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Aloin
- Family: Plantae - Asphodelaceae
- Kingdom: Plantae
-
Class: Quinone
- Subclass: Anthrone
| Canonical Smiles | OCc1cc(O)c2c(c1)C([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-CGISPIQUSA-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 calidophila | Asphodelaceae | Plantae | 1813110 |
Showing of synonyms
Aloin
Aloins
CHEBI:73222
W41H6S09F4
Aloinum
8015-61-0
10-(1',5'-Anhydroglucosyl)aloe-emodin-9-anthrone
10-beta-D-Glucopyranosyl-1,8-dihydroxy-3-hydroxymethyl-9(10H)-anthrone
10-beta-D-glucopyranosyl-1,8-dihydroxy-3-(hydroxymethyl)anthracen-9(10H)-one
(1S)-1,5-anhydro-1-[4,5-dihydroxy-2-(hydroxymethyl)-10-oxo-9,10-dihydroanthracen-9-yl]-D-glucitol
UNII-648RW354S9
EINECS 215-808-0
NSC227189
NSC631263
NSC 227189
NSC 631263
NSC 758464
(1S)-1,5-anhydro-1-(4,5-dihydroxy-2-(hydroxymethyl)-10-oxo-9,10-dihydroanthracen-9-yl)-D-glucitol
ALOIN (USP-RS)
ALOIN (MART.)
10-Glucopyranosyl-1,8-dihydroxy-3-(hydroxymethyl)-9(10H)-anthracenone
DTXSID6048755
10-beta-D-Glucopyranosyl-1,8-dihydroxy-3-hydroxymethyl-9(10H)-anthrone,(R)-
Alloin
Aloin, curaco
Aloin, Cape
452311-56-7
Barbaloin
UNII-W41H6S09F4
CHEMBL497001
10-(1,5'-Anhydroglucosyl)aloe-emodin-9-anthrone
10-beta-D-Glucopyranosyl-1,8-dihydroxy-3-(hydroxymethyl)-9(10H)-anthracenone
AI3-19097
1,8-dihydroxy-3-(hydroxymethyl)-10-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-10H-anthracen-9-one
9(10H)-Anthracenone, 10-glucopyranosyl-1,8-dihydroxy-3-(hydroxymethyl)-
Aloin A/B
SCHEMBL4974144
GTPL12498
HY-N6013
BDBM50269016
AKOS015895347
CCG-230807
DB15477
SMP1_000011
MS-27308
CS-0032167
EN300-19740121
BRD-A63615100-001-02-1
BRD-A63615100-001-03-9
Q27140379
1,8- Dihydroxy-3-hydroxymethyl-10-beta-D-glucopyranosyl-9-anthron
10-| cent-D-glucopyranosyl-1,8-dihydroxy-3-(hydroxymethyl)-9(10H)-anthracenone
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
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
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-leishmanial
Absorption
- Caco-2 (logPapp)
- -6.38
- 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
- -0.13
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Non-Penetrable
- Fraction Unbound (Human)
- 0.7
- Plasma Protein Binding
- 68.66
- 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
- 11.64
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Toxic
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- -1.97
- 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
- 4.84
- 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
- -31.27
- 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
- 571.29
- Hydration Free Energy
- -9.05
- Log(D) at pH=7.4
- -0.39
- Log(P)
- 0.68
- Log S
- -2.58
- Log(Vapor Pressure)
- -12.07
- Melting Point
- 184.61
- pKa Acid
- 4.18
- pKa Basic
- 7.28
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Nuclear receptor subfamily 4immunitygroup A member 1 | P22736 | NR4A1_HUMAN | Homo sapiens | 3 | 0.8549 |
| Nuclear receptor subfamily 4immunitygroup A member 1 | P22736 | NR4A1_HUMAN | Homo sapiens | 3 | 0.8549 |
| Basic phospholipase A2 VRV-PL-VIIIa | P59071 | PA2B8_DABRR | Daboia russelii | 2 | 0.7593 |
| Basic phospholipase A2 VRV-PL-VIIIa | P59071 | PA2B8_DABRR | Daboia russelii | 2 | 0.7593 |
| Pteridine reductase 1 | Q01782 | PTR1_LEIMA | Leishmania major | 4 | 0.7441 |
| Pteridine reductase 1 | Q01782 | PTR1_LEIMA | Leishmania major | 4 | 0.7441 |
| Galactoside O-acetyltransferase | P07464 | THGA_ECOLI | Escherichia coli | 4 | 0.7412 |
| Galactoside O-acetyltransferase | P07464 | THGA_ECOLI | Escherichia coli | 4 | 0.7412 |
| Lactotransferrin | P24627 | TRFL_BOVIN | Bos taurus | 2 | 0.7243 |
| Lactotransferrin | P24627 | TRFL_BOVIN | Bos taurus | 2 | 0.7243 |
| Basic phospholipase A2 VRV-PL-VIIIa | P59071 | PA2B8_DABRR | Daboia russelii | 2 | 0.7236 |
| Basic phospholipase A2 VRV-PL-VIIIa | P59071 | PA2B8_DABRR | Daboia russelii | 2 | 0.7236 |
| Epidermal growth factor receptor | P00533 | EGFR_HUMAN | Homo sapiens | 3 | 0.7143 |
| Epidermal growth factor receptor | P00533 | EGFR_HUMAN | Homo sapiens | 3 | 0.7143 |
| Genome polyprotein | O92972 | POLG_HCVJ4 | Hepatitis C virus genotype 1b | 3 | 0.7106 |
| Genome polyprotein | O92972 | POLG_HCVJ4 | Hepatitis C virus genotype 1b | 3 | 0.7106 |
| Mycocyclosin synthase | P9WPP7 | CP121_MYCTU | Mycobacterium tuberculosis | 3 | 0.7106 |
| Mycocyclosin synthase | P9WPP7 | CP121_MYCTU | Mycobacterium tuberculosis | 3 | 0.7106 |
| Cytohesin-2 | Q99418 | CYH2_HUMAN | Homo sapiens | 3 | 0.7102 |
| Cytohesin-2 | Q99418 | CYH2_HUMAN | Homo sapiens | 3 | 0.7102 |
| Gag-Pol polyprotein | P04584 | POL_HV2RO | Human immunodeficiency virus type 2 subtype A | 4 | 0.7085 |
| Gag-Pol polyprotein | P04584 | POL_HV2RO | Human immunodeficiency virus type 2 subtype A | 4 | 0.7085 |
| NADPH-dependent oxidoreductase 2-alkenal reductase | Q39172 | AER_ARATH | Arabidopsis thaliana | 3 | 0.7070 |
| NADPH-dependent oxidoreductase 2-alkenal reductase | Q39172 | AER_ARATH | Arabidopsis thaliana | 3 | 0.7070 |
| Mitochondrial poly(A) polymerase | F1NBW0 | F1NBW0_CHICK | Gallus gallus | 2 | 0.7029 |
| Mitochondrial poly(A) polymerase | F1NBW0 | F1NBW0_CHICK | Gallus gallus | 2 | 0.7029 |