Sinomenine

Details

• Internal ID: deda7b9a-9f99-4b91-86b7-a1f9edff7ea9
• Taxonomy: Alkaloids and derivatives > Morphinans
• IUPAC Name: (1R,9S,10S)-3-hydroxy-4,12-dimethoxy-17-methyl-17-azatetracyclo[7.5.3.01,10.02,7]heptadeca-2(7),3,5,11-tetraen-13-one
• SMILES (Canonical): CN1CCC23CC(=O)C(=CC2C1CC4=C3C(=C(C=C4)OC)O)OC
• SMILES (Isomeric): CN1CC[C@@]23CC(=O)C(=C[C@@H]2[C@@H]1CC4=C3C(=C(C=C4)OC)O)OC
• InChI: InChI=1S/C19H23NO4/c1-20-7-6-19-10-14(21)16(24-3)9-12(19)13(20)8-11-4-5-15(23-2)18(22)17(11)19/h4-5,9,12-13,22H,6-8,10H2,1-3H3/t12-,13+,19-/m1/s1
• InChI Key: INYYVPJSBIVGPH-QHRIQVFBSA-N
• Popularity: 798 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₉H₂₃NO₄
• Molecular Weight: 329.40 g/mol
• Exact Mass: 329.16270821 g/mol
• Topological Polar Surface Area (TPSA): 59.00 Ų
• XlogP: 2.20
• Atomic LogP (AlogP): 2.02
• H-Bond Acceptor: 5
• H-Bond Donor: 1
• Rotatable Bonds: 2

Synonyms

• 115-53-7
• Kukoline
• Cucoline
• Coculine
• Sabianine A
• morphinan-6-one, 7,8-didehydro-4-hydroxy-3,7-dimethoxy-17-methyl-, (9alpha,13alpha,14alpha)-
• 63LT81K70N
• (1R,9S,10S)-3-hydroxy-4,12-dimethoxy-17-methyl-17-azatetracyclo[7.5.3.01,10.02,7]heptadeca-2(7),3,5,11-tetraen-13-one
• cuculine
• (1R,9S,10S)-3-hydroxy-4,12-dimethoxy-17-methyl-17-azatetracyclo(7.5.3.01,10.02,7)heptadeca-2(7),3,5,11-tetraen-13-one
• RefChem:183169
• 4-hydroxy-3,7-dimethoxy-17-methylmorphin-7-en-6-one
• 204-094-6
• CCRIS 1550
• SINOMENIN
• CHEBI:9163
• CHEMBL248095
• (1R,9S,10R)-3-Hydroxy-4,12-dimethoxy-17-methyl-17-azatetracyclo[7.5.3.01,10.02,7]heptadeca-2(7),3,5,11-tetraen-13-one
• morphinan-6-one, 7,8-didehydro-4-hydroxy-3,7-dimethoxy-17-methyl-, (9alpha,13alpha,14alpha)-, hydrochloride
• NSC76021
• (9alpha,13alpha,14alpha)-7,8-Didehydro-4-hydroxy-3,7-dimethoxy-17-methylmorphinan-6-one
• SR-05000002170
• EINECS 204-094-6
• BRN 0095280
• UNII-63LT81K70N
• Sinomenine (Cucoline)
• SINOMENINE [MI]
• Spectrum2_001242
• Spectrum3_001134
• Spectrum4_001981
• Spectrum5_001621
• UPCMLD-DP085
• 7,8-Didehydro-4-hydroxy-3,7-dimethoxy-17-methyl-9-alpha,13-alpha,14-alpha-morphinan-6-one
• SINOMENINE [WHO-DD]
• BSPBio_002627
• KBioGR_002508
• 5-21-13-00516 (Beilstein Handbook Reference)
• SCHEMBL363812
• SPECTRUM1505253
• SPBio_001144
• NP51
• orb1305106
• SCHEMBL29474810
• UPCMLD-DP085:001
• BCBcMAP01_000195
• KBio3_002127
• DTXSID00871595
• BDBM224031
• ALBB-020908
• BCP20032
• MSK10242
• BDBM50241298
• CCG-39100
• NSC785175
• s2359
• AKOS000265568
• AKOS015960539
• AKOS016023715
• AC-8025
• FS09811
• NSC-785175
• 9-alpha,13-alpha,14-alpha-Morphinan-6-one, 7,8-didehydro-4-hydroxy-3,7-dimethoxy-17-methyl-
• Morphinan-6-one, 7,8-didehydro-4-hydroxy-3,7-dimethoxy-17-methyl-, (9|A,13|A,14|A)-
• SMP1_000273
• NCGC00161641-01
• NCGC00161641-02
• NCGC00161641-04
• NCGC00161641-05
• BS-42101
• HY-15122
• Sinomenine 100 microg/mL in Acetonitrile
• CS-0003778
• NS00018030
• SW219295-1
• C09643
• 115S537
• Sinomenine, 0.3 mol chloroform of crystallization
• Q7524904
• SR-05000002170-2
• SR-05000002170-3
• BRD-K83459933-001-02-1
• BRD-K83459933-001-05-4
• 7,8-didehydro-4-hydroxy-3,7-dimethoxy-17-methylmorphinan-6-one
• Morphinan-6-one, 7,8-didehydro-4-hydroxy-3,7-dimethoxy-17-methyl-, (9a,13a,14a)-
• (1R,9S,10S)-3-hydroxy-4,12-dimethoxy-17-methyl-17-azatetracyclo[7.5.3.0(1),(1)?.0(2),?]heptadeca-2(7),3,5,11-tetraen-13-one
• MORPHINAN-6-ONE, 7,8-DIDEHYDRO-4-HYDROXY-3,7-DIMETHOXY-17-METHYL-, (9.ALPHA.,13.ALPHA.,14.ALPHA.)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9473	94.73%
Caco-2	+	0.8388	83.88%
Blood Brain Barrier	+	0.9000	90.00%
Human oral bioavailability	-	0.6286	62.86%
Subcellular localzation	Mitochondria	0.6638	66.38%
OATP2B1 inhibitior	-	0.8589	85.89%
OATP1B1 inhibitior	+	0.9414	94.14%
OATP1B3 inhibitior	+	0.9424	94.24%
MATE1 inhibitior	-	0.8400	84.00%
OCT2 inhibitior	-	0.5250	52.50%
BSEP inhibitior	+	0.5750	57.50%
P-glycoprotein inhibitior	-	0.7714	77.14%
P-glycoprotein substrate	+	0.6233	62.33%
CYP3A4 substrate	+	0.6983	69.83%
CYP2C9 substrate	-	0.8223	82.23%
CYP2D6 substrate	+	0.3764	37.64%
CYP3A4 inhibition	-	0.8309	83.09%
CYP2C9 inhibition	-	0.9070	90.70%
CYP2C19 inhibition	-	0.9079	90.79%
CYP2D6 inhibition	+	0.6158	61.58%
CYP1A2 inhibition	-	0.6434	64.34%
CYP2C8 inhibition	-	0.9125	91.25%
CYP inhibitory promiscuity	-	0.9254	92.54%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9200	92.00%
Carcinogenicity (trinary)	Non-required	0.6559	65.59%
Eye corrosion	-	0.9921	99.21%
Eye irritation	-	0.9733	97.33%
Skin irritation	-	0.7486	74.86%
Skin corrosion	-	0.9398	93.98%
Ames mutagenesis	-	0.9200	92.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5821	58.21%
Micronuclear	-	0.6100	61.00%
Hepatotoxicity	-	0.7125	71.25%
skin sensitisation	-	0.8649	86.49%
Respiratory toxicity	+	0.9000	90.00%
Reproductive toxicity	+	0.9222	92.22%
Mitochondrial toxicity	+	0.8500	85.00%
Nephrotoxicity	-	0.7781	77.81%
Acute Oral Toxicity (c)	III	0.7166	71.66%
Estrogen receptor binding	-	0.6587	65.87%
Androgen receptor binding	-	0.6358	63.58%
Thyroid receptor binding	-	0.5000	50.00%
Glucocorticoid receptor binding	+	0.7581	75.81%
Aromatase binding	-	0.6286	62.86%
PPAR gamma	-	0.7011	70.11%
Honey bee toxicity	-	0.8452	84.52%
Biodegradation	-	0.9750	97.50%
Crustacea aquatic toxicity	+	0.6700	67.00%
Fish aquatic toxicity	+	0.9122	91.22%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1287622	Q9Y468	Lethal(3)malignant brain tumor-like protein 1	70.8 nM	Potency	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.92%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	95.45%	95.56%
CHEMBL5608	Q16288	NT-3 growth factor receptor	94.76%	95.89%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	93.71%	94.45%
CHEMBL2581	P07339	Cathepsin D	92.32%	98.95%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	91.27%	94.00%
CHEMBL4208	P20618	Proteasome component C5	89.96%	90.00%
CHEMBL3192	Q9BY41	Histone deacetylase 8	89.62%	93.99%
CHEMBL5469	Q14289	Protein tyrosine kinase 2 beta	89.48%	91.03%
CHEMBL1937	Q92769	Histone deacetylase 2	87.88%	94.75%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	87.79%	93.40%
CHEMBL2535	P11166	Glucose transporter	87.38%	98.75%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	87.32%	91.11%
CHEMBL217	P14416	Dopamine D2 receptor	87.19%	95.62%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	86.86%	85.14%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	86.71%	93.03%
CHEMBL4829	O00763	Acetyl-CoA carboxylase 2	86.38%	98.00%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	85.98%	90.71%
CHEMBL1293249	Q13887	Kruppel-like factor 5	85.90%	86.33%
CHEMBL253	P34972	Cannabinoid CB2 receptor	85.77%	97.25%
CHEMBL2056	P21728	Dopamine D1 receptor	85.64%	91.00%
CHEMBL1951	P21397	Monoamine oxidase A	84.42%	91.49%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	83.47%	89.62%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	82.69%	99.23%

Plants that contains it

• Menispermum dauricum
• Sinomenium acutum
• Stephania cephalantha
• Stephania tetrandra

Cross-Links

• PubChem: 5459308
• NPASS: NPC298339
• LOTUS: LTS0113046
• wikiData: Q7524904