Talaromannin B - Compound Card

Talaromannin B

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Talaromannin B

Structure
Zoomed Structure
  • Family: Fungi - Trichocomaceae
  • Kingdom: Fungi
  • Class: Alkaloid
    • Subclass: Cyclic Peptide
Canonical Smiles Cc1cc(O)c2c(c1)C(=O)c1c(C2=O)c(O)c(c(c1)O)c1c(O)cc2c(c1O)cc1c(c2O)C(=O)CC(C1)(C)O
InChI InChI=1S/C30H22O10/c1-10-3-14-21(16(31)4-10)28(38)22-15(25(14)35)7-18(33)24(29(22)39)23-17(32)6-13-12(27(23)37)5-11-8-30(2,40)9-19(34)20(11)26(13)36/h3-7,31-33,36-37,39-40H,8-9H2,1-2H3
InChIKey KEBSBWHDDWCBPX-UHFFFAOYSA-N
Formula C30H22O10
HBA 10
HBD 7
MW 542.5
Rotatable Bonds 1
TPSA 192.82
LogP 3.7
Number Rings 6
Number Aromatic Rings 4
Heavy Atom Count 40
Formal Charge 0
Fraction CSP3 0.17
Exact Mass 542.12
Number of Lipinski Rule Violations 2
# Species Family Kingdom NCBI Taxonomy ID
1 Talaromyces wortmannii Trichocomaceae Fungi 28567

Showing of synonyms

  • Bara R (2012). Natural Products from Endophytic Fungus Talaromyces wortmannii: Their Structure and mechanism of Actions. PhD Thesis, Institute for Pharmaceutical Biology and Biotechnology, University of Dusseldorf,2012, pp. 1-142.. [View]
Pubchem: 71717072

No compound-protein relationship available.

Structure

SMILES: c1cccc(C2=O)c1C(=O)c(c23)ccc(c3)-c(c4)ccc(c5)c4cc(c56)CCCC6=O

Level: 1

Mol. Weight: 542.5 g/mol

Structure

SMILES: c1cccc(c12)C(=O)c3c(C2=O)cccc3

Level: 0

Mol. Weight: 542.5 g/mol

Structure

SMILES: O=C1CCCc(c12)cc3c(c2)cccc3

Level: 0

Mol. Weight: 542.5 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-6.41
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Non-Absorbed
Madin-Darby Canine Kidney
-5.38
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
3.83

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.88
Plasma Protein Binding
75.3
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Inhibitor
CYP 1A2 Inhibitor
Non-Inhibitor
CYP 1A2 Substrate
Non-Substrate
CYP 2C19 Inhibitor
Non-Inhibitor
CYP 2C19 Substrate
Non-Substrate
CYP 2C9 Inhibitor
Inhibitor
CYP 2C9 Substrate
Non-Substrate
CYP 2D6 Inhibitor
Non-Inhibitor
CYP 2D6 Substrate
Non-Substrate
CYP 3A4 Inhibitor
Non-Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
10.75
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.34
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
0.88
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
6.1
Micronucleos
Toxic
NR-AhR
Toxic
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
-3071.02
Rat (Acute)
2.57
Rat (Chronic Oral)
4.58
Fathead Minnow
14.21
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
619.02
Hydration Free Energy
-3.17
Log(D) at pH=7.4
2.74
Log(P)
5.78
Log S
-6.51
Log(Vapor Pressure)
-8.85
Melting Point
313.57
pKa Acid
6.79
pKa Basic
5.18
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase F6MZ55 F6MZ55_9FIRM Sporomusa ovata 3 0.8925
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase F6MZ55 F6MZ55_9FIRM Sporomusa ovata 3 0.8925
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.8702
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.8702
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8571
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8571
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8515
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8515
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.8489
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.8489
Cytosolic purine 5'-nucleotidase P49902 5NTC_HUMAN Homo sapiens 3 0.8335
Cytosolic purine 5'-nucleotidase P49902 5NTC_HUMAN Homo sapiens 3 0.8335
Transcriptional regulator, PadR-like family A2RI36 A2RI36_LACLM Lactococcus lactis subsp. cremoris 3 0.8207
Transcriptional regulator, PadR-like family A2RI36 A2RI36_LACLM Lactococcus lactis subsp. cremoris 3 0.8207
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8111
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8111
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8082
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8082
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7930
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7930
Aldos-2-ulose dehydratase P84193 AUD_PHACH Phanerodontia chrysosporium 3 0.7871
Aldos-2-ulose dehydratase P84193 AUD_PHACH Phanerodontia chrysosporium 3 0.7871
Na(+):neurotransmitter symporter (Snf family) O67854 O67854_AQUAE Aquifex aeolicus 3 0.7675
Na(+):neurotransmitter symporter (Snf family) O67854 O67854_AQUAE Aquifex aeolicus 3 0.7675
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7563
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7563
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.7515
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.7515
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7484
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7484
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7465
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7465
Vitamin D-binding protein P02774 VTDB_HUMAN Homo sapiens 3 0.7346
Vitamin D-binding protein P02774 VTDB_HUMAN Homo sapiens 3 0.7346
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7297
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7297
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7247
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7247
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 4 0.7218
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 4 0.7218
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7187
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7187
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 2 0.7083
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 2 0.7083
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7078
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7078
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 2 0.7044
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 2 0.7044

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