Gymnastatin S - Compound Card

Gymnastatin S

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Gymnastatin S

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@@H](OC)O[C@H]2[C@]1(O)C=C(Cl)C(=O)[C@H]2Cl)\C)C
InChI InChI=1S/C24H35Cl2NO5/c1-5-6-7-8-9-15(2)12-16(3)10-11-19(28)27-18-13-20(31-4)32-23-21(26)22(29)17(25)14-24(18,23)30/h10-12,14-15,18,20-21,23,30H,5-9,13H2,1-4H3,(H,27,28)/b11-10+,16-12+/t15-,18-,20+,21-,23-,24+/m1/s1
InChIKey BQBNTNYXQBYKTD-PUIDAABOSA-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]
Pubchem: 101158691
Nmrshiftdb2: 70012422

No compound-protein relationship available.

Structure

SMILES: C1=CC(=O)CC(C12)OCCC2

Level: 0

Mol. Weight: 488.45 g/mol

Cytotoxic

Absorption

Caco-2 (logPapp)
-4.89
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.82
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.29

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.38
Plasma Protein Binding
74.3
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
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
2.84
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.11
Biodegradation
Safe
Carcinogenesis
Toxic
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.04
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
7.37
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
-37.74
Rat (Acute)
2.83
Rat (Chronic Oral)
2.06
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
457.82
Hydration Free Energy
-3.39
Log(D) at pH=7.4
4.26
Log(P)
4.96
Log S
-4.73
Log(Vapor Pressure)
-8.72
Melting Point
118.94
pKa Acid
7.56
pKa Basic
5.19
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Xylose isomerase P24300 XYLA_STRRU Streptomyces rubiginosus 3 0.9425
Xylose isomerase P24300 XYLA_STRRU Streptomyces rubiginosus 3 0.9425
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 3 0.8827
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 3 0.8827
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.8621
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.8621
Nuclear receptor subfamily 1 group I member 3 O35627 NR1I3_MOUSE Mus musculus 3 0.8111
Nuclear receptor subfamily 1 group I member 3 O35627 NR1I3_MOUSE Mus musculus 3 0.8111
Beta-lactoglobulin P02754 LACB_BOVIN Bos taurus 3 0.8050
Beta-lactoglobulin P02754 LACB_BOVIN Bos taurus 3 0.8050
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7981
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7981
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.7962
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.7962
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.7862
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.7862
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 2 0.7757
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 2 0.7757
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7745
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7745
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7725
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7725
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 2 0.7547
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 2 0.7547
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7450
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7450
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 2 0.7414
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 2 0.7414
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7388
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7388
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.7378
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.7378
Albumin P02768 ALBU_HUMAN Homo sapiens 2 0.7339
Albumin P02768 ALBU_HUMAN Homo sapiens 2 0.7339
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7324
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7324
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7318
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7318
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7290
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7290
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7284
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7284
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7270
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7270
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7257
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7257
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7248
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7248
Aldo-keto reductase family 1 member C1 Q04828 AK1C1_HUMAN Homo sapiens 2 0.7242
Aldo-keto reductase family 1 member C1 Q04828 AK1C1_HUMAN Homo sapiens 2 0.7242
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 2 0.7240
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 2 0.7240
Cellular retinoic acid-binding protein 2 P29373 RABP2_HUMAN Homo sapiens 2 0.7229
Cellular retinoic acid-binding protein 2 P29373 RABP2_HUMAN Homo sapiens 2 0.7229
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7213
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7213
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 2 0.7209
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 2 0.7209
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7190
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7190
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 2 0.7185
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 2 0.7185
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7176
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7176
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 2 0.7147
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 2 0.7147
Enoyl-[acyl-carrier-protein] reductase [NADH] P9WGR1 INHA_MYCTU Mycobacterium tuberculosis 2 0.7114
Enoyl-[acyl-carrier-protein] reductase [NADH] P9WGR1 INHA_MYCTU Mycobacterium tuberculosis 2 0.7114
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 2 0.7067
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 2 0.7067
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7047
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7047
Abscisic acid receptor PYL3 Q9SSM7 PYL3_ARATH Arabidopsis thaliana 2 0.7036
Abscisic acid receptor PYL3 Q9SSM7 PYL3_ARATH Arabidopsis thaliana 2 0.7036

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