NP-MRD: Showing NP-Card for Methoxycurvularin (NP0066437)

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Record Information

Version

2.0

Created at

2022-04-28 10:41:33 UTC

Updated at

2022-04-28 10:41:33 UTC

NP-MRD ID

NP0066437

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Methoxycurvularin

Description

11Beta-Methoxycurvularin 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. Methoxycurvularin is found in Penicillium sp. 511. Based on a literature review very few articles have been published on 11Beta-Methoxycurvularin.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 45 46  0  0  0  0  0  0  0  0999 V2000
   -3.1209   -3.3255   -0.3967 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4195   -2.1864   -0.7671 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4186   -1.9549    0.1653 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5345   -0.6654    0.8747 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8124    0.0834    0.6625 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5642    1.2215   -0.2990 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5549    2.2204    0.2206 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3859    3.4529    0.6389 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6620    2.6976   -0.7229 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6442    2.3916   -0.9723 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6145    3.1804   -0.7950 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0383    1.0337   -1.5003 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1394    0.4265   -0.7043 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3497    1.1145   -0.8862 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5189    0.7638   -0.2502 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6993    1.4813   -0.4645 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4878   -0.3096    0.5982 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2788   -1.0041    0.7848 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3679   -2.0667    1.6608 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0957   -0.6333    0.1282 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9398   -1.4707    0.4502 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7055   -1.7436    1.6905 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0406   -2.0797   -0.4449 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3968   -4.1608   -0.3779 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0071   -3.5150   -1.0161 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5029   -3.2436    0.6628 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4977   -2.7781    0.9352 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3909   -0.8517    1.9840 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7021   -0.0120    0.5619 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1228    0.5484    1.6312 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5774   -0.5637    0.2352 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5384    1.7022   -0.5397 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1760    0.7877   -1.2420 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1321    1.8596    1.1718 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9068    3.9885    1.4630 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5525    4.0904   -0.2616 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3972    3.1334    0.9749 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4278    1.1731   -2.5545 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1423    0.4526   -1.6028 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4292    1.9728   -1.5545 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2836    1.1416   -1.2377 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3928   -0.6037    1.1090 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6796   -2.7012    1.9385 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0242   -1.8370   -1.5071 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1551   -3.2112   -0.4452 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 13 20  2  0
 20 18  1  0
 18 19  1  0
 18 17  2  0
 17 15  1  0
 15 16  1  0
 15 14  2  0
 20 21  1  0
 21 22  2  0
 21 23  1  0
 23  3  1  0
 14 13  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  3 27  1  1
  4 28  1  0
  4 29  1  0
  5 30  1  0
  5 31  1  0
  6 32  1  0
  6 33  1  0
  7 34  1  1
  8 35  1  0
  8 36  1  0
  8 37  1  0
 12 38  1  0
 12 39  1  0
 19 43  1  0
 17 42  1  0
 16 41  1  0
 14 40  1  0
 23 44  1  0
 23 45  1  0
M  END


  Mrv1652304282212412D          

 23 24  0  0  1  0            999 V2000
    1.3381   -2.6026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4940   -1.7925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8704   -1.2524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0908   -1.5224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0651   -2.3325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5586   -2.8726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8446   -2.6026    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0263   -0.4422    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2736   -1.5224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8972   -2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4295   -0.7123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2090   -0.4422    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.8327   -0.9823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6768   -1.7925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3004   -2.3325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1445   -3.1427    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3649   -3.4127    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7413   -2.8726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3436   -2.3089    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9618   -3.1427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7681   -3.6828    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3649    0.3679    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1445    0.6379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  5  7  1  0  0  0  0
  3  8  1  0  0  0  0
  2  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 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  2  0  0  0  0
 18 20  1  0  0  0  0
  1 20  1  0  0  0  0
 16 21  1  6  0  0  0
 12 22  1  6  0  0  0
 22 23  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0066437

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CO[C@@H]1CCC[C@H](C)OC(=O)CC2=C(C(O)=CC(O)=C2)C(=O)C1

> <INCHI_IDENTIFIER>
InChI=1S/C17H22O6/c1-10-4-3-5-13(22-2)9-15(20)17-11(7-16(21)23-10)6-12(18)8-14(17)19/h6,8,10,13,18-19H,3-5,7,9H2,1-2H3/t10-,13+/m0/s1

> <INCHI_KEY>
LBVPDFGFLMFDPI-GXFFZTMASA-N

> <FORMULA>
C17H22O6

> <MOLECULAR_WEIGHT>
322.357

> <EXACT_MASS>
322.141638428

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
45

> <JCHEM_AVERAGE_POLARIZABILITY>
33.391242379793404

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(4S,8R)-11,13-dihydroxy-8-methoxy-4-methyl-2,4,5,6,7,8,9,10-octahydro-1H-3-benzoxacyclododecine-2,10-dione

> <ALOGPS_LOGP>
2.12

> <JCHEM_LOGP>
2.747004457

> <ALOGPS_LOGS>
-3.09

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.654851170940297

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.7715034033504935

> <JCHEM_PKA_STRONGEST_BASIC>
-4.125162807807409

> <JCHEM_POLAR_SURFACE_AREA>
93.06

> <JCHEM_REFRACTIVITY>
83.88309999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.60e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(4S,8R)-11,13-dihydroxy-8-methoxy-4-methyl-4,5,6,7,8,9-hexahydro-1H-3-benzoxacyclododecine-2,10-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0       2.498  -4.858   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.789  -3.346   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.625  -2.338   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.170  -2.842   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.121  -4.354   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.043  -5.362   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -1.577  -4.858   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0       1.916  -0.826   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       4.244  -2.842   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       5.408  -3.850   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       4.535  -1.330   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.990  -0.826   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.154  -1.834   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.863  -3.346   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.027  -4.354   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.736  -5.866   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       6.281  -6.370   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       5.117  -5.362   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       6.241  -4.310   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       3.662  -5.866   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       8.901  -6.874   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       6.281   0.687   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       7.736   1.191   0.000  0.00  0.00           C+0
CONECT    1    2    6   20                                                  
CONECT    2    1    3    9                                                  
CONECT    3    2    4    8                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5    1                                                       
CONECT    7    5                                                            
CONECT    8    3                                                            
CONECT    9    2   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13   22                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   21                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18    1                                                       
CONECT   21   16                                                            
CONECT   22   12   23                                                       
CONECT   23   22                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   48    0
END

View in JSmol

Synonyms

Value	Source
11b-Methoxycurvularin	Generator
11Β-methoxycurvularin	Generator
11-alpha-Methoxycurvularin	MeSH
11-beta-Methoxycurvularin	MeSH

Chemical Formula

C₁₇H₂₂O₆

Average Mass

322.3570 Da

Monoisotopic Mass

322.14164 Da

IUPAC Name

(4S,8R)-11,13-dihydroxy-8-methoxy-4-methyl-2,4,5,6,7,8,9,10-octahydro-1H-3-benzoxacyclododecine-2,10-dione

Traditional Name

(4S,8R)-11,13-dihydroxy-8-methoxy-4-methyl-4,5,6,7,8,9-hexahydro-1H-3-benzoxacyclododecine-2,10-dione

CAS Registry Number

Not Available

SMILES

CO[C@@H]1CCC[C@H](C)OC(=O)CC2=C(C(O)=CC(O)=C2)C(=O)C1

InChI Identifier

InChI=1S/C17H22O6/c1-10-4-3-5-13(22-2)9-15(20)17-11(7-16(21)23-10)6-12(18)8-14(17)19/h6,8,10,13,18-19H,3-5,7,9H2,1-2H3/t10-,13+/m0/s1

InChI Key

LBVPDFGFLMFDPI-GXFFZTMASA-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
Penicillium sp. 511	Fungi	KNApSAcK

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
Aryl alkyl ketone
Aryl ketone
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Benzenoid
Vinylogous acid
Carboxylic acid ester
Ketone
Lactone
Carboxylic acid derivative
Dialkyl ether
Ether
Oxacycle
Monocarboxylic acid or derivatives
Organoheterocyclic compound
Organic oxide
Hydrocarbon derivative
Organic oxygen compound
Carbonyl group
Organooxygen 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	2.12	ALOGPS
logP	2.75	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	7.77	ChemAxon
pKa (Strongest Basic)	-4.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	93.06 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	83.88 m³·mol⁻¹	ChemAxon
Polarizability	33.39 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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

26381199

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

14829839

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Methoxycurvularin (NP0066437)

MOL for NP0066437 (Methoxycurvularin)

3D MOL for NP0066437 (Methoxycurvularin)

3D SDF for NP0066437 (Methoxycurvularin)

3D-SDF for NP0066437 (Methoxycurvularin)

PDB for NP0066437 (Methoxycurvularin)

3D PDB for NP0066437 (Methoxycurvularin)

SMILES for NP0066437 (Methoxycurvularin)

INCHI for NP0066437 (Methoxycurvularin)

Structure for NP0066437 (Methoxycurvularin)

3D Structure for NP0066437 (Methoxycurvularin)