NP-MRD: Showing NP-Card for (+)-9-deoxygoniopypyrone (NP0039086)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2021-06-20 21:36:52 UTC

Updated at

2021-06-30 00:12:14 UTC

NP-MRD ID

NP0039086

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(+)-9-deoxygoniopypyrone

Provided By

JEOL Database JEOL Logo

Description

(+)-9-Deoxygoniopypyrone belongs to the class of organic compounds known as c-glycosyl compounds. These are glycoside in which a sugar group is bonded through one carbon to another group via a C-glycosidic bond. (+)-9-deoxygoniopypyrone is found in Goniothalamus tamirensis. (+)-9-deoxygoniopypyrone was first documented in 2003 (PMID: 12656612). Based on a literature review very few articles have been published on (+)-9-Deoxygoniopypyrone (PMID: 20410636).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202123363D          

 31 33  0  0  0  0            999 V2000
   -2.5723   -5.7676    0.0517 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8116   -4.8030    0.0774 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2174   -4.2548   -1.1955 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2706   -3.0793   -1.0181 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5066   -3.2137    0.2727 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5279   -3.1435    1.3745 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4644   -4.2368    1.2551 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2226   -1.7721    1.3420 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1054   -1.5968    2.4473 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8286   -1.4464   -0.0461 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.2442   -1.8564   -0.4266 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1121   -2.5703    0.4099 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4060   -2.8982   -0.0075 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8611   -2.5072   -1.2632 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0226   -1.7869   -2.1062 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7296   -1.4636   -1.6905 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9099   -1.7974   -1.1022 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6490   -5.0866   -1.6309 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0314   -4.0007   -1.8808 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4373   -3.0930   -1.8551 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2358   -2.4026    0.3780 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0445   -4.1683    0.2987 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0420   -3.2761    2.3477 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4204   -1.0374    1.5015 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6188   -0.7825    2.3005 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8820   -0.3478   -0.0698 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8054   -2.9118    1.3959 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0552   -3.4703    0.6514 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8658   -2.7687   -1.5838 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3709   -1.4797   -3.0887 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0865   -0.9027   -2.3677 H   0  0  0  0  0  0  0  0  0  0  0  0
 12 13  2  0  0  0  0
 15 16  1  0  0  0  0
 16 11  2  0  0  0  0
 11 12  1  0  0  0  0
 13 14  1  0  0  0  0
  5  6  1  0  0  0  0
  6  8  1  0  0  0  0
  8 10  1  0  0  0  0
 10 17  1  0  0  0  0
 17  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  3  1  0  0  0  0
  6  7  1  0  0  0  0
 10 11  1  0  0  0  0
  8  9  1  0  0  0  0
  7  2  1  0  0  0  0
  3  2  1  0  0  0  0
 14 15  2  0  0  0  0
  2  1  2  0  0  0  0
 12 27  1  0  0  0  0
 13 28  1  0  0  0  0
 14 29  1  0  0  0  0
 15 30  1  0  0  0  0
 16 31  1  0  0  0  0
  3 18  1  0  0  0  0
  3 19  1  0  0  0  0
  5 21  1  0  0  0  0
  5 22  1  0  0  0  0
 10 26  1  1  0  0  0
  4 20  1  6  0  0  0
  8 24  1  1  0  0  0
  9 25  1  0  0  0  0
  6 23  1  1  0  0  0
M  END

     RDKit          3D

 31 33  0  0  0  0  0  0  0  0999 V2000
   -2.5723   -5.7676    0.0517 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8116   -4.8030    0.0774 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2174   -4.2548   -1.1955 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2706   -3.0793   -1.0181 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5066   -3.2137    0.2727 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5279   -3.1435    1.3745 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4644   -4.2368    1.2551 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2226   -1.7721    1.3420 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1054   -1.5968    2.4473 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8286   -1.4464   -0.0461 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.2442   -1.8564   -0.4266 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1121   -2.5703    0.4099 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4060   -2.8982   -0.0075 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8611   -2.5072   -1.2632 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0226   -1.7869   -2.1062 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7296   -1.4636   -1.6905 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9099   -1.7974   -1.1022 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6490   -5.0866   -1.6309 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0314   -4.0007   -1.8808 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4373   -3.0930   -1.8551 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2358   -2.4026    0.3780 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0445   -4.1683    0.2987 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0420   -3.2761    2.3477 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4204   -1.0374    1.5015 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6188   -0.7825    2.3005 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8820   -0.3478   -0.0698 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8054   -2.9118    1.3959 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0552   -3.4703    0.6514 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8658   -2.7687   -1.5838 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3709   -1.4797   -3.0887 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0865   -0.9027   -2.3677 H   0  0  0  0  0  0  0  0  0  0  0  0
 12 13  2  0
 15 16  1  0
 16 11  2  0
 11 12  1  0
 13 14  1  0
  5  6  1  0
  6  8  1  0
  8 10  1  0
 10 17  1  0
 17  4  1  0
  4  5  1  0
  4  3  1  0
  6  7  1  0
 10 11  1  0
  8  9  1  0
  7  2  1  0
  3  2  1  0
 14 15  2  0
  2  1  2  0
 12 27  1  0
 13 28  1  0
 14 29  1  0
 15 30  1  0
 16 31  1  0
  3 18  1  0
  3 19  1  0
  5 21  1  0
  5 22  1  0
 10 26  1  1
  4 20  1  6
  8 24  1  1
  9 25  1  0
  6 23  1  1
M  END


  Mrv1652306202123363D          

 31 33  0  0  0  0            999 V2000
   -2.5723   -5.7676    0.0517 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8116   -4.8030    0.0774 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2174   -4.2548   -1.1955 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2706   -3.0793   -1.0181 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5066   -3.2137    0.2727 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5279   -3.1435    1.3745 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4644   -4.2368    1.2551 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2226   -1.7721    1.3420 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1054   -1.5968    2.4473 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8286   -1.4464   -0.0461 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.2442   -1.8564   -0.4266 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1121   -2.5703    0.4099 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4060   -2.8982   -0.0075 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8611   -2.5072   -1.2632 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0226   -1.7869   -2.1062 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7296   -1.4636   -1.6905 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9099   -1.7974   -1.1022 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6490   -5.0866   -1.6309 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0314   -4.0007   -1.8808 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4373   -3.0930   -1.8551 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2358   -2.4026    0.3780 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0445   -4.1683    0.2987 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0420   -3.2761    2.3477 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4204   -1.0374    1.5015 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6188   -0.7825    2.3005 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8820   -0.3478   -0.0698 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8054   -2.9118    1.3959 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0552   -3.4703    0.6514 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8658   -2.7687   -1.5838 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3709   -1.4797   -3.0887 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0865   -0.9027   -2.3677 H   0  0  0  0  0  0  0  0  0  0  0  0
 12 13  2  0  0  0  0
 15 16  1  0  0  0  0
 16 11  2  0  0  0  0
 11 12  1  0  0  0  0
 13 14  1  0  0  0  0
  5  6  1  0  0  0  0
  6  8  1  0  0  0  0
  8 10  1  0  0  0  0
 10 17  1  0  0  0  0
 17  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  3  1  0  0  0  0
  6  7  1  0  0  0  0
 10 11  1  0  0  0  0
  8  9  1  0  0  0  0
  7  2  1  0  0  0  0
  3  2  1  0  0  0  0
 14 15  2  0  0  0  0
  2  1  2  0  0  0  0
 12 27  1  0  0  0  0
 13 28  1  0  0  0  0
 14 29  1  0  0  0  0
 15 30  1  0  0  0  0
 16 31  1  0  0  0  0
  3 18  1  0  0  0  0
  3 19  1  0  0  0  0
  5 21  1  0  0  0  0
  5 22  1  0  0  0  0
 10 26  1  1  0  0  0
  4 20  1  6  0  0  0
  8 24  1  1  0  0  0
  9 25  1  0  0  0  0
  6 23  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0039086

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]O[C@]1([H])[C@@]([H])(O[C@]2([H])C([H])([H])C(=O)O[C@@]1([H])C2([H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H]

> <INCHI_IDENTIFIER>
InChI=1S/C13H14O4/c14-11-7-9-6-10(17-11)12(15)13(16-9)8-4-2-1-3-5-8/h1-5,9-10,12-13,15H,6-7H2/t9-,10-,12-,13-/m0/s1

> <INCHI_KEY>
ZPVLUTBGTWEMGV-UKJIMTQDSA-N

> <FORMULA>
C13H14O4

> <MOLECULAR_WEIGHT>
234.251

> <EXACT_MASS>
234.089208931

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
31

> <JCHEM_AVERAGE_POLARIZABILITY>
22.910712373799278

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,5S,7S,8S)-8-hydroxy-7-phenyl-2,6-dioxabicyclo[3.3.1]nonan-3-one

> <ALOGPS_LOGP>
0.82

> <JCHEM_LOGP>
0.9757887733333328

> <ALOGPS_LOGS>
-0.93

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.081005272300999

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6381682938955437

> <JCHEM_POLAR_SURFACE_AREA>
55.760000000000005

> <JCHEM_REFRACTIVITY>
59.07870000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.78e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,5S,7S,8S)-8-hydroxy-7-phenyl-2,6-dioxabicyclo[3.3.1]nonan-3-one

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 31 33  0  0  0  0  0  0  0  0999 V2000
   -2.5723   -5.7676    0.0517 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8116   -4.8030    0.0774 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2174   -4.2548   -1.1955 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2706   -3.0793   -1.0181 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5066   -3.2137    0.2727 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5279   -3.1435    1.3745 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4644   -4.2368    1.2551 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2226   -1.7721    1.3420 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1054   -1.5968    2.4473 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8286   -1.4464   -0.0461 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.2442   -1.8564   -0.4266 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1121   -2.5703    0.4099 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4060   -2.8982   -0.0075 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8611   -2.5072   -1.2632 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0226   -1.7869   -2.1062 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7296   -1.4636   -1.6905 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9099   -1.7974   -1.1022 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6490   -5.0866   -1.6309 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0314   -4.0007   -1.8808 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4373   -3.0930   -1.8551 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2358   -2.4026    0.3780 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0445   -4.1683    0.2987 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0420   -3.2761    2.3477 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4204   -1.0374    1.5015 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6188   -0.7825    2.3005 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8820   -0.3478   -0.0698 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8054   -2.9118    1.3959 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0552   -3.4703    0.6514 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8658   -2.7687   -1.5838 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3709   -1.4797   -3.0887 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0865   -0.9027   -2.3677 H   0  0  0  0  0  0  0  0  0  0  0  0
 12 13  2  0
 15 16  1  0
 16 11  2  0
 11 12  1  0
 13 14  1  0
  5  6  1  0
  6  8  1  0
  8 10  1  0
 10 17  1  0
 17  4  1  0
  4  5  1  0
  4  3  1  0
  6  7  1  0
 10 11  1  0
  8  9  1  0
  7  2  1  0
  3  2  1  0
 14 15  2  0
  2  1  2  0
 12 27  1  0
 13 28  1  0
 14 29  1  0
 15 30  1  0
 16 31  1  0
  3 18  1  0
  3 19  1  0
  5 21  1  0
  5 22  1  0
 10 26  1  1
  4 20  1  6
  8 24  1  1
  9 25  1  0
  6 23  1  1
M  END

HEADER    PROTEIN                                 20-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-JUN-21         0                                  
HETATM    1  O   UNK     0      -2.572  -5.768   0.052  0.00  0.00           O+0
HETATM    2  C   UNK     0      -1.812  -4.803   0.077  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.217  -4.255  -1.196  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.271  -3.079  -1.018  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.507  -3.214   0.273  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.528  -3.143   1.375  0.00  0.00           C+0
HETATM    7  O   UNK     0      -1.464  -4.237   1.255  0.00  0.00           O+0
HETATM    8  C   UNK     0      -1.223  -1.772   1.342  0.00  0.00           C+0
HETATM    9  O   UNK     0      -2.105  -1.597   2.447  0.00  0.00           O+0
HETATM   10  C   UNK     0      -1.829  -1.446  -0.046  0.00  0.00           C+0
HETATM   11  C   UNK     0      -3.244  -1.856  -0.427  0.00  0.00           C+0
HETATM   12  C   UNK     0      -4.112  -2.570   0.410  0.00  0.00           C+0
HETATM   13  C   UNK     0      -5.406  -2.898  -0.008  0.00  0.00           C+0
HETATM   14  C   UNK     0      -5.861  -2.507  -1.263  0.00  0.00           C+0
HETATM   15  C   UNK     0      -5.023  -1.787  -2.106  0.00  0.00           C+0
HETATM   16  C   UNK     0      -3.730  -1.464  -1.690  0.00  0.00           C+0
HETATM   17  O   UNK     0      -0.910  -1.797  -1.102  0.00  0.00           O+0
HETATM   18  H   UNK     0      -0.649  -5.087  -1.631  0.00  0.00           H+0
HETATM   19  H   UNK     0      -2.031  -4.001  -1.881  0.00  0.00           H+0
HETATM   20  H   UNK     0       0.437  -3.093  -1.855  0.00  0.00           H+0
HETATM   21  H   UNK     0       1.236  -2.403   0.378  0.00  0.00           H+0
HETATM   22  H   UNK     0       1.044  -4.168   0.299  0.00  0.00           H+0
HETATM   23  H   UNK     0      -0.042  -3.276   2.348  0.00  0.00           H+0
HETATM   24  H   UNK     0      -0.420  -1.037   1.502  0.00  0.00           H+0
HETATM   25  H   UNK     0      -2.619  -0.783   2.301  0.00  0.00           H+0
HETATM   26  H   UNK     0      -1.882  -0.348  -0.070  0.00  0.00           H+0
HETATM   27  H   UNK     0      -3.805  -2.912   1.396  0.00  0.00           H+0
HETATM   28  H   UNK     0      -6.055  -3.470   0.651  0.00  0.00           H+0
HETATM   29  H   UNK     0      -6.866  -2.769  -1.584  0.00  0.00           H+0
HETATM   30  H   UNK     0      -5.371  -1.480  -3.089  0.00  0.00           H+0
HETATM   31  H   UNK     0      -3.087  -0.903  -2.368  0.00  0.00           H+0
CONECT    1    2                                                            
CONECT    2    7    3    1                                                  
CONECT    3    4    2   18   19                                             
CONECT    4   17    5    3   20                                             
CONECT    5    6    4   21   22                                             
CONECT    6    5    8    7   23                                             
CONECT    7    6    2                                                       
CONECT    8    6   10    9   24                                             
CONECT    9    8   25                                                       
CONECT   10    8   17   11   26                                             
CONECT   11   16   12   10                                                  
CONECT   12   13   11   27                                                  
CONECT   13   12   14   28                                                  
CONECT   14   13   15   29                                                  
CONECT   15   16   14   30                                                  
CONECT   16   15   11   31                                                  
CONECT   17   10    4                                                       
CONECT   18    3                                                            
CONECT   19    3                                                            
CONECT   20    4                                                            
CONECT   21    5                                                            
CONECT   22    5                                                            
CONECT   23    6                                                            
CONECT   24    8                                                            
CONECT   25    9                                                            
CONECT   26   10                                                            
CONECT   27   12                                                            
CONECT   28   13                                                            
CONECT   29   14                                                            
CONECT   30   15                                                            
CONECT   31   16                                                            
MASTER        0    0    0    0    0    0    0    0   31    0   66    0
END

RDKit          3D

31 33  0  0  0  0  0  0  0  0999 V2000
   -2.5723   -5.7676    0.0517 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8116   -4.8030    0.0774 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2174   -4.2548   -1.1955 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2706   -3.0793   -1.0181 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5066   -3.2137    0.2727 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5279   -3.1435    1.3745 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4644   -4.2368    1.2551 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2226   -1.7721    1.3420 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1054   -1.5968    2.4473 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8286   -1.4464   -0.0461 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.2442   -1.8564   -0.4266 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1121   -2.5703    0.4099 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4060   -2.8982   -0.0075 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8611   -2.5072   -1.2632 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0226   -1.7869   -2.1062 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7296   -1.4636   -1.6905 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9099   -1.7974   -1.1022 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6490   -5.0866   -1.6309 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0314   -4.0007   -1.8808 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4373   -3.0930   -1.8551 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2358   -2.4026    0.3780 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0445   -4.1683    0.2987 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0420   -3.2761    2.3477 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4204   -1.0374    1.5015 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6188   -0.7825    2.3005 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8820   -0.3478   -0.0698 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8054   -2.9118    1.3959 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0552   -3.4703    0.6514 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8658   -2.7687   -1.5838 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3709   -1.4797   -3.0887 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0865   -0.9027   -2.3677 H   0  0  0  0  0  0  0  0  0  0  0  0
 12 13  2  0
 15 16  1  0
 16 11  2  0
 11 12  1  0
 13 14  1  0
  5  6  1  0
  6  8  1  0
  8 10  1  0
 10 17  1  0
 17  4  1  0
  4  5  1  0
  4  3  1  0
  6  7  1  0
 10 11  1  0
  8  9  1  0
  7  2  1  0
  3  2  1  0
 14 15  2  0
  2  1  2  0
 12 27  1  0
 13 28  1  0
 14 29  1  0
 15 30  1  0
 16 31  1  0
  3 18  1  0
  3 19  1  0
  5 21  1  0
  5 22  1  0
 10 26  1  1
  4 20  1  6
  8 24  1  1
  9 25  1  0
  6 23  1  1
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₃H₁₄O₄

Average Mass

234.2510 Da

Monoisotopic Mass

234.08921 Da

IUPAC Name

(1S,5S,7S,8S)-8-hydroxy-7-phenyl-2,6-dioxabicyclo[3.3.1]nonan-3-one

Traditional Name

(1S,5S,7S,8S)-8-hydroxy-7-phenyl-2,6-dioxabicyclo[3.3.1]nonan-3-one

CAS Registry Number

Not Available

SMILES

[H]O[C@]1([H])[C@@]([H])(O[C@]2([H])C([H])([H])C(=O)O[C@@]1([H])C2([H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H]

InChI Identifier

InChI=1S/C13H14O4/c14-11-7-9-6-10(17-11)12(15)13(16-9)8-4-2-1-3-5-8/h1-5,9-10,12-13,15H,6-7H2/t9-,10-,12-,13-/m0/s1

InChI Key

ZPVLUTBGTWEMGV-UKJIMTQDSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CDCl₃, 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
Goniothalamus tamirensis	JEOL database	Tai, B. H., et al, Chem. Pharm. Bull. 58, 521 (2010)

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as c-glycosyl compounds. These are glycoside in which a sugar group is bonded through one carbon to another group via a C-glycosidic bond.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

C-glycosyl compounds

Alternative Parents

Substituents

C-glycosyl compound
Delta valerolactone
Delta_valerolactone
Monocyclic benzene moiety
Benzenoid
Monosaccharide
Oxane
Carboxylic acid ester
Lactone
Secondary alcohol
Organoheterocyclic compound
Ether
Dialkyl ether
Oxacycle
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Alcohol
Carbonyl group
Hydrocarbon derivative
Organic oxide
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	0.82	ALOGPS
logP	0.98	ChemAxon
logS	-0.93	ALOGPS
pKa (Strongest Acidic)	13.08	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	55.76 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	59.08 m³·mol⁻¹	ChemAxon
Polarizability	22.91 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

9382115

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11207053

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Tai BH, Huyen VT, Huong TT, Nhiem NX, Choi EM, Kim JA, Long PQ, Cuong NM, Kim YH: New pyrano-pyrone from Goniothalamus tamirensis enhances the proliferation and differentiation of osteoblastic MC3T3-E1 cells. Chem Pharm Bull (Tokyo). 2010 Apr;58(4):521-5. doi: 10.1248/cpb.58.521. [PubMed:20410636 ]
Yamashita Y, Saito S, Ishitani H, Kobayashi S: Chiral hetero Diels-Alder products by enantioselective and diastereoselective zirconium catalysis. Scope, limitation, mechanism, and application to the concise synthesis of (+)-Prelactone C and (+)-9-deoxygoniopypyrone. J Am Chem Soc. 2003 Apr 2;125(13):3793-8. doi: 10.1021/ja028186k. [PubMed:12656612 ]
Tai, B. H., et al. (2010). Tai, B. H., et al, Chem. Pharm. Bull. 58, 521 (2010). Chem. Pharm. Bull..

Showing NP-Card for (+)-9-deoxygoniopypyrone (NP0039086)

MOL for NP0039086 ((+)-9-deoxygoniopypyrone)

3D MOL for NP0039086 ((+)-9-deoxygoniopypyrone)

3D SDF for NP0039086 ((+)-9-deoxygoniopypyrone)

3D-SDF for NP0039086 ((+)-9-deoxygoniopypyrone)

PDB for NP0039086 ((+)-9-deoxygoniopypyrone)

3D PDB for NP0039086 ((+)-9-deoxygoniopypyrone)

SMILES for NP0039086 ((+)-9-deoxygoniopypyrone)

INCHI for NP0039086 ((+)-9-deoxygoniopypyrone)

Structure for NP0039086 ((+)-9-deoxygoniopypyrone)

3D Structure for NP0039086 ((+)-9-deoxygoniopypyrone)