NP-MRD: Showing NP-Card for 9-(hydroxymethyl)-6-methyl-3-methylidene-2,7-dioxo-3ah,4h,5h,8h,9h,9ah,9bh-azuleno[4,5-b]furan-4-yl 2-(4-hydroxyphenyl)acetate (NP0243403)

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Record Information

Version

2.0

Created at

2022-09-07 03:56:38 UTC

Updated at

2022-09-07 03:56:38 UTC

NP-MRD ID

NP0243403

Secondary Accession Numbers

None

Natural Product Identification

Common Name

9-(hydroxymethyl)-6-methyl-3-methylidene-2,7-dioxo-3ah,4h,5h,8h,9h,9ah,9bh-azuleno[4,5-b]furan-4-yl 2-(4-hydroxyphenyl)acetate

Description

9-(Hydroxymethyl)-6-methyl-3-methylidene-2,7-dioxo-2H,3H,3aH,4H,5H,7H,8H,9H,9aH,9bH-azuleno[4,5-b]furan-4-yl 2-(4-hydroxyphenyl)acetate belongs to the class of organic compounds known as 1-hydroxy-2-unsubstituted benzenoids. These are phenols that are unsubstituted at the 2-position. 9-(hydroxymethyl)-6-methyl-3-methylidene-2,7-dioxo-3ah,4h,5h,8h,9h,9ah,9bh-azuleno[4,5-b]furan-4-yl 2-(4-hydroxyphenyl)acetate is found in Cichorium spinosum. 9-(Hydroxymethyl)-6-methyl-3-methylidene-2,7-dioxo-2H,3H,3aH,4H,5H,7H,8H,9H,9aH,9bH-azuleno[4,5-b]furan-4-yl 2-(4-hydroxyphenyl)acetate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004231514142D          

 30 33  0  0  0  0            999 V2000
    3.6754    3.7963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0304    3.2819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2140    2.4776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6996    1.8326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1541    1.1441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8642    0.3717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3882   -0.2656    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9493    1.3636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9864    2.1877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6749    2.6422    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8746    1.8326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4201    1.1441    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6248    1.3636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0202    0.8492    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5878    2.1877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1007    2.6422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3602    2.4776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5438    3.2819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2871    3.6399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8988    3.7963    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0217    4.6121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7897    4.9135    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3767    5.1265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4997    5.9423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1453    6.4566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0224    7.2724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7456    7.5738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8686    8.3896    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3906    7.0594    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2677    6.2437    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  1  0  0  0  0
  5  8  1  0  0  0  0
  8  9  1  0  0  0  0
  3  9  1  0  0  0  0
  9 10  2  0  0  0  0
  4 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 11 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
  2 19  1  0  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 27 29  1  0  0  0  0
 29 30  2  0  0  0  0
 24 30  1  0  0  0  0
M  END

     RDKit          3D

 54 57  0  0  0  0  0  0  0  0999 V2000
    0.0716    1.4029   -2.6681 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6872    1.3903   -1.6072 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2953    2.5337   -0.9613 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2382    3.7549   -1.2390 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0337    2.0454    0.1297 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6664    0.7352    0.4438 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0924    0.2043   -0.8321 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0647   -0.7339   -0.5677 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8458   -0.2683    0.5160 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1977   -0.0201    0.3458 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7127   -0.2157   -0.7839 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0681    0.4685    1.4423 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4641    0.6476    0.9830 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8583    1.8686    0.4611 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1559    2.0570    0.0269 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0943    1.0472    0.0969 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4136    1.2245   -0.3398 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7084   -0.1855    0.6204 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4043   -0.3766    1.0574 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5179   -2.0757   -0.1560 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9718   -2.1744   -0.4451 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4281   -3.3040   -1.2922 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9204   -1.3612   -0.0280 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3136   -1.5935   -0.3953 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7805   -2.3652   -1.2456 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0991   -0.6719    0.5010 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1632    0.5315    0.5063 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.5786    1.5356    1.5594 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8107    2.0632    1.1268 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8422   -0.1293    0.8322 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5062    0.5067   -3.1157 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3388    2.3215   -3.2033 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8718    0.7214    1.2476 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9031   -0.2920   -1.4141 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7194   -0.8348   -1.4615 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1056   -0.2750    2.2907 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6963    1.4252    1.8315 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1082    2.6521    0.4130 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4242    3.0244   -0.3741 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6569    2.1299   -0.7128 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4438   -0.9652    0.6714 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1217   -1.3380    1.4604 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3513   -2.2770    0.9364 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0433   -2.8643   -0.7035 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5342   -3.9552   -1.4864 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7829   -2.9868   -2.2874 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1492   -3.9663   -0.7585 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0839   -1.1192    1.4938 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0822   -0.4458    0.0876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0914    0.9976   -0.4888 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8514    2.3590    1.5571 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6586    1.0391    2.5334 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5741    1.5175    1.4947 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8503   -0.3783    1.9005 H   0  0  0  0  0  0  0  0  0  0  0  0
 22 21  1  0
 21 23  2  0
 23 30  1  0
 30 27  1  0
 27 28  1  0
 28 29  1  0
 27 26  1  0
 26 24  1  0
 24 25  2  0
 30  6  1  0
  6  5  1  0
  5  3  1  0
  3  4  2  0
  3  2  1  0
  2  1  2  3
  2  7  1  0
  7  8  1  0
  8 20  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  2  0
 20 21  1  0
 19 13  1  0
 24 23  1  0
  7  6  1  0
 22 45  1  0
 22 46  1  0
 22 47  1  0
 30 54  1  1
 27 50  1  6
 28 51  1  0
 28 52  1  0
 29 53  1  0
 26 48  1  0
 26 49  1  0
  6 33  1  1
  1 31  1  0
  1 32  1  0
  7 34  1  6
  8 35  1  6
 20 43  1  0
 20 44  1  0
 12 36  1  0
 12 37  1  0
 14 38  1  0
 15 39  1  0
 17 40  1  0
 18 41  1  0
 19 42  1  0
M  END


  Mrv1533004231514142D          

 30 33  0  0  0  0            999 V2000
    3.6754    3.7963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0304    3.2819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2140    2.4776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6996    1.8326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1541    1.1441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8642    0.3717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3882   -0.2656    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9493    1.3636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9864    2.1877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6749    2.6422    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8746    1.8326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4201    1.1441    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6248    1.3636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0202    0.8492    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5878    2.1877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1007    2.6422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3602    2.4776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5438    3.2819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2871    3.6399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8988    3.7963    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0217    4.6121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7897    4.9135    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3767    5.1265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4997    5.9423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1453    6.4566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0224    7.2724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7456    7.5738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8686    8.3896    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3906    7.0594    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2677    6.2437    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  1  0  0  0  0
  5  8  1  0  0  0  0
  8  9  1  0  0  0  0
  3  9  1  0  0  0  0
  9 10  2  0  0  0  0
  4 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 11 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
  2 19  1  0  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 27 29  1  0  0  0  0
 29 30  2  0  0  0  0
 24 30  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0243403

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1=C2C(C(CO)CC2=O)C2OC(=O)C(=C)C2C(C1)OC(=O)CC1=CC=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C23H24O7/c1-11-7-17(29-18(27)8-13-3-5-15(25)6-4-13)20-12(2)23(28)30-22(20)21-14(10-24)9-16(26)19(11)21/h3-6,14,17,20-22,24-25H,2,7-10H2,1H3

> <INCHI_KEY>
PUUMACFYOWTVCM-UHFFFAOYSA-N

> <FORMULA>
C23H24O7

> <MOLECULAR_WEIGHT>
412.438

> <EXACT_MASS>
412.152203113

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
54

> <JCHEM_AVERAGE_POLARIZABILITY>
42.10822616612544

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
9-(hydroxymethyl)-6-methyl-3-methylidene-2,7-dioxo-2H,3H,3aH,4H,5H,7H,8H,9H,9aH,9bH-azuleno[4,5-b]furan-4-yl 2-(4-hydroxyphenyl)acetate

> <ALOGPS_LOGP>
1.87

> <JCHEM_LOGP>
1.9220393936666675

> <ALOGPS_LOGS>
-3.42

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.426295204921654

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.496423242684362

> <JCHEM_PKA_STRONGEST_BASIC>
-2.610743987347594

> <JCHEM_POLAR_SURFACE_AREA>
110.13000000000001

> <JCHEM_REFRACTIVITY>
106.96969999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.57e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
9-(hydroxymethyl)-6-methyl-3-methylidene-2,7-dioxo-3aH,4H,5H,8H,9H,9aH,9bH-azuleno[4,5-b]furan-4-yl 2-(4-hydroxyphenyl)acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-APR-15         0                                  
HETATM    1  C   UNK     0       6.861   7.086   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.657   6.126   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.999   4.625   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.039   3.421   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.888   2.136   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.346   0.694   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       6.325  -0.496   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       7.372   2.545   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.441   4.084   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       8.726   4.932   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       3.499   3.421   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       2.651   2.136   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       1.166   2.545   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -0.038   1.585   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       1.097   4.084   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.188   4.932   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.539   4.625   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.882   6.126   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.269   6.794   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       1.678   7.086   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       1.907   8.609   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       3.341   9.172   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       0.703   9.569   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       0.933  11.092   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -0.271  12.052   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -0.042  13.575   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       1.392  14.138   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       1.621  15.661   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       2.596  13.178   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       2.366  11.655   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   19                                                  
CONECT    3    2    4    9                                                  
CONECT    4    3    5   11                                                  
CONECT    5    4    6    8                                                  
CONECT    6    5    7                                                       
CONECT    7    6                                                            
CONECT    8    5    9                                                       
CONECT    9    8    3   10                                                  
CONECT   10    9                                                            
CONECT   11    4   12   17                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   11   18                                                  
CONECT   18   17   19   20                                                  
CONECT   19   18    2                                                       
CONECT   20   18   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24                                                       
CONECT   24   23   25   30                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30                                                       
CONECT   30   29   24                                                       
MASTER        0    0    0    0    0    0    0    0   30    0   66    0
END

View in JSmol

Synonyms

Value	Source
9-(Hydroxymethyl)-6-methyl-3-methylidene-2,7-dioxo-2H,3H,3ah,4H,5H,7H,8H,9H,9ah,9BH-azuleno[4,5-b]furan-4-yl 2-(4-hydroxyphenyl)acetic acid	Generator

Chemical Formula

C₂₃H₂₄O₇

Average Mass

412.4380 Da

Monoisotopic Mass

412.15220 Da

IUPAC Name

9-(hydroxymethyl)-6-methyl-3-methylidene-2,7-dioxo-2H,3H,3aH,4H,5H,7H,8H,9H,9aH,9bH-azuleno[4,5-b]furan-4-yl 2-(4-hydroxyphenyl)acetate

Traditional Name

9-(hydroxymethyl)-6-methyl-3-methylidene-2,7-dioxo-3aH,4H,5H,8H,9H,9aH,9bH-azuleno[4,5-b]furan-4-yl 2-(4-hydroxyphenyl)acetate

CAS Registry Number

Not Available

SMILES

CC1=C2C(C(CO)CC2=O)C2OC(=O)C(=C)C2C(C1)OC(=O)CC1=CC=C(O)C=C1

InChI Identifier

InChI=1S/C23H24O7/c1-11-7-17(29-18(27)8-13-3-5-15(25)6-4-13)20-12(2)23(28)30-22(20)21-14(10-24)9-16(26)19(11)21/h3-6,14,17,20-22,24-25H,2,7-10H2,1H3

InChI Key

PUUMACFYOWTVCM-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
Cichorium spinosum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 1-hydroxy-2-unsubstituted benzenoids. These are phenols that are unsubstituted at the 2-position.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Phenols

Sub Class

1-hydroxy-2-unsubstituted benzenoids

Direct Parent

1-hydroxy-2-unsubstituted benzenoids

Alternative Parents

Substituents

1-hydroxy-2-unsubstituted benzenoid
Monocyclic benzene moiety
Dicarboxylic acid or derivatives
Gamma butyrolactone
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tetrahydrofuran
Carboxylic acid ester
Ketone
Lactone
Carboxylic acid derivative
Oxacycle
Organoheterocyclic compound
Hydrocarbon derivative
Organic oxide
Alcohol
Carbonyl group
Organic oxygen compound
Primary alcohol
Organooxygen 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	1.87	ALOGPS
logP	1.92	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	9.5	ChemAxon
pKa (Strongest Basic)	-2.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	110.13 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	106.97 m³·mol⁻¹	ChemAxon
Polarizability	42.11 Å³	ChemAxon
Number of Rings	4	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

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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 9-(hydroxymethyl)-6-methyl-3-methylidene-2,7-dioxo-3ah,4h,5h,8h,9h,9ah,9bh-azuleno[4,5-b]furan-4-yl 2-(4-hydroxyphenyl)acetate (NP0243403)

MOL for NP0243403 (9-(hydroxymethyl)-6-methyl-3-methylidene-2,7-dioxo-3ah,4h,5h,8h,9h,9ah,9bh-azuleno[4,5-b]furan-4-yl 2-(4-hydroxyphenyl)acetate)

3D MOL for NP0243403 (9-(hydroxymethyl)-6-methyl-3-methylidene-2,7-dioxo-3ah,4h,5h,8h,9h,9ah,9bh-azuleno[4,5-b]furan-4-yl 2-(4-hydroxyphenyl)acetate)

3D SDF for NP0243403 (9-(hydroxymethyl)-6-methyl-3-methylidene-2,7-dioxo-3ah,4h,5h,8h,9h,9ah,9bh-azuleno[4,5-b]furan-4-yl 2-(4-hydroxyphenyl)acetate)

3D-SDF for NP0243403 (9-(hydroxymethyl)-6-methyl-3-methylidene-2,7-dioxo-3ah,4h,5h,8h,9h,9ah,9bh-azuleno[4,5-b]furan-4-yl 2-(4-hydroxyphenyl)acetate)

PDB for NP0243403 (9-(hydroxymethyl)-6-methyl-3-methylidene-2,7-dioxo-3ah,4h,5h,8h,9h,9ah,9bh-azuleno[4,5-b]furan-4-yl 2-(4-hydroxyphenyl)acetate)

3D PDB for NP0243403 (9-(hydroxymethyl)-6-methyl-3-methylidene-2,7-dioxo-3ah,4h,5h,8h,9h,9ah,9bh-azuleno[4,5-b]furan-4-yl 2-(4-hydroxyphenyl)acetate)

SMILES for NP0243403 (9-(hydroxymethyl)-6-methyl-3-methylidene-2,7-dioxo-3ah,4h,5h,8h,9h,9ah,9bh-azuleno[4,5-b]furan-4-yl 2-(4-hydroxyphenyl)acetate)

INCHI for NP0243403 (9-(hydroxymethyl)-6-methyl-3-methylidene-2,7-dioxo-3ah,4h,5h,8h,9h,9ah,9bh-azuleno[4,5-b]furan-4-yl 2-(4-hydroxyphenyl)acetate)

Structure for NP0243403 (9-(hydroxymethyl)-6-methyl-3-methylidene-2,7-dioxo-3ah,4h,5h,8h,9h,9ah,9bh-azuleno[4,5-b]furan-4-yl 2-(4-hydroxyphenyl)acetate)

3D Structure for NP0243403 (9-(hydroxymethyl)-6-methyl-3-methylidene-2,7-dioxo-3ah,4h,5h,8h,9h,9ah,9bh-azuleno[4,5-b]furan-4-yl 2-(4-hydroxyphenyl)acetate)