NP-MRD: Showing NP-Card for methyl 2'-(furan-3-carbonyl)-5',8'-dihydroxy-3',8'-dimethoxy-2',2'',2'',5',8'a-pentamethyl-6'',7'-dioxo-4',4'a-dihydro-3'h-dispiro[oxirane-2,1'-naphthalene-6',3''-pyran]-3-carboxylate (NP0331059)

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Record Information

Version

1.0

Created at

2022-09-12 17:01:39 UTC

Updated at

2022-09-12 17:01:39 UTC

NP-MRD ID

NP0331059

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl 2'-(furan-3-carbonyl)-5',8'-dihydroxy-3',8'-dimethoxy-2',2'',2'',5',8'a-pentamethyl-6'',7'-dioxo-4',4'a-dihydro-3'h-dispiro[oxirane-2,1'-naphthalene-6',3''-pyran]-3-carboxylate

Description

Methyl 2'-(furan-3-carbonyl)-5',8'-dihydroxy-3',8'-dimethoxy-2',2'',2'',5',8'a-pentamethyl-6'',7'-dioxo-2',2'',3',4',4'a,5',6'',7',8',8'a-decahydrodispiro[oxirane-2,1'-naphthalene-6',3''-pyran]-3-carboxylate belongs to the class of organic compounds known as aryl alkyl ketones. These are ketones have the generic structure RC(=O)R', where R = aryl group and R'=alkyl group. methyl 2'-(furan-3-carbonyl)-5',8'-dihydroxy-3',8'-dimethoxy-2',2'',2'',5',8'a-pentamethyl-6'',7'-dioxo-4',4'a-dihydro-3'h-dispiro[oxirane-2,1'-naphthalene-6',3''-pyran]-3-carboxylate is found in Harrisonia abyssinica. It was first documented in 2022 (PMID: 36130844). Based on a literature review a significant number of articles have been published on methyl 2'-(furan-3-carbonyl)-5',8'-dihydroxy-3',8'-dimethoxy-2',2'',2'',5',8'a-pentamethyl-6'',7'-dioxo-2',2'',3',4',4'a,5',6'',7',8',8'a-decahydrodispiro[oxirane-2,1'-naphthalene-6',3''-pyran]-3-carboxylate (PMID: 36130843) (PMID: 36130842) (PMID: 36130841) (PMID: 36130840) (PMID: 36130836) (PMID: 36130839).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309122219012D          

 41 45  0  0  0  0            999 V2000
    1.7598   -1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5792   -2.0310    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0717   -1.3691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8215   -1.7132    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7447   -0.6116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0828   -0.1192    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8402    0.2078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5132    0.9652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8241    0.5117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9469    1.5652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1833    2.3556    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1442    1.3747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8265    0.6133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0042    0.6802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1863    1.4829    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5183    1.9121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0057    1.6271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6787    2.3846    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1712    3.0465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8252    1.5316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1521    0.7742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9716    0.6786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9234    1.5022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7743    0.8691    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2986   -0.0788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7910    0.5831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6105    0.4876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    7.7569   -0.3654    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    4.8800   -1.1895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5015   -1.6519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8061   -0.7407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6255   -1.5457    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9867   -0.6452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1840   -0.8357    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0349   -1.4688    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9967   -2.2929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6597    0.1123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1672   -0.5496    0.0000 C   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  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 12 16  2  0  0  0  0
  8 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 17 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
 22 25  1  0  0  0  0
 25 26  1  0  0  0  0
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 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 28 30  1  0  0  0  0
 30 31  1  0  0  0  0
 25 31  1  0  0  0  0
 31 32  1  0  0  0  0
 31 33  1  0  0  0  0
 25 34  1  0  0  0  0
 34 35  2  0  0  0  0
 34 36  1  0  0  0  0
 36 37  1  0  0  0  0
 36 38  1  0  0  0  0
 38 39  1  0  0  0  0
 36 40  1  0  0  0  0
 21 40  1  0  0  0  0
  7 40  1  0  0  0  0
 40 41  1  0  0  0  0
M  END

     RDKit          3D

 77 81  0  0  0  0  0  0  0  0999 V2000
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   -1.7285    4.0583    0.4013 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6593    3.0960    0.7543 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5117    3.5496    1.5828 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7515    1.7234    0.3007 C   0  0  1  0  0  0  0  0  0  0  0  0
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   -1.7710    0.8196   -0.2486 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3499    1.0644   -0.5096 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1795    2.0911   -1.6088 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3783   -0.1756   -1.0373 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4344   -0.7785   -2.0957 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5954   -1.4913   -1.3299 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3328   -2.0307   -2.3805 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0534   -3.3644   -2.5974 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2616   -0.6356   -0.3764 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.7510   -0.6277   -0.7736 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.5468    0.1252    0.0368 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4039    1.3423    0.0685 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.5258    0.5728    2.0208 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3890    0.7082    2.9519 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6946   -0.5378    1.9116 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3424   -0.9811    0.5699 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6720   -1.1879   -0.1447 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7099   -2.3092    0.7974 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4528    0.4207    1.0612 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4138   -0.2206    2.0900 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5139    1.5027    0.6716 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3255    2.5966    0.2717 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1736    1.9187    1.7467 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6070    2.3240    2.7961 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.0006    1.6200   -2.6149 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.9517   -1.2163   -1.6848 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.9502   -3.1972   -0.4766 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6979   -5.1938    1.0434 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3195   -2.6891    3.4584 H   0  0  0  0  0  0  0  0  0  0  0  0
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    1.8619   -0.8631   -3.1897 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8331   -2.0880   -1.9402 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9578    1.0311   -2.5569 H   0  0  0  0  0  0  0  0  0  0  0  0
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    1.6770   -2.3209    1.1368 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8846   -3.0454   -0.0448 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2654   -2.8474    1.6374 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9426    3.4605    0.4705 H   0  0  0  0  0  0  0  0  0  0  0  0
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    0.0010    2.8645    3.5814 H   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1652309122219012D          

 41 45  0  0  0  0            999 V2000
    1.7598   -1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5792   -2.0310    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0717   -1.3691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8215   -1.7132    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7447   -0.6116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0828   -0.1192    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8402    0.2078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5132    0.9652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8241    0.5117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9469    1.5652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1833    2.3556    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1442    1.3747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8265    0.6133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0042    0.6802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1863    1.4829    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5183    1.9121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0057    1.6271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6787    2.3846    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1712    3.0465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8252    1.5316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1521    0.7742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9716    0.6786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9234    1.5022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7743    0.8691    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2986   -0.0788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7910    0.5831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6105    0.4876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9375   -0.2699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7569   -0.3654    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4450   -0.9318    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6256   -0.8362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8800   -1.1895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5015   -1.6519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8061   -0.7407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6255   -1.5457    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9867   -0.6452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1840   -0.8357    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0349   -1.4688    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9967   -2.2929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6597    0.1123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1672   -0.5496    0.0000 C   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  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 12 16  2  0  0  0  0
  8 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 17 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
 22 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 28 30  1  0  0  0  0
 30 31  1  0  0  0  0
 25 31  1  0  0  0  0
 31 32  1  0  0  0  0
 31 33  1  0  0  0  0
 25 34  1  0  0  0  0
 34 35  2  0  0  0  0
 34 36  1  0  0  0  0
 36 37  1  0  0  0  0
 36 38  1  0  0  0  0
 38 39  1  0  0  0  0
 36 40  1  0  0  0  0
 21 40  1  0  0  0  0
  7 40  1  0  0  0  0
 40 41  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0331059

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1CC2C(C)(O)C3(C=CC(=O)OC3(C)C)C(=O)C(O)(OC)C2(C)C2(OC2C(=O)OC)C1(C)C(=O)C1=COC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C29H36O12/c1-23(2)27(11-9-18(30)40-23)22(33)29(35,38-8)25(4)16(26(27,5)34)13-17(36-6)24(3,19(31)15-10-12-39-14-15)28(25)20(41-28)21(32)37-7/h9-12,14,16-17,20,34-35H,13H2,1-8H3

> <INCHI_KEY>
WWAGAEMNVQWISE-UHFFFAOYSA-N

> <FORMULA>
C29H36O12

> <MOLECULAR_WEIGHT>
576.595

> <EXACT_MASS>
576.220676599

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
77

> <JCHEM_AVERAGE_POLARIZABILITY>
56.58135023459566

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl 2'-(furan-3-carbonyl)-5',8'-dihydroxy-3',8'-dimethoxy-2',2'',2'',5',8'a-pentamethyl-6'',7'-dioxo-2',2'',3',4',4'a,5',6'',7',8',8'a-decahydrodispiro[oxirane-2,1'-naphthalene-6',3''-pyran]-3-carboxylate

> <JCHEM_LOGP>
2.0276473246666664

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.006096862571844

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.875097831046233

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9583152668136075

> <JCHEM_POLAR_SURFACE_AREA>
171.32999999999998

> <JCHEM_REFRACTIVITY>
139.2741

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
methyl 2'-(furan-3-carbonyl)-5',8'-dihydroxy-3',8'-dimethoxy-2',2'',2'',5',8'a-pentamethyl-6'',7'-dioxo-4',4'a-dihydro-3'H-dispiro[oxirane-2,1'-naphthalene-6',3''-pyran]-3-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 12-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-SEP-22         0                                  
HETATM    1  C   UNK     0       3.285  -3.613   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       4.815  -3.791   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       5.734  -2.556   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       7.133  -3.198   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       5.123  -1.142   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       3.888  -0.222   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       5.302   0.388   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.691   1.802   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.405   0.955   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.634   2.922   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       4.076   4.397   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       2.136   2.566   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.543   1.145   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.008   1.270   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -0.348   2.768   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       0.967   3.569   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.611   3.037   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       5.000   4.451   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       5.920   5.687   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       7.140   2.859   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       7.751   1.445   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       9.280   1.267   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       9.190   2.804   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      10.779   1.622   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       9.891  -0.147   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      10.810   1.088   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      12.340   0.910   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      12.950  -0.504   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      14.480  -0.682   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0      12.031  -1.739   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      10.501  -1.561   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       9.109  -2.220   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      10.269  -3.083   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       8.971  -1.383   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       8.634  -2.885   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0       7.442  -1.204   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0       5.943  -1.560   0.000  0.00  0.00           O+0
HETATM   38  O   UNK     0       7.532  -2.742   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0       7.461  -4.280   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       6.831   0.210   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0       5.912  -1.026   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6    7                                                  
CONECT    6    5    7                                                       
CONECT    7    6    5    8   40                                             
CONECT    8    7    9   10   17                                             
CONECT    9    8                                                            
CONECT   10    8   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   16                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   12                                                       
CONECT   17    8   18   20                                                  
CONECT   18   17   19                                                       
CONECT   19   18                                                            
CONECT   20   17   21                                                       
CONECT   21   20   22   40                                                  
CONECT   22   21   23   24   25                                             
CONECT   23   22                                                            
CONECT   24   22                                                            
CONECT   25   22   26   31   34                                             
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31                                                       
CONECT   31   30   25   32   33                                             
CONECT   32   31                                                            
CONECT   33   31                                                            
CONECT   34   25   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34   37   38   40                                             
CONECT   37   36                                                            
CONECT   38   36   39                                                       
CONECT   39   38                                                            
CONECT   40   36   21    7   41                                             
CONECT   41   40                                                            
MASTER        0    0    0    0    0    0    0    0   41    0   90    0
END

View in JSmol

Synonyms

Value	Source
Methyl 2'-(furan-3-carbonyl)-5',8'-dihydroxy-3',8'-dimethoxy-2',2'',2'',5',8'a-pentamethyl-6'',7'-dioxo-2',2'',3',4',4'a,5',6'',7',8',8'a-decahydrodispiro[oxirane-2,1'-naphthalene-6',3''-pyran]-3-carboxylic acid	Generator

Chemical Formula

C₂₉H₃₆O₁₂

Average Mass

576.5950 Da

Monoisotopic Mass

576.22068 Da

IUPAC Name

methyl 2'-(furan-3-carbonyl)-5',8'-dihydroxy-3',8'-dimethoxy-2',2'',2'',5',8'a-pentamethyl-6'',7'-dioxo-2',2'',3',4',4'a,5',6'',7',8',8'a-decahydrodispiro[oxirane-2,1'-naphthalene-6',3''-pyran]-3-carboxylate

Traditional Name

methyl 2'-(furan-3-carbonyl)-5',8'-dihydroxy-3',8'-dimethoxy-2',2'',2'',5',8'a-pentamethyl-6'',7'-dioxo-4',4'a-dihydro-3'H-dispiro[oxirane-2,1'-naphthalene-6',3''-pyran]-3-carboxylate

CAS Registry Number

Not Available

SMILES

COC1CC2C(C)(O)C3(C=CC(=O)OC3(C)C)C(=O)C(O)(OC)C2(C)C2(OC2C(=O)OC)C1(C)C(=O)C1=COC=C1

InChI Identifier

InChI=1S/C29H36O12/c1-23(2)27(11-9-18(30)40-23)22(33)29(35,38-8)25(4)16(26(27,5)34)13-17(36-6)24(3,19(31)15-10-12-39-14-15)28(25)20(41-28)21(32)37-7/h9-12,14,16-17,20,34-35H,13H2,1-8H3

InChI Key

WWAGAEMNVQWISE-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Harrisonia abyssinica	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as aryl alkyl ketones. These are ketones have the generic structure RC(=O)R', where R = aryl group and R'=alkyl group.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Aryl alkyl ketones

Alternative Parents

Substituents

Aryl alkyl ketone
Dihydropyranone
Dicarboxylic acid or derivatives
Oxirane carboxylic acid
Oxirane carboxylic acid or derivatives
Pyran
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Methyl ester
Tertiary alcohol
Heteroaromatic compound
Cyclic alcohol
Furan
Carboxylic acid ester
Hemiacetal
Lactone
Ether
Oxirane
Dialkyl ether
Carboxylic acid derivative
Oxacycle
Organoheterocyclic compound
Organic oxide
Alcohol
Hydrocarbon derivative
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	2.03	ChemAxon
pKa (Strongest Acidic)	9.88	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	171.33 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	139.27 m³·mol⁻¹	ChemAxon
Polarizability	56.58 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

162870920

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Cani I, Righini M, Cenni P, Foschi M: Teaching NeuroImage: Partially Reversible Widespread Leukoencephalopathy Associated With Atypical Hemolytic Uremic Syndrome. Neurology. 2022 Sep 21. pii: WNL.0000000000201378. doi: 10.1212/WNL.0000000000201378. [PubMed:36130844 ]
Sasaki R, Morimoto S, Ozawa F, Okano H, Yoshida M, Ishiura H, Tsuji S, Kuzuhara S, Kokubo Y: APOE Alleles With Tau and Abeta Pathology In Patients With Amyotrophic Lateral Sclerosis and Parkinsonism-Dementia Complex in the Kii Peninsula. Neurology. 2022 Sep 21. pii: WNL.0000000000201156. doi: 10.1212/WNL.0000000000201156. [PubMed:36130843 ]
Zhang Z, Wang M, Gill D, Liu X: Genetically Predicted Smoking and Alcohol Consumption and Functional Outcome After Ischemic Stroke. Neurology. 2022 Sep 21. pii: WNL.0000000000201291. doi: 10.1212/WNL.0000000000201291. [PubMed:36130842 ]
Khamis S, Mitakidou MR, Champion M, Goyal S, Jones RL, Siddiqui A, Sabanathan S, Hedderly T, Lin JP, Jungbluth H, Papandreou A: Clinical Reasoning: A Teenage Girl With Progressive Hyperkinetic Movements, Seizures, and Encephalopathy. Neurology. 2022 Sep 21. pii: WNL.0000000000201385. doi: 10.1212/WNL.0000000000201385. [PubMed:36130841 ]
Rosenberg A, Ohlund-Wistbacka U, Hall A, Bonnard A, Hagman G, Ryden M, Thunborg C, Wiggenraad F, Sandebring-Matton A, Solomon A, Kivipelto M: beta-Amyloid, Tau, Neurodegeneration Classification and Eligibility for Anti-amyloid Treatment in a Memory Clinic Population. Neurology. 2022 Sep 21. pii: WNL.0000000000201043. doi: 10.1212/WNL.0000000000201043. [PubMed:36130840 ]
Yu H, Cai G, Wu J, Li Q: Clinical Phenotypic Variability and Significance of Pneumolabyrinth After Tympanum-Penetrating Injury. Ear Nose Throat J. 2022 Sep 21:1455613221128132. doi: 10.1177/01455613221128132. [PubMed:36130836 ]
Silverman A, Beres S: Child Neurology: Horner Syndrome in an Otherwise Well-Appearing Infant. Neurology. 2022 Sep 21. pii: WNL.0000000000201377. doi: 10.1212/WNL.0000000000201377. [PubMed:36130839 ]
Harada Y, Wang SH, Juel VC: Clinical Reasoning: A 36-Year-Old Man With Asymmetric Muscle Weakness. Neurology. 2022 Sep 21. pii: WNL.0000000000201379. doi: 10.1212/WNL.0000000000201379. [PubMed:36130838 ]
Guest O, Memon AA, Chukweubuka A, Zaheer M, Siddiqi N: Robotic low anterior resection for locally advanced rectal cancer - A video vignette. Colorectal Dis. 2022 Sep 21. doi: 10.1111/codi.16345. [PubMed:36130837 ]
Pellicori P, Kalra PR, Clark AL, Friday JM, Cleland JGF: Chronic kidney disease (CKD) and CKD-ism in heart failure - what a mess! Eur J Heart Fail. 2022 Sep 21. doi: 10.1002/ejhf.2696. [PubMed:36130835 ]
LOTUS database [Link]

Showing NP-Card for methyl 2'-(furan-3-carbonyl)-5',8'-dihydroxy-3',8'-dimethoxy-2',2'',2'',5',8'a-pentamethyl-6'',7'-dioxo-4',4'a-dihydro-3'h-dispiro[oxirane-2,1'-naphthalene-6',3''-pyran]-3-carboxylate (NP0331059)

MOL for NP0331059 (methyl 2'-(furan-3-carbonyl)-5',8'-dihydroxy-3',8'-dimethoxy-2',2'',2'',5',8'a-pentamethyl-6'',7'-dioxo-4',4'a-dihydro-3'h-dispiro[oxirane-2,1'-naphthalene-6',3''-pyran]-3-carboxylate)

3D MOL for NP0331059 (methyl 2'-(furan-3-carbonyl)-5',8'-dihydroxy-3',8'-dimethoxy-2',2'',2'',5',8'a-pentamethyl-6'',7'-dioxo-4',4'a-dihydro-3'h-dispiro[oxirane-2,1'-naphthalene-6',3''-pyran]-3-carboxylate)

3D SDF for NP0331059 (methyl 2'-(furan-3-carbonyl)-5',8'-dihydroxy-3',8'-dimethoxy-2',2'',2'',5',8'a-pentamethyl-6'',7'-dioxo-4',4'a-dihydro-3'h-dispiro[oxirane-2,1'-naphthalene-6',3''-pyran]-3-carboxylate)

3D-SDF for NP0331059 (methyl 2'-(furan-3-carbonyl)-5',8'-dihydroxy-3',8'-dimethoxy-2',2'',2'',5',8'a-pentamethyl-6'',7'-dioxo-4',4'a-dihydro-3'h-dispiro[oxirane-2,1'-naphthalene-6',3''-pyran]-3-carboxylate)

PDB for NP0331059 (methyl 2'-(furan-3-carbonyl)-5',8'-dihydroxy-3',8'-dimethoxy-2',2'',2'',5',8'a-pentamethyl-6'',7'-dioxo-4',4'a-dihydro-3'h-dispiro[oxirane-2,1'-naphthalene-6',3''-pyran]-3-carboxylate)

3D PDB for NP0331059 (methyl 2'-(furan-3-carbonyl)-5',8'-dihydroxy-3',8'-dimethoxy-2',2'',2'',5',8'a-pentamethyl-6'',7'-dioxo-4',4'a-dihydro-3'h-dispiro[oxirane-2,1'-naphthalene-6',3''-pyran]-3-carboxylate)

SMILES for NP0331059 (methyl 2'-(furan-3-carbonyl)-5',8'-dihydroxy-3',8'-dimethoxy-2',2'',2'',5',8'a-pentamethyl-6'',7'-dioxo-4',4'a-dihydro-3'h-dispiro[oxirane-2,1'-naphthalene-6',3''-pyran]-3-carboxylate)

INCHI for NP0331059 (methyl 2'-(furan-3-carbonyl)-5',8'-dihydroxy-3',8'-dimethoxy-2',2'',2'',5',8'a-pentamethyl-6'',7'-dioxo-4',4'a-dihydro-3'h-dispiro[oxirane-2,1'-naphthalene-6',3''-pyran]-3-carboxylate)

Structure for NP0331059 (methyl 2'-(furan-3-carbonyl)-5',8'-dihydroxy-3',8'-dimethoxy-2',2'',2'',5',8'a-pentamethyl-6'',7'-dioxo-4',4'a-dihydro-3'h-dispiro[oxirane-2,1'-naphthalene-6',3''-pyran]-3-carboxylate)

3D Structure for NP0331059 (methyl 2'-(furan-3-carbonyl)-5',8'-dihydroxy-3',8'-dimethoxy-2',2'',2'',5',8'a-pentamethyl-6'',7'-dioxo-4',4'a-dihydro-3'h-dispiro[oxirane-2,1'-naphthalene-6',3''-pyran]-3-carboxylate)