Aconitane-3,8,13,14,15-pentol, 4-(methoxymethyl)-20-methyl-1,6,16-trimethoxy-, 14-benzoate, (1-alpha,3-alpha,6-alpha,14-alpha,15-alpha,16-beta)-

Details

• Internal ID: f5ef78a4-6af3-4125-89ed-36ec7162ff7c
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids > Aconitane-type diterpenoid alkaloids
• IUPAC Name: [(1S,3R,4R,6S,7S,8R,10R,13R,14R,16S,17S,18R)-5,7,8,14-tetrahydroxy-6,16,18-trimethoxy-13-(methoxymethyl)-11-methyl-11-azahexacyclo[7.7.2.12,5.01,10.03,8.013,17]nonadecan-4-yl] benzoate
• SMILES (Canonical): CN1CC2(C(CC(C34C2C(C(C31)C5(C6C4CC(C6OC(=O)C7=CC=CC=C7)(C(C5O)OC)O)O)OC)OC)O)COC
• SMILES (Isomeric): CN1C[C@@]2([C@@H](C[C@@H]([C@@]34[C@@H]2[C@H](C([C@H]31)[C@@]5([C@@H]6C4CC([C@@H]6OC(=O)C7=CC=CC=C7)([C@H]([C@@H]5O)OC)O)O)OC)OC)O)COC
• InChI: InChI=1S/C31H43NO10/c1-32-13-28(14-38-2)17(33)11-18(39-3)30-16-12-29(36)25(42-27(35)15-9-7-6-8-10-15)19(16)31(37,24(34)26(29)41-5)20(23(30)32)21(40-4)22(28)30/h6-10,16-26,33-34,36-37H,11-14H2,1-5H3/t16?,17-,18+,19-,20?,21+,22-,23-,24+,25-,26+,28+,29?,30+,31-/m1/s1
• InChI Key: PULWZCUZNRVAHT-VBUZYTKISA-N
• Popularity: 27 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₁H₄₃NO₁₀
• Molecular Weight: 589.70 g/mol
• Exact Mass: 589.28869657 g/mol
• Topological Polar Surface Area (TPSA): 147.00 Ų
• XlogP: -0.70
• Atomic LogP (AlogP): -0.31
• H-Bond Acceptor: 11
• H-Bond Donor: 4
• Rotatable Bonds: 7

Synonyms

• PXJ8W3681R
• Mesaconine 14-benzoate
• 63238-67-5
• UNII-PXJ8W3681R
• O8-DEACETYLMESACONITINE
• 14-O-BENZOYLMESACONINE
• BRN 0072534
• 4-21-00-02898 (Beilstein Handbook Reference)
• ACONITANE-3,8,13,14,15-PENTOL, 4-(METHOXYMETHYL)-20-METHYL-1,6,16-TRIMETHOXY-, 14-BENZOATE, (1-.ALPHA.,3-.ALPHA.,6-.ALPHA.,14-.ALPHA.,15-.ALPHA.,16-.BETA.)-
• Aconitane-3,8,13,14,15-pentol, 4-(methoxymethyl)-20-methyl-1,6,16-trimethoxy-, 14-benzoate, (1-alpha,3-alpha,6-alpha,14-alpha,15-alpha,16-beta)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5232	52.32%
Caco-2	-	0.7984	79.84%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.5429	54.29%
Subcellular localzation	Lysosomes	0.6045	60.45%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9222	92.22%
OATP1B3 inhibitior	+	0.9481	94.81%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	+	0.8478	84.78%
P-glycoprotein inhibitior	-	0.4491	44.91%
P-glycoprotein substrate	+	0.6615	66.15%
CYP3A4 substrate	+	0.7156	71.56%
CYP2C9 substrate	-	0.8096	80.96%
CYP2D6 substrate	-	0.6820	68.20%
CYP3A4 inhibition	-	0.8990	89.90%
CYP2C9 inhibition	-	0.9101	91.01%
CYP2C19 inhibition	-	0.9009	90.09%
CYP2D6 inhibition	-	0.9148	91.48%
CYP1A2 inhibition	-	0.8996	89.96%
CYP2C8 inhibition	+	0.6329	63.29%
CYP inhibitory promiscuity	-	0.9639	96.39%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.5778	57.78%
Eye corrosion	-	0.9897	98.97%
Eye irritation	-	0.9208	92.08%
Skin irritation	-	0.7764	77.64%
Skin corrosion	-	0.9396	93.96%
Ames mutagenesis	-	0.6100	61.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6887	68.87%
Micronuclear	+	0.5800	58.00%
Hepatotoxicity	+	0.8250	82.50%
skin sensitisation	-	0.8683	86.83%
Respiratory toxicity	+	0.9222	92.22%
Reproductive toxicity	+	0.8889	88.89%
Mitochondrial toxicity	+	0.9875	98.75%
Nephrotoxicity	-	0.8993	89.93%
Acute Oral Toxicity (c)	I	0.5636	56.36%
Estrogen receptor binding	+	0.8167	81.67%
Androgen receptor binding	+	0.6461	64.61%
Thyroid receptor binding	+	0.6200	62.00%
Glucocorticoid receptor binding	-	0.7043	70.43%
Aromatase binding	+	0.7186	71.86%
PPAR gamma	+	0.7355	73.55%
Honey bee toxicity	-	0.8020	80.20%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.5455	54.55%
Fish aquatic toxicity	+	0.7935	79.35%

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	99.39%	96.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	97.91%	85.14%
CHEMBL2581	P07339	Cathepsin D	94.85%	98.95%
CHEMBL4040	P28482	MAP kinase ERK2	94.44%	83.82%
CHEMBL1293249	Q13887	Kruppel-like factor 5	93.82%	86.33%
CHEMBL4208	P20618	Proteasome component C5	92.76%	90.00%
CHEMBL221	P23219	Cyclooxygenase-1	91.72%	90.17%
CHEMBL1293277	O15118	Niemann-Pick C1 protein	89.71%	81.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.32%	95.56%
CHEMBL5028	O14672	ADAM10	86.90%	97.50%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	86.35%	99.23%
CHEMBL1293294	P51151	Ras-related protein Rab-9A	85.48%	87.67%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	85.38%	91.07%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	85.16%	96.00%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	84.53%	94.08%
CHEMBL253	P34972	Cannabinoid CB2 receptor	83.89%	97.25%
CHEMBL2535	P11166	Glucose transporter	83.02%	98.75%
CHEMBL2096618	P11274	Bcr/Abl fusion protein	81.39%	85.83%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	80.54%	94.00%

Plants that contains it

• Aconitum carmichaelii
• Aconitum jaluense
• Aconitum japonicum subsp. ibukiense

Cross-Links

• PubChem: 145925535
• LOTUS: LTS0016425
• wikiData: Q104393494