NP-MRD: Showing NP-Card for Uvarialeptone B (NP0333241)

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Record Information

Version

2.0

Created at

2024-05-13 01:51:17 UTC

Updated at

2026-02-04 07:13:15 UTC

NP-MRD ID

NP0333241

Natural Product DOI

https://doi.org/10.57994/2577

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Uvarialeptone B

Description

Uvarialeptone B belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units. Uvarialeptone B was first documented in 2024 (PMID: 38805684). Based on a literature review very few articles have been published on Uvarialeptone B.

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 01252304272D          

 60 68  0  0  1  0            999 V2000
    0.0000   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2676   -4.1832    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1530   -4.4086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5353   -3.5814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3301   -3.4687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7728   -4.2959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3603   -5.0103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5353   -5.0103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -4.8792    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0526   -5.6136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7670   -6.0261    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0906   -6.4548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -6.9417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -6.5292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -5.7042    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4289   -5.2917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.4667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -4.0542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.2292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.8167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -3.2292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -4.0542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1127   -4.4969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -6.1167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -6.9417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -5.2917    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0000   -6.1167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3764   -6.4386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -5.7042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -4.8792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -6.5292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1311   -4.2959    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6939   -4.2959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1064   -5.0103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9314   -5.0103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3439   -4.2959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9314   -3.5814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1064   -3.5814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8579   -3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  2  1  6  0  0  0
  3  4  1  0  0  0  0
  4  5  1  1  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  5 10  1  0  0  0  0
  4 11  1  0  0  0  0
 11 12  1  1  0  0  0
 12 13  1  0  0  0  0
 12 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 17 16  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 19 24  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 17 26  1  6  0  0  0
 26 27  1  0  0  0  0
 17 28  1  0  0  0  0
 28 25  1  0  0  0  0
 28 29  1  6  0  0  0
 29 30  1  0  0  0  0
 28 31  1  0  0  0  0
 14 31  1  0  0  0  0
 31 32  2  0  0  0  0
 15 33  2  0  0  0  0
 34 11  1  0  0  0  0
  3 34  1  0  0  0  0
 34 35  1  6  0  0  0
 35 36  2  0  0  0  0
 36 37  1  0  0  0  0
 37 38  2  0  0  0  0
 38 39  1  0  0  0  0
 39 40  2  0  0  0  0
 35 40  1  0  0  0  0
  2 41  2  0  0  0  0
 41 42  1  0  0  0  0
 42 43  1  0  0  0  0
 44 43  1  0  0  0  0
 44 45  1  0  0  0  0
 45 46  1  0  0  0  0
 46 47  1  0  0  0  0
 47 48  2  0  0  0  0
 48 49  1  0  0  0  0
 49 50  2  0  0  0  0
 46 51  2  0  0  0  0
 50 51  1  0  0  0  0
 51 52  1  0  0  0  0
 44 53  1  6  0  0  0
 53 54  1  0  0  0  0
 44 55  1  0  0  0  0
 55 52  1  0  0  0  0
 55 56  1  6  0  0  0
 56 57  1  0  0  0  0
 55 58  1  0  0  0  0
 41 58  1  0  0  0  0
 58 59  2  0  0  0  0
 42 60  2  0  0  0  0
M  END


  Mrv2104 01252304272D          

 60 68  0  0  1  0            999 V2000
    0.0000   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2676   -4.1832    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1530   -4.4086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5353   -3.5814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3301   -3.4687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7728   -4.2959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3603   -5.0103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5353   -5.0103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -4.8792    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0526   -5.6136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7670   -6.0261    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0906   -6.4548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.7145   -6.5292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.4289   -2.8167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.9314   -5.0103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3439   -4.2959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9314   -3.5814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1064   -3.5814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
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    4.2868   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  4  5  1  1  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  5 10  1  0  0  0  0
  4 11  1  0  0  0  0
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 17 16  1  0  0  0  0
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 17 26  1  6  0  0  0
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 28 25  1  0  0  0  0
 28 29  1  6  0  0  0
 29 30  1  0  0  0  0
 28 31  1  0  0  0  0
 14 31  1  0  0  0  0
 31 32  2  0  0  0  0
 15 33  2  0  0  0  0
 34 11  1  0  0  0  0
  3 34  1  0  0  0  0
 34 35  1  6  0  0  0
 35 36  2  0  0  0  0
 36 37  1  0  0  0  0
 37 38  2  0  0  0  0
 38 39  1  0  0  0  0
 39 40  2  0  0  0  0
 35 40  1  0  0  0  0
  2 41  2  0  0  0  0
 41 42  1  0  0  0  0
 42 43  1  0  0  0  0
 44 43  1  0  0  0  0
 44 45  1  0  0  0  0
 45 46  1  0  0  0  0
 46 47  1  0  0  0  0
 47 48  2  0  0  0  0
 48 49  1  0  0  0  0
 49 50  2  0  0  0  0
 46 51  2  0  0  0  0
 50 51  1  0  0  0  0
 51 52  1  0  0  0  0
 44 53  1  6  0  0  0
 53 54  1  0  0  0  0
 44 55  1  0  0  0  0
 55 52  1  0  0  0  0
 55 56  1  6  0  0  0
 56 57  1  0  0  0  0
 55 58  1  0  0  0  0
 41 58  1  0  0  0  0
 58 59  2  0  0  0  0
 42 60  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0333241

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CO[C@@]12CC(=O)\C(=C(/O)[C@H]3[C@H]([C@@H]([C@@H]3C3=CC=CC=C3)C(\O)=C3\C(=O)C[C@]4(OC)OC5=C(C[C@]4(OC)C3=O)C=CC=C5)C3=CC=CC=C3)C(=O)[C@@]1(CC1=C(O2)C=CC=C1)OC

> <INCHI_IDENTIFIER>
InChI=1S/C48H44O12/c1-55-45-23-29-19-11-13-21-33(29)59-47(45,57-3)25-31(49)37(43(45)53)41(51)39-35(27-15-7-5-8-16-27)40(36(39)28-17-9-6-10-18-28)42(52)38-32(50)26-48(58-4)46(56-2,44(38)54)24-30-20-12-14-22-34(30)60-48/h5-22,35-36,39-40,51-52H,23-26H2,1-4H3/b41-37+,42-38+/t35-,36-,39-,40-,45-,46+,47-,48+

> <INCHI_KEY>
ZHJDMMAKKFDSIF-BYHLZVORSA-N

> <FORMULA>
C48H44O12

> <MOLECULAR_WEIGHT>
812.868

> <EXACT_MASS>
812.283276857

> <JCHEM_ACCEPTOR_COUNT>
12

> <JCHEM_ATOM_COUNT>
104

> <JCHEM_AVERAGE_POLARIZABILITY>
83.05097110107793

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2E,4aS,9aS)-2-{[(1R,2R,3S,4S)-3-{[(2E,4aR,9aR)-4a,9a-dimethoxy-1,3-dioxo-2,3,4,4a,9,9a-hexahydro-1H-xanthen-2-ylidene](hydroxy)methyl}-2,4-diphenylcyclobutyl](hydroxy)methylidene}-4a,9a-dimethoxy-2,3,4,4a,9,9a-hexahydro-1H-xanthene-1,3-dione

> <JCHEM_LOGP>
7.821348271333335

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
9

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
3.0746672405728157

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.4348008954487437

> <JCHEM_PKA_STRONGEST_BASIC>
-3.938568139602631

> <JCHEM_POLAR_SURFACE_AREA>
164.11999999999998

> <JCHEM_REFRACTIVITY>
219.1097999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(2E,4aS,9aS)-2-{[(1R,2R,3S,4S)-3-{[(2E,4aR,9aR)-4a,9a-dimethoxy-1,3-dioxo-4,9-dihydroxanthen-2-ylidene](hydroxy)methyl}-2,4-diphenylcyclobutyl](hydroxy)methylidene}-4a,9a-dimethoxy-4,9-dihydroxanthene-1,3-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 25-JAN-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-JAN-23         0                                  
HETATM    1  O   UNK     0       0.000  -4.620   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.366  -7.809   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.019  -8.229   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.733  -6.685   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.216  -6.475   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.043  -8.019   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.273  -9.353   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.733  -9.353   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.334  -9.108   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.965 -10.479   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       3.298 -11.249   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       0.169 -12.049   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.000 -12.958   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.334 -12.188   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.334 -10.648   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       2.667  -9.878   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       2.667  -8.338   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.001  -7.568   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.001  -6.028   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.667  -5.258   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       1.334  -6.028   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       1.334  -7.568   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -0.210  -8.394   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       2.667 -11.418   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       2.667 -12.958   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       0.000  -9.878   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       0.000 -11.418   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      -0.703 -12.019   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -1.334 -10.648   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      -1.334  -9.108   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0      -1.334 -12.188   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       0.245  -8.019   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -1.295  -8.019   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      -2.065  -9.353   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      -3.605  -9.353   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      -4.375  -8.019   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      -3.605  -6.685   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      -2.065  -6.685   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   45  O   UNK     0       6.668  -2.310   0.000  0.00  0.00           O+0
HETATM   46  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0      10.669  -3.080   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0      10.669  -4.620   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0       9.336  -5.390   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM   53  O   UNK     0       5.335  -1.540   0.000  0.00  0.00           O+0
HETATM   54  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   55  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   56  O   UNK     0       5.335  -6.160   0.000  0.00  0.00           O+0
HETATM   57  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM   58  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   59  O   UNK     0       4.001  -6.930   0.000  0.00  0.00           O+0
HETATM   60  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   41                                                  
CONECT    3    2    4   34                                                  
CONECT    4    3    5   11                                                  
CONECT    5    4    6   10                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9    5                                                       
CONECT   11    4   12   34                                                  
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   31                                                  
CONECT   15   14   16   33                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   26   28                                             
CONECT   18   17   19                                                       
CONECT   19   18   20   24                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   19   23   25                                                  
CONECT   25   24   28                                                       
CONECT   26   17   27                                                       
CONECT   27   26                                                            
CONECT   28   17   25   29   31                                             
CONECT   29   28   30                                                       
CONECT   30   29                                                            
CONECT   31   28   14   32                                                  
CONECT   32   31                                                            
CONECT   33   15                                                            
CONECT   34   11    3   35                                                  
CONECT   35   34   36   40                                                  
CONECT   36   35   37                                                       
CONECT   37   36   38                                                       
CONECT   38   37   39                                                       
CONECT   39   38   40                                                       
CONECT   40   39   35                                                       
CONECT   41    2   42   58                                                  
CONECT   42   41   43   60                                                  
CONECT   43   42   44                                                       
CONECT   44   43   45   53   55                                             
CONECT   45   44   46                                                       
CONECT   46   45   47   51                                                  
CONECT   47   46   48                                                       
CONECT   48   47   49                                                       
CONECT   49   48   50                                                       
CONECT   50   49   51                                                       
CONECT   51   46   50   52                                                  
CONECT   52   51   55                                                       
CONECT   53   44   54                                                       
CONECT   54   53                                                            
CONECT   55   44   52   56   58                                             
CONECT   56   55   57                                                       
CONECT   57   56                                                            
CONECT   58   55   41   59                                                  
CONECT   59   58                                                            
CONECT   60   42                                                            
MASTER        0    0    0    0    0    0    0    0   60    0  136    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₄₈H₄₄O₁₂

Average Mass

812.8680 Da

Monoisotopic Mass

812.28328 Da

IUPAC Name

(2E,4aS,9aS)-2-{[(1R,2R,3S,4S)-3-{[(2E,4aR,9aR)-4a,9a-dimethoxy-1,3-dioxo-2,3,4,4a,9,9a-hexahydro-1H-xanthen-2-ylidene](hydroxy)methyl}-2,4-diphenylcyclobutyl](hydroxy)methylidene}-4a,9a-dimethoxy-2,3,4,4a,9,9a-hexahydro-1H-xanthene-1,3-dione

Traditional Name

(2E,4aS,9aS)-2-{[(1R,2R,3S,4S)-3-{[(2E,4aR,9aR)-4a,9a-dimethoxy-1,3-dioxo-4,9-dihydroxanthen-2-ylidene](hydroxy)methyl}-2,4-diphenylcyclobutyl](hydroxy)methylidene}-4a,9a-dimethoxy-4,9-dihydroxanthene-1,3-dione

CAS Registry Number

Not Available

SMILES

CO[C@@]12CC(=O)\C(=C(/O)[C@H]3[C@H]([C@@H]([C@@H]3C3=CC=CC=C3)C(\O)=C3\C(=O)C[C@]4(OC)OC5=C(C[C@]4(OC)C3=O)C=CC=C5)C3=CC=CC=C3)C(=O)[C@@]1(CC1=C(O2)C=CC=C1)OC

InChI Identifier

InChI=1S/C48H44O12/c1-55-45-23-29-19-11-13-21-33(29)59-47(45,57-3)25-31(49)37(43(45)53)41(51)39-35(27-15-7-5-8-16-27)40(36(39)28-17-9-6-10-18-28)42(52)38-32(50)26-48(58-4)46(56-2,44(38)54)24-30-20-12-14-22-34(30)60-48/h5-22,35-36,39-40,51-52H,23-26H2,1-4H3/b41-37+,42-38+/t35-,36-,39-,40-,45-,46+,47-,48+

InChI Key

ZHJDMMAKKFDSIF-BYHLZVORSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 500 MHz, CDCl3, experimental)	surat.lap@mfu.ac.th	Mae Fah Luang University	Surat Laphookhieo	2024-05-13	View Spectrum
NOESY NMR	[¹H, ¹H] NMR Spectrum (2D, 500 MHz, CDCl3, experimental)	surat.lap@mfu.ac.th	Mae Fah Luang University	Surat Laphookhieo	2024-05-13	View Spectrum
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 500 MHz, CDCl3, experimental)	surat.lap@mfu.ac.th	Mae Fah Luang University	Surat Laphookhieo	2024-05-13	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 500 MHz, CDCl3, experimental)	surat.lap@mfu.ac.th	Mae Fah Luang University	Surat Laphookhieo	2024-05-13	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl3, experimental)	surat.lap@mfu.ac.th	Mae Fah Luang University	Surat Laphookhieo	2024-05-13	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, CDCl3, experimental)	surat.lap@mfu.ac.th	Mae Fah Luang University	Surat Laphookhieo	2024-05-13	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View

Chemical Shift Submissions

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 500.0, Chloroform-d, simulated)	epoynton@sfu.ca	Not Available	Not Available	2026-02-04	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 125.0, Chloroform-d, simulated)	epoynton@sfu.ca	Not Available	Not Available	2026-02-04	View Spectrum

Species

Species of Origin

Species Name	Source	Reference
Uvaria leptopoda		Not Available
Uvaria leptopoda		Not Available

Chemical Taxonomy

Description

This compound belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Diterpenoids

Alternative Parents

Substituents

Diterpenoid
Xanthene
Dibenzopyran
1-benzopyran
Benzopyran
Chromane
Ketal
Alpha-branched alpha,beta-unsaturated-ketone
Benzenoid
Monocyclic benzene moiety
Vinylogous acid
Alpha,beta-unsaturated ketone
Enone
Acryloyl-group
Cyclic ketone
Ketone
Oxacycle
Organoheterocyclic compound
Ether
Dialkyl ether
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen 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	7.82	ChemAxon
pKa (Strongest Acidic)	2.43	ChemAxon
pKa (Strongest Basic)	-3.9	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	164.12 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	219.11 m³·mol⁻¹	ChemAxon
Polarizability	83.05 Å³	ChemAxon
Number of Rings	9	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Teerapongpisan P, Monkantha T, Yimklan S, Mah SH, Gunter NV, Promnart P, Deachathai S, Maneerat T, Duangyod T, Charoensup R, Baka A, Andersen RJ, Laphookhieo S: Tetrahydroxanthene-1,3(2H)-diones and Oxidized Hexadiene Derivatives from Uvaria leptopoda and Their Biological Activities. J Nat Prod. 2024 Jun 28;87(6):1611-1617. doi: 10.1021/acs.jnatprod.4c00248. Epub 2024 May 28. [PubMed:38805684 ]
DOI: 10.1021/acs.jnatprod.4c00248
PMID: 38805684

Showing NP-Card for Uvarialeptone B (NP0333241)

MOL for NP0333241 (Uvarialeptone B)

3D MOL for NP0333241 (Uvarialeptone B)

3D SDF for NP0333241 (Uvarialeptone B)

3D-SDF for NP0333241 (Uvarialeptone B)

PDB for NP0333241 (Uvarialeptone B)

3D PDB for NP0333241 (Uvarialeptone B)

SMILES for NP0333241 (Uvarialeptone B)

INCHI for NP0333241 (Uvarialeptone B)

Structure for NP0333241 (Uvarialeptone B)

3D Structure for NP0333241 (Uvarialeptone B)