NP-MRD: Showing NP-Card for (5r,9s,13s)-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane-5-carboxylic acid (NP0254154)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-07 18:13:42 UTC

Updated at

2022-09-07 18:13:42 UTC

NP-MRD ID

NP0254154

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(5r,9s,13s)-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane-5-carboxylic acid

Description

Ent-Kaur-16-en-19-oic acid, also known as argyrophilic 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. (5r,9s,13s)-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane-5-carboxylic acid is found in Alepidea serrata, Annona glabra, Annona reticulata, Annona squamosa, Apis mellifera, Aralia cordata, Argyrochosma pallens, Aspilia mossambicensis, Aspilia pluriseta, Bahia ambrosioides, Bedfordia arborescens, Calanticaria greggii, Calocephalus knappii, Hyptis spicigera, Casearia corymbosa, Chrozophora oblongifolia, Copaifera langsdorffii, Critonia hebebotrya, Croton tricolor, Dendroviguiera insignis, Disynaphia multicrenulata, Eleutherococcus trichodon, Eleutherococcus trifoliatus, Espeletia semiglobulata, Guizotia scabra, Helianthus annuus, Helianthus heterophyllus, Helianthus petiolaris, Helianthus porteri, Helianthus radula, Helianthus simulans, Helichrysum kraussii, Helichrysum reflexum, Iostephane heterophylla, Iostephane madrensis, Lasianthaea fruticosa, Loxothysanus sinuatus, Mikania hirsutissima, Mikania vitifolia, Mitrephora celebica, Montanoa frutescens, Montanoa leucantha, Montanoa speciosa, Montanoa tomentosa, Nassauvia darwinii, Othonna sedifolia, Oyedaea verbesinoides, Ozothamnus retusus, Ozothamnus scutellifolius, Pappobolus stuebelii, Perymeniopsis ovalifolia, Porella densifolia, Pseudognaphalium montevidense, Pseudognaphalium viravira, Pseudognaphalium viscosum, Robinsonia thurifera, Sagittaria trifolia, Senecio asperulus, Smallanthus sonchifolius, Solidago missouriensis, Solidago nemoralis, Solidago rugosa, Sphagneticola calendulacea, Sphagneticola trilobata, Stevia lucida, Stevia monardifolia, Viguiera dentata, Viguiera hypargyrea, Viguiera linearis, Dendroviguiera oaxacana, Aldama robusta, Dendroviguiera sylvatica, Wedelia acapulcensis, Wedelia chinensis, Wedelia prostrata, Xylopia aethiopica and Xylopia frutescens. Based on a literature review very few articles have been published on ent-Kaur-16-en-19-oic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 52 55  0  0  0  0  0  0  0  0999 V2000
    4.8277    0.5712    1.6518 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7212    0.3984    0.9737 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3360    0.5026    1.4716 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4501    0.5645    0.2153 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5001    1.6849    0.4085 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7725    1.3006    1.0876 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3670   -0.0047    0.6735 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6355   -0.7516   -0.3897 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9909   -2.2534   -0.2791 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9903   -0.3505   -1.7743 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9575    0.7591   -1.9318 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9943    0.9334   -0.9041 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8216    0.2529    0.3992 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.2881    1.1838    1.5367 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7010   -0.9145    0.4738 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4884   -1.2403   -0.4351 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6544   -1.6979    1.6173 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8344   -0.7521   -0.0618 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6922   -1.4840   -1.0361 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1403   -1.3429   -0.5642 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6185    0.0557   -0.4625 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4585    0.9836   -0.8522 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7742    0.8228    2.7114 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8256    0.4850    1.2454 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1642    1.3563    2.1342 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0482   -0.4102    2.0550 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3692    2.2033   -0.5643 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9986    2.4670    1.0568 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4656    2.1772    0.9434 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5597    1.3192    2.1984 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3579   -0.6851    1.5801 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4693   -2.7056   -1.1773 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5897   -2.6782    0.6491 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0428   -2.4578   -0.4735 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0529   -0.0533   -2.3349 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3672   -1.2131   -2.4066 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3928    1.7268   -2.1028 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4843    0.6436   -2.9305 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0215    0.6634   -1.2965 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1070    2.0412   -0.7003 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5851    1.2035    2.3730 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2672    0.8702    1.9555 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4930    2.2086    1.1094 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2752   -2.4651    1.8001 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9020   -1.3493    0.9017 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5945   -1.2088   -2.0800 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5469   -2.6056   -0.9990 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1806   -1.9110    0.4053 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8223   -1.9252   -1.2512 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5269    0.2845   -1.0370 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7106    2.0378   -0.6734 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1501    0.7593   -1.8627 H   0  0  0  0  0  0  0  0  0  0  0  0
  8  9  1  6
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13  7  1  0
  7  6  1  0
  6  5  1  0
  4  5  1  1
  4 22  1  0
 22 21  1  0
 21 20  1  0
 20 19  1  0
 19 18  1  0
 21  2  1  0
  2  1  2  3
  2  3  1  0
 13 15  1  6
 15 17  1  0
 15 16  2  0
  7  8  1  0
 18  4  1  0
 18  8  1  0
  3  4  1  0
  9 32  1  0
  9 33  1  0
  9 34  1  0
 10 35  1  0
 10 36  1  0
 11 37  1  0
 11 38  1  0
 12 39  1  0
 12 40  1  0
 14 41  1  0
 14 42  1  0
 14 43  1  0
  7 31  1  1
  6 29  1  0
  6 30  1  0
  5 27  1  0
  5 28  1  0
 22 51  1  0
 22 52  1  0
 21 50  1  6
 20 48  1  0
 20 49  1  0
 19 46  1  0
 19 47  1  0
 18 45  1  1
  1 23  1  0
  1 24  1  0
  3 25  1  0
  3 26  1  0
 17 44  1  0
M  END


  Mrv1652309072220132D          

 22 25  0  0  1  0            999 V2000
    0.0435   -0.0007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8566   -0.1407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4794    0.4660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2893    0.0832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5946    0.8699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4039    1.0366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9582    0.4175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7095   -0.3691    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4700   -1.1586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2663   -0.9778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0719   -0.7999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3206   -0.0133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7638    0.5954    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.3527    1.1732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6141    1.4067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8366    1.6827    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2418    1.9420    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8883   -0.5708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6431   -1.4156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7976   -1.5743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2377   -0.9152    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8140   -0.4494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  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  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  6  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
  7 13  1  0  0  0  0
 13 14  1  1  0  0  0
 13 15  1  6  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
  8 18  1  0  0  0  0
  4 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
 21  2  1  6  0  0  0
 21 22  1  0  0  0  0
  4 22  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0254154

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@]12CCC[C@](C)(C1CCC13C[C@H](CCC21)C(=C)C3)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C20H30O2/c1-13-11-20-10-7-15-18(2,16(20)6-5-14(13)12-20)8-4-9-19(15,3)17(21)22/h14-16H,1,4-12H2,2-3H3,(H,21,22)/t14-,15?,16?,18+,19+,20?/m0/s1

> <INCHI_KEY>
NIKHGUQULKYIGE-ZTJPGZAWSA-N

> <FORMULA>
C20H30O2

> <MOLECULAR_WEIGHT>
302.458

> <EXACT_MASS>
302.224580206

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
52

> <JCHEM_AVERAGE_POLARIZABILITY>
35.29571329617911

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(5R,9S,13S)-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.0^{1,10}.0^{4,9}]hexadecane-5-carboxylic acid

> <JCHEM_LOGP>
4.8078307643333345

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.839023750520022

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
87.36359999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(5R,9S,13S)-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.0^{1,10}.0^{4,9}]hexadecane-5-carboxylic acid

> <JCHEM_VEBER_RULE>
1

$$$$

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       0.081  -0.001   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.599  -0.263   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.761   0.870   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.273   0.155   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.843   1.624   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.354   1.935   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.389   0.779   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.924  -0.689   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.477  -2.163   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.964  -1.825   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.468  -1.493   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.932  -0.025   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.892   1.111   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.992   2.190   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.613   2.626   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       7.162   3.141   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       9.785   3.625   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       5.392  -1.066   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.934  -2.642   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.356  -2.939   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.310  -1.708   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       3.386  -0.839   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   21                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   18   22                                             
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   13                                                  
CONECT    8    7    9   10   18                                             
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12    7   14   15                                             
CONECT   14   13                                                            
CONECT   15   13   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15                                                            
CONECT   18    8    4   19                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20    2   22                                                  
CONECT   22   21    4                                                       
MASTER        0    0    0    0    0    0    0    0   22    0   50    0
END

View in JSmol

Synonyms

Value	Source
ent-Kaur-16-en-19-Oate	Generator
Argyrophilic acid	MeSH
Kaur-16-en-19-Oic acid	MeSH

Chemical Formula

C₂₀H₃₀O₂

Average Mass

302.4580 Da

Monoisotopic Mass

302.22458 Da

IUPAC Name

(5R,9S,13S)-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.0^{1,10}.0^{4,9}]hexadecane-5-carboxylic acid

Traditional Name

(5R,9S,13S)-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.0^{1,10}.0^{4,9}]hexadecane-5-carboxylic acid

CAS Registry Number

Not Available

SMILES

C[C@@]12CCC[C@](C)(C1CCC13C[C@H](CCC21)C(=C)C3)C(O)=O

InChI Identifier

InChI=1S/C20H30O2/c1-13-11-20-10-7-15-18(2,16(20)6-5-14(13)12-20)8-4-9-19(15,3)17(21)22/h14-16H,1,4-12H2,2-3H3,(H,21,22)/t14-,15?,16?,18+,19+,20?/m0/s1

InChI Key

NIKHGUQULKYIGE-ZTJPGZAWSA-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
Alepidea serrata	LOTUS Database	35616633
Annona glabra	LOTUS Database	35616633
Annona reticulata	LOTUS Database	35616633
Annona squamosa	LOTUS Database	35616633
Apis mellifera	LOTUS Database	35616633
Aralia cordata	LOTUS Database	35616633
Argyrochosma pallens	LOTUS Database	35616633
Aspilia mossambicensis	LOTUS Database	35616633
Aspilia pluriseta	LOTUS Database	35616633
Bahia ambrosioides	LOTUS Database	35616633
Bedfordia arborescens	LOTUS Database	35616633
Calanticaria greggii	LOTUS Database	35616633
Calocephalus knappii	LOTUS Database	35616633
Cantinoa americana	LOTUS Database	35616633
Casearia corymbosa	LOTUS Database	35616633
Chrozophora oblongifolia	LOTUS Database	35616633
Copaifera langsdorffii	LOTUS Database	35616633
Critonia hebebotrya	LOTUS Database	35616633
Croton tricolor	LOTUS Database	35616633
Dendroviguiera insignis	LOTUS Database	35616633
Disynaphia multicrenulata	LOTUS Database	35616633
Eleutherococcus trichodon	LOTUS Database	35616633
Eleutherococcus trifoliatus	LOTUS Database	35616633
Espeletia semiglobulata	LOTUS Database	35616633
Guizotia scabra	LOTUS Database	35616633
Helianthus annuus	LOTUS Database	35616633
Helianthus heterophyllus	LOTUS Database	35616633
Helianthus petiolaris	LOTUS Database	35616633
Helianthus porteri	LOTUS Database	35616633
Helianthus radula	LOTUS Database	35616633
Helianthus simulans	LOTUS Database	35616633
Helichrysum kraussii	LOTUS Database	35616633
Helichrysum reflexum	LOTUS Database	35616633
Iostephane heterophylla	LOTUS Database	35616633
Iostephane madrensis	LOTUS Database	35616633
Lasianthaea fruticosa	LOTUS Database	35616633
Loxothysanus sinuatus	LOTUS Database	35616633
Mikania hirsutissima	LOTUS Database	35616633
Mikania vitifolia	LOTUS Database	35616633
Mitrephora celebica	LOTUS Database	35616633
Montanoa frutescens	LOTUS Database	35616633
Montanoa leucantha	LOTUS Database	35616633
Montanoa speciosa	LOTUS Database	35616633
Montanoa tomentosa	LOTUS Database	35616633
Nassauvia darwinii	LOTUS Database	35616633
Othonna sedifolia	LOTUS Database	35616633
Oyedaea verbesinoides	LOTUS Database	35616633
Ozothamnus retusus	LOTUS Database	35616633
Ozothamnus scutellifolius	LOTUS Database	35616633
Pappobolus stuebelii	LOTUS Database	35616633
Perymeniopsis ovalifolia	LOTUS Database	35616633
Porella densifolia	LOTUS Database	35616633
Pseudognaphalium montevidense	LOTUS Database	35616633
Pseudognaphalium viravira	LOTUS Database	35616633
Pseudognaphalium viscosum	LOTUS Database	35616633
Robinsonia thurifera	LOTUS Database	35616633
Sagittaria trifolia	LOTUS Database	35616633
Senecio asperulus	LOTUS Database	35616633
Smallanthus sonchifolius	LOTUS Database	35616633
Solidago missouriensis	LOTUS Database	35616633
Solidago nemoralis	LOTUS Database	35616633
Solidago rugosa	LOTUS Database	35616633
Sphagneticola calendulacea	LOTUS Database	35616633
Sphagneticola trilobata	LOTUS Database	35616633
Stevia lucida	LOTUS Database	35616633
Stevia monardifolia	LOTUS Database	35616633
Viguiera dentata	LOTUS Database	35616633
Viguiera hypargyrea	LOTUS Database	35616633
Viguiera linearis	LOTUS Database	35616633
Viguiera oaxacana	LOTUS Database	35616633
Viguiera robusta	LOTUS Database	35616633
Viguiera sylvatica	LOTUS Database	35616633
Wedelia acapulcensis	LOTUS Database	35616633
Wedelia chinensis	LOTUS Database	35616633
Wedelia prostrata	LOTUS Database	35616633
Xylopia aethiopica	LOTUS Database	35616633
Xylopia frutescens	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

Kaurane diterpenoid
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
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	4.81	ChemAxon
pKa (Strongest Acidic)	4.84	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	37.3 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	87.36 m³·mol⁻¹	ChemAxon
Polarizability	35.3 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	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

C00000881

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

49775756

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (5r,9s,13s)-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane-5-carboxylic acid (NP0254154)

MOL for NP0254154 ((5r,9s,13s)-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane-5-carboxylic acid)

3D MOL for NP0254154 ((5r,9s,13s)-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane-5-carboxylic acid)

3D SDF for NP0254154 ((5r,9s,13s)-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane-5-carboxylic acid)

3D-SDF for NP0254154 ((5r,9s,13s)-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane-5-carboxylic acid)

PDB for NP0254154 ((5r,9s,13s)-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane-5-carboxylic acid)

3D PDB for NP0254154 ((5r,9s,13s)-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane-5-carboxylic acid)

SMILES for NP0254154 ((5r,9s,13s)-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane-5-carboxylic acid)

INCHI for NP0254154 ((5r,9s,13s)-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane-5-carboxylic acid)

Structure for NP0254154 ((5r,9s,13s)-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane-5-carboxylic acid)

3D Structure for NP0254154 ((5r,9s,13s)-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane-5-carboxylic acid)