NP-MRD: Showing NP-Card for (4s,6as,7r,11bs)-4-(methoxycarbonyl)-4,7-dimethyl-1h,2h,3h,4ah,5h,6h,6ah,7h,11h,11ah-phenanthro[3,2-b]furan-11b-carboxylic acid (NP0184992)

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Record Information

Version

2.0

Created at

2022-09-04 00:16:09 UTC

Updated at

2022-09-04 00:16:09 UTC

NP-MRD ID

NP0184992

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(4s,6as,7r,11bs)-4-(methoxycarbonyl)-4,7-dimethyl-1h,2h,3h,4ah,5h,6h,6ah,7h,11h,11ah-phenanthro[3,2-b]furan-11b-carboxylic acid

Description

Caesaljapin belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units. (4s,6as,7r,11bs)-4-(methoxycarbonyl)-4,7-dimethyl-1h,2h,3h,4ah,5h,6h,6ah,7h,11h,11ah-phenanthro[3,2-b]furan-11b-carboxylic acid was first documented in 2016 (PMID: 26481825). Based on a literature review a small amount of articles have been published on Caesaljapin (PMID: 30450403) (PMID: 30296708) (PMID: 26268793).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309042202162D          

 26 29  0  0  1  0            999 V2000
   -1.7270   -3.7504    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9142   -3.6091    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6302   -2.8345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1589   -2.2012    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1827   -2.6932    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1807   -3.5182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0976   -1.9173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4342   -1.2866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2463   -1.4318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5266   -2.2077    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0584   -1.5770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8008   -1.2171    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7781   -0.8011    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3387   -2.3529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8705   -1.7222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6826   -1.8674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3340   -1.3611    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0168   -1.8241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7875   -2.6166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9629   -2.6434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4311   -3.2741    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7114   -4.0500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6190   -3.1289    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0872   -3.7596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2751   -3.6143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9948   -2.8384    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  6  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  1  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 10 14  1  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
 19 20  1  0  0  0  0
 16 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  6  0  0  0
 21 23  1  0  0  0  0
 14 23  1  0  0  0  0
 23 24  1  6  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
  5 26  1  0  0  0  0
 10 26  1  0  0  0  0
M  END

     RDKit          3D

 54 57  0  0  0  0  0  0  0  0999 V2000
   -4.1038    2.4697   -1.9995 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2994    1.4232   -1.4921 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3785    1.0631   -0.1632 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2095    1.7305    0.5449 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5528   -0.0337    0.4248 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.9649   -0.1354    1.9052 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0242   -1.3186   -0.2109 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1506   -2.4902    0.0750 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8372   -2.1184    0.7642 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2638   -0.9824   -0.0209 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2308   -1.3673   -1.4363 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7948   -0.8538   -2.3960 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678   -2.4925   -1.7270 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1242   -0.5857    0.3628 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1038   -1.6809    0.6319 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2618   -0.9913    1.2318 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0056   -1.1994    2.2654 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9315   -0.2916    2.3939 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7853    0.5941    1.3517 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7092    0.1415    0.6038 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0259    0.5966   -0.6286 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4973    1.9827   -1.0383 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5730    0.4226   -0.6641 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7675    1.6755   -0.3770 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7117    1.3841   -0.5870 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1101    0.2416    0.2846 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.0965    2.5233   -3.0884 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8243    3.4480   -1.5094 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1422    2.2658   -1.6048 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7535    0.5690    2.1616 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0669    0.1535    2.5135 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2218   -1.1567    2.1931 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0284   -1.5494    0.2611 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2832   -1.1938   -1.2930 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8681   -2.9506   -0.8941 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6568   -3.2938    0.6565 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1907   -3.0103    0.6440 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9713   -1.9069    1.8326 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4656   -3.3597   -1.2512 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0536   -0.0057    1.3338 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4786   -2.1515   -0.3212 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6402   -2.4154    1.2887 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6743   -0.2326    3.1616 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3559    1.4750    1.1120 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4684   -0.0728   -1.4358 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5584    1.9204   -1.3980 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5209    2.6564   -0.1550 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9038    2.3621   -1.8676 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2590    0.0968   -1.6899 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0896    2.5457   -0.9536 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8916    1.9095    0.6996 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9843    1.3298   -1.6351 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2408    2.2975   -0.1785 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7518    0.5626    1.3184 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  5  3  1  6
  5  6  1  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 14  1  0
 14 15  1  0
 15 16  1  0
 16 20  2  0
 20 19  1  0
 19 18  2  0
 18 17  1  0
 20 21  1  0
 21 22  1  0
 21 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 10 11  1  6
 11 13  1  0
 11 12  2  0
 26  5  1  0
 26 10  1  0
 23 14  1  0
 17 16  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  6 30  1  0
  6 31  1  0
  6 32  1  0
  7 33  1  0
  7 34  1  0
  8 35  1  0
  8 36  1  0
  9 37  1  0
  9 38  1  0
 14 40  1  1
 15 41  1  0
 15 42  1  0
 19 44  1  0
 18 43  1  0
 21 45  1  6
 22 46  1  0
 22 47  1  0
 22 48  1  0
 23 49  1  6
 24 50  1  0
 24 51  1  0
 25 52  1  0
 25 53  1  0
 26 54  1  1
 13 39  1  0
M  END


  Mrv1652309042202162D          

 26 29  0  0  1  0            999 V2000
   -1.7270   -3.7504    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9142   -3.6091    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6302   -2.8345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1589   -2.2012    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1827   -2.6932    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1807   -3.5182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0976   -1.9173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4342   -1.2866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2463   -1.4318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5266   -2.2077    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0584   -1.5770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8008   -1.2171    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7781   -0.8011    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3387   -2.3529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8705   -1.7222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6826   -1.8674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3340   -1.3611    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0168   -1.8241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7875   -2.6166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9629   -2.6434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4311   -3.2741    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7114   -4.0500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6190   -3.1289    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0872   -3.7596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2751   -3.6143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9948   -2.8384    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  6  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  1  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 10 14  1  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
 19 20  1  0  0  0  0
 16 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  6  0  0  0
 21 23  1  0  0  0  0
 14 23  1  0  0  0  0
 23 24  1  6  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
  5 26  1  0  0  0  0
 10 26  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0184992

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)[C@@]1(C)CCC[C@@]2(C3CC4=C(C=CO4)[C@H](C)[C@@H]3CCC12)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C21H28O5/c1-12-13-5-6-17-20(2,19(24)25-3)8-4-9-21(17,18(22)23)15(13)11-16-14(12)7-10-26-16/h7,10,12-13,15,17H,4-6,8-9,11H2,1-3H3,(H,22,23)/t12-,13+,15?,17?,20+,21+/m1/s1

> <INCHI_KEY>
BUDZNKDGXHMPRO-ISGQYPEVSA-N

> <FORMULA>
C21H28O5

> <MOLECULAR_WEIGHT>
360.45

> <EXACT_MASS>
360.193674002

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
54

> <JCHEM_AVERAGE_POLARIZABILITY>
38.97339195631646

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S,6S,10S,11R)-6-(methoxycarbonyl)-6,11-dimethyl-15-oxatetracyclo[8.7.0.0^{2,7}.0^{12,16}]heptadeca-12(16),13-diene-2-carboxylic acid

> <JCHEM_LOGP>
4.032150132666667

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.704145891479741

> <JCHEM_PKA_STRONGEST_BASIC>
-2.815337751967681

> <JCHEM_POLAR_SURFACE_AREA>
76.74000000000001

> <JCHEM_REFRACTIVITY>
95.32999999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(2S,6S,10S,11R)-6-(methoxycarbonyl)-6,11-dimethyl-15-oxatetracyclo[8.7.0.0^{2,7}.0^{12,16}]heptadeca-12(16),13-diene-2-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-22         0                                  
HETATM    1  C   UNK     0      -3.224  -7.001   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -1.706  -6.737   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -1.176  -5.291   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -2.163  -4.109   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       0.341  -5.027   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.337  -6.567   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.182  -3.579   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.810  -2.402   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.326  -2.673   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.850  -4.121   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.842  -2.944   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       5.228  -2.272   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       3.319  -1.495   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       4.366  -4.392   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.358  -3.215   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.874  -3.486   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       8.090  -2.541   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       9.365  -3.405   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.937  -4.884   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       7.398  -4.934   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.405  -6.112   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       6.928  -7.560   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.889  -5.841   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       3.896  -7.018   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       2.380  -6.747   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       1.857  -5.298   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6    7   26                                             
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   14   26                                             
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11                                                            
CONECT   14   10   15   23                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   20                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   16   21                                                  
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   14   24                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25    5   10                                                  
MASTER        0    0    0    0    0    0    0    0   26    0   58    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₁H₂₈O₅

Average Mass

360.4500 Da

Monoisotopic Mass

360.19367 Da

IUPAC Name

(2S,6S,10S,11R)-6-(methoxycarbonyl)-6,11-dimethyl-15-oxatetracyclo[8.7.0.0^{2,7}.0^{12,16}]heptadeca-12(16),13-diene-2-carboxylic acid

Traditional Name

(2S,6S,10S,11R)-6-(methoxycarbonyl)-6,11-dimethyl-15-oxatetracyclo[8.7.0.0^{2,7}.0^{12,16}]heptadeca-12(16),13-diene-2-carboxylic acid

CAS Registry Number

Not Available

SMILES

COC(=O)[C@@]1(C)CCC[C@@]2(C3CC4=C(C=CO4)[C@H](C)[C@@H]3CCC12)C(O)=O

InChI Identifier

InChI=1S/C21H28O5/c1-12-13-5-6-17-20(2,19(24)25-3)8-4-9-21(17,18(22)23)15(13)11-16-14(12)7-10-26-16/h7,10,12-13,15,17H,4-6,8-9,11H2,1-3H3,(H,22,23)/t12-,13+,15?,17?,20+,21+/m1/s1

InChI Key

BUDZNKDGXHMPRO-ISGQYPEVSA-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

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Diterpenoids

Alternative Parents

Substituents

Diterpenoid
Naphthofuran
Benzofuran
Dicarboxylic acid or derivatives
Heteroaromatic compound
Furan
Methyl ester
Carboxylic acid ester
Organoheterocyclic compound
Oxacycle
Carboxylic acid
Carboxylic acid derivative
Hydrocarbon derivative
Organic oxide
Carbonyl group
Organic oxygen compound
Organooxygen 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	4.03	ChemAxon
pKa (Strongest Acidic)	4.7	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	76.74 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	95.33 m³·mol⁻¹	ChemAxon
Polarizability	38.97 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

5144265

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6712179

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Akihara Y, Kamikawa S, Harauchi Y, Ohta E, Nehira T, Omura H, Ohta S: HPLC profiles and spectroscopic data of cassane-type furanoditerpenoids. Data Brief. 2018 Oct 25;21:1076-1088. doi: 10.1016/j.dib.2018.10.068. eCollection 2018 Dec. [PubMed:30450403 ]
Akihara Y, Kamikawa S, Harauchi Y, Ohta E, Nehira T, Omura H, Ohta S: Hydroxylated furanoditerpenoids from pupal cases produced by the bruchid beetle Sulcobruchus sauteri inside the seeds of Caesalpinia decapetala. Phytochemistry. 2018 Dec;156:151-158. doi: 10.1016/j.phytochem.2018.09.007. Epub 2018 Oct 6. [PubMed:30296708 ]
Kamikawa S, Oshimo S, Ohta E, Nehira T, Omura H, Ohta S: Cassane diterpenoids from the roots of Caesalpinia decapetala var. japonica and structure revision of caesaljapin. Phytochemistry. 2016 Jan;121:50-7. doi: 10.1016/j.phytochem.2015.10.001. Epub 2015 Oct 22. [PubMed:26481825 ]
Wei H, Liu XQ, Zhu JJ, Gao LL, Wang ZM, Yan LH: A new cassane diterpenoid from the seeds of Caesalpinia decapetala. J Asian Nat Prod Res. 2016;18(4):371-5. doi: 10.1080/10286020.2015.1055255. Epub 2015 Aug 13. [PubMed:26268793 ]
LOTUS database [Link]

Showing NP-Card for (4s,6as,7r,11bs)-4-(methoxycarbonyl)-4,7-dimethyl-1h,2h,3h,4ah,5h,6h,6ah,7h,11h,11ah-phenanthro[3,2-b]furan-11b-carboxylic acid (NP0184992)

MOL for NP0184992 ((4s,6as,7r,11bs)-4-(methoxycarbonyl)-4,7-dimethyl-1h,2h,3h,4ah,5h,6h,6ah,7h,11h,11ah-phenanthro[3,2-b]furan-11b-carboxylic acid)

3D MOL for NP0184992 ((4s,6as,7r,11bs)-4-(methoxycarbonyl)-4,7-dimethyl-1h,2h,3h,4ah,5h,6h,6ah,7h,11h,11ah-phenanthro[3,2-b]furan-11b-carboxylic acid)

3D SDF for NP0184992 ((4s,6as,7r,11bs)-4-(methoxycarbonyl)-4,7-dimethyl-1h,2h,3h,4ah,5h,6h,6ah,7h,11h,11ah-phenanthro[3,2-b]furan-11b-carboxylic acid)

3D-SDF for NP0184992 ((4s,6as,7r,11bs)-4-(methoxycarbonyl)-4,7-dimethyl-1h,2h,3h,4ah,5h,6h,6ah,7h,11h,11ah-phenanthro[3,2-b]furan-11b-carboxylic acid)

PDB for NP0184992 ((4s,6as,7r,11bs)-4-(methoxycarbonyl)-4,7-dimethyl-1h,2h,3h,4ah,5h,6h,6ah,7h,11h,11ah-phenanthro[3,2-b]furan-11b-carboxylic acid)

3D PDB for NP0184992 ((4s,6as,7r,11bs)-4-(methoxycarbonyl)-4,7-dimethyl-1h,2h,3h,4ah,5h,6h,6ah,7h,11h,11ah-phenanthro[3,2-b]furan-11b-carboxylic acid)

SMILES for NP0184992 ((4s,6as,7r,11bs)-4-(methoxycarbonyl)-4,7-dimethyl-1h,2h,3h,4ah,5h,6h,6ah,7h,11h,11ah-phenanthro[3,2-b]furan-11b-carboxylic acid)

INCHI for NP0184992 ((4s,6as,7r,11bs)-4-(methoxycarbonyl)-4,7-dimethyl-1h,2h,3h,4ah,5h,6h,6ah,7h,11h,11ah-phenanthro[3,2-b]furan-11b-carboxylic acid)

Structure for NP0184992 ((4s,6as,7r,11bs)-4-(methoxycarbonyl)-4,7-dimethyl-1h,2h,3h,4ah,5h,6h,6ah,7h,11h,11ah-phenanthro[3,2-b]furan-11b-carboxylic acid)

3D Structure for NP0184992 ((4s,6as,7r,11bs)-4-(methoxycarbonyl)-4,7-dimethyl-1h,2h,3h,4ah,5h,6h,6ah,7h,11h,11ah-phenanthro[3,2-b]furan-11b-carboxylic acid)