NP-MRD: Showing NP-Card for 8alpha-(4-hydroxymethacryloyloxy)-10alpha-hydroxy-1,13-dimethoxy-hirsutin+ (NP0031682)

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Record Information

Version

2.0

Created at

2021-06-19 22:41:51 UTC

Updated at

2021-06-30 00:00:25 UTC

NP-MRD ID

NP0031682

Secondary Accession Numbers

None

Natural Product Identification

Common Name

8alpha-(4-hydroxymethacryloyloxy)-10alpha-hydroxy-1,13-dimethoxy-hirsutin+

Provided By

JEOL Database JEOL Logo

Description

8alpha-(4-hydroxymethacryloyloxy)-10alpha-hydroxy-1,13-dimethoxy-hirsutin+ is found in Vernonia triflosculosa. 8alpha-(4-hydroxymethacryloyloxy)-10alpha-hydroxy-1,13-dimethoxy-hirsutin+ was first documented in 2006 (Kos, O., et al.).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202100413D          

 58 60  0  0  0  0            999 V2000
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    1.1084    4.2385    2.2874 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.1722    2.3057    0.9513 O   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

 58 60  0  0  0  0  0  0  0  0999 V2000
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M  END


  Mrv1652306202100413D          

 58 60  0  0  0  0            999 V2000
    2.0491    4.8394    1.5384 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1084    4.2385    2.2874 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.5305    5.7541    1.8705 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3440    4.4602    0.5643 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7031    3.9832    4.3850 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2842    5.5916    3.9560 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2304    4.4824    3.2616 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0103    0.6702    1.2038 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0171    2.2999   -0.4351 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3580    2.1321   -1.4836 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1327    1.7757   -3.4109 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5542    1.9418   -2.3696 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3461    0.5156   -3.4097 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4959    0.2465   -2.8192 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6463    0.8583    0.9558 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1065    0.4063    1.6984 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1164   -0.8303    0.8784 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7418   -1.5172   -2.4699 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5197   -1.9292   -0.9574 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7741   -2.7040   -1.8812 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9358   -3.6528   -0.9776 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1146   -3.9931    1.3791 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4869   -2.8746    1.5163 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9984   -2.5275    2.3779 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9569   -3.2490    0.1582 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7067    1.6293   -0.7490 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6391    2.3384    0.4333 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2769    1.1439   -3.0394 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8905    2.8058   -3.5288 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5138    2.4388   -2.9103 H   0  0  0  0  0  0  0  0  0  0  0  0
 20 21  2  0  0  0  0
 25 26  1  0  0  0  0
 16 17  1  0  0  0  0
 26 27  1  0  0  0  0
  9  8  1  0  0  0  0
 27 28  1  0  0  0  0
  8 29  1  0  0  0  0
 13 30  1  0  0  0  0
 18 30  1  0  0  0  0
 29 21  1  0  0  0  0
 18 19  1  1  0  0  0
 13 14  1  1  0  0  0
 13 10  1  0  0  0  0
 10 12  1  6  0  0  0
 17 18  1  0  0  0  0
  8  7  1  0  0  0  0
 10  9  1  0  0  0  0
 14 15  1  0  0  0  0
 13 16  1  0  0  0  0
 10 11  1  0  0  0  0
 21 22  1  0  0  0  0
  7  5  1  0  0  0  0
 22 23  1  0  0  0  0
  5  2  1  0  0  0  0
 23 25  1  0  0  0  0
  5  6  2  0  0  0  0
 25 29  2  0  0  0  0
  2  1  2  3  0  0  0
 18 20  1  0  0  0  0
  2  3  1  0  0  0  0
 23 24  2  0  0  0  0
  3  4  1  0  0  0  0
 17 48  1  0  0  0  0
 17 49  1  0  0  0  0
 16 46  1  0  0  0  0
 16 47  1  0  0  0  0
  9 37  1  0  0  0  0
  9 38  1  0  0  0  0
 20 53  1  0  0  0  0
  8 36  1  1  0  0  0
 26 54  1  0  0  0  0
 26 55  1  0  0  0  0
 28 56  1  0  0  0  0
 28 57  1  0  0  0  0
 28 58  1  0  0  0  0
 19 50  1  0  0  0  0
 19 51  1  0  0  0  0
 19 52  1  0  0  0  0
 12 42  1  0  0  0  0
 15 43  1  0  0  0  0
 15 44  1  0  0  0  0
 15 45  1  0  0  0  0
 11 39  1  0  0  0  0
 11 40  1  0  0  0  0
 11 41  1  0  0  0  0
  1 31  1  0  0  0  0
  1 32  1  0  0  0  0
  3 33  1  0  0  0  0
  3 34  1  0  0  0  0
  4 35  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0031682

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC([H])([H])C(=C([H])[H])C(=O)O[C@]1([H])C2=C(C(=O)O\C2=C([H])\[C@]2(O[C@](OC([H])([H])[H])(C([H])([H])C2([H])[H])[C@@](O[H])(C([H])([H])[H])C1([H])[H])C([H])([H])[H])C([H])([H])OC([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C21H28O9/c1-12(10-22)17(23)28-15-9-20(3,25)21(27-5)7-6-19(2,30-21)8-14-16(15)13(11-26-4)18(24)29-14/h8,15,22,25H,1,6-7,9-11H2,2-5H3/b14-8+/t15-,19-,20+,21+/m0/s1

> <INCHI_KEY>
VIRRBXJHWACOBN-BWSBUGDESA-N

> <FORMULA>
C21H28O9

> <MOLECULAR_WEIGHT>
424.446

> <EXACT_MASS>
424.173332482

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
58

> <JCHEM_AVERAGE_POLARIZABILITY>
42.43843377971989

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,2E,8S,10R,11R)-10-hydroxy-11-methoxy-6-(methoxymethyl)-1,10-dimethyl-5-oxo-4,14-dioxatricyclo[9.2.1.0^{3,7}]tetradeca-2,6-dien-8-yl 2-(hydroxymethyl)prop-2-enoate

> <ALOGPS_LOGP>
0.63

> <JCHEM_LOGP>
0.40093165000000197

> <ALOGPS_LOGS>
-2.80

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.90220629034015

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.039148739802467

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8442370631838063

> <JCHEM_POLAR_SURFACE_AREA>
120.75000000000003

> <JCHEM_REFRACTIVITY>
106.096

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.80e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2E,8S,10R,11R)-10-hydroxy-11-methoxy-6-(methoxymethyl)-1,10-dimethyl-5-oxo-4,14-dioxatricyclo[9.2.1.0^{3,7}]tetradeca-2,6-dien-8-yl 2-(hydroxymethyl)prop-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 58 60  0  0  0  0  0  0  0  0999 V2000
    2.0491    4.8394    1.5384 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1084    4.2385    2.2874 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6547    4.7624    3.6165 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6802    5.2446    3.5331 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4236    2.9972    1.8437 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6716    2.6706    2.2804 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1722    2.3057    0.9513 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5748    1.0984    0.3898 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2929    1.5619   -0.8064 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0557    0.4984   -1.6370 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8243    1.2262   -2.7607 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0963   -0.3344   -2.3101 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0451   -0.3422   -0.7319 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.1314    0.5226   -0.3722 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7736    0.2072    0.8543 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5651   -1.6167   -1.3956 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5083   -2.6481   -1.0690 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8860   -2.1363    0.2360 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3949   -2.9358    1.4403 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6194   -2.2091    0.1869 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6136   -1.3108    0.0999 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9050   -1.8395   -0.0628 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7077   -0.7841   -0.3575 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8929   -0.8620   -0.6371 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9515    0.4624   -0.2684 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6484    1.7537   -0.4916 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9881    2.5188   -1.5041 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4506    2.1998   -2.8116 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6906    0.1327    0.0471 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3386   -0.8028    0.4254 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5305    5.7541    1.8705 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3440    4.4602    0.5643 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7031    3.9832    4.3850 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2842    5.5916    3.9560 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2304    4.4824    3.2616 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0103    0.6702    1.2038 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0171    2.2999   -0.4351 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3580    2.1321   -1.4836 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1327    1.7757   -3.4109 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5542    1.9418   -2.3696 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3461    0.5156   -3.4097 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4959    0.2465   -2.8192 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6463    0.8583    0.9558 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1065    0.4063    1.6984 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1164   -0.8303    0.8784 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7418   -1.5172   -2.4699 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5197   -1.9292   -0.9574 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7741   -2.7040   -1.8812 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9358   -3.6528   -0.9776 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1146   -3.9931    1.3791 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4869   -2.8746    1.5163 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9984   -2.5275    2.3779 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9569   -3.2490    0.1582 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7067    1.6293   -0.7490 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6391    2.3384    0.4333 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2769    1.1439   -3.0394 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8905    2.8058   -3.5288 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5138    2.4388   -2.9103 H   0  0  0  0  0  0  0  0  0  0  0  0
 20 21  2  0
 25 26  1  0
 16 17  1  0
 26 27  1  0
  9  8  1  0
 27 28  1  0
  8 29  1  0
 13 30  1  0
 18 30  1  0
 29 21  1  0
 18 19  1  1
 13 14  1  1
 13 10  1  0
 10 12  1  6
 17 18  1  0
  8  7  1  0
 10  9  1  0
 14 15  1  0
 13 16  1  0
 10 11  1  0
 21 22  1  0
  7  5  1  0
 22 23  1  0
  5  2  1  0
 23 25  1  0
  5  6  2  0
 25 29  2  0
  2  1  2  3
 18 20  1  0
  2  3  1  0
 23 24  2  0
  3  4  1  0
 17 48  1  0
 17 49  1  0
 16 46  1  0
 16 47  1  0
  9 37  1  0
  9 38  1  0
 20 53  1  0
  8 36  1  1
 26 54  1  0
 26 55  1  0
 28 56  1  0
 28 57  1  0
 28 58  1  0
 19 50  1  0
 19 51  1  0
 19 52  1  0
 12 42  1  0
 15 43  1  0
 15 44  1  0
 15 45  1  0
 11 39  1  0
 11 40  1  0
 11 41  1  0
  1 31  1  0
  1 32  1  0
  3 33  1  0
  3 34  1  0
  4 35  1  0
M  END

HEADER    PROTEIN                                 20-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-JUN-21         0                                  
HETATM    1  C   UNK     0       2.049   4.839   1.538  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.108   4.239   2.287  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.655   4.762   3.616  0.00  0.00           C+0
HETATM    4  O   UNK     0      -0.680   5.245   3.533  0.00  0.00           O+0
HETATM    5  C   UNK     0       0.424   2.997   1.844  0.00  0.00           C+0
HETATM    6  O   UNK     0      -0.672   2.671   2.280  0.00  0.00           O+0
HETATM    7  O   UNK     0       1.172   2.306   0.951  0.00  0.00           O+0
HETATM    8  C   UNK     0       0.575   1.098   0.390  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.293   1.562  -0.806  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.056   0.498  -1.637  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.824   1.226  -2.761  0.00  0.00           C+0
HETATM   12  O   UNK     0      -0.096  -0.334  -2.310  0.00  0.00           O+0
HETATM   13  C   UNK     0      -2.045  -0.342  -0.732  0.00  0.00           C+0
HETATM   14  O   UNK     0      -3.131   0.523  -0.372  0.00  0.00           O+0
HETATM   15  C   UNK     0      -3.774   0.207   0.854  0.00  0.00           C+0
HETATM   16  C   UNK     0      -2.565  -1.617  -1.396  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.508  -2.648  -1.069  0.00  0.00           C+0
HETATM   18  C   UNK     0      -0.886  -2.136   0.236  0.00  0.00           C+0
HETATM   19  C   UNK     0      -1.395  -2.936   1.440  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.619  -2.209   0.187  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.614  -1.311   0.100  0.00  0.00           C+0
HETATM   22  O   UNK     0       2.905  -1.839  -0.063  0.00  0.00           O+0
HETATM   23  C   UNK     0       3.708  -0.784  -0.358  0.00  0.00           C+0
HETATM   24  O   UNK     0       4.893  -0.862  -0.637  0.00  0.00           O+0
HETATM   25  C   UNK     0       2.951   0.462  -0.268  0.00  0.00           C+0
HETATM   26  C   UNK     0       3.648   1.754  -0.492  0.00  0.00           C+0
HETATM   27  O   UNK     0       2.988   2.519  -1.504  0.00  0.00           O+0
HETATM   28  C   UNK     0       3.451   2.200  -2.812  0.00  0.00           C+0
HETATM   29  C   UNK     0       1.691   0.133   0.047  0.00  0.00           C+0
HETATM   30  O   UNK     0      -1.339  -0.803   0.425  0.00  0.00           O+0
HETATM   31  H   UNK     0       2.531   5.754   1.871  0.00  0.00           H+0
HETATM   32  H   UNK     0       2.344   4.460   0.564  0.00  0.00           H+0
HETATM   33  H   UNK     0       0.703   3.983   4.385  0.00  0.00           H+0
HETATM   34  H   UNK     0       1.284   5.592   3.956  0.00  0.00           H+0
HETATM   35  H   UNK     0      -1.230   4.482   3.262  0.00  0.00           H+0
HETATM   36  H   UNK     0      -0.010   0.670   1.204  0.00  0.00           H+0
HETATM   37  H   UNK     0      -1.017   2.300  -0.435  0.00  0.00           H+0
HETATM   38  H   UNK     0       0.358   2.132  -1.484  0.00  0.00           H+0
HETATM   39  H   UNK     0      -1.133   1.776  -3.411  0.00  0.00           H+0
HETATM   40  H   UNK     0      -2.554   1.942  -2.370  0.00  0.00           H+0
HETATM   41  H   UNK     0      -2.346   0.516  -3.410  0.00  0.00           H+0
HETATM   42  H   UNK     0       0.496   0.247  -2.819  0.00  0.00           H+0
HETATM   43  H   UNK     0      -4.646   0.858   0.956  0.00  0.00           H+0
HETATM   44  H   UNK     0      -3.107   0.406   1.698  0.00  0.00           H+0
HETATM   45  H   UNK     0      -4.116  -0.830   0.878  0.00  0.00           H+0
HETATM   46  H   UNK     0      -2.742  -1.517  -2.470  0.00  0.00           H+0
HETATM   47  H   UNK     0      -3.520  -1.929  -0.957  0.00  0.00           H+0
HETATM   48  H   UNK     0      -0.774  -2.704  -1.881  0.00  0.00           H+0
HETATM   49  H   UNK     0      -1.936  -3.653  -0.978  0.00  0.00           H+0
HETATM   50  H   UNK     0      -1.115  -3.993   1.379  0.00  0.00           H+0
HETATM   51  H   UNK     0      -2.487  -2.875   1.516  0.00  0.00           H+0
HETATM   52  H   UNK     0      -0.998  -2.527   2.378  0.00  0.00           H+0
HETATM   53  H   UNK     0       0.957  -3.249   0.158  0.00  0.00           H+0
HETATM   54  H   UNK     0       4.707   1.629  -0.749  0.00  0.00           H+0
HETATM   55  H   UNK     0       3.639   2.338   0.433  0.00  0.00           H+0
HETATM   56  H   UNK     0       3.277   1.144  -3.039  0.00  0.00           H+0
HETATM   57  H   UNK     0       2.890   2.806  -3.529  0.00  0.00           H+0
HETATM   58  H   UNK     0       4.514   2.439  -2.910  0.00  0.00           H+0
CONECT    1    2   31   32                                                  
CONECT    2    5    1    3                                                  
CONECT    3    2    4   33   34                                             
CONECT    4    3   35                                                       
CONECT    5    7    2    6                                                  
CONECT    6    5                                                            
CONECT    7    8    5                                                       
CONECT    8    9   29    7   36                                             
CONECT    9    8   10   37   38                                             
CONECT   10   13   12    9   11                                             
CONECT   11   10   39   40   41                                             
CONECT   12   10   42                                                       
CONECT   13   30   14   10   16                                             
CONECT   14   13   15                                                       
CONECT   15   14   43   44   45                                             
CONECT   16   17   13   46   47                                             
CONECT   17   16   18   48   49                                             
CONECT   18   30   19   17   20                                             
CONECT   19   18   50   51   52                                             
CONECT   20   21   18   53                                                  
CONECT   21   20   29   22                                                  
CONECT   22   21   23                                                       
CONECT   23   22   25   24                                                  
CONECT   24   23                                                            
CONECT   25   26   23   29                                                  
CONECT   26   25   27   54   55                                             
CONECT   27   26   28                                                       
CONECT   28   27   56   57   58                                             
CONECT   29    8   21   25                                                  
CONECT   30   13   18                                                       
CONECT   31    1                                                            
CONECT   32    1                                                            
CONECT   33    3                                                            
CONECT   34    3                                                            
CONECT   35    4                                                            
CONECT   36    8                                                            
CONECT   37    9                                                            
CONECT   38    9                                                            
CONECT   39   11                                                            
CONECT   40   11                                                            
CONECT   41   11                                                            
CONECT   42   12                                                            
CONECT   43   15                                                            
CONECT   44   15                                                            
CONECT   45   15                                                            
CONECT   46   16                                                            
CONECT   47   16                                                            
CONECT   48   17                                                            
CONECT   49   17                                                            
CONECT   50   19                                                            
CONECT   51   19                                                            
CONECT   52   19                                                            
CONECT   53   20                                                            
CONECT   54   26                                                            
CONECT   55   26                                                            
CONECT   56   28                                                            
CONECT   57   28                                                            
CONECT   58   28                                                            
MASTER        0    0    0    0    0    0    0    0   58    0  120    0
END

RDKit          3D

58 60  0  0  0  0  0  0  0  0999 V2000
    2.0491    4.8394    1.5384 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1084    4.2385    2.2874 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6547    4.7624    3.6165 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6802    5.2446    3.5331 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4236    2.9972    1.8437 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6716    2.6706    2.2804 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1722    2.3057    0.9513 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5748    1.0984    0.3898 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2929    1.5619   -0.8064 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0557    0.4984   -1.6370 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8243    1.2262   -2.7607 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0963   -0.3344   -2.3101 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0451   -0.3422   -0.7319 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.1314    0.5226   -0.3722 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7736    0.2072    0.8543 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5651   -1.6167   -1.3956 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5083   -2.6481   -1.0690 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8860   -2.1363    0.2360 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3949   -2.9358    1.4403 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6194   -2.2091    0.1869 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6136   -1.3108    0.0999 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9050   -1.8395   -0.0628 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7077   -0.7841   -0.3575 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8929   -0.8620   -0.6371 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9515    0.4624   -0.2684 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6484    1.7537   -0.4916 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9881    2.5188   -1.5041 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4506    2.1998   -2.8116 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6906    0.1327    0.0471 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3386   -0.8028    0.4254 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5305    5.7541    1.8705 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3440    4.4602    0.5643 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7031    3.9832    4.3850 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2842    5.5916    3.9560 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2304    4.4824    3.2616 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0103    0.6702    1.2038 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0171    2.2999   -0.4351 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3580    2.1321   -1.4836 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1327    1.7757   -3.4109 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5542    1.9418   -2.3696 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3461    0.5156   -3.4097 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4959    0.2465   -2.8192 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6463    0.8583    0.9558 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1065    0.4063    1.6984 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1164   -0.8303    0.8784 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7418   -1.5172   -2.4699 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5197   -1.9292   -0.9574 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7741   -2.7040   -1.8812 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9358   -3.6528   -0.9776 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1146   -3.9931    1.3791 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4869   -2.8746    1.5163 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9984   -2.5275    2.3779 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9569   -3.2490    0.1582 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7067    1.6293   -0.7490 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6391    2.3384    0.4333 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2769    1.1439   -3.0394 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8905    2.8058   -3.5288 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5138    2.4388   -2.9103 H   0  0  0  0  0  0  0  0  0  0  0  0
 20 21  2  0
 25 26  1  0
 16 17  1  0
 26 27  1  0
  9  8  1  0
 27 28  1  0
  8 29  1  0
 13 30  1  0
 18 30  1  0
 29 21  1  0
 18 19  1  1
 13 14  1  1
 13 10  1  0
 10 12  1  6
 17 18  1  0
  8  7  1  0
 10  9  1  0
 14 15  1  0
 13 16  1  0
 10 11  1  0
 21 22  1  0
  7  5  1  0
 22 23  1  0
  5  2  1  0
 23 25  1  0
  5  6  2  0
 25 29  2  0
  2  1  2  3
 18 20  1  0
  2  3  1  0
 23 24  2  0
  3  4  1  0
 17 48  1  0
 17 49  1  0
 16 46  1  0
 16 47  1  0
  9 37  1  0
  9 38  1  0
 20 53  1  0
  8 36  1  1
 26 54  1  0
 26 55  1  0
 28 56  1  0
 28 57  1  0
 28 58  1  0
 19 50  1  0
 19 51  1  0
 19 52  1  0
 12 42  1  0
 15 43  1  0
 15 44  1  0
 15 45  1  0
 11 39  1  0
 11 40  1  0
 11 41  1  0
  1 31  1  0
  1 32  1  0
  3 33  1  0
  3 34  1  0
  4 35  1  0
M  END

View in JSmol View DFT Assignments 3D Conformers

Synonyms

Not Available

Chemical Formula

C₂₁H₂₈O₉

Average Mass

424.4460 Da

Monoisotopic Mass

424.17333 Da

IUPAC Name

(1S,2E,8S,10R,11R)-10-hydroxy-11-methoxy-6-(methoxymethyl)-1,10-dimethyl-5-oxo-4,14-dioxatricyclo[9.2.1.0^{3,7}]tetradeca-2,6-dien-8-yl 2-(hydroxymethyl)prop-2-enoate

Traditional Name

(1S,2E,8S,10R,11R)-10-hydroxy-11-methoxy-6-(methoxymethyl)-1,10-dimethyl-5-oxo-4,14-dioxatricyclo[9.2.1.0^{3,7}]tetradeca-2,6-dien-8-yl 2-(hydroxymethyl)prop-2-enoate

CAS Registry Number

Not Available

SMILES

[H]OC([H])([H])C(=C([H])[H])C(=O)O[C@]1([H])C2=C(C(=O)O\C2=C([H])\[C@]2(O[C@](OC([H])([H])[H])(C([H])([H])C2([H])[H])[C@@](O[H])(C([H])([H])[H])C1([H])[H])C([H])([H])[H])C([H])([H])OC([H])([H])[H]

InChI Identifier

InChI=1S/C21H28O9/c1-12(10-22)17(23)28-15-9-20(3,25)21(27-5)7-6-19(2,30-21)8-14-16(15)13(11-26-4)18(24)29-14/h8,15,22,25H,1,6-7,9-11H2,2-5H3/b14-8+/t15-,19-,20+,21+/m0/s1

InChI Key

VIRRBXJHWACOBN-BWSBUGDESA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 150 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 175 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 225 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 250 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, chcl3, 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
Vernonia triflosculosa	JEOL database	Kos, O., et al, Phytochemistry 67, 62 (2006)

Chemical Taxonomy

Classification

Not classified

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	0.63	ALOGPS
logP	0.4	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	13.04	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	120.75 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	106.1 m³·mol⁻¹	ChemAxon
Polarizability	42.44 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

Not Available

References

General References

Kos, O., et al. (2006). Kos, O., et al, Phytochemistry 67, 62 (2006) . Phytochem..

Showing NP-Card for 8alpha-(4-hydroxymethacryloyloxy)-10alpha-hydroxy-1,13-dimethoxy-hirsutin+ (NP0031682)

MOL for NP0031682 (8alpha-(4-hydroxymethacryloyloxy)-10alpha-hydroxy-1,13-dimethoxy-hirsutin+)

3D MOL for NP0031682 (8alpha-(4-hydroxymethacryloyloxy)-10alpha-hydroxy-1,13-dimethoxy-hirsutin+)

3D SDF for NP0031682 (8alpha-(4-hydroxymethacryloyloxy)-10alpha-hydroxy-1,13-dimethoxy-hirsutin+)

3D-SDF for NP0031682 (8alpha-(4-hydroxymethacryloyloxy)-10alpha-hydroxy-1,13-dimethoxy-hirsutin+)

PDB for NP0031682 (8alpha-(4-hydroxymethacryloyloxy)-10alpha-hydroxy-1,13-dimethoxy-hirsutin+)

3D PDB for NP0031682 (8alpha-(4-hydroxymethacryloyloxy)-10alpha-hydroxy-1,13-dimethoxy-hirsutin+)

SMILES for NP0031682 (8alpha-(4-hydroxymethacryloyloxy)-10alpha-hydroxy-1,13-dimethoxy-hirsutin+)

INCHI for NP0031682 (8alpha-(4-hydroxymethacryloyloxy)-10alpha-hydroxy-1,13-dimethoxy-hirsutin+)

Structure for NP0031682 (8alpha-(4-hydroxymethacryloyloxy)-10alpha-hydroxy-1,13-dimethoxy-hirsutin+)

3D Structure for NP0031682 (8alpha-(4-hydroxymethacryloyloxy)-10alpha-hydroxy-1,13-dimethoxy-hirsutin+)