9-hydroxycostunolide - Compound Card

9-hydroxycostunolide

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9-hydroxycostunolide

Structure
Zoomed Structure
  • Family: Asteraceae-Compositae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sesquiterpene Lactone
Canonical Smiles C/C/1=C\[C@H]2OC(=O)C(=C)[C@@H]2CC(/C(=C/CC1)/C)O
InChI InChI=1S/C15H20O3/c1-9-5-4-6-10(2)13(16)8-12-11(3)15(17)18-14(12)7-9/h6-7,12-14,16H,3-5,8H2,1-2H3/b9-7+,10-6+/t12-,13?,14+/m0/s1
InChIKey CHKPFVHCBRAVJP-QUIRBFQOSA-N
Formula C15H20O3
HBA 3
HBD 1
MW 248.32
Rotatable Bonds 0
TPSA 46.53
LogP 2.52
Number Rings 2
Number Aromatic Rings 0
Heavy Atom Count 18
Formal Charge 0
Fraction CSP3 0.53
Exact Mass 248.14
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Pluchea dioscoridis Asteraceae-Compositae Plantae —

Showing of synonyms

  • Bohlmann F, Metwally MA, et al. (1984). Eudesmanolides from Pluchea dioscoridis. Phytochemistry,1984,23(9),1975-1977. [View]
Pubchem: 163030325
Nmrshiftdb2: 70059454

No compound-protein relationship available.

Structure

SMILES: C=C1C(=O)OC(C12)C=CCCC=CCC2

Level: 0

Mol. Weight: 204.27 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.82
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.23
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.64

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.49
Plasma Protein Binding
45.79
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
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
7.03
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.03
Biodegradation
Toxic
Carcinogenesis
Toxic
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.35
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
4.27
Micronucleos
Safe
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
3.11
Rat (Acute)
2.29
Rat (Chronic Oral)
1.93
Fathead Minnow
4.49
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Toxic

General Properties

Boiling Point
324.11
Hydration Free Energy
-7.13
Log(D) at pH=7.4
1.81
Log(P)
2.26
Log S
-2.99
Log(Vapor Pressure)
-5.36
Melting Point
109.84
pKa Acid
9.11
pKa Basic
5.4
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8811
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8811
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.8802
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.8802
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8800
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8800
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.8588
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.8588
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.8310
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.8310
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.8293
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.8293
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.8056
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.8056
Abscisic acid receptor PYR1 O49686 PYR1_ARATH Arabidopsis thaliana 3 0.7979
Abscisic acid receptor PYR1 O49686 PYR1_ARATH Arabidopsis thaliana 3 0.7979
Gibberellin receptor GID1A Q9MAA7 GID1A_ARATH Arabidopsis thaliana 3 0.7895
Gibberellin receptor GID1A Q9MAA7 GID1A_ARATH Arabidopsis thaliana 3 0.7895
Multidrug transporter MdfA P0AEY8 MDFA_ECOLI Escherichia coli 3 0.7881
Multidrug transporter MdfA P0AEY8 MDFA_ECOLI Escherichia coli 3 0.7881
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.7833
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.7833
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7734
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7734
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7649
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7649
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7562
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7562
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7556
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7556
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7437
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7437
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 2 0.7421
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 2 0.7421
Nuclear receptor ROR-gamma P51449 RORG_HUMAN Homo sapiens 2 0.7371
Nuclear receptor ROR-gamma P51449 RORG_HUMAN Homo sapiens 2 0.7371
Vitamin D-binding protein P02774 VTDB_HUMAN Homo sapiens 2 0.7331
Vitamin D-binding protein P02774 VTDB_HUMAN Homo sapiens 2 0.7331
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7273
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7273
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 2 0.7181
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 2 0.7181
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7164
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7164
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7161
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7161
Gibberellin receptor GID1 Q6L545 GID1_ORYSJ Oryza sativa subsp. japonica 3 0.7123
Gibberellin receptor GID1 Q6L545 GID1_ORYSJ Oryza sativa subsp. japonica 3 0.7123
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.7120
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.7120
Abscisic acid receptor PYL3 Q9SSM7 PYL3_ARATH Arabidopsis thaliana 3 0.7075
Abscisic acid receptor PYL3 Q9SSM7 PYL3_ARATH Arabidopsis thaliana 3 0.7075
Abscisic acid receptor PYL9 Q84MC7 PYL9_ARATH Arabidopsis thaliana 3 0.7060
Abscisic acid receptor PYL9 Q84MC7 PYL9_ARATH Arabidopsis thaliana 3 0.7060
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 3 0.7019
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 3 0.7019
Aldo-keto reductase family 1 member C1 Q04828 AK1C1_HUMAN Homo sapiens 2 0.7015
Aldo-keto reductase family 1 member C1 Q04828 AK1C1_HUMAN Homo sapiens 2 0.7015
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7001
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7001

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