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Fumariline
- Family: Plantae - Fumariaceae
- Kingdom: Plantae
-
Class: Alkaloid
- Subclass: Isoquinoline Alkaloid
| Canonical Smiles | CN1CCc2c([C@@]31Cc1c(C3=O)c3OCOc3cc1)cc1c(c2)OCO1 |
|---|---|
| InChI | InChI=1S/C20H17NO5/c1-21-5-4-11-6-15-16(25-9-24-15)7-13(11)20(21)8-12-2-3-14-18(26-10-23-14)17(12)19(20)22/h2-3,6-7H,4-5,8-10H2,1H3/t20-/m0/s1 |
| InChIKey | GGQGUBWFVKJOER-FQEVSTJZSA-N |
| Formula | C20H17NO5 |
| HBA | 6 |
| HBD | 0 |
| MW | 351.36 |
| Rotatable Bonds | 0 |
| TPSA | 57.23 |
| LogP | 2.27 |
| Number Rings | 6 |
| Number Aromatic Rings | 2 |
| Heavy Atom Count | 26 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.35 |
| Exact Mass | 351.11 |
| 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
Fumariline
Fumarilin
20411-03-4
(+)-Fumariline
BRN 1093115
(7S)-6'-methylspiro[6H-cyclopenta[g][1,3]benzodioxole-7,5'-7,8-dihydro-[1,3]dioxolo[4,5-g]isoquinoline]-8-one
Spiro(1,3-dioxolo(4,5-g)isoquinoline-5(6H),7'-(7H)indeno(4,5-d)(1-3)dioxol)-8'(6'H)-one, 7,8-dihydro-6-methyl-, (S)-
Spiro[1,3-dioxolo[4,5-g]isoquinoline-5(6H),7'-[7H]indeno[4,5-d][1,3]dioxol]-8'(6'H)-one, 7,8-dihydro-6-methyl-, (S)-
Spiro(1,3-dioxolo(4,5-g)isoquinoline-5(6H),7'-(7H)indeno(4,5-d)(1-3)dioxol)-8'(6'H)-one,7,8-dihydro-6-methyl-, (S)-
Spiro[1,3-dioxolo[4,5-g]isoquinoline-5(6H),7'-[7H]indeno[4,5-d][1,3]dioxol]-8'(6'H)-one, 7,8-dihydro-6-methyl-, (+)-
(7S)-6'-methylspiro(6H-cyclopenta(g)(1,3)benzodioxole-7,5'-7,8-dihydro-(1,3)dioxolo(4,5-g)isoquinoline)-8-one
Spiro(1,3-dioxolo(4,5-g)isoquinoline-5(6H),7'-(7H)indeno(4,5-d)(1,3)dioxol)-8'(6'H)-one, 7,8-dihydro-6-methyl-, (+)-
Spiro(1,3-dioxolo(4,5-g)isoquinoline-5(6H),7'-(7H)indeno(4,5-d)(1,3)dioxol)-8'(6'H)-one, 7,8-dihydro-6-methyl-, (S)-
Ggqgubwfvkjoer-fqevstjzsa-n
DTXSID90942581
NS00094112
6-Methyl-7,8-dihydro-2H,2'H,6H-spiro[1,3-dioxolo[4,5-g]isoquinoline-5,7'-indeno[4,5-d][1,3]dioxol]-8'(6'H)-one
- 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)c3c2C(=O)C14c5c(CCN4)cc6c(c5)OCO6
Level: 0
Mol. Weight: 351.36 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -4.97
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.71
- Human Oral Bioavailability 50%
- Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -2.27
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 1.21
- Plasma Protein Binding
- 69.27
- Steady State Volume of Distribution
- -
Metabolism
- Breast Cancer Resistance Protein
- Non-Inhibitor
- CYP 1A2 Inhibitor
- Inhibitor
- CYP 1A2 Substrate
- Substrate
- CYP 2C19 Inhibitor
- Inhibitor
- CYP 2C19 Substrate
- Substrate
- CYP 2C9 Inhibitor
- Inhibitor
- CYP 2C9 Substrate
- Non-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
- 18.11
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Toxic
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- 1.61
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Toxic
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 0.61
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 5.95
- 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
- Safe
- T. Pyriformis
- -10.25
- Rat (Acute)
- 2.25
- Rat (Chronic Oral)
- 0.86
- Fathead Minnow
- 4.47
- Respiratory Disease
- Safe
- Skin Sensitisation
- Toxic
- SR-ARE
- Toxic
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Safe
- SR-p53
- Safe
General Properties
- Boiling Point
- 445.91
- Hydration Free Energy
- -5.32
- Log(D) at pH=7.4
- 2.6
- Log(P)
- 3.08
- Log S
- -4.24
- Log(Vapor Pressure)
- -10.83
- Melting Point
- 209.71
- pKa Acid
- 8.64
- pKa Basic
- 5.47
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 3 | 0.9441 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 3 | 0.9441 |
| Chitinase A | Q9AMP1 | Q9AMP1_VIBHA | Vibrio harveyi | 3 | 0.9225 |
| Chitinase A | Q9AMP1 | Q9AMP1_VIBHA | Vibrio harveyi | 3 | 0.9225 |
| Thymidylate synthase | P00469 | TYSY_LACCA | Lacticaseibacillus casei | 3 | 0.8743 |
| Thymidylate synthase | P00469 | TYSY_LACCA | Lacticaseibacillus casei | 3 | 0.8743 |
| NAD-capped RNA hydrolase NudC | P32664 | NUDC_ECOLI | Escherichia coli | 3 | 0.8508 |
| NAD-capped RNA hydrolase NudC | P32664 | NUDC_ECOLI | Escherichia coli | 3 | 0.8508 |
| Serine/threonine-protein kinase 10 | O94804 | STK10_HUMAN | Homo sapiens | 3 | 0.8366 |
| Serine/threonine-protein kinase 10 | O94804 | STK10_HUMAN | Homo sapiens | 3 | 0.8366 |
| Tetracycline repressor protein class H | P51561 | TETR8_PASMD | Pasteurella multocida | 3 | 0.8356 |
| Tetracycline repressor protein class H | P51561 | TETR8_PASMD | Pasteurella multocida | 3 | 0.8356 |
| Serine/threonine-protein kinase 24 | Q9Y6E0 | STK24_HUMAN | Homo sapiens | 3 | 0.8269 |
| Serine/threonine-protein kinase 24 | Q9Y6E0 | STK24_HUMAN | Homo sapiens | 3 | 0.8269 |
| Transthyretin | Q9PTT3 | Q9PTT3_SPAAU | Sparus aurata | 3 | 0.7985 |
| Transthyretin | Q9PTT3 | Q9PTT3_SPAAU | Sparus aurata | 3 | 0.7985 |
| Albumin | P02768 | ALBU_HUMAN | Homo sapiens | 3 | 0.7951 |
| Albumin | P02768 | ALBU_HUMAN | Homo sapiens | 3 | 0.7951 |
| Gag-Pol polyprotein | P03367 | POL_HV1BR | Human immunodeficiency virus type 1 group M subtype B | 3 | 0.7621 |
| Gag-Pol polyprotein | P03367 | POL_HV1BR | Human immunodeficiency virus type 1 group M subtype B | 3 | 0.7621 |
| Hepatocyte growth factor receptor | P08581 | MET_HUMAN | Homo sapiens | 4 | 0.7527 |
| Hepatocyte growth factor receptor | P08581 | MET_HUMAN | Homo sapiens | 4 | 0.7527 |
| cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A | Q9Y233 | PDE10_HUMAN | Homo sapiens | 3 | 0.7401 |
| cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A | Q9Y233 | PDE10_HUMAN | Homo sapiens | 3 | 0.7401 |
| Soluble acetylcholine receptor | Q8WSF8 | Q8WSF8_APLCA | Aplysia californica | 3 | 0.7385 |
| Soluble acetylcholine receptor | Q8WSF8 | Q8WSF8_APLCA | Aplysia californica | 3 | 0.7385 |
| Lanosterol 14-alpha demethylase | A6ZSR0 | A6ZSR0_YEAS7 | Saccharomyces cerevisiae | 3 | 0.7361 |
| Lanosterol 14-alpha demethylase | A6ZSR0 | A6ZSR0_YEAS7 | Saccharomyces cerevisiae | 3 | 0.7361 |
| Vascular endothelial growth factor receptor 2 | P35968 | VGFR2_HUMAN | Homo sapiens | 3 | 0.7314 |
| Vascular endothelial growth factor receptor 2 | P35968 | VGFR2_HUMAN | Homo sapiens | 3 | 0.7314 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 3 | 0.7310 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 3 | 0.7310 |
| cGMP-dependent 3',5'-cyclic phosphodiesterase | O00408 | PDE2A_HUMAN | Homo sapiens | 3 | 0.7302 |
| cGMP-dependent 3',5'-cyclic phosphodiesterase | O00408 | PDE2A_HUMAN | Homo sapiens | 3 | 0.7302 |
| Gag-Pol polyprotein | P03366 | POL_HV1B1 | Human immunodeficiency virus type 1 group M subtype B | 3 | 0.7191 |
| Gag-Pol polyprotein | P03366 | POL_HV1B1 | Human immunodeficiency virus type 1 group M subtype B | 3 | 0.7191 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 3 | 0.7190 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 3 | 0.7190 |
| Mitochondrial poly(A) polymerase | F1NBW0 | F1NBW0_CHICK | Gallus gallus | 2 | 0.7183 |
| Mitochondrial poly(A) polymerase | F1NBW0 | F1NBW0_CHICK | Gallus gallus | 2 | 0.7183 |
| Catechol O-methyltransferase | P22734 | COMT_RAT | Rattus norvegicus | 3 | 0.7167 |
| Catechol O-methyltransferase | P22734 | COMT_RAT | Rattus norvegicus | 3 | 0.7167 |
| Cytosolic purine 5'-nucleotidase | P49902 | 5NTC_HUMAN | Homo sapiens | 2 | 0.7094 |
| Cytosolic purine 5'-nucleotidase | P49902 | 5NTC_HUMAN | Homo sapiens | 2 | 0.7094 |
| Heat shock protein HSP 90-alpha | P07900 | HS90A_HUMAN | Homo sapiens | 3 | 0.7056 |
| Heat shock protein HSP 90-alpha | P07900 | HS90A_HUMAN | Homo sapiens | 3 | 0.7056 |
| Secoisolariciresinol dehydrogenase | Q94KL8 | SILD_PODPE | Podophyllum peltatum | 3 | 0.7038 |
| Secoisolariciresinol dehydrogenase | Q94KL8 | SILD_PODPE | Podophyllum peltatum | 3 | 0.7038 |
| Epidermal growth factor receptor | P00533 | EGFR_HUMAN | Homo sapiens | 3 | 0.7014 |
| Epidermal growth factor receptor | P00533 | EGFR_HUMAN | Homo sapiens | 3 | 0.7014 |
| Abscisic acid receptor PYL2 | O80992 | PYL2_ARATH | Arabidopsis thaliana | 3 | 0.7010 |
| Abscisic acid receptor PYL2 | O80992 | PYL2_ARATH | Arabidopsis thaliana | 3 | 0.7010 |