Ergosta-5,22-dien-3beta-ol - Compound Card

Ergosta-5,22-dien-3beta-ol

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Ergosta-5,22-dien-3beta-ol

Structure
Zoomed Structure
  • Family: Fungi - Lyophyllaceae
  • Kingdom: Fungi
  • Class: Steroid
    • Subclass: Sterol
Canonical Smiles O[C@H]1CC[C@]2(C(=CC[C@@H]3[C@@H]2CC[C@]2([C@H]3CC[C@@H]2[C@@H](/C=C\[C@@H](C(C)C)C)C)C)C1)C
InChI InChI=1S/C28H46O/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/h7-9,18-20,22-26,29H,10-17H2,1-6H3/b8-7-/t19-,20+,22-,23-,24+,25-,26-,27-,28+/m0/s1
InChIKey OILXMJHPFNGGTO-DQFGDDFMSA-N
Formula C28H46O
HBA 1
HBD 1
MW 398.68
Rotatable Bonds 4
TPSA 20.23
LogP 7.41
Number Rings 4
Number Aromatic Rings 0
Heavy Atom Count 29
Formal Charge 0
Fraction CSP3 0.86
Exact Mass 398.35
Number of Lipinski Rule Violations 1
# Species Family Kingdom NCBI Taxonomy ID
1 Termitomyces letestui Lyophyllaceae Fungi 2093650

Showing of synonyms

  • Baraza LD, Joseph CC, et al. (2007). Chemical constituents and biological activity of three Tanzanian wild mushroom species. Tanzanian Journal of Sciences,2007,33,1-7. [View]
Pubchem: 71300381
Nmrshiftdb2: 60021534

No compound-protein relationship available.

Structure

SMILES: C1CCC(C12)CCC3C2CC=C4C3CCCC4

Level: 0

Mol. Weight: 398.68 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.74
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.5
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.69

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.76
Plasma Protein Binding
82.1
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
9.87
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.15
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
1.74
Liver Injury II
Safe
hERG Blockers
Toxic
Daphnia Maga
6.01
Micronucleos
Safe
NR-AhR
Safe
NR-AR
Toxic
NR-AR-LBD
Safe
NR-Aromatase
Safe
NR-ER
Toxic
NR-ER-LBD
Safe
NR-GR
Safe
NR-PPAR-gamma
Safe
NR-TR
Toxic
T. Pyriformis
-20.69
Rat (Acute)
2.42
Rat (Chronic Oral)
1.77
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
396.54
Hydration Free Energy
-3.75
Log(D) at pH=7.4
6.52
Log(P)
8.62
Log S
-7.04
Log(Vapor Pressure)
-6.81
Melting Point
144.63
pKa Acid
12.94
pKa Basic
8.2
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 0.9395
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 3 0.9395
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.9101
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.9101
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.9092
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.9092
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.9075
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.9075
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.9063
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.9063
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8977
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8977
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8894
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8894
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8818
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8818
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8711
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8711
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8670
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8670
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8562
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8562
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8498
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8498
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8487
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8487
Steroid C26-monooxygenase P9WPP1 CP125_MYCTU Mycobacterium tuberculosis 3 0.8300
Steroid C26-monooxygenase P9WPP1 CP125_MYCTU Mycobacterium tuberculosis 3 0.8300
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8246
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8246
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.8052
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.8052
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7881
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7881
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.7691
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.7691
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 3 0.7530
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 3 0.7530
Oxysterols receptor LXR-beta P55055 NR1H2_HUMAN Homo sapiens 4 0.7517
Oxysterols receptor LXR-beta P55055 NR1H2_HUMAN Homo sapiens 4 0.7517
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7453
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7453
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7207
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7207
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7200
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7200
NPC intracellular cholesterol transporter 1 O15118 NPC1_HUMAN Homo sapiens 3 0.7162
NPC intracellular cholesterol transporter 1 O15118 NPC1_HUMAN Homo sapiens 3 0.7162
Beta-lactoglobulin P02754 LACB_BOVIN Bos taurus 3 0.7156
Beta-lactoglobulin P02754 LACB_BOVIN Bos taurus 3 0.7156
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7047
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7047
NPC intracellular cholesterol transporter 1 O15118 NPC1_HUMAN Homo sapiens 4 0.7046
NPC intracellular cholesterol transporter 1 O15118 NPC1_HUMAN Homo sapiens 4 0.7046
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7042
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7042
Soluble cytochrome b562 P0ABE7 C562_ECOLX Escherichia coli 4 0.7000
Soluble cytochrome b562 P0ABE7 C562_ECOLX Escherichia coli 4 0.7000

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