NP-MRD: Showing NP-Card for Fumaquinone (NP0005923)

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Record Information

Version

2.0

Created at

2020-12-09 03:02:17 UTC

Updated at

2021-07-15 16:53:21 UTC

NP-MRD ID

NP0005923

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Fumaquinone

Provided By

NPAtlas

Description

Fumaquinone is found in Streptomyces and Streptomyces fumanus. Fumaquinone was first documented in 2005 (PMID: 15981414). Based on a literature review a small amount of articles have been published on Fumaquinone (PMID: 20067528) (PMID: 20583743).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242118243D          

 40 41  0  0  0  0            999 V2000
    5.7663    0.7571    0.0380 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0036   -0.0342   -0.8432 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6454   -0.2392   -0.5910 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0045   -1.0213   -1.4433 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7037   -1.6433   -2.6042 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5781   -1.2904   -1.2543 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0202   -2.0506   -2.1091 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8388   -0.7123   -0.1391 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5595    0.1130    0.7423 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8976    0.6677    1.7955 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4365    0.4370    2.0042 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0745    1.0165    3.0829 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1350   -0.3708    1.1391 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5680   -0.6517    1.3331 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.3599    0.5387    0.9453 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3177    0.5720    0.0489 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0283    1.8443   -0.2392 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7168   -0.6491   -0.6771 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5031   -0.9721    0.0319 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2350   -1.7660   -0.7987 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9854    0.3743    0.5425 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5848    1.1137    1.3506 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8031    0.7624   -0.3818 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7308    0.2845    1.0340 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4111    1.8097    0.1025 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6638   -0.9742   -3.5135 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7951   -1.7741   -2.4086 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2495   -2.5974   -2.8701 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4785    1.2988    2.4584 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5462    1.6062    3.7080 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7617   -0.9455    2.3864 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8782   -1.5073    0.7054 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0862    1.4632    1.4870 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9977    1.9101    0.2952 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1890    1.9973   -1.3232 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4158    2.6899    0.1212 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4117   -0.4044   -1.5260 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8495   -1.1451   -1.0996 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2384   -1.3262    0.0530 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9707   -2.2448   -1.5833 H   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
  4  6  1  0  0  0  0
  6  7  2  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  2  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  3  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 13 19  2  0  0  0  0
 19 20  1  0  0  0  0
  9 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21  3  1  0  0  0  0
 19  8  1  0  0  0  0
  1 23  1  0  0  0  0
  1 24  1  0  0  0  0
  1 25  1  0  0  0  0
  5 26  1  0  0  0  0
  5 27  1  0  0  0  0
  5 28  1  0  0  0  0
 10 29  1  0  0  0  0
 12 30  1  0  0  0  0
 14 31  1  0  0  0  0
 14 32  1  0  0  0  0
 15 33  1  0  0  0  0
 17 34  1  0  0  0  0
 17 35  1  0  0  0  0
 17 36  1  0  0  0  0
 18 37  1  0  0  0  0
 18 38  1  0  0  0  0
 18 39  1  0  0  0  0
 20 40  1  0  0  0  0
M  END

     RDKit          3D

 40 41  0  0  0  0  0  0  0  0999 V2000
    5.7663    0.7571    0.0380 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0036   -0.0342   -0.8432 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6454   -0.2392   -0.5910 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0045   -1.0213   -1.4433 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7037   -1.6433   -2.6042 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5781   -1.2904   -1.2543 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0202   -2.0506   -2.1091 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8388   -0.7123   -0.1391 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5595    0.1130    0.7423 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8976    0.6677    1.7955 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4365    0.4370    2.0042 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0745    1.0165    3.0829 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1350   -0.3708    1.1391 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5680   -0.6517    1.3331 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3599    0.5387    0.9453 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3177    0.5720    0.0489 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0283    1.8443   -0.2392 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7168   -0.6491   -0.6771 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5031   -0.9721    0.0319 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2350   -1.7660   -0.7987 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9854    0.3743    0.5425 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5848    1.1137    1.3506 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8031    0.7624   -0.3818 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7308    0.2845    1.0340 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4111    1.8097    0.1025 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6638   -0.9742   -3.5135 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7951   -1.7741   -2.4086 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2495   -2.5974   -2.8701 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4785    1.2988    2.4584 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5462    1.6062    3.7080 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7617   -0.9455    2.3864 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8782   -1.5073    0.7054 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0862    1.4632    1.4870 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9977    1.9101    0.2952 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1890    1.9973   -1.3232 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4158    2.6899    0.1212 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4117   -0.4044   -1.5260 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8495   -1.1451   -1.0996 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2384   -1.3262    0.0530 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9707   -2.2448   -1.5833 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
  4  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  3
 16 17  1  0
 16 18  1  0
 13 19  2  0
 19 20  1  0
  9 21  1  0
 21 22  2  0
 21  3  1  0
 19  8  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  5 26  1  0
  5 27  1  0
  5 28  1  0
 10 29  1  0
 12 30  1  0
 14 31  1  0
 14 32  1  0
 15 33  1  0
 17 34  1  0
 17 35  1  0
 17 36  1  0
 18 37  1  0
 18 38  1  0
 18 39  1  0
 20 40  1  0
M  END


  Mrv1652306242118243D          

 40 41  0  0  0  0            999 V2000
    5.7663    0.7571    0.0380 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0036   -0.0342   -0.8432 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6454   -0.2392   -0.5910 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0045   -1.0213   -1.4433 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7037   -1.6433   -2.6042 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5781   -1.2904   -1.2543 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0202   -2.0506   -2.1091 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8388   -0.7123   -0.1391 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5595    0.1130    0.7423 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8976    0.6677    1.7955 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4365    0.4370    2.0042 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0745    1.0165    3.0829 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1350   -0.3708    1.1391 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5680   -0.6517    1.3331 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.3599    0.5387    0.9453 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3177    0.5720    0.0489 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0283    1.8443   -0.2392 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7168   -0.6491   -0.6771 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5031   -0.9721    0.0319 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2350   -1.7660   -0.7987 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9854    0.3743    0.5425 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5848    1.1137    1.3506 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8031    0.7624   -0.3818 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7308    0.2845    1.0340 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4111    1.8097    0.1025 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6638   -0.9742   -3.5135 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7951   -1.7741   -2.4086 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2495   -2.5974   -2.8701 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4785    1.2988    2.4584 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5462    1.6062    3.7080 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7617   -0.9455    2.3864 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8782   -1.5073    0.7054 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0862    1.4632    1.4870 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9977    1.9101    0.2952 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1890    1.9973   -1.3232 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4158    2.6899    0.1212 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4117   -0.4044   -1.5260 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8495   -1.1451   -1.0996 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2384   -1.3262    0.0530 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9707   -2.2448   -1.5833 H   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
  4  6  1  0  0  0  0
  6  7  2  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  2  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  3  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 13 19  2  0  0  0  0
 19 20  1  0  0  0  0
  9 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21  3  1  0  0  0  0
 19  8  1  0  0  0  0
  1 23  1  0  0  0  0
  1 24  1  0  0  0  0
  1 25  1  0  0  0  0
  5 26  1  0  0  0  0
  5 27  1  0  0  0  0
  5 28  1  0  0  0  0
 10 29  1  0  0  0  0
 12 30  1  0  0  0  0
 14 31  1  0  0  0  0
 14 32  1  0  0  0  0
 15 33  1  0  0  0  0
 17 34  1  0  0  0  0
 17 35  1  0  0  0  0
 17 36  1  0  0  0  0
 18 37  1  0  0  0  0
 18 38  1  0  0  0  0
 18 39  1  0  0  0  0
 20 40  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0005923

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C([H])C2=C(C(=O)C(=C(OC([H])([H])[H])C2=O)C([H])([H])[H])C(O[H])=C1C([H])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C17H18O5/c1-8(2)5-6-10-12(18)7-11-13(15(10)20)14(19)9(3)17(22-4)16(11)21/h5,7,18,20H,6H2,1-4H3

> <INCHI_KEY>
DZMXLHINHRMDEG-UHFFFAOYSA-N

> <FORMULA>
C17H18O5

> <MOLECULAR_WEIGHT>
302.326

> <EXACT_MASS>
302.11542368

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
40

> <JCHEM_AVERAGE_POLARIZABILITY>
32.23490795809022

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5,7-dihydroxy-2-methoxy-3-methyl-6-(3-methylbut-2-en-1-yl)-1,4-dihydronaphthalene-1,4-dione

> <ALOGPS_LOGP>
2.70

> <JCHEM_LOGP>
3.255474503999999

> <ALOGPS_LOGS>
-3.52

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.721868929483541

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.107781734701899

> <JCHEM_PKA_STRONGEST_BASIC>
-4.950742383860576

> <JCHEM_POLAR_SURFACE_AREA>
83.83000000000001

> <JCHEM_REFRACTIVITY>
85.46349999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.10e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5,7-dihydroxy-2-methoxy-3-methyl-6-(3-methylbut-2-en-1-yl)naphthalene-1,4-dione

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 40 41  0  0  0  0  0  0  0  0999 V2000
    5.7663    0.7571    0.0380 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0036   -0.0342   -0.8432 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6454   -0.2392   -0.5910 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0045   -1.0213   -1.4433 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7037   -1.6433   -2.6042 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5781   -1.2904   -1.2543 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0202   -2.0506   -2.1091 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8388   -0.7123   -0.1391 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5595    0.1130    0.7423 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8976    0.6677    1.7955 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4365    0.4370    2.0042 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0745    1.0165    3.0829 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1350   -0.3708    1.1391 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5680   -0.6517    1.3331 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3599    0.5387    0.9453 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3177    0.5720    0.0489 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0283    1.8443   -0.2392 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7168   -0.6491   -0.6771 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5031   -0.9721    0.0319 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2350   -1.7660   -0.7987 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9854    0.3743    0.5425 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5848    1.1137    1.3506 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8031    0.7624   -0.3818 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7308    0.2845    1.0340 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4111    1.8097    0.1025 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6638   -0.9742   -3.5135 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7951   -1.7741   -2.4086 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2495   -2.5974   -2.8701 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4785    1.2988    2.4584 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5462    1.6062    3.7080 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7617   -0.9455    2.3864 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8782   -1.5073    0.7054 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0862    1.4632    1.4870 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9977    1.9101    0.2952 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1890    1.9973   -1.3232 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4158    2.6899    0.1212 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4117   -0.4044   -1.5260 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8495   -1.1451   -1.0996 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2384   -1.3262    0.0530 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9707   -2.2448   -1.5833 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
  4  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  3
 16 17  1  0
 16 18  1  0
 13 19  2  0
 19 20  1  0
  9 21  1  0
 21 22  2  0
 21  3  1  0
 19  8  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  5 26  1  0
  5 27  1  0
  5 28  1  0
 10 29  1  0
 12 30  1  0
 14 31  1  0
 14 32  1  0
 15 33  1  0
 17 34  1  0
 17 35  1  0
 17 36  1  0
 18 37  1  0
 18 38  1  0
 18 39  1  0
 20 40  1  0
M  END

HEADER    PROTEIN                                 24-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-JUN-21         0                                  
HETATM    1  C   UNK     0       5.766   0.757   0.038  0.00  0.00           C+0
HETATM    2  O   UNK     0       5.004  -0.034  -0.843  0.00  0.00           O+0
HETATM    3  C   UNK     0       3.645  -0.239  -0.591  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.005  -1.021  -1.443  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.704  -1.643  -2.604  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.578  -1.290  -1.254  0.00  0.00           C+0
HETATM    7  O   UNK     0       1.020  -2.051  -2.109  0.00  0.00           O+0
HETATM    8  C   UNK     0       0.839  -0.712  -0.139  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.560   0.113   0.742  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.898   0.668   1.796  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.437   0.437   2.004  0.00  0.00           C+0
HETATM   12  O   UNK     0      -1.075   1.016   3.083  0.00  0.00           O+0
HETATM   13  C   UNK     0      -1.135  -0.371   1.139  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.568  -0.652   1.333  0.00  0.00           C+0
HETATM   15  C   UNK     0      -3.360   0.539   0.945  0.00  0.00           C+0
HETATM   16  C   UNK     0      -4.318   0.572   0.049  0.00  0.00           C+0
HETATM   17  C   UNK     0      -5.028   1.844  -0.239  0.00  0.00           C+0
HETATM   18  C   UNK     0      -4.717  -0.649  -0.677  0.00  0.00           C+0
HETATM   19  C   UNK     0      -0.503  -0.972   0.032  0.00  0.00           C+0
HETATM   20  O   UNK     0      -1.235  -1.766  -0.799  0.00  0.00           O+0
HETATM   21  C   UNK     0       2.985   0.374   0.543  0.00  0.00           C+0
HETATM   22  O   UNK     0       3.585   1.114   1.351  0.00  0.00           O+0
HETATM   23  H   UNK     0       6.803   0.762  -0.382  0.00  0.00           H+0
HETATM   24  H   UNK     0       5.731   0.285   1.034  0.00  0.00           H+0
HETATM   25  H   UNK     0       5.411   1.810   0.103  0.00  0.00           H+0
HETATM   26  H   UNK     0       3.664  -0.974  -3.514  0.00  0.00           H+0
HETATM   27  H   UNK     0       4.795  -1.774  -2.409  0.00  0.00           H+0
HETATM   28  H   UNK     0       3.249  -2.597  -2.870  0.00  0.00           H+0
HETATM   29  H   UNK     0       1.478   1.299   2.458  0.00  0.00           H+0
HETATM   30  H   UNK     0      -0.546   1.606   3.708  0.00  0.00           H+0
HETATM   31  H   UNK     0      -2.762  -0.946   2.386  0.00  0.00           H+0
HETATM   32  H   UNK     0      -2.878  -1.507   0.705  0.00  0.00           H+0
HETATM   33  H   UNK     0      -3.086   1.463   1.487  0.00  0.00           H+0
HETATM   34  H   UNK     0      -5.998   1.910   0.295  0.00  0.00           H+0
HETATM   35  H   UNK     0      -5.189   1.997  -1.323  0.00  0.00           H+0
HETATM   36  H   UNK     0      -4.416   2.690   0.121  0.00  0.00           H+0
HETATM   37  H   UNK     0      -5.412  -0.404  -1.526  0.00  0.00           H+0
HETATM   38  H   UNK     0      -3.849  -1.145  -1.100  0.00  0.00           H+0
HETATM   39  H   UNK     0      -5.238  -1.326   0.053  0.00  0.00           H+0
HETATM   40  H   UNK     0      -0.971  -2.245  -1.583  0.00  0.00           H+0
CONECT    1    2   23   24   25                                             
CONECT    2    1    3                                                       
CONECT    3    2    4   21                                                  
CONECT    4    3    5    6                                                  
CONECT    5    4   26   27   28                                             
CONECT    6    4    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   19                                                  
CONECT    9    8   10   21                                                  
CONECT   10    9   11   29                                                  
CONECT   11   10   12   13                                                  
CONECT   12   11   30                                                       
CONECT   13   11   14   19                                                  
CONECT   14   13   15   31   32                                             
CONECT   15   14   16   33                                                  
CONECT   16   15   17   18                                                  
CONECT   17   16   34   35   36                                             
CONECT   18   16   37   38   39                                             
CONECT   19   13   20    8                                                  
CONECT   20   19   40                                                       
CONECT   21    9   22    3                                                  
CONECT   22   21                                                            
CONECT   23    1                                                            
CONECT   24    1                                                            
CONECT   25    1                                                            
CONECT   26    5                                                            
CONECT   27    5                                                            
CONECT   28    5                                                            
CONECT   29   10                                                            
CONECT   30   12                                                            
CONECT   31   14                                                            
CONECT   32   14                                                            
CONECT   33   15                                                            
CONECT   34   17                                                            
CONECT   35   17                                                            
CONECT   36   17                                                            
CONECT   37   18                                                            
CONECT   38   18                                                            
CONECT   39   18                                                            
CONECT   40   20                                                            
MASTER        0    0    0    0    0    0    0    0   40    0   82    0
END

RDKit          3D

40 41  0  0  0  0  0  0  0  0999 V2000
    5.7663    0.7571    0.0380 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0036   -0.0342   -0.8432 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6454   -0.2392   -0.5910 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0045   -1.0213   -1.4433 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7037   -1.6433   -2.6042 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5781   -1.2904   -1.2543 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0202   -2.0506   -2.1091 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8388   -0.7123   -0.1391 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5595    0.1130    0.7423 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8976    0.6677    1.7955 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4365    0.4370    2.0042 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0745    1.0165    3.0829 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1350   -0.3708    1.1391 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5680   -0.6517    1.3331 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3599    0.5387    0.9453 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3177    0.5720    0.0489 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0283    1.8443   -0.2392 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7168   -0.6491   -0.6771 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5031   -0.9721    0.0319 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2350   -1.7660   -0.7987 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9854    0.3743    0.5425 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5848    1.1137    1.3506 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8031    0.7624   -0.3818 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7308    0.2845    1.0340 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4111    1.8097    0.1025 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6638   -0.9742   -3.5135 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7951   -1.7741   -2.4086 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2495   -2.5974   -2.8701 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4785    1.2988    2.4584 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5462    1.6062    3.7080 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7617   -0.9455    2.3864 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8782   -1.5073    0.7054 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0862    1.4632    1.4870 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9977    1.9101    0.2952 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1890    1.9973   -1.3232 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4158    2.6899    0.1212 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4117   -0.4044   -1.5260 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8495   -1.1451   -1.0996 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2384   -1.3262    0.0530 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9707   -2.2448   -1.5833 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
  4  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  3
 16 17  1  0
 16 18  1  0
 13 19  2  0
 19 20  1  0
  9 21  1  0
 21 22  2  0
 21  3  1  0
 19  8  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  5 26  1  0
  5 27  1  0
  5 28  1  0
 10 29  1  0
 12 30  1  0
 14 31  1  0
 14 32  1  0
 15 33  1  0
 17 34  1  0
 17 35  1  0
 17 36  1  0
 18 37  1  0
 18 38  1  0
 18 39  1  0
 20 40  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Not Available

Chemical Formula

C₁₇H₁₈O₅

Average Mass

302.3260 Da

Monoisotopic Mass

302.11542 Da

IUPAC Name

5,7-dihydroxy-2-methoxy-3-methyl-6-(3-methylbut-2-en-1-yl)-1,4-dihydronaphthalene-1,4-dione

Traditional Name

5,7-dihydroxy-2-methoxy-3-methyl-6-(3-methylbut-2-en-1-yl)naphthalene-1,4-dione

CAS Registry Number

Not Available

SMILES

COC1=C(C)C(=O)C2=C(O)C(CC=C(C)C)=C(O)C=C2C1=O

InChI Identifier

InChI=1S/C17H18O5/c1-8(2)5-6-10-12(18)7-11-13(15(10)20)14(19)9(3)17(22-4)16(11)21/h5,7,18,20H,6H2,1-4H3

InChI Key

DZMXLHINHRMDEG-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, 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
Streptomyces	NPAtlas	15981414
Streptomyces fumanus	LOTUS Database	35616633

Chemical Taxonomy

Classification

Not classified

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	2.7	ALOGPS
logP	3.26	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Acidic)	7.11	ChemAxon
pKa (Strongest Basic)	-5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	83.83 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	85.46 m³·mol⁻¹	ChemAxon
Polarizability	32.23 Å³	ChemAxon
Number of Rings	2	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

NPAtlas ID

NPA009207

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

9635678

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11460838

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Charan RD, Schlingmann G, Bernan VS, Feng X, Carter GT: Fumaquinone, a new prenylated naphthoquinone from Streptomyces fumanus. J Antibiot (Tokyo). 2005 Apr;58(4):271-4. doi: 10.1038/ja.2005.32. [PubMed:15981414 ]
Khan ST, Izumikawa M, Motohashi K, Mukai A, Takagi M, Shin-Ya K: Distribution of the 3-hydroxyl-3-methylglutaryl coenzyme A reductase gene and isoprenoid production in marine-derived Actinobacteria. FEMS Microbiol Lett. 2010 Mar;304(1):89-96. doi: 10.1111/j.1574-6968.2009.01886.x. Epub 2009 Dec 19. [PubMed:20067528 ]
Pena-Lopez M, Martinez MM, Sarandeses LA, Perez Sestelo J: A versatile synthesis of fumaquinone. J Org Chem. 2010 Aug 6;75(15):5337-9. doi: 10.1021/jo100779z. [PubMed:20583743 ]

Showing NP-Card for Fumaquinone (NP0005923)

MOL for NP0005923 (Fumaquinone)

3D MOL for NP0005923 (Fumaquinone)

3D SDF for NP0005923 (Fumaquinone)

3D-SDF for NP0005923 (Fumaquinone)

PDB for NP0005923 (Fumaquinone)

3D PDB for NP0005923 (Fumaquinone)

SMILES for NP0005923 (Fumaquinone)

INCHI for NP0005923 (Fumaquinone)

Structure for NP0005923 (Fumaquinone)

3D Structure for NP0005923 (Fumaquinone)