Ergosta-5(6),7,22-triene-3beta-ol - Compound Card

Ergosta-5(6),7,22-triene-3beta-ol

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Ergosta-5(6),7,22-triene-3beta-ol

Structure
Zoomed Structure
  • Family: Fungi - Trichosphaeriaceae
  • Kingdom: Fungi
  • Class: Steroid
    • Subclass: Sterol
Canonical Smiles O[C@H]1CC[C@]2(C(=CC=C3[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/C28H44O/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/h7-10,18-20,22,24-26,29H,11-17H2,1-6H3/b8-7+/t19-,20-,22-,24+,25+,26-,27-,28+/m0/s1
InChIKey DNVPQKQSNYMLRS-SECWYAQTSA-N
Formula C28H44O
HBA 1
HBD 1
MW 396.66
Rotatable Bonds 4
TPSA 20.23
LogP 7.33
Number Rings 4
Number Aromatic Rings 0
Heavy Atom Count 29
Formal Charge 0
Fraction CSP3 0.79
Exact Mass 396.34
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: 125126219
Nmrshiftdb2: 60061829

No compound-protein relationship available.

Structure

SMILES: C1CCC(C12)CCC3C2=CC=C4C3CCCC4

Level: 0

Mol. Weight: 396.66 g/mol

Anti-leishmanial

Absorption

Caco-2 (logPapp)
-4.73
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.55
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.77

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.83
Plasma Protein Binding
84.57
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
6.03
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.51
Biodegradation
Safe
Carcinogenesis
Toxic
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
1.13
Liver Injury II
Safe
hERG Blockers
Toxic
Daphnia Maga
6.22
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
-20.44
Rat (Acute)
3.31
Rat (Chronic Oral)
1.85
Fathead Minnow
4.29
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
406.32
Hydration Free Energy
-3.85
Log(D) at pH=7.4
6.07
Log(P)
8.09
Log S
-6.95
Log(Vapor Pressure)
-6.92
Melting Point
156.04
pKa Acid
12.39
pKa Basic
7.51
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.9484
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.9484
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 3 0.9454
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 3 0.9454
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.9355
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.9355
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.9258
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.9258
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.9079
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.9079
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.9067
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.9067
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.9011
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.9011
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8995
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8995
Steroid C26-monooxygenase P9WPP1 CP125_MYCTU Mycobacterium tuberculosis 3 0.8990
Steroid C26-monooxygenase P9WPP1 CP125_MYCTU Mycobacterium tuberculosis 3 0.8990
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8882
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8882
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8825
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8825
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8823
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8823
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8822
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8822
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8734
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8734
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8598
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8598
Retinol-binding protein 1 P02696 RET1_RAT Rattus norvegicus 3 0.8542
Retinol-binding protein 1 P02696 RET1_RAT Rattus norvegicus 3 0.8542
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.8500
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.8500
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8486
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8486
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8140
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8140
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 3 0.7979
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 3 0.7979
Japanin M1MR49 M1MR49_RHIAP Rhipicephalus appendiculatus 5 0.7972
Japanin M1MR49 M1MR49_RHIAP Rhipicephalus appendiculatus 5 0.7972
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.7867
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.7867
Beta-lactoglobulin P02754 LACB_BOVIN Bos taurus 3 0.7860
Beta-lactoglobulin P02754 LACB_BOVIN Bos taurus 3 0.7860
Lanosterol synthase P48449 ERG7_HUMAN Homo sapiens 4 0.7851
Lanosterol synthase P48449 ERG7_HUMAN Homo sapiens 4 0.7851
Beta-elicitin cryptogein P15570 ELIB_PHYCR Phytophthora cryptogea 4 0.7774
Beta-elicitin cryptogein P15570 ELIB_PHYCR Phytophthora cryptogea 4 0.7774
Retinol dehydratase Q26490 Q26490_SPOFR Spodoptera frugiperda 3 0.7639
Retinol dehydratase Q26490 Q26490_SPOFR Spodoptera frugiperda 3 0.7639
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7469
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7469
Nuclear receptor ROR-alpha P35398 RORA_HUMAN Homo sapiens 5 0.7450
Nuclear receptor ROR-alpha P35398 RORA_HUMAN Homo sapiens 5 0.7450
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.7414
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.7414
Aldo-keto reductase family 1 member C1 Q04828 AK1C1_HUMAN Homo sapiens 3 0.7405
Aldo-keto reductase family 1 member C1 Q04828 AK1C1_HUMAN Homo sapiens 3 0.7405
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7296
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7296
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7274
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7274
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7242
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7242
Lanosterol 14-alpha-demethylase Q385E8 Q385E8_TRYB2 Trypanosoma brucei brucei 4 0.7235
Lanosterol 14-alpha-demethylase Q385E8 Q385E8_TRYB2 Trypanosoma brucei brucei 4 0.7235
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7226
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7226
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7211
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7211
Peroxisome proliferator-activated receptor alpha Q07869 PPARA_HUMAN Homo sapiens 3 0.7156
Peroxisome proliferator-activated receptor alpha Q07869 PPARA_HUMAN Homo sapiens 3 0.7156
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 4 0.7131
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 4 0.7131
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 3 0.7083
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 3 0.7083
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7060
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7060
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7056
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7056
Cholesterol side-chain cleavage enzyme, mitochondrial P05108 CP11A_HUMAN Homo sapiens 3 0.7035
Cholesterol side-chain cleavage enzyme, mitochondrial P05108 CP11A_HUMAN Homo sapiens 3 0.7035
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7024
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7024
Vitamin D(3) 25-hydroxylase C4B644 CPVDH_PSEAH Pseudonocardia autotrophica 3 0.7003
Vitamin D(3) 25-hydroxylase C4B644 CPVDH_PSEAH Pseudonocardia autotrophica 3 0.7003

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