3alpha,5alpha-dihydroxycostic acid - Compound Card

3alpha,5alpha-dihydroxycostic acid

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3alpha,5alpha-dihydroxycostic acid

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sesquiterpene
Canonical Smiles OC(=O)C(=C)[C@@H]1CC[C@@]2([C@@](C1)(O)C(=C)CCC2)C
InChI InChI=1S/C15H22O3/c1-10-5-4-7-14(3)8-6-12(9-15(10,14)18)11(2)13(16)17/h12,18H,1-2,4-9H2,3H3,(H,16,17)/t12-,14-,15+/m1/s1
InChIKey UEQIFFFWXPAQCB-YUELXQCFSA-N
Formula C15H22O3
HBA 2
HBD 2
MW 250.34
Rotatable Bonds 2
TPSA 57.53
LogP 2.9
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 Jasonia montana Asteraceae Plantae 441235
2 Pluchea dioscoridis Asteraceae Plantae
3 Tarchonanthus camphoratus Asteraceae Plantae 41650

Showing of synonyms

  • Mahmoud AA (1997). 7-Epi-eudesmanes, eudesmanoic acids, eudesmanolides and other sesquiterpenenes from Pluchea dioscoridis. Phytochemistry,1997,45(8),1633-1638. [View]
  • Ahmed AA, Jakupovic J (1990). Sesqui- and monoterpenes from Jasonia montana. Phytochemistry,1990,29(11),3658-3661. [View]
  • Hegazy MEF, Tawfik WA, et al. (2015). Sesquiterpene acid derivatives from Tarchonanthus camphoratus. Research Journal of Pharmaceutical, Biological and Chemical Sciences,2015,6(1),659-663. [View]

No compound-protein relationship available.

Structure

SMILES: C=C1CCCC(C12)CCCC2

Level: 0

Mol. Weight: 250.34 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.72
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.54
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.06

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.46
Plasma Protein Binding
53.7
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
4.1
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.54
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
0.17
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
3.39
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
0.03
Rat (Acute)
2.38
Rat (Chronic Oral)
2.22
Fathead Minnow
3.92
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
326.05
Hydration Free Energy
-7.66
Log(D) at pH=7.4
0.16
Log(P)
2.94
Log S
-2.85
Log(Vapor Pressure)
-6.04
Melting Point
135.19
pKa Acid
3.96
pKa Basic
9.23
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.9515
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.9515
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.9386
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.9386
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.9364
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.9364
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.9359
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.9359
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.9335
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.9335
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.9316
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.9316
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.9309
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.9309
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.9264
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.9264
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 3 0.9088
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 3 0.9088
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8974
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8974
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.8962
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.8962
Aromatase P11511 CP19A_HUMAN Homo sapiens 3 0.8925
Aromatase P11511 CP19A_HUMAN Homo sapiens 3 0.8925
Prostaglandin reductase 2 Q8N8N7 PTGR2_HUMAN Homo sapiens 3 0.8739
Prostaglandin reductase 2 Q8N8N7 PTGR2_HUMAN Homo sapiens 3 0.8739
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8685
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8685
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.8602
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.8602
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.8596
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.8596
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.8543
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.8543
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.8439
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.8439
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.8429
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.8429
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8337
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8337
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.8283
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.8283
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.8251
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.8251
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.8226
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.8226
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.8034
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.8034
Phospholipase A2 P00593 PA21B_BOVIN Bos taurus 3 0.8001
Phospholipase A2 P00593 PA21B_BOVIN Bos taurus 3 0.8001
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.7963
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.7963
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7943
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7943
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7921
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7921
NPC intracellular cholesterol transporter 1 O15118 NPC1_HUMAN Homo sapiens 3 0.7910
NPC intracellular cholesterol transporter 1 O15118 NPC1_HUMAN Homo sapiens 3 0.7910
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7883
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7883
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7852
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7852
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7835
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7835
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7803
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7803
Androgen receptor O97775 ANDR_PANTR Pan troglodytes 3 0.7778
Androgen receptor O97775 ANDR_PANTR Pan troglodytes 3 0.7778
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7776
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7776
Androgen receptor O97775 ANDR_PANTR Pan troglodytes 3 0.7776
Androgen receptor O97775 ANDR_PANTR Pan troglodytes 3 0.7776
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7773
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7773
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7758
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7758
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7758
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7758
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7753
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7753
Androgen receptor O97775 ANDR_PANTR Pan troglodytes 3 0.7748
Androgen receptor O97775 ANDR_PANTR Pan troglodytes 3 0.7748
Androgen receptor O97775 ANDR_PANTR Pan troglodytes 3 0.7735
Androgen receptor O97775 ANDR_PANTR Pan troglodytes 3 0.7735
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.7725
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.7725
Androgen receptor O97775 ANDR_PANTR Pan troglodytes 3 0.7716
Androgen receptor O97775 ANDR_PANTR Pan troglodytes 3 0.7716
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7699
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7699
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7687
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7687
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7685
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7685
Abscisic acid receptor PYL3 Q9SSM7 PYL3_ARATH Arabidopsis thaliana 3 0.7678
Abscisic acid receptor PYL3 Q9SSM7 PYL3_ARATH Arabidopsis thaliana 3 0.7678
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.7664
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.7664
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7651
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7651
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7651
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7651
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7628
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7628
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7623
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7623
ADP-ribosylation factor 1 P84080 ARF1_BOVIN Bos taurus 3 0.7611
ADP-ribosylation factor 1 P84080 ARF1_BOVIN Bos taurus 3 0.7611
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7595
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7595
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7589
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7589
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7576
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7576
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7564
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7564
Androgen receptor O97775 ANDR_PANTR Pan troglodytes 3 0.7559
Androgen receptor O97775 ANDR_PANTR Pan troglodytes 3 0.7559
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7558
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7558
Androgen receptor O97775 ANDR_PANTR Pan troglodytes 3 0.7552
Androgen receptor O97775 ANDR_PANTR Pan troglodytes 3 0.7552
Androgen receptor O97775 ANDR_PANTR Pan troglodytes 3 0.7543
Androgen receptor O97775 ANDR_PANTR Pan troglodytes 3 0.7543
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7540
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7540
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7535
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7535
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7528
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7528
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7523
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7523
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7520
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7520
Androgen receptor P19091 ANDR_MOUSE Mus musculus 3 0.7513
Androgen receptor P19091 ANDR_MOUSE Mus musculus 3 0.7513
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7501
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7501
Glucocorticoid receptor P04150 GCR_HUMAN Homo sapiens 3 0.7500
Glucocorticoid receptor P04150 GCR_HUMAN Homo sapiens 3 0.7500
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7492
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7492
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7487
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7487
ADP-ribosylation factor 1 P84077 ARF1_HUMAN Homo sapiens 2 0.7465
ADP-ribosylation factor 1 P84077 ARF1_HUMAN Homo sapiens 2 0.7465
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7463
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7463
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7431
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7431
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7400
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7400
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7400
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7400
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.7398
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.7398
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7398
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7398
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7368
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7368
Nuclear receptor subfamily 1 group I member 3 O35627 NR1I3_MOUSE Mus musculus 2 0.7362
Nuclear receptor subfamily 1 group I member 3 O35627 NR1I3_MOUSE Mus musculus 2 0.7362
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7356
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7356
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7347
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7347
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7337
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7337
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7310
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7310
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7301
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7301
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7284
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7284
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7258
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7258
Retinol dehydratase Q26490 Q26490_SPOFR Spodoptera frugiperda 3 0.7236
Retinol dehydratase Q26490 Q26490_SPOFR Spodoptera frugiperda 3 0.7236
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7170
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7170
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7142
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7142
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7123
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7123
Nuclear receptor coactivator 2 Q15596 NCOA2_HUMAN Homo sapiens 3 0.7072
Nuclear receptor coactivator 2 Q15596 NCOA2_HUMAN Homo sapiens 3 0.7072
Aldo-keto reductase family 1 member C1 Q04828 AK1C1_HUMAN Homo sapiens 2 0.7063
Aldo-keto reductase family 1 member C1 Q04828 AK1C1_HUMAN Homo sapiens 2 0.7063
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 2 0.7057
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 2 0.7057
Fatty acid-binding protein 10-A, liver basic Q9I8L5 FA10A_DANRE Danio rerio 3 0.7025
Fatty acid-binding protein 10-A, liver basic Q9I8L5 FA10A_DANRE Danio rerio 3 0.7025
Glucocorticoid receptor P04150 GCR_HUMAN Homo sapiens 3 0.7017
Glucocorticoid receptor P04150 GCR_HUMAN Homo sapiens 3 0.7017

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