NP-MRD: Showing NP-Card for (6S,7R,8R,9S)-6-oxaspiro-7,8-dihydroxymegastigman-4-en-3-one (NP0042395)

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Record Information

Version

2.0

Created at

2021-06-21 00:04:17 UTC

Updated at

2021-06-30 00:17:27 UTC

NP-MRD ID

NP0042395

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(6S,7R,8R,9S)-6-oxaspiro-7,8-dihydroxymegastigman-4-en-3-one

Provided By

JEOL Database JEOL Logo

Description

Tubiflorone belongs to the class of organic compounds known as cyclohexenones. Cyclohexenones are compounds containing a cylohexenone moiety, which is a six-membered aliphatic ring that carries a ketone and has one endocyclic double bond. (6S,7R,8R,9S)-6-oxaspiro-7,8-dihydroxymegastigman-4-en-3-one is found in Kalanchoe tubiflora (Harvey) Hamet. (6S,7R,8R,9S)-6-oxaspiro-7,8-dihydroxymegastigman-4-en-3-one was first documented in 2013 (Huang, H.-C., et al.). Based on a literature review very few articles have been published on Tubiflorone.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306212102043D          

 37 38  0  0  0  0            999 V2000
   -1.2389   -0.8627    2.4295 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2646   -1.5229    1.0751 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1939   -2.8632    0.9891 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2062   -3.5686   -0.3126 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2271   -4.7981   -0.3225 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2204   -2.7590   -1.5879 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6915   -1.3199   -1.4004 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8528   -1.3817   -1.1969 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8966   -0.5504   -2.7235 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3875   -0.6250   -0.1636 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6599    0.6083    0.1049 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5819    1.7105    0.1136 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8958    2.9503   -0.4307 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7769    1.2721   -0.7152 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.9797    1.9635   -0.3969 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8769   -0.1929   -0.3223 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.6529   -0.9330   -1.2541 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2130   -1.5963    3.2430 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3502   -0.2322    2.5334 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1281   -0.2439    2.5811 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1215   -3.5051    1.8604 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6002   -3.2891   -2.3221 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2454   -2.7706   -1.9706 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2918   -0.3783   -1.1595 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1379   -1.8997   -0.2764 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3361   -1.9118   -2.0264 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5321    0.4793   -2.6491 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9452   -0.5222   -3.0311 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3462   -1.0289   -3.5427 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8784    1.9013    1.1525 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0209    3.1989    0.1795 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5284    2.7820   -1.4487 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5725    3.8097   -0.4388 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6099    1.3799   -1.7913 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8674    2.8909   -0.6723 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4128   -0.2652    0.6331 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5198   -0.4854   -1.2945 H   0  0  0  0  0  0  0  0  0  0  0  0
 10 11  1  1  0  0  0
 11 12  1  0  0  0  0
 10  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7 10  1  0  0  0  0
  7  8  1  1  0  0  0
  4  5  2  0  0  0  0
  2  1  1  0  0  0  0
 12 14  1  0  0  0  0
 12 13  1  0  0  0  0
 14 16  1  0  0  0  0
 14 15  1  0  0  0  0
 16 17  1  0  0  0  0
  7  9  1  0  0  0  0
 10 16  1  0  0  0  0
 12 30  1  1  0  0  0
 14 34  1  6  0  0  0
 16 36  1  1  0  0  0
  8 24  1  0  0  0  0
  8 25  1  0  0  0  0
  8 26  1  0  0  0  0
  9 27  1  0  0  0  0
  9 28  1  0  0  0  0
  9 29  1  0  0  0  0
  3 21  1  0  0  0  0
  1 18  1  0  0  0  0
  1 19  1  0  0  0  0
  1 20  1  0  0  0  0
  6 22  1  0  0  0  0
  6 23  1  0  0  0  0
 13 31  1  0  0  0  0
 13 32  1  0  0  0  0
 13 33  1  0  0  0  0
 15 35  1  0  0  0  0
 17 37  1  0  0  0  0
M  END

     RDKit          3D

 37 38  0  0  0  0  0  0  0  0999 V2000
   -1.2389   -0.8627    2.4295 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2646   -1.5229    1.0751 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1939   -2.8632    0.9891 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2062   -3.5686   -0.3126 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2271   -4.7981   -0.3225 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2204   -2.7590   -1.5879 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6915   -1.3199   -1.4004 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8528   -1.3817   -1.1969 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8966   -0.5504   -2.7235 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3875   -0.6250   -0.1636 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6599    0.6083    0.1049 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5819    1.7105    0.1136 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8958    2.9503   -0.4307 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7769    1.2721   -0.7152 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.9797    1.9635   -0.3969 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8769   -0.1929   -0.3223 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.6529   -0.9330   -1.2541 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2130   -1.5963    3.2430 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3502   -0.2322    2.5334 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1281   -0.2439    2.5811 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1215   -3.5051    1.8604 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6002   -3.2891   -2.3221 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2454   -2.7706   -1.9706 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2918   -0.3783   -1.1595 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1379   -1.8997   -0.2764 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3361   -1.9118   -2.0264 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5321    0.4793   -2.6491 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9452   -0.5222   -3.0311 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3462   -1.0289   -3.5427 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8784    1.9013    1.1525 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0209    3.1989    0.1795 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5284    2.7820   -1.4487 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5725    3.8097   -0.4388 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6099    1.3799   -1.7913 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8674    2.8909   -0.6723 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4128   -0.2652    0.6331 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5198   -0.4854   -1.2945 H   0  0  0  0  0  0  0  0  0  0  0  0
 10 11  1  1
 11 12  1  0
 10  2  1  0
  2  3  2  0
  3  4  1  0
  4  6  1  0
  6  7  1  0
  7 10  1  0
  7  8  1  1
  4  5  2  0
  2  1  1  0
 12 14  1  0
 12 13  1  0
 14 16  1  0
 14 15  1  0
 16 17  1  0
  7  9  1  0
 10 16  1  0
 12 30  1  1
 14 34  1  6
 16 36  1  1
  8 24  1  0
  8 25  1  0
  8 26  1  0
  9 27  1  0
  9 28  1  0
  9 29  1  0
  3 21  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  6 22  1  0
  6 23  1  0
 13 31  1  0
 13 32  1  0
 13 33  1  0
 15 35  1  0
 17 37  1  0
M  END


  Mrv1652306212102043D          

 37 38  0  0  0  0            999 V2000
   -1.2389   -0.8627    2.4295 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2646   -1.5229    1.0751 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1939   -2.8632    0.9891 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2062   -3.5686   -0.3126 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2271   -4.7981   -0.3225 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2204   -2.7590   -1.5879 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6915   -1.3199   -1.4004 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8528   -1.3817   -1.1969 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8966   -0.5504   -2.7235 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3875   -0.6250   -0.1636 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6599    0.6083    0.1049 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5819    1.7105    0.1136 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8958    2.9503   -0.4307 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7769    1.2721   -0.7152 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.9797    1.9635   -0.3969 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8769   -0.1929   -0.3223 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.6529   -0.9330   -1.2541 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2130   -1.5963    3.2430 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3502   -0.2322    2.5334 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1281   -0.2439    2.5811 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1215   -3.5051    1.8604 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6002   -3.2891   -2.3221 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2454   -2.7706   -1.9706 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2918   -0.3783   -1.1595 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1379   -1.8997   -0.2764 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3361   -1.9118   -2.0264 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5321    0.4793   -2.6491 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9452   -0.5222   -3.0311 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3462   -1.0289   -3.5427 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8784    1.9013    1.1525 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0209    3.1989    0.1795 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5284    2.7820   -1.4487 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5725    3.8097   -0.4388 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6099    1.3799   -1.7913 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8674    2.8909   -0.6723 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4128   -0.2652    0.6331 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5198   -0.4854   -1.2945 H   0  0  0  0  0  0  0  0  0  0  0  0
 10 11  1  1  0  0  0
 11 12  1  0  0  0  0
 10  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7 10  1  0  0  0  0
  7  8  1  1  0  0  0
  4  5  2  0  0  0  0
  2  1  1  0  0  0  0
 12 14  1  0  0  0  0
 12 13  1  0  0  0  0
 14 16  1  0  0  0  0
 14 15  1  0  0  0  0
 16 17  1  0  0  0  0
  7  9  1  0  0  0  0
 10 16  1  0  0  0  0
 12 30  1  1  0  0  0
 14 34  1  6  0  0  0
 16 36  1  1  0  0  0
  8 24  1  0  0  0  0
  8 25  1  0  0  0  0
  8 26  1  0  0  0  0
  9 27  1  0  0  0  0
  9 28  1  0  0  0  0
  9 29  1  0  0  0  0
  3 21  1  0  0  0  0
  1 18  1  0  0  0  0
  1 19  1  0  0  0  0
  1 20  1  0  0  0  0
  6 22  1  0  0  0  0
  6 23  1  0  0  0  0
 13 31  1  0  0  0  0
 13 32  1  0  0  0  0
 13 33  1  0  0  0  0
 15 35  1  0  0  0  0
 17 37  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0042395

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C13H20O4/c1-7-5-9(14)6-12(3,4)13(7)11(16)10(15)8(2)17-13/h5,8,10-11,15-16H,6H2,1-4H3/t8-,10-,11+,13-/m0/s1

> <INCHI_KEY>
UKBYGGQMJVALQC-MGAJZRQESA-N

> <FORMULA>
C13H20O4

> <MOLECULAR_WEIGHT>
240.299

> <EXACT_MASS>
240.136159124

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
37

> <JCHEM_AVERAGE_POLARIZABILITY>
25.40346518207071

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S,3R,4R,5S)-3,4-dihydroxy-2,6,10,10-tetramethyl-1-oxaspiro[4.5]dec-6-en-8-one

> <ALOGPS_LOGP>
0.72

> <JCHEM_LOGP>
0.7928170499999996

> <ALOGPS_LOGS>
-1.22

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.154446530605991

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.698386490907534

> <JCHEM_PKA_STRONGEST_BASIC>
-3.616210537296845

> <JCHEM_POLAR_SURFACE_AREA>
66.76

> <JCHEM_REFRACTIVITY>
63.0235

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.46e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3R,4R,5S)-3,4-dihydroxy-2,6,10,10-tetramethyl-1-oxaspiro[4.5]dec-6-en-8-one

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 37 38  0  0  0  0  0  0  0  0999 V2000
   -1.2389   -0.8627    2.4295 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2646   -1.5229    1.0751 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1939   -2.8632    0.9891 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2062   -3.5686   -0.3126 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2271   -4.7981   -0.3225 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2204   -2.7590   -1.5879 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6915   -1.3199   -1.4004 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8528   -1.3817   -1.1969 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8966   -0.5504   -2.7235 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3875   -0.6250   -0.1636 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6599    0.6083    0.1049 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5819    1.7105    0.1136 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8958    2.9503   -0.4307 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7769    1.2721   -0.7152 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.9797    1.9635   -0.3969 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8769   -0.1929   -0.3223 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.6529   -0.9330   -1.2541 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2130   -1.5963    3.2430 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3502   -0.2322    2.5334 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1281   -0.2439    2.5811 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1215   -3.5051    1.8604 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6002   -3.2891   -2.3221 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2454   -2.7706   -1.9706 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2918   -0.3783   -1.1595 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1379   -1.8997   -0.2764 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3361   -1.9118   -2.0264 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5321    0.4793   -2.6491 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9452   -0.5222   -3.0311 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3462   -1.0289   -3.5427 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8784    1.9013    1.1525 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0209    3.1989    0.1795 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5284    2.7820   -1.4487 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5725    3.8097   -0.4388 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6099    1.3799   -1.7913 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8674    2.8909   -0.6723 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4128   -0.2652    0.6331 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5198   -0.4854   -1.2945 H   0  0  0  0  0  0  0  0  0  0  0  0
 10 11  1  1
 11 12  1  0
 10  2  1  0
  2  3  2  0
  3  4  1  0
  4  6  1  0
  6  7  1  0
  7 10  1  0
  7  8  1  1
  4  5  2  0
  2  1  1  0
 12 14  1  0
 12 13  1  0
 14 16  1  0
 14 15  1  0
 16 17  1  0
  7  9  1  0
 10 16  1  0
 12 30  1  1
 14 34  1  6
 16 36  1  1
  8 24  1  0
  8 25  1  0
  8 26  1  0
  9 27  1  0
  9 28  1  0
  9 29  1  0
  3 21  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  6 22  1  0
  6 23  1  0
 13 31  1  0
 13 32  1  0
 13 33  1  0
 15 35  1  0
 17 37  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      -1.239  -0.863   2.430  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.265  -1.523   1.075  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.194  -2.863   0.989  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.206  -3.569  -0.313  0.00  0.00           C+0
HETATM    5  O   UNK     0      -1.227  -4.798  -0.323  0.00  0.00           O+0
HETATM    6  C   UNK     0      -1.220  -2.759  -1.588  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.692  -1.320  -1.400  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.853  -1.382  -1.197  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.897  -0.550  -2.724  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.387  -0.625  -0.164  0.00  0.00           C+0
HETATM   11  O   UNK     0      -0.660   0.608   0.105  0.00  0.00           O+0
HETATM   12  C   UNK     0      -1.582   1.710   0.114  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.896   2.950  -0.431  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.777   1.272  -0.715  0.00  0.00           C+0
HETATM   15  O   UNK     0      -3.980   1.964  -0.397  0.00  0.00           O+0
HETATM   16  C   UNK     0      -2.877  -0.193  -0.322  0.00  0.00           C+0
HETATM   17  O   UNK     0      -3.653  -0.933  -1.254  0.00  0.00           O+0
HETATM   18  H   UNK     0      -1.213  -1.596   3.243  0.00  0.00           H+0
HETATM   19  H   UNK     0      -0.350  -0.232   2.533  0.00  0.00           H+0
HETATM   20  H   UNK     0      -2.128  -0.244   2.581  0.00  0.00           H+0
HETATM   21  H   UNK     0      -1.121  -3.505   1.860  0.00  0.00           H+0
HETATM   22  H   UNK     0      -0.600  -3.289  -2.322  0.00  0.00           H+0
HETATM   23  H   UNK     0      -2.245  -2.771  -1.971  0.00  0.00           H+0
HETATM   24  H   UNK     0       1.292  -0.378  -1.159  0.00  0.00           H+0
HETATM   25  H   UNK     0       1.138  -1.900  -0.276  0.00  0.00           H+0
HETATM   26  H   UNK     0       1.336  -1.912  -2.026  0.00  0.00           H+0
HETATM   27  H   UNK     0      -0.532   0.479  -2.649  0.00  0.00           H+0
HETATM   28  H   UNK     0      -1.945  -0.522  -3.031  0.00  0.00           H+0
HETATM   29  H   UNK     0      -0.346  -1.029  -3.543  0.00  0.00           H+0
HETATM   30  H   UNK     0      -1.878   1.901   1.153  0.00  0.00           H+0
HETATM   31  H   UNK     0      -0.021   3.199   0.180  0.00  0.00           H+0
HETATM   32  H   UNK     0      -0.528   2.782  -1.449  0.00  0.00           H+0
HETATM   33  H   UNK     0      -1.573   3.810  -0.439  0.00  0.00           H+0
HETATM   34  H   UNK     0      -2.610   1.380  -1.791  0.00  0.00           H+0
HETATM   35  H   UNK     0      -3.867   2.891  -0.672  0.00  0.00           H+0
HETATM   36  H   UNK     0      -3.413  -0.265   0.633  0.00  0.00           H+0
HETATM   37  H   UNK     0      -4.520  -0.485  -1.295  0.00  0.00           H+0
CONECT    1    2   18   19   20                                             
CONECT    2   10    3    1                                                  
CONECT    3    2    4   21                                                  
CONECT    4    3    6    5                                                  
CONECT    5    4                                                            
CONECT    6    4    7   22   23                                             
CONECT    7    6   10    8    9                                             
CONECT    8    7   24   25   26                                             
CONECT    9    7   27   28   29                                             
CONECT   10   11    2    7   16                                             
CONECT   11   10   12                                                       
CONECT   12   11   14   13   30                                             
CONECT   13   12   31   32   33                                             
CONECT   14   12   16   15   34                                             
CONECT   15   14   35                                                       
CONECT   16   14   17   10   36                                             
CONECT   17   16   37                                                       
CONECT   18    1                                                            
CONECT   19    1                                                            
CONECT   20    1                                                            
CONECT   21    3                                                            
CONECT   22    6                                                            
CONECT   23    6                                                            
CONECT   24    8                                                            
CONECT   25    8                                                            
CONECT   26    8                                                            
CONECT   27    9                                                            
CONECT   28    9                                                            
CONECT   29    9                                                            
CONECT   30   12                                                            
CONECT   31   13                                                            
CONECT   32   13                                                            
CONECT   33   13                                                            
CONECT   34   14                                                            
CONECT   35   15                                                            
CONECT   36   16                                                            
CONECT   37   17                                                            
MASTER        0    0    0    0    0    0    0    0   37    0   76    0
END

RDKit          3D

37 38  0  0  0  0  0  0  0  0999 V2000
   -1.2389   -0.8627    2.4295 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2646   -1.5229    1.0751 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1939   -2.8632    0.9891 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2062   -3.5686   -0.3126 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2271   -4.7981   -0.3225 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2204   -2.7590   -1.5879 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6915   -1.3199   -1.4004 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8528   -1.3817   -1.1969 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8966   -0.5504   -2.7235 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3875   -0.6250   -0.1636 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6599    0.6083    0.1049 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5819    1.7105    0.1136 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8958    2.9503   -0.4307 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7769    1.2721   -0.7152 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.9797    1.9635   -0.3969 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8769   -0.1929   -0.3223 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.6529   -0.9330   -1.2541 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2130   -1.5963    3.2430 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3502   -0.2322    2.5334 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1281   -0.2439    2.5811 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1215   -3.5051    1.8604 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6002   -3.2891   -2.3221 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2454   -2.7706   -1.9706 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2918   -0.3783   -1.1595 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1379   -1.8997   -0.2764 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3361   -1.9118   -2.0264 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5321    0.4793   -2.6491 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9452   -0.5222   -3.0311 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3462   -1.0289   -3.5427 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8784    1.9013    1.1525 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0209    3.1989    0.1795 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5284    2.7820   -1.4487 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5725    3.8097   -0.4388 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6099    1.3799   -1.7913 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8674    2.8909   -0.6723 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4128   -0.2652    0.6331 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5198   -0.4854   -1.2945 H   0  0  0  0  0  0  0  0  0  0  0  0
 10 11  1  1
 11 12  1  0
 10  2  1  0
  2  3  2  0
  3  4  1  0
  4  6  1  0
  6  7  1  0
  7 10  1  0
  7  8  1  1
  4  5  2  0
  2  1  1  0
 12 14  1  0
 12 13  1  0
 14 16  1  0
 14 15  1  0
 16 17  1  0
  7  9  1  0
 10 16  1  0
 12 30  1  1
 14 34  1  6
 16 36  1  1
  8 24  1  0
  8 25  1  0
  8 26  1  0
  9 27  1  0
  9 28  1  0
  9 29  1  0
  3 21  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  6 22  1  0
  6 23  1  0
 13 31  1  0
 13 32  1  0
 13 33  1  0
 15 35  1  0
 17 37  1  0
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₃H₂₀O₄

Average Mass

240.2990 Da

Monoisotopic Mass

240.13616 Da

IUPAC Name

(2S,3R,4R,5S)-3,4-dihydroxy-2,6,10,10-tetramethyl-1-oxaspiro[4.5]dec-6-en-8-one

Traditional Name

(2S,3R,4R,5S)-3,4-dihydroxy-2,6,10,10-tetramethyl-1-oxaspiro[4.5]dec-6-en-8-one

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C13H20O4/c1-7-5-9(14)6-12(3,4)13(7)11(16)10(15)8(2)17-13/h5,8,10-11,15-16H,6H2,1-4H3/t8-,10-,11+,13-/m0/s1

InChI Key

UKBYGGQMJVALQC-MGAJZRQESA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CD₃OD, 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
Kalanchoe delagoensis	JEOL database	Huang, H.-C., et al, Phytochem. Lett. 6, 379 (2013)

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cyclohexenones. Cyclohexenones are compounds containing a cylohexenone moiety, which is a six-membered aliphatic ring that carries a ketone and has one endocyclic double bond.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Cyclohexenones

Alternative Parents

Substituents

Cyclohexenone
Tetrahydrofuran
Secondary alcohol
1,2-diol
Oxacycle
Organoheterocyclic compound
Ether
Dialkyl ether
Organic oxide
Hydrocarbon derivative
Alcohol
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic 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	0.72	ALOGPS
logP	0.79	ChemAxon
logS	-1.2	ALOGPS
pKa (Strongest Acidic)	12.7	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	66.76 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	63.02 m³·mol⁻¹	ChemAxon
Polarizability	25.4 Å³	ChemAxon
Number of Rings	2	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

102442816

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Huang, H.-C., et al. (2013). Huang, H.-C., et al, Phytochem. Lett. 6, 379 (2013). Phytochem..

Showing NP-Card for (6S,7R,8R,9S)-6-oxaspiro-7,8-dihydroxymegastigman-4-en-3-one (NP0042395)

MOL for NP0042395 ((6S,7R,8R,9S)-6-oxaspiro-7,8-dihydroxymegastigman-4-en-3-one)

3D MOL for NP0042395 ((6S,7R,8R,9S)-6-oxaspiro-7,8-dihydroxymegastigman-4-en-3-one)

3D SDF for NP0042395 ((6S,7R,8R,9S)-6-oxaspiro-7,8-dihydroxymegastigman-4-en-3-one)

3D-SDF for NP0042395 ((6S,7R,8R,9S)-6-oxaspiro-7,8-dihydroxymegastigman-4-en-3-one)

PDB for NP0042395 ((6S,7R,8R,9S)-6-oxaspiro-7,8-dihydroxymegastigman-4-en-3-one)

3D PDB for NP0042395 ((6S,7R,8R,9S)-6-oxaspiro-7,8-dihydroxymegastigman-4-en-3-one)

SMILES for NP0042395 ((6S,7R,8R,9S)-6-oxaspiro-7,8-dihydroxymegastigman-4-en-3-one)

INCHI for NP0042395 ((6S,7R,8R,9S)-6-oxaspiro-7,8-dihydroxymegastigman-4-en-3-one)

Structure for NP0042395 ((6S,7R,8R,9S)-6-oxaspiro-7,8-dihydroxymegastigman-4-en-3-one)

3D Structure for NP0042395 ((6S,7R,8R,9S)-6-oxaspiro-7,8-dihydroxymegastigman-4-en-3-one)