Codamine

Details

• Internal ID: 645da618-6b8c-42fc-8ba0-41ac826d28c6
• Taxonomy: Organoheterocyclic compounds > Isoquinolines and derivatives > Benzylisoquinolines
• IUPAC Name: (1S)-1-[(3,4-dimethoxyphenyl)methyl]-6-methoxy-2-methyl-3,4-dihydro-1H-isoquinolin-7-ol
• SMILES (Canonical): CN1CCC2=CC(=C(C=C2C1CC3=CC(=C(C=C3)OC)OC)O)OC
• SMILES (Isomeric): CN1CCC2=CC(=C(C=C2[C@@H]1CC3=CC(=C(C=C3)OC)OC)O)OC
• InChI: InChI=1S/C20H25NO4/c1-21-8-7-14-11-19(24-3)17(22)12-15(14)16(21)9-13-5-6-18(23-2)20(10-13)25-4/h5-6,10-12,16,22H,7-9H2,1-4H3/t16-/m0/s1
• InChI Key: OKORHWXYDBSYNO-INIZCTEOSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₅NO₄
• Molecular Weight: 343.40 g/mol
• Exact Mass: 343.17835828 g/mol
• Topological Polar Surface Area (TPSA): 51.20 Ų
• XlogP: 3.30
• Atomic LogP (AlogP): 3.19
• H-Bond Acceptor: 5
• H-Bond Donor: 1
• Rotatable Bonds: 5

Synonyms

• 21040-59-5
• L-(+)-codamine
• (S)-(+)-codamine
• 392KD8X3P8
• (S)-1-[(3,4-DIMETHOXYPHENYL)METHYL]-1,2,3,4-TETRAHYDRO-6-METHOXY-2-METHYLISOQUINOLIN-7-OL
• (1S)-1-[(3,4-dimethoxyphenyl)methyl]-6-methoxy-2-methyl-3,4-dihydro-1H-isoquinolin-7-ol
• 7-Isoquinolinol, 1-[(3,4-dimethoxyphenyl)methyl]-1,2,3,4-tetrahydro-6-methoxy-2-methyl-, (1S)-
• (S)-1-((3,4-Dimethoxyphenyl)methyl)-1,2,3,4-tetrahydro-6-methoxy-2-methylisoquinolin-7-ol
• 7-ISOQUINOLINOL, 1-((3,4-DIMETHOXYPHENYL)METHYL)-1,2,3,4-TETRAHYDRO-6-METHOXY-2-METHYL-, (1S)-
• 7-desmethyllaudanosine
• CODAMINE [MI]
• CODAMINE, (S)-
• CODAMINE, (+)-
• UNII-392KD8X3P8
• CHEMBL251624
• SCHEMBL15696578
• CHEBI:145336
• DTXSID801030735
• EINECS 244-165-9
• Q27256850
• 1,2,3,4-tetrahydro-6-methoxy-2-methyl-1-veratryl-7-isoquinolinol
• (1S)-1-(3,4-dimethoxybenzyl)-6-methoxy-2-methyl-1,2,3,4-tetrahydroisoquinolin-7-ol
• (1S)-1-((3,4-DIMETHOXYPHENYL)METHYL)-1,2,3,4-TETRAHYDRO-6-METHOXY-2-METHYL-7-ISOQUINOLINOL

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9237	92.37%
Caco-2	+	0.8488	84.88%
Blood Brain Barrier	+	0.7000	70.00%
Human oral bioavailability	-	0.5000	50.00%
Subcellular localzation	Mitochondria	0.6497	64.97%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9491	94.91%
OATP1B3 inhibitior	+	0.9451	94.51%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.5250	52.50%
BSEP inhibitior	+	0.6851	68.51%
P-glycoprotein inhibitior	+	0.7638	76.38%
P-glycoprotein substrate	+	0.6396	63.96%
CYP3A4 substrate	+	0.6316	63.16%
CYP2C9 substrate	+	0.7825	78.25%
CYP2D6 substrate	+	0.8432	84.32%
CYP3A4 inhibition	-	0.8633	86.33%
CYP2C9 inhibition	-	0.9182	91.82%
CYP2C19 inhibition	-	0.9014	90.14%
CYP2D6 inhibition	+	0.8958	89.58%
CYP1A2 inhibition	+	0.6094	60.94%
CYP2C8 inhibition	+	0.4569	45.69%
CYP inhibitory promiscuity	-	0.9136	91.36%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.7210	72.10%
Eye corrosion	-	0.9941	99.41%
Eye irritation	-	0.9528	95.28%
Skin irritation	-	0.7728	77.28%
Skin corrosion	-	0.9378	93.78%
Ames mutagenesis	-	0.7300	73.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8283	82.83%
Micronuclear	-	0.5600	56.00%
Hepatotoxicity	-	0.8125	81.25%
skin sensitisation	-	0.8992	89.92%
Respiratory toxicity	+	0.6111	61.11%
Reproductive toxicity	+	0.8556	85.56%
Mitochondrial toxicity	+	0.5375	53.75%
Nephrotoxicity	-	0.9229	92.29%
Acute Oral Toxicity (c)	III	0.8093	80.93%
Estrogen receptor binding	+	0.6956	69.56%
Androgen receptor binding	-	0.7371	73.71%
Thyroid receptor binding	+	0.7270	72.70%
Glucocorticoid receptor binding	+	0.7048	70.48%
Aromatase binding	-	0.5243	52.43%
PPAR gamma	+	0.6694	66.94%
Honey bee toxicity	-	0.9047	90.47%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	+	0.5500	55.00%
Fish aquatic toxicity	+	0.8707	87.07%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	99.30%	96.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	97.57%	85.14%
CHEMBL2581	P07339	Cathepsin D	96.24%	98.95%
CHEMBL5608	Q16288	NT-3 growth factor receptor	93.51%	95.89%
CHEMBL241	Q14432	Phosphodiesterase 3A	92.16%	92.94%
CHEMBL3192	Q9BY41	Histone deacetylase 8	91.15%	93.99%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	91.13%	94.45%
CHEMBL261	P00915	Carbonic anhydrase I	90.04%	96.76%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	90.01%	95.89%
CHEMBL2535	P11166	Glucose transporter	89.97%	98.75%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.70%	86.33%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	88.17%	94.00%
CHEMBL4208	P20618	Proteasome component C5	87.75%	90.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.87%	95.56%
CHEMBL5747	Q92793	CREB-binding protein	86.53%	95.12%
CHEMBL2056	P21728	Dopamine D1 receptor	84.51%	91.00%
CHEMBL3474	P14555	Phospholipase A2 group IIA	84.42%	94.05%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	84.15%	91.11%
CHEMBL3060	Q9Y345	Glycine transporter 2	83.86%	99.17%
CHEMBL253	P34972	Cannabinoid CB2 receptor	83.43%	97.25%
CHEMBL5555	O00767	Acyl-CoA desaturase	81.75%	97.50%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	81.51%	92.62%
CHEMBL217	P14416	Dopamine D2 receptor	81.02%	95.62%

Plants that contains it

• Aloe microstigma
• Bongardia chrysogonum
• Chrozophora plicata
• Cyperus nipponicus
• Dalbergia spruceana
• Dendrobium amplum
• Erythrophleum suaveolens
• Horsfieldia glabra
• Nuxia sphaerocephala
• Papaver somniferum
• Romneya coulteri
• Stephania pierrei
• Xylopia parviflora

Cross-Links

• PubChem: 20056510
• NPASS: NPC246587
• LOTUS: LTS0053962
• wikiData: Q27256850