Narceine

Details

• Internal ID: f3432e7f-422e-456d-a584-3ca5c0211a83
• Taxonomy: Phenylpropanoids and polyketides > Stilbenes
• IUPAC Name: 6-[2-[6-[2-(dimethylamino)ethyl]-4-methoxy-1,3-benzodioxol-5-yl]acetyl]-2,3-dimethoxybenzoic acid
• SMILES (Canonical): CN(C)CCC1=CC2=C(C(=C1CC(=O)C3=C(C(=C(C=C3)OC)OC)C(=O)O)OC)OCO2
• SMILES (Isomeric): CN(C)CCC1=CC2=C(C(=C1CC(=O)C3=C(C(=C(C=C3)OC)OC)C(=O)O)OC)OCO2
• InChI: InChI=1S/C23H27NO8/c1-24(2)9-8-13-10-18-22(32-12-31-18)20(29-4)15(13)11-16(25)14-6-7-17(28-3)21(30-5)19(14)23(26)27/h6-7,10H,8-9,11-12H2,1-5H3,(H,26,27)
• InChI Key: DEXMFYZAHXMZNM-UHFFFAOYSA-N
• Popularity: 328 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₃H₂₇NO₈
• Molecular Weight: 445.50 g/mol
• Exact Mass: 445.17366682 g/mol
• Topological Polar Surface Area (TPSA): 104.00 Ų
• XlogP: 0.50
• Atomic LogP (AlogP): 2.67
• H-Bond Acceptor: 8
• H-Bond Donor: 1
• Rotatable Bonds: 10

Synonyms

• Narcein
• 131-28-2
• UNII-CTT09X2F1M
• EINECS 205-021-0
• CTT09X2F1M
• BRN 0371009
• 6-[2-[6-[2-(dimethylamino)ethyl]-4-methoxy-1,3-benzodioxol-5-yl]acetyl]-2,3-dimethoxybenzoic acid
• NARCEINE [MI]
• 6-((6-(2-(Dimethylamino)ethyl)-2-methoxy-3,4-(methylenedioxy)phenyl)acetyl)-o-veratric acid
• NARCEINE [MART.]
• NARCEINE [WHO-DD]
• DTXSID40156833
• 5-19-09-00051 (Beilstein Handbook Reference)
• 2,3-Dimethoxy-6-((6-(2-dimethylaminoethyl)-2-methoxy-3,4-methylendioxyphenyl)acetyl)benzosaeure
• 6-[[6-[2-(Dimethylamino)ethyl]-4-methoxy-1,3-benzodioxol-5-yl]acetyl]-2,3-dimethoxybenzoic acid
• NARCEINE (MART.)
• o-Veratric acid, 6-((6-(2-(dimethylamino)ethyl)-2-methoxy-3,4-(methylenedioxy)phenyl)acetyl)-
• o-Veratric acid, 6-[[6-[2-(dimethylamino)ethyl]-2-methoxy-3,4-(methylenedioxy)phenyl]acetyl]-
• Benzoic acid, 6-[[6-[2-(dimethylamino)ethyl]-4-methoxy-1,3-benzodioxol-5-yl]acetyl]-2,3-dimethoxy-
• 6-((6-(2-(DIMETHYLAMINO)ETHYL)-4-METHOXY-1,3-BENZODIOXOL-5-YL)ACETYL)-2,3-DIMETHOXYBENZOIC ACID
• 6-(2-{6-[2-(dimethylamino)ethyl]-4-methoxy-2H-1,3-benzodioxol-5-yl}acetyl)-2,3-dimethoxybenzoic acid
• 6-[[6-[2-(Dimethylamino)ethyl]-4-methoxy-1,3-benzodioxol-5-yl]acetyl]-2,3-dimethoxybenzoic acid, 9CI
• Benzoic acid, 6-((6-(2-(dimethylamino)ethyl)-4-methoxy-1,3-benzodioxol-5-yl)acetyl)-2,3-dimethoxy-
• 6-((6-(2-(Dimethylamino)ethyl)-4-methoxy-1,3-benzodioxol-5-yl)acetyl)-2,3-dimethoxybenzoic acid, 9ci
• 6-(2-(6-(2-(dimethylamino)ethyl)-4-methoxy-1,3-benzodioxol-5-yl)acetyl)-2,3-dimethoxybenzoic acid
• 6-(2-(6-(2-(dimethylamino)ethyl)-4-methoxy-2H-1,3-benzodioxol-5-yl)acetyl)-2,3-dimethoxybenzoic acid
• 6-(2-(6-(2-(dimethylazaniumyl)ethyl)-4-methoxy-1,3-benzodioxol-5-yl)acetyl)-2,3-dimethoxybenzoate
• 6-[2-[6-[2-(dimethylazaniumyl)ethyl]-4-methoxy-1,3-benzodioxol-5-yl]acetyl]-2,3-dimethoxybenzoate
• RefChem:164828
• DTXCID2079324
• 205-021-0
• DEXMFYZAHXMZNM-UHFFFAOYSA-N
• CI 15511
• CHEBI:7480
• C09591
• SCHEMBL24919
• CHEMBL486305
• SCHEMBL29851225
• GTPL13150
• BDBM50480327
• NIH 10760
• AKOS022180680
• BENZOIC ACID,6-[2-[6-[2-(DIMETHYLAMINO)ETHYL]-4-METHOXY-1,3-BENZODIOXOL-5-YL]ACETYL]-2,3-DIMETHOXY-
• DB-042019
• CS-0026319
• NS00002615
• G83765
• Q907355
• 6-((6-[2-(Dimethylamino)ethyl]-4-methoxy-1,3-benzodioxol-5-yl)acetyl)-2,3-dimethoxybenzoic acid #
• 6-(2-(6-(2-(Dimethylamino)ethyl)-4-methoxybenzo[d][1,3]dioxol-5-yl)acetyl)-2,3-dimethoxybenzoic acid
• 6-[2-[6-(2-dimethylaminoethyl)-4-methoxy-1,3-benzodioxol-5-yl]acetyl]-2,3-dimethoxy-benzoic acid

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9303	93.03%
Caco-2	+	0.7149	71.49%
Blood Brain Barrier	+	0.6500	65.00%
Human oral bioavailability	+	0.6714	67.14%
Subcellular localzation	Mitochondria	0.6561	65.61%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9153	91.53%
OATP1B3 inhibitior	+	0.9059	90.59%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.5000	50.00%
BSEP inhibitior	+	0.7774	77.74%
P-glycoprotein inhibitior	+	0.7477	74.77%
P-glycoprotein substrate	-	0.7091	70.91%
CYP3A4 substrate	+	0.6218	62.18%
CYP2C9 substrate	-	0.8129	81.29%
CYP2D6 substrate	-	0.6663	66.63%
CYP3A4 inhibition	+	0.8047	80.47%
CYP2C9 inhibition	-	0.8448	84.48%
CYP2C19 inhibition	-	0.6966	69.66%
CYP2D6 inhibition	-	0.6068	60.68%
CYP1A2 inhibition	-	0.8091	80.91%
CYP2C8 inhibition	-	0.6075	60.75%
CYP inhibitory promiscuity	-	0.8575	85.75%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.8800	88.00%
Carcinogenicity (trinary)	Non-required	0.5463	54.63%
Eye corrosion	-	0.9914	99.14%
Eye irritation	-	0.9394	93.94%
Skin irritation	-	0.8272	82.72%
Skin corrosion	-	0.9449	94.49%
Ames mutagenesis	+	0.5046	50.46%
Human Ether-a-go-go-Related Gene inhibition	-	0.6346	63.46%
Micronuclear	-	0.5800	58.00%
Hepatotoxicity	+	0.5284	52.84%
skin sensitisation	-	0.8529	85.29%
Respiratory toxicity	+	0.7889	78.89%
Reproductive toxicity	+	0.8333	83.33%
Mitochondrial toxicity	+	0.7750	77.50%
Nephrotoxicity	-	0.7138	71.38%
Acute Oral Toxicity (c)	III	0.6943	69.43%
Estrogen receptor binding	+	0.8145	81.45%
Androgen receptor binding	-	0.5697	56.97%
Thyroid receptor binding	+	0.5169	51.69%
Glucocorticoid receptor binding	+	0.7333	73.33%
Aromatase binding	+	0.6899	68.99%
PPAR gamma	+	0.6961	69.61%
Honey bee toxicity	-	0.8642	86.42%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.8274	82.74%
Fish aquatic toxicity	+	0.9695	96.95%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4040	P28482	MAP kinase ERK2	98.26%	83.82%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.55%	96.09%
CHEMBL1255126	O15151	Protein Mdm4	94.39%	90.20%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.93%	86.33%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	91.45%	96.77%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.66%	95.56%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	90.58%	96.00%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	90.47%	91.11%
CHEMBL2581	P07339	Cathepsin D	87.44%	98.95%
CHEMBL4208	P20618	Proteasome component C5	86.86%	90.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	86.60%	94.45%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	86.51%	92.62%
CHEMBL3060	Q9Y345	Glycine transporter 2	86.16%	99.17%
CHEMBL3401	O75469	Pregnane X receptor	82.71%	94.73%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	81.67%	93.00%
CHEMBL2535	P11166	Glucose transporter	81.15%	98.75%
CHEMBL1806	P11388	DNA topoisomerase II alpha	80.76%	89.00%

Plants that contains it

• Papaver somniferum

Cross-Links

• PubChem: 8564
• NPASS: NPC18306
• LOTUS: LTS0064845
• wikiData: Q907355