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5,5’-bichrysophanol
- Family: Plantae - Liliaceae
- Kingdom: Plantae
-
Class: Anthracene
- Subclass: Anthraquinone
| Canonical Smiles | Cc1cc(O)c2c(c1)C(=O)c1c(C2=O)c(O)ccc1c1ccc(c2c1C(=O)c1cc(C)cc(c1C2=O)O)O |
|---|---|
| InChI | InChI=1S/C30H18O8/c1-11-7-15-21(19(33)9-11)29(37)25-17(31)5-3-13(23(25)27(15)35)14-4-6-18(32)26-24(14)28(36)16-8-12(2)10-20(34)22(16)30(26)38/h3-10,31-34H,1-2H3 |
| InChIKey | PTEBGWHDOZFDET-UHFFFAOYSA-N |
| Formula | C30H18O8 |
| HBA | 8 |
| HBD | 4 |
| MW | 506.47 |
| Rotatable Bonds | 1 |
| TPSA | 149.2 |
| LogP | 4.34 |
| Number Rings | 6 |
| Number Aromatic Rings | 4 |
| Heavy Atom Count | 38 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.07 |
| Exact Mass | 506.1 |
| Number of Lipinski Rule Violations | 1 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Asphodelus microcarpus | Liliaceae | Plantae | 49697 |
Showing of synonyms
5,5’-bichrysophanol
Dianhydrorugulosin
(+)-Dianhydrorugulosin
18693-26-0
(1,1'-Bianthracene)-9,9',10,10'-tetrone, 4,4',5,5'-tetrahydroxy-7,7'-dimethyl-, (+)-
(+)-4,4'5,5'-Tetrahydroxy-7,7'-dimethyl-(1,1'-bianthracene)-9,9',10,10'-tetrone
DTXSID20940156
4,4',5,5'-Tetrahydroxy-7,7'-dimethyl[1,1'-bianthracene]-9,9',10,10'-tetrone
- Rizk A, Hammouda F, et al. (1972). Anthraquinones of Asphodelus microcarpus. Phytochemistry, 1972, 11(6), 2122-2125. [View]
No compound-protein relationship available.
SMILES: c1cccc(C2=O)c1C(=O)c(c23)cccc3-c4cccc(c45)C(=O)c6c(C5=O)cccc6
Level: 1
Mol. Weight: 506.47 g/mol
SMILES: c1cccc(c12)C(=O)c3c(C2=O)cccc3
Level: 0
Mol. Weight: 506.47 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -5.61
- Human Oral Bioavailability 20%
- Non-Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.85
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- 0.85
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Non-Penetrable
- Fraction Unbound (Human)
- 1.22
- Plasma Protein Binding
- 86.08
- Steady State Volume of Distribution
- -
Metabolism
- Breast Cancer Resistance Protein
- Inhibitor
- CYP 1A2 Inhibitor
- Inhibitor
- CYP 1A2 Substrate
- Substrate
- CYP 2C19 Inhibitor
- Non-Inhibitor
- CYP 2C19 Substrate
- Non-Substrate
- CYP 2C9 Inhibitor
- Non-Inhibitor
- CYP 2C9 Substrate
- Substrate
- CYP 2D6 Inhibitor
- Inhibitor
- CYP 2D6 Substrate
- Non-Substrate
- CYP 3A4 Inhibitor
- Non-Inhibitor
- CYP 3A4 Substrate
- Non-Substrate
- OATP1B1
- Inhibitor
- OATP1B3
- Non-Inhibitor
Excretion
- Clearance
- 6.71
- Organic Cation Transporter 2
- Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- 0.62
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Toxic
- Liver Injury I (DILI)
- Toxic
- Eye Corrosion
- Safe
- Eye Irritation
- Toxic
- Maximum Tolerated Dose
- 0.97
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 6.15
- 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
- -1720.4
- Rat (Acute)
- 2.54
- Rat (Chronic Oral)
- 3.66
- Fathead Minnow
- 11.45
- Respiratory Disease
- Safe
- Skin Sensitisation
- Safe
- SR-ARE
- Toxic
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Toxic
- SR-p53
- Toxic
General Properties
- Boiling Point
- 618.5
- Hydration Free Energy
- -3.11
- Log(D) at pH=7.4
- 3.32
- Log(P)
- 7.03
- Log S
- -7.56
- Log(Vapor Pressure)
- -10.14
- Melting Point
- 353.52
- pKa Acid
- 7.25
- pKa Basic
- 2.7
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Chitinase A | Q9AMP1 | Q9AMP1_VIBHA | Vibrio harveyi | 3 | 0.9122 |
| Acetylcholinesterase | P21836 | ACES_MOUSE | Mus musculus | 3 | 0.8692 |
| Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase | Q9TQS6 | DHDH_MACFA | Macaca fascicularis | 3 | 0.8406 |
| cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A | Q9Y233 | PDE10_HUMAN | Homo sapiens | 3 | 0.7925 |
| Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha | Q04631 | FNTA_RAT | Rattus norvegicus | 3 | 0.7889 |
| Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha | Q4WP27 | Q4WP27_ASPFU | Aspergillus fumigatus | 3 | 0.7665 |
| Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha | Q4WP27 | Q4WP27_ASPFU | Aspergillus fumigatus | 3 | 0.7664 |
| Tyrosine-protein kinase SYK | P43405 | KSYK_HUMAN | Homo sapiens | 4 | 0.7619 |
| Basic phospholipase A2 VRV-PL-VIIIa | P59071 | PA2B8_DABRR | Daboia russelii | 2 | 0.7477 |
| Methionine aminopeptidase 2 | P50579 | MAP2_HUMAN | Homo sapiens | 3 | 0.7403 |
| Acetolactate synthase, chloroplastic | P17597 | ILVB_ARATH | Arabidopsis thaliana | 3 | 0.7381 |
| Cyclic dipeptide N-prenyltransferase | D1D8L6 | D1D8L6_ASPFM | Neosartorya fumigata | 3 | 0.7327 |
| Flavin-dependent monooxygenase | Q93L51 | TETX_BACT4 | Bacteroides thetaiotaomicron | 3 | 0.7297 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 3 | 0.7214 |
| UTP-monosaccharide-1-phosphate uridylyltransferase | D3G6S4 | D3G6S4_LEIMA | Leishmania major | 3 | 0.7107 |
| Riboflavin synthase | P0AFU8 | RISA_ECOLI | Escherichia coli | 3 | 0.7052 |