9alpha-Hydroxymatrine

Details

• Internal ID: 9a512420-c927-4344-8c13-eb106737b2f1
• Taxonomy: Alkaloids and derivatives > Lupin alkaloids > Matrine alkaloids
• IUPAC Name: (1R,2R,9S,15S,17S)-15-hydroxy-7,13-diazatetracyclo[7.7.1.02,7.013,17]heptadecan-6-one
• SMILES (Canonical): C1CC2C3CC(CN4C3C(CCC4)CN2C(=O)C1)O
• SMILES (Isomeric): C1C[C@@H]2[C@H]3C[C@@H](CN4[C@H]3[C@@H](CCC4)CN2C(=O)C1)O
• InChI: InChI=1S/C15H24N2O2/c18-11-7-12-13-4-1-5-14(19)17(13)8-10-3-2-6-16(9-11)15(10)12/h10-13,15,18H,1-9H2/t10-,11-,12+,13+,15-/m0/s1
• InChI Key: JTWPUVIWKODBID-WHPHWUKISA-N
• Popularity: 3 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₄N₂O₂
• Molecular Weight: 264.36 g/mol
• Exact Mass: 264.183778013 g/mol
• Topological Polar Surface Area (TPSA): 43.80 Ų
• XlogP: 0.60
• Atomic LogP (AlogP): 0.84
• H-Bond Acceptor: 3
• H-Bond Donor: 1
• Rotatable Bonds: 0

Synonyms

• 9|A-Hydroxymatrine
• 88509-92-6
• 1H,5H,10H-Dipyrido[2,1-f:3',2',1'-ij][1,6]naphthyridin-10-one, dodecahydro-2-hydroxy-, (2S,7aS,13aR,13bR,13cS)-
• 9??-Hydroxymatrine
• CHEMBL204747
• DTXSID901316455
• HY-N11671
• AKOS040734151
• CS-0676386

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9709	97.09%
Caco-2	+	0.7700	77.00%
Blood Brain Barrier	+	0.8944	89.44%
Human oral bioavailability	+	0.5571	55.71%
Subcellular localzation	Mitochondria	0.7308	73.08%
OATP2B1 inhibitior	-	0.8579	85.79%
OATP1B1 inhibitior	+	0.9201	92.01%
OATP1B3 inhibitior	+	0.9531	95.31%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	+	0.7000	70.00%
BSEP inhibitior	-	0.7908	79.08%
P-glycoprotein inhibitior	-	0.9576	95.76%
P-glycoprotein substrate	-	0.7025	70.25%
CYP3A4 substrate	+	0.5425	54.25%
CYP2C9 substrate	-	0.8144	81.44%
CYP2D6 substrate	+	0.4260	42.60%
CYP3A4 inhibition	-	0.9644	96.44%
CYP2C9 inhibition	-	0.9429	94.29%
CYP2C19 inhibition	-	0.8243	82.43%
CYP2D6 inhibition	-	0.8940	89.40%
CYP1A2 inhibition	-	0.8225	82.25%
CYP2C8 inhibition	-	0.9444	94.44%
CYP inhibitory promiscuity	-	0.9161	91.61%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6528	65.28%
Eye corrosion	-	0.9697	96.97%
Eye irritation	-	0.6518	65.18%
Skin irritation	-	0.7185	71.85%
Skin corrosion	-	0.8336	83.36%
Ames mutagenesis	-	0.8000	80.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6126	61.26%
Micronuclear	+	0.5400	54.00%
Hepatotoxicity	+	0.7750	77.50%
skin sensitisation	-	0.8966	89.66%
Respiratory toxicity	+	0.6444	64.44%
Reproductive toxicity	+	0.7778	77.78%
Mitochondrial toxicity	+	0.8625	86.25%
Nephrotoxicity	+	0.6673	66.73%
Acute Oral Toxicity (c)	III	0.7067	70.67%
Estrogen receptor binding	-	0.7209	72.09%
Androgen receptor binding	-	0.5496	54.96%
Thyroid receptor binding	-	0.6141	61.41%
Glucocorticoid receptor binding	-	0.5302	53.02%
Aromatase binding	-	0.8077	80.77%
PPAR gamma	-	0.7641	76.41%
Honey bee toxicity	-	0.8402	84.02%
Biodegradation	-	0.5500	55.00%
Crustacea aquatic toxicity	-	0.5100	51.00%
Fish aquatic toxicity	-	0.9796	97.96%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3137262	O60341	LSD1/CoREST complex	90.57%	97.09%
CHEMBL6136	O60341	Lysine-specific histone demethylase 1	90.08%	95.58%
CHEMBL3746	P80365	11-beta-hydroxysteroid dehydrogenase 2	89.70%	94.78%
CHEMBL4394	Q9NYA1	Sphingosine kinase 1	88.51%	96.03%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	87.74%	93.03%
CHEMBL217	P14416	Dopamine D2 receptor	87.07%	95.62%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.58%	95.56%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	86.56%	91.11%
CHEMBL2581	P07339	Cathepsin D	85.79%	98.95%
CHEMBL4235	P28845	11-beta-hydroxysteroid dehydrogenase 1	85.70%	97.98%
CHEMBL253	P34972	Cannabinoid CB2 receptor	85.23%	97.25%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	84.89%	96.09%
CHEMBL2140	P48775	Tryptophan 2,3-dioxygenase	83.99%	98.46%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	83.94%	93.04%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.51%	95.89%
CHEMBL1994	P08235	Mineralocorticoid receptor	82.28%	100.00%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	81.71%	93.00%
CHEMBL5255	O00206	Toll-like receptor 4	81.10%	92.50%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	81.09%	90.71%
CHEMBL1795139	Q8IU80	Transmembrane protease serine 6	80.63%	98.33%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	80.61%	99.23%
CHEMBL238	Q01959	Dopamine transporter	80.24%	95.88%

Plants that contains it

• Asimina parviflora
• Atraphaxis spinosa
• Baccharis neglecta
• Centaurea cuneifolia subsp. cuneifolia
• Chondrodendron tomentosum
• Clerodendrum bungei
• Diospyros ebenum
• Embelia parviflora
• Embelia schimperi
• Ephedra sinica
• Epilobium hirsutum
• Erysimum leptophyllum
• Erythrina melanacantha
• Esenbeckia leiocarpa
• Euphorbia jolkinii
• Faramea multiflora
• Gymnocalycium schickendantzii
• Haplophyllum obtusifolium
• Helichrysum tenuifolium
• Hypericum styphelioides
• Linnaea chinensis
• Lythrum salicaria
• Monsonia senegalensis
• Myrica rubra
• Onopordum acanthium
• Pancratium sickenbergeri
• Pinalia anomala
• Piper regnellii
• Plathymenia reticulata
• Pteridium esculentum
• Simarouba glauca
• Sophora davidii
• Sophora flavescens
• Sophora macrocarpa
• Sophora tonkinensis
• Stenocereus laevigatus
• Syzygium polycephaloides
• Varronia leucocephala
• Vellozia nanuzae
• Vernonanthura fagifolia

Cross-Links

• PubChem: 15385684
• NPASS: NPC168017
• LOTUS: LTS0187883
• wikiData: Q105135041