NP-MRD: Showing NP-Card for (+)-Sodwanone D (NP0083269)

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Record Information

Version

2.0

Created at

2022-04-29 04:18:44 UTC

Updated at

2022-04-29 04:18:44 UTC

NP-MRD ID

NP0083269

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(+)-Sodwanone D

Description

(9Abeta)-Octahydro-6beta-hydroxy-2,2,5aalpha,7beta-tetramethyl-6-[2-[[(9abeta)-decahydro-2,2,5aalpha-trimethyl-7-methylene-3-oxo-1-benzoxepin]-6alpha-yl]ethyl]-1-benzoxepin-3(2H)-one belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. (+)-Sodwanone D is found in Axinella weltneri. Based on a literature review very few articles have been published on (9abeta)-Octahydro-6beta-hydroxy-2,2,5aalpha,7beta-tetramethyl-6-[2-[[(9abeta)-decahydro-2,2,5aalpha-trimethyl-7-methylene-3-oxo-1-benzoxepin]-6alpha-yl]ethyl]-1-benzoxepin-3(2H)-one.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304292206182D          

 35 38  0  0  1  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652304292206182D          

 35 38  0  0  1  0            999 V2000
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   -1.9762   -6.0029    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2807   -4.7913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6567   -4.2516    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3494   -6.8952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0858   -6.7577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1775   -3.6476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  6  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
  6  7  1  6  0  0  0
  7  8  1  0  0  0  0
  9  8  1  6  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  6  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
  9 14  1  0  0  0  0
 14 15  2  0  0  0  0
 11 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
 20 21  1  0  0  0  0
 10 21  1  0  0  0  0
 17 22  1  0  0  0  0
 17 23  1  0  0  0  0
 10 24  1  6  0  0  0
  6 25  1  1  0  0  0
  5 26  1  1  0  0  0
  2 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 29 31  1  0  0  0  0
 31 32  1  0  0  0  0
  1 32  1  0  0  0  0
 28 33  1  0  0  0  0
 28 34  1  0  0  0  0
  1 35  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0083269

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C30H48O5/c1-19-9-11-24-28(7,16-14-22(31)26(3,4)34-24)21(19)13-18-30(33)20(2)10-12-25-29(30,8)17-15-23(32)27(5,6)35-25/h20-21,24-25,33H,1,9-18H2,2-8H3/t20-,21+,24-,25-,28-,29+,30-/m0/s1

> <INCHI_KEY>
IFCHJVPYNAHAND-XXDHPLDNSA-N

> <FORMULA>
C30H48O5

> <MOLECULAR_WEIGHT>
488.709

> <EXACT_MASS>
488.350174646

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
83

> <JCHEM_AVERAGE_POLARIZABILITY>
57.29548716662134

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(5aR,6S,7S,9aS)-6-{2-[(5aS,6R,9aS)-2,2,5a-trimethyl-7-methylidene-3-oxo-decahydro-1-benzoxepin-6-yl]ethyl}-6-hydroxy-2,2,5a,7-tetramethyl-decahydro-1-benzoxepin-3-one

> <ALOGPS_LOGP>
4.83

> <JCHEM_LOGP>
5.791706400000001

> <ALOGPS_LOGS>
-6.18

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
17.634721311916163

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.121188132478931

> <JCHEM_PKA_STRONGEST_BASIC>
-3.1830716273940762

> <JCHEM_POLAR_SURFACE_AREA>
72.83000000000001

> <JCHEM_REFRACTIVITY>
137.5468

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.25e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(5aR,6S,7S,9aS)-6-{2-[(5aS,6R,9aS)-2,2,5a-trimethyl-7-methylidene-3-oxo-hexahydro-1-benzoxepin-6-yl]ethyl}-6-hydroxy-2,2,5a,7-tetramethyl-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       0.288  -8.219   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.011  -9.579   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.550  -9.632   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.366  -8.326   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.643  -6.967   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.104  -6.913   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.104  -5.373   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.230  -4.603   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.230  -3.063   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.104  -2.293   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.104  -0.753   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.230   0.017   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.563  -0.753   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.563  -2.293   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -2.897  -3.063   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       2.308   0.207   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       3.810  -0.135   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.478  -1.523   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       6.018  -1.523   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       3.810  -2.910   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.308  -3.253   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.118   1.373   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       5.212   0.502   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       0.989  -3.828   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      -0.173  -6.052   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       3.459  -5.661   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       0.399 -10.992   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      -1.088 -11.394   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -2.329 -10.482   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      -3.689 -11.205   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      -2.391  -8.944   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -1.226  -7.936   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -0.652 -12.871   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -2.027 -12.614   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -0.331  -6.809   0.000  0.00  0.00           C+0
CONECT    1    2    6   32   35                                             
CONECT    2    1    3   27                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   26                                                  
CONECT    6    5    1    7   25                                             
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   14                                                  
CONECT   10    9   11   21   24                                             
CONECT   11   10   12   16                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13    9   15                                                  
CONECT   15   14                                                            
CONECT   16   11   17                                                       
CONECT   17   16   18   22   23                                             
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20   10                                                       
CONECT   22   17                                                            
CONECT   23   17                                                            
CONECT   24   10                                                            
CONECT   25    6                                                            
CONECT   26    5                                                            
CONECT   27    2   28                                                       
CONECT   28   27   29   33   34                                             
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   32                                                       
CONECT   32   31    1                                                       
CONECT   33   28                                                            
CONECT   34   28                                                            
CONECT   35    1                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   76    0
END

View in JSmol

Synonyms

Value	Source
(9Abeta)-octahydro-6b-hydroxy-2,2,5aalpha,7b-tetramethyl-6-[2-[[(9abeta)-decahydro-2,2,5aalpha-trimethyl-7-methylene-3-oxo-1-benzoxepin]-6a-yl]ethyl]-1-benzoxepin-3(2H)-one	Generator
(9Abeta)-octahydro-6β-hydroxy-2,2,5aalpha,7β-tetramethyl-6-[2-[[(9abeta)-decahydro-2,2,5aalpha-trimethyl-7-methylene-3-oxo-1-benzoxepin]-6α-yl]ethyl]-1-benzoxepin-3(2H)-one	Generator

Chemical Formula

C₃₀H₄₈O₅

Average Mass

488.7090 Da

Monoisotopic Mass

488.35017 Da

IUPAC Name

(5aR,6S,7S,9aS)-6-{2-[(5aS,6R,9aS)-2,2,5a-trimethyl-7-methylidene-3-oxo-decahydro-1-benzoxepin-6-yl]ethyl}-6-hydroxy-2,2,5a,7-tetramethyl-decahydro-1-benzoxepin-3-one

Traditional Name

(5aR,6S,7S,9aS)-6-{2-[(5aS,6R,9aS)-2,2,5a-trimethyl-7-methylidene-3-oxo-hexahydro-1-benzoxepin-6-yl]ethyl}-6-hydroxy-2,2,5a,7-tetramethyl-hexahydro-1-benzoxepin-3-one

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C30H48O5/c1-19-9-11-24-28(7,16-14-22(31)26(3,4)34-24)21(19)13-18-30(33)20(2)10-12-25-29(30,8)17-15-23(32)27(5,6)35-25/h20-21,24-25,33H,1,9-18H2,2-8H3/t20-,21+,24-,25-,28-,29+,30-/m0/s1

InChI Key

IFCHJVPYNAHAND-XXDHPLDNSA-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 triterpenoids. These are terpene molecules containing six isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Triterpenoids

Direct Parent

Triterpenoids

Alternative Parents

Substituents

Triterpenoid
Oxepane
Cyclic alcohol
Tertiary alcohol
Ketone
Cyclic ketone
Dialkyl ether
Ether
Oxacycle
Organoheterocyclic compound
Organic oxide
Alcohol
Organooxygen compound
Hydrocarbon derivative
Carbonyl group
Organic oxygen compound
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	4.83	ALOGPS
logP	5.79	ChemAxon
logS	-6.2	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	72.83 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	137.55 m³·mol⁻¹	ChemAxon
Polarizability	57.3 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

10475166

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

21773189

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for (+)-Sodwanone D (NP0083269)

MOL for NP0083269 ((+)-Sodwanone D)

3D MOL for NP0083269 ((+)-Sodwanone D)

3D SDF for NP0083269 ((+)-Sodwanone D)

3D-SDF for NP0083269 ((+)-Sodwanone D)

PDB for NP0083269 ((+)-Sodwanone D)

3D PDB for NP0083269 ((+)-Sodwanone D)

SMILES for NP0083269 ((+)-Sodwanone D)

INCHI for NP0083269 ((+)-Sodwanone D)

Structure for NP0083269 ((+)-Sodwanone D)

3D Structure for NP0083269 ((+)-Sodwanone D)