Sterigmatocystin - Compound Card

Sterigmatocystin

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Sterigmatocystin

Structure
Zoomed Structure
  • Family: Fungi - Trichocomaceae
  • Kingdom: Fungi
  • Class: Polyketide
    • Subclass: Xanthone Polyketide
Canonical Smiles COc1cc2O[C@@H]3[C@H](c2c2c1c(=O)c1c(o2)cccc1O)C=CO3
InChI InChI=1S/C18H12O6/c1-21-11-7-12-13(8-5-6-22-18(8)24-12)17-15(11)16(20)14-9(19)3-2-4-10(14)23-17/h2-8,18-19H,1H3/t8-,18+/m0/s1
InChIKey UTSVPXMQSFGQTM-DCXZOGHSSA-N
Formula C18H12O6
HBA 6
HBD 1
MW 324.29
Rotatable Bonds 1
TPSA 78.13
LogP 3.01
Number Rings 5
Number Aromatic Rings 3
Heavy Atom Count 24
Formal Charge 0
Fraction CSP3 0.17
Exact Mass 324.06
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Aspergillus sp Trichocomaceae Fungi 5065
2 Aspergillus versicolor Trichocomaceae Fungi 46472

Showing of synonyms

  • Abdelwahab M, Kurtán T, et al. (2018). Induced secondary metabolites from the endophytic fungus Aspergillus versicolor through bacterial co-culture and OSMAC approaches. Tetrahedron Letters,2018,59(27),2647-2652. [View]
  • 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]
CPRiL: 6648
Structure

SMILES: O1C=CC2C1Oc(c23)ccc4c3oc5c(c4=O)cccc5

Level: 0

Mol. Weight: 324.29 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.57
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.330
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-0.94

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.230
Plasma Protein Binding
70.92
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Inhibitor
CYP 1A2 Inhibitor
Non-Inhibitor
CYP 1A2 Substrate
Substrate
CYP 2C19 Inhibitor
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
Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
5.320
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.340
Biodegradation
Safe
Carcinogenesis
Toxic
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.580
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
4.630
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
0.010
Rat (Acute)
3.240
Rat (Chronic Oral)
2.340
Fathead Minnow
4.980
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Safe

General Properties

Boiling Point
473.530
Hydration Free Energy
-10.200
Log(D) at pH=7.4
1.880
Log(P)
3.53
Log S
-4.36
Log(Vapor Pressure)
-9.02
Melting Point
244.34
pKa Acid
6.73
pKa Basic
4.8
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform O02697 PK3CG_PIG Sus scrofa 3 0.9281
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.9267
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.9102
Biflaviolin synthase CYP158A1 Q9KZF5 C1581_STRCO Streptomyces coelicolor / M145) 3 0.8833
Thymidylate synthase P0A886 TYSY_ECO57 Escherichia coli O157:H7 3 0.8824
Nuclear receptor ROR-gamma P51449 RORG_HUMAN Homo sapiens 3 0.8806
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 4 0.8645
Gag-Pol polyprotein P04585 POL_HV1H2 Human immunodeficiency virus type 1 group M subtype B 3 0.8634
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.8633
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.8578
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.8575
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 4 0.8567
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.8495
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8372
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.8372
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 3 0.8326
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 3 0.8321
Proto-oncogene tyrosine-protein kinase Src P12931 SRC_HUMAN Homo sapiens 3 0.8316
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.8307
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.8303
Gag-Pol polyprotein P04585 POL_HV1H2 Human immunodeficiency virus type 1 group M subtype B 3 0.8239
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.8223
Gag-Pol polyprotein P04585 POL_HV1H2 Human immunodeficiency virus type 1 group M subtype B 3 0.8199
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.8103
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 4 0.8070
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.8043
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.8025
Stromelysin-1 P08254 MMP3_HUMAN Homo sapiens 3 0.8024
Gag-Pol polyprotein P04585 POL_HV1H2 Human immunodeficiency virus type 1 group M subtype B 3 0.8021
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.8019
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.8018
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.8016
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7994
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta P78356 PI42B_HUMAN Homo sapiens 4 0.7987
Protein ppBat Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron VPI-5482 3 0.7957
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 3 0.7945
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7925
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 4 0.7914
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7903
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 3 0.7883
Alcohol dehydrogenase E chain P00327 ADH1E_HORSE Equus caballus 4 0.7880
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.7845
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7845
Abscisic acid receptor PYL2 O80992 PYL2_ARATH Arabidopsis thaliana 3 0.7801
tRNA (adenine(9)-N1)-methyltransferase Q4J894 TRM10_SULAC Sulfolobus acidocaldarius 4 0.7793
Gag-Pol polyprotein P03366 POL_HV1B1 Human immunodeficiency virus type 1 group M subtype B 3 0.7773
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.7771
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7766
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7764
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 4 0.7699
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.7699
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7691
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7658
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7603
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.7588
NADPH--cytochrome P450 reductase P00388 NCPR_RAT Rattus norvegicus 4 0.7586
LIM domain kinase 1 P53667 LIMK1_HUMAN Homo sapiens 3 0.7580
ADP compounds hydrolase NudE P45799 NUDE_ECOLI Escherichia coli 3 0.7577
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.7568
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7517
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7517
Alcohol dehydrogenase E chain P00327 ADH1E_HORSE Equus caballus 4 0.7476
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7452
Putative ketoacyl reductase P16544 ACT3_STRCO Streptomyces coelicolor / M145) 3 0.7451
Nitroreductase domain-containing protein Q8DW21 Q8DW21_STRMU Streptococcus mutans serotype c 3 0.7448
Protein LlR18A P52778 L18A_LUPLU Lupinus luteus 3 0.7432
Dihydrofolate reductase P00374 DYR_HUMAN Homo sapiens 3 0.7424
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7397
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 4 0.7385
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7369
Mitogen-activated protein kinase 10 P53779 MK10_HUMAN Homo sapiens 3 0.7359
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7344
DNA mismatch repair protein MutS P23909 MUTS_ECOLI Escherichia coli 3 0.7333
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 3 0.7319
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.7295
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase P0AF12 MTNN_ECOLI Escherichia coli 3 0.7295
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 3 0.7289
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7284
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7269
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7268
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase F6MZ55 F6MZ55_9FIRM Sporomusa ovata 3 0.7265
NADPH--cytochrome P450 reductase P00388 NCPR_RAT Rattus norvegicus 4 0.7239
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7239
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7232
Serine/threonine-protein kinase toxin HipA P23874 HIPA_ECOLI Escherichia coli 3 0.7231
Cytohesin-2 Q99418 CYH2_HUMAN Homo sapiens 3 0.7230
Insulin receptor P06213 INSR_HUMAN Homo sapiens 4 0.7219
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7214
Sulfotransferase 1A1 P50225 ST1A1_HUMAN Homo sapiens 3 0.7206
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 4 0.7202
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 4 0.7196
DNA mismatch repair protein Msh2 P43246 MSH2_HUMAN Homo sapiens 3 0.7183
Abscisic acid receptor PYL1 Q8VZS8 PYL1_ARATH Arabidopsis thaliana 3 0.7182
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7168
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7166
Chloramphenicol acetyltransferase P62577 CAT_ECOLX Escherichia coli 2 0.7150
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7144
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7119
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 3 0.7118
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7108
Dodecin Q5SIE3 DODEC_THET8 Thermus thermophilus 4 0.7079
Transthyretin Q9PTT3 Q9PTT3_SPAAU Sparus aurata 3 0.7079
ActVA 6 protein Q53908 Q53908_STRCH Streptomyces coelicolor 4 0.7064
Abscisic acid receptor PYR1 O49686 PYR1_ARATH Arabidopsis thaliana 3 0.7063
Hygromycin-B 4-O-kinase P00557 KHYB_ECOLX Escherichia coli 3 0.7033
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7032
Oxysterols receptor LXR-beta P55055 NR1H2_HUMAN Homo sapiens 3 0.7029
Maltokinase A1TH50 MAK_MYCVP Mycolicibacterium vanbaalenii 3 0.7025
Sulfotransferase 1A1 P50225 ST1A1_HUMAN Homo sapiens 3 0.7025
Hygromycin-B 4-O-kinase P00557 KHYB_ECOLX Escherichia coli 3 0.7014
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7008
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7001
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 2 0.7000

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