NP-MRD: Showing NP-Card for (+)-4-Hydroxypanduratin A (NP0070656)

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Record Information

Version

2.0

Created at

2022-04-28 16:06:20 UTC

Updated at

2022-04-28 16:06:20 UTC

NP-MRD ID

NP0070656

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(+)-4-Hydroxypanduratin A

Description

4-Hydroxypanduratin A belongs to the class of organic compounds known as linear diarylheptanoids. These are diarylheptanoids with an open heptane chain. The two aromatic rings are linked only by the heptane chain. (+)-4-Hydroxypanduratin A is found in Boesenbergia rotunda and Boesenbergia rotunda (LINN.) MANSF. . (+)-4-Hydroxypanduratin A was first documented in 2006 (PMID: 16960369). Based on a literature review a significant number of articles have been published on 4-hydroxypanduratin A (PMID: 30606988) (PMID: 18591809) (PMID: 17978489) (PMID: 33271853) (PMID: 25883671) (PMID: 23390345).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282218062D          

 29 31  0  0  1  0            999 V2000
   -1.4289   -1.6500    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
   -2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -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
   -1.6585   -0.5701    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.2868   -0.0000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -0.0000    0.0000 C   0  0  1  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
   -1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    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
   -5.0013   -0.4125    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
   -6.4302   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4302   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  6  7  1  0  0  0  0
  5  8  1  0  0  0  0
  8  9  2  0  0  0  0
 10  8  1  1  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 10 15  1  0  0  0  0
 15 16  1  1  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 14 21  1  0  0  0  0
 11 22  1  6  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 22 27  1  0  0  0  0
  4 28  1  0  0  0  0
  2 29  1  0  0  0  0
M  END

     RDKit          3D

 57 59  0  0  0  0  0  0  0  0999 V2000
    3.5350    3.0498    0.5253 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8143    2.2866    1.5627 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3464    2.2286    2.9359 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6950    1.6606    1.2484 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1497    1.7124   -0.1333 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0452    0.3761   -0.8132 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9864    0.5629   -2.2677 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5308    1.8288   -2.9028 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4686   -0.3483   -3.0391 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0977   -1.6187   -2.5817 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4871   -1.6333   -1.1466 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3682   -3.0294   -0.6874 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8579   -3.6266   -0.6172 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9520   -4.9448   -0.1824 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1636   -5.6700    0.1818 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3943   -5.0627    0.1086 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4718   -3.7461   -0.3274 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2084   -0.6533   -0.2469 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7106   -0.3567    0.8639 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4337   -0.9823    1.9804 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8629    0.4909    0.9790 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3487    1.2112   -0.0759 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7940    1.1671   -1.3473 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4437    2.0405    0.0619 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0498    2.1368    1.2832 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1618    2.9763    1.4312 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6215    1.4518    2.3678 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5011    0.6043    2.2254 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1478   -0.0395    3.3690 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8724    2.4180   -0.3325 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4674    3.4895    0.9416 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8778    3.8589    0.1238 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2385    3.1964    3.4767 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4383    2.0004    2.9483 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8523    1.4564    3.5596 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1827    1.1155    2.0232 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2646    2.3299   -0.1073 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8846    2.3187   -0.7631 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1500   -0.0189   -0.6885 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9522    2.7166   -2.5334 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3770    1.7867   -3.9801 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6133    1.9303   -2.7115 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4529   -0.1555   -4.1224 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9687   -1.8640   -3.2580 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6584   -2.4215   -2.8278 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5723   -1.4070   -1.0990 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7145   -3.0512   -0.9030 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9316   -5.4142   -0.1288 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0563   -6.7103    0.5213 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2670   -5.6234    0.3913 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4895   -3.3248   -0.3606 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9787   -1.3775    0.3031 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1511    1.6933   -2.1135 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8048    2.6003   -0.7969 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4982    3.4910    0.6532 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1189    1.5443    3.3266 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5121   -0.6508    3.7022 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  1  0
  6 18  1  0
 18 11  1  0
 11 10  1  0
 10  9  1  0
  9  7  2  0
  7  8  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 18 19  1  0
 19 20  2  0
 19 21  1  0
 21 22  2  0
 22 23  1  0
 22 24  1  0
 24 25  2  0
 25 26  1  0
 25 27  1  0
 27 28  2  0
 28 29  1  0
  7  6  1  0
 17 12  1  0
 28 21  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  3 33  1  0
  3 34  1  0
  3 35  1  0
  4 36  1  0
  5 37  1  0
  5 38  1  0
  6 39  1  6
 18 52  1  1
 11 46  1  6
 10 44  1  0
 10 45  1  0
  9 43  1  0
  8 40  1  0
  8 41  1  0
  8 42  1  0
 13 47  1  0
 14 48  1  0
 15 49  1  0
 16 50  1  0
 17 51  1  0
 23 53  1  0
 24 54  1  0
 26 55  1  0
 27 56  1  0
 29 57  1  0
M  END


  Mrv1652304282218062D          

 29 31  0  0  1  0            999 V2000
   -1.4289   -1.6500    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
   -2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -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
   -1.6585   -0.5701    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.2868   -0.0000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -0.0000    0.0000 C   0  0  1  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
   -1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    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
   -5.0013   -0.4125    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
   -6.4302   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4302   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  6  7  1  0  0  0  0
  5  8  1  0  0  0  0
  8  9  2  0  0  0  0
 10  8  1  1  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 10 15  1  0  0  0  0
 15 16  1  1  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 14 21  1  0  0  0  0
 11 22  1  6  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 22 27  1  0  0  0  0
  4 28  1  0  0  0  0
  2 29  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0070656

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)=CC[C@H]1[C@H]([C@@H](CC=C1C)C1=CC=CC=C1)C(=O)C1=C(O)C=C(O)C=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C25H28O4/c1-15(2)9-11-19-16(3)10-12-20(17-7-5-4-6-8-17)23(19)25(29)24-21(27)13-18(26)14-22(24)28/h4-10,13-14,19-20,23,26-28H,11-12H2,1-3H3/t19-,20+,23-/m1/s1

> <INCHI_KEY>
AYPOOQWQTQIRFW-ZRCGQRJVSA-N

> <FORMULA>
C25H28O4

> <MOLECULAR_WEIGHT>
392.495

> <EXACT_MASS>
392.198759382

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
57

> <JCHEM_AVERAGE_POLARIZABILITY>
43.56471930280851

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-[(1R,2S,6R)-3-methyl-2-(3-methylbut-2-en-1-yl)-6-phenylcyclohex-3-ene-1-carbonyl]benzene-1,3,5-triol

> <ALOGPS_LOGP>
5.06

> <JCHEM_LOGP>
6.838126977666668

> <ALOGPS_LOGS>
-4.58

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.662782608336151

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.956471388855891

> <JCHEM_PKA_STRONGEST_BASIC>
-4.610644087143938

> <JCHEM_POLAR_SURFACE_AREA>
77.76

> <JCHEM_REFRACTIVITY>
117.3981

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.03e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-[(1R,2S,6R)-3-methyl-2-(3-methylbut-2-en-1-yl)-6-phenylcyclohex-3-ene-1-carbonyl]benzene-1,3,5-triol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -4.001  -5.390   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -5.335  -4.620   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -5.335  -3.080   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -4.001  -2.310   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -3.096  -1.064   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -6.668  -2.310   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -8.002  -3.080   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      -6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -8.002  -0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -8.002   1.540   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -6.668   2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -5.335   1.540   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -5.335  -0.000   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -4.001   2.310   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -9.336  -0.770   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -9.336  -2.310   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0     -10.669  -3.080   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0     -12.003  -2.310   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0     -12.003  -0.770   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0     -10.669  -0.000   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      -6.668  -5.390   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0      -1.334  -5.390   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3   29                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   28                                                  
CONECT    5    4    6    8                                                  
CONECT    6    5    1    7                                                  
CONECT    7    6                                                            
CONECT    8    5    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   15                                                  
CONECT   11   10   12   22                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   21                                                  
CONECT   15   14   10   16                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18                                                            
CONECT   21   14                                                            
CONECT   22   11   23   27                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   22                                                       
CONECT   28    4                                                            
CONECT   29    2                                                            
MASTER        0    0    0    0    0    0    0    0   29    0   62    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₅H₂₈O₄

Average Mass

392.4950 Da

Monoisotopic Mass

392.19876 Da

IUPAC Name

2-[(1R,2S,6R)-3-methyl-2-(3-methylbut-2-en-1-yl)-6-phenylcyclohex-3-ene-1-carbonyl]benzene-1,3,5-triol

Traditional Name

2-[(1R,2S,6R)-3-methyl-2-(3-methylbut-2-en-1-yl)-6-phenylcyclohex-3-ene-1-carbonyl]benzene-1,3,5-triol

CAS Registry Number

Not Available

SMILES

CC(C)=CC[C@H]1[C@H]([C@@H](CC=C1C)C1=CC=CC=C1)C(=O)C1=C(O)C=C(O)C=C1O

InChI Identifier

InChI=1S/C25H28O4/c1-15(2)9-11-19-16(3)10-12-20(17-7-5-4-6-8-17)23(19)25(29)24-21(27)13-18(26)14-22(24)28/h4-10,13-14,19-20,23,26-28H,11-12H2,1-3H3/t19-,20+,23-/m1/s1

InChI Key

AYPOOQWQTQIRFW-ZRCGQRJVSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Boesenbergia rotunda	LOTUS Database	35616633
Boesenbergia rotunda (LINN.) MANSF.	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as linear diarylheptanoids. These are diarylheptanoids with an open heptane chain. The two aromatic rings are linked only by the heptane chain.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Diarylheptanoids

Sub Class

Linear diarylheptanoids

Direct Parent

Linear diarylheptanoids

Alternative Parents

Substituents

Linear 1,7-diphenylheptane skeleton
Alkyl-phenylketone
Acylphloroglucinol derivative
Monocyclic monoterpenoid
Aromatic monoterpenoid
Monoterpenoid
Phenylketone
Phloroglucinol derivative
Benzenetriol
Benzoyl
Aryl alkyl ketone
Aryl ketone
Phenol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Benzenoid
Monocyclic benzene moiety
Vinylogous acid
Ketone
Polyol
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic 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	5.06	ALOGPS
logP	6.84	ChemAxon
logS	-4.6	ALOGPS
pKa (Strongest Acidic)	7.96	ChemAxon
pKa (Strongest Basic)	-4.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	77.76 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	117.4 m³·mol⁻¹	ChemAxon
Polarizability	43.56 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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

C00029276

Chemspider ID

552296

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

636530

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Tanigaki R, Takahashi R, Nguyen MTT, Nguyen NT, Do TVN, Nguyen HX, Kataoka T: 4-Hydroxypanduratin A and Isopanduratin A Inhibit Tumor Necrosis Factor alpha-Stimulated Gene Expression and the Nuclear Factor kappaB-Dependent Signaling Pathway in Human Lung Adenocarcinoma A549 Cells. Biol Pharm Bull. 2019;42(1):26-33. doi: 10.1248/bpb.b18-00457. [PubMed:30606988 ]
Morikawa T, Funakoshi K, Ninomiya K, Yasuda D, Miyagawa K, Matsuda H, Yoshikawa M: Medicinal foodstuffs. XXXIV. Structures of new prenylchalcones and prenylflavanones with TNF-alpha and aminopeptidase N inhibitory activities from Boesenbergia rotunda. Chem Pharm Bull (Tokyo). 2008 Jul;56(7):956-62. doi: 10.1248/cpb.56.956. [PubMed:18591809 ]
Yoon JH, Shim JS, Cho Y, Baek NI, Lee CW, Kim HS, Hwang JK: Depigmentation of melanocytes by isopanduratin A and 4-hydroxypanduratin A isolated from Kaempferia pandurata ROXB. Biol Pharm Bull. 2007 Nov;30(11):2141-5. doi: 10.1248/bpb.30.2141. [PubMed:17978489 ]
Adhikari D, Gong DS, Oh SH, Sung EH, Lee SO, Kim DW, Oak MH, Kim HJ: Vasorelaxant Effect of Boesenbergia rotunda and Its Active Ingredients on an Isolated Coronary Artery. Plants (Basel). 2020 Dec 1;9(12). pii: plants9121688. doi: 10.3390/plants9121688. [PubMed:33271853 ]
Tan BC, Tan SK, Wong SM, Ata N, Rahman NA, Khalid N: Distribution of Flavonoids and Cyclohexenyl Chalcone Derivatives in Conventional Propagated and In Vitro-Derived Field-Grown Boesenbergia rotunda (L.) Mansf. Evid Based Complement Alternat Med. 2015;2015:451870. doi: 10.1155/2015/451870. Epub 2015 Apr 7. [PubMed:25883671 ]
Seniya C, Mishra H, Yadav A, Sagar N, Chaturvedi B, Uchadia K, Wadhwa G: Antiviral potential of 4-hydroxypanduratin A, secondary metabolite of Fingerroot, Boesenbergia pandurata (Schult.), towards Japanese Encephalitis virus NS2B/NS3 protease. Bioinformation. 2013;9(1):54-60. doi: 10.6026/97320630009054. Epub 2013 Jan 9. [PubMed:23390345 ]
Kannappan P, Narayanan S: Mutation and docking studies on NS2b-NS3 complex from yellow fever virus towards drug discovery. Bioinformation. 2011;6(8):303-6. doi: 10.6026/97320630006303. Epub 2011 Jul 6. [PubMed:21769191 ]
Frimayanti N, Chee CF, Zain SM, Rahman NA: Design of new competitive dengue NS2B/NS3 protease inhibitors-a computational approach. Int J Mol Sci. 2011 Feb 9;12(2):1089-100. doi: 10.3390/ijms12021089. [PubMed:21541045 ]
Shim JS, Han YS, Hwang JK: The effect of 4-hydroxypanduratin A on the mitogen-activated protein kinase-dependent activation of matrix metalloproteinase-1 expression in human skin fibroblasts. J Dermatol Sci. 2009 Feb;53(2):129-34. doi: 10.1016/j.jdermsci.2008.09.002. Epub 2008 Dec 2. [PubMed:19054653 ]
Shindo K, Kato M, Kinoshita A, Kobayashi A, Koike Y: Analysis of antioxidant activities contained in the Boesenbergia pandurata Schult. Rhizome. Biosci Biotechnol Biochem. 2006 Sep;70(9):2281-4. doi: 10.1271/bbb.60086. Epub 2006 Sep 7. [PubMed:16960369 ]

Showing NP-Card for (+)-4-Hydroxypanduratin A (NP0070656)

MOL for NP0070656 ((+)-4-Hydroxypanduratin A)

3D MOL for NP0070656 ((+)-4-Hydroxypanduratin A)

3D SDF for NP0070656 ((+)-4-Hydroxypanduratin A)

3D-SDF for NP0070656 ((+)-4-Hydroxypanduratin A)

PDB for NP0070656 ((+)-4-Hydroxypanduratin A)

3D PDB for NP0070656 ((+)-4-Hydroxypanduratin A)

SMILES for NP0070656 ((+)-4-Hydroxypanduratin A)

INCHI for NP0070656 ((+)-4-Hydroxypanduratin A)

Structure for NP0070656 ((+)-4-Hydroxypanduratin A)

3D Structure for NP0070656 ((+)-4-Hydroxypanduratin A)