Cammaconine

Details

• Internal ID: 5a6349d2-603f-4456-8ed1-3f1c90476494
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids > Aconitane-type diterpenoid alkaloids
• IUPAC Name: (1S,2R,3R,4S,5S,6S,8S,9S,13S,16S,17R)-11-ethyl-13-(hydroxymethyl)-6,16-dimethoxy-11-azahexacyclo[7.7.2.12,5.01,10.03,8.013,17]nonadecane-4,8-diol
• SMILES (Canonical): CCN1CC2(CCC(C34C2CC(C31)C5(CC(C6CC4C5C6O)OC)O)OC)CO
• SMILES (Isomeric): CCN1C[C@@]2(CC[C@@H]([C@@]34[C@@H]2C[C@@H](C31)[C@]5(C[C@@H]([C@H]6C[C@@H]4[C@@H]5[C@H]6O)OC)O)OC)CO
• InChI: InChI=1S/C23H37NO5/c1-4-24-10-21(11-25)6-5-17(29-3)23-13-7-12-15(28-2)9-22(27,18(13)19(12)26)14(20(23)24)8-16(21)23/h12-20,25-27H,4-11H2,1-3H3/t12-,13-,14+,15+,16-,17+,18-,19+,20?,21+,22+,23-/m1/s1
• InChI Key: WCEASIFXIDFWHE-JPAZAREGSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₃H₃₇NO₅
• Molecular Weight: 407.50 g/mol
• Exact Mass: 407.26717328 g/mol
• Topological Polar Surface Area (TPSA): 82.40 Ų
• XlogP: 0.40
• Atomic LogP (AlogP): 0.88
• H-Bond Acceptor: 6
• H-Bond Donor: 3
• Rotatable Bonds: 4

Synonyms

• Columbiananine
• C08666
• CHEBI:3340
• DTXSID70954021
• Q27106034
• 20-ethyl-4-(hydroxymethyl)-1,16-dimethoxyaconitane-8,14-diol
• (1S,2R,3R,4S,5S,6S,8S,9S,13S,16S,17R)-11-ethyl-13-(hydroxymethyl)-6,16-dimethoxy-11-azahexacyclo[7.7.2.12,5.01,10.03,8.013,17]nonadecane-4,8-diol

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8195	81.95%
Caco-2	-	0.6008	60.08%
Blood Brain Barrier	+	0.6250	62.50%
Human oral bioavailability	+	0.5286	52.86%
Subcellular localzation	Lysosomes	0.8138	81.38%
OATP2B1 inhibitior	-	0.8586	85.86%
OATP1B1 inhibitior	+	0.9278	92.78%
OATP1B3 inhibitior	+	0.9437	94.37%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.6500	65.00%
BSEP inhibitior	-	0.6288	62.88%
P-glycoprotein inhibitior	-	0.8954	89.54%
P-glycoprotein substrate	+	0.6006	60.06%
CYP3A4 substrate	+	0.6762	67.62%
CYP2C9 substrate	-	0.8228	82.28%
CYP2D6 substrate	+	0.4019	40.19%
CYP3A4 inhibition	-	0.9444	94.44%
CYP2C9 inhibition	-	0.8888	88.88%
CYP2C19 inhibition	-	0.8956	89.56%
CYP2D6 inhibition	-	0.9195	91.95%
CYP1A2 inhibition	-	0.9164	91.64%
CYP2C8 inhibition	+	0.5121	51.21%
CYP inhibitory promiscuity	-	0.9524	95.24%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6521	65.21%
Eye corrosion	-	0.9852	98.52%
Eye irritation	-	0.9068	90.68%
Skin irritation	-	0.7748	77.48%
Skin corrosion	-	0.9289	92.89%
Ames mutagenesis	-	0.6648	66.48%
Human Ether-a-go-go-Related Gene inhibition	+	0.6844	68.44%
Micronuclear	+	0.5200	52.00%
Hepatotoxicity	-	0.6649	66.49%
skin sensitisation	-	0.8592	85.92%
Respiratory toxicity	+	0.6778	67.78%
Reproductive toxicity	+	0.8667	86.67%
Mitochondrial toxicity	+	0.9375	93.75%
Nephrotoxicity	-	0.7276	72.76%
Acute Oral Toxicity (c)	III	0.5327	53.27%
Estrogen receptor binding	+	0.7026	70.26%
Androgen receptor binding	+	0.6889	68.89%
Thyroid receptor binding	+	0.7106	71.06%
Glucocorticoid receptor binding	-	0.4659	46.59%
Aromatase binding	+	0.6753	67.53%
PPAR gamma	+	0.6081	60.81%
Honey bee toxicity	-	0.7694	76.94%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.5000	50.00%
Fish aquatic toxicity	-	0.8787	87.87%

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	99.19%	96.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	98.59%	97.25%
CHEMBL204	P00734	Thrombin	97.58%	96.01%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	96.24%	85.14%
CHEMBL5469	Q14289	Protein tyrosine kinase 2 beta	93.21%	91.03%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	92.76%	96.38%
CHEMBL3137262	O60341	LSD1/CoREST complex	92.50%	97.09%
CHEMBL226	P30542	Adenosine A1 receptor	91.91%	95.93%
CHEMBL4040	P28482	MAP kinase ERK2	91.61%	83.82%
CHEMBL241	Q14432	Phosphodiesterase 3A	90.99%	92.94%
CHEMBL1994	P08235	Mineralocorticoid receptor	90.26%	100.00%
CHEMBL2534	O15530	3-phosphoinositide dependent protein kinase-1	89.69%	95.36%
CHEMBL6136	O60341	Lysine-specific histone demethylase 1	89.39%	95.58%
CHEMBL5608	Q16288	NT-3 growth factor receptor	88.45%	95.89%
CHEMBL2815	P04629	Nerve growth factor receptor Trk-A	87.57%	87.16%
CHEMBL5888	Q99558	Mitogen-activated protein kinase kinase kinase 14	86.39%	100.00%
CHEMBL2730	P21980	Protein-glutamine gamma-glutamyltransferase	85.63%	92.38%
CHEMBL3820	P35557	Hexokinase type IV	85.07%	91.96%
CHEMBL221	P23219	Cyclooxygenase-1	84.96%	90.17%
CHEMBL1871	P10275	Androgen Receptor	83.98%	96.43%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	82.77%	95.83%
CHEMBL259	P32245	Melanocortin receptor 4	82.65%	95.38%
CHEMBL218	P21554	Cannabinoid CB1 receptor	82.63%	96.61%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	82.39%	95.89%
CHEMBL3430907	Q96GD4	Aurora kinase B/Inner centromere protein	82.22%	97.50%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	82.15%	97.14%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	81.47%	92.62%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	80.64%	89.62%
CHEMBL2781	P19634	Sodium/hydrogen exchanger 1	80.49%	90.24%
CHEMBL1907601	P11802	Cyclin-dependent kinase 4/cyclin D1	80.37%	98.99%

Plants that contains it

• Aconitum columbianum
• Aconitum contortum
• Aconitum dolichorhynchum
• Aconitum forrestii
• Aconitum karakolicum
• Aconitum liljestrandii
• Aconitum orientale
• Aconitum talassicum
• Hansenia weberbaueriana

Cross-Links

• PubChem: 441715
• LOTUS: LTS0076777
• wikiData: Q27106034