3beta-acetyloxy-1alpha,13-dihydroxygermacra-4,7(11),9-trien-6alpha,12-olide - Compound Card

3beta-acetyloxy-1alpha,13-dihydroxygermacra-4,7(11),9-trien-6alpha,12-olide

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3beta-acetyloxy-1alpha,13-dihydroxygermacra-4,7(11),9-trien-6alpha,12-olide

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sesquiterpene Lactone
Canonical Smiles OCC1=C2C/C=C(/C)\[C@@H](O)C[C@H](/C(=C\[C@H]2OC1=O)/C)OC(=O)C
InChI InChI=1S/C17H22O6/c1-9-4-5-12-13(8-18)17(21)23-16(12)6-10(2)15(7-14(9)20)22-11(3)19/h4,6,14-16,18,20H,5,7-8H2,1-3H3/b9-4-,10-6-/t14-,15+,16+/m0/s1
InChIKey UNANNKAWBHGWLX-KIWIWDGISA-N
Formula C17H22O6
HBA 6
HBD 2
MW 322.36
Rotatable Bonds 2
TPSA 93.06
LogP 1.18
Number Rings 2
Number Aromatic Rings 0
Heavy Atom Count 23
Formal Charge 0
Fraction CSP3 0.53
Exact Mass 322.14
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Achillea fragrantissima Asteraceae Plantae 282738

Showing of synonyms

  • Abdel-Mogib M, Jakupovic J, et al. (1989). Glaucolides from Achillea fragrantissima.. Phytochemistry,1989,28(12),3528-3530. [View]
Pubchem: 162921905
Nmrshiftdb2: 70069995

No compound-protein relationship available.

Structure

SMILES: C1C(=O)OC(C=12)C=CCCCC=CC2

Level: 0

Mol. Weight: 322.36 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.77
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.56
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.97

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.4
Plasma Protein Binding
34.04
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
Non-Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
6.2
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.81
Biodegradation
Toxic
Carcinogenesis
Toxic
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.06
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.34
Micronucleos
Toxic
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
-3.39
Rat (Acute)
2.38
Rat (Chronic Oral)
2.13
Fathead Minnow
4.0
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
368.92
Hydration Free Energy
-10.73
Log(D) at pH=7.4
0.54
Log(P)
1.08
Log S
-2.1
Log(Vapor Pressure)
-6.83
Melting Point
133.69
pKa Acid
7.93
pKa Basic
4.72
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Prolyl tripeptidyl peptidase Q7MUW6 PTP_PORGI Porphyromonas gingivalis 3 0.8734
Prolyl tripeptidyl peptidase Q7MUW6 PTP_PORGI Porphyromonas gingivalis 3 0.8734
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.7472
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.7472
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.7451
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.7451
Reaction center protein L chain P0C0Y7 RCEH_RHOSH Rhodobacter sphaeroides 3 0.7020
Reaction center protein L chain P0C0Y7 RCEH_RHOSH Rhodobacter sphaeroides 3 0.7020

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