DL-Tetrahydropalmatine

Details

• Internal ID: eceda99f-2355-425a-b637-a9625d2ed330
• Taxonomy: Alkaloids and derivatives > Protoberberine alkaloids and derivatives
• IUPAC Name: 2,3,9,10-tetramethoxy-6,8,13,13a-tetrahydro-5H-isoquinolino[2,1-b]isoquinoline
• SMILES (Canonical): COC1=C(C2=C(CC3C4=CC(=C(C=C4CCN3C2)OC)OC)C=C1)OC
• SMILES (Isomeric): COC1=C(C2=C(CC3C4=CC(=C(C=C4CCN3C2)OC)OC)C=C1)OC
• InChI: InChI=1S/C21H25NO4/c1-23-18-6-5-13-9-17-15-11-20(25-3)19(24-2)10-14(15)7-8-22(17)12-16(13)21(18)26-4/h5-6,10-11,17H,7-9,12H2,1-4H3
• InChI Key: AEQDJSLRWYMAQI-UHFFFAOYSA-N
• Popularity: 322 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₂₅NO₄
• Molecular Weight: 355.40 g/mol
• Exact Mass: 355.17835828 g/mol
• Topological Polar Surface Area (TPSA): 40.20 Ų
• XlogP: 3.20

Synonyms

• 2934-97-6
• 10097-84-4
• DL-Tetrahydropalmatine
• corydalis B
• ROTUNDINUM
• (+-)-Corydalis B
• Hyndarin
• 2,3,9,10-Tetramethoxy-5,8,13,13a-tetrahydro-6H-isoquino[3,2-a]isoquinoline
• UNII-78F8583LNQ
• Tetrahydropalmatine, (+/-)-
• CHEMBL187892
• 78F8583LNQ
• 2,3,9,10-tetramethoxy-6,8,13,13a-tetrahydro-5H-isoquinolino[2,1-b]isoquinoline
• 6H-Dibenzo[a,g]quinolizine,5,8,13,13a-tetrahydro-2,3,9,10-tetramethoxy-
• 2,3,9,10-Tetramethoxy-6,8,13,13a-tetrahydro-5H-isoquinolino[3,2-a]isoquinoline
• GNF-Pf-3943
• 6H-Dibenzo(a,g)quinolizine, 5,8,13,13a-tetrahydro-2,3,9,10-tetramethoxy-, (+-)-
• Tetrahydropalmatine, dl-
• dl-Tetrahydropalmatine hydrochloride
• Tetrahydropalmatine (6CI)
• 6H-Dibenzo[a,g]quinolizine, 5,8,13,13a-tetrahydro-2,3,9,10-tetramethoxy-
• Tetrahydropalmatine hydrochloride, (+/-)-
• Sodiumgluconate
• O(C)c1cc2c(CCN3Cc4c(ccc(OC)c4OC)CC23)cc1OC
• Berbine, 2,3,9,10-tetramethoxy-, hydrochloride, (.+.)-
• (-)-Tetrahydropalmatine;L-Tetrahydropalmatine
• Spectrum_001554
• SpecPlus_000956
• 6H-Dibenzo[a,g]quinolizine, 5,8,13,13a-tetrahydro-2,3,9,10-tetramethoxy-, hydrochloride, (.+.)-
• Spectrum2_000736
• Spectrum3_001650
• Spectrum4_001749
• Spectrum5_000578
• Tetrahydropalmatine ,(S)
• (.+/-.)-Corydalis B
• Oprea1_616043
• Oprea1_801288
• BSPBio_003379
• KBioGR_002198
• KBioSS_002034
• MLS006011812
• DivK1c_007052
• SCHEMBL230849
• SPECTRUM1504178
• SPBio_000692
• (.+/-.)-Tetrahydropalmatine
• MEGxp0_000623
• ACon1_002069
• CHEBI:91709
• KBio1_001996
• KBio2_002034
• KBio2_004602
• KBio2_007170
• KBio3_002599
• DTXSID20864207
• AEQDJSLRWYMAQI-UHFFFAOYSA-N
• HMS3428E01
• HMS3886C12
• BCP13567
• HY-N0300
• BBL028394
• BDBM50170666
• CCG-40142
• MFCD00214191
• s5559
• STK395032
• AKOS000276804
• AKOS016186982
• FD10012
• SDCCGMLS-0015237.P002
• NCGC00073008-02
• NCGC00073008-03
• NCGC00073008-04
• NCGC00095840-01
• NCGC00095840-02
• NCGC00095840-03
• AS-12924
• SMR004703491
• FT-0601094
• FT-0634567
• FT-0674470
• FT-0675040
• T3650
• A19519
• AB00053100-09
• Berbine, 2,3,9,10-tetramethoxy-, (.+.)-
• A819879
• Berbine, 2,3,9,10-tetramethoxy-, (.+/-.)-
• BRD-A43940795-001-02-8
• BRD-A43940795-001-03-6
• Q27163527
• 5,8,13,13a-Tetrahydro-2,3,9,10-tetramethoxy-6H- dibenzo[a,g]quinolizine
• 2,3,9,10-tetramethoxy-6,8,13,13a-tetrahydro-5H-isoquinolino[2,1-b]isoquinoline;Rotundine
• 6H-Dibenzo[a,g]quinolizine, 5,8,13,13a-tetrahydro-2,3,9,10-tetramethoxy-, (.+.)-
• 6H-Dibenzo[a,g]quinolizine, 5,8,13,13a-tetrahydro-2,3,9,10-tetramethoxy-, (.+/-.)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
No predicted properties yet!

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL4081	P13726	Coagulation factor III	14.98 nM; 22.78 nM; 14.98 nM	IC50; IC50; IC50	PMID: 23199480; via Super-PRED; via Super-PRED
CHEMBL340	P08684	Cytochrome P450 3A4	31622.8 nM; 31622.8 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL2056	P21728	Dopamine D1 receptor	153 nM	Ki	via Super-PRED
CHEMBL217	P14416	Dopamine D2 receptor	450 nM	IC50	via Super-PRED
CHEMBL1850	P21918	Dopamine D5 receptor	305 nM	Ki	via Super-PRED
CHEMBL287	Q99720	Sigma opioid receptor	2.5 nM	Ki	PMID: 16033255

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.20%	96.09%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	96.08%	93.40%
CHEMBL5747	Q92793	CREB-binding protein	94.59%	95.12%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.95%	86.33%
CHEMBL2535	P11166	Glucose transporter	91.17%	98.75%
CHEMBL4302	P08183	P-glycoprotein 1	90.11%	92.98%
CHEMBL241	Q14432	Phosphodiesterase 3A	89.22%	92.94%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	88.63%	89.62%
CHEMBL5608	Q16288	NT-3 growth factor receptor	87.41%	95.89%
CHEMBL3192	Q9BY41	Histone deacetylase 8	86.68%	93.99%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	86.65%	94.45%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	86.23%	95.89%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.07%	95.56%
CHEMBL2069156	Q14145	Kelch-like ECH-associated protein 1	85.33%	82.38%
CHEMBL2146302	O94925	Glutaminase kidney isoform, mitochondrial	83.90%	100.00%
CHEMBL2581	P07339	Cathepsin D	83.69%	98.95%
CHEMBL3438	Q05513	Protein kinase C zeta	83.36%	88.48%
CHEMBL4247	Q9UM73	ALK tyrosine kinase receptor	81.44%	96.86%
CHEMBL4681	P42330	Aldo-keto-reductase family 1 member C3	80.53%	89.05%

Plants that contains it

• Coptis chinensis
• Coptis deltoidea
• Coptis japonica
• Coptis teeta
• Corydalis ambigua
• Corydalis aurea
• Corydalis balansae
• Corydalis caseana
• Corydalis cava
• Corydalis decumbens
• Corydalis heterocarpa
• Corydalis nobilis
• Corydalis orthopoda
• Corydalis pallida
• Corydalis racemosa
• Corydalis saxicola
• Corydalis solida
• Corydalis ternata
• Corydalis turtschaninovii
• Corydalis yanhusuo
• Dicentra formosa
• Fibraurea recisa
• Glycyrrhiza uralensis
• Phellodendron amurense
• Phellodendron chinense
• Sinomenium acutum
• Stephania bancroftii
• Stephania venosa

Cross-Links

• PubChem: 5417
• NPASS: NPC16107
• ChEMBL: CHEMBL187892
• LOTUS: LTS0053701
• wikiData: Q27163527