(2R)-2-O-beta-D-glucopyranosyl-2H-1,4-benzoxazin-3(4H)-one - Compound Card

(2R)-2-O-beta-D-glucopyranosyl-2H-1,4-benzoxazin-3(4H)-one

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(2R)-2-O-beta-D-glucopyranosyl-2H-1,4-benzoxazin-3(4H)-one

Structure
Zoomed Structure
  • Family: Plantae - Acanthaceae
  • Kingdom: Plantae
  • Class: Alkaloid
Canonical Smiles OC[C@H]1OC([C@H]2Oc3ccccc3NC2=O)[C@@H]([C@H]([C@@H]1O)O)O
InChI InChI=1S/C14H17NO7/c16-5-8-9(17)10(18)11(19)12(22-8)13-14(20)15-6-3-1-2-4-7(6)21-13/h1-4,8-13,16-19H,5H2,(H,15,20)/t8-,9-,10+,11-,12?,13-/m1/s1
InChIKey SFAHCAMKUIRNCU-DMEHNAEFSA-N
Formula C14H17NO7
HBA 7
HBD 5
MW 311.29
Rotatable Bonds 2
TPSA 128.48
LogP -1.77
Number Rings 3
Number Aromatic Rings 1
Heavy Atom Count 22
Formal Charge 0
Fraction CSP3 0.5
Exact Mass 311.1
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Ruellia tuberosa Acanthaceae Plantae 441035

Showing of synonyms

  • Samy MN, Khalil HE, et al. (2013). Chemical constituents from the leaves of Ruellia tuberosa. Chemistry of Natural Compounds,2013,49(1),175-176. [View]
Pubchem: 162842377

No compound-protein relationship available.

Structure

SMILES: c1cccc(c12)OC(C(=O)N2)C3CCCCO3

Level: 1

Mol. Weight: 311.29 g/mol

Structure

SMILES: N1C(=O)COc(c12)cccc2

Level: 0

Mol. Weight: 311.29 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 311.29 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.23
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.770
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.22

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.770
Plasma Protein Binding
43.17
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
1.650
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-1.980
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
1.290
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
3.060
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
-3.450
Rat (Acute)
2.330
Rat (Chronic Oral)
3.200
Fathead Minnow
3.520
Respiratory Disease
Safe
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
466.940
Hydration Free Energy
-19.040
Log(D) at pH=7.4
-0.410
Log(P)
-1.31
Log S
-1.64
Log(Vapor Pressure)
-13.19
Melting Point
182.39
pKa Acid
6.28
pKa Basic
5.85
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Macrophage metalloelastase P39900 MMP12_HUMAN Homo sapiens 3 0.8675
Macrophage metalloelastase P39900 MMP12_HUMAN Homo sapiens 3 0.8675
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.8656
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.8656
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.8545
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.8545
Glucan 1,3-beta-glucosidase P29717 EXG1_CANAL Candida albicans 3 0.8312
Glucan 1,3-beta-glucosidase P29717 EXG1_CANAL Candida albicans 3 0.8312
Glutamate receptor 2 P19491 GRIA2_RAT Rattus norvegicus 3 0.8250
Glutamate receptor 2 P19491 GRIA2_RAT Rattus norvegicus 3 0.8250
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8132
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8132
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 4 0.7995
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 4 0.7995
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.7849
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.7849
Methionine aminopeptidase 2 P9WK19 MAP12_MYCTU Mycobacterium tuberculosis 3 0.7800
Methionine aminopeptidase 2 P9WK19 MAP12_MYCTU Mycobacterium tuberculosis 3 0.7800
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7716
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7716
Glucan 1,3-beta-glucosidase P29717 EXG1_CANAL Candida albicans 3 0.7682
Glucan 1,3-beta-glucosidase P29717 EXG1_CANAL Candida albicans 3 0.7682
beta-glucosidase Q92AS9 Q92AS9_LISIN Listeria innocua serovar 6a 3 0.7663
beta-glucosidase Q92AS9 Q92AS9_LISIN Listeria innocua serovar 6a 3 0.7663
Beta-galactosidase P00722 BGAL_ECOLI Escherichia coli 4 0.7655
Beta-galactosidase P00722 BGAL_ECOLI Escherichia coli 4 0.7655
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7603
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7603
Caffeoyl-CoA O-methyltransferase Q40313 CAMT_MEDSA Medicago sativa 3 0.7600
Caffeoyl-CoA O-methyltransferase Q40313 CAMT_MEDSA Medicago sativa 3 0.7600
Ribonuclease J H9CZL7 H9CZL7_DEIRD Deinococcus radiodurans 3 0.7585
Ribonuclease J H9CZL7 H9CZL7_DEIRD Deinococcus radiodurans 3 0.7585
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 3 0.7498
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 3 0.7498
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.7470
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.7470
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7407
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7407
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 3 0.7388
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 3 0.7388
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.7343
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.7343
Cytidine and deoxycytidylate deaminase zinc-binding region Q82Y41 Q82Y41_NITEU Nitrosomonas europaea 3 0.7335
Cytidine and deoxycytidylate deaminase zinc-binding region Q82Y41 Q82Y41_NITEU Nitrosomonas europaea 3 0.7335
Collagenase 3 P45452 MMP13_HUMAN Homo sapiens 3 0.7330
Collagenase 3 P45452 MMP13_HUMAN Homo sapiens 3 0.7330
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7327
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7327
Metallo-beta-lactamase type 2 C7C422 BLAN1_KLEPN Klebsiella pneumoniae 2 0.7326
Metallo-beta-lactamase type 2 C7C422 BLAN1_KLEPN Klebsiella pneumoniae 2 0.7326
Uncharacterized protein YML079W Q03629 YMH9_YEAST Saccharomyces cerevisiae 2 0.7239
Uncharacterized protein YML079W Q03629 YMH9_YEAST Saccharomyces cerevisiae 2 0.7239
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7236
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7236
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.7225
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.7225
Beta-hexosaminidase Q9KU37 NAGZ_VIBCH Vibrio cholerae serotype O1 3 0.7215
Beta-hexosaminidase Q9KU37 NAGZ_VIBCH Vibrio cholerae serotype O1 3 0.7215
L-lactate dehydrogenase A chain P04642 LDHA_RAT Rattus norvegicus 3 0.7145
L-lactate dehydrogenase A chain P04642 LDHA_RAT Rattus norvegicus 3 0.7145
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 2 0.7130
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 2 0.7130
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 2 0.7098
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 2 0.7098
F420-dependent methylenetetrahydromethanopterin dehydrogenase P94951 MTD_METKA Methanopyrus kandleri 2 0.7096
F420-dependent methylenetetrahydromethanopterin dehydrogenase P94951 MTD_METKA Methanopyrus kandleri 2 0.7096
Adenosylmethionine-8-amino-7-oxononanoate aminotransferase P12995 BIOA_ECOLI Escherichia coli 2 0.7093
Adenosylmethionine-8-amino-7-oxononanoate aminotransferase P12995 BIOA_ECOLI Escherichia coli 2 0.7093
Flavin-dependent monooxygenase Q93L51 TETX_BACT4 Bacteroides thetaiotaomicron 3 0.7079
Flavin-dependent monooxygenase Q93L51 TETX_BACT4 Bacteroides thetaiotaomicron 3 0.7079
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7067
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7067
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7047
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7047
Precorrin-3 methylase O68097 O68097_RHOCA Rhodobacter capsulatus 3 0.7046
Precorrin-3 methylase O68097 O68097_RHOCA Rhodobacter capsulatus 3 0.7046
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 2 0.7003
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 2 0.7003

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