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Esculin
- Family: Plantae - Asteraceae
- Kingdom: Plantae
-
Class: Coumarin
- Subclass: Coumarin Glycoside
| Canonical Smiles | OC[C@H]1O[C@@H](Oc2cc3ccc(=O)oc3cc2O)[C@@H]([C@H]([C@@H]1O)O)O |
|---|---|
| InChI | InChI=1S/C15H16O9/c16-5-10-12(19)13(20)14(21)15(24-10)23-9-3-6-1-2-11(18)22-8(6)4-7(9)17/h1-4,10,12-17,19-21H,5H2/t10-,12-,13+,14-,15-/m1/s1 |
| InChIKey | XHCADAYNFIFUHF-TVKJYDDYSA-N |
| Formula | C15H16O9 |
| HBA | 9 |
| HBD | 5 |
| MW | 340.28 |
| Rotatable Bonds | 3 |
| TPSA | 149.82 |
| LogP | -1.32 |
| Number Rings | 3 |
| Number Aromatic Rings | 2 |
| Heavy Atom Count | 24 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.4 |
| Exact Mass | 340.08 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Erigeron floribundus | Asteraceae | Plantae | 91244 |
Showing of synonyms
Esculin
531-75-9
Bicolorin
Enallachrome
Escosyl
Esculetin 6-O-glucoside
(-)-Esculin
6,7-Dihydroxycoumarin 6-glucoside
Aesculinum
Esculetin 6-beta-D-glucoside
6,7-Dihydroxycoumarin-6-O-glucoside
Aesculetin glukosid
CHEBI:4853
Esculina
7-Hydroxy-6-cumarinyl-glucosid
6-(beta-D-Glucopyranosyloxy)-7-hydroxy-cumarin
Esculetin glukosid
UNII-1Y1L18LQAF
1Y1L18LQAF
NSC-26665
CCRIS 5724
6-(beta-D-Glucopyranosyloxy)-7-hydroxy-2H-1-benzopyran-2-one
DTXSID7045318
7-Hydroxy-6-glucosyloxy-2H-chromen
EINECS 208-517-5
NSC 26665
7-Hydroxy-6-glucosyloxy-2H-chromene
DTXCID5025318
7-hydroxy-2-oxo-2H-chromen-6-yl beta-D-glucopyranoside
208-517-5
Aesculin
Esculoside
Crataegin
Esculine
Vitamin C2
Esculin hydrate
7-hydroxy-6-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-2H-chromen-2-one
Esculetin 6-b-D-glucoside
7-hydroxy-6-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-2-one
Venoplant
2H-1-Benzopyran-2-one, 6-(.beta.-D-glucopyranosyloxy)-7-hydroxy-
6-(.beta.-D-Glucopyranosyloxy)-7-hydroxy-2H-1-benzopyran-2-one
MFCD00149492
7-hydroxy-6-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2H-chromen-2-one
ESCULOSIDE [JAN]
6-[(2S,3R,4S,5S,6R)-6-(hydroxymethyl)-3,4,5-tris(oxidanyl)oxan-2-yl]oxy-7-oxidanyl-chromen-2-one
7-hydroxy-6-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy- 6-(hydroxymethyl)-2-tetrahydropyranyl]oxy}-2-chromenone
Esculetin-6-beta-D-glucopyranoside
SR-01000633930
NCGC00016491-01
CAS-531-75-9
Aesculin (Esculin)
Esculin (Standard)
MFCD00006879
Aesculin sesquihydrate
Spectrum_000361
6,7-Dihydroxycoumarine-6-glucopyranoside
ESCULIN [MI]
Spectrum2_000576
Spectrum3_000731
Spectrum4_001923
Spectrum5_000845
AESCULINUM [HPUS]
SCHEMBL2893
ESCULOSIDE [WHO-DD]
BSPBio_002282
KBioGR_002266
KBioSS_000841
DivK1c_000956
SPECTRUM1500901
SPBio_000392
CHEMBL482581
Esculetin-6-b-D-glucopyranoside
BCBcMAP01_000202
Esculetin 6-.beta.-D-glucoside
HMS502P18
HY-N0188R
KBio1_000956
KBio2_000841
KBio2_003409
KBio2_005977
KBio3_001502
NINDS_000956
HMS1921M16
2H-1-Benzopyran-2-one, 6-(beta-D-glucopyranosyloxy)-7-hydroxy-
EX-A6781
HY-N0188
Tox21_110453
BDBM50480261
CCG-38501
S2258
AKOS015895151
DB13155
SDCCGMLS-0066653.P001
IDI1_000956
SMP1_000008
NCGC00094874-04
7-hydroxy-6-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-chromen-2-one
CS-0007892
NS00009922
7-Hydroxycoumarin-6-yl beta-D-Glucopyranoside
C09264
EN300-116211
6-(.beta.-D-Glucopyranosyloxy)-7-hydroxy-cumarin
Q376432
SR-01000633930-1
SR-01000633930-3
BRD-K51742987-001-02-3
BRD-K51742987-002-02-1
Esculin, European Pharmacopoeia (EP) Reference Standard
Z1494829512
7OU
Pubchem:
5281417
Cas:
531-75-9
Gnps:
CCMSLIB00006458221
Zinc:
ZINC000003860441
Kegg Ligand:
C09264
Chebi:
4853
Nmrshiftdb2:
60023901
Metabolights:
MTBLC4853
Chembl:
CHEMBL482581
Comptox:
DTXSID7045318
Drugbank:
DB13155
Pdb Ligand:
7OU
Bindingdb:
50480261
Selleck:
Aesculin(Esculin)
CPRiL:
51603
SMILES: c1cc(=O)oc(c12)ccc(c2)OC3CCCCO3
Level: 1
Mol. Weight: 340.28 g/mol
SMILES: c1cccc(c12)oc(=O)cc2
Level: 0
Mol. Weight: 340.28 g/mol
SMILES: C1CCOCC1
Level: 0
Mol. Weight: 340.28 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -5.73
- Human Oral Bioavailability 20%
- Non-Bioavailable
- Human Intestinal Absorption
- Non-Absorbed
- Madin-Darby Canine Kidney
- -5.280
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -0.82
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Non-Penetrable
- Fraction Unbound (Human)
- 0.760
- Plasma Protein Binding
- 72.8
- 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
- 9.590
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Safe
- Bioconcentration Factor
- -1.710
- Biodegradation
- Toxic
- Carcinogenesis
- Safe
- Crustacean
- Safe
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 0.830
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 4.520
- 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
- -2.620
- Rat (Acute)
- 2.010
- Rat (Chronic Oral)
- 3.470
- Fathead Minnow
- 3.920
- Respiratory Disease
- Safe
- Skin Sensitisation
- Toxic
- SR-ARE
- Safe
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Safe
- SR-p53
- Toxic
General Properties
- Boiling Point
- 490.120
- Hydration Free Energy
- -15.270
- Log(D) at pH=7.4
- -0.570
- Log(P)
- -1.44
- Log S
- -2.35
- Log(Vapor Pressure)
- -11.89
- Melting Point
- 192.91
- pKa Acid
- 4.52
- pKa Basic
- 6.67
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 3 | 0.9767 |
| CREB-binding protein | Q92793 | CBP_HUMAN | Homo sapiens | 3 | 0.8981 |
| Tetracycline repressor protein class D | P0ACT4 | TETR4_ECOLX | Escherichia coli | 3 | 0.8939 |
| Mitogen-activated protein kinase 1 | P28482 | MK01_HUMAN | Homo sapiens | 3 | 0.8925 |
| Flavin-dependent monooxygenase | Q93L51 | TETX_BACT4 | Bacteroides thetaiotaomicron | 3 | 0.8881 |
| Pentaerythritol tetranitrate reductase | P71278 | P71278_ENTCL | Enterobacter cloacae | 3 | 0.8881 |
| Tetracycline repressor protein class D | P0ACT4 | TETR4_ECOLX | Escherichia coli | 3 | 0.8842 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 2 | 0.8767 |
| DNA polymerase III subunit epsilon | P03007 | DPO3E_ECOLI | Escherichia coli | 3 | 0.8690 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 3 | 0.8645 |
| Tyrosine-protein kinase JAK2 | O60674 | JAK2_HUMAN | Homo sapiens | 3 | 0.8338 |
| Tetracycline repressor protein class D | P0ACT4 | TETR4_ECOLX | Escherichia coli | 3 | 0.8223 |
| Serpin domain-containing protein | H0ZQY2 | H0ZQY2_TAEGU | Taeniopygia guttata | 3 | 0.8130 |
| L-lactate dehydrogenase A chain | P04642 | LDHA_RAT | Rattus norvegicus | 3 | 0.8044 |
| Acetylcholinesterase | P21836 | ACES_MOUSE | Mus musculus | 2 | 0.7999 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 2 | 0.7900 |
| Acetylcholinesterase | P04058 | ACES_TETCF | Tetronarce californica | 3 | 0.7865 |
| Endothiapepsin | P11838 | CARP_CRYPA | Cryphonectria parasitica | 3 | 0.7845 |
| Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase | Q9TQS6 | DHDH_MACFA | Macaca fascicularis | 3 | 0.7838 |
| beta-glucosidase | Q92AS9 | Q92AS9_LISIN | Listeria innocua serovar 6a | 3 | 0.7824 |
| Acetylcholinesterase | P04058 | ACES_TETCF | Tetronarce californica | 3 | 0.7721 |
| Poly [ADP-ribose] polymerase 1 | P26446 | PARP1_CHICK | Gallus gallus | 3 | 0.7663 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 2 | 0.7654 |
| AGAP003309-PA | A0A1U7F4W2 | A0A1U7F4W2_ANOGA | Anopheles gambiae | 3 | 0.7638 |
| Pancreatic alpha-amylase | P04746 | AMYP_HUMAN | Homo sapiens | 3 | 0.7619 |
| Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase | Q05603 | COBT_SALTY | Salmonella typhimurium | 2 | 0.7607 |
| Steroid Delta-isomerase | P00947 | SDIS_COMTE | Comamonas testosteroni | 2 | 0.7591 |
| Polyribonucleotide nucleotidyltransferase | A7ZS61 | PNP_ECO24 | Escherichia coli O139:H28 | 3 | 0.7560 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.7535 |
| NADPH dehydrogenase 1 | Q02899 | OYE1_SACPS | Saccharomyces pastorianus | 3 | 0.7513 |
| Endoplasmin | P41148 | ENPL_CANLF | Canis lupus familiaris | 3 | 0.7512 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 2 | 0.7512 |
| Basic phospholipase A2 VRV-PL-VIIIa | P59071 | PA2B8_DABRR | Daboia russelii | 3 | 0.7463 |
| Polymerase acidic protein | C3W5S0 | C3W5S0_I09A0 | Influenza A virus | 2 | 0.7454 |
| Adenosine 5'-monophosphoramidase HINT1 | P80912 | HINT1_RABIT | Oryctolagus cuniculus | 3 | 0.7414 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.7409 |
| Endoplasmin | P41148 | ENPL_CANLF | Canis lupus familiaris | 3 | 0.7370 |
| Mitochondrial poly(A) polymerase | F1NBW0 | F1NBW0_CHICK | Gallus gallus | 2 | 0.7360 |
| Tyrosine-protein kinase SYK | P43405 | KSYK_HUMAN | Homo sapiens | 3 | 0.7301 |
| Beta-galactoside-specific lectin 4 | Q6ITZ3 | ML4_VISAL | Viscum album | 2 | 0.7296 |
| HD domain protein | Q836G9 | Q836G9_ENTFA | Enterococcus faecalis | 3 | 0.7291 |
| Serine/threonine-protein kinase Chk1 | O14757 | CHK1_HUMAN | Homo sapiens | 3 | 0.7277 |
| Endoplasmin | P41148 | ENPL_CANLF | Canis lupus familiaris | 3 | 0.7248 |
| LIM domain kinase 1 | P53667 | LIMK1_HUMAN | Homo sapiens | 2 | 0.7231 |
| Prothrombin | P00734 | THRB_HUMAN | Homo sapiens | 3 | 0.7214 |
| Cathepsin S | P25774 | CATS_HUMAN | Homo sapiens | 3 | 0.7211 |
| Nucleoside diphosphate kinase A 2 | P52175 | NDKA2_BOVIN | Bos taurus | 3 | 0.7177 |
| Histone-lysine N-methyltransferase EHMT1 | Q9H9B1 | EHMT1_HUMAN | Homo sapiens | 2 | 0.7176 |
| Gag-Pol polyprotein | P04584 | POL_HV2RO | Human immunodeficiency virus type 2 subtype A | 3 | 0.7163 |
| Glycogen phosphorylase, muscle form | P00489 | PYGM_RABIT | Oryctolagus cuniculus | 3 | 0.7142 |
| Glucan 1,3-beta-glucosidase | P29717 | EXG1_CANAL | Candida albicans | 3 | 0.7135 |
| NTPase P4 | Q94M05 | Q94M05_9VIRU | Pseudomonas phage phi12 | 3 | 0.7115 |
| Glycogen phosphorylase, muscle form | P00489 | PYGM_RABIT | Oryctolagus cuniculus | 5 | 0.7076 |
| Glycogen phosphorylase, muscle form | P00489 | PYGM_RABIT | Oryctolagus cuniculus | 3 | 0.7056 |
| Glycogen phosphorylase, muscle form | P00489 | PYGM_RABIT | Oryctolagus cuniculus | 5 | 0.7048 |
| Phosphatidylinositol 5-phosphate 4-kinase type-2 beta | P78356 | PI42B_HUMAN | Homo sapiens | 3 | 0.7035 |
| Disks large homolog 1 | Q12959 | DLG1_HUMAN | Homo sapiens | 3 | 0.7026 |
| Uncharacterized protein YML079W | Q03629 | YMH9_YEAST | Saccharomyces cerevisiae | 3 | 0.7026 |
| Pentaerythritol tetranitrate reductase | P71278 | P71278_ENTCL | Enterobacter cloacae | 3 | 0.7026 |
| Ribosyldihydronicotinamide dehydrogenase [quinone] | P16083 | NQO2_HUMAN | Homo sapiens | 4 | 0.7003 |