5,6-O-difoliamenthoylmacfadienoside - Compound Card

5,6-O-difoliamenthoylmacfadienoside

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5,6-O-difoliamenthoylmacfadienoside

Structure
Zoomed Structure
  • Family: Plantae - Plantaginaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Iridoid Glycoside
Canonical Smiles OC/C=C(\CC/C=C(/C(=O)O[C@@H]1C2O[C@@]2(C2[C@]1(C=COC2O[C@@H]1OC(CO)[C@H](C([C@@H]1O)O)O)OC(=O)/C(=C/CC/C(=C\CO)/C)/C)CO)\C)/C
InChI InChI=1S/C35H50O15/c1-19(11-14-36)7-5-9-21(3)30(43)47-28-29-35(18-39,49-29)27-33(48-32-26(42)25(41)24(40)23(17-38)46-32)45-16-13-34(27,28)50-31(44)22(4)10-6-8-20(2)12-15-37/h9-13,16,23-29,32-33,36-42H,5-8,14-15,17-18H2,1-4H3/b19-11-,20-12-,21-9+,22-10+/t23?,24-,25?,26+,27?,28-,29?,32+,33?,34+,35-/m1/s1
InChIKey DBVXZTURNWWPHJ-FNDDTPBQSA-N
Formula C35H50O15
HBA 15
HBD 7
MW 710.77
Rotatable Bonds 16
TPSA 234.43
LogP -0.04
Number Rings 4
Number Aromatic Rings 0
Heavy Atom Count 50
Formal Charge 0
Fraction CSP3 0.66
Exact Mass 710.31
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: C12C(O2)CC3C1C(OC=C3)OC4CCCCO4

Level: 1

Mol. Weight: 710.77 g/mol

Structure

SMILES: C12C(O2)CC3C1COC=C3

Level: 0

Mol. Weight: 710.77 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 710.77 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.57
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-3.59
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
228.47

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.68
Plasma Protein Binding
37.83
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
Inhibitor
CYP 3A4 Substrate
Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
6.91
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-3.41
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.58
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.2
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
-419791.09
Rat (Acute)
3.0
Rat (Chronic Oral)
4.4
Fathead Minnow
543.74
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
42496.56
Hydration Free Energy
-2.92
Log(D) at pH=7.4
0.4
Log(P)
0.75
Log S
-2.89
Log(Vapor Pressure)
-1383.46
Melting Point
110.76
pKa Acid
3.72
pKa Basic
1.07
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 3 0.9248
Maltose/maltodextrin-binding periplasmic protein P0AEX9 MALE_ECOLI Escherichia coli 3 0.8238
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 3 0.8116
Aldos-2-ulose dehydratase P84193 AUD_PHACH Phanerodontia chrysosporium 3 0.7780
ADP-ribosylation factor 1 P84077 ARF1_HUMAN Homo sapiens 2 0.7774
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7559
Gag-Pol polyprotein P0C6F2 POL_HV1LW Human immunodeficiency virus type 1 group M subtype B 3 0.7495
Carnitine O-acetyltransferase P47934 CACP_MOUSE Mus musculus 2 0.7261
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.7211
Transcriptional activator, LuxR/UhpA family of regulators Q7NQP7 Q7NQP7_CHRVO Chromobacterium violaceum 2 0.7179
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 2 0.7166
Transcriptional activator, LuxR/UhpA family of regulators Q7NQP7 Q7NQP7_CHRVO Chromobacterium violaceum 2 0.7164
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.7105
Muconolactone Delta-isomerase Q8G9L0 Q8G9L0_RHOOP Rhodococcus opacus 2 0.7101
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7089
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 2 0.7026

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