NP-MRD: Showing NP-Card for (1r,2r,6s,7s,8r,10s,11s,12r,14s,16s,17r,18r)-6,7-dihydroxy-8-(hydroxymethyl)-4,18-dimethyl-14-[(1e,3e)-nona-1,3-dien-1-yl]-5-oxo-16-(prop-1-en-2-yl)-9,13,15,19-tetraoxahexacyclo[12.4.1.0¹,¹¹.0²,⁶.0⁸,¹⁰.0¹²,¹⁶]nonadec-3-en-17-yl benzoate (NP0229477)

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Record Information

Version

2.0

Created at

2022-09-06 09:32:59 UTC

Updated at

2022-09-06 09:32:59 UTC

NP-MRD ID

NP0229477

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,2r,6s,7s,8r,10s,11s,12r,14s,16s,17r,18r)-6,7-dihydroxy-8-(hydroxymethyl)-4,18-dimethyl-14-[(1e,3e)-nona-1,3-dien-1-yl]-5-oxo-16-(prop-1-en-2-yl)-9,13,15,19-tetraoxahexacyclo[12.4.1.0¹,¹¹.0²,⁶.0⁸,¹⁰.0¹²,¹⁶]nonadec-3-en-17-yl benzoate

Description

Yuanhuacine, also known as YHL-14, belongs to the class of organic compounds known as rhamnofolane and daphnane diterpenoids. These are diterpenoids with a structure based on one the rhamnofolane or daphnane skeleton. The rhamnofolane and daphnane skeletons are closely related, being formally derived from casbane by two cyclizations (6,10 and 5,14) followed by cleavage of the 1,15 (daphnane) or 2,15 (rhamnofolane) cyclopropane bonds. (1r,2r,6s,7s,8r,10s,11s,12r,14s,16s,17r,18r)-6,7-dihydroxy-8-(hydroxymethyl)-4,18-dimethyl-14-[(1e,3e)-nona-1,3-dien-1-yl]-5-oxo-16-(prop-1-en-2-yl)-9,13,15,19-tetraoxahexacyclo[12.4.1.0¹,¹¹.0²,⁶.0⁸,¹⁰.0¹²,¹⁶]nonadec-3-en-17-yl benzoate is found in Daphne genkwa, Daphne odora and Daphne oleoides. (1r,2r,6s,7s,8r,10s,11s,12r,14s,16s,17r,18r)-6,7-dihydroxy-8-(hydroxymethyl)-4,18-dimethyl-14-[(1e,3e)-nona-1,3-dien-1-yl]-5-oxo-16-(prop-1-en-2-yl)-9,13,15,19-tetraoxahexacyclo[12.4.1.0¹,¹¹.0²,⁶.0⁸,¹⁰.0¹²,¹⁶]nonadec-3-en-17-yl benzoate was first documented in 2018 (PMID: 29680963). Based on a literature review a small amount of articles have been published on Yuanhuacine (PMID: 35204693) (PMID: 35891417) (PMID: 35004606) (PMID: 34200174).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309062211332D          

 47 53  0  0  1  0            999 V2000
   -2.3935   -2.3696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.1048   -0.9539    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7319   -0.1217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2275    0.7233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6295    1.4437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2067    2.1521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  1  2  2  0  0  0  0
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M  END

     RDKit          3D

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 35  6  1  0
 47 42  1  0
  5  6  1  0
  4 17  1  0
 34 18  1  0
 21 19  1  0
 28 26  1  0
 15 65  1  0
 15 66  1  0
 15 67  1  0
 14 63  1  0
 14 64  1  0
 13 61  1  0
 13 62  1  0
 12 59  1  0
 12 60  1  0
 11 57  1  0
 11 58  1  0
 10 56  1  0
  9 55  1  0
  8 54  1  0
  7 53  1  0
 17 68  1  1
 18 69  1  6
 19 70  1  1
 22 71  1  0
 22 72  1  0
 23 73  1  0
 24 74  1  6
 25 75  1  0
 27 76  1  0
 33 81  1  1
 32 80  1  0
 31 77  1  0
 31 78  1  0
 31 79  1  0
 36 82  1  6
 37 83  1  0
 37 84  1  0
 37 85  1  0
 38 86  1  6
 43 87  1  0
 44 88  1  0
 45 89  1  0
 46 90  1  0
 47 91  1  0
  3 50  1  0
  3 51  1  0
  3 52  1  0
  1 48  1  0
  1 49  1  0
M  END


  Mrv1652309062211332D          

 47 53  0  0  1  0            999 V2000
   -2.3935   -2.3696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5018   -2.4036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6708   -3.2686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5534   -2.0169    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8891   -1.2388    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1048   -0.9539    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7319   -0.1217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2275    0.7233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6295    1.4437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2067    2.1521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6087    2.8725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1858    3.5809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5878    4.3013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1650    5.0097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5670    5.7301    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0110   -1.9829    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6465   -2.0371    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9411   -1.3680    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4360   -0.7080    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0238   -0.1290    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2285    0.0905    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8442    0.7880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7090    1.0739    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4749    0.4261    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7620    1.2741    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2574    0.0461    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8168    0.8442    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9779    0.4480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6548    1.0855    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5827   -0.1131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4810    0.0874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2360   -0.8617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4169   -0.7633    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1165   -1.3927    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5097   -0.5897    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3012   -2.5364    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9205   -3.1837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4614   -2.7524    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9697   -3.5612    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4749   -4.2577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3465   -4.1802    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8185   -5.0078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3407   -5.6803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6843   -6.4304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5056   -6.5079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9834   -5.8353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6398   -5.0852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  4  2  1  1  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  1  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
  6 16  1  0  0  0  0
 17 16  1  1  0  0  0
  4 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  1  0  0  0
 19 20  1  1  0  0  0
 20 21  1  0  0  0  0
 19 21  1  0  0  0  0
 21 22  1  6  0  0  0
 22 23  1  0  0  0  0
 21 24  1  0  0  0  0
 24 25  1  6  0  0  0
 24 26  1  0  0  0  0
 26 27  1  6  0  0  0
 26 28  1  0  0  0  0
 28 29  2  0  0  0  0
 28 30  1  0  0  0  0
 30 31  1  0  0  0  0
 30 32  2  0  0  0  0
 33 32  1  6  0  0  0
 26 33  1  0  0  0  0
 33 34  1  0  0  0  0
 18 34  1  0  0  0  0
 34 35  1  1  0  0  0
  6 35  1  0  0  0  0
 34 36  1  0  0  0  0
 36 37  1  6  0  0  0
 36 38  1  0  0  0  0
  4 38  1  0  0  0  0
 38 39  1  1  0  0  0
 39 40  1  0  0  0  0
 40 41  2  0  0  0  0
 40 42  1  0  0  0  0
 42 43  2  0  0  0  0
 43 44  1  0  0  0  0
 44 45  2  0  0  0  0
 45 46  1  0  0  0  0
 46 47  2  0  0  0  0
 42 47  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0229477

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCC\C=C\C=C\[C@]12O[C@@H]3[C@@H]4[C@@H]5O[C@]5(CO)[C@@H](O)[C@@]5(O)[C@@H](C=C(C)C5=O)[C@@]4(O1)[C@H](C)[C@@H](OC(=O)C1=CC=CC=C1)[C@@]3(O2)C(C)=C

> <INCHI_IDENTIFIER>
InChI=1S/C37H44O10/c1-6-7-8-9-10-11-15-18-34-45-30-26-29-33(20-38,44-29)32(41)35(42)25(19-22(4)27(35)39)37(26,47-34)23(5)28(36(30,46-34)21(2)3)43-31(40)24-16-13-12-14-17-24/h10-19,23,25-26,28-30,32,38,41-42H,2,6-9,20H2,1,3-5H3/b11-10+,18-15+/t23-,25-,26+,28-,29+,30-,32-,33+,34-,35-,36+,37+/m1/s1

> <INCHI_KEY>
CGSGRJNIABXQJQ-NSCQCFIPSA-N

> <FORMULA>
C37H44O10

> <MOLECULAR_WEIGHT>
648.749

> <EXACT_MASS>
648.293447617

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
91

> <JCHEM_AVERAGE_POLARIZABILITY>
70.0359851620872

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,2R,6S,7S,8R,10S,11S,12R,14S,16S,17R,18R)-6,7-dihydroxy-8-(hydroxymethyl)-4,18-dimethyl-14-[(1E,3E)-nona-1,3-dien-1-yl]-5-oxo-16-(prop-1-en-2-yl)-9,13,15,19-tetraoxahexacyclo[12.4.1.0^{1,11}.0^{2,6}.0^{8,10}.0^{12,16}]nonadec-3-en-17-yl benzoate

> <JCHEM_LOGP>
5.496266238999999

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.327888241603734

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.646350408684132

> <JCHEM_PKA_STRONGEST_BASIC>
-3.1497130859375035

> <JCHEM_POLAR_SURFACE_AREA>
144.28

> <JCHEM_REFRACTIVITY>
172.58879999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2R,6S,7S,8R,10S,11S,12R,14S,16S,17R,18R)-6,7-dihydroxy-8-(hydroxymethyl)-4,18-dimethyl-14-[(1E,3E)-nona-1,3-dien-1-yl]-5-oxo-16-(prop-1-en-2-yl)-9,13,15,19-tetraoxahexacyclo[12.4.1.0^{1,11}.0^{2,6}.0^{8,10}.0^{12,16}]nonadec-3-en-17-yl benzoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-22         0                                  
HETATM    1  C   UNK     0      -4.468  -4.423   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.803  -4.487   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -3.119  -6.101   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.033  -3.765   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -1.660  -2.312   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      -0.196  -1.781   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.366  -0.227   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.425   1.350   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.175   2.695   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.386   4.017   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.136   5.362   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.347   6.684   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.097   8.029   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.308   9.351   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.058  10.696   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -0.021  -3.701   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       1.207  -3.803   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.757  -2.554   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.681  -1.322   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       3.778  -0.241   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       2.293   0.169   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       3.443   1.471   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       5.057   2.005   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       0.886   0.795   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       1.422   2.378   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      -0.480   0.086   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      -1.525   1.576   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      -1.825   0.836   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      -3.089   2.026   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      -2.954  -0.211   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -4.631   0.163   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -2.307  -1.609   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -0.778  -1.425   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       0.217  -2.600   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       0.951  -1.101   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0       0.562  -4.735   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       1.718  -5.943   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      -0.861  -5.138   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0      -1.810  -6.648   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0      -0.886  -7.948   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0       0.647  -7.803   0.000  0.00  0.00           O+0
HETATM   42  C   UNK     0      -1.528  -9.348   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0      -0.636 -10.603   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0      -1.277 -12.003   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0      -2.810 -12.148   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0      -3.702 -10.893   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0      -3.061  -9.492   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   17   38                                             
CONECT    5    4    6                                                       
CONECT    6    5    7   16   35                                             
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14                                                            
CONECT   16    6   17                                                       
CONECT   17   16    4   18                                                  
CONECT   18   17   19   34                                                  
CONECT   19   18   20   21                                                  
CONECT   20   19   21                                                       
CONECT   21   20   19   22   24                                             
CONECT   22   21   23                                                       
CONECT   23   22                                                            
CONECT   24   21   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27   28   33                                             
CONECT   27   26                                                            
CONECT   28   26   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   33                                                       
CONECT   33   32   26   34                                                  
CONECT   34   33   18   35   36                                             
CONECT   35   34    6                                                       
CONECT   36   34   37   38                                                  
CONECT   37   36                                                            
CONECT   38   36    4   39                                                  
CONECT   39   38   40                                                       
CONECT   40   39   41   42                                                  
CONECT   41   40                                                            
CONECT   42   40   43   47                                                  
CONECT   43   42   44                                                       
CONECT   44   43   45                                                       
CONECT   45   44   46                                                       
CONECT   46   45   47                                                       
CONECT   47   46   42                                                       
MASTER        0    0    0    0    0    0    0    0   47    0  106    0
END

View in JSmol

Synonyms

Value	Source
YHL-14	MeSH
Yuanhuacin	MeSH
Yuanhuacin a	MeSH

Chemical Formula

C₃₇H₄₄O₁₀

Average Mass

648.7490 Da

Monoisotopic Mass

648.29345 Da

IUPAC Name

(1R,2R,6S,7S,8R,10S,11S,12R,14S,16S,17R,18R)-6,7-dihydroxy-8-(hydroxymethyl)-4,18-dimethyl-14-[(1E,3E)-nona-1,3-dien-1-yl]-5-oxo-16-(prop-1-en-2-yl)-9,13,15,19-tetraoxahexacyclo[12.4.1.0^{1,11}.0^{2,6}.0^{8,10}.0^{12,16}]nonadec-3-en-17-yl benzoate

Traditional Name

CAS Registry Number

Not Available

SMILES

CCCCC\C=C\C=C\[C@]12O[C@@H]3[C@@H]4[C@@H]5O[C@]5(CO)[C@@H](O)[C@@]5(O)[C@@H](C=C(C)C5=O)[C@@]4(O1)[C@H](C)[C@@H](OC(=O)C1=CC=CC=C1)[C@@]3(O2)C(C)=C

InChI Identifier

InChI=1S/C37H44O10/c1-6-7-8-9-10-11-15-18-34-45-30-26-29-33(20-38,44-29)32(41)35(42)25(19-22(4)27(35)39)37(26,47-34)23(5)28(36(30,46-34)21(2)3)43-31(40)24-16-13-12-14-17-24/h10-19,23,25-26,28-30,32,38,41-42H,2,6-9,20H2,1,3-5H3/b11-10+,18-15+/t23-,25-,26+,28-,29+,30-,32-,33+,34-,35-,36+,37+/m1/s1

InChI Key

CGSGRJNIABXQJQ-NSCQCFIPSA-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
Daphne genkwa	LOTUS Database	35616633
Daphne odora	LOTUS Database	35616633
Daphne oleoides	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as rhamnofolane and daphnane diterpenoids. These are diterpenoids with a structure based on one the rhamnofolane or daphnane skeleton. The rhamnofolane and daphnane skeletons are closely related, being formally derived from casbane by two cyclizations (6,10 and 5,14) followed by cleavage of the 1,15 (daphnane) or 2,15 (rhamnofolane) cyclopropane bonds.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Rhamnofolane and daphnane diterpenoids

Alternative Parents

Substituents

Daphnane diterpenoid
Benzoate ester
Benzoic acid or derivatives
Benzoyl
Carboxylic acid orthoester
Ortho ester
1,3-dioxepane
Dioxepane
Meta-dioxane
Benzenoid
Monocyclic benzene moiety
Tertiary alcohol
Cyclic alcohol
Meta-dioxolane
Secondary alcohol
Carboxylic acid ester
Orthocarboxylic acid derivative
Ketone
Dialkyl ether
Carboxylic acid derivative
Oxacycle
Monocarboxylic acid or derivatives
Organoheterocyclic compound
Oxirane
Ether
Primary alcohol
Organic oxide
Organic oxygen compound
Carbonyl group
Alcohol
Hydrocarbon derivative
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	5.5	ChemAxon
pKa (Strongest Acidic)	11.65	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	144.28 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	172.59 m³·mol⁻¹	ChemAxon
Polarizability	70.04 Å³	ChemAxon
Number of Rings	7	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	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

4513793

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5358691

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Bailly C: Yuanhuacin and Related Anti-Inflammatory and Anticancer Daphnane Diterpenes from Genkwa Flos-An Overview. Biomolecules. 2022 Jan 23;12(2). pii: biom12020192. doi: 10.3390/biom12020192. [PubMed:35204693 ]
Wang L, Lan XY, Ji J, Zhang CF, Li F, Wang CZ, Yuan CS: Anti-inflammatory and anti-angiogenic activities in vitro of eight diterpenes from Daphne genkwa based on hierarchical cluster and principal component analysis. J Nat Med. 2018 Jun;72(3):675-685. doi: 10.1007/s11418-018-1202-1. Epub 2018 Apr 21. [PubMed:29680963 ]
Tembeni B, Sciorillo A, Invernizzi L, Klimkait T, Urda L, Moyo P, Naidoo-Maharaj D, Levitties N, Gyampoh K, Zu G, Yuan Z, Mounzer K, Nkabinde S, Nkabinde M, Gqaleni N, Tietjen I, Montaner LJ, Maharaj V: HPLC-Based Purification and Isolation of Potent Anti-HIV and Latency Reversing Daphnane Diterpenes from the Medicinal Plant Gnidia sericocephala (Thymelaeaceae). Viruses. 2022 Jun 30;14(7):1437. doi: 10.3390/v14071437. [PubMed:35891417 ]
Yang Y, Li F, Yan M, Chen S, Cai D, Liu X, Han N, Yuan Z, Lu J, Zhang Y, Ma Q, Wang P, Lei H: Revealing the Toxicity-Enhancing Essence of Glycyrrhiza on Genkwa Flos Based on Ultra-high-performance Liquid Chromatography Coupled With Quadrupole-Orbitrap High-Resolution Mass Spectrometry and Self-Assembled Supramolecular Technology. Front Chem. 2021 Dec 23;9:740952. doi: 10.3389/fchem.2021.740952. eCollection 2021. [PubMed:35004606 ]
Fermaintt CS, Peramuna T, Cai S, Takahashi-Ruiz L, Essif JN, Grant CV, O'Keefe BR, Mooberry SL, Cichewicz RH, Risinger AL: Yuanhuacine Is a Potent and Selective Inhibitor of the Basal-Like 2 Subtype of Triple Negative Breast Cancer with Immunogenic Potential. Cancers (Basel). 2021 Jun 7;13(11):2834. doi: 10.3390/cancers13112834. [PubMed:34200174 ]
LOTUS database [Link]

Showing NP-Card for (1r,2r,6s,7s,8r,10s,11s,12r,14s,16s,17r,18r)-6,7-dihydroxy-8-(hydroxymethyl)-4,18-dimethyl-14-[(1e,3e)-nona-1,3-dien-1-yl]-5-oxo-16-(prop-1-en-2-yl)-9,13,15,19-tetraoxahexacyclo[12.4.1.0¹,¹¹.0²,⁶.0⁸,¹⁰.0¹²,¹⁶]nonadec-3-en-17-yl benzoate (NP0229477)

MOL for NP0229477 ((1r,2r,6s,7s,8r,10s,11s,12r,14s,16s,17r,18r)-6,7-dihydroxy-8-(hydroxymethyl)-4,18-dimethyl-14-[(1e,3e)-nona-1,3-dien-1-yl]-5-oxo-16-(prop-1-en-2-yl)-9,13,15,19-tetraoxahexacyclo[12.4.1.0¹,¹¹.0²,⁶.0⁸,¹⁰.0¹²,¹⁶]nonadec-3-en-17-yl benzoate)

3D MOL for NP0229477 ((1r,2r,6s,7s,8r,10s,11s,12r,14s,16s,17r,18r)-6,7-dihydroxy-8-(hydroxymethyl)-4,18-dimethyl-14-[(1e,3e)-nona-1,3-dien-1-yl]-5-oxo-16-(prop-1-en-2-yl)-9,13,15,19-tetraoxahexacyclo[12.4.1.0¹,¹¹.0²,⁶.0⁸,¹⁰.0¹²,¹⁶]nonadec-3-en-17-yl benzoate)

3D SDF for NP0229477 ((1r,2r,6s,7s,8r,10s,11s,12r,14s,16s,17r,18r)-6,7-dihydroxy-8-(hydroxymethyl)-4,18-dimethyl-14-[(1e,3e)-nona-1,3-dien-1-yl]-5-oxo-16-(prop-1-en-2-yl)-9,13,15,19-tetraoxahexacyclo[12.4.1.0¹,¹¹.0²,⁶.0⁸,¹⁰.0¹²,¹⁶]nonadec-3-en-17-yl benzoate)

3D-SDF for NP0229477 ((1r,2r,6s,7s,8r,10s,11s,12r,14s,16s,17r,18r)-6,7-dihydroxy-8-(hydroxymethyl)-4,18-dimethyl-14-[(1e,3e)-nona-1,3-dien-1-yl]-5-oxo-16-(prop-1-en-2-yl)-9,13,15,19-tetraoxahexacyclo[12.4.1.0¹,¹¹.0²,⁶.0⁸,¹⁰.0¹²,¹⁶]nonadec-3-en-17-yl benzoate)

PDB for NP0229477 ((1r,2r,6s,7s,8r,10s,11s,12r,14s,16s,17r,18r)-6,7-dihydroxy-8-(hydroxymethyl)-4,18-dimethyl-14-[(1e,3e)-nona-1,3-dien-1-yl]-5-oxo-16-(prop-1-en-2-yl)-9,13,15,19-tetraoxahexacyclo[12.4.1.0¹,¹¹.0²,⁶.0⁸,¹⁰.0¹²,¹⁶]nonadec-3-en-17-yl benzoate)

3D PDB for NP0229477 ((1r,2r,6s,7s,8r,10s,11s,12r,14s,16s,17r,18r)-6,7-dihydroxy-8-(hydroxymethyl)-4,18-dimethyl-14-[(1e,3e)-nona-1,3-dien-1-yl]-5-oxo-16-(prop-1-en-2-yl)-9,13,15,19-tetraoxahexacyclo[12.4.1.0¹,¹¹.0²,⁶.0⁸,¹⁰.0¹²,¹⁶]nonadec-3-en-17-yl benzoate)

SMILES for NP0229477 ((1r,2r,6s,7s,8r,10s,11s,12r,14s,16s,17r,18r)-6,7-dihydroxy-8-(hydroxymethyl)-4,18-dimethyl-14-[(1e,3e)-nona-1,3-dien-1-yl]-5-oxo-16-(prop-1-en-2-yl)-9,13,15,19-tetraoxahexacyclo[12.4.1.0¹,¹¹.0²,⁶.0⁸,¹⁰.0¹²,¹⁶]nonadec-3-en-17-yl benzoate)

INCHI for NP0229477 ((1r,2r,6s,7s,8r,10s,11s,12r,14s,16s,17r,18r)-6,7-dihydroxy-8-(hydroxymethyl)-4,18-dimethyl-14-[(1e,3e)-nona-1,3-dien-1-yl]-5-oxo-16-(prop-1-en-2-yl)-9,13,15,19-tetraoxahexacyclo[12.4.1.0¹,¹¹.0²,⁶.0⁸,¹⁰.0¹²,¹⁶]nonadec-3-en-17-yl benzoate)

Structure for NP0229477 ((1r,2r,6s,7s,8r,10s,11s,12r,14s,16s,17r,18r)-6,7-dihydroxy-8-(hydroxymethyl)-4,18-dimethyl-14-[(1e,3e)-nona-1,3-dien-1-yl]-5-oxo-16-(prop-1-en-2-yl)-9,13,15,19-tetraoxahexacyclo[12.4.1.0¹,¹¹.0²,⁶.0⁸,¹⁰.0¹²,¹⁶]nonadec-3-en-17-yl benzoate)

3D Structure for NP0229477 ((1r,2r,6s,7s,8r,10s,11s,12r,14s,16s,17r,18r)-6,7-dihydroxy-8-(hydroxymethyl)-4,18-dimethyl-14-[(1e,3e)-nona-1,3-dien-1-yl]-5-oxo-16-(prop-1-en-2-yl)-9,13,15,19-tetraoxahexacyclo[12.4.1.0¹,¹¹.0²,⁶.0⁸,¹⁰.0¹²,¹⁶]nonadec-3-en-17-yl benzoate)