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Rhein
- Family: Plantae - Leguminosae/Fabaceae
- Kingdom: Plantae
-
Class: Quinone
- Subclass: Anthraquinone
Canonical Smiles | Oc1cc(cc2c1C(=O)c1c(C2=O)cccc1O)C(=O)O |
---|---|
InChI | InChI=1S/C15H8O6/c16-9-3-1-2-7-11(9)14(19)12-8(13(7)18)4-6(15(20)21)5-10(12)17/h1-5,16-17H,(H,20,21) |
InChIKey | FCDLCPWAQCPTKC-UHFFFAOYSA-N |
Formula | C15H8O6 |
HBA | 5 |
HBD | 3 |
MW | 284.22 |
Rotatable Bonds | 1 |
TPSA | 111.9 |
LogP | 1.57 |
Number Rings | 3 |
Number Aromatic Rings | 2 |
Heavy Atom Count | 21 |
Formal Charge | 0 |
Fraction CSP3 | 0.0 |
Exact Mass | 284.03 |
Number of Lipinski Rule Violations | 0 |
# | Species | Family | Kingdom | NCBI Taxonomy ID |
---|---|---|---|---|
1 | Senna floribunda | Leguminosae/Fabaceae | Plantae | 2601732 |
2 | Senna Didymobotrya | Leguminosae/Fabaceae | Plantae | 72401 |
Showing of synonyms
Rhein
478-43-3
Monorhein
Rhubarb Yellow
Cassic acid
Rheic acid
1,8-Dihydroxy-3-carboxyanthraquinone
4,5-Dihydroxyanthraquinone-2-carboxylic acid
Chrysazin-3-carboxylic acid
1,8-Dihydroxyanthraquinone-3-carboxylic acid
Dipropionyl rhein
NSC 38629
Parietic acid
4,5-dihydroxy-9,10-dioxoanthracene-2-carboxylic acid
9,10-Dihydro-4,5-dihydroxy-9,10-dioxo-2-anthracenecarboxylic acid
CCRIS 5129
2-Anthracenecarboxylic acid, 9,10-dihydro-4,5-dihydroxy-9,10-dioxo-
EINECS 207-521-4
YM64C2P6UX
BRN 2222155
DTXSID4026000
4,5-Dihydroxy-2-anthraquinonecarboxylic acid
2-Anthroic acid, 9,10-dihydro-4,5-dihydroxy-9,10-dioxo-
NSC-38629
RHEIN [MI]
9,10-Dihydro-4,5-dihydroxy-9,10-dioxoanthracene-2-carboxylic acid
DTXCID606000
1,8-dihydroxy-3-carboxyl-9,10-anthraquinone
4-10-00-04088 (Beilstein Handbook Reference)
9,10-Dihydro-4,5-dihydroxy-9,10-dioxo-2-anthroic acid
2-Anthraquinonecarboxylic acid, 4,5-dihydroxy-
DIHYDROXY-3-CARBOXYLANTHRAQUINONE, 1,8-
RHEIN [INCI]
2-Anthroic acid, 9,10-dihydro-4,5-dihydroxy-9,10-dioxo-(8CI)
4,5-dihydroxy-9,10-dioxo-9,10-dihydroanthracene-2-carboxylic acid
MFCD00009618
Rhein (1,8-dihydroxy-3-carboxyl anthraquinone)
MLS000069639
CHEBI:8825
4,5-DiOH-anthraquinone-2-COOH
SMR000058210
Rheinic acid
1,8-DIHYDROXY-3-CARBOXYL ANTHRAQUINONE
C15H8O6
Rhein(Monorhein)
UNII-YM64C2P6UX
Rhein (Standard)
RHN
Rhein, technical grade
4ie7
ST057726
Regid855879
Rhein, analytical standard
SCHEMBL25253
US9238626, Rhein
Cid_10168
MLS006011744
CHEMBL418068
MEGxp0_001866
4,5-dihydroxy-9,10-dioxo-anthracene-2-carboxylic acid
ACon1_000217
BDBM32021
HY-N0105R
GLXC-05271
BCP28202
FDC16642
HY-N0105
MSK40045
NSC38629
Tox21_201098
4,5-Dihydroxy-9,10-dioxo-9,10-dihydroanthracene-2-carboxylicacid
BBL009695
LMPK13040015
S2400
STL141046
AKOS005259272
AC-7978
CS-5239
DB13174
FR27724
NCGC00018199-01
NCGC00018199-02
NCGC00018199-03
NCGC00018199-04
NCGC00018199-05
NCGC00018199-06
NCGC00018199-07
NCGC00023342-03
NCGC00023342-04
NCGC00258650-01
AS-11635
CAS-478-43-3
SY051290
DB-014981
D3986
NS00015851
4, 5-Dihydroxyanthraquinone-2-carboxylic acid
EN300-303248
Q720356
4,5-dihydroxy-9,10-dioxo-2-anthracenecarboxylic acid
4,5-dihydroxy-9,10-dioxoanthracene-2-carboxylicacid
BRD-K27335680-001-01-9
BRD-K27335680-001-10-0
2-Anthroic acid,10-dihydro-4,5-dihydroxy-9,10-dioxo-
4,5-dihydroxy-9,10-diketo-anthracene-2-carboxylic acid
2-Anthracenecarboxylic acid,10-dihydro-4,5-dihydroxy-9,10-dioxo-
4,5-Dihydroxy-9,10-dioxo-9,10-dihydro-2-anthracenecarboxylic acid
4,5-bis(oxidanyl)-9,10-bis(oxidanylidene)anthracene-2-carboxylic acid
4,5-Dihydroxy-9,10-dioxo-9,10-dihydro-2-anthracenecarboxylic acid #
9,10-Dihydro-4,5-dihydroxy-9,10-dioxo-2-anthracene carboxylic acid
9,10-Dihydro-4,5-dihydroxy-9,10-dioxo-2-anthracenecarboxylic acid, 9CI
9,10-Dihydro-4,5-dihydroxy-9,10-dioxo-2-anthracenecarboxylic Acid-13C6
Chrysazin-3-carboxyli c acid
- Tsegaye G, Alemayehu G. (2006). Phytochemical investigation on the stem bark of Senna floribunda. M.Sc. Thesis, Addis Ababa University, Ethiopia,2006. [View] [PubMed]
- Alemayehu G, Abegaz B, et al. (1989). Quinones of Senna Didymobotrya.. Bulletin of the Chemical Society of Ethiopia,1989,3(1),37-40. [View] [PubMed]
Pubchem:
10168
Cas:
478-43-3
Gnps:
CCMSLIB00006387381
Zinc:
ZINC000004098704
Kegg Ligand:
C10401
Chebi:
8825
Nmrshiftdb2:
60025881
Chembl:
CHEMBL418068
Comptox:
DTXSID4026000
Drugbank:
DB13174
Pdb Ligand:
RHN
Bindingdb:
32021
Selleck:
Rhein-Monorhein
CPRiL:
98272
SMILES: c1cccc(c12)C(=O)c3c(C2=O)cccc3
Level: 0
Mol. Weight: 284.22 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -5.08
- Human Oral Bioavailability 20%
- Non-Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.780
- Human Oral Bioavailability 50%
- Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -2.18
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Non-Penetrable
- Fraction Unbound (Human)
- 1.080
- Plasma Protein Binding
- 61.51
- Steady State Volume of Distribution
- -
Metabolism
- Breast Cancer Resistance Protein
- Inhibitor
- CYP 1A2 Inhibitor
- Inhibitor
- CYP 1A2 Substrate
- Non-Substrate
- CYP 2C19 Inhibitor
- Non-Inhibitor
- CYP 2C19 Substrate
- Non-Substrate
- CYP 2C9 Inhibitor
- Non-Inhibitor
- CYP 2C9 Substrate
- 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
- 5.240
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Toxic
- Avian
- Safe
- Bee
- Safe
- Bioconcentration Factor
- 0.140
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Toxic
- Liver Injury I (DILI)
- Toxic
- Eye Corrosion
- Safe
- Eye Irritation
- Toxic
- Maximum Tolerated Dose
- 1.160
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 5.020
- 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
- 3.060
- Rat (Acute)
- 2.340
- Rat (Chronic Oral)
- 3.620
- Fathead Minnow
- 4.070
- 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
- 448.780
- Hydration Free Energy
- -9.260
- Log(D) at pH=7.4
- -0.340
- Log(P)
- 3.52
- Log S
- -4.1
- Log(Vapor Pressure)
- -8.01
- Melting Point
- 281.78
- pKa Acid
- 7.32
- pKa Basic
- 2.92
Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
---|---|---|---|---|---|
Fibroblast growth factor receptor 1 | P11362 | FGFR1_HUMAN | Homo sapiens | 3 | 0.9583 |
Fibroblast growth factor receptor 1 | P11362 | FGFR1_HUMAN | Homo sapiens | 3 | 0.9583 |
Type IV / VI secretion system DotU domain-containing protein | Q9KN50 | Q9KN50_VIBCH | Vibrio cholerae serotype O1 | 3 | 0.9195 |
Type IV / VI secretion system DotU domain-containing protein | Q9KN50 | Q9KN50_VIBCH | Vibrio cholerae serotype O1 | 3 | 0.9195 |
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A | Q9Y233 | PDE10_HUMAN | Homo sapiens | 3 | 0.9147 |
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A | Q9Y233 | PDE10_HUMAN | Homo sapiens | 3 | 0.9147 |
Epidermal growth factor receptor | P00533 | EGFR_HUMAN | Homo sapiens | 3 | 0.9108 |
Epidermal growth factor receptor | P00533 | EGFR_HUMAN | Homo sapiens | 3 | 0.9108 |
Epidermal growth factor receptor | P00533 | EGFR_HUMAN | Homo sapiens | 3 | 0.9046 |
Epidermal growth factor receptor | P00533 | EGFR_HUMAN | Homo sapiens | 3 | 0.9046 |
Epidermal growth factor receptor | P00533 | EGFR_HUMAN | Homo sapiens | 3 | 0.8960 |
Epidermal growth factor receptor | P00533 | EGFR_HUMAN | Homo sapiens | 3 | 0.8960 |
Cytosolic purine 5'-nucleotidase | P49902 | 5NTC_HUMAN | Homo sapiens | 3 | 0.8910 |
Cytosolic purine 5'-nucleotidase | P49902 | 5NTC_HUMAN | Homo sapiens | 3 | 0.8910 |
Carbonic anhydrase 12 | O43570 | CAH12_HUMAN | Homo sapiens | 3 | 0.8817 |
Carbonic anhydrase 12 | O43570 | CAH12_HUMAN | Homo sapiens | 3 | 0.8817 |
Glycogen synthase kinase-3 beta | P49841 | GSK3B_HUMAN | Homo sapiens | 3 | 0.8779 |
Glycogen synthase kinase-3 beta | P49841 | GSK3B_HUMAN | Homo sapiens | 3 | 0.8779 |
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase | Q9TQS6 | DHDH_MACFA | Macaca fascicularis | 3 | 0.8758 |
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase | Q9TQS6 | DHDH_MACFA | Macaca fascicularis | 3 | 0.8758 |
Fatty acid-binding protein, intestinal | P12104 | FABPI_HUMAN | Homo sapiens | 3 | 0.8666 |
Fatty acid-binding protein, intestinal | P12104 | FABPI_HUMAN | Homo sapiens | 3 | 0.8666 |
3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 3 | 0.8497 |
3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 3 | 0.8497 |
2-phospho-L-lactate transferase | Q8PVT6 | COFD_METMA | Methanosarcina mazei | 3 | 0.8434 |
2-phospho-L-lactate transferase | Q8PVT6 | COFD_METMA | Methanosarcina mazei | 3 | 0.8434 |
3-phosphoinositide-dependent protein kinase 1 | O15530 | PDPK1_HUMAN | Homo sapiens | 4 | 0.8428 |
3-phosphoinositide-dependent protein kinase 1 | O15530 | PDPK1_HUMAN | Homo sapiens | 4 | 0.8428 |
ActVA 6 protein | Q53908 | Q53908_STRCH | Streptomyces coelicolor | 4 | 0.8424 |
ActVA 6 protein | Q53908 | Q53908_STRCH | Streptomyces coelicolor | 4 | 0.8424 |
ADP-ribosyl-[dinitrogen reductase] hydrolase | A7XNI2 | A7XNI2_AZOBR | Azospirillum brasilense | 3 | 0.8373 |
ADP-ribosyl-[dinitrogen reductase] hydrolase | A7XNI2 | A7XNI2_AZOBR | Azospirillum brasilense | 3 | 0.8373 |
Casein kinase II subunit alpha | P28523 | CSK2A_MAIZE | Zea mays | 4 | 0.8188 |
Casein kinase II subunit alpha | P28523 | CSK2A_MAIZE | Zea mays | 4 | 0.8188 |
Serine/threonine-protein kinase pim-1 | P11309 | PIM1_HUMAN | Homo sapiens | 3 | 0.8056 |
Serine/threonine-protein kinase pim-1 | P11309 | PIM1_HUMAN | Homo sapiens | 3 | 0.8056 |
Basic phospholipase A2 VRV-PL-VIIIa | P59071 | PA2B8_DABRR | Daboia russelii | 3 | 0.7984 |
Basic phospholipase A2 VRV-PL-VIIIa | P59071 | PA2B8_DABRR | Daboia russelii | 3 | 0.7984 |
Aklavinone 12-hydroxylase RdmE | Q54530 | DNRF_STREF | Streptomyces purpurascens | 4 | 0.7900 |
Aklavinone 12-hydroxylase RdmE | Q54530 | DNRF_STREF | Streptomyces purpurascens | 4 | 0.7900 |
Vascular endothelial growth factor receptor 2 | P35968 | VGFR2_HUMAN | Homo sapiens | 3 | 0.7752 |
Vascular endothelial growth factor receptor 2 | P35968 | VGFR2_HUMAN | Homo sapiens | 3 | 0.7752 |
Casein kinase II subunit alpha | P68400 | CSK21_HUMAN | Homo sapiens | 4 | 0.7697 |
Casein kinase II subunit alpha | P68400 | CSK21_HUMAN | Homo sapiens | 4 | 0.7697 |
11-beta-hydroxysteroid dehydrogenase 1 | P28845 | DHI1_HUMAN | Homo sapiens | 3 | 0.7575 |
11-beta-hydroxysteroid dehydrogenase 1 | P28845 | DHI1_HUMAN | Homo sapiens | 3 | 0.7575 |
GCN5-related N-acetyltransferase | B1YEL6 | B1YEL6_EXIS2 | Exiguobacterium sibiricum | 3 | 0.7555 |
GCN5-related N-acetyltransferase | B1YEL6 | B1YEL6_EXIS2 | Exiguobacterium sibiricum | 3 | 0.7555 |
Pancreatic alpha-amylase | P04746 | AMYP_HUMAN | Homo sapiens | 2 | 0.7540 |
Pancreatic alpha-amylase | P04746 | AMYP_HUMAN | Homo sapiens | 2 | 0.7540 |
GCN5-related N-acetyltransferase | B1YEL6 | B1YEL6_EXIS2 | Exiguobacterium sibiricum | 3 | 0.7520 |
GCN5-related N-acetyltransferase | B1YEL6 | B1YEL6_EXIS2 | Exiguobacterium sibiricum | 3 | 0.7520 |
Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 2 | 0.7500 |
Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 2 | 0.7500 |
Nucleoside diphosphate kinase | A5J299 | A5J299_PENVA | Penaeus vannamei | 3 | 0.7483 |
Nucleoside diphosphate kinase | A5J299 | A5J299_PENVA | Penaeus vannamei | 3 | 0.7483 |
Aklanonic acid methyl ester cyclase AcmA | O52646 | DNRD_STRGJ | Streptomyces galilaeus | 3 | 0.7474 |
Aklanonic acid methyl ester cyclase AcmA | O52646 | DNRD_STRGJ | Streptomyces galilaeus | 3 | 0.7474 |
Tyrosine-protein kinase Lck | P06239 | LCK_HUMAN | Homo sapiens | 3 | 0.7468 |
Tyrosine-protein kinase Lck | P06239 | LCK_HUMAN | Homo sapiens | 3 | 0.7468 |
4-hydroxyphenylacetate 3-monooxygenase | Q8YHT7 | Q8YHT7_BRUME | Brucella melitensis biotype 1 | 2 | 0.7447 |
4-hydroxyphenylacetate 3-monooxygenase | Q8YHT7 | Q8YHT7_BRUME | Brucella melitensis biotype 1 | 2 | 0.7447 |
Focal adhesion kinase 1 | Q00944 | FAK1_CHICK | Gallus gallus | 3 | 0.7442 |
Focal adhesion kinase 1 | Q00944 | FAK1_CHICK | Gallus gallus | 3 | 0.7442 |
HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.7365 |
HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.7365 |
Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 3 | 0.7348 |
Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 3 | 0.7348 |
Lactotransferrin | P24627 | TRFL_BOVIN | Bos taurus | 3 | 0.7344 |
Lactotransferrin | P24627 | TRFL_BOVIN | Bos taurus | 3 | 0.7344 |
Cathepsin S | P25774 | CATS_HUMAN | Homo sapiens | 3 | 0.7332 |
Cathepsin S | P25774 | CATS_HUMAN | Homo sapiens | 3 | 0.7332 |
Casein kinase II subunit alpha | P68400 | CSK21_HUMAN | Homo sapiens | 4 | 0.7310 |
Casein kinase II subunit alpha | P68400 | CSK21_HUMAN | Homo sapiens | 4 | 0.7310 |
Protein ppBat | Q8A8A4 | Q8A8A4_BACTN | Bacteroides thetaiotaomicron VPI-5482 | 3 | 0.7289 |
Protein ppBat | Q8A8A4 | Q8A8A4_BACTN | Bacteroides thetaiotaomicron VPI-5482 | 3 | 0.7289 |
Casein kinase II subunit alpha | P28523 | CSK2A_MAIZE | Zea mays | 4 | 0.7282 |
Casein kinase II subunit alpha | P28523 | CSK2A_MAIZE | Zea mays | 4 | 0.7282 |
Plasma membrane ATPase | Q42932 | Q42932_NICPL | Nicotiana plumbaginifolia | 3 | 0.7274 |
Plasma membrane ATPase | Q42932 | Q42932_NICPL | Nicotiana plumbaginifolia | 3 | 0.7274 |
CCA-adding enzyme | O28126 | CCA_ARCFU | Archaeoglobus fulgidus | 2 | 0.7273 |
CCA-adding enzyme | O28126 | CCA_ARCFU | Archaeoglobus fulgidus | 2 | 0.7273 |
Nitric oxide synthase oxygenase | O34453 | NOSO_BACSU | Bacillus subtilis | 3 | 0.7240 |
Nitric oxide synthase oxygenase | O34453 | NOSO_BACSU | Bacillus subtilis | 3 | 0.7240 |
Casein kinase II subunit alpha | P28523 | CSK2A_MAIZE | Zea mays | 4 | 0.7228 |
Casein kinase II subunit alpha | P28523 | CSK2A_MAIZE | Zea mays | 4 | 0.7228 |
Nitric oxide synthase oxygenase | O34453 | NOSO_BACSU | Bacillus subtilis | 3 | 0.7209 |
Nitric oxide synthase oxygenase | O34453 | NOSO_BACSU | Bacillus subtilis | 3 | 0.7209 |
Cyclin-dependent kinase 2 | P24941 | CDK2_HUMAN | Homo sapiens | 3 | 0.7183 |
Cyclin-dependent kinase 2 | P24941 | CDK2_HUMAN | Homo sapiens | 3 | 0.7183 |
Serine/threonine-protein kinase pim-1 | P11309 | PIM1_HUMAN | Homo sapiens | 4 | 0.7170 |
Serine/threonine-protein kinase pim-1 | P11309 | PIM1_HUMAN | Homo sapiens | 4 | 0.7170 |
Focal adhesion kinase 1 | Q00944 | FAK1_CHICK | Gallus gallus | 3 | 0.7152 |
Focal adhesion kinase 1 | Q00944 | FAK1_CHICK | Gallus gallus | 3 | 0.7152 |
Cyclin-dependent kinase 2 | P24941 | CDK2_HUMAN | Homo sapiens | 3 | 0.7094 |
Cyclin-dependent kinase 2 | P24941 | CDK2_HUMAN | Homo sapiens | 3 | 0.7094 |
Tyrosyl-DNA phosphodiesterase 2 | Q9JJX7 | TYDP2_MOUSE | Mus musculus | 2 | 0.7070 |
Tyrosyl-DNA phosphodiesterase 2 | Q9JJX7 | TYDP2_MOUSE | Mus musculus | 2 | 0.7070 |
Fibroblast growth factor receptor 2 | P21802 | FGFR2_HUMAN | Homo sapiens | 2 | 0.7067 |
Fibroblast growth factor receptor 2 | P21802 | FGFR2_HUMAN | Homo sapiens | 2 | 0.7067 |
Tetracycline repressor protein class D | P0ACT4 | TETR4_ECOLX | Escherichia coli | 3 | 0.7055 |
Tetracycline repressor protein class D | P0ACT4 | TETR4_ECOLX | Escherichia coli | 3 | 0.7055 |
UTP-monosaccharide-1-phosphate uridylyltransferase | D3G6S4 | D3G6S4_LEIMA | Leishmania major | 3 | 0.7034 |
UTP-monosaccharide-1-phosphate uridylyltransferase | D3G6S4 | D3G6S4_LEIMA | Leishmania major | 3 | 0.7034 |
Deoxynucleoside triphosphate triphosphohydrolase SAMHD1 | Q9Y3Z3 | SAMH1_HUMAN | Homo sapiens | 3 | 0.7032 |
Deoxynucleoside triphosphate triphosphohydrolase SAMHD1 | Q9Y3Z3 | SAMH1_HUMAN | Homo sapiens | 3 | 0.7032 |