NP-MRD: Showing NP-Card for Varixanthone (NP0004090)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2020-12-09 01:35:14 UTC

Updated at

2021-07-15 16:48:12 UTC

NP-MRD ID

NP0004090

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Varixanthone

Provided By

NPAtlas

Description

(2S)-1-[(3S,4R)-4,6-dihydroxy-12-methyl-5-oxo-3-(prop-1-en-2-yl)-2,3,4,5-tetrahydro-1,10-dioxatetraphen-9-yl]-3-hydroxy-3-methylbutan-2-yl formate belongs to the class of organic compounds known as 4-prenylated xanthones. These are organic compounds containing a C5-isoprenoid group linked to a xanthone moiety at the 4-position. Xanthone is a tricyclic compound made up of two benzene rings linearly fused to each other through a pyran ring that carries a ketone group. Varixanthone is found in Emericella variecolor and Emericella. Varixanthone was first documented in 2002 (PMID: 11908979). Based on a literature review very few articles have been published on (2S)-1-[(3S,4R)-4,6-dihydroxy-12-methyl-5-oxo-3-(prop-1-en-2-yl)-2,3,4,5-tetrahydro-1,10-dioxatetraphen-9-yl]-3-hydroxy-3-methylbutan-2-yl formate.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242118043D          

 62 65  0  0  0  0            999 V2000
   -6.9741   -0.2691   -1.0942 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8573   -0.9501   -0.9492 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6197   -2.1613   -1.7410 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8586   -0.4661    0.0558 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.6315   -1.4658    1.1324 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.8109   -0.8073    2.1189 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5545   -0.4197    1.6078 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4865   -0.3598    2.4823 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6643   -0.6857    3.9251 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2719    0.0077    1.9802 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0999    0.3124    0.6405 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0809    0.6563    0.1938 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3346    0.9566   -1.0585 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6171    1.3113   -1.4377 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6883    1.3218   -0.4165 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2341   -0.0460   -0.0902 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2105   -0.8502    0.3973 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8136   -2.0239   -0.2194 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3903   -2.3833   -1.2533 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3567    0.1493    0.9097 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.4358    1.0140    0.3003 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7915    0.8424    2.1248 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9424   -1.0604    1.2670 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8259    1.6163   -2.7504 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8329    1.5852   -3.6926 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5374    1.2283   -3.3211 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4069    1.2094   -4.2739 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3173    0.9202   -2.0042 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9513    0.5492   -1.5148 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8671    0.5064   -2.3342 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1811    0.2448   -0.2035 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4435   -0.1208    0.2495 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5819   -0.1319   -0.6658 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.8592    1.1975   -1.1353 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7136   -0.6063   -1.7984 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1680    0.6207   -0.5235 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2836   -2.1748   -2.6587 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9191   -3.0875   -1.1924 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6171   -2.3307   -2.1152 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2690    0.4566    0.5661 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1004   -2.3719    0.8132 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5620   -1.7336    1.6850 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2411    0.1071    4.5836 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7442   -0.7261    4.1574 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2029   -1.6684    4.1945 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5660    0.0594    2.6487 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4748    2.0308   -0.7422 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1920    1.6961    0.5302 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6935   -0.4417   -1.0306 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0153   -2.6205    0.1895 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3599    2.0701    0.6302 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4299    0.6321    0.5946 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4011    0.9421   -0.8177 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7671    0.4543    2.3283 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4147    0.6567    3.0332 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6750    1.9300    1.9414 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9094   -1.0328    1.3652 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8555    1.8955   -3.0243 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0742    1.8430   -4.7286 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3455    1.0111   -4.3173 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5033   -0.8318   -1.4946 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4477    1.7931   -0.4331 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 16 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 20 23  1  1  0  0  0
 14 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 29 31  1  0  0  0  0
 31 32  2  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 33  4  1  0  0  0  0
 32  7  1  0  0  0  0
 31 11  1  0  0  0  0
 28 13  1  0  0  0  0
  1 35  1  0  0  0  0
  1 36  1  0  0  0  0
  3 37  1  0  0  0  0
  3 38  1  0  0  0  0
  3 39  1  0  0  0  0
  4 40  1  1  0  0  0
  5 41  1  0  0  0  0
  5 42  1  0  0  0  0
  9 43  1  0  0  0  0
  9 44  1  0  0  0  0
  9 45  1  0  0  0  0
 10 46  1  0  0  0  0
 15 47  1  0  0  0  0
 15 48  1  0  0  0  0
 16 49  1  6  0  0  0
 18 50  1  0  0  0  0
 21 51  1  0  0  0  0
 21 52  1  0  0  0  0
 21 53  1  0  0  0  0
 22 54  1  0  0  0  0
 22 55  1  0  0  0  0
 22 56  1  0  0  0  0
 23 57  1  0  0  0  0
 24 58  1  0  0  0  0
 25 59  1  0  0  0  0
 27 60  1  0  0  0  0
 33 61  1  6  0  0  0
 34 62  1  0  0  0  0
M  END

     RDKit          3D

 62 65  0  0  0  0  0  0  0  0999 V2000
   -6.9741   -0.2691   -1.0942 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8573   -0.9501   -0.9492 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6197   -2.1613   -1.7410 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8586   -0.4661    0.0558 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.6315   -1.4658    1.1324 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8109   -0.8073    2.1189 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5545   -0.4197    1.6078 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4865   -0.3598    2.4823 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6643   -0.6857    3.9251 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2719    0.0077    1.9802 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0999    0.3124    0.6405 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0809    0.6563    0.1938 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3346    0.9566   -1.0585 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6171    1.3113   -1.4377 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6883    1.3218   -0.4165 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2341   -0.0460   -0.0902 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2105   -0.8502    0.3973 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8136   -2.0239   -0.2194 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3903   -2.3833   -1.2533 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3567    0.1493    0.9097 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.4358    1.0140    0.3003 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7915    0.8424    2.1248 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9424   -1.0604    1.2670 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8259    1.6163   -2.7504 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8329    1.5852   -3.6926 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5374    1.2283   -3.3211 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4069    1.2094   -4.2739 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3173    0.9202   -2.0042 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9513    0.5492   -1.5148 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8671    0.5064   -2.3342 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1811    0.2448   -0.2035 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4435   -0.1208    0.2495 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5819   -0.1319   -0.6658 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.8592    1.1975   -1.1353 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7136   -0.6063   -1.7984 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1680    0.6207   -0.5235 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2836   -2.1748   -2.6587 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9191   -3.0875   -1.1924 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6171   -2.3307   -2.1152 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2690    0.4566    0.5661 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1004   -2.3719    0.8132 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5620   -1.7336    1.6850 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2411    0.1071    4.5836 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7442   -0.7261    4.1574 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2029   -1.6684    4.1945 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5660    0.0594    2.6487 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4748    2.0308   -0.7422 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1920    1.6961    0.5302 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6935   -0.4417   -1.0306 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0153   -2.6205    0.1895 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3599    2.0701    0.6302 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4299    0.6321    0.5946 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4011    0.9421   -0.8177 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7671    0.4543    2.3283 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4147    0.6567    3.0332 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6750    1.9300    1.9414 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9094   -1.0328    1.3652 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8555    1.8955   -3.0243 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0742    1.8430   -4.7286 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3455    1.0111   -4.3173 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5033   -0.8318   -1.4946 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4477    1.7931   -0.4331 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 16 20  1  0
 20 21  1  0
 20 22  1  0
 20 23  1  1
 14 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  1  0
 26 28  2  0
 28 29  1  0
 29 30  2  0
 29 31  1  0
 31 32  2  0
 32 33  1  0
 33 34  1  0
 33  4  1  0
 32  7  1  0
 31 11  1  0
 28 13  1  0
  1 35  1  0
  1 36  1  0
  3 37  1  0
  3 38  1  0
  3 39  1  0
  4 40  1  1
  5 41  1  0
  5 42  1  0
  9 43  1  0
  9 44  1  0
  9 45  1  0
 10 46  1  0
 15 47  1  0
 15 48  1  0
 16 49  1  6
 18 50  1  0
 21 51  1  0
 21 52  1  0
 21 53  1  0
 22 54  1  0
 22 55  1  0
 22 56  1  0
 23 57  1  0
 24 58  1  0
 25 59  1  0
 27 60  1  0
 33 61  1  6
 34 62  1  0
M  END


  Mrv1652306242118043D          

 62 65  0  0  0  0            999 V2000
   -6.9741   -0.2691   -1.0942 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8573   -0.9501   -0.9492 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6197   -2.1613   -1.7410 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8586   -0.4661    0.0558 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.6315   -1.4658    1.1324 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.8109   -0.8073    2.1189 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5545   -0.4197    1.6078 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4865   -0.3598    2.4823 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6643   -0.6857    3.9251 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2719    0.0077    1.9802 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0999    0.3124    0.6405 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0809    0.6563    0.1938 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3346    0.9566   -1.0585 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6171    1.3113   -1.4377 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6883    1.3218   -0.4165 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2341   -0.0460   -0.0902 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2105   -0.8502    0.3973 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8136   -2.0239   -0.2194 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3903   -2.3833   -1.2533 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3567    0.1493    0.9097 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.4358    1.0140    0.3003 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7915    0.8424    2.1248 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9424   -1.0604    1.2670 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8259    1.6163   -2.7504 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8329    1.5852   -3.6926 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5374    1.2283   -3.3211 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4069    1.2094   -4.2739 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3173    0.9202   -2.0042 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9513    0.5492   -1.5148 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8671    0.5064   -2.3342 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1811    0.2448   -0.2035 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4435   -0.1208    0.2495 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5819   -0.1319   -0.6658 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.8592    1.1975   -1.1353 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7136   -0.6063   -1.7984 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1680    0.6207   -0.5235 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2836   -2.1748   -2.6587 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9191   -3.0875   -1.1924 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6171   -2.3307   -2.1152 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2690    0.4566    0.5661 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1004   -2.3719    0.8132 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5620   -1.7336    1.6850 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2411    0.1071    4.5836 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7442   -0.7261    4.1574 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2029   -1.6684    4.1945 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5660    0.0594    2.6487 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4748    2.0308   -0.7422 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1920    1.6961    0.5302 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6935   -0.4417   -1.0306 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0153   -2.6205    0.1895 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3599    2.0701    0.6302 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4299    0.6321    0.5946 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4011    0.9421   -0.8177 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7671    0.4543    2.3283 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4147    0.6567    3.0332 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6750    1.9300    1.9414 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9094   -1.0328    1.3652 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8555    1.8955   -3.0243 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0742    1.8430   -4.7286 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3455    1.0111   -4.3173 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5033   -0.8318   -1.4946 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4477    1.7931   -0.4331 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 16 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 20 23  1  1  0  0  0
 14 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 29 31  1  0  0  0  0
 31 32  2  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 33  4  1  0  0  0  0
 32  7  1  0  0  0  0
 31 11  1  0  0  0  0
 28 13  1  0  0  0  0
  1 35  1  0  0  0  0
  1 36  1  0  0  0  0
  3 37  1  0  0  0  0
  3 38  1  0  0  0  0
  3 39  1  0  0  0  0
  4 40  1  1  0  0  0
  5 41  1  0  0  0  0
  5 42  1  0  0  0  0
  9 43  1  0  0  0  0
  9 44  1  0  0  0  0
  9 45  1  0  0  0  0
 10 46  1  0  0  0  0
 15 47  1  0  0  0  0
 15 48  1  0  0  0  0
 16 49  1  6  0  0  0
 18 50  1  0  0  0  0
 21 51  1  0  0  0  0
 21 52  1  0  0  0  0
 21 53  1  0  0  0  0
 22 54  1  0  0  0  0
 22 55  1  0  0  0  0
 22 56  1  0  0  0  0
 23 57  1  0  0  0  0
 24 58  1  0  0  0  0
 25 59  1  0  0  0  0
 27 60  1  0  0  0  0
 33 61  1  6  0  0  0
 34 62  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0004090

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C2C(=O)C3=C4C(OC([H])([H])[C@]([H])(C(=C([H])[H])C([H])([H])[H])[C@@]4([H])O[H])=C(C([H])=C3OC2=C(C([H])=C1[H])C([H])([H])[C@]([H])(OC([H])=O)C(O[H])(C([H])([H])[H])C([H])([H])[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C26H28O8/c1-12(2)15-10-32-24-13(3)8-17-20(21(24)22(15)29)23(30)19-16(28)7-6-14(25(19)34-17)9-18(33-11-27)26(4,5)31/h6-8,11,15,18,22,28-29,31H,1,9-10H2,2-5H3/t15-,18+,22-/m1/s1

> <INCHI_KEY>
GOKVXLNHAYUYGV-FXCLAUTBSA-N

> <FORMULA>
C26H28O8

> <MOLECULAR_WEIGHT>
468.502

> <EXACT_MASS>
468.178417862

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
62

> <JCHEM_AVERAGE_POLARIZABILITY>
49.39137163404977

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S)-1-[(3S,4R)-4,6-dihydroxy-12-methyl-5-oxo-3-(prop-1-en-2-yl)-2,3,4,5-tetrahydro-1,10-dioxatetraphen-9-yl]-3-hydroxy-3-methylbutan-2-yl formate

> <ALOGPS_LOGP>
2.73

> <JCHEM_LOGP>
3.686497521333333

> <ALOGPS_LOGS>
-4.07

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.526569476027547

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.378922501008503

> <JCHEM_PKA_STRONGEST_BASIC>
-3.1085637408393385

> <JCHEM_POLAR_SURFACE_AREA>
122.52000000000002

> <JCHEM_REFRACTIVITY>
124.27899999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.98e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-1-[(3S,4R)-4,6-dihydroxy-12-methyl-5-oxo-3-(prop-1-en-2-yl)-3,4-dihydro-2H-1,10-dioxatetraphen-9-yl]-3-hydroxy-3-methylbutan-2-yl formate

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 62 65  0  0  0  0  0  0  0  0999 V2000
   -6.9741   -0.2691   -1.0942 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8573   -0.9501   -0.9492 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6197   -2.1613   -1.7410 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8586   -0.4661    0.0558 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.6315   -1.4658    1.1324 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8109   -0.8073    2.1189 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5545   -0.4197    1.6078 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4865   -0.3598    2.4823 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6643   -0.6857    3.9251 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2719    0.0077    1.9802 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0999    0.3124    0.6405 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0809    0.6563    0.1938 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3346    0.9566   -1.0585 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6171    1.3113   -1.4377 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6883    1.3218   -0.4165 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2341   -0.0460   -0.0902 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2105   -0.8502    0.3973 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8136   -2.0239   -0.2194 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3903   -2.3833   -1.2533 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3567    0.1493    0.9097 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.4358    1.0140    0.3003 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7915    0.8424    2.1248 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9424   -1.0604    1.2670 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8259    1.6163   -2.7504 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8329    1.5852   -3.6926 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5374    1.2283   -3.3211 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4069    1.2094   -4.2739 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3173    0.9202   -2.0042 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9513    0.5492   -1.5148 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8671    0.5064   -2.3342 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1811    0.2448   -0.2035 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4435   -0.1208    0.2495 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5819   -0.1319   -0.6658 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.8592    1.1975   -1.1353 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7136   -0.6063   -1.7984 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1680    0.6207   -0.5235 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2836   -2.1748   -2.6587 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9191   -3.0875   -1.1924 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6171   -2.3307   -2.1152 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2690    0.4566    0.5661 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1004   -2.3719    0.8132 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5620   -1.7336    1.6850 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2411    0.1071    4.5836 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7442   -0.7261    4.1574 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2029   -1.6684    4.1945 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5660    0.0594    2.6487 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4748    2.0308   -0.7422 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1920    1.6961    0.5302 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6935   -0.4417   -1.0306 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0153   -2.6205    0.1895 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3599    2.0701    0.6302 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4299    0.6321    0.5946 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4011    0.9421   -0.8177 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7671    0.4543    2.3283 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4147    0.6567    3.0332 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6750    1.9300    1.9414 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9094   -1.0328    1.3652 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8555    1.8955   -3.0243 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0742    1.8430   -4.7286 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3455    1.0111   -4.3173 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5033   -0.8318   -1.4946 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4477    1.7931   -0.4331 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 16 20  1  0
 20 21  1  0
 20 22  1  0
 20 23  1  1
 14 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  1  0
 26 28  2  0
 28 29  1  0
 29 30  2  0
 29 31  1  0
 31 32  2  0
 32 33  1  0
 33 34  1  0
 33  4  1  0
 32  7  1  0
 31 11  1  0
 28 13  1  0
  1 35  1  0
  1 36  1  0
  3 37  1  0
  3 38  1  0
  3 39  1  0
  4 40  1  1
  5 41  1  0
  5 42  1  0
  9 43  1  0
  9 44  1  0
  9 45  1  0
 10 46  1  0
 15 47  1  0
 15 48  1  0
 16 49  1  6
 18 50  1  0
 21 51  1  0
 21 52  1  0
 21 53  1  0
 22 54  1  0
 22 55  1  0
 22 56  1  0
 23 57  1  0
 24 58  1  0
 25 59  1  0
 27 60  1  0
 33 61  1  6
 34 62  1  0
M  END

HEADER    PROTEIN                                 24-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-JUN-21         0                                  
HETATM    1  C   UNK     0      -6.974  -0.269  -1.094  0.00  0.00           C+0
HETATM    2  C   UNK     0      -5.857  -0.950  -0.949  0.00  0.00           C+0
HETATM    3  C   UNK     0      -5.620  -2.161  -1.741  0.00  0.00           C+0
HETATM    4  C   UNK     0      -4.859  -0.466   0.056  0.00  0.00           C+0
HETATM    5  C   UNK     0      -4.632  -1.466   1.132  0.00  0.00           C+0
HETATM    6  O   UNK     0      -3.811  -0.807   2.119  0.00  0.00           O+0
HETATM    7  C   UNK     0      -2.555  -0.420   1.608  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.486  -0.360   2.482  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.664  -0.686   3.925  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.272   0.008   1.980  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.100   0.312   0.641  0.00  0.00           C+0
HETATM   12  O   UNK     0       1.081   0.656   0.194  0.00  0.00           O+0
HETATM   13  C   UNK     0       1.335   0.957  -1.059  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.617   1.311  -1.438  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.688   1.322  -0.417  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.234  -0.046  -0.090  0.00  0.00           C+0
HETATM   17  O   UNK     0       3.211  -0.850   0.397  0.00  0.00           O+0
HETATM   18  C   UNK     0       2.814  -2.024  -0.219  0.00  0.00           C+0
HETATM   19  O   UNK     0       3.390  -2.383  -1.253  0.00  0.00           O+0
HETATM   20  C   UNK     0       5.357   0.149   0.910  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.436   1.014   0.300  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.792   0.842   2.125  0.00  0.00           C+0
HETATM   23  O   UNK     0       5.942  -1.060   1.267  0.00  0.00           O+0
HETATM   24  C   UNK     0       2.826   1.616  -2.750  0.00  0.00           C+0
HETATM   25  C   UNK     0       1.833   1.585  -3.693  0.00  0.00           C+0
HETATM   26  C   UNK     0       0.537   1.228  -3.321  0.00  0.00           C+0
HETATM   27  O   UNK     0      -0.407   1.209  -4.274  0.00  0.00           O+0
HETATM   28  C   UNK     0       0.317   0.920  -2.004  0.00  0.00           C+0
HETATM   29  C   UNK     0      -0.951   0.549  -1.515  0.00  0.00           C+0
HETATM   30  O   UNK     0      -1.867   0.506  -2.334  0.00  0.00           O+0
HETATM   31  C   UNK     0      -1.181   0.245  -0.204  0.00  0.00           C+0
HETATM   32  C   UNK     0      -2.443  -0.121   0.250  0.00  0.00           C+0
HETATM   33  C   UNK     0      -3.582  -0.132  -0.666  0.00  0.00           C+0
HETATM   34  O   UNK     0      -3.859   1.198  -1.135  0.00  0.00           O+0
HETATM   35  H   UNK     0      -7.714  -0.606  -1.798  0.00  0.00           H+0
HETATM   36  H   UNK     0      -7.168   0.621  -0.524  0.00  0.00           H+0
HETATM   37  H   UNK     0      -6.284  -2.175  -2.659  0.00  0.00           H+0
HETATM   38  H   UNK     0      -5.919  -3.087  -1.192  0.00  0.00           H+0
HETATM   39  H   UNK     0      -4.617  -2.331  -2.115  0.00  0.00           H+0
HETATM   40  H   UNK     0      -5.269   0.457   0.566  0.00  0.00           H+0
HETATM   41  H   UNK     0      -4.100  -2.372   0.813  0.00  0.00           H+0
HETATM   42  H   UNK     0      -5.562  -1.734   1.685  0.00  0.00           H+0
HETATM   43  H   UNK     0      -1.241   0.107   4.584  0.00  0.00           H+0
HETATM   44  H   UNK     0      -2.744  -0.726   4.157  0.00  0.00           H+0
HETATM   45  H   UNK     0      -1.203  -1.668   4.194  0.00  0.00           H+0
HETATM   46  H   UNK     0       0.566   0.059   2.649  0.00  0.00           H+0
HETATM   47  H   UNK     0       4.475   2.031  -0.742  0.00  0.00           H+0
HETATM   48  H   UNK     0       3.192   1.696   0.530  0.00  0.00           H+0
HETATM   49  H   UNK     0       4.694  -0.442  -1.031  0.00  0.00           H+0
HETATM   50  H   UNK     0       2.015  -2.620   0.190  0.00  0.00           H+0
HETATM   51  H   UNK     0       6.360   2.070   0.630  0.00  0.00           H+0
HETATM   52  H   UNK     0       7.430   0.632   0.595  0.00  0.00           H+0
HETATM   53  H   UNK     0       6.401   0.942  -0.818  0.00  0.00           H+0
HETATM   54  H   UNK     0       3.767   0.454   2.328  0.00  0.00           H+0
HETATM   55  H   UNK     0       5.415   0.657   3.033  0.00  0.00           H+0
HETATM   56  H   UNK     0       4.675   1.930   1.941  0.00  0.00           H+0
HETATM   57  H   UNK     0       6.909  -1.033   1.365  0.00  0.00           H+0
HETATM   58  H   UNK     0       3.856   1.896  -3.024  0.00  0.00           H+0
HETATM   59  H   UNK     0       2.074   1.843  -4.729  0.00  0.00           H+0
HETATM   60  H   UNK     0      -1.345   1.011  -4.317  0.00  0.00           H+0
HETATM   61  H   UNK     0      -3.503  -0.832  -1.495  0.00  0.00           H+0
HETATM   62  H   UNK     0      -3.448   1.793  -0.433  0.00  0.00           H+0
CONECT    1    2   35   36                                                  
CONECT    2    1    3    4                                                  
CONECT    3    2   37   38   39                                             
CONECT    4    2    5   33   40                                             
CONECT    5    4    6   41   42                                             
CONECT    6    5    7                                                       
CONECT    7    6    8   32                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8   43   44   45                                             
CONECT   10    8   11   46                                                  
CONECT   11   10   12   31                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   28                                                  
CONECT   14   13   15   24                                                  
CONECT   15   14   16   47   48                                             
CONECT   16   15   17   20   49                                             
CONECT   17   16   18                                                       
CONECT   18   17   19   50                                                  
CONECT   19   18                                                            
CONECT   20   16   21   22   23                                             
CONECT   21   20   51   52   53                                             
CONECT   22   20   54   55   56                                             
CONECT   23   20   57                                                       
CONECT   24   14   25   58                                                  
CONECT   25   24   26   59                                                  
CONECT   26   25   27   28                                                  
CONECT   27   26   60                                                       
CONECT   28   26   29   13                                                  
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   32   11                                                  
CONECT   32   31   33    7                                                  
CONECT   33   32   34    4   61                                             
CONECT   34   33   62                                                       
CONECT   35    1                                                            
CONECT   36    1                                                            
CONECT   37    3                                                            
CONECT   38    3                                                            
CONECT   39    3                                                            
CONECT   40    4                                                            
CONECT   41    5                                                            
CONECT   42    5                                                            
CONECT   43    9                                                            
CONECT   44    9                                                            
CONECT   45    9                                                            
CONECT   46   10                                                            
CONECT   47   15                                                            
CONECT   48   15                                                            
CONECT   49   16                                                            
CONECT   50   18                                                            
CONECT   51   21                                                            
CONECT   52   21                                                            
CONECT   53   21                                                            
CONECT   54   22                                                            
CONECT   55   22                                                            
CONECT   56   22                                                            
CONECT   57   23                                                            
CONECT   58   24                                                            
CONECT   59   25                                                            
CONECT   60   27                                                            
CONECT   61   33                                                            
CONECT   62   34                                                            
MASTER        0    0    0    0    0    0    0    0   62    0  130    0
END

RDKit          3D

62 65  0  0  0  0  0  0  0  0999 V2000
   -6.9741   -0.2691   -1.0942 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8573   -0.9501   -0.9492 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6197   -2.1613   -1.7410 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8586   -0.4661    0.0558 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.6315   -1.4658    1.1324 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8109   -0.8073    2.1189 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5545   -0.4197    1.6078 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4865   -0.3598    2.4823 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6643   -0.6857    3.9251 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2719    0.0077    1.9802 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0999    0.3124    0.6405 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0809    0.6563    0.1938 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3346    0.9566   -1.0585 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6171    1.3113   -1.4377 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6883    1.3218   -0.4165 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2341   -0.0460   -0.0902 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2105   -0.8502    0.3973 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8136   -2.0239   -0.2194 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3903   -2.3833   -1.2533 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3567    0.1493    0.9097 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.4358    1.0140    0.3003 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7915    0.8424    2.1248 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9424   -1.0604    1.2670 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8259    1.6163   -2.7504 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8329    1.5852   -3.6926 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5374    1.2283   -3.3211 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4069    1.2094   -4.2739 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3173    0.9202   -2.0042 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9513    0.5492   -1.5148 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8671    0.5064   -2.3342 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1811    0.2448   -0.2035 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4435   -0.1208    0.2495 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5819   -0.1319   -0.6658 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.8592    1.1975   -1.1353 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7136   -0.6063   -1.7984 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1680    0.6207   -0.5235 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2836   -2.1748   -2.6587 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9191   -3.0875   -1.1924 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6171   -2.3307   -2.1152 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2690    0.4566    0.5661 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1004   -2.3719    0.8132 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5620   -1.7336    1.6850 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2411    0.1071    4.5836 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7442   -0.7261    4.1574 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2029   -1.6684    4.1945 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5660    0.0594    2.6487 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4748    2.0308   -0.7422 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1920    1.6961    0.5302 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6935   -0.4417   -1.0306 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0153   -2.6205    0.1895 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3599    2.0701    0.6302 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4299    0.6321    0.5946 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4011    0.9421   -0.8177 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7671    0.4543    2.3283 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4147    0.6567    3.0332 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6750    1.9300    1.9414 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9094   -1.0328    1.3652 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8555    1.8955   -3.0243 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0742    1.8430   -4.7286 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3455    1.0111   -4.3173 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5033   -0.8318   -1.4946 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4477    1.7931   -0.4331 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 16 20  1  0
 20 21  1  0
 20 22  1  0
 20 23  1  1
 14 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  1  0
 26 28  2  0
 28 29  1  0
 29 30  2  0
 29 31  1  0
 31 32  2  0
 32 33  1  0
 33 34  1  0
 33  4  1  0
 32  7  1  0
 31 11  1  0
 28 13  1  0
  1 35  1  0
  1 36  1  0
  3 37  1  0
  3 38  1  0
  3 39  1  0
  4 40  1  1
  5 41  1  0
  5 42  1  0
  9 43  1  0
  9 44  1  0
  9 45  1  0
 10 46  1  0
 15 47  1  0
 15 48  1  0
 16 49  1  6
 18 50  1  0
 21 51  1  0
 21 52  1  0
 21 53  1  0
 22 54  1  0
 22 55  1  0
 22 56  1  0
 23 57  1  0
 24 58  1  0
 25 59  1  0
 27 60  1  0
 33 61  1  6
 34 62  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Value	Source
(2S)-1-[(3S,4R)-4,6-Dihydroxy-12-methyl-5-oxo-3-(prop-1-en-2-yl)-2,3,4,5-tetrahydro-1,10-dioxatetraphen-9-yl]-3-hydroxy-3-methylbutan-2-yl formic acid	Generator
Vari-xanthone	MeSH

Chemical Formula

C₂₆H₂₈O₈

Average Mass

468.5020 Da

Monoisotopic Mass

468.17842 Da

IUPAC Name

(2S)-1-[(3S,4R)-4,6-dihydroxy-12-methyl-5-oxo-3-(prop-1-en-2-yl)-2,3,4,5-tetrahydro-1,10-dioxatetraphen-9-yl]-3-hydroxy-3-methylbutan-2-yl formate

Traditional Name

(2S)-1-[(3S,4R)-4,6-dihydroxy-12-methyl-5-oxo-3-(prop-1-en-2-yl)-3,4-dihydro-2H-1,10-dioxatetraphen-9-yl]-3-hydroxy-3-methylbutan-2-yl formate

CAS Registry Number

Not Available

SMILES

CC(=C)[C@H]1COC2=C([C@@H]1O)C1=C(OC3=C(C[C@H](OC=O)C(C)(C)O)C=CC(O)=C3C1=O)C=C2C

InChI Identifier

InChI=1S/C26H28O8/c1-12(2)15-10-32-24-13(3)8-17-20(21(24)22(15)29)23(30)19-16(28)7-6-14(25(19)34-17)9-18(33-11-27)26(4,5)31/h6-8,11,15,18,22,28-29,31H,1,9-10H2,2-5H3/t15-,18+,22-/m1/s1

InChI Key

GOKVXLNHAYUYGV-FXCLAUTBSA-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
Aspergillus stellatus	-	KNApSAcK
Emericella	NPAtlas	11908979

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 4-prenylated xanthones. These are organic compounds containing a C5-isoprenoid group linked to a xanthone moiety at the 4-position. Xanthone is a tricyclic compound made up of two benzene rings linearly fused to each other through a pyran ring that carries a ketone group.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzopyrans

Sub Class

1-benzopyrans

Direct Parent

4-prenylated xanthones

Alternative Parents

Substituents

4-prenylated xanthone
Pyranoxanthone
Chromone
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Phenol
Pyranone
Pyran
Benzenoid
Tertiary alcohol
Heteroaromatic compound
Vinylogous acid
Secondary alcohol
Carboxylic acid ester
Oxacycle
Monocarboxylic acid or derivatives
Ether
Carboxylic acid derivative
Alcohol
Hydrocarbon derivative
Organooxygen compound
Organic oxide
Carbonyl group
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	2.73	ALOGPS
logP	3.69	ChemAxon
logS	-4.1	ALOGPS
pKa (Strongest Acidic)	8.38	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	122.52 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	124.28 m³·mol⁻¹	ChemAxon
Polarizability	49.39 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

NPAtlas ID

NPA018794

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

8271705

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10096170

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Malmstrom J, Christophersen C, Barrero AF, Oltra JE, Justicia J, Rosales A: Bioactive metabolites from a marine-derived strain of the fungus Emericella variecolor. J Nat Prod. 2002 Mar;65(3):364-7. doi: 10.1021/np0103214. [PubMed:11908979 ]

Showing NP-Card for Varixanthone (NP0004090)

MOL for NP0004090 (Varixanthone)

3D MOL for NP0004090 (Varixanthone)

3D SDF for NP0004090 (Varixanthone)

3D-SDF for NP0004090 (Varixanthone)

PDB for NP0004090 (Varixanthone)

3D PDB for NP0004090 (Varixanthone)

SMILES for NP0004090 (Varixanthone)

INCHI for NP0004090 (Varixanthone)

Structure for NP0004090 (Varixanthone)

3D Structure for NP0004090 (Varixanthone)