NP-MRD: Showing NP-Card for n-{[(8e)-3,11-dimethyl-19-methylidene-7,13-dioxo-6,21-dioxabicyclo[15.3.1]henicosa-2,8,10,14-tetraen-5-yl](hydroxy)methyl}hexa-2,4-dienimidic acid (NP0201690)

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Record Information

Version

2.0

Created at

2022-09-04 20:46:45 UTC

Updated at

2022-09-04 20:46:46 UTC

NP-MRD ID

NP0201690

Secondary Accession Numbers

None

Natural Product Identification

Common Name

n-{[(8e)-3,11-dimethyl-19-methylidene-7,13-dioxo-6,21-dioxabicyclo[15.3.1]henicosa-2,8,10,14-tetraen-5-yl](hydroxy)methyl}hexa-2,4-dienimidic acid

Description

N-{[(8E)-3,11-dimethyl-19-methylidene-7,13-dioxo-6,21-dioxabicyclo[15.3.1]Henicosa-2,8,10,14-tetraen-5-yl](hydroxy)methyl}hexa-2,4-dienimidic acid belongs to the class of organic compounds known as macrolides and analogues. These are organic compounds containing a lactone ring of at least twelve members. n-{[(8e)-3,11-dimethyl-19-methylidene-7,13-dioxo-6,21-dioxabicyclo[15.3.1]henicosa-2,8,10,14-tetraen-5-yl](hydroxy)methyl}hexa-2,4-dienimidic acid is found in Cacospongia mycofijiensis. N-{[(8E)-3,11-dimethyl-19-methylidene-7,13-dioxo-6,21-dioxabicyclo[15.3.1]Henicosa-2,8,10,14-tetraen-5-yl](hydroxy)methyl}hexa-2,4-dienimidic acid is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004201504502D          

 36 37  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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  Mrv1533004201504502D          

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 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  4  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 22 21  1  4  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 24 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  4  0  0  0
 29 30  2  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
 11 33  1  0  0  0  0
 27 34  1  0  0  0  0
 20 35  1  0  0  0  0
 15 35  1  0  0  0  0
 13 36  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0201690

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC=CC=CC(=O)NC(O)C1CC(C)=CC2CC(=C)CC(CC=CC(=O)CC(C)=C\C=C\C(=O)O1)O2

> <INCHI_IDENTIFIER>
InChI=1S/C29H37NO6/c1-5-6-7-13-27(32)30-29(34)26-19-22(4)18-25-17-21(3)16-24(35-25)12-9-11-23(31)15-20(2)10-8-14-28(33)36-26/h5-11,13-14,18,24-26,29,34H,3,12,15-17,19H2,1-2,4H3,(H,30,32)/b6-5?,11-9?,13-7?,14-8+,20-10?,22-18?

> <INCHI_KEY>
NJZJMJVVSZTAGX-NWYZTTRESA-N

> <FORMULA>
C29H37NO6

> <MOLECULAR_WEIGHT>
495.616

> <EXACT_MASS>
495.262087915

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
73

> <JCHEM_AVERAGE_POLARIZABILITY>
53.51493944169927

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
N-{[(8E)-3,11-dimethyl-19-methylidene-7,13-dioxo-6,21-dioxabicyclo[15.3.1]henicosa-2,8,10,14-tetraen-5-yl](hydroxy)methyl}hexa-2,4-dienamide

> <ALOGPS_LOGP>
3.80

> <JCHEM_LOGP>
4.501819959333332

> <ALOGPS_LOGS>
-4.95

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.226369755174582

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.203692097964877

> <JCHEM_PKA_STRONGEST_BASIC>
-0.731986427494748

> <JCHEM_POLAR_SURFACE_AREA>
101.93

> <JCHEM_REFRACTIVITY>
145.68280000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.58e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
N-{[(8E)-3,11-dimethyl-19-methylidene-7,13-dioxo-6,21-dioxabicyclo[15.3.1]henicosa-2,8,10,14-tetraen-5-yl](hydroxy)methyl}hexa-2,4-dienamide

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 20-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-APR-15         0                                  
HETATM    1  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       6.668  -5.390   0.000  0.00  0.00           O+0
HETATM    8  N   UNK     0       5.335  -3.080   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       8.002  -3.080   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.001  -0.770   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  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -0.000   4.620   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.335   6.160   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       6.668   6.930   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       8.002   6.160   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       8.002   4.620   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       9.336   6.930   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      10.669   6.160   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      10.669   4.620   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       9.336   3.850   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       9.336   2.310   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       6.668   2.310   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0       8.002   0.000   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      12.003   6.930   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       4.001   2.310   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   33                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   36                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   35                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   21   35                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27                                                       
CONECT   27   26   28   34                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   11                                                       
CONECT   34   27                                                            
CONECT   35   20   15                                                       
CONECT   36   13                                                            
MASTER        0    0    0    0    0    0    0    0   36    0   74    0
END

View in JSmol

Synonyms

Value	Source
N-{[(8E)-3,11-dimethyl-19-methylidene-7,13-dioxo-6,21-dioxabicyclo[15.3.1]henicosa-2,8,10,14-tetraen-5-yl](hydroxy)methyl}hexa-2,4-dienimidate	Generator

Chemical Formula

C₂₉H₃₇NO₆

Average Mass

495.6160 Da

Monoisotopic Mass

495.26209 Da

IUPAC Name

N-{[(8E)-3,11-dimethyl-19-methylidene-7,13-dioxo-6,21-dioxabicyclo[15.3.1]henicosa-2,8,10,14-tetraen-5-yl](hydroxy)methyl}hexa-2,4-dienamide

Traditional Name

N-{[(8E)-3,11-dimethyl-19-methylidene-7,13-dioxo-6,21-dioxabicyclo[15.3.1]henicosa-2,8,10,14-tetraen-5-yl](hydroxy)methyl}hexa-2,4-dienamide

CAS Registry Number

Not Available

SMILES

CC=CC=CC(=O)NC(O)C1CC(C)=CC2CC(=C)CC(CC=CC(=O)CC(C)=C\C=C\C(=O)O1)O2

InChI Identifier

InChI=1S/C29H37NO6/c1-5-6-7-13-27(32)30-29(34)26-19-22(4)18-25-17-21(3)16-24(35-25)12-9-11-23(31)15-20(2)10-8-14-28(33)36-26/h5-11,13-14,18,24-26,29,34H,3,12,15-17,19H2,1-2,4H3,(H,30,32)/b6-5?,11-9?,13-7?,14-8+,20-10?,22-18?

InChI Key

NJZJMJVVSZTAGX-NWYZTTRESA-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
Cacospongia mycofijiensis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as macrolides and analogues. These are organic compounds containing a lactone ring of at least twelve members.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Macrolides and analogues

Sub Class

Not Available

Direct Parent

Macrolides and analogues

Alternative Parents

Substituents

Macrolide
Oxane
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Cyclic ketone
Lactone
Ketone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Monocarboxylic acid or derivatives
Ether
Dialkyl ether
Carboxylic acid derivative
Carboximidic acid derivative
Carboximidic acid
Alkanolamine
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Carbonyl group
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	3.8	ALOGPS
logP	4.5	ChemAxon
logS	-5	ALOGPS
pKa (Strongest Acidic)	12.2	ChemAxon
pKa (Strongest Basic)	-0.73	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	101.93 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	145.68 m³·mol⁻¹	ChemAxon
Polarizability	53.51 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for n-{[(8e)-3,11-dimethyl-19-methylidene-7,13-dioxo-6,21-dioxabicyclo[15.3.1]henicosa-2,8,10,14-tetraen-5-yl](hydroxy)methyl}hexa-2,4-dienimidic acid (NP0201690)

MOL for NP0201690 (n-{[(8e)-3,11-dimethyl-19-methylidene-7,13-dioxo-6,21-dioxabicyclo[15.3.1]henicosa-2,8,10,14-tetraen-5-yl](hydroxy)methyl}hexa-2,4-dienimidic acid)

3D MOL for NP0201690 (n-{[(8e)-3,11-dimethyl-19-methylidene-7,13-dioxo-6,21-dioxabicyclo[15.3.1]henicosa-2,8,10,14-tetraen-5-yl](hydroxy)methyl}hexa-2,4-dienimidic acid)

3D SDF for NP0201690 (n-{[(8e)-3,11-dimethyl-19-methylidene-7,13-dioxo-6,21-dioxabicyclo[15.3.1]henicosa-2,8,10,14-tetraen-5-yl](hydroxy)methyl}hexa-2,4-dienimidic acid)

3D-SDF for NP0201690 (n-{[(8e)-3,11-dimethyl-19-methylidene-7,13-dioxo-6,21-dioxabicyclo[15.3.1]henicosa-2,8,10,14-tetraen-5-yl](hydroxy)methyl}hexa-2,4-dienimidic acid)

PDB for NP0201690 (n-{[(8e)-3,11-dimethyl-19-methylidene-7,13-dioxo-6,21-dioxabicyclo[15.3.1]henicosa-2,8,10,14-tetraen-5-yl](hydroxy)methyl}hexa-2,4-dienimidic acid)

3D PDB for NP0201690 (n-{[(8e)-3,11-dimethyl-19-methylidene-7,13-dioxo-6,21-dioxabicyclo[15.3.1]henicosa-2,8,10,14-tetraen-5-yl](hydroxy)methyl}hexa-2,4-dienimidic acid)

SMILES for NP0201690 (n-{[(8e)-3,11-dimethyl-19-methylidene-7,13-dioxo-6,21-dioxabicyclo[15.3.1]henicosa-2,8,10,14-tetraen-5-yl](hydroxy)methyl}hexa-2,4-dienimidic acid)

INCHI for NP0201690 (n-{[(8e)-3,11-dimethyl-19-methylidene-7,13-dioxo-6,21-dioxabicyclo[15.3.1]henicosa-2,8,10,14-tetraen-5-yl](hydroxy)methyl}hexa-2,4-dienimidic acid)

Structure for NP0201690 (n-{[(8e)-3,11-dimethyl-19-methylidene-7,13-dioxo-6,21-dioxabicyclo[15.3.1]henicosa-2,8,10,14-tetraen-5-yl](hydroxy)methyl}hexa-2,4-dienimidic acid)

3D Structure for NP0201690 (n-{[(8e)-3,11-dimethyl-19-methylidene-7,13-dioxo-6,21-dioxabicyclo[15.3.1]henicosa-2,8,10,14-tetraen-5-yl](hydroxy)methyl}hexa-2,4-dienimidic acid)