Simplicilone A - Compound Card

Simplicilone A

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Simplicilone A

Structure
Zoomed Structure
  • Family: Fungi - Cordycipitaceae
  • Kingdom: Fungi
  • Class: Polyketide
    • Subclass: Tetracyclic Polyketide
Canonical Smiles C1CC[C@H]2[C@@H]([C@@H]1C)[C@H]1[C@H](C(=C2)C)[C@@]([C@@H]([C@@]2(C1=O)C(=O)[C@@H](N(C2=O)C)[C@@H](C)O)C)(C)O
InChI InChI=1S/C24H35NO5/c1-11-8-7-9-15-10-12(2)18-17(16(11)15)20(27)24(14(4)23(18,5)30)21(28)19(13(3)26)25(6)22(24)29/h10-11,13-19,26,30H,7-9H2,1-6H3/t11-,13-,14+,15-,16-,17+,18+,19+,23+,24-/m1/s1
InChIKey SXNQSYLKDWUURY-HADVBVATSA-N
Formula C24H35NO5
HBA 5
HBD 2
MW 417.55
Rotatable Bonds 1
TPSA 94.91
LogP 1.98
Number Rings 4
Number Aromatic Rings 0
Heavy Atom Count 30
Formal Charge 0
Fraction CSP3 0.79
Exact Mass 417.25
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Simplicillium subtropicum Cordycipitaceae Fungi 935212

Showing of synonyms

  • Anoumedem EGM, Mountessou BYG, et al. (2020). Simplicilones A and B Isolated from the Endophytic Fungus Simplicillium subtropicum SPC3. Antibiotics (Basel). 2020, 9(11), 753. [View] [PubMed]

No compound-protein relationship available.

Structure

SMILES: O=C1NCC(=O)C12C(=O)C3C(CC2)C=CC4C3CCCC4

Level: 0

Mol. Weight: 417.55 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.83
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.74
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.48

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.89
Plasma Protein Binding
65.44
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
Substrate
CYP 2C9 Inhibitor
Non-Inhibitor
CYP 2C9 Substrate
Non-Substrate
CYP 2D6 Inhibitor
Non-Inhibitor
CYP 2D6 Substrate
Non-Substrate
CYP 3A4 Inhibitor
Inhibitor
CYP 3A4 Substrate
Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
7.89
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.05
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.31
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
7.14
Micronucleos
Toxic
NR-AhR
Safe
NR-AR
Safe
NR-AR-LBD
Safe
NR-Aromatase
Safe
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Safe
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
-22.86
Rat (Acute)
2.76
Rat (Chronic Oral)
2.2
Fathead Minnow
3.74
Respiratory Disease
Safe
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
457.59
Hydration Free Energy
-6.51
Log(D) at pH=7.4
2.5
Log(P)
3.22
Log S
-3.09
Log(Vapor Pressure)
-9.23
Melting Point
180.74
pKa Acid
3.81
pKa Basic
4.5
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7922
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7881
Retinol dehydratase Q26490 Q26490_SPOFR Spodoptera frugiperda 3 0.7406
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 3 0.7343
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7146
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 4 0.7110
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 3 0.7073
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7010

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