Preussilide B - Compound Card

Preussilide B

Select a section from the left sidebar

Preussilide B

Structure
Zoomed Structure
  • Family: Fungi - Sporormiaceae
  • Kingdom: Fungi
  • Class: Polyketide
    • Subclass: Bicyclic Polyketide
Canonical Smiles CC(=O)CC1=C(C)C=C2[C@@H]([C@H]1/C=C(/C=C(/C=C/C(=O)O)\C)\C)[C@H](C)[C@@H]([C@@H](C2)C)O
InChI InChI=1S/C25H34O4/c1-14(7-8-23(27)28)9-15(2)10-22-21(13-18(5)26)16(3)11-20-12-17(4)25(29)19(6)24(20)22/h7-11,17,19,22,24-25,29H,12-13H2,1-6H3,(H,27,28)/b8-7+,14-9+,15-10+/t17-,19+,22+,24+,25-/m1/s1
InChIKey WPOOLKYXEKIQSJ-FKYFWVDISA-N
Formula C25H34O4
HBA 3
HBD 2
MW 398.54
Rotatable Bonds 6
TPSA 74.6
LogP 5.02
Number Rings 2
Number Aromatic Rings 0
Heavy Atom Count 29
Formal Charge 0
Fraction CSP3 0.52
Exact Mass 398.25
Number of Lipinski Rule Violations 1
# Species Family Kingdom NCBI Taxonomy ID
1 Preussia similis Sporormiaceae Fungi 269685

Showing of synonyms

  • Noumeur S.R, Helaly S.E, et al. (2017). Preussilides A−F, bicyclic polyketides from the endophytic fungus preussia similis with antiproliferative activity. Journal of natural products,2017, 80(5), 1531-1540. [View] [PubMed]
Pubchem: 132489953
Nmrshiftdb2: 70100288

No compound-protein relationship available.

Structure

SMILES: C1CCCC(C1=2)CC=CC2

Level: 0

Mol. Weight: 398.54 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.86
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.93
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-3.0

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.35
Plasma Protein Binding
94.32
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
Substrate
CYP 2D6 Inhibitor
Non-Inhibitor
CYP 2D6 Substrate
Non-Substrate
CYP 3A4 Inhibitor
Non-Inhibitor
CYP 3A4 Substrate
Substrate
OATP1B1
Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
-0.32
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.21
Biodegradation
Safe
Carcinogenesis
Toxic
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.02
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
3.89
Micronucleos
Safe
NR-AhR
Safe
NR-AR
Safe
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
-4.37
Rat (Acute)
3.1
Rat (Chronic Oral)
2.58
Fathead Minnow
4.69
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
454.29
Hydration Free Energy
-3.64
Log(D) at pH=7.4
1.57
Log(P)
4.23
Log S
-5.03
Log(Vapor Pressure)
-8.3
Melting Point
201.18
pKa Acid
6.82
pKa Basic
4.79
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.9891
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.8271
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 3 0.8262
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8248
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8191
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8083
Retinol-binding protein 1 P02696 RET1_RAT Rattus norvegicus 3 0.7754
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7737
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7682
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7575
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 3 0.7449
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.7447
Nuclear receptor ROR-gamma P51449 RORG_HUMAN Homo sapiens 2 0.7410
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 2 0.7332
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7301
Alcohol dehydrogenase 1C P00326 ADH1G_HUMAN Homo sapiens 3 0.7266
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7260
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.7219
Retinoic acid receptor RXR Q8T5C6 RXR_BIOGL Biomphalaria glabrata 3 0.7180
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7173
Ferrichrome outer membrane transporter/phage receptor P06971 FHUA_ECOLI Escherichia coli 3 0.7116
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7102
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7097

Download SDF