Indole-3-carboxylic acid-beta-D-glucoside - Compound Card

Indole-3-carboxylic acid-beta-D-glucoside

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Indole-3-carboxylic acid-beta-D-glucoside

Structure
Zoomed Structure
  • Family: Plantae - Lamiaceae
  • Kingdom: Plantae
  • Class: Alkaloid
    • Subclass: Indole Alkaloid Glucoside
Canonical Smiles OCC1OC(OC(=O)c2c[nH]c3c2cccc3)C(C(C1O)O)O
InChI InChI=1S/C15H17NO7/c17-6-10-11(18)12(19)13(20)15(22-10)23-14(21)8-5-16-9-4-2-1-3-7(8)9/h1-5,10-13,15-20H,6H2
InChIKey OQZPHKHJQADXAS-UHFFFAOYSA-N
Formula C15H17NO7
HBA 7
HBD 5
MW 323.3
Rotatable Bonds 3
TPSA 132.24
LogP -0.88
Number Rings 3
Number Aromatic Rings 2
Heavy Atom Count 23
Formal Charge 0
Fraction CSP3 0.4
Exact Mass 323.1
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Saccocalyx saturejoides Lamiaceae Plantae 751886

Showing of synonyms

  • Kherkhache H, Benabdelaziz I, et al. (2020). A new indole alkaloid, antioxidant and antibacterial activities of crude extracts from Saccocalyx satureioides. Natural product research, 2020, 34(11), 1528-1534. [View] [PubMed]
Pubchem: 75130936

No compound-protein relationship available.

Structure

SMILES: O1CCCCC1OC(=O)c2c[nH]c(c23)cccc3

Level: 1

Mol. Weight: 323.3 g/mol

Structure

SMILES: c1c[nH]c(c12)cccc2

Level: 0

Mol. Weight: 323.3 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 323.3 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.38
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-5.0
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.11

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.63
Plasma Protein Binding
-10.55
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
Inhibitor
CYP 1A2 Substrate
Non-Substrate
CYP 2C19 Inhibitor
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
7.03
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Safe
Bioconcentration Factor
-1.31
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.71
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
3.25
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
0.32
Rat (Acute)
2.22
Rat (Chronic Oral)
3.19
Fathead Minnow
3.76
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
435.62
Hydration Free Energy
-14.32
Log(D) at pH=7.4
0.24
Log(P)
0.2
Log S
-2.18
Log(Vapor Pressure)
-10.48
Melting Point
168.02
pKa Acid
5.31
pKa Basic
6.96
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Carbonic anhydrase 12 O43570 CAH12_HUMAN Homo sapiens 3 0.9281
Carminomycin 4-O-methyltransferase DnrK Q06528 DNRK_STRPE Streptomyces peucetius 3 0.8893
Thymidine kinase P0DTH5 KITH_HHV11 Human herpesvirus 1 3 0.8847
Aldos-2-ulose dehydratase P84193 AUD_PHACH Phanerodontia chrysosporium 3 0.8784
Gag-Pol polyprotein P04584 POL_HV2RO Human immunodeficiency virus type 2 subtype A 4 0.8577
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.8275
Prolyl tripeptidyl peptidase Q7MUW6 PTP_PORGI Porphyromonas gingivalis 3 0.8275
Glucan 1,3-beta-glucosidase P29717 EXG1_CANAL Candida albicans 3 0.8253
Proton-gated ion channel Q7NDN8 GLIC_GLOVI Gloeobacter violaceus 3 0.8252
Methionine aminopeptidase P0AE18 MAP1_ECOLI Escherichia coli 3 0.8178
Flavin-dependent monooxygenase Q93L51 TETX_BACT4 Bacteroides thetaiotaomicron 3 0.8017
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.8013
Beta-glucosidase 1A Q25BW5 BGL1A_PHACH Phanerodontia chrysosporium 3 0.7860
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7857
Methionine aminopeptidase P0AE18 MAP1_ECOLI Escherichia coli 3 0.7670
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 2 0.7636
Serine/threonine-protein kinase Chk2 O96017 CHK2_HUMAN Homo sapiens 2 0.7601
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7576
Gag-Pol polyprotein P05896 POL_SIVM1 Simian immunodeficiency virus 3 0.7527
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 3 0.7526
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase F6MZ55 F6MZ55_9FIRM Sporomusa ovata 2 0.7525
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 3 0.7514
4-diphosphocytidyl-2-C-methyl-D-erythritol kinase O67060 ISPE_AQUAE Aquifex aeolicus 3 0.7443
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7417
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 4 0.7385
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7332
Dihydropteroate synthase Q81VW8 Q81VW8_BACAN Bacillus anthracis 2 0.7327
Adenosine kinase Q9TVW2 ADK_TOXGO Toxoplasma gondii 4 0.7298
Adenosine 5'-monophosphoramidase HINT1 P80912 HINT1_RABIT Oryctolagus cuniculus 3 0.7297
Nitroreductase domain-containing protein Q8DW21 Q8DW21_STRMU Streptococcus mutans serotype c 3 0.7292
Multidrug efflux pump subunit AcrB P31224 ACRB_ECOLI Escherichia coli 3 0.7291
Disks large homolog 1 Q12959 DLG1_HUMAN Homo sapiens 3 0.7278
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7267
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7233
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7232
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7192
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7168
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7149
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 2 0.7148
Polymerase acidic protein Q5EP34 Q5EP34_9INFA Influenza A virus 2 0.7147
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.7147
Glutathione S-transferase P P09211 GSTP1_HUMAN Homo sapiens 2 0.7127
4-chlorobenzoyl CoA ligase Q8GN86 Q8GN86_9BURK Alcaligenes sp. AL3007 2 0.7105
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 3 0.7103
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 2 0.7085
ABC-type polar amino acid transport system, ATPase component Q8RCC2 Q8RCC2_CALS4 Caldanaerobacter subterraneus subsp. tengcongensis 2 0.7085
Dual specificity mitogen-activated protein kinase kinase 1 Q02750 MP2K1_HUMAN Homo sapiens 2 0.7040
Genome polyprotein P27395 POLG_JAEV1 Japanese encephalitis virus 2 0.7034
Pteridine reductase O76290 O76290_TRYBB Trypanosoma brucei brucei 2 0.7034
Purine nucleoside phosphorylase DeoD-type P0ABP9 DEOD_ECO57 Escherichia coli O157:H7 2 0.7025
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.7012

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