NP-MRD: Showing NP-Card for Emericellin (NP0066447)

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Record Information

Version

2.0

Created at

2022-04-28 10:42:46 UTC

Updated at

2022-04-28 10:42:47 UTC

NP-MRD ID

NP0066447

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Emericellin

Description

Emericellin, also known as variecoxanthone b, belongs to the class of organic compounds known as 4-prenylated xanthones. These are organic compounds containing a C5-isoprenoid group linked to a xanthone moiety at the 4-position. Xanthone is a tricyclic compound made up of two benzene rings linearly fused to each other through a pyran ring that carries a ketone group. Emericellin is an extremely weak basic (essentially neutral) compound (based on its pKa). Emericellin is found in Aspergillus nidulans, Aspergillus quadrilineatus, Aspergillus rugulosus, Aspergillus variecolor strain CBS 135-55, Emericella nidulans var.acristata and Aspergillus striatus. Emericellin was first documented in 2007 (PMID: 17277172). A xanthone that is xanthen-9-one bearing hydroxymethyl, 3,3-dimethylallyloxy, methyl, 3,3-dimethylallyl and hydroxy groups at positions 1, 2, 3, 5 and 8 respectively (PMID: 21351751).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 04121502112D          

 30 32  0  0  0  0            999 V2000
   -1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 O   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
    1.4289   -1.6500    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
    2.1434   -1.2375    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
    3.5724   -1.2375    0.0000 O   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
    5.0013   -1.2375    0.0000 C   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
    4.2868    0.0000    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
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  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  2  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 13 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  2  0  0  0  0
 12 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 24 26  1  0  0  0  0
 10 26  1  0  0  0  0
 26 27  2  0  0  0  0
  6 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
  2 30  1  0  0  0  0
M  END

     RDKit          3D

 58 60  0  0  0  0  0  0  0  0999 V2000
    6.0246   -0.5057    0.7997 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5844   -0.0688   -0.4899 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0917    0.0814   -0.6514 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8439    0.2019   -1.5216 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3696    0.1029   -1.5184 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8096   -0.3107   -0.3045 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4321   -0.4178   -0.1802 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7842   -1.5383   -0.5736 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5963   -2.6614   -1.1483 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4336   -1.6166   -0.4399 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2820   -0.5456    0.1005 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5806   -0.6824    0.2010 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3461    0.2571    0.6905 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7321    0.1312    0.8065 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3626   -1.1191    0.3561 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8299   -1.0249    0.5792 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6710   -1.1254   -0.4613 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1434   -1.0357   -0.2740 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1333   -1.3330   -1.8516 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4922    1.1523    1.3297 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8911    2.3181    1.7478 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4994    2.4543    1.6356 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8644    3.5969    2.0398 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7571    1.4219    1.1098 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3665    1.5971    1.0143 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1174    2.6595    1.4020 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4080    0.6030    0.5014 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7636    0.7113    0.3813 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5697    1.8300    0.8089 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1227    2.9548    1.3549 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3777    0.2715    1.2265 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8587   -0.6477    1.5563 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4942   -1.4710    0.6794 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4582   -0.9103   -0.9919 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5212    0.2770    0.3453 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3183    0.8424   -1.4037 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3496    0.5262   -2.4592 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1275   -0.7269   -2.2589 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9753    1.0531   -1.8980 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6515   -2.5795   -0.8022 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5609   -2.6408   -2.2421 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2120   -3.6283   -0.7183 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0599   -2.5293   -0.7642 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1188   -1.2817   -0.6937 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9646   -2.0129    0.9128 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2523   -0.8791    1.5465 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6735   -1.7952   -0.8845 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4361    0.0002   -0.5960 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4124   -1.1418    0.7955 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5461   -0.4345   -2.1544 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4955   -2.2463   -1.8813 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9574   -1.4637   -2.5528 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5750    1.0367    1.4128 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4622    3.1302    2.1599 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2869    4.4100    2.4341 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2470    1.3633    1.6476 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4232    2.0384    0.0631 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6658    3.3515    2.0839 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  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  2  3
 17 18  1  0
 17 19  1  0
 14 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  1  0
 22 24  2  0
 24 25  1  0
 25 26  2  0
 25 27  1  0
 27 28  2  0
 28 29  1  0
 29 30  1  0
 28  7  1  0
 27 11  1  0
 24 13  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
  3 34  1  0
  3 35  1  0
  3 36  1  0
  4 37  1  0
  5 38  1  0
  5 39  1  0
  9 40  1  0
  9 41  1  0
  9 42  1  0
 10 43  1  0
 15 44  1  0
 15 45  1  0
 16 46  1  0
 18 47  1  0
 18 48  1  0
 18 49  1  0
 19 50  1  0
 19 51  1  0
 19 52  1  0
 20 53  1  0
 21 54  1  0
 23 55  1  0
 29 56  1  0
 29 57  1  0
 30 58  1  0
M  END


  Mrv0541 04121502112D          

 30 32  0  0  0  0            999 V2000
   -1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 O   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
    1.4289   -1.6500    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
    2.1434   -1.2375    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
    3.5724   -1.2375    0.0000 O   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
    5.0013   -1.2375    0.0000 C   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
    4.2868    0.0000    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
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  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  2  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 13 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  2  0  0  0  0
 12 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 24 26  1  0  0  0  0
 10 26  1  0  0  0  0
 26 27  2  0  0  0  0
  6 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
  2 30  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0066447

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)=CCOC1=C(C)C=C2OC3=C(CC=C(C)C)C=CC(O)=C3C(=O)C2=C1CO

> <INCHI_IDENTIFIER>
InChI=1S/C25H28O5/c1-14(2)6-7-17-8-9-19(27)22-23(28)21-18(13-26)24(29-11-10-15(3)4)16(5)12-20(21)30-25(17)22/h6,8-10,12,26-27H,7,11,13H2,1-5H3

> <INCHI_KEY>
JZHBEPYIKRDWBE-UHFFFAOYSA-N

> <FORMULA>
C25H28O5

> <MOLECULAR_WEIGHT>
408.494

> <EXACT_MASS>
408.193674002

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
58

> <JCHEM_AVERAGE_POLARIZABILITY>
45.80308160405859

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
8-hydroxy-1-(hydroxymethyl)-3-methyl-5-(3-methylbut-2-en-1-yl)-2-[(3-methylbut-2-en-1-yl)oxy]-9H-xanthen-9-one

> <ALOGPS_LOGP>
4.34

> <JCHEM_LOGP>
5.984288344000001

> <ALOGPS_LOGS>
-5.20

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.352365998830912

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.377793356741568

> <JCHEM_PKA_STRONGEST_BASIC>
-3.0845167572409435

> <JCHEM_POLAR_SURFACE_AREA>
75.99

> <JCHEM_REFRACTIVITY>
120.47849999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.55e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
8-hydroxy-1-(hydroxymethyl)-3-methyl-5-(3-methylbut-2-en-1-yl)-2-[(3-methylbut-2-en-1-yl)oxy]xanthen-9-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 12-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-APR-15         0                                  
HETATM    1  C   UNK     0      -2.667  -7.700   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334  -6.930   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000  -7.700   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       1.334  -5.390   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       6.668  -2.310   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       9.336   2.310   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      10.669  -3.080   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      10.669  -4.620   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       9.336  -5.390   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       9.336  -6.930   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       6.668  -6.930   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       2.667  -7.700   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   30                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   27                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11   26                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   23                                                  
CONECT   13   12   14   19                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16                                                            
CONECT   19   13   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   12   24                                                  
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   10   27                                                  
CONECT   27   26    6   28                                                  
CONECT   28   27   29                                                       
CONECT   29   28                                                            
CONECT   30    2                                                            
MASTER        0    0    0    0    0    0    0    0   30    0   64    0
END

View in JSmol

Synonyms

Value	Source
Variecoxanthone b	ChEBI

Chemical Formula

C₂₅H₂₈O₅

Average Mass

408.4940 Da

Monoisotopic Mass

408.19367 Da

IUPAC Name

8-hydroxy-1-(hydroxymethyl)-3-methyl-5-(3-methylbut-2-en-1-yl)-2-[(3-methylbut-2-en-1-yl)oxy]-9H-xanthen-9-one

Traditional Name

8-hydroxy-1-(hydroxymethyl)-3-methyl-5-(3-methylbut-2-en-1-yl)-2-[(3-methylbut-2-en-1-yl)oxy]xanthen-9-one

CAS Registry Number

Not Available

SMILES

CC(C)=CCOC1=C(C)C=C2OC3=C(CC=C(C)C)C=CC(O)=C3C(=O)C2=C1CO

InChI Identifier

InChI=1S/C25H28O5/c1-14(2)6-7-17-8-9-19(27)22-23(28)21-18(13-26)24(29-11-10-15(3)4)16(5)12-20(21)30-25(17)22/h6,8-10,12,26-27H,7,11,13H2,1-5H3

InChI Key

JZHBEPYIKRDWBE-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
Aspergillus nidulans	Fungi	KNApSAcK
Aspergillus quadrilineatus	Fungi	KNApSAcK
Aspergillus rugulosus	Fungi	KNApSAcK
Aspergillus variecolor strain CBS 135-55	Fungi	KNApSAcK
Emericella nidulans var.acristata	-	KNApSAcK
Emericella striata	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 4-prenylated xanthones. These are organic compounds containing a C5-isoprenoid group linked to a xanthone moiety at the 4-position. Xanthone is a tricyclic compound made up of two benzene rings linearly fused to each other through a pyran ring that carries a ketone group.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzopyrans

Sub Class

1-benzopyrans

Direct Parent

4-prenylated xanthones

Alternative Parents

Substituents

4-prenylated xanthone
Chromone
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Pyranone
Pyran
Benzenoid
Heteroaromatic compound
Vinylogous acid
Ether
Oxacycle
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Alcohol
Organic oxide
Organic oxygen compound
Aromatic alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

aromatic ether (CHEBI:64512 )
phenols (CHEBI:64512 )
xanthones (CHEBI:64512 )

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	4.34	ALOGPS
logP	5.98	ChemAxon
logS	-5.2	ALOGPS
pKa (Strongest Acidic)	8.38	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	75.99 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	120.48 m³·mol⁻¹	ChemAxon
Polarizability	45.8 Å³	ChemAxon
Number of Rings	3	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

5491812

PDB ID

Not Available

ChEBI ID

64512

Good Scents ID

Not Available

References

General References

Sanchez JF, Entwistle R, Hung JH, Yaegashi J, Jain S, Chiang YM, Wang CC, Oakley BR: Genome-based deletion analysis reveals the prenyl xanthone biosynthesis pathway in Aspergillus nidulans. J Am Chem Soc. 2011 Mar 23;133(11):4010-7. doi: 10.1021/ja1096682. Epub 2011 Feb 25. [PubMed:21351751 ]
Marquez-Fernandez O, Trigos A, Ramos-Balderas JL, Viniegra-Gonzalez G, Deising HB, Aguirre J: Phosphopantetheinyl transferase CfwA/NpgA is required for Aspergillus nidulans secondary metabolism and asexual development. Eukaryot Cell. 2007 Apr;6(4):710-20. doi: 10.1128/EC.00362-06. Epub 2007 Feb 2. [PubMed:17277172 ]

Showing NP-Card for Emericellin (NP0066447)

MOL for NP0066447 (Emericellin)

3D MOL for NP0066447 (Emericellin)

3D SDF for NP0066447 (Emericellin)

3D-SDF for NP0066447 (Emericellin)

PDB for NP0066447 (Emericellin)

3D PDB for NP0066447 (Emericellin)

SMILES for NP0066447 (Emericellin)

INCHI for NP0066447 (Emericellin)

Structure for NP0066447 (Emericellin)

3D Structure for NP0066447 (Emericellin)