12,13-Dimethoxyibogamine

Details

• Internal ID: eabacef9-4e1a-43ef-b4a3-ec1b9d073755
• Taxonomy: Alkaloids and derivatives > Ibogan-type alkaloids
• IUPAC Name: (1R,15R,17S,18S)-17-ethyl-6,7-dimethoxy-3,13-diazapentacyclo[13.3.1.02,10.04,9.013,18]nonadeca-2(10),4,6,8-tetraene
• SMILES (Canonical): CCC1CC2CC3C1N(C2)CCC4=C3NC5=CC(=C(C=C45)OC)OC
• SMILES (Isomeric): CC[C@H]1C[C@@H]2C[C@@H]3[C@H]1N(C2)CCC4=C3NC5=CC(=C(C=C45)OC)OC
• InChI: InChI=1S/C21H28N2O2/c1-4-13-7-12-8-16-20-14(5-6-23(11-12)21(13)16)15-9-18(24-2)19(25-3)10-17(15)22-20/h9-10,12-13,16,21-22H,4-8,11H2,1-3H3/t12-,13+,16+,21+/m1/s1
• InChI Key: VLOWUTVRYMTRJO-HHNICDRHSA-N
• Popularity: 3 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₂₈N₂O₂
• Molecular Weight: 340.50 g/mol
• Exact Mass: 340.215078140 g/mol
• Topological Polar Surface Area (TPSA): 37.50 Ų
• XlogP: 3.90
• Atomic LogP (AlogP): 3.95
• H-Bond Acceptor: 3
• H-Bond Donor: 1
• Rotatable Bonds: 3

Synonyms

• Ibogaline
• 482-18-8
• F9CB5X4DA4
• (1R,15R,17S,18S)-17-ethyl-6,7-dimethoxy-3,13-diazapentacyclo[13.3.1.02,10.04,9.013,18]nonadeca-2(10),4,6,8-tetraene
• Methoxyibogaine
• 13-METHOXYIBOGAINE
• UNII-F9CB5X4DA4
• Ibogamine, 12,13-dimethoxy-
• DTXSID70964024
• DECARBOMETHOXYCONOPHARYNGINE

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9921	99.21%
Caco-2	+	0.8658	86.58%
Blood Brain Barrier	+	0.8750	87.50%
Human oral bioavailability	-	0.6286	62.86%
Subcellular localzation	Mitochondria	0.6598	65.98%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8805	88.05%
OATP1B3 inhibitior	+	0.9222	92.22%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	+	0.6000	60.00%
BSEP inhibitior	+	0.8508	85.08%
P-glycoprotein inhibitior	-	0.5993	59.93%
P-glycoprotein substrate	+	0.7863	78.63%
CYP3A4 substrate	+	0.5925	59.25%
CYP2C9 substrate	-	0.8153	81.53%
CYP2D6 substrate	+	0.6832	68.32%
CYP3A4 inhibition	+	0.6527	65.27%
CYP2C9 inhibition	-	0.8082	80.82%
CYP2C19 inhibition	-	0.8094	80.94%
CYP2D6 inhibition	+	0.7784	77.84%
CYP1A2 inhibition	-	0.5511	55.11%
CYP2C8 inhibition	-	0.6436	64.36%
CYP inhibitory promiscuity	+	0.5781	57.81%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6614	66.14%
Eye corrosion	-	0.9905	99.05%
Eye irritation	-	0.9464	94.64%
Skin irritation	-	0.7642	76.42%
Skin corrosion	-	0.9377	93.77%
Ames mutagenesis	-	0.6800	68.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8899	88.99%
Micronuclear	+	0.5900	59.00%
Hepatotoxicity	-	0.5000	50.00%
skin sensitisation	-	0.8866	88.66%
Respiratory toxicity	+	0.7889	78.89%
Reproductive toxicity	+	0.9333	93.33%
Mitochondrial toxicity	+	0.9000	90.00%
Nephrotoxicity	-	0.9248	92.48%
Acute Oral Toxicity (c)	II	0.5284	52.84%
Estrogen receptor binding	+	0.6679	66.79%
Androgen receptor binding	+	0.5901	59.01%
Thyroid receptor binding	+	0.5781	57.81%
Glucocorticoid receptor binding	+	0.6243	62.43%
Aromatase binding	-	0.5522	55.22%
PPAR gamma	-	0.7415	74.15%
Honey bee toxicity	-	0.8414	84.14%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	+	0.5600	56.00%
Fish aquatic toxicity	+	0.7865	78.65%

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	98.72%	96.09%
CHEMBL241	Q14432	Phosphodiesterase 3A	97.82%	92.94%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	94.10%	94.45%
CHEMBL255	P29275	Adenosine A2b receptor	93.98%	98.59%
CHEMBL3137262	O60341	LSD1/CoREST complex	93.12%	97.09%
CHEMBL5747	Q92793	CREB-binding protein	92.66%	95.12%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	91.82%	91.11%
CHEMBL3192	Q9BY41	Histone deacetylase 8	89.96%	93.99%
CHEMBL253	P34972	Cannabinoid CB2 receptor	89.21%	97.25%
CHEMBL1907	P15144	Aminopeptidase N	89.18%	93.31%
CHEMBL2041	P07949	Tyrosine-protein kinase receptor RET	88.31%	91.79%
CHEMBL2581	P07339	Cathepsin D	88.26%	98.95%
CHEMBL5608	Q16288	NT-3 growth factor receptor	87.16%	95.89%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	86.85%	93.40%
CHEMBL2069156	Q14145	Kelch-like ECH-associated protein 1	85.87%	82.38%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	85.79%	89.62%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.32%	95.56%
CHEMBL2535	P11166	Glucose transporter	84.17%	98.75%
CHEMBL1293249	Q13887	Kruppel-like factor 5	83.54%	86.33%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	82.97%	92.62%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	82.56%	94.00%
CHEMBL5925	P22413	Ectonucleotide pyrophosphatase/phosphodiesterase family member 1	82.51%	92.38%
CHEMBL1991	O14920	Inhibitor of nuclear factor kappa B kinase beta subunit	82.29%	97.15%
CHEMBL205	P00918	Carbonic anhydrase II	81.39%	98.44%
CHEMBL4895	P30530	Tyrosine-protein kinase receptor UFO	81.38%	90.95%
CHEMBL213	P08588	Beta-1 adrenergic receptor	81.35%	95.56%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	80.45%	85.14%

Plants that contains it

• Tabernaemontana africana
• Tabernaemontana bovina
• Tabernaemontana ciliata
• Tabernaemontana divaricata
• Tabernaemontana pachysiphon
• Tabernanthe iboga

Cross-Links

• PubChem: 193302
• LOTUS: LTS0246765
• wikiData: Q59354331