Aranorosin-2-methylether - Compound Card

Aranorosin-2-methylether

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Aranorosin-2-methylether

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]1CC2(O[C@H]1OC)[C@@H]1O[C@@H]1C(=O)[C@H]1[C@@H]2O1)\C)C
InChI InChI=1S/C24H35NO6/c1-5-6-7-8-9-14(2)12-15(3)10-11-17(26)25-16-13-24(31-23(16)28-4)21-19(29-21)18(27)20-22(24)30-20/h10-12,14,16,19-23H,5-9,13H2,1-4H3,(H,25,26)/b11-10+,15-12+/t14-,16+,19-,20+,21-,22+,23-,24?/m1/s1
InChIKey GKVIDXZWKPCOHE-ZBTRLJRXSA-N
Formula C24H35NO6
HBA 6
HBD 1
MW 433.55
Rotatable Bonds 10
TPSA 89.69
LogP 2.83
Number Rings 4
Number Aromatic Rings 0
Heavy Atom Count 31
Formal Charge 0
Fraction CSP3 0.75
Exact Mass 433.25
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: 101898623

No compound-protein relationship available.

Structure

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

Level: 0

Mol. Weight: 433.55 g/mol

Cytotoxic

Absorption

Caco-2 (logPapp)
-5.05
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.71
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
-2.73

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.67
Plasma Protein Binding
29.76
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
Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
14.97
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.94
Biodegradation
Safe
Carcinogenesis
Toxic
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.25
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
7.14
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
-91.4
Rat (Acute)
3.58
Rat (Chronic Oral)
1.67
Fathead Minnow
4.52
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
458.05
Hydration Free Energy
-2.75
Log(D) at pH=7.4
3.07
Log(P)
3.61
Log S
-4.31
Log(Vapor Pressure)
-8.2
Melting Point
113.18
pKa Acid
5.11
pKa Basic
2.15
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 3 0.9540
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 3 0.9540
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.9247
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.9247
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8953
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8953
Macrophage metalloelastase P39900 MMP12_HUMAN Homo sapiens 3 0.8916
Macrophage metalloelastase P39900 MMP12_HUMAN Homo sapiens 3 0.8916
Xylose isomerase P24300 XYLA_STRRU Streptomyces rubiginosus 3 0.8625
Xylose isomerase P24300 XYLA_STRRU Streptomyces rubiginosus 3 0.8625
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8409
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8409
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.8335
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.8335
Beta-lactoglobulin P02754 LACB_BOVIN Bos taurus 3 0.8253
Beta-lactoglobulin P02754 LACB_BOVIN Bos taurus 3 0.8253
Integrin alpha-L P20701 ITAL_HUMAN Homo sapiens 3 0.8164
Integrin alpha-L P20701 ITAL_HUMAN Homo sapiens 3 0.8164
Alcohol dehydrogenase 1C P00326 ADH1G_HUMAN Homo sapiens 2 0.8072
Alcohol dehydrogenase 1C P00326 ADH1G_HUMAN Homo sapiens 2 0.8072
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.8071
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.8071
Beta-lactoglobulin P02754 LACB_BOVIN Bos taurus 3 0.8062
Beta-lactoglobulin P02754 LACB_BOVIN Bos taurus 3 0.8062
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.8042
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.8042
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 2 0.8015
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 2 0.8015
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.8009
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.8009
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7986
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7986
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
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 2 0.7939
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 2 0.7939
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7936
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7936
Aldo-keto reductase family 1 member C1 Q04828 AK1C1_HUMAN Homo sapiens 2 0.7908
Aldo-keto reductase family 1 member C1 Q04828 AK1C1_HUMAN Homo sapiens 2 0.7908
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7835
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7835
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7816
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7816
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7813
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7813
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 3 0.7812
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 3 0.7812
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7809
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7809
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 2 0.7801
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 2 0.7801
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 2 0.7789
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 2 0.7789
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 2 0.7787
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 2 0.7787
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7777
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7777
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7750
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7750
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 2 0.7749
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 2 0.7749
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7722
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7722
3-ketosteroid dehydrogenase Q9RA02 Q9RA02_RHOER Rhodococcus erythropolis 2 0.7719
3-ketosteroid dehydrogenase Q9RA02 Q9RA02_RHOER Rhodococcus erythropolis 2 0.7719
Lanosterol 14-alpha-demethylase Q385E8 Q385E8_TRYB2 Trypanosoma brucei brucei 3 0.7716
Lanosterol 14-alpha-demethylase Q385E8 Q385E8_TRYB2 Trypanosoma brucei brucei 3 0.7716
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7703
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7703
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 2 0.7697
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 2 0.7697
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7694
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7694
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 2 0.7693
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 2 0.7693
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7683
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7683
Cellular retinoic acid-binding protein 2 P29373 RABP2_HUMAN Homo sapiens 2 0.7635
Cellular retinoic acid-binding protein 2 P29373 RABP2_HUMAN Homo sapiens 2 0.7635
4,4'-diapophytoene synthase A9JQL9 CRTM_STAAU Staphylococcus aureus 2 0.7627
4,4'-diapophytoene synthase A9JQL9 CRTM_STAAU Staphylococcus aureus 2 0.7627
Enoyl-[acyl-carrier-protein] reductase [NADH] P9WGR1 INHA_MYCTU Mycobacterium tuberculosis 2 0.7626
Enoyl-[acyl-carrier-protein] reductase [NADH] P9WGR1 INHA_MYCTU Mycobacterium tuberculosis 2 0.7626
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7624
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7624
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7588
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7588
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7575
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7575
Camphor 5-monooxygenase P00183 CPXA_PSEPU Pseudomonas putida 3 0.7551
Camphor 5-monooxygenase P00183 CPXA_PSEPU Pseudomonas putida 3 0.7551
Gastrotropin Q6IMW5 Q6IMW5_DANRE Danio rerio 2 0.7547
Gastrotropin Q6IMW5 Q6IMW5_DANRE Danio rerio 2 0.7547
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7546
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7546
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 2 0.7529
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 2 0.7529
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 2 0.7516
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 2 0.7516
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 2 0.7467
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 2 0.7467
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7459
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7459
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7420
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7420
Abscisic acid receptor PYL2 O80992 PYL2_ARATH Arabidopsis thaliana 2 0.7402
Abscisic acid receptor PYL2 O80992 PYL2_ARATH Arabidopsis thaliana 2 0.7402
Fatty acid-binding protein 10-A, liver basic Q9I8L5 FA10A_DANRE Danio rerio 2 0.7371
Fatty acid-binding protein 10-A, liver basic Q9I8L5 FA10A_DANRE Danio rerio 2 0.7371
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 2 0.7349
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 2 0.7349
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7318
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7318
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7311
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7311
Cellular retinol-binding protein type II Q8UVG6 Q8UVG6_DANRE Danio rerio 3 0.7305
Cellular retinol-binding protein type II Q8UVG6 Q8UVG6_DANRE Danio rerio 3 0.7305
Albumin P02768 ALBU_HUMAN Homo sapiens 2 0.7286
Albumin P02768 ALBU_HUMAN Homo sapiens 2 0.7286
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7249
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7249
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 2 0.7231
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 2 0.7231
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7169
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7169
Abscisic acid receptor PYL10 Q8H1R0 PYL10_ARATH Arabidopsis thaliana 3 0.7165
Abscisic acid receptor PYL10 Q8H1R0 PYL10_ARATH Arabidopsis thaliana 3 0.7165
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 2 0.7152
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 2 0.7152
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 2 0.7122
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 2 0.7122
Vitamin D3 receptor P13053 VDR_RAT Rattus norvegicus 3 0.7084
Vitamin D3 receptor P13053 VDR_RAT Rattus norvegicus 3 0.7084
Bacteriorhodopsin P02945 BACR_HALSA Halobacterium salinarum 3 0.7077
Bacteriorhodopsin P02945 BACR_HALSA Halobacterium salinarum 3 0.7077
Nuclear receptor ROR-beta P45446 RORB_RAT Rattus norvegicus 2 0.7049
Nuclear receptor ROR-beta P45446 RORB_RAT Rattus norvegicus 2 0.7049
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 2 0.7026
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 2 0.7026
Vitamin D3 receptor P13053 VDR_RAT Rattus norvegicus 3 0.7004
Vitamin D3 receptor P13053 VDR_RAT Rattus norvegicus 3 0.7004

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