(5S,8S,8aR)-5-hydroxy-3,8-dimethyl-5-[2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxypropan-2-yl]-1,4,6,7,8,8a-hexahydroazulen-2-one

Details

• Internal ID: 3dd9b6c9-2934-458d-857a-5ff1c3ae933e
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides
• IUPAC Name: (5S,8S,8aR)-5-hydroxy-3,8-dimethyl-5-[2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxypropan-2-yl]-1,4,6,7,8,8a-hexahydroazulen-2-one
• SMILES (Canonical): CC1CCC(CC2=C(C(=O)CC12)C)(C(C)(C)OC3C(C(C(C(O3)CO)O)O)O)O
• SMILES (Isomeric): C[C@H]1CC[C@](CC2=C(C(=O)C[C@H]12)C)(C(C)(C)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)O
• InChI: InChI=1S/C21H34O8/c1-10-5-6-21(27,8-13-11(2)14(23)7-12(10)13)20(3,4)29-19-18(26)17(25)16(24)15(9-22)28-19/h10,12,15-19,22,24-27H,5-9H2,1-4H3/t10-,12+,15+,16+,17-,18+,19-,21-/m0/s1
• InChI Key: STGKUWZEHAOKMQ-WWLLPVAZSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₃₄O₈
• Molecular Weight: 414.50 g/mol
• Exact Mass: 414.22536804 g/mol
• Topological Polar Surface Area (TPSA): 137.00 Ų
• XlogP: -0.70
• Atomic LogP (AlogP): 0.04
• H-Bond Acceptor: 8
• H-Bond Donor: 5
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8905	89.05%
Caco-2	-	0.7328	73.28%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	-	0.7429	74.29%
Subcellular localzation	Mitochondria	0.8221	82.21%
OATP2B1 inhibitior	-	0.8594	85.94%
OATP1B1 inhibitior	+	0.8835	88.35%
OATP1B3 inhibitior	+	0.8260	82.60%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.6068	60.68%
BSEP inhibitior	-	0.7691	76.91%
P-glycoprotein inhibitior	-	0.7471	74.71%
P-glycoprotein substrate	-	0.7599	75.99%
CYP3A4 substrate	+	0.6619	66.19%
CYP2C9 substrate	-	0.8060	80.60%
CYP2D6 substrate	-	0.8886	88.86%
CYP3A4 inhibition	-	0.8816	88.16%
CYP2C9 inhibition	-	0.6064	60.64%
CYP2C19 inhibition	-	0.8414	84.14%
CYP2D6 inhibition	-	0.9345	93.45%
CYP1A2 inhibition	-	0.7447	74.47%
CYP2C8 inhibition	-	0.7020	70.20%
CYP inhibitory promiscuity	-	0.9307	93.07%
UGT catelyzed	-	0.8000	80.00%
Carcinogenicity (binary)	-	0.9400	94.00%
Carcinogenicity (trinary)	Non-required	0.7032	70.32%
Eye corrosion	-	0.9896	98.96%
Eye irritation	-	0.9523	95.23%
Skin irritation	-	0.5526	55.26%
Skin corrosion	-	0.9421	94.21%
Ames mutagenesis	-	0.6854	68.54%
Human Ether-a-go-go-Related Gene inhibition	-	0.5224	52.24%
Micronuclear	-	0.8600	86.00%
Hepatotoxicity	-	0.5415	54.15%
skin sensitisation	-	0.8847	88.47%
Respiratory toxicity	+	0.5667	56.67%
Reproductive toxicity	+	0.7889	78.89%
Mitochondrial toxicity	+	0.6625	66.25%
Nephrotoxicity	-	0.6000	60.00%
Acute Oral Toxicity (c)	III	0.5890	58.90%
Estrogen receptor binding	+	0.5438	54.38%
Androgen receptor binding	+	0.6939	69.39%
Thyroid receptor binding	+	0.6295	62.95%
Glucocorticoid receptor binding	-	0.5262	52.62%
Aromatase binding	+	0.5982	59.82%
PPAR gamma	+	0.5314	53.14%
Honey bee toxicity	-	0.7954	79.54%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.5400	54.00%
Fish aquatic toxicity	+	0.9424	94.24%

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	97.71%	97.25%
CHEMBL220	P22303	Acetylcholinesterase	96.46%	94.45%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.98%	91.11%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	93.92%	93.04%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.72%	96.09%
CHEMBL2581	P07339	Cathepsin D	93.14%	98.95%
CHEMBL3137262	O60341	LSD1/CoREST complex	92.04%	97.09%
CHEMBL218	P21554	Cannabinoid CB1 receptor	89.49%	96.61%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	87.43%	97.14%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.70%	95.56%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	86.02%	94.00%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	84.22%	86.92%
CHEMBL5255	O00206	Toll-like receptor 4	84.07%	92.50%
CHEMBL1994	P08235	Mineralocorticoid receptor	83.66%	100.00%
CHEMBL226	P30542	Adenosine A1 receptor	83.41%	95.93%
CHEMBL1937	Q92769	Histone deacetylase 2	82.85%	94.75%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.52%	95.89%
CHEMBL4829	O00763	Acetyl-CoA carboxylase 2	82.38%	98.00%
CHEMBL259	P32245	Melanocortin receptor 4	81.95%	95.38%
CHEMBL5028	O14672	ADAM10	81.91%	97.50%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.65%	89.00%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	81.47%	96.21%
CHEMBL5966	P55899	IgG receptor FcRn large subunit p51	80.96%	90.93%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	80.29%	85.14%

Plants that contains it

• Gardenia jasminoides

Cross-Links

• PubChem: 162868507
• LOTUS: LTS0148488
• wikiData: Q105260253