NP-MRD: Showing NP-Card for 2-Isoprenylemodin (NP0051616)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-04-27 22:55:10 UTC

Updated at

2022-04-27 22:55:10 UTC

NP-MRD ID

NP0051616

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-Isoprenylemodin

Description

2-Isoprenylemodin belongs to the class of organic compounds known as hydroxyanthraquinones. Hydroxyanthraquinones are compounds containing a hydroxyanthraquinone moiety, which consists of an anthracene bearing a quinone, and hydroxyl group. Thus, 2-isoprenylemodin is considered to be an aromatic polyketide. 2-Isoprenylemodin is found in Psorospermum febrifugum , Psorospermum glaberrimum, Psorospermum tenuifolium and Vismia guaramirangae. Based on a literature review very few articles have been published on 2-isoprenylemodin.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 43 45  0  0  0  0  0  0  0  0999 V2000
   -5.7698    0.4392    0.4591 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9298   -0.7819    0.3489 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4784   -1.9874    1.0901 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8111   -0.8475   -0.3202 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2256    0.2861   -1.0615 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8721    0.6385   -0.6072 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6073    1.7087    0.2061 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5900    2.5492    0.6683 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2922    2.0004    0.6132 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7557    1.2288    0.2116 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4872    0.1524   -0.6067 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7985   -0.1570   -1.0222 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9907   -1.2535   -1.8447 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5845   -0.6991   -1.0632 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3503   -1.6937   -1.8171 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9670   -0.4397   -0.6739 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0107   -1.2515   -1.1126 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7111   -2.3345   -1.9405 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3128   -0.9948   -0.7399 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5431    0.0877    0.0776 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9411    0.3880    0.4918 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5110    0.8985    0.5171 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1948    0.6448    0.1445 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1426    1.5221    0.6263 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3589    2.5104    1.3731 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8023    0.9872   -0.5092 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8342    0.1888    0.6808 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3438    1.0868    1.2690 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6769   -1.6142    2.1337 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7767   -2.8330    1.0645 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4472   -2.2065    0.5903 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2763   -1.7981   -0.3303 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1933   -0.0079   -2.1523 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8904    1.1680   -1.0406 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5482    2.4134    0.4311 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0909    2.8473    1.2558 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8419   -1.5892   -2.2197 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4656   -2.9269   -2.2615 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1369   -1.6206   -1.0751 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1087    1.5018    0.5572 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6265    0.0582   -0.3141 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1978   -0.0161    1.4738 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6812    1.7465    1.1560 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
  5  6  1  0
  6 12  2  0
 12 13  1  0
 12 11  1  0
 11 10  2  0
 10  9  1  0
  9  7  2  0
  7  8  1  0
 10 24  1  0
 24 25  2  0
 24 23  1  0
 23 22  2  0
 22 20  1  0
 20 21  1  0
 20 19  2  0
 19 17  1  0
 17 18  1  0
 17 16  2  0
 16 14  1  0
 14 15  2  0
  7  6  1  0
 16 23  1  0
 14 11  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  3 29  1  0
  3 30  1  0
  3 31  1  0
  4 32  1  0
  5 33  1  0
  5 34  1  0
 13 37  1  0
  9 36  1  0
  8 35  1  0
 22 43  1  0
 21 40  1  0
 21 41  1  0
 21 42  1  0
 19 39  1  0
 18 38  1  0
M  END

  Mrv1652304282200552D          

 25 27  0  0  0  0            999 V2000
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.0000    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
    2.8579   -0.0000    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
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 O   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
    1.4289    0.8250    0.0000 C   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
    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
    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
   -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 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    2.4750    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    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  6  7  1  0  0  0  0
  5  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
  4 12  1  0  0  0  0
 12 13  2  0  0  0  0
 11 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 10 17  1  0  0  0  0
 17 18  1  0  0  0  0
 16 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 15 24  1  0  0  0  0
  2 25  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0051616

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)=CCC1=C(O)C2=C(C=C1O)C(=O)C1=CC(C)=CC(O)=C1C2=O

> <INCHI_IDENTIFIER>
InChI=1S/C20H18O5/c1-9(2)4-5-11-14(21)8-13-17(19(11)24)20(25)16-12(18(13)23)6-10(3)7-15(16)22/h4,6-8,21-22,24H,5H2,1-3H3

> <INCHI_KEY>
WQTDARJAYXTHNU-UHFFFAOYSA-N

> <FORMULA>
C20H18O5

> <MOLECULAR_WEIGHT>
338.359

> <EXACT_MASS>
338.11542368

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
43

> <JCHEM_AVERAGE_POLARIZABILITY>
35.730504280018025

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1,3,8-trihydroxy-6-methyl-2-(3-methylbut-2-en-1-yl)-9,10-dihydroanthracene-9,10-dione

> <ALOGPS_LOGP>
3.36

> <JCHEM_LOGP>
5.549998498333334

> <ALOGPS_LOGS>
-4.10

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.231507585219294

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.114059848017672

> <JCHEM_PKA_STRONGEST_BASIC>
-5.412343164638693

> <JCHEM_POLAR_SURFACE_AREA>
94.83

> <JCHEM_REFRACTIVITY>
96.37770000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.67e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-isoprenylemodin

> <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       8.002   1.540   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.002  -0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.335  -0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       6.668   3.850   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       4.001   3.850   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.667   0.000   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  O   UNK     0       4.001  -2.310   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -2.667   4.620   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -4.001   3.850   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -2.667   6.160   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3   25                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   12                                                  
CONECT    5    4    6    8                                                  
CONECT    6    5    1    7                                                  
CONECT    7    6                                                            
CONECT    8    5    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   17                                                  
CONECT   11   10   12   14                                                  
CONECT   12   11    4   13                                                  
CONECT   13   12                                                            
CONECT   14   11   15                                                       
CONECT   15   14   16   24                                                  
CONECT   16   15   17   19                                                  
CONECT   17   16   10   18                                                  
CONECT   18   17                                                            
CONECT   19   16   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21                                                            
CONECT   24   15                                                            
CONECT   25    2                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   54    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₁₈O₅

Average Mass

338.3590 Da

Monoisotopic Mass

338.11542 Da

IUPAC Name

1,3,8-trihydroxy-6-methyl-2-(3-methylbut-2-en-1-yl)-9,10-dihydroanthracene-9,10-dione

Traditional Name

2-isoprenylemodin

CAS Registry Number

Not Available

SMILES

CC(C)=CCC1=C(O)C2=C(C=C1O)C(=O)C1=CC(C)=CC(O)=C1C2=O

InChI Identifier

InChI=1S/C20H18O5/c1-9(2)4-5-11-14(21)8-13-17(19(11)24)20(25)16-12(18(13)23)6-10(3)7-15(16)22/h4,6-8,21-22,24H,5H2,1-3H3

InChI Key

WQTDARJAYXTHNU-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, 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
Psorospermum febrifugum	Plant	KNApSAcK
Psorospermum glaberrimum	Plant	KNApSAcK
Psorospermum tenuifolium	LOTUS Database	35616633
Vismia guaramirangae	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hydroxyanthraquinones. Hydroxyanthraquinones are compounds containing a hydroxyanthraquinone moiety, which consists of an anthracene bearing a quinone, and hydroxyl group.

Kingdom

Super Class

Class

Sub Class

Direct Parent

Hydroxyanthraquinones

Alternative Parents

Substituents

Hydroxyanthraquinone
Aryl ketone
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Vinylogous acid
Ketone
Polyol
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

hydroxyanthraquinones (CHEBI:1177 )
Anthracenes and phenanthrenes (C10360 )
Anthraquinone type (C10360 )
Anthracenes and phenanthrenes (LMPK13040010 )

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	3.36	ALOGPS
logP	5.55	ChemAxon
logS	-4.1	ALOGPS
pKa (Strongest Acidic)	7.11	ChemAxon
pKa (Strongest Basic)	-5.4	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	94.83 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	96.38 m³·mol⁻¹	ChemAxon
Polarizability	35.73 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	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

C00002832

Chemspider ID

391092

KEGG Compound ID

C10360

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

442750

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 2-Isoprenylemodin (NP0051616)

MOL for NP0051616 (2-Isoprenylemodin)

3D MOL for NP0051616 (2-Isoprenylemodin)

3D SDF for NP0051616 (2-Isoprenylemodin)

3D-SDF for NP0051616 (2-Isoprenylemodin)

PDB for NP0051616 (2-Isoprenylemodin)

3D PDB for NP0051616 (2-Isoprenylemodin)

SMILES for NP0051616 (2-Isoprenylemodin)

INCHI for NP0051616 (2-Isoprenylemodin)

Structure for NP0051616 (2-Isoprenylemodin)

3D Structure for NP0051616 (2-Isoprenylemodin)