asystasia gangetica subsp. micrantha
• Broussonetia papyrifera
• Cistanche salsa
• Crescentia cujete
• Kigelia africana subsp. africana
• Markhamia stipulata
• Penstemon albidus
• Penstemon auriberbis
• Physostegia virginiana
• Rehmannia glutinosa
• Scrophularia ilwensis
• Stachys grandidentata
• Stachys recta
• Stachys spinosa
• Stereospermum cylindricum
• Triaenophora rupestris
• Verbascum macrurum
• Verbascum nigrum
• Verbascum pyroliforme subsp. dudleyanum
• Verbascum spinosum
• Verbascum thapsus
• Verbascum undulatum
• Verbascum wiedemannianum
• Zaluzianskya capensis

Cross-Links

• PubChem: 6325127
• NPASS: NPC259296
• LOTUS: LTS0242528
• wikiData: Q104253128