NP-MRD: Showing NP-Card for Cylindrol A2 (NP0003896)

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Record Information

Version

2.0

Created at

2020-12-09 01:26:52 UTC

Updated at

2021-07-15 16:47:40 UTC

NP-MRD ID

NP0003896

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Cylindrol A2

Provided By

NPAtlas

Description

Cylindrol A2 is found in Cylindrocarpon lucidum and Thelonectria lucida. Based on a literature review very few articles have been published on (2R,3E)-5-(3-formyl-2,6-dihydroxy-4-methylphenyl)-3-methyl-1-[(1S,2R,6R)-1,2,6-trimethyl-3-oxocyclohexyl]pent-3-en-2-yl butanoate.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242117503D          

 71 72  0  0  0  0            999 V2000
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   -2.1974    5.0220   -1.9608 C   0  0  1  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

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 28 69  1  0
 30 70  1  0
 33 71  1  0
M  END


  Mrv1652306242117503D          

 71 72  0  0  0  0            999 V2000
   -2.8412    6.3062   -1.4961 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1974    5.0220   -1.9608 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1517    3.9880   -0.8562 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5221    2.7383   -1.3208 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1270    2.7157   -2.5342 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3527    1.6305   -0.5114 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7586    0.4855   -0.9918 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5267   -0.7599   -1.0311 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0922   -1.3308    0.2058 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0946   -1.6749    1.2832 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2019   -0.4888    0.7324 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.3115   -0.5450    2.2448 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5835   -0.9129    0.2159 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.9573   -2.2477    0.8854 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.7579   -3.1025    0.7182 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6592   -4.1229    1.3479 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7106   -2.6876   -0.2139 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6481   -3.7525   -0.2960 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6469    0.2689   -0.4228 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5100   -0.6808   -1.1232 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0380    0.9183    0.6337 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2818    0.8796    1.3254 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4106    0.0629    0.9276 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4533   -1.2753    1.1880 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3858   -1.9370    1.8445 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5543   -2.0074    0.8105 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6322   -1.3982    0.1634 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8083   -2.2263   -0.2301 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5779   -0.0451   -0.0938 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7254    0.5876   -0.7789 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7439   -0.0871   -1.1282 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4929    0.6880    0.2753 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4104    2.0447    0.0310 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2457    7.2057   -1.7621 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9944    6.3269   -0.3868 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8480    6.3774   -1.9422 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7561    4.5719   -2.8069 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1877    5.2640   -2.3378 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1222    3.8450   -0.3831 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4495    4.4167   -0.0809 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4952    0.7101   -2.0911 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8731   -1.5633   -1.5010 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3824   -0.6994   -1.7727 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6268   -2.4165    1.9523 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2429   -2.2200    0.8833 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8441   -0.8359    1.9498 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1145    0.5777    0.4746 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5107    0.0325    2.7482 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3387   -1.5612    2.6478 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2675   -0.0551    2.5217 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2918   -0.1731    0.6214 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6014   -1.0369   -0.8658 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1678   -2.1200    1.9467 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8260   -2.6234    0.3004 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1213   -2.5249   -1.2340 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0556   -4.6114   -0.8668 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4463   -4.1586    0.7367 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6910   -3.4231   -0.6996 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4502   -1.7386   -0.7307 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5262   -0.3453   -1.3543 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0659   -0.8296   -2.1747 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2364    1.6159    1.0407 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0768    0.5812    2.4228 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6973    1.9473    1.5238 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6138   -1.3512    2.1107 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6326   -3.0851    0.9986 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6219   -3.3045    0.0310 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8968   -2.1754   -1.3270 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7118   -1.8577    0.2769 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6673    1.6402   -0.9712 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1264    2.5440   -0.4184 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  9  8  1  6  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  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
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
  7 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 24 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  1  0  0  0  0
 30 31  2  0  0  0  0
 29 32  2  0  0  0  0
 32 33  1  0  0  0  0
 17  9  1  0  0  0  0
 32 23  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
  2 37  1  0  0  0  0
  2 38  1  0  0  0  0
  3 39  1  0  0  0  0
  3 40  1  0  0  0  0
  7 41  1  6  0  0  0
  8 42  1  0  0  0  0
  8 43  1  0  0  0  0
 10 44  1  0  0  0  0
 10 45  1  0  0  0  0
 10 46  1  0  0  0  0
 11 47  1  1  0  0  0
 12 48  1  0  0  0  0
 12 49  1  0  0  0  0
 12 50  1  0  0  0  0
 13 51  1  0  0  0  0
 13 52  1  0  0  0  0
 14 53  1  0  0  0  0
 14 54  1  0  0  0  0
 17 55  1  6  0  0  0
 18 56  1  0  0  0  0
 18 57  1  0  0  0  0
 18 58  1  0  0  0  0
 20 59  1  0  0  0  0
 20 60  1  0  0  0  0
 20 61  1  0  0  0  0
 21 62  1  0  0  0  0
 22 63  1  0  0  0  0
 22 64  1  0  0  0  0
 25 65  1  0  0  0  0
 26 66  1  0  0  0  0
 28 67  1  0  0  0  0
 28 68  1  0  0  0  0
 28 69  1  0  0  0  0
 30 70  1  0  0  0  0
 33 71  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0003896

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C(C(O[H])=C(C([H])=O)C(=C1[H])C([H])([H])[H])C([H])([H])C(\[H])=C(/C([H])([H])[H])[C@]([H])(OC(=O)C([H])([H])C([H])([H])C([H])([H])[H])C([H])([H])[C@]1(C([H])([H])[H])[C@]([H])(C(=O)C([H])([H])C([H])([H])[C@@]1([H])C([H])([H])[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C27H38O6/c1-7-8-25(31)33-24(14-27(6)18(4)10-12-22(29)19(27)5)16(2)9-11-20-23(30)13-17(3)21(15-28)26(20)32/h9,13,15,18-19,24,30,32H,7-8,10-12,14H2,1-6H3/b16-9+/t18-,19+,24-,27+/m1/s1

> <INCHI_KEY>
DBCUFKATVZDLLO-IIKQEKBQSA-N

> <FORMULA>
C27H38O6

> <MOLECULAR_WEIGHT>
458.595

> <EXACT_MASS>
458.266838944

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
71

> <JCHEM_AVERAGE_POLARIZABILITY>
51.25535384141767

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R,3E)-5-(3-formyl-2,6-dihydroxy-4-methylphenyl)-3-methyl-1-[(1S,2R,6R)-1,2,6-trimethyl-3-oxocyclohexyl]pent-3-en-2-yl butanoate

> <ALOGPS_LOGP>
5.18

> <JCHEM_LOGP>
6.767564714333334

> <ALOGPS_LOGS>
-5.25

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.074618364153624

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.325905799039513

> <JCHEM_PKA_STRONGEST_BASIC>
-5.749655812942868

> <JCHEM_POLAR_SURFACE_AREA>
100.90000000000002

> <JCHEM_REFRACTIVITY>
130.3747

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.55e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R,3E)-5-(3-formyl-2,6-dihydroxy-4-methylphenyl)-3-methyl-1-[(1S,2R,6R)-1,2,6-trimethyl-3-oxocyclohexyl]pent-3-en-2-yl butanoate

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 71 72  0  0  0  0  0  0  0  0999 V2000
   -2.8412    6.3062   -1.4961 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1974    5.0220   -1.9608 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1517    3.9880   -0.8562 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5221    2.7383   -1.3208 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1270    2.7157   -2.5342 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3527    1.6305   -0.5114 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7586    0.4855   -0.9918 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5267   -0.7599   -1.0311 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0922   -1.3308    0.2058 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0946   -1.6749    1.2832 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2019   -0.4888    0.7324 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.3115   -0.5450    2.2448 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5835   -0.9129    0.2159 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9573   -2.2477    0.8854 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7579   -3.1025    0.7182 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6592   -4.1229    1.3479 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7106   -2.6876   -0.2139 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6481   -3.7525   -0.2960 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6469    0.2689   -0.4228 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5100   -0.6808   -1.1232 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0380    0.9183    0.6337 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2818    0.8796    1.3254 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4106    0.0629    0.9276 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4533   -1.2753    1.1880 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3858   -1.9370    1.8445 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5543   -2.0074    0.8105 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6322   -1.3982    0.1634 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8083   -2.2263   -0.2301 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5779   -0.0451   -0.0938 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7254    0.5876   -0.7789 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7439   -0.0871   -1.1282 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4929    0.6880    0.2753 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4104    2.0447    0.0310 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2457    7.2057   -1.7621 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9944    6.3269   -0.3868 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8480    6.3774   -1.9422 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7561    4.5719   -2.8069 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1877    5.2640   -2.3378 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1222    3.8450   -0.3831 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4495    4.4167   -0.0809 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4952    0.7101   -2.0911 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8731   -1.5633   -1.5010 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3824   -0.6994   -1.7727 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6268   -2.4165    1.9523 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2429   -2.2200    0.8833 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8441   -0.8359    1.9498 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1145    0.5777    0.4746 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5107    0.0325    2.7482 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3387   -1.5612    2.6478 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2675   -0.0551    2.5217 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2918   -0.1731    0.6214 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6014   -1.0369   -0.8658 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1678   -2.1200    1.9467 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8260   -2.6234    0.3004 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1213   -2.5249   -1.2340 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0556   -4.6114   -0.8668 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4463   -4.1586    0.7367 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6910   -3.4231   -0.6996 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4502   -1.7386   -0.7307 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5262   -0.3453   -1.3543 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0659   -0.8296   -2.1747 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2364    1.6159    1.0407 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0768    0.5812    2.4228 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6973    1.9473    1.5238 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6138   -1.3512    2.1107 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6326   -3.0851    0.9986 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6219   -3.3045    0.0310 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8968   -2.1754   -1.3270 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7118   -1.8577    0.2769 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6673    1.6402   -0.9712 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1264    2.5440   -0.4184 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  9  8  1  6
  9 10  1  0
  9 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
 17 18  1  0
  7 19  1  0
 19 20  1  0
 19 21  2  0
 21 22  1  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 24 26  1  0
 26 27  2  0
 27 28  1  0
 27 29  1  0
 29 30  1  0
 30 31  2  0
 29 32  2  0
 32 33  1  0
 17  9  1  0
 32 23  1  0
  1 34  1  0
  1 35  1  0
  1 36  1  0
  2 37  1  0
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  3 39  1  0
  3 40  1  0
  7 41  1  6
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  8 43  1  0
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 11 47  1  1
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 17 55  1  6
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 25 65  1  0
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 28 67  1  0
 28 68  1  0
 28 69  1  0
 30 70  1  0
 33 71  1  0
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      -2.841   6.306  -1.496  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.197   5.022  -1.961  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.152   3.988  -0.856  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.522   2.738  -1.321  0.00  0.00           C+0
HETATM    5  O   UNK     0      -1.127   2.716  -2.534  0.00  0.00           O+0
HETATM    6  O   UNK     0      -1.353   1.631  -0.511  0.00  0.00           O+0
HETATM    7  C   UNK     0      -0.759   0.486  -0.992  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.527  -0.760  -1.031  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.092  -1.331   0.206  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.095  -1.675   1.283  0.00  0.00           C+0
HETATM   11  C   UNK     0      -3.202  -0.489   0.732  0.00  0.00           C+0
HETATM   12  C   UNK     0      -3.312  -0.545   2.245  0.00  0.00           C+0
HETATM   13  C   UNK     0      -4.583  -0.913   0.216  0.00  0.00           C+0
HETATM   14  C   UNK     0      -4.957  -2.248   0.885  0.00  0.00           C+0
HETATM   15  C   UNK     0      -3.758  -3.103   0.718  0.00  0.00           C+0
HETATM   16  O   UNK     0      -3.659  -4.123   1.348  0.00  0.00           O+0
HETATM   17  C   UNK     0      -2.711  -2.688  -0.214  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.648  -3.753  -0.296  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.647   0.269  -0.423  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.510  -0.681  -1.123  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.038   0.918   0.634  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.282   0.880   1.325  0.00  0.00           C+0
HETATM   23  C   UNK     0       3.411   0.063   0.928  0.00  0.00           C+0
HETATM   24  C   UNK     0       3.453  -1.275   1.188  0.00  0.00           C+0
HETATM   25  O   UNK     0       2.386  -1.937   1.845  0.00  0.00           O+0
HETATM   26  C   UNK     0       4.554  -2.007   0.811  0.00  0.00           C+0
HETATM   27  C   UNK     0       5.632  -1.398   0.163  0.00  0.00           C+0
HETATM   28  C   UNK     0       6.808  -2.226  -0.230  0.00  0.00           C+0
HETATM   29  C   UNK     0       5.578  -0.045  -0.094  0.00  0.00           C+0
HETATM   30  C   UNK     0       6.725   0.588  -0.779  0.00  0.00           C+0
HETATM   31  O   UNK     0       7.744  -0.087  -1.128  0.00  0.00           O+0
HETATM   32  C   UNK     0       4.493   0.688   0.275  0.00  0.00           C+0
HETATM   33  O   UNK     0       4.410   2.045   0.031  0.00  0.00           O+0
HETATM   34  H   UNK     0      -2.246   7.206  -1.762  0.00  0.00           H+0
HETATM   35  H   UNK     0      -2.994   6.327  -0.387  0.00  0.00           H+0
HETATM   36  H   UNK     0      -3.848   6.377  -1.942  0.00  0.00           H+0
HETATM   37  H   UNK     0      -2.756   4.572  -2.807  0.00  0.00           H+0
HETATM   38  H   UNK     0      -1.188   5.264  -2.338  0.00  0.00           H+0
HETATM   39  H   UNK     0      -3.122   3.845  -0.383  0.00  0.00           H+0
HETATM   40  H   UNK     0      -1.450   4.417  -0.081  0.00  0.00           H+0
HETATM   41  H   UNK     0      -0.495   0.710  -2.091  0.00  0.00           H+0
HETATM   42  H   UNK     0      -0.873  -1.563  -1.501  0.00  0.00           H+0
HETATM   43  H   UNK     0      -2.382  -0.699  -1.773  0.00  0.00           H+0
HETATM   44  H   UNK     0      -1.627  -2.417   1.952  0.00  0.00           H+0
HETATM   45  H   UNK     0      -0.243  -2.220   0.883  0.00  0.00           H+0
HETATM   46  H   UNK     0      -0.844  -0.836   1.950  0.00  0.00           H+0
HETATM   47  H   UNK     0      -3.115   0.578   0.475  0.00  0.00           H+0
HETATM   48  H   UNK     0      -2.511   0.033   2.748  0.00  0.00           H+0
HETATM   49  H   UNK     0      -3.339  -1.561   2.648  0.00  0.00           H+0
HETATM   50  H   UNK     0      -4.268  -0.055   2.522  0.00  0.00           H+0
HETATM   51  H   UNK     0      -5.292  -0.173   0.621  0.00  0.00           H+0
HETATM   52  H   UNK     0      -4.601  -1.037  -0.866  0.00  0.00           H+0
HETATM   53  H   UNK     0      -5.168  -2.120   1.947  0.00  0.00           H+0
HETATM   54  H   UNK     0      -5.826  -2.623   0.300  0.00  0.00           H+0
HETATM   55  H   UNK     0      -3.121  -2.525  -1.234  0.00  0.00           H+0
HETATM   56  H   UNK     0      -2.056  -4.611  -0.867  0.00  0.00           H+0
HETATM   57  H   UNK     0      -1.446  -4.159   0.737  0.00  0.00           H+0
HETATM   58  H   UNK     0      -0.691  -3.423  -0.700  0.00  0.00           H+0
HETATM   59  H   UNK     0       1.450  -1.739  -0.731  0.00  0.00           H+0
HETATM   60  H   UNK     0       2.526  -0.345  -1.354  0.00  0.00           H+0
HETATM   61  H   UNK     0       1.066  -0.830  -2.175  0.00  0.00           H+0
HETATM   62  H   UNK     0       0.236   1.616   1.041  0.00  0.00           H+0
HETATM   63  H   UNK     0       2.077   0.581   2.423  0.00  0.00           H+0
HETATM   64  H   UNK     0       2.697   1.947   1.524  0.00  0.00           H+0
HETATM   65  H   UNK     0       1.614  -1.351   2.111  0.00  0.00           H+0
HETATM   66  H   UNK     0       4.633  -3.085   0.999  0.00  0.00           H+0
HETATM   67  H   UNK     0       6.622  -3.305   0.031  0.00  0.00           H+0
HETATM   68  H   UNK     0       6.897  -2.175  -1.327  0.00  0.00           H+0
HETATM   69  H   UNK     0       7.712  -1.858   0.277  0.00  0.00           H+0
HETATM   70  H   UNK     0       6.667   1.640  -0.971  0.00  0.00           H+0
HETATM   71  H   UNK     0       5.126   2.544  -0.418  0.00  0.00           H+0
CONECT    1    2   34   35   36                                             
CONECT    2    1    3   37   38                                             
CONECT    3    2    4   39   40                                             
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8   19   41                                             
CONECT    8    7    9   42   43                                             
CONECT    9    8   10   11   17                                             
CONECT   10    9   44   45   46                                             
CONECT   11    9   12   13   47                                             
CONECT   12   11   48   49   50                                             
CONECT   13   11   14   51   52                                             
CONECT   14   13   15   53   54                                             
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18    9   55                                             
CONECT   18   17   56   57   58                                             
CONECT   19    7   20   21                                                  
CONECT   20   19   59   60   61                                             
CONECT   21   19   22   62                                                  
CONECT   22   21   23   63   64                                             
CONECT   23   22   24   32                                                  
CONECT   24   23   25   26                                                  
CONECT   25   24   65                                                       
CONECT   26   24   27   66                                                  
CONECT   27   26   28   29                                                  
CONECT   28   27   67   68   69                                             
CONECT   29   27   30   32                                                  
CONECT   30   29   31   70                                                  
CONECT   31   30                                                            
CONECT   32   29   33   23                                                  
CONECT   33   32   71                                                       
CONECT   34    1                                                            
CONECT   35    1                                                            
CONECT   36    1                                                            
CONECT   37    2                                                            
CONECT   38    2                                                            
CONECT   39    3                                                            
CONECT   40    3                                                            
CONECT   41    7                                                            
CONECT   42    8                                                            
CONECT   43    8                                                            
CONECT   44   10                                                            
CONECT   45   10                                                            
CONECT   46   10                                                            
CONECT   47   11                                                            
CONECT   48   12                                                            
CONECT   49   12                                                            
CONECT   50   12                                                            
CONECT   51   13                                                            
CONECT   52   13                                                            
CONECT   53   14                                                            
CONECT   54   14                                                            
CONECT   55   17                                                            
CONECT   56   18                                                            
CONECT   57   18                                                            
CONECT   58   18                                                            
CONECT   59   20                                                            
CONECT   60   20                                                            
CONECT   61   20                                                            
CONECT   62   21                                                            
CONECT   63   22                                                            
CONECT   64   22                                                            
CONECT   65   25                                                            
CONECT   66   26                                                            
CONECT   67   28                                                            
CONECT   68   28                                                            
CONECT   69   28                                                            
CONECT   70   30                                                            
CONECT   71   33                                                            
MASTER        0    0    0    0    0    0    0    0   71    0  144    0
END

RDKit          3D

71 72  0  0  0  0  0  0  0  0999 V2000
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   -2.1974    5.0220   -1.9608 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1517    3.9880   -0.8562 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5221    2.7383   -1.3208 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1270    2.7157   -2.5342 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3527    1.6305   -0.5114 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7586    0.4855   -0.9918 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5267   -0.7599   -1.0311 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0922   -1.3308    0.2058 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0946   -1.6749    1.2832 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2019   -0.4888    0.7324 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.3115   -0.5450    2.2448 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5835   -0.9129    0.2159 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9573   -2.2477    0.8854 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7579   -3.1025    0.7182 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6592   -4.1229    1.3479 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7106   -2.6876   -0.2139 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6481   -3.7525   -0.2960 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.5100   -0.6808   -1.1232 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.2818    0.8796    1.3254 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4106    0.0629    0.9276 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4533   -1.2753    1.1880 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3858   -1.9370    1.8445 O   0  0  0  0  0  0  0  0  0  0  0  0
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    6.8083   -2.2263   -0.2301 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5779   -0.0451   -0.0938 C   0  0  0  0  0  0  0  0  0  0  0  0
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    7.7439   -0.0871   -1.1282 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4929    0.6880    0.2753 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4104    2.0447    0.0310 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2457    7.2057   -1.7621 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.7561    4.5719   -2.8069 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.4495    4.4167   -0.0809 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4952    0.7101   -2.0911 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8731   -1.5633   -1.5010 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3824   -0.6994   -1.7727 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6268   -2.4165    1.9523 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2429   -2.2200    0.8833 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8441   -0.8359    1.9498 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.3387   -1.5612    2.6478 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.6910   -3.4231   -0.6996 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4502   -1.7386   -0.7307 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5262   -0.3453   -1.3543 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0659   -0.8296   -2.1747 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2364    1.6159    1.0407 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0768    0.5812    2.4228 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6973    1.9473    1.5238 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6138   -1.3512    2.1107 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6326   -3.0851    0.9986 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6219   -3.3045    0.0310 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8968   -2.1754   -1.3270 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7118   -1.8577    0.2769 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6673    1.6402   -0.9712 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1264    2.5440   -0.4184 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  9  8  1  6
  9 10  1  0
  9 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
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M  END

View in JSmol View NMR Assignments

Synonyms

Value	Source
(2R,3E)-5-(3-Formyl-2,6-dihydroxy-4-methylphenyl)-3-methyl-1-[(1S,2R,6R)-1,2,6-trimethyl-3-oxocyclohexyl]pent-3-en-2-yl butanoic acid	Generator

Chemical Formula

C₂₇H₃₈O₆

Average Mass

458.5950 Da

Monoisotopic Mass

458.26684 Da

IUPAC Name

(2R,3E)-5-(3-formyl-2,6-dihydroxy-4-methylphenyl)-3-methyl-1-[(1S,2R,6R)-1,2,6-trimethyl-3-oxocyclohexyl]pent-3-en-2-yl butanoate

Traditional Name

(2R,3E)-5-(3-formyl-2,6-dihydroxy-4-methylphenyl)-3-methyl-1-[(1S,2R,6R)-1,2,6-trimethyl-3-oxocyclohexyl]pent-3-en-2-yl butanoate

CAS Registry Number

Not Available

SMILES

CCCC(=O)O[C@H](C[C@@]1(C)[C@H](C)CCC(=O)[C@@H]1C)C(\C)=C\CC1=C(O)C=C(C)C(C=O)=C1O

InChI Identifier

InChI=1S/C27H38O6/c1-7-8-25(31)33-24(14-27(6)18(4)10-12-22(29)19(27)5)16(2)9-11-20-23(30)13-17(3)21(15-28)26(20)32/h9,13,15,18-19,24,30,32H,7-8,10-12,14H2,1-6H3/b16-9+/t18-,19+,24-,27+/m1/s1

InChI Key

DBCUFKATVZDLLO-IIKQEKBQSA-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
Cylindrocarpon lucidum	NPAtlas	11667727
Thelonectria lucida	LOTUS Database	35616633

Chemical Taxonomy

Classification

Not classified

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	5.18	ALOGPS
logP	6.77	ChemAxon
logS	-5.2	ALOGPS
pKa (Strongest Acidic)	7.33	ChemAxon
pKa (Strongest Basic)	-5.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	100.9 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	130.37 m³·mol⁻¹	ChemAxon
Polarizability	51.26 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

NPAtlas ID

NPA013359

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

8894051

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10718712

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for Cylindrol A2 (NP0003896)

MOL for NP0003896 (Cylindrol A2)

3D MOL for NP0003896 (Cylindrol A2)

3D SDF for NP0003896 (Cylindrol A2)

3D-SDF for NP0003896 (Cylindrol A2)

PDB for NP0003896 (Cylindrol A2)

3D PDB for NP0003896 (Cylindrol A2)

SMILES for NP0003896 (Cylindrol A2)

INCHI for NP0003896 (Cylindrol A2)

Structure for NP0003896 (Cylindrol A2)

3D Structure for NP0003896 (Cylindrol A2)