Tubocurarine

Details

• Internal ID: 8bc6e4ba-9060-4359-834e-11b142983184
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Ethers > Diarylethers
• IUPAC Name: (1S,16R)-10,25-dimethoxy-15,15,30-trimethyl-7,23-dioxa-30-aza-15-azoniaheptacyclo[22.6.2.23,6.18,12.118,22.027,31.016,34]hexatriaconta-3(36),4,6(35),8(34),9,11,18(33),19,21,24,26,31-dodecaene-9,21-diol
• SMILES (Canonical): CN1CCC2=CC(=C3C=C2C1CC4=CC=C(C=C4)OC5=C6C(CC7=CC(=C(C=C7)O)O3)[N+](CCC6=CC(=C5O)OC)(C)C)OC
• SMILES (Isomeric): CN1CCC2=CC(=C3C=C2[C@@H]1CC4=CC=C(C=C4)OC5=C6[C@@H](CC7=CC(=C(C=C7)O)O3)[N+](CCC6=CC(=C5O)OC)(C)C)OC
• InChI: InChI=1S/C37H40N2O6/c1-38-14-12-24-19-32(42-4)33-21-27(24)28(38)16-22-6-9-26(10-7-22)44-37-35-25(20-34(43-5)36(37)41)13-15-39(2,3)29(35)17-23-8-11-30(40)31(18-23)45-33/h6-11,18-21,28-29H,12-17H2,1-5H3,(H-,40,41)/p+1/t28-,29+/m0/s1
• InChI Key: JFJZZMVDLULRGK-URLMMPGGSA-O
• Popularity: 4,910 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₇H₄₁N₂O₆+
• Molecular Weight: 609.70 g/mol
• Exact Mass: 609.29646203 g/mol
• Topological Polar Surface Area (TPSA): 80.60 Ų
• XlogP: 6.00
• Atomic LogP (AlogP): 6.70
• H-Bond Acceptor: 7
• H-Bond Donor: 2
• Rotatable Bonds: 2

Synonyms

• d-Tubocurarine
• Tubocurarine chloride
• Tubocurarin
• (+)-Tubocurarine
• Tubocurarinum
• 57-95-4
• Delacurarine
• Tubarine
• Isoquinoline alkaloid
• Jexin
• D-Tubocurarine chloride
• Tubocurarine ion
• Tubocurarine cation
• CHEBI:9774
• Tubocurarine hydrochloride
• Dextrotubocurarine chloride
• (+)-Tubocurarine chloride
• Tubocurarina cloruro
• UNII-W9YXS298BM
• Tubocurarini chloridum
• 7',12'-Dihydroxy-6,6'-dimethoxy-2,2',2'-trimethyltubocuraranium
• W9YXS298BM
• Cloruro de tubocurarina
• Chlorure de tubocurarine
• tubocurarine HCl
• HSDB 2152
• Amerizol
• Tubaine (TN)
• Tubocuraranium, 7',12'-dihydroxy-6,6'-dimethoxy-2,2',2'-trimethyl-
• Tubocurarine chloride (TN)
• 6989-98-6
• (+)-Tubocurarine dichloride
• (+)-Tubocurarine chloride hydrochloride
• Tubocurarine chloride (INN)
• Tubocurarine chloride [INN]
• C37H41N2O6.ClH.Cl
• Tubocurarine chloride anhydrous
• 7',12'-dihydroxy-6,6'-dimethoxy-2,2',2'-trimethyltubocuraran-2'-ium
• (+) Tubocurarine
• 13H-4,6:21,24-Dietheno-8,12-metheno-1H-pyrido(3',2':14,15)(1,11)dioxacycloeicosino(2,3,4-ij)isoquinolinium, 2,3,13a,14,15,16,25,25a-octahydro-9,19-dihydroxy-18,29-dimethoxy-1,14,14-trimethyl-, (13aR,25aS)-
• 13H-4,6:21,24-Dietheno-8,12-metheno-1H-pyrido(3',2':14,15)(1,11)dioxacycloeicosino(2,3,4-ij)isoquinolinium, 2,3,13a,14,15,16,25,25a-octahydro-9,19-dihydroxy-18,29-dimethoxy-1,14,14-trimethyl-, (13aR-(13aR*,25aS*))-
• C37H41ClN2O6.ClH.5H2O
• C37-H41-N2-O6.Cl-H.Cl
• Tubocuraranium, 7',12'-dihydroxy-6,6'-dimethoxy-2,2',2'-trimethyl-, chloride, hydrochloride
• NCGC00163242-01
• Tubocurarine chloride [USAN:INN:BAN:JAN]
• C37-H41-N2-O6.Cl-H.Cl.5H2-O
• Metubine (TN)
• Tubarine (TN)
• TC9
• Delacurarine (TN)
• Tubocurarinum (TN)
• Spectrum_001966
• 2,2',2'-trimethyl-6,6'-bis(methyloxy)tubocuraran-2,2'-diium-7',12'-diol dichloride
• SpecPlus_000475
• Jex (TN)
• 13H-4,6:21,24-Dietheno-8, 12-metheno-1H-pyrido[3',2':14,15][1,11]dioxacycloeicosino [2,3,4-ij]isoquinolinium, 2,3,13a,14,15,16,25,25a-octahydro- 9,19-dihydroxy-18,29-dimethoxy-1,14,14-trimethyl -, chlorid
• 57-94-3
• Spectrum2_001335
• Spectrum3_001095
• Spectrum4_001922
• Spectrum5_000685
• Tubocuraranium, 7',12'-dihydroxy-6,6'-dimethoxy-2,2,2',2'-tetramethyl-, dichloride, pentahydrate
• D05HSC
• Epitope ID:174836
• TUBOCURARINE [HSDB]
• dimethoxy(trimethyl)[?]diol
• TUBOCURARINE [VANDF]
• BSPBio_002770
• KBioGR_002264
• KBioSS_002526
• MLS003882581
• DivK1c_006571
• SCHEMBL121375
• TUBOCURARINE [WHO-DD]
• SPBio_001489
• CHEMBL339427
• GTPL2294
• DTXSID0048393
• KBio1_001515
• KBio2_002518
• KBio2_005086
• KBio2_007654
• KBio3_001990
• C37H41N2O6
• HMS2089C06
• BDBM50366799
• PDSP1_001485
• PDSP2_001469
• C37-H41-N2-O6
• DB01199
• SDCCGMLS-0066631.P001
• NCGC00163242-02
• NCGC00178480-01
• SMR002533646
• SBI-0052455.P002
• LS-187260
• C07547
• AB00053831-03
• AB00053831_04
• Q421268
• SR-05000001878-4
• Tubocurarine, chloride, hydrochloride, (+)-(8CI)
• BRD-K99621550-003-03-4
• (1S,16R)-10,25-dimethoxy-15,15,30-trimethyl-7,23-dioxa-30-aza-15-azoniaheptacyclo[22.6.2.23,6.18,12.118,22.027,31.016,34]hexatriaconta-3(36),4,6(35),8(34),9,11,18(33),19,21,24,26,31-dodecaene-9,21-diol
• (1S,16R)-9,21-dihydroxy-10,25-dimethoxy-15,15,30-trimethyl-7,23-dioxa-15,30-diazaheptacyclo[22.6.2.2^{3,6}.1^{8,12}.1^{18,22}.0^{27,31}.0^{16,34}]hexatriaconta-3,5,8,10,12(34),18(33),19,21,24(32),25,27(31),35-dodecaen-15-ium
• 13H-4,6:21,24-Dietheno-8,12-metheno-1H-pyrido[3',2':14,15][1,11]dioxacycloeicosino[2,3,4-ij]isoquinolinium,2,3,13a,14,15,16,25,25a-octahydro-9,19-dihydroxy-18,29-dimethoxy-1,14,14-trimethyl-,(13ar,25a

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.9659	96.59%
Caco-2	-	0.6580	65.80%
Blood Brain Barrier	+	0.6000	60.00%
Human oral bioavailability	-	0.7000	70.00%
Subcellular localzation	Mitochondria	0.3935	39.35%
OATP2B1 inhibitior	-	0.8582	85.82%
OATP1B1 inhibitior	+	0.9397	93.97%
OATP1B3 inhibitior	+	0.9460	94.60%
MATE1 inhibitior	+	0.7200	72.00%
OCT2 inhibitior	-	0.6000	60.00%
BSEP inhibitior	+	0.9831	98.31%
P-glycoprotein inhibitior	+	0.8961	89.61%
P-glycoprotein substrate	+	0.6573	65.73%
CYP3A4 substrate	+	0.7032	70.32%
CYP2C9 substrate	+	0.7936	79.36%
CYP2D6 substrate	+	0.4658	46.58%
CYP3A4 inhibition	-	0.9284	92.84%
CYP2C9 inhibition	-	0.9480	94.80%
CYP2C19 inhibition	-	0.9136	91.36%
CYP2D6 inhibition	-	0.9231	92.31%
CYP1A2 inhibition	-	0.9365	93.65%
CYP2C8 inhibition	+	0.6897	68.97%
CYP inhibitory promiscuity	-	0.9794	97.94%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.6257	62.57%
Eye corrosion	-	0.9862	98.62%
Eye irritation	-	0.9410	94.10%
Skin irritation	-	0.7906	79.06%
Skin corrosion	-	0.9403	94.03%
Ames mutagenesis	+	0.7300	73.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.9185	91.85%
Micronuclear	+	0.6300	63.00%
Hepatotoxicity	-	0.9750	97.50%
skin sensitisation	-	0.8637	86.37%
Respiratory toxicity	+	0.8222	82.22%
Reproductive toxicity	+	0.7333	73.33%
Mitochondrial toxicity	+	0.7125	71.25%
Nephrotoxicity	-	0.9065	90.65%
Acute Oral Toxicity (c)	III	0.6856	68.56%
Estrogen receptor binding	+	0.6275	62.75%
Androgen receptor binding	+	0.7472	74.72%
Thyroid receptor binding	+	0.6453	64.53%
Glucocorticoid receptor binding	+	0.8757	87.57%
Aromatase binding	+	0.7295	72.95%
PPAR gamma	-	0.5839	58.39%
Honey bee toxicity	-	0.7062	70.62%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	+	0.6500	65.00%
Fish aquatic toxicity	+	0.8734	87.34%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1743126	Q96FL8	Multidrug and toxin extrusion protein 1	9400 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	99.47%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.40%	91.11%
CHEMBL3192	Q9BY41	Histone deacetylase 8	95.31%	93.99%
CHEMBL241	Q14432	Phosphodiesterase 3A	94.28%	92.94%
CHEMBL217	P14416	Dopamine D2 receptor	94.23%	95.62%
CHEMBL2056	P21728	Dopamine D1 receptor	94.07%	91.00%
CHEMBL2581	P07339	Cathepsin D	92.52%	98.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	92.10%	94.45%
CHEMBL5608	Q16288	NT-3 growth factor receptor	90.78%	95.89%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	90.32%	93.40%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	90.31%	85.14%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.92%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	89.44%	89.00%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	88.04%	89.62%
CHEMBL5469	Q14289	Protein tyrosine kinase 2 beta	87.85%	91.03%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	87.51%	94.00%
CHEMBL1163125	O60885	Bromodomain-containing protein 4	87.24%	97.31%
CHEMBL4208	P20618	Proteasome component C5	87.23%	90.00%
CHEMBL2535	P11166	Glucose transporter	87.21%	98.75%
CHEMBL2069156	Q14145	Kelch-like ECH-associated protein 1	87.00%	82.38%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	85.17%	92.62%
CHEMBL2041	P07949	Tyrosine-protein kinase receptor RET	83.88%	91.79%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	83.08%	95.78%
CHEMBL2335	P42785	Lysosomal Pro-X carboxypeptidase	83.05%	100.00%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	81.59%	99.15%
CHEMBL2085	P14174	Macrophage migration inhibitory factor	81.55%	80.78%
CHEMBL2413	P32246	C-C chemokine receptor type 1	81.34%	89.50%
CHEMBL261	P00915	Carbonic anhydrase I	80.78%	96.76%
CHEMBL5311	P37023	Serine/threonine-protein kinase receptor R3	80.66%	82.67%
CHEMBL3060	Q9Y345	Glycine transporter 2	80.41%	99.17%

Plants that contains it

• Phellodendron amurense
• Phellodendron chinense

Cross-Links

• PubChem: 6000
• NPASS: NPC90998
• ChEMBL: CHEMBL339427