NP-MRD: Showing NP-Card for (+)-Vannusal B (NP0082119)

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Record Information

Version

2.0

Created at

2022-04-29 03:10:33 UTC

Updated at

2022-04-29 03:10:33 UTC

NP-MRD ID

NP0082119

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(+)-Vannusal B

Description

(1R,2R,5S)-2-[(1R,1'R,2S,2'S,3R,3'R,6'S,9'R,10'R,12'S)-9'-formyl-2,2',12'-trihydroxy-3-(2-hydroxypropan-2-yl)spiro[cyclopentane-1,11'-tetracyclo[8.2.2.0¹,⁹.0³,⁷]Tetradecan]-7'-en-6'-yl]-5-(prop-1-en-2-yl)cyclopentyl acetate belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. (+)-Vannusal B is found in Euplotes vannus. Based on a literature review very few articles have been published on (1R,2R,5S)-2-[(1R,1'R,2S,2'S,3R,3'R,6'S,9'R,10'R,12'S)-9'-formyl-2,2',12'-trihydroxy-3-(2-hydroxypropan-2-yl)spiro[cyclopentane-1,11'-tetracyclo[8.2.2.0¹,⁹.0³,⁷]Tetradecan]-7'-en-6'-yl]-5-(prop-1-en-2-yl)cyclopentyl acetate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304292205102D          

 39 44  0  0  1  0            999 V2000
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  1  2  1  0  0  0  0
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  4 38  1  1  0  0  0
 38 39  2  0  0  0  0
M  END

     RDKit          3D

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M  END


  Mrv1652304292205102D          

 39 44  0  0  1  0            999 V2000
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    4.2235    4.4711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2504    4.7140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4254    4.7133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6622    5.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9097   -0.7642    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0996    0.3871    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7369    1.1280    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2075    0.4952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4421    0.8031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4984    1.6262    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2986    1.8270    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4917    2.7095    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7551    2.1767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1957    2.8323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0237    3.0165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0425    1.6459    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2225   -0.5141    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8021    0.6560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6247   -0.3106    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  2  1  1  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  1  1  1  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  1  0  0  0
  8  9  2  0  0  0  0
  4  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
  7 12  1  0  0  0  0
 10 13  1  6  0  0  0
 13 14  1  6  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  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
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
 16 22  1  6  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
  6 25  1  6  0  0  0
  5 26  1  0  0  0  0
 26 27  1  0  0  0  0
  3 27  1  0  0  0  0
 27 28  1  6  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 27 31  1  0  0  0  0
 31 32  1  6  0  0  0
 30 33  1  1  0  0  0
 33 34  1  0  0  0  0
 33 35  1  0  0  0  0
 33 36  1  0  0  0  0
 26 37  1  1  0  0  0
  4 38  1  1  0  0  0
 38 39  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0082119

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)O[C@@H]1[C@H](CC[C@H]1C(C)=C)[C@@H]1CC[C@H]2[C@H](O)[C@]34CC[C@H]([C@@]5(CC[C@H]([C@@H]5O)C(C)(C)O)[C@@H]3O)[C@]4(C=O)C=C12

> <INCHI_IDENTIFIER>
InChI=1S/C32H46O7/c1-16(2)18-6-8-20(25(18)39-17(3)34)19-7-9-21-22(19)14-30(15-33)24-11-13-32(30,26(21)35)28(37)31(24)12-10-23(27(31)36)29(4,5)38/h14-15,18-21,23-28,35-38H,1,6-13H2,2-5H3/t18-,19-,20+,21+,23+,24-,25-,26-,27-,28-,30+,31+,32+/m0/s1

> <INCHI_KEY>
BFLJNEGRKQOKAL-AHHCPIFVSA-N

> <FORMULA>
C32H46O7

> <MOLECULAR_WEIGHT>
542.713

> <EXACT_MASS>
542.324353821

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
85

> <JCHEM_AVERAGE_POLARIZABILITY>
60.337948718169656

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,2R,5S)-2-[(1R,1'R,2S,2'S,3R,3'R,6'S,9'R,10'R,12'S)-9'-formyl-2,2',12'-trihydroxy-3-(2-hydroxypropan-2-yl)spiro[cyclopentane-1,11'-tetracyclo[8.2.2.0^{1,9}.0^{3,7}]tetradecan]-7'-en-6'-yl]-5-(prop-1-en-2-yl)cyclopentyl acetate

> <ALOGPS_LOGP>
2.50

> <JCHEM_LOGP>
1.3742601363333333

> <ALOGPS_LOGS>
-3.73

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.249909999764412

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.720014532340109

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8046809661737955

> <JCHEM_POLAR_SURFACE_AREA>
124.29000000000002

> <JCHEM_REFRACTIVITY>
146.07460000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.01e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2R,5S)-2-[(1R,1'R,2S,2'S,3R,3'R,6'S,9'R,10'R,12'S)-9'-formyl-2,2',12'-trihydroxy-3-(2-hydroxypropan-2-yl)spiro[cyclopentane-1,11'-tetracyclo[8.2.2.0^{1,9}.0^{3,7}]tetradecan]-7'-en-6'-yl]-5-(prop-1-en-2-yl)cyclopentyl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-APR-22         0                                  
HETATM    1  C   UNK     0       8.182   1.895   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.504   3.279   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.968   3.384   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.991   2.170   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.313   0.664   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.778   0.189   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.921   1.221   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.600   2.727   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.135   3.201   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      10.933   3.498   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      12.078   2.469   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      11.453   1.061   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      11.092   5.030   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      12.425   5.801   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      12.104   7.307   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      10.572   7.467   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.947   6.059   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       8.441   5.738   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       7.409   6.881   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       5.903   6.560   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       7.884   8.346   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       9.801   8.800   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       8.261   8.798   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      10.570  10.134   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       9.165  -1.426   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       5.786   0.723   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       5.109   2.106   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       4.121   0.924   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       2.692   1.499   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       2.797   3.036   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       4.291   3.410   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       4.651   5.058   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       1.409   4.063   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       0.365   5.287   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       1.911   5.631   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       0.079   3.072   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0       6.015  -0.960   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0       5.231   1.225   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0       4.899  -0.580   0.000  0.00  0.00           O+0
CONECT    1    2    5                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4   27                                                  
CONECT    4    3    5    9   38                                             
CONECT    5    4    1    6   26                                             
CONECT    6    5    7   25                                                  
CONECT    7    6    8   12                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8    4                                                       
CONECT   10    8   11   13                                                  
CONECT   11   10   12                                                       
CONECT   12   11    7                                                       
CONECT   13   10   14   17                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   22                                                  
CONECT   17   16   13   18                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19                                                            
CONECT   22   16   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22                                                            
CONECT   25    6                                                            
CONECT   26    5   27   37                                                  
CONECT   27   26    3   28   31                                             
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31   33                                                  
CONECT   31   30   27   32                                                  
CONECT   32   31                                                            
CONECT   33   30   34   35   36                                             
CONECT   34   33                                                            
CONECT   35   33                                                            
CONECT   36   33                                                            
CONECT   37   26                                                            
CONECT   38    4   39                                                       
CONECT   39   38                                                            
MASTER        0    0    0    0    0    0    0    0   39    0   88    0
END

View in JSmol

Synonyms

Value	Source
(1R,2R,5S)-2-[(1R,1'r,2S,2's,3R,3'r,6's,9'r,10'r,12's)-9'-Formyl-2,2',12'-trihydroxy-3-(2-hydroxypropan-2-yl)spiro[cyclopentane-1,11'-tetracyclo[8.2.2.0,.0,]tetradecan]-7'-en-6'-yl]-5-(prop-1-en-2-yl)cyclopentyl acetic acid	Generator

Chemical Formula

C₃₂H₄₆O₇

Average Mass

542.7130 Da

Monoisotopic Mass

542.32435 Da

IUPAC Name

Traditional Name

CAS Registry Number

Not Available

SMILES

CC(=O)O[C@@H]1[C@H](CC[C@H]1C(C)=C)[C@@H]1CC[C@H]2[C@H](O)[C@]34CC[C@H]([C@@]5(CC[C@H]([C@@H]5O)C(C)(C)O)[C@@H]3O)[C@]4(C=O)C=C12

InChI Identifier

InChI=1S/C32H46O7/c1-16(2)18-6-8-20(25(18)39-17(3)34)19-7-9-21-22(19)14-30(15-33)24-11-13-32(30,26(21)35)28(37)31(24)12-10-23(27(31)36)29(4,5)38/h14-15,18-21,23-28,35-38H,1,6-13H2,2-5H3/t18-,19-,20+,21+,23+,24-,25-,26-,27-,28-,30+,31+,32+/m0/s1

InChI Key

BFLJNEGRKQOKAL-AHHCPIFVSA-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
Euplotes vannus	-	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Sesquiterpenoids

Alternative Parents

Substituents

Sesquiterpenoid
Tertiary alcohol
Cyclic alcohol
Secondary alcohol
Carboxylic acid ester
Polyol
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aldehyde
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	2.5	ALOGPS
logP	1.37	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	13.72	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	124.29 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	146.07 m³·mol⁻¹	ChemAxon
Polarizability	60.34 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	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

163028241

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for (+)-Vannusal B (NP0082119)

MOL for NP0082119 ((+)-Vannusal B)

3D MOL for NP0082119 ((+)-Vannusal B)

3D SDF for NP0082119 ((+)-Vannusal B)

3D-SDF for NP0082119 ((+)-Vannusal B)

PDB for NP0082119 ((+)-Vannusal B)

3D PDB for NP0082119 ((+)-Vannusal B)

SMILES for NP0082119 ((+)-Vannusal B)

INCHI for NP0082119 ((+)-Vannusal B)

Structure for NP0082119 ((+)-Vannusal B)

3D Structure for NP0082119 ((+)-Vannusal B)