1beta-hydroxyisocostic acid - Compound Card

1beta-hydroxyisocostic acid

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1beta-hydroxyisocostic acid

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sesquiterpene
Canonical Smiles CC1=CC[C@H]([C@]2(C1C[C@@H](CC2)C(=C)C(=O)O)C)O
InChI InChI=1S/C15H22O3/c1-9-4-5-13(16)15(3)7-6-11(8-12(9)15)10(2)14(17)18/h4,11-13,16H,2,5-8H2,1,3H3,(H,17,18)/t11-,12?,13-,15-/m1/s1
InChIKey CUDLWLJJPCDTLE-HTYKBFHYSA-N
Formula C15H22O3
HBA 2
HBD 2
MW 250.34
Rotatable Bonds 2
TPSA 57.53
LogP 2.76
Number Rings 2
Number Aromatic Rings 0
Heavy Atom Count 18
Formal Charge 0
Fraction CSP3 0.67
Exact Mass 250.16
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Xanthium pungens Asteraceae Plantae 1979456

Showing of synonyms

  • Ahmed AA, Jakupovic J, et al. (1990). Sesquiterpene lactones from Xanthium pungens. Phytochemistry,1990,29(7),2211-2215. [View]
Pubchem: 14633047

No compound-protein relationship available.

Structure

SMILES: C1=CCCC(C12)CCCC2

Level: 0

Mol. Weight: 250.34 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.69
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.45
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.54

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.62
Plasma Protein Binding
49.94
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
4.32
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.18
Biodegradation
Safe
Carcinogenesis
Toxic
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
-0.55
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
3.17
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
0.06
Rat (Acute)
2.42
Rat (Chronic Oral)
2.46
Fathead Minnow
3.93
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
331.98
Hydration Free Energy
-7.78
Log(D) at pH=7.4
0.25
Log(P)
3.25
Log S
-2.85
Log(Vapor Pressure)
-5.94
Melting Point
142.09
pKa Acid
4.37
pKa Basic
8.07
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 3 0.9322
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 3 0.9322
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.8604
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.8604
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8584
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8584
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8518
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8518
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8353
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8353
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.8313
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.8313
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.8167
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.8167
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.8012
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.8012
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7859
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7859
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7774
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7774
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7759
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7759
Prostaglandin reductase 2 Q8N8N7 PTGR2_HUMAN Homo sapiens 3 0.7752
Prostaglandin reductase 2 Q8N8N7 PTGR2_HUMAN Homo sapiens 3 0.7752
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7703
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7703
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.7626
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.7626
Streptavidin P22629 SAV_STRAV Streptomyces avidinii 3 0.7516
Streptavidin P22629 SAV_STRAV Streptomyces avidinii 3 0.7516
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7509
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7509
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7434
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7434
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7426
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7426
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7361
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7361
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7222
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7222
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7210
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7210
Streptavidin P22629 SAV_STRAV Streptomyces avidinii 3 0.7115
Streptavidin P22629 SAV_STRAV Streptomyces avidinii 3 0.7115
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7102
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7102
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7077
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7077
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7069
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7069
Streptavidin P22629 SAV_STRAV Streptomyces avidinii 2 0.7051
Streptavidin P22629 SAV_STRAV Streptomyces avidinii 2 0.7051
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.7043
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.7043
Predicted acetyltransferase Q97ML2 Q97ML2_CLOAB Clostridium acetobutylicum 3 0.7042
Predicted acetyltransferase Q97ML2 Q97ML2_CLOAB Clostridium acetobutylicum 3 0.7042
Abscisic acid receptor PYL9 Q84MC7 PYL9_ARATH Arabidopsis thaliana 3 0.7022
Abscisic acid receptor PYL9 Q84MC7 PYL9_ARATH Arabidopsis thaliana 3 0.7022

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