Ergosta-7,22-epidioxy-3beta-ol - Compound Card

Ergosta-7,22-epidioxy-3beta-ol

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Ergosta-7,22-epidioxy-3beta-ol

Structure
Zoomed Structure
  • Family: Fungi - Trichosphaeriaceae
  • Kingdom: Fungi
  • Class: Steroid
    • Subclass: Sterol
Canonical Smiles O[C@H]1CC[C@]2([C@]3(C1)OO[C@]1([C@@H]2CC[C@]2([C@@H]1CC[C@@H]2[C@H](/C=C/[C@@H](C(C)C)C)C)C)C=C3)C
InChI InChI=1S/C28H44O3/c1-18(2)19(3)7-8-20(4)22-9-10-23-25(22,5)13-12-24-26(6)14-11-21(29)17-27(26)15-16-28(23,24)31-30-27/h7-8,15-16,18-24,29H,9-14,17H2,1-6H3/b8-7+/t19-,20-,21-,22+,23-,24+,25+,26+,27-,28+/m0/s1
InChIKey VXOZCESVZIRHCJ-AEBOOECTSA-N
Formula C28H44O3
HBA 3
HBD 1
MW 428.66
Rotatable Bonds 4
TPSA 38.69
LogP 6.47
Number Rings 6
Number Aromatic Rings 0
Heavy Atom Count 31
Formal Charge 0
Fraction CSP3 0.86
Exact Mass 428.33
Number of Lipinski Rule Violations 1
# Species Family Kingdom NCBI Taxonomy ID
1 Nigrospora sphaerica Trichosphaeriaceae Fungi 114231

Showing of synonyms

  • Metwaly AM, Kadry HA, et al. (2014). Nigrosphaerin A a new isochromene derivative from the endophytic fungus Nigrospora sphaerica. Phytochemistry Letters,2014,7,1-5. [View]
Pubchem: 162977485

No compound-protein relationship available.

Structure

SMILES: C1CCC(C1C234)CCC3C5C(OO4)(C=C2)CCCC5

Level: 0

Mol. Weight: 428.66 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.71
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.62
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.41

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.58
Plasma Protein Binding
80.98
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
Non-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
12.4
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.76
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.13
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
5.71
Micronucleos
Safe
NR-AhR
Safe
NR-AR
Safe
NR-AR-LBD
Safe
NR-Aromatase
Safe
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Safe
NR-PPAR-gamma
Safe
NR-TR
Toxic
T. Pyriformis
-62.52
Rat (Acute)
3.09
Rat (Chronic Oral)
1.17
Fathead Minnow
3.92
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Toxic
SR-ATAD5
Toxic
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
434.99
Hydration Free Energy
-2.87
Log(D) at pH=7.4
5.55
Log(P)
7.6
Log S
-6.89
Log(Vapor Pressure)
-7.71
Melting Point
156.3
pKa Acid
9.95
pKa Basic
6.6
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.9304
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.9304
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.9294
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.9294
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.9184
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.9184
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 4 0.8557
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 4 0.8557
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 4 0.8443
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 4 0.8443
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8077
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8077
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 4 0.8046
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 4 0.8046
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.7985
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.7985
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7982
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7982
Beta-elicitin cryptogein P15570 ELIB_PHYCR Phytophthora cryptogea 4 0.7933
Beta-elicitin cryptogein P15570 ELIB_PHYCR Phytophthora cryptogea 4 0.7933
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7827
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7827
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 3 0.7811
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 3 0.7811
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7701
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7701
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7613
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7613
3-ketosteroid dehydrogenase Q9RA02 Q9RA02_RHOER Rhodococcus erythropolis 3 0.7471
3-ketosteroid dehydrogenase Q9RA02 Q9RA02_RHOER Rhodococcus erythropolis 3 0.7471
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7390
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7390
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 4 0.7372
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 4 0.7372
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7342
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7342
Integrin alpha-L P20701 ITAL_HUMAN Homo sapiens 3 0.7269
Integrin alpha-L P20701 ITAL_HUMAN Homo sapiens 3 0.7269
Steroid C26-monooxygenase P9WPP1 CP125_MYCTU Mycobacterium tuberculosis 3 0.7245
Steroid C26-monooxygenase P9WPP1 CP125_MYCTU Mycobacterium tuberculosis 3 0.7245
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.7242
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.7242
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.7206
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.7206
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7204
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7204
Lanosterol 14-alpha-demethylase Q385E8 Q385E8_TRYB2 Trypanosoma brucei brucei 4 0.7090
Lanosterol 14-alpha-demethylase Q385E8 Q385E8_TRYB2 Trypanosoma brucei brucei 4 0.7090
Oxysterols receptor LXR-beta P55055 NR1H2_HUMAN Homo sapiens 4 0.7044
Oxysterols receptor LXR-beta P55055 NR1H2_HUMAN Homo sapiens 4 0.7044
Nuclear receptor ROR-alpha P35398 RORA_HUMAN Homo sapiens 5 0.7042
Nuclear receptor ROR-alpha P35398 RORA_HUMAN Homo sapiens 5 0.7042

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