NP-MRD: Showing NP-Card for isopropyl 4-[(3r)-7,8-dihydroxy-6-methoxy-3,10-dimethyl-4-oxo-2h-naphtho[2,3-b]pyran-3-yl]butanoate (NP0281835)

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Record Information

Version

2.0

Created at

2022-09-09 08:25:21 UTC

Updated at

2022-09-09 08:25:21 UTC

NP-MRD ID

NP0281835

Secondary Accession Numbers

None

Natural Product Identification

Common Name

isopropyl 4-[(3r)-7,8-dihydroxy-6-methoxy-3,10-dimethyl-4-oxo-2h-naphtho[2,3-b]pyran-3-yl]butanoate

Description

Propan-2-yl 4-[(3R)-7,8-dihydroxy-6-methoxy-3,10-dimethyl-4-oxo-2H,3H,4H-naphtho[2,3-b]pyran-3-yl]butanoate belongs to the class of organic compounds known as naphthopyranones. Naphthopyranones are compounds containing a naphthopyran skeleton where a ring carbon bears a carboxylic acid group. Naphthtopyran is made up of the pyran ring fused to a naphthalene ring system. isopropyl 4-[(3r)-7,8-dihydroxy-6-methoxy-3,10-dimethyl-4-oxo-2h-naphtho[2,3-b]pyran-3-yl]butanoate is found in Lavandula angustifolia. Based on a literature review very few articles have been published on propan-2-yl 4-[(3R)-7,8-dihydroxy-6-methoxy-3,10-dimethyl-4-oxo-2H,3H,4H-naphtho[2,3-b]pyran-3-yl]butanoate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309092210252D          

 30 32  0  0  1  0            999 V2000
   -2.6216    1.1532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9037    0.3779    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3734   -0.2540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6556   -1.0293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4681   -1.1726    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1253   -1.6613    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4075   -2.4365    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3128   -1.5180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0307   -0.7428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2182   -0.5995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3121   -1.2315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0640    0.1757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4663    0.8077    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2788    0.6645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5610   -0.1108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1842    1.5830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.2150    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6283    1.7262    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3461    2.5015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3428    2.1387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0572    1.7262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7717    2.1387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4862    1.7262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4862    0.9012    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2007    2.1387    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9151    1.7262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6296    2.1387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9151    0.9012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1586    1.0942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8764    0.3190    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  2  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  2  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
  3 15  2  0  0  0  0
  9 15  1  0  0  0  0
 13 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  1  0  0  0
 18 20  1  6  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  1  0  0  0  0
 18 29  1  0  0  0  0
 29 30  1  0  0  0  0
 12 30  1  0  0  0  0
M  END

     RDKit          3D

 58 60  0  0  0  0  0  0  0  0999 V2000
   -5.5501   -2.2912    2.3666 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6987   -0.8763    2.3273 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6117   -0.2873    1.0571 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7378   -0.1245    0.2938 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9829   -0.5307    0.7448 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5664    0.4670   -0.9518 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6594    0.6544   -1.7578 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3284    0.8718   -1.4022 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2172    0.6914   -0.6051 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9533    1.0792   -1.0078 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7945    1.7129   -2.3499 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8352    0.9061   -0.2244 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9996    0.3089    1.0332 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2344   -0.0777    1.4455 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3409    0.1002    0.6567 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7995    0.1415    1.8144 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8442    0.2568    3.0400 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4903   -0.1736    1.1354 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4192   -1.6765    0.8582 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6107    0.1531    2.0606 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9811   -0.1342    1.6301 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5777    0.4997    0.4445 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0236    0.0161    0.3463 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4210   -0.7665    1.2116 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8518    0.4302   -0.6591 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1878    0.0145   -0.7926 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4222   -0.7791   -2.0603 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1577    1.1706   -0.6772 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5780    0.6099   -0.1276 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5646    1.2742   -0.5738 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1177   -2.7412    3.2079 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5104   -2.6140    2.4708 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9272   -2.7401    1.4062 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0323   -0.9531    1.6607 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6285    1.0693   -2.6636 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1697    1.3312   -2.3604 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2781    1.0506   -3.1126 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7269    1.7714   -2.6229 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2021    2.7375   -2.3834 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3288   -0.5260    2.4188 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3546   -2.1785    1.8238 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2160   -2.0134    0.1992 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5453   -1.8392    0.3307 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4005   -0.3029    3.0930 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5619    1.2676    2.3074 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1884   -1.2605    1.6403 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6533    0.1872    2.5116 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6410    1.5916    0.5741 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1817    0.1972   -0.5470 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4004   -0.6860    0.0575 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5035   -0.7663   -2.2629 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8621   -0.3593   -2.9206 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1092   -1.8079   -1.8808 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3025    1.4930    0.3646 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6580    2.0361   -1.2024 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.0952    0.9891   -1.2281 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3374    1.4295    0.0445 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9990   -0.0036   -0.9728 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3 15  2  0
 15 14  1  0
 14 13  2  0
 13 16  1  0
 16 17  2  0
 16 18  1  0
 18 19  1  6
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  2  0
 23 25  1  0
 25 26  1  0
 26 27  1  0
 26 28  1  0
 18 29  1  0
 29 30  1  0
 30 12  1  0
 12 10  2  0
 10 11  1  0
 10  9  1  0
  9  8  2  0
  8  6  1  0
  6  7  1  0
  6  4  2  0
  4  5  1  0
  4  3  1  0
  9 15  1  0
 12 13  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
 14 40  1  0
 19 41  1  0
 19 42  1  0
 19 43  1  0
 20 44  1  0
 20 45  1  0
 21 46  1  0
 21 47  1  0
 22 48  1  0
 22 49  1  0
 26 50  1  0
 27 51  1  0
 27 52  1  0
 27 53  1  0
 28 54  1  0
 28 55  1  0
 28 56  1  0
 29 57  1  0
 29 58  1  0
 11 37  1  0
 11 38  1  0
 11 39  1  0
  8 36  1  0
  7 35  1  0
  5 34  1  0
M  END


  Mrv1652309092210252D          

 30 32  0  0  1  0            999 V2000
   -2.6216    1.1532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9037    0.3779    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3734   -0.2540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6556   -1.0293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4681   -1.1726    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1253   -1.6613    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4075   -2.4365    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3128   -1.5180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0307   -0.7428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2182   -0.5995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3121   -1.2315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0640    0.1757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4663    0.8077    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2788    0.6645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5610   -0.1108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1842    1.5830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.2150    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6283    1.7262    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3461    2.5015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3428    2.1387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0572    1.7262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7717    2.1387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4862    1.7262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4862    0.9012    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2007    2.1387    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9151    1.7262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6296    2.1387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9151    0.9012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1586    1.0942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8764    0.3190    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  2  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  2  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
  3 15  2  0  0  0  0
  9 15  1  0  0  0  0
 13 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  1  0  0  0
 18 20  1  6  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  1  0  0  0  0
 18 29  1  0  0  0  0
 29 30  1  0  0  0  0
 12 30  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0281835

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C2C=C3C(=O)[C@](C)(CCCC(=O)OC(C)C)COC3=C(C)C2=CC(O)=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C23H28O7/c1-12(2)30-18(25)7-6-8-23(4)11-29-20-13(3)14-10-17(24)19(26)21(28-5)15(14)9-16(20)22(23)27/h9-10,12,24,26H,6-8,11H2,1-5H3/t23-/m1/s1

> <INCHI_KEY>
ZNFDBZPKXKIQNA-HSZRJFAPSA-N

> <FORMULA>
C23H28O7

> <MOLECULAR_WEIGHT>
416.47

> <EXACT_MASS>
416.183503242

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
58

> <JCHEM_AVERAGE_POLARIZABILITY>
45.53323043693948

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
propan-2-yl 4-[(3R)-7,8-dihydroxy-6-methoxy-3,10-dimethyl-4-oxo-2H,3H,4H-naphtho[2,3-b]pyran-3-yl]butanoate

> <JCHEM_LOGP>
4.081401910666667

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.82798365800025

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.961739809131334

> <JCHEM_PKA_STRONGEST_BASIC>
-4.6069211643805295

> <JCHEM_POLAR_SURFACE_AREA>
102.28999999999999

> <JCHEM_REFRACTIVITY>
111.46110000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
isopropyl 4-[(3R)-7,8-dihydroxy-6-methoxy-3,10-dimethyl-4-oxo-2H-naphtho[2,3-b]pyran-3-yl]butanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 09-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-SEP-22         0                                  
HETATM    1  C   UNK     0      -4.894   2.153   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -5.420   0.705   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -4.430  -0.474   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -4.957  -1.921   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -6.474  -2.189   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      -3.967  -3.101   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -4.494  -4.548   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -2.451  -2.834   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.924  -1.387   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.407  -1.119   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.583  -2.299   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.119   0.328   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.870   1.508   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.387   1.240   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -2.914  -0.207   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.344   2.955   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -1.334   4.135   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       1.173   3.222   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.646   4.669   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.506   3.992   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.840   3.222   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.174   3.992   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       6.508   3.222   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       6.508   1.682   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       7.841   3.992   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       9.175   3.222   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      10.509   3.992   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       9.175   1.682   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       2.163   2.043   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       1.636   0.595   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   15                                                  
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10   15                                                  
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   30                                                  
CONECT   13   12   14   16                                                  
CONECT   14   13   15                                                       
CONECT   15   14    3    9                                                  
CONECT   16   13   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19   20   29                                             
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26                                                            
CONECT   29   18   30                                                       
CONECT   30   29   12                                                       
MASTER        0    0    0    0    0    0    0    0   30    0   64    0
END

View in JSmol

Synonyms

Value	Source
Propan-2-yl 4-[(3R)-7,8-dihydroxy-6-methoxy-3,10-dimethyl-4-oxo-2H,3H,4H-naphtho[2,3-b]pyran-3-yl]butanoic acid	Generator

Chemical Formula

C₂₃H₂₈O₇

Average Mass

416.4700 Da

Monoisotopic Mass

416.18350 Da

IUPAC Name

propan-2-yl 4-[(3R)-7,8-dihydroxy-6-methoxy-3,10-dimethyl-4-oxo-2H,3H,4H-naphtho[2,3-b]pyran-3-yl]butanoate

Traditional Name

isopropyl 4-[(3R)-7,8-dihydroxy-6-methoxy-3,10-dimethyl-4-oxo-2H-naphtho[2,3-b]pyran-3-yl]butanoate

CAS Registry Number

Not Available

SMILES

COC1=C2C=C3C(=O)[C@](C)(CCCC(=O)OC(C)C)COC3=C(C)C2=CC(O)=C1O

InChI Identifier

InChI=1S/C23H28O7/c1-12(2)30-18(25)7-6-8-23(4)11-29-20-13(3)14-10-17(24)19(26)21(28-5)15(14)9-16(20)22(23)27/h9-10,12,24,26H,6-8,11H2,1-5H3/t23-/m1/s1

InChI Key

ZNFDBZPKXKIQNA-HSZRJFAPSA-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, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, 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
Lavandula angustifolia	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as naphthopyranones. Naphthopyranones are compounds containing a naphthopyran skeleton where a ring carbon bears a carboxylic acid group. Naphthtopyran is made up of the pyran ring fused to a naphthalene ring system.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Naphthopyrans

Sub Class

Naphthopyranones

Direct Parent

Naphthopyranones

Alternative Parents

Substituents

Benzochromone
Naphthopyranone
Chromone
2-naphthol
Chromane
Benzopyran
Naphthalene
1-benzopyran
Anisole
Aryl alkyl ketone
Aryl ketone
Pyranone
Alkyl aryl ether
Fatty acid ester
1-hydroxy-2-unsubstituted benzenoid
Benzenoid
Fatty acyl
Pyran
Ketone
Carboxylic acid ester
Oxacycle
Monocarboxylic acid or derivatives
Ether
Carboxylic acid derivative
Organooxygen compound
Organic oxide
Organic oxygen compound
Carbonyl group
Hydrocarbon derivative
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	4.08	ChemAxon
pKa (Strongest Acidic)	8.96	ChemAxon
pKa (Strongest Basic)	-4.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	102.29 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	111.46 m³·mol⁻¹	ChemAxon
Polarizability	45.53 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	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

163029461

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for isopropyl 4-[(3r)-7,8-dihydroxy-6-methoxy-3,10-dimethyl-4-oxo-2h-naphtho[2,3-b]pyran-3-yl]butanoate (NP0281835)

MOL for NP0281835 (isopropyl 4-[(3r)-7,8-dihydroxy-6-methoxy-3,10-dimethyl-4-oxo-2h-naphtho[2,3-b]pyran-3-yl]butanoate)

3D MOL for NP0281835 (isopropyl 4-[(3r)-7,8-dihydroxy-6-methoxy-3,10-dimethyl-4-oxo-2h-naphtho[2,3-b]pyran-3-yl]butanoate)

3D SDF for NP0281835 (isopropyl 4-[(3r)-7,8-dihydroxy-6-methoxy-3,10-dimethyl-4-oxo-2h-naphtho[2,3-b]pyran-3-yl]butanoate)

3D-SDF for NP0281835 (isopropyl 4-[(3r)-7,8-dihydroxy-6-methoxy-3,10-dimethyl-4-oxo-2h-naphtho[2,3-b]pyran-3-yl]butanoate)

PDB for NP0281835 (isopropyl 4-[(3r)-7,8-dihydroxy-6-methoxy-3,10-dimethyl-4-oxo-2h-naphtho[2,3-b]pyran-3-yl]butanoate)

3D PDB for NP0281835 (isopropyl 4-[(3r)-7,8-dihydroxy-6-methoxy-3,10-dimethyl-4-oxo-2h-naphtho[2,3-b]pyran-3-yl]butanoate)

SMILES for NP0281835 (isopropyl 4-[(3r)-7,8-dihydroxy-6-methoxy-3,10-dimethyl-4-oxo-2h-naphtho[2,3-b]pyran-3-yl]butanoate)

INCHI for NP0281835 (isopropyl 4-[(3r)-7,8-dihydroxy-6-methoxy-3,10-dimethyl-4-oxo-2h-naphtho[2,3-b]pyran-3-yl]butanoate)

Structure for NP0281835 (isopropyl 4-[(3r)-7,8-dihydroxy-6-methoxy-3,10-dimethyl-4-oxo-2h-naphtho[2,3-b]pyran-3-yl]butanoate)

3D Structure for NP0281835 (isopropyl 4-[(3r)-7,8-dihydroxy-6-methoxy-3,10-dimethyl-4-oxo-2h-naphtho[2,3-b]pyran-3-yl]butanoate)