(1R,12S,13R,14R,15E)-15-ethylidene-13-(hydroxymethyl)-3-methyl-3,17-diazapentacyclo[12.3.1.02,10.04,9.012,17]octadeca-2(10),4,6,8-tetraen-1-ol

Details

• Internal ID: 3d53f348-5992-4e24-92fc-cb0a1a895abc
• Taxonomy: Alkaloids and derivatives > Macroline alkaloids
• IUPAC Name: (1R,12S,13R,14R,15E)-15-ethylidene-13-(hydroxymethyl)-3-methyl-3,17-diazapentacyclo[12.3.1.02,10.04,9.012,17]octadeca-2(10),4,6,8-tetraen-1-ol
• SMILES (Canonical): CC=C1CN2C3CC4=C(C2(CC1C3CO)O)N(C5=CC=CC=C45)C
• SMILES (Isomeric): C/C=C\1/CN2[C@H]3CC4=C([C@@]2(C[C@@H]1[C@H]3CO)O)N(C5=CC=CC=C45)C
• InChI: InChI=1S/C20H24N2O2/c1-3-12-10-22-18-8-14-13-6-4-5-7-17(13)21(2)19(14)20(22,24)9-15(12)16(18)11-23/h3-7,15-16,18,23-24H,8-11H2,1-2H3/b12-3-/t15-,16+,18-,20+/m0/s1
• InChI Key: JQILJROVLDSOTD-WCZLNECCSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₄N₂O₂
• Molecular Weight: 324.40 g/mol
• Exact Mass: 324.183778013 g/mol
• Topological Polar Surface Area (TPSA): 48.60 Ų
• XlogP: 1.30
• Atomic LogP (AlogP): 2.14
• H-Bond Acceptor: 4
• H-Bond Donor: 2
• Rotatable Bonds: 1

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9691	96.91%
Caco-2	+	0.7585	75.85%
Blood Brain Barrier	+	0.7000	70.00%
Human oral bioavailability	-	0.5571	55.71%
Subcellular localzation	Mitochondria	0.6066	60.66%
OATP2B1 inhibitior	-	0.8602	86.02%
OATP1B1 inhibitior	+	0.9010	90.10%
OATP1B3 inhibitior	+	0.9425	94.25%
MATE1 inhibitior	-	0.9012	90.12%
OCT2 inhibitior	-	0.5000	50.00%
BSEP inhibitior	-	0.6615	66.15%
P-glycoprotein inhibitior	-	0.8234	82.34%
P-glycoprotein substrate	+	0.6368	63.68%
CYP3A4 substrate	+	0.6218	62.18%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7673	76.73%
CYP3A4 inhibition	-	0.8514	85.14%
CYP2C9 inhibition	-	0.8030	80.30%
CYP2C19 inhibition	-	0.6977	69.77%
CYP2D6 inhibition	-	0.6344	63.44%
CYP1A2 inhibition	-	0.6803	68.03%
CYP2C8 inhibition	-	0.5641	56.41%
CYP inhibitory promiscuity	-	0.6285	62.85%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9400	94.00%
Carcinogenicity (trinary)	Non-required	0.6171	61.71%
Eye corrosion	-	0.9884	98.84%
Eye irritation	-	0.9931	99.31%
Skin irritation	-	0.7750	77.50%
Skin corrosion	-	0.9176	91.76%
Ames mutagenesis	+	0.6700	67.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8594	85.94%
Micronuclear	+	0.6800	68.00%
Hepatotoxicity	-	0.5539	55.39%
skin sensitisation	-	0.8570	85.70%
Respiratory toxicity	+	0.8444	84.44%
Reproductive toxicity	+	0.9667	96.67%
Mitochondrial toxicity	+	0.9000	90.00%
Nephrotoxicity	-	0.6365	63.65%
Acute Oral Toxicity (c)	III	0.5895	58.95%
Estrogen receptor binding	-	0.5617	56.17%
Androgen receptor binding	+	0.6131	61.31%
Thyroid receptor binding	+	0.6546	65.46%
Glucocorticoid receptor binding	-	0.5244	52.44%
Aromatase binding	-	0.5366	53.66%
PPAR gamma	-	0.5957	59.57%
Honey bee toxicity	-	0.9117	91.17%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	+	0.5600	56.00%
Fish aquatic toxicity	-	0.5237	52.37%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL253	P34972	Cannabinoid CB2 receptor	98.10%	97.25%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	96.51%	95.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.44%	96.09%
CHEMBL3192	Q9BY41	Histone deacetylase 8	92.68%	93.99%
CHEMBL2581	P07339	Cathepsin D	91.51%	98.95%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	89.43%	95.83%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.02%	89.00%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	87.34%	91.11%
CHEMBL226	P30542	Adenosine A1 receptor	85.01%	95.93%
CHEMBL3137262	O60341	LSD1/CoREST complex	83.14%	97.09%
CHEMBL255	P29275	Adenosine A2b receptor	80.14%	98.59%

Plants that contains it

• Tabernaemontana solanifolia

Cross-Links

• PubChem: 162858937
• LOTUS: LTS0240353
• wikiData: Q105133499