(1R,2R,5S,9S,17S)-5-hydroxy-7,13-diazatetracyclo[7.7.1.02,7.013,17]heptadecan-6-one

Details

• Internal ID: c54fcc07-352a-45b9-9cdd-43d5f6abb95f
• Taxonomy: Alkaloids and derivatives > Lupin alkaloids > Matrine alkaloids
• IUPAC Name: (1R,2R,5S,9S,17S)-5-hydroxy-7,13-diazatetracyclo[7.7.1.02,7.013,17]heptadecan-6-one
• SMILES (Canonical): C1CC2CN3C(CCC(C3=O)O)C4C2N(C1)CCC4
• SMILES (Isomeric): C1C[C@H]2CN3[C@H](CC[C@@H](C3=O)O)[C@@H]4[C@H]2N(C1)CCC4
• InChI: InChI=1S/C15H24N2O2/c18-13-6-5-12-11-4-2-8-16-7-1-3-10(14(11)16)9-17(12)15(13)19/h10-14,18H,1-9H2/t10-,11+,12+,13-,14-/m0/s1
• InChI Key: WZKRTWRYJWGESZ-ZSLBOAEBSA-N
• Popularity: 2 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: 1.00
• Atomic LogP (AlogP): 0.84
• H-Bond Acceptor: 3
• H-Bond Donor: 1
• Rotatable Bonds: 0

Synonyms

• CHEMBL3590539

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9667	96.67%
Caco-2	+	0.6475	64.75%
Blood Brain Barrier	+	0.8444	84.44%
Human oral bioavailability	+	0.6000	60.00%
Subcellular localzation	Mitochondria	0.7899	78.99%
OATP2B1 inhibitior	-	0.8549	85.49%
OATP1B1 inhibitior	+	0.9356	93.56%
OATP1B3 inhibitior	+	0.9481	94.81%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	+	0.6000	60.00%
BSEP inhibitior	-	0.8482	84.82%
P-glycoprotein inhibitior	-	0.9530	95.30%
P-glycoprotein substrate	-	0.8024	80.24%
CYP3A4 substrate	-	0.5160	51.60%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	+	0.4475	44.75%
CYP3A4 inhibition	-	0.9617	96.17%
CYP2C9 inhibition	-	0.9393	93.93%
CYP2C19 inhibition	-	0.8409	84.09%
CYP2D6 inhibition	-	0.8364	83.64%
CYP1A2 inhibition	-	0.8756	87.56%
CYP2C8 inhibition	-	0.9613	96.13%
CYP inhibitory promiscuity	-	0.9470	94.70%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6377	63.77%
Eye corrosion	-	0.9778	97.78%
Eye irritation	-	0.7907	79.07%
Skin irritation	-	0.6877	68.77%
Skin corrosion	-	0.8485	84.85%
Ames mutagenesis	-	0.6700	67.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6427	64.27%
Micronuclear	+	0.5700	57.00%
Hepatotoxicity	+	0.8689	86.89%
skin sensitisation	-	0.8900	89.00%
Respiratory toxicity	+	0.6667	66.67%
Reproductive toxicity	+	0.8667	86.67%
Mitochondrial toxicity	+	0.8875	88.75%
Nephrotoxicity	+	0.7858	78.58%
Acute Oral Toxicity (c)	III	0.5844	58.44%
Estrogen receptor binding	-	0.5313	53.13%
Androgen receptor binding	-	0.5143	51.43%
Thyroid receptor binding	-	0.5620	56.20%
Glucocorticoid receptor binding	-	0.5317	53.17%
Aromatase binding	-	0.7789	77.89%
PPAR gamma	-	0.8092	80.92%
Honey bee toxicity	-	0.8883	88.83%
Biodegradation	-	0.5500	55.00%
Crustacea aquatic toxicity	+	0.6000	60.00%
Fish aquatic toxicity	-	0.9673	96.73%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	91.15%	98.95%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	89.98%	93.03%
CHEMBL3746	P80365	11-beta-hydroxysteroid dehydrogenase 2	87.67%	94.78%
CHEMBL253	P34972	Cannabinoid CB2 receptor	87.11%	97.25%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.00%	95.56%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	86.44%	93.04%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	86.21%	94.45%
CHEMBL238	Q01959	Dopamine transporter	86.19%	95.88%
CHEMBL5608	Q16288	NT-3 growth factor receptor	84.85%	95.89%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	84.82%	93.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	84.53%	97.09%
CHEMBL4394	Q9NYA1	Sphingosine kinase 1	84.46%	96.03%
CHEMBL217	P14416	Dopamine D2 receptor	82.22%	95.62%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	80.76%	99.23%
CHEMBL1902	P62942	FK506-binding protein 1A	80.65%	97.05%

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

Cross-Links

• PubChem: 10659287
• NPASS: NPC178632
• LOTUS: LTS0269890
• wikiData: Q104888254