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Aloin B
- Family: Plantae - Asphodelaceae
- Kingdom: Plantae
-
Class: Quinone
- Subclass: Anthraquinone Glycoside
| Canonical Smiles | OCc1cc(O)c2c(c1)[C@H]([C@@H]1O[C@H](CO)[C@H]([C@@H]([C@H]1O)O)O)c1c(C2=O)c(O)ccc1 |
|---|---|
| InChI | InChI=1S/C21H22O9/c22-6-8-4-10-14(21-20(29)19(28)17(26)13(7-23)30-21)9-2-1-3-11(24)15(9)18(27)16(10)12(25)5-8/h1-5,13-14,17,19-26,28-29H,6-7H2/t13-,14-,17-,19+,20-,21+/m1/s1 |
| InChIKey | AFHJQYHRLPMKHU-WEZNYRQKSA-N |
| Formula | C21H22O9 |
| HBA | 9 |
| HBD | 7 |
| MW | 418.4 |
| Rotatable Bonds | 3 |
| TPSA | 167.91 |
| LogP | -0.89 |
| Number Rings | 4 |
| Number Aromatic Rings | 2 |
| Heavy Atom Count | 30 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.38 |
| Exact Mass | 418.13 |
| Number of Lipinski Rule Violations | 1 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Aloe sinkatana | Asphodelaceae | Plantae | 210945 |
| 2 | Aloe sinkatana | Asphodelaceae | Plantae | 210945 |
| 3 | Aloe percrassa | Asphodelaceae | Plantae | 1593100 |
| 4 | Aloe species | Asphodelaceae | Plantae | 117795 |
Showing of synonyms
Aloin B
28371-16-6
Isobarbaloin
UNII-69VIB0J2WK
69VIB0J2WK
BARBALOIN B
CHEBI:74131
DTXSID70904581
9(10H)-Anthracenone, 10-beta-D-glucopyranosyl-1,8-dihydroxy-3-(hydroxymethyl)-, (R)-
(1S)-1,5-anhydro-1-[(9R)-4,5-dihydroxy-2-(hydroxymethyl)-10-oxo-9,10-dihydroanthracen-9-yl]-D-glucitol
(1S)-1,5-anhydro-1-((9R)-4,5-dihydroxy-2-(hydroxymethyl)-10-oxo-9,10-dihydroanthracen-9-yl)-D-glucitol
DTXCID901333710
(10R)-10-beta-D-GLUCOPYRANOSYL-1,8-DIHYDROXY-3-(HYDROXYMETHYL)-9(10H)-ANTHRACENONE
9(10H)-ANTHRACENONE, 10-beta-D-GLUCOPYRANOSYL-1,8-DIHYDROXY-3-(HYDROXYMETHYL)-, (10R)-
Barbaloin
CHEMBL3617994
(R)-1,8-dihydroxy-3-(hydroxymethyl)-10-((2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)anthracen-9(10H)-one
(10R)-1,8-dihydroxy-3-(hydroxymethyl)-10-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-10H-anthracen-9-one
Aloin-B
10R-beta-D-glucopyranosyl-1,8-dihydroxy-3-(hydroxymethyl)-9(10H)-anthracenone
Aloin, from Curacao aloe, ~50%
NCGC00183867-01
Aloin B (Standard)
ALOIN B [MI]
SCHEMBL181616
Aloin BIsobarbaloin
HY-N0886R
9(10H)-Anthracenone, 10-.beta.-D-glucopyranosyl-1,8-dihydroxy-3-(hydroxymethyl)-, (10S)-
HY-N0886
BDBM50120492
MSK164389
AKOS026749813
CS-3708
GS-6457
MA76227
NCGC00389730-01
AC-34434
NS00002298
C17778
H12077
Q27144440
1,8-Dihydroxy-10-(ss-D-glucopyranosyl)-3-(hydroxymethyl)-9(10H)-anthracenone
10-ss-D-Glucopyranosyl-1,8-dihydroxy-3-(hydroxymethyl)-9(10H)-anthracenone
(10R)-1,8-DIHYDROXY-3-(HYDROXYMETHYL)-10-[(2S,3R,4R,5S,6R)-3,4,5-TRIHYDROXY-6-(HYDROXYMETHYL)OXAN-2-YL]-9,10-DIHYDROANTHRACEN-9-ONE
(10R)-10-.BETA.-D-GLUCOPYRANOSYL-1,8-DIHYDROXY-3-(HYDROXYMETHYL)-9(10H)-ANTHRACENONE
9(10H)-ANTHRACENONE, 10-.BETA.-D-GLUCOPYRANOSYL-1,8-DIHYDROXY-3-(HYDROXYMETHYL)-, (10R)-
- Geremedhin G, Bisrat D, et al. (2014). Isolation, characterization and in vivo antimalarial evaluation of anthrones from the leaf latex of Aloe percrassa Todaro. Journal of Natural Remedies,2014,14(2),1-7. [View] [PubMed]
- ELhassan GOM, Adhikari A, et al. (2011). Phytochemical and biological studies on Aloe sinkatana Berger. The 14th NAPRECA Symposium and AAMPS Ethnoveterinary Medicine Symposium, At Nairobi, Kenya. August 2011. [View]
- ELhassan GOM, Adhikari A, et al. (2012). Phytochemistry and antiglycation activity of Aloe sinkatana Reynolds. Phytochemistry Letters,2012,5(4),725-728. [View]
- 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]
Pubchem:
14989
Cas:
28371-16-6
Gnps:
CCMSLIB00006425524
Zinc:
ZINC000004214775
Kegg Ligand:
C17778
Chebi:
74131
Nmrshiftdb2:
60028054
Metabolights:
MTBLC74131
Chembl:
CHEMBL3617994
Bindingdb:
50120492
CPRiL:
63299
SMILES: O1CCCCC1C(c(c23)cccc3)c4c(C2=O)cccc4
Level: 1
Mol. Weight: 418.4 g/mol
SMILES: c1cccc(c12)Cc3c(C2=O)cccc3
Level: 0
Mol. Weight: 418.4 g/mol
SMILES: C1CCOCC1
Level: 0
Mol. Weight: 418.4 g/mol
Anti-plasmodial
Absorption
- Caco-2 (logPapp)
- -6.34
- Human Oral Bioavailability 20%
- Non-Bioavailable
- Human Intestinal Absorption
- Non-Absorbed
- Madin-Darby Canine Kidney
- -5.79
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Substrate
- Skin Permeability
- -0.12
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Non-Penetrable
- Fraction Unbound (Human)
- 0.7
- Plasma Protein Binding
- 73.57
- 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
- Non-Substrate
- CYP 2D6 Inhibitor
- Non-Inhibitor
- CYP 2D6 Substrate
- Non-Substrate
- CYP 3A4 Inhibitor
- Non-Inhibitor
- CYP 3A4 Substrate
- Non-Substrate
- OATP1B1
- Non-Inhibitor
- OATP1B3
- Non-Inhibitor
Excretion
- Clearance
- 11.65
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Toxic
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- -2.04
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Safe
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 0.72
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 4.86
- 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
- -31.32
- Rat (Acute)
- 2.64
- Rat (Chronic Oral)
- 4.27
- Fathead Minnow
- 3.81
- Respiratory Disease
- Toxic
- Skin Sensitisation
- Safe
- SR-ARE
- Safe
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Safe
- SR-p53
- Safe
General Properties
- Boiling Point
- 572.85
- Hydration Free Energy
- -9.02
- Log(D) at pH=7.4
- -0.34
- Log(P)
- 0.69
- Log S
- -2.59
- Log(Vapor Pressure)
- -12.19
- Melting Point
- 185.56
- pKa Acid
- 4.21
- pKa Basic
- 7.24
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Epidermal growth factor receptor | P00533 | EGFR_HUMAN | Homo sapiens | 3 | 0.8340 |
| Epidermal growth factor receptor | P00533 | EGFR_HUMAN | Homo sapiens | 3 | 0.8340 |
| D-aminoacyl-tRNA deacylase | Q8IIS0 | DTD_PLAF7 | Plasmodium falciparum | 3 | 0.8030 |
| D-aminoacyl-tRNA deacylase | Q8IIS0 | DTD_PLAF7 | Plasmodium falciparum | 3 | 0.8030 |
| Riboflavin synthase | P0AFU8 | RISA_ECOLI | Escherichia coli | 3 | 0.7953 |
| Riboflavin synthase | P0AFU8 | RISA_ECOLI | Escherichia coli | 3 | 0.7953 |
| Basic phospholipase A2 VRV-PL-VIIIa | P59071 | PA2B8_DABRR | Daboia russelii | 2 | 0.7600 |
| Basic phospholipase A2 VRV-PL-VIIIa | P59071 | PA2B8_DABRR | Daboia russelii | 2 | 0.7600 |
| Mitochondrial poly(A) polymerase | F1NBW0 | F1NBW0_CHICK | Gallus gallus | 2 | 0.7257 |
| Mitochondrial poly(A) polymerase | F1NBW0 | F1NBW0_CHICK | Gallus gallus | 2 | 0.7257 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 3 | 0.7194 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 3 | 0.7194 |
| Purine nucleoside phosphorylase DeoD-type | P0ABP8 | DEOD_ECOLI | Escherichia coli | 3 | 0.7164 |
| Lethal(3)malignant brain tumor-like protein 1 | Q9Y468 | LMBL1_HUMAN | Homo sapiens | 3 | 0.7164 |
| Lethal(3)malignant brain tumor-like protein 1 | Q9Y468 | LMBL1_HUMAN | Homo sapiens | 3 | 0.7164 |
| Purine nucleoside phosphorylase DeoD-type | P0ABP8 | DEOD_ECOLI | Escherichia coli | 3 | 0.7164 |
| Cytosolic purine 5'-nucleotidase | P49902 | 5NTC_HUMAN | Homo sapiens | 2 | 0.7160 |
| Cytosolic purine 5'-nucleotidase | P49902 | 5NTC_HUMAN | Homo sapiens | 2 | 0.7160 |
| Ras-related protein Ral-B | P11234 | RALB_HUMAN | Homo sapiens | 3 | 0.7156 |
| Ras-related protein Ral-B | P11234 | RALB_HUMAN | Homo sapiens | 3 | 0.7156 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 3 | 0.7050 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 3 | 0.7050 |
| DNA-directed DNA polymerase | Q38087 | DPOL_BPR69 | Escherichia phage RB69 | 3 | 0.7040 |
| DNA-directed DNA polymerase | Q38087 | DPOL_BPR69 | Escherichia phage RB69 | 3 | 0.7040 |
| Glucose-1-phosphate thymidylyltransferase | Q9HU22 | Q9HU22_PSEAE | Pseudomonas aeruginosa | 3 | 0.7026 |
| Glucose-1-phosphate thymidylyltransferase | Q9HU22 | Q9HU22_PSEAE | Pseudomonas aeruginosa | 3 | 0.7026 |
| Thymidylate synthase | P00469 | TYSY_LACCA | Lacticaseibacillus casei | 3 | 0.7020 |
| Thymidylate synthase | P00469 | TYSY_LACCA | Lacticaseibacillus casei | 3 | 0.7020 |
| Chitinase | Q54276 | Q54276_SERMA | Serratia marcescens | 3 | 0.7014 |
| Chitinase | Q54276 | Q54276_SERMA | Serratia marcescens | 3 | 0.7014 |