(1R,4S,5R,9S,10S,12S,13S)-12-hydroxy-5,9,13-trimethyltetracyclo[11.2.1.01,10.04,9]hexadec-14-ene-5-carboxylic acid

Details

• Internal ID: c12207d1-8847-42da-8c5a-1c0c54b3c98f
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids
• IUPAC Name: (1R,4S,5R,9S,10S,12S,13S)-12-hydroxy-5,9,13-trimethyltetracyclo[11.2.1.01,10.04,9]hexadec-14-ene-5-carboxylic acid
• SMILES (Canonical): CC12CCCC(C1CCC34C2CC(C(C3)(C=C4)C)O)(C)C(=O)O
• SMILES (Isomeric): C[C@@]12CCC[C@@]([C@H]1CC[C@@]34[C@H]2C[C@@H]([C@@](C3)(C=C4)C)O)(C)C(=O)O
• InChI: InChI=1S/C20H30O3/c1-17-9-10-20(12-17)8-5-13-18(2,14(20)11-15(17)21)6-4-7-19(13,3)16(22)23/h9-10,13-15,21H,4-8,11-12H2,1-3H3,(H,22,23)/t13-,14-,15-,17+,18+,19+,20-/m0/s1
• InChI Key: AMWMHSPIXDEJLI-SBPXRTMWSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₃₀O₃
• Molecular Weight: 318.40 g/mol
• Exact Mass: 318.21949481 g/mol
• Topological Polar Surface Area (TPSA): 57.50 Ų
• XlogP: 4.50
• Atomic LogP (AlogP): 4.01
• H-Bond Acceptor: 2
• H-Bond Donor: 2
• Rotatable Bonds: 1

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9952	99.52%
Caco-2	+	0.7278	72.78%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	-	0.5857	58.57%
Subcellular localzation	Mitochondria	0.7311	73.11%
OATP2B1 inhibitior	-	0.8660	86.60%
OATP1B1 inhibitior	+	0.8463	84.63%
OATP1B3 inhibitior	+	0.9469	94.69%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	+	0.6000	60.00%
BSEP inhibitior	+	0.7227	72.27%
P-glycoprotein inhibitior	-	0.7863	78.63%
P-glycoprotein substrate	-	0.8118	81.18%
CYP3A4 substrate	+	0.6181	61.81%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8446	84.46%
CYP3A4 inhibition	-	0.8666	86.66%
CYP2C9 inhibition	-	0.8598	85.98%
CYP2C19 inhibition	-	0.8882	88.82%
CYP2D6 inhibition	-	0.9691	96.91%
CYP1A2 inhibition	-	0.7574	75.74%
CYP2C8 inhibition	-	0.7629	76.29%
CYP inhibitory promiscuity	-	0.9552	95.52%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.5983	59.83%
Eye corrosion	-	0.9949	99.49%
Eye irritation	-	0.9469	94.69%
Skin irritation	+	0.7222	72.22%
Skin corrosion	-	0.9393	93.93%
Ames mutagenesis	-	0.7300	73.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6819	68.19%
Micronuclear	-	0.9200	92.00%
Hepatotoxicity	-	0.6785	67.85%
skin sensitisation	-	0.6926	69.26%
Respiratory toxicity	+	0.5667	56.67%
Reproductive toxicity	+	0.9889	98.89%
Mitochondrial toxicity	+	0.9375	93.75%
Nephrotoxicity	-	0.7631	76.31%
Acute Oral Toxicity (c)	III	0.5508	55.08%
Estrogen receptor binding	+	0.8758	87.58%
Androgen receptor binding	+	0.5781	57.81%
Thyroid receptor binding	+	0.7335	73.35%
Glucocorticoid receptor binding	+	0.8234	82.34%
Aromatase binding	+	0.7226	72.26%
PPAR gamma	-	0.6197	61.97%
Honey bee toxicity	-	0.8982	89.82%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	-	0.7600	76.00%
Fish aquatic toxicity	+	0.9922	99.22%

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	93.23%	96.09%
CHEMBL221	P23219	Cyclooxygenase-1	90.19%	90.17%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	87.77%	96.38%
CHEMBL253	P34972	Cannabinoid CB2 receptor	86.72%	97.25%
CHEMBL4040	P28482	MAP kinase ERK2	83.77%	83.82%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	82.51%	99.23%
CHEMBL340	P08684	Cytochrome P450 3A4	82.29%	91.19%
CHEMBL1994	P08235	Mineralocorticoid receptor	82.27%	100.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	82.11%	94.45%
CHEMBL3137262	O60341	LSD1/CoREST complex	81.37%	97.09%

Plants that contains it

• Stevia aristata

Cross-Links

• PubChem: 162918509
• LOTUS: LTS0274351
• wikiData: Q104914967