NP-MRD: Showing NP-Card for Calbertolide B (NP0058932)

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Record Information

Version

2.0

Created at

2022-04-28 04:14:05 UTC

Updated at

2022-04-28 04:14:05 UTC

NP-MRD ID

NP0058932

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Calbertolide B

Description

Calbertolide B belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring. Calbertolide B is found in Calea berteriana. Based on a literature review very few articles have been published on Calbertolide B.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 43 45  0  0  0  0  0  0  0  0999 V2000
   -1.5460    3.0515    1.5073 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2426    2.2881    0.4696 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0906    1.0993    0.2078 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6603    0.0298    1.1644 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.7574   -0.2506    2.0247 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4811   -1.3061    1.4865 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6885   -1.5558    1.7765 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6067   -2.0240    0.5700 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9399   -3.0938   -0.1038 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3260   -1.2780    0.5964 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6130   -1.2922   -0.7221 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7853   -0.8021   -0.4881 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8067    0.4769    0.1970 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3481    0.2774   -1.1057 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8523    0.3253   -1.2678 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5376   -0.6216   -0.5138 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5392   -0.6317    0.8396 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3217   -1.7271    1.5200 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9440    0.1944    1.5498 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6429    1.0034   -2.2181 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1751    2.1787   -1.8119 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1280    2.5582   -0.4072 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8914    3.1280    0.0527 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9163    3.9158    1.6916 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3928    2.8292    2.1576 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0803    0.8146   -0.8375 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1539    1.4315    0.4093 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8354    0.3619    1.8521 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1984   -3.5381   -0.7557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9307   -3.4999    0.0061 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6636   -1.8266    1.3230 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5183   -2.3889   -0.9967 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1549   -0.8470   -1.5447 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3884   -1.5277    0.0960 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0330    0.0746   -2.3590 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2212    1.3561   -1.0593 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6079   -1.3876    2.5425 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2316   -1.9183    0.9239 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6591   -2.6008    1.5973 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0341    0.2283   -2.7725 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3500    1.3590   -3.0112 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1271    3.1177   -2.3785 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2217    2.0177   -2.2081 H   0  0  0  0  0  0  0  0  0  0  0  0
 18 17  1  0
 17 19  2  0
 17 16  1  0
 16 15  1  0
 14 15  1  1
 14 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 22  2  1  0
  2  1  2  3
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  2  3
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
 13 14  1  0
 10  4  1  0
 18 37  1  0
 18 38  1  0
 18 39  1  0
 15 35  1  0
 15 36  1  0
 20 40  1  0
 20 41  1  0
 21 42  1  0
 21 43  1  0
  1 24  1  0
  1 25  1  0
  3 26  1  0
  3 27  1  0
  4 28  1  1
  9 29  1  0
  9 30  1  0
 10 31  1  1
 11 32  1  0
 11 33  1  0
 12 34  1  1
M  END


  Mrv1652304282206142D          

 23 25  0  0  1  0            999 V2000
    4.5131   -0.6247    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.1772   -1.1143    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.8480   -0.6340    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5985    0.1524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0880    0.8165    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7735    0.1581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2932    0.8289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0853   -1.9341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3293   -2.2645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2374   -3.0843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6652   -1.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2577   -1.0576    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9093   -2.1053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2452   -1.6158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3371   -0.7959    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0931   -0.4656    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7571   -0.9551    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4290    0.0240    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5172   -0.7040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1869    0.0520    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6764    0.7161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3461    1.4720    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4963    0.6241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  6  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  1  6  1  6  0  0  0
  6  7  2  0  0  0  0
  2  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
  1 17  1  0  0  0  0
 16 18  1  1  0  0  0
 15 18  1  0  0  0  0
 15 19  1  6  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0058932

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)OC[C@@]12CCC(=O)C(=C)C[C@H]3OC(=O)C(=C)[C@H]3C[C@@H]1O2

> <INCHI_IDENTIFIER>
InChI=1S/C17H20O6/c1-9-6-14-12(10(2)16(20)22-14)7-15-17(23-15,5-4-13(9)19)8-21-11(3)18/h12,14-15H,1-2,4-8H2,3H3/t12-,14-,15+,17+/m1/s1

> <INCHI_KEY>
DGQROTBNZIJOHQ-UTXMOHQDSA-N

> <FORMULA>
C17H20O6

> <MOLECULAR_WEIGHT>
320.341

> <EXACT_MASS>
320.125988364

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
43

> <JCHEM_AVERAGE_POLARIZABILITY>
31.841855692912237

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
[(1R,3S,5S,11R)-9,14-dimethylidene-8,13-dioxo-4,12-dioxatricyclo[9.3.0.0^{3,5}]tetradecan-5-yl]methyl acetate

> <ALOGPS_LOGP>
0.96

> <JCHEM_LOGP>
1.5443434309999997

> <ALOGPS_LOGS>
-2.56

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.4029094367108

> <JCHEM_PKA_STRONGEST_BASIC>
-4.178501112813441

> <JCHEM_POLAR_SURFACE_AREA>
82.20000000000002

> <JCHEM_REFRACTIVITY>
79.1768

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.78e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[(1R,3S,5S,11R)-9,14-dimethylidene-8,13-dioxo-4,12-dioxatricyclo[9.3.0.0^{3,5}]tetradecan-5-yl]methyl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0       8.424  -1.166   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.664  -2.080   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      10.916  -1.183   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      10.450   0.284   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      11.364   1.524   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       8.910   0.295   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.014   1.547   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.493  -3.610   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.081  -4.227   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.910  -5.757   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.842  -3.313   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       6.081  -1.974   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       5.431  -3.930   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.191  -3.016   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.363  -1.486   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.774  -0.869   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.013  -1.783   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       4.534   0.045   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       2.832  -1.314   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       2.216   0.097   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       3.129   1.337   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       2.513   2.748   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       4.660   1.165   0.000  0.00  0.00           C+0
CONECT    1    2    6   17                                                  
CONECT    2    1    3    8                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    1    7                                                  
CONECT    7    6                                                            
CONECT    8    2    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   18   19                                             
CONECT   16   15   17   18                                                  
CONECT   17   16    1                                                       
CONECT   18   16   15                                                       
CONECT   19   15   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   50    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₇H₂₀O₆

Average Mass

320.3410 Da

Monoisotopic Mass

320.12599 Da

IUPAC Name

[(1R,3S,5S,11R)-9,14-dimethylidene-8,13-dioxo-4,12-dioxatricyclo[9.3.0.0^{3,5}]tetradecan-5-yl]methyl acetate

Traditional Name

[(1R,3S,5S,11R)-9,14-dimethylidene-8,13-dioxo-4,12-dioxatricyclo[9.3.0.0^{3,5}]tetradecan-5-yl]methyl acetate

CAS Registry Number

Not Available

SMILES

CC(=O)OC[C@@]12CCC(=O)C(=C)C[C@H]3OC(=O)C(=C)[C@H]3C[C@@H]1O2

InChI Identifier

InChI=1S/C17H20O6/c1-9-6-14-12(10(2)16(20)22-14)7-15-17(23-15,5-4-13(9)19)8-21-11(3)18/h12,14-15H,1-2,4-8H2,3H3/t12-,14-,15+,17+/m1/s1

InChI Key

DGQROTBNZIJOHQ-UTXMOHQDSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Calea berteriana	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Terpene lactones

Alternative Parents

Substituents

Terpene lactone
Germacrane sesquiterpenoid
Sesquiterpenoid
Dicarboxylic acid or derivatives
Gamma butyrolactone
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tetrahydrofuran
Carboxylic acid ester
Ketone
Cyclic ketone
Lactone
Carboxylic acid derivative
Dialkyl ether
Oxirane
Ether
Oxacycle
Organoheterocyclic compound
Organic oxygen compound
Hydrocarbon derivative
Carbonyl group
Organic oxide
Organooxygen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic 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
logP	0.96	ALOGPS
logP	1.54	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	18.4	ChemAxon
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	82.2 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	79.18 m³·mol⁻¹	ChemAxon
Polarizability	31.84 Å³	ChemAxon
Number of Rings	3	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

C00012391

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

101288320

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for Calbertolide B (NP0058932)

MOL for NP0058932 (Calbertolide B)

3D MOL for NP0058932 (Calbertolide B)

3D SDF for NP0058932 (Calbertolide B)

3D-SDF for NP0058932 (Calbertolide B)

PDB for NP0058932 (Calbertolide B)

3D PDB for NP0058932 (Calbertolide B)

SMILES for NP0058932 (Calbertolide B)

INCHI for NP0058932 (Calbertolide B)

Structure for NP0058932 (Calbertolide B)

3D Structure for NP0058932 (Calbertolide B)