Normacusine B

Details

• Internal ID: 5f8548be-378d-4ca3-8ebf-23038200c8aa
• Taxonomy: Alkaloids and derivatives > Macroline alkaloids
• IUPAC Name: [(15Z)-15-ethylidene-3,17-diazapentacyclo[12.3.1.02,10.04,9.012,17]octadeca-2(10),4,6,8-tetraen-13-yl]methanol
• SMILES (Canonical): CC=C1CN2C3CC1C(C2CC4=C3NC5=CC=CC=C45)CO
• SMILES (Isomeric): C/C=C/1\CN2C3CC1C(C2CC4=C3NC5=CC=CC=C45)CO
• InChI: InChI=1S/C19H22N2O/c1-2-11-9-21-17-8-14-12-5-3-4-6-16(12)20-19(14)18(21)7-13(11)15(17)10-22/h2-6,13,15,17-18,20,22H,7-10H2,1H3/b11-2+
• InChI Key: VXTDUGOBAOLMED-BIIKFXOESA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₉H₂₂N₂O
• Molecular Weight: 294.40 g/mol
• Exact Mass: 294.173213330 g/mol
• Topological Polar Surface Area (TPSA): 39.30 Ų
• XlogP: 2.10
• Atomic LogP (AlogP): 3.02
• H-Bond Acceptor: 2
• H-Bond Donor: 2
• Rotatable Bonds: 1

Synonyms

• Vellosiminol
• Tombozine
• Sarpagan-17-ol
• (19trans)-Sarpagan-17-ol #
• VXTDUGOBAOLMED-BIIKFXOESA-N
• Q15425759

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9860	98.60%
Caco-2	+	0.8471	84.71%
Blood Brain Barrier	+	0.9250	92.50%
Human oral bioavailability	-	0.7143	71.43%
Subcellular localzation	Mitochondria	0.4687	46.87%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8255	82.55%
OATP1B3 inhibitior	+	0.9411	94.11%
MATE1 inhibitior	-	0.8618	86.18%
OCT2 inhibitior	+	0.6750	67.50%
BSEP inhibitior	+	0.6097	60.97%
P-glycoprotein inhibitior	-	0.8669	86.69%
P-glycoprotein substrate	-	0.5376	53.76%
CYP3A4 substrate	+	0.6161	61.61%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	+	0.5254	52.54%
CYP3A4 inhibition	-	0.8232	82.32%
CYP2C9 inhibition	-	0.8453	84.53%
CYP2C19 inhibition	-	0.7814	78.14%
CYP2D6 inhibition	+	0.5742	57.42%
CYP1A2 inhibition	+	0.6374	63.74%
CYP2C8 inhibition	+	0.5000	50.00%
CYP inhibitory promiscuity	-	0.5686	56.86%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.6885	68.85%
Eye corrosion	-	0.9852	98.52%
Eye irritation	-	0.9809	98.09%
Skin irritation	-	0.7451	74.51%
Skin corrosion	-	0.9079	90.79%
Ames mutagenesis	+	0.5100	51.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8660	86.60%
Micronuclear	+	0.6500	65.00%
Hepatotoxicity	-	0.5841	58.41%
skin sensitisation	-	0.8435	84.35%
Respiratory toxicity	+	0.8667	86.67%
Reproductive toxicity	+	0.8667	86.67%
Mitochondrial toxicity	+	0.9500	95.00%
Nephrotoxicity	+	0.5930	59.30%
Acute Oral Toxicity (c)	III	0.6897	68.97%
Estrogen receptor binding	-	0.5712	57.12%
Androgen receptor binding	+	0.6518	65.18%
Thyroid receptor binding	-	0.5000	50.00%
Glucocorticoid receptor binding	-	0.7159	71.59%
Aromatase binding	-	0.6959	69.59%
PPAR gamma	-	0.5814	58.14%
Honey bee toxicity	-	0.9145	91.45%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.5000	50.00%
Fish aquatic toxicity	+	0.9226	92.26%

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	97.72%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	94.16%	97.09%
CHEMBL2581	P07339	Cathepsin D	93.47%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	92.75%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.61%	95.56%
CHEMBL253	P34972	Cannabinoid CB2 receptor	89.91%	97.25%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	88.75%	94.45%
CHEMBL3310	Q96DB2	Histone deacetylase 11	88.14%	88.56%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	85.29%	85.14%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.22%	89.00%
CHEMBL3192	Q9BY41	Histone deacetylase 8	83.43%	93.99%
CHEMBL228	P31645	Serotonin transporter	82.59%	95.51%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	82.22%	95.83%
CHEMBL2717	Q9HCR9	Phosphodiesterase 11A	81.31%	85.00%
CHEMBL255	P29275	Adenosine A2b receptor	80.11%	98.59%

Plants that contains it

• Alstonia angustifolia
• Alstonia yunnanensis
• Aspidosperma eburneum
• Gelsemium elegans
• Gelsemium sempervirens
• Melodinus tenuicaudatus
• Rauvolfia bahiensis
• Rauvolfia caffra
• Rauvolfia mannii
• Rauvolfia mombasiana
• Rauvolfia volkensii
• Sophora flavescens
• Strychnos atlantica
• Strychnos madagascariensis
• Strychnos nux-vomica
• Strychnos potatorum
• Strychnos trinervis
• Tabernaemontana africana
• Tabernaemontana corymbosa
• Tabernaemontana cymosa
• Tabernaemontana pachysiphon
• Tabernaemontana vanheurckii
• Vinca difformis
• Vinca minor

Cross-Links

• PubChem: 5318845
• NPASS: NPC181706
• LOTUS: LTS0025694
• wikiData: Q15425759