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Daphnodorin B
- Family: Plantae - Thymelaeaceae
- Kingdom: Plantae
-
Class: Flavonoid
- Subclass: Isoflavan
| Canonical Smiles | Oc1ccc(cc1)[C@H]1Oc2c(C[C@@H]1O)c(O)cc1c2c(c(o1)c1ccc(cc1)O)C(=O)c1c(O)cc(cc1O)O |
|---|---|
| InChI | InChI=1S/C30H22O10/c31-15-5-1-13(2-6-15)28-22(37)11-18-19(34)12-23-25(30(18)40-28)26(29(39-23)14-3-7-16(32)8-4-14)27(38)24-20(35)9-17(33)10-21(24)36/h1-10,12,22,28,31-37H,11H2/t22-,28+/m0/s1 |
| InChIKey | JBNFGJOTOPTIDE-RBISFHTESA-N |
| Formula | C30H22O10 |
| HBA | 10 |
| HBD | 7 |
| MW | 542.5 |
| Rotatable Bonds | 4 |
| TPSA | 181.05 |
| LogP | 4.6 |
| Number Rings | 6 |
| Number Aromatic Rings | 5 |
| Heavy Atom Count | 40 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.1 |
| Exact Mass | 542.12 |
| Number of Lipinski Rule Violations | 2 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Thymelaea hirsuta | Thymelaeaceae | Plantae | 69845 |
Showing of synonyms
Daphnodorin B
95733-02-1
[(2R,3S)-3,5-dihydroxy-2,8-bis(4-hydroxyphenyl)-3,4-dihydro-2H-furo[2,3-h]chromen-9-yl]-(2,4,6-trihydroxyphenyl)methanone
DTXSID50241941
Methanone, (3,4-dihydro-3,5-dihydroxy-2,8-bis(4-hydroxyphenyl)-2H-furo(2,3-h)-l-benzopyran-9-yl)(2,4,6-trihydroxyphenyl)-, trans-(-)-
((2R,3S)-3,5-dihydroxy-2,8-bis(4-hydroxyphenyl)-3,4-dihydro-2H-furo(2,3-h)chromen-9-yl)-(2,4,6-trihydroxyphenyl)methanone
DTXCID80164432
[(2r,3s)-3,5-dihydroxy-2,8-bis(4-hydroxyphenyl)-3,4-dihydro-2h-furo[2,3-h]chromen-9-yl](2,4,6-trihydroxyphenyl)methanone
NSC698798
SCHEMBL1229973
CHEMBL2273052
HY-N10961
AKOS040734025
NSC-698798
DA-52309
CS-0637794
[3,4-Dihydro-3,5-dihydro-2,8-bis(4-hydroxyphenyl)-2H-furo[2,3-h]benzopyran-9-yl](2,4,5-trihydroxyphenyl)methanone, trans-(-)
CPRiL:
345589
SMILES: c1ccccc1C(=O)c2c(-c3ccccc3)oc(c24)ccc5c4OC(CC5)c6ccccc6
Level: 3
Mol. Weight: 542.5 g/mol
SMILES: c1ccccc1C(=O)c2coc(c23)ccc4c3OC(CC4)c5ccccc5
Level: 2
Mol. Weight: 542.5 g/mol
SMILES: c1ccccc1C(=O)c2c(-c3ccccc3)oc(c24)ccc5c4OCCC5
Level: 2
Mol. Weight: 542.5 g/mol
SMILES: c1ccccc1-c(c2)oc(c23)ccc4c3OC(CC4)c5ccccc5
Level: 2
Mol. Weight: 542.5 g/mol
SMILES: c1ccccc1C(=O)c2coc(c23)ccc4c3OCCC4
Level: 1
Mol. Weight: 542.5 g/mol
SMILES: c1coc(c12)ccc3c2OC(CC3)c4ccccc4
Level: 1
Mol. Weight: 542.5 g/mol
SMILES: C1CCOc2c1ccc(c23)oc(c3)-c4ccccc4
Level: 1
Mol. Weight: 542.5 g/mol
SMILES: c1coc(c12)ccc3c2OCCC3
Level: 0
Mol. Weight: 542.5 g/mol
SMILES: c1ccccc1
Level: 0
Mol. Weight: 542.5 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -6.22
- Human Oral Bioavailability 20%
- Non-Bioavailable
- Human Intestinal Absorption
- Non-Absorbed
- Madin-Darby Canine Kidney
- -5.200
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- 5.53
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Non-Penetrable
- Fraction Unbound (Human)
- 1.110
- Plasma Protein Binding
- 92.09
- Steady State Volume of Distribution
- -
Metabolism
- Breast Cancer Resistance Protein
- Inhibitor
- CYP 1A2 Inhibitor
- Non-Inhibitor
- CYP 1A2 Substrate
- Non-Substrate
- CYP 2C19 Inhibitor
- Non-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
- Non-Inhibitor
- CYP 3A4 Substrate
- Non-Substrate
- OATP1B1
- Inhibitor
- OATP1B3
- Non-Inhibitor
Excretion
- Clearance
- 8.120
- Organic Cation Transporter 2
- Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- 1.000
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Toxic
- Liver Injury I (DILI)
- Toxic
- Eye Corrosion
- Safe
- Eye Irritation
- Toxic
- Maximum Tolerated Dose
- 1.030
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 6.020
- Micronucleos
- Toxic
- NR-AhR
- Safe
- NR-AR
- Safe
- NR-AR-LBD
- Safe
- NR-Aromatase
- Toxic
- NR-ER
- Toxic
- NR-ER-LBD
- Safe
- NR-GR
- Safe
- NR-PPAR-gamma
- Safe
- NR-TR
- Toxic
- T. Pyriformis
- -6472.620
- Rat (Acute)
- 2.360
- Rat (Chronic Oral)
- 3.900
- Fathead Minnow
- 19.800
- Respiratory Disease
- Safe
- Skin Sensitisation
- Safe
- SR-ARE
- Safe
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Toxic
- SR-p53
- Toxic
General Properties
- Boiling Point
- 559.860
- Hydration Free Energy
- -3.110
- Log(D) at pH=7.4
- 3.050
- Log(P)
- 4.75
- Log S
- -5.51
- Log(Vapor Pressure)
- -9.4
- Melting Point
- 288.63
- pKa Acid
- 8.64
- pKa Basic
- 6.53
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Histone deacetylase 4 | P56524 | HDAC4_HUMAN | Homo sapiens | 3 | 0.8966 |
| Multidrug-efflux transporter 1 regulator | P39075 | BMRR_BACSU | Bacillus subtilis | 3 | 0.8876 |
| D-aminoacyl-tRNA deacylase | Q8IIS0 | DTD_PLAF7 | Plasmodium falciparum | 3 | 0.8809 |
| Thymidylate synthase | P00469 | TYSY_LACCA | Lacticaseibacillus casei | 3 | 0.8684 |
| Homoserine dehydrogenase | P31116 | DHOM_YEAST | Saccharomyces cerevisiae | 4 | 0.8511 |
| Caspase-6 | P55212 | CASP6_HUMAN | Homo sapiens | 3 | 0.8419 |
| Polyribonucleotide nucleotidyltransferase | A7ZS61 | PNP_ECO24 | Escherichia coli O139:H28 | 4 | 0.8375 |
| Sterol 14alpha-demethylase | P9WPP9 | CP51_MYCTU | Mycobacterium tuberculosis | 4 | 0.8033 |
| Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha | Q04631 | FNTA_RAT | Rattus norvegicus | 3 | 0.7925 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 3 | 0.7775 |
| Endothiapepsin | P11838 | CARP_CRYPA | Cryphonectria parasitica | 4 | 0.7672 |
| Thymidylate synthase | P00469 | TYSY_LACCA | Lacticaseibacillus casei | 4 | 0.7540 |
| Streptogramin A acetyltransferase | P50870 | VATD_ENTFC | Enterococcus faecium | 3 | 0.7483 |
| Bromodomain-containing protein 2 | P25440 | BRD2_HUMAN | Homo sapiens | 3 | 0.7416 |
| Maltose/maltodextrin-binding periplasmic protein | P0AEX9 | MALE_ECOLI | Escherichia coli | 3 | 0.7305 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 3 | 0.7218 |
| High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A | O76083 | PDE9A_HUMAN | Homo sapiens | 3 | 0.7194 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 3 | 0.7163 |
| Beta-lactamase | Q9L5C8 | Q9L5C8_ECOLX | Escherichia coli | 3 | 0.7119 |
| Nitric oxide synthase oxygenase | O34453 | NOSO_BACSU | Bacillus subtilis | 4 | 0.7066 |