(2S,3R,4S,5S,6R)-2-[2-[(2R,4aR,8aR)-8-(hydroxymethyl)-4a-methyl-2,3,4,5,6,8a-hexahydro-1H-naphthalen-2-yl]propan-2-yloxy]-6-(hydroxymethyl)oxane-3,4,5-triol

Details

• Internal ID: 78000a8b-ec2c-4429-9edf-708b9d72bb7d
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids > Eudesmane, isoeudesmane or cycloeudesmane sesquiterpenoids
• IUPAC Name: (2S,3R,4S,5S,6R)-2-[2-[(2R,4aR,8aR)-8-(hydroxymethyl)-4a-methyl-2,3,4,5,6,8a-hexahydro-1H-naphthalen-2-yl]propan-2-yloxy]-6-(hydroxymethyl)oxane-3,4,5-triol
• SMILES (Canonical): CC12CCC=C(C1CC(CC2)C(C)(C)OC3C(C(C(C(O3)CO)O)O)O)CO
• SMILES (Isomeric): C[C@]12CCC=C([C@@H]1C[C@@H](CC2)C(C)(C)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)CO
• InChI: InChI=1S/C21H36O7/c1-20(2,28-19-18(26)17(25)16(24)15(11-23)27-19)13-6-8-21(3)7-4-5-12(10-22)14(21)9-13/h5,13-19,22-26H,4,6-11H2,1-3H3/t13-,14+,15-,16-,17+,18-,19+,21-/m1/s1
• InChI Key: PXMONFDWFWAIMC-MPSLSGHYSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₃₆O₇
• Molecular Weight: 400.50 g/mol
• Exact Mass: 400.24610348 g/mol
• Topological Polar Surface Area (TPSA): 120.00 Ų
• XlogP: 0.70
• Atomic LogP (AlogP): 0.72
• H-Bond Acceptor: 7
• H-Bond Donor: 5
• Rotatable Bonds: 5

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6476	64.76%
Caco-2	-	0.7760	77.60%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	-	0.7429	74.29%
Subcellular localzation	Mitochondria	0.7872	78.72%
OATP2B1 inhibitior	-	0.7203	72.03%
OATP1B1 inhibitior	+	0.8933	89.33%
OATP1B3 inhibitior	-	0.2827	28.27%
MATE1 inhibitior	-	0.9612	96.12%
OCT2 inhibitior	-	0.6000	60.00%
BSEP inhibitior	-	0.6642	66.42%
P-glycoprotein inhibitior	-	0.7929	79.29%
P-glycoprotein substrate	-	0.8247	82.47%
CYP3A4 substrate	+	0.6501	65.01%
CYP2C9 substrate	-	0.8025	80.25%
CYP2D6 substrate	-	0.8264	82.64%
CYP3A4 inhibition	-	0.9353	93.53%
CYP2C9 inhibition	-	0.8291	82.91%
CYP2C19 inhibition	-	0.8184	81.84%
CYP2D6 inhibition	-	0.9372	93.72%
CYP1A2 inhibition	-	0.7977	79.77%
CYP2C8 inhibition	+	0.5264	52.64%
CYP inhibitory promiscuity	-	0.8993	89.93%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.7077	70.77%
Eye corrosion	-	0.9899	98.99%
Eye irritation	-	0.9784	97.84%
Skin irritation	-	0.7058	70.58%
Skin corrosion	-	0.9551	95.51%
Ames mutagenesis	-	0.7324	73.24%
Human Ether-a-go-go-Related Gene inhibition	-	0.4280	42.80%
Micronuclear	-	0.8800	88.00%
Hepatotoxicity	-	0.5028	50.28%
skin sensitisation	-	0.8846	88.46%
Respiratory toxicity	+	0.5222	52.22%
Reproductive toxicity	+	0.8333	83.33%
Mitochondrial toxicity	-	0.6750	67.50%
Nephrotoxicity	-	0.7182	71.82%
Acute Oral Toxicity (c)	III	0.6882	68.82%
Estrogen receptor binding	-	0.4799	47.99%
Androgen receptor binding	+	0.5645	56.45%
Thyroid receptor binding	+	0.6474	64.74%
Glucocorticoid receptor binding	+	0.6037	60.37%
Aromatase binding	+	0.6821	68.21%
PPAR gamma	-	0.5275	52.75%
Honey bee toxicity	-	0.7466	74.66%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.5800	58.00%
Fish aquatic toxicity	+	0.9465	94.65%

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	99.45%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.57%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.89%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	96.43%	97.09%
CHEMBL218	P21554	Cannabinoid CB1 receptor	95.82%	96.61%
CHEMBL2996	Q05655	Protein kinase C delta	93.42%	97.79%
CHEMBL216	P11229	Muscarinic acetylcholine receptor M1	90.56%	94.23%
CHEMBL5608	Q16288	NT-3 growth factor receptor	87.91%	95.89%
CHEMBL2581	P07339	Cathepsin D	87.47%	98.95%
CHEMBL1871	P10275	Androgen Receptor	86.15%	96.43%
CHEMBL1994	P08235	Mineralocorticoid receptor	86.02%	100.00%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	85.46%	92.62%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	85.44%	94.45%
CHEMBL241	Q14432	Phosphodiesterase 3A	84.90%	92.94%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.88%	89.00%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	82.36%	95.83%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	82.35%	97.14%
CHEMBL237	P41145	Kappa opioid receptor	82.34%	98.10%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	81.67%	86.92%
CHEMBL3401	O75469	Pregnane X receptor	81.01%	94.73%

Plants that contains it

• Artemisia umbelliformis
• Juglans regia
• Onopordum anatolicum
• Salix japonica
• Tiliacora triandra
• Viburnum ayavacense

Cross-Links

• PubChem: 57391287
• NPASS: NPC302584
• LOTUS: LTS0187193
• wikiData: Q105216264