NP-MRD: Showing NP-Card for 10-hydroxy-7-methoxy-3-methyl-9-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3h,4h-naphtho[2,3-c]pyran-1-one (NP0184986)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

1.0

Created at

2022-09-04 00:15:41 UTC

Updated at

2022-09-04 00:15:42 UTC

NP-MRD ID

NP0184986

Secondary Accession Numbers

None

Natural Product Identification

Common Name

10-hydroxy-7-methoxy-3-methyl-9-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3h,4h-naphtho[2,3-c]pyran-1-one

Description

10-Hydroxy-7-methoxy-3-methyl-9-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1H,3H,4H-naphtho[2,3-c]pyran-1-one belongs to the class of organic compounds known as naphthopyranone glycosides. Naphthopyranone glycosides are compounds containing a carbohydrate moiety glycosidically linked to a naphthopyranone moiety. 10-hydroxy-7-methoxy-3-methyl-9-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3h,4h-naphtho[2,3-c]pyran-1-one is found in Eriocaulon buergerianum and Paepalanthus vellozioides. 10-Hydroxy-7-methoxy-3-methyl-9-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1H,3H,4H-naphtho[2,3-c]pyran-1-one is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004191518242D          

 31 34  0  0  0  0            999 V2000
    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 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
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 O   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 O   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   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   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
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 O   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    1.2375    0.0000 O   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
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    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
    5.0013   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -1.6500    0.0000 O   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
    6.4302   -2.8875    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   -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
  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  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
  9 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
  7 16  1  0  0  0  0
 16 17  1  0  0  0  0
  5 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 27 28  1  0  0  0  0
 21 28  1  0  0  0  0
 28 29  2  0  0  0  0
 29 30  1  0  0  0  0
 18 30  1  0  0  0  0
 30 31  2  0  0  0  0
  3 31  1  0  0  0  0
M  END

     RDKit          3D

 55 58  0  0  0  0  0  0  0  0999 V2000
    1.5021    5.7587   -0.5332 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4458    4.8409   -0.3933 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6898    3.4633   -0.2550 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3926    2.6269   -0.1228 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2722    1.2566    0.0196 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3029    0.3884    0.1532 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6810    0.6273    0.1814 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.2583    0.0049   -0.8662 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6815   -1.2483   -0.8070 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.8308   -1.4309   -1.8109 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8913   -0.5835   -1.5211 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1169   -1.8241    0.4895 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.5241   -1.7428    0.6167 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5339   -1.1768    1.7009 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3893   -1.8558    2.1605 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1941    0.2593    1.5403 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.2950    1.0664    1.8993 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0317    0.7454    0.0233 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1603   -0.6427    0.1674 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0419   -1.3999    0.2926 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4608   -1.1639    0.1724 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5626   -0.3641    0.0428 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3767    1.0252   -0.0989 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1172    1.5825   -0.1091 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9522    2.9566   -0.2501 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9382   -0.9035    0.0330 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0269   -2.2145    0.7398 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.3616   -2.8387    0.4053 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9581   -3.0794    0.3473 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6485   -2.5994    0.3334 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6926   -3.3812    0.4549 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0756    6.7721   -0.5819 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1911    5.6463    0.3082 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0292    5.4903   -1.4862 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3857    3.0417   -0.1284 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8487    1.7155    0.0702 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8717   -1.9207   -1.2173 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4175   -1.1908   -2.7980 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1652   -2.4993   -1.7795 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7259    0.2993   -1.9442 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8964   -2.9129    0.5660 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8048   -0.8134    0.8034 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2650   -1.2527    2.5588 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6087   -2.6258    2.7190 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3982    0.5100    2.2838 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4427    0.8727    2.8774 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1957   -2.3169    0.4003 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2563    1.6327   -0.1988 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8226    3.5649   -0.3495 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2061   -1.0379   -1.0504 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6222   -0.1754    0.5158 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0091   -2.0216    1.8319 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7875   -3.4182    1.2369 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2935   -3.4587   -0.5268 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1302   -2.0537    0.1566 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  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
  9 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
  5 18  2  0
 18 19  1  0
 19 20  1  0
 19 21  2  0
 21 30  1  0
 30 31  2  0
 30 29  1  0
 29 27  1  0
 27 28  1  0
 27 26  1  0
 26 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25  3  1  0
 16  7  1  0
 24 18  1  0
 22 21  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
  4 35  1  0
  7 36  1  6
  9 37  1  6
 10 38  1  0
 10 39  1  0
 11 40  1  0
 12 41  1  6
 13 42  1  0
 14 43  1  1
 15 44  1  0
 16 45  1  1
 17 46  1  0
 20 47  1  0
 27 52  1  1
 28 53  1  0
 28 54  1  0
 28 55  1  0
 26 50  1  0
 26 51  1  0
 23 48  1  0
 25 49  1  0
M  END


  Mrv1533004191518242D          

 31 34  0  0  0  0            999 V2000
    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 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
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 O   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 O   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   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   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
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 O   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    1.2375    0.0000 O   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
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    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
    5.0013   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -1.6500    0.0000 O   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
    6.4302   -2.8875    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   -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
  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  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
  9 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
  7 16  1  0  0  0  0
 16 17  1  0  0  0  0
  5 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 27 28  1  0  0  0  0
 21 28  1  0  0  0  0
 28 29  2  0  0  0  0
 29 30  1  0  0  0  0
 18 30  1  0  0  0  0
 30 31  2  0  0  0  0
  3 31  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0184986

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(OC2OC(CO)C(O)C(O)C2O)=C2C(O)=C3C(=O)OC(C)CC3=CC2=C1

> <INCHI_IDENTIFIER>
InChI=1S/C21H24O10/c1-8-3-9-4-10-5-11(28-2)6-12(14(10)17(24)15(9)20(27)29-8)30-21-19(26)18(25)16(23)13(7-22)31-21/h4-6,8,13,16,18-19,21-26H,3,7H2,1-2H3

> <INCHI_KEY>
XXMZRNKBDVODNC-UHFFFAOYSA-N

> <FORMULA>
C21H24O10

> <MOLECULAR_WEIGHT>
436.413

> <EXACT_MASS>
436.136946973

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
55

> <JCHEM_AVERAGE_POLARIZABILITY>
43.47122426462017

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
10-hydroxy-7-methoxy-3-methyl-9-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1H,3H,4H-naphtho[2,3-c]pyran-1-one

> <ALOGPS_LOGP>
0.08

> <JCHEM_LOGP>
0.8397930653333334

> <ALOGPS_LOGS>
-2.43

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.200349969885075

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.985176572158553

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9810923462647727

> <JCHEM_POLAR_SURFACE_AREA>
155.14

> <JCHEM_REFRACTIVITY>
104.83129999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.61e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
10-hydroxy-7-methoxy-3-methyl-9-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3H,4H-naphtho[2,3-c]pyran-1-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 19-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-APR-15         0                                  
HETATM    1  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       1.334  -5.390   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       4.001  -0.770   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       1.334  -0.770   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -2.667  -0.000   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       4.001   2.310   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       6.668  -0.770   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       9.336  -0.770   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      10.669  -3.080   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      10.669  -4.620   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      12.003  -5.390   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       9.336  -5.390   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   31                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   18                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   16                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   12                                                  
CONECT   10    9   11                                                       
CONECT   11   10                                                            
CONECT   12    9   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14    7   17                                                  
CONECT   17   16                                                            
CONECT   18    5   19   30                                                  
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22   28                                                  
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28                                                       
CONECT   28   27   21   29                                                  
CONECT   29   28   30                                                       
CONECT   30   29   18   31                                                  
CONECT   31   30    3                                                       
MASTER        0    0    0    0    0    0    0    0   31    0   68    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₁H₂₄O₁₀

Average Mass

436.4130 Da

Monoisotopic Mass

436.13695 Da

IUPAC Name

10-hydroxy-7-methoxy-3-methyl-9-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1H,3H,4H-naphtho[2,3-c]pyran-1-one

Traditional Name

10-hydroxy-7-methoxy-3-methyl-9-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3H,4H-naphtho[2,3-c]pyran-1-one

CAS Registry Number

Not Available

SMILES

COC1=CC(OC2OC(CO)C(O)C(O)C2O)=C2C(O)=C3C(=O)OC(C)CC3=CC2=C1

InChI Identifier

InChI=1S/C21H24O10/c1-8-3-9-4-10-5-11(28-2)6-12(14(10)17(24)15(9)20(27)29-8)30-21-19(26)18(25)16(23)13(7-22)31-21/h4-6,8,13,16,18-19,21-26H,3,7H2,1-2H3

InChI Key

XXMZRNKBDVODNC-UHFFFAOYSA-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
Eriocaulon buergerianum	LOTUS Database	35616633
Paepalanthus vellozioides	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as naphthopyranone glycosides. Naphthopyranone glycosides are compounds containing a carbohydrate moiety glycosidically linked to a naphthopyranone moiety.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Naphthopyrans

Sub Class

Naphthopyranones

Direct Parent

Naphthopyranone glycosides

Alternative Parents

Substituents

Naphthopyranone glycoside
Phenolic glycoside
Hexose monosaccharide
1-naphthol
O-glycosyl compound
Glycosyl compound
Naphthalene
Benzopyran
Isochromane
2-benzopyran
Anisole
Pyranone
Alkyl aryl ether
1-hydroxy-4-unsubstituted benzenoid
Pyran
Monosaccharide
Oxane
Benzenoid
Vinylogous acid
Carboxylic acid ester
Secondary alcohol
Lactone
Ether
Acetal
Carboxylic acid derivative
Oxacycle
Monocarboxylic acid or derivatives
Polyol
Organic oxygen compound
Primary alcohol
Alcohol
Hydrocarbon derivative
Organic oxide
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	0.08	ALOGPS
logP	0.84	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	8.99	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	155.14 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	104.83 m³·mol⁻¹	ChemAxon
Polarizability	43.47 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

85276322

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 10-hydroxy-7-methoxy-3-methyl-9-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3h,4h-naphtho[2,3-c]pyran-1-one (NP0184986)

MOL for NP0184986 (10-hydroxy-7-methoxy-3-methyl-9-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3h,4h-naphtho[2,3-c]pyran-1-one)

3D MOL for NP0184986 (10-hydroxy-7-methoxy-3-methyl-9-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3h,4h-naphtho[2,3-c]pyran-1-one)

3D SDF for NP0184986 (10-hydroxy-7-methoxy-3-methyl-9-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3h,4h-naphtho[2,3-c]pyran-1-one)

3D-SDF for NP0184986 (10-hydroxy-7-methoxy-3-methyl-9-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3h,4h-naphtho[2,3-c]pyran-1-one)

PDB for NP0184986 (10-hydroxy-7-methoxy-3-methyl-9-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3h,4h-naphtho[2,3-c]pyran-1-one)

3D PDB for NP0184986 (10-hydroxy-7-methoxy-3-methyl-9-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3h,4h-naphtho[2,3-c]pyran-1-one)

SMILES for NP0184986 (10-hydroxy-7-methoxy-3-methyl-9-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3h,4h-naphtho[2,3-c]pyran-1-one)

INCHI for NP0184986 (10-hydroxy-7-methoxy-3-methyl-9-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3h,4h-naphtho[2,3-c]pyran-1-one)

Structure for NP0184986 (10-hydroxy-7-methoxy-3-methyl-9-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3h,4h-naphtho[2,3-c]pyran-1-one)

3D Structure for NP0184986 (10-hydroxy-7-methoxy-3-methyl-9-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3h,4h-naphtho[2,3-c]pyran-1-one)