Aranorosin - Compound Card

Aranorosin

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Aranorosin

Structure
Zoomed Structure
  • Family: Fungi - Gymnoascaceae
  • Kingdom: Fungi
  • Class: Amide
    • Subclass: Acyl Amide
Canonical Smiles CCCCCC[C@H](/C=C(/C=C/C(=O)NC1CC2(OC1O)[C@@H]1O[C@@H]1C(=O)[C@H]1[C@@H]2O1)\C)C
InChI InChI=1S/C23H33NO6/c1-4-5-6-7-8-13(2)11-14(3)9-10-16(25)24-15-12-23(30-22(15)27)20-18(28-20)17(26)19-21(23)29-19/h9-11,13,15,18-22,27H,4-8,12H2,1-3H3,(H,24,25)/b10-9+,14-11+/t13-,15?,18-,19+,20-,21+,22?,23?/m1/s1
InChIKey JHTWWPWUODMKEO-PHJKOLFRSA-N
Formula C23H33NO6
HBA 6
HBD 2
MW 419.52
Rotatable Bonds 9
TPSA 100.69
LogP 2.18
Number Rings 4
Number Aromatic Rings 0
Heavy Atom Count 30
Formal Charge 0
Fraction CSP3 0.74
Exact Mass 419.23
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: 6444217
Nmrshiftdb2: 70012399
CPRiL: 275326
Structure

SMILES: O1CCCC12C3C(O3)C(=O)C4C2O4

Level: 0

Mol. Weight: 419.52 g/mol

Cytotoxic

Absorption

Caco-2 (logPapp)
-5.12
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.74
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
-2.81

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.65
Plasma Protein Binding
28.58
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
Non-Substrate
CYP 2C9 Inhibitor
Non-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
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
14.25
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.66
Biodegradation
Safe
Carcinogenesis
Toxic
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.22
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
6.8
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
-52.15
Rat (Acute)
3.58
Rat (Chronic Oral)
1.86
Fathead Minnow
4.48
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
458.12
Hydration Free Energy
-2.99
Log(D) at pH=7.4
2.18
Log(P)
2.98
Log S
-4.08
Log(Vapor Pressure)
-9.05
Melting Point
122.33
pKa Acid
4.74
pKa Basic
2.62
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.9404
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.9404
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8950
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8950
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 3 0.8911
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 3 0.8911
Cellular retinol-binding protein type II Q8UVG6 Q8UVG6_DANRE Danio rerio 4 0.8701
Cellular retinol-binding protein type II Q8UVG6 Q8UVG6_DANRE Danio rerio 4 0.8701
Macrophage metalloelastase P39900 MMP12_HUMAN Homo sapiens 3 0.8657
Macrophage metalloelastase P39900 MMP12_HUMAN Homo sapiens 3 0.8657
Integrin alpha-L P20701 ITAL_HUMAN Homo sapiens 3 0.8534
Integrin alpha-L P20701 ITAL_HUMAN Homo sapiens 3 0.8534
Xylose isomerase P24300 XYLA_STRRU Streptomyces rubiginosus 3 0.8533
Xylose isomerase P24300 XYLA_STRRU Streptomyces rubiginosus 3 0.8533
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8509
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8509
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.8173
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.8173
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8173
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8173
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.8070
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.8070
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.8067
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.8067
Ascorbate-specific PTS system EIIC component P39301 ULAA_ECOLI Escherichia coli 3 0.8028
Ascorbate-specific PTS system EIIC component P39301 ULAA_ECOLI Escherichia coli 3 0.8028
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.7983
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.7983
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7975
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7975
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7952
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7952
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 2 0.7935
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 2 0.7935
3-ketosteroid dehydrogenase Q9RA02 Q9RA02_RHOER Rhodococcus erythropolis 2 0.7918
3-ketosteroid dehydrogenase Q9RA02 Q9RA02_RHOER Rhodococcus erythropolis 2 0.7918
Aldo-keto reductase family 1 member C1 Q04828 AK1C1_HUMAN Homo sapiens 2 0.7896
Aldo-keto reductase family 1 member C1 Q04828 AK1C1_HUMAN Homo sapiens 2 0.7896
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7871
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7871
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7818
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7818
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7795
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7795
Retinol dehydratase Q26490 Q26490_SPOFR Spodoptera frugiperda 3 0.7780
Retinol dehydratase Q26490 Q26490_SPOFR Spodoptera frugiperda 3 0.7780
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7766
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7766
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 2 0.7761
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 2 0.7761
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7754
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7754
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7747
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7747
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7727
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7727
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7711
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7711
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 2 0.7702
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 2 0.7702
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 2 0.7699
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 2 0.7699
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 2 0.7614
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 2 0.7614
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 2 0.7614
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 2 0.7614
Beta-lactoglobulin P02754 LACB_BOVIN Bos taurus 2 0.7609
Beta-lactoglobulin P02754 LACB_BOVIN Bos taurus 2 0.7609
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7606
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7606
Cellular retinoic acid-binding protein 2 P29373 RABP2_HUMAN Homo sapiens 2 0.7582
Cellular retinoic acid-binding protein 2 P29373 RABP2_HUMAN Homo sapiens 2 0.7582
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 2 0.7578
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 2 0.7578
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 2 0.7472
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 2 0.7472
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7446
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7446
Soluble cytochrome b562 P0ABE7 C562_ECOLX Escherichia coli 2 0.7376
Soluble cytochrome b562 P0ABE7 C562_ECOLX Escherichia coli 2 0.7376
Oxysterols receptor LXR-beta P55055 NR1H2_HUMAN Homo sapiens 3 0.7366
Oxysterols receptor LXR-beta P55055 NR1H2_HUMAN Homo sapiens 3 0.7366
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7361
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7361
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 2 0.7351
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 2 0.7351
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 2 0.7329
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 2 0.7329
Enoyl-[acyl-carrier-protein] reductase [NADH] P9WGR1 INHA_MYCTU Mycobacterium tuberculosis 2 0.7323
Enoyl-[acyl-carrier-protein] reductase [NADH] P9WGR1 INHA_MYCTU Mycobacterium tuberculosis 2 0.7323
Vitamin D3 dihydroxylase P18326 CPXE_STRGO Streptomyces griseolus 3 0.7320
Vitamin D3 dihydroxylase P18326 CPXE_STRGO Streptomyces griseolus 3 0.7320
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 2 0.7314
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 2 0.7314
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 2 0.7314
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 2 0.7314
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 2 0.7304
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 2 0.7304
Fatty acid-binding protein 10-A, liver basic Q9I8L5 FA10A_DANRE Danio rerio 2 0.7301
Fatty acid-binding protein 10-A, liver basic Q9I8L5 FA10A_DANRE Danio rerio 2 0.7301
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7300
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7300
Nuclear receptor ROR-gamma P51449 RORG_HUMAN Homo sapiens 3 0.7297
Nuclear receptor ROR-gamma P51449 RORG_HUMAN Homo sapiens 3 0.7297
Prostaglandin reductase 2 Q8N8N7 PTGR2_HUMAN Homo sapiens 2 0.7278
Prostaglandin reductase 2 Q8N8N7 PTGR2_HUMAN Homo sapiens 2 0.7278
Abscisic acid receptor PYL2 O80992 PYL2_ARATH Arabidopsis thaliana 2 0.7272
Abscisic acid receptor PYL2 O80992 PYL2_ARATH Arabidopsis thaliana 2 0.7272
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 2 0.7249
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 2 0.7249
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7235
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7235
4,4'-diapophytoene synthase A9JQL9 CRTM_STAAU Staphylococcus aureus 2 0.7228
4,4'-diapophytoene synthase A9JQL9 CRTM_STAAU Staphylococcus aureus 2 0.7228
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7222
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7222
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7220
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7220
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.7210
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.7210
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7172
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7172
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7167
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7167
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 2 0.7161
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 2 0.7161
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7116
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7116
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 2 0.7115
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 2 0.7115
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7111
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7111
Retinoic acid receptor RXR Q8T5C6 RXR_BIOGL Biomphalaria glabrata 3 0.7111
Retinoic acid receptor RXR Q8T5C6 RXR_BIOGL Biomphalaria glabrata 3 0.7111
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7091
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7091
Abscisic acid receptor PYL3 Q9SSM7 PYL3_ARATH Arabidopsis thaliana 2 0.7071
Abscisic acid receptor PYL3 Q9SSM7 PYL3_ARATH Arabidopsis thaliana 2 0.7071
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7070
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7070
Lanosterol synthase P48449 ERG7_HUMAN Homo sapiens 3 0.7065
Lanosterol synthase P48449 ERG7_HUMAN Homo sapiens 3 0.7065
Retinol-binding protein 4 P18902 RET4_BOVIN Bos taurus 3 0.7056
Retinol-binding protein 4 P18902 RET4_BOVIN Bos taurus 3 0.7056
Camphor 5-monooxygenase P00183 CPXA_PSEPU Pseudomonas putida 3 0.7009
Camphor 5-monooxygenase P00183 CPXA_PSEPU Pseudomonas putida 3 0.7009

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