Thunaloside - Compound Card

Thunaloside

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Thunaloside

Structure
Zoomed Structure
  • Family: Plantae - Acanthaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Iridoid Glycoside
Canonical Smiles OCC1O[C@H](O[C@@H]2OC=CC3C2[C@@H](CO)[C@H](C3)O)[C@H](C([C@@H]1O)O)O
InChI InChI=1S/C15H24O9/c16-4-7-8(18)3-6-1-2-22-14(10(6)7)24-15-13(21)12(20)11(19)9(5-17)23-15/h1-2,6-21H,3-5H2/t6?,7-,8-,9?,10?,11+,12?,13-,14-,15+/m0/s1
InChIKey GCWUDVRYCRPVLH-PJOFICJMSA-N
Formula C15H24O9
HBA 9
HBD 6
MW 348.35
Rotatable Bonds 4
TPSA 149.07
LogP -2.72
Number Rings 3
Number Aromatic Rings 0
Heavy Atom Count 24
Formal Charge 0
Fraction CSP3 0.87
Exact Mass 348.14
Number of Lipinski Rule Violations 1
# Species Family Kingdom NCBI Taxonomy ID
1 Thunbergia grandiflora Acanthaceae Plantae 504049

Showing of synonyms

  • Ismail LD, El-Azlzi MM, et al. (1996). Iridoid glycosides from Thunbergia grandiflora. Phytochemistry,1996,42(4),1223-1225. [View] [PubMed]
Pubchem: 162909632

No compound-protein relationship available.

Structure

SMILES: C1CCC(C12)C(OC=C2)OC3CCCCO3

Level: 1

Mol. Weight: 348.35 g/mol

Structure

SMILES: C1CCC(C12)COC=C2

Level: 0

Mol. Weight: 348.35 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 348.35 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.29
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.91
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.36

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.77
Plasma Protein Binding
44.55
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
2.55
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-2.81
Biodegradation
Toxic
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
1.07
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
3.96
Micronucleos
Safe
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
-4.55
Rat (Acute)
2.21
Rat (Chronic Oral)
3.04
Fathead Minnow
2.34
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
438.6
Hydration Free Energy
-18.6
Log(D) at pH=7.4
-0.76
Log(P)
-1.97
Log S
-0.15
Log(Vapor Pressure)
-12.72
Melting Point
165.71
pKa Acid
7.18
pKa Basic
4.48
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Aldos-2-ulose dehydratase P84193 AUD_PHACH Phanerodontia chrysosporium 3 0.8928
Aldos-2-ulose dehydratase P84193 AUD_PHACH Phanerodontia chrysosporium 3 0.8928
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.8886
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.8886
Macrophage metalloelastase P39900 MMP12_HUMAN Homo sapiens 3 0.7365
Macrophage metalloelastase P39900 MMP12_HUMAN Homo sapiens 3 0.7365
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.7344
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.7344
Lysozyme C II P11941 LYSC2_ONCMY Oncorhynchus mykiss 3 0.7048
Lysozyme C II P11941 LYSC2_ONCMY Oncorhynchus mykiss 3 0.7048

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