20S-hydroxyergosta-4,6,24(28)-trien-3-one - Compound Card

20S-hydroxyergosta-4,6,24(28)-trien-3-one

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20S-hydroxyergosta-4,6,24(28)-trien-3-one

Structure
Zoomed Structure
  • Family: Plantae - Anacardiaceae
  • Kingdom: Plantae
  • Class: Steroid
    • Subclass: Phytosterol
Canonical Smiles C=C(C(C)C)CC[C@@](C1CCC2[C@]1(C)CCC1C2C=CC2=CC(=O)CC[C@]12C)(O)C
InChI InChI=1S/C28H42O2/c1-18(2)19(3)11-16-28(6,30)25-10-9-23-22-8-7-20-17-21(29)12-14-26(20,4)24(22)13-15-27(23,25)5/h7-8,17-18,22-25,30H,3,9-16H2,1-2,4-6H3/t22?,23?,24?,25?,26-,27-,28-/m0/s1
InChIKey OLCPAMPJEUEVSA-IEBGXPSSSA-N
Formula C28H42O2
HBA 2
HBD 1
MW 410.64
Rotatable Bonds 5
TPSA 37.3
LogP 6.65
Number Rings 4
Number Aromatic Rings 0
Heavy Atom Count 30
Formal Charge 0
Fraction CSP3 0.75
Exact Mass 410.32
Number of Lipinski Rule Violations 1
# Species Family Kingdom NCBI Taxonomy ID
1 Antrocaryon klaineanum Anacardiaceae Plantae 289695

Showing of synonyms

  • DouanlaPD, Tabopda TK, et al. (2015). Antrocarines A-F, antiplasmodial ergostane steroids from the stem bark of Antrocaryon klaineanum.. Phytochemistry,2015, 117, 521-526. [View] [PubMed]

No compound-protein relationship available.

Structure

SMILES: C1CCC(C12)CCC3C2C=CC=4C3CCC(=O)C4

Level: 0

Mol. Weight: 410.64 g/mol

Anti-plasmodial

Absorption

Caco-2 (logPapp)
-4.74
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.6
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.71

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.89
Plasma Protein Binding
85.32
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
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
Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
5.91
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.26
Biodegradation
Safe
Carcinogenesis
Toxic
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.86
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
6.44
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
-25.88
Rat (Acute)
2.6
Rat (Chronic Oral)
1.71
Fathead Minnow
4.5
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
429.15
Hydration Free Energy
-3.76
Log(D) at pH=7.4
5.24
Log(P)
5.86
Log S
-6.37
Log(Vapor Pressure)
-7.41
Melting Point
145.57
pKa Acid
11.28
pKa Basic
5.81
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.9617
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.9617
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.9129
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.9129
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.8991
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.8991
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8915
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8915
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8803
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8803
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.8729
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.8729
Nuclear receptor subfamily 1 group I member 3 O35627 NR1I3_MOUSE Mus musculus 3 0.8662
Nuclear receptor subfamily 1 group I member 3 O35627 NR1I3_MOUSE Mus musculus 3 0.8662
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.8268
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.8268
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.8153
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.8153
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.8111
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.8111
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8109
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8109
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.8087
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.8087
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 4 0.7983
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 4 0.7983
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7979
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7979
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7929
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7929
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7929
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7929
Retinol-binding protein 1 P02696 RET1_RAT Rattus norvegicus 3 0.7927
Retinol-binding protein 1 P02696 RET1_RAT Rattus norvegicus 3 0.7927
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 4 0.7856
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 4 0.7856
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7842
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7842
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.7803
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.7803
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 3 0.7788
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 3 0.7788
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 4 0.7744
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 4 0.7744
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 4 0.7726
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 4 0.7726
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 4 0.7698
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 4 0.7698
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7677
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7677
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7665
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7665
NPC intracellular cholesterol transporter 1 O15118 NPC1_HUMAN Homo sapiens 3 0.7618
NPC intracellular cholesterol transporter 1 O15118 NPC1_HUMAN Homo sapiens 3 0.7618
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 4 0.7614
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 4 0.7614
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 4 0.7607
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 4 0.7607
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 4 0.7594
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 4 0.7594
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 4 0.7568
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 4 0.7568
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 4 0.7562
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 4 0.7562
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 4 0.7552
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 4 0.7552
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7551
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7551
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 4 0.7534
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 4 0.7534
Androgen receptor P19091 ANDR_MOUSE Mus musculus 4 0.7525
Androgen receptor P19091 ANDR_MOUSE Mus musculus 4 0.7525
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 4 0.7514
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 4 0.7514
Retinol dehydratase Q26490 Q26490_SPOFR Spodoptera frugiperda 3 0.7492
Retinol dehydratase Q26490 Q26490_SPOFR Spodoptera frugiperda 3 0.7492
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 3 0.7488
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 3 0.7488
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 3 0.7469
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 3 0.7469
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 4 0.7437
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 4 0.7437
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7409
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7409
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 4 0.7400
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 4 0.7400
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 4 0.7395
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 4 0.7395
Androgen receptor O97775 ANDR_PANTR Pan troglodytes 4 0.7390
Androgen receptor O97775 ANDR_PANTR Pan troglodytes 4 0.7390
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7367
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7367
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 4 0.7356
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 4 0.7356
Aldo-keto reductase family 1 member C1 Q04828 AK1C1_HUMAN Homo sapiens 3 0.7350
Aldo-keto reductase family 1 member C1 Q04828 AK1C1_HUMAN Homo sapiens 3 0.7350
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7334
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7334
Androgen receptor O97775 ANDR_PANTR Pan troglodytes 4 0.7332
Androgen receptor O97775 ANDR_PANTR Pan troglodytes 4 0.7332
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 4 0.7321
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 4 0.7321
Androgen receptor O97775 ANDR_PANTR Pan troglodytes 4 0.7317
Androgen receptor O97775 ANDR_PANTR Pan troglodytes 4 0.7317
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.7308
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.7308
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 4 0.7288
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 4 0.7288
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 4 0.7269
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 4 0.7269
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 4 0.7260
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 4 0.7260
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 4 0.7248
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 4 0.7248
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 4 0.7239
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 4 0.7239
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 4 0.7225
Cholesterol side-chain cleavage enzyme, mitochondrial P05108 CP11A_HUMAN Homo sapiens 3 0.7225
Cholesterol side-chain cleavage enzyme, mitochondrial P05108 CP11A_HUMAN Homo sapiens 3 0.7225
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 4 0.7225
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 4 0.7215
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 4 0.7215
Androgen receptor O97775 ANDR_PANTR Pan troglodytes 4 0.7208
Androgen receptor O97775 ANDR_PANTR Pan troglodytes 4 0.7208
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 3 0.7143
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 3 0.7143
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7134
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7134
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7130
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7130
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 4 0.7102
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 4 0.7102
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.7096
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.7096
Lanosterol 14-alpha demethylase CYP51 P10614 CP51_YEAST Saccharomyces cerevisiae 3 0.7079
Lanosterol 14-alpha demethylase CYP51 P10614 CP51_YEAST Saccharomyces cerevisiae 3 0.7079
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 4 0.7073
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 4 0.7073
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 4 0.7067
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 4 0.7067
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7055
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7055
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 3 0.7033
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 3 0.7033
Gastrotropin P51161 FABP6_HUMAN Homo sapiens 3 0.7032
Gastrotropin P51161 FABP6_HUMAN Homo sapiens 3 0.7032
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.7007
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.7007

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