4-Hydroxy-18-norkaurane-17-oic acid

Details

• Internal ID: c4cab820-4159-4eb5-89d2-9398955a6a77
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids > Kaurane diterpenoids
• IUPAC Name: (1S,4S,5R,9S,10R,13R,14S)-5-hydroxy-5,9-dimethyltetracyclo[11.2.1.01,10.04,9]hexadecane-14-carboxylic acid
• SMILES (Canonical): CC12CCCC(C1CCC34C2CCC(C3)C(C4)C(=O)O)(C)O
• SMILES (Isomeric): C[C@@]12CCC[C@@]([C@H]1CC[C@]34[C@H]2CC[C@H](C3)[C@H](C4)C(=O)O)(C)O
• InChI: InChI=1S/C19H30O3/c1-17-7-3-8-18(2,22)14(17)6-9-19-10-12(4-5-15(17)19)13(11-19)16(20)21/h12-15,22H,3-11H2,1-2H3,(H,20,21)/t12-,13+,14+,15+,17-,18-,19+/m1/s1
• InChI Key: RLNDAGRLPOJRPI-ANXUHKRASA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₉H₃₀O₃
• Molecular Weight: 306.40 g/mol
• Exact Mass: 306.21949481 g/mol
• Topological Polar Surface Area (TPSA): 57.50 Ų
• XlogP: 4.10
• Atomic LogP (AlogP): 3.84
• H-Bond Acceptor: 2
• H-Bond Donor: 2
• Rotatable Bonds: 1

Synonyms

• 4-Hydroxy-18-norkaurane-17-oic acid

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9947	99.47%
Caco-2	+	0.6398	63.98%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	-	0.5286	52.86%
Subcellular localzation	Mitochondria	0.7340	73.40%
OATP2B1 inhibitior	-	0.8599	85.99%
OATP1B1 inhibitior	+	0.9285	92.85%
OATP1B3 inhibitior	+	0.9551	95.51%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.5000	50.00%
BSEP inhibitior	-	0.6966	69.66%
P-glycoprotein inhibitior	-	0.8849	88.49%
P-glycoprotein substrate	-	0.8828	88.28%
CYP3A4 substrate	+	0.5913	59.13%
CYP2C9 substrate	+	0.5617	56.17%
CYP2D6 substrate	-	0.8614	86.14%
CYP3A4 inhibition	-	0.9377	93.77%
CYP2C9 inhibition	-	0.8618	86.18%
CYP2C19 inhibition	-	0.9312	93.12%
CYP2D6 inhibition	-	0.9666	96.66%
CYP1A2 inhibition	-	0.7845	78.45%
CYP2C8 inhibition	-	0.7883	78.83%
CYP inhibitory promiscuity	-	0.9790	97.90%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6075	60.75%
Eye corrosion	-	0.9906	99.06%
Eye irritation	-	0.8893	88.93%
Skin irritation	+	0.5430	54.30%
Skin corrosion	-	0.9171	91.71%
Ames mutagenesis	-	0.7800	78.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7822	78.22%
Micronuclear	-	0.9200	92.00%
Hepatotoxicity	-	0.6625	66.25%
skin sensitisation	-	0.7285	72.85%
Respiratory toxicity	-	0.5556	55.56%
Reproductive toxicity	+	0.9056	90.56%
Mitochondrial toxicity	+	0.8500	85.00%
Nephrotoxicity	-	0.7500	75.00%
Acute Oral Toxicity (c)	III	0.7240	72.40%
Estrogen receptor binding	+	0.8671	86.71%
Androgen receptor binding	+	0.5210	52.10%
Thyroid receptor binding	+	0.6316	63.16%
Glucocorticoid receptor binding	+	0.7374	73.74%
Aromatase binding	+	0.6710	67.10%
PPAR gamma	-	0.5057	50.57%
Honey bee toxicity	-	0.9233	92.33%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.5800	58.00%
Fish aquatic toxicity	+	0.9675	96.75%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL253	P34972	Cannabinoid CB2 receptor	96.34%	97.25%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	93.06%	96.38%
CHEMBL218	P21554	Cannabinoid CB1 receptor	88.86%	96.61%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	87.46%	96.09%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	83.85%	82.69%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	83.79%	93.04%
CHEMBL340	P08684	Cytochrome P450 3A4	83.23%	91.19%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	80.55%	93.00%
CHEMBL5255	O00206	Toll-like receptor 4	80.35%	92.50%
CHEMBL3137262	O60341	LSD1/CoREST complex	80.11%	97.09%
CHEMBL268	P43235	Cathepsin K	80.02%	96.85%

Plants that contains it

• Annona glabra
• Annona squamosa

Cross-Links

• PubChem: 3001698
• NPASS: NPC196197
• LOTUS: LTS0254635
• wikiData: Q105240300