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Helminthosporin
- Family: Plantae - Asphodelaceae
- Kingdom: Plantae
-
Class: Quinone
- Subclass: Anthraquinone
| Canonical Smiles | Cc1cc(O)c2c(c1)C(=O)c1c(C2=O)c(O)ccc1O |
|---|---|
| InChI | InChI=1S/C15H10O5/c1-6-4-7-11(10(18)5-6)15(20)13-9(17)3-2-8(16)12(13)14(7)19/h2-5,16-18H,1H3 |
| InChIKey | YOOXNSPYGCZLAX-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 | Aloe dawei | Asphodelaceae | Plantae | 1331517 |
| 2 | Aloe secundiflora | Asphodelaceae | Plantae | 1593107 |
| 3 | Aloe saponaria | Asphodelaceae | Plantae | 1155789 |
| 4 | Aloe graminicola | Liliaceae | Plantae | 330741 |
| 5 | Aloe species | Liliaceae | Plantae | 117795 |
| 6 | Kniphofia reflexa | Asphodelaceae | Plantae | 49723 |
Showing of synonyms
Helminthosporin
518-80-9
1,5,8-trihydroxy-3-methylanthracene-9,10-dione
MCD0C88HYI
1,5,8-Trihydroxy-3-methylanthraquinone
NSC-132600
3-METHYL-1,5,8-TRIHYDROXYANTHRAQUINONE
9,10-Anthracenedione, 1,5,8-trihydroxy-3-methyl-
Anthraquinone, 1,5,8-trihydroxy-3-methyl-
UNII-MCD0C88HYI
NSC132600
NSC 132600
SCHEMBL9170655
DTXSID70199738
9, 1,5,8-trihydroxy-3-methyl-
Anthraquinone,5,8-trihydroxy-3-methyl-
Q27283860
1,5,8-TRIHYDROXY-3-METHYL-9,10-DIHYDROANTHRACENE-9,10-DIONE
- Yenesew A, Ogur JA, et al. (1993). (R)-Prechrysophanol from Aloe graminicola.. Phytochemistry,1993,34(5),1442-1444. [View] [PubMed]
- Dagne E, Yenesew A, et al. (1994). Anthraquinones, pre-anthraquinones and isoeleutherol in the roots of Aloe species.. Phytochemistry,1994,35(2),401-406. [View] [PubMed]
- Abdissa N, Induli M, et al. (2014). Cytotoxic quinones from the roots of Aloe dawei. Molecules,2014,19(3),3264-3273. [View] [PubMed]
- Sema D, Lannang A, et al. (2022). In Vitro and in Vivo Evaluation of the Antimalarial Activities of Kniphofia reflexa Hutchinson ex Codd. Natural Product Communications, 2022, 17(10). [View]
- Induli M, Cheloti M, et al. (2012). Naphthoquinones from the roots of Aloe secundiflora. Phytochemistry Letters,2012,5(3),506-509. [View] [PubMed]
- Dagne E. (1996). Review of the chemistry of Aloes of Africa. Bulletin of the Chemical Society of Ethiopia,1996,10(1),89-103. [View] [PubMed]
No compound-protein relationship available.
SMILES: c1cccc(c12)C(=O)c3c(C2=O)cccc3
Level: 0
Mol. Weight: 270.24 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -4.92
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.85
- Human Oral Bioavailability 50%
- Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -1.59
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Non-Penetrable
- Fraction Unbound (Human)
- 0.81
- Plasma Protein Binding
- 65.08
- 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
- Inhibitor
- CYP 3A4 Substrate
- Non-Substrate
- OATP1B1
- Non-Inhibitor
- OATP1B3
- Non-Inhibitor
Excretion
- Clearance
- 6.99
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Toxic
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- 0.89
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Toxic
- Liver Injury I (DILI)
- Toxic
- Eye Corrosion
- Safe
- Eye Irritation
- Toxic
- Maximum Tolerated Dose
- 0.99
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 4.88
- 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
- 4.72
- Rat (Acute)
- 2.52
- Rat (Chronic Oral)
- 3.37
- Fathead Minnow
- 4.1
- 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
- 429.93
- Hydration Free Energy
- -9.92
- Log(D) at pH=7.4
- 2.51
- Log(P)
- 3.79
- Log S
- -5.85
- Log(Vapor Pressure)
- -7.11
- Melting Point
- 227.75
- pKa Acid
- 6.53
- pKa Basic
- 5.12
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Flavin reductase (NADPH) | P30043 | BLVRB_HUMAN | Homo sapiens | 3 | 0.9436 |
| Flavin reductase (NADPH) | P30043 | BLVRB_HUMAN | Homo sapiens | 3 | 0.9436 |
| cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A | Q9Y233 | PDE10_HUMAN | Homo sapiens | 3 | 0.9301 |
| cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A | Q9Y233 | PDE10_HUMAN | Homo sapiens | 3 | 0.9301 |
| Fibroblast growth factor receptor 1 | P11362 | FGFR1_HUMAN | Homo sapiens | 3 | 0.9299 |
| Fibroblast growth factor receptor 1 | P11362 | FGFR1_HUMAN | Homo sapiens | 3 | 0.9299 |
| Serine/threonine-protein kinase Chk1 | O14757 | CHK1_HUMAN | Homo sapiens | 3 | 0.8803 |
| Serine/threonine-protein kinase Chk1 | O14757 | CHK1_HUMAN | Homo sapiens | 3 | 0.8803 |
| Nitric oxide synthase oxygenase | O34453 | NOSO_BACSU | Bacillus subtilis | 4 | 0.8798 |
| Nitric oxide synthase oxygenase | O34453 | NOSO_BACSU | Bacillus subtilis | 4 | 0.8798 |
| E3 ubiquitin-protein ligase Mdm2 | P56273 | MDM2_XENLA | Xenopus laevis | 3 | 0.8616 |
| E3 ubiquitin-protein ligase Mdm2 | P56273 | MDM2_XENLA | Xenopus laevis | 3 | 0.8616 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 3 | 0.8504 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 3 | 0.8504 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 3 | 0.8319 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 3 | 0.8319 |
| Cell division cycle 7-related protein kinase | O00311 | CDC7_HUMAN | Homo sapiens | 4 | 0.8234 |
| Cell division cycle 7-related protein kinase | O00311 | CDC7_HUMAN | Homo sapiens | 4 | 0.8234 |
| Nitric oxide synthase 1 | P29476 | NOS1_RAT | Rattus norvegicus | 5 | 0.8155 |
| Nitric oxide synthase 1 | P29476 | NOS1_RAT | Rattus norvegicus | 5 | 0.8155 |
| Sulfotransferase 1E1 | P49888 | ST1E1_HUMAN | Homo sapiens | 3 | 0.8108 |
| Sulfotransferase 1E1 | P49888 | ST1E1_HUMAN | Homo sapiens | 3 | 0.8108 |
| 3-phosphoinositide-dependent protein kinase 1 | O15530 | PDPK1_HUMAN | Homo sapiens | 4 | 0.8089 |
| 3-phosphoinositide-dependent protein kinase 1 | O15530 | PDPK1_HUMAN | Homo sapiens | 4 | 0.8089 |
| E3 ubiquitin-protein ligase Mdm2 | Q00987 | MDM2_HUMAN | Homo sapiens | 3 | 0.8039 |
| E3 ubiquitin-protein ligase Mdm2 | Q00987 | MDM2_HUMAN | Homo sapiens | 3 | 0.8039 |
| ActVA 6 protein | Q53908 | Q53908_STRCH | Streptomyces coelicolor | 4 | 0.8005 |
| ActVA 6 protein | Q53908 | Q53908_STRCH | Streptomyces coelicolor | 4 | 0.8005 |
| Sulfide-quinone reductase | B7JBP8 | SQRD_ACIF2 | Acidithiobacillus ferrooxidans) | 3 | 0.7987 |
| Sulfide-quinone reductase | B7JBP8 | SQRD_ACIF2 | Acidithiobacillus ferrooxidans) | 3 | 0.7987 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 3 | 0.7965 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 3 | 0.7965 |
| Protein ppBat | Q8A8A4 | Q8A8A4_BACTN | Bacteroides thetaiotaomicron VPI-5482 | 3 | 0.7767 |
| Protein ppBat | Q8A8A4 | Q8A8A4_BACTN | Bacteroides thetaiotaomicron VPI-5482 | 3 | 0.7767 |
| Casein kinase II subunit alpha | P28523 | CSK2A_MAIZE | Zea mays | 4 | 0.7754 |
| Casein kinase II subunit alpha | P28523 | CSK2A_MAIZE | Zea mays | 4 | 0.7754 |
| Prostaglandin E synthase 2 | Q9N0A4 | PGES2_MACFA | Macaca fascicularis | 3 | 0.7742 |
| Prostaglandin E synthase 2 | Q9N0A4 | PGES2_MACFA | Macaca fascicularis | 3 | 0.7742 |
| Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase | F6MZ55 | F6MZ55_9FIRM | Sporomusa ovata | 3 | 0.7721 |
| Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase | F6MZ55 | F6MZ55_9FIRM | Sporomusa ovata | 3 | 0.7721 |
| Glycogen synthase kinase-3 beta | P49841 | GSK3B_HUMAN | Homo sapiens | 3 | 0.7711 |
| Glycogen synthase kinase-3 beta | P49841 | GSK3B_HUMAN | Homo sapiens | 3 | 0.7711 |
| Transcriptional regulator, PadR-like family | A2RI36 | A2RI36_LACLM | Lactococcus lactis subsp. cremoris | 2 | 0.7702 |
| Transcriptional regulator, PadR-like family | A2RI36 | A2RI36_LACLM | Lactococcus lactis subsp. cremoris | 2 | 0.7702 |
| Casein kinase II subunit alpha | P28523 | CSK2A_MAIZE | Zea mays | 4 | 0.7678 |
| Casein kinase II subunit alpha | P28523 | CSK2A_MAIZE | Zea mays | 4 | 0.7678 |
| Tyrosine-protein kinase Lck | P06239 | LCK_HUMAN | Homo sapiens | 3 | 0.7672 |
| Tyrosine-protein kinase Lck | P06239 | LCK_HUMAN | Homo sapiens | 3 | 0.7672 |
| Ribosyldihydronicotinamide dehydrogenase [quinone] | P16083 | NQO2_HUMAN | Homo sapiens | 3 | 0.7622 |
| Ribosyldihydronicotinamide dehydrogenase [quinone] | P16083 | NQO2_HUMAN | Homo sapiens | 3 | 0.7622 |
| Vascular endothelial growth factor receptor 2 | P35968 | VGFR2_HUMAN | Homo sapiens | 3 | 0.7620 |
| Vascular endothelial growth factor receptor 2 | P35968 | VGFR2_HUMAN | Homo sapiens | 3 | 0.7620 |
| Methionine aminopeptidase 2 | P50579 | MAP2_HUMAN | Homo sapiens | 3 | 0.7582 |
| Methionine aminopeptidase 2 | P50579 | MAP2_HUMAN | Homo sapiens | 3 | 0.7582 |
| Polyprotein | Q80J95 | Q80J95_9CALI | Murine norovirus 1 | 3 | 0.7563 |
| Polyprotein | Q80J95 | Q80J95_9CALI | Murine norovirus 1 | 3 | 0.7563 |
| Tyrosine-protein kinase Lyn | P25911 | LYN_MOUSE | Mus musculus | 4 | 0.7560 |
| Tyrosine-protein kinase Lyn | P25911 | LYN_MOUSE | Mus musculus | 4 | 0.7560 |
| Cyclin-dependent kinase 9 | P50750 | CDK9_HUMAN | Homo sapiens | 3 | 0.7490 |
| Cyclin-dependent kinase 9 | P50750 | CDK9_HUMAN | Homo sapiens | 3 | 0.7490 |
| Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform | P48736 | PK3CG_HUMAN | Homo sapiens | 3 | 0.7435 |
| Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform | P48736 | PK3CG_HUMAN | Homo sapiens | 3 | 0.7435 |
| Mitogen-activated protein kinase 14 | Q16539 | MK14_HUMAN | Homo sapiens | 3 | 0.7434 |
| Mitogen-activated protein kinase 14 | Q16539 | MK14_HUMAN | Homo sapiens | 3 | 0.7434 |
| Riboflavin synthase | P0AFU8 | RISA_ECOLI | Escherichia coli | 3 | 0.7422 |
| Riboflavin synthase | P0AFU8 | RISA_ECOLI | Escherichia coli | 3 | 0.7422 |
| Serine/threonine-protein kinase pim-1 | P11309 | PIM1_HUMAN | Homo sapiens | 3 | 0.7398 |
| Serine/threonine-protein kinase pim-1 | P11309 | PIM1_HUMAN | Homo sapiens | 3 | 0.7398 |
| Mitogen-activated protein kinase 10 | P53779 | MK10_HUMAN | Homo sapiens | 3 | 0.7386 |
| Mitogen-activated protein kinase 10 | P53779 | MK10_HUMAN | Homo sapiens | 3 | 0.7386 |
| Mitogen-activated protein kinase 1 | P28482 | MK01_HUMAN | Homo sapiens | 3 | 0.7294 |
| Mitogen-activated protein kinase 1 | P28482 | MK01_HUMAN | Homo sapiens | 3 | 0.7294 |
| Fructose-1,6-bisphosphatase 1 | P00636 | F16P1_PIG | Sus scrofa | 3 | 0.7293 |
| Fructose-1,6-bisphosphatase 1 | P00636 | F16P1_PIG | Sus scrofa | 3 | 0.7293 |
| Nitric oxide synthase 1 | P29476 | NOS1_RAT | Rattus norvegicus | 5 | 0.7278 |
| Nitric oxide synthase 1 | P29476 | NOS1_RAT | Rattus norvegicus | 5 | 0.7278 |
| 4-hydroxyphenylacetate 3-monooxygenase | Q8YHT7 | Q8YHT7_BRUME | Brucella melitensis biotype 1 | 2 | 0.7242 |
| 4-hydroxyphenylacetate 3-monooxygenase | Q8YHT7 | Q8YHT7_BRUME | Brucella melitensis biotype 1 | 2 | 0.7242 |
| Cyclin-dependent kinase 2 | P24941 | CDK2_HUMAN | Homo sapiens | 3 | 0.7241 |
| Cyclin-dependent kinase 2 | P24941 | CDK2_HUMAN | Homo sapiens | 3 | 0.7241 |
| E3 ubiquitin-protein ligase Mdm2 | Q00987 | MDM2_HUMAN | Homo sapiens | 3 | 0.7234 |
| E3 ubiquitin-protein ligase Mdm2 | Q00987 | MDM2_HUMAN | Homo sapiens | 3 | 0.7234 |
| Glycogen synthase kinase-3 beta | P49841 | GSK3B_HUMAN | Homo sapiens | 2 | 0.7192 |
| Glycogen synthase kinase-3 beta | P49841 | GSK3B_HUMAN | Homo sapiens | 2 | 0.7192 |
| UTP-monosaccharide-1-phosphate uridylyltransferase | D3G6S4 | D3G6S4_LEIMA | Leishmania major | 3 | 0.7162 |
| UTP-monosaccharide-1-phosphate uridylyltransferase | D3G6S4 | D3G6S4_LEIMA | Leishmania major | 3 | 0.7162 |
| cGMP-specific 3',5'-cyclic phosphodiesterase | O76074 | PDE5A_HUMAN | Homo sapiens | 4 | 0.7148 |
| cGMP-specific 3',5'-cyclic phosphodiesterase | O76074 | PDE5A_HUMAN | Homo sapiens | 4 | 0.7148 |
| Bromodomain-containing protein 4 | O60885 | BRD4_HUMAN | Homo sapiens | 3 | 0.7140 |
| Bromodomain-containing protein 4 | O60885 | BRD4_HUMAN | Homo sapiens | 3 | 0.7140 |
| Alpha-ketoglutarate-dependent dioxygenase FTO | Q9C0B1 | FTO_HUMAN | Homo sapiens | 3 | 0.7128 |
| Alpha-ketoglutarate-dependent dioxygenase FTO | Q9C0B1 | FTO_HUMAN | Homo sapiens | 3 | 0.7128 |
| Aldo-keto reductase family 1 member C3 | P42330 | AK1C3_HUMAN | Homo sapiens | 3 | 0.7085 |
| Aldo-keto reductase family 1 member C3 | P42330 | AK1C3_HUMAN | Homo sapiens | 3 | 0.7085 |
| Casein kinase II subunit alpha | P68400 | CSK21_HUMAN | Homo sapiens | 4 | 0.7083 |
| Casein kinase II subunit alpha | P68400 | CSK21_HUMAN | Homo sapiens | 4 | 0.7083 |
| GCN5-related N-acetyltransferase | B1YEL6 | B1YEL6_EXIS2 | Exiguobacterium sibiricum | 3 | 0.7081 |
| GCN5-related N-acetyltransferase | B1YEL6 | B1YEL6_EXIS2 | Exiguobacterium sibiricum | 3 | 0.7081 |
| Enoyl-[acyl-carrier-protein] reductase [NADH] | P9WGR1 | INHA_MYCTU | Mycobacterium tuberculosis | 3 | 0.7069 |
| Enoyl-[acyl-carrier-protein] reductase [NADH] | P9WGR1 | INHA_MYCTU | Mycobacterium tuberculosis | 3 | 0.7069 |
| Calmodulin | P62157 | CALM_BOVIN | Bos taurus | 3 | 0.7061 |
| Calmodulin | P62157 | CALM_BOVIN | Bos taurus | 3 | 0.7061 |
| Cyclin-dependent kinase 2 | P24941 | CDK2_HUMAN | Homo sapiens | 3 | 0.7048 |
| Cyclin-dependent kinase 2 | P24941 | CDK2_HUMAN | Homo sapiens | 3 | 0.7048 |
| GCN5-related N-acetyltransferase | B1YEL6 | B1YEL6_EXIS2 | Exiguobacterium sibiricum | 3 | 0.7040 |
| GCN5-related N-acetyltransferase | B1YEL6 | B1YEL6_EXIS2 | Exiguobacterium sibiricum | 3 | 0.7040 |
| Nitric oxide synthase oxygenase | O34453 | NOSO_BACSU | Bacillus subtilis | 3 | 0.7028 |
| Nitric oxide synthase oxygenase | O34453 | NOSO_BACSU | Bacillus subtilis | 3 | 0.7028 |
| Thymidylate synthase | P00469 | TYSY_LACCA | Lacticaseibacillus casei | 3 | 0.7006 |
| Thymidylate synthase | P00469 | TYSY_LACCA | Lacticaseibacillus casei | 3 | 0.7006 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 2 | 0.7005 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 2 | 0.7005 |