NP-MRD: Showing NP-Card for upuborneol A (NP0041644)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2021-06-20 23:30:22 UTC

Updated at

2021-06-30 00:16:16 UTC

NP-MRD ID

NP0041644

Secondary Accession Numbers

None

Natural Product Identification

Common Name

upuborneol A

Provided By

JEOL Database JEOL Logo

Description

Upuborneol A belongs to the class of organic compounds known as benzofurans. These are organic compounds containing a benzene ring fused to a furan. Furan is a five-membered aromatic ring with four carbon atoms and one oxygen atom. upuborneol A is found in Upuna borneensis. upuborneol A was first documented in 2012 (Ito, T., et al.). Based on a literature review very few articles have been published on Upuborneol A.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306212101303D          

 38 40  0  0  0  0            999 V2000
   -2.5067    0.4504    0.6624 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0885   -0.9467    1.0301 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8251   -1.6702    1.7053 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7759   -1.4926    0.5784 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4480   -2.8348    0.8591 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2799   -3.6820    1.5487 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7650   -3.4025    0.4405 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6760   -2.6326   -0.2710 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8540   -3.1427   -0.7170 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3741   -1.3130   -0.5381 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1715   -0.7513   -0.1191 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0577    0.5645   -0.4956 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3919    0.9457   -0.9410 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1603   -0.3231   -1.3155 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0564    1.6625    0.1229 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8919    3.0819   -0.1280 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3488    3.7496    1.1325 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1545    3.0970    1.5642 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9612    3.2231   -1.3304 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2562    4.3768   -2.1094 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2665    1.9465   -2.0917 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2500    1.6463   -3.0450 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8608    1.1808    1.1535 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5306    0.6187    1.0119 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5052    0.5791   -0.4227 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0823   -3.1743    1.8125 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9666   -4.4435    0.6762 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9186   -4.0724   -0.4380 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2094   -0.2830   -1.0091 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0790   -0.5585   -2.3818 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8814    3.4976   -0.3533 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0730    3.6705    1.9498 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1280    4.8072    0.9613 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4034    2.1623    1.6994 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0966    3.2714   -1.0470 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7620    4.2789   -2.9461 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2131    2.0561   -2.6352 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5310    1.3369   -2.5468 H   0  0  0  0  0  0  0  0  0  0  0  0
 13 15  1  1  0  0  0
 13 21  1  0  0  0  0
 10  8  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 10  1  0  0  0  0
  4  2  1  0  0  0  0
  8  7  2  0  0  0  0
  2  3  2  0  0  0  0
 21 19  1  0  0  0  0
  2  1  1  0  0  0  0
  7  5  1  0  0  0  0
  5  6  1  0  0  0  0
 19 16  1  0  0  0  0
  8  9  1  0  0  0  0
  5  4  2  0  0  0  0
 21 22  1  0  0  0  0
  4 11  1  0  0  0  0
 16 17  1  0  0  0  0
 10 11  2  0  0  0  0
 19 20  1  0  0  0  0
 16 15  1  0  0  0  0
 17 18  1  0  0  0  0
 21 37  1  6  0  0  0
 19 35  1  1  0  0  0
 16 31  1  6  0  0  0
  7 27  1  0  0  0  0
 14 29  1  0  0  0  0
 14 30  1  0  0  0  0
  1 23  1  0  0  0  0
  1 24  1  0  0  0  0
  1 25  1  0  0  0  0
  6 26  1  0  0  0  0
  9 28  1  0  0  0  0
 22 38  1  0  0  0  0
 17 32  1  0  0  0  0
 17 33  1  0  0  0  0
 20 36  1  0  0  0  0
 18 34  1  0  0  0  0
M  END

     RDKit          3D

 38 40  0  0  0  0  0  0  0  0999 V2000
   -2.5067    0.4504    0.6624 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0885   -0.9467    1.0301 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8251   -1.6702    1.7053 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7759   -1.4926    0.5784 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4480   -2.8348    0.8591 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2799   -3.6820    1.5487 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7650   -3.4025    0.4405 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6760   -2.6326   -0.2710 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8540   -3.1427   -0.7170 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3741   -1.3130   -0.5381 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1715   -0.7513   -0.1191 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0577    0.5645   -0.4956 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3919    0.9457   -0.9410 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1603   -0.3231   -1.3155 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0564    1.6625    0.1229 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8919    3.0819   -0.1280 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3488    3.7496    1.1325 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1545    3.0970    1.5642 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9612    3.2231   -1.3304 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2562    4.3768   -2.1094 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2665    1.9465   -2.0917 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2500    1.6463   -3.0450 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8608    1.1808    1.1535 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5306    0.6187    1.0119 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5052    0.5791   -0.4227 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0823   -3.1743    1.8125 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9666   -4.4435    0.6762 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9186   -4.0724   -0.4380 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2094   -0.2830   -1.0091 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0790   -0.5585   -2.3818 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8814    3.4976   -0.3533 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0730    3.6705    1.9498 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1280    4.8072    0.9613 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4034    2.1623    1.6994 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0966    3.2714   -1.0470 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7620    4.2789   -2.9461 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2131    2.0561   -2.6352 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5310    1.3369   -2.5468 H   0  0  0  0  0  0  0  0  0  0  0  0
 13 15  1  1
 13 21  1  0
 10  8  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 10  1  0
  4  2  1  0
  8  7  2  0
  2  3  2  0
 21 19  1  0
  2  1  1  0
  7  5  1  0
  5  6  1  0
 19 16  1  0
  8  9  1  0
  5  4  2  0
 21 22  1  0
  4 11  1  0
 16 17  1  0
 10 11  2  0
 19 20  1  0
 16 15  1  0
 17 18  1  0
 21 37  1  6
 19 35  1  1
 16 31  1  6
  7 27  1  0
 14 29  1  0
 14 30  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  6 26  1  0
  9 28  1  0
 22 38  1  0
 17 32  1  0
 17 33  1  0
 20 36  1  0
 18 34  1  0
M  END


  Mrv1652306212101303D          

 38 40  0  0  0  0            999 V2000
   -2.5067    0.4504    0.6624 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0885   -0.9467    1.0301 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8251   -1.6702    1.7053 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7759   -1.4926    0.5784 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4480   -2.8348    0.8591 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2799   -3.6820    1.5487 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7650   -3.4025    0.4405 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6760   -2.6326   -0.2710 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8540   -3.1427   -0.7170 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3741   -1.3130   -0.5381 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1715   -0.7513   -0.1191 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0577    0.5645   -0.4956 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3919    0.9457   -0.9410 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1603   -0.3231   -1.3155 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0564    1.6625    0.1229 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8919    3.0819   -0.1280 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3488    3.7496    1.1325 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1545    3.0970    1.5642 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9612    3.2231   -1.3304 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2562    4.3768   -2.1094 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2665    1.9465   -2.0917 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2500    1.6463   -3.0450 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8608    1.1808    1.1535 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5306    0.6187    1.0119 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5052    0.5791   -0.4227 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0823   -3.1743    1.8125 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9666   -4.4435    0.6762 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9186   -4.0724   -0.4380 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2094   -0.2830   -1.0091 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0790   -0.5585   -2.3818 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8814    3.4976   -0.3533 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0730    3.6705    1.9498 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1280    4.8072    0.9613 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4034    2.1623    1.6994 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0966    3.2714   -1.0470 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7620    4.2789   -2.9461 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2131    2.0561   -2.6352 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5310    1.3369   -2.5468 H   0  0  0  0  0  0  0  0  0  0  0  0
 13 15  1  1  0  0  0
 13 21  1  0  0  0  0
 10  8  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 10  1  0  0  0  0
  4  2  1  0  0  0  0
  8  7  2  0  0  0  0
  2  3  2  0  0  0  0
 21 19  1  0  0  0  0
  2  1  1  0  0  0  0
  7  5  1  0  0  0  0
  5  6  1  0  0  0  0
 19 16  1  0  0  0  0
  8  9  1  0  0  0  0
  5  4  2  0  0  0  0
 21 22  1  0  0  0  0
  4 11  1  0  0  0  0
 16 17  1  0  0  0  0
 10 11  2  0  0  0  0
 19 20  1  0  0  0  0
 16 15  1  0  0  0  0
 17 18  1  0  0  0  0
 21 37  1  6  0  0  0
 19 35  1  1  0  0  0
 16 31  1  6  0  0  0
  7 27  1  0  0  0  0
 14 29  1  0  0  0  0
 14 30  1  0  0  0  0
  1 23  1  0  0  0  0
  1 24  1  0  0  0  0
  1 25  1  0  0  0  0
  6 26  1  0  0  0  0
  9 28  1  0  0  0  0
 22 38  1  0  0  0  0
 17 32  1  0  0  0  0
 17 33  1  0  0  0  0
 20 36  1  0  0  0  0
 18 34  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0041644

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C([H])C(O[H])=C(C(=O)C([H])([H])[H])C2=C1C([H])([H])[C@@]1(O2)O[C@]([H])(C([H])([H])O[H])[C@@]([H])(O[H])[C@]1([H])O[H]

> <INCHI_IDENTIFIER>
InChI=1S/C14H16O8/c1-5(16)10-8(18)2-7(17)6-3-14(22-12(6)10)13(20)11(19)9(4-15)21-14/h2,9,11,13,15,17-20H,3-4H2,1H3/t9-,11-,13+,14+/m1/s1

> <INCHI_KEY>
VYJJGUJNZQPYSP-RCCPXBDUSA-N

> <FORMULA>
C14H16O8

> <MOLECULAR_WEIGHT>
312.274

> <EXACT_MASS>
312.084517475

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
38

> <JCHEM_AVERAGE_POLARIZABILITY>
29.477028612889644

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1-[(2S,3'S,4'S,5'R)-3',4,4',6-tetrahydroxy-5'-(hydroxymethyl)-3H-spiro[1-benzofuran-2,2'-oxolane]-7-yl]ethan-1-one

> <ALOGPS_LOGP>
-0.46

> <JCHEM_LOGP>
-0.3220417713333336

> <ALOGPS_LOGS>
-1.20

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.011746214037792

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.932449243473393

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9813947537322125

> <JCHEM_POLAR_SURFACE_AREA>
136.68

> <JCHEM_REFRACTIVITY>
72.11300000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.96e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1-[(2S,3'S,4'S,5'R)-3',4,4',6-tetrahydroxy-5'-(hydroxymethyl)-3H-spiro[1-benzofuran-2,2'-oxolane]-7-yl]ethanone

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 38 40  0  0  0  0  0  0  0  0999 V2000
   -2.5067    0.4504    0.6624 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0885   -0.9467    1.0301 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8251   -1.6702    1.7053 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7759   -1.4926    0.5784 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4480   -2.8348    0.8591 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2799   -3.6820    1.5487 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7650   -3.4025    0.4405 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6760   -2.6326   -0.2710 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8540   -3.1427   -0.7170 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3741   -1.3130   -0.5381 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1715   -0.7513   -0.1191 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0577    0.5645   -0.4956 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3919    0.9457   -0.9410 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1603   -0.3231   -1.3155 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0564    1.6625    0.1229 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8919    3.0819   -0.1280 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3488    3.7496    1.1325 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1545    3.0970    1.5642 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9612    3.2231   -1.3304 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2562    4.3768   -2.1094 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2665    1.9465   -2.0917 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2500    1.6463   -3.0450 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8608    1.1808    1.1535 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5306    0.6187    1.0119 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5052    0.5791   -0.4227 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0823   -3.1743    1.8125 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9666   -4.4435    0.6762 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9186   -4.0724   -0.4380 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2094   -0.2830   -1.0091 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0790   -0.5585   -2.3818 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8814    3.4976   -0.3533 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0730    3.6705    1.9498 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1280    4.8072    0.9613 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4034    2.1623    1.6994 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0966    3.2714   -1.0470 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7620    4.2789   -2.9461 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2131    2.0561   -2.6352 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5310    1.3369   -2.5468 H   0  0  0  0  0  0  0  0  0  0  0  0
 13 15  1  1
 13 21  1  0
 10  8  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 10  1  0
  4  2  1  0
  8  7  2  0
  2  3  2  0
 21 19  1  0
  2  1  1  0
  7  5  1  0
  5  6  1  0
 19 16  1  0
  8  9  1  0
  5  4  2  0
 21 22  1  0
  4 11  1  0
 16 17  1  0
 10 11  2  0
 19 20  1  0
 16 15  1  0
 17 18  1  0
 21 37  1  6
 19 35  1  1
 16 31  1  6
  7 27  1  0
 14 29  1  0
 14 30  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  6 26  1  0
  9 28  1  0
 22 38  1  0
 17 32  1  0
 17 33  1  0
 20 36  1  0
 18 34  1  0
M  END

HEADER    PROTEIN                                 21-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   21-JUN-21         0                                  
HETATM    1  C   UNK     0      -2.507   0.450   0.662  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.088  -0.947   1.030  0.00  0.00           C+0
HETATM    3  O   UNK     0      -2.825  -1.670   1.705  0.00  0.00           O+0
HETATM    4  C   UNK     0      -0.776  -1.493   0.578  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.448  -2.835   0.859  0.00  0.00           C+0
HETATM    6  O   UNK     0      -1.280  -3.682   1.549  0.00  0.00           O+0
HETATM    7  C   UNK     0       0.765  -3.402   0.441  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.676  -2.633  -0.271  0.00  0.00           C+0
HETATM    9  O   UNK     0       2.854  -3.143  -0.717  0.00  0.00           O+0
HETATM   10  C   UNK     0       1.374  -1.313  -0.538  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.172  -0.751  -0.119  0.00  0.00           C+0
HETATM   12  O   UNK     0       0.058   0.565  -0.496  0.00  0.00           O+0
HETATM   13  C   UNK     0       1.392   0.946  -0.941  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.160  -0.323  -1.315  0.00  0.00           C+0
HETATM   15  O   UNK     0       2.056   1.663   0.123  0.00  0.00           O+0
HETATM   16  C   UNK     0       1.892   3.082  -0.128  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.349   3.750   1.133  0.00  0.00           C+0
HETATM   18  O   UNK     0       0.155   3.097   1.564  0.00  0.00           O+0
HETATM   19  C   UNK     0       0.961   3.223  -1.330  0.00  0.00           C+0
HETATM   20  O   UNK     0       1.256   4.377  -2.109  0.00  0.00           O+0
HETATM   21  C   UNK     0       1.266   1.946  -2.092  0.00  0.00           C+0
HETATM   22  O   UNK     0       0.250   1.646  -3.045  0.00  0.00           O+0
HETATM   23  H   UNK     0      -1.861   1.181   1.153  0.00  0.00           H+0
HETATM   24  H   UNK     0      -3.531   0.619   1.012  0.00  0.00           H+0
HETATM   25  H   UNK     0      -2.505   0.579  -0.423  0.00  0.00           H+0
HETATM   26  H   UNK     0      -2.082  -3.174   1.813  0.00  0.00           H+0
HETATM   27  H   UNK     0       0.967  -4.444   0.676  0.00  0.00           H+0
HETATM   28  H   UNK     0       2.919  -4.072  -0.438  0.00  0.00           H+0
HETATM   29  H   UNK     0       3.209  -0.283  -1.009  0.00  0.00           H+0
HETATM   30  H   UNK     0       2.079  -0.559  -2.382  0.00  0.00           H+0
HETATM   31  H   UNK     0       2.881   3.498  -0.353  0.00  0.00           H+0
HETATM   32  H   UNK     0       2.073   3.671   1.950  0.00  0.00           H+0
HETATM   33  H   UNK     0       1.128   4.807   0.961  0.00  0.00           H+0
HETATM   34  H   UNK     0       0.403   2.162   1.699  0.00  0.00           H+0
HETATM   35  H   UNK     0      -0.097   3.271  -1.047  0.00  0.00           H+0
HETATM   36  H   UNK     0       0.762   4.279  -2.946  0.00  0.00           H+0
HETATM   37  H   UNK     0       2.213   2.056  -2.635  0.00  0.00           H+0
HETATM   38  H   UNK     0      -0.531   1.337  -2.547  0.00  0.00           H+0
CONECT    1    2   23   24   25                                             
CONECT    2    4    3    1                                                  
CONECT    3    2                                                            
CONECT    4    2    5   11                                                  
CONECT    5    7    6    4                                                  
CONECT    6    5   26                                                       
CONECT    7    8    5   27                                                  
CONECT    8   10    7    9                                                  
CONECT    9    8   28                                                       
CONECT   10    8   14   11                                                  
CONECT   11   12    4   10                                                  
CONECT   12   11   13                                                       
CONECT   13   15   21   12   14                                             
CONECT   14   13   10   29   30                                             
CONECT   15   13   16                                                       
CONECT   16   19   17   15   31                                             
CONECT   17   16   18   32   33                                             
CONECT   18   17   34                                                       
CONECT   19   21   16   20   35                                             
CONECT   20   19   36                                                       
CONECT   21   13   19   22   37                                             
CONECT   22   21   38                                                       
CONECT   23    1                                                            
CONECT   24    1                                                            
CONECT   25    1                                                            
CONECT   26    6                                                            
CONECT   27    7                                                            
CONECT   28    9                                                            
CONECT   29   14                                                            
CONECT   30   14                                                            
CONECT   31   16                                                            
CONECT   32   17                                                            
CONECT   33   17                                                            
CONECT   34   18                                                            
CONECT   35   19                                                            
CONECT   36   20                                                            
CONECT   37   21                                                            
CONECT   38   22                                                            
MASTER        0    0    0    0    0    0    0    0   38    0   80    0
END

RDKit          3D

38 40  0  0  0  0  0  0  0  0999 V2000
   -2.5067    0.4504    0.6624 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0885   -0.9467    1.0301 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8251   -1.6702    1.7053 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7759   -1.4926    0.5784 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4480   -2.8348    0.8591 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2799   -3.6820    1.5487 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7650   -3.4025    0.4405 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6760   -2.6326   -0.2710 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8540   -3.1427   -0.7170 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3741   -1.3130   -0.5381 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1715   -0.7513   -0.1191 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0577    0.5645   -0.4956 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3919    0.9457   -0.9410 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1603   -0.3231   -1.3155 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0564    1.6625    0.1229 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8919    3.0819   -0.1280 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3488    3.7496    1.1325 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1545    3.0970    1.5642 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9612    3.2231   -1.3304 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2562    4.3768   -2.1094 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2665    1.9465   -2.0917 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2500    1.6463   -3.0450 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8608    1.1808    1.1535 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5306    0.6187    1.0119 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5052    0.5791   -0.4227 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0823   -3.1743    1.8125 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9666   -4.4435    0.6762 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9186   -4.0724   -0.4380 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2094   -0.2830   -1.0091 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0790   -0.5585   -2.3818 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8814    3.4976   -0.3533 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0730    3.6705    1.9498 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1280    4.8072    0.9613 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4034    2.1623    1.6994 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0966    3.2714   -1.0470 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7620    4.2789   -2.9461 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2131    2.0561   -2.6352 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5310    1.3369   -2.5468 H   0  0  0  0  0  0  0  0  0  0  0  0
 13 15  1  1
 13 21  1  0
 10  8  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 10  1  0
  4  2  1  0
  8  7  2  0
  2  3  2  0
 21 19  1  0
  2  1  1  0
  7  5  1  0
  5  6  1  0
 19 16  1  0
  8  9  1  0
  5  4  2  0
 21 22  1  0
  4 11  1  0
 16 17  1  0
 10 11  2  0
 19 20  1  0
 16 15  1  0
 17 18  1  0
 21 37  1  6
 19 35  1  1
 16 31  1  6
  7 27  1  0
 14 29  1  0
 14 30  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  6 26  1  0
  9 28  1  0
 22 38  1  0
 17 32  1  0
 17 33  1  0
 20 36  1  0
 18 34  1  0
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₄H₁₆O₈

Average Mass

312.2740 Da

Monoisotopic Mass

312.08452 Da

IUPAC Name

1-[(2S,3'S,4'S,5'R)-3',4,4',6-tetrahydroxy-5'-(hydroxymethyl)-3H-spiro[1-benzofuran-2,2'-oxolane]-7-yl]ethan-1-one

Traditional Name

1-[(2S,3'S,4'S,5'R)-3',4,4',6-tetrahydroxy-5'-(hydroxymethyl)-3H-spiro[1-benzofuran-2,2'-oxolane]-7-yl]ethanone

CAS Registry Number

Not Available

SMILES

[H]OC1=C([H])C(O[H])=C(C(=O)C([H])([H])[H])C2=C1C([H])([H])[C@@]1(O2)O[C@]([H])(C([H])([H])O[H])[C@@]([H])(O[H])[C@]1([H])O[H]

InChI Identifier

InChI=1S/C14H16O8/c1-5(16)10-8(18)2-7(17)6-3-14(22-12(6)10)13(20)11(19)9(4-15)21-14/h2,9,11,13,15,17-20H,3-4H2,1H3/t9-,11-,13+,14+/m1/s1

InChI Key

VYJJGUJNZQPYSP-RCCPXBDUSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Upuna borneensis	JEOL database	Ito, T., et al, Phytochem. Lett. 5, 325 (2012)

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzofurans. These are organic compounds containing a benzene ring fused to a furan. Furan is a five-membered aromatic ring with four carbon atoms and one oxygen atom.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzofurans

Sub Class

Not Available

Direct Parent

Benzofurans

Alternative Parents

Substituents

Acetophenone
Benzofuran
Coumaran
Aryl alkyl ketone
Aryl ketone
1-hydroxy-2-unsubstituted benzenoid
Ketal
Monosaccharide
Benzenoid
Tetrahydrofuran
Vinylogous acid
Ketone
Secondary alcohol
Polyol
Acetal
Oxacycle
Primary alcohol
Organooxygen compound
Hydrocarbon derivative
Organic oxide
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	-0.46	ALOGPS
logP	-0.32	ChemAxon
logS	-1.2	ALOGPS
pKa (Strongest Acidic)	7.93	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	136.68 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	72.11 m³·mol⁻¹	ChemAxon
Polarizability	29.48 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	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

102444342

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Ito, T., et al. (2012). Ito, T., et al, Phytochem. Lett. 5, 325 (2012). Phytochem..

Showing NP-Card for upuborneol A (NP0041644)

MOL for NP0041644 (upuborneol A)

3D MOL for NP0041644 (upuborneol A)

3D SDF for NP0041644 (upuborneol A)

3D-SDF for NP0041644 (upuborneol A)

PDB for NP0041644 (upuborneol A)

3D PDB for NP0041644 (upuborneol A)

SMILES for NP0041644 (upuborneol A)

INCHI for NP0041644 (upuborneol A)

Structure for NP0041644 (upuborneol A)

3D Structure for NP0041644 (upuborneol A)