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Shinpterocarpin
- Family: Plantae - Leguminosae/Fabaceae
- Kingdom: Plantae
-
Class: Flavonoid
- Subclass: Pterocarpan
| Canonical Smiles | Oc1ccc2c(c1)O[C@@H]1[C@H]2COc2c1ccc1c2C=CC(O1)(C)C |
|---|---|
| InChI | InChI=1S/C20H18O4/c1-20(2)8-7-13-16(24-20)6-5-14-18(13)22-10-15-12-4-3-11(21)9-17(12)23-19(14)15/h3-9,15,19,21H,10H2,1-2H3/t15-,19-/m0/s1 |
| InChIKey | QGPHRCQDTPCIQI-KXBFYZLASA-N |
| Formula | C20H18O4 |
| HBA | 4 |
| HBD | 1 |
| MW | 322.36 |
| Rotatable Bonds | 0 |
| TPSA | 47.92 |
| LogP | 4.19 |
| Number Rings | 5 |
| Number Aromatic Rings | 2 |
| Heavy Atom Count | 24 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.3 |
| Exact Mass | 322.12 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Erythrina abyssinica | Leguminosae/Fabaceae | Plantae | 1237573 |
| 2 | Erythrina sacleuxii | Leguminosae/Fabaceae | Plantae | 1899109 |
| 3 | Erythrina sacleuxii | Leguminosae/Fabaceae | Plantae | 1899109 |
Showing of synonyms
Shinpterocarpin
UNII-QNW54SFH39
QNW54SFH39
157414-04-5
2H,6H-Benzofuro(3,2-C)pyrano(2,3-H)(1)benzopyran-9-ol, 6a,11a-dihydro-2,2-dimethyl-, (6aR,7bR)-
CHEMBL591773
DA-57835
Q27287385
(2R,10R)-17,17-dimethyl-3,12,18-trioxapentacyclo[11.8.0.02,10.04,9.014,19]henicosa-1(13),4(9),5,7,14(19),15,20-heptaen-6-ol
- Yenesew A, Twinomuhwezi H, et al. (2009). 8-Methoxyneorautenol and radical scavenging flavonoids from Erythrina abyssinica.. Bulletin of the Chemical Society of Ethiopia,2009,23(2),205-210. [View] [PubMed]
- Andayi AW, Yenesew A, et al. (2006). Antiplasmodial flavonoids from Erythrina sacleuxii.. Planta Medica,2006,72(2),187-189. [View] [PubMed]
- Yenesew A, Midiwo JO, et al. (2000). Two isoflavanones from the stem bark of Erythrina sacleuxii.. Phytochemistry,2000,55(5),457-459. [View] [PubMed]
CPRiL:
449736
SMILES: c1cccc(c12)OC3C2COc4c3ccc5c4C=CCO5
Level: 0
Mol. Weight: 322.36 g/mol
Anti-plasmodial
Radical scavenging towards 2;2-diphenyl-1-picrylhydrazyl radical (dpph)
Absorption
- Caco-2 (logPapp)
- -4.78
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.530
- Human Oral Bioavailability 50%
- Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -1.92
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 1.100
- Plasma Protein Binding
- 79.41
- Steady State Volume of Distribution
- -
Metabolism
- Breast Cancer Resistance Protein
- Inhibitor
- CYP 1A2 Inhibitor
- Inhibitor
- CYP 1A2 Substrate
- Substrate
- CYP 2C19 Inhibitor
- Inhibitor
- CYP 2C19 Substrate
- 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
- 9.860
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- 1.750
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Toxic
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 0.280
- Liver Injury II
- Toxic
- hERG Blockers
- Toxic
- Daphnia Maga
- 6.640
- Micronucleos
- Toxic
- NR-AhR
- Toxic
- NR-AR
- Safe
- NR-AR-LBD
- Safe
- NR-Aromatase
- Safe
- NR-ER
- Safe
- NR-ER-LBD
- Safe
- NR-GR
- Toxic
- NR-PPAR-gamma
- Safe
- NR-TR
- Toxic
- T. Pyriformis
- 1.360
- Rat (Acute)
- 2.640
- Rat (Chronic Oral)
- 1.670
- Fathead Minnow
- 4.620
- Respiratory Disease
- Toxic
- Skin Sensitisation
- Toxic
- SR-ARE
- Toxic
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Toxic
- SR-p53
- Safe
General Properties
- Boiling Point
- 445.430
- Hydration Free Energy
- -7.910
- Log(D) at pH=7.4
- 3.900
- Log(P)
- 4.33
- Log S
- -5.06
- Log(Vapor Pressure)
- -8.54
- Melting Point
- 193.0
- pKa Acid
- 10.5
- pKa Basic
- 6.2
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Chitinase A | Q9AMP1 | Q9AMP1_VIBHA | Vibrio harveyi | 3 | 0.9574 |
| Chitinase A | Q9AMP1 | Q9AMP1_VIBHA | Vibrio harveyi | 3 | 0.9574 |
| Heat shock protein HSP 90-alpha | P07900 | HS90A_HUMAN | Homo sapiens | 3 | 0.9540 |
| Heat shock protein HSP 90-alpha | P07900 | HS90A_HUMAN | Homo sapiens | 3 | 0.9540 |
| Heat shock protein HSP 90-alpha | P07900 | HS90A_HUMAN | Homo sapiens | 3 | 0.8682 |
| Heat shock protein HSP 90-alpha | P07900 | HS90A_HUMAN | Homo sapiens | 3 | 0.8682 |
| Mycinamicin III 3''-O-methyltransferase | Q49492 | MYCF_MICGR | Micromonospora griseorubida | 2 | 0.8678 |
| Mycinamicin III 3''-O-methyltransferase | Q49492 | MYCF_MICGR | Micromonospora griseorubida | 2 | 0.8678 |
| Beta-lactamase | Q9L5C8 | Q9L5C8_ECOLX | Escherichia coli | 3 | 0.8487 |
| Beta-lactamase | Q9L5C8 | Q9L5C8_ECOLX | Escherichia coli | 3 | 0.8487 |
| Heat shock protein HSP 90-alpha | P07900 | HS90A_HUMAN | Homo sapiens | 3 | 0.8445 |
| Heat shock protein HSP 90-alpha | P07900 | HS90A_HUMAN | Homo sapiens | 3 | 0.8445 |
| Thymidylate synthase | P00469 | TYSY_LACCA | Lacticaseibacillus casei | 3 | 0.8402 |
| Thymidylate synthase | P00469 | TYSY_LACCA | Lacticaseibacillus casei | 3 | 0.8402 |
| Sulfotransferase 1A1 | P50225 | ST1A1_HUMAN | Homo sapiens | 3 | 0.8366 |
| Sulfotransferase 1A1 | P50225 | ST1A1_HUMAN | Homo sapiens | 3 | 0.8366 |
| Apoptosis regulator Bcl-2 | P10415 | BCL2_HUMAN | Homo sapiens | 3 | 0.8326 |
| Apoptosis regulator Bcl-2 | P10415 | BCL2_HUMAN | Homo sapiens | 3 | 0.8326 |
| Beta-2-microglobulin | P61769 | B2MG_HUMAN | Homo sapiens | 3 | 0.8188 |
| Beta-2-microglobulin | P61769 | B2MG_HUMAN | Homo sapiens | 3 | 0.8188 |
| Kinesin-like protein KIF11 | P52732 | KIF11_HUMAN | Homo sapiens | 3 | 0.8123 |
| Kinesin-like protein KIF11 | P52732 | KIF11_HUMAN | Homo sapiens | 3 | 0.8123 |
| Integrin alpha-L | P20701 | ITAL_HUMAN | Homo sapiens | 3 | 0.7967 |
| Integrin alpha-L | P20701 | ITAL_HUMAN | Homo sapiens | 3 | 0.7967 |
| histidine kinase | O32393 | O32393_ARTPT | Arthrospira platensis | 3 | 0.7902 |
| histidine kinase | O32393 | O32393_ARTPT | Arthrospira platensis | 3 | 0.7902 |
| Nodulin-13 | P93330 | NOD13_MEDTR | Medicago truncatula | 3 | 0.7880 |
| Nodulin-13 | P93330 | NOD13_MEDTR | Medicago truncatula | 3 | 0.7880 |
| Retinol dehydratase | Q26490 | Q26490_SPOFR | Spodoptera frugiperda | 3 | 0.7803 |
| Retinol dehydratase | Q26490 | Q26490_SPOFR | Spodoptera frugiperda | 3 | 0.7803 |
| Vitamin D3 dihydroxylase | P18326 | CPXE_STRGO | Streptomyces griseolus | 3 | 0.7663 |
| Vitamin D3 dihydroxylase | P18326 | CPXE_STRGO | Streptomyces griseolus | 3 | 0.7663 |
| Tyrosine-protein kinase JAK2 | O60674 | JAK2_HUMAN | Homo sapiens | 3 | 0.7657 |
| Tyrosine-protein kinase JAK2 | O60674 | JAK2_HUMAN | Homo sapiens | 3 | 0.7657 |
| Vitamin D3 dihydroxylase | P18326 | CPXE_STRGO | Streptomyces griseolus | 3 | 0.7624 |
| Vitamin D3 dihydroxylase | P18326 | CPXE_STRGO | Streptomyces griseolus | 3 | 0.7624 |
| Aldo-keto reductase family 1 member B10 | O60218 | AK1BA_HUMAN | Homo sapiens | 3 | 0.7607 |
| Aldo-keto reductase family 1 member B10 | O60218 | AK1BA_HUMAN | Homo sapiens | 3 | 0.7607 |
| Aldo-keto reductase family 1 member B1 | P15121 | ALDR_HUMAN | Homo sapiens | 3 | 0.7544 |
| Aldo-keto reductase family 1 member B1 | P15121 | ALDR_HUMAN | Homo sapiens | 3 | 0.7544 |
| prolyl oligopeptidase | Q9X6R4 | Q9X6R4_AERCA | Aeromonas caviae | 3 | 0.7520 |
| prolyl oligopeptidase | Q9X6R4 | Q9X6R4_AERCA | Aeromonas caviae | 3 | 0.7520 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 3 | 0.7514 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 3 | 0.7514 |
| Mitogen-activated protein kinase 14 | Q16539 | MK14_HUMAN | Homo sapiens | 3 | 0.7464 |
| Mitogen-activated protein kinase 14 | Q16539 | MK14_HUMAN | Homo sapiens | 3 | 0.7464 |
| TDP-4-oxo-6-deoxy-alpha-D-glucose-3,4-oxoisomerase | Q6T1W8 | FDTA_ANETH | Aneurinibacillus thermoaerophilus | 3 | 0.7433 |
| TDP-4-oxo-6-deoxy-alpha-D-glucose-3,4-oxoisomerase | Q6T1W8 | FDTA_ANETH | Aneurinibacillus thermoaerophilus | 3 | 0.7433 |
| Gag-Pol polyprotein | P03367 | POL_HV1BR | Human immunodeficiency virus type 1 group M subtype B | 3 | 0.7411 |
| Gag-Pol polyprotein | P03367 | POL_HV1BR | Human immunodeficiency virus type 1 group M subtype B | 3 | 0.7411 |
| Glutathione S-transferase P | P09211 | GSTP1_HUMAN | Homo sapiens | 2 | 0.7397 |
| Glutathione S-transferase P | P09211 | GSTP1_HUMAN | Homo sapiens | 2 | 0.7397 |
| Mitochondrial poly(A) polymerase | F1NBW0 | F1NBW0_CHICK | Gallus gallus | 2 | 0.7396 |
| Mitochondrial poly(A) polymerase | F1NBW0 | F1NBW0_CHICK | Gallus gallus | 2 | 0.7396 |
| Thymidylate synthase | P00469 | TYSY_LACCA | Lacticaseibacillus casei | 2 | 0.7393 |
| Thymidylate synthase | P00469 | TYSY_LACCA | Lacticaseibacillus casei | 2 | 0.7393 |
| Neocarzinostatin | P0A3R9 | NCZS_STRCZ | Streptomyces carzinostaticus | 3 | 0.7374 |
| Neocarzinostatin | P0A3R9 | NCZS_STRCZ | Streptomyces carzinostaticus | 3 | 0.7374 |
| Mitogen-activated protein kinase 14 | Q16539 | MK14_HUMAN | Homo sapiens | 3 | 0.7357 |
| Mitogen-activated protein kinase 14 | Q16539 | MK14_HUMAN | Homo sapiens | 3 | 0.7357 |
| Catechol O-methyltransferase | P22734 | COMT_RAT | Rattus norvegicus | 3 | 0.7283 |
| Catechol O-methyltransferase | P22734 | COMT_RAT | Rattus norvegicus | 3 | 0.7283 |
| Thymidylate synthase | P0A886 | TYSY_ECO57 | Escherichia coli O157:H7 | 3 | 0.7257 |
| Thymidylate synthase | P0A886 | TYSY_ECO57 | Escherichia coli O157:H7 | 3 | 0.7257 |
| Lanosterol 14-alpha-demethylase | Q385E8 | Q385E8_TRYB2 | Trypanosoma brucei brucei | 3 | 0.7255 |
| Lanosterol 14-alpha-demethylase | Q385E8 | Q385E8_TRYB2 | Trypanosoma brucei brucei | 3 | 0.7255 |
| Catechol O-methyltransferase | P22734 | COMT_RAT | Rattus norvegicus | 3 | 0.7240 |
| Catechol O-methyltransferase | P22734 | COMT_RAT | Rattus norvegicus | 3 | 0.7240 |
| Pteridine reductase | O76290 | O76290_TRYBB | Trypanosoma brucei brucei | 2 | 0.7224 |
| Pteridine reductase | O76290 | O76290_TRYBB | Trypanosoma brucei brucei | 2 | 0.7224 |
| Bromodomain-containing protein 4 | O60885 | BRD4_HUMAN | Homo sapiens | 3 | 0.7213 |
| Bromodomain-containing protein 4 | O60885 | BRD4_HUMAN | Homo sapiens | 3 | 0.7213 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 3 | 0.7209 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 3 | 0.7209 |
| Aldehyde dehydrogenase, mitochondrial | P05091 | ALDH2_HUMAN | Homo sapiens | 4 | 0.7206 |
| Aldehyde dehydrogenase, mitochondrial | P05091 | ALDH2_HUMAN | Homo sapiens | 4 | 0.7206 |
| Dihydrofolate reductase | Q83AB2 | Q83AB2_COXBU | Coxiella burnetii | 3 | 0.7200 |
| Cytosolic purine 5'-nucleotidase | P49902 | 5NTC_HUMAN | Homo sapiens | 2 | 0.7200 |
| Dihydrofolate reductase | Q83AB2 | Q83AB2_COXBU | Coxiella burnetii | 3 | 0.7200 |
| Cytosolic purine 5'-nucleotidase | P49902 | 5NTC_HUMAN | Homo sapiens | 2 | 0.7200 |
| tyrosine--tRNA ligase | Q4QFJ7 | Q4QFJ7_LEIMA | Leishmania major | 3 | 0.7193 |
| tyrosine--tRNA ligase | Q4QFJ7 | Q4QFJ7_LEIMA | Leishmania major | 3 | 0.7193 |
| 4-hydroxyphenylacetate 3-monooxygenase | Q8YHT7 | Q8YHT7_BRUME | Brucella melitensis biotype 1 | 2 | 0.7184 |
| 4-hydroxyphenylacetate 3-monooxygenase | Q8YHT7 | Q8YHT7_BRUME | Brucella melitensis biotype 1 | 2 | 0.7184 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 3 | 0.7161 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 3 | 0.7161 |
| Mitogen-activated protein kinase 14 | Q16539 | MK14_HUMAN | Homo sapiens | 3 | 0.7128 |
| Mitogen-activated protein kinase 14 | Q16539 | MK14_HUMAN | Homo sapiens | 3 | 0.7128 |
| Cytidylate kinase | Q5SL35 | KCY_THET8 | Thermus thermophilus | 3 | 0.7122 |
| Cytidylate kinase | Q5SL35 | KCY_THET8 | Thermus thermophilus | 3 | 0.7122 |
| Dihydrofolate reductase | P22906 | DYR_CANAX | Candida albicans | 3 | 0.7114 |
| 3-hydroxyanthranilate 3,4-dioxygenase | Q1LCS4 | 3HAO_CUPMC | Cupriavidus metallidurans | 2 | 0.7114 |
| Dihydrofolate reductase | P22906 | DYR_CANAX | Candida albicans | 3 | 0.7114 |
| 3-hydroxyanthranilate 3,4-dioxygenase | Q1LCS4 | 3HAO_CUPMC | Cupriavidus metallidurans | 2 | 0.7114 |
| Cytochrome P450 monooxygenase | Q5YNS8 | Q5YNS8_NOCFA | Nocardia farcinica | 3 | 0.7108 |
| Cytochrome P450 monooxygenase | Q5YNS8 | Q5YNS8_NOCFA | Nocardia farcinica | 3 | 0.7108 |
| Beta-1 adrenergic receptor | P07700 | ADRB1_MELGA | Meleagris gallopavo | 3 | 0.7102 |
| Beta-1 adrenergic receptor | P07700 | ADRB1_MELGA | Meleagris gallopavo | 3 | 0.7102 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 3 | 0.7096 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 3 | 0.7096 |
| Bromodomain adjacent to zinc finger domain protein 2B | Q9UIF8 | BAZ2B_HUMAN | Homo sapiens | 2 | 0.7095 |
| Bromodomain adjacent to zinc finger domain protein 2B | Q9UIF8 | BAZ2B_HUMAN | Homo sapiens | 2 | 0.7095 |
| Cytochrome P450 2C8 | P10632 | CP2C8_HUMAN | Homo sapiens | 3 | 0.7090 |
| Cytochrome P450 2C8 | P10632 | CP2C8_HUMAN | Homo sapiens | 3 | 0.7090 |
| Poly [ADP-ribose] polymerase tankyrase-1 | O95271 | TNKS1_HUMAN | Homo sapiens | 2 | 0.7047 |
| Poly [ADP-ribose] polymerase tankyrase-1 | O95271 | TNKS1_HUMAN | Homo sapiens | 2 | 0.7047 |
| Holliday junction branch migration complex subunit RuvB | Q9PMT7 | RUVB_CAMJE | Campylobacter jejuni subsp. jejuni serotype O:2 | 2 | 0.7045 |
| Holliday junction branch migration complex subunit RuvB | Q9PMT7 | RUVB_CAMJE | Campylobacter jejuni subsp. jejuni serotype O:2 | 2 | 0.7045 |
| cAMP-dependent protein kinase catalytic subunit alpha | P00517 | KAPCA_BOVIN | Bos taurus | 3 | 0.7039 |
| cAMP-dependent protein kinase catalytic subunit alpha | P00517 | KAPCA_BOVIN | Bos taurus | 3 | 0.7039 |
| Acetolactate synthase, chloroplastic | P17597 | ILVB_ARATH | Arabidopsis thaliana | 2 | 0.7001 |
| Acetolactate synthase, chloroplastic | P17597 | ILVB_ARATH | Arabidopsis thaliana | 2 | 0.7001 |