Ergosta-4,6,8(14),22-tetraene-3one - Compound Card

Ergosta-4,6,8(14),22-tetraene-3one

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Ergosta-4,6,8(14),22-tetraene-3one

Structure
Zoomed Structure
  • Family: Fungi - Trichosphaeriaceae
  • Kingdom: Fungi
  • Class: Steroid
    • Subclass: Sterol
Canonical Smiles CC([C@H](/C=C/[C@@H]([C@H]1CCC2=C3[C@H](CC[C@]12C)[C@@]1(C)CCC(=O)C=C1C=C3)C)C)C
InChI InChI=1S/C28H40O/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/h7-10,17-20,24,26H,11-16H2,1-6H3/b8-7+/t19-,20-,24+,26-,27-,28+/m0/s1
InChIKey OIMXTYUHMBQQJM-ZLCRMROVSA-N
Formula C28H40O
HBA 1
HBD 0
MW 392.63
Rotatable Bonds 4
TPSA 17.07
LogP 7.46
Number Rings 4
Number Aromatic Rings 0
Heavy Atom Count 29
Formal Charge 0
Fraction CSP3 0.68
Exact Mass 392.31
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: 162924309
Nmrshiftdb2: 60061826

No compound-protein relationship available.

Structure

SMILES: C1CC(=O)C=C(C=C2)C1C(C2=C34)CCC3CCC4

Level: 0

Mol. Weight: 392.63 g/mol

Antileukemia

Absorption

Caco-2 (logPapp)
-4.83
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.66
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.58

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
2.14
Plasma Protein Binding
90.86
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
Non-Inhibitor
CYP 1A2 Substrate
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
2.86
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
2.06
Biodegradation
Safe
Carcinogenesis
Toxic
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.63
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
6.9
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
-18.81
Rat (Acute)
2.5
Rat (Chronic Oral)
1.61
Fathead Minnow
4.7
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
438.4
Hydration Free Energy
-4.49
Log(D) at pH=7.4
5.52
Log(P)
7.4
Log S
-6.59
Log(Vapor Pressure)
-6.57
Melting Point
127.63
pKa Acid
11.33
pKa Basic
5.53
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 0.9645
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.9645
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.9400
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.9400
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.9099
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.9099
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 C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.9023
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.9023
Oxysterols receptor LXR-beta P55055 NR1H2_HUMAN Homo sapiens 4 0.8528
Oxysterols receptor LXR-beta P55055 NR1H2_HUMAN Homo sapiens 4 0.8528
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8250
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8250
Beta-elicitin cryptogein P15570 ELIB_PHYCR Phytophthora cryptogea 4 0.8190
Beta-elicitin cryptogein P15570 ELIB_PHYCR Phytophthora cryptogea 4 0.8190
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8114
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8114
NPC intracellular cholesterol transporter 1 O15118 NPC1_HUMAN Homo sapiens 3 0.7763
NPC intracellular cholesterol transporter 1 O15118 NPC1_HUMAN Homo sapiens 3 0.7763
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7639
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7639
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7633
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7633
Retinol dehydratase Q26490 Q26490_SPOFR Spodoptera frugiperda 3 0.7446
Retinol dehydratase Q26490 Q26490_SPOFR Spodoptera frugiperda 3 0.7446
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7288
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7288
Aldo-keto reductase family 1 member C1 Q04828 AK1C1_HUMAN Homo sapiens 3 0.7269
Aldo-keto reductase family 1 member C1 Q04828 AK1C1_HUMAN Homo sapiens 3 0.7269
Reaction center protein L chain P0C0Y7 RCEH_RHOSH Rhodobacter sphaeroides 2 0.7254
Reaction center protein L chain P0C0Y7 RCEH_RHOSH Rhodobacter sphaeroides 2 0.7254
Nuclear receptor ROR-gamma P51449 RORG_HUMAN Homo sapiens 3 0.7245
Nuclear receptor ROR-gamma P51449 RORG_HUMAN Homo sapiens 3 0.7245
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 2 0.7232
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 2 0.7232
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7063
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7063
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7051
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7051

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