(1S,3S,5R,8R,9S,10R,11R,14R,16S,17R,18R,19S)-5-methyl-12-methylidene-7-azaheptacyclo[9.6.2.01,8.05,17.07,16.09,14.014,18]nonadecane-3,10,19-triol

Details

• Internal ID: 28a670c9-7b34-4d5b-8e81-e583dd659fc7
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids > Villanovane, atisane, trachylobane or helvifulvane diterpenoids > Atisane diterpenoids
• IUPAC Name: (1S,3S,5R,8R,9S,10R,11R,14R,16S,17R,18R,19S)-5-methyl-12-methylidene-7-azaheptacyclo[9.6.2.01,8.05,17.07,16.09,14.014,18]nonadecane-3,10,19-triol
• SMILES (Canonical): CC12CC(CC34C1C5CC67C3C(C(C(C6C4N5C2)O)C(=C)C7)O)O
• SMILES (Isomeric): C[C@@]12C[C@@H](C[C@]34[C@@H]1[C@@H]5C[C@]67[C@H]3[C@@H]([C@H]([C@@H]([C@@H]6[C@H]4N5C2)O)C(=C)C7)O)O
• InChI: InChI=1S/C20H27NO3/c1-8-3-19-6-10-15-18(2)4-9(22)5-20(15)16(19)14(24)11(8)13(23)12(19)17(20)21(10)7-18/h9-17,22-24H,1,3-7H2,2H3/t9-,10-,11-,12+,13-,14+,15+,16+,17+,18-,19-,20-/m0/s1
• InChI Key: PIWJSAMCEMZIDO-APRJJLODSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₇NO₃
• Molecular Weight: 329.40 g/mol
• Exact Mass: 329.19909372 g/mol
• Topological Polar Surface Area (TPSA): 63.90 Ų
• XlogP: 0.50
• Atomic LogP (AlogP): 0.76
• H-Bond Acceptor: 4
• H-Bond Donor: 3
• Rotatable Bonds: 0

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9641	96.41%
Caco-2	-	0.5631	56.31%
Blood Brain Barrier	+	0.7500	75.00%
Human oral bioavailability	+	0.6857	68.57%
Subcellular localzation	Lysosomes	0.6089	60.89%
OATP2B1 inhibitior	-	0.8575	85.75%
OATP1B1 inhibitior	+	0.9075	90.75%
OATP1B3 inhibitior	+	0.9509	95.09%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.7000	70.00%
BSEP inhibitior	-	0.8362	83.62%
P-glycoprotein inhibitior	-	0.9045	90.45%
P-glycoprotein substrate	-	0.6109	61.09%
CYP3A4 substrate	+	0.6097	60.97%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	+	0.4754	47.54%
CYP3A4 inhibition	-	0.9791	97.91%
CYP2C9 inhibition	-	0.8620	86.20%
CYP2C19 inhibition	-	0.7974	79.74%
CYP2D6 inhibition	-	0.8372	83.72%
CYP1A2 inhibition	-	0.8490	84.90%
CYP2C8 inhibition	-	0.7481	74.81%
CYP inhibitory promiscuity	-	0.8372	83.72%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.4979	49.79%
Eye corrosion	-	0.9819	98.19%
Eye irritation	-	0.9243	92.43%
Skin irritation	-	0.7532	75.32%
Skin corrosion	-	0.8958	89.58%
Ames mutagenesis	-	0.5500	55.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4367	43.67%
Micronuclear	-	0.5400	54.00%
Hepatotoxicity	-	0.5875	58.75%
skin sensitisation	-	0.8122	81.22%
Respiratory toxicity	+	0.6111	61.11%
Reproductive toxicity	+	0.8111	81.11%
Mitochondrial toxicity	+	0.9750	97.50%
Nephrotoxicity	+	0.8401	84.01%
Acute Oral Toxicity (c)	III	0.5835	58.35%
Estrogen receptor binding	+	0.6637	66.37%
Androgen receptor binding	+	0.6465	64.65%
Thyroid receptor binding	+	0.7416	74.16%
Glucocorticoid receptor binding	+	0.6906	69.06%
Aromatase binding	+	0.6460	64.60%
PPAR gamma	+	0.5536	55.36%
Honey bee toxicity	-	0.8644	86.44%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	+	0.6000	60.00%
Fish aquatic toxicity	+	0.7239	72.39%

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	94.48%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	88.74%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	88.45%	97.25%
CHEMBL2815	P04629	Nerve growth factor receptor Trk-A	85.40%	87.16%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	84.67%	94.45%
CHEMBL241	Q14432	Phosphodiesterase 3A	83.31%	92.94%
CHEMBL221	P23219	Cyclooxygenase-1	82.87%	90.17%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.65%	95.89%
CHEMBL3746	P80365	11-beta-hydroxysteroid dehydrogenase 2	82.55%	94.78%
CHEMBL3137262	O60341	LSD1/CoREST complex	81.07%	97.09%
CHEMBL5600	P27448	Serine/threonine-protein kinase c-TAK1	80.85%	88.81%
CHEMBL2581	P07339	Cathepsin D	80.46%	98.95%

Plants that contains it

• Aconitum heterophyllum
• Aconitum tanguticum
• Delphinium cardinale
• Delphinium delavayi
• Delphinium elatum
• Delphinium fissum
• Delphinium flexuosum var. buschianum
• Delphinium occidentale
• Delphinium tatsienense

Cross-Links

• PubChem: 86567874
• LOTUS: LTS0133479
• wikiData: Q105191803