11,13-dehydromelitensin - Compound Card

11,13-dehydromelitensin

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11,13-dehydromelitensin

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sesquiterpenoid
Canonical Smiles OCC(=C)[C@@H]1[C@H]2OC(=O)C(=C)[C@@H]2[C@H](C[C@@]1(C)C=C)O
InChI InChI=1S/C15H20O4/c1-5-15(4)6-10(17)11-9(3)14(18)19-13(11)12(15)8(2)7-16/h5,10-13,16-17H,1-3,6-7H2,4H3/t10-,11+,12+,13-,15+/m0/s1
InChIKey GQBRDBUFLQZZBP-IHWVXMPCSA-N
Formula C15H20O4
HBA 4
HBD 2
MW 264.32
Rotatable Bonds 3
TPSA 66.76
LogP 1.21
Number Rings 2
Number Aromatic Rings 0
Heavy Atom Count 19
Formal Charge 0
Fraction CSP3 0.53
Exact Mass 264.14
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Centaurea maroccana Asteraceae Plantae 41503
2 Centaurea papposa Asteraceae Plantae 1006337

Showing of synonyms

  • Grafakou M.E, Barda C, et al. (2022). In vitro cytotoxic and anti-inflammatory activities of sesquiterpene lactones from Centaurea papposa (Coss.) Greuter. Natural product research, 2022, 36(12), 3211-3215. [View] [PubMed]
  • Bicha S, Chalard P, et al. (2013). Maroccanin: a new gamma-lactone and other constituents from Centaurea maroccana ball. (Asteraceae). Records of Natural Products,2013,7(2),114-118. [View]
Pubchem: 10333020
Nmrshiftdb2: 60027308

No compound-protein relationship available.

Structure

SMILES: C=C1C(=O)OC(C12)CCCC2

Level: 0

Mol. Weight: 264.32 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.8
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.310
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.63

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.470
Plasma Protein Binding
50.45
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
8.200
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.110
Biodegradation
Safe
Carcinogenesis
Toxic
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-1.050
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
4.000
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
1.200
Rat (Acute)
3.450
Rat (Chronic Oral)
1.770
Fathead Minnow
3.920
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
331.710
Hydration Free Energy
-10.360
Log(D) at pH=7.4
0.760
Log(P)
1.16
Log S
-2.34
Log(Vapor Pressure)
-6.6
Melting Point
120.01
pKa Acid
6.77
pKa Basic
4.17
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 3 0.8599
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 3 0.8599
Xylose isomerase P24300 XYLA_STRRU Streptomyces rubiginosus 3 0.8168
Xylose isomerase P24300 XYLA_STRRU Streptomyces rubiginosus 3 0.8168
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7426
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7426
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7308
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7308
Reaction center protein L chain P0C0Y7 RCEH_RHOSH Rhodobacter sphaeroides 3 0.7190
Reaction center protein L chain P0C0Y7 RCEH_RHOSH Rhodobacter sphaeroides 3 0.7190
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7114
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7114
Abscisic acid receptor PYL2 O80992 PYL2_ARATH Arabidopsis thaliana 2 0.7084
Abscisic acid receptor PYL2 O80992 PYL2_ARATH Arabidopsis thaliana 2 0.7084

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