NP-MRD: Showing NP-Card for (1r,2s,4r,5r,8r,9s,11r)-9-formyl-2-(hydroxymethyl)-13-isopropyl-5-methyltetracyclo[7.4.0.0²,¹¹.0⁴,⁸]tridec-12-ene-1-carboxylic acid (NP0252878)

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Record Information

Version

2.0

Created at

2022-09-07 16:33:23 UTC

Updated at

2022-09-07 16:33:23 UTC

NP-MRD ID

NP0252878

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,2s,4r,5r,8r,9s,11r)-9-formyl-2-(hydroxymethyl)-13-isopropyl-5-methyltetracyclo[7.4.0.0²,¹¹.0⁴,⁸]tridec-12-ene-1-carboxylic acid

Description

Sordaricin belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. (1r,2s,4r,5r,8r,9s,11r)-9-formyl-2-(hydroxymethyl)-13-isopropyl-5-methyltetracyclo[7.4.0.0²,¹¹.0⁴,⁸]tridec-12-ene-1-carboxylic acid is found in Garcinia dulcis. (1r,2s,4r,5r,8r,9s,11r)-9-formyl-2-(hydroxymethyl)-13-isopropyl-5-methyltetracyclo[7.4.0.0²,¹¹.0⁴,⁸]tridec-12-ene-1-carboxylic acid was first documented in 2009 (PMID: 19199657). Based on a literature review a small amount of articles have been published on sordaricin (PMID: 31478377) (PMID: 35546152) (PMID: 32358585) (PMID: 27072286).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309072218332D          

 24 27  0  0  1  0            999 V2000
   -0.9392   -0.3637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1153   -0.6664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0701   -1.6250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4919   -0.0010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4987    0.8014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2809    0.8789    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8202    1.4474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1871    0.7453    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7565    1.6984    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7084    2.6136    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9762    0.6426    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7059    1.0276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2975    0.4526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9335   -0.2878    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.3960   -1.0187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1169   -0.1703    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4542   -0.7157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7796   -0.0787    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5583    0.2598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5129    1.1925    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4013    0.0642    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2972   -0.8719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4775   -1.1208    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6454   -1.6897    0.0000 O   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
  2  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  1  0  0  0
  7  8  1  0  0  0  0
  8  9  1  1  0  0  0
  9 10  2  0  0  0  0
  8 11  1  0  0  0  0
 11 12  1  6  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  1  0  0  0
 14 16  1  0  0  0  0
 11 16  1  0  0  0  0
 16 17  1  1  0  0  0
 17 18  1  0  0  0  0
  6 18  1  0  0  0  0
 18 19  1  6  0  0  0
 19 20  1  0  0  0  0
 18 21  1  0  0  0  0
  4 21  1  0  0  0  0
  8 21  1  0  0  0  0
 21 22  1  1  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
M  END

     RDKit          3D

 52 55  0  0  0  0  0  0  0  0999 V2000
    3.5304   -1.3902    0.6005 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1931   -0.2446   -0.2965 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3769    0.7156   -0.2495 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9353    0.4615    0.0970 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8435    1.7644    0.4695 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3703    2.0449    0.3937 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0152    1.7796   -1.0429 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1298    0.2795   -1.1726 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5560   -0.2517   -2.3511 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1359    0.5036   -3.1078 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4973   -0.2246   -1.0469 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3753   -0.3118   -2.2141 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7149   -0.6455   -1.5314 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6087   -0.0812   -0.1197 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.7019   -1.1423    0.9318 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2947    0.6533   -0.1043 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5657    0.6415    1.1836 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0962    0.7670    1.1066 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4749    0.7004    2.5018 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8455    0.6939    2.5478 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5858   -0.1519    0.1313 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4859   -1.5494    0.3944 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0607   -1.9828    1.4462 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9802   -2.4871   -0.4853 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6599   -2.3139    0.0011 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5380   -1.2340    1.0875 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7640   -1.6101    1.3750 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1448   -0.6125   -1.3400 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0054    1.6844   -0.6502 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7513    0.8565    0.7754 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2028    0.3886   -0.8964 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6561    2.3980    0.7427 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0447    2.9504    0.8282 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8857    2.0476   -1.7157 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8248    2.3514   -1.4246 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5514   -1.2973   -2.5520 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4641   -1.2388   -0.5506 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1103   -1.2146   -2.8194 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4567    0.5893   -2.8183 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4950   -0.1690   -2.1261 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8123   -1.7391   -1.4237 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4678    0.6076    0.0124 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6356   -1.7262    0.7241 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8333   -1.8134    0.9739 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8907   -0.6303    1.9014 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4855    1.6595   -0.4820 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9404    1.5116    1.7905 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8010   -0.2515    1.7921 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0711   -0.2164    2.9704 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0456    1.5527    3.0829 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1251    0.2603    3.4004 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4878   -3.3327   -0.7414 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  6
  9 10  2  0
  8 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  1
 19 20  1  0
 18 21  1  0
 21 22  1  1
 22 24  1  0
 22 23  2  0
 21  4  1  0
 18  6  1  0
 21  8  1  0
 16 11  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  2 28  1  0
  3 29  1  0
  3 30  1  0
  3 31  1  0
  5 32  1  0
  6 33  1  1
  7 34  1  0
  7 35  1  0
  9 36  1  0
 11 37  1  1
 12 38  1  0
 12 39  1  0
 13 40  1  0
 13 41  1  0
 14 42  1  1
 15 43  1  0
 15 44  1  0
 15 45  1  0
 16 46  1  6
 17 47  1  0
 17 48  1  0
 19 49  1  0
 19 50  1  0
 20 51  1  0
 24 52  1  0
M  END


  Mrv1652309072218332D          

 24 27  0  0  1  0            999 V2000
   -0.9392   -0.3637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1153   -0.6664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0701   -1.6250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4919   -0.0010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4987    0.8014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2809    0.8789    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8202    1.4474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1871    0.7453    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7565    1.6984    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7084    2.6136    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9762    0.6426    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7059    1.0276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2975    0.4526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9335   -0.2878    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.3960   -1.0187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1169   -0.1703    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4542   -0.7157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7796   -0.0787    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5583    0.2598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5129    1.1925    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4013    0.0642    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2972   -0.8719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4775   -1.1208    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6454   -1.6897    0.0000 O   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
  2  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  1  0  0  0
  7  8  1  0  0  0  0
  8  9  1  1  0  0  0
  9 10  2  0  0  0  0
  8 11  1  0  0  0  0
 11 12  1  6  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  1  0  0  0
 14 16  1  0  0  0  0
 11 16  1  0  0  0  0
 16 17  1  1  0  0  0
 17 18  1  0  0  0  0
  6 18  1  0  0  0  0
 18 19  1  6  0  0  0
 19 20  1  0  0  0  0
 18 21  1  0  0  0  0
  4 21  1  0  0  0  0
  8 21  1  0  0  0  0
 21 22  1  1  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0252878

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)C1=C[C@H]2C[C@]3(C=O)[C@@H]4CC[C@@H](C)[C@H]4C[C@@]2(CO)[C@]13C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C20H28O4/c1-11(2)16-6-13-7-19(10-22)15-5-4-12(3)14(15)8-18(13,9-21)20(16,19)17(23)24/h6,10-15,21H,4-5,7-9H2,1-3H3,(H,23,24)/t12-,13+,14-,15-,18+,19+,20-/m1/s1

> <INCHI_KEY>
QIMCUSGGYZHVEF-VULLPXFTSA-N

> <FORMULA>
C20H28O4

> <MOLECULAR_WEIGHT>
332.44

> <EXACT_MASS>
332.198759382

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
52

> <JCHEM_AVERAGE_POLARIZABILITY>
36.4154104974543

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,2S,4R,5R,8R,9S,11R)-9-formyl-2-(hydroxymethyl)-5-methyl-13-(propan-2-yl)tetracyclo[7.4.0.0^{2,11}.0^{4,8}]tridec-12-ene-1-carboxylic acid

> <JCHEM_LOGP>
2.1871031466666664

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
15.06939699085115

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.4145231768292215

> <JCHEM_PKA_STRONGEST_BASIC>
-2.7805743757758696

> <JCHEM_POLAR_SURFACE_AREA>
74.6

> <JCHEM_REFRACTIVITY>
90.89779999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2S,4R,5R,8R,9S,11R)-9-formyl-2-(hydroxymethyl)-13-isopropyl-5-methyltetracyclo[7.4.0.0^{2,11}.0^{4,8}]tridec-12-ene-1-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  C   UNK     0      -1.753  -0.679   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.215  -1.244   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.131  -3.033   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.918  -0.002   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.931   1.496   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.391   1.641   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.398   2.702   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.083   1.391   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.145   3.170   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       5.056   4.879   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       5.556   1.200   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.918   1.918   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.022   0.845   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.342  -0.537   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.206  -1.902   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.818  -0.318   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.581  -1.336   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.322  -0.147   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.776   0.485   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       4.691   2.226   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       2.616   0.120   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.421  -1.627   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       0.891  -2.092   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       3.071  -3.154   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   21                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   18                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   11   21                                             
CONECT    9    8   10                                                       
CONECT   10    9                                                            
CONECT   11    8   12   16                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   11   17                                                  
CONECT   17   16   18                                                       
CONECT   18   17    6   19   21                                             
CONECT   19   18   20                                                       
CONECT   20   19                                                            
CONECT   21   18    4    8   22                                             
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   54    0
END

View in JSmol

Synonyms

Value	Source
(-)-Sordaricin	ChEBI

Chemical Formula

C₂₀H₂₈O₄

Average Mass

332.4400 Da

Monoisotopic Mass

332.19876 Da

IUPAC Name

(1R,2S,4R,5R,8R,9S,11R)-9-formyl-2-(hydroxymethyl)-5-methyl-13-(propan-2-yl)tetracyclo[7.4.0.0^{2,11}.0^{4,8}]tridec-12-ene-1-carboxylic acid

Traditional Name

(1R,2S,4R,5R,8R,9S,11R)-9-formyl-2-(hydroxymethyl)-13-isopropyl-5-methyltetracyclo[7.4.0.0^{2,11}.0^{4,8}]tridec-12-ene-1-carboxylic acid

CAS Registry Number

Not Available

SMILES

CC(C)C1=C[C@H]2C[C@]3(C=O)[C@@H]4CC[C@@H](C)[C@H]4C[C@@]2(CO)[C@]13C(O)=O

InChI Identifier

InChI=1S/C20H28O4/c1-11(2)16-6-13-7-19(10-22)15-5-4-12(3)14(15)8-18(13,9-21)20(16,19)17(23)24/h6,10-15,21H,4-5,7-9H2,1-3H3,(H,23,24)/t12-,13+,14-,15-,18+,19+,20-/m1/s1

InChI Key

QIMCUSGGYZHVEF-VULLPXFTSA-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
Garcinia dulcis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Sesquiterpenoids

Alternative Parents

Substituents

Sesquiterpenoid
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Carbonyl group
Aldehyde
Alcohol
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic 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	2.19	ChemAxon
pKa (Strongest Acidic)	4.41	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	74.6 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	90.9 m³·mol⁻¹	ChemAxon
Polarizability	36.42 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

C00034268

Chemspider ID

426018

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

485853

PDB ID

Not Available

ChEBI ID

140259

Good Scents ID

Not Available

References

General References

Zhang MQ, Xu KX, Xue Y, Cao F, Yang LJ, Hou XM, Wang CY, Shao CL: Sordarin Diterpene Glycosides with an Unusual 1,3-Dioxolan-4-one Ring from the Zoanthid-Derived Fungus Curvularia hawaiiensis TA26-15. J Nat Prod. 2019 Sep 27;82(9):2477-2482. doi: 10.1021/acs.jnatprod.9b00164. Epub 2019 Sep 3. [PubMed:31478377 ]
Sun Z, Jamieson CS, Ohashi M, Houk KN, Tang Y: Discovery and characterization of a terpene biosynthetic pathway featuring a norbornene-forming Diels-Alderase. Nat Commun. 2022 May 11;13(1):2568. doi: 10.1038/s41467-022-30288-6. [PubMed:35546152 ]
Ueno M, Kobayashi M, Fujie A, Shibata T: Cloning and heterologous expression of P450Lent4B11, a novel bacterial P450 gene, for hydroxylation of an antifungal agent sordaricin. J Antibiot (Tokyo). 2020 Sep;73(9):615-621. doi: 10.1038/s41429-020-0310-9. Epub 2020 May 1. [PubMed:32358585 ]
Kudo F, Matsuura Y, Hayashi T, Fukushima M, Eguchi T: Genome mining of the sordarin biosynthetic gene cluster from Sordaria araneosa Cain ATCC 36386: characterization of cycloaraneosene synthase and GDP-6-deoxyaltrose transferase. J Antibiot (Tokyo). 2016 Jul;69(7):541-8. doi: 10.1038/ja.2016.40. Epub 2016 Apr 13. [PubMed:27072286 ]
Schule A, Liang H, Vors JP, Ciufolini MA: Synthetic studies toward sordarin: building blocks for the terpenoid core and for analogues thereof. J Org Chem. 2009 Feb 20;74(4):1587-97. doi: 10.1021/jo801911s. [PubMed:19199657 ]
LOTUS database [Link]

Showing NP-Card for (1r,2s,4r,5r,8r,9s,11r)-9-formyl-2-(hydroxymethyl)-13-isopropyl-5-methyltetracyclo[7.4.0.0²,¹¹.0⁴,⁸]tridec-12-ene-1-carboxylic acid (NP0252878)

MOL for NP0252878 ((1r,2s,4r,5r,8r,9s,11r)-9-formyl-2-(hydroxymethyl)-13-isopropyl-5-methyltetracyclo[7.4.0.0²,¹¹.0⁴,⁸]tridec-12-ene-1-carboxylic acid)

3D MOL for NP0252878 ((1r,2s,4r,5r,8r,9s,11r)-9-formyl-2-(hydroxymethyl)-13-isopropyl-5-methyltetracyclo[7.4.0.0²,¹¹.0⁴,⁸]tridec-12-ene-1-carboxylic acid)

3D SDF for NP0252878 ((1r,2s,4r,5r,8r,9s,11r)-9-formyl-2-(hydroxymethyl)-13-isopropyl-5-methyltetracyclo[7.4.0.0²,¹¹.0⁴,⁸]tridec-12-ene-1-carboxylic acid)

3D-SDF for NP0252878 ((1r,2s,4r,5r,8r,9s,11r)-9-formyl-2-(hydroxymethyl)-13-isopropyl-5-methyltetracyclo[7.4.0.0²,¹¹.0⁴,⁸]tridec-12-ene-1-carboxylic acid)

PDB for NP0252878 ((1r,2s,4r,5r,8r,9s,11r)-9-formyl-2-(hydroxymethyl)-13-isopropyl-5-methyltetracyclo[7.4.0.0²,¹¹.0⁴,⁸]tridec-12-ene-1-carboxylic acid)

3D PDB for NP0252878 ((1r,2s,4r,5r,8r,9s,11r)-9-formyl-2-(hydroxymethyl)-13-isopropyl-5-methyltetracyclo[7.4.0.0²,¹¹.0⁴,⁸]tridec-12-ene-1-carboxylic acid)

SMILES for NP0252878 ((1r,2s,4r,5r,8r,9s,11r)-9-formyl-2-(hydroxymethyl)-13-isopropyl-5-methyltetracyclo[7.4.0.0²,¹¹.0⁴,⁸]tridec-12-ene-1-carboxylic acid)

INCHI for NP0252878 ((1r,2s,4r,5r,8r,9s,11r)-9-formyl-2-(hydroxymethyl)-13-isopropyl-5-methyltetracyclo[7.4.0.0²,¹¹.0⁴,⁸]tridec-12-ene-1-carboxylic acid)

Structure for NP0252878 ((1r,2s,4r,5r,8r,9s,11r)-9-formyl-2-(hydroxymethyl)-13-isopropyl-5-methyltetracyclo[7.4.0.0²,¹¹.0⁴,⁸]tridec-12-ene-1-carboxylic acid)

3D Structure for NP0252878 ((1r,2s,4r,5r,8r,9s,11r)-9-formyl-2-(hydroxymethyl)-13-isopropyl-5-methyltetracyclo[7.4.0.0²,¹¹.0⁴,⁸]tridec-12-ene-1-carboxylic acid)