NP-MRD: Showing NP-Card for Osmanthuside B (NP0335830)

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Record Information

Version

2.0

Created at

2024-09-11 03:26:45 UTC

Updated at

2024-09-11 03:26:45 UTC

NP-MRD ID

NP0335830

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Osmanthuside B

Description

Osmanthuside B was first documented in 2019 (PMID: 31007699). Based on a literature review a small amount of articles have been published on Osmanthuside B (PMID: 34609151) (PMID: 38872484) (PMID: 36935606) (PMID: 36364215).

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 05262305582D          

 42 45  0  0  0  0            999 V2000
   -2.1434   -6.1875    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   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145  -13.6125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000  -12.3750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.0000  -14.0250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145  -12.7875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.8579   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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 42 29  1  0  0  0  0
M  END


  Mrv2104 05262305582D          

 42 45  0  0  0  0            999 V2000
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    0.0000   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145  -13.6125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000  -12.3750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000  -14.0250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145  -12.7875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289  -12.3750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289  -11.5500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145  -12.7875    0.0000 C   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  -13.6125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -9.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -9.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.8579   -9.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434  -10.3125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -9.0750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.7145   -7.8375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -5.0013   -6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013   -7.8375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724  -10.3125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434  -11.1375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -7.4250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -9.9000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -7.8375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -8.6625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  7  2  1  0  0  0  0
  8  3  2  0  0  0  0
  9  4  1  0  0  0  0
 10  5  2  0  0  0  0
 11  6  2  0  0  0  0
 13 12  1  0  0  0  0
 15  1  1  0  0  0  0
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 16  6  1  0  0  0  0
 17  4  2  0  0  0  0
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 17 12  1  0  0  0  0
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 18  8  1  0  0  0  0
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 31 18  1  0  0  0  0
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 33 21  2  0  0  0  0
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 42 29  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0335830

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1OC(OC2C(O)C(OCCC3=CC=C(O)C=C3)OC(CO)C2OC(=O)\C=C\C2=CC=C(O)C=C2)C(O)C(O)C1O

> <INCHI_IDENTIFIER>
InChI=1/C29H36O13/c1-15-22(34)23(35)24(36)29(39-15)42-27-25(37)28(38-13-12-17-4-9-19(32)10-5-17)40-20(14-30)26(27)41-21(33)11-6-16-2-7-18(31)8-3-16/h2-11,15,20,22-32,34-37H,12-14H2,1H3/b11-6+

> <INCHI_KEY>
PRTREKIVGSNQRM-IZZDOVSWNA-N

> <FORMULA>
C29H36O13

> <MOLECULAR_WEIGHT>
592.594

> <EXACT_MASS>
592.215591219

> <JCHEM_ACCEPTOR_COUNT>
12

> <JCHEM_ATOM_COUNT>
78

> <JCHEM_AVERAGE_POLARIZABILITY>
60.10798124844398

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
5-hydroxy-2-(hydroxymethyl)-6-[2-(4-hydroxyphenyl)ethoxy]-4-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-3-yl (2E)-3-(4-hydroxyphenyl)prop-2-enoate

> <JCHEM_LOGP>
1.4265560036666671

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.258376036846569

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.334216615156752

> <JCHEM_PKA_STRONGEST_BASIC>
-2.981814819846054

> <JCHEM_POLAR_SURFACE_AREA>
204.82999999999993

> <JCHEM_REFRACTIVITY>
144.44129999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
5-hydroxy-2-(hydroxymethyl)-6-[2-(4-hydroxyphenyl)ethoxy]-4-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-3-yl (2E)-3-(4-hydroxyphenyl)prop-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 26-MAY-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-MAY-23         0                                  
HETATM    1  C   UNK     0      -4.001 -11.550   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000  -9.240   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.667  -9.240   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.334 -25.410   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000 -23.100   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.334 -11.550   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000  -7.700   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.667  -7.700   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000 -26.180   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.334 -23.870   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.667 -12.320   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.667 -23.100   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.667 -21.560   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.334 -16.170   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -5.335 -12.320   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.334 -10.010   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.334 -23.870   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.334 -25.410   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -2.667 -16.940   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -2.667 -13.860   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -6.668 -11.550   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -8.002 -12.320   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -8.002 -13.860   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -5.335 -18.480   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -4.001 -16.170   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -5.335 -16.940   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -4.001 -19.250   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -6.668 -14.630   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       0.000 -16.940   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0      -1.334  -5.390   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0       2.667 -26.180   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0      -1.334 -14.630   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0      -6.668 -10.010   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0      -9.336 -11.550   0.000  0.00  0.00           O+0
HETATM   36  O   UNK     0      -9.336 -14.630   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0      -6.668 -19.250   0.000  0.00  0.00           O+0
HETATM   38  O   UNK     0      -4.001 -20.790   0.000  0.00  0.00           O+0
HETATM   39  O   UNK     0      -5.335 -13.860   0.000  0.00  0.00           O+0
HETATM   40  O   UNK     0      -2.667 -18.480   0.000  0.00  0.00           O+0
HETATM   41  O   UNK     0      -4.001 -14.630   0.000  0.00  0.00           O+0
HETATM   42  O   UNK     0      -6.668 -16.170   0.000  0.00  0.00           O+0
CONECT    1   15                                                            
CONECT    2    7   16                                                       
CONECT    3    8   16                                                       
CONECT    4    9   17                                                       
CONECT    5   10   17                                                       
CONECT    6   11   16                                                       
CONECT    7    2   18                                                       
CONECT    8    3   18                                                       
CONECT    9    4   19                                                       
CONECT   10    5   19                                                       
CONECT   11    6   21                                                       
CONECT   12   13   17                                                       
CONECT   13   12   38                                                       
CONECT   14   20   30                                                       
CONECT   15    1   22   39                                                  
CONECT   16    2    3    6                                                  
CONECT   17    4    5   12                                                  
CONECT   18    7    8   31                                                  
CONECT   19    9   10   32                                                  
CONECT   20   14   26   40                                                  
CONECT   21   11   33   41                                                  
CONECT   22   15   23   34                                                  
CONECT   23   22   24   35                                                  
CONECT   24   23   29   36                                                  
CONECT   25   27   28   37                                                  
CONECT   26   20   27   41                                                  
CONECT   27   25   26   42                                                  
CONECT   28   25   38   40                                                  
CONECT   29   24   39   42                                                  
CONECT   30   14                                                            
CONECT   31   18                                                            
CONECT   32   19                                                            
CONECT   33   21                                                            
CONECT   34   22                                                            
CONECT   35   23                                                            
CONECT   36   24                                                            
CONECT   37   25                                                            
CONECT   38   13   28                                                       
CONECT   39   15   29                                                       
CONECT   40   20   28                                                       
CONECT   41   21   26                                                       
CONECT   42   27   29                                                       
MASTER        0    0    0    0    0    0    0    0   42    0   90    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₉H₃₆O₁₃

Average Mass

592.5940 Da

Monoisotopic Mass

592.21559 Da

IUPAC Name

5-hydroxy-2-(hydroxymethyl)-6-[2-(4-hydroxyphenyl)ethoxy]-4-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-3-yl (2E)-3-(4-hydroxyphenyl)prop-2-enoate

Traditional Name

5-hydroxy-2-(hydroxymethyl)-6-[2-(4-hydroxyphenyl)ethoxy]-4-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-3-yl (2E)-3-(4-hydroxyphenyl)prop-2-enoate

CAS Registry Number

Not Available

SMILES

CC1OC(OC2C(O)C(OCCC3=CC=C(O)C=C3)OC(CO)C2OC(=O)\C=C\C2=CC=C(O)C=C2)C(O)C(O)C1O

InChI Identifier

InChI=1/C29H36O13/c1-15-22(34)23(35)24(36)29(39-15)42-27-25(37)28(38-13-12-17-4-9-19(32)10-5-17)40-20(14-30)26(27)41-21(33)11-6-16-2-7-18(31)8-3-16/h2-11,15,20,22-32,34-37H,12-14H2,1H3/b11-6+

InChI Key

PRTREKIVGSNQRM-IZZDOVSWNA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Classification

Not classified

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	1.43	ChemAxon
pKa (Strongest Acidic)	9.33	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	204.83 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	144.44 m³·mol⁻¹	ChemAxon
Polarizability	60.11 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	No	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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Yang Y, Wu Y, Zhuang Y, Liu T: Discovery of Glycosyltransferases Involved in the Biosynthesis of Ligupurpuroside B. Org Lett. 2021 Oct 15;23(20):7851-7854. doi: 10.1021/acs.orglett.1c02873. Epub 2021 Oct 5. [PubMed:34609151 ]
Zhang Y, Wang Y, Yang S, Xiao Y, Guan H, Yue X, Wang X, Li X: The Difference of Chemical Components and Biological Activities of the Raw Products slices and the Wine Steam-Processed Product from Cistanche deserticola. Evid Based Complement Alternat Med. 2019 Mar 17;2019:2167947. doi: 10.1155/2019/2167947. eCollection 2019. [PubMed:31007699 ]
Liu Y, Han X, Zhao M, Liu L, Deng Z, Zhao Q, Yu Y: Functional characterization of polyphenol oxidase OfPPO2 supports its involvement in parallel biosynthetic pathways of acteoside. Plant J. 2024 Jul;119(2):927-941. doi: 10.1111/tpj.16807. Epub 2024 Jun 14. [PubMed:38872484 ]
Yang Y, Xi D, Wu Y, Liu T: Complete biosynthesis of the phenylethanoid glycoside verbascoside. Plant Commun. 2023 Jul 10;4(4):100592. doi: 10.1016/j.xplc.2023.100592. Epub 2023 Mar 20. [PubMed:36935606 ]
Lu SH, Zuo HJ, Huang J, Chen R, Pan JP, Li XX: Phenylethanoid and Phenylmethanoid Glycosides from the Leaves of Ligustrum robustum and Their Bioactivities. Molecules. 2022 Oct 31;27(21):7390. doi: 10.3390/molecules27217390. [PubMed:36364215 ]

Showing NP-Card for Osmanthuside B (NP0335830)

MOL for NP0335830 (Osmanthuside B)

3D MOL for NP0335830 (Osmanthuside B)

3D SDF for NP0335830 (Osmanthuside B)

3D-SDF for NP0335830 (Osmanthuside B)

PDB for NP0335830 (Osmanthuside B)

3D PDB for NP0335830 (Osmanthuside B)

SMILES for NP0335830 (Osmanthuside B)

INCHI for NP0335830 (Osmanthuside B)

Structure for NP0335830 (Osmanthuside B)

3D Structure for NP0335830 (Osmanthuside B)