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10,10'-chrysophanol bianthrone
- Family: Plantae - Asphodelaceae
- Kingdom: Plantae
-
Class: Anthraquinone
- Subclass: Isofuranonaphthoquinone
| Canonical Smiles | Cc1cc(O)c2c(c1)C(C1c3cccc(c3C(=O)c3c1cc(C)cc3O)O)c1c(C2=O)c(O)ccc1 |
|---|---|
| InChI | InChI=1S/C30H22O6/c1-13-9-17-23(15-5-3-7-19(31)25(15)29(35)27(17)21(33)11-13)24-16-6-4-8-20(32)26(16)30(36)28-18(24)10-14(2)12-22(28)34/h3-12,23-24,31-34H,1-2H3 |
| InChIKey | IXXWTERKUADIKZ-UHFFFAOYSA-N |
| Formula | C30H22O6 |
| HBA | 6 |
| HBD | 4 |
| MW | 478.5 |
| Rotatable Bonds | 1 |
| TPSA | 115.06 |
| LogP | 5.18 |
| Number Rings | 6 |
| Number Aromatic Rings | 4 |
| Heavy Atom Count | 36 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.13 |
| Exact Mass | 478.14 |
| Number of Lipinski Rule Violations | 1 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Bulbine capitata | Asphodelaceae | Plantae | 576756 |
Showing of synonyms
10,10'-chrysophanol bianthrone
NSC658573
Ararobinol
CHEMBL1981253
NSC-658573
10-(4,5-dihydroxy-2-methyl-10-oxo-9H-anthracen-9-yl)-1,8-dihydroxy-3-methyl-10H-anthracen-9-one
NCI60_020619
[9,9'-Bianthracene]-10,10'(9H,9'H)-dione, 4,4',5,5'-tetrahydroxy-2,2'-dimethyl-
- Bezabih M, Abegaz BM, et al. (2001). Antiplasmodial and Antioxidant Isofuranonaphthoquinones from the Roots of Bulbine capitata. Planta medica, 2001, 67(4), 340–344. [View]
CPRiL:
413989
SMILES: c1cccc(C2=O)c1C(c(c23)cccc3)C(c(c45)cccc5)c6c(C4=O)cccc6
Level: 1
Mol. Weight: 478.5 g/mol
SMILES: c1cccc(c12)Cc3c(C2=O)cccc3
Level: 0
Mol. Weight: 478.5 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -5.56
- Human Oral Bioavailability 20%
- Non-Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.9
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- 0.03
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Non-Penetrable
- Fraction Unbound (Human)
- 1.46
- Plasma Protein Binding
- 88.41
- Steady State Volume of Distribution
- -
Metabolism
- Breast Cancer Resistance Protein
- Inhibitor
- CYP 1A2 Inhibitor
- Inhibitor
- CYP 1A2 Substrate
- Non-Substrate
- CYP 2C19 Inhibitor
- Non-Inhibitor
- CYP 2C19 Substrate
- Non-Substrate
- CYP 2C9 Inhibitor
- Inhibitor
- CYP 2C9 Substrate
- 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
- 6.44
- Organic Cation Transporter 2
- Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- 1.18
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Toxic
- Liver Injury I (DILI)
- Toxic
- Eye Corrosion
- Safe
- Eye Irritation
- Toxic
- Maximum Tolerated Dose
- 0.69
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 6.23
- Micronucleos
- Toxic
- NR-AhR
- Safe
- 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
- -764.96
- Rat (Acute)
- 2.39
- Rat (Chronic Oral)
- 3.85
- Fathead Minnow
- 7.53
- 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
- 567.39
- Hydration Free Energy
- -3.22
- Log(D) at pH=7.4
- 3.78
- Log(P)
- 7.96
- Log S
- -5.26
- Log(Vapor Pressure)
- -10.67
- Melting Point
- 266.52
- pKa Acid
- 7.7
- pKa Basic
- 6.68
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Soluble acetylcholine receptor | Q8WSF8 | Q8WSF8_APLCA | Aplysia californica | 3 | 0.9071 |
| Acetylcholinesterase | P21836 | ACES_MOUSE | Mus musculus | 3 | 0.8591 |
| Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha | Q4WP27 | Q4WP27_ASPFU | Aspergillus fumigatus | 3 | 0.7655 |
| Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha | Q04631 | FNTA_RAT | Rattus norvegicus | 3 | 0.7603 |
| Riboflavin synthase | P0AFU8 | RISA_ECOLI | Escherichia coli | 3 | 0.7586 |
| Soluble acetylcholine receptor | Q8WSF8 | Q8WSF8_APLCA | Aplysia californica | 3 | 0.7550 |
| Basic phospholipase A2 VRV-PL-VIIIa | P59071 | PA2B8_DABRR | Daboia russelii | 2 | 0.7506 |
| Basic phospholipase A2 VRV-PL-VIIIa | P59071 | PA2B8_DABRR | Daboia russelii | 2 | 0.7496 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 2 | 0.7443 |
| HTH-type transcriptional regulator QacR | P0A0N4 | QACR_STAAU | Staphylococcus aureus | 3 | 0.7317 |
| HTH-type transcriptional regulator QacR | P0A0N3 | QACR_STAAM | Staphylococcus aureus | 3 | 0.7280 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 3 | 0.7276 |
| Acetolactate synthase, chloroplastic | P17597 | ILVB_ARATH | Arabidopsis thaliana | 2 | 0.7192 |
| Lactotransferrin | P24627 | TRFL_BOVIN | Bos taurus | 2 | 0.7102 |
| Nuclear receptor subfamily 4immunitygroup A member 1 | P22736 | NR4A1_HUMAN | Homo sapiens | 3 | 0.7037 |