3beta,7alpha,20beta-trihydroxyergosta-5,24(28)-diene - Compound Card

3beta,7alpha,20beta-trihydroxyergosta-5,24(28)-diene

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3beta,7alpha,20beta-trihydroxyergosta-5,24(28)-diene

Structure
Zoomed Structure
  • Family: Plantae - Meliaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Ergostane Steroid
Canonical Smiles O[C@H]1CC[C@]2(C(=C[C@H]([C@@H]3[C@@H]2CC[C@]2([C@H]3CC[C@@H]2[C@](CCC(=C)C(C)C)(O)C)C)O)C1)C
InChI InChI=1S/C28H46O3/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/h16-17,20-25,29-31H,3,7-15H2,1-2,4-6H3/t20-,21-,22-,23+,24-,25-,26-,27-,28-/m0/s1
InChIKey VSCQIKVLPQYCJG-NBXDYDPPSA-N
Formula C28H46O3
HBA 3
HBD 3
MW 430.67
Rotatable Bonds 5
TPSA 60.69
LogP 5.64
Number Rings 4
Number Aromatic Rings 0
Heavy Atom Count 31
Formal Charge 0
Fraction CSP3 0.86
Exact Mass 430.34
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: 163025660

No compound-protein relationship available.

Structure

SMILES: C1CCC(C12)CCC3C2CC=C4C3CCCC4

Level: 0

Mol. Weight: 430.67 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.77
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.61
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
-2.79

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.35
Plasma Protein Binding
80.48
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
11.0
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.44
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.25
Liver Injury II
Safe
hERG Blockers
Toxic
Daphnia Maga
5.77
Micronucleos
Safe
NR-AhR
Safe
NR-AR
Safe
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
-39.79
Rat (Acute)
3.61
Rat (Chronic Oral)
2.31
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
397.65
Hydration Free Energy
-3.19
Log(D) at pH=7.4
4.6
Log(P)
5.57
Log S
-5.62
Log(Vapor Pressure)
-8.48
Melting Point
173.05
pKa Acid
10.77
pKa Basic
7.27
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 3 0.9329
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.9096
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.9054
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.9022
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8806
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8758
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8632
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8596
Lanosterol 14-alpha-demethylase Q385E8 Q385E8_TRYB2 Trypanosoma brucei brucei 4 0.8586
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.8498
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8260
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8202
Retinol-binding protein 1 P02696 RET1_RAT Rattus norvegicus 3 0.8096
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7995
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7824
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7812
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7741
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7729
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7670
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 3 0.7630
NPC intracellular cholesterol transporter 1 O15118 NPC1_HUMAN Homo sapiens 3 0.7610
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 4 0.7591
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 3 0.7545
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7491
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.7457
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7452
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7390
Oxysterols receptor LXR-beta P55055 NR1H2_HUMAN Homo sapiens 4 0.7380
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.7378
NPC intracellular cholesterol transporter 1 O15118 NPC1_HUMAN Homo sapiens 4 0.7366
Nuclear receptor ROR-gamma P51449 RORG_HUMAN Homo sapiens 4 0.7347
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7250
Nuclear receptor ROR-alpha P35398 RORA_HUMAN Homo sapiens 5 0.7220
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.7162
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7137
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7130
Retinol dehydratase Q26490 Q26490_SPOFR Spodoptera frugiperda 3 0.7101
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7076
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7025
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7012

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