1-angeloyloxy-9-alphahydroxy-eudesma-4,11(13)-dien-6alpha,12-olide - Compound Card

1-angeloyloxy-9-alphahydroxy-eudesma-4,11(13)-dien-6alpha,12-olide

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1-angeloyloxy-9-alphahydroxy-eudesma-4,11(13)-dien-6alpha,12-olide

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sesquiterpene Lactone
Canonical Smiles C/C=C(\C(=O)OC1CC=C([C@H]2C1(C)[C@H](O)CC1[C@@H]2OC(=O)C1=C)C)/C
InChI InChI=1S/C20H26O5/c1-6-10(2)18(22)24-15-8-7-11(3)16-17-13(12(4)19(23)25-17)9-14(21)20(15,16)5/h6-7,13-17,21H,4,8-9H2,1-3,5H3/b10-6-/t13?,14-,15?,16-,17+,20?/m1/s1
InChIKey UUFLRDLXVUZQGL-PGVPMOMDSA-N
Formula C20H26O5
HBA 5
HBD 1
MW 346.42
Rotatable Bonds 2
TPSA 72.83
LogP 2.7
Number Rings 3
Number Aromatic Rings 0
Heavy Atom Count 25
Formal Charge 0
Fraction CSP3 0.6
Exact Mass 346.18
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Pluchea dioscoridis Asteraceae Plantae —

Showing of synonyms

  • Dawidar AA, Metwally M (1985). New alpha-cyclocostunolide and isocostic acid derivatives from Pluchea dioscoridis. Chemical and Pharmaceutical Bulletin,1985,33(11),5068-5070. [View]
Pubchem: 163003467

No compound-protein relationship available.

Structure

SMILES: C=C1C(=O)OC(C12)C3C(CC2)CCC=C3

Level: 0

Mol. Weight: 346.42 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.57
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.64
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.59

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.58
Plasma Protein Binding
53.81
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
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
10.96
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.14
Biodegradation
Safe
Carcinogenesis
Toxic
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.93
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.44
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
-3.47
Rat (Acute)
3.47
Rat (Chronic Oral)
1.86
Fathead Minnow
4.12
Respiratory Disease
Safe
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Toxic

General Properties

Boiling Point
359.25
Hydration Free Energy
-5.97
Log(D) at pH=7.4
2.61
Log(P)
3.26
Log S
-3.64
Log(Vapor Pressure)
-6.68
Melting Point
120.12
pKa Acid
9.14
pKa Basic
4.76
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 0.8537
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8537
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8394
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8394
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7433
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7433
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7091
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7091

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