Tetrahydropalmatine hydrochloride

Details

• Internal ID: 975c1d03-d738-44dc-a03d-eb3e452e23d7
• 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;hydrochloride
• SMILES (Canonical): COC1=C(C2=C(CC3C4=CC(=C(C=C4CCN3C2)OC)OC)C=C1)OC.Cl
• SMILES (Isomeric): COC1=C(C2=C(CC3C4=CC(=C(C=C4CCN3C2)OC)OC)C=C1)OC.Cl
• InChI: InChI=1S/C21H25NO4.ClH/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;1H
• InChI Key: MGSZZQQRTPWMEI-UHFFFAOYSA-N
• Popularity: 5 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₂₆ClNO₄
• Molecular Weight: 391.90 g/mol
• Exact Mass: 391.1550360 g/mol
• Topological Polar Surface Area (TPSA): 40.20 Ų
• XlogP: 0.00
• Atomic LogP (AlogP): 3.80
• H-Bond Acceptor: 5
• H-Bond Donor: 0
• Rotatable Bonds: 4

Synonyms

• 6024-85-7
• Tetrahydropalmatine HCl
• Tetrahydropalmatine (hydrochloride)
• dl-Tetrahydropalmatine hydrochloride
• 2506-20-9
• DL-Tetrahydropalmatine (hydrochloride)
• NSC-132057
• NSC-209411
• (+/-)-tetrahydropalmatine hydrochloride
• 2,3,9,10-tetramethoxy-6,8,13,13a-tetrahydro-5H-isoquinolino[2,1-b]isoquinoline;hydrochloride
• 2,3,9,10-Tetramethoxy-6,8,13,13a-tetrahydro-5H-isoquinolino[3,2-a]isoquinoline hydrochloride
• Tetrahydropalmatine hydrochloride, (+/-)-
• 2,3,9,10-Tetramethoxy-5,8,13,13a-tetrahydro-6H-isoquino[3,2-a]isoquinoline hydrochloride
• SMR000008833
• 4AA8F911N9
• WLN: T D6 B666 KN&TT&J GO1 HO1 PO1 QO1 &GH
• D-Tetrahydropalmatine hydrochloride
• MLS000029596
• O(C)c1cc2c(CCN3Cc4c(ccc(OC)c4OC)CC23)cc1OC
• NSC-132058
• Berbine, 2,3,9,10-tetramethoxy-, hydrochloride, (.+.)-
• 6H-Dibenzo[a,g]quinolizine, 5,8,13,13a-tetrahydro-2,3,9,10-tetramethoxy-, hydrochloride, (.+.)-
• MLS002535962
• SCHEMBL3502167
• CHEMBL1412574
• HY-N0300A
• Palmatine, hydrochloride, (+)-
• EX-A6787
• NSC132057
• NSC132058
• NSC209411
• s3854
• Palmatine, hydrochloride, (.+-.)-
• TETRAHYDROPALMATINE HCL [INCI]
• AKOS024399264
• AC-8031
• CCG-268548
• (D,L)-Tetrahydropalmatine hydrochloride
• CS-0018322
• FT-0698667
• Berbine,3,9,10-tetramethoxy-, hydrochloride
• C16053
• A832652
• Berbine,3,9,10-tetramethoxy-, hydrochloride, (+)-
• Q27259340
• TETRAHYDROPALMATINE DL-FORM HYDROCHLORIDE [MI]
• 13a.beta.-Berbine,3,9,10-tetramethoxy-, hydrochloride
• Berbine,3,9,10-tetramethoxy-, hydrochloride, (.+-.)-
• BERBINE, 2,3,9,10-TETRAMETHOXY-, HYDROCHLORIDE, (+/-)-
• 6H-Dibenzo[a, 5,8,13,13a-tetrahydro-2,3,9,10-tetramethoxy-, hydrochloride
• 6H-Dibenzo[a, 5,8,13,13a-tetrahydro-2,3,9,10-tetramethoxy-, hydrochloride, (.+-.)-
• 6H-Dibenzo[a, 5,8,13,13a-tetrahydro-2,3,9,10-tetramethoxy-, hydrochloride, (R)-
• 2,3,9,10-Tetramethoxy-5,8,13,13a-tetrahydro-6H-isoquinolino[3,2-a]isoquinoline hydrochloride
• 6H-DIBENZO(A,G)QUINOLIZINE, 5,8,13,13A-TETRAHYDRO-2,3,9,10-TETRAMETHOXY-, HYDROCHLORIDE (1:1)

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9685	96.85%
Caco-2	+	0.9145	91.45%
Blood Brain Barrier	+	0.6750	67.50%
Human oral bioavailability	-	0.8143	81.43%
Subcellular localzation	Mitochondria	0.5852	58.52%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9486	94.86%
OATP1B3 inhibitior	+	0.9496	94.96%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	+	0.6000	60.00%
BSEP inhibitior	+	0.6039	60.39%
P-glycoprotein inhibitior	+	0.6925	69.25%
P-glycoprotein substrate	+	0.5668	56.68%
CYP3A4 substrate	+	0.6004	60.04%
CYP2C9 substrate	+	0.7753	77.53%
CYP2D6 substrate	+	0.8760	87.60%
CYP3A4 inhibition	-	0.6427	64.27%
CYP2C9 inhibition	-	0.8975	89.75%
CYP2C19 inhibition	+	0.5314	53.14%
CYP2D6 inhibition	+	0.6808	68.08%
CYP1A2 inhibition	-	0.5320	53.20%
CYP2C8 inhibition	-	0.6498	64.98%
CYP inhibitory promiscuity	-	0.6938	69.38%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9100	91.00%
Carcinogenicity (trinary)	Non-required	0.5853	58.53%
Eye corrosion	-	0.9874	98.74%
Eye irritation	-	0.9719	97.19%
Skin irritation	-	0.7694	76.94%
Skin corrosion	-	0.9350	93.50%
Ames mutagenesis	-	0.6000	60.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.9074	90.74%
Micronuclear	-	0.5700	57.00%
Hepatotoxicity	-	0.7000	70.00%
skin sensitisation	-	0.8725	87.25%
Respiratory toxicity	+	0.8556	85.56%
Reproductive toxicity	+	0.8333	83.33%
Mitochondrial toxicity	+	0.8500	85.00%
Nephrotoxicity	-	0.6534	65.34%
Acute Oral Toxicity (c)	III	0.4943	49.43%
Estrogen receptor binding	+	0.6884	68.84%
Androgen receptor binding	-	0.4813	48.13%
Thyroid receptor binding	+	0.6218	62.18%
Glucocorticoid receptor binding	+	0.5908	59.08%
Aromatase binding	-	0.8005	80.05%
PPAR gamma	-	0.6837	68.37%
Honey bee toxicity	-	0.8685	86.85%
Biodegradation	-	0.9250	92.50%
Crustacea aquatic toxicity	+	0.7300	73.00%
Fish aquatic toxicity	+	0.7211	72.11%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1293235	P02545	Prelamin-A/C	14125.4 nM	Potency	via CMAUP
CHEMBL1963	P16473	Thyroid stimulating hormone receptor	39810.7 nM; 39810.7 nM	Potency; Potency	via CMAUP; via CMAUP

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.26%	96.09%
CHEMBL217	P14416	Dopamine D2 receptor	96.99%	95.62%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	95.82%	93.40%
CHEMBL5747	Q92793	CREB-binding protein	94.11%	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	90.46%	92.98%
CHEMBL241	Q14432	Phosphodiesterase 3A	89.22%	92.94%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	89.18%	89.62%
CHEMBL2056	P21728	Dopamine D1 receptor	89.17%	91.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	87.41%	95.89%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	86.65%	94.45%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.54%	95.56%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	86.23%	95.89%
CHEMBL3192	Q9BY41	Histone deacetylase 8	86.02%	93.99%
CHEMBL2069156	Q14145	Kelch-like ECH-associated protein 1	85.33%	82.38%
CHEMBL2146302	O94925	Glutaminase kidney isoform, mitochondrial	83.90%	100.00%
CHEMBL3438	Q05513	Protein kinase C zeta	82.11%	88.48%
CHEMBL2581	P07339	Cathepsin D	81.98%	98.95%
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

• Corydalis decumbens
• Corydalis pallida
• Corydalis turtschaninovii
• Corydalis yanhusuo
• Glycyrrhiza uralensis
• Phellodendron amurense
• Phellodendron chinense

Cross-Links

• PubChem: 6602555
• NPASS: NPC51957
• ChEMBL: CHEMBL1412574