[(1S,12R)-13-(hydroxymethyl)-16-methyl-3,17-diazapentacyclo[12.3.1.02,10.04,9.012,17]octadeca-2(10),4,6,8-tetraen-15-yl]methanol

Details

• Internal ID: 970fd971-4dea-4cf8-9c48-77ae97daa16d
• Taxonomy: Alkaloids and derivatives > Macroline alkaloids
• IUPAC Name: [(1S,12R)-13-(hydroxymethyl)-16-methyl-3,17-diazapentacyclo[12.3.1.02,10.04,9.012,17]octadeca-2(10),4,6,8-tetraen-15-yl]methanol
• SMILES (Canonical): CC1C(C2CC3N1C(C2CO)CC4=C3NC5=CC=CC=C45)CO
• SMILES (Isomeric): CC1C(C2C[C@@H]3N1[C@@H](C2CO)CC4=C3NC5=CC=CC=C45)CO
• InChI: InChI=1S/C19H24N2O2/c1-10-14(8-22)12-6-18-19-13(7-17(21(10)18)15(12)9-23)11-4-2-3-5-16(11)20-19/h2-5,10,12,14-15,17-18,20,22-23H,6-9H2,1H3/t10?,12?,14?,15?,17-,18+/m1/s1
• InChI Key: PBLXNPSLWYWTKM-TVNVQTOGSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₉H₂₄N₂O₂
• Molecular Weight: 312.40 g/mol
• Exact Mass: 312.183778013 g/mol
• Topological Polar Surface Area (TPSA): 59.50 Ų
• XlogP: 1.80
• Atomic LogP (AlogP): 2.07
• H-Bond Acceptor: 3
• H-Bond Donor: 3
• Rotatable Bonds: 2

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9893	98.93%
Caco-2	+	0.8226	82.26%
Blood Brain Barrier	+	0.8500	85.00%
Human oral bioavailability	-	0.7714	77.14%
Subcellular localzation	Mitochondria	0.5091	50.91%
OATP2B1 inhibitior	-	0.8600	86.00%
OATP1B1 inhibitior	+	0.8699	86.99%
OATP1B3 inhibitior	+	0.9395	93.95%
MATE1 inhibitior	-	0.8612	86.12%
OCT2 inhibitior	+	0.5750	57.50%
BSEP inhibitior	+	0.5508	55.08%
P-glycoprotein inhibitior	-	0.9522	95.22%
P-glycoprotein substrate	-	0.5282	52.82%
CYP3A4 substrate	+	0.5827	58.27%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	+	0.5754	57.54%
CYP3A4 inhibition	-	0.6003	60.03%
CYP2C9 inhibition	-	0.8998	89.98%
CYP2C19 inhibition	-	0.7358	73.58%
CYP2D6 inhibition	-	0.6279	62.79%
CYP1A2 inhibition	-	0.5885	58.85%
CYP2C8 inhibition	-	0.6241	62.41%
CYP inhibitory promiscuity	-	0.5738	57.38%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.6676	66.76%
Eye corrosion	-	0.9882	98.82%
Eye irritation	-	0.9561	95.61%
Skin irritation	-	0.7676	76.76%
Skin corrosion	-	0.9328	93.28%
Ames mutagenesis	-	0.5354	53.54%
Human Ether-a-go-go-Related Gene inhibition	+	0.8161	81.61%
Micronuclear	+	0.7000	70.00%
Hepatotoxicity	-	0.5091	50.91%
skin sensitisation	-	0.8801	88.01%
Respiratory toxicity	+	0.8778	87.78%
Reproductive toxicity	+	0.8667	86.67%
Mitochondrial toxicity	+	0.9500	95.00%
Nephrotoxicity	-	0.6361	63.61%
Acute Oral Toxicity (c)	III	0.6138	61.38%
Estrogen receptor binding	+	0.6438	64.38%
Androgen receptor binding	+	0.6603	66.03%
Thyroid receptor binding	-	0.5303	53.03%
Glucocorticoid receptor binding	-	0.5959	59.59%
Aromatase binding	-	0.6085	60.85%
PPAR gamma	-	0.5517	55.17%
Honey bee toxicity	-	0.8996	89.96%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	-	0.5100	51.00%
Fish aquatic toxicity	+	0.8367	83.67%

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	97.80%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.83%	91.11%
CHEMBL2581	P07339	Cathepsin D	93.87%	98.95%
CHEMBL3137262	O60341	LSD1/CoREST complex	93.68%	97.09%
CHEMBL3192	Q9BY41	Histone deacetylase 8	90.12%	93.99%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.78%	95.56%
CHEMBL1951	P21397	Monoamine oxidase A	88.13%	91.49%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.80%	89.00%
CHEMBL3310	Q96DB2	Histone deacetylase 11	85.15%	88.56%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	83.99%	94.45%
CHEMBL228	P31645	Serotonin transporter	82.63%	95.51%

Plants that contains it

• Rauvolfia caffra
• Rauvolfia serpentina

Cross-Links

• PubChem: 138113966
• LOTUS: LTS0141277
• wikiData: Q104392885