NP-MRD: Showing NP-Card for (-)-Cypellocarpin C (NP0081054)

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Record Information

Version

2.0

Created at

2022-04-29 02:02:20 UTC

Updated at

2022-04-29 02:02:21 UTC

NP-MRD ID

NP0081054

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(-)-Cypellocarpin C

Description

Cypellocarpin C belongs to the class of organic compounds known as saccharolipids. Saccharolipids are compounds in which fatty acids are linked directly to a sugar backbone, forming structures that are compatible with membrane bilayers. In the saccharolipids, a sugar substitutes for the glycerol backbone that is present in glycerolipids and glycerophospholipids. The most familiar saccharolipids contain an acylated glucosamine. In contrast to others glycolipids, the fatty acid is not glycosidically linked to the sugar moiety. (-)-Cypellocarpin C is found in Eucalyptus camaldulensis , Eucalyptus cypellocarpa and Eucalyptus maideni. (-)-Cypellocarpin C was first documented in 2007 (PMID: 17552153). Based on a literature review a small amount of articles have been published on cypellocarpin C (PMID: 20708173) (PMID: 29986399) (PMID: 28865624).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304292204022D          

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M  END

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 24 25  2  0  0  0  0
 24 26  1  0  0  0  0
 26 27  2  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
 30 31  1  0  0  0  0
 26 31  1  0  0  0  0
 29 32  1  6  0  0  0
 32 33  1  0  0  0  0
 32 34  1  0  0  0  0
 32 35  1  0  0  0  0
  2 36  1  6  0  0  0
  1 37  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0081054

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1=CC(=O)C2=C(O)C=C(O[C@@H]3O[C@H](COC(=O)C4=CC[C@@H](CC4)C(C)(C)O)[C@@H](O)[C@H](O)[C@H]3O)C=C2O1

> <INCHI_IDENTIFIER>
InChI=1S/C26H32O11/c1-12-8-16(27)20-17(28)9-15(10-18(20)35-12)36-25-23(31)22(30)21(29)19(37-25)11-34-24(32)13-4-6-14(7-5-13)26(2,3)33/h4,8-10,14,19,21-23,25,28-31,33H,5-7,11H2,1-3H3/t14-,19+,21+,22-,23+,25+/m0/s1

> <INCHI_KEY>
OUBDJJFZUQGQLU-ZHFYLPRNSA-N

> <FORMULA>
C26H32O11

> <MOLECULAR_WEIGHT>
520.531

> <EXACT_MASS>
520.19446185

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
69

> <JCHEM_AVERAGE_POLARIZABILITY>
52.792284770807115

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[(5-hydroxy-2-methyl-4-oxo-4H-chromen-7-yl)oxy]oxan-2-yl]methyl (4R)-4-(2-hydroxypropan-2-yl)cyclohex-1-ene-1-carboxylate

> <ALOGPS_LOGP>
1.35

> <JCHEM_LOGP>
1.9101490973333326

> <ALOGPS_LOGS>
-3.02

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.201652029749399

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.331252343260368

> <JCHEM_PKA_STRONGEST_BASIC>
-0.8730944129342285

> <JCHEM_POLAR_SURFACE_AREA>
172.20999999999998

> <JCHEM_REFRACTIVITY>
129.90030000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.94e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[(5-hydroxy-2-methyl-4-oxochromen-7-yl)oxy]oxan-2-yl]methyl (4R)-4-(2-hydroxypropan-2-yl)cyclohex-1-ene-1-carboxylate

> <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      -5.335  -3.080   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -6.668  -2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -6.668  -0.770   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -5.335   0.000   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      -4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -4.001  -2.310   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -2.667  -3.080   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0      -2.667   0.000   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       2.667  -0.000   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       5.335  -0.000   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       0.000  -4.620   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      -8.002   0.000   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -8.002   1.540   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      -9.336   2.310   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0     -10.669   1.540   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      -9.336   3.850   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0     -10.669   4.620   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0     -10.669   6.160   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -9.336   6.930   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -8.002   6.160   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -8.002   4.620   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -9.336   8.470   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -9.336  10.010   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -7.796   8.470   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0     -10.876   8.470   0.000  0.00  0.00           O+0
HETATM   36  O   UNK     0      -8.002  -3.080   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0      -5.335  -4.620   0.000  0.00  0.00           O+0
CONECT    1    2    6   37                                                  
CONECT    2    1    3   36                                                  
CONECT    3    2    4   22                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    8                                                  
CONECT    6    5    1    7                                                  
CONECT    7    6                                                            
CONECT    8    5    9                                                       
CONECT    9    8   10   14                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   21                                                  
CONECT   12   11   13   18                                                  
CONECT   13   12   14   15                                                  
CONECT   14   13    9                                                       
CONECT   15   13   16                                                       
CONECT   16   15   17   20                                                  
CONECT   17   16   18                                                       
CONECT   18   17   12   19                                                  
CONECT   19   18                                                            
CONECT   20   16                                                            
CONECT   21   11                                                            
CONECT   22    3   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27   31                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30   32                                                  
CONECT   30   29   31                                                       
CONECT   31   30   26                                                       
CONECT   32   29   33   34   35                                             
CONECT   33   32                                                            
CONECT   34   32                                                            
CONECT   35   32                                                            
CONECT   36    2                                                            
CONECT   37    1                                                            
MASTER        0    0    0    0    0    0    0    0   37    0   80    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₆H₃₂O₁₁

Average Mass

520.5310 Da

Monoisotopic Mass

520.19446 Da

IUPAC Name

[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[(5-hydroxy-2-methyl-4-oxo-4H-chromen-7-yl)oxy]oxan-2-yl]methyl (4R)-4-(2-hydroxypropan-2-yl)cyclohex-1-ene-1-carboxylate

Traditional Name

[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[(5-hydroxy-2-methyl-4-oxochromen-7-yl)oxy]oxan-2-yl]methyl (4R)-4-(2-hydroxypropan-2-yl)cyclohex-1-ene-1-carboxylate

CAS Registry Number

Not Available

SMILES

CC1=CC(=O)C2=C(O)C=C(O[C@@H]3O[C@H](COC(=O)C4=CC[C@@H](CC4)C(C)(C)O)[C@@H](O)[C@H](O)[C@H]3O)C=C2O1

InChI Identifier

InChI=1S/C26H32O11/c1-12-8-16(27)20-17(28)9-15(10-18(20)35-12)36-25-23(31)22(30)21(29)19(37-25)11-34-24(32)13-4-6-14(7-5-13)26(2,3)33/h4,8-10,14,19,21-23,25,28-31,33H,5-7,11H2,1-3H3/t14-,19+,21+,22-,23+,25+/m0/s1

InChI Key

OUBDJJFZUQGQLU-ZHFYLPRNSA-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
Eucalyptus camaldulensis	Plant	KNApSAcK
Eucalyptus cypellocarpa	Plant	KNApSAcK
Eucalyptus maideni	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as saccharolipids. Saccharolipids are compounds in which fatty acids are linked directly to a sugar backbone, forming structures that are compatible with membrane bilayers. In the saccharolipids, a sugar substitutes for the glycerol backbone that is present in glycerolipids and glycerophospholipids. The most familiar saccharolipids contain an acylated glucosamine. In contrast to others glycolipids, the fatty acid is not glycosidically linked to the sugar moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Saccharolipids

Sub Class

Not Available

Direct Parent

Saccharolipids

Alternative Parents

Substituents

Saccharolipid
Phenolic glycoside
Chromone
Glycosyl compound
O-glycosyl compound
Aromatic monoterpenoid
Benzopyran
Bicyclic monoterpenoid
Monoterpenoid
1-benzopyran
P-menthane monoterpenoid
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Pyranone
Monosaccharide
Oxane
Benzenoid
Pyran
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Tertiary alcohol
Vinylogous acid
Heteroaromatic compound
Secondary alcohol
Carboxylic acid ester
Polyol
Organoheterocyclic compound
Acetal
Monocarboxylic acid or derivatives
Oxacycle
Carboxylic acid derivative
Organic oxygen compound
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organooxygen 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	1.35	ALOGPS
logP	1.91	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	7.33	ChemAxon
pKa (Strongest Basic)	-0.87	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	172.21 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	129.9 m³·mol⁻¹	ChemAxon
Polarizability	52.79 Å³	ChemAxon
Number of Rings	4	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

C00046708

Chemspider ID

8801154

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10625791

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Hakki Z, Cao B, Heskes AM, Goodger JQ, Woodrow IE, Williams SJ: Synthesis of the monoterpenoid esters cypellocarpin C and cuniloside B and evidence for their widespread occurrence in Eucalyptus. Carbohydr Res. 2010 Sep 23;345(14):2079-84. doi: 10.1016/j.carres.2010.07.029. Epub 2010 Jul 21. [PubMed:20708173 ]
Yang XW, Guo QM: [Studies on chemical constituents in fruits of Eucalyptus globulus]. Zhongguo Zhong Yao Za Zhi. 2007 Mar;32(6):496-500. [PubMed:17552153 ]
Brezani V, Lelakova V, Hassan STS, Berchova-Bimova K, Novy P, Kloucek P, Marsik P, Dall'Acqua S, Hosek J, Smejkal K: Anti-Infectivity against Herpes Simplex Virus and Selected Microbes and Anti-Inflammatory Activities of Compounds Isolated from Eucalyptus globulus Labill. Viruses. 2018 Jul 6;10(7):360. doi: 10.3390/v10070360. [PubMed:29986399 ]
Agregan R, Munekata PES, Franco D, Dominguez R, Carballo J, Lorenzo JM: Phenolic compounds from three brown seaweed species using LC-DAD-ESI-MS/MS. Food Res Int. 2017 Sep;99(Pt 3):979-985. doi: 10.1016/j.foodres.2017.03.043. Epub 2017 Mar 24. [PubMed:28865624 ]

Showing NP-Card for (-)-Cypellocarpin C (NP0081054)

MOL for NP0081054 ((-)-Cypellocarpin C)

3D MOL for NP0081054 ((-)-Cypellocarpin C)

3D SDF for NP0081054 ((-)-Cypellocarpin C)

3D-SDF for NP0081054 ((-)-Cypellocarpin C)

PDB for NP0081054 ((-)-Cypellocarpin C)

3D PDB for NP0081054 ((-)-Cypellocarpin C)

SMILES for NP0081054 ((-)-Cypellocarpin C)

INCHI for NP0081054 ((-)-Cypellocarpin C)

Structure for NP0081054 ((-)-Cypellocarpin C)

3D Structure for NP0081054 ((-)-Cypellocarpin C)