8alpha-isobutanoyloxy-5alpha-chloro-4beta,10alpha-dihydroxy-1alpha,2alpha-epoxy-11,13-dehydroguaia-6alpha,12-olide - Compound Card

8alpha-isobutanoyloxy-5alpha-chloro-4beta,10alpha-dihydroxy-1alpha,2alpha-epoxy-11,13-dehydroguaia-6alpha,12-olide

Select a section from the left sidebar

8alpha-isobutanoyloxy-5alpha-chloro-4beta,10alpha-dihydroxy-1alpha,2alpha-epoxy-11,13-dehydroguaia-6alpha,12-olide

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sesquiterpene Lactone
Canonical Smiles O=C(C(C)C)O[C@H]1C[C@@](C)(O)[C@]23[C@]([C@@H]4[C@@H]1[C@H](C)C(=O)O4)(Cl)[C@@](C[C@@H]3O2)(C)O
InChI InChI=1S/C19H27ClO7/c1-8(2)14(21)25-10-6-17(5,24)19-11(27-19)7-16(4,23)18(19,20)13-12(10)9(3)15(22)26-13/h8-13,23-24H,6-7H2,1-5H3/t9-,10-,11-,12+,13-,16-,17+,18+,19+/m0/s1
InChIKey SKUDQVAPWPVZPH-HFDQNHLESA-N
Formula C19H27ClO7
HBA 7
HBD 2
MW 402.87
Rotatable Bonds 2
TPSA 105.59
LogP 1.16
Number Rings 4
Number Aromatic Rings 0
Heavy Atom Count 27
Formal Charge 0
Fraction CSP3 0.89
Exact Mass 402.14
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Otanthus maritimus Asteraceae Plantae 1155244

Showing of synonyms

  • Jakupovic J, Boeker R, et al. (1988). Highly oxygenated guaianolides from Otanthus maritimus. Phytochemistry,1988,27(4),1135-1140. [View]
Pubchem: 162983265
Nmrshiftdb2: 60056756

No compound-protein relationship available.

Structure

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

Level: 0

Mol. Weight: 402.87 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.13
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.750
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.22

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.300
Plasma Protein Binding
31.2
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
Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
10.250
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.450
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.130
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
6.140
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
-6.960
Rat (Acute)
4.720
Rat (Chronic Oral)
1.670
Fathead Minnow
3.830
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
389.270
Hydration Free Energy
-7.160
Log(D) at pH=7.4
0.500
Log(P)
1.37
Log S
-2.85
Log(Vapor Pressure)
-7.09
Melting Point
149.96
pKa Acid
5.34
pKa Basic
2.7
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7518
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7518
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7446
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7446
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.7418
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.7418
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7163
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7163

Download SDF