Foliamenthic acid - Compound Card

Foliamenthic acid

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Foliamenthic acid

Structure
Zoomed Structure
  • Family: Plantae - Plantaginaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Monoterpene
Canonical Smiles OCC=C(CCC=C(C(=O)O)C)C
InChI InChI=1S/C10H16O3/c1-8(6-7-11)4-3-5-9(2)10(12)13/h5-6,11H,3-4,7H2,1-2H3,(H,12,13)
InChIKey SMFMBDDFGPDMMD-UHFFFAOYSA-N
Formula C10H16O3
HBA 2
HBD 2
MW 184.23
Rotatable Bonds 5
TPSA 57.53
LogP 1.74
Number Rings 0
Number Aromatic Rings 0
Heavy Atom Count 13
Formal Charge 0
Fraction CSP3 0.5
Exact Mass 184.11
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]
Pubchem: 54313026

No compound-protein relationship available.

No scaffolds available.

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.61
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.19
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-3.68

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.36
Plasma Protein Binding
7.18
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
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
3.03
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Safe
Bioconcentration Factor
-0.09
Biodegradation
Toxic
Carcinogenesis
Toxic
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
0.5
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
2.07
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
0.2
Rat (Acute)
1.5
Rat (Chronic Oral)
1.79
Fathead Minnow
3.97
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
296.26
Hydration Free Energy
-8.54
Log(D) at pH=7.4
-1.15
Log(P)
1.72
Log S
-1.63
Log(Vapor Pressure)
-5.42
Melting Point
110.99
pKa Acid
4.98
pKa Basic
6.39
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Branched-chain-amino-acid aminotransferase, mitochondrial O15382 BCAT2_HUMAN Homo sapiens 3 0.9596
Streptavidin P22629 SAV_STRAV Streptomyces avidinii 3 0.9310
Streptavidin P22629 SAV_STRAV Streptomyces avidinii 3 0.9247
Gastrotropin Q6IMW5 Q6IMW5_DANRE Danio rerio 3 0.9231
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 3 0.9107
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 3 0.9056
Streptavidin P22629 SAV_STRAV Streptomyces avidinii 3 0.9037
Deacetoxycephalosporin C synthase P18548 CEFE_STRCL Streptomyces clavuligerus 3 0.9031
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.9015
Streptavidin P22629 SAV_STRAV Streptomyces avidinii 3 0.9009
Phospholipase A2 P00593 PA21B_BOVIN Bos taurus 3 0.8962
Soluble cytochrome b562 P0ABE7 C562_ECOLX Escherichia coli 3 0.8947
Streptavidin P22629 SAV_STRAV Streptomyces avidinii 3 0.8940
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.8846
Streptavidin P22629 SAV_STRAV Streptomyces avidinii 3 0.8761
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.8742
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.8716
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.8705
Streptavidin P22629 SAV_STRAV Streptomyces avidinii 3 0.8662
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.8639
Abscisic acid receptor PYR1 O49686 PYR1_ARATH Arabidopsis thaliana 3 0.8612
3-alpha-(or 20-beta)-hydroxysteroid dehydrogenase P19992 HSD_STREX Streptomyces exfoliatus 3 0.8597
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8520
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.8440
Reaction center protein L chain P0C0Y7 RCEH_RHOSH Rhodobacter sphaeroides 3 0.8410
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.8379
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 3 0.8365
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.8314
ADP-ribosylation factor 1 P84077 ARF1_HUMAN Homo sapiens 2 0.8294
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8269
Cytochrome P450 Q93H81 Q93H81_STRAX Streptomyces avermitilis 3 0.8233
Suppressor of disruption of TFIIS P53078 SDT1_YEAST Saccharomyces cerevisiae 3 0.8171
Aromatase P11511 CP19A_HUMAN Homo sapiens 3 0.8168
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.8134
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 3 0.8072
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.8071
Nuclear receptor subfamily 1 group I member 3 O35627 NR1I3_MOUSE Mus musculus 3 0.8033
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.7999
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7993
Abscisic acid receptor PYL2 O80992 PYL2_ARATH Arabidopsis thaliana 3 0.7967
Gastrotropin P51161 FABP6_HUMAN Homo sapiens 3 0.7962
Vitamin D3 dihydroxylase P18326 CPXE_STRGO Streptomyces griseolus 3 0.7920
Gibberellin receptor GID1A Q9MAA7 GID1A_ARATH Arabidopsis thaliana 3 0.7865
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 3 0.7863
ADP-ribosylation factor 1 P84080 ARF1_BOVIN Bos taurus 3 0.7861
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7845
Peroxisome proliferator-activated receptor alpha Q07869 PPARA_HUMAN Homo sapiens 3 0.7842
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7840
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 2 0.7826
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.7822
Avd protein A7YYL1 A7YYL1_XENTR Xenopus tropicalis 3 0.7817
Abscisic acid receptor PYR1 O49686 PYR1_ARATH Arabidopsis thaliana 3 0.7782
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7768
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7745
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7741
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7737
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7727
Chorismate mutase AroH P19080 AROH_BACSU Bacillus subtilis 3 0.7715
Vitamin D3 dihydroxylase P18326 CPXE_STRGO Streptomyces griseolus 3 0.7702
Streptavidin P22629 SAV_STRAV Streptomyces avidinii 2 0.7700
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7678
Regulatory protein SdiA P07026 SDIA_ECOLI Escherichia coli 3 0.7661
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7647
NPC intracellular cholesterol transporter 1 O15118 NPC1_HUMAN Homo sapiens 2 0.7644
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.7598
N-alpha-acetyltransferase 50 Q9GZZ1 NAA50_HUMAN Homo sapiens 3 0.7563
Steroid C26-monooxygenase P9WPP1 CP125_MYCTU Mycobacterium tuberculosis 3 0.7560
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7551
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7541
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 2 0.7533
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7526
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7523
Major pollen allergen Bet v 1-A P15494 BEV1A_BETPN Betula pendula 3 0.7509
Avidin P02701 AVID_CHICK Gallus gallus 3 0.7478
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7455
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7452
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 2 0.7451
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.7449
Integrin alpha-L P20701 ITAL_HUMAN Homo sapiens 2 0.7442
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.7430
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7429
Avidin P02701 AVID_CHICK Gallus gallus 3 0.7419
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7410
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7388
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.7379
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7376
Lactaldehyde dehydrogenase P25553 ALDA_ECOLI Escherichia coli 3 0.7375
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7375
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7358
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7350
Androgen receptor P19091 ANDR_MOUSE Mus musculus 3 0.7348
Trifunctional purine biosynthetic protein adenosine-3 P22102 PUR2_HUMAN Homo sapiens 3 0.7348
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7342
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 2 0.7335
Chorismate mutase AroH P19080 AROH_BACSU Bacillus subtilis 2 0.7334
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7331
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 2 0.7330
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7325
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7309
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7306
Geranyl diphosphate synthase large subunit Q9SBR3 Q9SBR3_MENPI Mentha piperita 3 0.7302
Nuclear receptor ROR-gamma P51449 RORG_HUMAN Homo sapiens 2 0.7301
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7294
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7294
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7281
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 2 0.7273
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7268
Carnitine O-acetyltransferase P47934 CACP_MOUSE Mus musculus 2 0.7267
Abscisic acid receptor PYL2 O80992 PYL2_ARATH Arabidopsis thaliana 3 0.7263
Nuclear receptor ROR-beta P45446 RORB_RAT Rattus norvegicus 2 0.7256
Streptavidin P22629 SAV_STRAV Streptomyces avidinii 3 0.7250
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7247
Muconolactone Delta-isomerase Q8G9L0 Q8G9L0_RHOOP Rhodococcus opacus 2 0.7240
Androgen receptor O97775 ANDR_PANTR Pan troglodytes 3 0.7237
Transcriptional activator, LuxR/UhpA family of regulators Q7NQP7 Q7NQP7_CHRVO Chromobacterium violaceum 2 0.7226
Streptavidin P22629 SAV_STRAV Streptomyces avidinii 3 0.7220
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7217
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7215
Ferric enterobactin-binding periplasmic protein FepB P0AEL6 FEPB_ECOLI Escherichia coli 3 0.7211
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7207
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7203
Vitamin D-binding protein P02774 VTDB_HUMAN Homo sapiens 2 0.7196
Aldo-keto reductase family 1 member C1 Q04828 AK1C1_HUMAN Homo sapiens 2 0.7191
2-aminohexano-6-lactam racemase Q7M181 ACLR_ACHOB Achromobacter obae 2 0.7179
11-beta-hydroxysteroid dehydrogenase 1 P50172 DHI1_MOUSE Mus musculus 3 0.7177
Androgen receptor O97775 ANDR_PANTR Pan troglodytes 3 0.7170
Prolyl tripeptidyl peptidase Q7MUW6 PTP_PORGI Porphyromonas gingivalis 2 0.7167
Transcriptional activator, LuxR/UhpA family of regulators Q7NQP7 Q7NQP7_CHRVO Chromobacterium violaceum 2 0.7167
Streptavidin P22629 SAV_STRAV Streptomyces avidinii 2 0.7164
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7161
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7161
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7161
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7158
Androgen receptor O97775 ANDR_PANTR Pan troglodytes 3 0.7153
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7148
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7139
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7136
Predicted acetyltransferase Q97ML2 Q97ML2_CLOAB Clostridium acetobutylicum 3 0.7131
Trichothecene 15-O-acetyltransferase TRI3 Q9C1B7 TRI3_FUSSP Fusarium sporotrichioides 2 0.7125
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7119
Angiotensin-converting enzyme Q10714 ACE_DROME Drosophila melanogaster 3 0.7119
Steroid 21-hydroxylase P08686 CP21A_HUMAN Homo sapiens 3 0.7113
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7106
Gibberellin receptor GID1 Q6L545 GID1_ORYSJ Oryza sativa subsp. japonica 3 0.7097
Androgen receptor O97775 ANDR_PANTR Pan troglodytes 3 0.7094
Androgen receptor O97775 ANDR_PANTR Pan troglodytes 3 0.7093
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7090
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7085
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.7081
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7081
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7079
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7072
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7065
N-acyl-aromatic-L-amino acid amidohydrolase (carboxylate-forming) Q91XE4 ACY3_MOUSE Mus musculus 2 0.7065
Methionine aminopeptidase 2 P9WK19 MAP12_MYCTU Mycobacterium tuberculosis 2 0.7062
Fatty acid-binding protein 10-A, liver basic Q9I8L5 FA10A_DANRE Danio rerio 2 0.7060
Avidin P02701 AVID_CHICK Gallus gallus 2 0.7059
Camphor 5-monooxygenase P00183 CPXA_PSEPU Pseudomonas putida 3 0.7052
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7048
4,4'-diapophytoene synthase A9JQL9 CRTM_STAAU Staphylococcus aureus 2 0.7041
Androgen receptor O97775 ANDR_PANTR Pan troglodytes 3 0.7040
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7034
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7028
ADP-ribosylation factor 1 P84080 ARF1_BOVIN Bos taurus 3 0.7021
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7018
Rhodopsin P02699 OPSD_BOVIN Bos taurus 2 0.7016
Abscisic acid receptor PYL9 Q84MC7 PYL9_ARATH Arabidopsis thaliana 3 0.7015
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7014
Glutamate receptor ionotropic, kainate 1 P22756 GRIK1_RAT Rattus norvegicus 2 0.7014
diphosphomevalonate decarboxylase Q9FD73 Q9FD73_STAEP Staphylococcus epidermidis 2 0.7013
Peptide deformylase P0A6K3 DEF_ECOLI Escherichia coli 3 0.7007
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7004
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.7004
Pantothenate synthetase P9WIL5 PANC_MYCTU Mycobacterium tuberculosis 3 0.7004

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