Tetraacetylaltersolanol A - Compound Card

Tetraacetylaltersolanol A

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Tetraacetylaltersolanol A

Structure
Zoomed Structure
  • Family: Fungi - Pleosporaceae
  • Kingdom: Fungi
  • Class: Polyketide
Canonical Smiles COc1cc(OC(=O)C)c2c(c1)C(=O)C1=C(C2=O)[C@H](OC(=O)C)[C@H]([C@@]([C@@H]1OC(=O)C)(C)O)OC(=O)C
InChI InChI=1S/C24H24O12/c1-9(25)33-15-8-13(32-6)7-14-16(15)20(30)17-18(19(14)29)22(35-11(3)27)24(5,31)23(36-12(4)28)21(17)34-10(2)26/h7-8,21-23,31H,1-6H3/t21-,22+,23+,24-/m0/s1
InChIKey BBNIRZPZESGMEK-KEZOAJOQSA-N
Formula C24H24O12
HBA 12
HBD 1
MW 504.44
Rotatable Bonds 5
TPSA 168.8
LogP 0.86
Number Rings 3
Number Aromatic Rings 1
Heavy Atom Count 36
Formal Charge 0
Fraction CSP3 0.42
Exact Mass 504.13
Number of Lipinski Rule Violations 2
# Species Family Kingdom NCBI Taxonomy ID
1 Stemphylium globuliferum Pleosporaceae Fungi 245170

Showing of synonyms

  • Teiten MH, Mack F, et al. (2013). Anticancer effect of altersolanol A, a metabolite produced by the endophytic fungus Stemphylium globuliferum, mediated by its pro-apoptotic and anti-invasive potential via the inhibition of NF-κB activity. Bioorganic and Medicinal Chemistry,2013,21(13),3850-3858. [View] [PubMed]
Pubchem: 73356552
Nmrshiftdb2: 70103396

No compound-protein relationship available.

Structure

SMILES: c1cccc(c12)C(=O)C3=C(C2=O)CCCC3

Level: 0

Mol. Weight: 504.44 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.12
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.590
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-3.09

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.330
Plasma Protein Binding
75.05
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
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
Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
7.730
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.140
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
1.860
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
6.550
Micronucleos
Toxic
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
Safe
T. Pyriformis
-197.320
Rat (Acute)
2.660
Rat (Chronic Oral)
3.090
Fathead Minnow
4.510
Respiratory Disease
Safe
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Toxic
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Toxic

General Properties

Boiling Point
479.290
Hydration Free Energy
-2.870
Log(D) at pH=7.4
1.040
Log(P)
1.62
Log S
-3.81
Log(Vapor Pressure)
-8.93
Melting Point
216.12
pKa Acid
5.27
pKa Basic
0.48
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.9273
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.9273
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.8894
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.8894
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.8589
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.8589
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8088
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8088
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7740
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7740
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.7358
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.7358
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta P78356 PI42B_HUMAN Homo sapiens 3 0.7357
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta P78356 PI42B_HUMAN Homo sapiens 3 0.7357
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7344
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7344
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7329
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7329
GMP synthase [glutamine-hydrolyzing] Q8IJR9 Q8IJR9_PLAF7 Plasmodium falciparum 4 0.7231
GMP synthase [glutamine-hydrolyzing] Q8IJR9 Q8IJR9_PLAF7 Plasmodium falciparum 4 0.7231
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 2 0.7164
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 2 0.7164
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7126
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7126
Metallo-beta-lactamase type 2 P26918 BLAB_AERHY Aeromonas hydrophila 2 0.7108
Metallo-beta-lactamase type 2 P26918 BLAB_AERHY Aeromonas hydrophila 2 0.7108
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 2 0.7095
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 2 0.7095
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 2 0.7082
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 2 0.7082
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 2 0.7009
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 2 0.7009
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 2 0.7001
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 2 0.7001

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