1beta-angeloyloxy-9alpha-hydroxy-alpha-cyclocostunolide - Compound Card

1beta-angeloyloxy-9alpha-hydroxy-alpha-cyclocostunolide

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1beta-angeloyloxy-9alpha-hydroxy-alpha-cyclocostunolide

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sesquiterpene Lactone
Canonical Smiles C/C=C(\C(=O)O[C@H]1C[C@@H]2O[C@@]2([C@H]2[C@@]1(C)[C@H](O)C[C@@H]1[C@@H]2OC(=O)C1=C)C)/C
InChI InChI=1S/C20H26O6/c1-6-9(2)17(22)24-13-8-14-20(5,26-14)16-15-11(10(3)18(23)25-15)7-12(21)19(13,16)4/h6,11-16,21H,3,7-8H2,1-2,4-5H3/b9-6-/t11-,12+,13-,14-,15-,16+,19-,20-/m0/s1
InChIKey LJFIXEDWUIJMPO-VMPDBILPSA-N
Formula C20H26O6
HBA 6
HBD 1
MW 362.42
Rotatable Bonds 2
TPSA 85.36
LogP 1.91
Number Rings 4
Number Aromatic Rings 0
Heavy Atom Count 26
Formal Charge 0
Fraction CSP3 0.7
Exact Mass 362.17
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Pluchea dioscoridis Asteraceae Plantae —

Showing of synonyms

  • Omar AA, Sarc TM, et al. (1983). A eudesmanolide from Pluchea dioscoridis. Phytochemistry,1983,22(3),779-780. [View]
Pubchem: 162889336
Nmrshiftdb2: 70080107

No compound-protein relationship available.

Structure

SMILES: O=C(O1)C(=C)C(CC2)C1C3C2CCC(O4)C34

Level: 0

Mol. Weight: 362.42 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.14
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.7
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.96

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.31
Plasma Protein Binding
37.89
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
14.84
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.52
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.88
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
5.23
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
-6.53
Rat (Acute)
4.79
Rat (Chronic Oral)
1.67
Fathead Minnow
3.92
Respiratory Disease
Safe
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Toxic

General Properties

Boiling Point
392.34
Hydration Free Energy
-5.74
Log(D) at pH=7.4
1.66
Log(P)
1.99
Log S
-3.0
Log(Vapor Pressure)
-7.27
Melting Point
127.27
pKa Acid
6.06
pKa Basic
3.34
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 4 0.8660
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 4 0.8660
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7974
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7974
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7797
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7797
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7731
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7731
Retinol-binding protein 1 P02696 RET1_RAT Rattus norvegicus 3 0.7556
Retinol-binding protein 1 P02696 RET1_RAT Rattus norvegicus 3 0.7556
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7491
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7491
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7416
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7416
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 2 0.7222
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 2 0.7222
Vitamin D3 receptor P13053 VDR_RAT Rattus norvegicus 3 0.7178
Vitamin D3 receptor P13053 VDR_RAT Rattus norvegicus 3 0.7178
Retinol-binding protein 1 P02696 RET1_RAT Rattus norvegicus 3 0.7173
Retinol-binding protein 1 P02696 RET1_RAT Rattus norvegicus 3 0.7173
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 2 0.7081
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 2 0.7081

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