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Fumaritine
- Family: Plantae - Fumariaceae
- Kingdom: Plantae
-
Class: Alkaloid
- Subclass: Isoquinoline Alkaloid
| Canonical Smiles | COc1cc2CCN(C3(c2cc1O)Cc1c(C3O)c2OCOc2cc1)C |
|---|---|
| InChI | InChI=1S/C20H21NO5/c1-21-6-5-11-7-16(24-2)14(22)8-13(11)20(21)9-12-3-4-15-18(26-10-25-15)17(12)19(20)23/h3-4,7-8,19,22-23H,5-6,9-10H2,1-2H3 |
| InChIKey | YUIGSRGRYOBFRF-UHFFFAOYSA-N |
| Formula | C20H21NO5 |
| HBA | 6 |
| HBD | 2 |
| MW | 355.39 |
| Rotatable Bonds | 1 |
| TPSA | 71.39 |
| LogP | 2.1 |
| Number Rings | 5 |
| Number Aromatic Rings | 2 |
| Heavy Atom Count | 26 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.4 |
| Exact Mass | 355.14 |
| 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
Fumaritine
24181-78-0
NSC634619
Fumaritine, (+)-
[7S,(-)]-3',4',6,8-Tetrahydro-6'-methoxy-2'-methylspiro[7H-indeno[4,5-d]-1,3-dioxole-7,1'(2'H)-isoquinoline]-7',8alpha-diol
Fumarophycinol
Fumaritin
Dihydroparfumine
Spiro[7H-indeno[4,5-d]-1,3-dioxole-7,1'(2'H)-isoquinoline]-7',8-diol, 3',4',6,8-tetrahydro-6'-methoxy-2'-methyl-, (7S-trans)-
O-Deacetylfumarophycine
YUIGSRGRYOBFRF-UHFFFAOYSA-N
AKOS040735235
6-methoxy-2-methylspiro[3,4-dihydroisoquinoline-1,7'-6,8-dihydrocyclopenta[g][1,3]benzodioxole]-7,8'-diol
Spiro[7H-indeno[4,5-d]-1,3-dioxole-7,1'(2'H)-isoquinoline]-7',8-diol, 3',4',6,8-tetrahydro-6'-methoxy-2'-methyl-
6-methoxy-2-methyl-spiro[3,4-dihydroisoquinoline-1,7'-6,8-dihydrocyclopenta[g][1,3]benzodioxole]-7,8'-diol
Spiro[7H-indeno[4,5-d]-1,3-dioxole-7,1'(2'H)-isoquinoline]-7',8-diol, 3',4',6,8-tetrahydro-6'-methoxy-2'-methyl-, trans-
- 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]
No compound-protein relationship available.
SMILES: C1c2ccc(OCO3)c3c2CC14c5c(CCN4)cccc5
Level: 0
Mol. Weight: 355.39 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -4.98
- Human Oral Bioavailability 20%
- Non-Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.750
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -1.29
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 0.770
- Plasma Protein Binding
- 26.25
- 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
- Substrate
- CYP 2D6 Inhibitor
- Inhibitor
- CYP 2D6 Substrate
- Substrate
- CYP 3A4 Inhibitor
- Inhibitor
- CYP 3A4 Substrate
- Substrate
- OATP1B1
- Non-Inhibitor
- OATP1B3
- Non-Inhibitor
Excretion
- Clearance
- 13.460
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- 2.270
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Toxic
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 0.670
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 9.800
- 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
- -8.120
- Rat (Acute)
- 2.330
- Rat (Chronic Oral)
- 1.610
- Fathead Minnow
- 4.420
- 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
- 427.680
- Hydration Free Energy
- -8.960
- Log(D) at pH=7.4
- 2.410
- Log(P)
- 1.82
- Log S
- -2.66
- Log(Vapor Pressure)
- -8.75
- Melting Point
- 204.98
- pKa Acid
- 9.31
- pKa Basic
- 6.58
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Chitinase A | Q9AMP1 | Q9AMP1_VIBHA | Vibrio harveyi | 3 | 0.9300 |
| Chitinase A | Q9AMP1 | Q9AMP1_VIBHA | Vibrio harveyi | 3 | 0.9300 |
| ATP-dependent molecular chaperone HSP82 | P02829 | HSP82_YEAST | Saccharomyces cerevisiae | 3 | 0.9197 |
| ATP-dependent molecular chaperone HSP82 | P02829 | HSP82_YEAST | Saccharomyces cerevisiae | 3 | 0.9197 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 3 | 0.9071 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 3 | 0.9071 |
| Thymidine phosphorylase | Q7CP66 | TYPH_SALTY | Salmonella typhimurium | 3 | 0.9018 |
| Thymidine phosphorylase | Q7CP66 | TYPH_SALTY | Salmonella typhimurium | 3 | 0.9018 |
| Lactotransferrin | P24627 | TRFL_BOVIN | Bos taurus | 3 | 0.8948 |
| Lactotransferrin | P24627 | TRFL_BOVIN | Bos taurus | 3 | 0.8948 |
| rRNA N-glycosylase | D9J2T9 | D9J2T9_MOMBA | Momordica balsamina | 3 | 0.8643 |
| rRNA N-glycosylase | D9J2T9 | D9J2T9_MOMBA | Momordica balsamina | 3 | 0.8643 |
| Tyrosine-protein kinase JAK2 | O60674 | JAK2_HUMAN | Homo sapiens | 3 | 0.8469 |
| Tyrosine-protein kinase JAK2 | O60674 | JAK2_HUMAN | Homo sapiens | 3 | 0.8469 |
| Tetracycline repressor protein class H | P51561 | TETR8_PASMD | Pasteurella multocida | 3 | 0.8468 |
| Tetracycline repressor protein class H | P51561 | TETR8_PASMD | Pasteurella multocida | 3 | 0.8468 |
| cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A | Q9Y233 | PDE10_HUMAN | Homo sapiens | 3 | 0.8457 |
| cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A | Q9Y233 | PDE10_HUMAN | Homo sapiens | 3 | 0.8457 |
| Pyridoxal kinase | P82197 | PDXK_SHEEP | Ovis aries | 3 | 0.8296 |
| Pyridoxal kinase | P82197 | PDXK_SHEEP | Ovis aries | 3 | 0.8296 |
| Sulfide-quinone reductase | B7JBP8 | SQRD_ACIF2 | Acidithiobacillus ferrooxidans) | 3 | 0.8158 |
| Sulfide-quinone reductase | B7JBP8 | SQRD_ACIF2 | Acidithiobacillus ferrooxidans) | 3 | 0.8158 |
| Uracil phosphoribosyltransferase | Q26998 | UPP_TOXGO | Toxoplasma gondii | 3 | 0.8100 |
| Uracil phosphoribosyltransferase | Q26998 | UPP_TOXGO | Toxoplasma gondii | 3 | 0.8100 |
| UDP-N-acetylmuramoyl-tripeptide--D-alanyl-D-alanine ligase | Q8DNV6 | Q8DNV6_STRR6 | Streptococcus pneumoniae | 3 | 0.7987 |
| UDP-N-acetylmuramoyl-tripeptide--D-alanyl-D-alanine ligase | Q8DNV6 | Q8DNV6_STRR6 | Streptococcus pneumoniae | 3 | 0.7987 |
| Homoserine dehydrogenase | P31116 | DHOM_YEAST | Saccharomyces cerevisiae | 3 | 0.7968 |
| Homoserine dehydrogenase | P31116 | DHOM_YEAST | Saccharomyces cerevisiae | 3 | 0.7968 |
| Calmodulin-domain protein kinase 1, putative | A3FQ16 | A3FQ16_CRYPI | Cryptosporidium parvum | 3 | 0.7916 |
| Calmodulin-domain protein kinase 1, putative | A3FQ16 | A3FQ16_CRYPI | Cryptosporidium parvum | 3 | 0.7916 |
| Purine nucleoside phosphorylase DeoD-type | O34925 | DEOD_BACSU | Bacillus subtilis | 3 | 0.7816 |
| Purine nucleoside phosphorylase DeoD-type | O34925 | DEOD_BACSU | Bacillus subtilis | 3 | 0.7816 |
| Rhodopsin kinase GRK1 | P28327 | GRK1_BOVIN | Bos taurus | 3 | 0.7751 |
| Rhodopsin kinase GRK1 | P28327 | GRK1_BOVIN | Bos taurus | 3 | 0.7751 |
| Glucose-1-phosphate thymidylyltransferase | Q9HU22 | Q9HU22_PSEAE | Pseudomonas aeruginosa | 4 | 0.7666 |
| Glucose-1-phosphate thymidylyltransferase | Q9HU22 | Q9HU22_PSEAE | Pseudomonas aeruginosa | 4 | 0.7666 |
| Abscisic acid receptor PYL2 | O80992 | PYL2_ARATH | Arabidopsis thaliana | 3 | 0.7611 |
| Abscisic acid receptor PYL2 | O80992 | PYL2_ARATH | Arabidopsis thaliana | 3 | 0.7611 |
| Putative S-adenosyl-L-methionine-dependent methyltransferase ML2640 | Q9CCZ4 | Y2640_MYCLE | Mycobacterium leprae | 3 | 0.7595 |
| Putative S-adenosyl-L-methionine-dependent methyltransferase ML2640 | Q9CCZ4 | Y2640_MYCLE | Mycobacterium leprae | 3 | 0.7595 |
| Cytosolic purine 5'-nucleotidase | P49902 | 5NTC_HUMAN | Homo sapiens | 2 | 0.7581 |
| Cytosolic purine 5'-nucleotidase | P49902 | 5NTC_HUMAN | Homo sapiens | 2 | 0.7581 |
| Gag-Pol polyprotein | P03367 | POL_HV1BR | Human immunodeficiency virus type 1 group M subtype B | 3 | 0.7566 |
| Gag-Pol polyprotein | P03367 | POL_HV1BR | Human immunodeficiency virus type 1 group M subtype B | 3 | 0.7566 |
| Catechol O-methyltransferase | P22734 | COMT_RAT | Rattus norvegicus | 3 | 0.7534 |
| Catechol O-methyltransferase | P22734 | COMT_RAT | Rattus norvegicus | 3 | 0.7534 |
| Protein mono-ADP-ribosyltransferase PARP3 | Q9Y6F1 | PARP3_HUMAN | Homo sapiens | 3 | 0.7527 |
| Protein mono-ADP-ribosyltransferase PARP3 | Q9Y6F1 | PARP3_HUMAN | Homo sapiens | 3 | 0.7527 |
| NAD(P)H-hydrate epimerase | Q8K4Z3 | NNRE_MOUSE | Mus musculus | 3 | 0.7499 |
| NAD(P)H-hydrate epimerase | Q8K4Z3 | NNRE_MOUSE | Mus musculus | 3 | 0.7499 |
| Heat shock protein HSP 90-alpha | P07900 | HS90A_HUMAN | Homo sapiens | 3 | 0.7472 |
| Heat shock protein HSP 90-alpha | P07900 | HS90A_HUMAN | Homo sapiens | 3 | 0.7472 |
| Thymidylate synthase | P0A886 | TYSY_ECO57 | Escherichia coli O157:H7 | 3 | 0.7428 |
| Thymidylate synthase | P0A886 | TYSY_ECO57 | Escherichia coli O157:H7 | 3 | 0.7428 |
| Lactoperoxidase | P80025 | PERL_BOVIN | Bos taurus | 3 | 0.7420 |
| Lactoperoxidase | P80025 | PERL_BOVIN | Bos taurus | 3 | 0.7420 |
| Mitochondrial poly(A) polymerase | F1NBW0 | F1NBW0_CHICK | Gallus gallus | 2 | 0.7404 |
| Mitochondrial poly(A) polymerase | F1NBW0 | F1NBW0_CHICK | Gallus gallus | 2 | 0.7404 |
| Basic phospholipase A2 VRV-PL-VIIIa | P59071 | PA2B8_DABRR | Daboia russelii | 2 | 0.7371 |
| Basic phospholipase A2 VRV-PL-VIIIa | P59071 | PA2B8_DABRR | Daboia russelii | 2 | 0.7371 |
| Heat shock protein HSP 90-alpha | P07900 | HS90A_HUMAN | Homo sapiens | 3 | 0.7367 |
| Heat shock protein HSP 90-alpha | P07900 | HS90A_HUMAN | Homo sapiens | 3 | 0.7367 |
| Pancreatic alpha-amylase | P04746 | AMYP_HUMAN | Homo sapiens | 2 | 0.7348 |
| Pancreatic alpha-amylase | P04746 | AMYP_HUMAN | Homo sapiens | 2 | 0.7348 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 3 | 0.7340 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 3 | 0.7340 |
| Gag-Pol polyprotein | P04584 | POL_HV2RO | Human immunodeficiency virus type 2 subtype A | 3 | 0.7328 |
| Gag-Pol polyprotein | P04584 | POL_HV2RO | Human immunodeficiency virus type 2 subtype A | 3 | 0.7328 |
| Soluble acetylcholine receptor | Q8WSF8 | Q8WSF8_APLCA | Aplysia californica | 3 | 0.7307 |
| Soluble acetylcholine receptor | Q8WSF8 | Q8WSF8_APLCA | Aplysia californica | 3 | 0.7307 |
| Soluble acetylcholine receptor | Q8WSF8 | Q8WSF8_APLCA | Aplysia californica | 2 | 0.7277 |
| Soluble acetylcholine receptor | Q8WSF8 | Q8WSF8_APLCA | Aplysia californica | 2 | 0.7277 |
| NADPH dehydrogenase 1 | Q02899 | OYE1_SACPS | Saccharomyces pastorianus | 3 | 0.7259 |
| NADPH dehydrogenase 1 | Q02899 | OYE1_SACPS | Saccharomyces pastorianus | 3 | 0.7259 |
| 4-hydroxyphenylacetate 3-monooxygenase | Q8YHT7 | Q8YHT7_BRUME | Brucella melitensis biotype 1 | 2 | 0.7217 |
| 4-hydroxyphenylacetate 3-monooxygenase | Q8YHT7 | Q8YHT7_BRUME | Brucella melitensis biotype 1 | 2 | 0.7217 |
| Pheromone-binding protein ASP1 | Q9U9J6 | Q9U9J6_APIME | Apis mellifera | 3 | 0.7208 |
| Pheromone-binding protein ASP1 | Q9U9J6 | Q9U9J6_APIME | Apis mellifera | 3 | 0.7208 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 3 | 0.7163 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 3 | 0.7163 |
| Abscisic acid receptor PYR1 | O49686 | PYR1_ARATH | Arabidopsis thaliana | 3 | 0.7161 |
| Abscisic acid receptor PYR1 | O49686 | PYR1_ARATH | Arabidopsis thaliana | 3 | 0.7161 |
| Ribonuclease J | H9CZL7 | H9CZL7_DEIRD | Deinococcus radiodurans | 3 | 0.7145 |
| Ribonuclease J | H9CZL7 | H9CZL7_DEIRD | Deinococcus radiodurans | 3 | 0.7145 |
| Heat shock protein HSP 90-alpha | P07900 | HS90A_HUMAN | Homo sapiens | 3 | 0.7132 |
| Heat shock protein HSP 90-alpha | P07900 | HS90A_HUMAN | Homo sapiens | 3 | 0.7132 |
| Flavoredoxin | Q72HI0 | Q72HI0_THET2 | Thermus thermophilus | 3 | 0.7116 |
| Flavoredoxin | Q72HI0 | Q72HI0_THET2 | Thermus thermophilus | 3 | 0.7116 |
| Mitomycin biosynthesis 6-O-methyltransferase | Q9X5T6 | MMCR_STRLA | Streptomyces lavendulae | 3 | 0.7103 |
| Mitomycin biosynthesis 6-O-methyltransferase | Q9X5T6 | MMCR_STRLA | Streptomyces lavendulae | 3 | 0.7103 |
| Protoporphyrinogen oxidase | P50336 | PPOX_HUMAN | Homo sapiens | 3 | 0.7087 |
| Protoporphyrinogen oxidase | P50336 | PPOX_HUMAN | Homo sapiens | 3 | 0.7087 |
| Putative cytochrome P450 | Q70AS3 | Q70AS3_STRPE | Streptomyces peucetius | 3 | 0.7085 |
| Putative cytochrome P450 | Q70AS3 | Q70AS3_STRPE | Streptomyces peucetius | 3 | 0.7085 |
| Beta-lactamase | P00811 | AMPC_ECOLI | Escherichia coli | 3 | 0.7082 |
| Beta-lactamase | P00811 | AMPC_ECOLI | Escherichia coli | 3 | 0.7082 |
| cGMP-dependent 3',5'-cyclic phosphodiesterase | O00408 | PDE2A_HUMAN | Homo sapiens | 3 | 0.7064 |
| cGMP-dependent 3',5'-cyclic phosphodiesterase | O00408 | PDE2A_HUMAN | Homo sapiens | 3 | 0.7064 |
| Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic | Q43088 | RBCMT_PEA | Pisum sativum | 3 | 0.7052 |
| Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic | Q43088 | RBCMT_PEA | Pisum sativum | 3 | 0.7052 |
| Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic | Q43088 | RBCMT_PEA | Pisum sativum | 3 | 0.7028 |
| Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic | Q43088 | RBCMT_PEA | Pisum sativum | 3 | 0.7028 |
| Glucan 1,3-beta-glucosidase | P29717 | EXG1_CANAL | Candida albicans | 2 | 0.7024 |
| Glucan 1,3-beta-glucosidase | P29717 | EXG1_CANAL | Candida albicans | 2 | 0.7024 |
| dTDP-4-dehydrorhamnose 3,5-epimerase | A0A6L7H6N0 | A0A1S0QLH9_BACAN | Bacillus anthracis | 3 | 0.7003 |
| dTDP-4-dehydrorhamnose 3,5-epimerase | A0A6L7H6N0 | A0A1S0QLH9_BACAN | Bacillus anthracis | 3 | 0.7003 |
| Dihydrofolate reductase | P00374 | DYR_HUMAN | Homo sapiens | 3 | 0.7002 |
| Dihydrofolate reductase | P00374 | DYR_HUMAN | Homo sapiens | 3 | 0.7002 |