NP-MRD: Showing NP-Card for 3,6-dihydroxy-1a-(3-methylbut-2-en-1-yl)-7ah-naphtho[2,3-b]oxirene-2,7-dione (NP0301358)

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Record Information

Version

2.0

Created at

2022-09-10 14:15:30 UTC

Updated at

2022-09-10 14:15:30 UTC

NP-MRD ID

NP0301358

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3,6-dihydroxy-1a-(3-methylbut-2-en-1-yl)-7ah-naphtho[2,3-b]oxirene-2,7-dione

Description

2,3-Epoxysesamone belongs to the class of organic compounds known as vitamin k compounds. These are quinone lipids containing a methylated naphthoquinone ring structure, and vary in the aliphatic side chain attached at the 3-position. 2,3-Epoxysesamone is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, 2,3-Epoxysesamone has been detected, but not quantified in, fats and oils. 3,6-dihydroxy-1a-(3-methylbut-2-en-1-yl)-7ah-naphtho[2,3-b]oxirene-2,7-dione is found in Sesamum indicum. This could make 2,3-epoxysesamone a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 34 36  0  0  0  0  0  0  0  0999 V2000
    4.0496    1.0624    0.2599 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6892   -0.3623    0.0355 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7492   -1.3157   -0.3909 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4411   -0.8022    0.2077 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3412    0.0821    0.6281 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2187    0.1251   -0.4037 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4822    0.5613   -1.6780 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2446    1.4017   -0.8457 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7066    1.5342   -1.0683 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1692    2.3688   -1.8726 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6326    0.6804   -0.3424 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9278    1.0691   -0.0590 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4393    2.2848   -0.4267 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7812    0.2006    0.6375 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3109   -1.0131    1.0217 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9851   -1.4077    0.7312 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5966   -2.6480    1.1598 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1508   -0.5599    0.0498 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7853   -0.9370   -0.2732 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4678   -2.1262   -0.4371 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1688    1.2958    1.3555 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3245    1.7596   -0.2203 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0269    1.2733   -0.2060 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5165   -1.3695    0.4260 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2493   -0.9726   -1.3306 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3171   -2.3217   -0.5501 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2096   -1.8467    0.0362 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6991    1.1138    0.8283 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8700   -0.2548    1.5879 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3066    2.3103   -0.5367 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9999    3.0126   -0.8968 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7804    0.5244    0.8445 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9687   -1.6769    1.5560 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7127   -3.0453    1.0477 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  6  5  1  1
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 12 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 16 18  2  0
 18 19  1  0
 19 20  2  0
  8  6  1  0
 18 11  1  0
 19  6  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  3 24  1  0
  3 25  1  0
  3 26  1  0
  4 27  1  0
  5 28  1  0
  5 29  1  0
  8 30  1  1
 13 31  1  0
 14 32  1  0
 15 33  1  0
 17 34  1  0
M  END


  Mrv0541 05061307042D          

 20 22  0  0  0  0            999 V2000
    0.1914    3.7934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    4.5079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    3.0789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0164    2.3645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0164    3.7934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  2  0  0  0  0
  6  5  1  0  0  0  0
  7  1  1  0  0  0  0
  7  2  1  0  0  0  0
  7  5  2  0  0  0  0
  8  3  1  0  0  0  0
  9  4  1  0  0  0  0
 10  8  2  0  0  0  0
 11  9  2  0  0  0  0
 11 10  1  0  0  0  0
 12 10  1  0  0  0  0
 13 11  1  0  0  0  0
 14 12  1  0  0  0  0
 15  6  1  0  0  0  0
 15 13  1  0  0  0  0
 15 14  1  0  0  0  0
 16  8  1  0  0  0  0
 17  9  1  0  0  0  0
 18 12  2  0  0  0  0
 19 13  2  0  0  0  0
 20 14  1  0  0  0  0
 20 15  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0301358

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)=CCC12OC1C(=O)C1=C(O)C=CC(O)=C1C2=O

> <INCHI_IDENTIFIER>
InChI=1S/C15H14O5/c1-7(2)5-6-15-13(19)11-9(17)4-3-8(16)10(11)12(18)14(15)20-15/h3-5,14,16-17H,6H2,1-2H3

> <INCHI_KEY>
TWESJUCJKWFWQV-UHFFFAOYSA-N

> <FORMULA>
C15H14O5

> <MOLECULAR_WEIGHT>
274.2687

> <EXACT_MASS>
274.084123558

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
27.334410420928975

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3,6-dihydroxy-1a-(3-methylbut-2-en-1-yl)-1aH,2H,7H,7aH-naphtho[2,3-b]oxirene-2,7-dione

> <ALOGPS_LOGP>
2.45

> <JCHEM_LOGP>
3.286870548333333

> <ALOGPS_LOGS>
-2.42

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.248150665461441

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.490848770938264

> <JCHEM_PKA_STRONGEST_BASIC>
-4.34630274573094

> <JCHEM_POLAR_SURFACE_AREA>
87.13

> <JCHEM_REFRACTIVITY>
72.0792

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.05e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3,6-dihydroxy-1a-(3-methylbut-2-en-1-yl)-7aH-naphtho[2,3-b]oxirene-2,7-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       0.357   7.081   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667   8.415   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.002   3.080   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667   5.747   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.897   4.414   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.897   7.081   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.668   0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.335   3.080   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.001   0.770   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.667   3.080   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       6.668  -0.770   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       6.668   5.390   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       4.001  -0.770   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       4.001   5.390   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       1.334   2.310   0.000  0.00  0.00           O+0
CONECT    1    7                                                            
CONECT    2    7                                                            
CONECT    3    4    8                                                       
CONECT    4    3    9                                                       
CONECT    5    6    7                                                       
CONECT    6    5   15                                                       
CONECT    7    1    2    5                                                  
CONECT    8    3   10   16                                                  
CONECT    9    4   11   17                                                  
CONECT   10    8   11   12                                                  
CONECT   11    9   10   13                                                  
CONECT   12   10   14   18                                                  
CONECT   13   11   15   19                                                  
CONECT   14   12   15   20                                                  
CONECT   15    6   13   14   20                                             
CONECT   16    8                                                            
CONECT   17    9                                                            
CONECT   18   12                                                            
CONECT   19   13                                                            
CONECT   20   14   15                                                       
MASTER        0    0    0    0    0    0    0    0   20    0   44    0
END

View in JSmol

Synonyms

Value	Source
2,3-Epoxy-2-prenylnaphthazarin	HMDB
3,6-Dihydroxy-1a-(3-methyl-2-butenyl)naphth[2,3-b]-2,7(1ah,7ah)-dione	HMDB
2,3-Epoxy-2,3-dihydro-5,8-dihydroxy-2-(3-methyl-2-butenyl)-1,4-naphthoquinone	HMDB
2,3-Epoxysesamone	MeSH

Chemical Formula

C₁₅H₁₄O₅

Average Mass

274.2687 Da

Monoisotopic Mass

274.08412 Da

IUPAC Name

3,6-dihydroxy-1a-(3-methylbut-2-en-1-yl)-1aH,2H,7H,7aH-naphtho[2,3-b]oxirene-2,7-dione

Traditional Name

3,6-dihydroxy-1a-(3-methylbut-2-en-1-yl)-7aH-naphtho[2,3-b]oxirene-2,7-dione

CAS Registry Number

Not Available

SMILES

CC(C)=CCC12OC1C(=O)C1=C(O)C=CC(O)=C1C2=O

InChI Identifier

InChI=1S/C15H14O5/c1-7(2)5-6-15-13(19)11-9(17)4-3-8(16)10(11)12(18)14(15)20-15/h3-5,14,16-17H,6H2,1-2H3

InChI Key

TWESJUCJKWFWQV-UHFFFAOYSA-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, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, 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
Sesamum indicum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as vitamin k compounds. These are quinone lipids containing a methylated naphthoquinone ring structure, and vary in the aliphatic side chain attached at the 3-position.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Quinone and hydroquinone lipids

Direct Parent

Vitamin K compounds

Alternative Parents

Substituents

Naphthoquinone
Naphthalene
Tetralin
Quinone
Aryl ketone
Aryl alkyl ketone
1-hydroxy-2-unsubstituted benzenoid
Benzenoid
Vinylogous acid
Ketone
Organoheterocyclic compound
Oxacycle
Ether
Oxirane
Dialkyl ether
Hydrocarbon derivative
Organooxygen compound
Organic oxide
Organic oxygen 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	2.45	ALOGPS
logP	3.29	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	9.49	ChemAxon
pKa (Strongest Basic)	-4.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	87.13 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	72.08 m³·mol⁻¹	ChemAxon
Polarizability	27.33 Å³	ChemAxon
Number of Rings	3	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

HMDB0033333

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB011360

KNApSAcK ID

Not Available

Chemspider ID

320321

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

360837

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 3,6-dihydroxy-1a-(3-methylbut-2-en-1-yl)-7ah-naphtho[2,3-b]oxirene-2,7-dione (NP0301358)

MOL for NP0301358 (3,6-dihydroxy-1a-(3-methylbut-2-en-1-yl)-7ah-naphtho[2,3-b]oxirene-2,7-dione)

3D MOL for NP0301358 (3,6-dihydroxy-1a-(3-methylbut-2-en-1-yl)-7ah-naphtho[2,3-b]oxirene-2,7-dione)

3D SDF for NP0301358 (3,6-dihydroxy-1a-(3-methylbut-2-en-1-yl)-7ah-naphtho[2,3-b]oxirene-2,7-dione)

3D-SDF for NP0301358 (3,6-dihydroxy-1a-(3-methylbut-2-en-1-yl)-7ah-naphtho[2,3-b]oxirene-2,7-dione)

PDB for NP0301358 (3,6-dihydroxy-1a-(3-methylbut-2-en-1-yl)-7ah-naphtho[2,3-b]oxirene-2,7-dione)

3D PDB for NP0301358 (3,6-dihydroxy-1a-(3-methylbut-2-en-1-yl)-7ah-naphtho[2,3-b]oxirene-2,7-dione)

SMILES for NP0301358 (3,6-dihydroxy-1a-(3-methylbut-2-en-1-yl)-7ah-naphtho[2,3-b]oxirene-2,7-dione)

INCHI for NP0301358 (3,6-dihydroxy-1a-(3-methylbut-2-en-1-yl)-7ah-naphtho[2,3-b]oxirene-2,7-dione)

Structure for NP0301358 (3,6-dihydroxy-1a-(3-methylbut-2-en-1-yl)-7ah-naphtho[2,3-b]oxirene-2,7-dione)

3D Structure for NP0301358 (3,6-dihydroxy-1a-(3-methylbut-2-en-1-yl)-7ah-naphtho[2,3-b]oxirene-2,7-dione)