Compound: Aloin A
SMILES: O=C1c2c(O)cc(CO)cc2[C@@H]([C@@H]3O[C@@H]([C@@H](O)[C@@H]([C@H]3O)O)CO)c4c1c(O)ccc4
InChIKey: AFHJQYHRLPMKHU-OSYMLPPYSA-N
Synonyms: Aloin A, 1415-73-2, Barbaloin, CHEBI:2991, DTXSID0045967, 648RW354S9, DTXCID8025967, NSC-407305, (1S)-1,5-anhydro-1-[(9S)-4,5-dihydroxy-2-(hydroxymethyl)-10-oxo-9,10-dihydroanthracen-9-yl]-D-glucitol, (1S)-1,5-anhydro-1-((9S)-4,5-dihydroxy-2-(hydroxymethyl)-10-oxo-9,10-dihydroanthracen-9-yl)-D-glucitol, RefChem:27143, Barbaloin A, (S)-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, 9(10H)-Anthracenone, 10-beta-D-glucopyranosyl-1,8-dihydroxy-3-(hydroxymethyl)-, (10S)-, CHEMBL2103763, MFCD00151160, 1,8-Dihydroxy-3-hydroxymethyl-10-(6-hydroxymethyl-3,4,5-trihydroxy-2-pyranyl)anthrone, Aloin [BAN], 5133-19-7, (10S)-1,8-dihydroxy-3-(hydroxymethyl)-10-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-10H-anthracen-9-one, (10S)-1,8-dihydroxy-3-(hydroxymethyl)-10-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]-10H-anthracen-9-one, Aloin, from Curacao aloe, ~50%, UNII-648RW354S9, 10-Glucopyranosyl-1,8-dihydroxy-3-(hydroxymethyl)-9(10H)-anthracenone, Barbaloin; Aloin, 9(10H)-Anthracenone, 10-.beta.-D-glucopyranosyl-1,8-dihydroxy-3-(hydroxymethyl)-, (10S)-, Aloin (Standard), NCGC00183867-01, Aloin (Barbaloin), EINECS 215-808-0, NSC 227189, NSC 631263, Aloin, analytical standard, ALOIN A [MI], DSSTox_CID_25967, DSSTox_RID_82951, DSSTox_GSID_48755, orb1310868, SCHEMBL14837254, SCHEMBL29386028, SCHEMBL29626884, HY-N0123R, 1,8-Dihydroxy-10-(beta-D-glucopyranosyl)-3-(hydroxymethyl)-9(10H)-anthracenone, 10-beta-D-Glucopyranosyl-1,8-dihydroxy-3-(hydroxymethyl)-9(10H)-anthracenone, AFHJQYHRLPMKHU-OSYMLPPYSA-N, HY-N0123, MSK40341, Tox21_111495, Tox21_113216, BDBM50598137, EBC-98040, s2375, AKOS022168218, CCG-268870, CS-3707, MA76226, NSC 758464, (R)-10-beta-D-Glucopyranosyl-1,8-dihydroxy-3-(hydroxymethyl)anthracen-9(10H)-one, 9(10H)-Anthracenone, 10-.beta.-D-glucopyranosyl-1,8-dihydroxy-3-(hydroxymethyl)-, (S)-, NCGC00183867-02, NCGC00183867-06, TS-07631, CAS-1415-73-2, CAS-8015-61-0, NS00066971, H10347, Q413888, Aloin, from Aloe barbadensis Miller leaves, >=97%, BRD-K02074536-001-01-9, Aloin, United States Pharmacopeia (USP) Reference Standard, (10S)-10-?-D-Glucopyranosyl-1,8-dihydroxy-3-(hydroxymethyl)-10H-anthracen-9-one, 10-.BETA.-D-Glucopyranosyl-1,8-dihydroxy-3-(hydroxymethyl)-9(10H)-anthracenone-, 10(S)-, 10-beta-D-Glucopyranosyl-1,8-dihydroxy-3-hydroxymethyl-9(10H)-anthrone,(R)-, 9(10H)-Anthracenone, 10-|A-D-glucopyranosyl-1,8-dihydroxy-3-(hydroxymethyl)-, (10S)-, (10S)-10-.BETA.-D-GLUCOPYRANOSYL-1,8-DIHYDROXY-3-(HYDROXYMETHYL)-9(10H)-ANTHRACENONE
Theoretical properties:
molecular_formula: C21H22O9
molecular_weight: 418.4 g/mol
exact_mass: 418.12638228 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 7
hydrogen_bond_acceptor_count: 9
rotatable_bond_count: 3
heavy_atom_count: 30
topological_polar_surface_area: 168 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
Descriptions:
{"pubchem": "Aloin A is a C-glycosyl compound that is beta-D-glucopyranose in which the anomeric hydroxy group is replaced by a 4,5-dihydroxy-2-(hydroxymethyl)-10-oxo-9,10-dihydroanthracen-9-yl moiety (the 9S diastereoisomer). It has a role as a metabolite and a laxative. It is a C-glycosyl compound, a member of phenols, a cyclic ketone and a member of anthracenes.", "chebi": "A <em>C</em>-glycosyl compound that is \u03b2-<small>D</small>-glucopyranose in which the anomeric hydroxy group is replaced by a 4,5-dihydroxy-2-(hydroxymethyl)-10-oxo-9,10-dihydroanthracen-9-yl moiety (the 9<i>S</i> diastereoisomer).", "chembl": "Unnamed Compound is a small molecule listed in the ChEMBL database but has not progressed to an approved clinical phase.", "wikipedia": "Aloin, also known as barbaloin, is a bitter, yellow-brown colored compound noted in the exudate of at least 68 Aloe species at levels from 0.1 to 6.6% of leaf dry weight (making between 3% and 35% of the total exudate), and in another 17 species at indeterminate levels [Reynolds, 1995b]. It is used as a stimulant-laxative, treating constipation by inducing bowel movements. The compound is present in what is commonly referred to as the aloe latex that exudes from cells adjacent to the vascular bundles, found under the rind of the leaf and in between it and the gel.\nWhen dried, it has been used as a bittering agent in commerce (alcoholic beverages) [21 CFR 172.510. Scientific names given include Aloe perryi, A. barbadensis (= A. vera), A. ferox, and hybrids of A. ferox with A. africana and A. spicata.]. Aloe is listed in federal regulations as a natural substance that may be \"safely used in food\" when used \"in the minimum quantity required to produce their intended physical or technical effect and in accordance with all the principles of good manufacturing practice.\" This food application is generally limited to use in quite small quantities as a flavoring in alcoholic beverages and may usually be identified only as a \"natural flavor.\"\nIn May 2002, the U.S. Food and Drug Administration (FDA) issued a ruling that aloe laxatives are no longer generally recognized as safe (GRAS) and effective, meaning that aloin-containing products are no longer available in over-the-counter drug products in the United States, because they may be carcinogenic and more data is needed to establish otherwise. Aloe vera leaf latex is a concentrate of an herb or other botanical, and so meets the statutory description of an ingredient that may be used in dietary supplements."}