Select a section from the left sidebar
Harunganol B
- Family: Plantae - Hypericaceae
- Kingdom: Plantae
-
Class: Quinone
- Subclass: Anthraquinone
| Canonical Smiles | CC(=CCc1c(C)c(CC=C(C)C)c(c2c1Cc1c(C2=O)c(O)cc(c1CC=C(C)C)O)O)C |
|---|---|
| InChI | InChI=1S/C30H36O4/c1-16(2)8-11-20-19(7)21(12-9-17(3)4)29(33)28-23(20)14-24-22(13-10-18(5)6)25(31)15-26(32)27(24)30(28)34/h8-10,15,31-33H,11-14H2,1-7H3 |
| InChIKey | BYQNZJZELQIDNF-UHFFFAOYSA-N |
| Formula | C30H36O4 |
| HBA | 4 |
| HBD | 3 |
| MW | 460.61 |
| Rotatable Bonds | 6 |
| TPSA | 77.76 |
| LogP | 6.77 |
| Number Rings | 3 |
| Number Aromatic Rings | 2 |
| Heavy Atom Count | 34 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.37 |
| Exact Mass | 460.26 |
| Number of Lipinski Rule Violations | 1 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Harungana madagascariensis | Hypericaceae | Plantae | 198768 |
| 2 | Harungana madagascariensis | Hypericaceae | Plantae | 198768 |
Showing of synonyms
Harunganol B
1,6,8-trihydroxy-3-methyl-2,4,5-tris(3-methylbut-2-enyl)-10H-anthracen-9-one
84393-25-9
CHEMBL126813
SCHEMBL12774927
BDBM50060857
1,3,8-trihydroxy-4,5,7-tris-(3,3-dimethylallyl)-6-methyl-anthrone
1,6,8-Trihydroxy-3-methyl-2,4,5-tris-(3-methyl-but-2-enyl)-10H-anthracen-9-one
4,5,7-trihydroxy-2-methyl-1,3,8-tris(3-methylbut-2-enyl)anthracen-10(9H)-one
- Kouam SF, Khan SN, et al. (2006). Alpha-glucosidase inhibitory anthranols, kenganthranols A-C, from the stem bark of Harungana madagascariensis.. Journal of natural products,2006, 69(2), 229-233. [View] [PubMed]
- Kouam SF, Ngadjui BT, et al. (2005). Prenylated anthronoid antioxidants from the stem bark of Harungana madagascariensis.. Phytochemistry,2005, 66(10), 1174-1179. [View] [PubMed]
Pubchem:
44349182
Cas:
84393-25-9
Zinc:
ZINC000013606530
Nmrshiftdb2:
60044258
Chembl:
CHEMBL126813
Bindingdb:
50060857
No compound-protein relationship available.
SMILES: c1cccc(c12)Cc3c(C2=O)cccc3
Level: 0
Mol. Weight: 460.61 g/mol
Antioxidant
Absorption
- Caco-2 (logPapp)
- -5.09
- Human Oral Bioavailability 20%
- Non-Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.87
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -1.86
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 1.01
- Plasma Protein Binding
- 67.21
- Steady State Volume of Distribution
- -
Metabolism
- Breast Cancer Resistance Protein
- Inhibitor
- CYP 1A2 Inhibitor
- Inhibitor
- CYP 1A2 Substrate
- Non-Substrate
- CYP 2C19 Inhibitor
- Inhibitor
- CYP 2C19 Substrate
- Substrate
- CYP 2C9 Inhibitor
- 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
- 5.27
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- 0.87
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Toxic
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Toxic
- Maximum Tolerated Dose
- 0.43
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 6.88
- Micronucleos
- Toxic
- NR-AhR
- Safe
- 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
- -96.3
- Rat (Acute)
- 1.89
- Rat (Chronic Oral)
- 3.15
- Fathead Minnow
- 5.78
- Respiratory Disease
- Toxic
- Skin Sensitisation
- Toxic
- SR-ARE
- Toxic
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Toxic
- SR-p53
- Toxic
General Properties
- Boiling Point
- 503.28
- Hydration Free Energy
- -3.47
- Log(D) at pH=7.4
- 4.86
- Log(P)
- 9.38
- Log S
- -6.88
- Log(Vapor Pressure)
- -9.34
- Melting Point
- 187.06
- pKa Acid
- 8.84
- pKa Basic
- 7.23
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.9155 |
| cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A | Q9Y233 | PDE10_HUMAN | Homo sapiens | 3 | 0.8932 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.8868 |
| Epidermal growth factor receptor | P00533 | EGFR_HUMAN | Homo sapiens | 3 | 0.8804 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.8794 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.8754 |
| Riboflavin synthase | P0AFU8 | RISA_ECOLI | Escherichia coli | 4 | 0.8714 |
| Epidermal growth factor receptor | P00533 | EGFR_HUMAN | Homo sapiens | 3 | 0.8682 |
| Retinol-binding protein 1 | P02696 | RET1_RAT | Rattus norvegicus | 3 | 0.8436 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.8339 |
| Photosynthetic reaction center cytochrome c subunit | P07173 | CYCR_BLAVI | Blastochloris viridis | 3 | 0.8250 |
| Ribosomal small subunit pseudouridine synthase A | P0AA43 | RSUA_ECOLI | Escherichia coli | 3 | 0.7964 |
| Fibroblast growth factor receptor 1 | P11362 | FGFR1_HUMAN | Homo sapiens | 3 | 0.7928 |
| Basic phospholipase A2 VRV-PL-VIIIa | P59071 | PA2B8_DABRR | Daboia russelii | 4 | 0.7825 |
| Aldo-keto reductase family 1 member C3 | P42330 | AK1C3_HUMAN | Homo sapiens | 3 | 0.7795 |
| Sodium-dependent dopamine transporter | Q7K4Y6 | DAT_DROME | Drosophila melanogaster | 2 | 0.7603 |
| Lactotransferrin | P24627 | TRFL_BOVIN | Bos taurus | 2 | 0.7581 |
| High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A | O76083 | PDE9A_HUMAN | Homo sapiens | 4 | 0.7579 |
| High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A | O76083 | PDE9A_HUMAN | Homo sapiens | 4 | 0.7576 |
| Heat shock protein HSP 90-alpha | P07900 | HS90A_HUMAN | Homo sapiens | 3 | 0.7506 |
| Vascular endothelial growth factor receptor 2 | P35968 | VGFR2_HUMAN | Homo sapiens | 3 | 0.7445 |
| Soluble cytochrome b562 | P0ABE7 | C562_ECOLX | Escherichia coli | 3 | 0.7371 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 2 | 0.7305 |
| 3-alpha-hydroxysteroid dehydrogenase | P23457 | DIDH_RAT | Rattus norvegicus | 2 | 0.7287 |
| Vitamin D(3) 25-hydroxylase | C4B644 | CPVDH_PSEAH | Pseudonocardia autotrophica | 3 | 0.7286 |
| Transcriptional regulator, PadR-like family | A2RI36 | A2RI36_LACLM | Lactococcus lactis subsp. cremoris | 2 | 0.7205 |
| prolyl oligopeptidase | Q9X6R4 | Q9X6R4_AERCA | Aeromonas caviae | 3 | 0.7190 |
| HTH-type transcriptional regulator QacR | P0A0N3 | QACR_STAAM | Staphylococcus aureus | 3 | 0.7186 |
| 11-beta-hydroxysteroid dehydrogenase 1 | P28845 | DHI1_HUMAN | Homo sapiens | 3 | 0.7179 |
| Casein kinase II subunit alpha | P68400 | CSK21_HUMAN | Homo sapiens | 3 | 0.7135 |
| Chitinase A | Q9AMP1 | Q9AMP1_VIBHA | Vibrio harveyi | 2 | 0.7086 |
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.7073 |
| CmeR | Q7B8P6 | Q7B8P6_CAMJU | Campylobacter jejuni | 2 | 0.7067 |
| Thymidylate synthase | P00469 | TYSY_LACCA | Lacticaseibacillus casei | 4 | 0.7066 |
| Basic phospholipase A2 VRV-PL-VIIIa | P59071 | PA2B8_DABRR | Daboia russelii | 3 | 0.7056 |
| Lactoperoxidase | P80025 | PERL_BOVIN | Bos taurus | 3 | 0.7048 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 3 | 0.7028 |
| Cathepsin S | P25774 | CATS_HUMAN | Homo sapiens | 3 | 0.7028 |
| UDP-galactopyranose mutase | Q48485 | GLF1_KLEPN | Klebsiella pneumoniae | 3 | 0.7013 |