NP-MRD: Showing NP-Card for (2r,3s,4s,5s,6s,7s,8r,9e)-11-(6-amino-2-hydroxy-3-methyl-5,8-dioxonaphthalen-1-yl)-3,5,7-trihydroxy-2,4,6,8,10-pentamethyl-11-oxoundec-9-enoic acid (NP0276720)

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Record Information

Version

2.0

Created at

2022-09-09 00:59:36 UTC

Updated at

2022-09-09 00:59:36 UTC

NP-MRD ID

NP0276720

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2r,3s,4s,5s,6s,7s,8r,9e)-11-(6-amino-2-hydroxy-3-methyl-5,8-dioxonaphthalen-1-yl)-3,5,7-trihydroxy-2,4,6,8,10-pentamethyl-11-oxoundec-9-enoic acid

Description

(2R,3S,4S,5S,6S,7S,8R,9E)-11-(6-amino-2-hydroxy-3-methyl-5,8-dioxo-5,8-dihydronaphthalen-1-yl)-3,5,7-trihydroxy-2,4,6,8,10-pentamethyl-11-oxoundec-9-enoic acid belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. Based on a literature review very few articles have been published on (2R,3S,4S,5S,6S,7S,8R,9E)-11-(6-amino-2-hydroxy-3-methyl-5,8-dioxo-5,8-dihydronaphthalen-1-yl)-3,5,7-trihydroxy-2,4,6,8,10-pentamethyl-11-oxoundec-9-enoic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309092202592D          

 37 38  0  0  1  0            999 V2000
   -6.4302    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4302    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013    0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.0013    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.2868   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.8579   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
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 29 36  1  0  0  0  0
 36 37  2  0  0  0  0
M  END

     RDKit          3D

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M  END


  Mrv1652309092202592D          

 37 38  0  0  1  0            999 V2000
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  6  7  1  1  0  0  0
  6  8  1  0  0  0  0
  8  9  1  6  0  0  0
  8 10  1  0  0  0  0
 10 11  1  1  0  0  0
 10 12  1  0  0  0  0
 12 13  1  6  0  0  0
 12 14  1  0  0  0  0
 14 15  1  1  0  0  0
 14 16  1  0  0  0  0
 16 17  1  1  0  0  0
 16 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
  2 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 24 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 23 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 31 33  1  0  0  0  0
 33 34  2  0  0  0  0
 34 35  1  0  0  0  0
 34 36  1  0  0  0  0
 29 36  1  0  0  0  0
 36 37  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0276720

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H](\C=C(/C)C(=O)C1=C(O)C(C)=CC2=C1C(=O)C=C(N)C2=O)[C@H](O)[C@H](C)[C@H](O)[C@H](C)[C@H](O)[C@@H](C)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C27H35NO9/c1-10(21(30)13(4)24(33)14(5)25(34)15(6)27(36)37)7-11(2)22(31)20-19-16(8-12(3)23(20)32)26(35)17(28)9-18(19)29/h7-10,13-15,21,24-25,30,32-34H,28H2,1-6H3,(H,36,37)/b11-7+/t10-,13+,14+,15-,21+,24+,25+/m1/s1

> <INCHI_KEY>
XPNRGDIMJUCLDI-YTCBPWMOSA-N

> <FORMULA>
C27H35NO9

> <MOLECULAR_WEIGHT>
517.575

> <EXACT_MASS>
517.231181711

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
72

> <JCHEM_AVERAGE_POLARIZABILITY>
54.343692431230195

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R,3S,4S,5S,6S,7S,8R,9E)-11-(6-amino-2-hydroxy-3-methyl-5,8-dioxo-5,8-dihydronaphthalen-1-yl)-3,5,7-trihydroxy-2,4,6,8,10-pentamethyl-11-oxoundec-9-enoic acid

> <JCHEM_LOGP>
1.802970416

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
5.563155986213015

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.4947018789913695

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9858614375232015

> <JCHEM_POLAR_SURFACE_AREA>
195.45

> <JCHEM_REFRACTIVITY>
138.42989999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(2R,3S,4S,5S,6S,7S,8R,9E)-11-(6-amino-2-hydroxy-3-methyl-5,8-dioxonaphthalen-1-yl)-3,5,7-trihydroxy-2,4,6,8,10-pentamethyl-11-oxoundec-9-enoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 09-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-SEP-22         0                                  
HETATM    1  C   UNK     0     -12.003   2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0     -12.003   0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0     -10.669  -0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -9.336   0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -9.336   2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -8.002  -0.000   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -8.002  -1.540   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -6.668   0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -6.668   2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -5.335  -0.000   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -5.335  -1.540   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -4.001   0.770   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -4.001   2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -2.667  -1.540   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      -1.334   0.770   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       1.334   0.770   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       0.000  -1.540   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0     -13.337  -0.000   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0     -13.337  -1.540   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0     -14.670   0.770   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0     -14.670   2.310   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0     -13.337   3.080   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0     -16.004   3.080   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0     -16.004   4.620   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0     -17.338   2.310   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0     -17.338   0.770   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0     -16.004  -0.000   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0     -16.004  -1.540   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0     -14.670  -2.310   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0     -17.338  -2.310   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0     -18.672  -1.540   0.000  0.00  0.00           C+0
HETATM   35  N   UNK     0     -20.005  -2.310   0.000  0.00  0.00           N+0
HETATM   36  C   UNK     0     -18.672  -0.000   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0     -20.005   0.770   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   21                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18                                                            
CONECT   21    2   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24   30                                                  
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29                                                       
CONECT   29   28   30   36                                                  
CONECT   30   29   23   31                                                  
CONECT   31   30   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   34                                                       
CONECT   34   33   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34   29   37                                                  
CONECT   37   36                                                            
MASTER        0    0    0    0    0    0    0    0   37    0   76    0
END

View in JSmol

Synonyms

Value	Source
(2R,3S,4S,5S,6S,7S,8R,9E)-11-(6-Amino-2-hydroxy-3-methyl-5,8-dioxo-5,8-dihydronaphthalen-1-yl)-3,5,7-trihydroxy-2,4,6,8,10-pentamethyl-11-oxoundec-9-enoate	Generator

Chemical Formula

C₂₇H₃₅NO₉

Average Mass

517.5750 Da

Monoisotopic Mass

517.23118 Da

IUPAC Name

(2R,3S,4S,5S,6S,7S,8R,9E)-11-(6-amino-2-hydroxy-3-methyl-5,8-dioxo-5,8-dihydronaphthalen-1-yl)-3,5,7-trihydroxy-2,4,6,8,10-pentamethyl-11-oxoundec-9-enoic acid

Traditional Name

(2R,3S,4S,5S,6S,7S,8R,9E)-11-(6-amino-2-hydroxy-3-methyl-5,8-dioxonaphthalen-1-yl)-3,5,7-trihydroxy-2,4,6,8,10-pentamethyl-11-oxoundec-9-enoic acid

CAS Registry Number

Not Available

SMILES

C[C@H](\C=C(/C)C(=O)C1=C(O)C(C)=CC2=C1C(=O)C=C(N)C2=O)[C@H](O)[C@H](C)[C@H](O)[C@H](C)[C@H](O)[C@@H](C)C(O)=O

InChI Identifier

InChI=1S/C27H35NO9/c1-10(21(30)13(4)24(33)14(5)25(34)15(6)27(36)37)7-11(2)22(31)20-19-16(8-12(3)23(20)32)26(35)17(28)9-18(19)29/h7-10,13-15,21,24-25,30,32-34H,28H2,1-6H3,(H,36,37)/b11-7+/t10-,13+,14+,15-,21+,24+,25+/m1/s1

InChI Key

XPNRGDIMJUCLDI-YTCBPWMOSA-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, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Sesquiterpenoids

Alternative Parents

Substituents

Sesquiterpenoid
Long-chain fatty acid
Naphthoquinone
Naphthalene
Quinone
Aryl ketone
Amino fatty acid
Beta-hydroxy acid
Branched fatty acid
Hydroxy fatty acid
Methyl-branched fatty acid
Fatty acyl
Hydroxy acid
Fatty acid
Unsaturated fatty acid
Benzenoid
Alpha-branched alpha,beta-unsaturated-ketone
Enone
Vinylogous amide
Vinylogous acid
Acryloyl-group
Alpha,beta-unsaturated ketone
Secondary alcohol
Amino acid
Ketone
Amino acid or derivatives
Carboxylic acid derivative
Carboxylic acid
Enamine
Polyol
Monocarboxylic acid or derivatives
Primary amine
Amine
Alcohol
Organic nitrogen compound
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Organooxygen compound
Organonitrogen compound
Organopnictogen compound
Primary aliphatic amine
Aromatic homopolycyclic compound

Molecular Framework

Aromatic 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	1.8	ChemAxon
pKa (Strongest Acidic)	4.49	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	195.45 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	138.43 m³·mol⁻¹	ChemAxon
Polarizability	54.34 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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

163190621

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2r,3s,4s,5s,6s,7s,8r,9e)-11-(6-amino-2-hydroxy-3-methyl-5,8-dioxonaphthalen-1-yl)-3,5,7-trihydroxy-2,4,6,8,10-pentamethyl-11-oxoundec-9-enoic acid (NP0276720)

MOL for NP0276720 ((2r,3s,4s,5s,6s,7s,8r,9e)-11-(6-amino-2-hydroxy-3-methyl-5,8-dioxonaphthalen-1-yl)-3,5,7-trihydroxy-2,4,6,8,10-pentamethyl-11-oxoundec-9-enoic acid)

3D MOL for NP0276720 ((2r,3s,4s,5s,6s,7s,8r,9e)-11-(6-amino-2-hydroxy-3-methyl-5,8-dioxonaphthalen-1-yl)-3,5,7-trihydroxy-2,4,6,8,10-pentamethyl-11-oxoundec-9-enoic acid)

3D SDF for NP0276720 ((2r,3s,4s,5s,6s,7s,8r,9e)-11-(6-amino-2-hydroxy-3-methyl-5,8-dioxonaphthalen-1-yl)-3,5,7-trihydroxy-2,4,6,8,10-pentamethyl-11-oxoundec-9-enoic acid)

3D-SDF for NP0276720 ((2r,3s,4s,5s,6s,7s,8r,9e)-11-(6-amino-2-hydroxy-3-methyl-5,8-dioxonaphthalen-1-yl)-3,5,7-trihydroxy-2,4,6,8,10-pentamethyl-11-oxoundec-9-enoic acid)

PDB for NP0276720 ((2r,3s,4s,5s,6s,7s,8r,9e)-11-(6-amino-2-hydroxy-3-methyl-5,8-dioxonaphthalen-1-yl)-3,5,7-trihydroxy-2,4,6,8,10-pentamethyl-11-oxoundec-9-enoic acid)

3D PDB for NP0276720 ((2r,3s,4s,5s,6s,7s,8r,9e)-11-(6-amino-2-hydroxy-3-methyl-5,8-dioxonaphthalen-1-yl)-3,5,7-trihydroxy-2,4,6,8,10-pentamethyl-11-oxoundec-9-enoic acid)

SMILES for NP0276720 ((2r,3s,4s,5s,6s,7s,8r,9e)-11-(6-amino-2-hydroxy-3-methyl-5,8-dioxonaphthalen-1-yl)-3,5,7-trihydroxy-2,4,6,8,10-pentamethyl-11-oxoundec-9-enoic acid)

INCHI for NP0276720 ((2r,3s,4s,5s,6s,7s,8r,9e)-11-(6-amino-2-hydroxy-3-methyl-5,8-dioxonaphthalen-1-yl)-3,5,7-trihydroxy-2,4,6,8,10-pentamethyl-11-oxoundec-9-enoic acid)

Structure for NP0276720 ((2r,3s,4s,5s,6s,7s,8r,9e)-11-(6-amino-2-hydroxy-3-methyl-5,8-dioxonaphthalen-1-yl)-3,5,7-trihydroxy-2,4,6,8,10-pentamethyl-11-oxoundec-9-enoic acid)

3D Structure for NP0276720 ((2r,3s,4s,5s,6s,7s,8r,9e)-11-(6-amino-2-hydroxy-3-methyl-5,8-dioxonaphthalen-1-yl)-3,5,7-trihydroxy-2,4,6,8,10-pentamethyl-11-oxoundec-9-enoic acid)