NP-MRD: Showing NP-Card for (+)-Sodwanone M (NP0083271)

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Record Information

Version

2.0

Created at

2022-04-29 04:18:50 UTC

Updated at

2022-04-29 04:18:51 UTC

NP-MRD ID

NP0083271

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(+)-Sodwanone M

Description

(5AR,6S,7S,9aS)-6-hydroxy-2,2,5a,7-tetramethyl-6-{2-[(1R,4R,5S,6S,9R)-4,5,10,10-tetramethyl-11,12-dioxatricyclo[7.2.1.0¹,⁶]Dodecan-5-yl]ethyl}-decahydro-1-benzoxepin-3-one belongs to the class of organic compounds known as oxepanes. Oxepanes are compounds containing an oxepane ring, which is a seven-member saturated aliphatic heterocycle with one oxygen and six carbon atoms. (+)-Sodwanone M is found in Axinella weltneri. Based on a literature review very few articles have been published on (5aR,6S,7S,9aS)-6-hydroxy-2,2,5a,7-tetramethyl-6-{2-[(1R,4R,5S,6S,9R)-4,5,10,10-tetramethyl-11,12-dioxatricyclo[7.2.1.0¹,⁶]Dodecan-5-yl]ethyl}-decahydro-1-benzoxepin-3-one.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304292206182D          

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M  END

     RDKit          3D

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M  END


  Mrv1652304292206182D          

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    4.9752   -1.8699    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5824   -1.7617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2846   -1.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4269   -1.5947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0587   -0.8120    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8935    0.0352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6533    0.4579    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0709   -0.0289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4124    0.7054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7367   -0.5133    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
  1  6  1  0  0  0  0
  4  7  1  1  0  0  0
  3  8  1  6  0  0  0
  8  9  1  0  0  0  0
 10  9  1  1  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  1  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 10 15  1  0  0  0  0
 15 16  1  6  0  0  0
 12 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 11 22  1  0  0  0  0
 18 23  1  0  0  0  0
 18 24  1  0  0  0  0
 11 25  1  1  0  0  0
 10 26  1  6  0  0  0
  3 27  1  1  0  0  0
  2 28  1  6  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
  1 32  1  0  0  0  0
 31 33  1  0  0  0  0
 31 34  1  0  0  0  0
 30 35  1  1  0  0  0
  1 35  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0083271

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]1CC[C@]23O[C@H](CC[C@H]2[C@@]1(C)CC[C@]1(O)[C@@H](C)CC[C@@H]2OC(C)(C)C(=O)CC[C@@]12C)C(C)(C)O3

> <INCHI_IDENTIFIER>
InChI=1S/C30H50O5/c1-19-13-16-30-21(10-12-23(34-30)26(5,6)35-30)27(19,7)17-18-29(32)20(2)9-11-24-28(29,8)15-14-22(31)25(3,4)33-24/h19-21,23-24,32H,9-18H2,1-8H3/t19-,20+,21+,23-,24+,27+,28-,29+,30-/m1/s1

> <INCHI_KEY>
SSNQBPLODCWZKY-CAZSBSGTSA-N

> <FORMULA>
C30H50O5

> <MOLECULAR_WEIGHT>
490.725

> <EXACT_MASS>
490.36582471

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
85

> <JCHEM_AVERAGE_POLARIZABILITY>
56.69055474378443

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(5aR,6S,7S,9aS)-6-hydroxy-2,2,5a,7-tetramethyl-6-{2-[(1R,4R,5S,6S,9R)-4,5,10,10-tetramethyl-11,12-dioxatricyclo[7.2.1.0^{1,6}]dodecan-5-yl]ethyl}-decahydro-1-benzoxepin-3-one

> <ALOGPS_LOGP>
5.80

> <JCHEM_LOGP>
6.126838107000001

> <ALOGPS_LOGS>
-6.36

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
17.723246558698243

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.1212889335476

> <JCHEM_PKA_STRONGEST_BASIC>
-3.1830382589251034

> <JCHEM_POLAR_SURFACE_AREA>
64.99000000000001

> <JCHEM_REFRACTIVITY>
136.7914

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.14e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(5aR,6S,7S,9aS)-6-hydroxy-2,2,5a,7-tetramethyl-6-{2-[(1R,4R,5S,6S,9R)-4,5,10,10-tetramethyl-11,12-dioxatricyclo[7.2.1.0^{1,6}]dodecan-5-yl]ethyl}-hexahydro-1-benzoxepin-3-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-APR-22         0                                  
HETATM    1  C   UNK     0       4.359  -0.230   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.119  -1.701   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.690  -1.749   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.529  -0.442   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.832   0.944   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.292   1.038   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.067  -0.523   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.962  -2.617   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.845  -4.153   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.117  -5.021   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      10.609  -5.402   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      11.025  -6.885   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.949  -7.987   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.457  -7.606   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.041  -6.123   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.549  -5.742   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      12.444  -7.484   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      13.797  -6.749   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      14.065  -5.232   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      15.548  -4.817   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      13.047  -4.077   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      11.509  -4.153   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      14.502  -8.118   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      15.319  -6.983   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      10.084  -3.955   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       9.287  -3.491   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       6.687  -3.289   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       4.265  -3.103   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       2.664  -2.977   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       1.976  -1.516   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       1.668   0.066   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       3.086   0.855   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       0.132  -0.054   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       0.770   1.317   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       3.242  -0.958   0.000  0.00  0.00           O+0
CONECT    1    2    6   32   35                                             
CONECT    2    1    3   28                                                  
CONECT    3    2    4    8   27                                             
CONECT    4    3    5    7                                                  
CONECT    5    4    6                                                       
CONECT    6    5    1                                                       
CONECT    7    4                                                            
CONECT    8    3    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   15   26                                             
CONECT   11   10   12   22   25                                             
CONECT   12   11   13   17                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   10   16                                                  
CONECT   16   15                                                            
CONECT   17   12   18                                                       
CONECT   18   17   19   23   24                                             
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22                                                       
CONECT   22   21   11                                                       
CONECT   23   18                                                            
CONECT   24   18                                                            
CONECT   25   11                                                            
CONECT   26   10                                                            
CONECT   27    3                                                            
CONECT   28    2   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31   35                                                  
CONECT   31   30   32   33   34                                             
CONECT   32   31    1                                                       
CONECT   33   31                                                            
CONECT   34   31                                                            
CONECT   35   30    1                                                       
MASTER        0    0    0    0    0    0    0    0   35    0   78    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₀H₅₀O₅

Average Mass

490.7250 Da

Monoisotopic Mass

490.36582 Da

IUPAC Name

(5aR,6S,7S,9aS)-6-hydroxy-2,2,5a,7-tetramethyl-6-{2-[(1R,4R,5S,6S,9R)-4,5,10,10-tetramethyl-11,12-dioxatricyclo[7.2.1.0^{1,6}]dodecan-5-yl]ethyl}-decahydro-1-benzoxepin-3-one

Traditional Name

(5aR,6S,7S,9aS)-6-hydroxy-2,2,5a,7-tetramethyl-6-{2-[(1R,4R,5S,6S,9R)-4,5,10,10-tetramethyl-11,12-dioxatricyclo[7.2.1.0^{1,6}]dodecan-5-yl]ethyl}-hexahydro-1-benzoxepin-3-one

CAS Registry Number

Not Available

SMILES

C[C@@H]1CC[C@]23O[C@H](CC[C@H]2[C@@]1(C)CC[C@]1(O)[C@@H](C)CC[C@@H]2OC(C)(C)C(=O)CC[C@@]12C)C(C)(C)O3

InChI Identifier

InChI=1S/C30H50O5/c1-19-13-16-30-21(10-12-23(34-30)26(5,6)35-30)27(19,7)17-18-29(32)20(2)9-11-24-28(29,8)15-14-22(31)25(3,4)33-24/h19-21,23-24,32H,9-18H2,1-8H3/t19-,20+,21+,23-,24+,27+,28-,29+,30-/m1/s1

InChI Key

SSNQBPLODCWZKY-CAZSBSGTSA-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
Axinella weltneri	Animalia	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as oxepanes. Oxepanes are compounds containing an oxepane ring, which is a seven-member saturated aliphatic heterocycle with one oxygen and six carbon atoms.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Oxepanes

Sub Class

Not Available

Direct Parent

Oxepanes

Alternative Parents

Substituents

Ketal
Oxepane
Oxane
Meta-dioxolane
Cyclic alcohol
Tertiary alcohol
Cyclic ketone
Ketone
Acetal
Oxacycle
Dialkyl ether
Ether
Organic oxygen compound
Organooxygen compound
Hydrocarbon derivative
Carbonyl group
Alcohol
Organic oxide
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	5.8	ALOGPS
logP	6.13	ChemAxon
logS	-6.4	ALOGPS
pKa (Strongest Acidic)	14.12	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	64.99 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	136.79 m³·mol⁻¹	ChemAxon
Polarizability	56.69 Å³	ChemAxon
Number of Rings	5	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

163087261

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for (+)-Sodwanone M (NP0083271)

MOL for NP0083271 ((+)-Sodwanone M)

3D MOL for NP0083271 ((+)-Sodwanone M)

3D SDF for NP0083271 ((+)-Sodwanone M)

3D-SDF for NP0083271 ((+)-Sodwanone M)

PDB for NP0083271 ((+)-Sodwanone M)

3D PDB for NP0083271 ((+)-Sodwanone M)

SMILES for NP0083271 ((+)-Sodwanone M)

INCHI for NP0083271 ((+)-Sodwanone M)

Structure for NP0083271 ((+)-Sodwanone M)

3D Structure for NP0083271 ((+)-Sodwanone M)