Stigmasta-4,6,8(14), 22-tetraen-3-one - Compound Card

Stigmasta-4,6,8(14), 22-tetraen-3-one

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Stigmasta-4,6,8(14), 22-tetraen-3-one

Structure
Zoomed Structure
  • Family: Fungi - Trichocomaceae
  • Kingdom: Fungi
  • Class: Steroid
    • Subclass: Phytosterol
Canonical Smiles CC[C@@H](C(C)C)C=C[C@H]([C@H]1CCC2=C3[C@H](CC[C@]12C)[C@@]1(C)CCC(=O)C=C1C=C3)C
InChI InChI=1S/C29H42O/c1-7-21(19(2)3)9-8-20(4)25-12-13-26-24-11-10-22-18-23(30)14-16-28(22,5)27(24)15-17-29(25,26)6/h8-11,18-21,25,27H,7,12-17H2,1-6H3/t20-,21-,25-,27+,28+,29-/m1/s1
InChIKey KULGJNLEWICRST-CPRBRYNJSA-N
Formula C29H42O
HBA 1
HBD 0
MW 406.65
Rotatable Bonds 5
TPSA 17.07
LogP 7.85
Number Rings 4
Number Aromatic Rings 0
Heavy Atom Count 30
Formal Charge 0
Fraction CSP3 0.69
Exact Mass 406.32
Number of Lipinski Rule Violations 1
# Species Family Kingdom NCBI Taxonomy ID
1 Aspergillus terreus Trichocomaceae Fungi 33178
2 Aspergillus versicolor Trichocomaceae Fungi 46472

Showing of synonyms

  • Mohamed G, Ibrahim S, et al. (2020). Antimicrobial metabolites from the endophytic fungus Aspergillus versicolor. Phytochemistry Letters,2020,35,152–155. [View]
  • Ibrahim S, Elkhayat E, et al. (2015). Aspernolides F and G, new butyrolactones from the endophytic fungus Aspergillus terreus. Phytochemistry Letters, 2015,14,84–90. [View]
Pubchem: 129881864

No compound-protein relationship available.

Structure

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

Level: 0

Mol. Weight: 406.65 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.86
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.67
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.75

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
2.28
Plasma Protein Binding
92.06
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
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
2.2
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
2.12
Biodegradation
Safe
Carcinogenesis
Toxic
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.67
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
7.11
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
-32.92
Rat (Acute)
2.33
Rat (Chronic Oral)
1.77
Fathead Minnow
4.59
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
447.59
Hydration Free Energy
-4.1
Log(D) at pH=7.4
5.56
Log(P)
8.01
Log S
-6.41
Log(Vapor Pressure)
-6.81
Melting Point
116.47
pKa Acid
11.54
pKa Basic
5.6
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 0.9649
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.9526
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.9160
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.9038
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.9036
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.8081
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8063
Retinol-binding protein 1 P02696 RET1_RAT Rattus norvegicus 3 0.7980
Beta-elicitin cryptogein P15570 ELIB_PHYCR Phytophthora cryptogea 4 0.7791
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 3 0.7754
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7722
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7717
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.7604
NPC intracellular cholesterol transporter 1 O15118 NPC1_HUMAN Homo sapiens 3 0.7406
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7373
Aldo-keto reductase family 1 member C1 Q04828 AK1C1_HUMAN Homo sapiens 3 0.7314
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 2 0.7302
Reaction center protein L chain P0C0Y7 RCEH_RHOSH Rhodobacter sphaeroides 2 0.7243
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7171
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7152
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 3 0.7150
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7133
Beta-lactoglobulin P02754 LACB_BOVIN Bos taurus 3 0.7073
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7070
Sodium-dependent dopamine transporter Q7K4Y6 DAT_DROME Drosophila melanogaster 2 0.7048
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.7041
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7026

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