NP-MRD: Showing NP-Card for Centratherolide-E (NP0350773)

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Record Information

Version

2.0

Created at

2025-02-28 23:58:12 UTC

Updated at

2025-03-02 00:05:02 UTC

NP-MRD ID

NP0350773

Natural Product DOI

https://doi.org/10.57994/3757

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Centratherolide-E

Description

Based on a literature review very few articles have been published on (2Z,4R,8R,9S,11S)-2-(hydroxymethyl)-11-methyl-7-methylidene-6,12-dioxo-5,14-dioxatricyclo[9.2.1.0,]Tetradeca-1(13),2-dien-9-yl (2Z)-2-(hydroxymethyl)but-2-enoate.

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 05292300052D          

 28 30  0  0  1  0            999 V2000
   -0.5874    0.4730    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1972    0.2181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1972   -0.6069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6821   -1.2744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4668   -1.5293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4668   -2.3543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7523   -2.7668    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2514   -1.2744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7363   -0.6069    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7363    0.2181    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5209    0.4730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0058   -0.1944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5209   -0.8619    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8308   -0.1944    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7759    1.2576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2514    0.8855    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7363    1.5529    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4007    2.3066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8857    2.9741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5501    3.7277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0350    4.3952    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7061    2.8878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1911    3.5553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5803    2.3928    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4668    1.1404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6821    0.8855    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4121   -0.1944    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1972    1.5529    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  1  0  0  0  0
  6  7  1  0  0  0  0
  5  8  2  0  0  0  0
  9  8  1  0  0  0  0
 10  9  1  0  0  0  0
 10 11  1  1  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
  9 13  1  6  0  0  0
 12 14  2  0  0  0  0
 11 15  2  0  0  0  0
 10 16  1  0  0  0  0
 16 17  1  6  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
 19 22  2  0  0  0  0
 22 23  1  0  0  0  0
 18 24  2  0  0  0  0
 16 25  1  0  0  0  0
 26 25  1  0  0  0  0
 26  2  1  0  0  0  0
 26 27  1  0  0  0  0
  4 27  1  0  0  0  0
 26 28  1  6  0  0  0
M  END


  Mrv2104 05292300052D          

 28 30  0  0  1  0            999 V2000
   -0.5874    0.4730    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1972    0.2181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1972   -0.6069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6821   -1.2744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4668   -1.5293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4668   -2.3543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7523   -2.7668    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2514   -1.2744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7363   -0.6069    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7363    0.2181    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5209    0.4730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0058   -0.1944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5209   -0.8619    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8308   -0.1944    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7759    1.2576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2514    0.8855    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7363    1.5529    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4007    2.3066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8857    2.9741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5501    3.7277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0350    4.3952    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7061    2.8878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1911    3.5553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5803    2.3928    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4668    1.1404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6821    0.8855    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4121   -0.1944    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1972    1.5529    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  1  0  0  0  0
  6  7  1  0  0  0  0
  5  8  2  0  0  0  0
  9  8  1  0  0  0  0
 10  9  1  0  0  0  0
 10 11  1  1  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
  9 13  1  6  0  0  0
 12 14  2  0  0  0  0
 11 15  2  0  0  0  0
 10 16  1  0  0  0  0
 16 17  1  6  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
 19 22  2  0  0  0  0
 22 23  1  0  0  0  0
 18 24  2  0  0  0  0
 16 25  1  0  0  0  0
 26 25  1  0  0  0  0
 26  2  1  0  0  0  0
 26 27  1  0  0  0  0
  4 27  1  0  0  0  0
 26 28  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0350773

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C\C=C(/CO)C(=O)O[C@H]1C[C@@]2(C)OC(=CC2=O)\C(CO)=C/[C@H]2OC(=O)C(=C)[C@H]12

> <INCHI_IDENTIFIER>
InChI=1S/C20H22O8/c1-4-11(8-21)19(25)27-15-7-20(3)16(23)6-13(28-20)12(9-22)5-14-17(15)10(2)18(24)26-14/h4-6,14-15,17,21-22H,2,7-9H2,1,3H3/b11-4+,12-5-/t14-,15+,17+,20-/m1/s1

> <INCHI_KEY>
RBPBHKBVZNHLLE-XZOIHQSRSA-N

> <FORMULA>
C20H22O8

> <MOLECULAR_WEIGHT>
390.388

> <EXACT_MASS>
390.131467668

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
50

> <JCHEM_AVERAGE_POLARIZABILITY>
38.41980578322136

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2Z,4R,8R,9S,11R)-2-(hydroxymethyl)-11-methyl-7-methylidene-6,12-dioxo-5,14-dioxatricyclo[9.2.1.0^{4,8}]tetradeca-1(13),2-dien-9-yl (2E)-2-(hydroxymethyl)but-2-enoate

> <JCHEM_LOGP>
0.5090294356666673

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.259945643087063

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.64746988032254

> <JCHEM_PKA_STRONGEST_BASIC>
-2.7895506138034865

> <JCHEM_POLAR_SURFACE_AREA>
119.36

> <JCHEM_REFRACTIVITY>
99.7765

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(2Z,4R,8R,9S,11R)-2-(hydroxymethyl)-11-methyl-7-methylidene-6,12-dioxo-5,14-dioxatricyclo[9.2.1.0^{4,8}]tetradeca-1(13),2-dien-9-yl (2E)-2-(hydroxymethyl)but-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-MAY-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-MAY-23         0                                  
HETATM    1  O   UNK     0      -1.097   0.883   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       0.368   0.407   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.368  -1.133   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.273  -2.379   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.738  -2.855   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.738  -4.395   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       1.404  -5.165   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       4.203  -2.379   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.108  -1.133   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.108   0.407   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.572   0.883   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.478  -0.363   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       6.572  -1.609   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       9.018  -0.363   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       7.048   2.348   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.203   1.653   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       5.108   2.899   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       4.481   4.306   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.387   5.552   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.760   6.958   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       5.665   8.204   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       6.918   5.391   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       7.823   6.636   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       2.950   4.467   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       2.738   2.129   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       1.273   1.653   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       0.769  -0.363   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       0.368   2.899   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   26                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   27                                                  
CONECT    5    4    6    8                                                  
CONECT    6    5    7                                                       
CONECT    7    6                                                            
CONECT    8    5    9                                                       
CONECT    9    8   10   13                                                  
CONECT   10    9   11   16                                                  
CONECT   11   10   12   15                                                  
CONECT   12   11   13   14                                                  
CONECT   13   12    9                                                       
CONECT   14   12                                                            
CONECT   15   11                                                            
CONECT   16   10   17   25                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   24                                                  
CONECT   19   18   20   22                                                  
CONECT   20   19   21                                                       
CONECT   21   20                                                            
CONECT   22   19   23                                                       
CONECT   23   22                                                            
CONECT   24   18                                                            
CONECT   25   16   26                                                       
CONECT   26   25    2   27   28                                             
CONECT   27   26    4                                                       
CONECT   28   26                                                            
MASTER        0    0    0    0    0    0    0    0   28    0   60    0
END

View in JSmol

Synonyms

Value	Source
(2Z,4R,8R,9S,11S)-2-(Hydroxymethyl)-11-methyl-7-methylidene-6,12-dioxo-5,14-dioxatricyclo[9.2.1.0,]tetradeca-1(13),2-dien-9-yl (2Z)-2-(hydroxymethyl)but-2-enoic acid	Generator

Chemical Formula

C₂₀H₂₂O₈

Average Mass

390.3880 Da

Monoisotopic Mass

390.13147 Da

IUPAC Name

(2Z,4R,8R,9S,11R)-2-(hydroxymethyl)-11-methyl-7-methylidene-6,12-dioxo-5,14-dioxatricyclo[9.2.1.0^{4,8}]tetradeca-1(13),2-dien-9-yl (2E)-2-(hydroxymethyl)but-2-enoate

Traditional Name

(2Z,4R,8R,9S,11R)-2-(hydroxymethyl)-11-methyl-7-methylidene-6,12-dioxo-5,14-dioxatricyclo[9.2.1.0^{4,8}]tetradeca-1(13),2-dien-9-yl (2E)-2-(hydroxymethyl)but-2-enoate

CAS Registry Number

Not Available

SMILES

C\C=C(/CO)C(=O)O[C@H]1C[C@@]2(C)OC(=CC2=O)\C(CO)=C/[C@H]2OC(=O)C(=C)[C@H]12

InChI Identifier

InChI=1S/C20H22O8/c1-4-11(8-21)19(25)27-15-7-20(3)16(23)6-13(28-20)12(9-22)5-14-17(15)10(2)18(24)26-14/h4-6,14-15,17,21-22H,2,7-9H2,1,3H3/b11-4+,12-5-/t14-,15+,17+,20-/m1/s1

InChI Key

RBPBHKBVZNHLLE-XZOIHQSRSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 600 MHz, C2D6OS, experimental)	quan.khong@nih.gov	National Cancer Institute at Frederick	Quan T. Khong	2025-03-01	View Spectrum
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, C2D6OS, experimental)	quan.khong@nih.gov	National Cancer Institute at Frederick	Quan T. Khong	2025-03-01	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, C2D6OS, experimental)	quan.khong@nih.gov	National Cancer Institute at Frederick	Quan T. Khong	2025-03-01	View Spectrum
NOESY NMR	[¹H, ¹H] NMR Spectrum (2D, 600 MHz, C2D6OS, experimental)	quan.khong@nih.gov	National Cancer Institute at Frederick	Quan T. Khong	2025-03-01	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, C2D6OS, experimental)	quan.khong@nih.gov	National Cancer Institute at Frederick	Quan T. Khong	2025-02-28	View Spectrum
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, C2D6OS, experimental)	quan.khong@nih.gov	National Cancer Institute at Frederick	Quan T. Khong	2025-02-28	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, C2D6OS, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View

Chemical Shift Submissions

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 600, C2D6OS, simulated)	quan.khong@nih.gov	National Cancer Institute at Frederick	Quan T. Khong	2025-02-28	View Spectrum

Species

Species of Origin

Species Name	Source	Reference
Centratherum punctatum		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	0.51	ChemAxon
pKa (Strongest Acidic)	14.65	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	119.36 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	99.78 m³·mol⁻¹	ChemAxon
Polarizability	38.42 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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

162843654

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for Centratherolide-E (NP0350773)

MOL for NP0350773 (Centratherolide-E)

3D MOL for NP0350773 (Centratherolide-E)

3D SDF for NP0350773 (Centratherolide-E)

3D-SDF for NP0350773 (Centratherolide-E)

PDB for NP0350773 (Centratherolide-E)

3D PDB for NP0350773 (Centratherolide-E)

SMILES for NP0350773 (Centratherolide-E)

INCHI for NP0350773 (Centratherolide-E)

Structure for NP0350773 (Centratherolide-E)

3D Structure for NP0350773 (Centratherolide-E)