Noscapine

Details

• Internal ID: d0b84c74-57ce-47de-9a5e-2b6ade328c4c
• Taxonomy: Alkaloids and derivatives > Phthalide isoquinolines
• IUPAC Name: (3S)-6,7-dimethoxy-3-[(5R)-4-methoxy-6-methyl-7,8-dihydro-5H-[1,3]dioxolo[4,5-g]isoquinolin-5-yl]-3H-2-benzofuran-1-one
• SMILES (Canonical): CN1CCC2=CC3=C(C(=C2C1C4C5=C(C(=C(C=C5)OC)OC)C(=O)O4)OC)OCO3
• SMILES (Isomeric): CN1CCC2=CC3=C(C(=C2[C@@H]1[C@@H]4C5=C(C(=C(C=C5)OC)OC)C(=O)O4)OC)OCO3
• InChI: InChI=1S/C22H23NO7/c1-23-8-7-11-9-14-20(29-10-28-14)21(27-4)15(11)17(23)18-12-5-6-13(25-2)19(26-3)16(12)22(24)30-18/h5-6,9,17-18H,7-8,10H2,1-4H3/t17-,18+/m1/s1
• InChI Key: AKNNEGZIBPJZJG-MSOLQXFVSA-N
• Popularity: 2,156 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₂H₂₃NO₇
• Molecular Weight: 413.40 g/mol
• Exact Mass: 413.14745207 g/mol
• Topological Polar Surface Area (TPSA): 75.70 Ų
• XlogP: 2.70
• Atomic LogP (AlogP): 2.88
• H-Bond Acceptor: 8
• H-Bond Donor: 0
• Rotatable Bonds: 4

Synonyms

• 128-62-1
• NARCOTINE
• Tusscapine
• Methoxyhydrastine
• Terbenol
• Capval
• Coscopin
• Narcompren
• Narcosine
• Vadebex
• (-)-Narcotine
• Longatin
• Narcotin
• Narkotin
• Noscapalin
• Noscapin
• Opianine
• Opianin
• Narcotussin
• Nectadon
• Nicolane
• Nipaxon
• Lyobex
• Opian
• alpha-Narcotine
• O-Methylnarcotoline
• Coscotabs
• Noscapinum
• Key-tusscapine
• Longactin
• Noscapal
• Noscapina
• Hederix (free base)
• (-)-alpha-narcotine
• L-alpha-Narcotine
• Narcotinum
• Noscopine
• Noskapin
• (-)-.alpha.-Narcotine
• NSC 5366
• NSC-5366
• L-alpha-Noscapine
• 8-Methoxyhydrastin
• .alpha.-Narcotine
• Coscopin (VAN)
• dl-Narcotine
• (+-)-Noscapine
• (+/-)-Noscapine
• L-.alpha.-Narcotine
• (-)-alpha-Norcotine
• (+-)-alpha-Narcotine
• Noscapinum [INN-Latin]
• (S,R)-Noscapine
• Noscapina [INN-Spanish]
• UNII-A4C6WE7BZN
• A4C6WE7BZN
• UNII-8V32U4AOQU
• 8V32U4AOQU
• alpha-Gnoscopine
• CCRIS 9304
• (S)-6,7-dimethoxy-3-((R)-4-methoxy-6-methyl-5,6,7,8-tetrahydro-[1,3]dioxolo[4,5-g]isoquinolin-5-yl)isobenzofuran-1(3H)-one
• DTXSID4023385
• CHEBI:73237
• HSDB 3372
• Noscapine [USP:INN:BAN:JAN]
• Noscapine dl-form
• NSC5366
• EINECS 204-899-2
• (3S)-6,7-dimethoxy-3-[(5R)-4-methoxy-6-methyl-5,6,7,8-tetrahydro[1,3]dioxolo[4,5-g]isoquinolin-5-yl]-2-benzofuran-1(3H)-one
• (3S)-6,7-dimethoxy-3-[(5R)-4-methoxy-6-methyl-7,8-dihydro-5H-[1,3]dioxolo[4,5-g]isoquinolin-5-yl]-3H-2-benzofuran-1-one
• Noscapine HCl
• BRN 0099933
• (3S)-6,7-dimethoxy-3-[(5R)-4-methoxy-6-methyl-2H,5H,6H,7H,8H-[1,3]dioxolo[4,5-g]isoquinolin-5-yl]-1,3-dihydro-2-benzofuran-1-one
• 1(3H)-Isobenzofuranone, 6,7-dimethoxy-3-((5R)-5,6,7,8-tetrahydro-4-methoxy-6-methyl-1,3-dioxolo(4,5-g)isoquinolin-5-yl)-, (3S)-rel-
• 1(3H)-Isobenzofuranone, 6,7-dimethoxy-3-(5,6,7,8-tetrahydro-4-methoxy-6-methyl-1,3-dioxolo(4,5-g)-isoquinolin-5-yl), (S-(R*,S*))-
• 1(3H)-Isobenzofuranone, 6,7-dimethoxy-3-(5,6,7,8-tetrahydro-4-methoxy-6-methyl-1,3-dioxolo(4,5-g)isoquinolin-5-yl)-, (R*,S*)-
• 4-27-00-06838 (Beilstein Handbook Reference)
• DTXCID303385
• 6035-40-1
• C22H23NO7
• Narcotine alkaloid
• .alpha.-Gnoscopine
• NSC 96350
• Noscapine (narcotine)
• (-)-3-(2-Methyl-6,7-methylendioxy-8-methoxy-1-isochinolyl)-6,7-dimethoxyphthalid
• Narcotine, (+-)-
• 5-(6,7-Dimethoxyphthalidyl)-5,6,7,8-tetrahydro-4-methoxy-8-methyl-1,3-dioxolo(4,5-g)isoquinoline
• L-alpha-2-Methyl-8-methoxy-6,7-methylenedioxy-1-(6,7-dimethoxy-3-phthalidyl)-1,2,3,4-tetrahydroisoquinaline
• SMR000059119
• Narcotine, (.+.)-
• (-)-.alpha.-Norcotine
• Noscapine [INN:BAN:JAN]
• 1(3H)-Isobenzofuranone, 6,7-dimethoxy-3-(5,6,7,8-tetrahydro-4-methoxy-6-methyl-1,3-dioxolo(4,5-g)isoquinolin-5-yl)-, (S-(R*,S*))-
• 1(3H)-Isobenzofuranone, 6,7-dimethoxy-3-(5,6,7,8-tetrahydro-4-methoxy-6-methyl-1,3-dioxolo[4,5-g]isoquinolin-5-yl)-, [S-(R*,S*)]-
• C22-H23-N-O7
• NSC-96350
• methoxyhydra-stine
• .beta.-Narcotine
• Noscapine (TN)
• (-)-noscapine
• NCGC00016388-01
• [S-(R*,S*)]-6,7-Dimethoxy-3-(5,6,7,8-tetrahydro-4-methoxy-6-methyl-1,3-dioxolo[4,5-g]isoquinolin-5-yl)-1(3H)-Isobenzofuranone
• 08N
• 1(3H)-Isobenzofuranone, 6,7-dimethoxy-3-((5R)-5,6,7,8-tetrahydro-4-methoxy-6-methyl-1,3-dioxolo(4,5-g)isoquinolin-5-yl)-, (3S)-
• 1(3H)-Isobenzofuranone, 6,7-dimethoxy-3-[(5R)-5,6,7,8-tetrahydro-4-methoxy-6-methyl-1,3-dioxolo[4,5-g]isoquinolin-5-yl]-, (3S)-
• CAS-128-62-1
• Prestwick_959
• (-)-a-Narcotine
• 1-.alpha.-Narcotine
• Tocris-1697
• NOSCAPINE [INN]
• NOSCAPINE [JAN]
• NOSCAPINE [MI]
• NOSCAPINE [HSDB]
• Prestwick0_000563
• Prestwick1_000563
• Prestwick2_000563
• Prestwick3_000563
• NARCOTINUM [HPUS]
• CBMicro_048259
• D0Y8AW
• NOSCAPINE [MART.]
• NOSCAPINE [USP-RS]
• NOSCAPINE [WHO-DD]
• NOSCAPINE [WHO-IP]
• SCHEMBL4559
• Noscapine [BAN:INN:JAN]
• (S,R)-Noscapine, 97%
• Lopac0_000840
• BSPBio_000346
• MLS000069475
• MLS001060855
• SPBio_002565
• Noscapine (JP15/USP/INN)
• Noscapine (JP17/USP/INN)
• BPBio1_000382
• CHEMBL364713
• NOSCAPINE DL-FORM [MI]
• NOSCAPINE [EP MONOGRAPH]
• NOSCAPINE, (+/-)-
• GTPL10212
• NOSCAPINE [USP MONOGRAPH]
• NOSCAPINUM [WHO-IP LATIN]
• DTXSID901032089
• HMS1569B08
• HMS2096B08
• HMS2269P05
• 1(3H)-Isobenzofuranone, 6,7-dimethoxy-3-(5,6,7,8-tetrahydro-4-methoxy-6-methyl-1,3-dioxolo[4,5-g]isoquinolin-5-yl)-, (R*,S*)-(.+.)-
• 6,7-Dimethoxy-3-(4-methoxy-6-methyl-5,6,7,8-tetrahydro[1,3]dioxolo[4,5-g]isoquinolin-5-yl)-2-benzofuran-1(3H)-one, (S-(R*,S*))- #
• Phthalide, 6,7-dimethoxy-3-(5,6,7,8-tetrahydro-4-methoxy-6-methyl-1,3-dioxolo(4,5-g)isoquinolin-5-yl)-
• (+/-)-.ALPHA.-NARCOTINE
• Tox21_110413
• BBL012344
• BDBM50424716
• CB3304
• MFCD00069316
• NSC121869
• STK054401
• Noscapine 1.0 mg/ml in Acetonitrile
• AKOS000278036
• Tox21_110413_1
• CCG-204096
• CS-5115
• DB06174
• NSC-121869
• SDCCGSBI-0048054.P004
• NCGC00023230-02
• NCGC00023230-04
• NCGC00023230-05
• NCGC00023230-07
• NCGC00023230-08
• NCGC00023230-10
• NCGC00023230-14
• (3S)-6,7-Dimethoxy-3-[(5R)-5,6,7,8-tetrahydro-4-methoxy-6-methyl-1,3-dioxolo[4,5-g]isoquinolin-5-yl]-1(3H)-isobenzofuranone
• AC-20272
• AC-33191
• HY-13716
• NCI60_004322
• VS-03291
• BIM-0048054.P001
• C09592
• D01036
• EN300-24402818
• SR-01000075529-6
• W-201012
• BRD-K89237706-001-03-8
• Q60998699
• Noscapine, European Pharmacopoeia (EP) Reference Standard
• Noscapine, United States Pharmacopeia (USP) Reference Standard
• WLN: T C566 DO FO KN EH & & TJ HO1 K1 J-DT56 BVO DHJ HO1 IO1
• (3S)-3-[(5R)-6-methyl-4-(methyloxy)-5,6,7,8-tetrahydro[1,3]dioxolo[4,5-g]isoquinolin-5-yl]-6,7-bis(methyloxy)-2-benzofuran-1(3H)-one
• (3S)-6,7-dimethoxy-3-[(5R)-4-methoxy-6-methyl-7,8-dihydro-5H-[1,3]dioxolo[4,5-g]isoquinolin-5-yl]-3H-isobenzofuran-1-one
• 1(3H)-Isobenzofuranone, 6,7-dimethoxy-3-(5,6,7,8- tetrahydro-4-methoxy-6-methyl-1,3-dioxolo[4,5-g]isoquinolin -5-yl)-, [S-(R,S)]-
• 1(3H)-Isobenzofuranone, 6,7-dimethoxy-3-(5,6,7,8-tetrahydro-4-methoxy-6-methyl-1,3-dioxolo(4,5-g)isoquinolin-5-yl)-, (R*,S*)-(+-)-
• 1(3H)-Isobenzofuranone,7-dimethoxy-3-(5,6,7,8-tetrahydro-4-methoxy-6-methyl-1,3-dioxolo[4,5-g]isoquinolin-5-yl)-, [S-(R*,S*)]-
• Phthalide,7-dimethoxy-3-(5,6,7,8-tetrahydro-4-methoxy-6-methyl-1,3-dioxolo[4,5-g]isoquinolin-5-yl)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9222	92.22%
Caco-2	+	0.8962	89.62%
Blood Brain Barrier	+	0.7500	75.00%
Human oral bioavailability	-	0.6286	62.86%
Subcellular localzation	Lysosomes	0.4513	45.13%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9419	94.19%
OATP1B3 inhibitior	+	0.9444	94.44%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.7250	72.50%
BSEP inhibitior	+	0.8956	89.56%
P-glycoprotein inhibitior	+	0.9512	95.12%
P-glycoprotein substrate	-	0.9123	91.23%
CYP3A4 substrate	+	0.6682	66.82%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	+	0.3512	35.12%
CYP3A4 inhibition	+	0.7961	79.61%
CYP2C9 inhibition	+	0.8949	89.49%
CYP2C19 inhibition	+	0.8993	89.93%
CYP2D6 inhibition	-	0.8620	86.20%
CYP1A2 inhibition	-	0.9045	90.45%
CYP2C8 inhibition	-	0.7358	73.58%
CYP inhibitory promiscuity	+	0.5373	53.73%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.5368	53.68%
Eye corrosion	-	0.9893	98.93%
Eye irritation	-	0.9658	96.58%
Skin irritation	-	0.7998	79.98%
Skin corrosion	-	0.9449	94.49%
Ames mutagenesis	+	0.6300	63.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5240	52.40%
Micronuclear	+	0.5374	53.74%
Hepatotoxicity	-	0.9250	92.50%
skin sensitisation	-	0.8716	87.16%
Respiratory toxicity	+	0.8889	88.89%
Reproductive toxicity	+	0.8222	82.22%
Mitochondrial toxicity	+	0.8250	82.50%
Nephrotoxicity	-	0.7848	78.48%
Acute Oral Toxicity (c)	III	0.7672	76.72%
Estrogen receptor binding	+	0.8551	85.51%
Androgen receptor binding	-	0.8512	85.12%
Thyroid receptor binding	-	0.5934	59.34%
Glucocorticoid receptor binding	+	0.8866	88.66%
Aromatase binding	-	0.5575	55.75%
PPAR gamma	+	0.7370	73.70%
Honey bee toxicity	-	0.8096	80.96%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	+	0.6600	66.00%
Fish aquatic toxicity	+	0.8049	80.49%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL3356	P05177	Cytochrome P450 1A2	31622.78 nM	AC50	via CMAUP
CHEMBL3622	P33261	Cytochrome P450 2C19	400.3 nM	IC50	via CMAUP
CHEMBL3397	P11712	Cytochrome P450 2C9	8177.3 nM	IC50	via CMAUP
CHEMBL340	P08684	Cytochrome P450 3A4	1995.3 nM; 1995.3 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL4040	P28482	MAP kinase ERK2	31622.8 nM	Potency	via CMAUP
CHEMBL1743126	Q96FL8	Multidrug and toxin extrusion protein 1	34500 nM	IC50	PMID: 23241029
CHEMBL1743122	O15244	Solute carrier family 22 member 2	2600 nM	IC50	PMID: 23241029

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.02%	96.09%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	97.98%	93.40%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	97.90%	96.77%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	97.19%	95.56%
CHEMBL3192	Q9BY41	Histone deacetylase 8	95.67%	93.99%
CHEMBL2581	P07339	Cathepsin D	91.99%	98.95%
CHEMBL2146302	O94925	Glutaminase kidney isoform, mitochondrial	91.32%	100.00%
CHEMBL261	P00915	Carbonic anhydrase I	91.18%	96.76%
CHEMBL2535	P11166	Glucose transporter	90.50%	98.75%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	90.25%	94.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	90.10%	95.89%
CHEMBL5311	P37023	Serine/threonine-protein kinase receptor R3	89.88%	82.67%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	89.84%	85.14%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	88.62%	92.62%
CHEMBL2056	P21728	Dopamine D1 receptor	87.41%	91.00%
CHEMBL4247	Q9UM73	ALK tyrosine kinase receptor	87.19%	96.86%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.11%	86.33%
CHEMBL2069156	Q14145	Kelch-like ECH-associated protein 1	86.16%	82.38%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	85.67%	99.23%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	83.68%	97.14%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	83.23%	95.78%
CHEMBL253	P34972	Cannabinoid CB2 receptor	82.94%	97.25%
CHEMBL2335	P42785	Lysosomal Pro-X carboxypeptidase	82.83%	100.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.26%	89.00%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	82.20%	89.62%
CHEMBL5925	P22413	Ectonucleotide pyrophosphatase/phosphodiesterase family member 1	81.97%	92.38%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	81.86%	94.45%
CHEMBL5555	O00767	Acyl-CoA desaturase	81.29%	97.50%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	81.12%	95.89%
CHEMBL3137262	O60341	LSD1/CoREST complex	80.77%	97.09%
CHEMBL4306	P22460	Voltage-gated potassium channel subunit Kv1.5	80.67%	94.03%
CHEMBL2083	P15090	Fatty acid binding protein adipocyte	80.57%	95.71%
CHEMBL4895	P30530	Tyrosine-protein kinase receptor UFO	80.31%	90.95%
CHEMBL5203	P33316	dUTP pyrophosphatase	80.00%	99.18%

Plants that contains it

• Aloe microstigma
• Chrozophora plicata
• Citrus × aurantium
• Corydalis cava
• Corydalis heterocarpa
• Corydalis solida
• Dovyalis hebecarpa
• Eremophila oppositifolia
• Ixeris repens
• Papaver oreophilum
• Papaver orientale
• Papaver rhoeas
• Papaver somniferum
• Roemeria carica
• Taxillus sutchuenensis var. duclouxii

Cross-Links

• PubChem: 275196
• NPASS: NPC202771
• ChEMBL: CHEMBL364713
• LOTUS: LTS0246977
• wikiData: Q415619