Cimifugin 3-methylbutanoate - Compound Card

Cimifugin 3-methylbutanoate

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Cimifugin 3-methylbutanoate

Structure
Zoomed Structure
  • Family: Plantae - Apiaceae
  • Kingdom: Plantae
  • Class: Furanochromone
Canonical Smiles COc1c2C[C@H](Oc2cc2c1c(=O)cc(o2)COC(=O)CC(C)C)C(O)(C)C
InChI InChI=1S/C21H26O7/c1-11(2)6-18(23)26-10-12-7-14(22)19-16(27-12)9-15-13(20(19)25-5)8-17(28-15)21(3,4)24/h7,9,11,17,24H,6,8,10H2,1-5H3/t17-/m0/s1
InChIKey NHUJMCLEPMGPOW-KRWDZBQOSA-N
Formula C21H26O7
HBA 7
HBD 1
MW 390.43
Rotatable Bonds 6
TPSA 95.2
LogP 2.97
Number Rings 3
Number Aromatic Rings 2
Heavy Atom Count 28
Formal Charge 0
Fraction CSP3 0.52
Exact Mass 390.17
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Ammi visnaga Apiaceae Plantae 1053409

Showing of synonyms

  • Sellami HK, Napolitano A, et al. (2013). Influence of growing conditions on metabolite profile of Ammi visnaga umbels with special reference to bioactive furanochromones and pyranocoumarins. Phytochemistry,2013,95,197-206. [View] [PubMed]
Pubchem: 73212328
Nmrshiftdb2: 70049950

No compound-protein relationship available.

Structure

SMILES: C1COc(c12)cc3c(c2)c(=O)cco3

Level: 0

Mol. Weight: 390.43 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.79
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.59
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.87

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.93
Plasma Protein Binding
74.33
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
Inhibitor
CYP 1A2 Substrate
Substrate
CYP 2C19 Inhibitor
Non-Inhibitor
CYP 2C19 Substrate
Non-Substrate
CYP 2C9 Inhibitor
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
5.79
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.68
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.49
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
6.79
Micronucleos
Toxic
NR-AhR
Toxic
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
-4.32
Rat (Acute)
2.96
Rat (Chronic Oral)
1.92
Fathead Minnow
4.59
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
442.32
Hydration Free Energy
-7.39
Log(D) at pH=7.4
2.77
Log(P)
3.09
Log S
-4.49
Log(Vapor Pressure)
-7.63
Melting Point
147.93
pKa Acid
9.21
pKa Basic
5.53
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.9483
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.9483
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.9063
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.9063
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 3 0.8843
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 3 0.8843
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8797
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8797
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8794
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8794
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.8748
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.8748
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.8675
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.8675
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 3 0.8562
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 3 0.8562
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 4 0.8544
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 4 0.8544
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 3 0.8524
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 3 0.8524
11-beta-hydroxysteroid dehydrogenase 1 P50172 DHI1_MOUSE Mus musculus 3 0.8417
11-beta-hydroxysteroid dehydrogenase 1 P50172 DHI1_MOUSE Mus musculus 3 0.8417
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 4 0.8253
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 4 0.8253
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8250
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8250
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8049
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8049
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7955
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7955
Cholesterol side-chain cleavage enzyme, mitochondrial P05108 CP11A_HUMAN Homo sapiens 3 0.7909
Cholesterol side-chain cleavage enzyme, mitochondrial P05108 CP11A_HUMAN Homo sapiens 3 0.7909
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 4 0.7878
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 4 0.7878
2-phospho-L-lactate transferase Q8PVT6 COFD_METMA Methanosarcina mazei 3 0.7870
2-phospho-L-lactate transferase Q8PVT6 COFD_METMA Methanosarcina mazei 3 0.7870
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.7819
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.7819
HTH-type transcriptional regulator EthR P9WMC1 ETHR_MYCTU Mycobacterium tuberculosis 3 0.7655
HTH-type transcriptional regulator EthR P9WMC1 ETHR_MYCTU Mycobacterium tuberculosis 3 0.7655
ActVA 6 protein Q53908 Q53908_STRCH Streptomyces coelicolor 3 0.7574
ActVA 6 protein Q53908 Q53908_STRCH Streptomyces coelicolor 3 0.7574
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7547
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7547
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7535
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7535
Peptidyl-prolyl cis-trans isomerase FKBP5 Q13451 FKBP5_HUMAN Homo sapiens 3 0.7494
Peptidyl-prolyl cis-trans isomerase FKBP5 Q13451 FKBP5_HUMAN Homo sapiens 3 0.7494
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.7463
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.7463
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7455
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7455
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7417
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7417
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7414
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7414
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 2 0.7407
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 2 0.7407
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 3 0.7400
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 3 0.7400
Phytohormone-binding protein CSBP A0A1S3THR8 PHBP_VIGRR Vigna radiata var. radiata 2 0.7389
Phytohormone-binding protein CSBP A0A1S3THR8 PHBP_VIGRR Vigna radiata var. radiata 2 0.7389
Histone-lysine N-methyltransferase SETD7 Q8WTS6 SETD7_HUMAN Homo sapiens 3 0.7386
Histone-lysine N-methyltransferase SETD7 Q8WTS6 SETD7_HUMAN Homo sapiens 3 0.7386
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7337
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7337
Acyl-homoserine-lactone synthase Q4VSJ8 Q4VSJ8_BURGL Burkholderia glumae 4 0.7331
Acyl-homoserine-lactone synthase Q4VSJ8 Q4VSJ8_BURGL Burkholderia glumae 4 0.7331
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 2 0.7317
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 2 0.7317
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 2 0.7299
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 2 0.7299
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7267
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7267
Jasmonoyl--L-amino acid synthetase JAR1 Q9SKE2 JAR1_ARATH Arabidopsis thaliana 3 0.7223
Jasmonoyl--L-amino acid synthetase JAR1 Q9SKE2 JAR1_ARATH Arabidopsis thaliana 3 0.7223
D-alanyl-D-alanine carboxypeptidase P15555 DAC_STRSR Streptomyces sp 2 0.7202
D-alanyl-D-alanine carboxypeptidase P15555 DAC_STRSR Streptomyces sp 2 0.7202
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.7201
CCA-adding enzyme O28126 CCA_ARCFU Archaeoglobus fulgidus 2 0.7201
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.7201
CCA-adding enzyme O28126 CCA_ARCFU Archaeoglobus fulgidus 2 0.7201
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.7200
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.7200
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.7123
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.7123
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7109
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7109
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7084
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7084
Kynurenine/alpha-aminoadipate aminotransferase, mitochondrial Q8N5Z0 AADAT_HUMAN Homo sapiens 2 0.7064
Kynurenine/alpha-aminoadipate aminotransferase, mitochondrial Q8N5Z0 AADAT_HUMAN Homo sapiens 2 0.7064
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7061
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7061
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7044
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7044
GMP reductase Q81JJ9 GUAC_BACAN Bacillus anthracis 2 0.7037
GMP reductase Q81JJ9 GUAC_BACAN Bacillus anthracis 2 0.7037
Abscisic acid receptor PYL3 Q9SSM7 PYL3_ARATH Arabidopsis thaliana 3 0.7036
Abscisic acid receptor PYL3 Q9SSM7 PYL3_ARATH Arabidopsis thaliana 3 0.7036
Macrophage metalloelastase P39900 MMP12_HUMAN Homo sapiens 3 0.7029
Macrophage metalloelastase P39900 MMP12_HUMAN Homo sapiens 3 0.7029
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7026
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7026
Genome polyprotein P26663 POLG_HCVBK Hepatitis C virus genotype 1b 3 0.7013
Genome polyprotein P26663 POLG_HCVBK Hepatitis C virus genotype 1b 3 0.7013
Multidrug transporter MdfA P0AEY8 MDFA_ECOLI Escherichia coli 3 0.7001
Multidrug transporter MdfA P0AEY8 MDFA_ECOLI Escherichia coli 3 0.7001

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