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Neorautenol
- Family: Plantae - Leguminosae/Fabaceae
- Kingdom: Plantae
-
Class: Flavonoid
- Subclass: Pterocarpan
| Canonical Smiles | Oc1ccc2c(c1)O[C@@H]1[C@H]2COc2c1cc1C=CC(Oc1c2)(C)C |
|---|---|
| InChI | InChI=1S/C20H18O4/c1-20(2)6-5-11-7-14-17(9-16(11)24-20)22-10-15-13-4-3-12(21)8-18(13)23-19(14)15/h3-9,15,19,21H,10H2,1-2H3/t15-,19-/m0/s1 |
| InChIKey | OGFFMQWYZCTXCM-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 burttii | Leguminosae/Fabaceae | Plantae | 2590687 |
| 2 | Erythrina burttii | Leguminosae/Fabaceae | Plantae | 2590687 |
| 3 | Erythrina schliebenii | Leguminosae/Fabaceae | Plantae | 2590720 |
Showing of synonyms
Neorautenol
53766-52-2
(2R,10R)-17,17-dimethyl-3,12,16-trioxapentacyclo[11.8.0.02,10.04,9.015,20]henicosa-1(13),4(9),5,7,14,18,20-heptaen-6-ol
(2R,10R)-17,17-dimethyl-3,12,16-trioxapentacyclo(11.8.0.02,10.04,9.015,20)henicosa-1(13),4(9),5,7,14,18,20-heptaen-6-ol
CHEMBL1098728
BDBM50317432
XN161719
(-)-Neorautenol
(7aR,12aS)-7a,12a-Dihydro-3,3-dimethyl-3H,7H-benzofuro[3,2-c]pyrano[3,2-g][1]benzopyran-10-ol
- Yenesew A, Derese S, et al. (2005). Antimicrobial flavonoids from the stem bark of Erythrina burttii.. Fitoterapia,2005,76(5),469-472. [View] [PubMed]
- Nyandoro SS, Munissi JJ, et al. (2017). Flavonoids from Erythrina schliebenii.. Journal of Natural Products,2017,80(2),377-383. [View] [PubMed]
- Yenesew A, Midiwo JO, et al. (1998). Two prenylated flavanones from stem bark of Erythrina burttii. Phytochemistry,1998,48(8),1489-1443. [View] [PubMed]
Pubchem:
11500744
Cas:
53766-52-2
Zinc:
ZINC000014613195
Nmrshiftdb2:
60072155
Chembl:
CHEMBL1098728
Bindingdb:
50317432
CPRiL:
286413
SMILES: c1cccc(c12)OC3C2COc4c3cc5c(c4)OCC=C5
Level: 0
Mol. Weight: 322.36 g/mol
Antimicrobial
Absorption
- Caco-2 (logPapp)
- -4.77
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.560
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -1.78
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 1.110
- Plasma Protein Binding
- 81.54
- 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
- 10.290
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- 1.770
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Toxic
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 0.360
- Liver Injury II
- Toxic
- hERG Blockers
- Toxic
- Daphnia Maga
- 6.550
- 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
- 1.400
- Rat (Acute)
- 2.480
- Rat (Chronic Oral)
- 1.580
- Fathead Minnow
- 4.650
- 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
- 449.090
- Hydration Free Energy
- -8.240
- Log(D) at pH=7.4
- 3.960
- Log(P)
- 4.17
- Log S
- -5.1
- Log(Vapor Pressure)
- -8.67
- Melting Point
- 204.52
- pKa Acid
- 10.59
- pKa Basic
- 6.4
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Heat shock protein HSP 90-alpha | P07900 | HS90A_HUMAN | Homo sapiens | 3 | 0.9538 |
| Heat shock protein HSP 90-alpha | P07900 | HS90A_HUMAN | Homo sapiens | 3 | 0.9538 |
| Chitinase A | Q9AMP1 | Q9AMP1_VIBHA | Vibrio harveyi | 3 | 0.9397 |
| Chitinase A | Q9AMP1 | Q9AMP1_VIBHA | Vibrio harveyi | 3 | 0.9397 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.8503 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.8503 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 3 | 0.8467 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 3 | 0.8467 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.8460 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.8460 |
| Beta-2-microglobulin | P61769 | B2MG_HUMAN | Homo sapiens | 3 | 0.8355 |
| Beta-2-microglobulin | P61769 | B2MG_HUMAN | Homo sapiens | 3 | 0.8355 |
| Sulfotransferase 1A1 | P50225 | ST1A1_HUMAN | Homo sapiens | 3 | 0.8230 |
| Sulfotransferase 1A1 | P50225 | ST1A1_HUMAN | Homo sapiens | 3 | 0.8230 |
| Pancreatic alpha-amylase | P04746 | AMYP_HUMAN | Homo sapiens | 3 | 0.8160 |
| Pancreatic alpha-amylase | P04746 | AMYP_HUMAN | Homo sapiens | 3 | 0.8160 |
| CmeR | Q7B8P6 | Q7B8P6_CAMJU | Campylobacter jejuni | 3 | 0.8145 |
| CmeR | Q7B8P6 | Q7B8P6_CAMJU | Campylobacter jejuni | 3 | 0.8145 |
| Chalcone--flavanone isomerase 1 | P28012 | CFI1_MEDSA | Medicago sativa | 4 | 0.8125 |
| Chalcone--flavanone isomerase 1 | P28012 | CFI1_MEDSA | Medicago sativa | 4 | 0.8125 |
| Aldehyde dehydrogenase, dimeric NADP-preferring | P30838 | AL3A1_HUMAN | Homo sapiens | 3 | 0.7985 |
| Aldehyde dehydrogenase, dimeric NADP-preferring | P30838 | AL3A1_HUMAN | Homo sapiens | 3 | 0.7985 |
| Rhodopsin | P02699 | OPSD_BOVIN | Bos taurus | 3 | 0.7952 |
| Rhodopsin | P02699 | OPSD_BOVIN | Bos taurus | 3 | 0.7952 |
| Phospholipase A2, major isoenzyme | P00592 | PA21B_PIG | Sus scrofa | 3 | 0.7951 |
| Phospholipase A2, major isoenzyme | P00592 | PA21B_PIG | Sus scrofa | 3 | 0.7951 |
| Achbp | I6L8L2 | I6L8L2_CAPTE | Capitella teleta | 3 | 0.7911 |
| Achbp | I6L8L2 | I6L8L2_CAPTE | Capitella teleta | 3 | 0.7911 |
| Proliferating cell nuclear antigen | P12004 | PCNA_HUMAN | Homo sapiens | 3 | 0.7860 |
| Proliferating cell nuclear antigen | P12004 | PCNA_HUMAN | Homo sapiens | 3 | 0.7860 |
| Chalcone--flavanone isomerase 1 | P28012 | CFI1_MEDSA | Medicago sativa | 3 | 0.7828 |
| Chalcone--flavanone isomerase 1 | P28012 | CFI1_MEDSA | Medicago sativa | 3 | 0.7828 |
| Soluble cytochrome b562 | P0ABE7 | C562_ECOLX | Escherichia coli | 4 | 0.7771 |
| Soluble cytochrome b562 | P0ABE7 | C562_ECOLX | Escherichia coli | 4 | 0.7771 |
| Beta-1 adrenergic receptor | P07700 | ADRB1_MELGA | Meleagris gallopavo | 3 | 0.7767 |
| Beta-1 adrenergic receptor | P07700 | ADRB1_MELGA | Meleagris gallopavo | 3 | 0.7767 |
| Kinesin-like protein KIF11 | P52732 | KIF11_HUMAN | Homo sapiens | 3 | 0.7762 |
| Kinesin-like protein KIF11 | P52732 | KIF11_HUMAN | Homo sapiens | 3 | 0.7762 |
| Tyrosine-protein kinase JAK2 | O60674 | JAK2_HUMAN | Homo sapiens | 3 | 0.7689 |
| Tyrosine-protein kinase JAK2 | O60674 | JAK2_HUMAN | Homo sapiens | 3 | 0.7689 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 2 | 0.7654 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 2 | 0.7654 |
| Nuclear receptor coactivator 2 | Q15596 | NCOA2_HUMAN | Homo sapiens | 3 | 0.7648 |
| Nuclear receptor coactivator 2 | Q15596 | NCOA2_HUMAN | Homo sapiens | 3 | 0.7648 |
| Retinol dehydratase | Q26490 | Q26490_SPOFR | Spodoptera frugiperda | 3 | 0.7628 |
| Retinol dehydratase | Q26490 | Q26490_SPOFR | Spodoptera frugiperda | 3 | 0.7628 |
| Dihydrofolate reductase | P22906 | DYR_CANAX | Candida albicans | 3 | 0.7615 |
| Dihydrofolate reductase | P22906 | DYR_CANAX | Candida albicans | 3 | 0.7615 |
| Beta-lactoglobulin | P02754 | LACB_BOVIN | Bos taurus | 3 | 0.7543 |
| Beta-lactoglobulin | P02754 | LACB_BOVIN | Bos taurus | 3 | 0.7543 |
| Bromodomain adjacent to zinc finger domain protein 2B | Q9UIF8 | BAZ2B_HUMAN | Homo sapiens | 2 | 0.7540 |
| Bromodomain adjacent to zinc finger domain protein 2B | Q9UIF8 | BAZ2B_HUMAN | Homo sapiens | 2 | 0.7540 |
| Enoyl-ACP reductase | Q9BH77 | Q9BH77_PLAFA | Plasmodium falciparum | 3 | 0.7471 |
| Enoyl-ACP reductase | Q9BH77 | Q9BH77_PLAFA | Plasmodium falciparum | 3 | 0.7471 |
| NADPH-dependent 7-cyano-7-deazaguanine reductase | Q9KTK0 | QUEF_VIBCH | Vibrio cholerae serotype O1 | 3 | 0.7426 |
| NADPH-dependent 7-cyano-7-deazaguanine reductase | Q9KTK0 | QUEF_VIBCH | Vibrio cholerae serotype O1 | 3 | 0.7426 |
| Nuclear receptor ROR-alpha | P35398 | RORA_HUMAN | Homo sapiens | 3 | 0.7396 |
| Nuclear receptor ROR-alpha | P35398 | RORA_HUMAN | Homo sapiens | 3 | 0.7396 |
| Catechol O-methyltransferase | P22734 | COMT_RAT | Rattus norvegicus | 3 | 0.7285 |
| Catechol O-methyltransferase | P22734 | COMT_RAT | Rattus norvegicus | 3 | 0.7285 |
| Avidin | P02701 | AVID_CHICK | Gallus gallus | 2 | 0.7261 |
| Avidin | P02701 | AVID_CHICK | Gallus gallus | 2 | 0.7261 |
| Probable NDP-rhamnosyltransferase | Q9ALM8 | Q9ALM8_SACSN | Saccharopolyspora spinosa | 3 | 0.7247 |
| Probable NDP-rhamnosyltransferase | Q9ALM8 | Q9ALM8_SACSN | Saccharopolyspora spinosa | 3 | 0.7247 |
| Cytidylate kinase | Q5SL35 | KCY_THET8 | Thermus thermophilus | 3 | 0.7241 |
| Cytidylate kinase | Q5SL35 | KCY_THET8 | Thermus thermophilus | 3 | 0.7241 |
| Catechol O-methyltransferase | P22734 | COMT_RAT | Rattus norvegicus | 3 | 0.7239 |
| Catechol O-methyltransferase | P22734 | COMT_RAT | Rattus norvegicus | 3 | 0.7239 |
| Gag-Pol polyprotein | P04584 | POL_HV2RO | Human immunodeficiency virus type 2 subtype A | 3 | 0.7234 |
| Gag-Pol polyprotein | P04584 | POL_HV2RO | Human immunodeficiency virus type 2 subtype A | 3 | 0.7234 |
| Dihydrofolate reductase | P0A017 | DYR_STAAU | Staphylococcus aureus | 3 | 0.7209 |
| Dihydrofolate reductase | P0A017 | DYR_STAAU | Staphylococcus aureus | 3 | 0.7209 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 3 | 0.7193 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 3 | 0.7193 |
| Vitamin D3 dihydroxylase | P18326 | CPXE_STRGO | Streptomyces griseolus | 3 | 0.7170 |
| Vitamin D3 dihydroxylase | P18326 | CPXE_STRGO | Streptomyces griseolus | 3 | 0.7170 |
| Aldo-keto reductase family 1 member B1 | P15121 | ALDR_HUMAN | Homo sapiens | 3 | 0.7164 |
| Aldo-keto reductase family 1 member B1 | P15121 | ALDR_HUMAN | Homo sapiens | 3 | 0.7164 |
| Thymidylate synthase | P00469 | TYSY_LACCA | Lacticaseibacillus casei | 3 | 0.7158 |
| Thymidylate synthase | P00469 | TYSY_LACCA | Lacticaseibacillus casei | 3 | 0.7158 |
| Ectonucleotide pyrophosphatase/phosphodiesterase family member 2 | Q9R1E6 | ENPP2_MOUSE | Mus musculus | 3 | 0.7119 |
| Ectonucleotide pyrophosphatase/phosphodiesterase family member 2 | Q9R1E6 | ENPP2_MOUSE | Mus musculus | 3 | 0.7119 |
| Cytochrome P450 130 | P9WPN5 | CP130_MYCTU | Mycobacterium tuberculosis | 3 | 0.7085 |
| Cytochrome P450 130 | P9WPN5 | CP130_MYCTU | Mycobacterium tuberculosis | 3 | 0.7085 |
| Soluble acetylcholine receptor | Q8WSF8 | Q8WSF8_APLCA | Aplysia californica | 2 | 0.7064 |
| Soluble acetylcholine receptor | Q8WSF8 | Q8WSF8_APLCA | Aplysia californica | 2 | 0.7064 |
| Nitric oxide synthase 1 | P29476 | NOS1_RAT | Rattus norvegicus | 3 | 0.7062 |
| Nitric oxide synthase 1 | P29476 | NOS1_RAT | Rattus norvegicus | 3 | 0.7062 |
| Phytohormone-binding protein CSBP | A0A1S3THR8 | PHBP_VIGRR | Vigna radiata var. radiata | 2 | 0.7037 |
| Phytohormone-binding protein CSBP | A0A1S3THR8 | PHBP_VIGRR | Vigna radiata var. radiata | 2 | 0.7037 |
| Gag-Pol polyprotein | P12497 | POL_HV1N5 | Human immunodeficiency virus type 1 group M subtype B | 3 | 0.7029 |
| Gag-Pol polyprotein | P12497 | POL_HV1N5 | Human immunodeficiency virus type 1 group M subtype B | 3 | 0.7029 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 3 | 0.7028 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 3 | 0.7028 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 3 | 0.7009 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 3 | 0.7009 |
| CmeR | Q7B8P6 | Q7B8P6_CAMJU | Campylobacter jejuni | 2 | 0.7001 |
| CmeR | Q7B8P6 | Q7B8P6_CAMJU | Campylobacter jejuni | 2 | 0.7001 |