NP-MRD: Showing NP-Card for (+)-palitantin (NP0342018)

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Record Information

Version

2.0

Created at

2024-12-04 19:46:17 UTC

Updated at

2026-02-19 09:01:37 UTC

NP-MRD ID

NP0342018

Natural Product DOI

https://doi.org/10.57994/3511

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(+)-palitantin

Description

Palitantin belongs to the class of organic compounds known as cyclic alcohols and derivatives. These are organic compounds containing an aliphatic ring substituted with at least one hydroxyl group. (+)-palitantin was first documented in 2007 (PMID: 17919000). Based on a literature review a significant number of articles have been published on Palitantin (PMID: 26669092) (PMID: 33322355) (PMID: 33892608) (PMID: 23558202) (PMID: 39615703).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 40 40  0  0  0  0  0  0  0  0999 V2000
    6.2793   -0.2110    0.1578 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7708   -0.1088    0.1422 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2320   -0.9382    1.2797 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7517   -0.8987    1.3446 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9973   -0.2296    0.5209 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5333   -0.2064    0.6060 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2060    0.4813   -0.2434 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6534    0.5022   -0.1566 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1662   -0.3172    1.0052 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6524   -0.2955    1.1323 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.9859    0.2765    2.3609 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3755    0.4572    0.0672 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.5651    1.7917    0.4454 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7694    0.4135   -1.2555 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3462    0.7224   -2.2753 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3419   -0.0402   -1.3815 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7422    0.3599   -2.6835 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4443   -0.0479   -2.8455 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6812   -0.2293    1.1956 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7368    0.6537   -0.3940 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6323   -1.1431   -0.3667 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3765   -0.4863   -0.8244 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5144    0.9700    0.2681 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5244   -1.9915    1.0896 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6464   -0.5397    2.2148 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2783   -1.4648    2.1293 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4567    0.3345   -0.2601 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0885   -0.7703    1.3850 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3104    1.0414   -1.0033 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0602    1.5369   -0.0021 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7898   -1.3510    0.8648 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6773    0.0752    1.9201 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0224   -1.3432    1.1706 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8565    1.2748    2.3462 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4060    0.0141   -0.0138 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9696    2.3316   -0.2515 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4052   -1.1654   -1.2755 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8353    1.4863   -2.7353 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3232   -0.0721   -3.5369 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2164   -0.8729   -2.3496 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  1  0
 17 18  1  0
 16  8  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  0
  2 23  1  0
  3 24  1  0
  3 25  1  0
  4 26  1  0
  5 27  1  0
  6 28  1  0
  7 29  1  0
  8 30  1  1
  9 31  1  0
  9 32  1  0
 10 33  1  1
 11 34  1  0
 12 35  1  6
 13 36  1  0
 16 37  1  1
 17 38  1  0
 17 39  1  0
 18 40  1  0
M  END


  Mrv1652309072217102D          

 18 18  0  0  1  0            999 V2000
   -1.4289    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    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  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
    1.4289   -0.0000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 O   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
    0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  1  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
   -0.7145    2.0625    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
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  8  7  1  6  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  1  0  0  0
 10 12  1  0  0  0  0
 12 13  1  1  0  0  0
 12 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
  8 16  1  0  0  0  0
 16 17  1  1  0  0  0
 17 18  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0342018

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCC\C=C\C=C\[C@@H]1C[C@@H](O)[C@@H](O)C(=O)[C@H]1CO

> <INCHI_IDENTIFIER>
InChI=1S/C14H22O4/c1-2-3-4-5-6-7-10-8-12(16)14(18)13(17)11(10)9-15/h4-7,10-12,14-16,18H,2-3,8-9H2,1H3/b5-4+,7-6+/t10-,11+,12-,14-/m1/s1

> <INCHI_KEY>
MPOXQBRZHHNMER-XZQMCIKJSA-N

> <FORMULA>
C14H22O4

> <MOLECULAR_WEIGHT>
254.326

> <EXACT_MASS>
254.151809188

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
40

> <JCHEM_AVERAGE_POLARIZABILITY>
28.414770272598737

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2R,3S,5R,6R)-3-[(1E,3E)-hepta-1,3-dien-1-yl]-5,6-dihydroxy-2-(hydroxymethyl)cyclohexan-1-one

> <JCHEM_LOGP>
1.0350276316666667

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.612727805611136

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.396312128511639

> <JCHEM_PKA_STRONGEST_BASIC>
-2.6713938949249423

> <JCHEM_POLAR_SURFACE_AREA>
77.76

> <JCHEM_REFRACTIVITY>
71.83810000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(2R,3S,5R,6R)-3-[(1E,3E)-hepta-1,3-dien-1-yl]-5,6-dihydroxy-2-(hydroxymethyl)cyclohexan-1-one

> <JCHEM_VEBER_RULE>
0

$$$$

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      -2.667  10.780   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.667   9.240   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.334   8.470   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.334   6.930   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   6.160   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       4.001  -0.770   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -1.334   3.850   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   16                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14    8   17                                                  
CONECT   17   16   18                                                       
CONECT   18   17                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   36    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₄H₂₂O₄

Average Mass

254.3260 Da

Monoisotopic Mass

254.15181 Da

IUPAC Name

(2R,3S,5R,6R)-3-[(1E,3E)-hepta-1,3-dien-1-yl]-5,6-dihydroxy-2-(hydroxymethyl)cyclohexan-1-one

Traditional Name

(2R,3S,5R,6R)-3-[(1E,3E)-hepta-1,3-dien-1-yl]-5,6-dihydroxy-2-(hydroxymethyl)cyclohexan-1-one

CAS Registry Number

Not Available

SMILES

CCC\C=C\C=C\[C@@H]1C[C@@H](O)[C@@H](O)C(=O)[C@H]1CO

InChI Identifier

InChI=1S/C14H22O4/c1-2-3-4-5-6-7-10-8-12(16)14(18)13(17)11(10)9-15/h4-7,10-12,14-16,18H,2-3,8-9H2,1H3/b5-4+,7-6+/t10-,11+,12-,14-/m1/s1

InChI Key

MPOXQBRZHHNMER-XZQMCIKJSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
NOESY NMR	[¹H, ¹H] NMR Spectrum (2D, 500 MHz, CDCl3, experimental)	[email protected]	Not Available	Pedro Martins Santucci	2024-12-04	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 500 MHz, CDCl3, experimental)	[email protected]	Not Available	Pedro Martins Santucci	2024-12-04	View Spectrum
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 500 MHz, CDCl3, experimental)	[email protected]	Not Available	Pedro Martins Santucci	2024-12-04	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl3, experimental)	[email protected]	Not Available	Pedro Martins Santucci	2024-12-04	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, CDCl3, experimental)	[email protected]	Not Available	Pedro Martins Santucci	2024-12-04	View Spectrum

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

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 600.0, Chloroform-d, simulated)	[email protected]	Not Available	Not Available	2026-02-19	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 150.0, Chloroform-d, simulated)	[email protected]	Not Available	Not Available	2026-02-19	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 499.84106, CDCl₃, simulated)	[email protected]	Not Available	Pedro Martins Santucci	2024-12-04	View Spectrum

Species

Species of Origin

Species Name	Source	Reference
Penicillium sp. AMF1a		Not Available
Penicillium sp. AMF1a		Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cyclic alcohols and derivatives. These are organic compounds containing an aliphatic ring substituted with at least one hydroxyl group.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Alcohols and polyols

Direct Parent

Cyclic alcohols and derivatives

Alternative Parents

Substituents

Cyclic alcohol
Cyclic ketone
Secondary alcohol
Ketone
Organic oxide
Hydrocarbon derivative
Primary alcohol
Carbonyl group
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic 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	1.04	ChemAxon
pKa (Strongest Acidic)	12.4	ChemAxon
pKa (Strongest Basic)	-2.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	77.76 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	71.84 m³·mol⁻¹	ChemAxon
Polarizability	28.41 Å³	ChemAxon
Number of Rings	1	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

4942905

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6438427

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Li H, Doucet B, Flewelling AJ, Jean S, Webster D, Robichaud GA, Johnson JA, Gray CA: Antimycobacterial Natural Products from Endophytes of the Medicinal Plant Aralia nudicaulis. Nat Prod Commun. 2015 Oct;10(10):1641-2. [PubMed:26669092 ]
Yang LJ, Peng XY, Zhang YH, Liu ZQ, Li X, Gu YC, Shao CL, Han Z, Wang CY: Antimicrobial and Antioxidant Polyketides from a Deep-Sea-Derived Fungus Aspergillus versicolor SH0105. Mar Drugs. 2020 Dec 11;18(12). pii: md18120636. doi: 10.3390/md18120636. [PubMed:33322355 ]
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DOI: 10.1016/j.fitote.2024.106310
PII: s0367326x24004933

Showing NP-Card for (+)-palitantin (NP0342018)

MOL for NP0342018 ((+)-palitantin)

3D MOL for NP0342018 ((+)-palitantin)

3D SDF for NP0342018 ((+)-palitantin)

3D-SDF for NP0342018 ((+)-palitantin)

PDB for NP0342018 ((+)-palitantin)

3D PDB for NP0342018 ((+)-palitantin)

SMILES for NP0342018 ((+)-palitantin)

INCHI for NP0342018 ((+)-palitantin)

Structure for NP0342018 ((+)-palitantin)

3D Structure for NP0342018 ((+)-palitantin)