NP-MRD: Showing NP-Card for Neohelmanthicin B (NP0074149)

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Record Information

Version

2.0

Created at

2022-04-28 19:18:58 UTC

Updated at

2022-04-28 19:18:58 UTC

NP-MRD ID

NP0074149

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Neohelmanthicin B

Description

Octanoic acid (1S,2R)-1-methyl-2-[[(1S,2R)-1-methyl-2-[[(Z)-2-methyl-2-butenoyl]oxy]-2-(7-methoxy-1,3-benzodioxole-5-yl)ethyl]oxycarbonyl]-2-hydroxypropyl ester belongs to the class of organic compounds known as benzodioxoles. These are organic compounds containing a benzene ring fused to either isomers of dioxole. Dioxole is a five-membered unsaturated ring of two oxygen atoms and three carbon atoms. Neohelmanthicin B is found in Thapsia garganica. Based on a literature review very few articles have been published on Octanoic acid (1S,2R)-1-methyl-2-[[(1S,2R)-1-methyl-2-[[(Z)-2-methyl-2-butenoyl]oxy]-2-(7-methoxy-1,3-benzodioxole-5-yl)ethyl]oxycarbonyl]-2-hydroxypropyl ester.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282221182D          

 39 40  0  0  1  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652304282221182D          

 39 40  0  0  1  0            999 V2000
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    2.4454    0.1105    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2704    1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    3.7125    0.0000 O   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 O   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
   -0.7145    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    4.9500    0.0000 C   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  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  4  9  1  0  0  0  0
  3 10  1  0  0  0  0
 10 11  1  0  0  0  0
  1 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  1  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  1  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 18 31  1  6  0  0  0
 18 32  1  6  0  0  0
 12 33  1  6  0  0  0
 33 34  1  0  0  0  0
 34 35  2  0  0  0  0
 34 36  1  0  0  0  0
 36 37  2  0  0  0  0
 37 38  1  0  0  0  0
 36 39  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0074149

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCCCCC(=O)O[C@@H](C)[C@@](C)(O)C(=O)O[C@@H](C)[C@H](OC(=O)C(\C)=C/C)C1=CC(OC)=C2OCOC2=C1

> <INCHI_IDENTIFIER>
InChI=1S/C29H42O10/c1-8-10-11-12-13-14-24(30)38-20(5)29(6,33)28(32)37-19(4)25(39-27(31)18(3)9-2)21-15-22(34-7)26-23(16-21)35-17-36-26/h9,15-16,19-20,25,33H,8,10-14,17H2,1-7H3/b18-9-/t19-,20-,25-,29+/m0/s1

> <INCHI_KEY>
XUNRIPMOCLNINU-BOPPCVMBSA-N

> <FORMULA>
C29H42O10

> <MOLECULAR_WEIGHT>
550.645

> <EXACT_MASS>
550.277797552

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
81

> <JCHEM_AVERAGE_POLARIZABILITY>
59.96760301677605

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,3R)-3-hydroxy-4-{[(1R,2S)-1-(7-methoxy-2H-1,3-benzodioxol-5-yl)-1-{[(2Z)-2-methylbut-2-enoyl]oxy}propan-2-yl]oxy}-3-methyl-4-oxobutan-2-yl octanoate

> <ALOGPS_LOGP>
5.20

> <JCHEM_LOGP>
6.030212700999998

> <ALOGPS_LOGS>
-5.25

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.640131644089044

> <JCHEM_PKA_STRONGEST_BASIC>
-4.268406418875451

> <JCHEM_POLAR_SURFACE_AREA>
126.82

> <JCHEM_REFRACTIVITY>
142.1219

> <JCHEM_ROTATABLE_BOND_COUNT>
18

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.07e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3R)-3-hydroxy-4-{[(1R,2S)-1-(7-methoxy-2H-1,3-benzodioxol-5-yl)-1-{[(2Z)-2-methylbut-2-enoyl]oxy}propan-2-yl]oxy}-3-methyl-4-oxobutan-2-yl octanoate

> <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       4.001   6.930   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.001   8.470   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.335   9.240   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.668   8.470   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.668   6.930   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.335   6.160   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       8.133   6.454   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       9.038   7.700   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       8.133   8.946   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0       5.335  10.780   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       6.668  11.550   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.667   6.160   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       4.001   3.850   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.668   0.770   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       8.002   1.540   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       9.336   0.770   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       9.336  -0.770   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      10.669   1.540   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      12.003   0.770   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      13.337   1.540   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      14.670   0.770   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      16.004   1.540   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      17.338   0.770   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      18.672   1.540   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       4.565   0.206   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       6.105   2.874   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       1.334   6.930   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       0.000   6.160   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       0.000   4.620   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0      -1.334   6.930   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      -1.334   8.470   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       0.000   9.240   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      -2.667   6.160   0.000  0.00  0.00           C+0
CONECT    1    2    6   12                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4   10                                                  
CONECT    4    3    5    9                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5    1                                                       
CONECT    7    5    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8    4                                                       
CONECT   10    3   11                                                       
CONECT   11   10                                                            
CONECT   12    1   13   33                                                  
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19   31   32                                             
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29                                                            
CONECT   31   18                                                            
CONECT   32   18                                                            
CONECT   33   12   34                                                       
CONECT   34   33   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34   37   39                                                  
CONECT   37   36   38                                                       
CONECT   38   37                                                            
CONECT   39   36                                                            
MASTER        0    0    0    0    0    0    0    0   39    0   80    0
END

View in JSmol

Synonyms

Value	Source
Octanoate (1S,2R)-1-methyl-2-[[(1S,2R)-1-methyl-2-[[(Z)-2-methyl-2-butenoyl]oxy]-2-(7-methoxy-1,3-benzodioxole-5-yl)ethyl]oxycarbonyl]-2-hydroxypropyl ester	Generator

Chemical Formula

C₂₉H₄₂O₁₀

Average Mass

550.6450 Da

Monoisotopic Mass

550.27780 Da

IUPAC Name

(2S,3R)-3-hydroxy-4-{[(1R,2S)-1-(7-methoxy-2H-1,3-benzodioxol-5-yl)-1-{[(2Z)-2-methylbut-2-enoyl]oxy}propan-2-yl]oxy}-3-methyl-4-oxobutan-2-yl octanoate

Traditional Name

(2S,3R)-3-hydroxy-4-{[(1R,2S)-1-(7-methoxy-2H-1,3-benzodioxol-5-yl)-1-{[(2Z)-2-methylbut-2-enoyl]oxy}propan-2-yl]oxy}-3-methyl-4-oxobutan-2-yl octanoate

CAS Registry Number

Not Available

SMILES

CCCCCCCC(=O)O[C@@H](C)[C@@](C)(O)C(=O)O[C@@H](C)[C@H](OC(=O)C(\C)=C/C)C1=CC(OC)=C2OCOC2=C1

InChI Identifier

InChI=1S/C29H42O10/c1-8-10-11-12-13-14-24(30)38-20(5)29(6,33)28(32)37-19(4)25(39-27(31)18(3)9-2)21-15-22(34-7)26-23(16-21)35-17-36-26/h9,15-16,19-20,25,33H,8,10-14,17H2,1-7H3/b18-9-/t19-,20-,25-,29+/m0/s1

InChI Key

XUNRIPMOCLNINU-BOPPCVMBSA-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
Thapsia garganica	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzodioxoles. These are organic compounds containing a benzene ring fused to either isomers of dioxole. Dioxole is a five-membered unsaturated ring of two oxygen atoms and three carbon atoms.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzodioxoles

Sub Class

Not Available

Direct Parent

Benzodioxoles

Alternative Parents

Substituents

Benzodioxole
Tricarboxylic acid or derivatives
Anisole
Alkyl aryl ether
Fatty acid ester
Fatty acyl
Benzenoid
Enoate ester
Tertiary alcohol
Alpha,beta-unsaturated carboxylic ester
Carboxylic acid ester
Acetal
Oxacycle
Ether
Carboxylic acid derivative
Organooxygen compound
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Alcohol
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
logP	5.2	ALOGPS
logP	6.03	ChemAxon
logS	-5.2	ALOGPS
pKa (Strongest Acidic)	11.64	ChemAxon
pKa (Strongest Basic)	-4.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	126.82 Å²	ChemAxon
Rotatable Bond Count	18	ChemAxon
Refractivity	142.12 m³·mol⁻¹	ChemAxon
Polarizability	59.97 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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

13088150

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

15946301

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Neohelmanthicin B (NP0074149)

MOL for NP0074149 (Neohelmanthicin B)

3D MOL for NP0074149 (Neohelmanthicin B)

3D SDF for NP0074149 (Neohelmanthicin B)

3D-SDF for NP0074149 (Neohelmanthicin B)

PDB for NP0074149 (Neohelmanthicin B)

3D PDB for NP0074149 (Neohelmanthicin B)

SMILES for NP0074149 (Neohelmanthicin B)

INCHI for NP0074149 (Neohelmanthicin B)

Structure for NP0074149 (Neohelmanthicin B)

3D Structure for NP0074149 (Neohelmanthicin B)