NP-MRD: Showing NP-Card for 6a,9-dihydroxy-9-methyl-3,6-dimethylidene-2-oxo-3ah,4h,5h,9ah,9bh-azuleno[4,5-b]furan-4-yl 4-(acetyloxy)-2-methylbut-2-enoate (NP0165294)

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Record Information

Version

2.0

Created at

2022-09-03 00:23:10 UTC

Updated at

2022-09-03 00:23:10 UTC

NP-MRD ID

NP0165294

Secondary Accession Numbers

None

Natural Product Identification

Common Name

6a,9-dihydroxy-9-methyl-3,6-dimethylidene-2-oxo-3ah,4h,5h,9ah,9bh-azuleno[4,5-b]furan-4-yl 4-(acetyloxy)-2-methylbut-2-enoate

Description

6A,9-dihydroxy-9-methyl-3,6-dimethylidene-2-oxo-2H,3H,3aH,4H,5H,6H,6aH,9H,9aH,9bH-azuleno[4,5-b]furan-4-yl 4-(acetyloxy)-2-methylbut-2-enoate belongs to the class of organic compounds known as guaianolides and derivatives. These are diterpene lactones with a structure characterized by the presence of a gamma-lactone fused to a guaiane, forming 3,6,9-trimethyl-azuleno[4,5-b]furan-2-one or a derivative. 6a,9-dihydroxy-9-methyl-3,6-dimethylidene-2-oxo-3ah,4h,5h,9ah,9bh-azuleno[4,5-b]furan-4-yl 4-(acetyloxy)-2-methylbut-2-enoate is found in Calea jamaicensis. 6A,9-dihydroxy-9-methyl-3,6-dimethylidene-2-oxo-2H,3H,3aH,4H,5H,6H,6aH,9H,9aH,9bH-azuleno[4,5-b]furan-4-yl 4-(acetyloxy)-2-methylbut-2-enoate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004261513022D          

 30 32  0  0  0  0            999 V2000
    0.4219    6.5960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2990    5.7802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4690    5.4788    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9440    5.2658    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8210    4.4500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4660    3.9357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3431    3.1199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5751    2.8185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9881    2.6055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7560    2.9069    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8651    1.7897    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5101    1.2753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2534    1.6333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9967    1.2753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6417    1.7897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1803    0.4710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8016    1.0138    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9527    0.1811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9157   -0.6430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1204   -0.8625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4218   -1.6305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3881   -1.2426    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6659   -0.1740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8409   -0.1740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3864   -0.8625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5912   -0.6430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9461   -1.1574    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5541    0.1811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8656    0.6356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3265    0.4710    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
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  6  5  1  4  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
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 20 23  1  0  0  0  0
 16 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 26 28  1  0  0  0  0
 28 29  2  0  0  0  0
 28 30  1  0  0  0  0
 12 30  1  0  0  0  0
 24 30  1  0  0  0  0
M  END

     RDKit          3D

 56 58  0  0  0  0  0  0  0  0999 V2000
    0.6541    2.2479    1.3519 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5324    1.6818    1.3762 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3722    1.5259    2.5536 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9941    1.7053    3.7604 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6622    1.1460    2.1271 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4572    0.4538    0.9299 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2532    1.0973    0.2478 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4753    0.0506   -0.4942 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9092    0.1827   -0.3734 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7008   -0.8030    0.1894 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1050   -1.8324    0.5900 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1681   -0.6602    0.3161 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8687    0.5374   -0.1492 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8392   -1.6512    0.8656 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2932   -1.6968    1.0781 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9599   -0.5565    0.6351 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3105   -0.3441    0.7141 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9760    0.8964    0.2243 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0387   -1.2326    1.2234 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9233    0.0226   -1.9522 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3815   -0.0582   -2.0663 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9125    0.3826   -3.1922 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3397   -0.5687   -1.0753 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8923   -1.7508   -0.4679 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6827   -0.8565   -1.6094 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5776   -0.5153   -0.6981 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9204    0.0349    0.5321 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.8435   -1.0041    1.5932 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6571    1.1514    0.9147 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5998    0.4969   -0.0135 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0987    2.6526    2.2558 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2431    2.3418    0.4508 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1403   -0.6140    1.1174 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6771    1.8714   -0.4460 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7504   -0.9373   -0.0709 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0984    1.2216   -0.5793 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3853    1.1163    0.6429 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5611    0.2807   -0.9856 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2411   -2.5266    1.1944 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6782   -2.6083    0.5440 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5357   -1.8611    2.1535 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8720    1.7372    0.9515 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4145    1.2099   -0.6872 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.0362    0.7475    0.0100 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4916   -0.8620   -2.4719 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5808    0.9452   -2.4926 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2954    0.7887   -4.0022 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9842    0.3463   -3.3222 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0589   -2.5119   -1.0594 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9238   -1.2927   -2.6117 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6488   -0.6164   -0.8158 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8867   -1.5188    1.6258 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6127   -1.7922    1.3420 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1547   -0.6219    2.5886 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6207    0.9681    0.7692 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6845    1.4527   -0.5629 H   0  0  0  0  0  0  0  0  0  0  0  0
 18 17  1  0
 17 19  2  0
 17 16  1  0
 16 15  1  0
 15 14  1  0
 14 12  2  0
 12 13  1  0
 12 10  1  0
 10 11  2  0
 10  9  1  0
  9  8  1  0
  8 20  1  0
 20 21  1  0
 21 22  2  3
 21 23  1  0
 23 24  1  1
 23 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  1  0
 27 29  1  1
 27 30  1  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
 30 23  1  0
  7  6  1  0
 18 42  1  0
 18 43  1  0
 18 44  1  0
 15 40  1  0
 15 41  1  0
 14 39  1  0
 13 36  1  0
 13 37  1  0
 13 38  1  0
  8 35  1  1
 20 45  1  0
 20 46  1  0
 22 47  1  0
 22 48  1  0
 24 49  1  0
 25 50  1  0
 26 51  1  0
 28 52  1  0
 28 53  1  0
 28 54  1  0
 29 55  1  0
 30 56  1  6
  6 33  1  1
  1 31  1  0
  1 32  1  0
  7 34  1  6
M  END


  Mrv1533004261513022D          

 30 32  0  0  0  0            999 V2000
    0.4219    6.5960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2990    5.7802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4690    5.4788    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9440    5.2658    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8210    4.4500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4660    3.9357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3431    3.1199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5751    2.8185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9881    2.6055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7560    2.9069    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8651    1.7897    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5101    1.2753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2534    1.6333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9967    1.2753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6417    1.7897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1803    0.4710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8016    1.0138    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9527    0.1811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9157   -0.6430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1204   -0.8625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4218   -1.6305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3881   -1.2426    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6659   -0.1740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8409   -0.1740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3864   -0.8625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5912   -0.6430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9461   -1.1574    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5541    0.1811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8656    0.6356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3265    0.4710    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
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  6  5  1  4  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
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 20 23  1  0  0  0  0
 16 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 26 28  1  0  0  0  0
 28 29  2  0  0  0  0
 28 30  1  0  0  0  0
 12 30  1  0  0  0  0
 24 30  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0165294

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)OCC=C(C)C(=O)OC1CC(=C)C2(O)C=CC(C)(O)C2C2OC(=O)C(=C)C12

> <INCHI_IDENTIFIER>
InChI=1S/C22H26O8/c1-11(6-9-28-14(4)23)19(24)29-15-10-12(2)22(27)8-7-21(5,26)18(22)17-16(15)13(3)20(25)30-17/h6-8,15-18,26-27H,2-3,9-10H2,1,4-5H3

> <INCHI_KEY>
PZTCNOMGZILQIK-UHFFFAOYSA-N

> <FORMULA>
C22H26O8

> <MOLECULAR_WEIGHT>
418.442

> <EXACT_MASS>
418.162767797

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
56

> <JCHEM_AVERAGE_POLARIZABILITY>
42.024732170630145

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
6a,9-dihydroxy-9-methyl-3,6-dimethylidene-2-oxo-2H,3H,3aH,4H,5H,6H,6aH,9H,9aH,9bH-azuleno[4,5-b]furan-4-yl 4-(acetyloxy)-2-methylbut-2-enoate

> <ALOGPS_LOGP>
1.26

> <JCHEM_LOGP>
1.1510991380000009

> <ALOGPS_LOGS>
-2.80

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.391145365148585

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.375556378446802

> <JCHEM_PKA_STRONGEST_BASIC>
-3.145924440963258

> <JCHEM_POLAR_SURFACE_AREA>
119.36000000000001

> <JCHEM_REFRACTIVITY>
106.15680000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.67e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6a,9-dihydroxy-9-methyl-3,6-dimethylidene-2-oxo-3aH,4H,5H,9aH,9bH-azuleno[4,5-b]furan-4-yl 4-(acetyloxy)-2-methylbut-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 26-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-APR-15         0                                  
HETATM    1  C   UNK     0       0.788  12.312   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.558  10.790   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -0.876  10.227   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       1.762   9.830   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       1.533   8.307   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.737   7.347   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.507   5.824   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.073   5.261   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.711   4.864   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       5.145   5.426   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       3.482   3.341   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       4.686   2.381   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.073   3.049   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.461   2.381   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.665   3.341   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.803   0.879   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       8.963   1.892   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       9.245   0.338   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       9.176  -1.200   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       7.691  -1.610   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       8.254  -3.044   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       6.325  -2.319   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       6.843  -0.325   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       5.303  -0.325   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       4.455  -1.610   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       2.970  -1.200   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       1.766  -2.161   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       2.901   0.338   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       1.616   1.186   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       4.343   0.879   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13   30                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   18   23                                             
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   22   23                                             
CONECT   21   20                                                            
CONECT   22   20                                                            
CONECT   23   20   16   24                                                  
CONECT   24   23   25   30                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   12   24                                                  
MASTER        0    0    0    0    0    0    0    0   30    0   64    0
END

View in JSmol

Synonyms

Value	Source
6a,9-Dihydroxy-9-methyl-3,6-dimethylidene-2-oxo-2H,3H,3ah,4H,5H,6H,6ah,9H,9ah,9BH-azuleno[4,5-b]furan-4-yl 4-(acetyloxy)-2-methylbut-2-enoic acid	Generator

Chemical Formula

C₂₂H₂₆O₈

Average Mass

418.4420 Da

Monoisotopic Mass

418.16277 Da

IUPAC Name

6a,9-dihydroxy-9-methyl-3,6-dimethylidene-2-oxo-2H,3H,3aH,4H,5H,6H,6aH,9H,9aH,9bH-azuleno[4,5-b]furan-4-yl 4-(acetyloxy)-2-methylbut-2-enoate

Traditional Name

6a,9-dihydroxy-9-methyl-3,6-dimethylidene-2-oxo-3aH,4H,5H,9aH,9bH-azuleno[4,5-b]furan-4-yl 4-(acetyloxy)-2-methylbut-2-enoate

CAS Registry Number

Not Available

SMILES

CC(=O)OCC=C(C)C(=O)OC1CC(=C)C2(O)C=CC(C)(O)C2C2OC(=O)C(=C)C12

InChI Identifier

InChI=1S/C22H26O8/c1-11(6-9-28-14(4)23)19(24)29-15-10-12(2)22(27)8-7-21(5,26)18(22)17-16(15)13(3)20(25)30-17/h6-8,15-18,26-27H,2-3,9-10H2,1,4-5H3

InChI Key

PZTCNOMGZILQIK-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
Calea jamaicensis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as guaianolides and derivatives. These are diterpene lactones with a structure characterized by the presence of a gamma-lactone fused to a guaiane, forming 3,6,9-trimethyl-azuleno[4,5-b]furan-2-one or a derivative.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Guaianolides and derivatives

Alternative Parents

Substituents

Guaianolide-skeleton
Guaiane sesquiterpenoid
Sesquiterpenoid
Tricarboxylic acid or derivatives
Fatty acid ester
Fatty acyl
Gamma butyrolactone
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Cyclic alcohol
Tetrahydrofuran
Tertiary alcohol
Carboxylic acid ester
Lactone
Oxacycle
Organoheterocyclic compound
Carboxylic acid derivative
Organic oxide
Organic oxygen compound
Hydrocarbon derivative
Alcohol
Carbonyl group
Organooxygen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic 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	1.26	ALOGPS
logP	1.15	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	13.38	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	119.36 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	106.16 m³·mol⁻¹	ChemAxon
Polarizability	42.02 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	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

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 6a,9-dihydroxy-9-methyl-3,6-dimethylidene-2-oxo-3ah,4h,5h,9ah,9bh-azuleno[4,5-b]furan-4-yl 4-(acetyloxy)-2-methylbut-2-enoate (NP0165294)

MOL for NP0165294 (6a,9-dihydroxy-9-methyl-3,6-dimethylidene-2-oxo-3ah,4h,5h,9ah,9bh-azuleno[4,5-b]furan-4-yl 4-(acetyloxy)-2-methylbut-2-enoate)

3D MOL for NP0165294 (6a,9-dihydroxy-9-methyl-3,6-dimethylidene-2-oxo-3ah,4h,5h,9ah,9bh-azuleno[4,5-b]furan-4-yl 4-(acetyloxy)-2-methylbut-2-enoate)

3D SDF for NP0165294 (6a,9-dihydroxy-9-methyl-3,6-dimethylidene-2-oxo-3ah,4h,5h,9ah,9bh-azuleno[4,5-b]furan-4-yl 4-(acetyloxy)-2-methylbut-2-enoate)

3D-SDF for NP0165294 (6a,9-dihydroxy-9-methyl-3,6-dimethylidene-2-oxo-3ah,4h,5h,9ah,9bh-azuleno[4,5-b]furan-4-yl 4-(acetyloxy)-2-methylbut-2-enoate)

PDB for NP0165294 (6a,9-dihydroxy-9-methyl-3,6-dimethylidene-2-oxo-3ah,4h,5h,9ah,9bh-azuleno[4,5-b]furan-4-yl 4-(acetyloxy)-2-methylbut-2-enoate)

3D PDB for NP0165294 (6a,9-dihydroxy-9-methyl-3,6-dimethylidene-2-oxo-3ah,4h,5h,9ah,9bh-azuleno[4,5-b]furan-4-yl 4-(acetyloxy)-2-methylbut-2-enoate)

SMILES for NP0165294 (6a,9-dihydroxy-9-methyl-3,6-dimethylidene-2-oxo-3ah,4h,5h,9ah,9bh-azuleno[4,5-b]furan-4-yl 4-(acetyloxy)-2-methylbut-2-enoate)

INCHI for NP0165294 (6a,9-dihydroxy-9-methyl-3,6-dimethylidene-2-oxo-3ah,4h,5h,9ah,9bh-azuleno[4,5-b]furan-4-yl 4-(acetyloxy)-2-methylbut-2-enoate)

Structure for NP0165294 (6a,9-dihydroxy-9-methyl-3,6-dimethylidene-2-oxo-3ah,4h,5h,9ah,9bh-azuleno[4,5-b]furan-4-yl 4-(acetyloxy)-2-methylbut-2-enoate)

3D Structure for NP0165294 (6a,9-dihydroxy-9-methyl-3,6-dimethylidene-2-oxo-3ah,4h,5h,9ah,9bh-azuleno[4,5-b]furan-4-yl 4-(acetyloxy)-2-methylbut-2-enoate)