Aranorosinol B - Compound Card

Aranorosinol B

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Aranorosinol 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]1O)[C@@H]1O[C@@H]1[C@]([C@H]1[C@@H]2O1)(O)CC(=O)C)\C)C
InChI InChI=1S/C26H39NO7/c1-5-6-7-8-9-15(2)12-16(3)10-11-19(29)27-18-14-26(34-24(18)30)22-20(32-22)25(31,13-17(4)28)21-23(26)33-21/h10-12,15,18,20-24,30-31H,5-9,13-14H2,1-4H3,(H,27,29)/b11-10+,16-12+/t15-,18+,20-,21+,22+,23-,24+,25+,26-/m1/s1
InChIKey YFJWRMZGLWVCSQ-DUOGUPTFSA-N
Formula C26H39NO7
HBA 7
HBD 3
MW 477.6
Rotatable Bonds 11
TPSA 120.92
LogP 2.32
Number Rings 4
Number Aromatic Rings 0
Heavy Atom Count 34
Formal Charge 0
Fraction CSP3 0.77
Exact Mass 477.27
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: 162851894

No compound-protein relationship available.

Structure

SMILES: O1CCCC12C3C(O3)CC4C2O4

Level: 0

Mol. Weight: 477.6 g/mol

Cytotoxic

Absorption

Caco-2 (logPapp)
-5.19
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.78
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
-2.53

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.73
Plasma Protein Binding
41.31
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
Non-Inhibitor
CYP 2D6 Substrate
Non-Substrate
CYP 3A4 Inhibitor
Non-Inhibitor
CYP 3A4 Substrate
Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
12.52
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.04
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.35
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
6.86
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
-274.79
Rat (Acute)
3.96
Rat (Chronic Oral)
2.14
Fathead Minnow
4.09
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
489.75
Hydration Free Energy
-2.9
Log(D) at pH=7.4
2.19
Log(P)
2.68
Log S
-4.14
Log(Vapor Pressure)
-9.92
Melting Point
134.74
pKa Acid
4.77
pKa Basic
2.96
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.9758
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.9758
Integrin alpha-L P20701 ITAL_HUMAN Homo sapiens 3 0.9655
Integrin alpha-L P20701 ITAL_HUMAN Homo sapiens 3 0.9655
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 3 0.9195
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 3 0.9195
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.8982
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.8982
Beta-lactoglobulin P02754 LACB_BOVIN Bos taurus 3 0.8814
Beta-lactoglobulin P02754 LACB_BOVIN Bos taurus 3 0.8814
Beta-lactoglobulin P02754 LACB_BOVIN Bos taurus 3 0.8436
Beta-lactoglobulin P02754 LACB_BOVIN Bos taurus 3 0.8436
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8414
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8414
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.8372
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.8372
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8197
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8197
Abscisic acid receptor PYL10 Q8H1R0 PYL10_ARATH Arabidopsis thaliana 3 0.8137
Abscisic acid receptor PYL10 Q8H1R0 PYL10_ARATH Arabidopsis thaliana 3 0.8137
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.8064
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.8064
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 2 0.8006
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 2 0.8006
Abscisic acid receptor PYL3 Q9SSM7 PYL3_ARATH Arabidopsis thaliana 3 0.7974
Abscisic acid receptor PYL3 Q9SSM7 PYL3_ARATH Arabidopsis thaliana 3 0.7974
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7968
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7968
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7956
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7956
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 2 0.7944
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 2 0.7944
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7939
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7939
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7933
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7933
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 2 0.7903
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 2 0.7903
Aldo-keto reductase family 1 member C1 Q04828 AK1C1_HUMAN Homo sapiens 2 0.7901
Aldo-keto reductase family 1 member C1 Q04828 AK1C1_HUMAN Homo sapiens 2 0.7901
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7874
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7874
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7854
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7854
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7848
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7848
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 2 0.7843
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 2 0.7843
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7841
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7841
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7838
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7838
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7829
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7829
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.7819
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7819
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.7819
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7819
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 2 0.7813
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 2 0.7813
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7771
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7771
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7746
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7746
Camphor 5-monooxygenase P00183 CPXA_PSEPU Pseudomonas putida 3 0.7735
Camphor 5-monooxygenase P00183 CPXA_PSEPU Pseudomonas putida 3 0.7735
Lysozyme C II P11941 LYSC2_ONCMY Oncorhynchus mykiss 3 0.7728
Lysozyme C II P11941 LYSC2_ONCMY Oncorhynchus mykiss 3 0.7728
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 2 0.7704
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 2 0.7704
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 2 0.7694
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 2 0.7694
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7672
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7672
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 2 0.7663
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 2 0.7663
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 2 0.7639
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 2 0.7639
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 2 0.7632
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 2 0.7632
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7599
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7599
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7597
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7597
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7597
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7597
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 2 0.7594
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 2 0.7594
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.7541
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.7541
Cellular retinol-binding protein type II Q8UVG6 Q8UVG6_DANRE Danio rerio 3 0.7539
Cellular retinol-binding protein type II Q8UVG6 Q8UVG6_DANRE Danio rerio 3 0.7539
Cellular retinoic acid-binding protein 2 P29373 RABP2_HUMAN Homo sapiens 2 0.7538
Cellular retinoic acid-binding protein 2 P29373 RABP2_HUMAN Homo sapiens 2 0.7538
Abscisic acid receptor PYL2 O80992 PYL2_ARATH Arabidopsis thaliana 2 0.7513
Abscisic acid receptor PYL2 O80992 PYL2_ARATH Arabidopsis thaliana 2 0.7513
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7473
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7473
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 2 0.7464
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 2 0.7464
4,4'-diapophytoene synthase A9JQL9 CRTM_STAAU Staphylococcus aureus 2 0.7463
4,4'-diapophytoene synthase A9JQL9 CRTM_STAAU Staphylococcus aureus 2 0.7463
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 2 0.7407
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 2 0.7407
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7393
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7393
Thyroid hormone receptor alpha P04625 THA_CHICK Gallus gallus 3 0.7388
Thyroid hormone receptor alpha P04625 THA_CHICK Gallus gallus 3 0.7388
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 2 0.7386
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 2 0.7386
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7375
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7375
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 2 0.7348
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 2 0.7348
Nuclear receptor ROR-gamma P51449 RORG_HUMAN Homo sapiens 3 0.7338
Nuclear receptor ROR-gamma P51449 RORG_HUMAN Homo sapiens 3 0.7338
Vitamin D3 dihydroxylase P18326 CPXE_STRGO Streptomyces griseolus 3 0.7309
Vitamin D3 dihydroxylase P18326 CPXE_STRGO Streptomyces griseolus 3 0.7309
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 2 0.7293
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 2 0.7293
Abscisic acid receptor PYR1 O49686 PYR1_ARATH Arabidopsis thaliana 2 0.7287
Abscisic acid receptor PYR1 O49686 PYR1_ARATH Arabidopsis thaliana 2 0.7287
Rhodopsin P02699 OPSD_BOVIN Bos taurus 2 0.7268
Rhodopsin P02699 OPSD_BOVIN Bos taurus 2 0.7268
Alcohol dehydrogenase 1C P00326 ADH1G_HUMAN Homo sapiens 2 0.7264
Alcohol dehydrogenase 1C P00326 ADH1G_HUMAN Homo sapiens 2 0.7264
Periplasmic pH-dependent serine endoprotease DegQ P39099 DEGQ_ECOLI Escherichia coli 4 0.7261
Periplasmic pH-dependent serine endoprotease DegQ P39099 DEGQ_ECOLI Escherichia coli 4 0.7261
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7248
Abscisic acid receptor PYL3 Q9SSM7 PYL3_ARATH Arabidopsis thaliana 2 0.7248
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7248
Abscisic acid receptor PYL3 Q9SSM7 PYL3_ARATH Arabidopsis thaliana 2 0.7248
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 2 0.7245
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 2 0.7245
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 2 0.7221
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 2 0.7221
Lanosterol synthase P48449 ERG7_HUMAN Homo sapiens 3 0.7211
Lanosterol synthase P48449 ERG7_HUMAN Homo sapiens 3 0.7211
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 2 0.7196
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 2 0.7196
Enoyl-[acyl-carrier-protein] reductase [NADH] P9WGR1 INHA_MYCTU Mycobacterium tuberculosis 2 0.7187
Enoyl-[acyl-carrier-protein] reductase [NADH] P9WGR1 INHA_MYCTU Mycobacterium tuberculosis 2 0.7187
Beta-lactoglobulin P02754 LACB_BOVIN Bos taurus 3 0.7179
Beta-lactoglobulin P02754 LACB_BOVIN Bos taurus 3 0.7179
Retinol-binding protein 4 P18902 RET4_BOVIN Bos taurus 3 0.7174
Retinol-binding protein 4 P18902 RET4_BOVIN Bos taurus 3 0.7174
Fatty acid-binding protein 10-A, liver basic Q9I8L5 FA10A_DANRE Danio rerio 2 0.7160
Fatty acid-binding protein 10-A, liver basic Q9I8L5 FA10A_DANRE Danio rerio 2 0.7160
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7159
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7159
Endoplasmin, putative Q8I0V4 Q8I0V4_PLAF7 Plasmodium falciparum 3 0.7157
Endoplasmin, putative Q8I0V4 Q8I0V4_PLAF7 Plasmodium falciparum 3 0.7157
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7124
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7124
Macrophage metalloelastase P39900 MMP12_HUMAN Homo sapiens 3 0.7097
Macrophage metalloelastase P39900 MMP12_HUMAN Homo sapiens 3 0.7097
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 2 0.7064
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 2 0.7064
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7060
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7060
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7050
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7050
Abscisic acid receptor PYL2 O80992 PYL2_ARATH Arabidopsis thaliana 3 0.7041
Abscisic acid receptor PYL2 O80992 PYL2_ARATH Arabidopsis thaliana 3 0.7041
Nuclear receptor subfamily 5 group A member 2 O00482 NR5A2_HUMAN Homo sapiens 3 0.7020
Nuclear receptor subfamily 5 group A member 2 O00482 NR5A2_HUMAN Homo sapiens 3 0.7020
Abscisic acid receptor PYR1 O49686 PYR1_ARATH Arabidopsis thaliana 3 0.7019
Abscisic acid receptor PYR1 O49686 PYR1_ARATH Arabidopsis thaliana 3 0.7019
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 2 0.7006
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 2 0.7006
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7002
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7002

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