Dihydroisocoumarin glucoside - Compound Card

Dihydroisocoumarin glucoside

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Dihydroisocoumarin glucoside

Structure
Zoomed Structure
  • Family: Plantae - Asphodelaceae
  • Kingdom: Plantae
  • Class: Coumarin
Canonical Smiles OC[C@H]1OC(Oc2cc(O)cc(c2C(=O)C)CC2OC(=O)c3c(C2)cc(cc3O)O)[C@@H]([C@H]([C@@H]1O)O)O
InChI InChI=1S/C24H26O12/c1-9(26)18-10(4-14-5-11-3-12(27)6-15(29)19(11)23(33)34-14)2-13(28)7-16(18)35-24-22(32)21(31)20(30)17(8-25)36-24/h2-3,6-7,14,17,20-22,24-25,27-32H,4-5,8H2,1H3/t14?,17-,20-,21+,22-,24?/m1/s1
InChIKey LMZXJMGFKWTFDY-NCTLFSKISA-N
Formula C24H26O12
HBA 12
HBD 7
MW 506.46
Rotatable Bonds 6
TPSA 203.44
LogP -0.49
Number Rings 4
Number Aromatic Rings 2
Heavy Atom Count 36
Formal Charge 0
Fraction CSP3 0.42
Exact Mass 506.14
Number of Lipinski Rule Violations 3
# Species Family Kingdom NCBI Taxonomy ID
1 Aloe hildebrandtii Asphodelaceae Plantae 1593080

Showing of synonyms

  • 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.

Structure

SMILES: c1cccc(c12)CC(OC2=O)Cc3cc(ccc3)OC4CCCCO4

Level: 2

Mol. Weight: 506.46 g/mol

Structure

SMILES: c1ccccc1CC(OC2=O)Cc(c23)cccc3

Level: 1

Mol. Weight: 506.46 g/mol

Structure

SMILES: c1ccccc1OC2CCCCO2

Level: 1

Mol. Weight: 506.46 g/mol

Structure

SMILES: c1cccc(c12)CCOC2=O

Level: 0

Mol. Weight: 506.46 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 506.46 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 506.46 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-6.99
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Non-Absorbed
Madin-Darby Canine Kidney
-5.32
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
-0.54

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.8
Plasma Protein Binding
51.72
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
11.66
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-2.25
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.57
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.03
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
-376.83
Rat (Acute)
2.25
Rat (Chronic Oral)
3.97
Fathead Minnow
4.27
Respiratory Disease
Safe
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
627.76
Hydration Free Energy
-3.37
Log(D) at pH=7.4
0.29
Log(P)
0.17
Log S
-3.66
Log(Vapor Pressure)
-12.09
Melting Point
207.4
pKa Acid
5.25
pKa Basic
6.62
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.9092
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.9092
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 3 0.9030
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 3 0.9030
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.9015
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.9015
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8954
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8954
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8945
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8945
Flavin-dependent monooxygenase Q93L51 TETX_BACT4 Bacteroides thetaiotaomicron 3 0.8741
Flavin-dependent monooxygenase Q93L51 TETX_BACT4 Bacteroides thetaiotaomicron 3 0.8741
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.8562
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.8562
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8527
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8527
Flavoredoxin Q72HI0 Q72HI0_THET2 Thermus thermophilus 3 0.8509
Flavoredoxin Q72HI0 Q72HI0_THET2 Thermus thermophilus 3 0.8509
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 4 0.8500
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 4 0.8500
Carbonyl reductase [NADPH] 1 P16152 CBR1_HUMAN Homo sapiens 3 0.8495
Carbonyl reductase [NADPH] 1 P16152 CBR1_HUMAN Homo sapiens 3 0.8495
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.8448
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.8448
Glucan 1,3-beta-glucosidase P29717 EXG1_CANAL Candida albicans 3 0.8420
Glucan 1,3-beta-glucosidase P29717 EXG1_CANAL Candida albicans 3 0.8420
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8415
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8415
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.8371
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.8371
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8355
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8355
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 3 0.8353
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 3 0.8353
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase F6MZ55 F6MZ55_9FIRM Sporomusa ovata 3 0.8331
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase F6MZ55 F6MZ55_9FIRM Sporomusa ovata 3 0.8331
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.8321
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.8321
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase Q81LL4 MTNN_BACAN Bacillus anthracis 3 0.8229
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase Q81LL4 MTNN_BACAN Bacillus anthracis 3 0.8229
Purine nucleoside phosphorylase DeoD-type P0ABP8 DEOD_ECOLI Escherichia coli 3 0.8130
Purine nucleoside phosphorylase DeoD-type P0ABP8 DEOD_ECOLI Escherichia coli 3 0.8130
Rhodopsin kinase GRK1 P28327 GRK1_BOVIN Bos taurus 3 0.8118
Rhodopsin kinase GRK1 P28327 GRK1_BOVIN Bos taurus 3 0.8118
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.8108
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.8108
Cyclic dipeptide N-prenyltransferase D1D8L6 D1D8L6_ASPFM Neosartorya fumigata 3 0.7993
Cyclic dipeptide N-prenyltransferase D1D8L6 D1D8L6_ASPFM Neosartorya fumigata 3 0.7993
Histone deacetylase 4 P56524 HDAC4_HUMAN Homo sapiens 3 0.7909
Histone deacetylase 4 P56524 HDAC4_HUMAN Homo sapiens 3 0.7909
Stromelysin-1 P08254 MMP3_HUMAN Homo sapiens 3 0.7903
Stromelysin-1 P08254 MMP3_HUMAN Homo sapiens 3 0.7903
Purine nucleoside phosphorylase DeoD-type P0ABP9 DEOD_ECO57 Escherichia coli O157:H7 3 0.7889
Purine nucleoside phosphorylase DeoD-type P0ABP9 DEOD_ECO57 Escherichia coli O157:H7 3 0.7889
beta-glucosidase Q92AS9 Q92AS9_LISIN Listeria innocua serovar 6a 3 0.7858
beta-glucosidase Q92AS9 Q92AS9_LISIN Listeria innocua serovar 6a 3 0.7858
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 4 0.7852
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 4 0.7852
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.7795
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.7795
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7778
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7778
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7773
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7773
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7735
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7735
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.7710
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.7710
L-lactate dehydrogenase A chain P04642 LDHA_RAT Rattus norvegicus 3 0.7706
L-lactate dehydrogenase A chain P04642 LDHA_RAT Rattus norvegicus 3 0.7706
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7694
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7694
Nitric oxide synthase 3 P29474 NOS3_HUMAN Homo sapiens 3 0.7681
Nitric oxide synthase 3 P29474 NOS3_HUMAN Homo sapiens 3 0.7681
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.7565
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.7565
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7564
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7564
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7497
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7497
Carbonyl reductase [NADPH] 1 P16152 CBR1_HUMAN Homo sapiens 3 0.7488
Carbonyl reductase [NADPH] 1 P16152 CBR1_HUMAN Homo sapiens 3 0.7488
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 3 0.7392
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 3 0.7392
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7381
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7381
Nitric oxide synthase 1 P29476 NOS1_RAT Rattus norvegicus 3 0.7367
Nitric oxide synthase 1 P29476 NOS1_RAT Rattus norvegicus 3 0.7367
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.7345
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.7345
Proton-gated ion channel Q7NDN8 GLIC_GLOVI Gloeobacter violaceus 3 0.7311
Proton-gated ion channel Q7NDN8 GLIC_GLOVI Gloeobacter violaceus 3 0.7311
Seminal ribonuclease P00669 RNS_BOVIN Bos taurus 3 0.7278
Seminal ribonuclease P00669 RNS_BOVIN Bos taurus 3 0.7278
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7259
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7259
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 2 0.7258
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 2 0.7258
Kynurenine/alpha-aminoadipate aminotransferase, mitochondrial Q8N5Z0 AADAT_HUMAN Homo sapiens 2 0.7252
Kynurenine/alpha-aminoadipate aminotransferase, mitochondrial Q8N5Z0 AADAT_HUMAN Homo sapiens 2 0.7252
Vitamin D-binding protein P02774 VTDB_HUMAN Homo sapiens 3 0.7220
Vitamin D-binding protein P02774 VTDB_HUMAN Homo sapiens 3 0.7220
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 3 0.7220
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 3 0.7220
Multidrug efflux pump subunit AcrB P31224 ACRB_ECOLI Escherichia coli 3 0.7217
Multidrug efflux pump subunit AcrB P31224 ACRB_ECOLI Escherichia coli 3 0.7217
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.7215
Xylose isomerase P24300 XYLA_STRRU Streptomyces rubiginosus 3 0.7215
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.7215
Xylose isomerase P24300 XYLA_STRRU Streptomyces rubiginosus 3 0.7215
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7174
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7174
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7159
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7159
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta P78356 PI42B_HUMAN Homo sapiens 3 0.7158
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta P78356 PI42B_HUMAN Homo sapiens 3 0.7158
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7156
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7156
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7146
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7146
5-methylthioadenosine/S-adenosylhomocysteine deaminase Q7NZ90 Q7NZ90_CHRVO Chromobacterium violaceum 3 0.7145
5-methylthioadenosine/S-adenosylhomocysteine deaminase Q7NZ90 Q7NZ90_CHRVO Chromobacterium violaceum 3 0.7145
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 2 0.7133
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 2 0.7133
Thymidine phosphorylase Q7CP66 TYPH_SALTY Salmonella typhimurium 3 0.7127
Thymidine phosphorylase Q7CP66 TYPH_SALTY Salmonella typhimurium 3 0.7127
Avidin P02701 AVID_CHICK Gallus gallus 3 0.7120
Avidin P02701 AVID_CHICK Gallus gallus 3 0.7120
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.7093
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.7093
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.7048
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.7048
Secoisolariciresinol dehydrogenase Q94KL8 SILD_PODPE Podophyllum peltatum 4 0.7043
Secoisolariciresinol dehydrogenase Q94KL8 SILD_PODPE Podophyllum peltatum 4 0.7043
Serine/threonine-protein kinase PLK1 P53350 PLK1_HUMAN Homo sapiens 3 0.7009
Serine/threonine-protein kinase PLK1 P53350 PLK1_HUMAN Homo sapiens 3 0.7009
DNA topoisomerase 4 subunit B H7C794 PARE_ENTFA Enterococcus faecalis 3 0.7007
DNA topoisomerase 4 subunit B H7C794 PARE_ENTFA Enterococcus faecalis 3 0.7007
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7004
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7004
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.7002
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.7002

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