(1S,5S,8R,9S,11R,14S,16S,17S,18R,19S)-5-(hydroxymethyl)-12-methylidene-7-azaheptacyclo[9.6.2.01,8.05,17.07,16.09,14.014,18]nonadecan-19-ol

Details

• Internal ID: 2e393e4b-d7d8-4727-87d0-aaad8060bf56
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids > Villanovane, atisane, trachylobane or helvifulvane diterpenoids > Atisane diterpenoids
• IUPAC Name: (1S,5S,8R,9S,11R,14S,16S,17S,18R,19S)-5-(hydroxymethyl)-12-methylidene-7-azaheptacyclo[9.6.2.01,8.05,17.07,16.09,14.014,18]nonadecan-19-ol
• SMILES (Canonical): C=C1CC23CC4C5C6(CCCC57C2C(C1CC3C7N4C6)O)CO
• SMILES (Isomeric): C=C1C[C@@]23C[C@H]4[C@@H]5[C@]6(CCC[C@@]57[C@@H]2[C@H]([C@@H]1C[C@@H]3[C@H]7N4C6)O)CO
• InChI: InChI=1S/C20H27NO2/c1-10-6-19-7-13-15-18(9-22)3-2-4-20(15)16(19)14(23)11(10)5-12(19)17(20)21(13)8-18/h11-17,22-23H,1-9H2/t11-,12-,13+,14+,15-,16-,17-,18+,19+,20+/m1/s1
• InChI Key: WCHIUNLZAZRMKU-RXWAOHGHSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₇NO₂
• Molecular Weight: 313.40 g/mol
• Exact Mass: 313.204179104 g/mol
• Topological Polar Surface Area (TPSA): 43.70 Ų
• XlogP: 1.40
• Atomic LogP (AlogP): 1.79
• H-Bond Acceptor: 3
• 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	+	0.9620	96.20%
Caco-2	-	0.5371	53.71%
Blood Brain Barrier	+	0.8000	80.00%
Human oral bioavailability	+	0.5429	54.29%
Subcellular localzation	Mitochondria	0.4995	49.95%
OATP2B1 inhibitior	-	0.8586	85.86%
OATP1B1 inhibitior	+	0.8632	86.32%
OATP1B3 inhibitior	+	0.9479	94.79%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	+	0.6000	60.00%
BSEP inhibitior	-	0.8157	81.57%
P-glycoprotein inhibitior	-	0.9383	93.83%
P-glycoprotein substrate	-	0.5736	57.36%
CYP3A4 substrate	+	0.6336	63.36%
CYP2C9 substrate	-	0.8100	81.00%
CYP2D6 substrate	+	0.5000	50.00%
CYP3A4 inhibition	-	0.8867	88.67%
CYP2C9 inhibition	-	0.8311	83.11%
CYP2C19 inhibition	-	0.8761	87.61%
CYP2D6 inhibition	-	0.7667	76.67%
CYP1A2 inhibition	-	0.7702	77.02%
CYP2C8 inhibition	-	0.5722	57.22%
CYP inhibitory promiscuity	-	0.7147	71.47%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.5675	56.75%
Eye corrosion	-	0.9766	97.66%
Eye irritation	-	0.7396	73.96%
Skin irritation	-	0.7191	71.91%
Skin corrosion	-	0.8728	87.28%
Ames mutagenesis	-	0.5700	57.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6944	69.44%
Micronuclear	+	0.5600	56.00%
Hepatotoxicity	-	0.5947	59.47%
skin sensitisation	-	0.8040	80.40%
Respiratory toxicity	+	0.6111	61.11%
Reproductive toxicity	+	0.7889	78.89%
Mitochondrial toxicity	+	0.9375	93.75%
Nephrotoxicity	+	0.5466	54.66%
Acute Oral Toxicity (c)	III	0.5999	59.99%
Estrogen receptor binding	+	0.6561	65.61%
Androgen receptor binding	+	0.7122	71.22%
Thyroid receptor binding	+	0.6580	65.80%
Glucocorticoid receptor binding	+	0.8265	82.65%
Aromatase binding	+	0.5814	58.14%
PPAR gamma	+	0.6030	60.30%
Honey bee toxicity	-	0.8178	81.78%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.6600	66.00%
Fish aquatic toxicity	-	0.5113	51.13%

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	97.20%	97.25%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.52%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.74%	97.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	88.60%	91.11%
CHEMBL238	Q01959	Dopamine transporter	86.63%	95.88%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	85.78%	95.50%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	83.42%	93.04%
CHEMBL1994	P08235	Mineralocorticoid receptor	80.34%	100.00%
CHEMBL299	P17252	Protein kinase C alpha	80.15%	98.03%

Plants that contains it

• Delphinium davisii
• Delphinium virgatum

Cross-Links

• PubChem: 101714437
• LOTUS: LTS0014036
• wikiData: Q105301783