11beta,13-dihydrocynaropicrin - Compound Card

11beta,13-dihydrocynaropicrin

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11beta,13-dihydrocynaropicrin

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sesquiterpene Lactone
Canonical Smiles OCC(=C)C(=O)O[C@H]1CC(=C)[C@H]2[C@@H]([C@@H]3[C@@H]1[C@@H](C)C(=O)O3)C(=C)[C@H](C2)O
InChI InChI=1S/C19H24O6/c1-8-5-14(24-18(22)9(2)7-20)16-11(4)19(23)25-17(16)15-10(3)13(21)6-12(8)15/h11-17,20-21H,1-3,5-7H2,4H3/t11-,12+,13+,14+,15+,16-,17-/m1/s1
InChIKey CCBNOSMFTUQQLZ-DVHVHUQNSA-N
Formula C19H24O6
HBA 6
HBD 2
MW 348.4
Rotatable Bonds 3
TPSA 93.06
LogP 1.14
Number Rings 3
Number Aromatic Rings 0
Heavy Atom Count 25
Formal Charge 0
Fraction CSP3 0.58
Exact Mass 348.16
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Cheirolophus uliginosus Asteraceae Plantae 65003

Showing of synonyms

  • Marco JA, Sanz-Cervera JF, et al. (1994). Sesquiterpene lactones, lignans and aromatic esters ftrom Cheirolophus species. Phytochemistry,1994,37(4),1101-1107. [View]
Pubchem: 14164984
Nmrshiftdb2: 60072554

No compound-protein relationship available.

Structure

SMILES: C=C1CCC2C(=C)CCC(C3C12)CC(=O)O3

Level: 0

Mol. Weight: 348.4 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.55
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.680
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.54

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.530
Plasma Protein Binding
52.88
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
Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
10.540
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.690
Biodegradation
Safe
Carcinogenesis
Toxic
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.630
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.150
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
-3.720
Rat (Acute)
3.890
Rat (Chronic Oral)
2.050
Fathead Minnow
3.920
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
390.900
Hydration Free Energy
-7.870
Log(D) at pH=7.4
0.900
Log(P)
0.6
Log S
-2.68
Log(Vapor Pressure)
-8.28
Melting Point
154.47
pKa Acid
6.84
pKa Basic
4.07
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 3 0.8740
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 3 0.8740
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.8537
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.8537
Xylose isomerase P24300 XYLA_STRRU Streptomyces rubiginosus 3 0.8148
Xylose isomerase P24300 XYLA_STRRU Streptomyces rubiginosus 3 0.8148
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.7913
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.7913
Trichothecene 15-O-acetyltransferase TRI3 Q9C1B7 TRI3_FUSSP Fusarium sporotrichioides 3 0.7304
Trichothecene 15-O-acetyltransferase TRI3 Q9C1B7 TRI3_FUSSP Fusarium sporotrichioides 3 0.7304
Cysteine synthase P45040 CYSK_HAEIN Haemophilus influenzae 3 0.7266
Cysteine synthase P45040 CYSK_HAEIN Haemophilus influenzae 3 0.7266
Ferrichrome outer membrane transporter/phage receptor P06971 FHUA_ECOLI Escherichia coli 3 0.7264
Ferrichrome outer membrane transporter/phage receptor P06971 FHUA_ECOLI Escherichia coli 3 0.7264
Reaction center protein L chain P0C0Y7 RCEH_RHOSH Rhodobacter sphaeroides 3 0.7169
Reaction center protein L chain P0C0Y7 RCEH_RHOSH Rhodobacter sphaeroides 3 0.7169

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