8alpha-O-(4-hydroxy-2-methylenebutanoyloxy)melitensin - Compound Card

8alpha-O-(4-hydroxy-2-methylenebutanoyloxy)melitensin

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8alpha-O-(4-hydroxy-2-methylenebutanoyloxy)melitensin

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)(C=C)[C@@H]([C@@H]2[C@@H]1[C@H](C)C(=O)O2)C(=C)CO
InChI InChI=1S/C20H28O6/c1-6-20(5)9-14(25-18(23)11(2)7-8-21)15-13(4)19(24)26-17(15)16(20)12(3)10-22/h6,13-17,21-22H,1-3,7-10H2,4-5H3/t13-,14-,15+,16+,17-,20+/m0/s1
InChIKey VKSVJJJVFPRTAL-XFNMEUKGSA-N
Formula C20H28O6
HBA 6
HBD 2
MW 364.44
Rotatable Bonds 7
TPSA 93.06
LogP 1.78
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

Showing of synonyms

  • Djeddi S, Karioti A, et al. (2008). A novel sesquiterpene lactone from Centaurea pullata: Structure elucidation, antimicrobial activity, and prediction of pharmacokinetic properties. Bioorganic and Medicinal Chemistry,2008,16,3725-3731. [View] [PubMed]
Pubchem: 25113751
Nmrshiftdb2: 70021820

No compound-protein relationship available.

Structure

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

Level: 0

Mol. Weight: 364.44 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.65
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.650
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.49

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.490
Plasma Protein Binding
60.8
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
Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
10.380
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.210
Biodegradation
Safe
Carcinogenesis
Toxic
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.310
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.680
Micronucleos
Safe
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
-2.150
Rat (Acute)
3.600
Rat (Chronic Oral)
2.150
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
387.310
Hydration Free Energy
-7.600
Log(D) at pH=7.4
1.520
Log(P)
1.59
Log S
-3.05
Log(Vapor Pressure)
-7.95
Melting Point
96.8
pKa Acid
8.48
pKa Basic
4.34
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 0.9128
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 3 0.9128
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 3 0.8689
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 3 0.8689
ADP-ribosylation factor 1 P84080 ARF1_BOVIN Bos taurus 3 0.8639
ADP-ribosylation factor 1 P84080 ARF1_BOVIN Bos taurus 3 0.8639
Reaction center protein L chain P0C0Y7 RCEH_RHOSH Rhodobacter sphaeroides 3 0.8529
Reaction center protein L chain P0C0Y7 RCEH_RHOSH Rhodobacter sphaeroides 3 0.8529
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.7936
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.7936
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7763
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7763
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.7626
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.7626
Xylose isomerase P24300 XYLA_STRRU Streptomyces rubiginosus 3 0.7475
Xylose isomerase P24300 XYLA_STRRU Streptomyces rubiginosus 3 0.7475
Glycogenin-1 P46976 GLYG_HUMAN Homo sapiens 3 0.7437
Glycogenin-1 P46976 GLYG_HUMAN Homo sapiens 3 0.7437
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7425
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7425
14-3-3 protein gamma P61981 1433G_HUMAN Homo sapiens 3 0.7135
14-3-3 protein gamma P61981 1433G_HUMAN Homo sapiens 3 0.7135
Cysteine synthase P45040 CYSK_HAEIN Haemophilus influenzae 3 0.7133
Cysteine synthase P45040 CYSK_HAEIN Haemophilus influenzae 3 0.7133
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7021
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7021

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