6-O-angeloylantirrhinoside - Compound Card

6-O-angeloylantirrhinoside

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6-O-angeloylantirrhinoside

Structure
Zoomed Structure
  • Family: Plantae - Plantaginaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Iridoid Glycoside
Canonical Smiles OCC1O[C@@H](O[C@@H]2OC=C[C@@]3([C@H]2[C@@]2(C)O[C@H]2[C@H]3OC(=O)/C(=C\C)/C)O)[C@H](C([C@@H]1O)O)O
InChI InChI=1S/C20H28O11/c1-4-8(2)16(25)29-15-14-19(3,31-14)13-18(27-6-5-20(13,15)26)30-17-12(24)11(23)10(22)9(7-21)28-17/h4-6,9-15,17-18,21-24,26H,7H2,1-3H3/b8-4-/t9?,10-,11?,12+,13-,14+,15-,17+,18+,19-,20+/m1/s1
InChIKey AGHYMWGLKMZUEF-GITJHEKRSA-N
Formula C20H28O11
HBA 11
HBD 5
MW 444.43
Rotatable Bonds 5
TPSA 167.67
LogP -1.93
Number Rings 4
Number Aromatic Rings 0
Heavy Atom Count 31
Formal Charge 0
Fraction CSP3 0.75
Exact Mass 444.16
Number of Lipinski Rule Violations 1
# Species Family Kingdom NCBI Taxonomy ID
1 Linaria tingitana Plantaginaceae Plantae 1070266

Showing of synonyms

  • Hanfer M, Cheriet T, et al. (2017). Iridoids and anti-inflammatory properties of n-butanol extract of Linaria tingitana Boiss. & Reut. Natural product research, 2017, 31(17), 2008-2015. [View] [PubMed]

No compound-protein relationship available.

Structure

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

Level: 1

Mol. Weight: 444.43 g/mol

Structure

SMILES: C12C(O2)CC3C1COC=C3

Level: 0

Mol. Weight: 444.43 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 444.43 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.38
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.86
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.67

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.78
Plasma Protein Binding
32.2
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
5.68
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-1.73
Biodegradation
Toxic
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
1.03
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
4.76
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
-59.76
Rat (Acute)
2.86
Rat (Chronic Oral)
3.12
Fathead Minnow
3.87
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
465.63
Hydration Free Energy
-5.07
Log(D) at pH=7.4
-0.8
Log(P)
-0.45
Log S
-1.53
Log(Vapor Pressure)
-12.78
Melting Point
116.5
pKa Acid
5.7
pKa Basic
2.04
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.8977
Aldos-2-ulose dehydratase P84193 AUD_PHACH Phanerodontia chrysosporium 3 0.8928
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.8568
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.7910
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7651
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7602
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7495
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.7415
Lysozyme C II P11941 LYSC2_ONCMY Oncorhynchus mykiss 3 0.7301
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7271
Raucaffricine-O-beta-D-glucosidase Q9SPP9 RG1_RAUSE Rauvolfia serpentina 4 0.7077
Retinol-binding protein 1 P09455 RET1_HUMAN Homo sapiens 3 0.7049

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