(1S,4S,5S,9R,10R,12S,13S)-13-hydroxy-5,9,10,13-tetramethyltetracyclo[10.2.2.01,10.04,9]hexadecane-5-carboxylic acid

Details

• Internal ID: c99eda0d-a862-4df1-bc80-6f0cbcf73dda
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids > Villanovane, atisane, trachylobane or helvifulvane diterpenoids > Atisane diterpenoids
• IUPAC Name: (1S,4S,5S,9R,10R,12S,13S)-13-hydroxy-5,9,10,13-tetramethyltetracyclo[10.2.2.01,10.04,9]hexadecane-5-carboxylic acid
• SMILES (Canonical): CC1(CCCC2(C1CCC34C2(CC(CC3)C(C4)(C)O)C)C)C(=O)O
• SMILES (Isomeric): C[C@@]1(CCC[C@@]2([C@@H]1CC[C@]34[C@]2(C[C@H](CC3)[C@@](C4)(C)O)C)C)C(=O)O
• InChI: InChI=1S/C21H34O3/c1-17(16(22)23)8-5-9-18(2)15(17)7-11-21-10-6-14(12-20(18,21)4)19(3,24)13-21/h14-15,24H,5-13H2,1-4H3,(H,22,23)/t14-,15+,17-,18+,19-,20-,21+/m0/s1
• InChI Key: GWYVTGCQCDQIFZ-DWBADUGPSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₃₄O₃
• Molecular Weight: 334.50 g/mol
• Exact Mass: 334.25079494 g/mol
• Topological Polar Surface Area (TPSA): 57.50 Ų
• XlogP: 4.90
• Atomic LogP (AlogP): 4.63
• 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	+	0.9939	99.39%
Caco-2	+	0.8560	85.60%
Blood Brain Barrier	+	0.6000	60.00%
Human oral bioavailability	+	0.5429	54.29%
Subcellular localzation	Mitochondria	0.8234	82.34%
OATP2B1 inhibitior	-	0.8559	85.59%
OATP1B1 inhibitior	+	0.8934	89.34%
OATP1B3 inhibitior	+	0.9740	97.40%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	+	0.5250	52.50%
BSEP inhibitior	-	0.5476	54.76%
P-glycoprotein inhibitior	-	0.8073	80.73%
P-glycoprotein substrate	-	0.8525	85.25%
CYP3A4 substrate	+	0.6287	62.87%
CYP2C9 substrate	+	0.5617	56.17%
CYP2D6 substrate	-	0.8614	86.14%
CYP3A4 inhibition	-	0.8538	85.38%
CYP2C9 inhibition	-	0.8822	88.22%
CYP2C19 inhibition	-	0.9625	96.25%
CYP2D6 inhibition	-	0.9758	97.58%
CYP1A2 inhibition	-	0.8006	80.06%
CYP2C8 inhibition	-	0.7185	71.85%
CYP inhibitory promiscuity	-	0.9812	98.12%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6577	65.77%
Eye corrosion	-	0.9920	99.20%
Eye irritation	-	0.8690	86.90%
Skin irritation	+	0.7033	70.33%
Skin corrosion	-	0.9262	92.62%
Ames mutagenesis	-	0.6100	61.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5254	52.54%
Micronuclear	-	0.9500	95.00%
Hepatotoxicity	-	0.5967	59.67%
skin sensitisation	-	0.6574	65.74%
Respiratory toxicity	-	0.5222	52.22%
Reproductive toxicity	+	0.8556	85.56%
Mitochondrial toxicity	+	0.7500	75.00%
Nephrotoxicity	+	0.5584	55.84%
Acute Oral Toxicity (c)	III	0.7596	75.96%
Estrogen receptor binding	+	0.9044	90.44%
Androgen receptor binding	+	0.6829	68.29%
Thyroid receptor binding	+	0.6637	66.37%
Glucocorticoid receptor binding	+	0.7757	77.57%
Aromatase binding	+	0.8224	82.24%
PPAR gamma	-	0.6067	60.67%
Honey bee toxicity	-	0.9300	93.00%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.6100	61.00%
Fish aquatic toxicity	+	0.9776	97.76%

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	92.83%	96.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	88.34%	97.25%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.02%	95.56%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	84.24%	82.69%
CHEMBL4979	P13866	Sodium/glucose cotransporter 1	83.87%	98.24%
CHEMBL340	P08684	Cytochrome P450 3A4	82.96%	91.19%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	82.75%	91.11%
CHEMBL218	P21554	Cannabinoid CB1 receptor	81.21%	96.61%
CHEMBL3137262	O60341	LSD1/CoREST complex	80.58%	97.09%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	80.53%	99.23%

Plants that contains it

• Xylopia aromatica

Cross-Links

• PubChem: 163066602
• LOTUS: LTS0029670
• wikiData: Q105022921