(22E,24R)-stigmasta-5,7,22-trien-3beta-ol - Compound Card

(22E,24R)-stigmasta-5,7,22-trien-3beta-ol

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(22E,24R)-stigmasta-5,7,22-trien-3beta-ol

Structure
Zoomed Structure
  • Family: Fungi - Trichocomaceae
  • Kingdom: Fungi
  • Class: Steroid
    • Subclass: Phytosterol
Canonical Smiles CC[C@H](C(C)C)/C=C/[C@H](C1CC[C@@H]2[C@]1(C)CC[C@H]1C2=CC=C2[C@]1(C)CC[C@@H](C2)O)C
InChI InChI=1S/C29H46O/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/h8-11,19-21,23,25-27,30H,7,12-18H2,1-6H3/b9-8+/t20-,21+,23+,25?,26+,27+,28+,29-/m1/s1
InChIKey OQMZNAMGEHIHNN-IVZJHVLKSA-N
Formula C29H46O
HBA 1
HBD 1
MW 410.69
Rotatable Bonds 5
TPSA 20.23
LogP 7.72
Number Rings 4
Number Aromatic Rings 0
Heavy Atom Count 30
Formal Charge 0
Fraction CSP3 0.79
Exact Mass 410.35
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]

No compound-protein relationship available.

Structure

SMILES: C1CCC(C12)CCC3C2=CC=C4C3CCCC4

Level: 0

Mol. Weight: 410.69 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.76
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.57
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.98

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.93
Plasma Protein Binding
84.46
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
4.61
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.7
Biodegradation
Safe
Carcinogenesis
Toxic
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.96
Liver Injury II
Safe
hERG Blockers
Toxic
Daphnia Maga
6.47
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
-33.11
Rat (Acute)
3.02
Rat (Chronic Oral)
1.99
Fathead Minnow
4.6
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
411.31
Hydration Free Energy
-3.84
Log(D) at pH=7.4
6.18
Log(P)
8.4
Log S
-6.83
Log(Vapor Pressure)
-7.08
Melting Point
144.63
pKa Acid
12.54
pKa Basic
7.38
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 3 0.9482
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.9453
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.9362
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.9315
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.9307
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.9293
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.9194
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.9192
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.9190
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.9171
Steroid C26-monooxygenase P9WPP1 CP125_MYCTU Mycobacterium tuberculosis 3 0.9138
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.9118
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.9072
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8882
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8809
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8763
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8595
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8364
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8207
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8164
Oxysterols receptor LXR-beta P55055 NR1H2_HUMAN Homo sapiens 4 0.8049
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7799
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 3 0.7793
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.7741
Beta-elicitin cryptogein P15570 ELIB_PHYCR Phytophthora cryptogea 4 0.7657
Beta-lactoglobulin P02754 LACB_BOVIN Bos taurus 3 0.7636
Alcohol dehydrogenase 1C P00326 ADH1G_HUMAN Homo sapiens 3 0.7503
Japanin M1MR49 M1MR49_RHIAP Rhipicephalus appendiculatus 5 0.7443
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7414
Beta-lactoglobulin P02754 LACB_BOVIN Bos taurus 3 0.7413
Vitamin D(3) 25-hydroxylase C4B644 CPVDH_PSEAH Pseudonocardia autotrophica 3 0.7268
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7159
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7150
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 3 0.7126
Nuclear receptor ROR-alpha P35398 RORA_HUMAN Homo sapiens 5 0.7066

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