4,6,24(28)-ergostatrien-3-one - Compound Card

4,6,24(28)-ergostatrien-3-one

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4,6,24(28)-ergostatrien-3-one

Structure
Zoomed Structure
  • Family: Plantae - Anacardiaceae
  • Kingdom: Plantae
  • Class: Steroid
    • Subclass: Phytosterol
Canonical Smiles C=C(C(C)C)CC[C@H]([C@H]1CC[C@@H]2[C@]1(C)CC[C@H]1[C@H]2C=CC2=CC(=O)CC[C@]12C)C
InChI InChI=1S/C28H42O/c1-18(2)19(3)7-8-20(4)24-11-12-25-23-10-9-21-17-22(29)13-15-27(21,5)26(23)14-16-28(24,25)6/h9-10,17-18,20,23-26H,3,7-8,11-16H2,1-2,4-6H3/t20-,23+,24-,25+,26+,27+,28-/m1/s1
InChIKey CWYDRTXCOXFPDB-QVMRCSLBSA-N
Formula C28H42O
HBA 1
HBD 0
MW 394.64
Rotatable Bonds 5
TPSA 17.07
LogP 7.54
Number Rings 4
Number Aromatic Rings 0
Heavy Atom Count 29
Formal Charge 0
Fraction CSP3 0.75
Exact Mass 394.32
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)CCC3C2C=CC=4C3CCC(=O)C4

Level: 0

Mol. Weight: 394.64 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.88
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.59
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.77

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
2.23
Plasma Protein Binding
84.44
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Inhibitor
CYP 1A2 Inhibitor
Non-Inhibitor
CYP 1A2 Substrate
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
6.32
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.72
Biodegradation
Safe
Carcinogenesis
Toxic
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
1.08
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
6.85
Micronucleos
Safe
NR-AhR
Safe
NR-AR
Toxic
NR-AR-LBD
Toxic
NR-Aromatase
Safe
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Toxic
NR-PPAR-gamma
Safe
NR-TR
Toxic
T. Pyriformis
-16.97
Rat (Acute)
2.16
Rat (Chronic Oral)
1.79
Fathead Minnow
4.02
Respiratory Disease
Safe
Skin Sensitisation
Toxic
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
440.16
Hydration Free Energy
-4.26
Log(D) at pH=7.4
5.82
Log(P)
7.09
Log S
-6.32
Log(Vapor Pressure)
-7.06
Melting Point
114.42
pKa Acid
11.68
pKa Basic
6.55
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 0.9625
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.9625
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.9601
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.9601
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.9337
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.9337
Beta-lactoglobulin P02754 LACB_BOVIN Bos taurus 3 0.8869
Beta-lactoglobulin P02754 LACB_BOVIN Bos taurus 3 0.8869
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8863
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8863
NPC intracellular cholesterol transporter 1 O15118 NPC1_HUMAN Homo sapiens 3 0.8684
NPC intracellular cholesterol transporter 1 O15118 NPC1_HUMAN Homo sapiens 3 0.8684
Oxysterols receptor LXR-beta P55055 NR1H2_HUMAN Homo sapiens 4 0.8559
Oxysterols receptor LXR-beta P55055 NR1H2_HUMAN Homo sapiens 4 0.8559
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8537
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8537
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.8304
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.8304
Beta-lactoglobulin P02754 LACB_BOVIN Bos taurus 3 0.8282
Beta-lactoglobulin P02754 LACB_BOVIN Bos taurus 3 0.8282
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8272
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8272
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.8246
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.8246
Retinol dehydratase Q26490 Q26490_SPOFR Spodoptera frugiperda 3 0.8177
Retinol dehydratase Q26490 Q26490_SPOFR Spodoptera frugiperda 3 0.8177
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.8087
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.8087
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 3 0.8052
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 3 0.8052
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 3 0.8009
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 3 0.8009
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.8002
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.8002
Cholesterol side-chain cleavage enzyme, mitochondrial P05108 CP11A_HUMAN Homo sapiens 3 0.7968
Cholesterol side-chain cleavage enzyme, mitochondrial P05108 CP11A_HUMAN Homo sapiens 3 0.7968
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7950
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7950
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 3 0.7938
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 3 0.7938
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7919
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7919
Steroid C26-monooxygenase P9WPP1 CP125_MYCTU Mycobacterium tuberculosis 3 0.7868
Steroid C26-monooxygenase P9WPP1 CP125_MYCTU Mycobacterium tuberculosis 3 0.7868
NPC intracellular cholesterol transporter 1 O15118 NPC1_HUMAN Homo sapiens 4 0.7838
NPC intracellular cholesterol transporter 1 O15118 NPC1_HUMAN Homo sapiens 4 0.7838
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7795
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7795
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.7794
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.7794
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7774
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7774
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.7754
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.7754
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7754
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7754
Methyl-branched lipid omega-hydroxylase P9WPP3 CP124_MYCTU Mycobacterium tuberculosis 3 0.7749
Methyl-branched lipid omega-hydroxylase P9WPP3 CP124_MYCTU Mycobacterium tuberculosis 3 0.7749
Retinol-binding protein 1 P02696 RET1_RAT Rattus norvegicus 3 0.7700
Retinol-binding protein 1 P02696 RET1_RAT Rattus norvegicus 3 0.7700
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7649
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7649
Lanosterol 14-alpha-demethylase Q385E8 Q385E8_TRYB2 Trypanosoma brucei brucei 3 0.7627
Lanosterol 14-alpha-demethylase Q385E8 Q385E8_TRYB2 Trypanosoma brucei brucei 3 0.7627
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7591
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7591
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7570
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7570
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7545
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7545
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 2 0.7493
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 2 0.7493
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 2 0.7352
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 2 0.7352
Soluble cytochrome b562 P0ABE7 C562_ECOLX Escherichia coli 2 0.7284
Soluble cytochrome b562 P0ABE7 C562_ECOLX Escherichia coli 2 0.7284
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7282
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7282
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7235
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7235
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7180
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7180
Sodium-dependent dopamine transporter Q7K4Y6 DAT_DROME Drosophila melanogaster 2 0.7141
Sodium-dependent dopamine transporter Q7K4Y6 DAT_DROME Drosophila melanogaster 2 0.7141
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7140
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7140
Nuclear receptor coactivator 2 Q15596 NCOA2_HUMAN Homo sapiens 3 0.7139
Nuclear receptor coactivator 2 Q15596 NCOA2_HUMAN Homo sapiens 3 0.7139
Cholesterol side-chain cleavage enzyme, mitochondrial P00189 CP11A_BOVIN Bos taurus 3 0.7116
Cholesterol side-chain cleavage enzyme, mitochondrial P00189 CP11A_BOVIN Bos taurus 3 0.7116
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7104
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7104
Reaction center protein L chain P0C0Y7 RCEH_RHOSH Rhodobacter sphaeroides 2 0.7066
Reaction center protein L chain P0C0Y7 RCEH_RHOSH Rhodobacter sphaeroides 2 0.7066

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