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Busseihydroquinone D
- Family: Plantae - Rubiaceae
- Kingdom: Plantae
-
Class: Quinone
- Subclass: Naphthohydroquinone
| Canonical Smiles | O=C/C(=C/1\CCC2(C1=Cc1c(O2)ccc2c1c(OC)cc(c2O)C(=O)O)C)/C |
|---|---|
| InChI | InChI=1S/C22H20O6/c1-11(10-23)12-6-7-22(2)16(12)8-14-17(28-22)5-4-13-19(14)18(27-3)9-15(20(13)24)21(25)26/h4-5,8-10,24H,6-7H2,1-3H3,(H,25,26)/b12-11+ |
| InChIKey | ZSKLSJMYNRFZJZ-VAWYXSNFSA-N |
| Formula | C22H20O6 |
| HBA | 5 |
| HBD | 2 |
| MW | 380.4 |
| Rotatable Bonds | 3 |
| TPSA | 93.06 |
| LogP | 4.1 |
| Number Rings | 4 |
| Number Aromatic Rings | 2 |
| Heavy Atom Count | 28 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.27 |
| Exact Mass | 380.13 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Pentas bussei | Rubiaceae | Plantae | 387051 |
| 2 | Pentas bussei | Rubiaceae | Plantae | 387051 |
Showing of synonyms
Busseihydroquinone D
(15E)-6-hydroxy-3-methoxy-12-methyl-15-(1-oxopropan-2-ylidene)-11-oxatetracyclo(8.7.0.02,7.012,16)heptadeca-1(10),2,4,6,8,16-hexaene-5-carboxylic acid
(15E)-6-hydroxy-3-methoxy-12-methyl-15-(1-oxopropan-2-ylidene)-11-oxatetracyclo[8.7.0.02,7.012,16]heptadeca-1(10),2,4,6,8,16-hexaene-5-carboxylic acid
CHEMBL2071296
- Endale M, Ekberg A, et al. (2012). Busseihydroquinones A-D from the roots of Pentas bussei. Journal of Natural Products,2012,75(7),1299-1304. [View] [PubMed]
- Abdissa N, Pan F, et al. (2016). Naphthalene derivatives from the roots of Pentas parvifolia and Pentas bussei. Journal of Natural Products,2016,79(9),2181-2187. [View] [PubMed]
No compound-protein relationship available.
SMILES: C=C1CCC(C1=2)Oc3c(C2)c4c(cc3)cccc4
Level: 0
Mol. Weight: 380.4 g/mol
Antimalarial
Absorption
- Caco-2 (logPapp)
- -4.73
- Human Oral Bioavailability 20%
- Non-Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.9
- Human Oral Bioavailability 50%
- Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -0.58
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Non-Penetrable
- Fraction Unbound (Human)
- 1.14
- Plasma Protein Binding
- 49.67
- Steady State Volume of Distribution
- -
Metabolism
- Breast Cancer Resistance Protein
- Non-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
- 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
- 3.74
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- -0.37
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Toxic
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 0.16
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 5.34
- 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
- -8.64
- Rat (Acute)
- 2.69
- Rat (Chronic Oral)
- 3.37
- Fathead Minnow
- 4.9
- Respiratory Disease
- Toxic
- Skin Sensitisation
- Safe
- SR-ARE
- Toxic
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Safe
- SR-p53
- Safe
General Properties
- Boiling Point
- 446.19
- Hydration Free Energy
- -5.03
- Log(D) at pH=7.4
- 1.84
- Log(P)
- 5.21
- Log S
- -4.02
- Log(Vapor Pressure)
- -8.08
- Melting Point
- 205.26
- pKa Acid
- 7.24
- pKa Basic
- 5.07
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Anthranilate phosphoribosyltransferase | P9WFX5 | TRPD_MYCTU | Mycobacterium tuberculosis | 3 | 0.8768 |
| Anthranilate phosphoribosyltransferase | P9WFX5 | TRPD_MYCTU | Mycobacterium tuberculosis | 3 | 0.8768 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 3 | 0.8432 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 3 | 0.8432 |
| Fatty acid-binding protein, liver | P80226 | FABPL_CHICK | Gallus gallus | 3 | 0.8286 |
| Fatty acid-binding protein, liver | P80226 | FABPL_CHICK | Gallus gallus | 3 | 0.8286 |
| High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A | O76083 | PDE9A_HUMAN | Homo sapiens | 3 | 0.8117 |
| High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A | O76083 | PDE9A_HUMAN | Homo sapiens | 3 | 0.8117 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 2 | 0.7761 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 2 | 0.7761 |
| Beta-galactoside-specific lectin 4 | Q6ITZ3 | ML4_VISAL | Viscum album | 3 | 0.7444 |
| Beta-galactoside-specific lectin 4 | Q6ITZ3 | ML4_VISAL | Viscum album | 3 | 0.7444 |
| rRNA N-glycosylase | D9J2T9 | D9J2T9_MOMBA | Momordica balsamina | 3 | 0.7394 |
| rRNA N-glycosylase | D9J2T9 | D9J2T9_MOMBA | Momordica balsamina | 3 | 0.7394 |
| 3-phosphoinositide-dependent protein kinase 1 | O15530 | PDPK1_HUMAN | Homo sapiens | 3 | 0.7225 |
| 3-phosphoinositide-dependent protein kinase 1 | O15530 | PDPK1_HUMAN | Homo sapiens | 3 | 0.7225 |
| Methylketone synthase I | E0YCS2 | E0YCS2_SOLHA | Solanum habrochaites | 3 | 0.7098 |
| Methylketone synthase I | E0YCS2 | E0YCS2_SOLHA | Solanum habrochaites | 3 | 0.7098 |
| Class 10 plant pathogenesis-related protein 2B | Q9LLQ2 | P102B_LUPLU | Lupinus luteus | 2 | 0.7012 |
| Class 10 plant pathogenesis-related protein 2B | Q9LLQ2 | P102B_LUPLU | Lupinus luteus | 2 | 0.7012 |