NP-MRD: Showing NP-Card for Pittosporanoside B1 (NP0058328)

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Record Information

Version

2.0

Created at

2022-04-28 03:41:43 UTC

Updated at

2022-04-28 03:41:43 UTC

NP-MRD ID

NP0058328

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Pittosporanoside B1

Description

(2R,3R,4S,5S,6R)-3-(acetyloxy)-2-{[(1R,2E,6E,10S)-3,7-dimethyl-10-(propan-2-yl)cyclodeca-2,6-dien-1-yl]oxy}-5-hydroxy-6-methyloxan-4-yl (2Z)-2-methylbut-2-enoate belongs to the class of organic compounds known as terpene glycosides. These are prenol lipids containing a carbohydrate moiety glycosidically bound to a terpene backbone. Pittosporanoside B1 is found in Pittosporum tobira . Based on a literature review very few articles have been published on (2R,3R,4S,5S,6R)-3-(acetyloxy)-2-{[(1R,2E,6E,10S)-3,7-dimethyl-10-(propan-2-yl)cyclodeca-2,6-dien-1-yl]oxy}-5-hydroxy-6-methyloxan-4-yl (2Z)-2-methylbut-2-enoate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282205412D          

 35 36  0  0  1  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652304282205412D          

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  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  1 10  1  0  0  0  0
  9 11  1  0  0  0  0
  6 12  1  6  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
  5 15  1  6  0  0  0
 16 15  1  1  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 16 21  1  0  0  0  0
 20 22  1  1  0  0  0
 19 23  1  1  0  0  0
 18 24  1  1  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 27 30  1  0  0  0  0
 17 31  1  6  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 32 34  1  0  0  0  0
  3 35  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0058328

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C\C=C(\C)C(=O)O[C@H]1[C@@H](O)[C@@H](C)O[C@@H](O[C@H]2\C=C(C)\CC\C=C(C)\CC[C@H]2C(C)C)[C@@H]1OC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C28H44O7/c1-9-19(6)27(31)35-25-24(30)20(7)32-28(26(25)33-21(8)29)34-23-15-18(5)12-10-11-17(4)13-14-22(23)16(2)3/h9,11,15-16,20,22-26,28,30H,10,12-14H2,1-8H3/b17-11+,18-15+,19-9-/t20-,22+,23+,24+,25+,26-,28+/m1/s1

> <INCHI_KEY>
CCINNFNVGBXOKP-VMQRTCFXSA-N

> <FORMULA>
C28H44O7

> <MOLECULAR_WEIGHT>
492.653

> <EXACT_MASS>
492.308703757

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
79

> <JCHEM_AVERAGE_POLARIZABILITY>
54.01331071205419

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R,3R,4S,5S,6R)-3-(acetyloxy)-2-{[(1R,2E,6E,10S)-3,7-dimethyl-10-(propan-2-yl)cyclodeca-2,6-dien-1-yl]oxy}-5-hydroxy-6-methyloxan-4-yl (2Z)-2-methylbut-2-enoate

> <ALOGPS_LOGP>
5.03

> <JCHEM_LOGP>
6.004452366666665

> <ALOGPS_LOGS>
-4.91

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.104323673851098

> <JCHEM_PKA_STRONGEST_BASIC>
-3.627968825057528

> <JCHEM_POLAR_SURFACE_AREA>
91.29000000000002

> <JCHEM_REFRACTIVITY>
135.79479999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
6.04e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R,3R,4S,5S,6R)-3-(acetyloxy)-5-hydroxy-2-{[(1R,2E,6E,10S)-10-isopropyl-3,7-dimethylcyclodeca-2,6-dien-1-yl]oxy}-6-methyloxan-4-yl (2Z)-2-methylbut-2-enoate

> <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      -2.667   4.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.667   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -5.335   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -5.335   1.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -4.001   2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -4.001   3.850   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.469   2.471   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -3.375  -3.717   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      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -0.000  -4.620   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -2.667  -3.080   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      -4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -1.334  -6.930   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       1.334  -5.390   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       2.667  -3.080   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      -0.000  -0.000   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -0.000   1.540   0.000  0.00  0.00           C+0
CONECT    1    2   10                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4   35                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   15                                                  
CONECT    6    5    7   12                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9    1                                                       
CONECT   11    9                                                            
CONECT   12    6   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12                                                            
CONECT   15    5   16                                                       
CONECT   16   15   17   21                                                  
CONECT   17   16   18   31                                                  
CONECT   18   17   19   24                                                  
CONECT   19   18   20   23                                                  
CONECT   20   19   21   22                                                  
CONECT   21   20   16                                                       
CONECT   22   20                                                            
CONECT   23   19                                                            
CONECT   24   18   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28   30                                                  
CONECT   28   27   29                                                       
CONECT   29   28                                                            
CONECT   30   27                                                            
CONECT   31   17   32                                                       
CONECT   32   31   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32                                                            
CONECT   35    3                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   72    0
END

View in JSmol

Synonyms

Value	Source
(2R,3R,4S,5S,6R)-3-(Acetyloxy)-2-{[(1R,2E,6E,10S)-3,7-dimethyl-10-(propan-2-yl)cyclodeca-2,6-dien-1-yl]oxy}-5-hydroxy-6-methyloxan-4-yl (2Z)-2-methylbut-2-enoic acid	Generator

Chemical Formula

C₂₈H₄₄O₇

Average Mass

492.6530 Da

Monoisotopic Mass

492.30870 Da

IUPAC Name

(2R,3R,4S,5S,6R)-3-(acetyloxy)-2-{[(1R,2E,6E,10S)-3,7-dimethyl-10-(propan-2-yl)cyclodeca-2,6-dien-1-yl]oxy}-5-hydroxy-6-methyloxan-4-yl (2Z)-2-methylbut-2-enoate

Traditional Name

(2R,3R,4S,5S,6R)-3-(acetyloxy)-5-hydroxy-2-{[(1R,2E,6E,10S)-10-isopropyl-3,7-dimethylcyclodeca-2,6-dien-1-yl]oxy}-6-methyloxan-4-yl (2Z)-2-methylbut-2-enoate

CAS Registry Number

Not Available

SMILES

C\C=C(\C)C(=O)O[C@H]1[C@@H](O)[C@@H](C)O[C@@H](O[C@H]2\C=C(C)\CC\C=C(C)\CC[C@H]2C(C)C)[C@@H]1OC(C)=O

InChI Identifier

InChI=1S/C28H44O7/c1-9-19(6)27(31)35-25-24(30)20(7)32-28(26(25)33-21(8)29)34-23-15-18(5)12-10-11-17(4)13-14-22(23)16(2)3/h9,11,15-16,20,22-26,28,30H,10,12-14H2,1-8H3/b17-11+,18-15+,19-9-/t20-,22+,23+,24+,25+,26-,28+/m1/s1

InChI Key

CCINNFNVGBXOKP-VMQRTCFXSA-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
Pittosporum tobira	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as terpene glycosides. These are prenol lipids containing a carbohydrate moiety glycosidically bound to a terpene backbone.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene glycosides

Direct Parent

Terpene glycosides

Alternative Parents

Substituents

Terpene glycoside
Germacrane sesquiterpenoid
Sesquiterpenoid
Hexose monosaccharide
Glycosyl compound
O-glycosyl compound
Fatty acid ester
Dicarboxylic acid or derivatives
Fatty acyl
Monosaccharide
Oxane
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Carboxylic acid ester
Secondary alcohol
Acetal
Organoheterocyclic compound
Oxacycle
Carboxylic acid derivative
Alcohol
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
Organooxygen compound
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic 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	5.03	ALOGPS
logP	6	ChemAxon
logS	-4.9	ALOGPS
pKa (Strongest Acidic)	13.1	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	91.29 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	135.79 m³·mol⁻¹	ChemAxon
Polarizability	54.01 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	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

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

14587402

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Pittosporanoside B1 (NP0058328)

MOL for NP0058328 (Pittosporanoside B1)

3D MOL for NP0058328 (Pittosporanoside B1)

3D SDF for NP0058328 (Pittosporanoside B1)

3D-SDF for NP0058328 (Pittosporanoside B1)

PDB for NP0058328 (Pittosporanoside B1)

3D PDB for NP0058328 (Pittosporanoside B1)

SMILES for NP0058328 (Pittosporanoside B1)

INCHI for NP0058328 (Pittosporanoside B1)

Structure for NP0058328 (Pittosporanoside B1)

3D Structure for NP0058328 (Pittosporanoside B1)