14-chloro-10beta-hydroxy-10(14)-dihydrozaluzanin D - Compound Card

14-chloro-10beta-hydroxy-10(14)-dihydrozaluzanin D

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14-chloro-10beta-hydroxy-10(14)-dihydrozaluzanin D

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sesquiterpene Lactone
Canonical Smiles ClC[C@]1(O)CC[C@@H]2[C@@H]([C@@H]3[C@H]1C[C@@H](C3=C)OC(=O)C)OC(=O)C2=C
InChI InChI=1S/C17H21ClO5/c1-8-11-4-5-17(21,7-18)12-6-13(22-10(3)19)9(2)14(12)15(11)23-16(8)20/h11-15,21H,1-2,4-7H2,3H3/t11-,12+,13-,14-,15-,17+/m0/s1
InChIKey AAGASLNRMNLPPK-XCNHXOCXSA-N
Formula C17H21ClO5
HBA 5
HBD 1
MW 340.8
Rotatable Bonds 2
TPSA 72.83
LogP 1.97
Number Rings 3
Number Aromatic Rings 0
Heavy Atom Count 23
Formal Charge 0
Fraction CSP3 0.65
Exact Mass 340.11
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Centaurea acaulis Asteraceae Plantae 2969722

Showing of synonyms

  • Bentamène A, Benayache S, et al. (2005). A new guaianolide and other sesquiterpene lactones from Centaurea acaulis L. (Asteraceae). Biochemical Systematics and Ecology,2005,33,1061-1065. [View]
Pubchem: 162816966
Nmrshiftdb2: 70103400

No compound-protein relationship available.

Structure

SMILES: O=C(O1)C(=C)C(C1C23)CCCC3CCC2=C

Level: 0

Mol. Weight: 340.8 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.69
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.76
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.35

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.54
Plasma Protein Binding
40.56
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
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
10.33
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.12
Biodegradation
Safe
Carcinogenesis
Toxic
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.78
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
5.43
Micronucleos
Toxic
NR-AhR
Safe
NR-AR
Safe
NR-AR-LBD
Toxic
NR-Aromatase
Safe
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Toxic
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
-0.36
Rat (Acute)
3.73
Rat (Chronic Oral)
1.43
Fathead Minnow
3.92
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Toxic

General Properties

Boiling Point
367.04
Hydration Free Energy
-6.44
Log(D) at pH=7.4
1.42
Log(P)
1.81
Log S
-2.98
Log(Vapor Pressure)
-7.2
Melting Point
144.58
pKa Acid
8.03
pKa Basic
4.94
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
ADP-ribosylation factor 1 P84080 ARF1_BOVIN Bos taurus 3 0.8540
ADP-ribosylation factor 1 P84080 ARF1_BOVIN Bos taurus 3 0.8540
Trichothecene 15-O-acetyltransferase TRI3 Q9C1B7 TRI3_FUSSP Fusarium sporotrichioides 3 0.8150
Trichothecene 15-O-acetyltransferase TRI3 Q9C1B7 TRI3_FUSSP Fusarium sporotrichioides 3 0.8150
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7632
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7632
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.7506
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.7506
N-alpha-acetyltransferase 50 Q9GZZ1 NAA50_HUMAN Homo sapiens 3 0.7484
N-alpha-acetyltransferase 50 Q9GZZ1 NAA50_HUMAN Homo sapiens 3 0.7484
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7361
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7361
Abscisic acid receptor PYL2 O80992 PYL2_ARATH Arabidopsis thaliana 2 0.7201
Abscisic acid receptor PYL2 O80992 PYL2_ARATH Arabidopsis thaliana 2 0.7201
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7175
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7175

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