NP-MRD: Showing NP-Card for 11,12-dihydroxy-16-methyl-8-[2-(4-methyl-3,6-dihydro-2h-pyran-2-yl)ethenyl]-14-methylidene-6,9,22-trioxatricyclo[16.3.1.1⁷,¹⁰]tricosa-3,20-dien-5-one (NP0175824)

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Record Information

Version

2.0

Created at

2022-09-03 13:23:15 UTC

Updated at

2022-09-03 13:23:15 UTC

NP-MRD ID

NP0175824

Secondary Accession Numbers

None

Natural Product Identification

Common Name

11,12-dihydroxy-16-methyl-8-[2-(4-methyl-3,6-dihydro-2h-pyran-2-yl)ethenyl]-14-methylidene-6,9,22-trioxatricyclo[16.3.1.1⁷,¹⁰]tricosa-3,20-dien-5-one

Description

11,12-Dihydroxy-16-methyl-8-[2-(4-methyl-3,6-dihydro-2H-pyran-2-yl)ethenyl]-14-methylidene-6,9,22-trioxatricyclo[16.3.1.1⁷,¹⁰]Tricosa-3,20-dien-5-one 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. 11,12-dihydroxy-16-methyl-8-[2-(4-methyl-3,6-dihydro-2h-pyran-2-yl)ethenyl]-14-methylidene-6,9,22-trioxatricyclo[16.3.1.1⁷,¹⁰]tricosa-3,20-dien-5-one is found in Cacospongia mycofijiensis. 11,12-Dihydroxy-16-methyl-8-[2-(4-methyl-3,6-dihydro-2H-pyran-2-yl)ethenyl]-14-methylidene-6,9,22-trioxatricyclo[16.3.1.1⁷,¹⁰]Tricosa-3,20-dien-5-one is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004161506172D          

 37 40  0  0  0  0            999 V2000
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    1.8743    3.1608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1533004161506172D          

 37 40  0  0  0  0            999 V2000
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    6.8303    5.7596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4510   -0.4850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1588   -0.9089    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8702   -1.0709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3464   -1.7447    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1240   -1.4229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3025   -1.4984    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2342   -2.3205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5047   -1.2883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0833    1.4475    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
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
 10  9  1  4  0  0  0
 10 11  2  0  0  0  0
 11 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
 18 19  1  0  0  0  0
 15 19  1  0  0  0  0
 20 19  1  4  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 22 27  1  0  0  0  0
 24 28  1  0  0  0  0
 17 29  1  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  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
  2 36  1  0  0  0  0
  8 37  1  0  0  0  0
  4 37  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0175824

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1CC2CC=CC(CC=CC(=O)OC3CC(OC3C=CC3CC(C)=CCO3)C(O)C(O)CC(=C)C1)O2

> <INCHI_IDENTIFIER>
InChI=1S/C30H42O7/c1-19-12-13-34-23(15-19)10-11-26-27-18-28(36-26)30(33)25(31)17-21(3)14-20(2)16-24-8-4-6-22(35-24)7-5-9-29(32)37-27/h4-6,9-12,20,22-28,30-31,33H,3,7-8,13-18H2,1-2H3

> <INCHI_KEY>
JNPMYSILHRFUPH-UHFFFAOYSA-N

> <FORMULA>
C30H42O7

> <MOLECULAR_WEIGHT>
514.659

> <EXACT_MASS>
514.293053692

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
79

> <JCHEM_AVERAGE_POLARIZABILITY>
57.04489462927586

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
11,12-dihydroxy-16-methyl-8-[2-(4-methyl-3,6-dihydro-2H-pyran-2-yl)ethenyl]-14-methylidene-6,9,22-trioxatricyclo[16.3.1.1⁷,¹⁰]tricosa-3,20-dien-5-one

> <ALOGPS_LOGP>
3.64

> <JCHEM_LOGP>
3.867419202

> <ALOGPS_LOGS>
-4.50

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.951382369105012

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.154948814581434

> <JCHEM_PKA_STRONGEST_BASIC>
-3.2102741021842425

> <JCHEM_POLAR_SURFACE_AREA>
94.45000000000002

> <JCHEM_REFRACTIVITY>
144.973

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.63e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
11,12-dihydroxy-16-methyl-8-[2-(4-methyl-3,6-dihydro-2H-pyran-2-yl)ethenyl]-14-methylidene-6,9,22-trioxatricyclo[16.3.1.1⁷,¹⁰]tricosa-3,20-dien-5-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 16-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   16-APR-15         0                                  
HETATM    1  C   UNK     0       0.459  -2.621   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.543  -1.527   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.655  -0.269   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.250   1.216   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.739   0.824   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.823   1.918   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.418   3.404   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.929   3.796   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.106   5.243   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.499   5.900   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.032   6.041   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.522   5.649   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       7.166   7.048   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       7.787   4.771   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       8.676   3.514   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.888   2.190   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.904   1.032   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      10.319   1.640   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      10.178   3.174   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      11.336   4.189   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      11.035   5.700   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      12.193   6.715   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      11.893   8.225   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      13.050   9.241   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      14.509   8.746   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      14.809   7.235   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      13.651   6.220   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      12.750  10.751   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       8.309  -0.905   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       9.630  -1.697   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       7.224  -1.999   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       8.113  -3.257   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       5.832  -2.656   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       4.298  -2.797   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       4.170  -4.332   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       2.809  -2.405   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0      -0.156   2.702   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   36                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   37                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   37                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16   19                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   29                                                  
CONECT   18   17   19                                                       
CONECT   19   18   15   20                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   27                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25   28                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   22                                                       
CONECT   28   24                                                            
CONECT   29   17   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   34                                                       
CONECT   34   33   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34    2                                                       
CONECT   37    8    4                                                       
MASTER        0    0    0    0    0    0    0    0   37    0   80    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₀H₄₂O₇

Average Mass

514.6590 Da

Monoisotopic Mass

514.29305 Da

IUPAC Name

11,12-dihydroxy-16-methyl-8-[2-(4-methyl-3,6-dihydro-2H-pyran-2-yl)ethenyl]-14-methylidene-6,9,22-trioxatricyclo[16.3.1.1⁷,¹⁰]tricosa-3,20-dien-5-one

Traditional Name

11,12-dihydroxy-16-methyl-8-[2-(4-methyl-3,6-dihydro-2H-pyran-2-yl)ethenyl]-14-methylidene-6,9,22-trioxatricyclo[16.3.1.1⁷,¹⁰]tricosa-3,20-dien-5-one

CAS Registry Number

Not Available

SMILES

CC1CC2CC=CC(CC=CC(=O)OC3CC(OC3C=CC3CC(C)=CCO3)C(O)C(O)CC(=C)C1)O2

InChI Identifier

InChI=1S/C30H42O7/c1-19-12-13-34-23(15-19)10-11-26-27-18-28(36-26)30(33)25(31)17-21(3)14-20(2)16-24-8-4-6-22(35-24)7-5-9-29(32)37-27/h4-6,9-12,20,22-28,30-31,33H,3,7-8,13-18H2,1-2H3

InChI Key

JNPMYSILHRFUPH-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
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
Pyran
Oxolane
Enoate ester
Alpha,beta-unsaturated carboxylic ester
1,2-diol
Carboxylic acid ester
Lactone
Secondary alcohol
Monocarboxylic acid or derivatives
Ether
Dialkyl ether
Carboxylic acid derivative
Oxacycle
Organoheterocyclic compound
Organic oxide
Organooxygen compound
Organic oxygen compound
Alcohol
Hydrocarbon derivative
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	3.64	ALOGPS
logP	3.87	ChemAxon
logS	-4.5	ALOGPS
pKa (Strongest Acidic)	13.15	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	94.45 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	144.97 m³·mol⁻¹	ChemAxon
Polarizability	57.04 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	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

73864483

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 11,12-dihydroxy-16-methyl-8-[2-(4-methyl-3,6-dihydro-2h-pyran-2-yl)ethenyl]-14-methylidene-6,9,22-trioxatricyclo[16.3.1.1⁷,¹⁰]tricosa-3,20-dien-5-one (NP0175824)

MOL for NP0175824 (11,12-dihydroxy-16-methyl-8-[2-(4-methyl-3,6-dihydro-2h-pyran-2-yl)ethenyl]-14-methylidene-6,9,22-trioxatricyclo[16.3.1.1⁷,¹⁰]tricosa-3,20-dien-5-one)

3D MOL for NP0175824 (11,12-dihydroxy-16-methyl-8-[2-(4-methyl-3,6-dihydro-2h-pyran-2-yl)ethenyl]-14-methylidene-6,9,22-trioxatricyclo[16.3.1.1⁷,¹⁰]tricosa-3,20-dien-5-one)

3D SDF for NP0175824 (11,12-dihydroxy-16-methyl-8-[2-(4-methyl-3,6-dihydro-2h-pyran-2-yl)ethenyl]-14-methylidene-6,9,22-trioxatricyclo[16.3.1.1⁷,¹⁰]tricosa-3,20-dien-5-one)

3D-SDF for NP0175824 (11,12-dihydroxy-16-methyl-8-[2-(4-methyl-3,6-dihydro-2h-pyran-2-yl)ethenyl]-14-methylidene-6,9,22-trioxatricyclo[16.3.1.1⁷,¹⁰]tricosa-3,20-dien-5-one)

PDB for NP0175824 (11,12-dihydroxy-16-methyl-8-[2-(4-methyl-3,6-dihydro-2h-pyran-2-yl)ethenyl]-14-methylidene-6,9,22-trioxatricyclo[16.3.1.1⁷,¹⁰]tricosa-3,20-dien-5-one)

3D PDB for NP0175824 (11,12-dihydroxy-16-methyl-8-[2-(4-methyl-3,6-dihydro-2h-pyran-2-yl)ethenyl]-14-methylidene-6,9,22-trioxatricyclo[16.3.1.1⁷,¹⁰]tricosa-3,20-dien-5-one)

SMILES for NP0175824 (11,12-dihydroxy-16-methyl-8-[2-(4-methyl-3,6-dihydro-2h-pyran-2-yl)ethenyl]-14-methylidene-6,9,22-trioxatricyclo[16.3.1.1⁷,¹⁰]tricosa-3,20-dien-5-one)

INCHI for NP0175824 (11,12-dihydroxy-16-methyl-8-[2-(4-methyl-3,6-dihydro-2h-pyran-2-yl)ethenyl]-14-methylidene-6,9,22-trioxatricyclo[16.3.1.1⁷,¹⁰]tricosa-3,20-dien-5-one)

Structure for NP0175824 (11,12-dihydroxy-16-methyl-8-[2-(4-methyl-3,6-dihydro-2h-pyran-2-yl)ethenyl]-14-methylidene-6,9,22-trioxatricyclo[16.3.1.1⁷,¹⁰]tricosa-3,20-dien-5-one)

3D Structure for NP0175824 (11,12-dihydroxy-16-methyl-8-[2-(4-methyl-3,6-dihydro-2h-pyran-2-yl)ethenyl]-14-methylidene-6,9,22-trioxatricyclo[16.3.1.1⁷,¹⁰]tricosa-3,20-dien-5-one)