NP-MRD: Showing NP-Card for 6-hydroxy-5-(methoxycarbonyl)-5,9-dimethylpentacyclo[11.2.1.0¹,¹⁰.0⁴,⁹.0¹²,¹⁴]hexadecane-13-carboxylic acid (NP0259277)

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Record Information

Version

2.0

Created at

2022-09-08 01:05:31 UTC

Updated at

2022-09-08 01:05:32 UTC

NP-MRD ID

NP0259277

Secondary Accession Numbers

None

Natural Product Identification

Common Name

6-hydroxy-5-(methoxycarbonyl)-5,9-dimethylpentacyclo[11.2.1.0¹,¹⁰.0⁴,⁹.0¹²,¹⁴]hexadecane-13-carboxylic acid

Description

6-Hydroxy-5-(methoxycarbonyl)-5,9-dimethylpentacyclo[11.2.1.0¹,¹⁰.0⁴,⁹.0¹²,¹⁴]Hexadecane-13-carboxylic acid belongs to the class of organic compounds known as kaurane diterpenoids. These are diterpene alkaloids with a structure that is based on the kaurane skeleton. Kaurane is a tetracyclic compound that arises by cyclisation of a pimarane precursor followed by rearrangement. It possesses a [3,2,1]-bicyclic ring system with C15-C16 bridge connected to C13, forming the five-membered ring D. 6-hydroxy-5-(methoxycarbonyl)-5,9-dimethylpentacyclo[11.2.1.0¹,¹⁰.0⁴,⁹.0¹²,¹⁴]hexadecane-13-carboxylic acid is found in Mallotus nudiflorus. 6-Hydroxy-5-(methoxycarbonyl)-5,9-dimethylpentacyclo[11.2.1.0¹,¹⁰.0⁴,⁹.0¹²,¹⁴]Hexadecane-13-carboxylic acid is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004181501432D          

 26 30  0  0  0  0            999 V2000
    5.2489   -1.4556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4693   -1.1858    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3131   -0.3757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9366    0.1646    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5335   -0.1059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4032   -0.9205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9346    0.6151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7595    0.6282    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5108    1.3229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6859    1.3098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2848    0.5889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8914    1.3140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7086   -0.1190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2789   -0.8247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4299   -0.7421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8668   -0.0150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0658    0.4437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6620    0.6943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0949    1.0618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8220    1.3138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3803    0.6512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4573    0.0498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2330   -0.5410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2547   -0.1619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4700   -0.9583    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8367    0.4228    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
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
  5 13  1  0  0  0  0
 13 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  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 11 21  1  0  0  0  0
 16 21  1  0  0  0  0
 19 22  1  0  0  0  0
 18 22  1  0  0  0  0
 22 23  1  0  0  0  0
 16 23  1  0  0  0  0
 22 24  1  0  0  0  0
 24 25  2  0  0  0  0
 24 26  1  0  0  0  0
M  END

     RDKit          3D

 56 60  0  0  0  0  0  0  0  0999 V2000
   -4.1798    1.8593    1.7380 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3602    1.1713    0.8016 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3911   -0.2057    0.6432 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1969   -0.8197    1.3855 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5231   -0.9005   -0.3439 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.9005   -2.3953   -0.2005 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8932   -0.5505   -1.7501 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.2582   -1.6825   -2.5182 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9406    0.2740   -2.5219 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4974    0.1092   -2.1895 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2684    0.2257   -0.6983 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5131    1.6320   -0.2928 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1706   -0.2174   -0.4664 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1907    0.4901   -1.2610 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5507    0.3922   -0.6508 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6911    0.8179    0.7371 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3677    0.9697    1.4037 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5669   -0.2629    0.9678 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5129   -0.6030    1.9366 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8812   -0.6493    1.4836 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0860   -0.8080    0.0001 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7115   -1.2931    1.0330 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8317   -0.6238    0.3223 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.1695   -1.2102    0.4091 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3863   -2.4413    0.2457 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2528   -0.3887    0.6818 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6017    2.2754    2.5674 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7454    2.6229    1.1561 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9454    1.1710    2.1877 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9303   -2.5276   -0.5719 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2159   -2.9498   -0.8701 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8411   -2.7042    0.8520 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8642    0.0291   -1.6920 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5094   -1.9821   -3.0906 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0314   -0.0129   -3.6151 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2660    1.3573   -2.5499 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1595   -0.8810   -2.5016 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0683    0.9123   -2.7012 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6916    1.8084    0.7683 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3787    2.0319   -0.8593 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3508    2.2701   -0.5727 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1628   -1.2962   -0.8177 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0055    1.5518   -1.4850 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2624    0.0040   -2.2800 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3752    0.5999   -1.3973 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5880    1.3317    1.1312 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5453    0.8294    2.5093 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8481    1.9085    1.2485 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7672   -1.5853    2.4358 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5757    0.1348    2.7926 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4302   -1.5179    1.9572 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4688    0.2412    1.8081 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6026   -1.8028   -0.2502 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3992   -2.2529    0.6213 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9731   -1.4020    2.0954 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2480    0.5296    0.2281 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  1
  5  6  1  0
  5  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  1
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 22  1  0
 22 23  1  0
 23 24  1  6
 24 26  1  0
 24 25  2  0
 18 19  1  1
 19 20  1  0
 20 21  1  0
 21  5  1  0
 21 11  1  0
 18 13  1  0
 23 15  1  0
 23 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  1
  8 34  1  0
  9 35  1  0
  9 36  1  0
 10 37  1  0
 10 38  1  0
 12 39  1  0
 12 40  1  0
 12 41  1  0
 13 42  1  6
 14 43  1  0
 14 44  1  0
 15 45  1  6
 16 46  1  6
 17 47  1  0
 17 48  1  0
 22 54  1  0
 22 55  1  0
 26 56  1  0
 19 49  1  0
 19 50  1  0
 20 51  1  0
 20 52  1  0
 21 53  1  6
M  END


  Mrv1533004181501432D          

 26 30  0  0  0  0            999 V2000
    5.2489   -1.4556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4693   -1.1858    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3131   -0.3757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9366    0.1646    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5335   -0.1059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4032   -0.9205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9346    0.6151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7595    0.6282    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5108    1.3229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6859    1.3098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2848    0.5889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8914    1.3140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7086   -0.1190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2789   -0.8247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4299   -0.7421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8668   -0.0150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0658    0.4437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6620    0.6943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0949    1.0618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8220    1.3138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3803    0.6512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4573    0.0498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2330   -0.5410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2547   -0.1619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4700   -0.9583    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8367    0.4228    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
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
  5 13  1  0  0  0  0
 13 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  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 11 21  1  0  0  0  0
 16 21  1  0  0  0  0
 19 22  1  0  0  0  0
 18 22  1  0  0  0  0
 22 23  1  0  0  0  0
 16 23  1  0  0  0  0
 22 24  1  0  0  0  0
 24 25  2  0  0  0  0
 24 26  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0259277

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)C1(C)C(O)CCC2(C)C3CC4C5CC3(CC45C(O)=O)CCC12

> <INCHI_IDENTIFIER>
InChI=1S/C21H30O5/c1-18-6-5-15(22)19(2,17(25)26-3)13(18)4-7-20-9-12-11(8-14(18)20)21(12,10-20)16(23)24/h11-15,22H,4-10H2,1-3H3,(H,23,24)

> <INCHI_KEY>
VURGZLDGPWHDST-UHFFFAOYSA-N

> <FORMULA>
C21H30O5

> <MOLECULAR_WEIGHT>
362.466

> <EXACT_MASS>
362.209324066

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
56

> <JCHEM_AVERAGE_POLARIZABILITY>
39.34926521200141

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
6-hydroxy-5-(methoxycarbonyl)-5,9-dimethylpentacyclo[11.2.1.0¹,¹⁰.0⁴,⁹.0¹²,¹⁴]hexadecane-13-carboxylic acid

> <ALOGPS_LOGP>
2.32

> <JCHEM_LOGP>
2.4964551470000007

> <ALOGPS_LOGS>
-4.12

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
14.453826117701837

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.2337719133817435

> <JCHEM_PKA_STRONGEST_BASIC>
-3.0376964561589688

> <JCHEM_POLAR_SURFACE_AREA>
83.83

> <JCHEM_REFRACTIVITY>
93.60739999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.72e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6-hydroxy-5-(methoxycarbonyl)-5,9-dimethylpentacyclo[11.2.1.0¹,¹⁰.0⁴,⁹.0¹²,¹⁴]hexadecane-13-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 18-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   18-APR-15         0                                  
HETATM    1  C   UNK     0       9.798  -2.717   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       8.343  -2.213   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       8.051  -0.701   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       9.215   0.307   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       6.596  -0.198   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.353  -1.718   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.345   1.148   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       8.884   1.173   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       6.553   2.469   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.014   2.445   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.265   1.099   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.531   2.453   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.056  -0.222   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.254  -1.539   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.669  -1.385   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.618  -0.028   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.123   0.828   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.236   1.296   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -0.177   1.982   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.534   2.452   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.577   1.216   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -0.854   0.093   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.435  -1.010   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -2.342  -0.302   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      -2.744  -1.789   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0      -3.429   0.789   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6    7   13                                             
CONECT    6    5                                                            
CONECT    7    5    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   13   21                                             
CONECT   12   11                                                            
CONECT   13   11    5   14                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   21   23                                             
CONECT   17   16   18                                                       
CONECT   18   17   19   22                                                  
CONECT   19   18   20   22                                                  
CONECT   20   19   21                                                       
CONECT   21   20   11   16                                                  
CONECT   22   19   18   23   24                                             
CONECT   23   22   16                                                       
CONECT   24   22   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24                                                            
MASTER        0    0    0    0    0    0    0    0   26    0   60    0
END

View in JSmol

Synonyms

Value	Source
6-Hydroxy-5-(methoxycarbonyl)-5,9-dimethylpentacyclo[11.2.1.0,.0,.0,]hexadecane-13-carboxylate	Generator
6-Hydroxy-5-(methoxycarbonyl)-5,9-dimethylpentacyclo[11.2.1.0¹,¹⁰.0⁴,⁹.0¹²,¹⁴]hexadecane-13-carboxylate	Generator

Chemical Formula

C₂₁H₃₀O₅

Average Mass

362.4660 Da

Monoisotopic Mass

362.20932 Da

IUPAC Name

6-hydroxy-5-(methoxycarbonyl)-5,9-dimethylpentacyclo[11.2.1.0¹,¹⁰.0⁴,⁹.0¹²,¹⁴]hexadecane-13-carboxylic acid

Traditional Name

6-hydroxy-5-(methoxycarbonyl)-5,9-dimethylpentacyclo[11.2.1.0¹,¹⁰.0⁴,⁹.0¹²,¹⁴]hexadecane-13-carboxylic acid

CAS Registry Number

Not Available

SMILES

COC(=O)C1(C)C(O)CCC2(C)C3CC4C5CC3(CC45C(O)=O)CCC12

InChI Identifier

InChI=1S/C21H30O5/c1-18-6-5-15(22)19(2,17(25)26-3)13(18)4-7-20-9-12-11(8-14(18)20)21(12,10-20)16(23)24/h11-15,22H,4-10H2,1-3H3,(H,23,24)

InChI Key

VURGZLDGPWHDST-UHFFFAOYSA-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
Trewia nudiflora	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as kaurane diterpenoids. These are diterpene alkaloids with a structure that is based on the kaurane skeleton. Kaurane is a tetracyclic compound that arises by cyclisation of a pimarane precursor followed by rearrangement. It possesses a [3,2,1]-bicyclic ring system with C15-C16 bridge connected to C13, forming the five-membered ring D.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Kaurane diterpenoids

Alternative Parents

Substituents

Atisane diterpenoid
Kaurane diterpenoid
Steroid acid
Villanovane, atisane, trachylobane or helvifulvane diterpenoid
3-carboxy steroid
Steroid
Alkaloid or derivatives
Beta-hydroxy acid
Cyclopropanecarboxylic acid
Cyclopropanecarboxylic acid or derivatives
Dicarboxylic acid or derivatives
Hydroxy acid
Cyclic alcohol
Methyl ester
Carboxylic acid ester
Secondary alcohol
Carboxylic acid
Carboxylic acid derivative
Organic oxide
Organic oxygen compound
Alcohol
Carbonyl group
Organooxygen compound
Hydrocarbon derivative
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	2.32	ALOGPS
logP	2.5	ChemAxon
logS	-4.1	ALOGPS
pKa (Strongest Acidic)	4.23	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	83.83 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	93.61 m³·mol⁻¹	ChemAxon
Polarizability	39.35 Å³	ChemAxon
Number of Rings	5	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

75090376

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 6-hydroxy-5-(methoxycarbonyl)-5,9-dimethylpentacyclo[11.2.1.0¹,¹⁰.0⁴,⁹.0¹²,¹⁴]hexadecane-13-carboxylic acid (NP0259277)

MOL for NP0259277 (6-hydroxy-5-(methoxycarbonyl)-5,9-dimethylpentacyclo[11.2.1.0¹,¹⁰.0⁴,⁹.0¹²,¹⁴]hexadecane-13-carboxylic acid)

3D MOL for NP0259277 (6-hydroxy-5-(methoxycarbonyl)-5,9-dimethylpentacyclo[11.2.1.0¹,¹⁰.0⁴,⁹.0¹²,¹⁴]hexadecane-13-carboxylic acid)

3D SDF for NP0259277 (6-hydroxy-5-(methoxycarbonyl)-5,9-dimethylpentacyclo[11.2.1.0¹,¹⁰.0⁴,⁹.0¹²,¹⁴]hexadecane-13-carboxylic acid)

3D-SDF for NP0259277 (6-hydroxy-5-(methoxycarbonyl)-5,9-dimethylpentacyclo[11.2.1.0¹,¹⁰.0⁴,⁹.0¹²,¹⁴]hexadecane-13-carboxylic acid)

PDB for NP0259277 (6-hydroxy-5-(methoxycarbonyl)-5,9-dimethylpentacyclo[11.2.1.0¹,¹⁰.0⁴,⁹.0¹²,¹⁴]hexadecane-13-carboxylic acid)

3D PDB for NP0259277 (6-hydroxy-5-(methoxycarbonyl)-5,9-dimethylpentacyclo[11.2.1.0¹,¹⁰.0⁴,⁹.0¹²,¹⁴]hexadecane-13-carboxylic acid)

SMILES for NP0259277 (6-hydroxy-5-(methoxycarbonyl)-5,9-dimethylpentacyclo[11.2.1.0¹,¹⁰.0⁴,⁹.0¹²,¹⁴]hexadecane-13-carboxylic acid)

INCHI for NP0259277 (6-hydroxy-5-(methoxycarbonyl)-5,9-dimethylpentacyclo[11.2.1.0¹,¹⁰.0⁴,⁹.0¹²,¹⁴]hexadecane-13-carboxylic acid)

Structure for NP0259277 (6-hydroxy-5-(methoxycarbonyl)-5,9-dimethylpentacyclo[11.2.1.0¹,¹⁰.0⁴,⁹.0¹²,¹⁴]hexadecane-13-carboxylic acid)

3D Structure for NP0259277 (6-hydroxy-5-(methoxycarbonyl)-5,9-dimethylpentacyclo[11.2.1.0¹,¹⁰.0⁴,⁹.0¹²,¹⁴]hexadecane-13-carboxylic acid)