[(1S,5R,8R,9S,10R,11S,13R,14S,16S,17R,18S,19S)-10,13-dihydroxy-5-methyl-12-methylidene-3-oxo-7-azaheptacyclo[9.6.2.01,8.05,17.07,16.09,14.014,18]nonadecan-19-yl] benzoate

Details

• Internal ID: 8c656e62-0c16-4d7b-b7da-d8411bd303cc
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids > Villanovane, atisane, trachylobane or helvifulvane diterpenoids > Atisane diterpenoids > Hetisine-type diterpenoid alkaloids
• IUPAC Name: [(1S,5R,8R,9S,10R,11S,13R,14S,16S,17R,18S,19S)-10,13-dihydroxy-5-methyl-12-methylidene-3-oxo-7-azaheptacyclo[9.6.2.01,8.05,17.07,16.09,14.014,18]nonadecan-19-yl] benzoate
• SMILES (Canonical): CC12CC(=O)CC34C1C5CC67C3C(C(C(C6C4N5C2)O)C(=C)C7O)OC(=O)C8=CC=CC=C8
• SMILES (Isomeric): C[C@@]12CC(=O)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)[C@H]7O)OC(=O)C8=CC=CC=C8
• InChI: InChI=1S/C27H29NO5/c1-12-16-18(30)17-22-27-9-14(29)8-25(2)11-28(22)15(20(25)27)10-26(17,23(12)31)21(27)19(16)33-24(32)13-6-4-3-5-7-13/h3-7,15-23,30-31H,1,8-11H2,2H3/t15-,16-,17+,18-,19+,20+,21+,22+,23+,25-,26+,27-/m0/s1
• InChI Key: JLPNEAKFLNGJNM-HVBPDPATSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₇H₂₉NO₅
• Molecular Weight: 447.50 g/mol
• Exact Mass: 447.20457303 g/mol
• Topological Polar Surface Area (TPSA): 87.10 Ų
• XlogP: 1.20
• Atomic LogP (AlogP): 1.81
• H-Bond Acceptor: 6
• H-Bond Donor: 2
• Rotatable Bonds: 2

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9449	94.49%
Caco-2	-	0.8233	82.33%
Blood Brain Barrier	+	0.6250	62.50%
Human oral bioavailability	+	0.5143	51.43%
Subcellular localzation	Mitochondria	0.6668	66.68%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8773	87.73%
OATP1B3 inhibitior	+	0.9322	93.22%
MATE1 inhibitior	-	0.8620	86.20%
OCT2 inhibitior	-	0.7500	75.00%
BSEP inhibitior	-	0.7382	73.82%
P-glycoprotein inhibitior	-	0.6674	66.74%
P-glycoprotein substrate	-	0.5066	50.66%
CYP3A4 substrate	+	0.6860	68.60%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7306	73.06%
CYP3A4 inhibition	-	0.9348	93.48%
CYP2C9 inhibition	-	0.8670	86.70%
CYP2C19 inhibition	-	0.8500	85.00%
CYP2D6 inhibition	-	0.9150	91.50%
CYP1A2 inhibition	-	0.8538	85.38%
CYP2C8 inhibition	+	0.6004	60.04%
CYP inhibitory promiscuity	-	0.8341	83.41%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.4664	46.64%
Eye corrosion	-	0.9881	98.81%
Eye irritation	-	0.9525	95.25%
Skin irritation	-	0.7495	74.95%
Skin corrosion	-	0.9326	93.26%
Ames mutagenesis	-	0.5900	59.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4366	43.66%
Micronuclear	+	0.6500	65.00%
Hepatotoxicity	-	0.5214	52.14%
skin sensitisation	-	0.8479	84.79%
Respiratory toxicity	+	0.7556	75.56%
Reproductive toxicity	+	0.8667	86.67%
Mitochondrial toxicity	+	0.9625	96.25%
Nephrotoxicity	+	0.6472	64.72%
Acute Oral Toxicity (c)	III	0.5343	53.43%
Estrogen receptor binding	+	0.6613	66.13%
Androgen receptor binding	+	0.6917	69.17%
Thyroid receptor binding	+	0.5729	57.29%
Glucocorticoid receptor binding	+	0.5955	59.55%
Aromatase binding	+	0.6268	62.68%
PPAR gamma	+	0.5546	55.46%
Honey bee toxicity	-	0.8343	83.43%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.6200	62.00%
Fish aquatic toxicity	+	0.9902	99.02%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL221	P23219	Cyclooxygenase-1	98.14%	90.17%
CHEMBL2581	P07339	Cathepsin D	97.08%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.24%	96.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	94.63%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.36%	95.56%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	88.44%	99.23%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	85.98%	94.08%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	85.77%	94.62%
CHEMBL4208	P20618	Proteasome component C5	84.66%	90.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.74%	95.89%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	83.37%	91.07%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	83.30%	91.11%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	81.93%	82.69%
CHEMBL5028	O14672	ADAM10	81.86%	97.50%
CHEMBL3137262	O60341	LSD1/CoREST complex	81.12%	97.09%
CHEMBL3475	P05121	Plasminogen activator inhibitor-1	80.82%	83.00%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	80.75%	97.14%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	80.23%	93.03%

Plants that contains it

• Aconitum napellus
• Clarkia speciosa
• Delphinium gracile
• Delphinium verdunense
• Hibiscus syriacus
• Malvaviscus arboreus
• Nidularium innocentii
• Phaseolus vulgaris
• Vaccinium angustifolium
• Vaccinium arboreum
• Vaccinium corymbosum
• Vaccinium myrtillus
• Vaccinium uliginosum
• Visnea mocanera
• Vitis vinifera

Cross-Links

• PubChem: 101933335
• LOTUS: LTS0272884
• wikiData: Q105216427