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

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

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(2R)-2-O-beta-D-glucopyranosyl-4-hydroxy-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]([C@H]([C@@H]1O)O)O)[C@H]1Oc2ccccc2N(C1=O)O
InChI InChI=1S/C14H17NO8/c16-5-8-9(17)10(18)11(19)12(23-8)13-14(20)15(21)6-3-1-2-4-7(6)22-13/h1-4,8-13,16-19,21H,5H2/t8-,9-,10+,11-,12?,13-/m1/s1
InChIKey MDURBJSVWZOREE-DMEHNAEFSA-N
Formula C14H17NO8
HBA 8
HBD 5
MW 327.29
Rotatable Bonds 2
TPSA 139.92
LogP -1.99
Number Rings 3
Number Aromatic Rings 1
Heavy Atom Count 23
Formal Charge 0
Fraction CSP3 0.5
Exact Mass 327.1
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: 162817636
CPRiL: 155143
Structure

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

Level: 1

Mol. Weight: 327.29 g/mol

Structure

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

Level: 0

Mol. Weight: 327.29 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 327.29 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.16
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.880
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-0.75

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.500
Plasma Protein Binding
53.82
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
4.090
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-1.870
Biodegradation
Safe
Carcinogenesis
Toxic
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
1.170
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
3.860
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
-3.740
Rat (Acute)
2.070
Rat (Chronic Oral)
3.390
Fathead Minnow
3.970
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Safe

General Properties

Boiling Point
429.200
Hydration Free Energy
-17.500
Log(D) at pH=7.4
-1.110
Log(P)
-0.59
Log S
-1.94
Log(Vapor Pressure)
-11.85
Melting Point
188.61
pKa Acid
4.52
pKa Basic
4.57
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Proton-gated ion channel Q7NDN8 GLIC_GLOVI Gloeobacter violaceus 3 0.9186
Proton-gated ion channel Q7NDN8 GLIC_GLOVI Gloeobacter violaceus 3 0.9186
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.9153
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.9153
Glutamate receptor 2 P19491 GRIA2_RAT Rattus norvegicus 3 0.8812
Glutamate receptor 2 P19491 GRIA2_RAT Rattus norvegicus 3 0.8812
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 3 0.8722
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 3 0.8722
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.8584
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.8584
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.8548
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.8548
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.8534
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.8534
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.8465
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.8465
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.8459
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.8459
Glutamate receptor 2 P19491 GRIA2_RAT Rattus norvegicus 3 0.8378
Glutamate receptor 2 P19491 GRIA2_RAT Rattus norvegicus 3 0.8378
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.8342
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.8342
Gag-Pol polyprotein P04584 POL_HV2RO Human immunodeficiency virus type 2 subtype A 4 0.7950
Gag-Pol polyprotein P04584 POL_HV2RO Human immunodeficiency virus type 2 subtype A 4 0.7950
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 3 0.7885
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 3 0.7885
Purine nucleoside phosphorylase DeoD-type P0ABP9 DEOD_ECO57 Escherichia coli O157:H7 3 0.7818
Purine nucleoside phosphorylase DeoD-type P0ABP9 DEOD_ECO57 Escherichia coli O157:H7 3 0.7818
Macrophage metalloelastase P39900 MMP12_HUMAN Homo sapiens 3 0.7752
Macrophage metalloelastase P39900 MMP12_HUMAN Homo sapiens 3 0.7752
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7715
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7715
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7562
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7562
beta-glucosidase Q92AS9 Q92AS9_LISIN Listeria innocua serovar 6a 3 0.7489
beta-glucosidase Q92AS9 Q92AS9_LISIN Listeria innocua serovar 6a 3 0.7489
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7480
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7480
Flavin-dependent monooxygenase Q93L51 TETX_BACT4 Bacteroides thetaiotaomicron 3 0.7459
Flavin-dependent monooxygenase Q93L51 TETX_BACT4 Bacteroides thetaiotaomicron 3 0.7459
Chloramphenicol 3-O phosphotransferase Q56148 CPT_STRVP Streptomyces venezuelae 3 0.7434
Chloramphenicol 3-O phosphotransferase Q56148 CPT_STRVP Streptomyces venezuelae 3 0.7434
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.7416
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.7416
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 4 0.7407
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 4 0.7407
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.7362
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.7362
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 3 0.7350
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 3 0.7350
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.7306
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.7306
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7284
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7284
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.7272
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.7272
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 2 0.7233
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 2 0.7233
Glutamate receptor 2 P19491 GRIA2_RAT Rattus norvegicus 3 0.7194
Glutamate receptor 2 P19491 GRIA2_RAT Rattus norvegicus 3 0.7194
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 2 0.7192
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 2 0.7192
Penicillin V acylase P12256 PAC_LYSSH Lysinibacillus sphaericus 3 0.7128
Penicillin V acylase P12256 PAC_LYSSH Lysinibacillus sphaericus 3 0.7128
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7126
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7126
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 4 0.7125
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 4 0.7125
Tryptophan synthase alpha chain P00929 TRPA_SALTY Salmonella typhimurium 2 0.7115
Tryptophan synthase alpha chain P00929 TRPA_SALTY Salmonella typhimurium 2 0.7115
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7105
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7105
L-lactate dehydrogenase A chain P04642 LDHA_RAT Rattus norvegicus 3 0.7085
L-lactate dehydrogenase A chain P04642 LDHA_RAT Rattus norvegicus 3 0.7085
5-methyltetrahydropteroyltriglutamate--homocysteine methyltransferase 1 O50008 METE1_ARATH Arabidopsis thaliana 2 0.7067
5-methyltetrahydropteroyltriglutamate--homocysteine methyltransferase 1 O50008 METE1_ARATH Arabidopsis thaliana 2 0.7067
Adenosine kinase Q9TVW2 ADK_TOXGO Toxoplasma gondii 3 0.7065
Adenosine kinase Q9TVW2 ADK_TOXGO Toxoplasma gondii 3 0.7065
Class 10 plant pathogenesis-related protein 2B Q9LLQ2 P102B_LUPLU Lupinus luteus 3 0.7062
Class 10 plant pathogenesis-related protein 2B Q9LLQ2 P102B_LUPLU Lupinus luteus 3 0.7062
Cobalt-precorrin-4 C(11)-methyltransferase O87696 CBIF_BACME Priestia megaterium 3 0.7049
Cobalt-precorrin-4 C(11)-methyltransferase O87696 CBIF_BACME Priestia megaterium 3 0.7049
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 3 0.7048
Glutamate receptor 3 P19492 GRIA3_RAT Rattus norvegicus 3 0.7048
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 3 0.7048
Glutamate receptor 3 P19492 GRIA3_RAT Rattus norvegicus 3 0.7048
Prolyl tripeptidyl peptidase Q7MUW6 PTP_PORGI Porphyromonas gingivalis 2 0.7043
Prolyl tripeptidyl peptidase Q7MUW6 PTP_PORGI Porphyromonas gingivalis 2 0.7043
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 2 0.7028
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 2 0.7028
Protein RecA Q59560 RECA_MYCS2 Mycolicibacterium smegmatis155) 4 0.7001
Protein RecA Q59560 RECA_MYCS2 Mycolicibacterium smegmatis155) 4 0.7001

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