11beta,13-dihydro 19-desoxycnicin - Compound Card

11beta,13-dihydro 19-desoxycnicin

Select a section from the left sidebar

11beta,13-dihydro 19-desoxycnicin

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sesquiterpene Lactone
Canonical Smiles OCCC(=C)C(=O)O[C@H]1C/C(=C/CC/C(=C/C2[C@@H]1[C@H](C)C(=O)O2)/CO)/C
InChI InChI=1S/C20H28O6/c1-12-5-4-6-15(11-22)10-17-18(14(3)20(24)26-17)16(9-12)25-19(23)13(2)7-8-21/h5,10,14,16-18,21-22H,2,4,6-9,11H2,1,3H3/b12-5+,15-10-/t14-,16-,17?,18+/m0/s1
InChIKey DTSRWZQRWMWHDL-JTVSCNHPSA-N
Formula C20H28O6
HBA 6
HBD 2
MW 364.44
Rotatable Bonds 5
TPSA 93.06
LogP 2.06
Number Rings 2
Number Aromatic Rings 0
Heavy Atom Count 26
Formal Charge 0
Fraction CSP3 0.6
Exact Mass 364.19
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Centaurea pullata Asteraceae Plantae 347528
2 Centaurea pullata Asteraceae Plantae 347528

Showing of synonyms

  • Djeddi S, Karioti A, et al. (2007). Minor sesquiterpene lactones from Centaurea pullata and their antimicrobial activity. Journal of Natural Products,2007,70,1796-1799. [View] [PubMed]
  • Benayache F, Benayache S, et al. (1992). Sesquiterpene lactones from Centaurea pullata. Phytochemistry,1992,31(12),4359-4360. [View]
Pubchem: 163087130

No compound-protein relationship available.

Structure

SMILES: C1C(=O)OC(C12)C=CCCC=CCC2

Level: 0

Mol. Weight: 364.44 g/mol

Antimicrobial

Absorption

Caco-2 (logPapp)
-4.65
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.620
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.77

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.580
Plasma Protein Binding
45.4
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
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
9.380
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.640
Biodegradation
Toxic
Carcinogenesis
Toxic
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.410
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.850
Micronucleos
Toxic
NR-AhR
Safe
NR-AR
Safe
NR-AR-LBD
Safe
NR-Aromatase
Safe
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Toxic
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
-2.430
Rat (Acute)
2.570
Rat (Chronic Oral)
2.220
Fathead Minnow
4.250
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
407.650
Hydration Free Energy
-8.020
Log(D) at pH=7.4
1.400
Log(P)
1.72
Log S
-3.17
Log(Vapor Pressure)
-7.7
Melting Point
100.72
pKa Acid
9.11
pKa Basic
4.98
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.9371
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.9371
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 3 0.9120
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 3 0.9120
Xylose isomerase P24300 XYLA_STRRU Streptomyces rubiginosus 3 0.8977
Xylose isomerase P24300 XYLA_STRRU Streptomyces rubiginosus 3 0.8977
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.8920
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.8920
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.8554
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.8554
Peptidoglycan recognition protein 1 Q9GK12 PGRP1_CAMDR Camelus dromedarius 3 0.8310
Peptidoglycan recognition protein 1 Q9GK12 PGRP1_CAMDR Camelus dromedarius 3 0.8310
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7809
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7809
Angiotensin-converting enzyme Q10714 ACE_DROME Drosophila melanogaster 3 0.7674
Angiotensin-converting enzyme Q10714 ACE_DROME Drosophila melanogaster 3 0.7674
Quorum-sensing transcriptional activator Q8XBD0 Q8XBD0_ECO57 Escherichia coli O157:H7 3 0.7534
Quorum-sensing transcriptional activator Q8XBD0 Q8XBD0_ECO57 Escherichia coli O157:H7 3 0.7534
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7515
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7515
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7394
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7394
Carbonic anhydrase 1 P00915 CAH1_HUMAN Homo sapiens 3 0.7303
Carbonic anhydrase 1 P00915 CAH1_HUMAN Homo sapiens 3 0.7303
Prolyl tripeptidyl peptidase Q7MUW6 PTP_PORGI Porphyromonas gingivalis 2 0.7294
Prolyl tripeptidyl peptidase Q7MUW6 PTP_PORGI Porphyromonas gingivalis 2 0.7294
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7292
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7292
Cysteine synthase P45040 CYSK_HAEIN Haemophilus influenzae 3 0.7191
Cysteine synthase P45040 CYSK_HAEIN Haemophilus influenzae 3 0.7191
Abscisic acid receptor PYL3 Q9SSM7 PYL3_ARATH Arabidopsis thaliana 3 0.7158
Abscisic acid receptor PYL3 Q9SSM7 PYL3_ARATH Arabidopsis thaliana 3 0.7158
Chitinase Q54276 Q54276_SERMA Serratia marcescens 3 0.7113
Chitinase Q54276 Q54276_SERMA Serratia marcescens 3 0.7113
Integrin beta-1-binding protein 1 O14713 ITBP1_HUMAN Homo sapiens 3 0.7101
Integrin beta-1-binding protein 1 O14713 ITBP1_HUMAN Homo sapiens 3 0.7101
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7101
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7101
ADP-ribosylation factor 1 P84080 ARF1_BOVIN Bos taurus 3 0.7041
ADP-ribosylation factor 1 P84080 ARF1_BOVIN Bos taurus 3 0.7041

Download SDF