(1S,3S,4R,5S,6R)-5-[(E,3R)-3-hydroxybut-1-enyl]-4-(hydroxymethyl)-4,6-dimethylcyclohexane-1,3-diol

Details

• Internal ID: 07896c71-ab00-433c-ad01-bbe3b00ca470
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids
• IUPAC Name: (1S,3S,4R,5S,6R)-5-[(E,3R)-3-hydroxybut-1-enyl]-4-(hydroxymethyl)-4,6-dimethylcyclohexane-1,3-diol
• SMILES (Canonical): CC1C(CC(C(C1C=CC(C)O)(C)CO)O)O
• SMILES (Isomeric): C[C@H]1[C@H](C[C@@H]([C@@]([C@H]1/C=C/[C@@H](C)O)(C)CO)O)O
• InChI: InChI=1S/C13H24O4/c1-8(15)4-5-10-9(2)11(16)6-12(17)13(10,3)7-14/h4-5,8-12,14-17H,6-7H2,1-3H3/b5-4+/t8-,9-,10+,11+,12+,13+/m1/s1
• InChI Key: LSSSDBQTAUBGLM-CLMANZCASA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₃H₂₄O₄
• Molecular Weight: 244.33 g/mol
• Exact Mass: 244.16745924 g/mol
• Topological Polar Surface Area (TPSA): 80.90 Ų
• XlogP: 0.70
• Atomic LogP (AlogP): 0.30
• H-Bond Acceptor: 4
• H-Bond Donor: 4
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9269	92.69%
Caco-2	-	0.5809	58.09%
Blood Brain Barrier	+	0.5885	58.85%
Human oral bioavailability	-	0.7286	72.86%
Subcellular localzation	Mitochondria	0.6135	61.35%
OATP2B1 inhibitior	-	0.8530	85.30%
OATP1B1 inhibitior	+	0.9075	90.75%
OATP1B3 inhibitior	+	0.9385	93.85%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.8593	85.93%
BSEP inhibitior	-	0.8998	89.98%
P-glycoprotein inhibitior	-	0.9472	94.72%
P-glycoprotein substrate	-	0.7417	74.17%
CYP3A4 substrate	+	0.5332	53.32%
CYP2C9 substrate	-	0.8052	80.52%
CYP2D6 substrate	-	0.7722	77.22%
CYP3A4 inhibition	-	0.5124	51.24%
CYP2C9 inhibition	-	0.8573	85.73%
CYP2C19 inhibition	-	0.8416	84.16%
CYP2D6 inhibition	-	0.9270	92.70%
CYP1A2 inhibition	-	0.8254	82.54%
CYP2C8 inhibition	-	0.9309	93.09%
CYP inhibitory promiscuity	-	0.8883	88.83%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.8728	87.28%
Carcinogenicity (trinary)	Non-required	0.6897	68.97%
Eye corrosion	-	0.9852	98.52%
Eye irritation	-	0.9585	95.85%
Skin irritation	-	0.7335	73.35%
Skin corrosion	-	0.9593	95.93%
Ames mutagenesis	-	0.6900	69.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6302	63.02%
Micronuclear	-	0.8800	88.00%
Hepatotoxicity	-	0.5393	53.93%
skin sensitisation	-	0.7038	70.38%
Respiratory toxicity	-	0.5889	58.89%
Reproductive toxicity	+	0.6444	64.44%
Mitochondrial toxicity	-	0.5500	55.00%
Nephrotoxicity	-	0.7414	74.14%
Acute Oral Toxicity (c)	III	0.7681	76.81%
Estrogen receptor binding	-	0.7108	71.08%
Androgen receptor binding	-	0.7356	73.56%
Thyroid receptor binding	-	0.5000	50.00%
Glucocorticoid receptor binding	-	0.7045	70.45%
Aromatase binding	-	0.8087	80.87%
PPAR gamma	-	0.8010	80.10%
Honey bee toxicity	-	0.7787	77.87%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.8300	83.00%
Fish aquatic toxicity	+	0.8594	85.94%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	95.50%	85.14%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.06%	96.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	93.39%	97.25%
CHEMBL221	P23219	Cyclooxygenase-1	90.77%	90.17%
CHEMBL2996	Q05655	Protein kinase C delta	88.96%	97.79%
CHEMBL3137262	O60341	LSD1/CoREST complex	88.91%	97.09%
CHEMBL299	P17252	Protein kinase C alpha	87.13%	98.03%
CHEMBL6136	O60341	Lysine-specific histone demethylase 1	86.81%	95.58%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	85.96%	91.11%
CHEMBL2581	P07339	Cathepsin D	85.04%	98.95%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	82.61%	91.07%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	81.69%	96.47%

Plants that contains it

• Melissa officinalis

Cross-Links

• PubChem: 162952250
• LOTUS: LTS0000027
• wikiData: Q105156745