NP-MRD: Showing NP-Card for (1s,4s,5s,6r,9r,10r,13r)-10-hydroxy-5,9,14-trimethyl-6-[(2-methylpropanoyl)oxy]tetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadec-14-ene-5-carboxylic acid (NP0235980)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-06 18:46:06 UTC

Updated at

2022-09-06 18:46:06 UTC

NP-MRD ID

NP0235980

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,4s,5s,6r,9r,10r,13r)-10-hydroxy-5,9,14-trimethyl-6-[(2-methylpropanoyl)oxy]tetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadec-14-ene-5-carboxylic acid

Description

(1S,4S,5S,6R,9R,10R,13R)-10-hydroxy-5,9,14-trimethyl-6-[(2-methylpropanoyl)oxy]tetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]Hexadec-14-ene-5-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. (1s,4s,5s,6r,9r,10r,13r)-10-hydroxy-5,9,14-trimethyl-6-[(2-methylpropanoyl)oxy]tetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadec-14-ene-5-carboxylic acid is found in Polymnia canadensis. Based on a literature review very few articles have been published on (1S,4S,5S,6R,9R,10R,13R)-10-hydroxy-5,9,14-trimethyl-6-[(2-methylpropanoyl)oxy]tetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]Hexadec-14-ene-5-carboxylic acid.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309062220462D          

 29 32  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  1  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  2  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
    4.4487    1.3579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4599    1.0381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4246    1.8624    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1914    0.6566    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3206   -0.0133    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.1262    0.1646    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6831   -0.4441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4887   -0.2662    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4344   -1.2307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9913   -1.8394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6288   -1.4086    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
    4.2663   -0.9778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7095   -0.3691    0.0000 C   0  0  2  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
    2.8883   -0.5708    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0004   -1.3882    0.0000 O   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  2  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  1  0  0  0  0
  2  3  2  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
  7  6  1  6  0  0  0
  7  8  1  0  0  0  0
  8  9  1  1  0  0  0
  8 10  1  6  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
  8 13  1  0  0  0  0
 13 14  1  6  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 13 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
  7 22  1  0  0  0  0
 22 23  1  6  0  0  0
 22 24  1  0  0  0  0
  4 24  1  0  0  0  0
 24 25  1  1  0  0  0
 24 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
  2 28  1  0  0  0  0
 28 29  1  6  0  0  0
  4 29  1  6  0  0  0
M  END


  Mrv1652309062220462D          

 29 32  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  1  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  2  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
    4.4487    1.3579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4599    1.0381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4246    1.8624    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1914    0.6566    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3206   -0.0133    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.1262    0.1646    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6831   -0.4441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4887   -0.2662    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4344   -1.2307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9913   -1.8394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6288   -1.4086    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
    4.2663   -0.9778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7095   -0.3691    0.0000 C   0  0  2  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
    2.8883   -0.5708    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0004   -1.3882    0.0000 O   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  2  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  1  0  0  0  0
  2  3  2  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
  7  6  1  6  0  0  0
  7  8  1  0  0  0  0
  8  9  1  1  0  0  0
  8 10  1  6  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
  8 13  1  0  0  0  0
 13 14  1  6  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 13 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
  7 22  1  0  0  0  0
 22 23  1  6  0  0  0
 22 24  1  0  0  0  0
  4 24  1  0  0  0  0
 24 25  1  1  0  0  0
 24 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
  2 28  1  0  0  0  0
 28 29  1  6  0  0  0
  4 29  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0235980

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)C(=O)O[C@@H]1CC[C@]2(C)[C@H](CC[C@@]34C[C@@H](CC[C@@]23O)C(C)=C4)[C@]1(C)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C24H36O5/c1-14(2)19(25)29-18-8-9-21(4)17(22(18,5)20(26)27)7-10-23-12-15(3)16(13-23)6-11-24(21,23)28/h12,14,16-18,28H,6-11,13H2,1-5H3,(H,26,27)/t16-,17+,18-,21-,22+,23-,24-/m1/s1

> <INCHI_KEY>
ISOHYHVXOVWOIT-AJFVNCRVSA-N

> <FORMULA>
C24H36O5

> <MOLECULAR_WEIGHT>
404.547

> <EXACT_MASS>
404.256274259

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
65

> <JCHEM_AVERAGE_POLARIZABILITY>
45.361269825093004

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,4S,5S,6R,9R,10R,13R)-10-hydroxy-5,9,14-trimethyl-6-[(2-methylpropanoyl)oxy]tetracyclo[11.2.1.0^{1,10}.0^{4,9}]hexadec-14-ene-5-carboxylic acid

> <JCHEM_LOGP>
4.200341257666667

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.507292991818409

> <JCHEM_PKA_STRONGEST_BASIC>
0.5648493901620024

> <JCHEM_POLAR_SURFACE_AREA>
83.83

> <JCHEM_REFRACTIVITY>
109.67859999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1S,4S,5S,6R,9R,10R,13R)-10-hydroxy-5,9,14-trimethyl-6-[(2-methylpropanoyl)oxy]tetracyclo[11.2.1.0^{1,10}.0^{4,9}]hexadec-14-ene-5-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-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       8.892   1.111   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.304   2.535   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      10.192   1.938   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      10.126   3.476   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      11.557   1.226   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       9.932  -0.025   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      11.436   0.307   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      12.475  -0.829   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      13.979  -0.497   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      12.011  -2.297   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      13.050  -3.434   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      10.507  -2.629   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       9.468  -1.493   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       7.964  -1.825   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       6.924  -0.689   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       6.477  -2.163   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       5.392  -1.066   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       5.601  -2.591   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       4.934  -2.642   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       3.356  -2.939   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       2.310  -1.708   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       3.386  -0.839   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   28                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   24   29                                             
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   22                                                  
CONECT    8    7    9   10   13                                             
CONECT    9    8                                                            
CONECT   10    8   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10                                                            
CONECT   13    8   14   20                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17                                                            
CONECT   20   13   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21    7   23   24                                             
CONECT   23   22                                                            
CONECT   24   22    4   25   26                                             
CONECT   25   24                                                            
CONECT   26   24   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27    2   29                                                  
CONECT   29   28    4                                                       
MASTER        0    0    0    0    0    0    0    0   29    0   64    0
END

View in JSmol

Synonyms

Value	Source
(1S,4S,5S,6R,9R,10R,13R)-10-Hydroxy-5,9,14-trimethyl-6-[(2-methylpropanoyl)oxy]tetracyclo[11.2.1.0,.0,]hexadec-14-ene-5-carboxylate	Generator

Chemical Formula

C₂₄H₃₆O₅

Average Mass

404.5470 Da

Monoisotopic Mass

404.25627 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

CC(C)C(=O)O[C@@H]1CC[C@]2(C)[C@H](CC[C@@]34C[C@@H](CC[C@@]23O)C(C)=C4)[C@]1(C)C(O)=O

InChI Identifier

InChI=1S/C24H36O5/c1-14(2)19(25)29-18-8-9-21(4)17(22(18,5)20(26)27)7-10-23-12-15(3)16(13-23)6-11-24(21,23)28/h12,14,16-18,28H,6-11,13H2,1-5H3,(H,26,27)/t16-,17+,18-,21-,22+,23-,24-/m1/s1

InChI Key

ISOHYHVXOVWOIT-AJFVNCRVSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Polymnia canadensis	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
Steroid
Dicarboxylic acid or derivatives
Tertiary alcohol
Cyclic alcohol
Carboxylic acid ester
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
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

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

162845516

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1s,4s,5s,6r,9r,10r,13r)-10-hydroxy-5,9,14-trimethyl-6-[(2-methylpropanoyl)oxy]tetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadec-14-ene-5-carboxylic acid (NP0235980)

MOL for NP0235980 ((1s,4s,5s,6r,9r,10r,13r)-10-hydroxy-5,9,14-trimethyl-6-[(2-methylpropanoyl)oxy]tetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadec-14-ene-5-carboxylic acid)

3D MOL for NP0235980 ((1s,4s,5s,6r,9r,10r,13r)-10-hydroxy-5,9,14-trimethyl-6-[(2-methylpropanoyl)oxy]tetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadec-14-ene-5-carboxylic acid)

3D SDF for NP0235980 ((1s,4s,5s,6r,9r,10r,13r)-10-hydroxy-5,9,14-trimethyl-6-[(2-methylpropanoyl)oxy]tetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadec-14-ene-5-carboxylic acid)

3D-SDF for NP0235980 ((1s,4s,5s,6r,9r,10r,13r)-10-hydroxy-5,9,14-trimethyl-6-[(2-methylpropanoyl)oxy]tetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadec-14-ene-5-carboxylic acid)

PDB for NP0235980 ((1s,4s,5s,6r,9r,10r,13r)-10-hydroxy-5,9,14-trimethyl-6-[(2-methylpropanoyl)oxy]tetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadec-14-ene-5-carboxylic acid)

3D PDB for NP0235980 ((1s,4s,5s,6r,9r,10r,13r)-10-hydroxy-5,9,14-trimethyl-6-[(2-methylpropanoyl)oxy]tetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadec-14-ene-5-carboxylic acid)

SMILES for NP0235980 ((1s,4s,5s,6r,9r,10r,13r)-10-hydroxy-5,9,14-trimethyl-6-[(2-methylpropanoyl)oxy]tetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadec-14-ene-5-carboxylic acid)

INCHI for NP0235980 ((1s,4s,5s,6r,9r,10r,13r)-10-hydroxy-5,9,14-trimethyl-6-[(2-methylpropanoyl)oxy]tetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadec-14-ene-5-carboxylic acid)

Structure for NP0235980 ((1s,4s,5s,6r,9r,10r,13r)-10-hydroxy-5,9,14-trimethyl-6-[(2-methylpropanoyl)oxy]tetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadec-14-ene-5-carboxylic acid)

3D Structure for NP0235980 ((1s,4s,5s,6r,9r,10r,13r)-10-hydroxy-5,9,14-trimethyl-6-[(2-methylpropanoyl)oxy]tetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadec-14-ene-5-carboxylic acid)