Phtalidiisoquinoline - Compound Card

Phtalidiisoquinoline

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Phtalidiisoquinoline

Structure
Zoomed Structure
  • Family: Fumariaceae
  • Kingdom: Plantae
  • Class: Alkaloid
    • Subclass: Isoquinoline Alkaloid
Canonical Smiles COc1cc2CCN(C(c2cc1OC)C1OC(=O)c2c1cc1OCOc1c2)C
InChI InChI=1S/C21H21NO6/c1-22-5-4-11-6-15(24-2)16(25-3)7-12(11)19(22)20-13-8-17-18(27-10-26-17)9-14(13)21(23)28-20/h6-9,19-20H,4-5,10H2,1-3H3
InChIKey AGPVTPPNIRQNPQ-UHFFFAOYSA-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 capreolata Fumariaceae Plantae 1053349
2 Fumaria bastardii Fumariaceae Plantae 1155334

Showing of synonyms

  • Maiza-Benabdesselam F, Khentache S, et al. (2007). Antioxidant activities of alkaloid extracts of two Algerian species of Fumaria : Fumaria capreolata and Fumaria bastardii. Records of Natural Products,2007,1(2-3),28-35. [View]
Pubchem: 73077655

No compound-protein relationship available.

Structure

SMILES: O1COc(c2)c1cc(c23)C(OC3=O)C4NCCc(c45)cccc5

Level: 1

Mol. Weight: 309.32 g/mol

Structure

SMILES: O=C1OCc(c12)cc3c(c2)OCO3

Level: 0

Mol. Weight: 178.14 g/mol

Structure

SMILES: C1CNCc(c12)cccc2

Level: 0

Mol. Weight: 133.19 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.87
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.780
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.8

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.890
Plasma Protein Binding
26.36
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
Non-Substrate
CYP 3A4 Inhibitor
Inhibitor
CYP 3A4 Substrate
Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
14.160
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
2.420
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.730
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
8.800
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
-24.580
Rat (Acute)
2.210
Rat (Chronic Oral)
1.210
Fathead Minnow
4.950
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
430.510
Hydration Free Energy
-5.140
Log(D) at pH=7.4
3.210
Log(P)
1.78
Log S
-3.43
Log(Vapor Pressure)
-9.15
Melting Point
172.84
pKa Acid
8.28
pKa Basic
5.9
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 0.9150
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 3 0.9150
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.9082
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.9082
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.9080
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.9080
Stromelysin-1 P08254 MMP3_HUMAN Homo sapiens 3 0.8989
Stromelysin-1 P08254 MMP3_HUMAN Homo sapiens 3 0.8989
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 3 0.8960
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 3 0.8960
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8952
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8952
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8906
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8906
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8800
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8800
Activin receptor type-1 Q04771 ACVR1_HUMAN Homo sapiens 3 0.8758
Activin receptor type-1 Q04771 ACVR1_HUMAN Homo sapiens 3 0.8758
Abscisic acid receptor PYL1 Q8VZS8 PYL1_ARATH Arabidopsis thaliana 3 0.8644
Abscisic acid receptor PYL1 Q8VZS8 PYL1_ARATH Arabidopsis thaliana 3 0.8644
Abscisic acid receptor PYL2 O80992 PYL2_ARATH Arabidopsis thaliana 3 0.8557
Abscisic acid receptor PYL2 O80992 PYL2_ARATH Arabidopsis thaliana 3 0.8557
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.8418
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.8418
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8409
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8409
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.8371
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.8371
Pantothenate synthetase P9WIL5 PANC_MYCTU Mycobacterium tuberculosis 3 0.8264
Pantothenate synthetase P9WIL5 PANC_MYCTU Mycobacterium tuberculosis 3 0.8264
Nodulin-13 P93330 NOD13_MEDTR Medicago truncatula 3 0.8246
Nodulin-13 P93330 NOD13_MEDTR Medicago truncatula 3 0.8246
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 3 0.8218
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 3 0.8218
Protein ppBat Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron VPI-5482 3 0.8217
Protein ppBat Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron VPI-5482 3 0.8217
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8212
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8212
Aurora kinase A O14965 AURKA_HUMAN Homo sapiens 3 0.8193
Aurora kinase A O14965 AURKA_HUMAN Homo sapiens 3 0.8193
Diphtheria toxin P00588 DTX_CORBE Corynephage beta 3 0.8159
Diphtheria toxin P00588 DTX_CORBE Corynephage beta 3 0.8159
NADPH dehydrogenase 1 Q02899 OYE1_SACPS Saccharomyces pastorianus 3 0.8157
NADPH dehydrogenase 1 Q02899 OYE1_SACPS Saccharomyces pastorianus 3 0.8157
Glycogen synthase Q9V2J8 Q9V2J8_PYRAB Pyrococcus abyssi 3 0.8152
Glycogen synthase Q9V2J8 Q9V2J8_PYRAB Pyrococcus abyssi 3 0.8152
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8133
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8133
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.8114
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.8114
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 3 0.8082
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 3 0.8082
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.8079
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.8079
L-lactate dehydrogenase A chain P04642 LDHA_RAT Rattus norvegicus 3 0.8034
L-lactate dehydrogenase A chain P04642 LDHA_RAT Rattus norvegicus 3 0.8034
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.7940
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.7940
Mitomycin biosynthesis 6-O-methyltransferase Q9X5T6 MMCR_STRLA Streptomyces lavendulae 3 0.7933
Mitomycin biosynthesis 6-O-methyltransferase Q9X5T6 MMCR_STRLA Streptomyces lavendulae 3 0.7933
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7903
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7903
Glycogen synthase Q9V2J8 Q9V2J8_PYRAB Pyrococcus abyssi 3 0.7875
Glycogen synthase Q9V2J8 Q9V2J8_PYRAB Pyrococcus abyssi 3 0.7875
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7866
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7866
Activin receptor type-1 Q04771 ACVR1_HUMAN Homo sapiens 4 0.7832
Activin receptor type-1 Q04771 ACVR1_HUMAN Homo sapiens 4 0.7832
Nucleoprotein P33469 NCAP_CVHOC Human coronavirus OC43 4 0.7813
Nucleoprotein P33469 NCAP_CVHOC Human coronavirus OC43 4 0.7813
Transcriptional regulator, PadR-like family A2RI36 A2RI36_LACLM Lactococcus lactis subsp. cremoris 2 0.7797
Transcriptional regulator, PadR-like family A2RI36 A2RI36_LACLM Lactococcus lactis subsp. cremoris 2 0.7797
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7788
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7788
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7760
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7760
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 3 0.7674
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 3 0.7674
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 4 0.7648
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 4 0.7648
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7631
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7631
Protein mono-ADP-ribosyltransferase PARP3 Q9Y6F1 PARP3_HUMAN Homo sapiens 4 0.7604
Protein mono-ADP-ribosyltransferase PARP3 Q9Y6F1 PARP3_HUMAN Homo sapiens 4 0.7604
Proto-oncogene tyrosine-protein kinase Src P00523 SRC_CHICK Gallus gallus 3 0.7597
Proto-oncogene tyrosine-protein kinase Src P00523 SRC_CHICK Gallus gallus 3 0.7597
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 3 0.7560
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 3 0.7560
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.7541
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.7541
Serine/threonine-protein kinase 10 O94804 STK10_HUMAN Homo sapiens 3 0.7527
Serine/threonine-protein kinase 10 O94804 STK10_HUMAN Homo sapiens 3 0.7527
Poly [ADP-ribose] polymerase 1 P09874 PARP1_HUMAN Homo sapiens 3 0.7499
Poly [ADP-ribose] polymerase 1 P09874 PARP1_HUMAN Homo sapiens 3 0.7499
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.7456
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.7456
Flavoredoxin Q72HI0 Q72HI0_THET2 Thermus thermophilus 3 0.7441
Flavoredoxin Q72HI0 Q72HI0_THET2 Thermus thermophilus 3 0.7441
UDP-galactopyranose mutase Q48485 GLF1_KLEPN Klebsiella pneumoniae 3 0.7426
UDP-galactopyranose mutase Q48485 GLF1_KLEPN Klebsiella pneumoniae 3 0.7426
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 3 0.7423
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 3 0.7423
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7410
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7410
Exotoxin A P11439 TOXA_PSEAE Pseudomonas aeruginosa 4 0.7385
Exotoxin A P11439 TOXA_PSEAE Pseudomonas aeruginosa 4 0.7385
Catechol O-methyltransferase P22734 COMT_RAT Rattus norvegicus 3 0.7374
Catechol O-methyltransferase P22734 COMT_RAT Rattus norvegicus 3 0.7374
Proto-oncogene tyrosine-protein kinase Src P00523 SRC_CHICK Gallus gallus 3 0.7341
Proto-oncogene tyrosine-protein kinase Src P00523 SRC_CHICK Gallus gallus 3 0.7341
UDP-N-acetylmuramoyl-tripeptide--D-alanyl-D-alanine ligase Q8DNV6 Q8DNV6_STRR6 Streptococcus pneumoniae 3 0.7323
UDP-N-acetylmuramoyl-tripeptide--D-alanyl-D-alanine ligase Q8DNV6 Q8DNV6_STRR6 Streptococcus pneumoniae 3 0.7323
Thymidylate synthase P0A886 TYSY_ECO57 Escherichia coli O157:H7 3 0.7307
Thymidylate synthase P0A886 TYSY_ECO57 Escherichia coli O157:H7 3 0.7307
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7298
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7298
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7289
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7289
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7274
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7274
Vitamin D3 dihydroxylase P18326 CPXE_STRGO Streptomyces griseolus 3 0.7264
Vitamin D3 dihydroxylase P18326 CPXE_STRGO Streptomyces griseolus 3 0.7264
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7259
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7259
3-ketosteroid dehydrogenase Q9RA02 Q9RA02_RHOER Rhodococcus erythropolis 3 0.7248
3-ketosteroid dehydrogenase Q9RA02 Q9RA02_RHOER Rhodococcus erythropolis 3 0.7248
Lactoperoxidase P80025 PERL_BOVIN Bos taurus 3 0.7242
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7242
Lactoperoxidase P80025 PERL_BOVIN Bos taurus 3 0.7242
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7242
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 4 0.7220
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 4 0.7220
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7211
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7211
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7203
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7203
4-hydroxyphenylacetate 3-monooxygenase Q8YHT7 Q8YHT7_BRUME Brucella melitensis biotype 1 2 0.7202
4-hydroxyphenylacetate 3-monooxygenase Q8YHT7 Q8YHT7_BRUME Brucella melitensis biotype 1 2 0.7202
NAD(P)H dehydrogenase [quinone] 1 P15559 NQO1_HUMAN Homo sapiens 3 0.7171
NAD(P)H dehydrogenase [quinone] 1 P15559 NQO1_HUMAN Homo sapiens 3 0.7171
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7163
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7163
Glucose-1-phosphate thymidylyltransferase Q9HU22 Q9HU22_PSEAE Pseudomonas aeruginosa 3 0.7152
Glucose-1-phosphate thymidylyltransferase Q9HU22 Q9HU22_PSEAE Pseudomonas aeruginosa 3 0.7152
Na(+):neurotransmitter symporter (Snf family) O67854 O67854_AQUAE Aquifex aeolicus 3 0.7152
Na(+):neurotransmitter symporter (Snf family) O67854 O67854_AQUAE Aquifex aeolicus 3 0.7152
[Pyruvate dehydrogenase (acetyl-transferring)] kinase isozyme 2, mitochondrial Q15119 PDK2_HUMAN Homo sapiens 2 0.7097
[Pyruvate dehydrogenase (acetyl-transferring)] kinase isozyme 2, mitochondrial Q15119 PDK2_HUMAN Homo sapiens 2 0.7097
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.7091
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.7091
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7085
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7085
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 2 0.7053
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 2 0.7053
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.7053
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.7053
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7051
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7051
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7029
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7029
Chalcone--flavanone isomerase 1 P28012 CFI1_MEDSA Medicago sativa 3 0.7022
Chalcone--flavanone isomerase 1 P28012 CFI1_MEDSA Medicago sativa 3 0.7022
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7018
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7018
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7014
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7014
Bromodomain adjacent to zinc finger domain protein 2B Q9UIF8 BAZ2B_HUMAN Homo sapiens 3 0.7005
Bromodomain adjacent to zinc finger domain protein 2B Q9UIF8 BAZ2B_HUMAN Homo sapiens 3 0.7005

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