Jatrorrhizine

Details

• Internal ID: 2b9232b9-3a74-4ec6-9ca8-07446978aed6
• Taxonomy: Alkaloids and derivatives > Protoberberine alkaloids and derivatives
• IUPAC Name: 2,9,10-trimethoxy-5,6-dihydroisoquinolino[2,1-b]isoquinolin-7-ium-3-ol
• SMILES (Canonical): COC1=C(C2=C[N+]3=C(C=C2C=C1)C4=CC(=C(C=C4CC3)O)OC)OC
• SMILES (Isomeric): COC1=C(C2=C[N+]3=C(C=C2C=C1)C4=CC(=C(C=C4CC3)O)OC)OC
• InChI: InChI=1S/C20H19NO4/c1-23-18-5-4-12-8-16-14-10-19(24-2)17(22)9-13(14)6-7-21(16)11-15(12)20(18)25-3/h4-5,8-11H,6-7H2,1-3H3/p+1
• InChI Key: MXTLAHSTUOXGQF-UHFFFAOYSA-O
• Popularity: 223 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₀NO₄+
• Molecular Weight: 338.40 g/mol
• Exact Mass: 338.13923312 g/mol
• Topological Polar Surface Area (TPSA): 51.80 Ų
• XlogP: 3.40
• Atomic LogP (AlogP): 3.08
• H-Bond Acceptor: 4
• H-Bond Donor: 1
• Rotatable Bonds: 3

Synonyms

• 3621-38-3
• neprotin
• jateorrhizine
• Yatrorizine
• 2,9,10-trimethoxy-5,6-dihydroisoquinolino[2,1-b]isoquinolin-7-ium-3-ol
• 3-Hydroxy-2,9,10-trimethoxy-5,6-dihydroisoquinolino[3,2-a]isoquinolin-7-ium
• 7,8,13,13a-tetradehydro-3-hydroxy-2,9,10-trimethoxyberbinium
• UNII-091S1F8V5Q
• CHEBI:6087
• CHEMBL251055
• GNF-PF-220
• 091S1F8V5Q
• Dibenzo[a,g]quinolizinium, 5,6-dihydro-3-hydroxy-2,9,10-trimethoxy-
• EINECS 222-817-3
• 3-Hydroxy-2,9,10-trimethoxy-5,6-dihydroisoquinolino-[3,2-a]isoquinolin-7-ium
• 5,6-Dihydro-3-hydroxy-2,9,10-trimethoxydibenzo[a,g]quinolizinium
• NSC150445
• NSC209410
• NSC645313
• Jateorhizine
• Jatrochizine
• Jatrorhizine
• Neprotine
• O(C)c1cc2c(CCn3cc4c(ccc(OC)c4OC)cc23)cc1O
• 5,6-DIHYDRO-3-HYDROXY-2,9,10-TRIMETHOXYDIBENZO(A,G)QUINOLIZINIUM
• Dehydrocorypalmine
• Berbinium, 7,8,13,13a-tetradehydro-3-hydroxy-2,9,10-trimethoxy-
• Jatrorrhizine (Neprotine)
• JATRORRHIZINE [MI]
• D0V0NM
• MLS000563433
• SCHEMBL564128
• MEGxp0_001765
• DTXSID40189767
• MXTLAHSTUOXGQF-UHFFFAOYSA-O
• HMS2224L17
• HMS3354I18
• HMS3885O10
• HY-N0749
• BDBM50226670
• s3884
• AKOS015896759
• CCG-267897
• NCGC00247622-01
• NCI60_042074
• SMR000232285
• 4-trans-n-Pentylcyclohexyl-4-ethylbiphenyl
• CS-0009780
• FT-0686648
• C09553
• Q10910369
• 7,8,13,13a-tetrahydro-3-hydroxy-2,9,10-trimethoxyberbinium
• 5,6-dihydro-3-hydroxy-2,9,10-trimethoxy-dibenzo[a,g]quinolizinium
• 7,8,13,13|A-Tetradehydro-3-hydroxy-2,9,10-trimethoxyberbinium
• 2,9,10-trimethoxy-5,6-dihydroisoquinolino[3,2-a]isoquinolin-7-ium-3-ol
• Berbinium, 7,8,13,13a-tetradehydro-3-hydroxy-2,9,10-trimethoxy- (8CI)
• 2,9,10-Trimethoxy-5,6-dihydro-7lambda~5~-isoquino[3,2-a]isoquinolin-3-ol hydrochloride

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.6158	61.58%
Caco-2	+	0.9270	92.70%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	+	0.6000	60.00%
Subcellular localzation	Mitochondria	0.6307	63.07%
OATP2B1 inhibitior	-	0.8757	87.57%
OATP1B1 inhibitior	+	0.9321	93.21%
OATP1B3 inhibitior	+	0.9488	94.88%
MATE1 inhibitior	-	0.7800	78.00%
OCT2 inhibitior	+	0.5750	57.50%
BSEP inhibitior	+	0.7120	71.20%
P-glycoprotein inhibitior	-	0.5595	55.95%
P-glycoprotein substrate	-	0.6983	69.83%
CYP3A4 substrate	+	0.5398	53.98%
CYP2C9 substrate	-	0.8169	81.69%
CYP2D6 substrate	+	0.3688	36.88%
CYP3A4 inhibition	-	0.8912	89.12%
CYP2C9 inhibition	-	0.9122	91.22%
CYP2C19 inhibition	-	0.8948	89.48%
CYP2D6 inhibition	+	0.6800	68.00%
CYP1A2 inhibition	-	0.6780	67.80%
CYP2C8 inhibition	+	0.5000	50.00%
CYP inhibitory promiscuity	-	0.7205	72.05%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9400	94.00%
Carcinogenicity (trinary)	Non-required	0.5946	59.46%
Eye corrosion	-	0.9884	98.84%
Eye irritation	-	0.8564	85.64%
Skin irritation	-	0.7571	75.71%
Skin corrosion	-	0.9432	94.32%
Ames mutagenesis	-	0.6800	68.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6374	63.74%
Micronuclear	+	0.6000	60.00%
Hepatotoxicity	+	0.5125	51.25%
skin sensitisation	-	0.9114	91.14%
Respiratory toxicity	+	0.5778	57.78%
Reproductive toxicity	+	0.8000	80.00%
Mitochondrial toxicity	+	0.7125	71.25%
Nephrotoxicity	-	0.8792	87.92%
Acute Oral Toxicity (c)	III	0.7143	71.43%
Estrogen receptor binding	+	0.9418	94.18%
Androgen receptor binding	+	0.7691	76.91%
Thyroid receptor binding	+	0.6904	69.04%
Glucocorticoid receptor binding	+	0.8413	84.13%
Aromatase binding	-	0.6509	65.09%
PPAR gamma	+	0.6930	69.30%
Honey bee toxicity	-	0.9126	91.26%
Biodegradation	-	0.9750	97.50%
Crustacea aquatic toxicity	+	0.6200	62.00%
Fish aquatic toxicity	-	0.7441	74.41%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL340	P08684	Cytochrome P450 3A4	2100 nM	IC50	PMID: 17994701
CHEMBL2392	P06746	DNA polymerase beta	39810.7 nM	Potency	via CMAUP
CHEMBL2362978	P43351	DNA repair protein RAD52 homolog	15210 nM	AC50	via CMAUP
CHEMBL1293226	B2RXH2	Lysine-specific demethylase 4D-like	12589.3 nM	Potency	via CMAUP
CHEMBL2608	P10253	Lysosomal alpha-glucosidase	7079.5 nM	Potency	via CMAUP
CHEMBL1293224	P10636	Microtubule-associated protein tau	15848.9 nM	Potency	via CMAUP
CHEMBL1293235	P02545	Prelamin-A/C	11220.2 nM	Potency	via CMAUP
CHEMBL1293232	Q16637	Survival motor neuron protein	3162.3 nM	Potency	via CMAUP

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL1951	P21397	Monoamine oxidase A	98.23%	91.49%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.99%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.36%	95.56%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	91.44%	89.62%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	90.94%	94.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	90.54%	96.09%
CHEMBL241	Q14432	Phosphodiesterase 3A	89.88%	92.94%
CHEMBL2535	P11166	Glucose transporter	89.82%	98.75%
CHEMBL3192	Q9BY41	Histone deacetylase 8	89.76%	93.99%
CHEMBL5747	Q92793	CREB-binding protein	89.74%	95.12%
CHEMBL1937	Q92769	Histone deacetylase 2	86.60%	94.75%
CHEMBL1293249	Q13887	Kruppel-like factor 5	86.54%	86.33%
CHEMBL2056	P21728	Dopamine D1 receptor	86.15%	91.00%
CHEMBL2581	P07339	Cathepsin D	85.74%	98.95%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	84.80%	99.15%
CHEMBL261	P00915	Carbonic anhydrase I	82.64%	96.76%
CHEMBL3438	Q05513	Protein kinase C zeta	81.89%	88.48%
CHEMBL3060	Q9Y345	Glycine transporter 2	81.86%	99.17%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.79%	95.89%
CHEMBL4208	P20618	Proteasome component C5	80.53%	90.00%

Plants that contains it

• Aloe microstigma subsp. microstigma
• Anaxagorea luzonensis
• Androsace septentrionalis
• Argyreia nervosa
• Astragalus thracicus
• Berberis amurensis
• Berberis fortunei
• Berberis japonica
• Berberis julianae
• Berberis oblonga
• Berberis thunbergii
• Bupleurum scorzonerifolium
• Calocephalus knappii
• Carapichea ipecacuanha
• Coleostephus myconis
• Coptis chinensis
• Coptis deltoidea
• Coptis japonica
• Coptis omeiensis
• Coptis teeta
• Corydalis decumbens
• Corydalis ternata
• Corydalis turtschaninovii
• Corydalis yanhusuo
• Croton regelianus
• Elettaria cardamomum
• Erythrina chiriquensis
• Eupatorium album
• Euphorbia fortissima
• Fibraurea recisa
• Hemionitis schaffneri
• Lathyrus aphaca
• Ligularia nelumbifolia
• Macrozamia spiralis
• Magnolia biondii
• Melianthus major
• Neocussonia longipedicellata
• Orobanche arenaria
• Panax quinquefolius
• Phellodendron amurense
• Phellodendron chinense
• Phoradendron reichenbachianum
• Pilosocereus chrysacanthus
• Piper retrofractum
• Plectranthus ernstii
• Pseudofumaria lutea
• Radula voluta
• Sideritis ferrensis
• Stephania tetrandra
• Thalictrum atriplex
• Thalictrum faberi
• Thalictrum foliolosum
• Thalictrum glandulosissimum
• Thalictrum lucidum
• Thalictrum microgynum
• Thalictrum petaloideum
• Thalictrum simplex
• Theobroma speciosum
• Tinospora hainanensis
• Tinospora sagittata

Cross-Links

• PubChem: 72323
• NPASS: NPC13826
• ChEMBL: CHEMBL251055