Ajacine

Details

• Internal ID: 05fd56b1-4ccb-44f8-8052-9f6b89ca318c
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids > Aconitane-type diterpenoid alkaloids
• IUPAC Name: [(1S,2R,3R,4S,5R,6S,8R,9S,10S,13S,16S,17R,18S)-11-ethyl-8,9-dihydroxy-4,6,16,18-tetramethoxy-11-azahexacyclo[7.7.2.12,5.01,10.03,8.013,17]nonadecan-13-yl]methyl 2-acetamidobenzoate
• SMILES (Canonical): CCN1CC2(CCC(C34C2C(C(C31)(C5(CC(C6CC4C5C6OC)OC)O)O)OC)OC)COC(=O)C7=CC=CC=C7NC(=O)C
• SMILES (Isomeric): CCN1C[C@@]2(CC[C@@H]([C@@]34[C@@H]2[C@@H]([C@@]([C@H]31)([C@]5(C[C@@H]([C@H]6C[C@@H]4[C@@H]5[C@H]6OC)OC)O)O)OC)OC)COC(=O)C7=CC=CC=C7NC(=O)C
• InChI: InChI=1S/C34H48N2O9/c1-7-36-16-31(17-45-29(38)19-10-8-9-11-22(19)35-18(2)37)13-12-24(42-4)33-21-14-20-23(41-3)15-32(39,25(21)26(20)43-5)34(40,30(33)36)28(44-6)27(31)33/h8-11,20-21,23-28,30,39-40H,7,12-17H2,1-6H3,(H,35,37)/t20-,21-,23+,24+,25-,26+,27-,28+,30+,31+,32-,33+,34-/m1/s1
• InChI Key: NUXFDCYXMLVOFU-AYBRVATOSA-N
• Popularity: 16 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₄H₄₈N₂O₉
• Molecular Weight: 628.80 g/mol
• Exact Mass: 628.33598111 g/mol
• Topological Polar Surface Area (TPSA): 136.00 Ų
• XlogP: 1.40
• Atomic LogP (AlogP): 2.09
• H-Bond Acceptor: 10
• H-Bond Donor: 3
• Rotatable Bonds: 9

Synonyms

• Pontaconitine A
• N-(Acetylanthraniloyl)lycoctonine
• UNII-GP3SE3H2BB
• GP3SE3H2BB
• 509-17-1
• Aconitane-7,8-diol, 4-(((2-(acetylamino)benzoyl)oxy)methyl)-20-ethyl-1,6,14,16-tetramethoxy-, (1alpha,6beta,14alpha,16eta)-
• AJACINE [MI]
• N-ACETYLANTHRANILIC ACID ESTER
• Q27279213
• [(1S,2R,3R,4S,5R,6S,8R,9S,10S,13S,16S,17R,18S)-11-ethyl-8,9-dihydroxy-4,6,16,18-tetramethoxy-11-azahexacyclo[7.7.2.12,5.01,10.03,8.013,17]nonadecan-13-yl]methyl 2-acetamidobenzoate
• ACONITANE-7,8-DIOL, 4-(((2-(ACETYLAMINO)BENZOYL)OXY)METHYL)-20-ETHYL-1,6,14,16-TETRAMETHOXY-, (1.ALPHA.,6.BETA.,14.ALPHA.,16.BETA.)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5988	59.88%
Caco-2	-	0.8312	83.12%
Blood Brain Barrier	-	0.8500	85.00%
Human oral bioavailability	-	0.5857	58.57%
Subcellular localzation	Mitochondria	0.5690	56.90%
OATP2B1 inhibitior	-	0.8587	85.87%
OATP1B1 inhibitior	+	0.8610	86.10%
OATP1B3 inhibitior	+	0.9353	93.53%
MATE1 inhibitior	-	0.7846	78.46%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	+	0.9828	98.28%
P-glycoprotein inhibitior	+	0.7028	70.28%
P-glycoprotein substrate	+	0.7638	76.38%
CYP3A4 substrate	+	0.7362	73.62%
CYP2C9 substrate	+	0.5928	59.28%
CYP2D6 substrate	-	0.8044	80.44%
CYP3A4 inhibition	-	0.7761	77.61%
CYP2C9 inhibition	-	0.8456	84.56%
CYP2C19 inhibition	-	0.8740	87.40%
CYP2D6 inhibition	-	0.8667	86.67%
CYP1A2 inhibition	-	0.8812	88.12%
CYP2C8 inhibition	+	0.8114	81.14%
CYP inhibitory promiscuity	-	0.9336	93.36%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9300	93.00%
Carcinogenicity (trinary)	Non-required	0.6572	65.72%
Eye corrosion	-	0.9892	98.92%
Eye irritation	-	0.9312	93.12%
Skin irritation	-	0.7827	78.27%
Skin corrosion	-	0.9388	93.88%
Ames mutagenesis	-	0.6640	66.40%
Human Ether-a-go-go-Related Gene inhibition	+	0.8094	80.94%
Micronuclear	+	0.8100	81.00%
Hepatotoxicity	-	0.6890	68.90%
skin sensitisation	-	0.8809	88.09%
Respiratory toxicity	+	0.7889	78.89%
Reproductive toxicity	+	0.9556	95.56%
Mitochondrial toxicity	+	0.9750	97.50%
Nephrotoxicity	-	0.6577	65.77%
Acute Oral Toxicity (c)	III	0.6035	60.35%
Estrogen receptor binding	+	0.8348	83.48%
Androgen receptor binding	+	0.7686	76.86%
Thyroid receptor binding	+	0.5882	58.82%
Glucocorticoid receptor binding	+	0.6669	66.69%
Aromatase binding	+	0.7495	74.95%
PPAR gamma	+	0.7402	74.02%
Honey bee toxicity	-	0.7357	73.57%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	+	0.5700	57.00%
Fish aquatic toxicity	+	0.8759	87.59%

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	99.29%	96.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	95.54%	97.25%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	94.99%	85.14%
CHEMBL221	P23219	Cyclooxygenase-1	93.97%	90.17%
CHEMBL3137262	O60341	LSD1/CoREST complex	93.46%	97.09%
CHEMBL2095172	P14867	GABA-A receptor; alpha-1/beta-2/gamma-2	92.15%	92.67%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	90.40%	97.14%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.86%	86.33%
CHEMBL340	P08684	Cytochrome P450 3A4	89.67%	91.19%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	88.73%	93.03%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	87.33%	91.11%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	86.76%	82.69%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	85.92%	99.23%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	85.65%	97.21%
CHEMBL2581	P07339	Cathepsin D	84.60%	98.95%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	83.79%	94.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	83.00%	94.45%
CHEMBL2378	P30307	Dual specificity phosphatase Cdc25C	82.87%	96.67%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	82.77%	91.07%
CHEMBL5028	O14672	ADAM10	82.42%	97.50%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	82.20%	89.62%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.10%	95.89%
CHEMBL3922	P50579	Methionine aminopeptidase 2	80.75%	97.28%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	80.69%	92.62%
CHEMBL230	P35354	Cyclooxygenase-2	80.46%	89.63%

Plants that contains it

• Aconitum umbrosum
• Delphinium majus
• Delphinium omeiense
• Delphinium poltaratzkii
• Delphinium tatsienense
• Delphinium umbrosum

Cross-Links

• PubChem: 101667972
• LOTUS: LTS0249539
• wikiData: Q27279213