NP-MRD: Showing NP-Card for [4S-(4alpha,4aalpha,5alpha,8abeta)]-4,4a,5,6,7,8,8a,9-Octahydro-3,4a,5-trimethyl-9-oxonaphtho[2,3-b]furan-4-yl ester 3-methyl-2-butenoic acid (NP0061787)

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Record Information

Version

2.0

Created at

2022-04-28 06:30:27 UTC

Updated at

2022-04-28 06:30:28 UTC

NP-MRD ID

NP0061787

Secondary Accession Numbers

None

Natural Product Identification

Common Name

[4S-(4alpha,4aalpha,5alpha,8abeta)]-4,4a,5,6,7,8,8a,9-Octahydro-3,4a,5-trimethyl-9-oxonaphtho[2,3-b]furan-4-yl ester 3-methyl-2-butenoic acid

Description

(4S,4aR,5S,8aR)-3,4a,5-trimethyl-9-oxo-4H,4aH,5H,6H,7H,8H,8aH,9H-naphtho[2,3-b]furan-4-yl 3-methylbut-2-enoate belongs to the class of organic compounds known as eremophilane, 8,9-secoeremophilane and furoeremophilane sesquiterpenoids. These are sesquiterpenoids with a structure based either on the eremophilane skeleton, its 8,9-seco derivative, or the furoeremophilane skeleton. Eremophilanes have been shown to be derived from eudesmanes by migration of the methyl group at C-10 to C-5. [4S-(4alpha,4aalpha,5alpha,8abeta)]-4,4a,5,6,7,8,8a,9-Octahydro-3,4a,5-trimethyl-9-oxonaphtho[2,3-b]furan-4-yl ester 3-methyl-2-butenoic acid is found in Pittocaulon praecox, Senecio praecox, Senecio rosmarinifolius and Senecio superandinus. Based on a literature review very few articles have been published on (4S,4aR,5S,8aR)-3,4a,5-trimethyl-9-oxo-4H,4aH,5H,6H,7H,8H,8aH,9H-naphtho[2,3-b]furan-4-yl 3-methylbut-2-enoate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282208302D          

 24 26  0  0  1  0            999 V2000
    4.7812    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    2.3479    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3523    1.9354    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3523    1.1104    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0668    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -0.1271    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    2.3479    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6378    3.1729    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    3.5854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2089    3.1729    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    4.4104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2089    4.8229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4944    4.4104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2089    5.6479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    2.1904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    0.8555    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8838    2.9750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    2.7604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    3.1729    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  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  1  0  0  0
  1  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
  4 11  1  0  0  0  0
 11 12  1  1  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 10 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
  9 21  1  0  0  0  0
 19 22  1  0  0  0  0
  4 23  1  1  0  0  0
  3 24  1  1  0  0  0
M  END

     RDKit          3D

 50 52  0  0  0  0  0  0  0  0999 V2000
    4.3419   -0.0277   -1.8511 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2944   -0.5434   -0.4606 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5155   -1.1342    0.1354 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1522   -0.4511    0.1901 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9323    0.1209   -0.3576 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8145    0.5954   -1.5110 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7674    0.1829    0.3906 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3920    0.7228   -0.1202 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7922    1.9956    0.5609 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0296    3.0436    1.0203 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4505    3.2317    0.9765 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9516    3.9318    1.5569 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1618    3.4420    1.4224 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1180    2.2646    0.8217 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1845    1.3284    0.4476 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3428    1.3612    0.9134 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7759    0.3105   -0.5532 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.8183   -0.6193   -0.9633 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7779   -1.9812   -0.3288 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4104   -2.5352   -0.1899 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2926   -1.6031   -0.6209 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0074   -2.3135   -0.3069 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4934   -0.2900    0.0087 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7471   -0.4343    1.5197 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5803   -0.5973   -2.4469 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0654    1.0458   -1.8913 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3561   -0.1381   -2.2928 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3992   -0.5113   -0.1001 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4557   -1.2080    1.2308 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7222   -2.1618   -0.2500 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1319   -0.8276    1.1942 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3060    1.0292   -1.2021 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7645    4.1803    1.4053 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7735    3.0627   -0.0692 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8745    2.3974    1.6039 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6863    4.8901    2.0175 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4132    0.9218   -1.4374 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8610   -0.2285   -0.7715 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7744   -0.7772   -2.0677 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3367   -1.9760    0.6536 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3710   -2.6610   -0.9805 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2305   -2.8733    0.8497 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2607   -3.4673   -0.8130 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3677   -1.5099   -1.7234 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4341   -2.0846    0.6634 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2526   -3.4250   -0.2589 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6946   -2.2684   -1.1754 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2897   -1.4013    1.8804 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8268   -0.3756    1.7615 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2487    0.3667    2.1021 H   0  0  0  0  0  0  0  0  0  0  0  0
 22 21  1  0
 21 20  1  0
 20 19  1  0
 19 18  1  0
 18 17  1  0
 17 15  1  0
 15 16  2  0
 15 14  1  0
 14  9  2  0
  9  8  1  0
  8  7  1  0
  7  5  1  0
  5  6  2  0
  5  4  1  0
  4  2  2  3
  2  1  1  0
  2  3  1  0
  8 23  1  0
 23 24  1  1
  9 10  1  0
 10 11  1  0
 10 12  2  0
 12 13  1  0
 23 21  1  0
 23 17  1  0
 13 14  1  0
 22 45  1  0
 22 46  1  0
 22 47  1  0
 21 44  1  6
 20 42  1  0
 20 43  1  0
 19 40  1  0
 19 41  1  0
 18 38  1  0
 18 39  1  0
 17 37  1  6
  8 32  1  6
  4 31  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  3 28  1  0
  3 29  1  0
  3 30  1  0
 24 48  1  0
 24 49  1  0
 24 50  1  0
 11 33  1  0
 11 34  1  0
 11 35  1  0
 12 36  1  0
M  END


  Mrv1652304282208302D          

 24 26  0  0  1  0            999 V2000
    4.7812    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    2.3479    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3523    1.9354    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3523    1.1104    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0668    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -0.1271    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    2.3479    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6378    3.1729    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    3.5854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2089    3.1729    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    4.4104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2089    4.8229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4944    4.4104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2089    5.6479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    2.1904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    0.8555    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8838    2.9750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    2.7604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    3.1729    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  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  1  0  0  0
  1  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
  4 11  1  0  0  0  0
 11 12  1  1  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 10 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
  9 21  1  0  0  0  0
 19 22  1  0  0  0  0
  4 23  1  1  0  0  0
  3 24  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0061787

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H]1CCC[C@H]2C(=O)C3=C([C@@H](OC(=O)C=C(C)C)[C@]12C)C(C)=CO3

> <INCHI_IDENTIFIER>
InChI=1S/C20H26O4/c1-11(2)9-15(21)24-19-16-12(3)10-23-18(16)17(22)14-8-6-7-13(4)20(14,19)5/h9-10,13-14,19H,6-8H2,1-5H3/t13-,14-,19+,20+/m0/s1

> <INCHI_KEY>
OKMDXLNHYGVDON-AFHBHXEDSA-N

> <FORMULA>
C20H26O4

> <MOLECULAR_WEIGHT>
330.424

> <EXACT_MASS>
330.183109317

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
50

> <JCHEM_AVERAGE_POLARIZABILITY>
36.58869226895267

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(4S,4aR,5S,8aR)-3,4a,5-trimethyl-9-oxo-4H,4aH,5H,6H,7H,8H,8aH,9H-naphtho[2,3-b]furan-4-yl 3-methylbut-2-enoate

> <ALOGPS_LOGP>
4.18

> <JCHEM_LOGP>
4.683120129999999

> <ALOGPS_LOGS>
-4.31

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.641392243634506

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9468329749951265

> <JCHEM_POLAR_SURFACE_AREA>
56.510000000000005

> <JCHEM_REFRACTIVITY>
92.4216

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.62e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(4S,4aR,5S,8aR)-3,4a,5-trimethyl-9-oxo-4H,5H,6H,7H,8H,8aH-naphtho[2,3-b]furan-4-yl 3-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       8.925   2.073   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.925   3.613   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.591   4.383   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.258   3.613   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.258   2.073   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.591   1.303   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.924   1.303   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       4.924  -0.237   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       3.590   2.073   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.590   3.613   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.924   4.383   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       4.924   5.923   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       3.590   6.693   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       2.257   5.923   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       3.590   8.233   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.257   9.003   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.923   8.233   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.257  10.543   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.126   4.089   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.220   2.843   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       2.126   1.597   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       1.650   5.553   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       6.258   5.153   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       7.591   5.923   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4   24                                                  
CONECT    4    3    5   11   23                                             
CONECT    5    4    6    7                                                  
CONECT    6    5    1                                                       
CONECT    7    5    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   21                                                  
CONECT   10    9   11   19                                                  
CONECT   11   10    4   12                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16                                                            
CONECT   19   10   20   22                                                  
CONECT   20   19   21                                                       
CONECT   21   20    9                                                       
CONECT   22   19                                                            
CONECT   23    4                                                            
CONECT   24    3                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   52    0
END

View in JSmol

Synonyms

Value	Source
(4S,4AR,5S,8ar)-3,4a,5-trimethyl-9-oxo-4H,4ah,5H,6H,7H,8H,8ah,9H-naphtho[2,3-b]furan-4-yl 3-methylbut-2-enoic acid	Generator

Chemical Formula

C₂₀H₂₆O₄

Average Mass

330.4240 Da

Monoisotopic Mass

330.18311 Da

IUPAC Name

(4S,4aR,5S,8aR)-3,4a,5-trimethyl-9-oxo-4H,4aH,5H,6H,7H,8H,8aH,9H-naphtho[2,3-b]furan-4-yl 3-methylbut-2-enoate

Traditional Name

(4S,4aR,5S,8aR)-3,4a,5-trimethyl-9-oxo-4H,5H,6H,7H,8H,8aH-naphtho[2,3-b]furan-4-yl 3-methylbut-2-enoate

CAS Registry Number

Not Available

SMILES

C[C@H]1CCC[C@H]2C(=O)C3=C([C@@H](OC(=O)C=C(C)C)[C@]12C)C(C)=CO3

InChI Identifier

InChI=1S/C20H26O4/c1-11(2)9-15(21)24-19-16-12(3)10-23-18(16)17(22)14-8-6-7-13(4)20(14,19)5/h9-10,13-14,19H,6-8H2,1-5H3/t13-,14-,19+,20+/m0/s1

InChI Key

OKMDXLNHYGVDON-AFHBHXEDSA-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
Pittocaulon praecox	LOTUS Database	35616633
Senecio praecox	Plant	KNApSAcK
Senecio rosmarinifolius	LOTUS Database	35616633
Senecio superandinus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as eremophilane, 8,9-secoeremophilane and furoeremophilane sesquiterpenoids. These are sesquiterpenoids with a structure based either on the eremophilane skeleton, its 8,9-seco derivative, or the furoeremophilane skeleton. Eremophilanes have been shown to be derived from eudesmanes by migration of the methyl group at C-10 to C-5.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Eremophilane, 8,9-secoeremophilane and furoeremophilane sesquiterpenoids

Alternative Parents

Substituents

Furoeremophilane sesquiterpenoid
Naphthofuran
Benzofuran
Aryl ketone
Aryl alkyl ketone
Fatty acid ester
Fatty acyl
Furan
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Heteroaromatic compound
Ketone
Carboxylic acid ester
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Oxacycle
Organoheterocyclic compound
Organic oxygen compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Carbonyl group
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	4.18	ALOGPS
logP	4.68	ChemAxon
logS	-4.3	ALOGPS
pKa (Strongest Acidic)	14.64	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	56.51 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	92.42 m³·mol⁻¹	ChemAxon
Polarizability	36.59 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

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

14190083

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for [4S-(4alpha,4aalpha,5alpha,8abeta)]-4,4a,5,6,7,8,8a,9-Octahydro-3,4a,5-trimethyl-9-oxonaphtho[2,3-b]furan-4-yl ester 3-methyl-2-butenoic acid (NP0061787)

MOL for NP0061787 ([4S-(4alpha,4aalpha,5alpha,8abeta)]-4,4a,5,6,7,8,8a,9-Octahydro-3,4a,5-trimethyl-9-oxonaphtho[2,3-b]furan-4-yl ester 3-methyl-2-butenoic acid)

3D MOL for NP0061787 ([4S-(4alpha,4aalpha,5alpha,8abeta)]-4,4a,5,6,7,8,8a,9-Octahydro-3,4a,5-trimethyl-9-oxonaphtho[2,3-b]furan-4-yl ester 3-methyl-2-butenoic acid)

3D SDF for NP0061787 ([4S-(4alpha,4aalpha,5alpha,8abeta)]-4,4a,5,6,7,8,8a,9-Octahydro-3,4a,5-trimethyl-9-oxonaphtho[2,3-b]furan-4-yl ester 3-methyl-2-butenoic acid)

3D-SDF for NP0061787 ([4S-(4alpha,4aalpha,5alpha,8abeta)]-4,4a,5,6,7,8,8a,9-Octahydro-3,4a,5-trimethyl-9-oxonaphtho[2,3-b]furan-4-yl ester 3-methyl-2-butenoic acid)

PDB for NP0061787 ([4S-(4alpha,4aalpha,5alpha,8abeta)]-4,4a,5,6,7,8,8a,9-Octahydro-3,4a,5-trimethyl-9-oxonaphtho[2,3-b]furan-4-yl ester 3-methyl-2-butenoic acid)

3D PDB for NP0061787 ([4S-(4alpha,4aalpha,5alpha,8abeta)]-4,4a,5,6,7,8,8a,9-Octahydro-3,4a,5-trimethyl-9-oxonaphtho[2,3-b]furan-4-yl ester 3-methyl-2-butenoic acid)

SMILES for NP0061787 ([4S-(4alpha,4aalpha,5alpha,8abeta)]-4,4a,5,6,7,8,8a,9-Octahydro-3,4a,5-trimethyl-9-oxonaphtho[2,3-b]furan-4-yl ester 3-methyl-2-butenoic acid)

INCHI for NP0061787 ([4S-(4alpha,4aalpha,5alpha,8abeta)]-4,4a,5,6,7,8,8a,9-Octahydro-3,4a,5-trimethyl-9-oxonaphtho[2,3-b]furan-4-yl ester 3-methyl-2-butenoic acid)

Structure for NP0061787 ([4S-(4alpha,4aalpha,5alpha,8abeta)]-4,4a,5,6,7,8,8a,9-Octahydro-3,4a,5-trimethyl-9-oxonaphtho[2,3-b]furan-4-yl ester 3-methyl-2-butenoic acid)

3D Structure for NP0061787 ([4S-(4alpha,4aalpha,5alpha,8abeta)]-4,4a,5,6,7,8,8a,9-Octahydro-3,4a,5-trimethyl-9-oxonaphtho[2,3-b]furan-4-yl ester 3-methyl-2-butenoic acid)