NP-MRD: Showing NP-Card for Catalpin (NP0140257)

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Record Information

Version

2.0

Created at

2022-06-29 21:16:37 UTC

Updated at

2022-06-29 21:16:38 UTC

NP-MRD ID

NP0140257

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Catalpin

Description

Catalpin belongs to the class of organic compounds known as iridoids and derivatives. These are monoterpenes containing a skeleton structurally characterized by the presence of a cylopentane fused to a pyran ( forming a 4,7-dimethylcyclopenta[c]pyran), or a derivative where the pentane moiety is open. Catalpin is found in Catalpa ovata. Catalpin was first documented in 1989 (PMID: 2692858). Based on a literature review very few articles have been published on Catalpin.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 41 44  0  0  0  0  0  0  0  0999 V2000
    1.0470   -1.7882    0.3308 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5786   -0.6775    0.0635 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7392    0.3182   -0.3957 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6263    0.1134   -0.5579 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0698    0.2465   -2.0098 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5521    0.4444   -1.8833 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.0714    1.2571   -2.8823 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3032   -0.8663   -1.7788 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4119   -0.4778   -1.0272 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8068    0.1100    0.0873 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.3229   -0.9006    0.8613 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3526   -0.6125    1.7539 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.9191   -0.6802    3.0496 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6952    0.7120    1.6289 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4877    1.0785    0.1992 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8053    1.0295   -0.5116 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0136   -0.4861    0.2416 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5983    0.7171   -0.0465 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9610    0.8679    0.1326 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7687   -0.1510    0.5938 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1463    0.0196    0.7690 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1602   -1.3565    0.8786 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7866   -1.5094    0.6985 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8654   -0.9288   -0.2637 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6251    1.1549   -2.4241 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7892   -0.6512   -2.5973 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9912    0.9522   -3.0635 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7269   -1.5674   -1.1648 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5877   -1.2660   -2.7692 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5956    0.7137    0.5859 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6046   -1.4595    1.7432 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2850   -0.3254    3.7250 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7481    0.6906    2.2193 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3413    1.4747    2.0938 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0722    2.1101    0.1446 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2113    2.0523   -0.6367 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9929    1.5522   -0.4151 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4580    1.8249   -0.0912 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5446    0.9117    0.5496 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7544   -2.1822    1.2424 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3182   -2.4650    0.9265 H   0  0  0  0  0  0  0  0  0  0  0  0
 13 12  1  0
 12 14  1  0
 14 15  1  0
 15  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  6
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 10 16  1  0
  4  3  1  0
  3  2  1  0
  2  1  2  0
  2 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 20 22  1  0
 22 23  2  0
 11 12  1  0
 23 17  1  0
 16 15  1  0
 16  6  1  0
 13 32  1  0
 12 31  1  1
 14 33  1  0
 14 34  1  0
 15 35  1  1
  4 24  1  1
  5 25  1  0
  5 26  1  0
  7 27  1  0
  8 28  1  0
  8 29  1  0
 10 30  1  1
 16 36  1  6
 18 37  1  0
 19 38  1  0
 21 39  1  0
 22 40  1  0
 23 41  1  0
M  END


  Mrv1652306292223162D          

 23 26  0  0  1  0            999 V2000
    1.6818    0.1942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9031   -0.0783    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2621   -0.0183    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5806   -0.7793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0447   -1.3174    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7497   -0.8890    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3751   -1.4271    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0565   -2.1881    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2343   -2.1203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1538   -1.1546    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3071   -0.3439    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0858   -0.0714    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6603   -1.7459    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7013    0.6801    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5257    0.6489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9109   -0.0807    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9650    1.3472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7894    1.3160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2286    2.0144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8435    2.7439    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0190    2.7751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5798    2.0768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2827    3.4423    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  6  5  1  6  0  0  0
  2  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  6  0  0  0
  8  9  1  0  0  0  0
  5  9  1  0  0  0  0
  7 10  1  0  0  0  0
 10 11  1  0  0  0  0
  1 11  1  0  0  0  0
 11 12  1  1  0  0  0
  5 13  1  1  0  0  0
  3 14  1  1  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  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 17 22  1  0  0  0  0
 20 23  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0140257

> <DATABASE_NAME>
NP-MRD

> <SMILES>
O[C@@H]1C[C@H]2[C@@H](C[C@@]3(O)CO[C@@H](O1)[C@@H]23)OC(=O)C1=CC=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C16H18O7/c17-9-3-1-8(2-4-9)14(19)22-11-6-16(20)7-21-15-13(16)10(11)5-12(18)23-15/h1-4,10-13,15,17-18,20H,5-7H2/t10-,11+,12-,13+,15-,16+/m0/s1

> <INCHI_KEY>
ZGEFAWWFLHUTII-ZNOBHYIQSA-N

> <FORMULA>
C16H18O7

> <MOLECULAR_WEIGHT>
322.313

> <EXACT_MASS>
322.10525292

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
41

> <JCHEM_AVERAGE_POLARIZABILITY>
31.191264919814376

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,4S,6R,7R,9S,11S)-4,9-dihydroxy-2,10-dioxatricyclo[5.3.1.0^{4,11}]undecan-6-yl 4-hydroxybenzoate

> <ALOGPS_LOGP>
-0.13

> <JCHEM_LOGP>
0.6161567913333337

> <ALOGPS_LOGS>
-1.37

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.364723498876575

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.496531875654627

> <JCHEM_PKA_STRONGEST_BASIC>
-3.4412825717576485

> <JCHEM_POLAR_SURFACE_AREA>
105.45

> <JCHEM_REFRACTIVITY>
76.53120000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.38e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,4S,6R,7R,9S,11S)-4,9-dihydroxy-2,10-dioxatricyclo[5.3.1.0^{4,11}]undecan-6-yl 4-hydroxybenzoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-JUN-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-JUN-22         0                                  
HETATM    1  C   UNK     0       3.139   0.362   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.686  -0.146   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.489  -0.034   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.084  -1.455   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.083  -2.459   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.399  -1.659   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.567  -2.664   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       1.972  -4.084   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       0.437  -3.958   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       4.020  -2.155   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       4.307  -0.642   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       5.760  -0.133   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      -1.233  -3.259   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0      -1.309   1.269   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      -2.848   1.211   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -3.567  -0.151   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      -3.668   2.515   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -5.207   2.457   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -6.027   3.760   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -5.308   5.122   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -3.769   5.180   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -2.949   3.877   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -6.128   6.426   0.000  0.00  0.00           O+0
CONECT    1    2   11                                                       
CONECT    2    1    3    6                                                  
CONECT    3    2    4   14                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    9   13                                             
CONECT    6    5    2    7                                                  
CONECT    7    6    8   10                                                  
CONECT    8    7    9                                                       
CONECT    9    8    5                                                       
CONECT   10    7   11                                                       
CONECT   11   10    1   12                                                  
CONECT   12   11                                                            
CONECT   13    5                                                            
CONECT   14    3   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   22                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   23                                                  
CONECT   21   20   22                                                       
CONECT   22   21   17                                                       
CONECT   23   20                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   52    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₆H₁₈O₇

Average Mass

322.3130 Da

Monoisotopic Mass

322.10525 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

O[C@@H]1C[C@H]2[C@@H](C[C@@]3(O)CO[C@@H](O1)[C@@H]23)OC(=O)C1=CC=C(O)C=C1

InChI Identifier

InChI=1S/C16H18O7/c17-9-3-1-8(2-4-9)14(19)22-11-6-16(20)7-21-15-13(16)10(11)5-12(18)23-15/h1-4,10-13,15,17-18,20H,5-7H2/t10-,11+,12-,13+,15-,16+/m0/s1

InChI Key

ZGEFAWWFLHUTII-ZNOBHYIQSA-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
Catalpa ovata	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as iridoids and derivatives. These are monoterpenes containing a skeleton structurally characterized by the presence of a cylopentane fused to a pyran ( forming a 4,7-dimethylcyclopenta[c]pyran), or a derivative where the pentane moiety is open.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Monoterpenoids

Direct Parent

Iridoids and derivatives

Alternative Parents

Substituents

P-hydroxybenzoic acid alkyl ester
P-hydroxybenzoic acid ester
Iridoid-skeleton
Aromatic monoterpenoid
Benzoate ester
Benzoic acid or derivatives
Furopyran
Benzoyl
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Benzenoid
Oxane
Pyran
Tertiary alcohol
Tetrahydrofuran
Cyclic alcohol
Furan
Carboxylic acid ester
Hemiacetal
Monocarboxylic acid or derivatives
Acetal
Oxacycle
Carboxylic acid derivative
Organoheterocyclic compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Alcohol
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic 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

28425491

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

71716362

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Nozaka T, Watanabe F, Ishino M, Morimoto I, Kondoh H, Koyama K, Natori S: A mutagenic new iridoid in the water extract of catalpae fructus. Chem Pharm Bull (Tokyo). 1989 Oct;37(10):2838-40. doi: 10.1248/cpb.37.2838. [PubMed:2692858 ]

Showing NP-Card for Catalpin (NP0140257)

MOL for NP0140257 (Catalpin)

3D MOL for NP0140257 (Catalpin)

3D SDF for NP0140257 (Catalpin)

3D-SDF for NP0140257 (Catalpin)

PDB for NP0140257 (Catalpin)

3D PDB for NP0140257 (Catalpin)

SMILES for NP0140257 (Catalpin)

INCHI for NP0140257 (Catalpin)

Structure for NP0140257 (Catalpin)

3D Structure for NP0140257 (Catalpin)