NP-MRD: Showing NP-Card for nardoaristolone A (NP0042236)

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Record Information

Version

2.0

Created at

2021-06-20 23:56:52 UTC

Updated at

2021-06-30 00:17:12 UTC

NP-MRD ID

NP0042236

Secondary Accession Numbers

None

Natural Product Identification

Common Name

nardoaristolone A

Provided By

JEOL Database JEOL Logo

Description

Nardokanshone A belongs to the class of organic compounds known as 2'-hydroxychalcones. These are organic compounds containing chalcone skeleton that carries a hydroxyl group at the 2'-position. nardoaristolone A is found in Nardostachys chinensis Batal. nardoaristolone A was first documented in 2013 (Liu, M.-L. et al.). Based on a literature review very few articles have been published on Nardokanshone A.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306212101563D          

 73 78  0  0  0  0            999 V2000
    5.2135    3.7517    5.0431 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0377    3.7710    5.8432 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0522    2.8841    5.5098 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0787    1.9901    4.4420 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9944    1.1324    4.2124 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8703    1.1479    5.0478 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

 73 78  0  0  0  0  0  0  0  0999 V2000
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  9 10  2  0
 36 69  1  0
 36 70  1  0
 35 67  1  0
 35 68  1  0
 33 63  1  6
 37 71  1  1
 34 64  1  0
 34 65  1  0
 34 66  1  0
 26 52  1  1
 27 53  1  1
 32 60  1  0
 32 61  1  0
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 29 54  1  0
 29 55  1  0
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 14 48  1  0
 13 47  1  0
  8 46  1  0
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  5 44  1  0
  4 43  1  0
 39 73  1  0
 38 72  1  0
  1 40  1  0
  1 41  1  0
  1 42  1  0
 17 49  1  0
 17 50  1  0
 17 51  1  0
 30 57  1  0
 30 58  1  0
 30 59  1  0
M  END


  Mrv1652306212101563D          

 73 78  0  0  0  0            999 V2000
    5.2135    3.7517    5.0431 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0377    3.7710    5.8432 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0522    2.8841    5.5098 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0787    1.9901    4.4420 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9944    1.1324    4.2124 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8703    1.1479    5.0478 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3060    0.2924    4.8252 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2870   -0.8790    4.1714 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5464   -1.6489    4.0041 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5282   -1.4572    4.7200 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6039   -2.7273    2.9889 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4796   -3.8050    3.1726 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3109   -3.9110    4.2595 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5581   -4.8511    2.2400 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7769   -4.8372    1.0802 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7525   -5.8184    0.1356 O   0  0  0  0  0  0  0  0  0  0  0  0
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    0.2190   -1.9281   -0.0108 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6924   -1.5870   -0.1667 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5491   -2.3191   -0.6473 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0742   -0.1927    0.2653 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0920    0.0553    0.8875 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1146    0.8489   -0.1432 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1841    0.5015   -0.8440 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9411    1.2249   -1.6058 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7028    2.6938   -1.9041 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8112    0.5831   -2.6575 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6769   -0.9685   -0.9103 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1422   -0.9105   -0.3443 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7355   -1.5042   -2.3782 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6196   -0.6792   -3.3245 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.2219   -3.8722   -1.6653 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0367   -3.4549   -0.2206 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8477    2.0591    6.1099 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9306    2.9145    6.3394 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7110    2.7775    5.0944 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9903    4.0287    4.0075 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9038    4.4993    5.4458 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9220    1.9304    3.7610 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0534    0.4610    3.3604 H   0  0  0  0  0  0  0  0  0  0  0  0
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    0.6233   -1.3025    3.7678 H   0  0  0  0  0  0  0  0  0  0  0  0
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    1.0529    1.6553    0.5849 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0243    1.1594   -0.6101 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0972    3.1793   -1.1312 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1791    2.8046   -2.8593 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6556    3.2301   -1.9657 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3040    0.6009   -3.6279 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7460    1.1457   -2.7614 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0909   -0.4477   -2.4454 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7793   -0.2497   -0.9429 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6321   -1.8858   -0.3153 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1622   -0.4903    0.6682 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2720   -1.4800   -2.8005 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6840   -0.7960   -3.0985 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.4737   -1.0103   -4.3591 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2074   -3.3116   -3.4740 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2009   -3.1016   -2.0492 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7396   -3.8488   -2.1968 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5610   -4.9095   -1.7332 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9381   -3.9979    0.1022 H   0  0  0  0  0  0  0  0  0  0  0  0
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 22 24  1  0  0  0  0
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 27 26  1  0  0  0  0
 22 23  2  0  0  0  0
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 24 25  2  0  0  0  0
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 15 16  1  0  0  0  0
 21 37  1  0  0  0  0
 12 13  1  0  0  0  0
 21 31  1  0  0  0  0
 11  9  1  0  0  0  0
  9  8  1  0  0  0  0
 36 35  1  0  0  0  0
  8  7  2  0  0  0  0
 31 32  1  1  0  0  0
  7  6  1  0  0  0  0
 21 22  1  0  0  0  0
  6  5  2  0  0  0  0
 28 29  1  1  0  0  0
  5  4  1  0  0  0  0
 31 27  1  0  0  0  0
  4  3  2  0  0  0  0
 37 18  1  0  0  0  0
  3 39  1  0  0  0  0
 26 24  1  0  0  0  0
 39 38  2  0  0  0  0
 38  6  1  0  0  0  0
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 36 37  1  0  0  0  0
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 19 11  2  0  0  0  0
 16 17  1  0  0  0  0
 35 33  1  0  0  0  0
 28 30  1  0  0  0  0
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 39 73  1  0  0  0  0
 38 72  1  0  0  0  0
  1 40  1  0  0  0  0
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  1 42  1  0  0  0  0
 17 49  1  0  0  0  0
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 30 57  1  0  0  0  0
 30 58  1  0  0  0  0
 30 59  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0042236

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C([H])C(OC([H])([H])[H])=C2C(O[C@]34C(=O)C(=O)[C@]5([H])[C@@]([H])(C5(C([H])([H])[H])C([H])([H])[H])[C@@]3(C([H])([H])[H])[C@]([H])(C([H])([H])[H])C([H])([H])C([H])([H])[C@]24[H])=C1C(=O)C(\[H])=C(/[H])C1=C([H])C([H])=C(OC([H])([H])[H])C([H])=C1[H]

> <INCHI_IDENTIFIER>
InChI=1S/C32H34O7/c1-16-7-13-19-23-22(38-6)15-21(34)24(20(33)14-10-17-8-11-18(37-5)12-9-17)27(23)39-32(19)29(36)26(35)25-28(30(25,2)3)31(16,32)4/h8-12,14-16,19,25,28,34H,7,13H2,1-6H3/b14-10+/t16-,19-,25-,28+,31-,32-/m1/s1

> <INCHI_KEY>
OEMIDZJNDHSUOP-GUFAUONASA-N

> <FORMULA>
C32H34O7

> <MOLECULAR_WEIGHT>
530.617

> <EXACT_MASS>
530.230453435

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
73

> <JCHEM_AVERAGE_POLARIZABILITY>
57.366528436489844

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,4R,6S,7R,8R,11R)-15-hydroxy-13-methoxy-16-[(2E)-3-(4-methoxyphenyl)prop-2-enoyl]-5,5,7,8-tetramethyl-18-oxapentacyclo[9.7.0.0^{1,7}.0^{4,6}.0^{12,17}]octadeca-12,14,16-triene-2,3-dione

> <ALOGPS_LOGP>
5.57

> <JCHEM_LOGP>
6.7445344280000015

> <ALOGPS_LOGS>
-6.01

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
16.914067052813554

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.132545645410369

> <JCHEM_PKA_STRONGEST_BASIC>
-4.414252864576157

> <JCHEM_POLAR_SURFACE_AREA>
99.13

> <JCHEM_REFRACTIVITY>
146.17739999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.15e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,4R,6S,7R,8R,11R)-15-hydroxy-13-methoxy-16-[(2E)-3-(4-methoxyphenyl)prop-2-enoyl]-5,5,7,8-tetramethyl-18-oxapentacyclo[9.7.0.0^{1,7}.0^{4,6}.0^{12,17}]octadeca-12,14,16-triene-2,3-dione

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 73 78  0  0  0  0  0  0  0  0999 V2000
    5.2135    3.7517    5.0431 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0377    3.7710    5.8432 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0522    2.8841    5.5098 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0787    1.9901    4.4420 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9944    1.1324    4.2124 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8703    1.1479    5.0478 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3060    0.2924    4.8252 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2870   -0.8790    4.1714 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5464   -1.6489    4.0041 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5282   -1.4572    4.7200 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6039   -2.7273    2.9889 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4796   -3.8050    3.1726 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3109   -3.9110    4.2595 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5581   -4.8511    2.2400 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7769   -4.8372    1.0802 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.5491   -2.3191   -0.6473 O   0  0  0  0  0  0  0  0  0  0  0  0
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    0.8477    2.0591    6.1099 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9306    2.9145    6.3394 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7110    2.7775    5.0944 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.2433    0.6628    5.2389 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.0243    1.1594   -0.6101 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0972    3.1793   -1.1312 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1791    2.8046   -2.8593 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6556    3.2301   -1.9657 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3040    0.6009   -3.6279 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7460    1.1457   -2.7614 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0909   -0.4477   -2.4454 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7793   -0.2497   -0.9429 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6321   -1.8858   -0.3153 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1622   -0.4903    0.6682 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2720   -1.4800   -2.8005 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6840   -0.7960   -3.0985 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3739    0.3856   -3.2883 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4737   -1.0103   -4.3591 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2074   -3.3116   -3.4740 H   0  0  0  0  0  0  0  0  0  0  0  0
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    0.7396   -3.8488   -2.1968 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5610   -4.9095   -1.7332 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9381   -3.9979    0.1022 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0095    2.1116    6.7777 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8976    3.6109    7.1738 H   0  0  0  0  0  0  0  0  0  0  0  0
 22 24  1  0
 12 14  2  0
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  6  5  2  0
 28 29  1  1
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  4  3  2  0
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 39 38  2  0
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  3  2  1  0
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  2  1  1  0
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 30 59  1  0
M  END

HEADER    PROTEIN                                 21-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   21-JUN-21         0                                  
HETATM    1  C   UNK     0       5.213   3.752   5.043  0.00  0.00           C+0
HETATM    2  O   UNK     0       4.038   3.771   5.843  0.00  0.00           O+0
HETATM    3  C   UNK     0       3.052   2.884   5.510  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.079   1.990   4.442  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.994   1.132   4.212  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.870   1.148   5.048  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.306   0.292   4.825  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.287  -0.879   4.171  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.546  -1.649   4.004  0.00  0.00           C+0
HETATM   10  O   UNK     0      -2.528  -1.457   4.720  0.00  0.00           O+0
HETATM   11  C   UNK     0      -1.604  -2.727   2.989  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.480  -3.805   3.173  0.00  0.00           C+0
HETATM   13  O   UNK     0      -3.311  -3.911   4.260  0.00  0.00           O+0
HETATM   14  C   UNK     0      -2.558  -4.851   2.240  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.777  -4.837   1.080  0.00  0.00           C+0
HETATM   16  O   UNK     0      -1.753  -5.818   0.136  0.00  0.00           O+0
HETATM   17  C   UNK     0      -2.552  -6.972   0.370  0.00  0.00           C+0
HETATM   18  C   UNK     0      -0.952  -3.740   0.864  0.00  0.00           C+0
HETATM   19  C   UNK     0      -0.872  -2.712   1.809  0.00  0.00           C+0
HETATM   20  O   UNK     0      -0.051  -1.681   1.406  0.00  0.00           O+0
HETATM   21  C   UNK     0       0.219  -1.928  -0.011  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.692  -1.587  -0.167  0.00  0.00           C+0
HETATM   23  O   UNK     0       2.549  -2.319  -0.647  0.00  0.00           O+0
HETATM   24  C   UNK     0       2.074  -0.193   0.265  0.00  0.00           C+0
HETATM   25  O   UNK     0       3.092   0.055   0.888  0.00  0.00           O+0
HETATM   26  C   UNK     0       1.115   0.849  -0.143  0.00  0.00           C+0
HETATM   27  C   UNK     0      -0.184   0.501  -0.844  0.00  0.00           C+0
HETATM   28  C   UNK     0       0.941   1.225  -1.606  0.00  0.00           C+0
HETATM   29  C   UNK     0       0.703   2.694  -1.904  0.00  0.00           C+0
HETATM   30  C   UNK     0       1.811   0.583  -2.658  0.00  0.00           C+0
HETATM   31  C   UNK     0      -0.677  -0.969  -0.910  0.00  0.00           C+0
HETATM   32  C   UNK     0      -2.142  -0.911  -0.344  0.00  0.00           C+0
HETATM   33  C   UNK     0      -0.736  -1.504  -2.378  0.00  0.00           C+0
HETATM   34  C   UNK     0      -1.620  -0.679  -3.325  0.00  0.00           C+0
HETATM   35  C   UNK     0      -1.182  -2.975  -2.429  0.00  0.00           C+0
HETATM   36  C   UNK     0      -0.222  -3.872  -1.665  0.00  0.00           C+0
HETATM   37  C   UNK     0       0.037  -3.455  -0.221  0.00  0.00           C+0
HETATM   38  C   UNK     0       0.848   2.059   6.110  0.00  0.00           C+0
HETATM   39  C   UNK     0       1.931   2.914   6.339  0.00  0.00           C+0
HETATM   40  H   UNK     0       5.711   2.777   5.094  0.00  0.00           H+0
HETATM   41  H   UNK     0       4.990   4.029   4.008  0.00  0.00           H+0
HETATM   42  H   UNK     0       5.904   4.499   5.446  0.00  0.00           H+0
HETATM   43  H   UNK     0       3.922   1.930   3.761  0.00  0.00           H+0
HETATM   44  H   UNK     0       2.053   0.461   3.360  0.00  0.00           H+0
HETATM   45  H   UNK     0      -1.243   0.663   5.239  0.00  0.00           H+0
HETATM   46  H   UNK     0       0.623  -1.303   3.768  0.00  0.00           H+0
HETATM   47  H   UNK     0      -3.300  -3.050   4.737  0.00  0.00           H+0
HETATM   48  H   UNK     0      -3.244  -5.664   2.458  0.00  0.00           H+0
HETATM   49  H   UNK     0      -3.616  -6.716   0.392  0.00  0.00           H+0
HETATM   50  H   UNK     0      -2.393  -7.662  -0.465  0.00  0.00           H+0
HETATM   51  H   UNK     0      -2.248  -7.485   1.288  0.00  0.00           H+0
HETATM   52  H   UNK     0       1.053   1.655   0.585  0.00  0.00           H+0
HETATM   53  H   UNK     0      -1.024   1.159  -0.610  0.00  0.00           H+0
HETATM   54  H   UNK     0       0.097   3.179  -1.131  0.00  0.00           H+0
HETATM   55  H   UNK     0       0.179   2.805  -2.859  0.00  0.00           H+0
HETATM   56  H   UNK     0       1.656   3.230  -1.966  0.00  0.00           H+0
HETATM   57  H   UNK     0       1.304   0.601  -3.628  0.00  0.00           H+0
HETATM   58  H   UNK     0       2.746   1.146  -2.761  0.00  0.00           H+0
HETATM   59  H   UNK     0       2.091  -0.448  -2.445  0.00  0.00           H+0
HETATM   60  H   UNK     0      -2.779  -0.250  -0.943  0.00  0.00           H+0
HETATM   61  H   UNK     0      -2.632  -1.886  -0.315  0.00  0.00           H+0
HETATM   62  H   UNK     0      -2.162  -0.490   0.668  0.00  0.00           H+0
HETATM   63  H   UNK     0       0.272  -1.480  -2.801  0.00  0.00           H+0
HETATM   64  H   UNK     0      -2.684  -0.796  -3.099  0.00  0.00           H+0
HETATM   65  H   UNK     0      -1.374   0.386  -3.288  0.00  0.00           H+0
HETATM   66  H   UNK     0      -1.474  -1.010  -4.359  0.00  0.00           H+0
HETATM   67  H   UNK     0      -1.207  -3.312  -3.474  0.00  0.00           H+0
HETATM   68  H   UNK     0      -2.201  -3.102  -2.049  0.00  0.00           H+0
HETATM   69  H   UNK     0       0.740  -3.849  -2.197  0.00  0.00           H+0
HETATM   70  H   UNK     0      -0.561  -4.910  -1.733  0.00  0.00           H+0
HETATM   71  H   UNK     0       0.938  -3.998   0.102  0.00  0.00           H+0
HETATM   72  H   UNK     0      -0.010   2.112   6.778  0.00  0.00           H+0
HETATM   73  H   UNK     0       1.898   3.611   7.174  0.00  0.00           H+0
CONECT    1    2   40   41   42                                             
CONECT    2    3    1                                                       
CONECT    3    4   39    2                                                  
CONECT    4    5    3   43                                                  
CONECT    5    6    4   44                                                  
CONECT    6    7    5   38                                                  
CONECT    7    8    6   45                                                  
CONECT    8    9    7   46                                                  
CONECT    9   11    8   10                                                  
CONECT   10    9                                                            
CONECT   11    9   19   12                                                  
CONECT   12   14   13   11                                                  
CONECT   13   12   47                                                       
CONECT   14   12   15   48                                                  
CONECT   15   14   18   16                                                  
CONECT   16   15   17                                                       
CONECT   17   16   49   50   51                                             
CONECT   18   15   37   19                                                  
CONECT   19   20   18   11                                                  
CONECT   20   21   19                                                       
CONECT   21   20   37   31   22                                             
CONECT   22   24   23   21                                                  
CONECT   23   22                                                            
CONECT   24   22   25   26                                                  
CONECT   25   24                                                            
CONECT   26   27   28   24   52                                             
CONECT   27   26   28   31   53                                             
CONECT   28   27   26   29   30                                             
CONECT   29   28   54   55   56                                             
CONECT   30   28   57   58   59                                             
CONECT   31   33   21   32   27                                             
CONECT   32   31   60   61   62                                             
CONECT   33   31   34   35   63                                             
CONECT   34   33   64   65   66                                             
CONECT   35   36   33   67   68                                             
CONECT   36   35   37   69   70                                             
CONECT   37   21   18   36   71                                             
CONECT   38   39    6   72                                                  
CONECT   39    3   38   73                                                  
CONECT   40    1                                                            
CONECT   41    1                                                            
CONECT   42    1                                                            
CONECT   43    4                                                            
CONECT   44    5                                                            
CONECT   45    7                                                            
CONECT   46    8                                                            
CONECT   47   13                                                            
CONECT   48   14                                                            
CONECT   49   17                                                            
CONECT   50   17                                                            
CONECT   51   17                                                            
CONECT   52   26                                                            
CONECT   53   27                                                            
CONECT   54   29                                                            
CONECT   55   29                                                            
CONECT   56   29                                                            
CONECT   57   30                                                            
CONECT   58   30                                                            
CONECT   59   30                                                            
CONECT   60   32                                                            
CONECT   61   32                                                            
CONECT   62   32                                                            
CONECT   63   33                                                            
CONECT   64   34                                                            
CONECT   65   34                                                            
CONECT   66   34                                                            
CONECT   67   35                                                            
CONECT   68   35                                                            
CONECT   69   36                                                            
CONECT   70   36                                                            
CONECT   71   37                                                            
CONECT   72   38                                                            
CONECT   73   39                                                            
MASTER        0    0    0    0    0    0    0    0   73    0  156    0
END

RDKit          3D

73 78  0  0  0  0  0  0  0  0999 V2000
    5.2135    3.7517    5.0431 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0377    3.7710    5.8432 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0522    2.8841    5.5098 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0787    1.9901    4.4420 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9944    1.1324    4.2124 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8703    1.1479    5.0478 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3060    0.2924    4.8252 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2870   -0.8790    4.1714 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5464   -1.6489    4.0041 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5282   -1.4572    4.7200 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6039   -2.7273    2.9889 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4796   -3.8050    3.1726 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3109   -3.9110    4.2595 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5581   -4.8511    2.2400 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7769   -4.8372    1.0802 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7525   -5.8184    0.1356 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5518   -6.9722    0.3695 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9521   -3.7397    0.8643 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8718   -2.7124    1.8087 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0514   -1.6811    1.4056 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2190   -1.9281   -0.0108 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6924   -1.5870   -0.1667 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5491   -2.3191   -0.6473 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0742   -0.1927    0.2653 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0920    0.0553    0.8875 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1146    0.8489   -0.1432 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1841    0.5015   -0.8440 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9411    1.2249   -1.6058 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7028    2.6938   -1.9041 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8112    0.5831   -2.6575 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6769   -0.9685   -0.9103 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1422   -0.9105   -0.3443 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7355   -1.5042   -2.3782 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6196   -0.6792   -3.3245 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1819   -2.9754   -2.4294 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2219   -3.8722   -1.6653 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0367   -3.4549   -0.2206 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8477    2.0591    6.1099 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9306    2.9145    6.3394 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7110    2.7775    5.0944 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9903    4.0287    4.0075 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9038    4.4993    5.4458 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9220    1.9304    3.7610 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0534    0.4610    3.3604 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2433    0.6628    5.2389 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6233   -1.3025    3.7678 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3003   -3.0501    4.7375 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2438   -5.6644    2.4581 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6159   -6.7156    0.3915 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3932   -7.6623   -0.4648 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2476   -7.4847    1.2882 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0529    1.6553    0.5849 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0243    1.1594   -0.6101 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0972    3.1793   -1.1312 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1791    2.8046   -2.8593 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6556    3.2301   -1.9657 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3040    0.6009   -3.6279 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7460    1.1457   -2.7614 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0909   -0.4477   -2.4454 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7793   -0.2497   -0.9429 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6321   -1.8858   -0.3153 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1622   -0.4903    0.6682 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2720   -1.4800   -2.8005 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6840   -0.7960   -3.0985 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3739    0.3856   -3.2883 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4737   -1.0103   -4.3591 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2074   -3.3116   -3.4740 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2009   -3.1016   -2.0492 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7396   -3.8488   -2.1968 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5610   -4.9095   -1.7332 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9381   -3.9979    0.1022 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0095    2.1116    6.7777 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8976    3.6109    7.1738 H   0  0  0  0  0  0  0  0  0  0  0  0
 22 24  1  0
 12 14  2  0
 33 31  1  0
 14 15  1  0
 15 18  2  0
 33 34  1  0
 21 20  1  1
 19 20  1  0
 27 26  1  0
 22 23  2  0
 27 28  1  0
 24 25  2  0
 26 28  1  0
 15 16  1  0
 21 37  1  0
 12 13  1  0
 21 31  1  0
 11  9  1  0
  9  8  1  0
 36 35  1  0
  8  7  2  0
 31 32  1  1
  7  6  1  0
 21 22  1  0
  6  5  2  0
 28 29  1  1
  5  4  1  0
 31 27  1  0
  4  3  2  0
 37 18  1  0
  3 39  1  0
 26 24  1  0
 39 38  2  0
 38  6  1  0
 18 19  1  0
  3  2  1  0
 36 37  1  0
  2  1  1  0
 19 11  2  0
 16 17  1  0
 35 33  1  0
 28 30  1  0
 11 12  1  0
  9 10  2  0
 36 69  1  0
 36 70  1  0
 35 67  1  0
 35 68  1  0
 33 63  1  6
 37 71  1  1
 34 64  1  0
 34 65  1  0
 34 66  1  0
 26 52  1  1
 27 53  1  1
 32 60  1  0
 32 61  1  0
 32 62  1  0
 29 54  1  0
 29 55  1  0
 29 56  1  0
 14 48  1  0
 13 47  1  0
  8 46  1  0
  7 45  1  0
  5 44  1  0
  4 43  1  0
 39 73  1  0
 38 72  1  0
  1 40  1  0
  1 41  1  0
  1 42  1  0
 17 49  1  0
 17 50  1  0
 17 51  1  0
 30 57  1  0
 30 58  1  0
 30 59  1  0
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₂H₃₄O₇

Average Mass

530.6170 Da

Monoisotopic Mass

530.23045 Da

IUPAC Name

(1S,4R,6S,7R,8R,11R)-15-hydroxy-13-methoxy-16-[(2E)-3-(4-methoxyphenyl)prop-2-enoyl]-5,5,7,8-tetramethyl-18-oxapentacyclo[9.7.0.0^{1,7}.0^{4,6}.0^{12,17}]octadeca-12,14,16-triene-2,3-dione

Traditional Name

(1S,4R,6S,7R,8R,11R)-15-hydroxy-13-methoxy-16-[(2E)-3-(4-methoxyphenyl)prop-2-enoyl]-5,5,7,8-tetramethyl-18-oxapentacyclo[9.7.0.0^{1,7}.0^{4,6}.0^{12,17}]octadeca-12,14,16-triene-2,3-dione

CAS Registry Number

Not Available

SMILES

[H]OC1=C([H])C(OC([H])([H])[H])=C2C(O[C@]34C(=O)C(=O)[C@]5([H])[C@@]([H])(C5(C([H])([H])[H])C([H])([H])[H])[C@@]3(C([H])([H])[H])[C@]([H])(C([H])([H])[H])C([H])([H])C([H])([H])[C@]24[H])=C1C(=O)C(\[H])=C(/[H])C1=C([H])C([H])=C(OC([H])([H])[H])C([H])=C1[H]

InChI Identifier

InChI=1S/C32H34O7/c1-16-7-13-19-23-22(38-6)15-21(34)24(20(33)14-10-17-8-11-18(37-5)12-9-17)27(23)39-32(19)29(36)26(35)25-28(30(25,2)3)31(16,32)4/h8-12,14-16,19,25,28,34H,7,13H2,1-6H3/b14-10+/t16-,19-,25-,28+,31-,32-/m1/s1

InChI Key

OEMIDZJNDHSUOP-GUFAUONASA-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

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Nardostachys chinensis Batal	JEOL database	Liu, M.-L. et al, Org. Lett. 15, 1000 (2013)

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 2'-hydroxychalcones. These are organic compounds containing chalcone skeleton that carries a hydroxyl group at the 2'-position.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Linear 1,3-diarylpropanoids

Sub Class

Chalcones and dihydrochalcones

Direct Parent

2'-Hydroxychalcones

Alternative Parents

Substituents

2'-hydroxychalcone
Cinnamic acid or derivatives
Monoterpenoid
Carane monoterpenoid
Aromatic monoterpenoid
Coumaran
Phenoxy compound
Phenol ether
Styrene
Aryl ketone
Methoxybenzene
Anisole
Alkyl aryl ether
Phenol
1-hydroxy-2-unsubstituted benzenoid
Benzenoid
Monocyclic benzene moiety
Alpha,beta-unsaturated ketone
Vinylogous acid
Acryloyl-group
Enone
Ketone
Oxacycle
Organoheterocyclic compound
Ether
Organic oxide
Organic oxygen compound
Organooxygen compound
Carbonyl group
Hydrocarbon derivative
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	5.57	ALOGPS
logP	6.74	ChemAxon
logS	-6	ALOGPS
pKa (Strongest Acidic)	7.13	ChemAxon
pKa (Strongest Basic)	-4.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	99.13 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	146.18 m³·mol⁻¹	ChemAxon
Polarizability	57.37 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	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

30652119

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

71583359

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Liu, M.-L. et al. (2013). Liu, M.-L. et al, Org. Lett. 15, 1000 (2013). Org. Lett..

Showing NP-Card for nardoaristolone A (NP0042236)

MOL for NP0042236 (nardoaristolone A)

3D MOL for NP0042236 (nardoaristolone A)

3D SDF for NP0042236 (nardoaristolone A)

3D-SDF for NP0042236 (nardoaristolone A)

PDB for NP0042236 (nardoaristolone A)

3D PDB for NP0042236 (nardoaristolone A)

SMILES for NP0042236 (nardoaristolone A)

INCHI for NP0042236 (nardoaristolone A)

Structure for NP0042236 (nardoaristolone A)

3D Structure for NP0042236 (nardoaristolone A)