NP-MRD: Showing NP-Card for [4R-[4alpha(E),5aalpha,6alpha,9abeta,9balpha]]-2,4,5,5a,6,7,8,9,9a,9b-Decahydro-6-hydroxy-3-(hydroxymethyl)-5a-methyl-9-methylene-2-oxonaphtho[1,2-b]furan-4-yl ester 2-methyl-2-butenoic acid (NP0059542)

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Record Information

Version

2.0

Created at

2022-04-28 04:45:47 UTC

Updated at

2022-04-28 04:45:48 UTC

NP-MRD ID

NP0059542

Secondary Accession Numbers

None

Natural Product Identification

Common Name

[4R-[4alpha(E),5aalpha,6alpha,9abeta,9balpha]]-2,4,5,5a,6,7,8,9,9a,9b-Decahydro-6-hydroxy-3-(hydroxymethyl)-5a-methyl-9-methylene-2-oxonaphtho[1,2-b]furan-4-yl ester 2-methyl-2-butenoic acid

Description

Trichomatolide A belongs to the class of organic compounds known as naphthofurans. Naphthofurans are compounds containing a furan ring fused to a naphthalene moiety. Furan is a 5 membered- ring aromatic ring with four carbon and one oxygen atoms. Naphthalene is a polycyclic aromatic hydrocarbon made up of two fused benzene rings. [4R-[4alpha(E),5aalpha,6alpha,9abeta,9balpha]]-2,4,5,5a,6,7,8,9,9a,9b-Decahydro-6-hydroxy-3-(hydroxymethyl)-5a-methyl-9-methylene-2-oxonaphtho[1,2-b]furan-4-yl ester 2-methyl-2-butenoic acid is found in Calea trichomata. Based on a literature review very few articles have been published on Trichomatolide A.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282206452D          

 26 28  0  0  1  0            999 V2000
    5.1704    0.3867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7804    1.1137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9558    1.1395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5658    1.8665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5212    0.4383    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9112   -0.2887    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.7358   -0.3145    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.1258   -1.0415    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4766   -0.9900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6520   -0.9642    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2620   -0.2372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4608   -0.0406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4002    0.7822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6989    1.2168    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1640    1.0941    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6966    0.4640    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8307   -0.5732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0544   -0.2939    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2174   -1.6655    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6073   -2.3925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4319   -2.4182    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1727   -3.0937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3481   -3.0679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9135   -3.7692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5627   -3.8207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3012   -1.0157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  5  3  1  1  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  1  7  1  0  0  0  0
  7  8  1  1  0  0  0
  6  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 16 15  1  6  0  0  0
  5 16  1  0  0  0  0
 11 16  1  0  0  0  0
 12 17  1  0  0  0  0
 17 18  1  0  0  0  0
 10 19  1  1  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 22 25  1  0  0  0  0
  6 26  1  1  0  0  0
M  END

     RDKit          3D

 52 54  0  0  0  0  0  0  0  0999 V2000
   -3.1483    2.0736   -1.5242 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2010    0.8934   -0.9210 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3455   -0.0296   -1.1540 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9392   -1.4573   -1.3051 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8046   -1.8740   -0.4007 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4250   -3.1558   -0.7702 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6323   -0.8984   -0.5046 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4005   -0.7218   -2.0122 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4642   -1.4868    0.1704 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4894   -0.5584    0.8674 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6221   -0.2606    0.0772 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9043   -0.5588    0.4986 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0816   -1.1102    1.6140 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0594   -0.2284   -0.3626 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8659    0.4211   -1.6787 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2913   -0.5062    0.0243 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4713   -0.1842   -0.8235 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1475    0.7241    1.2352 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0934    1.4966    2.2821 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7109    1.3012    3.5424 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1257    1.2293    4.6560 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9524    2.6626    2.1089 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1355    3.6021    2.9096 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5491    2.5538    0.8749 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0526    1.4062    0.2569 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1425    0.4205    0.0105 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3149    2.7411   -1.3520 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9210    2.3912   -2.1893 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8557    0.2970   -2.0865 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1089    0.0989   -0.3337 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8161   -2.0882   -1.0200 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7058   -1.7340   -2.3625 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1706   -1.8130    0.6433 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1460   -3.6313    0.0548 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2135   -0.1019   -2.3854 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4934   -1.7307   -2.4673 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3923   -0.3151   -2.2113 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7842   -2.2895    0.8977 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1332   -2.0444   -0.5968 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8626   -1.0340    1.7958 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2381   -0.2645   -2.4616 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8158    0.7317   -1.8427 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4884    1.3411   -1.6965 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4282   -0.9892    1.0041 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3928   -0.2916   -0.1921 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5506   -0.9853   -1.5999 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4156    0.8201   -1.2700 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4290    2.1401    3.6760 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2901    0.3755    3.4851 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9442    0.7333    4.4981 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4974    1.6844   -0.6659 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6174    0.2039    1.0070 H   0  0  0  0  0  0  0  0  0  0  0  0
 17 16  1  0
 16 14  2  0
 14 15  1  0
 14 12  1  0
 12 13  2  0
 12 11  1  0
 11 10  1  0
 10  9  1  0
  9  7  1  0
  7  8  1  6
  7  5  1  0
  5  6  1  0
  5  4  1  0
  4  3  1  0
  3  2  1  0
  2  1  2  3
  2 26  1  0
 26 25  1  0
 25 24  1  0
 24 22  1  0
 22 23  2  0
 22 19  1  0
 19 20  1  0
 20 21  1  0
 19 18  2  0
 18 10  1  0
 26  7  1  0
 18 25  1  0
 17 45  1  0
 17 46  1  0
 17 47  1  0
 16 44  1  0
 15 41  1  0
 15 42  1  0
 15 43  1  0
 10 40  1  1
  9 38  1  0
  9 39  1  0
  8 35  1  0
  8 36  1  0
  8 37  1  0
  5 33  1  1
  6 34  1  0
  4 31  1  0
  4 32  1  0
  3 29  1  0
  3 30  1  0
  1 27  1  0
  1 28  1  0
 26 52  1  1
 25 51  1  6
 20 48  1  0
 20 49  1  0
 21 50  1  0
M  END


  Mrv1652304282206452D          

 26 28  0  0  1  0            999 V2000
    5.1704    0.3867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7804    1.1137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9558    1.1395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5658    1.8665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5212    0.4383    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9112   -0.2887    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.7358   -0.3145    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.1258   -1.0415    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4766   -0.9900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6520   -0.9642    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2620   -0.2372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4608   -0.0406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4002    0.7822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6989    1.2168    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1640    1.0941    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6966    0.4640    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8307   -0.5732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0544   -0.2939    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2174   -1.6655    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6073   -2.3925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4319   -2.4182    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1727   -3.0937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3481   -3.0679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9135   -3.7692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5627   -3.8207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3012   -1.0157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  5  3  1  1  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  1  7  1  0  0  0  0
  7  8  1  1  0  0  0
  6  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 16 15  1  6  0  0  0
  5 16  1  0  0  0  0
 11 16  1  0  0  0  0
 12 17  1  0  0  0  0
 17 18  1  0  0  0  0
 10 19  1  1  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 22 25  1  0  0  0  0
  6 26  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0059542

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C\C=C(/C)C(=O)O[C@@H]1C[C@@]2(C)[C@H](O)CCC(=C)[C@@H]2[C@H]2OC(=O)C(CO)=C12

> <INCHI_IDENTIFIER>
InChI=1S/C20H26O6/c1-5-10(2)18(23)25-13-8-20(4)14(22)7-6-11(3)16(20)17-15(13)12(9-21)19(24)26-17/h5,13-14,16-17,21-22H,3,6-9H2,1-2,4H3/b10-5+/t13-,14-,16-,17+,20+/m1/s1

> <INCHI_KEY>
DWQGFLLRGZHSCV-BMVFIXOLSA-N

> <FORMULA>
C20H26O6

> <MOLECULAR_WEIGHT>
362.422

> <EXACT_MASS>
362.172938557

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
52

> <JCHEM_AVERAGE_POLARIZABILITY>
38.36838018019116

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(4R,5aR,6R,9aS,9bR)-6-hydroxy-3-(hydroxymethyl)-5a-methyl-9-methylidene-2-oxo-2H,4H,5H,5aH,6H,7H,8H,9H,9aH,9bH-naphtho[1,2-b]furan-4-yl (2E)-2-methylbut-2-enoate

> <ALOGPS_LOGP>
1.90

> <JCHEM_LOGP>
1.8828352309999996

> <ALOGPS_LOGS>
-2.70

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.522409807025632

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.147194816706152

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8646041316435173

> <JCHEM_POLAR_SURFACE_AREA>
93.06

> <JCHEM_REFRACTIVITY>
95.48479999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.17e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(4R,5aR,6R,9aS,9bR)-6-hydroxy-3-(hydroxymethyl)-5a-methyl-9-methylidene-2-oxo-4H,5H,6H,7H,8H,9aH,9bH-naphtho[1,2-b]furan-4-yl (2E)-2-methylbut-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0       9.651   0.722   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.923   2.079   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.384   2.127   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.656   3.484   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.573   0.818   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.301  -0.539   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.840  -0.587   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       9.568  -1.944   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       6.490  -1.848   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.950  -1.800   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.222  -0.443   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.727  -0.076   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.614   1.460   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       1.305   2.271   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       4.039   2.042   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       5.034   0.866   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.551  -1.070   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       0.102  -0.549   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       4.139  -3.109   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       4.867  -4.466   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       6.406  -4.514   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       4.056  -5.775   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.517  -5.727   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       1.705  -7.036   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       4.784  -7.132   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       8.029  -1.896   0.000  0.00  0.00           C+0
CONECT    1    2    7                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   16                                                  
CONECT    6    5    7    9   26                                             
CONECT    7    6    1    8                                                  
CONECT    8    7                                                            
CONECT    9    6   10                                                       
CONECT   10    9   11   19                                                  
CONECT   11   10   12   16                                                  
CONECT   12   11   13   17                                                  
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15    5   11                                                  
CONECT   17   12   18                                                       
CONECT   18   17                                                            
CONECT   19   10   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23   25                                                  
CONECT   23   22   24                                                       
CONECT   24   23                                                            
CONECT   25   22                                                            
CONECT   26    6                                                            
MASTER        0    0    0    0    0    0    0    0   26    0   56    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₂₆O₆

Average Mass

362.4220 Da

Monoisotopic Mass

362.17294 Da

IUPAC Name

(4R,5aR,6R,9aS,9bR)-6-hydroxy-3-(hydroxymethyl)-5a-methyl-9-methylidene-2-oxo-2H,4H,5H,5aH,6H,7H,8H,9H,9aH,9bH-naphtho[1,2-b]furan-4-yl (2E)-2-methylbut-2-enoate

Traditional Name

(4R,5aR,6R,9aS,9bR)-6-hydroxy-3-(hydroxymethyl)-5a-methyl-9-methylidene-2-oxo-4H,5H,6H,7H,8H,9aH,9bH-naphtho[1,2-b]furan-4-yl (2E)-2-methylbut-2-enoate

CAS Registry Number

Not Available

SMILES

C\C=C(/C)C(=O)O[C@@H]1C[C@@]2(C)[C@H](O)CCC(=C)[C@@H]2[C@H]2OC(=O)C(CO)=C12

InChI Identifier

InChI=1S/C20H26O6/c1-5-10(2)18(23)25-13-8-20(4)14(22)7-6-11(3)16(20)17-15(13)12(9-21)19(24)26-17/h5,13-14,16-17,21-22H,3,6-9H2,1-2,4H3/b10-5+/t13-,14-,16-,17+,20+/m1/s1

InChI Key

DWQGFLLRGZHSCV-BMVFIXOLSA-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
Calea trichomata	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as naphthofurans. Naphthofurans are compounds containing a furan ring fused to a naphthalene moiety. Furan is a 5 membered- ring aromatic ring with four carbon and one oxygen atoms. Naphthalene is a polycyclic aromatic hydrocarbon made up of two fused benzene rings.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Naphthofurans

Sub Class

Not Available

Direct Parent

Naphthofurans

Alternative Parents

Substituents

Naphthofuran
Fatty acid ester
2-furanone
Dicarboxylic acid or derivatives
Fatty acyl
Cyclic alcohol
Dihydrofuran
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Lactone
Carboxylic acid ester
Secondary alcohol
Oxacycle
Carboxylic acid derivative
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Alcohol
Primary alcohol
Organic oxygen compound
Carbonyl group
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic 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	1.9	ALOGPS
logP	1.88	ChemAxon
logS	-2.7	ALOGPS
pKa (Strongest Acidic)	12.15	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	93.06 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	95.48 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

C00013090

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

101288309

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for [4R-[4alpha(E),5aalpha,6alpha,9abeta,9balpha]]-2,4,5,5a,6,7,8,9,9a,9b-Decahydro-6-hydroxy-3-(hydroxymethyl)-5a-methyl-9-methylene-2-oxonaphtho[1,2-b]furan-4-yl ester 2-methyl-2-butenoic acid (NP0059542)

MOL for NP0059542 ([4R-[4alpha(E),5aalpha,6alpha,9abeta,9balpha]]-2,4,5,5a,6,7,8,9,9a,9b-Decahydro-6-hydroxy-3-(hydroxymethyl)-5a-methyl-9-methylene-2-oxonaphtho[1,2-b]furan-4-yl ester 2-methyl-2-butenoic acid)

3D MOL for NP0059542 ([4R-[4alpha(E),5aalpha,6alpha,9abeta,9balpha]]-2,4,5,5a,6,7,8,9,9a,9b-Decahydro-6-hydroxy-3-(hydroxymethyl)-5a-methyl-9-methylene-2-oxonaphtho[1,2-b]furan-4-yl ester 2-methyl-2-butenoic acid)

3D SDF for NP0059542 ([4R-[4alpha(E),5aalpha,6alpha,9abeta,9balpha]]-2,4,5,5a,6,7,8,9,9a,9b-Decahydro-6-hydroxy-3-(hydroxymethyl)-5a-methyl-9-methylene-2-oxonaphtho[1,2-b]furan-4-yl ester 2-methyl-2-butenoic acid)

3D-SDF for NP0059542 ([4R-[4alpha(E),5aalpha,6alpha,9abeta,9balpha]]-2,4,5,5a,6,7,8,9,9a,9b-Decahydro-6-hydroxy-3-(hydroxymethyl)-5a-methyl-9-methylene-2-oxonaphtho[1,2-b]furan-4-yl ester 2-methyl-2-butenoic acid)

PDB for NP0059542 ([4R-[4alpha(E),5aalpha,6alpha,9abeta,9balpha]]-2,4,5,5a,6,7,8,9,9a,9b-Decahydro-6-hydroxy-3-(hydroxymethyl)-5a-methyl-9-methylene-2-oxonaphtho[1,2-b]furan-4-yl ester 2-methyl-2-butenoic acid)

3D PDB for NP0059542 ([4R-[4alpha(E),5aalpha,6alpha,9abeta,9balpha]]-2,4,5,5a,6,7,8,9,9a,9b-Decahydro-6-hydroxy-3-(hydroxymethyl)-5a-methyl-9-methylene-2-oxonaphtho[1,2-b]furan-4-yl ester 2-methyl-2-butenoic acid)

SMILES for NP0059542 ([4R-[4alpha(E),5aalpha,6alpha,9abeta,9balpha]]-2,4,5,5a,6,7,8,9,9a,9b-Decahydro-6-hydroxy-3-(hydroxymethyl)-5a-methyl-9-methylene-2-oxonaphtho[1,2-b]furan-4-yl ester 2-methyl-2-butenoic acid)

INCHI for NP0059542 ([4R-[4alpha(E),5aalpha,6alpha,9abeta,9balpha]]-2,4,5,5a,6,7,8,9,9a,9b-Decahydro-6-hydroxy-3-(hydroxymethyl)-5a-methyl-9-methylene-2-oxonaphtho[1,2-b]furan-4-yl ester 2-methyl-2-butenoic acid)

Structure for NP0059542 ([4R-[4alpha(E),5aalpha,6alpha,9abeta,9balpha]]-2,4,5,5a,6,7,8,9,9a,9b-Decahydro-6-hydroxy-3-(hydroxymethyl)-5a-methyl-9-methylene-2-oxonaphtho[1,2-b]furan-4-yl ester 2-methyl-2-butenoic acid)

3D Structure for NP0059542 ([4R-[4alpha(E),5aalpha,6alpha,9abeta,9balpha]]-2,4,5,5a,6,7,8,9,9a,9b-Decahydro-6-hydroxy-3-(hydroxymethyl)-5a-methyl-9-methylene-2-oxonaphtho[1,2-b]furan-4-yl ester 2-methyl-2-butenoic acid)