(7R)-11-hydroxy-sydonic acid methyl ester - Compound Card

(7R)-11-hydroxy-sydonic acid methyl ester

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(7R)-11-hydroxy-sydonic acid methyl ester

Structure
Zoomed Structure
  • Family: Fungi - Trichocomaceae
  • Kingdom: Fungi
  • Class: Terpenoid
    • Subclass: Meroterpenoid
Canonical Smiles COC(=O)c1ccc(c(c1)O)[C@@](CCCC(O)(C)C)(O)C
InChI InChI=1S/C16H24O5/c1-15(2,19)8-5-9-16(3,20)12-7-6-11(10-13(12)17)14(18)21-4/h6-7,10,17,19-20H,5,8-9H2,1-4H3/t16-/m1/s1
InChIKey VEIQUPXZHBFTEP-MRXNPFEDSA-N
Formula C16H24O5
HBA 5
HBD 3
MW 296.36
Rotatable Bonds 6
TPSA 86.99
LogP 2.33
Number Rings 1
Number Aromatic Rings 1
Heavy Atom Count 21
Formal Charge 0
Fraction CSP3 0.56
Exact Mass 296.16
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Aspergillus versicolor Trichocomaceae Fungi 46472

Showing of synonyms

  • Elsbaey M, Tanaka C, et al. (2019). New secondary metabolites from the mangrove endophytic fungus Aspergillus versicolor. Phytochemistry Letters,2019,32,70-76. [View]
Pubchem: 146682510
Nmrshiftdb2: 60048238

No compound-protein relationship available.

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 296.36 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.76
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.660
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.41

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.120
Plasma Protein Binding
39.7
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
6.570
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.660
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
0.140
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
4.170
Micronucleos
Safe
NR-AhR
Safe
NR-AR
Safe
NR-AR-LBD
Safe
NR-Aromatase
Safe
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Safe
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
0.190
Rat (Acute)
1.890
Rat (Chronic Oral)
2.480
Fathead Minnow
4.000
Respiratory Disease
Safe
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
340.730
Hydration Free Energy
-10.720
Log(D) at pH=7.4
1.870
Log(P)
2.5
Log S
-2.46
Log(Vapor Pressure)
-5.81
Melting Point
104.9
pKa Acid
8.92
pKa Basic
7.09
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 0.9240
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.9115
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 3 0.8910
L-lactate dehydrogenase A chain P04642 LDHA_RAT Rattus norvegicus 3 0.8890
Prolyl tripeptidyl peptidase Q7MUW6 PTP_PORGI Porphyromonas gingivalis 3 0.8876
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8864
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.8849
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 3 0.8835
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.8820
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.8715
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8678
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8664
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 3 0.8645
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 4 0.8586
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8573
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.8487
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.8421
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.8413
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.8369
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 3 0.8344
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.8292
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.8291
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase P0AF12 MTNN_ECOLI Escherichia coli 3 0.8264
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.8254
Retinol-binding protein 4 P18902 RET4_BOVIN Bos taurus 4 0.8237
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8208
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.8190
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.8121
Xylose isomerase P24300 XYLA_STRRU Streptomyces rubiginosus 3 0.8116
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8104
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.8093
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8082
Mitogen-activated protein kinase kinase kinase 5 Q99683 M3K5_HUMAN Homo sapiens 3 0.8076
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.8075
NADPH dehydrogenase 1 Q02899 OYE1_SACPS Saccharomyces pastorianus 3 0.8031
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7988
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7985
Cytidine and deoxycytidylate deaminase zinc-binding region Q82Y41 Q82Y41_NITEU Nitrosomonas europaea 3 0.7922
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7904
ADP-ribosylation factor 1 P84077 ARF1_HUMAN Homo sapiens 2 0.7903
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7891
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7845
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.7843
Cytochrome P450 Q93H81 Q93H81_STRAX Streptomyces avermitilis 3 0.7817
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7765
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.7730
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7712
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7670
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 3 0.7649
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7640
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7636
Dihydroorotate dehydrogenase (quinone), mitochondrial Q08210 PYRD_PLAF7 Plasmodium falciparum 3 0.7617
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7609
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.7598
S-adenosylmethionine decarboxylase proenzyme P17707 DCAM_HUMAN Homo sapiens 3 0.7590
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7588
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7578
Steroid C26-monooxygenase P9WPP1 CP125_MYCTU Mycobacterium tuberculosis 3 0.7572
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7572
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7571
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7569
Methionine aminopeptidase 1 P53582 MAP11_HUMAN Homo sapiens 3 0.7550
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7549
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7540
Aldo-keto reductase family 1 member C1 Q04828 AK1C1_HUMAN Homo sapiens 2 0.7534
Norsolorinic acid synthase Q12053 AFLC_ASPPU Aspergillus parasiticus 3 0.7532
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.7526
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 4 0.7511
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.7510
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7500
Poly [ADP-ribose] polymerase 1 P09874 PARP1_HUMAN Homo sapiens 3 0.7487
RNA-dependent RNA polymerase Q6A562 Q6A562_9VIRU Thosea asigna virus 2 0.7478
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7467
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 3 0.7464
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7447
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 2 0.7442
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7425
chitinase B0Y2Y2 B0Y2Y2_ASPFC Aspergillus fumigatus 3 0.7423
Retinol dehydratase Q26490 Q26490_SPOFR Spodoptera frugiperda 3 0.7413
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 3 0.7413
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 4 0.7403
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.7396
Nuclear receptor ROR-gamma P51449 RORG_HUMAN Homo sapiens 3 0.7395
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7385
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7358
N-alpha-acetyltransferase 50 Q9GZZ1 NAA50_HUMAN Homo sapiens 3 0.7356
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7342
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7339
Metallo-beta-lactamase type 2 P26918 BLAB_AERHY Aeromonas hydrophila 2 0.7334
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7303
Vitamin D3 receptor P13053 VDR_RAT Rattus norvegicus 3 0.7298
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7273
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7271
Glutamate receptor 3 P19492 GRIA3_RAT Rattus norvegicus 3 0.7266
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.7251
Retinol-binding protein 1 P09455 RET1_HUMAN Homo sapiens 3 0.7245
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.7245
4-hydroxy-7-methoxy-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-2-yl glucoside beta-D-glucosidase 1, chloroplastic P49235 HGGL1_MAIZE Zea mays 2 0.7236
Flavoredoxin Q72HI0 Q72HI0_THET2 Thermus thermophilus 3 0.7235
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 2 0.7231
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7226
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7223
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7215
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 2 0.7214
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7209
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7201
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 3 0.7200
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 2 0.7191
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.7191
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7190
HTH-type transcriptional regulator EthR P9WMC1 ETHR_MYCTU Mycobacterium tuberculosis 3 0.7187
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7183
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 3 0.7181
Serine/threonine-protein kinase toxin HipA P23874 HIPA_ECOLI Escherichia coli 3 0.7160
LIM domain kinase 1 P53667 LIMK1_HUMAN Homo sapiens 2 0.7134
UDP-N-acetylmuramoyl-L-alanyl-D-glutamate--LD-lysine ligase Q9WY79 MURE_THEMA Thermotoga maritima 3 0.7124
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7123
Thyroid hormone receptor alpha P04625 THA_CHICK Gallus gallus 3 0.7106
High affinity 3',5'-cyclic-AMP phosphodiesterase 7A Q13946 PDE7A_HUMAN Homo sapiens 3 0.7105
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.7097
Pyridoxal kinase O00764 PDXK_HUMAN Homo sapiens 2 0.7089
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7075
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 2 0.7074
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 2 0.7071
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7070
N-acetyltransferase domain-containing protein Q9HV14 Q9HV14_PSEAE Pseudomonas aeruginosa 3 0.7069
Integrin alpha-L P20701 ITAL_HUMAN Homo sapiens 3 0.7057
Methionine aminopeptidase 2 P50579 MAP2_HUMAN Homo sapiens 3 0.7046
Kynurenine/alpha-aminoadipate aminotransferase, mitochondrial Q8N5Z0 AADAT_HUMAN Homo sapiens 2 0.7037
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 2 0.7032
Ferrichrome outer membrane transporter/phage receptor P06971 FHUA_ECOLI Escherichia coli 3 0.7026
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 2 0.7019
Lanosterol synthase P48449 ERG7_HUMAN Homo sapiens 3 0.7018
GTP 3',8-cyclase P69848 MOAA_STAA8 Staphylococcus aureus 3 0.7014
Toxoflavin degrading enzyme E3SET7 E3SET7_PAEPO Paenibacillus polymyxa 3 0.7014
Chitinase Q54276 Q54276_SERMA Serratia marcescens 3 0.7011
Catalase-peroxidase Q3JNW6 KATG_BURP1 Burkholderia pseudomallei 2 0.7004
Aromatase P11511 CP19A_HUMAN Homo sapiens 3 0.7003
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.7002
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7001
5-methyltetrahydropteroyltriglutamate--homocysteine methyltransferase 1 O50008 METE1_ARATH Arabidopsis thaliana 2 0.7001

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