14-Hydroxy-6,12-muuroloadien-15-oic acid

Details

• Internal ID: 401a2c44-5856-4faa-b6fa-75919c281771
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids
• IUPAC Name: (4aS,5S,8S,8aR)-8-(3-hydroxyprop-1-en-2-yl)-5-methyl-3,4,4a,5,6,7,8,8a-octahydronaphthalene-2-carboxylic acid
• SMILES (Canonical): CC1CCC(C2C1CCC(=C2)C(=O)O)C(=C)CO
• SMILES (Isomeric): C[C@H]1CC[C@@H]([C@@H]2[C@H]1CCC(=C2)C(=O)O)C(=C)CO
• InChI: InChI=1S/C15H22O3/c1-9-3-5-13(10(2)8-16)14-7-11(15(17)18)4-6-12(9)14/h7,9,12-14,16H,2-6,8H2,1H3,(H,17,18)/t9-,12-,13+,14-/m0/s1
• InChI Key: JSCXVSJJZJIGJC-WTDIUWLJSA-N
• Popularity: 3 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₂O₃
• Molecular Weight: 250.33 g/mol
• Exact Mass: 250.15689456 g/mol
• Topological Polar Surface Area (TPSA): 57.50 Ų
• XlogP: 3.10
• Atomic LogP (AlogP): 2.62
• H-Bond Acceptor: 2
• H-Bond Donor: 2
• Rotatable Bonds: 3

Synonyms

• CHEBI:69354
• Q27137695
• (4aS)-5beta-Methyl-8alpha-[1-(hydroxymethyl)ethenyl]-3,4,4aalpha,5,6,7,8,8aalpha-octahydronaphthalene-2-carboxylic acid
• (4aS,5S,8S,8aR)-8-(3-hydroxyprop-1-en-2-yl)-5-methyl-3,4,4a,5,6,7,8,8a-octahydronaphthalene-2-carboxylic acid
• (4aS,5S,8S,8aR)-8-[1-(hydroxymethyl)vinyl]-5-methyl-3,4,4a,5,6,7,8,8a-octahydronaphthalene-2-carboxylic acid

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9918	99.18%
Caco-2	+	0.6821	68.21%
Blood Brain Barrier	+	0.6750	67.50%
Human oral bioavailability	+	0.5429	54.29%
Subcellular localzation	Mitochondria	0.5492	54.92%
OATP2B1 inhibitior	-	0.8559	85.59%
OATP1B1 inhibitior	+	0.9230	92.30%
OATP1B3 inhibitior	+	0.8923	89.23%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.5695	56.95%
BSEP inhibitior	-	0.9344	93.44%
P-glycoprotein inhibitior	-	0.9392	93.92%
P-glycoprotein substrate	-	0.8275	82.75%
CYP3A4 substrate	-	0.5000	50.00%
CYP2C9 substrate	-	0.7724	77.24%
CYP2D6 substrate	-	0.9110	91.10%
CYP3A4 inhibition	-	0.7083	70.83%
CYP2C9 inhibition	-	0.6929	69.29%
CYP2C19 inhibition	-	0.7701	77.01%
CYP2D6 inhibition	-	0.8687	86.87%
CYP1A2 inhibition	-	0.6242	62.42%
CYP2C8 inhibition	-	0.8109	81.09%
CYP inhibitory promiscuity	-	0.7356	73.56%
UGT catelyzed	-	0.7000	70.00%
Carcinogenicity (binary)	-	0.9300	93.00%
Carcinogenicity (trinary)	Non-required	0.6659	66.59%
Eye corrosion	-	0.9432	94.32%
Eye irritation	-	0.5415	54.15%
Skin irritation	-	0.8075	80.75%
Skin corrosion	-	0.9723	97.23%
Ames mutagenesis	-	0.8078	80.78%
Human Ether-a-go-go-Related Gene inhibition	-	0.7058	70.58%
Micronuclear	-	0.9200	92.00%
Hepatotoxicity	+	0.5428	54.28%
skin sensitisation	-	0.5347	53.47%
Respiratory toxicity	+	0.5667	56.67%
Reproductive toxicity	-	0.5079	50.79%
Mitochondrial toxicity	+	0.5750	57.50%
Nephrotoxicity	-	0.6893	68.93%
Acute Oral Toxicity (c)	III	0.6128	61.28%
Estrogen receptor binding	-	0.7220	72.20%
Androgen receptor binding	+	0.6122	61.22%
Thyroid receptor binding	-	0.5446	54.46%
Glucocorticoid receptor binding	+	0.6691	66.91%
Aromatase binding	-	0.6937	69.37%
PPAR gamma	-	0.7512	75.12%
Honey bee toxicity	-	0.9138	91.38%
Biodegradation	-	0.6000	60.00%
Crustacea aquatic toxicity	-	0.6500	65.00%
Fish aquatic toxicity	+	1.0000	100.00%

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	97.48%	96.09%
CHEMBL4040	P28482	MAP kinase ERK2	97.17%	83.82%
CHEMBL2581	P07339	Cathepsin D	88.04%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	86.25%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.69%	95.56%
CHEMBL3137262	O60341	LSD1/CoREST complex	85.39%	97.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	80.87%	100.00%

Plants that contains it

• Eremophila mitchellii

Cross-Links

• PubChem: 70698100
• NPASS: NPC146589
• LOTUS: LTS0192669
• wikiData: Q103818482