Divinatorin A

Details

• Internal ID: 83ffd727-48d1-4ee9-bf5a-43886144b59b
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids > Colensane and clerodane diterpenoids
• IUPAC Name: (4S,4aR,5S,6R,8aR)-5-[2-(furan-3-yl)ethyl]-4-hydroxy-5,6,8a-trimethyl-3,4,4a,6,7,8-hexahydronaphthalene-1-carboxylic acid
• SMILES (Canonical): CC1CCC2(C(C1(C)CCC3=COC=C3)C(CC=C2C(=O)O)O)C
• SMILES (Isomeric): C[C@@H]1CC[C@@]2([C@@H]([C@@]1(C)CCC3=COC=C3)[C@H](CC=C2C(=O)O)O)C
• InChI: InChI=1S/C20H28O4/c1-13-6-9-20(3)15(18(22)23)4-5-16(21)17(20)19(13,2)10-7-14-8-11-24-12-14/h4,8,11-13,16-17,21H,5-7,9-10H2,1-3H3,(H,22,23)/t13-,16+,17-,19+,20+/m1/s1
• InChI Key: FMOMDZQOXKGTDA-MWEXJPOMSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₈O₄
• Molecular Weight: 332.40 g/mol
• Exact Mass: 332.19875937 g/mol
• Topological Polar Surface Area (TPSA): 70.70 Ų
• XlogP: 4.50
• Atomic LogP (AlogP): 4.05
• H-Bond Acceptor: 3
• H-Bond Donor: 2
• Rotatable Bonds: 4

Synonyms

• CHEMBL466786
• (4S,4aR,5S,6R,8aR)-5-[2-(furan-3-yl)ethyl]-4-hydroxy-5,6,8a-trimethyl-3,4,4a,6,7,8-hexahydronaphthalene-1-carboxylic acid

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9911	99.11%
Caco-2	+	0.6910	69.10%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	-	0.5000	50.00%
Subcellular localzation	Mitochondria	0.6485	64.85%
OATP2B1 inhibitior	-	0.8670	86.70%
OATP1B1 inhibitior	+	0.7123	71.23%
OATP1B3 inhibitior	+	0.9492	94.92%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.7000	70.00%
BSEP inhibitior	-	0.7209	72.09%
P-glycoprotein inhibitior	-	0.8378	83.78%
P-glycoprotein substrate	-	0.6573	65.73%
CYP3A4 substrate	+	0.6142	61.42%
CYP2C9 substrate	-	0.7953	79.53%
CYP2D6 substrate	-	0.8881	88.81%
CYP3A4 inhibition	+	0.7761	77.61%
CYP2C9 inhibition	-	0.9142	91.42%
CYP2C19 inhibition	-	0.8227	82.27%
CYP2D6 inhibition	-	0.9049	90.49%
CYP1A2 inhibition	-	0.6319	63.19%
CYP2C8 inhibition	+	0.4768	47.68%
CYP inhibitory promiscuity	-	0.6783	67.83%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.5053	50.53%
Eye corrosion	-	0.9964	99.64%
Eye irritation	-	0.9675	96.75%
Skin irritation	+	0.6491	64.91%
Skin corrosion	-	0.9397	93.97%
Ames mutagenesis	-	0.6670	66.70%
Human Ether-a-go-go-Related Gene inhibition	+	0.6925	69.25%
Micronuclear	-	0.8000	80.00%
Hepatotoxicity	+	0.5277	52.77%
skin sensitisation	-	0.7932	79.32%
Respiratory toxicity	+	0.6222	62.22%
Reproductive toxicity	+	0.9444	94.44%
Mitochondrial toxicity	+	0.9750	97.50%
Nephrotoxicity	-	0.5941	59.41%
Acute Oral Toxicity (c)	III	0.5235	52.35%
Estrogen receptor binding	+	0.8017	80.17%
Androgen receptor binding	+	0.5999	59.99%
Thyroid receptor binding	+	0.6104	61.04%
Glucocorticoid receptor binding	+	0.7817	78.17%
Aromatase binding	+	0.8047	80.47%
PPAR gamma	-	0.5356	53.56%
Honey bee toxicity	-	0.8917	89.17%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	-	0.6700	67.00%
Fish aquatic toxicity	+	0.9963	99.63%

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	95.84%	96.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	95.02%	97.25%
CHEMBL2581	P07339	Cathepsin D	94.72%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.11%	91.11%
CHEMBL221	P23219	Cyclooxygenase-1	91.87%	90.17%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	89.89%	93.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	86.71%	94.45%
CHEMBL3137262	O60341	LSD1/CoREST complex	85.26%	97.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	84.08%	86.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.12%	89.00%

Plants that contains it

• Salvia divinorum

Cross-Links

• PubChem: 10882157
• LOTUS: LTS0207499
• wikiData: Q104399400