6′-O-trans-cinnamoylmacfadienoside - Compound Card

6′-O-trans-cinnamoylmacfadienoside

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6′-O-trans-cinnamoylmacfadienoside

Structure
Zoomed Structure
  • Family: Plantae - Plantaginaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Iridoid Glycoside
Canonical Smiles OC[C@]12OC1[C@H]([C@]1(C2C(OC=C1)O[C@@H]1OC(COC(=O)/C=C/c2ccccc2)[C@H](C([C@@H]1O)O)O)O)O
InChI InChI=1S/C24H28O12/c25-11-24-18-22(32-9-8-23(18,31)19(30)20(24)36-24)35-21-17(29)16(28)15(27)13(34-21)10-33-14(26)7-6-12-4-2-1-3-5-12/h1-9,13,15-22,25,27-31H,10-11H2/b7-6+/t13?,15-,16?,17+,18?,19-,20?,21+,22?,23+,24-/m1/s1
InChIKey UKQNLZINVPRJIZ-QSQXGTBPSA-N
Formula C24H28O12
HBA 12
HBD 6
MW 508.48
Rotatable Bonds 7
TPSA 187.9
LogP -2.21
Number Rings 5
Number Aromatic Rings 1
Heavy Atom Count 36
Formal Charge 0
Fraction CSP3 0.54
Exact Mass 508.16
Number of Lipinski Rule Violations 3
# 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: c1ccccc1C=CC(=O)OCC2CCCC(O2)OC(OC=C3)C4C3CC(O5)C45

Level: 2

Mol. Weight: 508.48 g/mol

Structure

SMILES: O1CCCCC1COC(=O)C=Cc2ccccc2

Level: 1

Mol. Weight: 508.48 g/mol

Structure

SMILES: C12C(O2)CC3C1C(OC=C3)OC4CCCCO4

Level: 1

Mol. Weight: 508.48 g/mol

Structure

SMILES: C12C(O2)CC3C1COC=C3

Level: 0

Mol. Weight: 508.48 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 508.48 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 508.48 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.7
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Non-Absorbed
Madin-Darby Canine Kidney
-4.81
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-0.96

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.85
Plasma Protein Binding
29.92
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
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
6.22
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-1.74
Biodegradation
Toxic
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.9
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
4.62
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
Safe
T. Pyriformis
-1040.6
Rat (Acute)
2.68
Rat (Chronic Oral)
3.47
Fathead Minnow
3.27
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Toxic
SR-ATAD5
Toxic
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
529.28
Hydration Free Energy
-3.19
Log(D) at pH=7.4
-0.32
Log(P)
-0.26
Log S
-1.86
Log(Vapor Pressure)
-13.53
Melting Point
142.18
pKa Acid
4.42
pKa Basic
3.53
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.8953
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.8745
Class B acid phosphatase Q540U1 APHA_SALTM Salmonella typhimurium 2 0.8279
Methionine aminopeptidase P0AE18 MAP1_ECOLI Escherichia coli 3 0.8085
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.7962
Purine nucleoside phosphorylase Q8I3X4 Q8I3X4_PLAF7 Plasmodium falciparum 3 0.7915
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 3 0.7798
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 2 0.7653
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 2 0.7638
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7627
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 2 0.7525
Valacyclovir hydrolase Q86WA6 BPHL_HUMAN Homo sapiens 2 0.7469
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 2 0.7394
14-3-3 protein gamma P61981 1433G_HUMAN Homo sapiens 3 0.7331
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 2 0.7293
Plasma membrane ATPase Q42932 Q42932_NICPL Nicotiana plumbaginifolia 2 0.7282
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7279
Single-stranded-DNA-specific exonuclease RecJ D0EM60 D0EM60_DEIRD Deinococcus radiodurans 2 0.7273
F420-dependent methylenetetrahydromethanopterin dehydrogenase P94951 MTD_METKA Methanopyrus kandleri 2 0.7257
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 3 0.7231
NAD(P) transhydrogenase subunit alpha part 1 Q2RSB2 PNTAA_RHORT Rhodospirillum rubrum 3 0.7214
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 2 0.7197
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 2 0.7191
Polymerase basic protein 2 P31345 PB2_I75A3 Influenza A virus 2 0.7073
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 2 0.7027

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