7alpha,20(S)-dihydroxy-4,24(28)-ergostadien-3-one - Compound Card

7alpha,20(S)-dihydroxy-4,24(28)-ergostadien-3-one

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7alpha,20(S)-dihydroxy-4,24(28)-ergostadien-3-one

Structure
Zoomed Structure
  • Family: Plantae - Anacardiaceae
  • Kingdom: Plantae
  • Class: Steroid
    • Subclass: Phytosterol
Canonical Smiles C=C(C(C)C)CC[C@@](C1CC[C@@H]2[C@]1(C)CCC1[C@H]2[C@H](O)CC2=CC(=O)CC[C@]12C)(O)C
InChI InChI=1S/C28H44O3/c1-17(2)18(3)9-14-28(6,31)24-8-7-21-25-22(11-13-27(21,24)5)26(4)12-10-20(29)15-19(26)16-23(25)30/h15,17,21-25,30-31H,3,7-14,16H2,1-2,4-6H3/t21-,22?,23+,24?,25-,26-,27-,28-/m0/s1
InChIKey DJEAQUHZHIKDFT-ROIBBSGTSA-N
Formula C28H44O3
HBA 3
HBD 2
MW 428.66
Rotatable Bonds 5
TPSA 57.53
LogP 5.85
Number Rings 4
Number Aromatic Rings 0
Heavy Atom Count 31
Formal Charge 0
Fraction CSP3 0.82
Exact Mass 428.33
Number of Lipinski Rule Violations 1
# Species Family Kingdom NCBI Taxonomy ID
1 Antrocaryon klaineanum Anacardiaceae Plantae 289695

Showing of synonyms

  • Fouokeng Y, Akak CM, et al. (2017). The structure of antrocarine E, an ergostane isolated from Antrocaryon klaineanum Pierre (Anacardiaceae).. Fitoterapia,2017, 117, 61-64. [View] [PubMed]

No compound-protein relationship available.

Structure

SMILES: C1CCC(C12)CCC3C2CCC=4C3CCC(=O)C4

Level: 0

Mol. Weight: 428.66 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.72
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.51
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.69

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.51
Plasma Protein Binding
80.03
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
9.71
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.12
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.48
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
6.09
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
-38.1
Rat (Acute)
3.3
Rat (Chronic Oral)
1.83
Fathead Minnow
3.92
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
444.09
Hydration Free Energy
-3.54
Log(D) at pH=7.4
4.5
Log(P)
5.22
Log S
-5.44
Log(Vapor Pressure)
-8.19
Melting Point
163.73
pKa Acid
10.54
pKa Basic
6.38
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.9615
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.9615
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.9549
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.9549
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.9395
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.9395
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.9253
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.9253
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.9169
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.9169
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8722
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8722
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8428
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8428
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.8369
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.8369
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8358
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8358
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 4 0.8300
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 4 0.8300
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 4 0.8243
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 4 0.8243
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8191
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8191
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 4 0.8124
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 4 0.8124
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.8064
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.8064
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 4 0.8059
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 4 0.8059
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 4 0.8019
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 4 0.8019
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 4 0.8012
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 4 0.8012
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 4 0.8009
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 4 0.8009
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8001
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8001
Androgen receptor O97775 ANDR_PANTR Pan troglodytes 4 0.7984
Androgen receptor O97775 ANDR_PANTR Pan troglodytes 4 0.7984
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 4 0.7979
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 4 0.7979
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 4 0.7972
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 4 0.7972
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7963
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7963
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.7944
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 4 0.7944
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 4 0.7944
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.7944
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 4 0.7915
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 4 0.7915
Androgen receptor O97775 ANDR_PANTR Pan troglodytes 4 0.7906
Androgen receptor O97775 ANDR_PANTR Pan troglodytes 4 0.7906
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 4 0.7904
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 4 0.7904
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.7895
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.7895
Androgen receptor O97775 ANDR_PANTR Pan troglodytes 4 0.7888
Androgen receptor O97775 ANDR_PANTR Pan troglodytes 4 0.7888
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 4 0.7887
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7887
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 4 0.7887
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7887
Androgen receptor O97775 ANDR_PANTR Pan troglodytes 4 0.7886
Androgen receptor O97775 ANDR_PANTR Pan troglodytes 4 0.7886
Androgen receptor O97775 ANDR_PANTR Pan troglodytes 4 0.7869
Androgen receptor O97775 ANDR_PANTR Pan troglodytes 4 0.7869
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 3 0.7867
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 3 0.7867
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 4 0.7860
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 4 0.7860
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 4 0.7859
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 4 0.7859
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 4 0.7821
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 4 0.7821
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 4 0.7818
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 4 0.7818
Retinol-binding protein 1 P02696 RET1_RAT Rattus norvegicus 3 0.7808
Retinol-binding protein 1 P02696 RET1_RAT Rattus norvegicus 3 0.7808
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 4 0.7806
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 4 0.7806
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 4 0.7796
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 4 0.7796
Androgen receptor O97775 ANDR_PANTR Pan troglodytes 4 0.7764
Androgen receptor O97775 ANDR_PANTR Pan troglodytes 4 0.7764
Androgen receptor O97775 ANDR_PANTR Pan troglodytes 4 0.7750
Androgen receptor O97775 ANDR_PANTR Pan troglodytes 4 0.7750
Androgen receptor P19091 ANDR_MOUSE Mus musculus 4 0.7747
Androgen receptor P19091 ANDR_MOUSE Mus musculus 4 0.7747
Integrin alpha-L P20701 ITAL_HUMAN Homo sapiens 3 0.7725
Integrin alpha-L P20701 ITAL_HUMAN Homo sapiens 3 0.7725
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 4 0.7721
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 4 0.7721
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 4 0.7718
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 4 0.7718
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 3 0.7703
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 3 0.7703
Androgen receptor O97775 ANDR_PANTR Pan troglodytes 4 0.7664
Androgen receptor O97775 ANDR_PANTR Pan troglodytes 4 0.7664
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 4 0.7651
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 4 0.7651
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7647
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7647
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 3 0.7632
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 3 0.7632
Oxysterols receptor LXR-beta P55055 NR1H2_HUMAN Homo sapiens 3 0.7629
Oxysterols receptor LXR-beta P55055 NR1H2_HUMAN Homo sapiens 3 0.7629
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 4 0.7625
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 4 0.7625
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 4 0.7585
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 4 0.7585
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.7582
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.7582
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7519
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7519
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 4 0.7489
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 4 0.7489
NPC intracellular cholesterol transporter 1 O15118 NPC1_HUMAN Homo sapiens 3 0.7470
NPC intracellular cholesterol transporter 1 O15118 NPC1_HUMAN Homo sapiens 3 0.7470
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 4 0.7469
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 4 0.7469
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 4 0.7461
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 4 0.7461
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 4 0.7412
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 4 0.7412
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 4 0.7402
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 4 0.7402
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 4 0.7372
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 4 0.7372
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 4 0.7359
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 4 0.7359
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 4 0.7357
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 4 0.7357
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.7317
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.7317
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.7282
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.7282
Cholesterol side-chain cleavage enzyme, mitochondrial P00189 CP11A_BOVIN Bos taurus 3 0.7280
Cholesterol side-chain cleavage enzyme, mitochondrial P00189 CP11A_BOVIN Bos taurus 3 0.7280
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 3 0.7200
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 3 0.7200
Lanosterol 14-alpha-demethylase Q385E8 Q385E8_TRYB2 Trypanosoma brucei brucei 3 0.7181
Lanosterol 14-alpha-demethylase Q385E8 Q385E8_TRYB2 Trypanosoma brucei brucei 3 0.7181
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.7175
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.7175
Vitamin D3 receptor P13053 VDR_RAT Rattus norvegicus 3 0.7166
Vitamin D3 receptor P13053 VDR_RAT Rattus norvegicus 3 0.7166
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 3 0.7136
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 3 0.7136
Nuclear receptor ROR-alpha P35398 RORA_HUMAN Homo sapiens 4 0.7115
Nuclear receptor ROR-alpha P35398 RORA_HUMAN Homo sapiens 4 0.7115
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7105
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7105
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7080
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7080
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7042
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7042

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