6-O-trans-p-coumaroyl antirrinoside - Compound Card

6-O-trans-p-coumaroyl antirrinoside

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6-O-trans-p-coumaroyl antirrinoside

Structure
Zoomed Structure
  • Family: Plantae - Plantaginaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Monoterpene
Canonical Smiles O([C@H]1[C@@H]2[C@]3(O[C@H]3[C@H]([C@@]2(C=CO1)O)O)C)C(=O)/C=C\c1ccc(cc1)O
InChI InChI=1S/C18H18O7/c1-17-13-16(23-9-8-18(13,22)14(21)15(17)25-17)24-12(20)7-4-10-2-5-11(19)6-3-10/h2-9,13-16,19,21-22H,1H3/b7-4-/t13-,14-,15+,16+,17-,18+/m1/s1
InChIKey HUGRLBUUDIQGDH-VRDWOPQJSA-N
Formula C18H18O7
HBA 7
HBD 3
MW 346.34
Rotatable Bonds 3
TPSA 108.75
LogP 0.7
Number Rings 4
Number Aromatic Rings 1
Heavy Atom Count 25
Formal Charge 0
Fraction CSP3 0.39
Exact Mass 346.11
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]

No compound-protein relationship available.

Structure

SMILES: C12C(O2)CC3C1C(OC=C3)OC(=O)C=Cc4ccccc4

Level: 1

Mol. Weight: 346.34 g/mol

Structure

SMILES: C12C(O2)CC3C1COC=C3

Level: 0

Mol. Weight: 346.34 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 346.34 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.07
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.56
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.83

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.89
Plasma Protein Binding
24.97
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
Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
12.26
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.01
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.35
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.86
Micronucleos
Toxic
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
Toxic
T. Pyriformis
-4.92
Rat (Acute)
3.18
Rat (Chronic Oral)
2.57
Fathead Minnow
4.06
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
401.06
Hydration Free Energy
-10.82
Log(D) at pH=7.4
0.23
Log(P)
1.51
Log S
-2.7
Log(Vapor Pressure)
-8.38
Melting Point
137.56
pKa Acid
6.21
pKa Basic
0.88
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.8847
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.8795
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.8651
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.8451
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.8431
Flavin-dependent monooxygenase Q93L51 TETX_BACT4 Bacteroides thetaiotaomicron 3 0.8386
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.8349
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8240
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7954
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7907
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7832
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.7786
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.7781
Carbonic anhydrase 1 P00915 CAH1_HUMAN Homo sapiens 3 0.7754
Gag-Pol polyprotein P05896 POL_SIVM1 Simian immunodeficiency virus 4 0.7683
Ras-related protein Ral-B P11234 RALB_HUMAN Homo sapiens 3 0.7566
Disks large homolog 1 Q12959 DLG1_HUMAN Homo sapiens 3 0.7564
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7538
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7511
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 3 0.7439
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7414
Trichothecene 15-O-acetyltransferase TRI3 Q9C1B7 TRI3_FUSSP Fusarium sporotrichioides 3 0.7413
Cytochrome P450 S6BVH1 S6BVH1_RHOER Rhodococcus erythropolis 3 0.7392
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7383
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7375
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7370
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7366
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7356
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7348
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.7348
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7330
Purine nucleoside phosphorylase DeoD-type P0ABP9 DEOD_ECO57 Escherichia coli O157:H7 3 0.7325
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 2 0.7315
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 2 0.7302
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 4 0.7281
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7250
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7229
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 3 0.7229
Glutathione S-transferase Q8ILQ7 GST_PLAFA Plasmodium falciparum 3 0.7220
Gag-Pol polyprotein P03367 POL_HV1BR Human immunodeficiency virus type 1 group M subtype B 3 0.7218
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7198
Cyclic GMP-AMP phosphodiesterase SMPDL3A Q92484 ASM3A_HUMAN Homo sapiens 2 0.7195
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7151
Prolyl tripeptidyl peptidase Q7MUW6 PTP_PORGI Porphyromonas gingivalis 3 0.7141
Coagulation factor X P00742 FA10_HUMAN Homo sapiens 2 0.7122
Serine/threonine-protein kinase Chk2 O96017 CHK2_HUMAN Homo sapiens 2 0.7109
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 3 0.7104
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 2 0.7097
Holliday junction branch migration complex subunit RuvB Q9PMT7 RUVB_CAMJE Campylobacter jejuni subsp. jejuni serotype O:2 2 0.7087
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7070
Dihydropteroate synthase Q81VW8 Q81VW8_BACAN Bacillus anthracis 2 0.7062
Thymidine kinase P0DTH5 KITH_HHV11 Human herpesvirus 1 2 0.7050
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 2 0.7046
Leucine--tRNA ligase P07813 SYL_ECOLI Escherichia coli 3 0.7044
Genome polyprotein Q8QL64 Q8QL64_9FLAV Modoc virus 3 0.7040
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7019
Protocatechuate 3,4-dioxygenase beta chain P00437 PCXB_PSEPU Pseudomonas putida 2 0.7018
Putative FAD-dependent oxygenase EncM Q9KHK2 Q9KHK2_9ACTN Streptomyces maritimus 3 0.7010

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