Apiumetin - Compound Card

Apiumetin

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Apiumetin

Structure
Zoomed Structure
  • Family: Plantae - Apiaceae
  • Kingdom: Plantae
  • Class: Coumarin
Canonical Smiles CC(=C)C1Cc2c(O1)c(O)c1c(c2)ccc(=O)o1
InChI InChI=1S/C14H12O4/c1-7(2)10-6-9-5-8-3-4-11(15)18-13(8)12(16)14(9)17-10/h3-5,10,16H,1,6H2,2H3
InChIKey VIUKEEZPYOJNOJ-UHFFFAOYSA-N
Formula C14H12O4
HBA 4
HBD 1
MW 244.25
Rotatable Bonds 1
TPSA 59.67
LogP 2.38
Number Rings 3
Number Aromatic Rings 2
Heavy Atom Count 18
Formal Charge 0
Fraction CSP3 0.21
Exact Mass 244.07
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Ammi majus Apiaceae Plantae 48026

Showing of synonyms

  • Elgamal MHA, Shalaby NMM, et al. (1993). Coumarins and coumarin glucosides from the fruits of Ammi majus. Phytochemistry,1993,34(3),819-823. [View]
Pubchem: 131752966
Chebi: 174260
Nmrshiftdb2: 60081772

No compound-protein relationship available.

Structure

SMILES: C1COc(c12)cc3c(c2)ccc(=O)o3

Level: 0

Mol. Weight: 244.25 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.77
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.36
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.04

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.98
Plasma Protein Binding
56.52
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
Inhibitor
CYP 1A2 Substrate
Substrate
CYP 2C19 Inhibitor
Inhibitor
CYP 2C19 Substrate
Substrate
CYP 2C9 Inhibitor
Non-Inhibitor
CYP 2C9 Substrate
Substrate
CYP 2D6 Inhibitor
Non-Inhibitor
CYP 2D6 Substrate
Substrate
CYP 3A4 Inhibitor
Non-Inhibitor
CYP 3A4 Substrate
Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
9.32
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.2
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
0.82
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.84
Micronucleos
Toxic
NR-AhR
Safe
NR-AR
Safe
NR-AR-LBD
Safe
NR-Aromatase
Safe
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Toxic
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
4.4
Rat (Acute)
2.49
Rat (Chronic Oral)
1.78
Fathead Minnow
4.27
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
374.64
Hydration Free Energy
-8.61
Log(D) at pH=7.4
1.67
Log(P)
2.75
Log S
-3.43
Log(Vapor Pressure)
-6.99
Melting Point
191.58
pKa Acid
6.69
pKa Basic
4.71
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.9266
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.9266
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.9163
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.9163
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.9013
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.9013
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8936
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8936
Biflaviolin synthase CYP158A2 Q9FCA6 C1582_STRCO Streptomyces coelicolor / M145) 3 0.8894
Biflaviolin synthase CYP158A2 Q9FCA6 C1582_STRCO Streptomyces coelicolor / M145) 3 0.8894
Biflaviolin synthase CYP158A2 Q9FCA6 C1582_STRCO Streptomyces coelicolor / M145) 3 0.8841
Biflaviolin synthase CYP158A2 Q9FCA6 C1582_STRCO Streptomyces coelicolor / M145) 3 0.8841
Sulfide-quinone reductase B7JBP8 SQRD_ACIF2 Acidithiobacillus ferrooxidans) 3 0.8776
Sulfide-quinone reductase B7JBP8 SQRD_ACIF2 Acidithiobacillus ferrooxidans) 3 0.8776
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8736
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8736
Biflaviolin synthase CYP158A1 Q9KZF5 C1581_STRCO Streptomyces coelicolor / M145) 3 0.8658
Biflaviolin synthase CYP158A1 Q9KZF5 C1581_STRCO Streptomyces coelicolor / M145) 3 0.8658
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8508
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8508
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.8493
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.8493
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.8317
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.8317
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.8278
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.8278
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8277
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8277
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.8276
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.8276
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.8243
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.8243
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.8221
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.8221
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 3 0.8212
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 3 0.8212
Biphenyl-2,3-diol 1,2-dioxygenase P17297 BPHC_PSES1 Pseudomonas sp 3 0.8088
Biphenyl-2,3-diol 1,2-dioxygenase P17297 BPHC_PSES1 Pseudomonas sp 3 0.8088
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.8083
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.8083
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.8071
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.8071
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8058
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8058
Na(+):neurotransmitter symporter (Snf family) O67854 O67854_AQUAE Aquifex aeolicus 3 0.8053
Na(+):neurotransmitter symporter (Snf family) O67854 O67854_AQUAE Aquifex aeolicus 3 0.8053
Uridine phosphorylase Q5XA29 Q5XA29_STRP6 Streptococcus pyogenes serotype M6 4 0.8031
Uridine phosphorylase Q5XA29 Q5XA29_STRP6 Streptococcus pyogenes serotype M6 4 0.8031
Pteridine reductase, putative Q581W1 Q581W1_TRYB2 Trypanosoma brucei brucei 3 0.8018
Pteridine reductase, putative Q581W1 Q581W1_TRYB2 Trypanosoma brucei brucei 3 0.8018
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7989
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7989
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7958
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7958
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7878
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7878
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 3 0.7842
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 3 0.7842
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7824
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7824
NAD(P)H-hydrate epimerase Q8K4Z3 NNRE_MOUSE Mus musculus 3 0.7806
NAD(P)H-hydrate epimerase Q8K4Z3 NNRE_MOUSE Mus musculus 3 0.7806
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.7724
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.7724
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.7721
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.7721
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7656
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7656
Soluble cytochrome b562 P0ABE7 C562_ECOLX Escherichia coli 3 0.7648
Soluble cytochrome b562 P0ABE7 C562_ECOLX Escherichia coli 3 0.7648
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 3 0.7620
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 3 0.7620
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7558
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7558
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 2 0.7540
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 2 0.7540
NAD(P)H-hydrate epimerase Q8K4Z3 NNRE_MOUSE Mus musculus 3 0.7534
NAD(P)H-hydrate epimerase Q8K4Z3 NNRE_MOUSE Mus musculus 3 0.7534
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 2 0.7532
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 2 0.7532
Estrogen receptor P03372 ESR1_HUMAN Homo sapiens 4 0.7528
Estrogen receptor P03372 ESR1_HUMAN Homo sapiens 4 0.7528
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase F6MZ55 F6MZ55_9FIRM Sporomusa ovata 3 0.7509
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase F6MZ55 F6MZ55_9FIRM Sporomusa ovata 3 0.7509
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.7507
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.7507
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7495
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7495
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7489
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7489
Biphenyl-2,3-diol 1,2-dioxygenase P17297 BPHC_PSES1 Pseudomonas sp 3 0.7484
Biphenyl-2,3-diol 1,2-dioxygenase P17297 BPHC_PSES1 Pseudomonas sp 3 0.7484
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7476
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7476
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.7474
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.7474
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7454
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7454
CREB-binding protein Q92793 CBP_HUMAN Homo sapiens 3 0.7452
CREB-binding protein Q92793 CBP_HUMAN Homo sapiens 3 0.7452
Sulfotransferase 1A1 P50225 ST1A1_HUMAN Homo sapiens 2 0.7447
Sulfotransferase 1A1 P50225 ST1A1_HUMAN Homo sapiens 2 0.7447
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.7424
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.7424
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7419
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7419
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 2 0.7410
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 2 0.7410
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7404
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7404
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7382
Putative S-adenosyl-L-methionine-dependent methyltransferase ML2640 Q9CCZ4 Y2640_MYCLE Mycobacterium leprae 3 0.7382
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7382
Putative S-adenosyl-L-methionine-dependent methyltransferase ML2640 Q9CCZ4 Y2640_MYCLE Mycobacterium leprae 3 0.7382
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 2 0.7379
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 2 0.7379
NADH:flavin oxidoreductase Sye1 Q8EEC8 Q8EEC8_SHEON Shewanella oneidensis 3 0.7375
NADH:flavin oxidoreductase Sye1 Q8EEC8 Q8EEC8_SHEON Shewanella oneidensis 3 0.7375
Ribonuclease J H9CZL7 H9CZL7_DEIRD Deinococcus radiodurans 3 0.7355
Ribonuclease J H9CZL7 H9CZL7_DEIRD Deinococcus radiodurans 3 0.7355
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.7325
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7325
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.7325
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7325
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7311
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 2 0.7311
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 2 0.7311
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7311
Aminoglycoside N(3)-acetyltransferase A0A3P1UCA6 Q81P86_BACAN Bacillus anthracis 3 0.7253
Aminoglycoside N(3)-acetyltransferase A0A3P1UCA6 Q81P86_BACAN Bacillus anthracis 3 0.7253
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.7252
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.7252
Thymidine kinase P0DTH5 KITH_HHV11 Human herpesvirus 1 2 0.7251
Thymidine kinase P0DTH5 KITH_HHV11 Human herpesvirus 1 2 0.7251
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.7243
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.7243
Uncharacterized protein Q3F0V8 Q3F0V8_BACTI Bacillus thuringiensis serovar israelensis ATCC 35646 3 0.7231
Uncharacterized protein Q3F0V8 Q3F0V8_BACTI Bacillus thuringiensis serovar israelensis ATCC 35646 3 0.7231
Multidrug transporter MdfA P0AEY8 MDFA_ECOLI Escherichia coli 3 0.7231
Multidrug transporter MdfA P0AEY8 MDFA_ECOLI Escherichia coli 3 0.7231
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7229
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7229
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.7181
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.7181
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha Q04631 FNTA_RAT Rattus norvegicus 3 0.7177
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha Q04631 FNTA_RAT Rattus norvegicus 3 0.7177
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 2 0.7167
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 2 0.7167
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7166
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7166
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.7164
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.7164
Carbonic anhydrase 1 P00915 CAH1_HUMAN Homo sapiens 2 0.7147
Carbonic anhydrase 1 P00915 CAH1_HUMAN Homo sapiens 2 0.7147
Estrogen receptor P03372 ESR1_HUMAN Homo sapiens 2 0.7122
Estrogen receptor P03372 ESR1_HUMAN Homo sapiens 2 0.7122
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7122
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7122
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7112
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7112
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 2 0.7108
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 2 0.7108
L-lactate dehydrogenase Q5SJA1 LDH_THET8 Thermus thermophilus 3 0.7104
L-lactate dehydrogenase Q5SJA1 LDH_THET8 Thermus thermophilus 3 0.7104
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 2 0.7081
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 2 0.7081
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 3 0.7062
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 3 0.7062

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