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8-hydroxypalmatine

Family: Plantae - Annonaceae
Kingdom: Plantae
Class: Alkaloid
- Subclass: Protoberberine Alkaloid

Canonical Smiles	COc1cc2CCN3[C@H](c2cc1OC)Cc1c(C3O)c(OC)c(cc1)OC
InChI	InChI=1S/C21H25NO5/c1-24-16-6-5-13-9-15-14-11-18(26-3)17(25-2)10-12(14)7-8-22(15)21(23)19(13)20(16)27-4/h5-6,10-11,15,21,23H,7-9H2,1-4H3/t15-,21?/m0/s1
InChIKey	ULTSSEXKHZKTST-ZDGMYTEDSA-N
Formula	C₂₁H₂₅NO₅
HBA	6
HBD	1
MW	371.43
Rotatable Bonds	4
TPSA	60.39
LogP	2.87
Number Rings	4
Number Aromatic Rings	2
Heavy Atom Count	27
Formal Charge	0
Fraction CSP3	0.43
Exact Mass	371.17
Number of Lipinski Rule Violations	0

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Enantia chlorantha	Annonaceae	Plantae	306909

Showing of synonyms

Nkwengoua ET, Ngantchou I, et al. (2009). In vitro inhibitory effects of palmatine from Enantia chlorantha on Trypanosoma cruzi and Leishmania infantum. Natural product research,2009, 23(12), 1144-1150. [View] [PubMed]

No compound-protein relationship available.

SMILES: c1cccc(c12)CCN3C2Cc4c(C3)cccc4

Level: 0

Mol. Weight: 371.43 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -4.61
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.700
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Substrate
Skin Permeability: -1.64

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 0.940
Plasma Protein Binding: 44.72
Steady State Volume of Distribution: -

Metabolism

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

Excretion

Clearance: 8.340
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: 1.120
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.340
Liver Injury II: Toxic
hERG Blockers: Toxic
Daphnia Maga: 8.450
Micronucleos: Toxic
NR-AhR: Safe
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: Safe
T. Pyriformis: -10.290
Rat (Acute): 2.480
Rat (Chronic Oral): 1.560
Fathead Minnow: 4.510
Respiratory Disease: Toxic
Skin Sensitisation: Safe
SR-ARE: Safe
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Safe
SR-p53: Safe

General Properties

Boiling Point: 434.340
Hydration Free Energy: -7.770
Log(D) at pH=7.4: 2.140
Log(P): 1.97
Log S: -1.25
Log(Vapor Pressure): -7.93
Melting Point: 182.58
pKa Acid: 11.84
pKa Basic: 7.34

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	0.9450
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	3	0.9292
UDP-N-acetylglucosamine 1-carboxyvinyltransferase	P33038	MURA_ENTCC	Enterobacter cloacae subsp. cloacae	3	0.9214
Pantothenate synthetase	P9WIL5	PANC_MYCTU	Mycobacterium tuberculosis	3	0.9088
3-hydroxybenzoate 4-monooxygenase	Q6SSJ6	MOBA_COMTE	Comamonas testosteroni	3	0.9078
Aspartate aminotransferase	P00509	AAT_ECOLI	Escherichia coli	3	0.8840
Serine/threonine-protein kinase pim-1	P11309	PIM1_HUMAN	Homo sapiens	4	0.8782
Steroid C26-monooxygenase	P9WPP1	CP125_MYCTU	Mycobacterium tuberculosis	3	0.8735
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	4	0.8700
Mitogen-activated protein kinase 8	P45983	MK08_HUMAN	Homo sapiens	3	0.8619
Aldehyde dehydrogenase, mitochondrial	P05091	ALDH2_HUMAN	Homo sapiens	4	0.8564
Thermolysin	P00800	THER_BACTH	Bacillus thermoproteolyticus	3	0.8553
Cytochrome P450	S6BVH1	S6BVH1_RHOER	Rhodococcus erythropolis	3	0.8496
FMN-dependent NAD(P)H:quinone oxidoreductase 1	Q9I5F3	AZOR1_PSEAE	Pseudomonas aeruginosa	3	0.8402
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.8388
Acetylornithine/succinyldiaminopimelate aminotransferase	P40732	ARGD_SALTY	Salmonella typhimurium	3	0.8388
NADPH dehydrogenase 1	Q02899	OYE1_SACPS	Saccharomyces pastorianus	3	0.8385
Aldehyde dehydrogenase, mitochondrial	P05091	ALDH2_HUMAN	Homo sapiens	4	0.8364
Stromelysin-1	P08254	MMP3_HUMAN	Homo sapiens	3	0.8344
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	3	0.8334
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.8017
Peroxisome proliferator-activated receptor gamma	P37231	PPARG_HUMAN	Homo sapiens	4	0.8008
Beta-ketoacyl-[acyl-carrier-protein] synthase III	Q820T1	FABH_ENTFA	Enterococcus faecalis	3	0.7985
Major pollen allergen Bet v 1-A	P15494	BEV1A_BETPN	Betula pendula	3	0.7920
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7912
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.7780
Rhodopsin kinase GRK1	P28327	GRK1_BOVIN	Bos taurus	3	0.7771
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7642
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	3	0.7635
Phosphodiesterase	Q8WQX9	Q8WQX9_9TRYP	Trypanosoma brucei	4	0.7620
Caspase-3	P42574	CASP3_HUMAN	Homo sapiens	2	0.7583
Lactoperoxidase	P80025	PERL_BOVIN	Bos taurus	3	0.7562
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	3	0.7496
L-lactate dehydrogenase (cytochrome)	P00175	CYB2_YEAST	Saccharomyces cerevisiae	3	0.7487
Pantothenate synthetase	P9WIL4	PANC_MYCTO	Mycobacterium tuberculosis	3	0.7423
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	3	0.7404
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7385
Aldo-keto reductase family 1 member B1	P15121	ALDR_HUMAN	Homo sapiens	3	0.7370
HTH-type transcriptional regulator TtgR	Q9AIU0	TTGR_PSEPT	Pseudomonas putida	3	0.7328
Glucan 1,3-beta-glucosidase	P29717	EXG1_CANAL	Candida albicans	2	0.7286
Fibroblast growth factor receptor 1	P11362	FGFR1_HUMAN	Homo sapiens	3	0.7280
Cytochrome P450 1A1	P04798	CP1A1_HUMAN	Homo sapiens	3	0.7274
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	2	0.7255
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	4	0.7237
Protein mono-ADP-ribosyltransferase PARP3	Q9Y6F1	PARP3_HUMAN	Homo sapiens	3	0.7223
Protein mono-ADP-ribosyltransferase PARP10	Q53GL7	PAR10_HUMAN	Homo sapiens	3	0.7215
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7200
Chalcone--flavanone isomerase 1	P28012	CFI1_MEDSA	Medicago sativa	3	0.7196
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	3	0.7182
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	3	0.7178
Serine/threonine-protein kinase 24	Q9Y6E0	STK24_HUMAN	Homo sapiens	3	0.7144
Glycogen phosphorylase, muscle form	P00489	PYGM_RABIT	Oryctolagus cuniculus	3	0.7100
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7086
Diphtheria toxin	P00588	DTX_CORBE	Corynephage beta	3	0.7044
Focal adhesion kinase 1	Q05397	FAK1_HUMAN	Homo sapiens	2	0.7041
Capsid protein	Q9WBP8	Q9WBP8_9VIRU	Adeno-associated virus - 1	3	0.7032
Anthocyanidin 3-O-glucosyltransferase UFGT	P51094	UFOG_VITVI	Vitis vinifera	3	0.7029
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7016

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