2-(-3,6-dihydroxy-hepta-1,4-dien-1-yl)-3,6-dihydroxy-5-(dimethylallyl)benzaldehyde - Compound Card

2-(-3,6-dihydroxy-hepta-1,4-dien-1-yl)-3,6-dihydroxy-5-(dimethylallyl)benzaldehyde

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2-(-3,6-dihydroxy-hepta-1,4-dien-1-yl)-3,6-dihydroxy-5-(dimethylallyl)benzaldehyde

Structure
Zoomed Structure
  • Family: Plantae - Umbelliferae
  • Kingdom: Plantae
  • Class: Benzenoid
Canonical Smiles O=Cc1c(/C=C/C(/C=C/C(O)C)O)c(O)cc(c1O)CC=C(C)C
InChI InChI=1S/C19H24O5/c1-12(2)4-6-14-10-18(23)16(17(11-20)19(14)24)9-8-15(22)7-5-13(3)21/h4-5,7-11,13,15,21-24H,6H2,1-3H3/b7-5+,9-8+
InChIKey MFFBRVYDIQYKMR-ZIRGRKGMSA-N
Formula C19H24O5
HBA 5
HBD 4
MW 332.4
Rotatable Bonds 7
TPSA 97.99
LogP 2.73
Number Rings 1
Number Aromatic Rings 1
Heavy Atom Count 24
Formal Charge 0
Fraction CSP3 0.32
Exact Mass 332.16
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Ammi majus Umbelliferae Plantae 48026

Showing of synonyms

  • Fathallah N, Raafat M.M, et al. (2019). Bio-Guided Fractionation of Prenylated Benzaldehyde Derivatives as Potent Antimicrobial and Antibiofilm from Ammi majus L. Fruits-Associated Aspergillus amstelodami. Molecules, 2019,24(22),4114. [View] [PubMed]

No compound-protein relationship available.

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 332.4 g/mol

Antimicrobial

Absorption

Caco-2 (logPapp)
-4.84
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.69
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.83

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.42
Plasma Protein Binding
13.9
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
Inhibitor
CYP 2D6 Substrate
Non-Substrate
CYP 3A4 Inhibitor
Non-Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
9.88
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.36
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
0.11
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
6.19
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
1.63
Rat (Acute)
2.15
Rat (Chronic Oral)
2.72
Fathead Minnow
4.65
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
417.79
Hydration Free Energy
-13.03
Log(D) at pH=7.4
1.43
Log(P)
2.92
Log S
-2.92
Log(Vapor Pressure)
-7.39
Melting Point
124.76
pKa Acid
6.78
pKa Basic
5.02
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.9338
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.9138
Chitinase Q54276 Q54276_SERMA Serratia marcescens 3 0.8967
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 3 0.8924
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 4 0.8876
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.8856
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 3 0.8797
NADPH dehydrogenase 1 Q02899 OYE1_SACPS Saccharomyces pastorianus 3 0.8773
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.8770
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.8752
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.8570
Uncharacterized protein YML079W Q03629 YMH9_YEAST Saccharomyces cerevisiae 3 0.8369
S-adenosylmethionine decarboxylase proenzyme P17707 DCAM_HUMAN Homo sapiens 3 0.8354
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 3 0.8335
Na(+):neurotransmitter symporter (Snf family) O67854 O67854_AQUAE Aquifex aeolicus 3 0.8288
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.8277
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.8261
Methionine aminopeptidase 1 P53582 MAP11_HUMAN Homo sapiens 3 0.8169
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 3 0.8168
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.8096
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.8034
Methionine aminopeptidase 2 P50579 MAP2_HUMAN Homo sapiens 3 0.8029
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.8015
Acetylcholine-binding protein P58154 ACHP_LYMST Lymnaea stagnalis 3 0.7974
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 3 0.7963
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7945
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 3 0.7909
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.7905
Beta-galactoside-specific lectin 1 P81446 ML1_VISAL Viscum album 3 0.7745
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7713
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.7651
Sepiapterin reductase Q64105 SPRE_MOUSE Mus musculus 3 0.7646
Thymidine phosphorylase Q7CP66 TYPH_SALTY Salmonella typhimurium 3 0.7596
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7586
3-phosphoinositide-dependent protein kinase 1 O15530 PDPK1_HUMAN Homo sapiens 3 0.7550
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7541
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 3 0.7534
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 2 0.7528
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 4 0.7506
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 2 0.7497
Purine nucleoside phosphorylase P00491 PNPH_HUMAN Homo sapiens 3 0.7491
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7486
Sodium-dependent dopamine transporter Q7K4Y6 DAT_DROME Drosophila melanogaster 2 0.7461
Alpha amylase B8CZ54 B8CZ54_HALOH Halothermothrix orenii 3 0.7453
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 3 0.7430
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 3 0.7414
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7407
Purine nucleoside phosphorylase P00491 PNPH_HUMAN Homo sapiens 3 0.7399
ActVA 6 protein Q53908 Q53908_STRCH Streptomyces coelicolor 3 0.7380
Benzoylformate decarboxylase P20906 MDLC_PSEPU Pseudomonas putida 3 0.7379
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.7352
Fatty acid-binding protein, adipocyte P15090 FABP4_HUMAN Homo sapiens 2 0.7341
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7331
Genome polyprotein Q2YHF0 POLG_DEN4T Dengue virus type 4 3 0.7306
Soluble cytochrome b562 P0ABE7 C562_ECOLX Escherichia coli 3 0.7296
Kynurenine/alpha-aminoadipate aminotransferase, mitochondrial Q8N5Z0 AADAT_HUMAN Homo sapiens 2 0.7295
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7293
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7291
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.7283
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7267
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7228
Beta-hexosaminidase Q9KU37 NAGZ_VIBCH Vibrio cholerae serotype O1 3 0.7210
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7209
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7208
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7198
Nucleoside diphosphate kinase P15266 NDK_MYXXA Myxococcus xanthus 3 0.7180
L-lactate dehydrogenase A chain P13491 LDHA_RABIT Oryctolagus cuniculus 2 0.7179
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.7174
Methionine aminopeptidase 2 P50579 MAP2_HUMAN Homo sapiens 3 0.7173
Bromodomain adjacent to zinc finger domain protein 2B Q9UIF8 BAZ2B_HUMAN Homo sapiens 2 0.7158
Beta-lactoglobulin P02754 LACB_BOVIN Bos taurus 3 0.7153
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 3 0.7148
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.7142
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7123
RNA-dependent RNA polymerase Q6A562 Q6A562_9VIRU Thosea asigna virus 2 0.7106
Biflaviolin synthase CYP158A2 Q9FCA6 C1582_STRCO Streptomyces coelicolor / M145) 3 0.7101
Prolyl endopeptidase P23687 PPCE_PIG Sus scrofa 3 0.7092
ADP compounds hydrolase NudE P45799 NUDE_ECOLI Escherichia coli 2 0.7080
Flavin-dependent monooxygenase Q93L51 TETX_BACT4 Bacteroides thetaiotaomicron 2 0.7076
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 2 0.7073
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7059
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.7052
Methionine aminopeptidase 2 P9WK19 MAP12_MYCTU Mycobacterium tuberculosis 3 0.7051
Prolyl tripeptidyl peptidase Q7MUW6 PTP_PORGI Porphyromonas gingivalis 2 0.7051
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 2 0.7031
D-alanyl-D-alanine carboxypeptidase P15555 DAC_STRSR Streptomyces sp 2 0.7018
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7017
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7015
Cytochrome P450 Q93H81 Q93H81_STRAX Streptomyces avermitilis 3 0.7015
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7008
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 2 0.7002

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