Picriside B - Compound Card

Picriside B

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Picriside B

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sesquiterpene Lactone
Canonical Smiles OC[C@H]1O[C@@H](OC/C/2=C\[C@H]3OC(=O)C(=C)[C@@H]3CC/C(=C/CC2)/C)[C@@H]([C@H]([C@@H]1O)O)O
InChI InChI=1S/C21H30O8/c1-11-4-3-5-13(8-15-14(7-6-11)12(2)20(26)28-15)10-27-21-19(25)18(24)17(23)16(9-22)29-21/h4,8,14-19,21-25H,2-3,5-7,9-10H2,1H3/b11-4+,13-8-/t14-,15+,16+,17+,18-,19+,21+/m0/s1
InChIKey OEDNDLHBXUIYOG-VXBUZGHMSA-N
Formula C21H30O8
HBA 8
HBD 4
MW 410.46
Rotatable Bonds 4
TPSA 125.68
LogP 0.35
Number Rings 3
Number Aromatic Rings 0
Heavy Atom Count 29
Formal Charge 0
Fraction CSP3 0.67
Exact Mass 410.19
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Launaea arborescens Asteraceae Plantae 43199

Showing of synonyms

  • Bitam F, Ciavatta ML, et al. (2008). Chemical characterisation of the terpenoid constituents of the Algerian plant Launaea arborescens. Phytochemistry,2008,69,2984-2992. [View] [PubMed]
Pubchem: 21636024
Nmrshiftdb2: 60081497

No compound-protein relationship available.

Structure

SMILES: C=C1C(=O)OC(C12)C=C(CCC=CCC2)COC3CCCCO3

Level: 1

Mol. Weight: 410.46 g/mol

Structure

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

Level: 0

Mol. Weight: 410.46 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 410.46 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.05
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.860
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.6

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.800
Plasma Protein Binding
61.6
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
3.180
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-2.590
Biodegradation
Toxic
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.230
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
5.250
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
-17.640
Rat (Acute)
2.640
Rat (Chronic Oral)
3.120
Fathead Minnow
3.980
Respiratory Disease
Safe
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Toxic

General Properties

Boiling Point
477.390
Hydration Free Energy
-9.350
Log(D) at pH=7.4
1.510
Log(P)
0.47
Log S
-2.17
Log(Vapor Pressure)
-12.6
Melting Point
156.62
pKa Acid
6.31
pKa Basic
5.91
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.8449
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.8449
Xylose isomerase P24300 XYLA_STRRU Streptomyces rubiginosus 3 0.8299
Xylose isomerase P24300 XYLA_STRRU Streptomyces rubiginosus 3 0.8299
Laminarinase Q9WXN1 Q9WXN1_THEMA Thermotoga maritima 3 0.8226
Laminarinase Q9WXN1 Q9WXN1_THEMA Thermotoga maritima 3 0.8226
beta-glucosidase Q92AS9 Q92AS9_LISIN Listeria innocua serovar 6a 3 0.7872
beta-glucosidase Q92AS9 Q92AS9_LISIN Listeria innocua serovar 6a 3 0.7872
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 3 0.7863
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 3 0.7863
Gag-Pol polyprotein P0C6F2 POL_HV1LW Human immunodeficiency virus type 1 group M subtype B 3 0.7856
Gag-Pol polyprotein P0C6F2 POL_HV1LW Human immunodeficiency virus type 1 group M subtype B 3 0.7856
Putative b-glycan phosphorylase Q21MB1 Q21MB1_SACD2 Saccharophagus degradans 4 0.7101
Putative b-glycan phosphorylase Q21MB1 Q21MB1_SACD2 Saccharophagus degradans 4 0.7101

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