Sophoranol

Details

• Internal ID: aec9e0ca-d613-4439-ba2b-d8e96e3d6cf9
• Taxonomy: Alkaloids and derivatives > Lupin alkaloids > Matrine alkaloids
• IUPAC Name: (1R,2R,9R,17R)-9-hydroxy-7,13-diazatetracyclo[7.7.1.02,7.013,17]heptadecan-6-one
• SMILES (Canonical): C1CC2C3CCCN4C3C(CCC4)(CN2C(=O)C1)O
• SMILES (Isomeric): C1C[C@@H]2[C@H]3CCCN4[C@H]3[C@@](CCC4)(CN2C(=O)C1)O
• InChI: InChI=1S/C15H24N2O2/c18-13-6-1-5-12-11-4-2-8-16-9-3-7-15(19,14(11)16)10-17(12)13/h11-12,14,19H,1-10H2/t11-,12-,14-,15-/m1/s1
• InChI Key: VQYBAEAOOJBSTR-QHSBEEBCSA-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: 0.50
• Atomic LogP (AlogP): 0.99
• H-Bond Acceptor: 3
• H-Bond Donor: 1
• Rotatable Bonds: 0

Synonyms

• 3411-37-8
• (+)-Sophoranol
• 5-Hydroxymatrine
• (7AR,13aR,13bR,13cR)-dodecahydro-7a-hydroxy-1H,5H,10H-dipyrido[2,1-f:3 inverted exclamation marka,2 inverted exclamation marka,1 inverted exclamation marka-ij][1,6]naphthyridin-10-one
• SCHEMBL564487
• CHEMBL3590537
• CHEBI:80905
• AKOS040760715
• HY-126033
• CS-0090291
• C17069
• Q27151403
• (1R,2R,9R,17R)-9-hydroxy-7,13-diazatetracyclo[7.7.1.0?,?.0??,??]heptadecan-6-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9758	97.58%
Caco-2	+	0.7078	70.78%
Blood Brain Barrier	+	0.8694	86.94%
Human oral bioavailability	-	0.5143	51.43%
Subcellular localzation	Mitochondria	0.7412	74.12%
OATP2B1 inhibitior	-	0.8565	85.65%
OATP1B1 inhibitior	+	0.9166	91.66%
OATP1B3 inhibitior	+	0.9516	95.16%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	+	0.6250	62.50%
BSEP inhibitior	-	0.6595	65.95%
P-glycoprotein inhibitior	-	0.9427	94.27%
P-glycoprotein substrate	-	0.8247	82.47%
CYP3A4 substrate	+	0.5645	56.45%
CYP2C9 substrate	-	0.8056	80.56%
CYP2D6 substrate	+	0.3748	37.48%
CYP3A4 inhibition	-	0.8462	84.62%
CYP2C9 inhibition	-	0.9332	93.32%
CYP2C19 inhibition	-	0.9030	90.30%
CYP2D6 inhibition	-	0.7128	71.28%
CYP1A2 inhibition	-	0.9071	90.71%
CYP2C8 inhibition	-	0.9404	94.04%
CYP inhibitory promiscuity	-	0.9594	95.94%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6310	63.10%
Eye corrosion	-	0.9823	98.23%
Eye irritation	-	0.7841	78.41%
Skin irritation	-	0.7174	71.74%
Skin corrosion	-	0.8353	83.53%
Ames mutagenesis	-	0.8500	85.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6337	63.37%
Micronuclear	+	0.5600	56.00%
Hepatotoxicity	+	0.6960	69.60%
skin sensitisation	-	0.8693	86.93%
Respiratory toxicity	+	0.7000	70.00%
Reproductive toxicity	+	0.8222	82.22%
Mitochondrial toxicity	+	0.8875	88.75%
Nephrotoxicity	-	0.6571	65.71%
Acute Oral Toxicity (c)	III	0.6318	63.18%
Estrogen receptor binding	-	0.5897	58.97%
Androgen receptor binding	+	0.5668	56.68%
Thyroid receptor binding	-	0.6459	64.59%
Glucocorticoid receptor binding	+	0.6572	65.72%
Aromatase binding	-	0.7740	77.40%
PPAR gamma	-	0.6181	61.81%
Honey bee toxicity	-	0.9088	90.88%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	-	0.5700	57.00%
Fish aquatic toxicity	-	0.9716	97.16%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL253	P34972	Cannabinoid CB2 receptor	94.53%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	92.64%	91.11%
CHEMBL2581	P07339	Cathepsin D	92.22%	98.95%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	89.99%	93.04%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	89.74%	93.03%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.49%	95.56%
CHEMBL217	P14416	Dopamine D2 receptor	86.98%	95.62%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	86.00%	94.45%
CHEMBL3137262	O60341	LSD1/CoREST complex	85.90%	97.09%
CHEMBL5103	Q969S8	Histone deacetylase 10	85.31%	90.08%
CHEMBL2781	P19634	Sodium/hydrogen exchanger 1	84.12%	90.24%
CHEMBL3746	P80365	11-beta-hydroxysteroid dehydrogenase 2	84.05%	94.78%
CHEMBL238	Q01959	Dopamine transporter	84.00%	95.88%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.83%	95.89%
CHEMBL1937	Q92769	Histone deacetylase 2	83.15%	94.75%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	82.58%	90.71%
CHEMBL1902	P62942	FK506-binding protein 1A	81.82%	97.05%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	81.55%	96.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	81.25%	100.00%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	81.23%	95.50%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	81.07%	93.00%
CHEMBL3012	Q13946	Phosphodiesterase 7A	80.82%	99.29%
CHEMBL4588	P22894	Matrix metalloproteinase 8	80.71%	94.66%

Plants that contains it

• Actinidia polygama
• Asimina parviflora
• Atraphaxis spinosa
• Baccharis neglecta
• Centaurea cuneifolia subsp. cuneifolia
• Chondrodendron tomentosum
• Clerodendrum bungei
• Cuscuta australis
• Cuscuta chilensis
• 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 macrocarpa
• Sophora tonkinensis
• Stenocereus laevigatus
• Syzygium polycephaloides
• Varronia leucocephala
• Vellozia nanuzae
• Vernonanthura fagifolia

Cross-Links

• PubChem: 12442899
• NPASS: NPC124359
• LOTUS: LTS0166977
• wikiData: Q27151403