Ergosta-6,22-diene-3beta,5alpha,8alpha-triol - Compound Card

Ergosta-6,22-diene-3beta,5alpha,8alpha-triol

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Ergosta-6,22-diene-3beta,5alpha,8alpha-triol

Structure
Zoomed Structure
  • Family: Fungi - Trichosphaeriaceae
  • Kingdom: Fungi
  • Class: Steroid
    • Subclass: Sterol
Canonical Smiles O[C@H]1CC[C@]2([C@@](C1)(O)CC[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)O)C
InChI InChI=1S/C28H48O3/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(26,30)15-16-28(23,24)31/h7-8,18-24,29-31H,9-17H2,1-6H3/b8-7+/t19-,20-,21-,22+,23-,24+,25+,26+,27+,28-/m0/s1
InChIKey PJARFCFHURTCPY-UOEQHSOYSA-N
Formula C28H48O3
HBA 3
HBD 3
MW 432.69
Rotatable Bonds 4
TPSA 60.69
LogP 5.72
Number Rings 4
Number Aromatic Rings 0
Heavy Atom Count 31
Formal Charge 0
Fraction CSP3 0.93
Exact Mass 432.36
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: 162904367
Nmrshiftdb2: 60061823

No compound-protein relationship available.

Structure

SMILES: C1CCC(C12)CCC3C2CCC4C3CCCC4

Level: 0

Mol. Weight: 432.69 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.7
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.69
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.05

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.29
Plasma Protein Binding
87.73
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
8.73
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.36
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.6
Liver Injury II
Safe
hERG Blockers
Toxic
Daphnia Maga
5.59
Micronucleos
Safe
NR-AhR
Safe
NR-AR
Toxic
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
-40.07
Rat (Acute)
3.07
Rat (Chronic Oral)
1.6
Fathead Minnow
3.83
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
451.6
Hydration Free Energy
-3.97
Log(D) at pH=7.4
4.95
Log(P)
6.79
Log S
-5.81
Log(Vapor Pressure)
-8.31
Melting Point
181.26
pKa Acid
10.78
pKa Basic
8.5
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 0.9458
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.9458
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8570
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8570
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 3 0.8219
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 3 0.8219
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8186
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8186
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8122
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8122
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8114
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8114
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.8008
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.8008
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
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7620
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7620
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7523
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7523
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7411
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7411
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.7350
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.7350
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 3 0.7324
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 3 0.7324
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7261
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7261
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7171
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7171
Integrin alpha-L P20701 ITAL_HUMAN Homo sapiens 3 0.7093
Integrin alpha-L P20701 ITAL_HUMAN Homo sapiens 3 0.7093
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7083
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7083
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 3 0.7057
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 3 0.7057

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