2-Methylisocrotonic acid [(2S)-6beta-hydroxy-2alpha,9abeta-dimethoxy-3,4abeta,5beta-trimethyl-2,4,4a,5,6,7,8,8abeta,9,9a-decahydronaphtho[2,3-b]furan]-4beta-yl ester

Details

• Internal ID: bb330474-9fbf-402b-9230-c53f1ebddbc2
• Taxonomy: Organoheterocyclic compounds > Naphthofurans
• IUPAC Name: [(2S,4S,4aS,5R,6S,8aR,9aS)-6-hydroxy-2,9a-dimethoxy-3,4a,5-trimethyl-2,4,5,6,7,8,8a,9-octahydrobenzo[f][1]benzofuran-4-yl] (Z)-2-methylbut-2-enoate
• SMILES (Canonical): CC=C(C)C(=O)OC1C2=C(C(OC2(CC3C1(C(C(CC3)O)C)C)OC)OC)C
• SMILES (Isomeric): C/C=C(/C)\C(=O)O[C@@H]1C2=C([C@H](O[C@]2(C[C@@H]3[C@]1([C@H]([C@H](CC3)O)C)C)OC)OC)C
• InChI: InChI=1S/C22H34O6/c1-8-12(2)19(24)27-18-17-13(3)20(25-6)28-22(17,26-7)11-15-9-10-16(23)14(4)21(15,18)5/h8,14-16,18,20,23H,9-11H2,1-7H3/b12-8-/t14-,15+,16-,18+,20-,21+,22-/m0/s1
• InChI Key: MEKWGZJWKCYLQM-JPUWCAHSSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₂H₃₄O₆
• Molecular Weight: 394.50 g/mol
• Exact Mass: 394.23553880 g/mol
• Topological Polar Surface Area (TPSA): 74.20 Ų
• XlogP: 2.20
• Atomic LogP (AlogP): 3.34
• H-Bond Acceptor: 6
• H-Bond Donor: 1
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9950	99.50%
Caco-2	+	0.7692	76.92%
Blood Brain Barrier	+	0.6000	60.00%
Human oral bioavailability	-	0.5429	54.29%
Subcellular localzation	Mitochondria	0.7290	72.90%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8696	86.96%
OATP1B3 inhibitior	+	0.9499	94.99%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.6500	65.00%
BSEP inhibitior	+	0.6860	68.60%
P-glycoprotein inhibitior	-	0.4568	45.68%
P-glycoprotein substrate	-	0.5474	54.74%
CYP3A4 substrate	+	0.6722	67.22%
CYP2C9 substrate	-	0.7984	79.84%
CYP2D6 substrate	-	0.8849	88.49%
CYP3A4 inhibition	-	0.6675	66.75%
CYP2C9 inhibition	-	0.8551	85.51%
CYP2C19 inhibition	-	0.8972	89.72%
CYP2D6 inhibition	-	0.9486	94.86%
CYP1A2 inhibition	-	0.6831	68.31%
CYP2C8 inhibition	+	0.4657	46.57%
CYP inhibitory promiscuity	-	0.8836	88.36%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.4810	48.10%
Eye corrosion	-	0.9861	98.61%
Eye irritation	-	0.9083	90.83%
Skin irritation	-	0.5205	52.05%
Skin corrosion	-	0.9104	91.04%
Ames mutagenesis	-	0.5164	51.64%
Human Ether-a-go-go-Related Gene inhibition	-	0.4490	44.90%
Micronuclear	-	0.7100	71.00%
Hepatotoxicity	+	0.5450	54.50%
skin sensitisation	-	0.8086	80.86%
Respiratory toxicity	+	0.5333	53.33%
Reproductive toxicity	+	0.9778	97.78%
Mitochondrial toxicity	+	0.8375	83.75%
Nephrotoxicity	+	0.4522	45.22%
Acute Oral Toxicity (c)	III	0.3236	32.36%
Estrogen receptor binding	+	0.8142	81.42%
Androgen receptor binding	+	0.6825	68.25%
Thyroid receptor binding	+	0.6473	64.73%
Glucocorticoid receptor binding	+	0.8334	83.34%
Aromatase binding	+	0.7045	70.45%
PPAR gamma	+	0.7256	72.56%
Honey bee toxicity	-	0.5224	52.24%
Biodegradation	-	0.9250	92.50%
Crustacea aquatic toxicity	-	0.5355	53.55%
Fish aquatic toxicity	+	0.9340	93.40%

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	97.32%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.95%	96.09%
CHEMBL340	P08684	Cytochrome P450 3A4	91.23%	91.19%
CHEMBL241	Q14432	Phosphodiesterase 3A	88.67%	92.94%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.48%	89.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	85.42%	97.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.97%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	83.65%	86.33%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	83.29%	93.00%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	82.72%	97.14%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	82.66%	95.50%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	81.59%	91.07%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.23%	95.89%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	80.93%	94.45%
CHEMBL1994	P08235	Mineralocorticoid receptor	80.69%	100.00%

Plants that contains it

• Acacia paradoxa
• Adonis sutchuenensis
• Astragalus ernestii
• Berneuxia thibetica
• Bongardia chrysogonum
• Eragrostis curvula
• Fritillaria meleagris
• Isophysis tasmanica
• Matricaria discoidea
• Metasequoia glyptostroboides
• Petasites japonicus
• Philenoptera laxiflora
• Plantago lundborgii
• Sideritis arborescens
• Solanum pseudoquina
• Triadica sebifera

Cross-Links

• PubChem: 101942895
• NPASS: NPC96700
• LOTUS: LTS0102492
• wikiData: Q105162285