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Jatrorrhizine

Family: Plantae - Menispermaceae
Kingdom: Plantae
Class: Alkaloid
- Subclass: Isoquinoline Alkaloid

Canonical Smiles	COc1cc2c(cc1O)CC[n+]1c2cc2ccc(c(c2c1)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
InChIKey	MXTLAHSTUOXGQF-UHFFFAOYSA-O
Formula	C₂₀H₂₀NO₄+
HBA	4
HBD	1
MW	338.38
Rotatable Bonds	3
TPSA	51.8
LogP	3.08
Number Rings	4
Number Aromatic Rings	3
Heavy Atom Count	25
Formal Charge	1
Fraction CSP3	0.25
Exact Mass	338.14
Number of Lipinski Rule Violations	0

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Enantia chlorantha	Annonaceae	Plantae	306909
2	Penianthus longifolius	Menispermaceae	Plantae	461618

Showing of synonyms

Djoumessi AK, Nono RN, et al. (2023). Constituents of the Stem Bark of Trichilia monadelpha (Thonn.) J. J. De Wilde (Meliaceae) and Their Antibacterial and Antiplasmodial Activities. Metabolites 2023, 13, 298. [View] [PubMed]
Nyongbela KD, Samje M, et al. (2019). Evaluation of anti-onchocercal activity of pseudopalmatine, a quaternary protoberberine alkaloid of Enantia chlorantha (Syn. Annickia chlorantha). Journal of the Cameroon Academy of Sciences, 2019, 14(3). [View]

Pubchem: 72323

Cas: 3621-38-3

Gnps: CCMSLIB00006514955

Zinc: ZINC000000338122

Kegg Ligand: C09553

Chebi: 6087

Nmrshiftdb2: 70121310

Metabolights: MTBLC6087

Chembl: CHEMBL251055

Comptox: DTXSID40189767

Bindingdb: 50226670

CPRiL: 73353

SMILES: c1cccc(c12)CC[n+]3c2cc4c(c3)cccc4

Level: 0

Mol. Weight: 338.38 g/mol

Antimalarial

Absorption

Caco-2 (logPapp): -5.14
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.570
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -1.92

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 1.180
Plasma Protein Binding: 68.8
Steady State Volume of Distribution: -

Metabolism

Breast Cancer Resistance Protein: Non-Inhibitor
CYP 1A2 Inhibitor: Inhibitor
CYP 1A2 Substrate: Substrate
CYP 2C19 Inhibitor: Non-Inhibitor
CYP 2C19 Substrate: Non-Substrate
CYP 2C9 Inhibitor: Non-Inhibitor
CYP 2C9 Substrate: Substrate
CYP 2D6 Inhibitor: Non-Inhibitor
CYP 2D6 Substrate: Substrate
CYP 3A4 Inhibitor: Non-Inhibitor
CYP 3A4 Substrate: Non-Substrate
OATP1B1: Non-Inhibitor
OATP1B3: Non-Inhibitor

Excretion

Clearance: 7.170
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: 1.490
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Toxic
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.790
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 8.310
Micronucleos: Toxic
NR-AhR: Toxic
NR-AR: Safe
NR-AR-LBD: Safe
NR-Aromatase: Safe
NR-ER: Safe
NR-ER-LBD: Safe
NR-GR: Safe
NR-PPAR-gamma: Safe
NR-TR: Toxic
T. Pyriformis: -1.680
Rat (Acute): 2.640
Rat (Chronic Oral): 1.730
Fathead Minnow: 4.980
Respiratory Disease: Toxic
Skin Sensitisation: Toxic
SR-ARE: Safe
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Toxic
SR-p53: Safe

General Properties

Boiling Point: 441.220
Hydration Free Energy: -7.980
Log(D) at pH=7.4: 2.580
Log(P): -0.2
Log S: -1.31
Log(Vapor Pressure): -8.56
Melting Point: 220.47
pKa Acid: 9.4
pKa Basic: 5.49

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
HTH-type transcriptional regulator TtgR	Q9AIU0	TTGR_PSEPT	Pseudomonas putida	3	0.9627
Mitogen-activated protein kinase 8	P45983	MK08_HUMAN	Homo sapiens	3	0.9348
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.9325
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.9278
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	3	0.9235
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	3	0.9220
Estrogen receptor	P03372	ESR1_HUMAN	Homo sapiens	4	0.9178
Steroid C26-monooxygenase	P9WPP1	CP125_MYCTU	Mycobacterium tuberculosis	3	0.9127
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.9066
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.9041
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.9034
Lactoperoxidase	A0A452E9Y6	PERL_CAPHI	Capra hircus	3	0.9011
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8934
Mitogen-activated protein kinase 8	P45983	MK08_HUMAN	Homo sapiens	3	0.8926
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	3	0.8902
Mitogen-activated protein kinase 8	P45983	MK08_HUMAN	Homo sapiens	3	0.8882
Non-receptor tyrosine-protein kinase TYK2	P29597	TYK2_HUMAN	Homo sapiens	3	0.8872
Phytohormone-binding protein CSBP	A0A1S3THR8	PHBP_VIGRR	Vigna radiata var. radiata	3	0.8843
TetR family transcriptional regulator	Q58L87	Q58L87_MYCSM	Mycolicibacterium smegmatis	3	0.8777
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8772
Tyrosine-protein kinase SYK	P43405	KSYK_HUMAN	Homo sapiens	3	0.8748
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8735
Major pollen allergen Bet v 1-A	P15494	BEV1A_BETPN	Betula pendula	3	0.8714
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.8707
Non-receptor tyrosine-protein kinase TYK2	P29597	TYK2_HUMAN	Homo sapiens	3	0.8675
Transthyretin	P02766	TTHY_HUMAN	Homo sapiens	4	0.8674
Serine/threonine-protein kinase pim-1	P11309	PIM1_HUMAN	Homo sapiens	4	0.8661
Neocarzinostatin	P0A3R9	NCZS_STRCZ	Streptomyces carzinostaticus	3	0.8661
Peroxisome proliferator-activated receptor gamma	P37231	PPARG_HUMAN	Homo sapiens	4	0.8639
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8622
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.8549
Non-receptor tyrosine-protein kinase TYK2	P29597	TYK2_HUMAN	Homo sapiens	3	0.8529
Serine/threonine-protein kinase pim-1	P11309	PIM1_HUMAN	Homo sapiens	3	0.8491
Bromodomain adjacent to zinc finger domain protein 2B	Q9UIF8	BAZ2B_HUMAN	Homo sapiens	3	0.8443
Histamine N-methyltransferase	P50135	HNMT_HUMAN	Homo sapiens	4	0.8417
Transthyretin	P02767	TTHY_RAT	Rattus norvegicus	3	0.8395
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	3	0.8389
Non-receptor tyrosine-protein kinase TYK2	P29597	TYK2_HUMAN	Homo sapiens	4	0.8296
Proto-oncogene tyrosine-protein kinase Src	P00523	SRC_CHICK	Gallus gallus	3	0.8207
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.8179
Mitogen-activated protein kinase 1	P28482	MK01_HUMAN	Homo sapiens	3	0.8165
tyrosine--tRNA ligase	Q4QFJ7	Q4QFJ7_LEIMA	Leishmania major	3	0.8161
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	4	0.8149
Purine nucleoside phosphorylase	P00491	PNPH_HUMAN	Homo sapiens	3	0.8135
Acetylcholinesterase	P21836	ACES_MOUSE	Mus musculus	2	0.8120
cAMP-dependent protein kinase catalytic subunit alpha	P00517	KAPCA_BOVIN	Bos taurus	4	0.8070
CREB-binding protein	Q92793	CBP_HUMAN	Homo sapiens	3	0.8061
Hypoxanthine phosphoribosyltransferase	Q4DRC4	Q4DRC4_TRYCC	Trypanosoma cruzi	3	0.8030
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	4	0.8026
Mycocyclosin synthase	P9WPP7	CP121_MYCTU	Mycobacterium tuberculosis	3	0.7996
Mitogen-activated protein kinase 1	P28482	MK01_HUMAN	Homo sapiens	3	0.7990
Tyrosine-protein kinase Lck	P06239	LCK_HUMAN	Homo sapiens	3	0.7983
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	3	0.7913
Gag-Pol polyprotein	O12158	POL_HV192	Human immunodeficiency virus type 1 group M subtype C	3	0.7864
Protoporphyrinogen oxidase	P50336	PPOX_HUMAN	Homo sapiens	3	0.7863
Mitogen-activated protein kinase 14	Q16539	MK14_HUMAN	Homo sapiens	3	0.7838
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7825
Methionine adenosyltransferase 2 subunit beta	Q9NZL9	MAT2B_HUMAN	Homo sapiens	4	0.7820
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7782
Tyrosine-protein kinase JAK3	P52333	JAK3_HUMAN	Homo sapiens	3	0.7751
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	3	0.7705
HTH-type transcriptional regulator TtgR	Q9AIU0	TTGR_PSEPT	Pseudomonas putida	3	0.7691
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.7658
Mycocyclosin synthase	P9WPP7	CP121_MYCTU	Mycobacterium tuberculosis	3	0.7657
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7633
Protoporphyrinogen oxidase	P50336	PPOX_HUMAN	Homo sapiens	3	0.7629
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.7627
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7624
Matrix metalloproteinase-9	P14780	MMP9_HUMAN	Homo sapiens	3	0.7618
Mitogen-activated protein kinase 14	Q16539	MK14_HUMAN	Homo sapiens	3	0.7589
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	3	0.7584
Phosphodiesterase	Q8WQX9	Q8WQX9_9TRYP	Trypanosoma brucei	3	0.7574
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	3	0.7569
Calmodulin	P62157	CALM_BOVIN	Bos taurus	3	0.7563
Nodulin-13	P93330	NOD13_MEDTR	Medicago truncatula	3	0.7557
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	3	0.7543
Chalcone--flavanone isomerase 1	P28012	CFI1_MEDSA	Medicago sativa	3	0.7541
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	3	0.7538
Transcriptional regulator, PadR-like family	A2RI36	A2RI36_LACLM	Lactococcus lactis subsp. cremoris	2	0.7536
Glycogen phosphorylase, muscle form	P00489	PYGM_RABIT	Oryctolagus cuniculus	3	0.7529
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7520
Pancreatic alpha-amylase	P04746	AMYP_HUMAN	Homo sapiens	2	0.7500
Riboflavin synthase	P0AFU8	RISA_ECOLI	Escherichia coli	3	0.7473
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7472
Tubulin alpha-1B chain	P81947	TBA1B_BOVIN	Bos taurus	3	0.7470
Estrogen receptor	P03372	ESR1_HUMAN	Homo sapiens	3	0.7466
Squalene synthase	P37268	FDFT_HUMAN	Homo sapiens	3	0.7463
Tubulin alpha-1B chain	P81947	TBA1B_BOVIN	Bos taurus	4	0.7457
Histone deacetylase 4	P56524	HDAC4_HUMAN	Homo sapiens	3	0.7451
Aldehyde dehydrogenase, mitochondrial	P05091	ALDH2_HUMAN	Homo sapiens	3	0.7431
MAP kinase-activated protein kinase 2	P49137	MAPK2_HUMAN	Homo sapiens	3	0.7417
Serine/threonine-protein kinase Chk2	O96017	CHK2_HUMAN	Homo sapiens	3	0.7402
4-hydroxyphenylacetate 3-monooxygenase	Q8YHT7	Q8YHT7_BRUME	Brucella melitensis biotype 1	2	0.7397
Thymidine phosphorylase	Q7CP66	TYPH_SALTY	Salmonella typhimurium	3	0.7396
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	3	0.7388
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7387
Estrogen receptor	P03372	ESR1_HUMAN	Homo sapiens	3	0.7368
Nuclear receptor subfamily 4immunitygroup A member 1	P22736	NR4A1_HUMAN	Homo sapiens	2	0.7363
Genome polyprotein	O92972	POLG_HCVJ4	Hepatitis C virus genotype 1b	3	0.7356
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7356
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7351
Methionine aminopeptidase 2	P50579	MAP2_HUMAN	Homo sapiens	3	0.7349
FMN-dependent NAD(P)H:quinone oxidoreductase 1	Q9I5F3	AZOR1_PSEAE	Pseudomonas aeruginosa	2	0.7347
Mitogen-activated protein kinase 14	Q16539	MK14_HUMAN	Homo sapiens	3	0.7345
S-norcoclaurine synthase	Q67A25	NCS_THLFG	Thalictrum flavum subsp. glaucum	3	0.7335
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	3	0.7324
Histone-lysine N-methyltransferase EHMT1	Q9H9B1	EHMT1_HUMAN	Homo sapiens	3	0.7286
Homoserine dehydrogenase	P31116	DHOM_YEAST	Saccharomyces cerevisiae	3	0.7280
Aldo-keto reductase family 1 member B1	P15121	ALDR_HUMAN	Homo sapiens	2	0.7267
Pteridine reductase, putative	Q581W1	Q581W1_TRYB2	Trypanosoma brucei brucei	3	0.7264
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7244
Cis-2,3-dihydrobiphenyl-2,3-diol dehydrogenase	Q46381	BPHB_COMTE	Comamonas testosteroni	3	0.7235
Focal adhesion kinase 1	Q00944	FAK1_CHICK	Gallus gallus	3	0.7229
Histone-lysine N-methyltransferase EHMT2	Q96KQ7	EHMT2_HUMAN	Homo sapiens	3	0.7229
Macrophage metalloelastase	P39900	MMP12_HUMAN	Homo sapiens	3	0.7216
WxcM-like protein	Q12KT8	Q12KT8_SHEDO	Shewanella denitrificans	3	0.7210
Serine/threonine-protein kinase 24	Q9Y6E0	STK24_HUMAN	Homo sapiens	3	0.7201
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7201
UDP-N-acetylmuramoyl-tripeptide--D-alanyl-D-alanine ligase	Q8DNV6	Q8DNV6_STRR6	Streptococcus pneumoniae	2	0.7196
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7187
4,4'-diapophytoene synthase	A9JQL9	CRTM_STAAU	Staphylococcus aureus	2	0.7185
Histone-lysine N-methyltransferase 2A	Q03164	KMT2A_HUMAN	Homo sapiens	3	0.7175
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7174
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7171
Histone-lysine N-methyltransferase SETD7	Q8WTS6	SETD7_HUMAN	Homo sapiens	3	0.7162
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7155
Gag-Pol polyprotein	P03366	POL_HV1B1	Human immunodeficiency virus type 1 group M subtype B	3	0.7146
Serine/threonine-protein kinase Nek2	P51955	NEK2_HUMAN	Homo sapiens	3	0.7137
Histone-lysine N-methyltransferase, H3 lysine-9 specific SUVH4	Q8GZB6	SUVH4_ARATH	Arabidopsis thaliana	3	0.7135
Histone-lysine N-methyltransferase EHMT1	Q9H9B1	EHMT1_HUMAN	Homo sapiens	3	0.7132
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7131
Aminoglycoside 3'-phosphotransferase AphA1-IAB	B0VD92	B0VD92_ACIBY	Acinetobacter baumannii	3	0.7130
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	3	0.7127
Focal adhesion kinase 1	Q05397	FAK1_HUMAN	Homo sapiens	3	0.7126
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	3	0.7124
AppA, antirepressor of ppsR, sensor of blue light	Q3J677	Q3J677_RHOS4	Rhodobacter sphaeroides	5	0.7120
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7119
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	P48736	PK3CG_HUMAN	Homo sapiens	4	0.7112
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7100
Genome polyprotein	P26663	POLG_HCVBK	Hepatitis C virus genotype 1b	2	0.7092
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	3	0.7092
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	3	0.7090
Non-receptor tyrosine-protein kinase TYK2	P29597	TYK2_HUMAN	Homo sapiens	3	0.7086
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	4	0.7084
rRNA N-glycosylase	D9J2T9	D9J2T9_MOMBA	Momordica balsamina	3	0.7081
Serine/threonine-protein kinase Chk2	O96017	CHK2_HUMAN	Homo sapiens	3	0.7079
Neuropilin-1	O14786	NRP1_HUMAN	Homo sapiens	3	0.7072
Eukaryotic translation initiation factor 4E-1	P29557	IF4E1_WHEAT	Triticum aestivum	4	0.7071
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7062
Myeloperoxidase	P05164	PERM_HUMAN	Homo sapiens	4	0.7056
Histone-lysine N-methyltransferase EHMT1	Q9H9B1	EHMT1_HUMAN	Homo sapiens	3	0.7055
DNA (cytosine-5)-methyltransferase 3A	O88508	DNM3A_MOUSE	Mus musculus	3	0.7034
Transthyretin	Q9PTT3	Q9PTT3_SPAAU	Sparus aurata	3	0.7028
Carbonic anhydrase 12	O43570	CAH12_HUMAN	Homo sapiens	3	0.7023
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7011
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	3	0.7010
Urokinase-type plasminogen activator	P00749	UROK_HUMAN	Homo sapiens	2	0.7000

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