NP-MRD: Showing NP-Card for (+)-Dihydromelitensin (NP0058564)

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Record Information

Version

2.0

Created at

2022-04-28 03:54:35 UTC

Updated at

2022-04-28 03:54:35 UTC

NP-MRD ID

NP0058564

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(+)-Dihydromelitensin

Description

Dehydromelitensin belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units. (+)-Dihydromelitensin is found in Centaurea aspera, Centaurea napifolia, Centaurea paui and Onopordon corymbosum. (+)-Dihydromelitensin was first documented in 2012 (PMID: 23074887). Based on a literature review a small amount of articles have been published on Dehydromelitensin (PMID: 29552061) (PMID: 28693338) (PMID: 25146768) (PMID: 22334063).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 39 40  0  0  0  0  0  0  0  0999 V2000
   -2.4370    1.9557   -0.3440 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5829    1.5665    0.5850 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0751    0.1635    0.6917 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.2219   -0.7066    1.1382 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0114    0.0803    1.7551 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1725    0.9746    1.4595 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0947    2.2021    2.0948 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2364    1.2015   -0.0173 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6444    1.3922   -0.5053 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6917    1.8684    0.1246 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5881    0.9136   -1.8829 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4954    1.0808   -2.7526 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3576    0.2435   -2.0592 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9061   -0.0760   -0.7461 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5867   -0.2644   -0.6669 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9675   -1.6637   -1.0250 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7451   -1.9145   -2.0808 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4838   -2.8414   -0.2542 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9603   -4.0382   -0.8115 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8348    1.2720   -1.1058 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7805    2.9610   -0.3949 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2261    2.2780    1.3063 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0553   -0.0098    1.4645 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9430   -1.2229    2.0619 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5846   -1.3682    0.3231 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4618    0.4501    2.6991 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2940   -0.9644    1.9240 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0782    0.4463    1.8208 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8330    2.3662    2.7267 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6005    2.0039   -0.3781 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6777    2.2100    1.1491 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6341    1.9299   -0.3980 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4616   -0.9497   -0.3415 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0252    0.3975   -1.4415 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0828   -1.0446   -2.6613 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0256   -2.9118   -2.3485 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8057   -2.8619    0.8004 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6280   -2.8969   -0.2454 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4969   -4.2228   -1.6639 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  4  1  1
  3  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  8 14  1  0
 14 13  1  0
 13 11  1  0
 11 12  2  0
 11  9  1  0
  9 10  2  3
 14 15  1  0
 15 16  1  0
 16 17  2  3
 16 18  1  0
 18 19  1  0
  3  2  1  0
  2  1  2  3
 15  3  1  0
  9  8  1  0
  4 23  1  0
  4 24  1  0
  4 25  1  0
  5 26  1  0
  5 27  1  0
  6 28  1  1
  7 29  1  0
  8 30  1  6
 14 33  1  1
 10 31  1  0
 10 32  1  0
 15 34  1  6
 17 35  1  0
 17 36  1  0
 18 37  1  0
 18 38  1  0
 19 39  1  0
  2 22  1  0
  1 20  1  0
  1 21  1  0
M  END


  Mrv1652304282205542D          

 19 20  0  0  1  0            999 V2000
    0.7145   -0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0000   -0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0000    0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8661    1.5246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6906    1.4958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2534    0.8538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7846    1.0799    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2695    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0945    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7846   -0.2549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0396   -1.0396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  5  7  1  6  0  0  0
  7  8  2  0  0  0  0
  5  9  1  1  0  0  0
  4 10  1  1  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
  3 14  1  6  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
  2 17  1  1  0  0  0
 17 18  2  0  0  0  0
  1 19  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0058564

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@]1(C[C@H](O)[C@@H]2[C@H](OC(=O)C2=C)[C@H]1C(=C)CO)C=C

> <INCHI_IDENTIFIER>
InChI=1S/C15H20O4/c1-5-15(4)6-10(17)11-9(3)14(18)19-13(11)12(15)8(2)7-16/h5,10-13,16-17H,1-3,6-7H2,4H3/t10-,11+,12+,13-,15+/m0/s1

> <INCHI_KEY>
GQBRDBUFLQZZBP-IHWVXMPCSA-N

> <FORMULA>
C15H20O4

> <MOLECULAR_WEIGHT>
264.321

> <EXACT_MASS>
264.136159124

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
39

> <JCHEM_AVERAGE_POLARIZABILITY>
28.12695558796351

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3aR,4S,6S,7R,7aR)-6-ethenyl-4-hydroxy-7-(3-hydroxyprop-1-en-2-yl)-6-methyl-3-methylidene-octahydro-1-benzofuran-2-one

> <ALOGPS_LOGP>
0.90

> <JCHEM_LOGP>
0.9697340116666665

> <ALOGPS_LOGS>
-1.97

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.304228845268057

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.609481849160431

> <JCHEM_PKA_STRONGEST_BASIC>
-2.728348832709301

> <JCHEM_POLAR_SURFACE_AREA>
66.76

> <JCHEM_REFRACTIVITY>
71.31210000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.81e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3aR,4S,6S,7R,7aR)-6-ethenyl-4-hydroxy-7-(3-hydroxyprop-1-en-2-yl)-6-methyl-3-methylidene-tetrahydro-3aH-1-benzofuran-2-one

> <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       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.000  -0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.000   1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.483   2.846   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.022   2.792   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.206   1.594   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       2.667   6.160   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0      -1.465   2.016   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      -2.370   0.770   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -3.910   0.770   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      -1.465  -0.476   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.941  -1.941   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
CONECT    1    2    6   19                                                  
CONECT    2    1    3   17                                                  
CONECT    3    2    4   14                                                  
CONECT    4    3    5   10                                                  
CONECT    5    4    6    7    9                                             
CONECT    6    5    1                                                       
CONECT    7    5    8                                                       
CONECT    8    7                                                            
CONECT    9    5                                                            
CONECT   10    4   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12                                                            
CONECT   14    3   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15    2   18                                                  
CONECT   18   17                                                            
CONECT   19    1                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   40    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₅H₂₀O₄

Average Mass

264.3210 Da

Monoisotopic Mass

264.13616 Da

IUPAC Name

(3aR,4S,6S,7R,7aR)-6-ethenyl-4-hydroxy-7-(3-hydroxyprop-1-en-2-yl)-6-methyl-3-methylidene-octahydro-1-benzofuran-2-one

Traditional Name

(3aR,4S,6S,7R,7aR)-6-ethenyl-4-hydroxy-7-(3-hydroxyprop-1-en-2-yl)-6-methyl-3-methylidene-tetrahydro-3aH-1-benzofuran-2-one

CAS Registry Number

Not Available

SMILES

C[C@]1(C[C@H](O)[C@@H]2[C@H](OC(=O)C2=C)[C@H]1C(=C)CO)C=C

InChI Identifier

InChI=1S/C15H20O4/c1-5-15(4)6-10(17)11-9(3)14(18)19-13(11)12(15)8(2)7-16/h5,10-13,16-17H,1-3,6-7H2,4H3/t10-,11+,12+,13-,15+/m0/s1

InChI Key

GQBRDBUFLQZZBP-IHWVXMPCSA-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
Centaurea aspera	LOTUS Database	35616633
Centaurea napifolia	LOTUS Database	35616633
Centaurea paui	LOTUS Database	35616633
Onopordon corymbosum	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Diterpenoids

Alternative Parents

Substituents

Diterpenoid
Elemanolide-skeleton
Benzofuran
Gamma butyrolactone
Cyclic alcohol
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tetrahydrofuran
Carboxylic acid ester
Lactone
Secondary alcohol
Monocarboxylic acid or derivatives
Organoheterocyclic compound
Oxacycle
Carboxylic acid derivative
Hydrocarbon derivative
Organic oxide
Alcohol
Carbonyl group
Organooxygen compound
Primary alcohol
Organic oxygen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic 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	0.9	ALOGPS
logP	0.97	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	14.61	ChemAxon
pKa (Strongest Basic)	-2.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	66.76 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	71.31 m³·mol⁻¹	ChemAxon
Polarizability	28.13 Å³	ChemAxon
Number of Rings	2	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

C00011976

Chemspider ID

8508479

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10333020

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Njeh F, Mhalla D, Hammouda IB, Trigui M, Mezghani-Jarraya R: Antibacterial Activity of Onopordum Espinae: Identification of Hispidulin and Dehydromelitensin-8-(4ꞌ-Hydroxy-Methacrylate). Iran J Pharm Res. 2017 Fall;16(4):1531-1537. [PubMed:29552061 ]
Bordignon A, Frederich M, Ledoux A, Campos PE, Clerc P, Hermann T, Quetin-Leclercq J, Cieckiewicz E: In vitro antiplasmodial and cytotoxic activities of sesquiterpene lactones from Vernonia fimbrillifera Less. (Asteraceae). Nat Prod Res. 2018 Jun;32(12):1463-1466. doi: 10.1080/14786419.2017.1350665. Epub 2017 Jul 10. [PubMed:28693338 ]
Watanabe Y, Novaes P, Varela RM, Molinillo JM, Kato-Noguchi H, Macias FA: Phytotoxic potential of Onopordum acanthium L. (Asteraceae). Chem Biodivers. 2014 Aug;11(8):1247-55. doi: 10.1002/cbdv.201400070. [PubMed:25146768 ]
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Showing NP-Card for (+)-Dihydromelitensin (NP0058564)

MOL for NP0058564 ((+)-Dihydromelitensin)

3D MOL for NP0058564 ((+)-Dihydromelitensin)

3D SDF for NP0058564 ((+)-Dihydromelitensin)

3D-SDF for NP0058564 ((+)-Dihydromelitensin)

PDB for NP0058564 ((+)-Dihydromelitensin)

3D PDB for NP0058564 ((+)-Dihydromelitensin)

SMILES for NP0058564 ((+)-Dihydromelitensin)

INCHI for NP0058564 ((+)-Dihydromelitensin)

Structure for NP0058564 ((+)-Dihydromelitensin)

3D Structure for NP0058564 ((+)-Dihydromelitensin)