[(1R,3S,4S,6R,7S,8R)-3-(chloromethyl)-6,8-dihydroxy-10-methylidene-2,9-dioxatricyclo[4.3.1.03,7]decan-4-yl] acetate

Details

• Internal ID: cbf6110c-d7e5-439a-87bb-d719d504057a
• Taxonomy: Organoheterocyclic compounds > Oxepanes
• IUPAC Name: [(1R,3S,4S,6R,7S,8R)-3-(chloromethyl)-6,8-dihydroxy-10-methylidene-2,9-dioxatricyclo[4.3.1.03,7]decan-4-yl] acetate
• SMILES (Canonical): CC(=O)OC1CC2(C3C1(OC(C2=C)OC3O)CCl)O
• SMILES (Isomeric): CC(=O)O[C@H]1C[C@]2([C@H]3[C@@]1(O[C@@H](C2=C)O[C@H]3O)CCl)O
• InChI: InChI=1S/C12H15ClO6/c1-5-10-18-9(15)8-11(5,16)3-7(17-6(2)14)12(8,4-13)19-10/h7-10,15-16H,1,3-4H2,2H3/t7-,8-,9+,10-,11-,12+/m0/s1
• InChI Key: ZTKRNEHDDSFTES-ANNWIZPPSA-N
• Popularity: 3 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₂H₁₅ClO₆
• Molecular Weight: 290.69 g/mol
• Exact Mass: 290.0557159 g/mol
• Topological Polar Surface Area (TPSA): 85.20 Ų
• XlogP: -0.90
• Atomic LogP (AlogP): -0.09
• H-Bond Acceptor: 6
• H-Bond Donor: 2
• Rotatable Bonds: 2

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8941	89.41%
Caco-2	-	0.7786	77.86%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	-	0.5571	55.71%
Subcellular localzation	Mitochondria	0.6135	61.35%
OATP2B1 inhibitior	-	0.8547	85.47%
OATP1B1 inhibitior	+	0.8951	89.51%
OATP1B3 inhibitior	+	0.9336	93.36%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.9281	92.81%
P-glycoprotein inhibitior	-	0.9037	90.37%
P-glycoprotein substrate	-	0.8073	80.73%
CYP3A4 substrate	+	0.6468	64.68%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8766	87.66%
CYP3A4 inhibition	-	0.7444	74.44%
CYP2C9 inhibition	-	0.8678	86.78%
CYP2C19 inhibition	-	0.7744	77.44%
CYP2D6 inhibition	-	0.9029	90.29%
CYP1A2 inhibition	-	0.8535	85.35%
CYP2C8 inhibition	-	0.8101	81.01%
CYP inhibitory promiscuity	-	0.8185	81.85%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9200	92.00%
Carcinogenicity (trinary)	Non-required	0.5158	51.58%
Eye corrosion	-	0.9838	98.38%
Eye irritation	-	0.9408	94.08%
Skin irritation	-	0.6380	63.80%
Skin corrosion	-	0.9145	91.45%
Ames mutagenesis	-	0.5800	58.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7699	76.99%
Micronuclear	-	0.6500	65.00%
Hepatotoxicity	+	0.5687	56.87%
skin sensitisation	-	0.7778	77.78%
Respiratory toxicity	-	0.6667	66.67%
Reproductive toxicity	+	0.8556	85.56%
Mitochondrial toxicity	+	0.7750	77.50%
Nephrotoxicity	+	0.8610	86.10%
Acute Oral Toxicity (c)	III	0.3649	36.49%
Estrogen receptor binding	+	0.6155	61.55%
Androgen receptor binding	+	0.5190	51.90%
Thyroid receptor binding	-	0.4911	49.11%
Glucocorticoid receptor binding	-	0.5248	52.48%
Aromatase binding	-	0.5946	59.46%
PPAR gamma	-	0.4869	48.69%
Honey bee toxicity	-	0.8026	80.26%
Biodegradation	-	0.6250	62.50%
Crustacea aquatic toxicity	-	0.5905	59.05%
Fish aquatic toxicity	+	0.9626	96.26%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.96%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.12%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	87.56%	94.45%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	86.11%	96.95%
CHEMBL218	P21554	Cannabinoid CB1 receptor	85.77%	96.61%
CHEMBL1293249	Q13887	Kruppel-like factor 5	85.72%	86.33%
CHEMBL340	P08684	Cytochrome P450 3A4	83.74%	91.19%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	83.55%	92.62%
CHEMBL3922	P50579	Methionine aminopeptidase 2	82.54%	97.28%
CHEMBL2581	P07339	Cathepsin D	82.49%	98.95%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	82.27%	95.50%
CHEMBL3401	O75469	Pregnane X receptor	81.64%	94.73%

Plants that contains it

• Valeriana jatamansi
• Valeriana officinalis

Cross-Links

• PubChem: 49831711
• NPASS: NPC223700
• LOTUS: LTS0122567
• wikiData: Q105382996