Ergosterol-5,8-endoperoxide - Compound Card

Ergosterol-5,8-endoperoxide

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Ergosterol-5,8-endoperoxide

Structure
Zoomed Structure
  • Family: Lamiaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Triterpenoid
Canonical Smiles CC(C/C=C/C[C@H]1CC[C@@H]2[C@]1(C)CCC1[C@]32OO[C@]2([C@]1(C)CCC(C2)O)C=C3)C
InChI InChI=1S/C26H40O3/c1-18(2)7-5-6-8-19-9-10-21-23(19,3)13-12-22-24(4)14-11-20(27)17-25(24)15-16-26(21,22)29-28-25/h5-6,15-16,18-22,27H,7-14,17H2,1-4H3/b6-5+/t19-,20?,21+,22?,23+,24+,25+,26-/m0/s1
InChIKey OAKBMFLEIZVVAO-VLBAKGEXSA-N
Formula C26H40O3
HBA 3
HBD 1
MW 400.6
Rotatable Bonds 4
TPSA 38.69
LogP 5.98
Number Rings 6
Number Aromatic Rings 0
Heavy Atom Count 29
Formal Charge 0
Fraction CSP3 0.85
Exact Mass 400.3
Number of Lipinski Rule Violations 1
# Species Family Kingdom NCBI Taxonomy ID
1 Ajuga remota Lamiaceae Plantae 38595

Showing of synonyms

  • Kuria KA, Chepkwony H, et al. (2002). The antiplasmodial activity of isolates from Ajuga remota.. Journal of Natural Products,2002,65(5),789-793. [View] [PubMed]
Pubchem: 10386291

No compound-protein relationship available.

Structure

SMILES: C1CCC(C1C234)CCC3C5C(OO4)(C=C2)CCCC5

Level: 0

Mol. Weight: 260.38 g/mol

Anti-plasmodial

Absorption

Caco-2 (logPapp)
-4.7
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.51
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.82

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.49
Plasma Protein Binding
70.33
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
Non-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
13.27
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.89
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.86
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
5.76
Micronucleos
Safe
NR-AhR
Safe
NR-AR
Toxic
NR-AR-LBD
Safe
NR-Aromatase
Safe
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Toxic
NR-PPAR-gamma
Safe
NR-TR
Toxic
T. Pyriformis
-25.13
Rat (Acute)
2.45
Rat (Chronic Oral)
1.44
Fathead Minnow
3.92
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
422.5
Hydration Free Energy
-4.04
Log(D) at pH=7.4
5.19
Log(P)
6.52
Log S
-6.27
Log(Vapor Pressure)
-7.32
Melting Point
126.43
pKa Acid
10.23
pKa Basic
6.94
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Nuclear receptor subfamily 1 group I member 3 O35627 NR1I3_MOUSE Mus musculus 3 0.9225
Nuclear receptor subfamily 1 group I member 3 O35627 NR1I3_MOUSE Mus musculus 3 0.9225
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8913
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8913
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.8856
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.8856
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8844
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8844
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8697
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8697
Lanosterol 14-alpha-demethylase Q385E8 Q385E8_TRYB2 Trypanosoma brucei brucei 4 0.8668
Lanosterol 14-alpha-demethylase Q385E8 Q385E8_TRYB2 Trypanosoma brucei brucei 4 0.8668
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.8638
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.8638
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8621
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8621
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8620
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8620
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.8460
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.8460
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8430
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8430
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8424
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8424
Beta-lactoglobulin P02754 LACB_BOVIN Bos taurus 3 0.8359
Beta-lactoglobulin P02754 LACB_BOVIN Bos taurus 3 0.8359
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.8358
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.8358
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8322
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8322
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 3 0.8288
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 3 0.8288
Steroid C26-monooxygenase P9WPP1 CP125_MYCTU Mycobacterium tuberculosis 3 0.8246
Steroid C26-monooxygenase P9WPP1 CP125_MYCTU Mycobacterium tuberculosis 3 0.8246
Retinol dehydratase Q26490 Q26490_SPOFR Spodoptera frugiperda 3 0.8186
Retinol dehydratase Q26490 Q26490_SPOFR Spodoptera frugiperda 3 0.8186
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8158
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8158
Cholesterol side-chain cleavage enzyme, mitochondrial P05108 CP11A_HUMAN Homo sapiens 3 0.8132
Cholesterol side-chain cleavage enzyme, mitochondrial P05108 CP11A_HUMAN Homo sapiens 3 0.8132
Steroid C26-monooxygenase P9WPP1 CP125_MYCTU Mycobacterium tuberculosis 3 0.8124
Steroid C26-monooxygenase P9WPP1 CP125_MYCTU Mycobacterium tuberculosis 3 0.8124
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 3 0.8050
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 3 0.8050
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.8003
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.8003
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7973
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7973
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 3 0.7956
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 3 0.7956
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7856
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7856
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7723
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7723
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7702
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7702
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 3 0.7559
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 3 0.7559
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7541
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7541
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7484
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7484
Vitamin D(3) 25-hydroxylase C4B644 CPVDH_PSEAH Pseudonocardia autotrophica 3 0.7455
Vitamin D(3) 25-hydroxylase C4B644 CPVDH_PSEAH Pseudonocardia autotrophica 3 0.7455
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7411
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7411
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7406
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7406
Gastrotropin P51161 FABP6_HUMAN Homo sapiens 3 0.7344
Gastrotropin P51161 FABP6_HUMAN Homo sapiens 3 0.7344
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7304
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7304
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.7272
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.7272
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7266
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7266
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7233
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7233
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7231
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7231
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7229
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7229
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7219
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7219
4,4'-diapophytoene synthase A9JQL9 CRTM_STAAU Staphylococcus aureus 2 0.7203
4,4'-diapophytoene synthase A9JQL9 CRTM_STAAU Staphylococcus aureus 2 0.7203
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7202
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7202
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7192
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7192
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7184
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7184
Androgen receptor O97775 ANDR_PANTR Pan troglodytes 3 0.7157
Androgen receptor O97775 ANDR_PANTR Pan troglodytes 3 0.7157
Androgen receptor O97775 ANDR_PANTR Pan troglodytes 3 0.7150
Androgen receptor O97775 ANDR_PANTR Pan troglodytes 3 0.7150
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7122
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7122
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7118
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7118
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7113
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7113
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7106
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7106
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7104
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7104
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7099
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7099
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7091
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7091
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7056
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7056
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7032
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7032
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7022
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7022

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