NP-MRD: Showing NP-Card for (-)-Deoxypodorhizone (NP0051503)

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Record Information

Version

2.0

Created at

2022-04-27 22:50:42 UTC

Updated at

2022-04-27 22:50:42 UTC

NP-MRD ID

NP0051503

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(-)-Deoxypodorhizone

Description

Dihydroanhydropodorhizol, also known as yatein, belongs to the class of organic compounds known as dibenzylbutyrolactone lignans. These are lignan compounds containing a 3,4-dibenzyloxolan-2-one moiety. Dihydroanhydropodorhizol is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. (-)-Deoxypodorhizone is found in Anthriscus sylvestris, Apis cerana, Bupleurum scorzonerifolium , Bursera schlechtendalii, Bursera simaruba , Calocedrus formosana, Chaerophyllum aureum, Chamaecyparis obtusa, Condea verticillata, Eriope blanchetii, Hernandia nymphaeifolia , Hernandia ovigera , Hyptis verticillata , Illigera luzonensis, Juniperus brevifolia, Juniperus chinensis, Juniperus communis, Juniperus phoenicea , Juniperus sabina, Juniperus spp., Juniperus thurifera, Juniperus thurifera var.africana, Libocedrus yateensis, Lychnophora ericoides, Macrococculus pomiferus, Piper cubeba , Piper guineense, Podolepis rugata, Thuja occidentalis and Thuja plicata. (-)-Deoxypodorhizone was first documented in 2003 (PMID: 12956064). Based on a literature review a small amount of articles have been published on dihydroanhydropodorhizol (PMID: 16540181) (PMID: 25420758) (PMID: 26091020).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282200502D          

 29 32  0  0  1  0            999 V2000
    3.4990    1.1104    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5852    1.9309    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.3922    2.1025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7278    2.8561    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8047    1.3880    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2527    0.7749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9721    2.4830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1437    3.2899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5306    3.8420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7021    4.6489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4867    4.9039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0998    4.3518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9283    3.5449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8844    4.6068    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4975    4.0547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6582    5.7108    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4429    5.9658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0890    5.2010    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2605    6.0079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7845    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435    2.1904    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6284    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435    0.8555    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  2  7  1  1  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
  8 13  1  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 11 16  1  0  0  0  0
 16 17  1  0  0  0  0
 10 18  1  0  0  0  0
 18 19  1  0  0  0  0
  1 20  1  6  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 21 26  1  0  0  0  0
 24 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 23 29  1  0  0  0  0
M  END

     RDKit          3D

 53 56  0  0  0  0  0  0  0  0999 V2000
   -3.0400    3.5842   -0.4909 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2090    2.5813    0.4904 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7379    1.2855    0.3234 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0634    0.8817   -0.8272 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5997   -0.4058   -0.9840 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8887   -0.8318   -2.1945 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6034   -0.6595   -2.1323 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1178   -0.8766   -3.5072 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7097   -1.9136   -3.8780 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7932    0.2755   -4.2019 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6736    1.3680   -3.2841 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9962    0.7875   -1.9217 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4780    0.9251   -1.7390 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0275    0.1931   -0.5956 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4751   -1.1057   -0.7285 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9987   -1.8146    0.3386 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0961   -1.2439    1.5965 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6523    0.0512    1.7387 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1246    0.7612    0.6570 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8552    0.3895    3.0767 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7454   -0.5825    3.6435 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5753   -1.7237    2.8277 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8378   -1.2822    0.0616 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5056   -0.8930    1.2073 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7507   -1.7638    2.2641 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2852   -3.0935    2.1298 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9653    0.3989    1.3532 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6320    0.7853    2.4983 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0189    0.7093    2.6858 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9830    3.9421   -0.4488 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6686    4.4499   -0.1669 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3707    3.2909   -1.4865 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9107    1.6140   -1.6065 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0758   -1.9058   -2.4497 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2301   -0.2682   -3.1116 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0807   -1.3327   -1.3940 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4683    2.0922   -3.6101 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2921    1.8604   -3.3505 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4109    1.2653   -1.1144 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9505    0.6120   -2.7132 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6929    2.0327   -1.6823 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4389   -1.6397   -1.6848 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3495   -2.8323    0.2349 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7878    1.7620    0.7923 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4785   -0.8488    4.6668 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7948   -0.2117    3.5484 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4828   -2.2860   -0.0472 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1938   -3.1767    2.2056 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5749   -3.5337    1.1453 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8211   -3.7201    2.8976 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2280    1.0127    3.7423 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4053   -0.3344    2.6045 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6038    1.3686    2.0292 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7 12  1  0
 12 13  1  0
 13 14  1  0
 14 19  2  0
 19 18  1  0
 18 17  2  0
 17 22  1  0
 22 21  1  0
 21 20  1  0
 17 16  1  0
 16 15  2  0
 12 11  1  0
 11 10  1  0
 10  8  1  0
  8  9  2  0
  5 23  2  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 24 27  2  0
 27 28  1  0
 28 29  1  0
 27  3  1  0
  8  7  1  0
 15 14  1  0
 20 18  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  4 33  1  0
  6 34  1  0
  6 35  1  0
  7 36  1  1
 12 39  1  1
 13 40  1  0
 13 41  1  0
 19 44  1  0
 21 45  1  0
 21 46  1  0
 16 43  1  0
 15 42  1  0
 11 37  1  0
 11 38  1  0
 23 47  1  0
 26 48  1  0
 26 49  1  0
 26 50  1  0
 29 51  1  0
 29 52  1  0
 29 53  1  0
M  END


  Mrv1652304282200502D          

 29 32  0  0  1  0            999 V2000
    3.4990    1.1104    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5852    1.9309    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.3922    2.1025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7278    2.8561    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8047    1.3880    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2527    0.7749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9721    2.4830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1437    3.2899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5306    3.8420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7021    4.6489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4867    4.9039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0998    4.3518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9283    3.5449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8844    4.6068    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4975    4.0547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6582    5.7108    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4429    5.9658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0890    5.2010    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2605    6.0079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7845    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435    2.1904    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6284    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435    0.8555    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  2  7  1  1  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
  8 13  1  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 11 16  1  0  0  0  0
 16 17  1  0  0  0  0
 10 18  1  0  0  0  0
 18 19  1  0  0  0  0
  1 20  1  6  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 21 26  1  0  0  0  0
 24 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 23 29  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0051503

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(C[C@@H]2[C@@H](CC3=CC4=C(OCO4)C=C3)COC2=O)=CC(OC)=C1OC

> <INCHI_IDENTIFIER>
InChI=1S/C22H24O7/c1-24-19-9-14(10-20(25-2)21(19)26-3)7-16-15(11-27-22(16)23)6-13-4-5-17-18(8-13)29-12-28-17/h4-5,8-10,15-16H,6-7,11-12H2,1-3H3/t15-,16+/m0/s1

> <INCHI_KEY>
GMLDZDDTZKXJLU-JKSUJKDBSA-N

> <FORMULA>
C22H24O7

> <MOLECULAR_WEIGHT>
400.427

> <EXACT_MASS>
400.152203113

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
53

> <JCHEM_AVERAGE_POLARIZABILITY>
42.22959598385423

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3R,4R)-4-[(2H-1,3-benzodioxol-5-yl)methyl]-3-[(3,4,5-trimethoxyphenyl)methyl]oxolan-2-one

> <ALOGPS_LOGP>
3.52

> <JCHEM_LOGP>
3.3644753563333327

> <ALOGPS_LOGS>
-4.83

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.267266841885663

> <JCHEM_POLAR_SURFACE_AREA>
72.45000000000002

> <JCHEM_REFRACTIVITY>
103.90270000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.93e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
yatein

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0       6.531   2.073   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.692   3.604   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.199   3.925   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       8.825   5.331   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0       8.969   2.591   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       7.938   1.446   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.548   4.635   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.868   6.141   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.724   7.172   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.044   8.678   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.509   9.154   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.653   8.123   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.333   6.617   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       9.118   8.599   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      10.262   7.569   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       6.829  10.660   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       8.293  11.136   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       3.899   9.708   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       4.220  11.215   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.198   1.303   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.864   2.073   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.530   1.303   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       1.197   2.073   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       1.197   3.613   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       2.530   4.383   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       3.864   3.613   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      -0.268   4.089   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      -1.173   2.843   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      -0.268   1.597   0.000  0.00  0.00           O+0
CONECT    1    2    6   20                                                  
CONECT    2    1    3    7                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    1                                                       
CONECT    7    2    8                                                       
CONECT    8    7    9   13                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   18                                                  
CONECT   11   10   12   16                                                  
CONECT   12   11   13   14                                                  
CONECT   13   12    8                                                       
CONECT   14   12   15                                                       
CONECT   15   14                                                            
CONECT   16   11   17                                                       
CONECT   17   16                                                            
CONECT   18   10   19                                                       
CONECT   19   18                                                            
CONECT   20    1   21                                                       
CONECT   21   20   22   26                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24   29                                                  
CONECT   24   23   25   27                                                  
CONECT   25   24   26                                                       
CONECT   26   25   21                                                       
CONECT   27   24   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   23                                                       
MASTER        0    0    0    0    0    0    0    0   29    0   64    0
END

View in JSmol

Synonyms

Value	Source
(-)-Yatein	ChEBI
(-)-Deoxypodorhizone	ChEBI
Yatein	ChEBI
(3R,4R)-4-(1,3-Benzodioxol-5-ylmethyl)-3-(3,4,5-trimethoxybenzyl)dihydrofuran-2(3H)-one	Kegg

Chemical Formula

C₂₂H₂₄O₇

Average Mass

400.4270 Da

Monoisotopic Mass

400.15220 Da

IUPAC Name

(3R,4R)-4-[(2H-1,3-benzodioxol-5-yl)methyl]-3-[(3,4,5-trimethoxyphenyl)methyl]oxolan-2-one

Traditional Name

yatein

CAS Registry Number

Not Available

SMILES

COC1=CC(C[C@@H]2[C@@H](CC3=CC4=C(OCO4)C=C3)COC2=O)=CC(OC)=C1OC

InChI Identifier

InChI=1S/C22H24O7/c1-24-19-9-14(10-20(25-2)21(19)26-3)7-16-15(11-27-22(16)23)6-13-4-5-17-18(8-13)29-12-28-17/h4-5,8-10,15-16H,6-7,11-12H2,1-3H3/t15-,16+/m0/s1

InChI Key

GMLDZDDTZKXJLU-JKSUJKDBSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Anthriscus sylvestris	LOTUS Database	35616633
Apis cerana	LOTUS Database	35616633
Bupleurum scorzonerifolium	Plant	KNApSAcK
Bursera schlechtendalii	Plant	KNApSAcK
Bursera simaruba	Plant	KNApSAcK
Calocedrus formosana	Plant	KNApSAcK
Chaerophyllum aureum	LOTUS Database	35616633
Chamaecyparis obtusa	LOTUS Database	35616633
Condea verticillata	LOTUS Database	35616633
Eriope blanchetii	LOTUS Database	35616633
Hernandia nymphaeifolia	Plant	KNApSAcK
Hernandia ovigera	Plant	KNApSAcK
Hyptis verticillata	Plant	KNApSAcK
Illigera luzonensis	LOTUS Database	35616633
Juniperus brevifolia	LOTUS Database	35616633
Juniperus chinensis	Plant	KNApSAcK
Juniperus communis	LOTUS Database	35616633
Juniperus phoenicea	Plant	KNApSAcK
Juniperus sabina	LOTUS Database	35616633
Juniperus spp.	Plant	KNApSAcK
Juniperus thurifera	LOTUS Database	35616633
Juniperus thurifera var.africana	Plant	KNApSAcK
Libocedrus yateensis	Plant	KNApSAcK
Lychnophora ericoides	LOTUS Database	35616633
Macrococculus pomiferus	Plant	KNApSAcK
Piper cubeba	Plant	KNApSAcK
Piper guineense	LOTUS Database	35616633
Podolepis rugata	LOTUS Database	35616633
Thuja occidentalis	Plant	KNApSAcK
Thuja plicata	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as dibenzylbutyrolactone lignans. These are lignan compounds containing a 3,4-dibenzyloxolan-2-one moiety.

Kingdom

Organic compounds

Super Class

Lignans, neolignans and related compounds

Class

Furanoid lignans

Sub Class

Tetrahydrofuran lignans

Direct Parent

Dibenzylbutyrolactone lignans

Alternative Parents

Substituents

Dibenzylbutyrolactone
Lignan lactone
Benzodioxole
Phenoxy compound
Anisole
Methoxybenzene
Phenol ether
Alkyl aryl ether
Monocyclic benzene moiety
Benzenoid
Gamma butyrolactone
Tetrahydrofuran
Carboxylic acid ester
Lactone
Acetal
Oxacycle
Carboxylic acid derivative
Organoheterocyclic compound
Ether
Monocarboxylic acid or derivatives
Carbonyl group
Organic oxide
Organooxygen compound
Hydrocarbon derivative
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

lignan (CHEBI:4553 )
Lignans (C10557 )

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	3.52	ALOGPS
logP	3.36	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Basic)	-4.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	72.45 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	103.9 m³·mol⁻¹	ChemAxon
Polarizability	42.23 Å³	ChemAxon
Number of Rings	4	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

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

442835

PDB ID

Not Available

ChEBI ID

4553

Good Scents ID

Not Available

References

General References

Sakakibara N, Suzuki S, Umezawa T, Shimada M: Biosynthesis of yatein in Anthriscus sylvestris. Org Biomol Chem. 2003 Jul 21;1(14):2474-85. doi: 10.1039/b304411d. [PubMed:12956064 ]
Kuo YC, Kuo YH, Lin YL, Tsai WJ: Yatein from Chamaecyparis obtusa suppresses herpes simplex virus type 1 replication in HeLa cells by interruption the immediate-early gene expression. Antiviral Res. 2006 Jul;70(3):112-20. doi: 10.1016/j.antiviral.2006.01.011. Epub 2006 Feb 20. [PubMed:16540181 ]
Donoso-Fierro C, Tiezzi A, Ovidi E, Ceccarelli D, Triggiani D, Mastrogiovanni F, Taddei AR, Perez C, Becerra J, Silva M, Passarella D: Antiproliferative activity of yatein isolated from Austrocedrus chilensis against murine myeloma cells: cytological studies and chemical investigations. Pharm Biol. 2015 Mar;53(3):378-85. doi: 10.3109/13880209.2014.922588. Epub 2014 Nov 25. [PubMed:25420758 ]
Liu Y, Young K, Rakotondraibe LH, Brodie PJ, Wiley JD, Cassera MB, Callmander MW, Rakotondrajaona R, Rakotobe E, Rasamison VE, TenDyke K, Shen Y, Kingston DG: Antiproliferative Compounds from Cleistanthus boivinianus from the Madagascar Dry Forest. J Nat Prod. 2015 Jul 24;78(7):1543-7. doi: 10.1021/np501020m. Epub 2015 Jun 19. [PubMed:26091020 ]

Showing NP-Card for (-)-Deoxypodorhizone (NP0051503)

MOL for NP0051503 ((-)-Deoxypodorhizone)

3D MOL for NP0051503 ((-)-Deoxypodorhizone)

3D SDF for NP0051503 ((-)-Deoxypodorhizone)

3D-SDF for NP0051503 ((-)-Deoxypodorhizone)

PDB for NP0051503 ((-)-Deoxypodorhizone)

3D PDB for NP0051503 ((-)-Deoxypodorhizone)

SMILES for NP0051503 ((-)-Deoxypodorhizone)

INCHI for NP0051503 ((-)-Deoxypodorhizone)

Structure for NP0051503 ((-)-Deoxypodorhizone)

3D Structure for NP0051503 ((-)-Deoxypodorhizone)