NP-MRD: Showing NP-Card for (+)-Mellerin A (NP0079549)

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Record Information

Version

2.0

Created at

2022-04-29 00:33:51 UTC

Updated at

2022-04-29 00:33:51 UTC

NP-MRD ID

NP0079549

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(+)-Mellerin A

Description

Mellerin A belongs to the class of organic compounds known as phorbol esters. These are tigliane diterpenoids which are esters of phorbol. (+)-Mellerin A is found in Neoboutonia melleri. Based on a literature review very few articles have been published on Mellerin A.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304292202332D          

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M  END

     RDKit          3D

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 28 29  1  0  0  0  0
 13 30  1  1  0  0  0
  8 31  1  0  0  0  0
 31 32  1  0  0  0  0
  4 33  1  6  0  0  0
  1 34  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0079549

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCCCCC(=O)O[C@@]12C[C@@H](C)[C@]3(O)[C@@H]4C=C(C)C(=O)[C@@]4(O)CC(CO)=C[C@H]3[C@@H]1C2(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C28H42O6/c1-6-7-8-9-10-11-22(30)34-27-14-18(3)28(33)20(23(27)25(27,4)5)13-19(16-29)15-26(32)21(28)12-17(2)24(26)31/h12-13,18,20-21,23,29,32-33H,6-11,14-16H2,1-5H3/t18-,20+,21-,23-,26-,27+,28-/m1/s1

> <INCHI_KEY>
VJTBJVHQCFQKLQ-XTNHTTTKSA-N

> <FORMULA>
C28H42O6

> <MOLECULAR_WEIGHT>
474.638

> <EXACT_MASS>
474.298139072

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
76

> <JCHEM_AVERAGE_POLARIZABILITY>
54.86732492217423

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,2S,6R,10S,11R,13S,15R)-1,6-dihydroxy-8-(hydroxymethyl)-4,12,12,15-tetramethyl-5-oxotetracyclo[8.5.0.0^{2,6}.0^{11,13}]pentadeca-3,8-dien-13-yl octanoate

> <ALOGPS_LOGP>
3.65

> <JCHEM_LOGP>
3.6169687179999994

> <ALOGPS_LOGS>
-4.74

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.007139468928134

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.57463336323649

> <JCHEM_PKA_STRONGEST_BASIC>
-2.73161300855332

> <JCHEM_POLAR_SURFACE_AREA>
104.06

> <JCHEM_REFRACTIVITY>
131.29809999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.61e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2S,6R,10S,11R,13S,15R)-1,6-dihydroxy-8-(hydroxymethyl)-4,12,12,15-tetramethyl-5-oxotetracyclo[8.5.0.0^{2,6}.0^{11,13}]pentadeca-3,8-dien-13-yl octanoate

> <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       2.472  -9.184   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.396  -7.951   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.509  -6.692   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.038  -7.146   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.015  -8.686   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -0.245  -9.572   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      -0.235  -6.279   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.350  -4.743   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.779  -3.695   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.302  -3.925   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.072  -5.259   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       3.940  -6.531   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       4.612  -5.259   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.382  -3.925   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.612  -2.591   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.072  -2.591   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.842  -1.258   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.959   0.004   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.725   0.004   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       5.946  -1.821   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       7.279  -2.591   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       7.279  -4.131   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       8.613  -1.821   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       9.947  -2.591   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      11.280  -1.821   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      12.614  -2.591   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      13.948  -1.821   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      15.281  -2.591   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      16.615  -1.821   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       5.382  -6.592   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -1.783  -4.180   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      -2.013  -2.657   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0      -0.329  -7.855   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       2.926 -10.655   0.000  0.00  0.00           C+0
CONECT    1    2    5   34                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4   11                                                  
CONECT    4    3    5    7   33                                             
CONECT    5    4    1    6                                                  
CONECT    6    5                                                            
CONECT    7    4    8                                                       
CONECT    8    7    9   31                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   16                                                  
CONECT   11   10    3   12   13                                             
CONECT   12   11                                                            
CONECT   13   11   14   30                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   17   20                                             
CONECT   16   15   10   17                                                  
CONECT   17   16   15   18   19                                             
CONECT   18   17                                                            
CONECT   19   17                                                            
CONECT   20   15   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28                                                            
CONECT   30   13                                                            
CONECT   31    8   32                                                       
CONECT   32   31                                                            
CONECT   33    4                                                            
CONECT   34    1                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   74    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₈H₄₂O₆

Average Mass

474.6380 Da

Monoisotopic Mass

474.29814 Da

IUPAC Name

(1R,2S,6R,10S,11R,13S,15R)-1,6-dihydroxy-8-(hydroxymethyl)-4,12,12,15-tetramethyl-5-oxotetracyclo[8.5.0.0^{2,6}.0^{11,13}]pentadeca-3,8-dien-13-yl octanoate

Traditional Name

(1R,2S,6R,10S,11R,13S,15R)-1,6-dihydroxy-8-(hydroxymethyl)-4,12,12,15-tetramethyl-5-oxotetracyclo[8.5.0.0^{2,6}.0^{11,13}]pentadeca-3,8-dien-13-yl octanoate

CAS Registry Number

Not Available

SMILES

CCCCCCCC(=O)O[C@@]12C[C@@H](C)[C@]3(O)[C@@H]4C=C(C)C(=O)[C@@]4(O)CC(CO)=C[C@H]3[C@@H]1C2(C)C

InChI Identifier

InChI=1S/C28H42O6/c1-6-7-8-9-10-11-22(30)34-27-14-18(3)28(33)20(23(27)25(27,4)5)13-19(16-29)15-26(32)21(28)12-17(2)24(26)31/h12-13,18,20-21,23,29,32-33H,6-11,14-16H2,1-5H3/t18-,20+,21-,23-,26-,27+,28-/m1/s1

InChI Key

VJTBJVHQCFQKLQ-XTNHTTTKSA-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
Neoboutonia melleri	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phorbol esters. These are tigliane diterpenoids which are esters of phorbol.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Phorbol esters

Alternative Parents

Substituents

Phorbol ester
Fatty acid ester
Fatty acyl
Cyclic alcohol
Tertiary alcohol
Carboxylic acid ester
Ketone
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organooxygen compound
Organic oxide
Organic oxygen compound
Alcohol
Carbonyl group
Hydrocarbon derivative
Primary alcohol
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic 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	3.65	ALOGPS
logP	3.62	ChemAxon
logS	-4.7	ALOGPS
pKa (Strongest Acidic)	12.57	ChemAxon
pKa (Strongest Basic)	-2.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	104.06 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	131.3 m³·mol⁻¹	ChemAxon
Polarizability	54.87 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	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

C00044231

Chemspider ID

90635803

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

102317132

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for (+)-Mellerin A (NP0079549)

MOL for NP0079549 ((+)-Mellerin A)

3D MOL for NP0079549 ((+)-Mellerin A)

3D SDF for NP0079549 ((+)-Mellerin A)

3D-SDF for NP0079549 ((+)-Mellerin A)

PDB for NP0079549 ((+)-Mellerin A)

3D PDB for NP0079549 ((+)-Mellerin A)

SMILES for NP0079549 ((+)-Mellerin A)

INCHI for NP0079549 ((+)-Mellerin A)

Structure for NP0079549 ((+)-Mellerin A)

3D Structure for NP0079549 ((+)-Mellerin A)