NP-MRD: Showing NP-Card for cladoic acid (NP0333608)

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Record Information

Version

2.0

Created at

2024-07-16 01:45:18 UTC

Updated at

2025-12-20 14:41:06 UTC

NP-MRD ID

NP0333608

Natural Product DOI

https://doi.org/10.57994/3087

Secondary Accession Numbers

None

Natural Product Identification

Common Name

cladoic acid

Description

Cladoic acid is also known as cladoate. cladoic acid was first documented in 2024 (PMID: 39101838). Based on a literature review very few articles have been published on cladoic acid.

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 03302304192D          

 29 30  0  0  1  0            999 V2000
   -2.8579    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.0000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7145    0.4125    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4289   -0.8250    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0000   -0.8250    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    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  1  0  0  0  0
  3  5  2  0  0  0  0
  2  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 11 10  1  0  0  0  0
 11 12  1  1  0  0  0
 11 13  1  0  0  0  0
 13 14  1  6  0  0  0
 15 13  1  0  0  0  0
 15 16  1  1  0  0  0
 17 15  1  0  0  0  0
 17 18  1  6  0  0  0
 19 17  1  0  0  0  0
 19 20  1  1  0  0  0
 19 21  1  0  0  0  0
 21 11  1  0  0  0  0
 21 22  1  6  0  0  0
 21 23  1  0  0  0  0
 23 24  1  6  0  0  0
 23 25  1  0  0  0  0
 26 25  1  0  0  0  0
 26 27  1  6  0  0  0
 28 26  1  0  0  0  0
 19 28  1  0  0  0  0
 28 29  1  1  0  0  0
M  END


  Mrv2104 03302304192D          

 29 30  0  0  1  0            999 V2000
   -2.8579    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.0000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7145    0.4125    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4289   -0.8250    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0000   -0.8250    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    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  1  0  0  0  0
  3  5  2  0  0  0  0
  2  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 11 10  1  0  0  0  0
 11 12  1  1  0  0  0
 11 13  1  0  0  0  0
 13 14  1  6  0  0  0
 15 13  1  0  0  0  0
 15 16  1  1  0  0  0
 17 15  1  0  0  0  0
 17 18  1  6  0  0  0
 19 17  1  0  0  0  0
 19 20  1  1  0  0  0
 19 21  1  0  0  0  0
 21 11  1  0  0  0  0
 21 22  1  6  0  0  0
 21 23  1  0  0  0  0
 23 24  1  6  0  0  0
 23 25  1  0  0  0  0
 26 25  1  0  0  0  0
 26 27  1  6  0  0  0
 28 26  1  0  0  0  0
 19 28  1  0  0  0  0
 28 29  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0333608

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@]1(\C=C\C=C\C=C(/C)C(O)=O)[C@@H](C)[C@H](O)[C@@H](O)[C@@]2([H])[C@H](O)[C@@H](C)C[C@@H](C)[C@]12[H]

> <INCHI_IDENTIFIER>
InChI=1S/C21H32O5/c1-11(21(25)26)8-6-5-7-9-15-14(4)19(23)20(24)17-16(15)12(2)10-13(3)18(17)22/h5-9,12-20,22-24H,10H2,1-4H3,(H,25,26)/b6-5+,9-7+,11-8+/t12-,13+,14-,15+,16-,17-,18-,19+,20+/m1/s1

> <INCHI_KEY>
NRPIVQWEMAFMCD-OKWAWBIYSA-N

> <FORMULA>
C21H32O5

> <MOLECULAR_WEIGHT>
364.482

> <EXACT_MASS>
364.22497413

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
58

> <JCHEM_AVERAGE_POLARIZABILITY>
41.48570391807149

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2E,4E,6E)-7-[(1R,2R,3S,4S,4aR,5R,6S,8R,8aR)-3,4,5-trihydroxy-2,6,8-trimethyl-decahydronaphthalen-1-yl]-2-methylhepta-2,4,6-trienoic acid

> <JCHEM_LOGP>
2.2587161419999995

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
13.559094229385462

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.196851240331975

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9703082808482115

> <JCHEM_POLAR_SURFACE_AREA>
97.99000000000001

> <JCHEM_REFRACTIVITY>
103.62310000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(2E,4E,6E)-7-[(1R,2R,3S,4S,4aR,5R,6S,8R,8aR)-3,4,5-trihydroxy-2,6,8-trimethyl-decahydronaphthalen-1-yl]-2-methylhepta-2,4,6-trienoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 30-MAR-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   30-MAR-23         0                                  
HETATM    1  C   UNK     0      -5.335   6.160   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.001   6.930   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -4.001   8.470   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -5.335   9.240   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      -2.667   9.240   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      -2.667   6.160   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.667   4.620   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM   12  H   UNK     0       1.334   0.770   0.000  0.00  0.00           H+0
HETATM   13  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -2.667  -3.080   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       0.000  -4.620   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   20  H   UNK     0       2.667  -1.540   0.000  0.00  0.00           H+0
HETATM   21  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   22  H   UNK     0       0.000  -1.540   0.000  0.00  0.00           H+0
HETATM   23  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    6                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3                                                            
CONECT    6    2    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   13   21                                             
CONECT   12   11                                                            
CONECT   13   11   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20   21   28                                             
CONECT   20   19                                                            
CONECT   21   19   11   22   23                                             
CONECT   22   21                                                            
CONECT   23   21   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   19   29                                                  
CONECT   29   28                                                            
MASTER        0    0    0    0    0    0    0    0   29    0   60    0
END

View in JSmol

Synonyms

Value	Source
Cladoate	Generator

Chemical Formula

C₂₁H₃₂O₅

Average Mass

364.4820 Da

Monoisotopic Mass

364.22497 Da

IUPAC Name

(2E,4E,6E)-7-[(1R,2R,3S,4S,4aR,5R,6S,8R,8aR)-3,4,5-trihydroxy-2,6,8-trimethyl-decahydronaphthalen-1-yl]-2-methylhepta-2,4,6-trienoic acid

Traditional Name

(2E,4E,6E)-7-[(1R,2R,3S,4S,4aR,5R,6S,8R,8aR)-3,4,5-trihydroxy-2,6,8-trimethyl-decahydronaphthalen-1-yl]-2-methylhepta-2,4,6-trienoic acid

CAS Registry Number

Not Available

SMILES

[H][C@]1(\C=C\C=C\C=C(/C)C(O)=O)[C@@H](C)[C@H](O)[C@@H](O)[C@@]2([H])[C@H](O)[C@@H](C)C[C@@H](C)[C@]12[H]

InChI Identifier

InChI=1S/C21H32O5/c1-11(21(25)26)8-6-5-7-9-15-14(4)19(23)20(24)17-16(15)12(2)10-13(3)18(17)22/h5-9,12-20,22-24H,10H2,1-4H3,(H,25,26)/b6-5+,9-7+,11-8+/t12-,13+,14-,15+,16-,17-,18-,19+,20+/m1/s1

InChI Key

NRPIVQWEMAFMCD-OKWAWBIYSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, CD3OD, experimental)	urabe@pu-toyama.ac.jp	Toyama Prefectural University	Daisuke Urabe	2024-07-16	View Spectrum
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 500 MHz, CD3OD, experimental)	urabe@pu-toyama.ac.jp	Toyama Prefectural University	Daisuke Urabe	2024-07-16	View Spectrum
NOESY NMR	[¹H, ¹H] NMR Spectrum (2D, 500 MHz, CD3OD, experimental)	urabe@pu-toyama.ac.jp	Toyama Prefectural University	Daisuke Urabe	2024-07-16	View Spectrum
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 500 MHz, CD3OD, experimental)	urabe@pu-toyama.ac.jp	Toyama Prefectural University	Daisuke Urabe	2024-07-16	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 500 MHz, CD3OD, experimental)	urabe@pu-toyama.ac.jp	Toyama Prefectural University	Daisuke Urabe	2024-07-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CD3OD, experimental)	urabe@pu-toyama.ac.jp	Toyama Prefectural University	Daisuke Urabe	2024-07-16	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

This compound belongs to the class of organic compounds known as hydroxy fatty acids. These are fatty acids in which the chain bears a hydroxyl group.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acids and conjugates

Direct Parent

Hydroxy fatty acids

Alternative Parents

Substituents

Methyl-branched fatty acid
Hydroxy fatty acid
Branched fatty acid
Unsaturated fatty acid
Cyclic alcohol
Secondary alcohol
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
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	2.26	ChemAxon
pKa (Strongest Acidic)	4.2	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	97.99 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	103.62 m³·mol⁻¹	ChemAxon
Polarizability	41.49 Å³	ChemAxon
Number of Rings	2	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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Rana MM, Lu S, Menjivar TA, Fukaya K, Nakajima-Shimada J, Urabe D, Igarashi Y: Cladoic Acid, an Anti-Trypanosoma cruzi Polyketide from Cladosporium sp. TP-F2020. J Nat Prod. 2024 Aug 23;87(8):2126-2131. doi: 10.1021/acs.jnatprod.4c00567. Epub 2024 Aug 5. [PubMed:39101838 ]
DOI: 10.1021/acs.jnatprod.4c00567
PMID: 39101838

Showing NP-Card for cladoic acid (NP0333608)

MOL for NP0333608 (cladoic acid)

3D MOL for NP0333608 (cladoic acid)

3D SDF for NP0333608 (cladoic acid)

3D-SDF for NP0333608 (cladoic acid)

PDB for NP0333608 (cladoic acid)

3D PDB for NP0333608 (cladoic acid)

SMILES for NP0333608 (cladoic acid)

INCHI for NP0333608 (cladoic acid)

Structure for NP0333608 (cladoic acid)

3D Structure for NP0333608 (cladoic acid)