NP-MRD: Showing NP-Card for 3-hydroxy-4,6,7-trimethyl-13-(2-methyl-3-oxodec-8-enoyl)-8,15-dioxa-13-azatetracyclo[7.6.1.0⁵,¹⁶.0¹⁰,¹⁴]hexadeca-1(16),2,4-triene-2-carboxylic acid (NP0243294)

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Record Information

Version

2.0

Created at

2022-09-07 03:48:47 UTC

Updated at

2022-09-07 03:48:47 UTC

NP-MRD ID

NP0243294

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3-hydroxy-4,6,7-trimethyl-13-(2-methyl-3-oxodec-8-enoyl)-8,15-dioxa-13-azatetracyclo[7.6.1.0⁵,¹⁶.0¹⁰,¹⁴]hexadeca-1(16),2,4-triene-2-carboxylic acid

Description

3-Hydroxy-4,6,7-trimethyl-13-(2-methyl-3-oxodec-8-enoyl)-8,15-dioxa-13-azatetracyclo[7.6.1.0⁵,¹⁶.0¹⁰,¹⁴]Hexadeca-1(16),2,4-triene-2-carboxylic acid belongs to the class of organic compounds known as salicylic acid and derivatives. Salicylic acid and derivatives are compounds containing a 2-hydroxybenzoic acid moiety or a derivative thereof. 3-hydroxy-4,6,7-trimethyl-13-(2-methyl-3-oxodec-8-enoyl)-8,15-dioxa-13-azatetracyclo[7.6.1.0⁵,¹⁶.0¹⁰,¹⁴]hexadeca-1(16),2,4-triene-2-carboxylic acid is found in Penicillium citrinum. 3-Hydroxy-4,6,7-trimethyl-13-(2-methyl-3-oxodec-8-enoyl)-8,15-dioxa-13-azatetracyclo[7.6.1.0⁵,¹⁶.0¹⁰,¹⁴]Hexadeca-1(16),2,4-triene-2-carboxylic acid is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004171506182D          

 36 39  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1533004171506182D          

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    0.7731   -7.2509    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8350   -8.2071    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  4  0  0  0
  2  3  2  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
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 14 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 17 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  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  1  0  0  0  0
 21 28  1  0  0  0  0
 28 29  2  0  0  0  0
 29 30  1  0  0  0  0
 29 31  1  0  0  0  0
 31 32  1  0  0  0  0
 31 33  2  0  0  0  0
 20 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  2  0  0  0  0
 34 36  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0243294

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC=CCCCCC(=O)C(C)C(=O)N1CCC2C1OC1=C3C2OC(C)C(C)C3=C(C)C(O)=C1C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C28H37NO7/c1-6-7-8-9-10-11-19(30)15(3)26(32)29-13-12-18-24-21-20(14(2)17(5)35-24)16(4)23(31)22(28(33)34)25(21)36-27(18)29/h6-7,14-15,17-18,24,27,31H,8-13H2,1-5H3,(H,33,34)

> <INCHI_KEY>
SUQZYGYUFVUJGV-UHFFFAOYSA-N

> <FORMULA>
C28H37NO7

> <MOLECULAR_WEIGHT>
499.604

> <EXACT_MASS>
499.257002535

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
73

> <JCHEM_AVERAGE_POLARIZABILITY>
53.80143132697832

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-hydroxy-4,6,7-trimethyl-13-(2-methyl-3-oxodec-8-enoyl)-8,15-dioxa-13-azatetracyclo[7.6.1.0⁵,¹⁶.0¹⁰,¹⁴]hexadeca-1(16),2,4-triene-2-carboxylic acid

> <ALOGPS_LOGP>
4.02

> <JCHEM_LOGP>
5.987105545333334

> <ALOGPS_LOGS>
-4.19

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
10.954999067153386

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.4633812165613453

> <JCHEM_PKA_STRONGEST_BASIC>
-3.72987065470616

> <JCHEM_POLAR_SURFACE_AREA>
113.37000000000002

> <JCHEM_REFRACTIVITY>
135.8573

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.26e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-hydroxy-4,6,7-trimethyl-13-(2-methyl-3-oxodec-8-enoyl)-8,15-dioxa-13-azatetracyclo[7.6.1.0⁵,¹⁶.0¹⁰,¹⁴]hexadeca-1(16),2,4-triene-2-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 17-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-APR-15         0                                  
HETATM    1  C   UNK     0     -11.888  -6.525   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0     -10.555  -7.295   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0     -10.555  -8.835   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -9.221  -9.605   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -7.887  -8.835   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -6.554  -9.605   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -5.220  -8.835   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -3.886  -9.605   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -3.886 -11.145   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      -2.552  -8.835   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.552  -7.295   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.219  -9.605   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -1.219 -11.145   0.000  0.00  0.00           O+0
HETATM   14  N   UNK     0       0.115  -8.835   0.000  0.00  0.00           N+0
HETATM   15  C   UNK     0       0.276  -7.303   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.782  -6.983   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.552  -8.317   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.522  -9.461   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       1.998 -10.926   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       3.504 -11.246   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.534 -10.102   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.059  -8.637   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       5.089  -7.493   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       6.595  -7.813   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       7.626  -6.668   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       7.071  -9.277   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       8.578  -9.598   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       6.041 -10.422   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       6.517 -11.886   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       8.023 -12.207   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       5.486 -13.031   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       5.962 -14.496   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       3.980 -12.711   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       2.949 -13.855   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       1.443 -13.535   0.000  0.00  0.00           O+0
HETATM   36  O   UNK     0       3.425 -15.320   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    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   18                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   22                                                  
CONECT   18   17   14   19                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   33                                                  
CONECT   21   20   22   28                                                  
CONECT   22   21   17   23                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   21   29                                                  
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   20   34                                                  
CONECT   34   33   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34                                                            
MASTER        0    0    0    0    0    0    0    0   36    0   78    0
END

View in JSmol

Synonyms

Value	Source
3-Hydroxy-4,6,7-trimethyl-13-(2-methyl-3-oxodec-8-enoyl)-8,15-dioxa-13-azatetracyclo[7.6.1.0,.0,]hexadeca-1(16),2,4-triene-2-carboxylate	Generator
3-Hydroxy-4,6,7-trimethyl-13-(2-methyl-3-oxodec-8-enoyl)-8,15-dioxa-13-azatetracyclo[7.6.1.0⁵,¹⁶.0¹⁰,¹⁴]hexadeca-1(16),2,4-triene-2-carboxylate	Generator

Chemical Formula

C₂₈H₃₇NO₇

Average Mass

499.6040 Da

Monoisotopic Mass

499.25700 Da

IUPAC Name

3-hydroxy-4,6,7-trimethyl-13-(2-methyl-3-oxodec-8-enoyl)-8,15-dioxa-13-azatetracyclo[7.6.1.0⁵,¹⁶.0¹⁰,¹⁴]hexadeca-1(16),2,4-triene-2-carboxylic acid

Traditional Name

3-hydroxy-4,6,7-trimethyl-13-(2-methyl-3-oxodec-8-enoyl)-8,15-dioxa-13-azatetracyclo[7.6.1.0⁵,¹⁶.0¹⁰,¹⁴]hexadeca-1(16),2,4-triene-2-carboxylic acid

CAS Registry Number

Not Available

SMILES

CC=CCCCCC(=O)C(C)C(=O)N1CCC2C1OC1=C3C2OC(C)C(C)C3=C(C)C(O)=C1C(O)=O

InChI Identifier

InChI=1S/C28H37NO7/c1-6-7-8-9-10-11-19(30)15(3)26(32)29-13-12-18-24-21-20(14(2)17(5)35-24)16(4)23(31)22(28(33)34)25(21)36-27(18)29/h6-7,14-15,17-18,24,27,31H,8-13H2,1-5H3,(H,33,34)

InChI Key

SUQZYGYUFVUJGV-UHFFFAOYSA-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

Species Name	Source	Reference
Penicillium citrinum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as salicylic acid and derivatives. Salicylic acid and derivatives are compounds containing a 2-hydroxybenzoic acid moiety or a derivative thereof.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzoic acids and derivatives

Direct Parent

Salicylic acid and derivatives

Alternative Parents

Substituents

Chromane
Benzopyran
Isochromane
Salicylic acid or derivatives
1-benzopyran
2-benzopyran
N-acylpyrrolidine
Phenol
1,3-dicarbonyl compound
Pyrrolidine
Tertiary carboxylic acid amide
Vinylogous acid
Carboxamide group
Ketone
Azacycle
Organoheterocyclic compound
Oxacycle
Carboxylic acid derivative
Carboxylic acid
Ether
Dialkyl ether
Organic oxygen compound
Hydrocarbon derivative
Organonitrogen compound
Organooxygen compound
Carbonyl group
Organic oxide
Organic nitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic 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	4.02	ALOGPS
logP	5.99	ChemAxon
logS	-4.2	ALOGPS
pKa (Strongest Acidic)	2.46	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	113.37 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	135.86 m³·mol⁻¹	ChemAxon
Polarizability	53.8 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	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

73024562

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 3-hydroxy-4,6,7-trimethyl-13-(2-methyl-3-oxodec-8-enoyl)-8,15-dioxa-13-azatetracyclo[7.6.1.0⁵,¹⁶.0¹⁰,¹⁴]hexadeca-1(16),2,4-triene-2-carboxylic acid (NP0243294)

MOL for NP0243294 (3-hydroxy-4,6,7-trimethyl-13-(2-methyl-3-oxodec-8-enoyl)-8,15-dioxa-13-azatetracyclo[7.6.1.0⁵,¹⁶.0¹⁰,¹⁴]hexadeca-1(16),2,4-triene-2-carboxylic acid)

3D MOL for NP0243294 (3-hydroxy-4,6,7-trimethyl-13-(2-methyl-3-oxodec-8-enoyl)-8,15-dioxa-13-azatetracyclo[7.6.1.0⁵,¹⁶.0¹⁰,¹⁴]hexadeca-1(16),2,4-triene-2-carboxylic acid)

3D SDF for NP0243294 (3-hydroxy-4,6,7-trimethyl-13-(2-methyl-3-oxodec-8-enoyl)-8,15-dioxa-13-azatetracyclo[7.6.1.0⁵,¹⁶.0¹⁰,¹⁴]hexadeca-1(16),2,4-triene-2-carboxylic acid)

3D-SDF for NP0243294 (3-hydroxy-4,6,7-trimethyl-13-(2-methyl-3-oxodec-8-enoyl)-8,15-dioxa-13-azatetracyclo[7.6.1.0⁵,¹⁶.0¹⁰,¹⁴]hexadeca-1(16),2,4-triene-2-carboxylic acid)

PDB for NP0243294 (3-hydroxy-4,6,7-trimethyl-13-(2-methyl-3-oxodec-8-enoyl)-8,15-dioxa-13-azatetracyclo[7.6.1.0⁵,¹⁶.0¹⁰,¹⁴]hexadeca-1(16),2,4-triene-2-carboxylic acid)

3D PDB for NP0243294 (3-hydroxy-4,6,7-trimethyl-13-(2-methyl-3-oxodec-8-enoyl)-8,15-dioxa-13-azatetracyclo[7.6.1.0⁵,¹⁶.0¹⁰,¹⁴]hexadeca-1(16),2,4-triene-2-carboxylic acid)

SMILES for NP0243294 (3-hydroxy-4,6,7-trimethyl-13-(2-methyl-3-oxodec-8-enoyl)-8,15-dioxa-13-azatetracyclo[7.6.1.0⁵,¹⁶.0¹⁰,¹⁴]hexadeca-1(16),2,4-triene-2-carboxylic acid)

INCHI for NP0243294 (3-hydroxy-4,6,7-trimethyl-13-(2-methyl-3-oxodec-8-enoyl)-8,15-dioxa-13-azatetracyclo[7.6.1.0⁵,¹⁶.0¹⁰,¹⁴]hexadeca-1(16),2,4-triene-2-carboxylic acid)

Structure for NP0243294 (3-hydroxy-4,6,7-trimethyl-13-(2-methyl-3-oxodec-8-enoyl)-8,15-dioxa-13-azatetracyclo[7.6.1.0⁵,¹⁶.0¹⁰,¹⁴]hexadeca-1(16),2,4-triene-2-carboxylic acid)

3D Structure for NP0243294 (3-hydroxy-4,6,7-trimethyl-13-(2-methyl-3-oxodec-8-enoyl)-8,15-dioxa-13-azatetracyclo[7.6.1.0⁵,¹⁶.0¹⁰,¹⁴]hexadeca-1(16),2,4-triene-2-carboxylic acid)