Foliamenthoic acid 1-O-beta-D-glucopyranosyl ester 8-O-beta-D-glucopyranoside - Compound Card

Foliamenthoic acid 1-O-beta-D-glucopyranosyl ester 8-O-beta-D-glucopyranoside

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Foliamenthoic acid 1-O-beta-D-glucopyranosyl ester 8-O-beta-D-glucopyranoside

Structure
Zoomed Structure
  • Family: Plantae - Plantaginaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Monoterpene
Canonical Smiles OC/C=C(/CC/C=C(/C(=O)OCC1OC(O)[C@H](C([C@@H]1O)O)O)\C)\C
InChI InChI=1S/C16H26O8/c1-9(6-7-17)4-3-5-10(2)15(21)23-8-11-12(18)13(19)14(20)16(22)24-11/h5-6,11-14,16-20,22H,3-4,7-8H2,1-2H3/b9-6+,10-5+/t11?,12-,13?,14+,16?/m1/s1
InChIKey VHGCKOCWKLWVCS-LSRUFGOOSA-N
Formula C16H26O8
HBA 8
HBD 5
MW 346.38
Rotatable Bonds 7
TPSA 136.68
LogP -1.01
Number Rings 1
Number Aromatic Rings 0
Heavy Atom Count 24
Formal Charge 0
Fraction CSP3 0.69
Exact Mass 346.16
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Anarrhinum pedatum Plantaginaceae Plantae 2500742

Showing of synonyms

  • Beladjila K.A, Berrehal D, et al. (2019). Antiangiogenic Activity of Compounds Isolated from Anarrhinum pedatum. Journal of natural products, 2019, 82(3), 510-519. [View] [PubMed]

No compound-protein relationship available.

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 346.38 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.06
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.45
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.1

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.68
Plasma Protein Binding
39.08
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
3.93
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Safe
Bioconcentration Factor
-1.98
Biodegradation
Toxic
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
1.07
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
4.33
Micronucleos
Safe
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
-1.76
Rat (Acute)
1.43
Rat (Chronic Oral)
3.07
Fathead Minnow
4.08
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
440.29
Hydration Free Energy
-20.1
Log(D) at pH=7.4
-0.01
Log(P)
-0.55
Log S
-1.49
Log(Vapor Pressure)
-11.78
Melting Point
135.01
pKa Acid
6.77
pKa Basic
5.4
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.9215
Xylose isomerase P24300 XYLA_STRRU Streptomyces rubiginosus 3 0.9127
Macrophage metalloelastase P39900 MMP12_HUMAN Homo sapiens 3 0.8774
Lysozyme C II P11941 LYSC2_ONCMY Oncorhynchus mykiss 3 0.8746
Vitamin D-binding protein P02774 VTDB_HUMAN Homo sapiens 3 0.8576
ADP-ribosylation factor 1 P84077 ARF1_HUMAN Homo sapiens 2 0.8477
Ascorbate-specific PTS system EIIC component P39301 ULAA_ECOLI Escherichia coli 3 0.8116
TamL D3Y1I2 D3Y1I2_9ACTN Streptomyces sp. 307-9 3 0.8109
Aldos-2-ulose dehydratase P84193 AUD_PHACH Phanerodontia chrysosporium 3 0.7488
Beta-glucosidase Q8T0W7 Q8T0W7_9NEOP Neotermes koshunensis 3 0.7453
Beta-glucosidase A Q08638 BGLA_THEMA Thermotoga maritima 3 0.7442
Chorismate mutase AroH P19080 AROH_BACSU Bacillus subtilis 2 0.7342
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 2 0.7338
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7335
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 2 0.7312
Chitinase Q54276 Q54276_SERMA Serratia marcescens 3 0.7288
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 2 0.7287
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 2 0.7250
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 2 0.7248
Muconolactone Delta-isomerase Q8G9L0 Q8G9L0_RHOOP Rhodococcus opacus 2 0.7238
2-aminohexano-6-lactam racemase Q7M181 ACLR_ACHOB Achromobacter obae 2 0.7212
Carnitine O-acetyltransferase P47934 CACP_MOUSE Mus musculus 2 0.7210
Glycogenin-1 P46976 GLYG_HUMAN Homo sapiens 3 0.7210
Transcriptional activator, LuxR/UhpA family of regulators Q7NQP7 Q7NQP7_CHRVO Chromobacterium violaceum 2 0.7188
Deacetoxycephalosporin C synthase P18548 CEFE_STRCL Streptomyces clavuligerus 2 0.7168
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7150
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7150
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7103
Cytochrome P450 Q93H81 Q93H81_STRAX Streptomyces avermitilis 2 0.7082
Avidin P02701 AVID_CHICK Gallus gallus 2 0.7059
3-alpha-(or 20-beta)-hydroxysteroid dehydrogenase P19992 HSD_STREX Streptomyces exfoliatus 2 0.7048
Lactose operon repressor P03023 LACI_ECOLI Escherichia coli 3 0.7037
Transcriptional activator, LuxR/UhpA family of regulators Q7NQP7 Q7NQP7_CHRVO Chromobacterium violaceum 2 0.7037
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 2 0.7004

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