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name Structure Reference Source Properties Activities Metabolism

3,4,5-trihydroxy-6-({10-hydroxy-4-methyl-12-oxa-4-azapentacyclo[9.6.1.0¹,¹³.0?,¹?.0?,¹?]octadeca-7(18),8,10,15-tetraen-14-yl}oxy)oxane-2-carboxylic acid

AlkaPlorer ID: AK002785

Synonym: None

IUPAC Name: (2S,3S,4S,5R,6R)-6-[[(4R,4aR,7S,7aR,12bS)-9-hydroxy-3-methyl-2,4,4a,7,7a,13-hexahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-7-yl]oxy]-3,4,5-trihydroxyoxane-2-carboxylic acid

Structure

SMILES: CN1CC[C@]23C4=C5C=CC(O)=C4O[C@H]2[C@@H](O[C@@H]2O[C@H](C(=O)O)[C@@H](O)[C@H](O)[C@H]2O)C=C[C@H]3[C@H]1C5

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InChI: InChI=1S/C23H27NO9/c1-24-7-6-23-10-3-5-13(31-22-17(28)15(26)16(27)19(33-22)21(29)30)20(23)32-18-12(25)4-2-9(14(18)23)8-11(10)24/h2-5,10-11,13,15-17,19-20,22,25-28H,6-8H2,1H3,(H,29,30)/t10-,11+,13-,15-,16-,17+,19-,20-,22+,23-/m0/s1

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InChIKey: GNJCUHZOSOYIEC-GAROZEBRSA-N

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Source

Species Genus Family Order Class Phylum Kingdom Domain
Mytilus edulis Mytilus Mytilidae Mytilida Bivalvia Mollusca Metazoa Eukaryota

Properties Information

Molecule Weight: 461.4670000000001

TPSA？: 149.15

MolLogP？: -0.8853999999999989

Number of H-Donors: 5

Number of H-Acceptors: 9

RingCount: 6

Activities Information

Organism Target Name Standard Type Standard Value Standard Units doi
Homo sapiens Mu opioid receptor Ki 12.9 nM 10.1016/j.bmcl.2005.01.072
Homo sapiens Mu opioid receptor Ki 63.0 nM 10.1021/jm501535r
Homo sapiens Opioid receptors; mu & delta Selectivity 12.5 None 10.1016/j.bmcl.2005.01.072
Homo sapiens Opioid receptors; mu & delta Selectivity 12.5 None 10.1021/jm049554t
Homo sapiens Opioid receptors; mu & delta Selectivity 316.0 None 10.1016/j.bmcl.2005.01.072
Homo sapiens Opioid receptors; mu & kappa Selectivity 316.0 None 10.1021/jm049554t
Homo sapiens Plasma K(p,uu,CSF) 0.1 None 10.1021/jm901036q
Homo sapiens UDP-glucuronosyltransferase 2B7 Activity nan None None
Homo sapiens UDP-glucuronosyltransferase 2B7 Km 240000.0 nM 10.1016/j.pharmthera.2004.10.013
Homo sapiens UDP-glucuronosyltransferase 2B7 Km 630000.0 nM 10.1016/j.pharmthera.2004.10.013
Homo sapiens UDP-glucuronosyltransferase 2B7 Km 970000.0 nM 10.1016/j.pharmthera.2004.10.013
Homo sapiens UDP-glucuronosyltransferase 2B7 Km 1300000.0 nM 10.1016/j.pharmthera.2004.10.013
Homo sapiens UDP-glucuronosyltransferase 2B7 Km 13700000.0 nM 10.1016/j.pharmthera.2004.10.013
Homo sapiens UDP-glucuronosyltransferase 2B7 Vmax 7.0 pmol/min/mg protein 10.1016/j.pharmthera.2004.10.013
Homo sapiens UDP-glucuronosyltransferase 2B7 Vmax 22.0 pmol/min/mg protein 10.1016/j.pharmthera.2004.10.013
Homo sapiens UDP-glucuronosyltransferase 2B7 Vmax 47.0 pmol/min/mg protein 10.1016/j.pharmthera.2004.10.013
Homo sapiens UDP-glucuronosyltransferase 2B7 Vmax 78.0 pmol/min/mg protein 10.1016/j.pharmthera.2004.10.013
Homo sapiens UDP-glucuronosyltransferase 2B7 Vmax 99.0 pmol/min/mg protein 10.1016/j.pharmthera.2004.10.013
Mus musculus Mus musculus AUEC 937.0 A% min-1 10.1016/s0960-894x(03)00056-8
Mus musculus Mus musculus AUEC 1359.0 A% min-1 10.1016/s0960-894x(03)00056-8
Mus musculus Mus musculus ED50 2.7 mg.kg-1 10.1016/j.ejmech.2011.05.076
Mus musculus Mus musculus Permeability nan None 10.1021/jm990968+
Rattus norvegicus Brain AUC 323.08 ng.hr.mL-1 10.1021/jm501535r
Rattus norvegicus Brain Fu 0.87 None 10.1124/dmd.110.035998
Rattus norvegicus Brain Kp 0.86 None 10.1124/dmd.110.035998
Rattus norvegicus Brain Vd 0.98 L.kg-1 10.1124/dmd.110.035998
Rattus norvegicus Brain Vdu 0.99 ml 10.1021/jm901036q
Rattus norvegicus Mu opioid receptor Ki 1.5 nM 10.1016/s0960-894x(03)00056-8
Rattus norvegicus Mu opioid receptor Ki 26.0 nM 10.1016/s0960-894x(03)00056-8
Rattus norvegicus Plasma Cp(f) 2.1 uM 10.1021/jm901036q
Rattus norvegicus Plasma Fu 0.98 None 10.1021/jm901036q
Rattus norvegicus Plasma K(p,uu,CSF) 0.017 None 10.1021/jm901036q
Rattus norvegicus Rattus norvegicus Activity nan None 10.1021/jm8011245
None ADMET AUC 2584.69 ng.hr.mL-1 10.1021/jm501535r
None ADMET BPR 0.008 None 10.1021/jm901036q
None ADMET BPR 0.05 None 10.1021/acs.jmedchem.0c01367
None ADMET CL 2.2 mL.min-1.kg-1 10.1124/dmd.108.020479
None ADMET K(p,uu,brain) 0.008 None 10.1021/jm901036q
None ADMET K(p,uu,brain) 0.56 None 10.1021/jm501535r
None ADMET MRT 0.91 hr 10.1124/dmd.108.020479
None ADMET T1/2 1.4 hr 10.1124/dmd.108.020479
None ADMET Vdss 0.12 L.kg-1 10.1124/dmd.108.020479
None No relevant target CLogP 1.0 None 10.1016/S0960-894X(01)80191-8
None No relevant target CLogP 1.3 None 10.1016/S0960-894X(01)80191-8
None No relevant target CLogP 1.6 None 10.1016/S0960-894X(01)80191-8
None No relevant target Ki 134896288.26 nM 10.1021/jm00108a005
None No relevant target Ki 426579518.8 nM 10.1021/jm00108a005
None No relevant target Ki 457088189.61 nM 10.1021/jm00108a005
None No relevant target Ki 478630092.32 nM 10.1021/jm00108a005
None No relevant target Ki 524807460.25 nM 10.1021/jm00108a005
None No relevant target Ki 602559586.07 nM 10.1021/jm00108a005
None No relevant target pKa -2.0 None 10.1021/jm960073m
None No relevant target pKa -1.21 None 10.1021/jm960073m
None No relevant target pKa -0.79 None 10.1021/jm960073m
None No relevant target pKa -0.76 None 10.1021/jm960073m
None No relevant target pKa -0.53 None 10.1021/jm960073m
None No relevant target pKa -0.33 None 10.1021/jm960073m
None No relevant target pKa -0.22 None 10.1021/jm960073m
None No relevant target pKa -0.19 None 10.1021/jm960073m
None No relevant target pKa -0.15 None 10.1021/jm960073m
None No relevant target pKa -0.04 None 10.1021/jm960073m
None No relevant target pKa 0.03 None 10.1021/jm960073m
None No relevant target pKa 2.77 None 10.1007/s11095-013-1232-z
None No relevant target pKa 2.77 None 10.1021/jm960073m
None No relevant target pKa 3.23 None 10.1021/jm00108a005
None No relevant target pKa 4.3 None 10.1124/dmd.110.035998
None No relevant target pKa 8.22 None 10.1021/jm960073m
None No relevant target pKa 9.0 None 10.1124/dmd.110.035998
None No relevant target pKa 9.42 None 10.1021/jm960073m
None Nucleic Acid Kp 0.05 None 10.1021/jm501535r
None Unchecked EC50 72.3 nM 10.1016/j.bmcl.2005.01.072
None Unchecked EC50 72.3 None 10.1021/jm049554t
None Unchecked EC50 190.0 nM 10.1016/j.bmcl.2005.01.072
None Unchecked EC50 190.0 None 10.1021/jm049554t
None Unchecked EC50 10000.0 nM 10.1016/j.bmcl.2005.01.072
None Unchecked EC50 10000.0 None 10.1021/jm049554t
None Unchecked Emax 45.0 % 10.1016/j.bmcl.2005.01.072
None Unchecked Emax 45.0 None 10.1021/jm049554t
None Unchecked Emax 80.0 % 10.1016/j.bmcl.2005.01.072
None Unchecked Emax 80.0 None 10.1021/jm049554t
None Unchecked Emax nan None 10.1016/j.bmcl.2005.01.072
None Unchecked Emax nan None 10.1021/jm049554t
None Unchecked Ki 170.0 nM 10.1016/j.bmcl.2005.01.072
None Unchecked Ki 4060.0 nM 10.1016/j.bmcl.2005.01.072
None Unchecked Ki 12900.0 nM 10.1021/jm049554t
None Unchecked Ki 170000.0 nM 10.1021/jm049554t
None Unchecked Ki 4060000.0 nM 10.1021/jm049554t

Metabolism Information

AKRT ID Reaction Reaction Link ID
AKRT010574 CN1CC[C@]23c4c5ccc(O)c4O[C@H]2[C@@H](O)C=C[C@H]3[C@H]1C5.O=C(O)[C@H]1O[C@H](OP(=O)(O)OP(=O)(O)OC[C@H]2O[C@@H](n3ccc(=O)[nH]c3=O)[C@H](O)[C@@H]2O)[C@H](O)[C@@H](O)[C@@H]1O>>CN1CC[C@]23c4c5ccc(O)c4O[C@H]2[C@@H](O[C@@H]2O[C@H](C(=O)O)[C@@H](O)[C@H](O)[C@H]2O)C=C[C@H]3[C@H]1C5 R08263