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 - Meliaceae
  • Kingdom: Plantae
  • Class: Terpene
    • Subclass: Triterpene
Canonical Smiles C=C(C(C)C)CC[C@]([C@H]1CC[C@@H]2[C@]1(C)CC[C@H]1[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-MRPYZOCESA-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 Entandrophragma congoënse Meliaceae Plantae 2590899

Showing of synonyms

  • Happi GM, Talontsi FM, et al. (2018). seco-Tiaminic acids B and C: Identification of two novel 3,4-seco-tirucallane triterpenoids isolated from the root of Entandrophragma congoënse (Meliaceae).. Fitoterapia,2018, 124, 17-22. [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)
-4.7
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.51
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.75

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.52
Plasma Protein Binding
83.11
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
10.47
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.35
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.67
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
5.85
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
-37.71
Rat (Acute)
3.13
Rat (Chronic Oral)
1.97
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
432.67
Hydration Free Energy
-3.21
Log(D) at pH=7.4
4.62
Log(P)
5.04
Log S
-5.71
Log(Vapor Pressure)
-8.37
Melting Point
163.68
pKa Acid
10.56
pKa Basic
6.07
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 0.9176
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.9000
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8982
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8976
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8947
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8813
Vitamin D(3) 25-hydroxylase C4B644 CPVDH_PSEAH Pseudonocardia autotrophica 3 0.8669
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8630
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.8320
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 4 0.8256
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 4 0.8187
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 4 0.8163
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 4 0.8100
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8087
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 4 0.8058
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 4 0.8053
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 4 0.8013
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 4 0.8013
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7984
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 4 0.7982
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.7978
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.7953
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 4 0.7943
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7938
Androgen receptor O97775 ANDR_PANTR Pan troglodytes 4 0.7923
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 4 0.7914
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 4 0.7912
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 4 0.7900
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.7892
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 4 0.7875
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 4 0.7862
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 3 0.7853
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7849
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 4 0.7847
Androgen receptor O97775 ANDR_PANTR Pan troglodytes 4 0.7843
Androgen receptor O97775 ANDR_PANTR Pan troglodytes 4 0.7813
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 4 0.7801
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7798
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 4 0.7792
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 4 0.7763
Androgen receptor O97775 ANDR_PANTR Pan troglodytes 4 0.7752
Androgen receptor O97775 ANDR_PANTR Pan troglodytes 4 0.7749
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 4 0.7740
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 4 0.7719
Androgen receptor O97775 ANDR_PANTR Pan troglodytes 4 0.7708
Androgen receptor O97775 ANDR_PANTR Pan troglodytes 4 0.7692
Androgen receptor P19091 ANDR_MOUSE Mus musculus 4 0.7691
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 4 0.7681
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7673
Androgen receptor O97775 ANDR_PANTR Pan troglodytes 4 0.7667
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 4 0.7597
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 4 0.7597
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 4 0.7592
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 3 0.7550
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.7544
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.7539
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 4 0.7534
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.7457
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 3 0.7403
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 4 0.7402
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7401
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.7364
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 4 0.7277
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 4 0.7258
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7208
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7133
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 4 0.7079
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 3 0.7033
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7025
Lanosterol 14-alpha-demethylase Q385E8 Q385E8_TRYB2 Trypanosoma brucei brucei 3 0.7019

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