[(1S,12S,13S,14R,15E)-15-ethylidene-7-methoxy-3-methyl-3,17-diazapentacyclo[12.3.1.02,10.04,9.012,17]octadeca-2(10),4(9),5,7-tetraen-13-yl]methanol

Details

• Internal ID: 512c5f35-6a91-4c53-86f7-0c2f4e3c143e
• Taxonomy: Alkaloids and derivatives > Macroline alkaloids
• IUPAC Name: [(1S,12S,13S,14R,15E)-15-ethylidene-7-methoxy-3-methyl-3,17-diazapentacyclo[12.3.1.02,10.04,9.012,17]octadeca-2(10),4(9),5,7-tetraen-13-yl]methanol
• SMILES (Canonical): CC=C1CN2C3CC1C(C2CC4=C3N(C5=C4C=C(C=C5)OC)C)CO
• SMILES (Isomeric): C/C=C\1/CN2[C@H]3C[C@@H]1[C@@H]([C@@H]2CC4=C3N(C5=C4C=C(C=C5)OC)C)CO
• InChI: InChI=1S/C21H26N2O2/c1-4-12-10-23-19-9-16-15-7-13(25-3)5-6-18(15)22(2)21(16)20(23)8-14(12)17(19)11-24/h4-7,14,17,19-20,24H,8-11H2,1-3H3/b12-4-/t14-,17-,19-,20-/m0/s1
• InChI Key: QWVWSERSLAJTNG-MBJKCFRWSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₂₆N₂O₂
• Molecular Weight: 338.40 g/mol
• Exact Mass: 338.199428076 g/mol
• Topological Polar Surface Area (TPSA): 37.60 Ų
• XlogP: 2.00
• Atomic LogP (AlogP): 3.04
• H-Bond Acceptor: 4
• H-Bond Donor: 1
• Rotatable Bonds: 2

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9677	96.77%
Caco-2	+	0.8221	82.21%
Blood Brain Barrier	+	0.9358	93.58%
Human oral bioavailability	-	0.5000	50.00%
Subcellular localzation	Mitochondria	0.6910	69.10%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8587	85.87%
OATP1B3 inhibitior	+	0.9377	93.77%
MATE1 inhibitior	-	0.7218	72.18%
OCT2 inhibitior	+	0.6000	60.00%
BSEP inhibitior	+	0.8632	86.32%
P-glycoprotein inhibitior	-	0.5363	53.63%
P-glycoprotein substrate	+	0.7315	73.15%
CYP3A4 substrate	+	0.6459	64.59%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	+	0.5168	51.68%
CYP3A4 inhibition	-	0.5228	52.28%
CYP2C9 inhibition	-	0.7845	78.45%
CYP2C19 inhibition	-	0.6915	69.15%
CYP2D6 inhibition	+	0.7056	70.56%
CYP1A2 inhibition	+	0.6255	62.55%
CYP2C8 inhibition	+	0.5299	52.99%
CYP inhibitory promiscuity	+	0.7224	72.24%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.6278	62.78%
Eye corrosion	-	0.9877	98.77%
Eye irritation	-	0.9909	99.09%
Skin irritation	-	0.7765	77.65%
Skin corrosion	-	0.9300	93.00%
Ames mutagenesis	-	0.6200	62.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8703	87.03%
Micronuclear	+	0.5800	58.00%
Hepatotoxicity	-	0.5750	57.50%
skin sensitisation	-	0.8589	85.89%
Respiratory toxicity	+	0.8222	82.22%
Reproductive toxicity	+	0.9000	90.00%
Mitochondrial toxicity	+	0.8750	87.50%
Nephrotoxicity	-	0.6401	64.01%
Acute Oral Toxicity (c)	III	0.6947	69.47%
Estrogen receptor binding	+	0.6883	68.83%
Androgen receptor binding	+	0.7142	71.42%
Thyroid receptor binding	+	0.6187	61.87%
Glucocorticoid receptor binding	+	0.7161	71.61%
Aromatase binding	-	0.5000	50.00%
PPAR gamma	-	0.5000	50.00%
Honey bee toxicity	-	0.8622	86.22%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	+	0.5100	51.00%
Fish aquatic toxicity	+	0.8207	82.07%

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	98.90%	96.09%
CHEMBL226	P30542	Adenosine A1 receptor	97.04%	95.93%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.74%	95.56%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	93.40%	91.11%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	92.97%	86.92%
CHEMBL253	P34972	Cannabinoid CB2 receptor	91.00%	97.25%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	90.70%	85.14%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.47%	97.09%
CHEMBL3438	Q05513	Protein kinase C zeta	89.26%	88.48%
CHEMBL2581	P07339	Cathepsin D	88.00%	98.95%
CHEMBL1907	P15144	Aminopeptidase N	87.26%	93.31%
CHEMBL4208	P20618	Proteasome component C5	86.58%	90.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	86.52%	95.89%
CHEMBL3060	Q9Y345	Glycine transporter 2	85.94%	99.17%
CHEMBL1293249	Q13887	Kruppel-like factor 5	84.19%	86.33%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	84.19%	93.00%
CHEMBL255	P29275	Adenosine A2b receptor	83.92%	98.59%
CHEMBL3192	Q9BY41	Histone deacetylase 8	83.51%	93.99%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	83.35%	95.89%
CHEMBL2335	P42785	Lysosomal Pro-X carboxypeptidase	82.13%	100.00%
CHEMBL4681	P42330	Aldo-keto-reductase family 1 member C3	82.11%	89.05%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	80.27%	95.83%

Plants that contains it

• Alstonia angustifolia
• Alstonia balansae
• Alstonia macrophylla

Cross-Links

• PubChem: 11537380
• LOTUS: LTS0264748
• wikiData: Q105229426