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Alpha-hydrastine

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

Canonical Smiles	COc1c(OC)ccc2c1C(=O)O[C@H]2[C@@H]1N(C)CCc2c1cc1OCOc1c2
InChI	InChI=1S/C21H21NO6/c1-22-7-6-11-8-15-16(27-10-26-15)9-13(11)18(22)19-12-4-5-14(24-2)20(25-3)17(12)21(23)28-19/h4-5,8-9,18-19H,6-7,10H2,1-3H3/t18-,19-/m1/s1
InChIKey	JZUTXVTYJDCMDU-RTBURBONSA-N
Formula	C₂₁H₂₁NO₆
HBA	7
HBD	0
MW	383.4
Rotatable Bonds	3
TPSA	66.46
LogP	2.87
Number Rings	5
Number Aromatic Rings	2
Heavy Atom Count	28
Formal Charge	0
Fraction CSP3	0.38
Exact Mass	383.14
Number of Lipinski Rule Violations	0

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Fumaria parviflora	Fumariaceae	Plantae	1464625
2	Fumaria parviflora	Papaveraceae	Plantae	1464625

Showing of synonyms

Elsaid M.B, Elnaggar D.M, et al. (2022). Production of isoquinoline alkaloids from the in vitro conserved Fumaria parviflora and their in vitro wound healing activity. Natural product research, 2022, 36(10), 2575-2579. [View] [PubMed]

Pubchem: 442247

Cas: 60594-55-0

Zinc: ZINC000019796064

Kegg Ligand: C09462

Chebi: 126

Nmrshiftdb2: 70128863

Chembl: CHEMBL475536

No compound-protein relationship available.

SMILES: c1cccc(c12)C(OC2=O)C(NCC3)c(c4)c3cc(c45)OCO5

Level: 1

Mol. Weight: 383.4 g/mol

SMILES: O1COc(c12)cc3c(c2)CCNC3

Level: 0

Mol. Weight: 383.4 g/mol

SMILES: O=C1OCc(c12)cccc2

Level: 0

Mol. Weight: 383.4 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -4.95
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.780
Human Oral Bioavailability 50%: Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -2.39

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 0.790
Plasma Protein Binding: 61.01
Steady State Volume of Distribution: -

Metabolism

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

Excretion

Clearance: 13.700
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: 2.290
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.570
Liver Injury II: Toxic
hERG Blockers: Toxic
Daphnia Maga: 10.810
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: -28.430
Rat (Acute): 2.400
Rat (Chronic Oral): 1.160
Fathead Minnow: 4.880
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: 442.860
Hydration Free Energy: -5.500
Log(D) at pH=7.4: 2.400
Log(P): 1.93
Log S: -3.49
Log(Vapor Pressure): -9.39
Melting Point: 164.49
pKa Acid: 9.03
pKa Basic: 6.74

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Pheromone-binding protein ASP1	Q9U9J6	Q9U9J6_APIME	Apis mellifera	3	0.9466
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.9254
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.9205
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.9201
UDP-N-acetylmuramoyl-tripeptide--D-alanyl-D-alanine ligase	Q8DNV6	Q8DNV6_STRR6	Streptococcus pneumoniae	3	0.9117
Phospholipase A2, major isoenzyme	P00592	PA21B_PIG	Sus scrofa	3	0.8920
Protoporphyrinogen oxidase	P50336	PPOX_HUMAN	Homo sapiens	3	0.8762
Abscisic acid receptor PYL1	Q8VZS8	PYL1_ARATH	Arabidopsis thaliana	3	0.8720
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.8635
Nodulin-13	P93330	NOD13_MEDTR	Medicago truncatula	3	0.8620
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	3	0.8569
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.8552
Nuclear receptor subfamily 4immunitygroup A member 1	P22736	NR4A1_HUMAN	Homo sapiens	3	0.8534
11-beta-hydroxysteroid dehydrogenase 1	P28845	DHI1_HUMAN	Homo sapiens	3	0.8399
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8373
Mitogen-activated protein kinase 8	P45983	MK08_HUMAN	Homo sapiens	3	0.8312
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.8297
Protoporphyrinogen oxidase	P50336	PPOX_HUMAN	Homo sapiens	3	0.8279
Cytohesin-2	Q99418	CYH2_HUMAN	Homo sapiens	4	0.8237
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	3	0.8234
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8182
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8181
Serine/threonine-protein kinase pim-1	P11309	PIM1_HUMAN	Homo sapiens	4	0.8151
Thymidylate synthase	P0A886	TYSY_ECO57	Escherichia coli O157:H7	3	0.8148
Proto-oncogene tyrosine-protein kinase Src	P00523	SRC_CHICK	Gallus gallus	3	0.8099
Tyrosine-protein kinase Lck	P06239	LCK_HUMAN	Homo sapiens	4	0.8072
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8018
NAD(P)H dehydrogenase [quinone] 1	P15559	NQO1_HUMAN	Homo sapiens	4	0.8003
Chloramphenicol 3-O phosphotransferase	Q56148	CPT_STRVP	Streptomyces venezuelae	3	0.7982
Pantothenate synthetase	P9WIL5	PANC_MYCTU	Mycobacterium tuberculosis	3	0.7982
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7969
Mitogen-activated protein kinase kinase kinase 5	Q99683	M3K5_HUMAN	Homo sapiens	3	0.7964
Acetolactate synthase catalytic subunit, mitochondrial	P07342	ILVB_YEAST	Saccharomyces cerevisiae	3	0.7956
Abscisic acid receptor PYL2	O80992	PYL2_ARATH	Arabidopsis thaliana	3	0.7911
Mycocyclosin synthase	P9WPP7	CP121_MYCTU	Mycobacterium tuberculosis	3	0.7854
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	3	0.7836
Rhodopsin kinase GRK1	P28327	GRK1_BOVIN	Bos taurus	3	0.7774
Peroxisome proliferator-activated receptor gamma	P37231	PPARG_HUMAN	Homo sapiens	4	0.7773
Mitogen-activated protein kinase 10	P53779	MK10_HUMAN	Homo sapiens	3	0.7728
Transcriptional regulator, PadR-like family	A2RI36	A2RI36_LACLM	Lactococcus lactis subsp. cremoris	2	0.7727
Mitomycin biosynthesis 6-O-methyltransferase	Q9X5T6	MMCR_STRLA	Streptomyces lavendulae	3	0.7695
Capsid protein	Q9WBP8	Q9WBP8_9VIRU	Adeno-associated virus - 1	3	0.7674
histidine kinase	O32393	O32393_ARTPT	Arthrospira platensis	3	0.7590
HLA class I histocompatibility antigen, B alpha chain	P01889	HLAB_HUMAN	Homo sapiens	3	0.7575
Chalcone--flavanone isomerase 1	P28012	CFI1_MEDSA	Medicago sativa	3	0.7572
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7564
Mitogen-activated protein kinase 14	Q16539	MK14_HUMAN	Homo sapiens	3	0.7545
Riboflavin synthase	P0AFU8	RISA_ECOLI	Escherichia coli	3	0.7534
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7526
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	3	0.7508
Genome polyprotein	O92972	POLG_HCVJ4	Hepatitis C virus genotype 1b	3	0.7473
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.7465
4-hydroxyphenylacetate 3-monooxygenase	Q8YHT7	Q8YHT7_BRUME	Brucella melitensis biotype 1	2	0.7448
CmeR	Q7B8P6	Q7B8P6_CAMJU	Campylobacter jejuni	3	0.7444
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7440
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7435
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	2	0.7435
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7430
Succinate dehydrogenase [ubiquinone] iron-sulfur subunit, mitochondrial	Q33862	Q33862_ASCSU	Ascaris suum	3	0.7429
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7418
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.7387
Serine/threonine-protein kinase SKY1	Q03656	SKY1_YEAST	Saccharomyces cerevisiae	3	0.7378
Mitochondrial poly(A) polymerase	F1NBW0	F1NBW0_CHICK	Gallus gallus	2	0.7352
Homoserine dehydrogenase	P31116	DHOM_YEAST	Saccharomyces cerevisiae	3	0.7343
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	3	0.7318
Aurora kinase A	O14965	AURKA_HUMAN	Homo sapiens	3	0.7311
Kynurenine/alpha-aminoadipate aminotransferase, mitochondrial	Q8N5Z0	AADAT_HUMAN	Homo sapiens	2	0.7305
Glucan 1,3-beta-glucosidase	P29717	EXG1_CANAL	Candida albicans	2	0.7267
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	2	0.7257
Serine/threonine-protein kinase 24	Q9Y6E0	STK24_HUMAN	Homo sapiens	3	0.7249
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7231
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.7208
Beta-lactamase	Q9L5C8	Q9L5C8_ECOLX	Escherichia coli	3	0.7208
Focal adhesion kinase 1	Q00944	FAK1_CHICK	Gallus gallus	3	0.7205
Serine/threonine-protein kinase pim-1	P11309	PIM1_HUMAN	Homo sapiens	3	0.7185
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7184
3-phosphoinositide-dependent protein kinase 1	O15530	PDPK1_HUMAN	Homo sapiens	3	0.7173
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.7169
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.7168
Abscisic acid receptor PYR1	O49686	PYR1_ARATH	Arabidopsis thaliana	3	0.7155
Serine/threonine-protein kinase 24	Q9Y6E0	STK24_HUMAN	Homo sapiens	3	0.7148
Metallo-beta-lactamase type 2	P52699	BLAB_SERMA	Serratia marcescens	3	0.7147
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7146
Mycocyclosin synthase	P9WPP7	CP121_MYCTU	Mycobacterium tuberculosis	3	0.7138
Glucose-1-phosphate thymidylyltransferase	Q9HU22	Q9HU22_PSEAE	Pseudomonas aeruginosa	3	0.7136
Neuropilin-1	O14786	NRP1_HUMAN	Homo sapiens	3	0.7112
Tyrosine-protein kinase Lck	P06239	LCK_HUMAN	Homo sapiens	3	0.7107
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7105
Protein ppBat	Q8A8A4	Q8A8A4_BACTN	Bacteroides thetaiotaomicron VPI-5482	3	0.7098
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7096
Pancreatic alpha-amylase	P04746	AMYP_HUMAN	Homo sapiens	2	0.7086
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7084
Beta-galactoside-specific lectin 4	Q6ITZ3	ML4_VISAL	Viscum album	2	0.7076
Uncharacterized protein	Q3F0V8	Q3F0V8_BACTI	Bacillus thuringiensis serovar israelensis ATCC 35646	3	0.7067
Gag-Pol polyprotein	P03367	POL_HV1BR	Human immunodeficiency virus type 1 group M subtype B	3	0.7061
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7038
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7031
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	2	0.7027
Metallo-beta-lactamase type 2	C7C422	BLAN1_KLEPN	Klebsiella pneumoniae	2	0.7025
HTH-type transcriptional regulator EthR	P9WMC1	ETHR_MYCTU	Mycobacterium tuberculosis	3	0.7023
Albumin	P02768	ALBU_HUMAN	Homo sapiens	3	0.7017
Phenylalanine-4-hydroxylase	P00439	PH4H_HUMAN	Homo sapiens	3	0.7007

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