[(1R,2S,3S,4S,5S,8R,9S,10R,11R,14R,16S,17R,18R,19R)-2,19-diacetyloxy-3-hydroxy-5-methyl-12-methylidene-4-(2-methylpropanoyloxy)-7-azaheptacyclo[9.6.2.01,8.05,17.07,16.09,14.014,18]nonadecan-10-yl] benzoate

Details

• Internal ID: 32bb6d1a-18b1-43ce-bebd-ef5739dbfa6a
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids > Villanovane, atisane, trachylobane or helvifulvane diterpenoids > Atisane diterpenoids > Hetisine-type diterpenoid alkaloids
• IUPAC Name: [(1R,2S,3S,4S,5S,8R,9S,10R,11R,14R,16S,17R,18R,19R)-2,19-diacetyloxy-3-hydroxy-5-methyl-12-methylidene-4-(2-methylpropanoyloxy)-7-azaheptacyclo[9.6.2.01,8.05,17.07,16.09,14.014,18]nonadecan-10-yl] benzoate
• SMILES (Canonical): CC(C)C(=O)OC1C(C(C23C4C1(CN5C4CC67C2C(C(C(C6C35)OC(=O)C8=CC=CC=C8)C(=C)C7)OC(=O)C)C)OC(=O)C)O
• SMILES (Isomeric): CC(C)C(=O)O[C@@H]1[C@@H]([C@H]([C@]23[C@H]4[C@]1(CN5[C@H]4C[C@]67[C@H]2[C@H]([C@H]([C@@H]([C@@H]6[C@H]35)OC(=O)C8=CC=CC=C8)C(=C)C7)OC(=O)C)C)OC(=O)C)O
• InChI: InChI=1S/C35H41NO9/c1-15(2)31(40)45-29-23(39)30(43-18(5)38)35-26-20-13-34-12-16(3)21(25(27(34)35)42-17(4)37)24(44-32(41)19-10-8-7-9-11-19)22(34)28(35)36(20)14-33(26,29)6/h7-11,15,20-30,39H,3,12-14H2,1-2,4-6H3/t20-,21-,22+,23-,24-,25-,26+,27+,28+,29+,30+,33+,34-,35+/m0/s1
• InChI Key: HHFRTFPVERTNQD-BVUAMGLSSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₅H₄₁NO₉
• Molecular Weight: 619.70 g/mol
• Exact Mass: 619.27813189 g/mol
• Topological Polar Surface Area (TPSA): 129.00 Ų
• XlogP: 3.50
• Atomic LogP (AlogP): 2.92
• H-Bond Acceptor: 10
• H-Bond Donor: 1
• Rotatable Bonds: 6

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8719	87.19%
Caco-2	-	0.8164	81.64%
Blood Brain Barrier	+	0.7250	72.50%
Human oral bioavailability	-	0.7000	70.00%
Subcellular localzation	Mitochondria	0.6500	65.00%
OATP2B1 inhibitior	-	0.8559	85.59%
OATP1B1 inhibitior	+	0.8628	86.28%
OATP1B3 inhibitior	+	0.9054	90.54%
MATE1 inhibitior	-	0.8820	88.20%
OCT2 inhibitior	-	0.6500	65.00%
BSEP inhibitior	+	0.7945	79.45%
P-glycoprotein inhibitior	+	0.7539	75.39%
P-glycoprotein substrate	+	0.5788	57.88%
CYP3A4 substrate	+	0.6973	69.73%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7189	71.89%
CYP3A4 inhibition	-	0.8082	80.82%
CYP2C9 inhibition	-	0.8382	83.82%
CYP2C19 inhibition	-	0.8490	84.90%
CYP2D6 inhibition	-	0.8785	87.85%
CYP1A2 inhibition	-	0.8285	82.85%
CYP2C8 inhibition	+	0.6327	63.27%
CYP inhibitory promiscuity	-	0.7332	73.32%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9300	93.00%
Carcinogenicity (trinary)	Non-required	0.4658	46.58%
Eye corrosion	-	0.9864	98.64%
Eye irritation	-	0.9138	91.38%
Skin irritation	-	0.7483	74.83%
Skin corrosion	-	0.9297	92.97%
Ames mutagenesis	-	0.5983	59.83%
Human Ether-a-go-go-Related Gene inhibition	-	0.3930	39.30%
Micronuclear	-	0.5100	51.00%
Hepatotoxicity	+	0.5214	52.14%
skin sensitisation	-	0.8297	82.97%
Respiratory toxicity	+	0.6778	67.78%
Reproductive toxicity	+	0.7889	78.89%
Mitochondrial toxicity	+	0.9000	90.00%
Nephrotoxicity	+	0.7225	72.25%
Acute Oral Toxicity (c)	III	0.6244	62.44%
Estrogen receptor binding	+	0.7570	75.70%
Androgen receptor binding	+	0.7035	70.35%
Thyroid receptor binding	+	0.5664	56.64%
Glucocorticoid receptor binding	+	0.6504	65.04%
Aromatase binding	+	0.6472	64.72%
PPAR gamma	+	0.6972	69.72%
Honey bee toxicity	-	0.7593	75.93%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.6200	62.00%
Fish aquatic toxicity	+	0.9957	99.57%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL221	P23219	Cyclooxygenase-1	97.96%	90.17%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.88%	96.09%
CHEMBL2581	P07339	Cathepsin D	97.79%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	94.92%	86.33%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	92.52%	91.11%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	92.06%	94.08%
CHEMBL204	P00734	Thrombin	91.68%	96.01%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.81%	95.56%
CHEMBL240	Q12809	HERG	89.99%	89.76%
CHEMBL340	P08684	Cytochrome P450 3A4	89.71%	91.19%
CHEMBL5608	Q16288	NT-3 growth factor receptor	88.70%	95.89%
CHEMBL3475	P05121	Plasminogen activator inhibitor-1	88.62%	83.00%
CHEMBL253	P34972	Cannabinoid CB2 receptor	86.55%	97.25%
CHEMBL5028	O14672	ADAM10	86.26%	97.50%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	85.03%	93.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	84.76%	99.23%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	83.90%	94.62%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	83.33%	97.14%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	81.77%	96.47%
CHEMBL4267	P37173	TGF-beta receptor type II	81.54%	88.18%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	80.07%	82.69%

Plants that contains it

• Ancistrocladus barteri
• Ancistrocladus tectorius
• Delphinium verdunense
• Triphyophyllum peltatum

Cross-Links

• PubChem: 163104266
• LOTUS: LTS0158988
• wikiData: Q105276455