NP-MRD: Showing NP-Card for (-)-Domesticulide B (NP0074125)

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Record Information

Version

2.0

Created at

2022-04-28 19:17:52 UTC

Updated at

2022-04-28 19:17:52 UTC

NP-MRD ID

NP0074125

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(-)-Domesticulide B

Description

Methyl (2S)-2-[(1R,2S)-2-[(1R,4aS,6R,8aS)-1-(furan-3-yl)-4a-hydroxy-8a-methyl-5-methylidene-3-oxo-octahydro-1H-2-benzopyran-6-yl]-2,6,6-trimethyl-5-oxocyclohex-3-en-1-yl]-2-(acetyloxy)acetate belongs to the class of organic compounds known as benzopyrans. These are organic compounds containing a benzene ring fused to a pyran ring. Pyran a six-membered heterocyclic, non-aromatic ring, made up of five carbon atoms and one oxygen atom and containing two double bonds. (-)-Domesticulide B is found in Lansium domesticum and Lansium domesticum Corr. . Based on a literature review very few articles have been published on methyl (2S)-2-[(1R,2S)-2-[(1R,4aS,6R,8aS)-1-(furan-3-yl)-4a-hydroxy-8a-methyl-5-methylidene-3-oxo-octahydro-1H-2-benzopyran-6-yl]-2,6,6-trimethyl-5-oxocyclohex-3-en-1-yl]-2-(acetyloxy)acetate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282221172D          

 38 41  0  0  1  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652304282221172D          

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  1  2  2  0  0  0  0
  1  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  1  0  0  0  0
  1  7  1  0  0  0  0
  6  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
  5 12  1  0  0  0  0
 10 13  1  1  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  2  0  0  0  0
 16 18  1  0  0  0  0
 18 19  2  0  0  0  0
 13 19  1  1  0  0  0
 15 20  1  0  0  0  0
 15 21  1  0  0  0  0
 14 22  1  6  0  0  0
 22 23  1  6  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 24 26  1  0  0  0  0
 22 27  1  0  0  0  0
 27 28  2  0  0  0  0
 27 29  1  0  0  0  0
 29 30  1  0  0  0  0
 13 31  1  1  0  0  0
  6 32  1  1  0  0  0
  5 33  1  6  0  0  0
  4 34  1  6  0  0  0
 34 35  2  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  2  0  0  0  0
 34 38  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0074125

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)[C@@H](OC(C)=O)[C@H]1C(C)(C)C(=O)C=C[C@@]1(C)[C@H]1CC[C@@]2(C)[C@@H](OC(=O)C[C@]2(O)C1=C)C1=COC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C29H36O9/c1-16-19(8-12-28(6)24(18-10-13-36-15-18)38-21(32)14-29(16,28)34)27(5)11-9-20(31)26(3,4)23(27)22(25(33)35-7)37-17(2)30/h9-11,13,15,19,22-24,34H,1,8,12,14H2,2-7H3/t19-,22-,23-,24-,27-,28-,29-/m0/s1

> <INCHI_KEY>
VTJUVXVINSZWCE-HTUYVMPMSA-N

> <FORMULA>
C29H36O9

> <MOLECULAR_WEIGHT>
528.598

> <EXACT_MASS>
528.235932739

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
74

> <JCHEM_AVERAGE_POLARIZABILITY>
54.0685749441176

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl (2S)-2-[(1R,2S)-2-[(1R,4aS,6R,8aS)-1-(furan-3-yl)-4a-hydroxy-8a-methyl-5-methylidene-3-oxo-octahydro-1H-2-benzopyran-6-yl]-2,6,6-trimethyl-5-oxocyclohex-3-en-1-yl]-2-(acetyloxy)acetate

> <ALOGPS_LOGP>
3.46

> <JCHEM_LOGP>
3.3773920053333315

> <ALOGPS_LOGS>
-4.38

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.482024846457179

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8861324094073924

> <JCHEM_POLAR_SURFACE_AREA>
129.34000000000003

> <JCHEM_REFRACTIVITY>
135.20469999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.21e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(S)-(methyl [(1R,2S)-2-[(1R,4aS,6R,8aS)-1-(furan-3-yl)-4a-hydroxy-8a-methyl-5-methylidene-3-oxo-tetrahydro-1H-2-benzopyran-6-yl]-2,6,6-trimethyl-5-oxocyclohex-3-en-1-yl](acetyloxy)acetate)

> <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      16.741   4.212   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      17.921   3.222   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      17.009   5.729   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      15.829   6.719   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      14.382   6.192   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      14.114   4.675   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      15.294   3.685   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      12.667   4.149   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      12.400   2.632   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      11.487   5.138   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      11.755   6.655   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      13.202   7.182   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      10.040   4.612   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.500   4.612   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.730   3.278   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.500   1.944   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       7.730   0.611   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      10.040   1.944   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      10.810   3.278   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.371   4.001   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.371   2.555   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       7.730   5.945   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       6.190   5.945   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       5.420   7.279   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       3.880   7.279   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       6.190   8.613   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       8.500   7.279   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       7.730   8.613   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0      10.040   7.279   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      10.810   5.945   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       9.773   6.128   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      13.847   3.159   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      14.649   7.708   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      16.096   8.235   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      17.480   8.910   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      17.266  10.435   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0      15.749  10.703   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      15.026   9.343   0.000  0.00  0.00           C+0
CONECT    1    2    3    7                                                  
CONECT    2    1                                                            
CONECT    3    1    4                                                       
CONECT    4    3    5   34                                                  
CONECT    5    4    6   12   33                                             
CONECT    6    5    7    8   32                                             
CONECT    7    6    1                                                       
CONECT    8    6    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   13                                                  
CONECT   11   10   12                                                       
CONECT   12   11    5                                                       
CONECT   13   10   14   19   31                                             
CONECT   14   13   15   22                                                  
CONECT   15   14   16   20   21                                             
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18   13                                                       
CONECT   20   15                                                            
CONECT   21   15                                                            
CONECT   22   14   23   27                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24                                                            
CONECT   27   22   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30                                                       
CONECT   30   29                                                            
CONECT   31   13                                                            
CONECT   32    6                                                            
CONECT   33    5                                                            
CONECT   34    4   35   38                                                  
CONECT   35   34   36                                                       
CONECT   36   35   37                                                       
CONECT   37   36   38                                                       
CONECT   38   37   34                                                       
MASTER        0    0    0    0    0    0    0    0   38    0   82    0
END

View in JSmol

Synonyms

Value	Source
Methyl (2S)-2-[(1R,2S)-2-[(1R,4as,6R,8as)-1-(furan-3-yl)-4a-hydroxy-8a-methyl-5-methylidene-3-oxo-octahydro-1H-2-benzopyran-6-yl]-2,6,6-trimethyl-5-oxocyclohex-3-en-1-yl]-2-(acetyloxy)acetic acid	Generator

Chemical Formula

C₂₉H₃₆O₉

Average Mass

528.5980 Da

Monoisotopic Mass

528.23593 Da

IUPAC Name

methyl (2S)-2-[(1R,2S)-2-[(1R,4aS,6R,8aS)-1-(furan-3-yl)-4a-hydroxy-8a-methyl-5-methylidene-3-oxo-octahydro-1H-2-benzopyran-6-yl]-2,6,6-trimethyl-5-oxocyclohex-3-en-1-yl]-2-(acetyloxy)acetate

Traditional Name

(S)-(methyl [(1R,2S)-2-[(1R,4aS,6R,8aS)-1-(furan-3-yl)-4a-hydroxy-8a-methyl-5-methylidene-3-oxo-tetrahydro-1H-2-benzopyran-6-yl]-2,6,6-trimethyl-5-oxocyclohex-3-en-1-yl](acetyloxy)acetate)

CAS Registry Number

Not Available

SMILES

COC(=O)[C@@H](OC(C)=O)[C@H]1C(C)(C)C(=O)C=C[C@@]1(C)[C@H]1CC[C@@]2(C)[C@@H](OC(=O)C[C@]2(O)C1=C)C1=COC=C1

InChI Identifier

InChI=1S/C29H36O9/c1-16-19(8-12-28(6)24(18-10-13-36-15-18)38-21(32)14-29(16,28)34)27(5)11-9-20(31)26(3,4)23(27)22(25(33)35-7)37-17(2)30/h9-11,13,15,19,22-24,34H,1,8,12,14H2,2-7H3/t19-,22-,23-,24-,27-,28-,29-/m0/s1

InChI Key

VTJUVXVINSZWCE-HTUYVMPMSA-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
Lansium domesticum	LOTUS Database	35616633
Lansium domesticum Corr.	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzopyrans. These are organic compounds containing a benzene ring fused to a pyran ring. Pyran a six-membered heterocyclic, non-aromatic ring, made up of five carbon atoms and one oxygen atom and containing two double bonds.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzopyrans

Sub Class

Not Available

Direct Parent

Benzopyrans

Alternative Parents

Substituents

Benzopyran
Tricarboxylic acid or derivatives
Cyclohexenone
Delta_valerolactone
Delta valerolactone
Oxane
Heteroaromatic compound
Methyl ester
Tertiary alcohol
Furan
Cyclic alcohol
Cyclic ketone
Lactone
Ketone
Carboxylic acid ester
Oxacycle
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
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	3.46	ALOGPS
logP	3.38	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Acidic)	13.48	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	129.34 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	135.2 m³·mol⁻¹	ChemAxon
Polarizability	54.07 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	Yes	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

162997450

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for (-)-Domesticulide B (NP0074125)

MOL for NP0074125 ((-)-Domesticulide B)

3D MOL for NP0074125 ((-)-Domesticulide B)

3D SDF for NP0074125 ((-)-Domesticulide B)

3D-SDF for NP0074125 ((-)-Domesticulide B)

PDB for NP0074125 ((-)-Domesticulide B)

3D PDB for NP0074125 ((-)-Domesticulide B)

SMILES for NP0074125 ((-)-Domesticulide B)

INCHI for NP0074125 ((-)-Domesticulide B)

Structure for NP0074125 ((-)-Domesticulide B)

3D Structure for NP0074125 ((-)-Domesticulide B)