NP-MRD: Showing NP-Card for α-conidendrin (NP0189963)

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Record Information

Version

1.0

Created at

2022-09-04 06:33:15 UTC

Updated at

2022-09-04 06:33:15 UTC

NP-MRD ID

NP0189963

Secondary Accession Numbers

None

Natural Product Identification

Common Name

α-conidendrin

Description

Alpha-Conidendrin, also known as α-conidendrin, belongs to the class of organic compounds known as lignan lactones. These are lignans that contain a lactone moiety. They include 1-aryltetralin lactones, dibenzylbutyrolactone lignans, and podophyllotoxins, among others. α-conidendrin is found in Abies holophylla, Dolomiaea souliei, Taxus mairei, Taxus wallichiana and Tsuga heterophylla. It was first documented in 2012 (PMID: 22949834). Alpha-Conidendrin is an extremely weak basic (essentially neutral) compound (based on its pKa) (PMID: 32552421) (PMID: 31971313) (PMID: 30920215) (PMID: 27774796).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309272006312D          

 28 31  0  0  0  0            999 V2000
10002.4616 9999.3897    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10002.4616 9997.7374    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10003.1803 9998.1513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.8846 9997.3252    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9998.8846 9999.8036    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
10001.030310001.8686    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.746910001.4555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.602110002.6947    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.6013 9999.3891    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9999.6013 9997.7391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.3158 9998.1515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.3158 9998.9766    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.315310001.4550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.600810001.8674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.886310001.4549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.886210000.6299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.600710000.2174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.315310000.6300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.0316 9999.3892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.0316 9997.7391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.7461 9998.1516    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.7461 9998.9767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.1022 9999.2315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.6173 9998.5640    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.1022 9997.8966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.8868 9998.1515    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9998.8868 9998.9765    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9997.8472 9997.1120    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0  0  0  0
  6  7  1  0  0  0  0
  9 12  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 13  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 19  1  0  0  0  0
 13  6  1  0  0  0  0
 14  8  1  0  0  0  0
  1 22  1  0  0  0  0
 21  2  1  0  0  0  0
  9 17  1  1  0  0  0
 19 12  2  0  0  0  0
 11 20  2  0  0  0  0
 23 27  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 28  2  0  0  0  0
  9 27  1  0  0  0  0
 27  5  1  1  0  0  0
 26 10  1  0  0  0  0
 26  4  1  6  0  0  0
M  END

     RDKit          3D

 46 49  0  0  0  0  0  0  0  0999 V2000
    4.4051    1.6112    2.0860 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3082    2.1292    0.7777 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3512    1.7122   -0.1315 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4095    0.7511    0.1686 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4434    0.3153   -0.7167 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4781   -0.7178   -0.3056 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7500   -0.1804    0.3009 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8001    1.0882    0.7931 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9661    1.5870    1.3645 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0005    2.8975    1.8671 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0916    0.7980    1.4397 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2723    1.2369    1.9934 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4117    0.4331    2.0680 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0349   -0.4830    0.9407 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8602   -0.9645    0.3729 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9023   -2.3781   -0.1431 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6029   -2.8258   -0.7031 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6597   -3.7452   -1.8260 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5583   -4.5722   -2.0829 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4887   -3.5263   -2.5672 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0665   -2.2645   -2.2208 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0212   -1.6106   -1.4026 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4491    0.8973   -1.9679 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3709    1.8633   -2.3164 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3210    2.2685   -1.3951 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2597    3.2456   -1.7355 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8810    0.6114    2.0547 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0186    2.2492    2.7430 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3838    1.4907    2.5262 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4358    0.3192    1.1546 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9812   -1.3360    0.4958 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0339    1.7814    0.7781 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8354    3.2483    2.2739 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7682    0.0740    1.0744 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2150    1.0264    2.5536 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2109   -0.4568    2.7179 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9126   -1.1414    0.9832 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1014   -3.0006    0.7792 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7639   -2.5147   -0.7905 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1298   -3.1322    0.0765 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0522   -2.3575   -1.7693 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1693   -1.7187   -3.1890 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7624   -1.1584   -2.0300 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7024    0.5851   -2.7055 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3733    2.3249   -3.3128 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9463    3.5395   -1.0721 H   0  0  0  0  0  0  0  0  0  0  0  0
 22 21  1  0
 21 20  1  0
 20 18  1  0
 18 19  2  0
 18 17  1  0
 17 16  1  0
 16 15  1  0
 15 14  2  0
 14 11  1  0
 11 12  1  0
 12 13  1  0
 11  9  2  0
  9 10  1  0
  9  8  1  0
  8  7  2  0
  7  6  1  0
  6  5  1  0
  5  4  2  0
  4  3  1  0
  3  2  1  0
  2  1  1  0
  3 25  2  0
 25 26  1  0
 25 24  1  0
 24 23  2  0
 17 22  1  0
  7 15  1  0
 23  5  1  0
  6 22  1  0
 22 43  1  6
 21 41  1  0
 21 42  1  0
 17 40  1  1
 16 38  1  0
 16 39  1  0
 14 37  1  0
 13 34  1  0
 13 35  1  0
 13 36  1  0
 10 33  1  0
  8 32  1  0
  6 31  1  1
  4 30  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
 26 46  1  0
 24 45  1  0
 23 44  1  0
M  END


  Mrv1652309272006312D          

 28 31  0  0  0  0            999 V2000
10002.4616 9999.3897    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10002.4616 9997.7374    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10003.1803 9998.1513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.8846 9997.3252    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9998.8846 9999.8036    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
10001.030310001.8686    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.746910001.4555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.602110002.6947    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.6013 9999.3891    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9999.6013 9997.7391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.3158 9998.1515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.3158 9998.9766    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.315310001.4550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.600810001.8674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.886310001.4549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.886210000.6299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.600710000.2174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.315310000.6300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.0316 9999.3892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.0316 9997.7391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.7461 9998.1516    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.7461 9998.9767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.1022 9999.2315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.6173 9998.5640    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.1022 9997.8966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.8868 9998.1515    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9998.8868 9998.9765    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9997.8472 9997.1120    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0  0  0  0
  6  7  1  0  0  0  0
  9 12  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 13  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 19  1  0  0  0  0
 13  6  1  0  0  0  0
 14  8  1  0  0  0  0
  1 22  1  0  0  0  0
 21  2  1  0  0  0  0
  9 17  1  1  0  0  0
 19 12  2  0  0  0  0
 11 20  2  0  0  0  0
 23 27  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 28  2  0  0  0  0
  9 27  1  0  0  0  0
 27  5  1  1  0  0  0
 26 10  1  0  0  0  0
 26  4  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0189963

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@]12COC(=O)[C@]1([H])CC1=CC(OC)=C(O)C=C1[C@@H]2C1=CC(OC)=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C20H20O6/c1-24-17-6-10(3-4-15(17)21)19-12-8-16(22)18(25-2)7-11(12)5-13-14(19)9-26-20(13)23/h3-4,6-8,13-14,19,21-22H,5,9H2,1-2H3/t13-,14+,19+/m1/s1

> <INCHI_KEY>
CAYMSCGTKZIVTN-TYILLQQXSA-N

> <FORMULA>
C20H20O6

> <MOLECULAR_WEIGHT>
356.374

> <EXACT_MASS>
356.125988364

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
46

> <JCHEM_AVERAGE_POLARIZABILITY>
36.69244156560514

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3aR,4S,9aR)-6-hydroxy-4-(4-hydroxy-3-methoxyphenyl)-7-methoxy-1H,3H,3aH,4H,9H,9aH-naphtho[2,3-c]furan-1-one

> <ALOGPS_LOGP>
2.68

> <JCHEM_LOGP>
2.7393597640000005

> <ALOGPS_LOGS>
-4.26

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.194051213775195

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.587003085502715

> <JCHEM_PKA_STRONGEST_BASIC>
-4.590109739506539

> <JCHEM_POLAR_SURFACE_AREA>
85.22

> <JCHEM_REFRACTIVITY>
94.22

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.94e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3aR,4S,9aR)-6-hydroxy-4-(4-hydroxy-3-methoxyphenyl)-7-methoxy-3H,3aH,4H,9H,9aH-naphtho[2,3-c]furan-1-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 27-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-SEP-20         0                                  
HETATM    1  O   UNK     0    8671.2628665.527   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0    8671.2628662.443   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0    8672.6038663.216   0.000  0.00  0.00           C+0
HETATM    4  H   UNK     0    8664.5858661.674   0.000  0.00  0.00           H+0
HETATM    5  H   UNK     0    8664.5858666.300   0.000  0.00  0.00           H+0
HETATM    6  O   UNK     0    8668.5908670.155   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0    8669.9288669.384   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0    8665.9248671.697   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0    8665.9228665.526   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8665.9228662.446   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8667.2568663.216   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8667.2568664.756   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8667.2558669.383   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8665.9218670.152   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8664.5888669.382   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8664.5888667.842   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8665.9218667.072   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    8667.2558667.843   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0    8668.5928665.527   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0    8668.5928662.446   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0    8669.9268663.216   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0    8669.9268664.757   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0    8663.1248665.232   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0    8662.2198663.986   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0    8663.1248662.740   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0    8664.5898663.216   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0    8664.5898664.756   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0    8662.6488661.276   0.000  0.00  0.00           O+0
CONECT    1   22                                                            
CONECT    2    3   21                                                       
CONECT    3    2                                                            
CONECT    4   26                                                            
CONECT    5   27                                                            
CONECT    6    7   13                                                       
CONECT    7    6                                                            
CONECT    8   14                                                            
CONECT    9   12   17   27                                                  
CONECT   10   11   26                                                       
CONECT   11   10   12   20                                                  
CONECT   12    9   11   19                                                  
CONECT   13   14   18    6                                                  
CONECT   14   13   15    8                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18    9                                                  
CONECT   18   17   13                                                       
CONECT   19   22   12                                                       
CONECT   20   21   11                                                       
CONECT   21   20   22    2                                                  
CONECT   22   21   19    1                                                  
CONECT   23   27   24                                                       
CONECT   24   23   25                                                       
CONECT   25   26   24   28                                                  
CONECT   26   25   27   10    4                                             
CONECT   27   23   26    9    5                                             
CONECT   28   25                                                            
MASTER        0    0    0    0    0    0    0    0   28    0   62    0
END

View in JSmol

Synonyms

Value	Source
a-Conidendrin	Generator
Α-conidendrin	Generator
Conidendrin	MeSH
alpha-Conidendrin	PhytoBank
(-)-alpha-Conidendrin	PhytoBank
(-)-α-Conidendrin	PhytoBank

Chemical Formula

C₂₀H₂₀O₆

Average Mass

356.3740 Da

Monoisotopic Mass

356.12599 Da

IUPAC Name

(3aR,4S,9aR)-6-hydroxy-4-(4-hydroxy-3-methoxyphenyl)-7-methoxy-1H,3H,3aH,4H,9H,9aH-naphtho[2,3-c]furan-1-one

Traditional Name

(3aR,4S,9aR)-6-hydroxy-4-(4-hydroxy-3-methoxyphenyl)-7-methoxy-3H,3aH,4H,9H,9aH-naphtho[2,3-c]furan-1-one

CAS Registry Number

Not Available

SMILES

[H][C@]12COC(=O)[C@]1([H])CC1=CC(OC)=C(O)C=C1[C@@H]2C1=CC(OC)=C(O)C=C1

InChI Identifier

InChI=1S/C20H20O6/c1-24-17-6-10(3-4-15(17)21)19-12-8-16(22)18(25-2)7-11(12)5-13-14(19)9-26-20(13)23/h3-4,6-8,13-14,19,21-22H,5,9H2,1-2H3/t13-,14+,19+/m1/s1

InChI Key

CAYMSCGTKZIVTN-TYILLQQXSA-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
Abies holophylla	LOTUS Database	35616633
Dolomiaea souliei	LOTUS Database	35616633
Taxus mairei	LOTUS Database	35616633
Taxus wallichiana	LOTUS Database	35616633
Tsuga heterophylla	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as lignan lactones. These are lignans that contain a lactone moiety. They include 1-aryltetralin lactones, dibenzylbutyrolactone lignans, and podophyllotoxins, among others.

Kingdom

Organic compounds

Super Class

Lignans, neolignans and related compounds

Class

Lignan lactones

Sub Class

Not Available

Direct Parent

Lignan lactones

Alternative Parents

Substituents

Lignan lactone
1-aryltetralin lignan
Naphthofuran
Methoxyphenol
Tetralin
Phenoxy compound
Anisole
Methoxybenzene
Phenol ether
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Phenol
Monocyclic benzene moiety
Gamma butyrolactone
Benzenoid
Tetrahydrofuran
Lactone
Carboxylic acid ester
Carboxylic acid derivative
Oxacycle
Ether
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

lignan (CHEBI:70199 )

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	2.68	ALOGPS
logP	2.74	ChemAxon
logS	-4.3	ALOGPS
pKa (Strongest Acidic)	9.59	ChemAxon
pKa (Strongest Basic)	-4.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	85.22 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	94.22 m³·mol⁻¹	ChemAxon
Polarizability	36.69 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	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

402423

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

457194

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Shirakata H, Nishiwaki H, Yamauchi S: Syntheses of all eight stereoisomers of conidendrin. Biosci Biotechnol Biochem. 2020 Oct;84(10):1986-1996. doi: 10.1080/09168451.2020.1777081. Epub 2020 Jun 17. [PubMed:32552421 ]
Hafezi K, Hemmati AA, Abbaszadeh H, Valizadeh A, Makvandi M: Anticancer activity and molecular mechanisms of alpha-conidendrin, a polyphenolic compound present in Taxus yunnanensis, on human breast cancer cell lines. Phytother Res. 2020 Jun;34(6):1397-1408. doi: 10.1002/ptr.6613. Epub 2020 Jan 23. [PubMed:31971313 ]
Hartmann P, Lazzarotto M, Steiner L, Cigan E, Poschenrieder S, Sagmeister P, Fuchs M: TRIP-Catalyzed Asymmetric Synthesis of (+)-Yatein, (-)-alpha-Conidendrin, (+)-Isostegane, and (+)-Neoisostegane. J Org Chem. 2019 May 3;84(9):5831-5837. doi: 10.1021/acs.joc.9b00065. Epub 2019 Apr 5. [PubMed:30920215 ]
Hu CL, Xiong J, Xu P, Cheng KJ, Yang GX, Hu JF: Lignans from the shed trunk barks of the critically endangered plant Abies beshanzuensis and their anti-neuroinflammatory activities. Nat Prod Res. 2017 Jun;31(12):1358-1364. doi: 10.1080/14786419.2016.1247082. Epub 2016 Oct 23. [PubMed:27774796 ]
Sandberg T, Eklund P, Hotokka M: Conformational solvation studies of LIGNOLs with molecular dynamics and conductor-like screening model. Int J Mol Sci. 2012;13(8):9845-9863. doi: 10.3390/ijms13089845. Epub 2012 Aug 7. [PubMed:22949834 ]
LOTUS database [Link]

Showing NP-Card for α-conidendrin (NP0189963)

MOL for NP0189963 (α-conidendrin)

3D MOL for NP0189963 (α-conidendrin)

3D SDF for NP0189963 (α-conidendrin)

3D-SDF for NP0189963 (α-conidendrin)

PDB for NP0189963 (α-conidendrin)

3D PDB for NP0189963 (α-conidendrin)

SMILES for NP0189963 (α-conidendrin)

INCHI for NP0189963 (α-conidendrin)

Structure for NP0189963 (α-conidendrin)

3D Structure for NP0189963 (α-conidendrin)