Isoshamixanthone - Compound Card

Isoshamixanthone

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Isoshamixanthone

Structure
Zoomed Structure
  • Family: Fungi - Trichocomaceae
  • Kingdom: Fungi
  • Class: Xanthone
    • Subclass: Pyrano Xanthone
Canonical Smiles CC(=CCc1ccc2c(c1O)c(=O)c1c(o2)cc(c2c1[C@@H](O)[C@@H](CO2)C(=C)C)C)C
InChI InChI=1S/C25H26O5/c1-12(2)6-7-15-8-9-17-20(22(15)26)24(28)19-18(30-17)10-14(5)25-21(19)23(27)16(11-29-25)13(3)4/h6,8-10,16,23,26-27H,3,7,11H2,1-2,4-5H3/t16-,23-/m0/s1
InChIKey UAGOXGIYOPSKFF-HJPURHCSSA-N
Formula C25H26O5
HBA 5
HBD 2
MW 406.48
Rotatable Bonds 3
TPSA 79.9
LogP 5.09
Number Rings 4
Number Aromatic Rings 3
Heavy Atom Count 30
Formal Charge 0
Fraction CSP3 0.32
Exact Mass 406.18
Number of Lipinski Rule Violations 1
# Species Family Kingdom NCBI Taxonomy ID
1 Aspergillus sp Trichocomaceae Fungi 5065

Showing of synonyms

  • Kamel R.A, Abdel-Razek A.S, et al. (2020). Isoshamixanthone: a new pyrano xanthone from endophytic Aspergillus sp. ASCLA and absolute configuration of epiisoshamixanthone. Nat Prod Res,2020,34(8),1080-1090. [View] [PubMed]
Pubchem: 162885344

No compound-protein relationship available.

Structure

SMILES: C1CCOc(c1c23)ccc3oc4c(c2=O)cccc4

Level: 0

Mol. Weight: 406.48 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.87
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.59
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.04

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.34
Plasma Protein Binding
79.4
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Inhibitor
CYP 1A2 Inhibitor
Inhibitor
CYP 1A2 Substrate
Non-Substrate
CYP 2C19 Inhibitor
Inhibitor
CYP 2C19 Substrate
Non-Substrate
CYP 2C9 Inhibitor
Inhibitor
CYP 2C9 Substrate
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
3.34
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.3
Biodegradation
Safe
Carcinogenesis
Toxic
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.57
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.63
Micronucleos
Toxic
NR-AhR
Toxic
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
-21.79
Rat (Acute)
2.26
Rat (Chronic Oral)
2.38
Fathead Minnow
5.3
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Toxic

General Properties

Boiling Point
509.2
Hydration Free Energy
-5.09
Log(D) at pH=7.4
3.47
Log(P)
6.98
Log S
-5.95
Log(Vapor Pressure)
-10.44
Melting Point
186.54
pKa Acid
7.1
pKa Basic
6.32
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Flavin reductase (NADPH) P30043 BLVRB_HUMAN Homo sapiens 3 0.9614
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.8836
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.8605
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8505
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.8489
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.8418
Aldo-keto reductase family 1 member B10 O60218 AK1BA_HUMAN Homo sapiens 3 0.8024
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.7966
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7947
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7916
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.7774
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.7712
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7671
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 3 0.7670
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7603
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 3 0.7562
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7556
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7507
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 3 0.7504
Angiotensin-converting enzyme Q10714 ACE_DROME Drosophila melanogaster 3 0.7404
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 3 0.7384
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7381
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 2 0.7345
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 2 0.7341
Calmodulin P62157 CALM_BOVIN Bos taurus 3 0.7323
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 4 0.7309
Lanosterol 14-alpha-demethylase Q385E8 Q385E8_TRYB2 Trypanosoma brucei brucei 3 0.7294
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7278
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7275
Chloramphenicol acetyltransferase P62577 CAT_ECOLX Escherichia coli 3 0.7265
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 3 0.7221
Na(+):neurotransmitter symporter (Snf family) O67854 O67854_AQUAE Aquifex aeolicus 3 0.7219
Aldo-keto reductase family 1 member B1 P80276 ALDR_PIG Sus scrofa 3 0.7195
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7182
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7164
Flavin-dependent monooxygenase Q93L51 TETX_BACT4 Bacteroides thetaiotaomicron 3 0.7156
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7101
Protein S100-A13 Q99584 S10AD_HUMAN Homo sapiens 2 0.7098
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7086
4-hydroxyphenylacetate 3-monooxygenase Q8YHT7 Q8YHT7_BRUME Brucella melitensis biotype 1 2 0.7069
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7062
Carbonyl reductase [NADPH] 1 P16152 CBR1_HUMAN Homo sapiens 2 0.7046
E3 ubiquitin-protein ligase Mdm2 P56273 MDM2_XENLA Xenopus laevis 3 0.7044
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 3 0.7043
Carbonyl reductase [NADPH] 1 P16152 CBR1_HUMAN Homo sapiens 2 0.7034

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