NP-MRD: Showing NP-Card for (1as,7ar)-3-hydroxy-1a-(3-methylbut-2-en-1-yl)-7ah-naphtho[2,3-b]oxirene-2,7-dione (NP0305281)

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Record Information

Version

2.0

Created at

2022-09-10 20:58:36 UTC

Updated at

2022-09-10 20:58:36 UTC

NP-MRD ID

NP0305281

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1as,7ar)-3-hydroxy-1a-(3-methylbut-2-en-1-yl)-7ah-naphtho[2,3-b]oxirene-2,7-dione

Description

CHEMBL2023567 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. (1as,7ar)-3-hydroxy-1a-(3-methylbut-2-en-1-yl)-7ah-naphtho[2,3-b]oxirene-2,7-dione is found in Diospyros maritima. Based on a literature review very few articles have been published on CHEMBL2023567.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 33 35  0  0  0  0  0  0  0  0999 V2000
   -3.6465   -0.8265    0.2701 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0450    0.1363   -0.6740 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5277    0.0894   -2.1038 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1169    1.0163   -0.3027 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6855    1.0155    1.1068 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2158    0.7404    1.2654 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0986    0.7644    2.7193 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6261    1.7413    1.8025 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0729    1.6219    1.6403 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8387    2.2939    2.3604 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6555    0.7299    0.6500 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9651    0.8485    0.2528 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4481   -0.0254   -0.6840 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6430   -1.0259   -1.2386 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3344   -1.1115   -0.8133 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5398   -2.1052   -1.3660 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8132   -0.2492    0.1281 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4212   -0.3719    0.5532 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1551   -1.4524    0.2731 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2390   -0.3198    1.0725 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2495   -1.5807   -0.2607 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8489   -1.3899    0.8103 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6083   -0.1605   -2.0757 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9384   -0.6269   -2.7014 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4428    1.1375   -2.4903 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7315    1.6833   -1.0578 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3282    0.3548    1.7217 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8915    2.0509    1.5087 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2266    2.7744    1.9699 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5629    1.6281    0.6961 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4708    0.0657   -0.9954 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0695   -1.7002   -1.9818 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8841   -2.7541   -2.0561 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
 13 14  2  0
 14 15  1  0
 15 16  1  0
 15 17  2  0
 17 18  1  0
 18 19  2  0
  8  6  1  0
 17 11  1  0
 18  6  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  3 23  1  0
  3 24  1  0
  3 25  1  0
  4 26  1  0
  5 27  1  0
  5 28  1  0
  8 29  1  1
 12 30  1  0
 13 31  1  0
 14 32  1  0
 16 33  1  0
M  END


  Mrv1652309102222582D          

 19 21  0  0  1  0            999 V2000
    5.3329    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5079    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0954    0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0954    1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2704    1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  2  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
    2.8579    0.0000    0.0000 C   0  0  1  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   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 O   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
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    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
  2  4  2  0  0  0  0
  4  5  1  0  0  0  0
  6  5  1  6  0  0  0
  6  7  1  0  0  0  0
  8  7  1  1  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  2  0  0  0  0
 11 17  1  0  0  0  0
 17 18  1  0  0  0  0
  6 18  1  0  0  0  0
 18 19  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0305281

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)=CC[C@]12O[C@H]1C(=O)C1=CC=CC(O)=C1C2=O

> <INCHI_IDENTIFIER>
InChI=1S/C15H14O4/c1-8(2)6-7-15-13(18)11-9(4-3-5-10(11)16)12(17)14(15)19-15/h3-6,14,16H,7H2,1-2H3/t14-,15+/m0/s1

> <INCHI_KEY>
LFQYQHFKJJMVTR-LSDHHAIUSA-N

> <FORMULA>
C15H14O4

> <MOLECULAR_WEIGHT>
258.273

> <EXACT_MASS>
258.089208931

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
33

> <JCHEM_AVERAGE_POLARIZABILITY>
26.25285396741052

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <JCHEM_LOGP>
2.94043587

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.616084159813443

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.049964192754377

> <JCHEM_PKA_STRONGEST_BASIC>
-4.346265872061151

> <JCHEM_POLAR_SURFACE_AREA>
66.9

> <JCHEM_REFRACTIVITY>
70.0983

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 10-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-SEP-22         0                                  
HETATM    1  C   UNK     0       9.955   1.540   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.415   1.540   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.645   0.206   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.645   2.874   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.105   2.874   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       6.668   0.770   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       4.001  -2.310   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.000   0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       4.001   3.850   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8   18                                             
CONECT    7    6    8                                                       
CONECT    8    7    6    9                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   17                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   11   18                                                  
CONECT   18   17    6   19                                                  
CONECT   19   18                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   42    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₅H₁₄O₄

Average Mass

258.2730 Da

Monoisotopic Mass

258.08921 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

CC(C)=CC[C@]12O[C@H]1C(=O)C1=CC=CC(O)=C1C2=O

InChI Identifier

InChI=1S/C15H14O4/c1-8(2)6-7-15-13(18)11-9(4-3-5-10(11)16)12(17)14(15)19-15/h3-6,14,16H,7H2,1-2H3/t14-,15+/m0/s1

InChI Key

LFQYQHFKJJMVTR-LSDHHAIUSA-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
Diospyros maritima	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-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
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

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

28500773

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

70685624

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1as,7ar)-3-hydroxy-1a-(3-methylbut-2-en-1-yl)-7ah-naphtho[2,3-b]oxirene-2,7-dione (NP0305281)

MOL for NP0305281 ((1as,7ar)-3-hydroxy-1a-(3-methylbut-2-en-1-yl)-7ah-naphtho[2,3-b]oxirene-2,7-dione)

3D MOL for NP0305281 ((1as,7ar)-3-hydroxy-1a-(3-methylbut-2-en-1-yl)-7ah-naphtho[2,3-b]oxirene-2,7-dione)

3D SDF for NP0305281 ((1as,7ar)-3-hydroxy-1a-(3-methylbut-2-en-1-yl)-7ah-naphtho[2,3-b]oxirene-2,7-dione)

3D-SDF for NP0305281 ((1as,7ar)-3-hydroxy-1a-(3-methylbut-2-en-1-yl)-7ah-naphtho[2,3-b]oxirene-2,7-dione)

PDB for NP0305281 ((1as,7ar)-3-hydroxy-1a-(3-methylbut-2-en-1-yl)-7ah-naphtho[2,3-b]oxirene-2,7-dione)

3D PDB for NP0305281 ((1as,7ar)-3-hydroxy-1a-(3-methylbut-2-en-1-yl)-7ah-naphtho[2,3-b]oxirene-2,7-dione)

SMILES for NP0305281 ((1as,7ar)-3-hydroxy-1a-(3-methylbut-2-en-1-yl)-7ah-naphtho[2,3-b]oxirene-2,7-dione)

INCHI for NP0305281 ((1as,7ar)-3-hydroxy-1a-(3-methylbut-2-en-1-yl)-7ah-naphtho[2,3-b]oxirene-2,7-dione)

Structure for NP0305281 ((1as,7ar)-3-hydroxy-1a-(3-methylbut-2-en-1-yl)-7ah-naphtho[2,3-b]oxirene-2,7-dione)

3D Structure for NP0305281 ((1as,7ar)-3-hydroxy-1a-(3-methylbut-2-en-1-yl)-7ah-naphtho[2,3-b]oxirene-2,7-dione)