NP-MRD: Showing NP-Card for (1s,3s,6r,8r,9s)-2-benzoyl-1,3,8,10-tetrahydroxy-9-(4-methoxy-6-oxopyran-2-yl)-5-oxatricyclo[4.3.1.0³,⁸]decan-4-one (NP0325828)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-12 06:53:15 UTC

Updated at

2022-09-12 06:53:15 UTC

NP-MRD ID

NP0325828

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,3s,6r,8r,9s)-2-benzoyl-1,3,8,10-tetrahydroxy-9-(4-methoxy-6-oxopyran-2-yl)-5-oxatricyclo[4.3.1.0³,⁸]decan-4-one

Description

(1S,3S,6R,8R,9S)-2-benzoyl-1,3,8,10-tetrahydroxy-9-(4-methoxy-2-oxo-2H-pyran-6-yl)-5-oxatricyclo[4.3.1.0³,⁸]Decan-4-one belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group. (1s,3s,6r,8r,9s)-2-benzoyl-1,3,8,10-tetrahydroxy-9-(4-methoxy-6-oxopyran-2-yl)-5-oxatricyclo[4.3.1.0³,⁸]decan-4-one is found in Enterococcus faecalis and Enterococcus gallinarum. Based on a literature review very few articles have been published on (1S,3S,6R,8R,9S)-2-benzoyl-1,3,8,10-tetrahydroxy-9-(4-methoxy-2-oxo-2H-pyran-6-yl)-5-oxatricyclo[4.3.1.0³,⁸]Decan-4-one.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309122208532D          

 32 36  0  0  1  0            999 V2000
    3.5157    3.2816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7836    2.9013    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7469    2.0771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1297    1.7173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9576    0.9875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2460    0.4923    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2537    0.9583    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5344    1.3305    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2336    0.3411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0245    0.0007    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6851    0.6626    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4101   -0.2733    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1320   -0.1575    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2771   -1.0246    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4161    1.0084    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5821    1.9072    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1044    0.7332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9541    1.1274    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7024    0.0502    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7484    1.5302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7208    2.4489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9312    3.3388    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0828    2.6925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6848    2.1284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4743    2.3678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6618    3.1712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0598    3.7353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2702    3.4959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6735    0.4287    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4056    0.8090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1010    0.3652    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4423    1.6332    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  1  0  0  0  0
  4  5  2  0  0  0  0
  6  5  1  6  0  0  0
  6  7  1  0  0  0  0
  7  8  1  6  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  1  0  0  0
 12 13  1  0  0  0  0
  6 13  1  0  0  0  0
 13 14  1  1  0  0  0
 13 15  1  0  0  0  0
 15 16  1  6  0  0  0
 15 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
 11 19  1  0  0  0  0
 15 20  1  0  0  0  0
  7 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 23 28  1  0  0  0  0
  5 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 30 32  1  0  0  0  0
  3 32  2  0  0  0  0
M  END

     RDKit          3D

 52 56  0  0  0  0  0  0  0  0999 V2000
    5.7649    2.9019    1.8889 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4130    2.6274    1.6851 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9454    1.4029    1.1989 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5985    1.1655    1.0091 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0946   -0.0391    0.5275 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6311   -0.1272    0.3837 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1729   -0.2933   -1.0495 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5066    0.7569   -1.8631 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6548   -1.5894   -1.6775 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9390   -1.4232   -2.1135 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3789   -2.8047   -0.8663 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5807   -2.6143    0.6280 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0034   -1.3035    1.0231 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1074   -1.1712    2.4106 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4335   -1.2415    0.4464 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3007   -0.7697    1.4020 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8282   -2.5919   -0.0259 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8309   -3.1426    0.4404 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0154   -3.1578   -0.9901 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3374   -0.3896   -0.8005 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8548    0.9807   -0.6551 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0578    1.9881   -0.7370 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2536    1.2956   -0.4117 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6779    2.5822   -0.1611 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0089    2.8843    0.0405 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9672    1.9016   -0.0023 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5667    0.6141   -0.2508 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2080    0.3172   -0.4552 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9338   -0.9713    0.2482 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2203   -0.8099    0.4054 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0383   -1.7496    0.1218 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7966    0.3606    0.8800 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3128    2.5720    0.9733 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9151    3.9871    2.0028 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0905    2.3341    2.7965 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8942    1.9769    1.2541 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1215    0.7741    0.7811 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3761    0.5016   -2.7913 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0219   -1.6853   -2.6095 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3920   -2.3026   -2.2240 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0333   -3.6155   -1.1962 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6196   -2.7739    0.9325 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0093   -3.4229    1.1325 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7851   -0.4741    2.6102 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7465   -1.5138    1.8894 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8194   -0.9125   -1.6733 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9112    3.3695   -0.1267 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3322    3.8952    0.2362 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0262    2.1119    0.1537 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3011   -0.1785   -0.2898 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9407   -0.7077   -0.6664 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8700    0.4752    1.0038 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3 32  2  0
 32 30  1  0
 30 31  2  0
 30 29  1  0
 29  5  1  0
  5  4  2  0
  5  6  1  0
  6 13  1  0
 13 14  1  1
 13 12  1  0
 12 11  1  0
 11 19  1  0
 19 17  1  0
 17 18  2  0
 17 15  1  0
 15 16  1  1
 15 20  1  0
 20 21  1  0
 21 22  2  0
 21 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 20  7  1  0
  7  8  1  6
  7  9  1  0
  9 10  1  0
  4  3  1  0
  7  6  1  0
 15 13  1  0
 28 23  1  0
  9 11  1  0
  1 33  1  0
  1 34  1  0
  1 35  1  0
 32 52  1  0
  4 36  1  0
  6 37  1  1
 14 44  1  0
 12 42  1  0
 12 43  1  0
 11 41  1  6
 16 45  1  0
 20 46  1  6
 24 47  1  0
 25 48  1  0
 26 49  1  0
 27 50  1  0
 28 51  1  0
  8 38  1  0
  9 39  1  6
 10 40  1  0
M  END


  Mrv1652309122208532D          

 32 36  0  0  1  0            999 V2000
    3.5157    3.2816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7836    2.9013    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7469    2.0771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1297    1.7173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9576    0.9875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2460    0.4923    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2537    0.9583    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5344    1.3305    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2336    0.3411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0245    0.0007    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6851    0.6626    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4101   -0.2733    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1320   -0.1575    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2771   -1.0246    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4161    1.0084    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5821    1.9072    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1044    0.7332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9541    1.1274    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7024    0.0502    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7484    1.5302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7208    2.4489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9312    3.3388    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0828    2.6925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6848    2.1284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4743    2.3678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6618    3.1712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0598    3.7353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2702    3.4959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6735    0.4287    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4056    0.8090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1010    0.3652    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4423    1.6332    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  1  0  0  0  0
  4  5  2  0  0  0  0
  6  5  1  6  0  0  0
  6  7  1  0  0  0  0
  7  8  1  6  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  1  0  0  0
 12 13  1  0  0  0  0
  6 13  1  0  0  0  0
 13 14  1  1  0  0  0
 13 15  1  0  0  0  0
 15 16  1  6  0  0  0
 15 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
 11 19  1  0  0  0  0
 15 20  1  0  0  0  0
  7 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 23 28  1  0  0  0  0
  5 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 30 32  1  0  0  0  0
  3 32  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0325828

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(=O)OC(=C1)[C@@H]1[C@]2(O)C[C@H]3OC(=O)[C@]2(O)C(C(=O)C2=CC=CC=C2)[C@]1(O)C3O

> <INCHI_IDENTIFIER>
InChI=1S/C22H20O10/c1-30-11-7-12(31-14(23)8-11)16-20(27)9-13-18(25)21(16,28)17(22(20,29)19(26)32-13)15(24)10-5-3-2-4-6-10/h2-8,13,16-18,25,27-29H,9H2,1H3/t13-,16-,17?,18?,20-,21+,22-/m1/s1

> <INCHI_KEY>
CTBBEXWJRAPJIZ-LSJIUZMMSA-N

> <FORMULA>
C22H20O10

> <MOLECULAR_WEIGHT>
444.392

> <EXACT_MASS>
444.105646844

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
52

> <JCHEM_AVERAGE_POLARIZABILITY>
41.36613270501202

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,3S,6R,8R,9S)-2-benzoyl-1,3,8,10-tetrahydroxy-9-(4-methoxy-2-oxo-2H-pyran-6-yl)-5-oxatricyclo[4.3.1.0^{3,8}]decan-4-one

> <JCHEM_LOGP>
-1.4361866920000002

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
5.69334753497505

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.655880308668445

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6830156566232777

> <JCHEM_POLAR_SURFACE_AREA>
159.82

> <JCHEM_REFRACTIVITY>
106.1762

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1S,3S,6R,8R,9S)-2-benzoyl-1,3,8,10-tetrahydroxy-9-(4-methoxy-6-oxopyran-2-yl)-5-oxatricyclo[4.3.1.0^{3,8}]decan-4-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 12-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-SEP-22         0                                  
HETATM    1  C   UNK     0       6.563   6.126   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       5.196   5.416   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       5.128   3.877   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.975   3.206   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.654   1.843   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.326   0.919   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.474   1.789   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -0.998   2.484   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -0.436   0.637   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -1.912   0.001   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       1.279   1.237   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.766  -0.510   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.113  -0.294   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       2.384  -1.913   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       2.643   1.882   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       2.953   3.560   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       3.928   1.369   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       5.514   2.104   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       3.178   0.094   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       1.397   2.856   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.345   4.571   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       1.738   6.232   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      -0.154   5.026   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -1.278   3.973   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -2.752   4.420   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -3.102   5.920   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -1.978   6.973   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -0.504   6.526   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       4.991   0.800   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       6.357   1.510   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       7.655   0.682   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       6.426   3.049   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   32                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   29                                                  
CONECT    6    5    7   13                                                  
CONECT    7    6    8    9   20                                             
CONECT    8    7                                                            
CONECT    9    7   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   19                                                  
CONECT   12   11   13                                                       
CONECT   13   12    6   14   15                                             
CONECT   14   13                                                            
CONECT   15   13   16   17   20                                             
CONECT   16   15                                                            
CONECT   17   15   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   11                                                       
CONECT   20   15    7   21                                                  
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24   28                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   23                                                       
CONECT   29    5   30                                                       
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30    3                                                       
MASTER        0    0    0    0    0    0    0    0   32    0   72    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₂H₂₀O₁₀

Average Mass

444.3920 Da

Monoisotopic Mass

444.10565 Da

IUPAC Name

(1S,3S,6R,8R,9S)-2-benzoyl-1,3,8,10-tetrahydroxy-9-(4-methoxy-2-oxo-2H-pyran-6-yl)-5-oxatricyclo[4.3.1.0^{3,8}]decan-4-one

Traditional Name

(1S,3S,6R,8R,9S)-2-benzoyl-1,3,8,10-tetrahydroxy-9-(4-methoxy-6-oxopyran-2-yl)-5-oxatricyclo[4.3.1.0^{3,8}]decan-4-one

CAS Registry Number

Not Available

SMILES

COC1=CC(=O)OC(=C1)[C@@H]1[C@]2(O)C[C@H]3OC(=O)[C@]2(O)C(C(=O)C2=CC=CC=C2)[C@]1(O)C3O

InChI Identifier

InChI=1S/C22H20O10/c1-30-11-7-12(31-14(23)8-11)16-20(27)9-13-18(25)21(16,28)17(22(20,29)19(26)32-13)15(24)10-5-3-2-4-6-10/h2-8,13,16-18,25,27-29H,9H2,1H3/t13-,16-,17?,18?,20-,21+,22-/m1/s1

InChI Key

CTBBEXWJRAPJIZ-LSJIUZMMSA-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
Enterococcus faecalis	LOTUS Database	35616633
Enterococcus gallinarum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Alkyl-phenylketones

Alternative Parents

Substituents

Alkyl-phenylketone
Aryl alkyl ketone
Caprolactone
Benzoyl
Pyranone
Oxepane
Delta_valerolactone
Delta valerolactone
Alkyl aryl ether
Benzenoid
Pyran
Oxane
Monocyclic benzene moiety
Heteroaromatic compound
Vinylogous ester
Tertiary alcohol
Cyclic alcohol
Secondary alcohol
Lactone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Polyol
Monocarboxylic acid or derivatives
Ether
Carboxylic acid derivative
Organic oxide
Hydrocarbon derivative
Alcohol
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	-1.4	ChemAxon
pKa (Strongest Acidic)	4.66	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	159.82 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	106.18 m³·mol⁻¹	ChemAxon
Polarizability	41.37 Å³	ChemAxon
Number of Rings	5	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

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

163185573

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1s,3s,6r,8r,9s)-2-benzoyl-1,3,8,10-tetrahydroxy-9-(4-methoxy-6-oxopyran-2-yl)-5-oxatricyclo[4.3.1.0³,⁸]decan-4-one (NP0325828)

MOL for NP0325828 ((1s,3s,6r,8r,9s)-2-benzoyl-1,3,8,10-tetrahydroxy-9-(4-methoxy-6-oxopyran-2-yl)-5-oxatricyclo[4.3.1.0³,⁸]decan-4-one)

3D MOL for NP0325828 ((1s,3s,6r,8r,9s)-2-benzoyl-1,3,8,10-tetrahydroxy-9-(4-methoxy-6-oxopyran-2-yl)-5-oxatricyclo[4.3.1.0³,⁸]decan-4-one)

3D SDF for NP0325828 ((1s,3s,6r,8r,9s)-2-benzoyl-1,3,8,10-tetrahydroxy-9-(4-methoxy-6-oxopyran-2-yl)-5-oxatricyclo[4.3.1.0³,⁸]decan-4-one)

3D-SDF for NP0325828 ((1s,3s,6r,8r,9s)-2-benzoyl-1,3,8,10-tetrahydroxy-9-(4-methoxy-6-oxopyran-2-yl)-5-oxatricyclo[4.3.1.0³,⁸]decan-4-one)

PDB for NP0325828 ((1s,3s,6r,8r,9s)-2-benzoyl-1,3,8,10-tetrahydroxy-9-(4-methoxy-6-oxopyran-2-yl)-5-oxatricyclo[4.3.1.0³,⁸]decan-4-one)

3D PDB for NP0325828 ((1s,3s,6r,8r,9s)-2-benzoyl-1,3,8,10-tetrahydroxy-9-(4-methoxy-6-oxopyran-2-yl)-5-oxatricyclo[4.3.1.0³,⁸]decan-4-one)

SMILES for NP0325828 ((1s,3s,6r,8r,9s)-2-benzoyl-1,3,8,10-tetrahydroxy-9-(4-methoxy-6-oxopyran-2-yl)-5-oxatricyclo[4.3.1.0³,⁸]decan-4-one)

INCHI for NP0325828 ((1s,3s,6r,8r,9s)-2-benzoyl-1,3,8,10-tetrahydroxy-9-(4-methoxy-6-oxopyran-2-yl)-5-oxatricyclo[4.3.1.0³,⁸]decan-4-one)

Structure for NP0325828 ((1s,3s,6r,8r,9s)-2-benzoyl-1,3,8,10-tetrahydroxy-9-(4-methoxy-6-oxopyran-2-yl)-5-oxatricyclo[4.3.1.0³,⁸]decan-4-one)

3D Structure for NP0325828 ((1s,3s,6r,8r,9s)-2-benzoyl-1,3,8,10-tetrahydroxy-9-(4-methoxy-6-oxopyran-2-yl)-5-oxatricyclo[4.3.1.0³,⁸]decan-4-one)