1beta-hydroxycostic acid - Compound Card

1beta-hydroxycostic acid

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1beta-hydroxycostic acid

Structure
Zoomed Structure
  • Family: Asteraceae-Compositae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sesquiterpene
Canonical Smiles C=C1CC[C@H]([C@]2([C@H]1C[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/h11-13,16H,1-2,4-8H2,3H3,(H,17,18)/t11-,12+,13-,15-/m1/s1
InChIKey GQPJZGWMHPSVIQ-QVHKTLOISA-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-Compositae 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: 14633051
Nmrshiftdb2: 60022692

No compound-protein relationship available.

Structure

SMILES: C=C1CCCC(C12)CCCC2

Level: 0

Mol. Weight: 150.26 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.67
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.49
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.43

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.56
Plasma Protein Binding
57.69
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
4.69
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.53
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
-0.46
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
2.87
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
-1.76
Rat (Acute)
2.63
Rat (Chronic Oral)
2.51
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
334.36
Hydration Free Energy
-7.26
Log(D) at pH=7.4
0.03
Log(P)
2.96
Log S
-2.87
Log(Vapor Pressure)
-6.22
Melting Point
134.35
pKa Acid
4.34
pKa Basic
8.12
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 3 0.9158
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 3 0.9158
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.9157
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.9157
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.8906
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.8906
Prostaglandin reductase 2 Q8N8N7 PTGR2_HUMAN Homo sapiens 3 0.8841
Prostaglandin reductase 2 Q8N8N7 PTGR2_HUMAN Homo sapiens 3 0.8841
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8788
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8788
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8560
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8560
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.8365
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.8365
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.8205
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.8205
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.8179
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.8179
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8122
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8122
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7998
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7998
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7996
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7996
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 D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7699
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7699
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7692
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7692
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.7671
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.7671
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7650
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7650
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7641
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7641
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7585
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7585
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7487
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7487
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7463
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7463
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7392
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7392
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.7383
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.7383
ADP-ribosylation factor 1 P84080 ARF1_BOVIN Bos taurus 3 0.7374
ADP-ribosylation factor 1 P84080 ARF1_BOVIN Bos taurus 3 0.7374
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7364
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7364
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7289
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7289
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 2 0.7276
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 2 0.7276
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7275
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7275
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7220
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7220
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7200
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7200
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7200
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7200
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7176
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7176
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7126
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7126
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7115
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7115
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 2 0.7080
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 2 0.7080
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 2 0.7067
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 2 0.7067
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7011
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7011

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