20S-hydroxy-4,6,24(28)-ergostatrien-3-one - Compound Card

20S-hydroxy-4,6,24(28)-ergostatrien-3-one

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20S-hydroxy-4,6,24(28)-ergostatrien-3-one

Structure
Zoomed Structure
  • Family: Plantae - Meliaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Ergostane Steroid
Canonical Smiles C=C(C(C)C)CC[C@@]([C@H]1CC[C@@H]2[C@]1(C)CC[C@H]1[C@H]2C=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-RMIXPHLWSA-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 Entandrophragma angolense Meliaceae Plantae 587577

Showing of synonyms

  • Happi GM, Wouamba SCN, et al. (2020). Ergostane-type steroids from the Cameroonian 'white tiama' Entandrophragma angolense.. Steroids,2020, 156, 108584. [View] [PubMed]
Pubchem: 122390697

No compound-protein relationship available.

Structure

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

Level: 0

Mol. Weight: 410.64 g/mol

Antiviral

Absorption

Caco-2 (logPapp)
-4.84
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
-2.7

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.89
Plasma Protein Binding
86.19
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
6.26
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.82
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
Toxic
Daphnia Maga
6.36
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
-24.84
Rat (Acute)
2.58
Rat (Chronic Oral)
1.72
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
439.58
Hydration Free Energy
-3.75
Log(D) at pH=7.4
5.32
Log(P)
5.95
Log S
-6.35
Log(Vapor Pressure)
-7.64
Melting Point
150.79
pKa Acid
11.19
pKa Basic
5.72
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 0.9626
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.9562
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.9411
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.9084
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8821
Vitamin D(3) 25-hydroxylase C4B644 CPVDH_PSEAH Pseudonocardia autotrophica 3 0.8778
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 4 0.8721
Retinol-binding protein 1 P02696 RET1_RAT Rattus norvegicus 3 0.8630
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8613
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 4 0.8448
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.8430
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.8427
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8383
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 4 0.8345
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8317
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.8245
NPC intracellular cholesterol transporter 1 O15118 NPC1_HUMAN Homo sapiens 3 0.8244
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 4 0.8243
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 4 0.8224
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 4 0.8189
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.8186
Androgen receptor O97775 ANDR_PANTR Pan troglodytes 4 0.8172
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 4 0.8170
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 4 0.8124
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8053
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 4 0.8039
Androgen receptor O97775 ANDR_PANTR Pan troglodytes 4 0.8039
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 4 0.8036
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8036
Beta-lactoglobulin P02754 LACB_BOVIN Bos taurus 3 0.8028
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.8027
Beta-elicitin cryptogein P15570 ELIB_PHYCR Phytophthora cryptogea 4 0.8018
Androgen receptor O97775 ANDR_PANTR Pan troglodytes 4 0.8002
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 4 0.7985
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 4 0.7976
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.7953
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 4 0.7950
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7930
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 4 0.7924
Androgen receptor O97775 ANDR_PANTR Pan troglodytes 4 0.7920
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 4 0.7914
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 4 0.7894
Androgen receptor O97775 ANDR_PANTR Pan troglodytes 4 0.7836
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 4 0.7829
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7822
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 4 0.7804
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.7801
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.7783
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 4 0.7779
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7765
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 4 0.7745
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 3 0.7741
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 4 0.7738
Androgen receptor P19091 ANDR_MOUSE Mus musculus 4 0.7727
Androgen receptor O97775 ANDR_PANTR Pan troglodytes 4 0.7706
Lanosterol 14-alpha-demethylase Q385E8 Q385E8_TRYB2 Trypanosoma brucei brucei 3 0.7692
Retinol dehydratase Q26490 Q26490_SPOFR Spodoptera frugiperda 3 0.7659
Androgen receptor O97775 ANDR_PANTR Pan troglodytes 4 0.7657
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7643
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7634
Androgen receptor O97775 ANDR_PANTR Pan troglodytes 4 0.7592
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 4 0.7571
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7563
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 4 0.7559
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 4 0.7509
Cholesterol side-chain cleavage enzyme, mitochondrial P05108 CP11A_HUMAN Homo sapiens 3 0.7489
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 4 0.7418
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7410
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7363
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 2 0.7354
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 3 0.7325
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 4 0.7313
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 3 0.7307
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 4 0.7306
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.7301
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 4 0.7280
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7220
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7207
Nuclear receptor coactivator 2 Q15596 NCOA2_HUMAN Homo sapiens 3 0.7204
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 4 0.7150
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7091
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 4 0.7083
Vitamin D3 receptor P13053 VDR_RAT Rattus norvegicus 3 0.7021
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7006
4,4'-diapophytoene synthase A9JQL9 CRTM_STAAU Staphylococcus aureus 2 0.7001

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