NP-MRD: Showing NP-Card for (2r,2as,4as,6s,7br)-2a-hydroxy-3,6-bis(hydroxymethyl)-6,7b-dimethyl-1h,2h,4ah,5h,7h,7ah-cyclobuta[e]inden-2-yl 2,4-dihydroxy-6-methylbenzoate (NP0157356)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-02 14:43:06 UTC

Updated at

2022-09-02 14:43:06 UTC

NP-MRD ID

NP0157356

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2r,2as,4as,6s,7br)-2a-hydroxy-3,6-bis(hydroxymethyl)-6,7b-dimethyl-1h,2h,4ah,5h,7h,7ah-cyclobuta[e]inden-2-yl 2,4-dihydroxy-6-methylbenzoate

Description

14-Hydroxydihydromelleolide belongs to the class of organic compounds known as melleolides and analogues. Melleolides and analogues are compounds with a structure characterized by the presence of a 2-hydroxy-4-methoxy-6-methylbenzoic acid derivative linked to a 3,6,6,7b-tetramethyl-cyclobuta[e]indene moiety. (2r,2as,4as,6s,7br)-2a-hydroxy-3,6-bis(hydroxymethyl)-6,7b-dimethyl-1h,2h,4ah,5h,7h,7ah-cyclobuta[e]inden-2-yl 2,4-dihydroxy-6-methylbenzoate is found in Desarmillaria tabescens. Based on a literature review very few articles have been published on 14-Hydroxydihydromelleolide.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022216432D          

 30 33  0  0  1  0            999 V2000
   -1.1423   -1.8493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7036   -1.2447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5079   -1.4284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0691   -0.8238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8734   -1.0075    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8261   -0.0354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0218    0.1484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7788    0.9368    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4606   -0.4563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6563   -0.2725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4133    0.5159    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0950   -0.8772    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7092   -0.6934    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1480    0.0052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8467   -0.4336    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0897    0.3548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6711   -0.4642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2455    0.1279    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9862   -0.2354    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2702    0.5392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7863   -0.4368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3607    0.1553    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8695   -1.0521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0567   -1.1935    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6180   -1.8922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7935   -1.8615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3548   -2.5601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5303   -2.5295    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4079   -1.1322    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8032   -1.6935    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  2  0  0  0  0
  2  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
 13 12  1  6  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  1  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  6  0  0  0
 19 21  1  1  0  0  0
 21 22  1  0  0  0  0
 19 23  1  0  0  0  0
 24 23  1  1  0  0  0
 17 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 26 29  1  0  0  0  0
 13 29  1  0  0  0  0
 15 29  1  0  0  0  0
 29 30  1  1  0  0  0
M  END

     RDKit          3D

 60 63  0  0  0  0  0  0  0  0999 V2000
    4.8797   -2.8407    1.2574 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2369   -1.5126    0.7164 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5652   -1.0642    0.8069 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9562    0.1592    0.3213 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2628    0.6094    0.4070 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9938    0.9386   -0.2632 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6487    0.5024   -0.3638 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7629    1.3518   -0.9698 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2742   -0.7261    0.1292 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8896   -1.1827    0.0681 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5915   -2.3286    0.5334 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8282   -0.4745   -0.4606 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5596   -1.0362   -0.4643 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2199   -0.9043   -1.7497 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4315   -0.9332   -0.8614 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7968   -2.3750   -0.5540 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6205   -0.1856   -1.3079 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.6795   -0.2899   -0.2259 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5213    0.9601   -0.3648 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.8588    0.5128   -0.9451 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8151    1.6043    0.9720 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5145    0.6297    1.7205 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7998    1.8876   -1.3123 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4169    1.2716   -1.5593 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3950    1.8828   -0.6936 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5737    1.1824    0.0862 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3925    1.9831    0.8921 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2311    1.7819    2.2555 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5790   -0.2879    0.1898 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8831   -0.7625    1.4803 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5086   -3.4969    0.4496 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8166   -3.3277    1.6530 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1438   -2.8055    2.0812 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2958   -1.7136    1.2773 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6306    1.1442    1.1876 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2693    1.9077   -0.6558 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8242    1.3080   -1.1830 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5151   -2.0930   -0.0457 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0040    0.0624   -2.2365 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0664   -1.8041   -2.3762 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0300   -3.0940   -0.9090 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0715   -2.4809    0.4993 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7238   -2.6547   -1.1352 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0258   -0.6512   -2.2188 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2617   -1.2121   -0.2621 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2115   -0.2405    0.7923 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6826    1.1847   -0.6849 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0706   -0.4985   -0.5414 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7166    0.3820   -2.0459 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4498    2.4756    0.7982 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8515    1.8313    1.4827 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1386   -0.2737    1.5550 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6907    2.8604   -0.7894 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3819    1.9754   -2.2412 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1687    1.4810   -2.6123 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3467    2.9879   -0.7283 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2665    3.0449    0.6972 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4318    1.7108    0.6597 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2855    2.6116    2.7803 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0628   -0.9749    1.9886 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  4  6  2  0
  6  7  1  0
  7  8  1  0
  7  9  2  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  1
 15 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  6
 19 21  1  0
 21 22  1  0
 19 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  1  0
 26 29  1  0
 29 30  1  1
  9  2  1  0
 29 13  1  0
 29 15  1  0
 24 17  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
  3 34  1  0
  5 35  1  0
  6 36  1  0
  8 37  1  0
 13 38  1  1
 14 39  1  0
 14 40  1  0
 16 41  1  0
 16 42  1  0
 16 43  1  0
 17 44  1  6
 18 45  1  0
 18 46  1  0
 20 47  1  0
 20 48  1  0
 20 49  1  0
 21 50  1  0
 21 51  1  0
 22 52  1  0
 23 53  1  0
 23 54  1  0
 24 55  1  6
 25 56  1  0
 27 57  1  0
 27 58  1  0
 28 59  1  0
 30 60  1  0
M  END


  Mrv1652309022216432D          

 30 33  0  0  1  0            999 V2000
   -1.1423   -1.8493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7036   -1.2447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5079   -1.4284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0691   -0.8238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8734   -1.0075    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8261   -0.0354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0218    0.1484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7788    0.9368    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4606   -0.4563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6563   -0.2725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4133    0.5159    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0950   -0.8772    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7092   -0.6934    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1480    0.0052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8467   -0.4336    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0897    0.3548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6711   -0.4642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2455    0.1279    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9862   -0.2354    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2702    0.5392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7863   -0.4368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3607    0.1553    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8695   -1.0521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0567   -1.1935    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6180   -1.8922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7935   -1.8615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3548   -2.5601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5303   -2.5295    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4079   -1.1322    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8032   -1.6935    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  2  0  0  0  0
  2  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
 13 12  1  6  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  1  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  6  0  0  0
 19 21  1  1  0  0  0
 21 22  1  0  0  0  0
 19 23  1  0  0  0  0
 24 23  1  1  0  0  0
 17 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 26 29  1  0  0  0  0
 13 29  1  0  0  0  0
 15 29  1  0  0  0  0
 29 30  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0157356

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1=CC(O)=CC(O)=C1C(=O)O[C@@H]1C[C@]2(C)C3C[C@@](C)(CO)C[C@H]3C=C(CO)[C@]12O

> <INCHI_IDENTIFIER>
InChI=1S/C23H30O7/c1-12-4-15(26)6-17(27)19(12)20(28)30-18-9-22(3)16-8-21(2,11-25)7-13(16)5-14(10-24)23(18,22)29/h4-6,13,16,18,24-27,29H,7-11H2,1-3H3/t13-,16?,18-,21+,22-,23+/m1/s1

> <INCHI_KEY>
HDGURVCSOJDUHT-GJQGFOMNSA-N

> <FORMULA>
C23H30O7

> <MOLECULAR_WEIGHT>
418.486

> <EXACT_MASS>
418.199153306

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
60

> <JCHEM_AVERAGE_POLARIZABILITY>
44.27678792227961

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2R,2aS,4aS,6S,7bR)-2a-hydroxy-3,6-bis(hydroxymethyl)-6,7b-dimethyl-1H,2H,2aH,4aH,5H,6H,7H,7aH,7bH-cyclobuta[e]inden-2-yl 2,4-dihydroxy-6-methylbenzoate

> <ALOGPS_LOGP>
1.54

> <JCHEM_LOGP>
2.512910555666666

> <ALOGPS_LOGS>
-3.75

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.554231214184195

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.697521853596001

> <JCHEM_PKA_STRONGEST_BASIC>
-1.3868863713154456

> <JCHEM_POLAR_SURFACE_AREA>
127.45000000000002

> <JCHEM_REFRACTIVITY>
110.80439999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.44e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R,2aS,4aS,6S,7bR)-2a-hydroxy-3,6-bis(hydroxymethyl)-6,7b-dimethyl-1H,2H,4aH,5H,7H,7aH-cyclobuta[e]inden-2-yl 2,4-dihydroxy-6-methylbenzoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  C   UNK     0      -2.132  -3.452   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -3.180  -2.323   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -4.681  -2.666   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -5.729  -1.538   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -7.230  -1.881   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      -5.275  -0.066   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -3.774   0.277   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -3.321   1.749   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -2.726  -0.852   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.225  -0.509   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -0.771   0.963   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      -0.177  -1.637   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       1.324  -1.294   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.143   0.010   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.447  -0.809   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.901   0.662   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.986  -0.867   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.058   0.239   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       7.441  -0.439   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       7.971   1.006   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       8.934  -0.815   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      10.007   0.290   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       7.223  -1.964   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       5.706  -2.228   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       4.887  -3.532   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       3.348  -3.475   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       2.529  -4.779   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       0.990  -4.722   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       2.628  -2.113   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       1.499  -3.161   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    9                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7    2   10                                                  
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14   29                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   17   29                                             
CONECT   16   15                                                            
CONECT   17   15   18   24                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   21   23                                             
CONECT   20   19                                                            
CONECT   21   19   22                                                       
CONECT   22   21                                                            
CONECT   23   19   24                                                       
CONECT   24   23   17   25                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27   29                                                  
CONECT   27   26   28                                                       
CONECT   28   27                                                            
CONECT   29   26   13   15   30                                             
CONECT   30   29                                                            
MASTER        0    0    0    0    0    0    0    0   30    0   66    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₃H₃₀O₇

Average Mass

418.4860 Da

Monoisotopic Mass

418.19915 Da

IUPAC Name

(2R,2aS,4aS,6S,7bR)-2a-hydroxy-3,6-bis(hydroxymethyl)-6,7b-dimethyl-1H,2H,2aH,4aH,5H,6H,7H,7aH,7bH-cyclobuta[e]inden-2-yl 2,4-dihydroxy-6-methylbenzoate

Traditional Name

(2R,2aS,4aS,6S,7bR)-2a-hydroxy-3,6-bis(hydroxymethyl)-6,7b-dimethyl-1H,2H,4aH,5H,7H,7aH-cyclobuta[e]inden-2-yl 2,4-dihydroxy-6-methylbenzoate

CAS Registry Number

Not Available

SMILES

CC1=CC(O)=CC(O)=C1C(=O)O[C@@H]1C[C@]2(C)C3C[C@@](C)(CO)C[C@H]3C=C(CO)[C@]12O

InChI Identifier

InChI=1S/C23H30O7/c1-12-4-15(26)6-17(27)19(12)20(28)30-18-9-22(3)16-8-21(2,11-25)7-13(16)5-14(10-24)23(18,22)29/h4-6,13,16,18,24-27,29H,7-11H2,1-3H3/t13-,16?,18-,21+,22-,23+/m1/s1

InChI Key

HDGURVCSOJDUHT-GJQGFOMNSA-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
Desarmillaria tabescens	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as melleolides and analogues. Melleolides and analogues are compounds with a structure characterized by the presence of a 2-hydroxy-4-methoxy-6-methylbenzoic acid derivative linked to a 3,6,6,7b-tetramethyl-cyclobuta[e]indene moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Melleolides and analogues

Alternative Parents

Substituents

Melleolide-skeleton
P-hydroxybenzoic acid alkyl ester
P-hydroxybenzoic acid ester
O-hydroxybenzoic acid ester
Dihydroxybenzoic acid
Salicylic acid or derivatives
Benzoate ester
Benzoic acid or derivatives
M-cresol
Resorcinol
Benzoyl
Phenol
1-hydroxy-2-unsubstituted benzenoid
Toluene
1-hydroxy-4-unsubstituted benzenoid
Benzenoid
Monocyclic benzene moiety
Vinylogous acid
Tertiary alcohol
Cyclobutanol
Carboxylic acid ester
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Alcohol
Organooxygen compound
Primary alcohol
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
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	1.54	ALOGPS
logP	2.51	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	8.7	ChemAxon
pKa (Strongest Basic)	-1.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	127.45 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	110.8 m³·mol⁻¹	ChemAxon
Polarizability	44.28 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

78437154

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

102068113

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2r,2as,4as,6s,7br)-2a-hydroxy-3,6-bis(hydroxymethyl)-6,7b-dimethyl-1h,2h,4ah,5h,7h,7ah-cyclobuta[e]inden-2-yl 2,4-dihydroxy-6-methylbenzoate (NP0157356)

MOL for NP0157356 ((2r,2as,4as,6s,7br)-2a-hydroxy-3,6-bis(hydroxymethyl)-6,7b-dimethyl-1h,2h,4ah,5h,7h,7ah-cyclobuta[e]inden-2-yl 2,4-dihydroxy-6-methylbenzoate)

3D MOL for NP0157356 ((2r,2as,4as,6s,7br)-2a-hydroxy-3,6-bis(hydroxymethyl)-6,7b-dimethyl-1h,2h,4ah,5h,7h,7ah-cyclobuta[e]inden-2-yl 2,4-dihydroxy-6-methylbenzoate)

3D SDF for NP0157356 ((2r,2as,4as,6s,7br)-2a-hydroxy-3,6-bis(hydroxymethyl)-6,7b-dimethyl-1h,2h,4ah,5h,7h,7ah-cyclobuta[e]inden-2-yl 2,4-dihydroxy-6-methylbenzoate)

3D-SDF for NP0157356 ((2r,2as,4as,6s,7br)-2a-hydroxy-3,6-bis(hydroxymethyl)-6,7b-dimethyl-1h,2h,4ah,5h,7h,7ah-cyclobuta[e]inden-2-yl 2,4-dihydroxy-6-methylbenzoate)

PDB for NP0157356 ((2r,2as,4as,6s,7br)-2a-hydroxy-3,6-bis(hydroxymethyl)-6,7b-dimethyl-1h,2h,4ah,5h,7h,7ah-cyclobuta[e]inden-2-yl 2,4-dihydroxy-6-methylbenzoate)

3D PDB for NP0157356 ((2r,2as,4as,6s,7br)-2a-hydroxy-3,6-bis(hydroxymethyl)-6,7b-dimethyl-1h,2h,4ah,5h,7h,7ah-cyclobuta[e]inden-2-yl 2,4-dihydroxy-6-methylbenzoate)

SMILES for NP0157356 ((2r,2as,4as,6s,7br)-2a-hydroxy-3,6-bis(hydroxymethyl)-6,7b-dimethyl-1h,2h,4ah,5h,7h,7ah-cyclobuta[e]inden-2-yl 2,4-dihydroxy-6-methylbenzoate)

INCHI for NP0157356 ((2r,2as,4as,6s,7br)-2a-hydroxy-3,6-bis(hydroxymethyl)-6,7b-dimethyl-1h,2h,4ah,5h,7h,7ah-cyclobuta[e]inden-2-yl 2,4-dihydroxy-6-methylbenzoate)

Structure for NP0157356 ((2r,2as,4as,6s,7br)-2a-hydroxy-3,6-bis(hydroxymethyl)-6,7b-dimethyl-1h,2h,4ah,5h,7h,7ah-cyclobuta[e]inden-2-yl 2,4-dihydroxy-6-methylbenzoate)

3D Structure for NP0157356 ((2r,2as,4as,6s,7br)-2a-hydroxy-3,6-bis(hydroxymethyl)-6,7b-dimethyl-1h,2h,4ah,5h,7h,7ah-cyclobuta[e]inden-2-yl 2,4-dihydroxy-6-methylbenzoate)