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Islandicin
- Family: Plantae - Liliaceae
- Kingdom: Plantae
-
Class: Quinone
- Subclass: Anthraquinone
| Canonical Smiles | Oc1c(C)cc(c2c1C(=O)c1cccc(c1C2=O)O)O |
|---|---|
| InChI | InChI=1S/C15H10O5/c1-6-5-9(17)11-12(13(6)18)14(19)7-3-2-4-8(16)10(7)15(11)20/h2-5,16-18H,1H3 |
| InChIKey | FHFHNVHRVKQQHN-UHFFFAOYSA-N |
| Formula | C15H10O5 |
| HBA | 5 |
| HBD | 3 |
| MW | 270.24 |
| Rotatable Bonds | 0 |
| TPSA | 94.83 |
| LogP | 1.89 |
| Number Rings | 3 |
| Number Aromatic Rings | 2 |
| Heavy Atom Count | 20 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.07 |
| Exact Mass | 270.05 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Bulbine abyssinica | Asphodelaceae | Plantae | 2511937 |
| 2 | Rumex abysinicus | Polygonaceae | Plantae | 273505 |
| 3 | Kniphofia species | Liliaceae | Plantae | 49723 |
| 4 | Kniphofia species | Liliaceae | Plantae | 49723 |
Showing of synonyms
Islandicin
Rhodomycin
1,4,5-Trihydroxy-2-methylanthracene-9,10-dione
Funiculosin (anthraquinone)
1,4,5-Trihydroxy-2-methylanthraquinone
CCRIS 3476
VVJ2ULR2M5
EINECS 207-506-2
BRN 2059061
1,4,5-Trihydroxy-2-methyl-9,10-anthracenedione
UNII-VVJ2ULR2M5
NSC-264955
DTXSID70197214
4-08-00-03572 (Beilstein Handbook Reference)
DTXCID80119705
1401-16-7
Epsilon-rhodomycin
Fhfhnvhrvkqqhn-uhfffaoysa-n
Rhodomycelin
476-56-2
FUNICULOSIN
ISLANDIN
NSC 264955
NSC264955
ANTHRAQUINONE, 1,4,5-TRIHYDROXY-2-METHYL-
9,10-Anthracenedione, 1,4,5-trihydroxy-2-methyl-
CHEBI:80733
Funiculosin (VAN)
1,4,5-Trihydroxy-2-methylanthra-9,10-quinone
CHEMBL477724
SCHEMBL9172900
9, 1,4,5-trihydroxy-2-methyl-
Anthraquinone,4,5-trihydroxy-2-methyl-
NCI60_002123
DB-051465
NS00031712
1,4,5-Trihydroxy-2-methylanthra-9,10-quinone #
1,4,5-trihydroxy-2-methyl-anthracene-9,10-dione
Q27149783
1,4,5-trihydroxy-2-methyl-9,10-dihydroanthracene-9,10-dione
- Yenesew A, Wondimu A, et al. (1988). A comparative study of anthraquinones in rhizomes of Kniphofia species.. Biochemical systematics and ecology,1988,16(2),157-159. [View] [PubMed]
- Berhanu E, Fetene M, et al. (1986). Anthraquinones as taxonomic markers in Ethiopian Kniphofia species.. Phytochemistry,1986,25(4),847-850. [View] [PubMed]
- Bizuayehu Z, Ashebir F. (2012). Phytochemical investigation on the root of Rumex abyssinicus (Makmako). M.Sc. Thesis, Addis Ababa University, Ethiopia,2012. [View] [PubMed]
- Wanjohi JM, Yenesew A, et al. (2005). Three dimeric anthracene derivatives from the fruits of Bulbine abyssinica. Tetrahedron,2005,61(10),2667-2674. [View] [PubMed]
Pubchem:
10151
Cas:
1401-16-7
Zinc:
ZINC000005212248
Kegg Ligand:
C16796
Chebi:
80733
Nmrshiftdb2:
60060499
Chembl:
CHEMBL477724
Comptox:
DTXSID70197214
CPRiL:
20289
SMILES: c1cccc(c12)C(=O)c3c(C2=O)cccc3
Level: 0
Mol. Weight: 270.24 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -4.72
- Human Oral Bioavailability 20%
- Non-Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.790
- Human Oral Bioavailability 50%
- Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -1.39
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Non-Penetrable
- Fraction Unbound (Human)
- 0.920
- Plasma Protein Binding
- 62.53
- Steady State Volume of Distribution
- -
Metabolism
- Breast Cancer Resistance Protein
- Inhibitor
- CYP 1A2 Inhibitor
- Inhibitor
- CYP 1A2 Substrate
- Substrate
- CYP 2C19 Inhibitor
- 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
- Non-Inhibitor
- OATP1B3
- Non-Inhibitor
Excretion
- Clearance
- 7.390
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Toxic
- Avian
- Safe
- Bee
- Safe
- Bioconcentration Factor
- 1.140
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Toxic
- Liver Injury I (DILI)
- Toxic
- Eye Corrosion
- Safe
- Eye Irritation
- Toxic
- Maximum Tolerated Dose
- 1.240
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 5.370
- 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
- 4.580
- Rat (Acute)
- 2.620
- Rat (Chronic Oral)
- 3.440
- Fathead Minnow
- 4.170
- Respiratory Disease
- Safe
- Skin Sensitisation
- Safe
- SR-ARE
- Toxic
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Toxic
- SR-p53
- Safe
General Properties
- Boiling Point
- 420.310
- Hydration Free Energy
- -9.140
- Log(D) at pH=7.4
- 2.550
- Log(P)
- 3.83
- Log S
- -5.52
- Log(Vapor Pressure)
- -7.19
- Melting Point
- 205.5
- pKa Acid
- 5.63
- pKa Basic
- 5.49
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A | Q9Y233 | PDE10_HUMAN | Homo sapiens | 3 | 0.9289 |
| cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A | Q9Y233 | PDE10_HUMAN | Homo sapiens | 3 | 0.9289 |
| Flavin reductase (NADPH) | P30043 | BLVRB_HUMAN | Homo sapiens | 3 | 0.9125 |
| Flavin reductase (NADPH) | P30043 | BLVRB_HUMAN | Homo sapiens | 3 | 0.9125 |
| Sulfide-quinone reductase | B7JBP8 | SQRD_ACIF2 | Acidithiobacillus ferrooxidans) | 3 | 0.8698 |
| Sulfide-quinone reductase | B7JBP8 | SQRD_ACIF2 | Acidithiobacillus ferrooxidans) | 3 | 0.8698 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 3 | 0.8573 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 3 | 0.8573 |
| Nitric oxide synthase 1 | P29476 | NOS1_RAT | Rattus norvegicus | 5 | 0.8428 |
| Nitric oxide synthase 1 | P29476 | NOS1_RAT | Rattus norvegicus | 5 | 0.8428 |
| Fibroblast growth factor receptor 1 | P11362 | FGFR1_HUMAN | Homo sapiens | 3 | 0.8371 |
| Fibroblast growth factor receptor 1 | P11362 | FGFR1_HUMAN | Homo sapiens | 3 | 0.8371 |
| Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase | F6MZ55 | F6MZ55_9FIRM | Sporomusa ovata | 3 | 0.8364 |
| Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase | F6MZ55 | F6MZ55_9FIRM | Sporomusa ovata | 3 | 0.8364 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 3 | 0.8306 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 3 | 0.8306 |
| Protein ppBat | Q8A8A4 | Q8A8A4_BACTN | Bacteroides thetaiotaomicron VPI-5482 | 3 | 0.8184 |
| Protein ppBat | Q8A8A4 | Q8A8A4_BACTN | Bacteroides thetaiotaomicron VPI-5482 | 3 | 0.8184 |
| ActVA 6 protein | Q53908 | Q53908_STRCH | Streptomyces coelicolor | 4 | 0.8096 |
| ActVA 6 protein | Q53908 | Q53908_STRCH | Streptomyces coelicolor | 4 | 0.8096 |
| 11-beta-hydroxysteroid dehydrogenase 1 | P28845 | DHI1_HUMAN | Homo sapiens | 3 | 0.8024 |
| 11-beta-hydroxysteroid dehydrogenase 1 | P28845 | DHI1_HUMAN | Homo sapiens | 3 | 0.8024 |
| 3-phosphoinositide-dependent protein kinase 1 | O15530 | PDPK1_HUMAN | Homo sapiens | 4 | 0.7978 |
| 3-phosphoinositide-dependent protein kinase 1 | O15530 | PDPK1_HUMAN | Homo sapiens | 4 | 0.7978 |
| Nitric oxide synthase oxygenase | O34453 | NOSO_BACSU | Bacillus subtilis | 4 | 0.7927 |
| Nitric oxide synthase oxygenase | O34453 | NOSO_BACSU | Bacillus subtilis | 4 | 0.7927 |
| Cell division cycle 7-related protein kinase | O00311 | CDC7_HUMAN | Homo sapiens | 4 | 0.7869 |
| Cell division cycle 7-related protein kinase | O00311 | CDC7_HUMAN | Homo sapiens | 4 | 0.7869 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 3 | 0.7813 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 3 | 0.7813 |
| Sulfotransferase 1E1 | P49888 | ST1E1_HUMAN | Homo sapiens | 3 | 0.7730 |
| Sulfotransferase 1E1 | P49888 | ST1E1_HUMAN | Homo sapiens | 3 | 0.7730 |
| Cathepsin S | P25774 | CATS_HUMAN | Homo sapiens | 3 | 0.7726 |
| Cathepsin S | P25774 | CATS_HUMAN | Homo sapiens | 3 | 0.7726 |
| Cytosolic purine 5'-nucleotidase | P49902 | 5NTC_HUMAN | Homo sapiens | 2 | 0.7614 |
| Cytosolic purine 5'-nucleotidase | P49902 | 5NTC_HUMAN | Homo sapiens | 2 | 0.7614 |
| Mitogen-activated protein kinase 10 | P53779 | MK10_HUMAN | Homo sapiens | 3 | 0.7589 |
| Mitogen-activated protein kinase 10 | P53779 | MK10_HUMAN | Homo sapiens | 3 | 0.7589 |
| Calmodulin | P62157 | CALM_BOVIN | Bos taurus | 3 | 0.7558 |
| Calmodulin | P62157 | CALM_BOVIN | Bos taurus | 3 | 0.7558 |
| Bromodomain-containing protein 4 | O60885 | BRD4_HUMAN | Homo sapiens | 4 | 0.7544 |
| Bromodomain-containing protein 4 | O60885 | BRD4_HUMAN | Homo sapiens | 4 | 0.7544 |
| Thiamine-phosphate synthase | P39594 | THIE_BACSU | Bacillus subtilis | 3 | 0.7532 |
| Thiamine-phosphate synthase | P39594 | THIE_BACSU | Bacillus subtilis | 3 | 0.7532 |
| Vascular endothelial growth factor receptor 2 | P35968 | VGFR2_HUMAN | Homo sapiens | 3 | 0.7489 |
| Vascular endothelial growth factor receptor 2 | P35968 | VGFR2_HUMAN | Homo sapiens | 3 | 0.7489 |
| Bromodomain-containing protein 4 | O60885 | BRD4_HUMAN | Homo sapiens | 3 | 0.7476 |
| Bromodomain-containing protein 4 | O60885 | BRD4_HUMAN | Homo sapiens | 3 | 0.7476 |
| Bromodomain-containing protein 4 | O60885 | BRD4_HUMAN | Homo sapiens | 3 | 0.7454 |
| Bromodomain-containing protein 4 | O60885 | BRD4_HUMAN | Homo sapiens | 3 | 0.7454 |
| Nitric oxide synthase 1 | P29476 | NOS1_RAT | Rattus norvegicus | 5 | 0.7449 |
| Nitric oxide synthase 1 | P29476 | NOS1_RAT | Rattus norvegicus | 5 | 0.7449 |
| Bromodomain-containing protein 4 | O60885 | BRD4_HUMAN | Homo sapiens | 3 | 0.7443 |
| Bromodomain-containing protein 4 | O60885 | BRD4_HUMAN | Homo sapiens | 3 | 0.7443 |
| Serine/threonine-protein kinase Chk1 | O14757 | CHK1_HUMAN | Homo sapiens | 3 | 0.7430 |
| Serine/threonine-protein kinase Chk1 | O14757 | CHK1_HUMAN | Homo sapiens | 3 | 0.7430 |
| Nuclear receptor subfamily 4immunitygroup A member 1 | P22736 | NR4A1_HUMAN | Homo sapiens | 3 | 0.7402 |
| Nuclear receptor subfamily 4immunitygroup A member 1 | P22736 | NR4A1_HUMAN | Homo sapiens | 3 | 0.7402 |
| Transcriptional regulator, PadR-like family | A2RI36 | A2RI36_LACLM | Lactococcus lactis subsp. cremoris | 2 | 0.7401 |
| Transcriptional regulator, PadR-like family | A2RI36 | A2RI36_LACLM | Lactococcus lactis subsp. cremoris | 2 | 0.7401 |
| Tyrosine-protein kinase Lck | P06239 | LCK_HUMAN | Homo sapiens | 3 | 0.7368 |
| Tyrosine-protein kinase Lck | P06239 | LCK_HUMAN | Homo sapiens | 3 | 0.7368 |
| Stromelysin-1 | P08254 | MMP3_HUMAN | Homo sapiens | 3 | 0.7363 |
| Stromelysin-1 | P08254 | MMP3_HUMAN | Homo sapiens | 3 | 0.7363 |
| Serine/threonine-protein kinase pim-1 | P11309 | PIM1_HUMAN | Homo sapiens | 3 | 0.7279 |
| Serine/threonine-protein kinase pim-1 | P11309 | PIM1_HUMAN | Homo sapiens | 3 | 0.7279 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 2 | 0.7272 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 2 | 0.7272 |
| Carbonic anhydrase 12 | O43570 | CAH12_HUMAN | Homo sapiens | 2 | 0.7230 |
| Carbonic anhydrase 12 | O43570 | CAH12_HUMAN | Homo sapiens | 2 | 0.7230 |
| 4-hydroxyphenylacetate 3-monooxygenase | Q8YHT7 | Q8YHT7_BRUME | Brucella melitensis biotype 1 | 2 | 0.7147 |
| 4-hydroxyphenylacetate 3-monooxygenase | Q8YHT7 | Q8YHT7_BRUME | Brucella melitensis biotype 1 | 2 | 0.7147 |
| Casein kinase II subunit alpha | P68400 | CSK21_HUMAN | Homo sapiens | 4 | 0.7120 |
| Casein kinase II subunit alpha | P68400 | CSK21_HUMAN | Homo sapiens | 4 | 0.7120 |
| Aklavinone 12-hydroxylase RdmE | Q54530 | DNRF_STREF | Streptomyces purpurascens | 4 | 0.7119 |
| Aklavinone 12-hydroxylase RdmE | Q54530 | DNRF_STREF | Streptomyces purpurascens | 4 | 0.7119 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 2 | 0.7095 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 2 | 0.7095 |
| Fructose-1,6-bisphosphatase 1 | P00636 | F16P1_PIG | Sus scrofa | 3 | 0.7086 |
| Fructose-1,6-bisphosphatase 1 | P00636 | F16P1_PIG | Sus scrofa | 3 | 0.7086 |
| Alpha-ketoglutarate-dependent dioxygenase FTO | Q9C0B1 | FTO_HUMAN | Homo sapiens | 3 | 0.7048 |
| Alpha-ketoglutarate-dependent dioxygenase FTO | Q9C0B1 | FTO_HUMAN | Homo sapiens | 3 | 0.7048 |
| Cyclin-dependent kinase 2 | P24941 | CDK2_HUMAN | Homo sapiens | 3 | 0.7041 |
| Cyclin-dependent kinase 2 | P24941 | CDK2_HUMAN | Homo sapiens | 3 | 0.7041 |
| Serine/threonine-protein kinase Chk1 | O14757 | CHK1_HUMAN | Homo sapiens | 3 | 0.7037 |
| Serine/threonine-protein kinase Chk1 | O14757 | CHK1_HUMAN | Homo sapiens | 3 | 0.7037 |
| Tyrosine 3-monooxygenase | P04177 | TY3H_RAT | Rattus norvegicus | 3 | 0.7028 |
| Tyrosine 3-monooxygenase | P04177 | TY3H_RAT | Rattus norvegicus | 3 | 0.7028 |
| cAMP-dependent protein kinase catalytic subunit alpha | P00517 | KAPCA_BOVIN | Bos taurus | 3 | 0.7027 |
| cAMP-dependent protein kinase catalytic subunit alpha | P00517 | KAPCA_BOVIN | Bos taurus | 3 | 0.7027 |
| Cyclin-dependent kinase 2 | P24941 | CDK2_HUMAN | Homo sapiens | 3 | 0.7009 |
| Cyclin-dependent kinase 2 | P24941 | CDK2_HUMAN | Homo sapiens | 3 | 0.7009 |
| Casein kinase II subunit alpha | P28523 | CSK2A_MAIZE | Zea mays | 4 | 0.7008 |
| Casein kinase II subunit alpha | P28523 | CSK2A_MAIZE | Zea mays | 4 | 0.7008 |