11beta-hydroxy-13-chloro-11,13-dihydrohymenin - Compound Card

11beta-hydroxy-13-chloro-11,13-dihydrohymenin

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11beta-hydroxy-13-chloro-11,13-dihydrohymenin

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sesquiterpene Lactone
Canonical Smiles CC(=O)O[C@H]1CC(C)(C)[C@]23[C@@H]([C@@H]4[C@@H]1[C@H](C)C(=O)O4)[C@]([C@@H]([C@@H]3O2)Cl)(C)O
InChI InChI=1S/C18H25ClO6/c1-7-10-9(23-8(2)20)6-16(3,4)18-12(11(10)24-15(7)21)17(5,22)13(19)14(18)25-18/h7,9-14,22H,6H2,1-5H3/t7-,9-,10+,11-,12-,13+,14-,17-,18+/m0/s1
InChIKey GYJPVLCGWHSLHU-DOXVLSEESA-N
Formula C18H25ClO6
HBA 6
HBD 1
MW 372.85
Rotatable Bonds 1
TPSA 85.36
LogP 1.65
Number Rings 4
Number Aromatic Rings 0
Heavy Atom Count 25
Formal Charge 0
Fraction CSP3 0.89
Exact Mass 372.13
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Ambrosia maritima Asteraceae Plantae 1028380

Showing of synonyms

  • Mahmoud AA, Ahmed AA, et al. (1999). A new chlorosesquiterpene lactone from Ambrosia maritima.. Fitoterapia,1999,70,575-578. [View]
Pubchem: 162992226
Nmrshiftdb2: 60072100

No compound-protein relationship available.

Structure

SMILES: C123C(O3)CCC1C4C(CC(=O)O4)CCC2

Level: 0

Mol. Weight: 372.85 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.2
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.77
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.48

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.3
Plasma Protein Binding
27.71
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
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
Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
12.38
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.78
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.02
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
6.39
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
-2.81
Rat (Acute)
4.47
Rat (Chronic Oral)
1.56
Fathead Minnow
3.84
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Toxic
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
386.1
Hydration Free Energy
-6.28
Log(D) at pH=7.4
1.34
Log(P)
1.4
Log S
-3.01
Log(Vapor Pressure)
-6.89
Melting Point
143.94
pKa Acid
5.31
pKa Basic
2.64
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Trichothecene 15-O-acetyltransferase TRI3 Q9C1B7 TRI3_FUSSP Fusarium sporotrichioides 3 0.7523
Trichothecene 15-O-acetyltransferase TRI3 Q9C1B7 TRI3_FUSSP Fusarium sporotrichioides 3 0.7523
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7285
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7285
Angiotensin-converting enzyme Q10714 ACE_DROME Drosophila melanogaster 3 0.7208
Angiotensin-converting enzyme Q10714 ACE_DROME Drosophila melanogaster 3 0.7208
Quorum-sensing transcriptional activator Q8XBD0 Q8XBD0_ECO57 Escherichia coli O157:H7 3 0.7024
Quorum-sensing transcriptional activator Q8XBD0 Q8XBD0_ECO57 Escherichia coli O157:H7 3 0.7024

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