7,20S-dihydroxyergosta-4,24(28)-dien-3-one - Compound Card

7,20S-dihydroxyergosta-4,24(28)-dien-3-one

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7,20S-dihydroxyergosta-4,24(28)-dien-3-one

Structure
Zoomed Structure
  • Family: Anacardiaceae
  • Kingdom: Plantae
  • Class: Steroid
    • Subclass: Phytosterol
Canonical Smiles C=C(C(C)C)CC[C@@](C1CCC2[C@]1(C)CCC1C2[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+/m1/s1
InChIKey DJEAQUHZHIKDFT-JPFHJHKFSA-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
2 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]
  • Fouokeng Y, Feusso HMF, et al. (2019). In vitro antimalarial, antitrypanosomal and HIV-1 integrase inhibitory activities of two Cameroonian medicinal plants: Antrocaryon klaineanum (Anacardiaceae) and Diospyros conocarpa (Ebenaceae).. South African Journal of Botany, 2019, 122, 510-517. [View]

No compound-protein relationship available.

Structure

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

Level: 0

Mol. Weight: 244.38 g/mol

Anti-plasmodial

Absorption

Caco-2 (logPapp)
-4.71
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
-2.7

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.51
Plasma Protein Binding
76.61
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
9.52
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.36
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
Safe
Daphnia Maga
6.14
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
-38.32
Rat (Acute)
3.3
Rat (Chronic Oral)
1.83
Fathead Minnow
4.07
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
438.84
Hydration Free Energy
-3.55
Log(D) at pH=7.4
4.49
Log(P)
5.14
Log S
-5.45
Log(Vapor Pressure)
-8.04
Melting Point
162.23
pKa Acid
10.52
pKa Basic
6.48
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.9309
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.9309
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.9089
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.9089
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8597
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8597
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8182
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8182
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.8139
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.8139
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.8118
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.8118
Vitamin D(3) 25-hydroxylase C4B644 CPVDH_PSEAH Pseudonocardia autotrophica 3 0.7959
Vitamin D(3) 25-hydroxylase C4B644 CPVDH_PSEAH Pseudonocardia autotrophica 3 0.7959
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7944
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7944
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7930
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7930
Camphor 5-monooxygenase P00183 CPXA_PSEPU Pseudomonas putida 3 0.7865
Camphor 5-monooxygenase P00183 CPXA_PSEPU Pseudomonas putida 3 0.7865
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.7756
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.7756
Retinol-binding protein 1 P02696 RET1_RAT Rattus norvegicus 3 0.7683
Retinol-binding protein 1 P02696 RET1_RAT Rattus norvegicus 3 0.7683
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 3 0.7425
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 3 0.7425
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 3 0.7381
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 3 0.7381
Beta-lactoglobulin P02754 LACB_BOVIN Bos taurus 3 0.7331
Beta-lactoglobulin P02754 LACB_BOVIN Bos taurus 3 0.7331
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7316
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7316
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7251
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7251
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7222
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7222
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7206
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7206
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.7154
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.7154
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7136
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7136
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7110
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7110
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.7063
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.7063
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.7035
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.7035

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