3alpha,4alpha-epoxy-1alpha-hydroxy-9alpha-isovaleryloxy-alpha-cyclocostunolide - Compound Card

3alpha,4alpha-epoxy-1alpha-hydroxy-9alpha-isovaleryloxy-alpha-cyclocostunolide

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3alpha,4alpha-epoxy-1alpha-hydroxy-9alpha-isovaleryloxy-alpha-cyclocostunolide

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sesquiterpene Lactone
Canonical Smiles CC(CC(=O)O[C@@H]1CC2C(=C)C(=O)O[C@@H]2[C@@H]2C1(C)[C@@H](O)C[C@@H]1[C@@]2(C)O1)C
InChI InChI=1S/C20H28O6/c1-9(2)6-15(22)24-13-7-11-10(3)18(23)25-16(11)17-19(13,4)12(21)8-14-20(17,5)26-14/h9,11-14,16-17,21H,3,6-8H2,1-2,4-5H3/t11?,12-,13+,14+,16-,17+,19?,20+/m0/s1
InChIKey CBQFGDQOTBNMNS-UOOYFLOOSA-N
Formula C20H28O6
HBA 6
HBD 1
MW 364.44
Rotatable Bonds 3
TPSA 85.36
LogP 1.99
Number Rings 4
Number Aromatic Rings 0
Heavy Atom Count 26
Formal Charge 0
Fraction CSP3 0.8
Exact Mass 364.19
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: 162936387

No compound-protein relationship available.

Structure

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

Level: 0

Mol. Weight: 364.44 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.06
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.66
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.79

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.3
Plasma Protein Binding
35.29
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
15.63
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.93
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.81
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
5.08
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
-2.45
Rat (Acute)
5.1
Rat (Chronic Oral)
1.7
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
395.43
Hydration Free Energy
-5.67
Log(D) at pH=7.4
1.77
Log(P)
2.44
Log S
-3.15
Log(Vapor Pressure)
-6.81
Melting Point
114.4
pKa Acid
5.93
pKa Basic
4.3
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.8532
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.8532
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.8515
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.8515
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 4 0.8282
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 4 0.8282
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7891
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7891
Retinol dehydratase Q26490 Q26490_SPOFR Spodoptera frugiperda 3 0.7788
Retinol dehydratase Q26490 Q26490_SPOFR Spodoptera frugiperda 3 0.7788
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.7429
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.7429
Beta-elicitin cryptogein P15570 ELIB_PHYCR Phytophthora cryptogea 3 0.7402
Beta-elicitin cryptogein P15570 ELIB_PHYCR Phytophthora cryptogea 3 0.7402
Lysozyme C II P11941 LYSC2_ONCMY Oncorhynchus mykiss 3 0.7346
Lysozyme C II P11941 LYSC2_ONCMY Oncorhynchus mykiss 3 0.7346
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7304
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7304
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7247
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7247
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7159
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7159
Vitamin D3 receptor P13053 VDR_RAT Rattus norvegicus 3 0.7135
Vitamin D3 receptor P13053 VDR_RAT Rattus norvegicus 3 0.7135
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7122
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7122
Trichothecene 15-O-acetyltransferase TRI3 Q9C1B7 TRI3_FUSSP Fusarium sporotrichioides 3 0.7061
Trichothecene 15-O-acetyltransferase TRI3 Q9C1B7 TRI3_FUSSP Fusarium sporotrichioides 3 0.7061
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7037
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7037
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7007
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7007

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