5-beta-D-glucopyranosyloxy-7-methoxy-6H-benzopyran-2-one - Compound Card

5-beta-D-glucopyranosyloxy-7-methoxy-6H-benzopyran-2-one

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5-beta-D-glucopyranosyloxy-7-methoxy-6H-benzopyran-2-one

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Coumarin
    • Subclass: Coumarin Glucoside
Canonical Smiles OCC1OC(Oc2cc(OC)cc3c2ccc(=O)o3)C(C(C1O)O)O
InChI InChI=1S/C16H18O9/c1-22-7-4-9-8(2-3-12(18)23-9)10(5-7)24-16-15(21)14(20)13(19)11(6-17)25-16/h2-5,11,13-17,19-21H,6H2,1H3
InChIKey CVUNWLJTMGUQOF-UHFFFAOYSA-N
Formula C16H18O9
HBA 9
HBD 4
MW 354.31
Rotatable Bonds 4
TPSA 138.82
LogP -1.02
Number Rings 3
Number Aromatic Rings 2
Heavy Atom Count 25
Formal Charge 0
Fraction CSP3 0.44
Exact Mass 354.1
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Artemisia herba-alba Asteraceae Plantae 72329

Showing of synonyms

  • Mohamed T.A, Abd El Aty A.A, et al. (2021). New antimicrobial metabolites from the medicinal herb Artemisia herba-Alba. Natural product research, 2021, 35(12), 1959-1967. [View] [PubMed]

No compound-protein relationship available.

Structure

SMILES: c1cc(=O)oc(c12)cccc2OC3CCCCO3

Level: 1

Mol. Weight: 354.31 g/mol

Structure

SMILES: c1cccc(c12)oc(=O)cc2

Level: 0

Mol. Weight: 354.31 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 354.31 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.59
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Non-Absorbed
Madin-Darby Canine Kidney
-4.81
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.31

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.78
Plasma Protein Binding
8.94
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-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
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
5.0
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.56
Biodegradation
Toxic
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
1.16
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
4.42
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
0.24
Rat (Acute)
2.11
Rat (Chronic Oral)
3.23
Fathead Minnow
4.08
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
458.75
Hydration Free Energy
-14.28
Log(D) at pH=7.4
-0.13
Log(P)
-0.75
Log S
-2.42
Log(Vapor Pressure)
-9.72
Melting Point
177.2
pKa Acid
5.54
pKa Basic
3.96
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 0.9087
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.9039
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.8942
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.8787
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.8784
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.8765
Aldos-2-ulose dehydratase P84193 AUD_PHACH Phanerodontia chrysosporium 3 0.8623
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8599
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.8340
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 3 0.8262
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.8152
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.8100
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.8046
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.8026
Adenosine 5'-monophosphoramidase HINT1 P80912 HINT1_RABIT Oryctolagus cuniculus 3 0.7891
Toxoflavin degrading enzyme E3SET7 E3SET7_PAEPO Paenibacillus polymyxa 3 0.7866
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.7738
Carminomycin 4-O-methyltransferase DnrK Q06528 DNRK_STRPE Streptomyces peucetius 3 0.7708
N-alpha-acetyltransferase 50 Q9GZZ1 NAA50_HUMAN Homo sapiens 3 0.7602
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.7516
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.7512
Thymidine kinase P0DTH5 KITH_HHV11 Human herpesvirus 1 3 0.7509
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 4 0.7485
Beta-galactosidase P00722 BGAL_ECOLI Escherichia coli 4 0.7462
Pteridine reductase, putative Q581W1 Q581W1_TRYB2 Trypanosoma brucei brucei 2 0.7433
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.7419
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 2 0.7413
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.7348
CREB-binding protein Q92793 CBP_HUMAN Homo sapiens 3 0.7279
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7233
Thymidylate synthase P0A884 TYSY_ECOLI Escherichia coli 4 0.7215
cGMP-dependent protein kinase 1 Q13976 KGP1_HUMAN Homo sapiens 2 0.7210
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 3 0.7195
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7141
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.7123
Gag-Pol polyprotein P04584 POL_HV2RO Human immunodeficiency virus type 2 subtype A 3 0.7069
Metallo-beta-lactamase type 2 C7C422 BLAN1_KLEPN Klebsiella pneumoniae 2 0.7046
CCA-adding enzyme O28126 CCA_ARCFU Archaeoglobus fulgidus 2 0.7026
[LysW]-aminoadipate kinase O50147 LYSZ_THET2 Thermus thermophilus 3 0.7011
Glutamate receptor 2 P19491 GRIA2_RAT Rattus norvegicus 2 0.7004

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