Gymnastatin B - Compound Card

Gymnastatin B

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Gymnastatin B

Structure
Zoomed Structure
  • Family: Fungi - Gymnoascaceae
  • Kingdom: Fungi
  • Class: Amide
    • Subclass: Acyl Amide
Canonical Smiles CCCCCC[C@H](/C=C(/C=C/C(=O)N[C@H]1C[C@@]2(O[C@H]1OC)C=C(Cl)C(=O)[C@@H]([C@H]2O)Cl)\C)C
InChI InChI=1S/C24H35Cl2NO5/c1-5-6-7-8-9-15(2)12-16(3)10-11-19(28)27-18-14-24(32-23(18)31-4)13-17(25)21(29)20(26)22(24)30/h10-13,15,18,20,22-23,30H,5-9,14H2,1-4H3,(H,27,28)/b11-10+,16-12+/t15-,18+,20+,22-,23-,24+/m1/s1
InChIKey HCHKYWWJMUJBHB-NBSJDVKISA-N
Formula C24H35Cl2NO5
HBA 5
HBD 2
MW 488.45
Rotatable Bonds 10
TPSA 84.86
LogP 4.39
Number Rings 2
Number Aromatic Rings 0
Heavy Atom Count 32
Formal Charge 0
Fraction CSP3 0.67
Exact Mass 487.19
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Gymnascella dankaliensis Gymnoascaceae Fungi 166389

Showing of synonyms

  • Hammerschmidt L, Aly AH, et al. (2015). Cytotoxic acyl amides from the soil fungus Gymnascella dankaliensis. Bioorganic and Medicinal Chemistry,2015,23,712-719. [View] [PubMed]

No compound-protein relationship available.

Structure

SMILES: O1CCCC12C=CC(=O)CC2

Level: 0

Mol. Weight: 488.45 g/mol

Cytotoxic

Absorption

Caco-2 (logPapp)
-4.97
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.84
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.57

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.4
Plasma Protein Binding
73.5
Steady State Volume of Distribution
-

Metabolism

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

Excretion

Clearance
3.57
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.06
Biodegradation
Safe
Carcinogenesis
Toxic
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.0
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
7.85
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
Toxic
T. Pyriformis
-44.89
Rat (Acute)
2.85
Rat (Chronic Oral)
2.12
Fathead Minnow
4.51
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Toxic
SR-ATAD5
Toxic
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
464.66
Hydration Free Energy
-3.21
Log(D) at pH=7.4
4.29
Log(P)
4.98
Log S
-4.61
Log(Vapor Pressure)
-8.86
Melting Point
117.95
pKa Acid
7.77
pKa Basic
4.8
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Mexicain P84346 MEX1_JACME Jacaratia mexicana 3 0.9234
Mexicain P84346 MEX1_JACME Jacaratia mexicana 3 0.9234
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 3 0.9228
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 3 0.9228
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.9216
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.9216
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 3 0.9194
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 3 0.9194
Xylose isomerase P24300 XYLA_STRRU Streptomyces rubiginosus 3 0.9054
Xylose isomerase P24300 XYLA_STRRU Streptomyces rubiginosus 3 0.9054
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8987
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8987
Macrophage metalloelastase P39900 MMP12_HUMAN Homo sapiens 3 0.8911
Macrophage metalloelastase P39900 MMP12_HUMAN Homo sapiens 3 0.8911
Beta-lactoglobulin P02754 LACB_BOVIN Bos taurus 3 0.8834
Beta-lactoglobulin P02754 LACB_BOVIN Bos taurus 3 0.8834
Sodium/potassium-transporting ATPase subunit alpha Q4H132 Q4H132_SQUAC Squalus acanthias 3 0.8724
Sodium/potassium-transporting ATPase subunit alpha Q4H132 Q4H132_SQUAC Squalus acanthias 3 0.8724
Pyridoxal kinase, putative C4LVZ4 C4LVZ4_ENTHI Entamoeba histolytica 3 0.8723
Pyridoxal kinase, putative C4LVZ4 C4LVZ4_ENTHI Entamoeba histolytica 3 0.8723
Integrin alpha-L P20701 ITAL_HUMAN Homo sapiens 3 0.8512
Integrin alpha-L P20701 ITAL_HUMAN Homo sapiens 3 0.8512
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8379
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8379
Beta-lactoglobulin P02754 LACB_BOVIN Bos taurus 3 0.8271
Beta-lactoglobulin P02754 LACB_BOVIN Bos taurus 3 0.8271
Cellular retinol-binding protein type II Q8UVG6 Q8UVG6_DANRE Danio rerio 4 0.8268
Cellular retinol-binding protein type II Q8UVG6 Q8UVG6_DANRE Danio rerio 4 0.8268
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.8210
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.8210
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.8094
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.8094
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.8073
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.8073
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.8035
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.8035
Alcohol dehydrogenase 1C P00326 ADH1G_HUMAN Homo sapiens 2 0.8006
Alcohol dehydrogenase 1C P00326 ADH1G_HUMAN Homo sapiens 2 0.8006
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 2 0.7994
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 2 0.7994
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7978
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7978
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7973
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7973
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7943
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7943
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 2 0.7928
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 2 0.7928
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7926
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7926
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7912
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7912
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.7908
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.7908
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.7900
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.7900
Aldo-keto reductase family 1 member C1 Q04828 AK1C1_HUMAN Homo sapiens 2 0.7899
Aldo-keto reductase family 1 member C1 Q04828 AK1C1_HUMAN Homo sapiens 2 0.7899
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7867
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7867
Retinol-binding protein 2 P50120 RET2_HUMAN Homo sapiens 3 0.7861
Retinol-binding protein 2 P50120 RET2_HUMAN Homo sapiens 3 0.7861
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 2 0.7845
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 2 0.7845
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 2 0.7826
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 2 0.7826
Retinol-binding protein 1 P02696 RET1_RAT Rattus norvegicus 3 0.7818
Retinol-binding protein 1 P02696 RET1_RAT Rattus norvegicus 3 0.7818
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7812
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7812
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7806
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7806
Retinol-binding protein 4 P18902 RET4_BOVIN Bos taurus 3 0.7797
Retinol-binding protein 4 P18902 RET4_BOVIN Bos taurus 3 0.7797
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 2 0.7784
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 2 0.7784
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7773
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7773
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7764
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7764
Gastrotropin Q6IMW5 Q6IMW5_DANRE Danio rerio 3 0.7762
Gastrotropin Q6IMW5 Q6IMW5_DANRE Danio rerio 3 0.7762
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7694
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7694
Bacteriorhodopsin P02945 BACR_HALSA Halobacterium salinarum 3 0.7691
Bacteriorhodopsin P02945 BACR_HALSA Halobacterium salinarum 3 0.7691
Cellular retinoic acid-binding protein 2 P29373 RABP2_HUMAN Homo sapiens 2 0.7675
Cellular retinoic acid-binding protein 2 P29373 RABP2_HUMAN Homo sapiens 2 0.7675
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7623
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7623
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7619
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7619
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 2 0.7606
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 2 0.7606
Lanosterol 14-alpha-demethylase Q385E8 Q385E8_TRYB2 Trypanosoma brucei brucei 3 0.7598
Lanosterol 14-alpha-demethylase Q385E8 Q385E8_TRYB2 Trypanosoma brucei brucei 3 0.7598
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 2 0.7594
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 2 0.7594
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.7584
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.7584
Chorismate mutase AroH P19080 AROH_BACSU Bacillus subtilis 3 0.7569
Chorismate mutase AroH P19080 AROH_BACSU Bacillus subtilis 3 0.7569
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7565
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7565
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7563
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7563
Soluble cytochrome b562 P0ABE7 C562_ECOLX Escherichia coli 2 0.7559
Soluble cytochrome b562 P0ABE7 C562_ECOLX Escherichia coli 2 0.7559
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 2 0.7553
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 2 0.7553
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7547
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7547
Albumin P02768 ALBU_HUMAN Homo sapiens 2 0.7535
Albumin P02768 ALBU_HUMAN Homo sapiens 2 0.7535
4,4'-diapophytoene synthase A9JQL9 CRTM_STAAU Staphylococcus aureus 2 0.7528
4,4'-diapophytoene synthase A9JQL9 CRTM_STAAU Staphylococcus aureus 2 0.7528
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7521
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7521
Rhodopsin P02699 OPSD_BOVIN Bos taurus 3 0.7520
Rhodopsin P02699 OPSD_BOVIN Bos taurus 3 0.7520
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7470
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7470
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 2 0.7426
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 2 0.7426
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 2 0.7415
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 2 0.7415
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7406
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7406
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7384
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7384
Enoyl-[acyl-carrier-protein] reductase [NADH] P9WGR1 INHA_MYCTU Mycobacterium tuberculosis 2 0.7371
Enoyl-[acyl-carrier-protein] reductase [NADH] P9WGR1 INHA_MYCTU Mycobacterium tuberculosis 2 0.7371
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 2 0.7347
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 2 0.7347
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 2 0.7332
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 2 0.7332
Beta-lactoglobulin P02754 LACB_BOVIN Bos taurus 3 0.7321
Beta-lactoglobulin P02754 LACB_BOVIN Bos taurus 3 0.7321
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 2 0.7318
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 2 0.7318
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 2 0.7308
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 2 0.7308
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 2 0.7300
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 2 0.7300
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7269
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7269
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 2 0.7267
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 2 0.7267
3-hydroxy-3-methylglutaryl-coenzyme A reductase P13702 MVAA_PSEMV Pseudomonas mevalonii 3 0.7256
3-hydroxy-3-methylglutaryl-coenzyme A reductase P13702 MVAA_PSEMV Pseudomonas mevalonii 3 0.7256
Trichodiene synthase P13513 TRI5_FUSSP Fusarium sporotrichioides 2 0.7240
Trichodiene synthase P13513 TRI5_FUSSP Fusarium sporotrichioides 2 0.7240
Retinoic acid receptor RXR-alpha P28700 RXRA_MOUSE Mus musculus 3 0.7228
Retinoic acid receptor RXR-alpha P28700 RXRA_MOUSE Mus musculus 3 0.7228
Retinoic acid receptor beta P10826 RARB_HUMAN Homo sapiens 3 0.7218
Retinoic acid receptor beta P10826 RARB_HUMAN Homo sapiens 3 0.7218
Retinol-binding protein 4 P18902 RET4_BOVIN Bos taurus 3 0.7169
Retinol-binding protein 4 P18902 RET4_BOVIN Bos taurus 3 0.7169
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7152
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7152
Nuclear receptor subfamily 1 group I member 3 O35627 NR1I3_MOUSE Mus musculus 3 0.7126
Nuclear receptor subfamily 1 group I member 3 O35627 NR1I3_MOUSE Mus musculus 3 0.7126
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 2 0.7121
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 2 0.7121
Lactoylglutathione lyase Q04760 LGUL_HUMAN Homo sapiens 3 0.7095
Lactoylglutathione lyase Q04760 LGUL_HUMAN Homo sapiens 3 0.7095
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7067
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7067
Vitamin D3 receptor P13053 VDR_RAT Rattus norvegicus 3 0.7057
Vitamin D3 receptor P13053 VDR_RAT Rattus norvegicus 3 0.7057
Abscisic acid receptor PYL10 Q8H1R0 PYL10_ARATH Arabidopsis thaliana 3 0.7030
Abscisic acid receptor PYL10 Q8H1R0 PYL10_ARATH Arabidopsis thaliana 3 0.7030
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7025
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7025
Retinol dehydratase Q26490 Q26490_SPOFR Spodoptera frugiperda 3 0.7023
Retinol dehydratase Q26490 Q26490_SPOFR Spodoptera frugiperda 3 0.7023

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