NP-MRD: Showing NP-Card for Flagranone A (NP0003142)

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Record Information

Version

2.0

Created at

2020-12-09 00:31:12 UTC

Updated at

2021-07-15 16:45:37 UTC

NP-MRD ID

NP0003142

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Flagranone A

Provided By

NPAtlas

Description

(2E,4E,6E)-1-{4-[(acetyloxy)methyl]-2,5-dioxo-7-oxabicyclo[4.1.0]Hept-3-en-1-yl}-3,7,11-trimethyldodeca-2,4,6,10-tetraen-1-yl acetate belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. Flagranone A is found in Arthrobotrys flagrans. Based on a literature review very few articles have been published on (2E,4E,6E)-1-{4-[(acetyloxy)methyl]-2,5-dioxo-7-oxabicyclo[4.1.0]Hept-3-en-1-yl}-3,7,11-trimethyldodeca-2,4,6,10-tetraen-1-yl acetate.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242117453D          

 65 66  0  0  0  0            999 V2000
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    8.5848    0.1545    0.8224 O   0  0  0  0  0  0  0  0  0  0  0  0
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    6.2212   -0.3004    0.5911 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1652306242117453D          

 65 66  0  0  0  0            999 V2000
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    0.8200    0.8292    1.1755 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1510   -0.2234    0.5067 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2829   -0.7184   -0.0997 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5759   -0.4916    0.4654 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7032   -0.9065   -0.0438 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7089   -1.6848   -1.2998 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9947   -0.5141    0.6096 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.7822    0.2772   -0.4305 C   0  0  2  0  0  0  0  0  0  0  0  0
   -8.0019    0.7999    0.1744 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2445    0.6334   -0.1796 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.3732    1.2611    0.5810 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5994   -0.1927   -1.3586 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9114    0.9343   -1.2634 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4119    2.1558   -0.8914 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7060    3.2412   -1.8443 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6335    2.3691    0.3223 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9293   -1.8879   -1.5645 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7151   -0.7793   -1.4721 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.0095   -0.6725   -0.8215 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0477   -0.9149   -1.4866 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.6672   -2.3991    0.8538 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.8103   -0.7900   -0.0564 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.1938   -0.8214    1.6991 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0941    0.8091    2.1353 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1806    1.5750    0.5614 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3678   -0.6567    2.5132 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8400    0.3695    0.6716 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1619   -1.3995   -1.3011 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3265    0.1366    1.7594 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0527    1.4977    0.4307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1206    1.1100    1.6538 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4312    0.2822    1.4172 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1298   -1.2676   -0.9866 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6536    0.0683    1.4070 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8433   -1.0000   -2.1802 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5636   -2.3918   -1.2511 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7964   -2.2940   -1.4551 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7561    0.1985    1.4146 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5402   -1.3583    1.0206 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9765   -0.3584   -1.3168 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1218    1.1452   -0.6915 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8391    1.4324    1.0824 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.2318    0.5726    0.7243 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.9590    1.6328    1.5617 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.7254    2.1367   -0.0024 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8058   -0.1925   -2.1524 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.5284    0.1574   -1.8110 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6918   -1.2821   -1.0818 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6717    2.9212   -2.8892 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6445    3.7558   -1.5715 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9170    4.0461   -1.7011 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4636    0.0879   -2.1504 H   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
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  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
 13 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  3  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
 11 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 29  2  0  0  0  0
 10 30  1  6  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 32  6  1  0  0  0  0
 31 10  1  0  0  0  0
  1 34  1  0  0  0  0
  1 35  1  0  0  0  0
  1 36  1  0  0  0  0
  5 37  1  0  0  0  0
  5 38  1  0  0  0  0
  7 39  1  0  0  0  0
 11 40  1  1  0  0  0
 12 41  1  0  0  0  0
 14 42  1  0  0  0  0
 14 43  1  0  0  0  0
 14 44  1  0  0  0  0
 15 45  1  0  0  0  0
 16 46  1  0  0  0  0
 17 47  1  0  0  0  0
 19 48  1  0  0  0  0
 19 49  1  0  0  0  0
 19 50  1  0  0  0  0
 20 51  1  0  0  0  0
 20 52  1  0  0  0  0
 21 53  1  0  0  0  0
 21 54  1  0  0  0  0
 22 55  1  0  0  0  0
 24 56  1  0  0  0  0
 24 57  1  0  0  0  0
 24 58  1  0  0  0  0
 25 59  1  0  0  0  0
 25 60  1  0  0  0  0
 25 61  1  0  0  0  0
 28 62  1  0  0  0  0
 28 63  1  0  0  0  0
 28 64  1  0  0  0  0
 31 65  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0003142

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]/C(=C(/[H])\C(=C(/[H])[C@]([H])(OC(=O)C([H])([H])[H])[C@@]12O[C@]1([H])C(=O)C(=C([H])C2=O)C([H])([H])OC(=O)C([H])([H])[H])\C([H])([H])[H])/C(/[H])=C(\C([H])([H])[H])C([H])([H])C([H])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C26H32O7/c1-16(2)9-7-10-17(3)11-8-12-18(4)13-23(32-20(6)28)26-22(29)14-21(15-31-19(5)27)24(30)25(26)33-26/h8-9,11-14,23,25H,7,10,15H2,1-6H3/b12-8+,17-11+,18-13+/t23-,25+,26+/m0/s1

> <INCHI_KEY>
PJRVHWMZLRRRMF-ZQEGAJDDSA-N

> <FORMULA>
C26H32O7

> <MOLECULAR_WEIGHT>
456.535

> <EXACT_MASS>
456.21480337

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
65

> <JCHEM_AVERAGE_POLARIZABILITY>
51.005151718004676

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,4E,6E)-1-[(1R,6S)-4-[(acetyloxy)methyl]-2,5-dioxo-7-oxabicyclo[4.1.0]hept-3-en-1-yl]-3,7,11-trimethyldodeca-2,4,6,10-tetraen-1-yl acetate

> <ALOGPS_LOGP>
3.89

> <JCHEM_LOGP>
4.1593379520000004

> <ALOGPS_LOGS>
-5.32

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.991232611980418

> <JCHEM_PKA_STRONGEST_BASIC>
-4.363907724126243

> <JCHEM_POLAR_SURFACE_AREA>
99.27000000000001

> <JCHEM_REFRACTIVITY>
127.32709999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
12

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.20e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,4E,6E)-1-[(1R,6S)-4-[(acetyloxy)methyl]-2,5-dioxo-7-oxabicyclo[4.1.0]hept-3-en-1-yl]-3,7,11-trimethyldodeca-2,4,6,10-tetraen-1-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 65 66  0  0  0  0  0  0  0  0999 V2000
   10.5639   -1.2993    0.9152 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1366   -1.0108    1.2673 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4503   -1.8008    1.9534 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5848    0.1545    0.8224 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2893    0.5621    1.0635 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2212   -0.3004    0.5911 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3347   -0.8296    1.4532 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3167   -1.6732    0.8152 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9704   -2.7830    1.2915 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6919   -1.1717   -0.4371 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6200   -0.1099   -0.2934 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2760   -0.5728   -0.4583 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1001   -0.4035    0.0092 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8200    0.8292    1.1755 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1510   -0.2234    0.5067 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2829   -0.7184   -0.0997 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5759   -0.4916    0.4654 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7032   -0.9065   -0.0438 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7089   -1.6848   -1.2998 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9947   -0.5141    0.6096 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7822    0.2772   -0.4305 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0019    0.7999    0.1744 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2445    0.6334   -0.1796 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.3732    1.2611    0.5810 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5994   -0.1927   -1.3586 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9114    0.9343   -1.2634 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4119    2.1558   -0.8914 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7060    3.2412   -1.8443 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6335    2.3691    0.3223 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9293   -1.8879   -1.5645 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7151   -0.7793   -1.4721 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.0095   -0.6725   -0.8215 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0477   -0.9149   -1.4866 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.6672   -2.3991    0.8538 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.8103   -0.7900   -0.0564 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.1938   -0.8214    1.6991 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0941    0.8091    2.1353 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1806    1.5750    0.5614 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3678   -0.6567    2.5132 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8400    0.3695    0.6716 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1619   -1.3995   -1.3011 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3265    0.1366    1.7594 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0527    1.4977    0.4307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1206    1.1100    1.6538 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4312    0.2822    1.4172 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1298   -1.2676   -0.9866 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6536    0.0683    1.4070 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8433   -1.0000   -2.1802 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5636   -2.3918   -1.2511 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7964   -2.2940   -1.4551 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7561    0.1985    1.4146 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5402   -1.3583    1.0206 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9765   -0.3584   -1.3168 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1218    1.1452   -0.6915 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8391    1.4324    1.0824 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.2318    0.5726    0.7243 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.9590    1.6328    1.5617 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.7254    2.1367   -0.0024 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8058   -0.1925   -2.1524 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.5284    0.1574   -1.8110 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6918   -1.2821   -1.0818 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6717    2.9212   -2.8892 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6445    3.7558   -1.5715 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9170    4.0461   -1.7011 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4636    0.0879   -2.1504 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 13 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  2  3
 23 24  1  0
 23 25  1  0
 11 26  1  0
 26 27  1  0
 27 28  1  0
 27 29  2  0
 10 30  1  6
 30 31  1  0
 31 32  1  0
 32 33  2  0
 32  6  1  0
 31 10  1  0
  1 34  1  0
  1 35  1  0
  1 36  1  0
  5 37  1  0
  5 38  1  0
  7 39  1  0
 11 40  1  1
 12 41  1  0
 14 42  1  0
 14 43  1  0
 14 44  1  0
 15 45  1  0
 16 46  1  0
 17 47  1  0
 19 48  1  0
 19 49  1  0
 19 50  1  0
 20 51  1  0
 20 52  1  0
 21 53  1  0
 21 54  1  0
 22 55  1  0
 24 56  1  0
 24 57  1  0
 24 58  1  0
 25 59  1  0
 25 60  1  0
 25 61  1  0
 28 62  1  0
 28 63  1  0
 28 64  1  0
 31 65  1  6
M  END

HEADER    PROTEIN                                 24-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-JUN-21         0                                  
HETATM    1  C   UNK     0      10.564  -1.299   0.915  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.137  -1.011   1.267  0.00  0.00           C+0
HETATM    3  O   UNK     0       8.450  -1.801   1.953  0.00  0.00           O+0
HETATM    4  O   UNK     0       8.585   0.155   0.822  0.00  0.00           O+0
HETATM    5  C   UNK     0       7.289   0.562   1.063  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.221  -0.300   0.591  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.335  -0.830   1.453  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.317  -1.673   0.815  0.00  0.00           C+0
HETATM    9  O   UNK     0       3.970  -2.783   1.292  0.00  0.00           O+0
HETATM   10  C   UNK     0       3.692  -1.172  -0.437  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.620  -0.110  -0.293  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.276  -0.573  -0.458  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.100  -0.404   0.009  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.820   0.829   1.176  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.151  -0.223   0.507  0.00  0.00           C+0
HETATM   16  C   UNK     0      -2.283  -0.718  -0.100  0.00  0.00           C+0
HETATM   17  C   UNK     0      -3.576  -0.492   0.465  0.00  0.00           C+0
HETATM   18  C   UNK     0      -4.703  -0.907  -0.044  0.00  0.00           C+0
HETATM   19  C   UNK     0      -4.709  -1.685  -1.300  0.00  0.00           C+0
HETATM   20  C   UNK     0      -5.995  -0.514   0.610  0.00  0.00           C+0
HETATM   21  C   UNK     0      -6.782   0.277  -0.431  0.00  0.00           C+0
HETATM   22  C   UNK     0      -8.002   0.800   0.174  0.00  0.00           C+0
HETATM   23  C   UNK     0      -9.245   0.633  -0.180  0.00  0.00           C+0
HETATM   24  C   UNK     0     -10.373   1.261   0.581  0.00  0.00           C+0
HETATM   25  C   UNK     0      -9.599  -0.193  -1.359  0.00  0.00           C+0
HETATM   26  O   UNK     0       2.911   0.934  -1.263  0.00  0.00           O+0
HETATM   27  C   UNK     0       3.412   2.156  -0.891  0.00  0.00           C+0
HETATM   28  C   UNK     0       3.706   3.241  -1.844  0.00  0.00           C+0
HETATM   29  O   UNK     0       3.634   2.369   0.322  0.00  0.00           O+0
HETATM   30  O   UNK     0       3.929  -1.888  -1.565  0.00  0.00           O+0
HETATM   31  C   UNK     0       4.715  -0.779  -1.472  0.00  0.00           C+0
HETATM   32  C   UNK     0       6.010  -0.673  -0.822  0.00  0.00           C+0
HETATM   33  O   UNK     0       7.048  -0.915  -1.487  0.00  0.00           O+0
HETATM   34  H   UNK     0      10.667  -2.399   0.854  0.00  0.00           H+0
HETATM   35  H   UNK     0      10.810  -0.790  -0.056  0.00  0.00           H+0
HETATM   36  H   UNK     0      11.194  -0.821   1.699  0.00  0.00           H+0
HETATM   37  H   UNK     0       7.094   0.809   2.135  0.00  0.00           H+0
HETATM   38  H   UNK     0       7.181   1.575   0.561  0.00  0.00           H+0
HETATM   39  H   UNK     0       5.368  -0.657   2.513  0.00  0.00           H+0
HETATM   40  H   UNK     0       2.840   0.370   0.672  0.00  0.00           H+0
HETATM   41  H   UNK     0       1.162  -1.399  -1.301  0.00  0.00           H+0
HETATM   42  H   UNK     0       1.327   0.137   1.759  0.00  0.00           H+0
HETATM   43  H   UNK     0       1.053   1.498   0.431  0.00  0.00           H+0
HETATM   44  H   UNK     0      -0.121   1.110   1.654  0.00  0.00           H+0
HETATM   45  H   UNK     0      -1.431   0.282   1.417  0.00  0.00           H+0
HETATM   46  H   UNK     0      -2.130  -1.268  -0.987  0.00  0.00           H+0
HETATM   47  H   UNK     0      -3.654   0.068   1.407  0.00  0.00           H+0
HETATM   48  H   UNK     0      -4.843  -1.000  -2.180  0.00  0.00           H+0
HETATM   49  H   UNK     0      -5.564  -2.392  -1.251  0.00  0.00           H+0
HETATM   50  H   UNK     0      -3.796  -2.294  -1.455  0.00  0.00           H+0
HETATM   51  H   UNK     0      -5.756   0.199   1.415  0.00  0.00           H+0
HETATM   52  H   UNK     0      -6.540  -1.358   1.021  0.00  0.00           H+0
HETATM   53  H   UNK     0      -6.976  -0.358  -1.317  0.00  0.00           H+0
HETATM   54  H   UNK     0      -6.122   1.145  -0.692  0.00  0.00           H+0
HETATM   55  H   UNK     0      -7.839   1.432   1.082  0.00  0.00           H+0
HETATM   56  H   UNK     0     -11.232   0.573   0.724  0.00  0.00           H+0
HETATM   57  H   UNK     0      -9.959   1.633   1.562  0.00  0.00           H+0
HETATM   58  H   UNK     0     -10.725   2.137  -0.002  0.00  0.00           H+0
HETATM   59  H   UNK     0      -8.806  -0.193  -2.152  0.00  0.00           H+0
HETATM   60  H   UNK     0     -10.528   0.157  -1.811  0.00  0.00           H+0
HETATM   61  H   UNK     0      -9.692  -1.282  -1.082  0.00  0.00           H+0
HETATM   62  H   UNK     0       3.672   2.921  -2.889  0.00  0.00           H+0
HETATM   63  H   UNK     0       4.644   3.756  -1.571  0.00  0.00           H+0
HETATM   64  H   UNK     0       2.917   4.046  -1.701  0.00  0.00           H+0
HETATM   65  H   UNK     0       4.464   0.088  -2.150  0.00  0.00           H+0
CONECT    1    2   34   35   36                                             
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   37   38                                             
CONECT    6    5    7   32                                                  
CONECT    7    6    8   39                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   30   31                                             
CONECT   11   10   12   26   40                                             
CONECT   12   11   13   41                                                  
CONECT   13   12   14   15                                                  
CONECT   14   13   42   43   44                                             
CONECT   15   13   16   45                                                  
CONECT   16   15   17   46                                                  
CONECT   17   16   18   47                                                  
CONECT   18   17   19   20                                                  
CONECT   19   18   48   49   50                                             
CONECT   20   18   21   51   52                                             
CONECT   21   20   22   53   54                                             
CONECT   22   21   23   55                                                  
CONECT   23   22   24   25                                                  
CONECT   24   23   56   57   58                                             
CONECT   25   23   59   60   61                                             
CONECT   26   11   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27   62   63   64                                             
CONECT   29   27                                                            
CONECT   30   10   31                                                       
CONECT   31   30   32   10   65                                             
CONECT   32   31   33    6                                                  
CONECT   33   32                                                            
CONECT   34    1                                                            
CONECT   35    1                                                            
CONECT   36    1                                                            
CONECT   37    5                                                            
CONECT   38    5                                                            
CONECT   39    7                                                            
CONECT   40   11                                                            
CONECT   41   12                                                            
CONECT   42   14                                                            
CONECT   43   14                                                            
CONECT   44   14                                                            
CONECT   45   15                                                            
CONECT   46   16                                                            
CONECT   47   17                                                            
CONECT   48   19                                                            
CONECT   49   19                                                            
CONECT   50   19                                                            
CONECT   51   20                                                            
CONECT   52   20                                                            
CONECT   53   21                                                            
CONECT   54   21                                                            
CONECT   55   22                                                            
CONECT   56   24                                                            
CONECT   57   24                                                            
CONECT   58   24                                                            
CONECT   59   25                                                            
CONECT   60   25                                                            
CONECT   61   25                                                            
CONECT   62   28                                                            
CONECT   63   28                                                            
CONECT   64   28                                                            
CONECT   65   31                                                            
MASTER        0    0    0    0    0    0    0    0   65    0  132    0
END

RDKit          3D

65 66  0  0  0  0  0  0  0  0999 V2000
   10.5639   -1.2993    0.9152 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1366   -1.0108    1.2673 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4503   -1.8008    1.9534 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5848    0.1545    0.8224 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2893    0.5621    1.0635 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2212   -0.3004    0.5911 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3347   -0.8296    1.4532 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3167   -1.6732    0.8152 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9704   -2.7830    1.2915 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6919   -1.1717   -0.4371 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6200   -0.1099   -0.2934 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2760   -0.5728   -0.4583 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1001   -0.4035    0.0092 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8200    0.8292    1.1755 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1510   -0.2234    0.5067 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2829   -0.7184   -0.0997 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5759   -0.4916    0.4654 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7032   -0.9065   -0.0438 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7089   -1.6848   -1.2998 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9947   -0.5141    0.6096 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7822    0.2772   -0.4305 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0019    0.7999    0.1744 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2445    0.6334   -0.1796 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.3732    1.2611    0.5810 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5994   -0.1927   -1.3586 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9114    0.9343   -1.2634 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4119    2.1558   -0.8914 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7060    3.2412   -1.8443 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6335    2.3691    0.3223 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9293   -1.8879   -1.5645 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7151   -0.7793   -1.4721 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.0095   -0.6725   -0.8215 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0477   -0.9149   -1.4866 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.6672   -2.3991    0.8538 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.8103   -0.7900   -0.0564 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.1938   -0.8214    1.6991 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0941    0.8091    2.1353 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1806    1.5750    0.5614 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3678   -0.6567    2.5132 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8400    0.3695    0.6716 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1619   -1.3995   -1.3011 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3265    0.1366    1.7594 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0527    1.4977    0.4307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1206    1.1100    1.6538 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4312    0.2822    1.4172 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1298   -1.2676   -0.9866 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6536    0.0683    1.4070 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8433   -1.0000   -2.1802 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5636   -2.3918   -1.2511 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7964   -2.2940   -1.4551 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7561    0.1985    1.4146 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5402   -1.3583    1.0206 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9765   -0.3584   -1.3168 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1218    1.1452   -0.6915 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8391    1.4324    1.0824 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.2318    0.5726    0.7243 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.9590    1.6328    1.5617 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.7254    2.1367   -0.0024 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8058   -0.1925   -2.1524 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.5284    0.1574   -1.8110 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6918   -1.2821   -1.0818 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6717    2.9212   -2.8892 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6445    3.7558   -1.5715 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9170    4.0461   -1.7011 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4636    0.0879   -2.1504 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 13 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  2  3
 23 24  1  0
 23 25  1  0
 11 26  1  0
 26 27  1  0
 27 28  1  0
 27 29  2  0
 10 30  1  6
 30 31  1  0
 31 32  1  0
 32 33  2  0
 32  6  1  0
 31 10  1  0
  1 34  1  0
  1 35  1  0
  1 36  1  0
  5 37  1  0
  5 38  1  0
  7 39  1  0
 11 40  1  1
 12 41  1  0
 14 42  1  0
 14 43  1  0
 14 44  1  0
 15 45  1  0
 16 46  1  0
 17 47  1  0
 19 48  1  0
 19 49  1  0
 19 50  1  0
 20 51  1  0
 20 52  1  0
 21 53  1  0
 21 54  1  0
 22 55  1  0
 24 56  1  0
 24 57  1  0
 24 58  1  0
 25 59  1  0
 25 60  1  0
 25 61  1  0
 28 62  1  0
 28 63  1  0
 28 64  1  0
 31 65  1  6
M  END

View in JSmol View NMR Assignments

Synonyms

Value	Source
(2E,4E,6E)-1-{4-[(acetyloxy)methyl]-2,5-dioxo-7-oxabicyclo[4.1.0]hept-3-en-1-yl}-3,7,11-trimethyldodeca-2,4,6,10-tetraen-1-yl acetic acid	Generator

Chemical Formula

C₂₆H₃₂O₇

Average Mass

456.5350 Da

Monoisotopic Mass

456.21480 Da

IUPAC Name

(1S,4E,6E)-1-[(1R,6S)-4-[(acetyloxy)methyl]-2,5-dioxo-7-oxabicyclo[4.1.0]hept-3-en-1-yl]-3,7,11-trimethyldodeca-2,4,6,10-tetraen-1-yl acetate

Traditional Name

(1S,4E,6E)-1-[(1R,6S)-4-[(acetyloxy)methyl]-2,5-dioxo-7-oxabicyclo[4.1.0]hept-3-en-1-yl]-3,7,11-trimethyldodeca-2,4,6,10-tetraen-1-yl acetate

CAS Registry Number

Not Available

SMILES

CC(C)=CCC\C(C)=C\C=C\C(\C)=C\C(OC(C)=O)C12OC1C(=O)C(COC(C)=O)=CC2=O

InChI Identifier

InChI=1S/C26H32O7/c1-16(2)9-7-10-17(3)11-8-12-18(4)13-23(32-20(6)28)26-22(29)14-21(15-31-19(5)27)24(30)25(26)33-26/h8-9,11-14,23,25H,7,10,15H2,1-6H3/b12-8+,17-11+,18-13+

InChI Key

PJRVHWMZLRRRMF-ZQEGAJDDSA-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
Arthrobotrys flagrans	NPAtlas	10656575

Species Where Detected

Species Name	Source	Reference
Duddingtonia flagrans	KNApSAcK Database	22123792

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Sesquiterpenoids

Alternative Parents

Substituents

Sesquiterpenoid
Farsesane sesquiterpenoid
Fatty alcohol ester
Cyclohexenone
Dicarboxylic acid or derivatives
Carboxylic acid ester
Ketone
Carboxylic acid derivative
Dialkyl ether
Oxirane
Ether
Oxacycle
Organoheterocyclic compound
Organic oxygen compound
Hydrocarbon derivative
Carbonyl group
Organooxygen compound
Organic oxide
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	3.89	ALOGPS
logP	4.16	ChemAxon
logS	-5.3	ALOGPS
pKa (Strongest Acidic)	14.99	ChemAxon
pKa (Strongest Basic)	-4.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	99.27 Å²	ChemAxon
Rotatable Bond Count	12	ChemAxon
Refractivity	127.33 m³·mol⁻¹	ChemAxon
Polarizability	51.01 Å³	ChemAxon
Number of Rings	2	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

NPAtlas ID

NPA000145

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

8751156

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10575770

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for Flagranone A (NP0003142)

MOL for NP0003142 (Flagranone A)

3D MOL for NP0003142 (Flagranone A)

3D SDF for NP0003142 (Flagranone A)

3D-SDF for NP0003142 (Flagranone A)

PDB for NP0003142 (Flagranone A)

3D PDB for NP0003142 (Flagranone A)

SMILES for NP0003142 (Flagranone A)

INCHI for NP0003142 (Flagranone A)

Structure for NP0003142 (Flagranone A)

3D Structure for NP0003142 (Flagranone A)