NP-MRD: Showing NP-Card for burselignan (NP0031617)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2021-06-19 22:38:48 UTC

Updated at

2021-06-30 00:00:18 UTC

NP-MRD ID

NP0031617

Secondary Accession Numbers

None

Natural Product Identification

Common Name

burselignan

Provided By

JEOL Database JEOL Logo

Description

Burselignan belongs to the class of organic compounds known as 9,9p-dihydroxyaryltetralin lignans. These are lignans with a structure based on the 1-phenyltetralin skeleton carrying a hydroxyl group at the 9- and the 9'- position. burselignan is found in Abies sachalinensis, Araucaria angustifolia, Bauhinia tarapotensis, Betula pendula , Bursera tonkinensis, Coptis japonica var. dissecta , Cryptomeria japonica, Cynomorium songaricum, Daphne feddei, Datura metel, Fagraea racemosa, Fitzroya cupressoides, Gaultheria yunnanensis, Hedyotis chrysotricha, Heritiera littoralis , Isatis indigotica , Justicia diffusa var. prostrata, Justicia flava , Justicia glauca, Justicia tranquebariensis , Larix dahurica, Larix olgensis var. koreana, Larix leptolepis, Larix sibirica, Lippia sidoides, Melodinus morsei, Mitragyna africanus WILLD., Picea excelsa , Pinus massoniana, Pinus sibirica, Pinus sylvestris , Podocarpus spicatus, Punica granatum , Reseda suffruticosa, Rubia akane , Rubia yunnanensis, Salacia prinoides, Schisandra nigra, Sedum sarmentosum , Symplocos lancifolia, Taxus baccata , Taxus brevifolia , Taxus cuspidata , Taxus floridana, Taxus mairei , Tinospora smilacina , Tripterygium regelii, Tripterygium wilfordii , Ulmus davidiana var. japonica, Urtica dioica and Wikstroemia glabra. burselignan was first documented in 2005 (PMID: 16289147). Based on a literature review a significant number of articles have been published on Burselignan (PMID: 30725571) (PMID: 29933676) (PMID: 27309187) (PMID: 26762060) (PMID: 21809578) (PMID: 19673382).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202100383D          

 50 52  0  0  0  0            999 V2000
   -2.7791    4.2591   -0.4721 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7050    5.1927   -0.4469 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4381    4.6680   -0.4761 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1047    3.3145   -0.3941 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2413    2.8971   -0.4360 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6405    1.4201   -0.3349 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7771    0.5215   -1.2154 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8636    0.6469   -2.6120 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0778   -0.1509   -3.4332 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1934    0.0052   -4.7881 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8077   -1.0932   -2.9072 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5115   -1.8118   -3.8389 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3903   -2.8133   -3.3394 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8991   -1.2229   -1.5222 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1200   -0.4149   -0.6679 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2296   -0.6349    0.8223 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3435    0.5111    1.6781 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2961    0.1055    3.1582 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2519   -0.9006    3.4544 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7479    0.8831    1.1273 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5495    1.8298    2.0326 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9993    1.1308    3.1932 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2452    3.8734   -0.5788 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9203    5.2270   -0.6514 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5883    5.6092   -0.5946 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2949    6.9439   -0.6670 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7940    3.6533    0.4399 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7136    4.8271   -0.5091 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7367    3.6289   -1.3669 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8819    2.5622   -0.3110 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6563    1.3356   -0.7521 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5387    1.3690   -3.0650 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4294   -0.6441   -5.1685 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1871   -2.3712   -2.7323 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8412   -3.5771   -2.7787 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8594   -3.3037   -4.1978 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5661   -1.9511   -1.0709 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2896   -1.5739    1.0546 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2865   -0.7725    1.0854 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3215    1.3767    1.5805 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4740    0.9659    3.8123 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6938   -0.2859    3.4165 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1192   -0.4382    3.4585 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3187   -0.0580    1.0780 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9484    2.6854    2.3564 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4447    2.1922    1.5179 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5375    1.7624    3.7059 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2932    3.5859   -0.6369 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6974    5.9780   -0.7581 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6805    6.9871   -0.6318 H   0  0  0  0  0  0  0  0  0  0  0  0
 11 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15  7  1  0  0  0  0
  5 23  1  0  0  0  0
 25 26  1  0  0  0  0
 24 25  1  0  0  0  0
  3  2  1  0  0  0  0
  2  1  1  0  0  0  0
 15 16  1  0  0  0  0
  7  6  1  0  0  0  0
  6 20  1  0  0  0  0
 20 17  1  0  0  0  0
 17 16  1  0  0  0  0
 25  3  2  0  0  0  0
 11 12  1  0  0  0  0
  7  8  2  0  0  0  0
 12 13  1  0  0  0  0
 23 24  2  0  0  0  0
  9 10  1  0  0  0  0
  8  9  1  0  0  0  0
 17 18  1  0  0  0  0
  3  4  1  0  0  0  0
 20 21  1  0  0  0  0
  9 11  2  0  0  0  0
 18 19  1  0  0  0  0
  4  5  2  0  0  0  0
 21 22  1  0  0  0  0
  6  5  1  0  0  0  0
 23 48  1  0  0  0  0
 24 49  1  0  0  0  0
  4 30  1  0  0  0  0
 26 50  1  0  0  0  0
  1 27  1  0  0  0  0
  1 28  1  0  0  0  0
  1 29  1  0  0  0  0
  8 32  1  0  0  0  0
 14 37  1  0  0  0  0
  6 31  1  6  0  0  0
 20 44  1  6  0  0  0
 17 40  1  1  0  0  0
 16 38  1  0  0  0  0
 16 39  1  0  0  0  0
 13 34  1  0  0  0  0
 13 35  1  0  0  0  0
 13 36  1  0  0  0  0
 10 33  1  0  0  0  0
 18 41  1  0  0  0  0
 18 42  1  0  0  0  0
 21 45  1  0  0  0  0
 21 46  1  0  0  0  0
 19 43  1  0  0  0  0
 22 47  1  0  0  0  0
M  END

     RDKit          3D

 50 52  0  0  0  0  0  0  0  0999 V2000
   -2.7791    4.2591   -0.4721 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7050    5.1927   -0.4469 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4381    4.6680   -0.4761 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1047    3.3145   -0.3941 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2413    2.8971   -0.4360 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6405    1.4201   -0.3349 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7771    0.5215   -1.2154 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8636    0.6469   -2.6120 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0778   -0.1509   -3.4332 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1934    0.0052   -4.7881 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8077   -1.0932   -2.9072 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5115   -1.8118   -3.8389 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3903   -2.8133   -3.3394 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8991   -1.2229   -1.5222 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1200   -0.4149   -0.6679 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2296   -0.6349    0.8223 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3435    0.5111    1.6781 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2961    0.1055    3.1582 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2519   -0.9006    3.4544 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7479    0.8831    1.1273 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5495    1.8298    2.0326 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9993    1.1308    3.1932 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2452    3.8734   -0.5788 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9203    5.2270   -0.6514 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5883    5.6092   -0.5946 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2949    6.9439   -0.6670 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7940    3.6533    0.4399 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7136    4.8271   -0.5091 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7367    3.6289   -1.3669 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8819    2.5622   -0.3110 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6563    1.3356   -0.7521 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5387    1.3690   -3.0650 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4294   -0.6441   -5.1685 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1871   -2.3712   -2.7323 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8412   -3.5771   -2.7787 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8594   -3.3037   -4.1978 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5661   -1.9511   -1.0709 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2896   -1.5739    1.0546 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2865   -0.7725    1.0854 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3215    1.3767    1.5805 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4740    0.9659    3.8123 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6938   -0.2859    3.4165 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1192   -0.4382    3.4585 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3187   -0.0580    1.0780 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9484    2.6854    2.3564 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4447    2.1922    1.5179 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5375    1.7624    3.7059 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2932    3.5859   -0.6369 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6974    5.9780   -0.7581 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6805    6.9871   -0.6318 H   0  0  0  0  0  0  0  0  0  0  0  0
 11 14  1  0
 14 15  2  0
 15  7  1  0
  5 23  1  0
 25 26  1  0
 24 25  1  0
  3  2  1  0
  2  1  1  0
 15 16  1  0
  7  6  1  0
  6 20  1  0
 20 17  1  0
 17 16  1  0
 25  3  2  0
 11 12  1  0
  7  8  2  0
 12 13  1  0
 23 24  2  0
  9 10  1  0
  8  9  1  0
 17 18  1  0
  3  4  1  0
 20 21  1  0
  9 11  2  0
 18 19  1  0
  4  5  2  0
 21 22  1  0
  6  5  1  0
 23 48  1  0
 24 49  1  0
  4 30  1  0
 26 50  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  8 32  1  0
 14 37  1  0
  6 31  1  6
 20 44  1  6
 17 40  1  1
 16 38  1  0
 16 39  1  0
 13 34  1  0
 13 35  1  0
 13 36  1  0
 10 33  1  0
 18 41  1  0
 18 42  1  0
 21 45  1  0
 21 46  1  0
 19 43  1  0
 22 47  1  0
M  END


  Mrv1652306202100383D          

 50 52  0  0  0  0            999 V2000
   -2.7791    4.2591   -0.4721 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7050    5.1927   -0.4469 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4381    4.6680   -0.4761 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1047    3.3145   -0.3941 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2413    2.8971   -0.4360 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6405    1.4201   -0.3349 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7771    0.5215   -1.2154 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8636    0.6469   -2.6120 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0778   -0.1509   -3.4332 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1934    0.0052   -4.7881 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8077   -1.0932   -2.9072 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5115   -1.8118   -3.8389 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3903   -2.8133   -3.3394 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8991   -1.2229   -1.5222 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1200   -0.4149   -0.6679 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2296   -0.6349    0.8223 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3435    0.5111    1.6781 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2961    0.1055    3.1582 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2519   -0.9006    3.4544 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7479    0.8831    1.1273 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5495    1.8298    2.0326 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9993    1.1308    3.1932 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2452    3.8734   -0.5788 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9203    5.2270   -0.6514 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5883    5.6092   -0.5946 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2949    6.9439   -0.6670 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7940    3.6533    0.4399 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7136    4.8271   -0.5091 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7367    3.6289   -1.3669 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8819    2.5622   -0.3110 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6563    1.3356   -0.7521 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5387    1.3690   -3.0650 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4294   -0.6441   -5.1685 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1871   -2.3712   -2.7323 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8412   -3.5771   -2.7787 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8594   -3.3037   -4.1978 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5661   -1.9511   -1.0709 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2896   -1.5739    1.0546 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2865   -0.7725    1.0854 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3215    1.3767    1.5805 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4740    0.9659    3.8123 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6938   -0.2859    3.4165 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1192   -0.4382    3.4585 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3187   -0.0580    1.0780 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9484    2.6854    2.3564 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4447    2.1922    1.5179 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5375    1.7624    3.7059 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2932    3.5859   -0.6369 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6974    5.9780   -0.7581 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6805    6.9871   -0.6318 H   0  0  0  0  0  0  0  0  0  0  0  0
 11 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15  7  1  0  0  0  0
  5 23  1  0  0  0  0
 25 26  1  0  0  0  0
 24 25  1  0  0  0  0
  3  2  1  0  0  0  0
  2  1  1  0  0  0  0
 15 16  1  0  0  0  0
  7  6  1  0  0  0  0
  6 20  1  0  0  0  0
 20 17  1  0  0  0  0
 17 16  1  0  0  0  0
 25  3  2  0  0  0  0
 11 12  1  0  0  0  0
  7  8  2  0  0  0  0
 12 13  1  0  0  0  0
 23 24  2  0  0  0  0
  9 10  1  0  0  0  0
  8  9  1  0  0  0  0
 17 18  1  0  0  0  0
  3  4  1  0  0  0  0
 20 21  1  0  0  0  0
  9 11  2  0  0  0  0
 18 19  1  0  0  0  0
  4  5  2  0  0  0  0
 21 22  1  0  0  0  0
  6  5  1  0  0  0  0
 23 48  1  0  0  0  0
 24 49  1  0  0  0  0
  4 30  1  0  0  0  0
 26 50  1  0  0  0  0
  1 27  1  0  0  0  0
  1 28  1  0  0  0  0
  1 29  1  0  0  0  0
  8 32  1  0  0  0  0
 14 37  1  0  0  0  0
  6 31  1  6  0  0  0
 20 44  1  6  0  0  0
 17 40  1  1  0  0  0
 16 38  1  0  0  0  0
 16 39  1  0  0  0  0
 13 34  1  0  0  0  0
 13 35  1  0  0  0  0
 13 36  1  0  0  0  0
 10 33  1  0  0  0  0
 18 41  1  0  0  0  0
 18 42  1  0  0  0  0
 21 45  1  0  0  0  0
 21 46  1  0  0  0  0
 19 43  1  0  0  0  0
 22 47  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0031617

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C(OC([H])([H])[H])C([H])=C(C([H])=C1[H])[C@]1([H])C2=C([H])C(O[H])=C(OC([H])([H])[H])C([H])=C2C([H])([H])[C@@]([H])(C([H])([H])O[H])[C@]1([H])C([H])([H])O[H]

> <INCHI_IDENTIFIER>
InChI=1S/C20H24O6/c1-25-18-6-11(3-4-16(18)23)20-14-8-17(24)19(26-2)7-12(14)5-13(9-21)15(20)10-22/h3-4,6-8,13,15,20-24H,5,9-10H2,1-2H3/t13-,15-,20+/m0/s1

> <INCHI_KEY>
OGFXBIXJCWAUCH-ZQGRQUNCSA-N

> <FORMULA>
C20H24O6

> <MOLECULAR_WEIGHT>
360.406

> <EXACT_MASS>
360.157288493

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
50

> <JCHEM_AVERAGE_POLARIZABILITY>
38.36632901980841

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(6R,7R,8R)-8-(4-hydroxy-3-methoxyphenyl)-6,7-bis(hydroxymethyl)-3-methoxy-5,6,7,8-tetrahydronaphthalen-2-ol

> <ALOGPS_LOGP>
1.79

> <JCHEM_LOGP>
1.780438335666667

> <ALOGPS_LOGS>
-4.12

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.460471755201329

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.83820407739868

> <JCHEM_PKA_STRONGEST_BASIC>
-2.603686461041046

> <JCHEM_POLAR_SURFACE_AREA>
99.38000000000001

> <JCHEM_REFRACTIVITY>
97.8726

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.74e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(6R,7R,8R)-8-(4-hydroxy-3-methoxyphenyl)-6,7-bis(hydroxymethyl)-3-methoxy-5,6,7,8-tetrahydronaphthalen-2-ol

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 50 52  0  0  0  0  0  0  0  0999 V2000
   -2.7791    4.2591   -0.4721 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7050    5.1927   -0.4469 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4381    4.6680   -0.4761 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1047    3.3145   -0.3941 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2413    2.8971   -0.4360 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6405    1.4201   -0.3349 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7771    0.5215   -1.2154 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8636    0.6469   -2.6120 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0778   -0.1509   -3.4332 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1934    0.0052   -4.7881 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8077   -1.0932   -2.9072 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5115   -1.8118   -3.8389 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3903   -2.8133   -3.3394 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8991   -1.2229   -1.5222 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1200   -0.4149   -0.6679 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2296   -0.6349    0.8223 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3435    0.5111    1.6781 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2961    0.1055    3.1582 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2519   -0.9006    3.4544 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7479    0.8831    1.1273 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5495    1.8298    2.0326 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9993    1.1308    3.1932 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2452    3.8734   -0.5788 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9203    5.2270   -0.6514 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5883    5.6092   -0.5946 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2949    6.9439   -0.6670 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7940    3.6533    0.4399 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7136    4.8271   -0.5091 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7367    3.6289   -1.3669 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8819    2.5622   -0.3110 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6563    1.3356   -0.7521 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5387    1.3690   -3.0650 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4294   -0.6441   -5.1685 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1871   -2.3712   -2.7323 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8412   -3.5771   -2.7787 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8594   -3.3037   -4.1978 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5661   -1.9511   -1.0709 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2896   -1.5739    1.0546 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2865   -0.7725    1.0854 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3215    1.3767    1.5805 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4740    0.9659    3.8123 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6938   -0.2859    3.4165 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1192   -0.4382    3.4585 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3187   -0.0580    1.0780 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9484    2.6854    2.3564 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4447    2.1922    1.5179 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5375    1.7624    3.7059 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2932    3.5859   -0.6369 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6974    5.9780   -0.7581 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6805    6.9871   -0.6318 H   0  0  0  0  0  0  0  0  0  0  0  0
 11 14  1  0
 14 15  2  0
 15  7  1  0
  5 23  1  0
 25 26  1  0
 24 25  1  0
  3  2  1  0
  2  1  1  0
 15 16  1  0
  7  6  1  0
  6 20  1  0
 20 17  1  0
 17 16  1  0
 25  3  2  0
 11 12  1  0
  7  8  2  0
 12 13  1  0
 23 24  2  0
  9 10  1  0
  8  9  1  0
 17 18  1  0
  3  4  1  0
 20 21  1  0
  9 11  2  0
 18 19  1  0
  4  5  2  0
 21 22  1  0
  6  5  1  0
 23 48  1  0
 24 49  1  0
  4 30  1  0
 26 50  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  8 32  1  0
 14 37  1  0
  6 31  1  6
 20 44  1  6
 17 40  1  1
 16 38  1  0
 16 39  1  0
 13 34  1  0
 13 35  1  0
 13 36  1  0
 10 33  1  0
 18 41  1  0
 18 42  1  0
 21 45  1  0
 21 46  1  0
 19 43  1  0
 22 47  1  0
M  END

HEADER    PROTEIN                                 20-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-JUN-21         0                                  
HETATM    1  C   UNK     0      -2.779   4.259  -0.472  0.00  0.00           C+0
HETATM    2  O   UNK     0      -1.705   5.193  -0.447  0.00  0.00           O+0
HETATM    3  C   UNK     0      -0.438   4.668  -0.476  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.105   3.314  -0.394  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.241   2.897  -0.436  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.641   1.420  -0.335  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.777   0.522  -1.215  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.864   0.647  -2.612  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.078  -0.151  -3.433  0.00  0.00           C+0
HETATM   10  O   UNK     0       0.193   0.005  -4.788  0.00  0.00           O+0
HETATM   11  C   UNK     0      -0.808  -1.093  -2.907  0.00  0.00           C+0
HETATM   12  O   UNK     0      -1.512  -1.812  -3.839  0.00  0.00           O+0
HETATM   13  C   UNK     0      -2.390  -2.813  -3.339  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.899  -1.223  -1.522  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.120  -0.415  -0.668  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.230  -0.635   0.822  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.344   0.511   1.678  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.296   0.106   3.158  0.00  0.00           C+0
HETATM   19  O   UNK     0       1.252  -0.901   3.454  0.00  0.00           O+0
HETATM   20  C   UNK     0       1.748   0.883   1.127  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.550   1.830   2.033  0.00  0.00           C+0
HETATM   22  O   UNK     0       2.999   1.131   3.193  0.00  0.00           O+0
HETATM   23  C   UNK     0       2.245   3.873  -0.579  0.00  0.00           C+0
HETATM   24  C   UNK     0       1.920   5.227  -0.651  0.00  0.00           C+0
HETATM   25  C   UNK     0       0.588   5.609  -0.595  0.00  0.00           C+0
HETATM   26  O   UNK     0       0.295   6.944  -0.667  0.00  0.00           O+0
HETATM   27  H   UNK     0      -2.794   3.653   0.440  0.00  0.00           H+0
HETATM   28  H   UNK     0      -3.714   4.827  -0.509  0.00  0.00           H+0
HETATM   29  H   UNK     0      -2.737   3.629  -1.367  0.00  0.00           H+0
HETATM   30  H   UNK     0      -0.882   2.562  -0.311  0.00  0.00           H+0
HETATM   31  H   UNK     0       2.656   1.336  -0.752  0.00  0.00           H+0
HETATM   32  H   UNK     0       1.539   1.369  -3.065  0.00  0.00           H+0
HETATM   33  H   UNK     0      -0.429  -0.644  -5.168  0.00  0.00           H+0
HETATM   34  H   UNK     0      -3.187  -2.371  -2.732  0.00  0.00           H+0
HETATM   35  H   UNK     0      -1.841  -3.577  -2.779  0.00  0.00           H+0
HETATM   36  H   UNK     0      -2.859  -3.304  -4.198  0.00  0.00           H+0
HETATM   37  H   UNK     0      -1.566  -1.951  -1.071  0.00  0.00           H+0
HETATM   38  H   UNK     0       0.290  -1.574   1.055  0.00  0.00           H+0
HETATM   39  H   UNK     0      -1.287  -0.773   1.085  0.00  0.00           H+0
HETATM   40  H   UNK     0      -0.322   1.377   1.581  0.00  0.00           H+0
HETATM   41  H   UNK     0       0.474   0.966   3.812  0.00  0.00           H+0
HETATM   42  H   UNK     0      -0.694  -0.286   3.417  0.00  0.00           H+0
HETATM   43  H   UNK     0       2.119  -0.438   3.458  0.00  0.00           H+0
HETATM   44  H   UNK     0       2.319  -0.058   1.078  0.00  0.00           H+0
HETATM   45  H   UNK     0       1.948   2.685   2.356  0.00  0.00           H+0
HETATM   46  H   UNK     0       3.445   2.192   1.518  0.00  0.00           H+0
HETATM   47  H   UNK     0       3.538   1.762   3.706  0.00  0.00           H+0
HETATM   48  H   UNK     0       3.293   3.586  -0.637  0.00  0.00           H+0
HETATM   49  H   UNK     0       2.697   5.978  -0.758  0.00  0.00           H+0
HETATM   50  H   UNK     0      -0.681   6.987  -0.632  0.00  0.00           H+0
CONECT    1    2   27   28   29                                             
CONECT    2    3    1                                                       
CONECT    3    2   25    4                                                  
CONECT    4    3    5   30                                                  
CONECT    5   23    4    6                                                  
CONECT    6    7   20    5   31                                             
CONECT    7   15    6    8                                                  
CONECT    8    7    9   32                                                  
CONECT    9   10    8   11                                                  
CONECT   10    9   33                                                       
CONECT   11   14   12    9                                                  
CONECT   12   11   13                                                       
CONECT   13   12   34   35   36                                             
CONECT   14   11   15   37                                                  
CONECT   15   14    7   16                                                  
CONECT   16   15   17   38   39                                             
CONECT   17   20   16   18   40                                             
CONECT   18   17   19   41   42                                             
CONECT   19   18   43                                                       
CONECT   20    6   17   21   44                                             
CONECT   21   20   22   45   46                                             
CONECT   22   21   47                                                       
CONECT   23    5   24   48                                                  
CONECT   24   25   23   49                                                  
CONECT   25   26   24    3                                                  
CONECT   26   25   50                                                       
CONECT   27    1                                                            
CONECT   28    1                                                            
CONECT   29    1                                                            
CONECT   30    4                                                            
CONECT   31    6                                                            
CONECT   32    8                                                            
CONECT   33   10                                                            
CONECT   34   13                                                            
CONECT   35   13                                                            
CONECT   36   13                                                            
CONECT   37   14                                                            
CONECT   38   16                                                            
CONECT   39   16                                                            
CONECT   40   17                                                            
CONECT   41   18                                                            
CONECT   42   18                                                            
CONECT   43   19                                                            
CONECT   44   20                                                            
CONECT   45   21                                                            
CONECT   46   21                                                            
CONECT   47   22                                                            
CONECT   48   23                                                            
CONECT   49   24                                                            
CONECT   50   26                                                            
MASTER        0    0    0    0    0    0    0    0   50    0  104    0
END

RDKit          3D

50 52  0  0  0  0  0  0  0  0999 V2000
   -2.7791    4.2591   -0.4721 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7050    5.1927   -0.4469 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4381    4.6680   -0.4761 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1047    3.3145   -0.3941 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2413    2.8971   -0.4360 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6405    1.4201   -0.3349 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7771    0.5215   -1.2154 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8636    0.6469   -2.6120 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0778   -0.1509   -3.4332 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1934    0.0052   -4.7881 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8077   -1.0932   -2.9072 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5115   -1.8118   -3.8389 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3903   -2.8133   -3.3394 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8991   -1.2229   -1.5222 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1200   -0.4149   -0.6679 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2296   -0.6349    0.8223 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3435    0.5111    1.6781 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2961    0.1055    3.1582 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2519   -0.9006    3.4544 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7479    0.8831    1.1273 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5495    1.8298    2.0326 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9993    1.1308    3.1932 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2452    3.8734   -0.5788 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9203    5.2270   -0.6514 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5883    5.6092   -0.5946 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2949    6.9439   -0.6670 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7940    3.6533    0.4399 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7136    4.8271   -0.5091 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7367    3.6289   -1.3669 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8819    2.5622   -0.3110 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6563    1.3356   -0.7521 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5387    1.3690   -3.0650 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4294   -0.6441   -5.1685 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1871   -2.3712   -2.7323 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8412   -3.5771   -2.7787 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8594   -3.3037   -4.1978 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5661   -1.9511   -1.0709 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2896   -1.5739    1.0546 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2865   -0.7725    1.0854 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3215    1.3767    1.5805 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4740    0.9659    3.8123 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6938   -0.2859    3.4165 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1192   -0.4382    3.4585 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3187   -0.0580    1.0780 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9484    2.6854    2.3564 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4447    2.1922    1.5179 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5375    1.7624    3.7059 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2932    3.5859   -0.6369 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6974    5.9780   -0.7581 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6805    6.9871   -0.6318 H   0  0  0  0  0  0  0  0  0  0  0  0
 11 14  1  0
 14 15  2  0
 15  7  1  0
  5 23  1  0
 25 26  1  0
 24 25  1  0
  3  2  1  0
  2  1  1  0
 15 16  1  0
  7  6  1  0
  6 20  1  0
 20 17  1  0
 17 16  1  0
 25  3  2  0
 11 12  1  0
  7  8  2  0
 12 13  1  0
 23 24  2  0
  9 10  1  0
  8  9  1  0
 17 18  1  0
  3  4  1  0
 20 21  1  0
  9 11  2  0
 18 19  1  0
  4  5  2  0
 21 22  1  0
  6  5  1  0
 23 48  1  0
 24 49  1  0
  4 30  1  0
 26 50  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  8 32  1  0
 14 37  1  0
  6 31  1  6
 20 44  1  6
 17 40  1  1
 16 38  1  0
 16 39  1  0
 13 34  1  0
 13 35  1  0
 13 36  1  0
 10 33  1  0
 18 41  1  0
 18 42  1  0
 21 45  1  0
 21 46  1  0
 19 43  1  0
 22 47  1  0
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₂₄O₆

Average Mass

360.4060 Da

Monoisotopic Mass

360.15729 Da

IUPAC Name

(6R,7R,8R)-8-(4-hydroxy-3-methoxyphenyl)-6,7-bis(hydroxymethyl)-3-methoxy-5,6,7,8-tetrahydronaphthalen-2-ol

Traditional Name

(6R,7R,8R)-8-(4-hydroxy-3-methoxyphenyl)-6,7-bis(hydroxymethyl)-3-methoxy-5,6,7,8-tetrahydronaphthalen-2-ol

CAS Registry Number

Not Available

SMILES

[H]OC1=C(OC([H])([H])[H])C([H])=C(C([H])=C1[H])[C@]1([H])C2=C([H])C(O[H])=C(OC([H])([H])[H])C([H])=C2C([H])([H])[C@@]([H])(C([H])([H])O[H])[C@]1([H])C([H])([H])O[H]

InChI Identifier

InChI=1S/C20H24O6/c1-25-18-6-11(3-4-16(18)23)20-14-8-17(24)19(26-2)7-12(14)5-13(9-21)15(20)10-22/h3-4,6-8,13,15,20-24H,5,9-10H2,1-2H3/t13-,15-,20+/m0/s1

InChI Key

OGFXBIXJCWAUCH-ZQGRQUNCSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CD₃OD, 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
Abies sachalinensis	Plant	KNApSAcK
Araucaria angustifolia	Plant	KNApSAcK
Bauhinia tarapotensis	Plant	KNApSAcK
Betula pendula	Plant	KNApSAcK
Bursera tonkinensis	JEOL database	Jutiviboonsuk, A., et al, Phytochemistry 66, 2745 (2005)
Coptis japonica var. dissecta	Plant	KNApSAcK
Cryptomeria japonica	Plant	KNApSAcK
Cynomorium songaricum	Plant	KNApSAcK
Daphne feddei	Plant	KNApSAcK
Datura metel	LOTUS Database	35616633
Fagraea racemosa	Plant	KNApSAcK
Fitzroya cupressoides	Plant	KNApSAcK
Gaultheria yunnanensis	Plant	KNApSAcK
Hedyotis chrysotricha	Plant	KNApSAcK
Heritiera littoralis	Plant	KNApSAcK
Isatis tinctoria	Plant	KNApSAcK
Justicia diffusa var. prostrata	Plant	KNApSAcK
Justicia flava	Plant	KNApSAcK
Justicia glauca	Plant	KNApSAcK
Justicia tranquebariensis	Plant	KNApSAcK
Larix dahurica	Plant	KNApSAcK
Larix gmelinii var. olgensis	Plant	KNApSAcK
Larix leptolepis	Plant	KNApSAcK
Larix sibirica	Plant	KNApSAcK
Lippia sidoides	Plant	KNApSAcK
Melodinus morsei	Plant	KNApSAcK
Mitragyna africanus WILLD.	Plant	KNApSAcK
Picea abies	Plant	KNApSAcK
Pinus massoniana	Plant	KNApSAcK
Pinus sibirica	Plant	KNApSAcK
Pinus sylvestris	Plant	KNApSAcK
Podocarpus spicatus	Plant	KNApSAcK
Punica granatum	Plant	KNApSAcK
Reseda suffruticosa	Plant	KNApSAcK
Rubia akane	Plant	KNApSAcK
Rubia yunnanensis	Plant	KNApSAcK
Salacia prinoides	Plant	KNApSAcK
Schisandra nigra	Plant	KNApSAcK
Sedum sarmentosum	Plant	KNApSAcK
Symplocos lancifolia	Plant	KNApSAcK
Taxus baccata	Plant	KNApSAcK
Taxus brevifolia	Plant	KNApSAcK
Taxus cuspidata	Plant	KNApSAcK
Taxus floridana	Plant	KNApSAcK
Taxus mairei	Plant	KNApSAcK
Tinospora smilacina	Plant	KNApSAcK
Tripterygium regelii	Plant	KNApSAcK
Tripterygium wilfordii	Plant	KNApSAcK
Ulmus davidiana var. japonica	Plant	KNApSAcK
Urtica dioica	Plant	KNApSAcK
Wikstroemia glabra	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 9,9p-dihydroxyaryltetralin lignans. These are lignans with a structure based on the 1-phenyltetralin skeleton carrying a hydroxyl group at the 9- and the 9'- position.

Kingdom

Organic compounds

Super Class

Lignans, neolignans and related compounds

Class

Aryltetralin lignans

Sub Class

9,9p-dihydroxyaryltetralin lignans

Direct Parent

9,9p-dihydroxyaryltetralin lignans

Alternative Parents

Substituents

9,9p-dihydroxyaryltetralin lignan
Methoxyphenol
Tetralin
Phenoxy compound
Anisole
Methoxybenzene
Phenol ether
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Phenol
Monocyclic benzene moiety
Benzenoid
Ether
Organic oxygen compound
Alcohol
Hydrocarbon derivative
Organooxygen compound
Primary alcohol
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic 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	1.79	ALOGPS
logP	1.78	ChemAxon
logS	-4.1	ALOGPS
pKa (Strongest Acidic)	9.84	ChemAxon
pKa (Strongest Basic)	-2.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	99.38 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	97.87 m³·mol⁻¹	ChemAxon
Polarizability	38.37 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	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

9806609

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11631864

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Pan Y, Zhang Y, Fan C, Zhang Y, Yan S, Jin H, Zhang W: Lignans from the Whole Plants of Hedyotis uncinella. Nat Prod Commun. 2016 Aug;11(8):1115-1116. [PubMed:30725571 ]
Chen Y, Fan CL, Wang Y, Zhang XQ, Huang XJ, Ye WC: [Chemical constituents from roots of Isatis indigotica]. Zhongguo Zhong Yao Za Zhi. 2018 May;43(10):2091-2096. doi: 10.19540/j.cnki.cjcmm.20180116.001. [PubMed:29933676 ]
Zhang CF, Zhou J, Yang JZ, Li CJ, Ma J, Zhang D, Li L, Zhang DM: Three new lignanosides from the aerial parts of Lespedeza cuneata. J Asian Nat Prod Res. 2016 Oct;18(10):913-20. doi: 10.1080/10286020.2016.1187603. Epub 2016 Jun 16. [PubMed:27309187 ]
Zhang YM, Zhang PZ: [Lignans from Stem Bark of Styrax perkinsiae]. Zhong Yao Cai. 2015 Jun;38(6):1202-5. [PubMed:26762060 ]
Cao X, Li C, Yang J, Wei B, Luo Y, Zhang D: [Study on chemical constituents from leaves of Tripterygium wilfordii]. Zhongguo Zhong Yao Za Zhi. 2011 Apr;36(8):1028-31. [PubMed:21809578 ]
Ouyang F, Liu Y, Xiao H, Yu H, Wang N, Yao X: [Lignans from stems of Sambucus williamsii]. Zhongguo Zhong Yao Za Zhi. 2009 May;34(10):1225-7. [PubMed:19673382 ]
Jutiviboonsuk A, Zhang H, Tan GT, Ma C, Van Hung N, Manh Cuong N, Bunyapraphatsara N, Soejarto DD, Fong HH: Bioactive constituents from roots of Bursera tonkinensis. Phytochemistry. 2005 Dec;66(23):2745-51. doi: 10.1016/j.phytochem.2005.09.025. Epub 2005 Nov 9. [PubMed:16289147 ]
Jutiviboonsuk, A., et al. (2005). Jutiviboonsuk, A., et al, Phytochemistry 66, 2745 (2005) . Phytochem..

Showing NP-Card for burselignan (NP0031617)

MOL for NP0031617 (burselignan)

3D MOL for NP0031617 (burselignan)

3D SDF for NP0031617 (burselignan)

3D-SDF for NP0031617 (burselignan)

PDB for NP0031617 (burselignan)

3D PDB for NP0031617 (burselignan)

SMILES for NP0031617 (burselignan)

INCHI for NP0031617 (burselignan)

Structure for NP0031617 (burselignan)

3D Structure for NP0031617 (burselignan)