3-oxo-gamma-costic acid beta-D-glucopyranoside ester - Compound Card

3-oxo-gamma-costic acid beta-D-glucopyranoside ester

Select a section from the left sidebar

3-oxo-gamma-costic acid beta-D-glucopyranoside ester

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sesquiterpene Glycoside
Canonical Smiles OC1O[C@H](COC(=O)C(=C)[C@@H]2CC[C@@]3(C(=C(C)C(=O)CC3)C2)C)[C@H]([C@@H]([C@H]1O)O)O
InChI InChI=1S/C21H30O8/c1-10(12-4-6-21(3)7-5-14(22)11(2)13(21)8-12)19(26)28-9-15-16(23)17(24)18(25)20(27)29-15/h12,15-18,20,23-25,27H,1,4-9H2,2-3H3/t12-,15-,16-,17+,18-,20?,21+/m1/s1
InChIKey LYYVFRHZNWNCHV-HGGQRQHSSA-N
Formula C21H30O8
HBA 8
HBD 4
MW 410.46
Rotatable Bonds 4
TPSA 133.52
LogP 0.37
Number Rings 3
Number Aromatic Rings 0
Heavy Atom Count 29
Formal Charge 0
Fraction CSP3 0.71
Exact Mass 410.19
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Chiliadenus montanus Asteraceae Plantae 1458965

Showing of synonyms

  • Hegazy MEF, Matsuda H, et al. (2014). Chemical constituents and their antibacterial and antifungal activity from the Egyptian herbal medicine Chiliadenus montanus. Phytochemistry,2014,103,154-161. [View] [PubMed]
Pubchem: 162816983
Nmrshiftdb2: 70083419

No compound-protein relationship available.

Structure

SMILES: C1C(=O)CCC(C=12)CCC(C2)C(=C)C(=O)OCC3CCCCO3

Level: 1

Mol. Weight: 410.46 g/mol

Structure

SMILES: C1CCCC(C1=2)CCC(=O)C2

Level: 0

Mol. Weight: 410.46 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 410.46 g/mol

Antimicrobial

Absorption

Caco-2 (logPapp)
-5.16
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.91
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.83

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.74
Plasma Protein Binding
79.64
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
3.2
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
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
0.5
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.01
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
-13.87
Rat (Acute)
3.06
Rat (Chronic Oral)
3.41
Fathead Minnow
4.06
Respiratory Disease
Safe
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
456.78
Hydration Free Energy
-10.61
Log(D) at pH=7.4
1.35
Log(P)
0.21
Log S
-2.45
Log(Vapor Pressure)
-11.81
Melting Point
169.69
pKa Acid
5.52
pKa Basic
5.97
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.9122
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.9122
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.8642
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.8642
Aldos-2-ulose dehydratase P84193 AUD_PHACH Phanerodontia chrysosporium 3 0.8598
Aldos-2-ulose dehydratase P84193 AUD_PHACH Phanerodontia chrysosporium 3 0.8598
Cytochrome P450 Q93H81 Q93H81_STRAX Streptomyces avermitilis 3 0.8431
Cytochrome P450 Q93H81 Q93H81_STRAX Streptomyces avermitilis 3 0.8431
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.8015
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.8015
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7693
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7693
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7685
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7685
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7545
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7545
N-alpha-acetyltransferase 50 Q9GZZ1 NAA50_HUMAN Homo sapiens 3 0.7532
N-alpha-acetyltransferase 50 Q9GZZ1 NAA50_HUMAN Homo sapiens 3 0.7532
Lysosomal acid glucosylceramidase P04062 GLCM_HUMAN Homo sapiens 3 0.7402
Lysosomal acid glucosylceramidase P04062 GLCM_HUMAN Homo sapiens 3 0.7402
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7394
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7394
Abscisic acid receptor PYL9 Q84MC7 PYL9_ARATH Arabidopsis thaliana 3 0.7268
Abscisic acid receptor PYL9 Q84MC7 PYL9_ARATH Arabidopsis thaliana 3 0.7268
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7258
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7258
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7248
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7248
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7143
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7143

Download SDF