NP-MRD: Showing NP-Card for (1s,11r,12s,13r)-11-hydroxy-3,17,18-trimethoxy-12,13-dimethyl-5,7-dioxapentacyclo[10.7.0.0¹,¹⁵.0²,¹⁰.0⁴,⁸]nonadeca-2,4(8),9,15,17-pentaen-19-one (NP0330482)

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Record Information

Version

2.0

Created at

2022-09-12 15:52:58 UTC

Updated at

2022-09-12 15:52:58 UTC

NP-MRD ID

NP0330482

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,11r,12s,13r)-11-hydroxy-3,17,18-trimethoxy-12,13-dimethyl-5,7-dioxapentacyclo[10.7.0.0¹,¹⁵.0²,¹⁰.0⁴,⁸]nonadeca-2,4(8),9,15,17-pentaen-19-one

Description

(1S,11R,12S,13R)-11-hydroxy-3,17,18-trimethoxy-12,13-dimethyl-5,7-dioxapentacyclo[10.7.0.0¹,¹⁵.0²,¹⁰.0⁴,⁸]Nonadeca-2,4(8),9,15,17-pentaen-19-one belongs to the class of organic compounds known as hydrolyzable tannins. These are tannins with a structure characterized by either of the following models. In model 1, the structure contains galloyl units (in some cases, shikimic acid units) that are linked to diverse polyol carbohydrate-, catechin-, or triterpenoid units. In model 2, contains at least two galloyl units C-C coupled to each other, and do not contain a glycosidically linked catechin unit. (1s,11r,12s,13r)-11-hydroxy-3,17,18-trimethoxy-12,13-dimethyl-5,7-dioxapentacyclo[10.7.0.0¹,¹⁵.0²,¹⁰.0⁴,⁸]nonadeca-2,4(8),9,15,17-pentaen-19-one is found in Kadsura heteroclita. Based on a literature review very few articles have been published on (1S,11R,12S,13R)-11-hydroxy-3,17,18-trimethoxy-12,13-dimethyl-5,7-dioxapentacyclo[10.7.0.0¹,¹⁵.0²,¹⁰.0⁴,⁸]Nonadeca-2,4(8),9,15,17-pentaen-19-one.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309122217532D          

 29 33  0  0  1  0            999 V2000
    0.9909   -2.8847    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5307   -2.2281    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6324   -1.3263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2343   -0.7620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9811   -1.4134    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6577   -0.7354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0466    0.0413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6869    0.4727    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2570    0.2804    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6551   -0.2838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8429   -1.0872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0675    0.1142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0878    0.9245    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6618    1.3542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9064    1.0272    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5298    1.8205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5082    1.5915    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5790    2.4575    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2308    1.1934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0102    1.4641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6343    0.9245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4790    0.1142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6997   -0.1564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0634   -0.9590    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7501   -1.5637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0756    0.3831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2016   -0.2838    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8035    0.2804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4528    1.0272    0.0000 O   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  1  0  0  0  0
  4  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  6  0  0  0
 10 11  2  0  0  0  0
  3 11  1  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  1  0  0  0
 13 15  1  0  0  0  0
  9 15  1  0  0  0  0
 15 16  1  1  0  0  0
 15 17  1  0  0  0  0
 17 18  1  6  0  0  0
 17 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 23 26  2  0  0  0  0
 19 26  1  0  0  0  0
  9 26  1  0  0  0  0
 22 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 21 29  1  0  0  0  0
M  END

     RDKit          3D

 53 57  0  0  0  0  0  0  0  0999 V2000
   -4.0590    2.2356    1.5172 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8704    1.0278    0.8121 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6339    0.5849    0.3764 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0626    1.0350   -0.7226 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6877    1.9928   -1.5018 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8693    1.5970   -2.1873 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7461    0.5453   -1.1761 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2504    0.9604   -2.2344 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0385   -0.4235   -0.3753 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7606   -0.8915    0.8466 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9293   -0.4225    1.1709 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2128   -1.9163    1.3797 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4328   -2.7249    0.0915 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7115   -3.7142    0.0258 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2864   -1.7462   -1.0574 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7347   -2.1538   -2.0623 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6065   -1.4042   -1.6799 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3535   -2.5240   -2.0126 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2689   -0.5505   -0.6791 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6189   -0.2944   -0.4506 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9859    0.5714    0.5605 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0248    1.1768    1.3365 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7009    0.8985    1.0805 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7403    1.5104    1.8643 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2469    2.7623    1.4172 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3006    0.0465    0.0882 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6574    1.9937    2.2736 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9816    2.2298    1.7992 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2051    1.0388    1.0482 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7172    3.1087    0.9070 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5345    2.2449    2.4910 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1461    2.3296    1.7143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2780    2.4364   -2.7728 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7225    0.7059   -2.8028 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6376    1.3914   -1.3878 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3978   -0.8057    2.0813 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2591   -2.5223    2.1535 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1580   -1.4309    1.7055 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4119   -3.2134    0.1213 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6376   -3.1245   -0.1584 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8102   -4.1338    1.0629 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5501   -4.5122   -0.7192 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5930   -3.2206   -2.2976 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7773   -1.9051   -1.7878 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4982   -1.6048   -3.0187 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3925   -0.7597   -2.5596 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9181   -2.3631   -2.8245 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3655   -0.7753   -1.0662 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8372    2.8550    1.6338 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8489    3.5361    1.9256 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4078    2.8846    0.3342 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6932    2.3619    2.6162 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9313    3.0760    1.0997 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  1  0
  4  7  1  0
  7  8  2  0
  9  7  1  6
  9 10  1  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  1  6
 15 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 27  1  0
 27 28  1  0
 28 29  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 23 26  2  0
 10 11  2  0
 11  3  1  0
 15  9  1  0
 26 19  1  0
 26  9  1  0
 29 21  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  6 33  1  0
  6 34  1  0
  6 35  1  0
 12 37  1  0
 12 38  1  0
 13 39  1  1
 14 40  1  0
 14 41  1  0
 14 42  1  0
 16 43  1  0
 16 44  1  0
 16 45  1  0
 17 46  1  6
 18 47  1  0
 20 48  1  0
 28 52  1  0
 28 53  1  0
 25 49  1  0
 25 50  1  0
 25 51  1  0
 11 36  1  0
M  END


  Mrv1652309122217532D          

 29 33  0  0  1  0            999 V2000
    0.9909   -2.8847    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5307   -2.2281    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6324   -1.3263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2343   -0.7620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9811   -1.4134    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6577   -0.7354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0466    0.0413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6869    0.4727    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2570    0.2804    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6551   -0.2838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8429   -1.0872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0675    0.1142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0878    0.9245    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6618    1.3542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9064    1.0272    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5298    1.8205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5082    1.5915    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5790    2.4575    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2308    1.1934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0102    1.4641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6343    0.9245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4790    0.1142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6997   -0.1564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0634   -0.9590    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7501   -1.5637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0756    0.3831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2016   -0.2838    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8035    0.2804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4528    1.0272    0.0000 O   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  1  0  0  0  0
  4  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  6  0  0  0
 10 11  2  0  0  0  0
  3 11  1  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  1  0  0  0
 13 15  1  0  0  0  0
  9 15  1  0  0  0  0
 15 16  1  1  0  0  0
 15 17  1  0  0  0  0
 17 18  1  6  0  0  0
 17 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 23 26  2  0  0  0  0
 19 26  1  0  0  0  0
  9 26  1  0  0  0  0
 22 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 21 29  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0330482

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(OC)C(=O)[C@@]23C(C[C@@H](C)[C@]2(C)[C@H](O)C2=CC4=C(OCO4)C(OC)=C32)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C22H24O7/c1-10-6-11-7-13(25-3)17(26-4)20(24)22(11)15-12(19(23)21(10,22)2)8-14-16(18(15)27-5)29-9-28-14/h7-8,10,19,23H,6,9H2,1-5H3/t10-,19-,21-,22+/m1/s1

> <INCHI_KEY>
ZIWBGKHKHFLTJE-IWEJOQTDSA-N

> <FORMULA>
C22H24O7

> <MOLECULAR_WEIGHT>
400.427

> <EXACT_MASS>
400.152203113

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
53

> <JCHEM_AVERAGE_POLARIZABILITY>
40.98089385884019

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,11R,12S,13R)-11-hydroxy-3,17,18-trimethoxy-12,13-dimethyl-5,7-dioxapentacyclo[10.7.0.0^{1,15}.0^{2,10}.0^{4,8}]nonadeca-2,4(8),9,15,17-pentaen-19-one

> <JCHEM_LOGP>
1.4871256123333327

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.802710634206587

> <JCHEM_PKA_STRONGEST_BASIC>
-3.322494368598038

> <JCHEM_POLAR_SURFACE_AREA>
83.45000000000002

> <JCHEM_REFRACTIVITY>
105.87259999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1S,11R,12S,13R)-11-hydroxy-3,17,18-trimethoxy-12,13-dimethyl-5,7-dioxapentacyclo[10.7.0.0^{1,15}.0^{2,10}.0^{4,8}]nonadeca-2,4(8),9,15,17-pentaen-19-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       1.850  -5.385   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       2.857  -4.159   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       3.047  -2.476   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.171  -1.422   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       5.565  -2.638   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       6.828  -1.373   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.820   0.077   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       5.015   0.882   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       2.346   0.523   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.223  -0.530   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.573  -2.029   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.126   0.213   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.164   1.726   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.235   2.528   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.692   1.917   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.989   3.398   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.815   2.971   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       2.947   4.587   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       4.164   2.228   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.619   2.733   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.784   1.726   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       6.494   0.213   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       5.039  -0.292   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       5.718  -1.790   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       7.000  -2.919   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       3.874   0.715   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       7.843  -0.530   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       8.967   0.523   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       8.312   1.917   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   11                                                  
CONECT    4    3    5    7                                                  
CONECT    5    4    6                                                       
CONECT    6    5                                                            
CONECT    7    4    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   15   26                                             
CONECT   10    9   11   12                                                  
CONECT   11   10    3                                                       
CONECT   12   10   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13    9   16   17                                             
CONECT   16   15                                                            
CONECT   17   15   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20   26                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22   29                                                  
CONECT   22   21   23   27                                                  
CONECT   23   22   24   26                                                  
CONECT   24   23   25                                                       
CONECT   25   24                                                            
CONECT   26   23   19    9                                                  
CONECT   27   22   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   21                                                       
MASTER        0    0    0    0    0    0    0    0   29    0   66    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₂H₂₄O₇

Average Mass

400.4270 Da

Monoisotopic Mass

400.15220 Da

IUPAC Name

(1S,11R,12S,13R)-11-hydroxy-3,17,18-trimethoxy-12,13-dimethyl-5,7-dioxapentacyclo[10.7.0.0^{1,15}.0^{2,10}.0^{4,8}]nonadeca-2,4(8),9,15,17-pentaen-19-one

Traditional Name

(1S,11R,12S,13R)-11-hydroxy-3,17,18-trimethoxy-12,13-dimethyl-5,7-dioxapentacyclo[10.7.0.0^{1,15}.0^{2,10}.0^{4,8}]nonadeca-2,4(8),9,15,17-pentaen-19-one

CAS Registry Number

Not Available

SMILES

COC1=C(OC)C(=O)[C@@]23C(C[C@@H](C)[C@]2(C)[C@H](O)C2=CC4=C(OCO4)C(OC)=C32)=C1

InChI Identifier

InChI=1S/C22H24O7/c1-10-6-11-7-13(25-3)17(26-4)20(24)22(11)15-12(19(23)21(10,22)2)8-14-16(18(15)27-5)29-9-28-14/h7-8,10,19,23H,6,9H2,1-5H3/t10-,19-,21-,22+/m1/s1

InChI Key

ZIWBGKHKHFLTJE-IWEJOQTDSA-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
Kadsura heteroclita	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hydrolyzable tannins. These are tannins with a structure characterized by either of the following models. In model 1, the structure contains galloyl units (in some cases, shikimic acid units) that are linked to diverse polyol carbohydrate-, catechin-, or triterpenoid units. In model 2, contains at least two galloyl units C-C coupled to each other, and do not contain a glycosidically linked catechin unit.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Tannins

Sub Class

Hydrolyzable tannins

Direct Parent

Hydrolyzable tannins

Alternative Parents

Substituents

Hydrolyzable tannin
Benzodioxole
Indane
Anisole
Alkyl aryl ether
Benzenoid
Vinylogous ester
Ketone
Secondary alcohol
Acetal
Organoheterocyclic compound
Oxacycle
Ether
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Organooxygen compound
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	1.49	ChemAxon
pKa (Strongest Acidic)	13.8	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	83.45 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	105.87 m³·mol⁻¹	ChemAxon
Polarizability	40.98 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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

162889048

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1s,11r,12s,13r)-11-hydroxy-3,17,18-trimethoxy-12,13-dimethyl-5,7-dioxapentacyclo[10.7.0.0¹,¹⁵.0²,¹⁰.0⁴,⁸]nonadeca-2,4(8),9,15,17-pentaen-19-one (NP0330482)

MOL for NP0330482 ((1s,11r,12s,13r)-11-hydroxy-3,17,18-trimethoxy-12,13-dimethyl-5,7-dioxapentacyclo[10.7.0.0¹,¹⁵.0²,¹⁰.0⁴,⁸]nonadeca-2,4(8),9,15,17-pentaen-19-one)

3D MOL for NP0330482 ((1s,11r,12s,13r)-11-hydroxy-3,17,18-trimethoxy-12,13-dimethyl-5,7-dioxapentacyclo[10.7.0.0¹,¹⁵.0²,¹⁰.0⁴,⁸]nonadeca-2,4(8),9,15,17-pentaen-19-one)

3D SDF for NP0330482 ((1s,11r,12s,13r)-11-hydroxy-3,17,18-trimethoxy-12,13-dimethyl-5,7-dioxapentacyclo[10.7.0.0¹,¹⁵.0²,¹⁰.0⁴,⁸]nonadeca-2,4(8),9,15,17-pentaen-19-one)

3D-SDF for NP0330482 ((1s,11r,12s,13r)-11-hydroxy-3,17,18-trimethoxy-12,13-dimethyl-5,7-dioxapentacyclo[10.7.0.0¹,¹⁵.0²,¹⁰.0⁴,⁸]nonadeca-2,4(8),9,15,17-pentaen-19-one)

PDB for NP0330482 ((1s,11r,12s,13r)-11-hydroxy-3,17,18-trimethoxy-12,13-dimethyl-5,7-dioxapentacyclo[10.7.0.0¹,¹⁵.0²,¹⁰.0⁴,⁸]nonadeca-2,4(8),9,15,17-pentaen-19-one)

3D PDB for NP0330482 ((1s,11r,12s,13r)-11-hydroxy-3,17,18-trimethoxy-12,13-dimethyl-5,7-dioxapentacyclo[10.7.0.0¹,¹⁵.0²,¹⁰.0⁴,⁸]nonadeca-2,4(8),9,15,17-pentaen-19-one)

SMILES for NP0330482 ((1s,11r,12s,13r)-11-hydroxy-3,17,18-trimethoxy-12,13-dimethyl-5,7-dioxapentacyclo[10.7.0.0¹,¹⁵.0²,¹⁰.0⁴,⁸]nonadeca-2,4(8),9,15,17-pentaen-19-one)

INCHI for NP0330482 ((1s,11r,12s,13r)-11-hydroxy-3,17,18-trimethoxy-12,13-dimethyl-5,7-dioxapentacyclo[10.7.0.0¹,¹⁵.0²,¹⁰.0⁴,⁸]nonadeca-2,4(8),9,15,17-pentaen-19-one)

Structure for NP0330482 ((1s,11r,12s,13r)-11-hydroxy-3,17,18-trimethoxy-12,13-dimethyl-5,7-dioxapentacyclo[10.7.0.0¹,¹⁵.0²,¹⁰.0⁴,⁸]nonadeca-2,4(8),9,15,17-pentaen-19-one)

3D Structure for NP0330482 ((1s,11r,12s,13r)-11-hydroxy-3,17,18-trimethoxy-12,13-dimethyl-5,7-dioxapentacyclo[10.7.0.0¹,¹⁵.0²,¹⁰.0⁴,⁸]nonadeca-2,4(8),9,15,17-pentaen-19-one)