5beta-hydroxy-4-oxo-11(13)- dehydroiphionan-12-oic acid - Compound Card

5beta-hydroxy-4-oxo-11(13)- dehydroiphionan-12-oic acid

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5beta-hydroxy-4-oxo-11(13)- dehydroiphionan-12-oic acid

Structure
Zoomed Structure
  • Family: Asteraceae-Compositae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sesquiterpene
Canonical Smiles C=C([C@@H]1CC[C@@]2([C@@](C1)(O)C(CC2)C(=O)C)C)C(=O)O
InChI InChI=1S/C15H22O4/c1-9(13(17)18)11-4-6-14(3)7-5-12(10(2)16)15(14,19)8-11/h11-12,19H,1,4-8H2,2-3H3,(H,17,18)/t11-,12?,14+,15+/m1/s1
InChIKey YLMSJTAFOFIDRW-PYZCBOGGSA-N
Formula C15H22O4
HBA 3
HBD 2
MW 266.34
Rotatable Bonds 3
TPSA 74.6
LogP 2.16
Number Rings 2
Number Aromatic Rings 0
Heavy Atom Count 19
Formal Charge 0
Fraction CSP3 0.73
Exact Mass 266.15
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Jasonia candicans Asteraceae-Compositae Plantae 557631

Showing of synonyms

  • Ahmed AA, Mahmoud AA (1998). Jasonol, a rare tricyclic eudesmane sesquiterpene and six other new sesquiterpenoids from Jasonia candicans. Tetrahedron,1998,54,8141-8152. [View]
Pubchem: 15161369

No compound-protein relationship available.

Structure

SMILES: C1CCC(C12)CCCC2

Level: 0

Mol. Weight: 124.23 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.79
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.66
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.83

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.45
Plasma Protein Binding
51.8
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
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
4.19
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.84
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.64
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
2.9
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
-0.41
Rat (Acute)
2.1
Rat (Chronic Oral)
2.25
Fathead Minnow
3.89
Respiratory Disease
Safe
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
341.15
Hydration Free Energy
-8.7
Log(D) at pH=7.4
-0.71
Log(P)
1.66
Log S
-2.05
Log(Vapor Pressure)
-6.61
Melting Point
157.2
pKa Acid
3.68
pKa Basic
8.57
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Branched-chain-amino-acid aminotransferase, mitochondrial O15382 BCAT2_HUMAN Homo sapiens 3 0.8782
Branched-chain-amino-acid aminotransferase, mitochondrial O15382 BCAT2_HUMAN Homo sapiens 3 0.8782
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.8647
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.8647
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.8581
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.8581
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.8516
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.8516
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8344
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8344
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.8258
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.8258
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.8010
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.8010
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7974
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7974
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7973
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7973
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7972
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7972
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.7943
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.7943
Streptavidin P22629 SAV_STRAV Streptomyces avidinii 3 0.7841
Streptavidin P22629 SAV_STRAV Streptomyces avidinii 3 0.7841
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7679
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7679
Prostaglandin reductase 2 Q8N8N7 PTGR2_HUMAN Homo sapiens 3 0.7656
Prostaglandin reductase 2 Q8N8N7 PTGR2_HUMAN Homo sapiens 3 0.7656
3-alpha-(or 20-beta)-hydroxysteroid dehydrogenase P19992 HSD_STREX Streptomyces exfoliatus 3 0.7573
3-alpha-(or 20-beta)-hydroxysteroid dehydrogenase P19992 HSD_STREX Streptomyces exfoliatus 3 0.7573
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7518
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7518
N-alpha-acetyltransferase 50 Q9GZZ1 NAA50_HUMAN Homo sapiens 3 0.7485
N-alpha-acetyltransferase 50 Q9GZZ1 NAA50_HUMAN Homo sapiens 3 0.7485
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7466
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7466
Streptavidin P22629 SAV_STRAV Streptomyces avidinii 3 0.7439
Streptavidin P22629 SAV_STRAV Streptomyces avidinii 3 0.7439
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7315
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7315
Streptavidin P22629 SAV_STRAV Streptomyces avidinii 3 0.7313
Streptavidin P22629 SAV_STRAV Streptomyces avidinii 3 0.7313
NPC intracellular cholesterol transporter 1 O15118 NPC1_HUMAN Homo sapiens 3 0.7282
NPC intracellular cholesterol transporter 1 O15118 NPC1_HUMAN Homo sapiens 3 0.7282
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 2 0.7241
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 2 0.7241
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7199
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7199
Gastrotropin Q6IMW5 Q6IMW5_DANRE Danio rerio 2 0.7095
Gastrotropin Q6IMW5 Q6IMW5_DANRE Danio rerio 2 0.7095
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7066
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7066
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7056
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7056
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7023
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7023
Fatty acid-binding protein 10-A, liver basic Q9I8L5 FA10A_DANRE Danio rerio 3 0.7007
Fatty acid-binding protein 10-A, liver basic Q9I8L5 FA10A_DANRE Danio rerio 3 0.7007

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