NP-MRD: Showing NP-Card for Swietenin D (NP0066539)

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Record Information

Version

2.0

Created at

2022-04-28 10:47:35 UTC

Updated at

2022-04-28 10:47:35 UTC

NP-MRD ID

NP0066539

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Swietenin D

Description

Swietenin D belongs to the class of organic compounds known as naphthopyrans. Naphthopyrans are compounds containing a pyran ring fused to a naphthalene moiety. Furan is a 6 membered-ring non-aromatic ring with five carbon and one oxygen atoms. Naphthalene is a polycyclic aromatic hydrocarbon made up of two fused benzene rings. Swietenin D is found in Swietenia mahagoni and Swietenia mahagoni JACQ. . Based on a literature review very few articles have been published on Swietenin D.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282212472D          

 40 44  0  0  1  0            999 V2000
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 38 40  1  0  0  0  0
M  END

     RDKit          3D

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M  END


  Mrv1652304282212472D          

 40 44  0  0  1  0            999 V2000
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    6.3958    3.2761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8095    1.6013    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5428    0.8206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7334    0.6612    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0856    0.1993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8950    0.3587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8189   -0.5814    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  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  6  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  1  8  1  0  0  0  0
  8  9  1  1  0  0  0
  4  9  1  0  0  0  0
  9 10  2  0  0  0  0
 11  6  1  6  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
  5 14  1  0  0  0  0
 12 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
 11 19  1  0  0  0  0
 15 20  1  1  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 20 24  2  0  0  0  0
 12 25  1  1  0  0  0
  4 26  1  1  0  0  0
  3 27  1  1  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 28 30  1  0  0  0  0
 30 31  1  0  0  0  0
 27 32  1  6  0  0  0
  2 33  1  0  0  0  0
  2 34  1  0  0  0  0
  1 35  1  6  0  0  0
 35 36  1  0  0  0  0
 36 37  2  0  0  0  0
 36 38  1  0  0  0  0
 38 39  2  0  0  0  0
 38 40  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0066539

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)[C@H](O)[C@H]1C(C)(C)[C@H](OC(=O)C(C)=C)[C@@H]2C=C3[C@H](CC[C@]4(C)[C@H]3CC(=O)O[C@H]4C3=COC=C3)[C@@]1(C)C2=O

> <INCHI_IDENTIFIER>
InChI=1S/C31H38O9/c1-15(2)27(35)40-26-18-12-17-19(31(6,24(18)34)23(29(26,3)4)22(33)28(36)37-7)8-10-30(5)20(17)13-21(32)39-25(30)16-9-11-38-14-16/h9,11-12,14,18-20,22-23,25-26,33H,1,8,10,13H2,2-7H3/t18-,19+,20+,22-,23+,25+,26-,30-,31-/m1/s1

> <INCHI_KEY>
VQIHLSVRJTYSPL-IUFUNHPJSA-N

> <FORMULA>
C31H38O9

> <MOLECULAR_WEIGHT>
554.636

> <EXACT_MASS>
554.251582804

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
78

> <JCHEM_AVERAGE_POLARIZABILITY>
57.56617707606922

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,2S,5R,6R,10S,13S,14R,16S)-6-(furan-3-yl)-16-[(1R)-1-hydroxy-2-methoxy-2-oxoethyl]-1,5,15,15-tetramethyl-8,17-dioxo-7-oxatetracyclo[11.3.1.0^{2,11}.0^{5,10}]heptadec-11-en-14-yl 2-methylprop-2-enoate

> <ALOGPS_LOGP>
2.74

> <JCHEM_LOGP>
4.114084623666665

> <ALOGPS_LOGS>
-4.29

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.821737186142048

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.397481210921786

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8887308288581393

> <JCHEM_POLAR_SURFACE_AREA>
129.34000000000003

> <JCHEM_REFRACTIVITY>
142.50140000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.87e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2S,5R,6R,10S,13S,14R,16S)-6-(furan-3-yl)-16-[(1R)-1-hydroxy-2-methoxy-2-oxoethyl]-1,5,15,15-tetramethyl-8,17-dioxo-7-oxatetracyclo[11.3.1.0^{2,11}.0^{5,10}]heptadec-11-en-14-yl 2-methylprop-2-enoate

> <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       9.831   4.149   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      10.515   5.529   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.023   6.988   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.643   7.672   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.184   7.179   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.500   5.800   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.992   4.340   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.372   3.657   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.009   5.630   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      10.191   4.643   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       4.963   5.702   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.110   6.984   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.794   8.364   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.331   8.462   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.573   6.886   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       1.889   5.506   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       2.742   4.224   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       2.059   2.844   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       4.279   4.322   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.720   8.168   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.181   8.232   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -0.234   9.715   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       1.048  10.568   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       2.256   9.612   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       3.257   8.266   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       8.747   9.208   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      11.183   8.001   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      10.885   9.512   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       9.428  10.010   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0      12.045  10.525   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      11.747  12.036   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      12.640   7.503   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      11.847   4.756   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      11.939   6.115   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      10.844   2.989   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0      10.347   1.532   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0       8.836   1.234   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0      11.360   0.372   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      12.871   0.670   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      10.862  -1.085   0.000  0.00  0.00           C+0
CONECT    1    2    8   35                                                  
CONECT    2    1    3   33   34                                             
CONECT    3    2    4   27                                                  
CONECT    4    3    5    9   26                                             
CONECT    5    4    6   14                                                  
CONECT    6    5    7   11                                                  
CONECT    7    6    8                                                       
CONECT    8    7    1    9                                                  
CONECT    9    8    4   10                                                  
CONECT   10    9                                                            
CONECT   11    6   12   19                                                  
CONECT   12   11   13   15   25                                             
CONECT   13   12   14                                                       
CONECT   14   13    5                                                       
CONECT   15   12   16   20                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   11                                                       
CONECT   20   15   21   24                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   20                                                       
CONECT   25   12                                                            
CONECT   26    4                                                            
CONECT   27    3   28   32                                                  
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31                                                       
CONECT   31   30                                                            
CONECT   32   27                                                            
CONECT   33    2                                                            
CONECT   34    2                                                            
CONECT   35    1   36                                                       
CONECT   36   35   37   38                                                  
CONECT   37   36                                                            
CONECT   38   36   39   40                                                  
CONECT   39   38                                                            
CONECT   40   38                                                            
MASTER        0    0    0    0    0    0    0    0   40    0   88    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₁H₃₈O₉

Average Mass

554.6360 Da

Monoisotopic Mass

554.25158 Da

IUPAC Name

(1R,2S,5R,6R,10S,13S,14R,16S)-6-(furan-3-yl)-16-[(1R)-1-hydroxy-2-methoxy-2-oxoethyl]-1,5,15,15-tetramethyl-8,17-dioxo-7-oxatetracyclo[11.3.1.0^{2,11}.0^{5,10}]heptadec-11-en-14-yl 2-methylprop-2-enoate

Traditional Name

CAS Registry Number

Not Available

SMILES

COC(=O)[C@H](O)[C@H]1C(C)(C)[C@H](OC(=O)C(C)=C)[C@@H]2C=C3[C@H](CC[C@]4(C)[C@H]3CC(=O)O[C@H]4C3=COC=C3)[C@@]1(C)C2=O

InChI Identifier

InChI=1S/C31H38O9/c1-15(2)27(35)40-26-18-12-17-19(31(6,24(18)34)23(29(26,3)4)22(33)28(36)37-7)8-10-30(5)20(17)13-21(32)39-25(30)16-9-11-38-14-16/h9,11-12,14,18-20,22-23,25-26,33H,1,8,10,13H2,2-7H3/t18-,19+,20+,22-,23+,25+,26-,30-,31-/m1/s1

InChI Key

VQIHLSVRJTYSPL-IUFUNHPJSA-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
Swietenia mahagoni	LOTUS Database	35616633
Swietenia mahagoni JACQ.	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as naphthopyrans. Naphthopyrans are compounds containing a pyran ring fused to a naphthalene moiety. Furan is a 6 membered-ring non-aromatic ring with five carbon and one oxygen atoms. Naphthalene is a polycyclic aromatic hydrocarbon made up of two fused benzene rings.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Naphthopyrans

Sub Class

Not Available

Direct Parent

Naphthopyrans

Alternative Parents

Substituents

Naphthopyran
Naphthalene
Tricarboxylic acid or derivatives
Delta valerolactone
Delta_valerolactone
Cyclohexenone
Oxane
Pyran
Furan
Heteroaromatic compound
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Methyl ester
Lactone
Ketone
Secondary alcohol
Carboxylic acid ester
Oxacycle
Carboxylic acid derivative
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Alcohol
Organic oxygen compound
Carbonyl group
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	2.74	ALOGPS
logP	4.11	ChemAxon
logS	-4.3	ALOGPS
pKa (Strongest Acidic)	12.4	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	142.5 m³·mol⁻¹	ChemAxon
Polarizability	57.57 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	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00024106

Chemspider ID

10404655

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

23259002

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Swietenin D (NP0066539)

MOL for NP0066539 (Swietenin D)

3D MOL for NP0066539 (Swietenin D)

3D SDF for NP0066539 (Swietenin D)

3D-SDF for NP0066539 (Swietenin D)

PDB for NP0066539 (Swietenin D)

3D PDB for NP0066539 (Swietenin D)

SMILES for NP0066539 (Swietenin D)

INCHI for NP0066539 (Swietenin D)

Structure for NP0066539 (Swietenin D)

3D Structure for NP0066539 (Swietenin D)