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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 03:35:28 UTC

Update Date

2021-09-26 22:59:44 UTC

HMDB ID

HMDB0249101

Secondary Accession Numbers

None

Metabolite Identification

Common Name

beta-Apopolygamatin

Description

9-(2H-1,3-benzodioxol-5-yl)-7,8-dimethoxy-1H,3H,4H,9H-naphtho[2,3-c]furan-1-one belongs to the class of organic compounds known as naphthofurans. Naphthofurans are compounds containing a furan ring fused to a naphthalene moiety. Furan is a 5 membered- ring aromatic ring with four carbon and one oxygen atoms. Naphthalene is a polycyclic aromatic hydrocarbon made up of two fused benzene rings. Based on a literature review very few articles have been published on 9-(2H-1,3-benzodioxol-5-yl)-7,8-dimethoxy-1H,3H,4H,9H-naphtho[2,3-c]furan-1-one. This compound has been identified in human blood as reported by (PMID: 31557052 ). Beta-apopolygamatin is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically beta-Apopolygamatin is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

  Mrv1533004261501532D          

 27 31  0  0  0  0            999 V2000
   -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   -1.2375    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 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
    2.8579   -1.6500    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
    3.5724   -2.8875    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
    2.8579   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6864   -4.9320    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8659   -5.0182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5303   -4.2645    0.0000 O   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
    2.1434   -2.8875    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
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3570   -1.4924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6119   -2.2771    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8419   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3570   -0.1576    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
  6  7  1  0  0  0  0
  7  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
 11 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
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 14 18  1  0  0  0  0
 18 19  2  0  0  0  0
 11 19  1  0  0  0  0
 10 20  1  0  0  0  0
  6 20  1  0  0  0  0
 20 21  2  0  0  0  0
  3 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
  9 24  1  0  0  0  0
 24 25  2  0  0  0  0
 24 26  1  0  0  0  0
 26 27  1  0  0  0  0
  8 27  1  0  0  0  0
M  END

HMDB0249101
     RDKit          3D
beta-Apopolygamatin
 45 49  0  0  0  0  0  0  0  0999 V2000
   -4.4101   -2.8126   -0.1355 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1092   -2.3189   -0.1167 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7297   -1.0755    0.3380 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6134   -0.1593    0.8368 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1737    1.0572    1.2723 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8318    1.3879    1.2198 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9105    0.4565    0.7104 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3630   -0.7694    0.2708 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5079   -1.7266   -0.2387 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4258   -1.7702   -1.6741 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5031    0.8148    0.7429 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4515    0.0561   -0.0414 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8090    0.4917   -1.3125 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7429   -0.1961   -2.0559 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3390   -1.3403   -1.5368 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9956   -1.7857   -0.2792 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0525   -1.0793    0.4556 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7323   -2.9256   -0.0249 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6495   -3.1479   -1.0909 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3004   -2.2028   -2.0845 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7122    2.2805    0.6129 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2536    3.1364    0.8710 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0640    4.4212    0.2127 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4966    4.4037    0.2928 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9058    3.0568    0.2241 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0540    2.6721   -0.1035 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4177    2.7361    1.7194 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3516   -3.9264   -0.2168 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9896   -2.4306   -0.9959 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9948   -2.5766    0.7760 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6586   -0.4290    0.8736 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8870    1.7816    1.6679 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1998   -2.4836   -2.0533 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5751   -2.1101   -1.9704 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6410   -0.8053   -2.1416 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8074    0.6250    1.8441 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3198    1.3739   -1.6911 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0391    0.1274   -3.0552 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7544   -1.4031    1.4588 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6833   -3.0214   -0.7237 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4364   -4.1523   -1.4960 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3534    5.2927    0.7362 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2228    4.4438   -0.8483 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1188    2.6111    2.7727 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2601    3.4217    1.5703 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
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
  7 11  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
 16 18  1  0
 18 19  1  0
 19 20  1  0
 11 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  2  0
 22 27  1  0
  8  3  1  0
 17 12  1  0
 25 21  1  0
 27  6  1  0
 20 15  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
  4 31  1  0
  5 32  1  0
 10 33  1  0
 10 34  1  0
 10 35  1  0
 11 36  1  0
 13 37  1  0
 14 38  1  0
 17 39  1  0
 19 40  1  0
 19 41  1  0
 23 42  1  0
 23 43  1  0
 27 44  1  0
 27 45  1  0
M  END

  Mrv1533004261501532D          

 27 31  0  0  0  0            999 V2000
   -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   -1.2375    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 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
    2.8579   -1.6500    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
    3.5724   -2.8875    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
    2.8579   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6864   -4.9320    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8659   -5.0182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5303   -4.2645    0.0000 O   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
    2.1434   -2.8875    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
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3570   -1.4924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6119   -2.2771    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8419   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3570   -0.1576    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
  6  7  1  0  0  0  0
  7  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
 11 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
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 14 18  1  0  0  0  0
 18 19  2  0  0  0  0
 11 19  1  0  0  0  0
 10 20  1  0  0  0  0
  6 20  1  0  0  0  0
 20 21  2  0  0  0  0
  3 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
  9 24  1  0  0  0  0
 24 25  2  0  0  0  0
 24 26  1  0  0  0  0
 26 27  1  0  0  0  0
  8 27  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0249101

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=CC=C2CC3=C(C(C4=CC=C5OCOC5=C4)C2=C1OC)C(=O)OC3

> <INCHI_IDENTIFIER>
InChI=1S/C21H18O6/c1-23-15-6-4-11-7-13-9-25-21(22)19(13)17(18(11)20(15)24-2)12-3-5-14-16(8-12)27-10-26-14/h3-6,8,17H,7,9-10H2,1-2H3

> <INCHI_KEY>
URJOZSLMTIRWFW-UHFFFAOYSA-N

> <FORMULA>
C21H18O6

> <MOLECULAR_WEIGHT>
366.369

> <EXACT_MASS>
366.1103383

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
45

> <JCHEM_AVERAGE_POLARIZABILITY>
37.317957215539316

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
9-(2H-1,3-benzodioxol-5-yl)-7,8-dimethoxy-1H,3H,4H,9H-naphtho[2,3-c]furan-1-one

> <ALOGPS_LOGP>
2.96

> <JCHEM_LOGP>
3.0877408143333342

> <ALOGPS_LOGS>
-4.25

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.067137268553637

> <JCHEM_PKA_STRONGEST_BASIC>
-4.362982035018254

> <JCHEM_POLAR_SURFACE_AREA>
63.22

> <JCHEM_REFRACTIVITY>
96.5574

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.08e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
9-(2H-1,3-benzodioxol-5-yl)-7,8-dimethoxy-3H,4H,9H-naphtho[2,3-c]furan-1-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0249101
     RDKit          3D
beta-Apopolygamatin
 45 49  0  0  0  0  0  0  0  0999 V2000
   -4.4101   -2.8126   -0.1355 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1092   -2.3189   -0.1167 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7297   -1.0755    0.3380 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6134   -0.1593    0.8368 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1737    1.0572    1.2723 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8318    1.3879    1.2198 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9105    0.4565    0.7104 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3630   -0.7694    0.2708 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5079   -1.7266   -0.2387 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4258   -1.7702   -1.6741 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5031    0.8148    0.7429 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4515    0.0561   -0.0414 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8090    0.4917   -1.3125 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7429   -0.1961   -2.0559 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3390   -1.3403   -1.5368 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9956   -1.7857   -0.2792 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0525   -1.0793    0.4556 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7323   -2.9256   -0.0249 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6495   -3.1479   -1.0909 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3004   -2.2028   -2.0845 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7122    2.2805    0.6129 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2536    3.1364    0.8710 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0640    4.4212    0.2127 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4966    4.4037    0.2928 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9058    3.0568    0.2241 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0540    2.6721   -0.1035 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4177    2.7361    1.7194 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3516   -3.9264   -0.2168 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9896   -2.4306   -0.9959 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9948   -2.5766    0.7760 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6586   -0.4290    0.8736 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8870    1.7816    1.6679 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1998   -2.4836   -2.0533 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5751   -2.1101   -1.9704 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6410   -0.8053   -2.1416 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8074    0.6250    1.8441 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3198    1.3739   -1.6911 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0391    0.1274   -3.0552 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7544   -1.4031    1.4588 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6833   -3.0214   -0.7237 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4364   -4.1523   -1.4960 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3534    5.2927    0.7362 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2228    4.4438   -0.8483 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1188    2.6111    2.7727 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2601    3.4217    1.5703 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
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
  7 11  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
 16 18  1  0
 18 19  1  0
 19 20  1  0
 11 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  2  0
 22 27  1  0
  8  3  1  0
 17 12  1  0
 25 21  1  0
 27  6  1  0
 20 15  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
  4 31  1  0
  5 32  1  0
 10 33  1  0
 10 34  1  0
 10 35  1  0
 11 36  1  0
 13 37  1  0
 14 38  1  0
 17 39  1  0
 19 40  1  0
 19 41  1  0
 23 42  1  0
 23 43  1  0
 27 44  1  0
 27 45  1  0
M  END

HEADER    PROTEIN                                 26-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-APR-15         0                                  
HETATM    1  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.335  -7.700   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       5.015  -9.206   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       3.483  -9.367   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       2.857  -7.960   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       8.133  -2.786   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       8.609  -4.251   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       9.038  -1.540   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       8.133  -0.294   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   21                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   20                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   27                                                  
CONECT    9    8   10   24                                                  
CONECT   10    9   11   20                                                  
CONECT   11   10   12   19                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   18                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   14   19                                                  
CONECT   19   18   11                                                       
CONECT   20   10    6   21                                                  
CONECT   21   20    3   22                                                  
CONECT   22   21   23                                                       
CONECT   23   22                                                            
CONECT   24    9   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27                                                       
CONECT   27   26    8                                                       
MASTER        0    0    0    0    0    0    0    0   27    0   62    0
END

COMPND    HMDB0249101
HETATM    1  C1  UNL     1      -4.410  -2.813  -0.135  1.00  0.00           C  
HETATM    2  O1  UNL     1      -3.109  -2.319  -0.117  1.00  0.00           O  
HETATM    3  C2  UNL     1      -2.730  -1.075   0.338  1.00  0.00           C  
HETATM    4  C3  UNL     1      -3.613  -0.159   0.837  1.00  0.00           C  
HETATM    5  C4  UNL     1      -3.174   1.057   1.272  1.00  0.00           C  
HETATM    6  C5  UNL     1      -1.832   1.388   1.220  1.00  0.00           C  
HETATM    7  C6  UNL     1      -0.910   0.457   0.710  1.00  0.00           C  
HETATM    8  C7  UNL     1      -1.363  -0.769   0.271  1.00  0.00           C  
HETATM    9  O2  UNL     1      -0.508  -1.727  -0.239  1.00  0.00           O  
HETATM   10  C8  UNL     1      -0.426  -1.770  -1.674  1.00  0.00           C  
HETATM   11  C9  UNL     1       0.503   0.815   0.743  1.00  0.00           C  
HETATM   12  C10 UNL     1       1.451   0.056  -0.041  1.00  0.00           C  
HETATM   13  C11 UNL     1       1.809   0.492  -1.313  1.00  0.00           C  
HETATM   14  C12 UNL     1       2.743  -0.196  -2.056  1.00  0.00           C  
HETATM   15  C13 UNL     1       3.339  -1.340  -1.537  1.00  0.00           C  
HETATM   16  C14 UNL     1       2.996  -1.786  -0.279  1.00  0.00           C  
HETATM   17  C15 UNL     1       2.053  -1.079   0.456  1.00  0.00           C  
HETATM   18  O3  UNL     1       3.732  -2.926  -0.025  1.00  0.00           O  
HETATM   19  C16 UNL     1       4.649  -3.148  -1.091  1.00  0.00           C  
HETATM   20  O4  UNL     1       4.300  -2.203  -2.084  1.00  0.00           O  
HETATM   21  C17 UNL     1       0.712   2.281   0.613  1.00  0.00           C  
HETATM   22  C18 UNL     1      -0.254   3.136   0.871  1.00  0.00           C  
HETATM   23  C19 UNL     1       0.064   4.421   0.213  1.00  0.00           C  
HETATM   24  O5  UNL     1       1.497   4.404   0.293  1.00  0.00           O  
HETATM   25  C20 UNL     1       1.906   3.057   0.224  1.00  0.00           C  
HETATM   26  O6  UNL     1       3.054   2.672  -0.103  1.00  0.00           O  
HETATM   27  C21 UNL     1      -1.418   2.736   1.719  1.00  0.00           C  
HETATM   28  H1  UNL     1      -4.352  -3.926  -0.217  1.00  0.00           H  
HETATM   29  H2  UNL     1      -4.990  -2.431  -0.996  1.00  0.00           H  
HETATM   30  H3  UNL     1      -4.995  -2.577   0.776  1.00  0.00           H  
HETATM   31  H4  UNL     1      -4.659  -0.429   0.874  1.00  0.00           H  
HETATM   32  H5  UNL     1      -3.887   1.782   1.668  1.00  0.00           H  
HETATM   33  H6  UNL     1      -1.200  -2.484  -2.053  1.00  0.00           H  
HETATM   34  H7  UNL     1       0.575  -2.110  -1.970  1.00  0.00           H  
HETATM   35  H8  UNL     1      -0.641  -0.805  -2.142  1.00  0.00           H  
HETATM   36  H9  UNL     1       0.807   0.625   1.844  1.00  0.00           H  
HETATM   37  H10 UNL     1       1.320   1.374  -1.691  1.00  0.00           H  
HETATM   38  H11 UNL     1       3.039   0.127  -3.055  1.00  0.00           H  
HETATM   39  H12 UNL     1       1.754  -1.403   1.459  1.00  0.00           H  
HETATM   40  H13 UNL     1       5.683  -3.021  -0.724  1.00  0.00           H  
HETATM   41  H14 UNL     1       4.436  -4.152  -1.496  1.00  0.00           H  
HETATM   42  H15 UNL     1      -0.353   5.293   0.736  1.00  0.00           H  
HETATM   43  H16 UNL     1      -0.223   4.444  -0.848  1.00  0.00           H  
HETATM   44  H17 UNL     1      -1.119   2.611   2.773  1.00  0.00           H  
HETATM   45  H18 UNL     1      -2.260   3.422   1.570  1.00  0.00           H  
CONECT    1    2   28   29   30
CONECT    2    3
CONECT    3    4    4    8
CONECT    4    5   31
CONECT    5    6    6   32
CONECT    6    7   27
CONECT    7    8    8   11
CONECT    8    9
CONECT    9   10
CONECT   10   33   34   35
CONECT   11   12   21   36
CONECT   12   13   13   17
CONECT   13   14   37
CONECT   14   15   15   38
CONECT   15   16   20
CONECT   16   17   17   18
CONECT   17   39
CONECT   18   19
CONECT   19   20   40   41
CONECT   21   22   22   25
CONECT   22   23   27
CONECT   23   24   42   43
CONECT   24   25
CONECT   25   26   26
CONECT   27   44   45
END

HMDB0249101
     RDKit          3D
beta-Apopolygamatin
 45 49  0  0  0  0  0  0  0  0999 V2000
   -4.4101   -2.8126   -0.1355 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1092   -2.3189   -0.1167 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7297   -1.0755    0.3380 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6134   -0.1593    0.8368 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1737    1.0572    1.2723 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8318    1.3879    1.2198 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9105    0.4565    0.7104 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3630   -0.7694    0.2708 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5079   -1.7266   -0.2387 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4258   -1.7702   -1.6741 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5031    0.8148    0.7429 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4515    0.0561   -0.0414 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8090    0.4917   -1.3125 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7429   -0.1961   -2.0559 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3390   -1.3403   -1.5368 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9956   -1.7857   -0.2792 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0525   -1.0793    0.4556 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7323   -2.9256   -0.0249 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6495   -3.1479   -1.0909 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3004   -2.2028   -2.0845 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7122    2.2805    0.6129 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2536    3.1364    0.8710 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0640    4.4212    0.2127 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4966    4.4037    0.2928 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9058    3.0568    0.2241 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0540    2.6721   -0.1035 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4177    2.7361    1.7194 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3516   -3.9264   -0.2168 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9896   -2.4306   -0.9959 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9948   -2.5766    0.7760 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6586   -0.4290    0.8736 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8870    1.7816    1.6679 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1998   -2.4836   -2.0533 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5751   -2.1101   -1.9704 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6410   -0.8053   -2.1416 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8074    0.6250    1.8441 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3198    1.3739   -1.6911 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0391    0.1274   -3.0552 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7544   -1.4031    1.4588 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6833   -3.0214   -0.7237 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4364   -4.1523   -1.4960 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3534    5.2927    0.7362 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2228    4.4438   -0.8483 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1188    2.6111    2.7727 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2601    3.4217    1.5703 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
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
  7 11  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
 16 18  1  0
 18 19  1  0
 19 20  1  0
 11 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  2  0
 22 27  1  0
  8  3  1  0
 17 12  1  0
 25 21  1  0
 27  6  1  0
 20 15  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
  4 31  1  0
  5 32  1  0
 10 33  1  0
 10 34  1  0
 10 35  1  0
 11 36  1  0
 13 37  1  0
 14 38  1  0
 17 39  1  0
 19 40  1  0
 19 41  1  0
 23 42  1  0
 23 43  1  0
 27 44  1  0
 27 45  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₂₁H₁₈O₆

Average Molecular Weight

366.369

Monoisotopic Molecular Weight

366.1103383

IUPAC Name

9-(2H-1,3-benzodioxol-5-yl)-7,8-dimethoxy-1H,3H,4H,9H-naphtho[2,3-c]furan-1-one

Traditional Name

9-(2H-1,3-benzodioxol-5-yl)-7,8-dimethoxy-3H,4H,9H-naphtho[2,3-c]furan-1-one

CAS Registry Number

Not Available

SMILES

COC1=CC=C2CC3=C(C(C4=CC=C5OCOC5=C4)C2=C1OC)C(=O)OC3

InChI Identifier

InChI=1S/C21H18O6/c1-23-15-6-4-11-7-13-9-25-21(22)19(13)17(18(11)20(15)24-2)12-3-5-14-16(8-12)27-10-26-14/h3-6,8,17H,7,9-10H2,1-2H3

InChI Key

URJOZSLMTIRWFW-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as naphthofurans. Naphthofurans are compounds containing a furan ring fused to a naphthalene moiety. Furan is a 5 membered- ring aromatic ring with four carbon and one oxygen atoms. Naphthalene is a polycyclic aromatic hydrocarbon made up of two fused benzene rings.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Naphthofurans

Sub Class

Not Available

Direct Parent

Naphthofurans

Alternative Parents

Substituents

Naphthofuran
Naphthalene
Benzodioxole
Anisole
Alkyl aryl ether
2-furanone
Benzenoid
Dihydrofuran
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Lactone
Carboxylic acid ester
Monocarboxylic acid or derivatives
Ether
Acetal
Carboxylic acid derivative
Oxacycle
Carbonyl group
Hydrocarbon derivative
Organic oxygen compound
Organic oxide
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (PMID: 31557052)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular 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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	2.96	ALOGPS
logP	3.09	ChemAxon
logS	-4.2	ALOGPS
pKa (Strongest Acidic)	13.07	ChemAxon
pKa (Strongest Basic)	-4.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	63.22 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	96.56 m³·mol⁻¹	ChemAxon
Polarizability	37.32 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	187.306	30932474
DeepCCS	[M-H]-	184.948	30932474
DeepCCS	[M-2H]-	218.765	30932474
DeepCCS	[M+Na]+	193.993	30932474
AllCCS	[M+H]+	185.0	32859911
AllCCS	[M+H-H2O]+	181.9	32859911
AllCCS	[M+NH4]+	187.8	32859911
AllCCS	[M+Na]+	188.7	32859911
AllCCS	[M-H]-	190.1	32859911
AllCCS	[M+Na-2H]-	189.3	32859911
AllCCS	[M+HCOO]-	188.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
beta-Apopolygamatin	COC1=CC=C2CC3=C(C(C4=CC=C5OCOC5=C4)C2=C1OC)C(=O)OC3	4690.5	Standard polar	33892256
beta-Apopolygamatin	COC1=CC=C2CC3=C(C(C4=CC=C5OCOC5=C4)C2=C1OC)C(=O)OC3	3046.8	Standard non polar	33892256
beta-Apopolygamatin	COC1=CC=C2CC3=C(C(C4=CC=C5OCOC5=C4)C2=C1OC)C(=O)OC3	3176.7	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - beta-Apopolygamatin GC-MS (Non-derivatized) - 70eV, Positive	splash10-000i-0019000000-c6a15dfcfc1811a2b966	2021-09-24	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - beta-Apopolygamatin GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - beta-Apopolygamatin 10V, Negative-QTOF	splash10-01b9-0009000000-537eb9d8d64e3adf0390	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - beta-Apopolygamatin 20V, Negative-QTOF	splash10-014i-0009000000-3cc6fd73f94bd9f1ef98	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - beta-Apopolygamatin 40V, Negative-QTOF	splash10-01di-0049000000-1d57fb51cafaf3758ce9	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - beta-Apopolygamatin 10V, Positive-QTOF	splash10-014j-0089000000-a900bb64ff25e297c921	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - beta-Apopolygamatin 20V, Positive-QTOF	splash10-014i-0129000000-8f99722df861cac6ca21	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - beta-Apopolygamatin 40V, Positive-QTOF	splash10-000i-0119000000-c26ab70b6591882253b2	2021-10-12	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

10761270

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

22024150

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for beta-Apopolygamatin (HMDB0249101)

MOL for HMDB0249101 (beta-Apopolygamatin)

3D MOL for HMDB0249101 (beta-Apopolygamatin)

3D SDF for HMDB0249101 (beta-Apopolygamatin)

3D-SDF for HMDB0249101 (beta-Apopolygamatin)

PDB for HMDB0249101 (beta-Apopolygamatin)

3D PDB for HMDB0249101 (beta-Apopolygamatin)

SMILES for HMDB0249101 (beta-Apopolygamatin)

INCHI for HMDB0249101 (beta-Apopolygamatin)

Structure for HMDB0249101 (beta-Apopolygamatin)

3D Structure for HMDB0249101 (beta-Apopolygamatin)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra