NP-MRD: Showing NP-Card for Orlandin (NP0078647)

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Record Information

Version

2.0

Created at

2022-04-28 23:40:49 UTC

Updated at

2024-09-03 04:19:35 UTC

NP-MRD ID

NP0078647

Natural Product DOI

https://doi.org/10.57994/1809

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Orlandin

Description

Orlandin belongs to the class of organic compounds known as 7-hydroxycoumarins. These are coumarins that contain one or more hydroxyl groups attached to the C7 position the coumarin skeleton. Orlandin is found in Cladosporium herbarum IFB-E002 and Ficus benghalensis. Orlandin was first documented in 1979 (PMID: 447931). Orlandin is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004171523102D          

 30 33  0  0  0  0            999 V2000
    3.5724   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.1250    0.0000 C   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
    3.5724   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 O   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 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    0.0000 C   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
    0.0000   -2.4750    0.0000 O   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
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 O   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
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   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    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    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
    4.2868   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 O   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    0.8250    0.0000 O   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  2  1  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
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  3  9  1  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  1  0  0  0  0
 13 15  2  0  0  0  0
  8 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
 27 28  1  0  0  0  0
 16 28  1  0  0  0  0
 22 28  2  0  0  0  0
 23 29  1  0  0  0  0
 29 30  1  0  0  0  0
M  END

     RDKit          3D

 48 51  0  0  0  0  0  0  0  0999 V2000
    5.9578    2.2091   -0.1415 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1142    1.1310   -0.4759 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8237    1.1001   -0.0266 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3396    2.1244    0.7570 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0352    2.0757    1.2008 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6279    3.0496    1.9266 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2356    1.0812    0.9001 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6711    0.1000    0.1598 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7680   -0.9166   -0.1165 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5960   -0.8868    0.3954 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9594   -1.4322    1.6050 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0163   -2.0441    2.3843 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2546   -1.3950    2.0736 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2654   -0.7953    1.3327 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6703   -0.7649    1.8604 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9157   -0.2462    0.1216 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9013    0.3589   -0.6403 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2134    0.4112   -0.1938 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2562    1.0040   -0.9082 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5182    0.9012   -1.8521 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1999    0.8188   -2.2429 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8801    1.3339   -3.3755 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2822    0.2436   -1.5106 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5975   -0.2843   -0.3549 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2167   -1.9568   -0.8966 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3764   -3.0053   -1.2145 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5060   -1.9857   -1.3809 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4119   -0.9802   -1.1123 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7994   -1.0197   -1.6386 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9629    0.0663   -0.3283 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9394    2.3213    0.9734 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0106    1.9850   -0.4019 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6514    3.1683   -0.5813 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9645    2.9673    1.0309 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9740   -2.0928    2.0789 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5333   -1.8261    3.0262 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6619   -1.2879    2.8685 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0044    0.2524    2.0986 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3681   -1.3724    1.2617 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0985    1.2187   -0.1968 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6803    0.2240   -1.6032 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9731    1.8981   -1.4725 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2704    1.3820   -2.4707 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5694   -2.9889   -0.8620 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8169   -2.8388   -2.0001 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8829   -1.9690   -2.2472 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0015   -0.2136   -2.3761 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5654   -1.1233   -0.8576 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8 30  2  0
 30 28  1  0
 28 29  1  0
 28 27  2  0
 27 25  1  0
 25 26  1  0
 25  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
 14 16  1  0
 16 24  2  0
 24 23  1  0
 23 21  1  0
 21 22  2  0
 21 20  1  0
 20 17  2  0
 17 18  1  0
 18 19  1  0
 30  3  1  0
 24 10  1  0
  9  8  1  0
 17 16  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
  4 34  1  0
 29 46  1  0
 29 47  1  0
 29 48  1  0
 27 45  1  0
 26 44  1  0
 12 35  1  0
 13 36  1  0
 15 37  1  0
 15 38  1  0
 15 39  1  0
 20 43  1  0
 19 40  1  0
 19 41  1  0
 19 42  1  0
M  END


  Mrv1533004171523102D          

 30 33  0  0  0  0            999 V2000
    3.5724   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.1250    0.0000 C   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
    3.5724   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 O   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 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    0.0000 C   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
    0.0000   -2.4750    0.0000 O   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
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 O   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
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   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    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    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
    4.2868   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 O   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    0.8250    0.0000 O   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  2  1  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
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  3  9  1  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  1  0  0  0  0
 13 15  2  0  0  0  0
  8 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
 27 28  1  0  0  0  0
 16 28  1  0  0  0  0
 22 28  2  0  0  0  0
 23 29  1  0  0  0  0
 29 30  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0078647

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(=O)OC2=C1C(C)=CC(O)=C2C1=C(O)C=C(C)C2=C1OC(=O)C=C2OC

> <INCHI_IDENTIFIER>
InChI=1S/C22H18O8/c1-9-5-11(23)19(21-17(9)13(27-3)7-15(25)29-21)20-12(24)6-10(2)18-14(28-4)8-16(26)30-22(18)20/h5-8,23-24H,1-4H3

> <INCHI_KEY>
SSGXAFNGBRRLQM-UHFFFAOYSA-N

> <FORMULA>
C22H18O8

> <MOLECULAR_WEIGHT>
410.378

> <EXACT_MASS>
410.10016754

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
48

> <JCHEM_AVERAGE_POLARIZABILITY>
40.87181345381423

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
7-hydroxy-8-(7-hydroxy-4-methoxy-5-methyl-2-oxo-2H-chromen-8-yl)-4-methoxy-5-methyl-2H-chromen-2-one

> <ALOGPS_LOGP>
3.31

> <JCHEM_LOGP>
2.378971892666666

> <ALOGPS_LOGS>
-4.19

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
7.730873069725519

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.8883865749401325

> <JCHEM_PKA_STRONGEST_BASIC>
-4.542715915095442

> <JCHEM_POLAR_SURFACE_AREA>
111.52000000000001

> <JCHEM_REFRACTIVITY>
109.50659999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.64e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
orlandin

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 17-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-APR-15         0                                  
HETATM    1  C   UNK     0       6.668 -10.010   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       5.335  -9.240   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       5.335  -7.700   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       8.002  -4.620   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0       5.335  -4.620   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.667  -9.240   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       0.000  -4.620   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       8.002  -3.080   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0       5.335  -3.080   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       5.335   1.540   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    9                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9   15                                                  
CONECT    9    8    3   10                                                  
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13    8   16                                                  
CONECT   16   15   17   28                                                  
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23   28                                                  
CONECT   23   22   24   29                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28                                                       
CONECT   28   27   16   22                                                  
CONECT   29   23   30                                                       
CONECT   30   29                                                            
MASTER        0    0    0    0    0    0    0    0   30    0   66    0
END

View in JSmol

Synonyms

Value	Source
7-Hydroxy-8-(7-hydroxy-4-methoxy-5-methyl-2-oxochromen-8-yl)-4-methoxy-5-methylchromen-2-one	ChEBI
Bis(8,8'-(7-hydroxy-4-methoxy-5-methylcoumarin))	MeSH

Chemical Formula

C₂₂H₁₈O₈

Average Mass

410.3780 Da

Monoisotopic Mass

410.10017 Da

IUPAC Name

7-hydroxy-8-(7-hydroxy-4-methoxy-5-methyl-2-oxo-2H-chromen-8-yl)-4-methoxy-5-methyl-2H-chromen-2-one

Traditional Name

orlandin

CAS Registry Number

Not Available

SMILES

COC1=CC(=O)OC2=C1C(C)=CC(O)=C2C1=C(O)C=C(C)C2=C1OC(=O)C=C2OC

InChI Identifier

InChI=1S/C22H18O8/c1-9-5-11(23)19(21-17(9)13(27-3)7-15(25)29-21)20-12(24)6-10(2)18-14(28-4)8-16(26)30-22(18)20/h5-8,23-24H,1-4H3

InChI Key

SSGXAFNGBRRLQM-UHFFFAOYSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, C2D6OS, experimental)	[email protected]	南方医科大学	Jing Yi	2024-02-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, C2D6OS, experimental)	[email protected]	南方医科大学	Jing Yi	2024-02-22	View Spectrum

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
Cladosporium herbarum IFB-E002	Fungi	KNApSAcK
Ficus benghalensis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 7-hydroxycoumarins. These are coumarins that contain one or more hydroxyl groups attached to the C7 position the coumarin skeleton.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Coumarins and derivatives

Sub Class

Hydroxycoumarins

Direct Parent

7-hydroxycoumarins

Alternative Parents

Substituents

7-hydroxycoumarin
Benzopyran
1-benzopyran
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Pyranone
Benzenoid
Pyran
Heteroaromatic compound
Vinylogous ester
Lactone
Ether
Oxacycle
Organoheterocyclic compound
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

8,8'-bicoumarins (CHEBI:64473 )

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	3.31	ALOGPS
logP	2.38	ChemAxon
logS	-4.2	ALOGPS
pKa (Strongest Acidic)	6.89	ChemAxon
pKa (Strongest Basic)	-4.5	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	111.52 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	109.51 m³·mol⁻¹	ChemAxon
Polarizability	40.87 Å³	ChemAxon
Number of Rings	4	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

Not Available

PDB ID

Not Available

ChEBI ID

64473

Good Scents ID

Not Available

References

General References

Cutler HG, Crumley FG, Cox RH, Hernandez O, Cole RJ, Dorner JW: Orlandin: a nontoxic fungal metabolite with plant growth inhibiting properties. J Agric Food Chem. 1979 May-Jun;27(3):592-5. doi: 10.1021/jf60223a043. [PubMed:447931 ]
DOI: 10.1016/j.phytol.2024.02.002

Showing NP-Card for Orlandin (NP0078647)

MOL for NP0078647 (Orlandin)

3D MOL for NP0078647 (Orlandin)

3D SDF for NP0078647 (Orlandin)

3D-SDF for NP0078647 (Orlandin)

PDB for NP0078647 (Orlandin)

3D PDB for NP0078647 (Orlandin)

SMILES for NP0078647 (Orlandin)

INCHI for NP0078647 (Orlandin)

Structure for NP0078647 (Orlandin)

3D Structure for NP0078647 (Orlandin)