5alpha-hydroxycostic acid - Compound Card

5alpha-hydroxycostic acid

Select a section from the left sidebar

5alpha-hydroxycostic 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-BPLDGKMQSA-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 Chiliadenus montanus Asteraceae Plantae 1458965
2 Jasonia montana Asteraceae Plantae 441235
3 Pluchea dioscoridis Asteraceae Plantae
4 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]
  • Hegazy MEF, Matsuda H, et al. (2014). Chemical constituents and their antibacterial and antifungal activity from the Egyptian herbal medicine Chiliadenus montanus. Phytochemistry,2014,103,154-161. [View] [PubMed]
  • 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

Antimicrobial

Absorption

Caco-2 (logPapp)
-4.71
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
-2.05

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.46
Plasma Protein Binding
54.01
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
4.09
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.5
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
3.38
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
-0.01
Rat (Acute)
2.36
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
325.81
Hydration Free Energy
-7.68
Log(D) at pH=7.4
0.24
Log(P)
2.9
Log S
-2.8
Log(Vapor Pressure)
-6.04
Melting Point
141.26
pKa Acid
3.94
pKa Basic
9.22
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 3 0.9497
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 3 0.9497
Prostaglandin reductase 2 Q8N8N7 PTGR2_HUMAN Homo sapiens 3 0.9309
Prostaglandin reductase 2 Q8N8N7 PTGR2_HUMAN Homo sapiens 3 0.9309
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.9288
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.9288
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.9093
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.9093
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.8981
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.8981
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8931
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8931
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.8925
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.8925
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.8913
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.8913
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.8909
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.8909
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.8877
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.8877
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.8803
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.8803
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8667
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8667
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8607
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8607
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8542
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8542
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8503
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8503
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.8462
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.8462
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.8060
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.8060
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7955
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7955
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7937
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7937
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7836
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7836
ADP-ribosylation factor 1 P84080 ARF1_BOVIN Bos taurus 3 0.7805
ADP-ribosylation factor 1 P84080 ARF1_BOVIN Bos taurus 3 0.7805
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7787
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7787
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7780
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7780
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.7748
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.7748
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7742
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7742
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7733
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7733
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7702
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7702
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7696
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7696
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7676
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7676
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7672
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7672
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7665
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7665
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7656
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7656
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.7655
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.7655
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7641
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7641
Nuclear receptor subfamily 1 group I member 3 O35627 NR1I3_MOUSE Mus musculus 2 0.7605
Nuclear receptor subfamily 1 group I member 3 O35627 NR1I3_MOUSE Mus musculus 2 0.7605
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.7603
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.7603
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7595
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7595
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7580
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7580
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7572
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7572
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7562
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7562
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7556
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7556
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7539
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7539
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7535
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7535
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7534
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7534
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7523
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7523
Androgen receptor O97775 ANDR_PANTR Pan troglodytes 3 0.7489
Androgen receptor O97775 ANDR_PANTR Pan troglodytes 3 0.7489
Soluble cytochrome b562 P0ABE7 C562_ECOLX Escherichia coli 2 0.7483
Soluble cytochrome b562 P0ABE7 C562_ECOLX Escherichia coli 2 0.7483
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7482
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7482
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7479
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7479
Androgen receptor O97775 ANDR_PANTR Pan troglodytes 3 0.7473
Androgen receptor O97775 ANDR_PANTR Pan troglodytes 3 0.7473
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7470
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7470
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7452
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7452
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.7438
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.7438
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7437
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7437
Androgen receptor O97775 ANDR_PANTR Pan troglodytes 3 0.7431
Androgen receptor O97775 ANDR_PANTR Pan troglodytes 3 0.7431
Androgen receptor O97775 ANDR_PANTR Pan troglodytes 3 0.7428
Androgen receptor O97775 ANDR_PANTR Pan troglodytes 3 0.7428
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7428
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7428
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7424
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7424
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7418
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7418
Androgen receptor O97775 ANDR_PANTR Pan troglodytes 3 0.7413
Androgen receptor O97775 ANDR_PANTR Pan troglodytes 3 0.7413
Androgen receptor P19091 ANDR_MOUSE Mus musculus 3 0.7404
Androgen receptor P19091 ANDR_MOUSE Mus musculus 3 0.7404
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7402
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7402
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7395
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7395
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7371
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7371
Androgen receptor O97775 ANDR_PANTR Pan troglodytes 3 0.7362
Androgen receptor O97775 ANDR_PANTR Pan troglodytes 3 0.7362
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7357
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7357
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.7336
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.7336
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7333
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7333
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7329
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7329
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7325
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7325
Androgen receptor O97775 ANDR_PANTR Pan troglodytes 3 0.7306
Androgen receptor O97775 ANDR_PANTR Pan troglodytes 3 0.7306
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7295
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7295
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7291
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7291
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7287
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7287
Androgen receptor O97775 ANDR_PANTR Pan troglodytes 3 0.7254
Androgen receptor O97775 ANDR_PANTR Pan troglodytes 3 0.7254
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7235
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7235
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 2 0.7222
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 2 0.7222
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 2 0.7209
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 2 0.7209
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7200
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7200
Avidin P02701 AVID_CHICK Gallus gallus 3 0.7193
Avidin P02701 AVID_CHICK Gallus gallus 3 0.7193
Glucocorticoid receptor P04150 GCR_HUMAN Homo sapiens 3 0.7185
Glucocorticoid receptor P04150 GCR_HUMAN Homo sapiens 3 0.7185
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7145
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7145
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7136
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7136
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7084
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7084
Nuclear receptor ROR-gamma P51449 RORG_HUMAN Homo sapiens 2 0.7059
Nuclear receptor ROR-gamma P51449 RORG_HUMAN Homo sapiens 2 0.7059
NPC intracellular cholesterol transporter 1 O15118 NPC1_HUMAN Homo sapiens 3 0.7037
NPC intracellular cholesterol transporter 1 O15118 NPC1_HUMAN Homo sapiens 3 0.7037
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7022
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7022

Download SDF