NP-MRD: Showing NP-Card for Oxalicine B (NP0005766)

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Record Information

Version

2.0

Created at

2020-12-09 02:55:21 UTC

Updated at

2021-07-15 16:52:55 UTC

NP-MRD ID

NP0005766

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Oxalicine B

Provided By

NPAtlas

Description

(2S,3S,4'aS,5'R,6'R,8'aR)-3,6'-dihydroxy-2',8'a-dimethyl-6'-(prop-1-en-2-yl)-6-(pyridin-3-yl)-3,4,4',4'a,6',7',8',8'a-octahydrodispiro[furo[3,2-c]pyran-2,1'-naphthalene-5',3''-oxane]-4,6''-dione belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring. Oxalicine B is found in Penicillium thiersii. Based on a literature review very few articles have been published on (2S,3S,4'aS,5'R,6'R,8'aR)-3,6'-dihydroxy-2',8'a-dimethyl-6'-(prop-1-en-2-yl)-6-(pyridin-3-yl)-3,4,4',4'a,6',7',8',8'a-octahydrodispiro[furo[3,2-c]pyran-2,1'-naphthalene-5',3''-oxane]-4,6''-dione.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242118223D          

 71 76  0  0  0  0            999 V2000
   -4.7472    1.7176   -0.8775 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2054    1.8494    0.3005 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7991    3.0006    1.1272 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0932    1.0690    0.8533 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.4247    1.0297    2.2759 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8951    1.9768    0.8308 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6289    1.3939    0.3688 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7967    0.4650   -0.8478 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3201    1.2957   -1.9556 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6744   -0.6302   -0.3603 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8797   -1.5870   -1.5108 C   0  0  1  0  0  0  0  0  0  0  0  0
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    7.1288   -1.5455    4.2784 H   0  0  0  0  0  0  0  0  0  0  0  0
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    2.0257    2.6112   -2.1231 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2054   -2.0739    1.4809 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1186   -0.5521    2.4056 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8101   -1.9485    3.3213 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7851   -0.7317    2.4831 H   0  0  0  0  0  0  0  0  0  0  0  0
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 15  8  1  0  0  0  0
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  1 39  1  0  0  0  0
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  3 41  1  0  0  0  0
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 34 68  1  0  0  0  0
 34 69  1  0  0  0  0
 38 70  1  0  0  0  0
 38 71  1  0  0  0  0
M  END

     RDKit          3D

 71 76  0  0  0  0  0  0  0  0999 V2000
   -4.7472    1.7176   -0.8775 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2054    1.8494    0.3005 C   0  0  0  0  0  0  0  0  0  0  0  0
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 30 15  1  0
 25 20  1  0
  1 39  1  0
  1 40  1  0
  3 41  1  0
  3 42  1  0
  3 43  1  0
  5 44  1  0
  6 45  1  0
  6 46  1  0
  7 47  1  0
  7 48  1  0
  9 49  1  0
  9 50  1  0
  9 51  1  0
 10 52  1  1
 11 53  1  0
 11 54  1  0
 12 55  1  0
 14 56  1  0
 14 57  1  0
 14 58  1  0
 18 59  1  0
 21 60  1  0
 22 61  1  0
 23 62  1  0
 25 63  1  0
 30 64  1  6
 31 65  1  0
 33 66  1  0
 33 67  1  0
 34 68  1  0
 34 69  1  0
 38 70  1  0
 38 71  1  0
M  END


  Mrv1652306242118223D          

 71 76  0  0  0  0            999 V2000
   -4.7472    1.7176   -0.8775 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2054    1.8494    0.3005 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7991    3.0006    1.1272 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0932    1.0690    0.8533 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.4247    1.0297    2.2759 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8951    1.9768    0.8308 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6289    1.3939    0.3688 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7967    0.4650   -0.8478 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3201    1.2957   -1.9556 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6744   -0.6302   -0.3603 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8797   -1.5870   -1.5108 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5458   -2.1447   -1.8253 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5584   -1.4740   -1.6242 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8956   -2.1385   -1.9797 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5656   -0.1102   -1.0714 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2648   -0.2064    0.1906 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6128   -0.0452    0.0303 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7168   -0.3254    0.8618 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9928   -0.0596    0.4420 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1822   -0.3423    1.2930 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0834   -0.8834    2.5436 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2377   -1.1094    3.2740 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4783   -0.8029    2.7712 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5359   -0.2740    1.5434 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.4398   -0.0459    0.8167 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1512    0.4609   -0.7510 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1603    0.7402   -1.5606 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3390    1.2408   -2.7037 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8344    0.4983   -1.2045 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5208    0.7014   -1.8619 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2366    2.0407   -1.9847 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9278   -0.3080    0.3788 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.7519   -1.1378    1.7027 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.0430   -1.5015    2.3361 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.5794   -2.6010    1.4478 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1809   -3.5865    1.8909 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3067   -2.3446    0.1323 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1413   -0.9589   -0.2386 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.5568    1.0317   -1.6643 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5699    2.4351   -1.1584 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9887    2.5618    2.1224 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1165    3.8492    1.1452 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7613    3.3315    0.7310 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1601    1.8887    2.6245 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7015    2.4220    1.8307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0937    2.9059    0.2076 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0360    2.2141   -0.0058 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0157    0.8913    1.1570 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7268    1.2219   -2.8949 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3078    0.8920   -2.2519 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4984    2.3244   -1.6329 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9850   -1.2167    0.3355 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4870   -2.4896   -1.2174 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3486   -1.1096   -2.3993 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4547   -3.1785   -2.2504 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3935   -2.2704   -1.0006 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5027   -1.4930   -2.6115 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6949   -3.1267   -2.4110 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5116   -0.7480    1.8235 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1048   -1.1292    2.9439 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1288   -1.5455    4.2784 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.3668   -0.9945    3.3725 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5499    0.3820   -0.1658 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6325    0.3266   -2.8998 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0257    2.6112   -2.1231 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2054   -2.0739    1.4809 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1186   -0.5521    2.4056 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8101   -1.9485    3.3213 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7851   -0.7317    2.4831 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0369   -1.0615   -1.3488 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0845   -0.4824    0.0642 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  1  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  6  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  1  1  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 19 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 27 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 10 32  1  0  0  0  0
 32 33  1  1  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  2  0  0  0  0
 35 37  1  0  0  0  0
 37 38  1  0  0  0  0
 32  4  1  0  0  0  0
 15  8  1  0  0  0  0
 29 17  2  0  0  0  0
 38 32  1  0  0  0  0
 30 15  1  0  0  0  0
 25 20  1  0  0  0  0
  1 39  1  0  0  0  0
  1 40  1  0  0  0  0
  3 41  1  0  0  0  0
  3 42  1  0  0  0  0
  3 43  1  0  0  0  0
  5 44  1  0  0  0  0
  6 45  1  0  0  0  0
  6 46  1  0  0  0  0
  7 47  1  0  0  0  0
  7 48  1  0  0  0  0
  9 49  1  0  0  0  0
  9 50  1  0  0  0  0
  9 51  1  0  0  0  0
 10 52  1  1  0  0  0
 11 53  1  0  0  0  0
 11 54  1  0  0  0  0
 12 55  1  0  0  0  0
 14 56  1  0  0  0  0
 14 57  1  0  0  0  0
 14 58  1  0  0  0  0
 18 59  1  0  0  0  0
 21 60  1  0  0  0  0
 22 61  1  0  0  0  0
 23 62  1  0  0  0  0
 25 63  1  0  0  0  0
 30 64  1  6  0  0  0
 31 65  1  0  0  0  0
 33 66  1  0  0  0  0
 33 67  1  0  0  0  0
 34 68  1  0  0  0  0
 34 69  1  0  0  0  0
 38 70  1  0  0  0  0
 38 71  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0005766

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]O[C@@]1([H])C2=C(O[C@]11C(=C([H])C([H])([H])[C@@]3([H])[C@@]1(C([H])([H])[H])C([H])([H])C([H])([H])[C@@](O[H])(C(=C([H])[H])C([H])([H])[H])[C@@]31C([H])([H])OC(=O)C([H])([H])C1([H])[H])C([H])([H])[H])C([H])=C(OC2=O)C1=C([H])C([H])=C([H])N=C1[H]

> <INCHI_IDENTIFIER>
InChI=1S/C30H33NO7/c1-17(2)29(35)12-11-27(4)22(28(29)10-9-23(32)36-16-28)8-7-18(3)30(27)25(33)24-21(38-30)14-20(37-26(24)34)19-6-5-13-31-15-19/h5-7,13-15,22,25,33,35H,1,8-12,16H2,2-4H3/t22-,25-,27+,28-,29+,30+/m0/s1

> <INCHI_KEY>
GADSICAILMLRQB-GVRUMSNVSA-N

> <FORMULA>
C30H33NO7

> <MOLECULAR_WEIGHT>
519.594

> <EXACT_MASS>
519.225702407

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
71

> <JCHEM_AVERAGE_POLARIZABILITY>
55.184428879035615

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,3S,4'aS,5'R,6'R,8'aR)-3,6'-dihydroxy-2',8'a-dimethyl-6'-(prop-1-en-2-yl)-6-(pyridin-3-yl)-3,4,4',4'a,6',7',8',8'a-octahydrodispiro[furo[3,2-c]pyran-2,1'-naphthalene-5',3''-oxane]-4,6''-dione

> <ALOGPS_LOGP>
2.91

> <JCHEM_LOGP>
1.966110912000001

> <ALOGPS_LOGS>
-4.55

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.836217521058074

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.875640807277918

> <JCHEM_PKA_STRONGEST_BASIC>
4.206318632956978

> <JCHEM_POLAR_SURFACE_AREA>
115.18

> <JCHEM_REFRACTIVITY>
140.08810000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.45e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3S,4'aS,5'R,6'R,8'aR)-3,6'-dihydroxy-2',8'a-dimethyl-6'-(prop-1-en-2-yl)-6-(pyridin-3-yl)-4',4'a,7',8'-tetrahydro-3H-dispiro[furo[3,2-c]pyran-2,1'-naphthalene-5',3''-oxane]-4,6''-dione

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 71 76  0  0  0  0  0  0  0  0999 V2000
   -4.7472    1.7176   -0.8775 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2054    1.8494    0.3005 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7991    3.0006    1.1272 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0932    1.0690    0.8533 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.4247    1.0297    2.2759 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8951    1.9768    0.8308 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6289    1.3939    0.3688 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7967    0.4650   -0.8478 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3201    1.2957   -1.9556 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6744   -0.6302   -0.3603 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8797   -1.5870   -1.5108 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5458   -2.1447   -1.8253 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5584   -1.4740   -1.6242 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8956   -2.1385   -1.9797 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5656   -0.1102   -1.0714 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2648   -0.2064    0.1906 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6128   -0.0452    0.0303 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7168   -0.3254    0.8618 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9928   -0.0596    0.4420 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1822   -0.3423    1.2930 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0834   -0.8834    2.5436 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2377   -1.1094    3.2740 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4783   -0.8029    2.7712 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5359   -0.2740    1.5434 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.4398   -0.0459    0.8167 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1512    0.4609   -0.7510 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1603    0.7402   -1.5606 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3390    1.2408   -2.7037 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8344    0.4983   -1.2045 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5208    0.7014   -1.8619 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2366    2.0407   -1.9847 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9278   -0.3080    0.3788 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.7519   -1.1378    1.7027 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0430   -1.5015    2.3361 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5794   -2.6010    1.4478 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1809   -3.5865    1.8909 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3067   -2.3446    0.1323 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1413   -0.9589   -0.2386 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5568    1.0317   -1.6643 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5699    2.4351   -1.1584 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9887    2.5618    2.1224 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1165    3.8492    1.1452 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7613    3.3315    0.7310 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1601    1.8887    2.6245 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7015    2.4220    1.8307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0937    2.9059    0.2076 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0360    2.2141   -0.0058 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0157    0.8913    1.1570 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7268    1.2219   -2.8949 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3078    0.8920   -2.2519 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4984    2.3244   -1.6329 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9850   -1.2167    0.3355 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4870   -2.4896   -1.2174 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3486   -1.1096   -2.3993 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4547   -3.1785   -2.2504 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3935   -2.2704   -1.0006 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5027   -1.4930   -2.6115 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6949   -3.1267   -2.4110 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5116   -0.7480    1.8235 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1048   -1.1292    2.9439 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1288   -1.5455    4.2784 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.3668   -0.9945    3.3725 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5499    0.3820   -0.1658 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6325    0.3266   -2.8998 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0257    2.6112   -2.1231 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2054   -2.0739    1.4809 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1186   -0.5521    2.4056 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8101   -1.9485    3.3213 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7851   -0.7317    2.4831 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0369   -1.0615   -1.3488 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0845   -0.4824    0.0642 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  2  4  1  0
  4  5  1  1
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  6
  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  1  1
 16 17  1  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 19 26  1  0
 26 27  1  0
 27 28  2  0
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 29 30  1  0
 30 31  1  0
 10 32  1  0
 32 33  1  1
 33 34  1  0
 34 35  1  0
 35 36  2  0
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 37 38  1  0
 32  4  1  0
 15  8  1  0
 29 17  2  0
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 30 15  1  0
 25 20  1  0
  1 39  1  0
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 21 60  1  0
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 30 64  1  6
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 33 66  1  0
 33 67  1  0
 34 68  1  0
 34 69  1  0
 38 70  1  0
 38 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      -4.747   1.718  -0.878  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.205   1.849   0.301  0.00  0.00           C+0
HETATM    3  C   UNK     0      -4.799   3.001   1.127  0.00  0.00           C+0
HETATM    4  C   UNK     0      -3.093   1.069   0.853  0.00  0.00           C+0
HETATM    5  O   UNK     0      -3.425   1.030   2.276  0.00  0.00           O+0
HETATM    6  C   UNK     0      -1.895   1.977   0.831  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.629   1.394   0.369  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.797   0.465  -0.848  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.320   1.296  -1.956  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.674  -0.630  -0.360  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.880  -1.587  -1.511  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.546  -2.145  -1.825  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.558  -1.474  -1.624  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.896  -2.139  -1.980  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.566  -0.110  -1.071  0.00  0.00           C+0
HETATM   16  O   UNK     0       1.265  -0.206   0.191  0.00  0.00           O+0
HETATM   17  C   UNK     0       2.613  -0.045   0.030  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.717  -0.325   0.862  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.993  -0.060   0.442  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.182  -0.342   1.293  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.083  -0.883   2.544  0.00  0.00           C+0
HETATM   22  C   UNK     0       7.238  -1.109   3.274  0.00  0.00           C+0
HETATM   23  C   UNK     0       8.478  -0.803   2.771  0.00  0.00           C+0
HETATM   24  N   UNK     0       8.536  -0.274   1.543  0.00  0.00           N+0
HETATM   25  C   UNK     0       7.440  -0.046   0.817  0.00  0.00           C+0
HETATM   26  O   UNK     0       5.151   0.461  -0.751  0.00  0.00           O+0
HETATM   27  C   UNK     0       4.160   0.740  -1.561  0.00  0.00           C+0
HETATM   28  O   UNK     0       4.339   1.241  -2.704  0.00  0.00           O+0
HETATM   29  C   UNK     0       2.834   0.498  -1.204  0.00  0.00           C+0
HETATM   30  C   UNK     0       1.521   0.701  -1.862  0.00  0.00           C+0
HETATM   31  O   UNK     0       1.237   2.041  -1.985  0.00  0.00           O+0
HETATM   32  C   UNK     0      -2.928  -0.308   0.379  0.00  0.00           C+0
HETATM   33  C   UNK     0      -2.752  -1.138   1.703  0.00  0.00           C+0
HETATM   34  C   UNK     0      -4.043  -1.502   2.336  0.00  0.00           C+0
HETATM   35  C   UNK     0      -4.579  -2.601   1.448  0.00  0.00           C+0
HETATM   36  O   UNK     0      -5.181  -3.587   1.891  0.00  0.00           O+0
HETATM   37  O   UNK     0      -4.307  -2.345   0.132  0.00  0.00           O+0
HETATM   38  C   UNK     0      -4.141  -0.959  -0.239  0.00  0.00           C+0
HETATM   39  H   UNK     0      -4.557   1.032  -1.664  0.00  0.00           H+0
HETATM   40  H   UNK     0      -5.570   2.435  -1.158  0.00  0.00           H+0
HETATM   41  H   UNK     0      -4.989   2.562   2.122  0.00  0.00           H+0
HETATM   42  H   UNK     0      -4.117   3.849   1.145  0.00  0.00           H+0
HETATM   43  H   UNK     0      -5.761   3.332   0.731  0.00  0.00           H+0
HETATM   44  H   UNK     0      -3.160   1.889   2.624  0.00  0.00           H+0
HETATM   45  H   UNK     0      -1.702   2.422   1.831  0.00  0.00           H+0
HETATM   46  H   UNK     0      -2.094   2.906   0.208  0.00  0.00           H+0
HETATM   47  H   UNK     0       0.036   2.214  -0.006  0.00  0.00           H+0
HETATM   48  H   UNK     0      -0.016   0.891   1.157  0.00  0.00           H+0
HETATM   49  H   UNK     0      -0.727   1.222  -2.895  0.00  0.00           H+0
HETATM   50  H   UNK     0      -2.308   0.892  -2.252  0.00  0.00           H+0
HETATM   51  H   UNK     0      -1.498   2.324  -1.633  0.00  0.00           H+0
HETATM   52  H   UNK     0      -0.985  -1.217   0.336  0.00  0.00           H+0
HETATM   53  H   UNK     0      -2.487  -2.490  -1.217  0.00  0.00           H+0
HETATM   54  H   UNK     0      -2.349  -1.110  -2.399  0.00  0.00           H+0
HETATM   55  H   UNK     0      -0.455  -3.179  -2.250  0.00  0.00           H+0
HETATM   56  H   UNK     0       2.393  -2.270  -1.001  0.00  0.00           H+0
HETATM   57  H   UNK     0       2.503  -1.493  -2.611  0.00  0.00           H+0
HETATM   58  H   UNK     0       1.695  -3.127  -2.411  0.00  0.00           H+0
HETATM   59  H   UNK     0       3.512  -0.748   1.823  0.00  0.00           H+0
HETATM   60  H   UNK     0       5.105  -1.129   2.944  0.00  0.00           H+0
HETATM   61  H   UNK     0       7.129  -1.546   4.278  0.00  0.00           H+0
HETATM   62  H   UNK     0       9.367  -0.995   3.373  0.00  0.00           H+0
HETATM   63  H   UNK     0       7.550   0.382  -0.166  0.00  0.00           H+0
HETATM   64  H   UNK     0       1.633   0.327  -2.900  0.00  0.00           H+0
HETATM   65  H   UNK     0       2.026   2.611  -2.123  0.00  0.00           H+0
HETATM   66  H   UNK     0      -2.205  -2.074   1.481  0.00  0.00           H+0
HETATM   67  H   UNK     0      -2.119  -0.552   2.406  0.00  0.00           H+0
HETATM   68  H   UNK     0      -3.810  -1.948   3.321  0.00  0.00           H+0
HETATM   69  H   UNK     0      -4.785  -0.732   2.483  0.00  0.00           H+0
HETATM   70  H   UNK     0      -4.037  -1.062  -1.349  0.00  0.00           H+0
HETATM   71  H   UNK     0      -5.085  -0.482   0.064  0.00  0.00           H+0
CONECT    1    2   39   40                                                  
CONECT    2    1    3    4                                                  
CONECT    3    2   41   42   43                                             
CONECT    4    2    5    6   32                                             
CONECT    5    4   44                                                       
CONECT    6    4    7   45   46                                             
CONECT    7    6    8   47   48                                             
CONECT    8    7    9   10   15                                             
CONECT    9    8   49   50   51                                             
CONECT   10    8   11   32   52                                             
CONECT   11   10   12   53   54                                             
CONECT   12   11   13   55                                                  
CONECT   13   12   14   15                                                  
CONECT   14   13   56   57   58                                             
CONECT   15   13   16    8   30                                             
CONECT   16   15   17                                                       
CONECT   17   16   18   29                                                  
CONECT   18   17   19   59                                                  
CONECT   19   18   20   26                                                  
CONECT   20   19   21   25                                                  
CONECT   21   20   22   60                                                  
CONECT   22   21   23   61                                                  
CONECT   23   22   24   62                                                  
CONECT   24   23   25                                                       
CONECT   25   24   20   63                                                  
CONECT   26   19   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30   17                                                  
CONECT   30   29   31   15   64                                             
CONECT   31   30   65                                                       
CONECT   32   10   33    4   38                                             
CONECT   33   32   34   66   67                                             
CONECT   34   33   35   68   69                                             
CONECT   35   34   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35   38                                                       
CONECT   38   37   32   70   71                                             
CONECT   39    1                                                            
CONECT   40    1                                                            
CONECT   41    3                                                            
CONECT   42    3                                                            
CONECT   43    3                                                            
CONECT   44    5                                                            
CONECT   45    6                                                            
CONECT   46    6                                                            
CONECT   47    7                                                            
CONECT   48    7                                                            
CONECT   49    9                                                            
CONECT   50    9                                                            
CONECT   51    9                                                            
CONECT   52   10                                                            
CONECT   53   11                                                            
CONECT   54   11                                                            
CONECT   55   12                                                            
CONECT   56   14                                                            
CONECT   57   14                                                            
CONECT   58   14                                                            
CONECT   59   18                                                            
CONECT   60   21                                                            
CONECT   61   22                                                            
CONECT   62   23                                                            
CONECT   63   25                                                            
CONECT   64   30                                                            
CONECT   65   31                                                            
CONECT   66   33                                                            
CONECT   67   33                                                            
CONECT   68   34                                                            
CONECT   69   34                                                            
CONECT   70   38                                                            
CONECT   71   38                                                            
MASTER        0    0    0    0    0    0    0    0   71    0  152    0
END

RDKit          3D

71 76  0  0  0  0  0  0  0  0999 V2000
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    7.1288   -1.5455    4.2784 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.3668   -0.9945    3.3725 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5499    0.3820   -0.1658 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6325    0.3266   -2.8998 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0257    2.6112   -2.1231 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2054   -2.0739    1.4809 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1186   -0.5521    2.4056 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8101   -1.9485    3.3213 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7851   -0.7317    2.4831 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0369   -1.0615   -1.3488 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0845   -0.4824    0.0642 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  2  4  1  0
  4  5  1  1
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  6
  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  1  1
 16 17  1  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 19 26  1  0
 26 27  1  0
 27 28  2  0
 27 29  1  0
 29 30  1  0
 30 31  1  0
 10 32  1  0
 32 33  1  1
 33 34  1  0
 34 35  1  0
 35 36  2  0
 35 37  1  0
 37 38  1  0
 32  4  1  0
 15  8  1  0
 29 17  2  0
 38 32  1  0
 30 15  1  0
 25 20  1  0
  1 39  1  0
  1 40  1  0
  3 41  1  0
  3 42  1  0
  3 43  1  0
  5 44  1  0
  6 45  1  0
  6 46  1  0
  7 47  1  0
  7 48  1  0
  9 49  1  0
  9 50  1  0
  9 51  1  0
 10 52  1  1
 11 53  1  0
 11 54  1  0
 12 55  1  0
 14 56  1  0
 14 57  1  0
 14 58  1  0
 18 59  1  0
 21 60  1  0
 22 61  1  0
 23 62  1  0
 25 63  1  0
 30 64  1  6
 31 65  1  0
 33 66  1  0
 33 67  1  0
 34 68  1  0
 34 69  1  0
 38 70  1  0
 38 71  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Not Available

Chemical Formula

C₃₀H₃₃NO₇

Average Mass

519.5940 Da

Monoisotopic Mass

519.22570 Da

IUPAC Name

(2S,3S,4'aS,5'R,6'R,8'aR)-3,6'-dihydroxy-2',8'a-dimethyl-6'-(prop-1-en-2-yl)-6-(pyridin-3-yl)-3,4,4',4'a,6',7',8',8'a-octahydrodispiro[furo[3,2-c]pyran-2,1'-naphthalene-5',3''-oxane]-4,6''-dione

Traditional Name

(2S,3S,4'aS,5'R,6'R,8'aR)-3,6'-dihydroxy-2',8'a-dimethyl-6'-(prop-1-en-2-yl)-6-(pyridin-3-yl)-4',4'a,7',8'-tetrahydro-3H-dispiro[furo[3,2-c]pyran-2,1'-naphthalene-5',3''-oxane]-4,6''-dione

CAS Registry Number

Not Available

SMILES

CC(=C)[C@]1(O)CC[C@]2(C)[C@H](CC=C(C)[C@]22OC3=C([C@@H]2O)C(=O)OC(=C3)C2=CN=CC=C2)[C@@]11CCC(=O)OC1

InChI Identifier

InChI=1S/C30H33NO7/c1-17(2)29(35)12-11-27(4)22(28(29)10-9-23(32)36-16-28)8-7-18(3)30(27)25(33)24-21(38-30)14-20(37-26(24)34)19-6-5-13-31-15-19/h5-7,13-15,22,25,33,35H,1,8-12,16H2,2-4H3/t22-,25-,27+,28-,29+,30+/m0/s1

InChI Key

GADSICAILMLRQB-GVRUMSNVSA-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
Penicillium thiersii	NPAtlas	15787428

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Terpene lactones

Alternative Parents

Substituents

Terpene lactone
Sesquiterpenoid
Alkyl aryl ether
Delta valerolactone
Delta_valerolactone
Pyranone
Oxane
Pyridine
Pyran
Cyclic alcohol
Heteroaromatic compound
Vinylogous ester
Tertiary alcohol
Carboxylic acid ester
Lactone
Secondary alcohol
Carboxylic acid derivative
Ether
Oxacycle
Monocarboxylic acid or derivatives
Azacycle
Organoheterocyclic compound
Hydrocarbon derivative
Organic nitrogen compound
Organic oxide
Organopnictogen compound
Carbonyl group
Organonitrogen compound
Organooxygen compound
Alcohol
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	2.91	ALOGPS
logP	1.97	ChemAxon
logS	-4.6	ALOGPS
pKa (Strongest Acidic)	12.88	ChemAxon
pKa (Strongest Basic)	4.21	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	115.18 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	140.09 m³·mol⁻¹	ChemAxon
Polarizability	55.18 Å³	ChemAxon
Number of Rings	6	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

NPA019881

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

10216970

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

21593946

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for Oxalicine B (NP0005766)

MOL for NP0005766 (Oxalicine B)

3D MOL for NP0005766 (Oxalicine B)

3D SDF for NP0005766 (Oxalicine B)

3D-SDF for NP0005766 (Oxalicine B)

PDB for NP0005766 (Oxalicine B)

3D PDB for NP0005766 (Oxalicine B)

SMILES for NP0005766 (Oxalicine B)

INCHI for NP0005766 (Oxalicine B)

Structure for NP0005766 (Oxalicine B)

3D Structure for NP0005766 (Oxalicine B)