(4R,4aR,5S)-4,9-dihydroxy-3,4a-dimethyl-5,6,7,8-tetrahydro-4H-benzo[f][1]benzofuran-5-carboxylic acid

Details

• Internal ID: 3eb84ce1-1523-4192-85bd-585366682ea3
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids > Eremophilane, 8,9-secoeremophilane and furoeremophilane sesquiterpenoids
• IUPAC Name: (4R,4aR,5S)-4,9-dihydroxy-3,4a-dimethyl-5,6,7,8-tetrahydro-4H-benzo[f][1]benzofuran-5-carboxylic acid
• SMILES (Canonical): CC1=COC2=C1C(C3(C(CCCC3=C2O)C(=O)O)C)O
• SMILES (Isomeric): CC1=COC2=C1[C@@H]([C@@]3([C@H](CCCC3=C2O)C(=O)O)C)O
• InChI: InChI=1S/C15H18O5/c1-7-6-20-12-10(7)13(17)15(2)8(11(12)16)4-3-5-9(15)14(18)19/h6,9,13,16-17H,3-5H2,1-2H3,(H,18,19)/t9-,13+,15+/m1/s1
• InChI Key: MRZYPKDTXGJJEW-DVJZZOLTSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₁₈O₅
• Molecular Weight: 278.30 g/mol
• Exact Mass: 278.11542367 g/mol
• Topological Polar Surface Area (TPSA): 90.90 Ų
• XlogP: 1.10
• Atomic LogP (AlogP): 2.80
• H-Bond Acceptor: 4
• H-Bond Donor: 3
• Rotatable Bonds: 1

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9912	99.12%
Caco-2	-	0.6147	61.47%
Blood Brain Barrier	+	0.5355	53.55%
Human oral bioavailability	+	0.5714	57.14%
Subcellular localzation	Mitochondria	0.8172	81.72%
OATP2B1 inhibitior	-	0.8518	85.18%
OATP1B1 inhibitior	+	0.8628	86.28%
OATP1B3 inhibitior	+	0.8962	89.62%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.7071	70.71%
BSEP inhibitior	-	0.7970	79.70%
P-glycoprotein inhibitior	-	0.9387	93.87%
P-glycoprotein substrate	-	0.8841	88.41%
CYP3A4 substrate	+	0.6211	62.11%
CYP2C9 substrate	-	0.8155	81.55%
CYP2D6 substrate	-	0.8381	83.81%
CYP3A4 inhibition	-	0.8272	82.72%
CYP2C9 inhibition	-	0.6052	60.52%
CYP2C19 inhibition	-	0.6292	62.92%
CYP2D6 inhibition	-	0.8276	82.76%
CYP1A2 inhibition	+	0.8236	82.36%
CYP2C8 inhibition	-	0.7083	70.83%
CYP inhibitory promiscuity	-	0.5732	57.32%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.9400	94.00%
Carcinogenicity (trinary)	Non-required	0.4422	44.22%
Eye corrosion	-	0.9890	98.90%
Eye irritation	-	0.8473	84.73%
Skin irritation	-	0.5460	54.60%
Skin corrosion	-	0.9031	90.31%
Ames mutagenesis	-	0.5900	59.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5932	59.32%
Micronuclear	-	0.6200	62.00%
Hepatotoxicity	+	0.5532	55.32%
skin sensitisation	-	0.7423	74.23%
Respiratory toxicity	+	0.5556	55.56%
Reproductive toxicity	+	0.8111	81.11%
Mitochondrial toxicity	+	0.7875	78.75%
Nephrotoxicity	-	0.7506	75.06%
Acute Oral Toxicity (c)	I	0.3095	30.95%
Estrogen receptor binding	+	0.5503	55.03%
Androgen receptor binding	+	0.5753	57.53%
Thyroid receptor binding	-	0.5876	58.76%
Glucocorticoid receptor binding	+	0.6190	61.90%
Aromatase binding	-	0.5582	55.82%
PPAR gamma	+	0.5707	57.07%
Honey bee toxicity	-	0.9483	94.83%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.6700	67.00%
Fish aquatic toxicity	+	0.9945	99.45%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4040	P28482	MAP kinase ERK2	99.73%	83.82%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.02%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.92%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.52%	89.00%
CHEMBL2581	P07339	Cathepsin D	86.42%	98.95%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	84.75%	99.23%
CHEMBL3137262	O60341	LSD1/CoREST complex	83.90%	97.09%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	82.59%	90.71%
CHEMBL3359	P21462	Formyl peptide receptor 1	82.15%	93.56%
CHEMBL1994	P08235	Mineralocorticoid receptor	81.70%	100.00%
CHEMBL5255	O00206	Toll-like receptor 4	80.10%	92.50%

Plants that contains it

• Ligularia intermedia

Cross-Links

• PubChem: 162955019
• LOTUS: LTS0099496
• wikiData: Q105171033