Methyl 17,18-dihydroxy-1,3,11,12,14,15,16,17,18,19,20,21-dodecahydroyohimban-19-carboxylate

Details

• Internal ID: b23f4a9f-a409-4d80-ae58-297d0937ef62
• Taxonomy: Alkaloids and derivatives > Yohimbine alkaloids
• IUPAC Name: methyl 17,18-dihydroxy-1,3,11,12,14,15,16,17,18,19,20,21-dodecahydroyohimban-19-carboxylate
• SMILES (Canonical): COC(=O)C1C2CC3C4=C(CCN3CC2CC(C1O)O)C5=CC=CC=C5N4
• SMILES (Isomeric): COC(=O)C1C2CC3C4=C(CCN3CC2CC(C1O)O)C5=CC=CC=C5N4
• InChI: InChI=1S/C21H26N2O4/c1-27-21(26)18-14-9-16-19-13(12-4-2-3-5-15(12)22-19)6-7-23(16)10-11(14)8-17(24)20(18)25/h2-5,11,14,16-18,20,22,24-25H,6-10H2,1H3
• InChI Key: MMVZFQGCDSDHSV-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₂₆N₂O₄
• Molecular Weight: 370.40 g/mol
• Exact Mass: 370.18925731 g/mol
• Topological Polar Surface Area (TPSA): 85.80 Ų
• XlogP: 2.00
• Atomic LogP (AlogP): 1.62
• H-Bond Acceptor: 5
• H-Bond Donor: 3
• Rotatable Bonds: 1

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8986	89.86%
Caco-2	+	0.7575	75.75%
Blood Brain Barrier	-	0.7000	70.00%
Human oral bioavailability	-	0.8714	87.14%
Subcellular localzation	Mitochondria	0.6057	60.57%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9121	91.21%
OATP1B3 inhibitior	+	0.9250	92.50%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	+	0.8411	84.11%
P-glycoprotein inhibitior	-	0.7753	77.53%
P-glycoprotein substrate	+	0.8743	87.43%
CYP3A4 substrate	+	0.7618	76.18%
CYP2C9 substrate	-	0.8550	85.50%
CYP2D6 substrate	+	0.4336	43.36%
CYP3A4 inhibition	-	0.9285	92.85%
CYP2C9 inhibition	-	0.9078	90.78%
CYP2C19 inhibition	-	0.9244	92.44%
CYP2D6 inhibition	+	0.5588	55.88%
CYP1A2 inhibition	-	0.8849	88.49%
CYP2C8 inhibition	-	0.6050	60.50%
CYP inhibitory promiscuity	-	0.9474	94.74%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6040	60.40%
Eye corrosion	-	0.9905	99.05%
Eye irritation	-	0.9906	99.06%
Skin irritation	-	0.7539	75.39%
Skin corrosion	-	0.9455	94.55%
Ames mutagenesis	-	0.6578	65.78%
Human Ether-a-go-go-Related Gene inhibition	+	0.8462	84.62%
Micronuclear	+	0.6600	66.00%
Hepatotoxicity	-	0.8000	80.00%
skin sensitisation	-	0.8874	88.74%
Respiratory toxicity	+	0.9444	94.44%
Reproductive toxicity	+	0.9778	97.78%
Mitochondrial toxicity	+	0.9875	98.75%
Nephrotoxicity	+	0.7105	71.05%
Acute Oral Toxicity (c)	II	0.4475	44.75%
Estrogen receptor binding	+	0.6139	61.39%
Androgen receptor binding	+	0.7696	76.96%
Thyroid receptor binding	-	0.5272	52.72%
Glucocorticoid receptor binding	-	0.4911	49.11%
Aromatase binding	-	0.7629	76.29%
PPAR gamma	-	0.7371	73.71%
Honey bee toxicity	-	0.8124	81.24%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	+	0.5600	56.00%
Fish aquatic toxicity	-	0.5672	56.72%

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	98.47%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.18%	91.11%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	96.97%	85.14%
CHEMBL1914	P06276	Butyrylcholinesterase	95.78%	95.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	95.12%	95.56%
CHEMBL2535	P11166	Glucose transporter	93.86%	98.75%
CHEMBL2581	P07339	Cathepsin D	93.40%	98.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	90.39%	94.45%
CHEMBL3137262	O60341	LSD1/CoREST complex	89.10%	97.09%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	86.98%	99.23%
CHEMBL5028	O14672	ADAM10	85.77%	97.50%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	84.48%	94.08%
CHEMBL255	P29275	Adenosine A2b receptor	84.05%	98.59%

Plants that contains it

• Rauvolfia serpentina

Cross-Links

• PubChem: 24011655
• LOTUS: LTS0038178
• wikiData: Q105168137