NP-MRD: Showing NP-Card for (2s,3ar,4s,5r,7ar)-2-amino-n-(7,8-dimethoxy-2-oxochromen-3-yl)-3a,4,5-trihydroxy-3,4,5,7a-tetrahydro-1-benzothiophene-2-carboximidic acid (NP0272327)

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Record Information

Version

2.0

Created at

2022-09-08 18:54:42 UTC

Updated at

2022-09-08 18:54:42 UTC

NP-MRD ID

NP0272327

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2s,3ar,4s,5r,7ar)-2-amino-n-(7,8-dimethoxy-2-oxochromen-3-yl)-3a,4,5-trihydroxy-3,4,5,7a-tetrahydro-1-benzothiophene-2-carboximidic acid

Description

N-(2-Oxo-7,8-dimethoxy-2H-1-benzopyran-3-yl)-2-amino-3aalpha,4beta,5alpha-trihydroxy-2,3,3a,4,5,7aalpha-hexahydrobenzo[b]thiophene-2alpha-carboxamide belongs to the class of organic compounds known as coumarins and derivatives. These are polycyclic aromatic compounds containing a 1-benzopyran moiety with a ketone group at the C2 carbon atom (1-benzopyran-2-one). (2s,3ar,4s,5r,7ar)-2-amino-n-(7,8-dimethoxy-2-oxochromen-3-yl)-3a,4,5-trihydroxy-3,4,5,7a-tetrahydro-1-benzothiophene-2-carboximidic acid is found in Aspergillus unilateralis. Based on a literature review very few articles have been published on N-(2-Oxo-7,8-dimethoxy-2H-1-benzopyran-3-yl)-2-amino-3aalpha,4beta,5alpha-trihydroxy-2,3,3a,4,5,7aalpha-hexahydrobenzo[b]thiophene-2alpha-carboxamide.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309082220542D          

 31 34  0  0  1  0            999 V2000
    0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.0513   -0.7537    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2308    0.6674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    1.3349    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.9088    1.5064    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5442    2.1418    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.7596    2.3968    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1573    2.6939    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.9858    3.5009    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9420    2.4389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1135    1.6320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5004    1.0799    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.5004    0.2549    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  9  8  1  4  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 12 10  1  6  0  0  0
 12 13  1  1  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  6  0  0  0
 15 17  1  0  0  0  0
 17 18  1  1  0  0  0
 17 19  1  0  0  0  0
 19 20  1  6  0  0  0
 19 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 15 23  1  0  0  0  0
 23 24  1  1  0  0  0
 12 24  1  0  0  0  0
  8 25  1  0  0  0  0
 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
 27 28  1  0  0  0  0
  6 28  1  0  0  0  0
 28 29  2  0  0  0  0
  3 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
M  END

     RDKit          3D

 53 56  0  0  0  0  0  0  0  0999 V2000
   -7.6616   -2.3149   -1.4281 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0449   -1.0628   -1.3544 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7013   -1.0055   -0.9805 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9758   -2.1388   -0.6854 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6512   -2.0186   -0.3220 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0269   -0.7724   -0.2459 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7036   -0.6373    0.1159 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1425    0.6114    0.1740 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2122    0.8418    0.5373 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0624    1.4026   -0.2489 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6515    1.7966   -1.4896 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4444    1.6057    0.1998 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7753    3.0205    0.1886 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4726    0.8516   -0.5624 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8242   -0.3994    0.1743 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7397   -1.2477    0.1483 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0235   -1.0450   -0.4119 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.3530   -0.5913   -1.6813 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2603   -0.9619    0.4371 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.1600   -1.9264    1.4663 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4060    0.3535    1.1202 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3184    0.8342    1.7197 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0996   -0.0278    1.6163 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6685    1.0530    1.9363 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9618    1.6876   -0.1429 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4599    2.8518   -0.0947 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2199    1.5299   -0.4846 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7902    0.3447   -0.5503 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1247    0.2447   -0.9182 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8346    1.3796   -1.2090 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5203    2.0246   -0.1299 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8611   -2.6448   -0.3781 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6443   -2.1641   -1.9609 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0594   -3.0739   -1.9794 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4272   -3.1200   -0.7340 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0228   -2.8673   -0.0772 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1187   -1.5129    0.3509 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9809    1.2676   -2.2958 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4495    3.4907   -0.6802 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5059    3.5020    1.0555 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0199    0.5520   -1.5319 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3908    1.4358   -0.7819 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8940   -1.9919   -0.4902 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8075   -2.1450   -0.5338 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7229   -1.2915   -2.2628 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1644   -1.2320   -0.1365 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7650   -2.6837    1.3227 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3583    0.8986    1.1298 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3479    1.7746    2.2312 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1265   -0.9077    2.2453 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2759    2.7310   -0.4898 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7566    2.4872    0.5086 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0195    1.2114    0.4346 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 12 10  1  6
 12 13  1  0
 12 14  1  0
 14 15  1  0
 15 16  1  1
 15 23  1  0
 23 24  1  0
 23 22  1  0
 22 21  2  0
 21 19  1  0
 19 20  1  0
 19 17  1  0
 17 18  1  0
  8 25  1  0
 25 26  2  0
 25 27  1  0
 27 28  1  0
 28 29  2  0
 29 30  1  0
 30 31  1  0
 29  3  1  0
 28  6  1  0
 24 12  1  0
 17 15  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
  4 35  1  0
  5 36  1  0
  7 37  1  0
 11 38  1  0
 13 39  1  0
 13 40  1  0
 14 41  1  0
 14 42  1  0
 16 43  1  0
 23 50  1  1
 22 49  1  0
 21 48  1  0
 19 46  1  6
 20 47  1  0
 17 44  1  6
 18 45  1  0
 31 51  1  0
 31 52  1  0
 31 53  1  0
M  END


  Mrv1652309082220542D          

 31 34  0  0  1  0            999 V2000
    0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.0513   -0.7537    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2308    0.6674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    1.3349    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.9088    1.5064    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5442    2.1418    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.7596    2.3968    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1573    2.6939    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.9858    3.5009    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9420    2.4389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1135    1.6320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5004    1.0799    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.5004    0.2549    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  9  8  1  4  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 12 10  1  6  0  0  0
 12 13  1  1  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  6  0  0  0
 15 17  1  0  0  0  0
 17 18  1  1  0  0  0
 17 19  1  0  0  0  0
 19 20  1  6  0  0  0
 19 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 15 23  1  0  0  0  0
 23 24  1  1  0  0  0
 12 24  1  0  0  0  0
  8 25  1  0  0  0  0
 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
 27 28  1  0  0  0  0
  6 28  1  0  0  0  0
 28 29  2  0  0  0  0
  3 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0272327

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC=C2C=C(N=C(O)[C@]3(N)C[C@]4(O)[C@H](S3)C=C[C@@H](O)[C@@H]4O)C(=O)OC2=C1OC

> <INCHI_IDENTIFIER>
InChI=1S/C20H22N2O8S/c1-28-12-5-3-9-7-10(17(25)30-14(9)15(12)29-2)22-18(26)20(21)8-19(27)13(31-20)6-4-11(23)16(19)24/h3-7,11,13,16,23-24,27H,8,21H2,1-2H3,(H,22,26)/t11-,13-,16+,19+,20+/m1/s1

> <INCHI_KEY>
LDSUQPVEEKUWMR-JKRAONCPSA-N

> <FORMULA>
C20H22N2O8S

> <MOLECULAR_WEIGHT>
450.46

> <EXACT_MASS>
450.10968685

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
53

> <JCHEM_AVERAGE_POLARIZABILITY>
43.74889763764793

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,3aR,4S,5R,7aR)-2-amino-N-(7,8-dimethoxy-2-oxo-2H-chromen-3-yl)-3a,4,5-trihydroxy-2,3,3a,4,5,7a-hexahydro-1-benzothiophene-2-carboximidic acid

> <JCHEM_LOGP>
-2.0961300070810442

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.676367950281737

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.9610138323527462

> <JCHEM_PKA_STRONGEST_BASIC>
7.032659083400405

> <JCHEM_POLAR_SURFACE_AREA>
164.05999999999997

> <JCHEM_REFRACTIVITY>
111.9459

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3aR,4S,5R,7aR)-2-amino-N-(7,8-dimethoxy-2-oxochromen-3-yl)-3a,4,5-trihydroxy-3,4,5,7a-tetrahydro-1-benzothiophene-2-carboximidic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 08-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-SEP-22         0                                  
HETATM    1  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0       8.002  -0.000   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       9.336  -2.310   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      10.669  -0.000   0.000  0.00  0.00           C+0
HETATM   13  N   UNK     0      11.296  -1.407   0.000  0.00  0.00           N+0
HETATM   14  C   UNK     0       9.764   1.246   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      10.669   2.492   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       9.163   2.812   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      10.349   3.998   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       8.885   4.474   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      11.494   5.029   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      11.174   6.535   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      12.958   4.553   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      13.279   3.046   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      12.134   2.016   0.000  0.00  0.00           C+0
HETATM   24  S   UNK     0      12.134   0.476   0.000  0.00  0.00           S+0
HETATM   25  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       8.002  -3.080   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0       5.335  -3.080   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   29                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   28                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   25                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   14   24                                             
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16   17   23                                             
CONECT   16   15                                                            
CONECT   17   15   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   15   24                                                  
CONECT   24   23   12                                                       
CONECT   25    8   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28                                                       
CONECT   28   27    6   29                                                  
CONECT   29   28    3   30                                                  
CONECT   30   29   31                                                       
CONECT   31   30                                                            
MASTER        0    0    0    0    0    0    0    0   31    0   68    0
END

View in JSmol

Synonyms

Value	Source
N-(2-oxo-7,8-Dimethoxy-2H-1-benzopyran-3-yl)-2-amino-3aalpha,4b,5a-trihydroxy-2,3,3a,4,5,7aalpha-hexahydrobenzo[b]thiophene-2a-carboxamide	Generator
N-(2-oxo-7,8-Dimethoxy-2H-1-benzopyran-3-yl)-2-amino-3aalpha,4β,5α-trihydroxy-2,3,3a,4,5,7aalpha-hexahydrobenzo[b]thiophene-2α-carboxamide	Generator

Chemical Formula

C₂₀H₂₂N₂O₈S

Average Mass

450.4600 Da

Monoisotopic Mass

450.10969 Da

IUPAC Name

(2S,3aR,4S,5R,7aR)-2-amino-N-(7,8-dimethoxy-2-oxo-2H-chromen-3-yl)-3a,4,5-trihydroxy-2,3,3a,4,5,7a-hexahydro-1-benzothiophene-2-carboximidic acid

Traditional Name

(2S,3aR,4S,5R,7aR)-2-amino-N-(7,8-dimethoxy-2-oxochromen-3-yl)-3a,4,5-trihydroxy-3,4,5,7a-tetrahydro-1-benzothiophene-2-carboximidic acid

CAS Registry Number

Not Available

SMILES

COC1=CC=C2C=C(N=C(O)[C@]3(N)C[C@]4(O)[C@H](S3)C=C[C@@H](O)[C@@H]4O)C(=O)OC2=C1OC

InChI Identifier

InChI=1S/C20H22N2O8S/c1-28-12-5-3-9-7-10(17(25)30-14(9)15(12)29-2)22-18(26)20(21)8-19(27)13(31-20)6-4-11(23)16(19)24/h3-7,11,13,16,23-24,27H,8,21H2,1-2H3,(H,22,26)/t11-,13-,16+,19+,20+/m1/s1

InChI Key

LDSUQPVEEKUWMR-JKRAONCPSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Aspergillus unilateralis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as coumarins and derivatives. These are polycyclic aromatic compounds containing a 1-benzopyran moiety with a ketone group at the C2 carbon atom (1-benzopyran-2-one).

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Coumarins and derivatives

Sub Class

Not Available

Direct Parent

Coumarins and derivatives

Alternative Parents

Substituents

Coumarin
Alpha-amino acid or derivatives
Benzopyran
1-benzopyran
Anisole
N-arylamide
Alkyl aryl ether
Pyranone
Pyran
Benzenoid
Heteroaromatic compound
Tertiary alcohol
Thiolane
Carboxamide group
Lactone
Secondary alcohol
Secondary carboxylic acid amide
Hemithioaminal
Organoheterocyclic compound
Oxacycle
Polyol
Thioether
Dialkylthioether
Carboxylic acid derivative
Ether
Organic oxygen compound
Hydrocarbon derivative
Organic nitrogen compound
Alcohol
Carbonyl group
Organic oxide
Organopnictogen compound
Organonitrogen compound
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	-2.1	ChemAxon
pKa (Strongest Acidic)	1.96	ChemAxon
pKa (Strongest Basic)	7.03	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	164.06 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	111.95 m³·mol⁻¹	ChemAxon
Polarizability	43.75 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

9457357

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11282360

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2s,3ar,4s,5r,7ar)-2-amino-n-(7,8-dimethoxy-2-oxochromen-3-yl)-3a,4,5-trihydroxy-3,4,5,7a-tetrahydro-1-benzothiophene-2-carboximidic acid (NP0272327)

MOL for NP0272327 ((2s,3ar,4s,5r,7ar)-2-amino-n-(7,8-dimethoxy-2-oxochromen-3-yl)-3a,4,5-trihydroxy-3,4,5,7a-tetrahydro-1-benzothiophene-2-carboximidic acid)

3D MOL for NP0272327 ((2s,3ar,4s,5r,7ar)-2-amino-n-(7,8-dimethoxy-2-oxochromen-3-yl)-3a,4,5-trihydroxy-3,4,5,7a-tetrahydro-1-benzothiophene-2-carboximidic acid)

3D SDF for NP0272327 ((2s,3ar,4s,5r,7ar)-2-amino-n-(7,8-dimethoxy-2-oxochromen-3-yl)-3a,4,5-trihydroxy-3,4,5,7a-tetrahydro-1-benzothiophene-2-carboximidic acid)

3D-SDF for NP0272327 ((2s,3ar,4s,5r,7ar)-2-amino-n-(7,8-dimethoxy-2-oxochromen-3-yl)-3a,4,5-trihydroxy-3,4,5,7a-tetrahydro-1-benzothiophene-2-carboximidic acid)

PDB for NP0272327 ((2s,3ar,4s,5r,7ar)-2-amino-n-(7,8-dimethoxy-2-oxochromen-3-yl)-3a,4,5-trihydroxy-3,4,5,7a-tetrahydro-1-benzothiophene-2-carboximidic acid)

3D PDB for NP0272327 ((2s,3ar,4s,5r,7ar)-2-amino-n-(7,8-dimethoxy-2-oxochromen-3-yl)-3a,4,5-trihydroxy-3,4,5,7a-tetrahydro-1-benzothiophene-2-carboximidic acid)

SMILES for NP0272327 ((2s,3ar,4s,5r,7ar)-2-amino-n-(7,8-dimethoxy-2-oxochromen-3-yl)-3a,4,5-trihydroxy-3,4,5,7a-tetrahydro-1-benzothiophene-2-carboximidic acid)

INCHI for NP0272327 ((2s,3ar,4s,5r,7ar)-2-amino-n-(7,8-dimethoxy-2-oxochromen-3-yl)-3a,4,5-trihydroxy-3,4,5,7a-tetrahydro-1-benzothiophene-2-carboximidic acid)

Structure for NP0272327 ((2s,3ar,4s,5r,7ar)-2-amino-n-(7,8-dimethoxy-2-oxochromen-3-yl)-3a,4,5-trihydroxy-3,4,5,7a-tetrahydro-1-benzothiophene-2-carboximidic acid)

3D Structure for NP0272327 ((2s,3ar,4s,5r,7ar)-2-amino-n-(7,8-dimethoxy-2-oxochromen-3-yl)-3a,4,5-trihydroxy-3,4,5,7a-tetrahydro-1-benzothiophene-2-carboximidic acid)