NP-MRD: Showing NP-Card for (1s,2r,5s,9s,10r,13r,14r,15r,18s)-2,6,6,9-tetramethyl-15-(prop-1-en-2-yl)pentacyclo[11.7.0.0²,¹⁰.0⁵,⁹.0¹⁴,¹⁸]icos-7-ene-1,18-dicarboxylic acid (NP0307454)

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Record Information

Version

2.0

Created at

2022-09-11 00:35:18 UTC

Updated at

2022-09-11 00:35:18 UTC

NP-MRD ID

NP0307454

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,2r,5s,9s,10r,13r,14r,15r,18s)-2,6,6,9-tetramethyl-15-(prop-1-en-2-yl)pentacyclo[11.7.0.0²,¹⁰.0⁵,⁹.0¹⁴,¹⁸]icos-7-ene-1,18-dicarboxylic acid

Description

Ceanothenic Acid, also known as ceanothenate, belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. (1s,2r,5s,9s,10r,13r,14r,15r,18s)-2,6,6,9-tetramethyl-15-(prop-1-en-2-yl)pentacyclo[11.7.0.0²,¹⁰.0⁵,⁹.0¹⁴,¹⁸]icos-7-ene-1,18-dicarboxylic acid is found in Ziziphus mauritiana. (1s,2r,5s,9s,10r,13r,14r,15r,18s)-2,6,6,9-tetramethyl-15-(prop-1-en-2-yl)pentacyclo[11.7.0.0²,¹⁰.0⁵,⁹.0¹⁴,¹⁸]icos-7-ene-1,18-dicarboxylic acid was first documented in 2009 (PMID: 19359121). Based on a literature review a small amount of articles have been published on Ceanothenic Acid (PMID: 27452452) (PMID: 22989532) (PMID: 21665400).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309112202352D          

 33 37  0  0  1  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652309112202352D          

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 12 13  1  0  0  0  0
 13 14  1  1  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 13 17  1  0  0  0  0
 17 18  1  1  0  0  0
 18 19  1  0  0  0  0
 20 19  1  6  0  0  0
 20 21  1  0  0  0  0
 21 22  1  6  0  0  0
 21 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 25 28  1  0  0  0  0
 21 28  1  0  0  0  0
 28 29  1  6  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 20 31  1  0  0  0  0
 13 31  1  0  0  0  0
 31 32  1  6  0  0  0
 17 33  1  0  0  0  0
 33  4  1  6  0  0  0
  7 33  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0307454

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=C)[C@@H]1CC[C@@]2(CC[C@@]3([C@H](CC[C@@H]4[C@@]5(C)C=CC(C)(C)[C@@H]5CC[C@@]34C)[C@@H]12)C(O)=O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C29H42O4/c1-17(2)18-9-12-28(23(30)31)15-16-29(24(32)33)19(22(18)28)7-8-21-26(5)14-13-25(3,4)20(26)10-11-27(21,29)6/h13-14,18-22H,1,7-12,15-16H2,2-6H3,(H,30,31)(H,32,33)/t18-,19+,20-,21+,22+,26-,27+,28-,29+/m0/s1

> <INCHI_KEY>
CMDOQXSBVNWCEM-AKDRKZOISA-N

> <FORMULA>
C29H42O4

> <MOLECULAR_WEIGHT>
454.651

> <EXACT_MASS>
454.308309832

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
75

> <JCHEM_AVERAGE_POLARIZABILITY>
52.029499673547036

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,2R,5S,9S,10R,13R,14R,15R,18S)-2,6,6,9-tetramethyl-15-(prop-1-en-2-yl)pentacyclo[11.7.0.0^{2,10}.0^{5,9}.0^{14,18}]icos-7-ene-1,18-dicarboxylic acid

> <JCHEM_LOGP>
6.255752424333334

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
4.947917613235357

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.276810972966621

> <JCHEM_POLAR_SURFACE_AREA>
74.6

> <JCHEM_REFRACTIVITY>
129.34279999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2R,5S,9S,10R,13R,14R,15R,18S)-2,6,6,9-tetramethyl-15-(prop-1-en-2-yl)pentacyclo[11.7.0.0^{2,10}.0^{5,9}.0^{14,18}]icos-7-ene-1,18-dicarboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 11-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-22         0                                  
HETATM    1  C   UNK     0       5.980   0.205   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.124  -0.825   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.589  -0.349   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.804  -2.331   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.397  -2.958   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.558  -4.489   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.064  -4.810   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.159  -6.055   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       6.785  -7.462   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0       4.628  -5.894   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       7.834  -6.143   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.374  -6.143   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      10.144  -4.810   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.914  -6.143   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      12.160  -7.048   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0      10.144  -7.477   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       9.374  -3.476   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      10.144  -2.142   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      11.684  -2.142   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      12.454  -3.476   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      13.994  -3.476   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      13.368  -2.069   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      15.025  -2.331   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      16.432  -2.958   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      16.271  -4.489   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      17.811  -4.489   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      16.432  -6.021   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      14.764  -4.810   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      13.994  -6.143   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      12.454  -6.143   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      11.684  -4.810   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      11.845  -6.341   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       7.834  -3.476   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   33                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   11   33                                             
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11    7   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   17   31                                             
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14                                                            
CONECT   17   13   18   33                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   31                                                  
CONECT   21   20   22   23   28                                             
CONECT   22   21                                                            
CONECT   23   21   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26   27   28                                             
CONECT   26   25                                                            
CONECT   27   25                                                            
CONECT   28   25   21   29                                                  
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   20   13   32                                             
CONECT   32   31                                                            
CONECT   33   17    4    7                                                  
MASTER        0    0    0    0    0    0    0    0   33    0   74    0
END

View in JSmol

Synonyms

Value	Source
Ceanothenate	Generator

Chemical Formula

C₂₉H₄₂O₄

Average Mass

454.6510 Da

Monoisotopic Mass

454.30831 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

CC(=C)[C@@H]1CC[C@@]2(CC[C@@]3([C@H](CC[C@@H]4[C@@]5(C)C=CC(C)(C)[C@@H]5CC[C@@]34C)[C@@H]12)C(O)=O)C(O)=O

InChI Identifier

InChI=1S/C29H42O4/c1-17(2)18-9-12-28(23(30)31)15-16-29(24(32)33)19(22(18)28)7-8-21-26(5)14-13-25(3,4)20(26)10-11-27(21,29)6/h13-14,18-22H,1,7-12,15-16H2,2-6H3,(H,30,31)(H,32,33)/t18-,19+,20-,21+,22+,26-,27+,28-,29+/m0/s1

InChI Key

CMDOQXSBVNWCEM-AKDRKZOISA-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
Ziziphus mauritiana	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Triterpenoids

Direct Parent

Triterpenoids

Alternative Parents

Substituents

Triterpenoid
19-hydroxysteroid
19-oxosteroid
3-carboxy steroid
Steroid acid
18-oxosteroid
18-hydroxysteroid
Hydroxysteroid
Oxosteroid
Steroid
Dicarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Carbonyl group
Organic oxide
Organooxygen compound
Organic oxygen 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

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

28663319

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

71451218

PDB ID

Not Available

ChEBI ID

168974

Good Scents ID

Not Available

References

General References

Muhammad D, Lalun N, Bobichon H, Le Magrex Debar E, Gangloff SC, Nour M, Voutquenne-Nazabadioko L: Triterpenoids from the leaves of Alphitonia xerocarpus Baill and their biological activity. Phytochemistry. 2016 Sep;129:45-57. doi: 10.1016/j.phytochem.2016.07.005. Epub 2016 Jul 21. [PubMed:27452452 ]
Ji CJ, Zeng GZ, Han J, He WJ, Zhang YM, Tan NH: Zizimauritic acids A-C, three novel nortriterpenes from Ziziphus mauritiana. Bioorg Med Chem Lett. 2012 Oct 15;22(20):6377-80. doi: 10.1016/j.bmcl.2012.08.074. Epub 2012 Aug 26. [PubMed:22989532 ]
Guo S, Duan JA, Tang Y, Qian Y, Zhao J, Qian D, Su S, Shang E: Simultaneous qualitative and quantitative analysis of triterpenic acids, saponins and flavonoids in the leaves of two Ziziphus species by HPLC-PDA-MS/ELSD. J Pharm Biomed Anal. 2011 Sep 10;56(2):264-70. doi: 10.1016/j.jpba.2011.05.025. Epub 2011 May 20. [PubMed:21665400 ]
Guo S, Duan JA, Tang Y, Su S, Shang E, Ni S, Qian D: High-performance liquid chromatography--two wavelength detection of triterpenoid acids from the fruits of Ziziphus jujuba containing various cultivars in different regions and classification using chemometric analysis. J Pharm Biomed Anal. 2009 Jul 12;49(5):1296-302. doi: 10.1016/j.jpba.2009.03.006. Epub 2009 Mar 20. [PubMed:19359121 ]
LOTUS database [Link]

Showing NP-Card for (1s,2r,5s,9s,10r,13r,14r,15r,18s)-2,6,6,9-tetramethyl-15-(prop-1-en-2-yl)pentacyclo[11.7.0.0²,¹⁰.0⁵,⁹.0¹⁴,¹⁸]icos-7-ene-1,18-dicarboxylic acid (NP0307454)

MOL for NP0307454 ((1s,2r,5s,9s,10r,13r,14r,15r,18s)-2,6,6,9-tetramethyl-15-(prop-1-en-2-yl)pentacyclo[11.7.0.0²,¹⁰.0⁵,⁹.0¹⁴,¹⁸]icos-7-ene-1,18-dicarboxylic acid)

3D MOL for NP0307454 ((1s,2r,5s,9s,10r,13r,14r,15r,18s)-2,6,6,9-tetramethyl-15-(prop-1-en-2-yl)pentacyclo[11.7.0.0²,¹⁰.0⁵,⁹.0¹⁴,¹⁸]icos-7-ene-1,18-dicarboxylic acid)

3D SDF for NP0307454 ((1s,2r,5s,9s,10r,13r,14r,15r,18s)-2,6,6,9-tetramethyl-15-(prop-1-en-2-yl)pentacyclo[11.7.0.0²,¹⁰.0⁵,⁹.0¹⁴,¹⁸]icos-7-ene-1,18-dicarboxylic acid)

3D-SDF for NP0307454 ((1s,2r,5s,9s,10r,13r,14r,15r,18s)-2,6,6,9-tetramethyl-15-(prop-1-en-2-yl)pentacyclo[11.7.0.0²,¹⁰.0⁵,⁹.0¹⁴,¹⁸]icos-7-ene-1,18-dicarboxylic acid)

PDB for NP0307454 ((1s,2r,5s,9s,10r,13r,14r,15r,18s)-2,6,6,9-tetramethyl-15-(prop-1-en-2-yl)pentacyclo[11.7.0.0²,¹⁰.0⁵,⁹.0¹⁴,¹⁸]icos-7-ene-1,18-dicarboxylic acid)

3D PDB for NP0307454 ((1s,2r,5s,9s,10r,13r,14r,15r,18s)-2,6,6,9-tetramethyl-15-(prop-1-en-2-yl)pentacyclo[11.7.0.0²,¹⁰.0⁵,⁹.0¹⁴,¹⁸]icos-7-ene-1,18-dicarboxylic acid)

SMILES for NP0307454 ((1s,2r,5s,9s,10r,13r,14r,15r,18s)-2,6,6,9-tetramethyl-15-(prop-1-en-2-yl)pentacyclo[11.7.0.0²,¹⁰.0⁵,⁹.0¹⁴,¹⁸]icos-7-ene-1,18-dicarboxylic acid)

INCHI for NP0307454 ((1s,2r,5s,9s,10r,13r,14r,15r,18s)-2,6,6,9-tetramethyl-15-(prop-1-en-2-yl)pentacyclo[11.7.0.0²,¹⁰.0⁵,⁹.0¹⁴,¹⁸]icos-7-ene-1,18-dicarboxylic acid)

Structure for NP0307454 ((1s,2r,5s,9s,10r,13r,14r,15r,18s)-2,6,6,9-tetramethyl-15-(prop-1-en-2-yl)pentacyclo[11.7.0.0²,¹⁰.0⁵,⁹.0¹⁴,¹⁸]icos-7-ene-1,18-dicarboxylic acid)

3D Structure for NP0307454 ((1s,2r,5s,9s,10r,13r,14r,15r,18s)-2,6,6,9-tetramethyl-15-(prop-1-en-2-yl)pentacyclo[11.7.0.0²,¹⁰.0⁵,⁹.0¹⁴,¹⁸]icos-7-ene-1,18-dicarboxylic acid)