(+)-12alpha-Hydroxysophocarpine

Details

• Internal ID: 06af5cb7-aa32-4ca0-b36f-fad2380b3e82
• Taxonomy: Alkaloids and derivatives > Lupin alkaloids > Matrine alkaloids
• IUPAC Name: (1S,2S,3S,9S,17S)-3-hydroxy-7,13-diazatetracyclo[7.7.1.02,7.013,17]heptadec-4-en-6-one
• SMILES (Canonical): C1CC2CN3C(C4C2N(C1)CCC4)C(C=CC3=O)O
• SMILES (Isomeric): C1C[C@H]2CN3[C@@H]([C@@H]4[C@H]2N(C1)CCC4)[C@H](C=CC3=O)O
• InChI: InChI=1S/C15H22N2O2/c18-12-5-6-13(19)17-9-10-3-1-7-16-8-2-4-11(14(10)16)15(12)17/h5-6,10-12,14-15,18H,1-4,7-9H2/t10-,11-,12-,14-,15-/m0/s1
• InChI Key: RAGVUCIHXGJGEQ-YLXLXVFQSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₂N₂O₂
• Molecular Weight: 262.35 g/mol
• Exact Mass: 262.168127949 g/mol
• Topological Polar Surface Area (TPSA): 43.80 Ų
• XlogP: 0.60
• Atomic LogP (AlogP): 0.62
• H-Bond Acceptor: 3
• H-Bond Donor: 1
• Rotatable Bonds: 0

Synonyms

• CHEMBL441175
• J3.497.995B

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9681	96.81%
Caco-2	+	0.8614	86.14%
Blood Brain Barrier	+	0.8444	84.44%
Human oral bioavailability	+	0.6000	60.00%
Subcellular localzation	Mitochondria	0.5686	56.86%
OATP2B1 inhibitior	-	0.8605	86.05%
OATP1B1 inhibitior	+	0.9065	90.65%
OATP1B3 inhibitior	+	0.9524	95.24%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	+	0.7000	70.00%
BSEP inhibitior	-	0.8933	89.33%
P-glycoprotein inhibitior	-	0.9634	96.34%
P-glycoprotein substrate	-	0.7642	76.42%
CYP3A4 substrate	+	0.5575	55.75%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7741	77.41%
CYP3A4 inhibition	-	0.9411	94.11%
CYP2C9 inhibition	-	0.9160	91.60%
CYP2C19 inhibition	-	0.8607	86.07%
CYP2D6 inhibition	-	0.9257	92.57%
CYP1A2 inhibition	-	0.8155	81.55%
CYP2C8 inhibition	-	0.9665	96.65%
CYP inhibitory promiscuity	-	0.8132	81.32%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6336	63.36%
Eye corrosion	-	0.9697	96.97%
Eye irritation	-	0.9018	90.18%
Skin irritation	-	0.6559	65.59%
Skin corrosion	-	0.8766	87.66%
Ames mutagenesis	-	0.7500	75.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6170	61.70%
Micronuclear	+	0.5700	57.00%
Hepatotoxicity	+	0.7689	76.89%
skin sensitisation	-	0.8802	88.02%
Respiratory toxicity	+	0.7444	74.44%
Reproductive toxicity	+	0.7111	71.11%
Mitochondrial toxicity	+	0.8750	87.50%
Nephrotoxicity	+	0.6339	63.39%
Acute Oral Toxicity (c)	II	0.5105	51.05%
Estrogen receptor binding	-	0.8425	84.25%
Androgen receptor binding	-	0.6197	61.97%
Thyroid receptor binding	-	0.6164	61.64%
Glucocorticoid receptor binding	-	0.6208	62.08%
Aromatase binding	-	0.9095	90.95%
PPAR gamma	-	0.6771	67.71%
Honey bee toxicity	-	0.9242	92.42%
Biodegradation	-	0.6250	62.50%
Crustacea aquatic toxicity	+	0.5600	56.00%
Fish aquatic toxicity	-	0.8731	87.31%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	96.30%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.95%	95.56%
CHEMBL253	P34972	Cannabinoid CB2 receptor	87.92%	97.25%
CHEMBL5608	Q16288	NT-3 growth factor receptor	85.84%	95.89%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	85.66%	93.03%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	85.40%	93.04%
CHEMBL2140	P48775	Tryptophan 2,3-dioxygenase	84.93%	98.46%
CHEMBL1994	P08235	Mineralocorticoid receptor	84.89%	100.00%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	83.36%	90.71%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	82.75%	96.09%
CHEMBL1871	P10275	Androgen Receptor	82.28%	96.43%
CHEMBL3137262	O60341	LSD1/CoREST complex	82.03%	97.09%
CHEMBL1795139	Q8IU80	Transmembrane protease serine 6	81.45%	98.33%

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 flavescens
• Sophora tonkinensis
• Stenocereus laevigatus
• Syzygium polycephaloides
• Varronia leucocephala
• Vellozia nanuzae
• Vernonanthura fagifolia

Cross-Links

• PubChem: 44408595
• NPASS: NPC144714
• LOTUS: LTS0194659
• wikiData: Q105232605