NP-MRD: Showing NP-Card for 4-chloro-1-hydroxy-3-methoxy-6-methyl-8-methoxycarbonyl-xanthen-9-one (NP0016532)

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Record Information

Version

2.0

Created at

2021-01-06 01:29:15 UTC

Updated at

2021-07-15 17:22:58 UTC

NP-MRD ID

NP0016532

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4-chloro-1-hydroxy-3-methoxy-6-methyl-8-methoxycarbonyl-xanthen-9-one

Provided By

NPAtlas

Description

4-chloro-1-hydroxy-3-methoxy-6-methyl-8-methoxycarbonyl-xanthen-9-one is found in Penicillium and Penicillium citrinum. 4-chloro-1-hydroxy-3-methoxy-6-methyl-8-methoxycarbonyl-xanthen-9-one was first documented in 2017 (PMID: 28465625). Based on a literature review very few articles have been published on 4-chloro-1-hydroxy-3-methoxy-6-methyl-8-methoxycarbonyl-xanthen-9-one.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242104153D          

 37 39  0  0  0  0            999 V2000
   -3.1092   -3.7889   -0.2301 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4380   -2.5764    0.0152 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9374   -1.3840   -0.4208 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0672   -1.3940   -1.0795 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3922   -0.0482   -0.2522 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3133    1.0202   -0.1067 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9608    2.3119    0.1404 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0080    3.3924    0.2826 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6340    2.6232    0.2595 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7024    1.6152    0.1229 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5681    1.8833    0.2266 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5136    0.9927    0.1049 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8475    1.3943    0.2365 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2618    3.0492    0.5574 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.8330    0.4559    0.1077 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1658    0.8504    0.2378 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2272   -0.0802    0.1139 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5200   -0.8428   -0.1436 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1873   -1.3037   -0.2859 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9802   -2.6201   -0.5356 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2236   -0.3336   -0.1504 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1087   -0.7005   -0.2739 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4250   -1.8882   -0.5110 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0680    0.2845   -0.1321 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1717   -4.4234    0.6954 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5372   -4.3802   -1.0040 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1556   -3.6103   -0.5491 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3646    0.7863   -0.1985 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8839    2.9559    0.7847 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5550    4.2237    0.8457 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2122    3.7387   -0.7514 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3411    3.6382    0.4556 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1567    0.3307    0.5465 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4131   -0.3887   -0.9230 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0007   -1.0244    0.6907 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2916   -1.6154   -0.2515 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1953   -3.1436   -0.6653 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
  3  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
  7  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 15 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  5  1  0  0  0  0
 24 10  2  0  0  0  0
 21 12  1  0  0  0  0
  1 25  1  0  0  0  0
  1 26  1  0  0  0  0
  1 27  1  0  0  0  0
  6 28  1  0  0  0  0
  8 29  1  0  0  0  0
  8 30  1  0  0  0  0
  8 31  1  0  0  0  0
  9 32  1  0  0  0  0
 17 33  1  0  0  0  0
 17 34  1  0  0  0  0
 17 35  1  0  0  0  0
 18 36  1  0  0  0  0
 20 37  1  0  0  0  0
M  END

     RDKit          3D

 37 39  0  0  0  0  0  0  0  0999 V2000
   -3.1092   -3.7889   -0.2301 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4380   -2.5764    0.0152 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9374   -1.3840   -0.4208 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0672   -1.3940   -1.0795 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3922   -0.0482   -0.2522 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3133    1.0202   -0.1067 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9608    2.3119    0.1404 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0080    3.3924    0.2826 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6340    2.6232    0.2595 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7024    1.6152    0.1229 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5681    1.8833    0.2266 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5136    0.9927    0.1049 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8475    1.3943    0.2365 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2618    3.0492    0.5574 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.8330    0.4559    0.1077 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1658    0.8504    0.2378 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2272   -0.0802    0.1139 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5200   -0.8428   -0.1436 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1873   -1.3037   -0.2859 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9802   -2.6201   -0.5356 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2236   -0.3336   -0.1504 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1087   -0.7005   -0.2739 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4250   -1.8882   -0.5110 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0680    0.2845   -0.1321 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1717   -4.4234    0.6954 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5372   -4.3802   -1.0040 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1556   -3.6103   -0.5491 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3646    0.7863   -0.1985 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8839    2.9559    0.7847 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5550    4.2237    0.8457 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2122    3.7387   -0.7514 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3411    3.6382    0.4556 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1567    0.3307    0.5465 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4131   -0.3887   -0.9230 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0007   -1.0244    0.6907 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2916   -1.6154   -0.2515 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1953   -3.1436   -0.6653 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
  3  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  7  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 15 18  2  0
 18 19  1  0
 19 20  1  0
 19 21  2  0
 21 22  1  0
 22 23  2  0
 22 24  1  0
 24  5  1  0
 24 10  2  0
 21 12  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  6 28  1  0
  8 29  1  0
  8 30  1  0
  8 31  1  0
  9 32  1  0
 17 33  1  0
 17 34  1  0
 17 35  1  0
 18 36  1  0
 20 37  1  0
M  END


  Mrv1652306242104153D          

 37 39  0  0  0  0            999 V2000
   -3.1092   -3.7889   -0.2301 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4380   -2.5764    0.0152 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9374   -1.3840   -0.4208 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0672   -1.3940   -1.0795 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3922   -0.0482   -0.2522 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3133    1.0202   -0.1067 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9608    2.3119    0.1404 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0080    3.3924    0.2826 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6340    2.6232    0.2595 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7024    1.6152    0.1229 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5681    1.8833    0.2266 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5136    0.9927    0.1049 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8475    1.3943    0.2365 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2618    3.0492    0.5574 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.8330    0.4559    0.1077 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1658    0.8504    0.2378 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2272   -0.0802    0.1139 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5200   -0.8428   -0.1436 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1873   -1.3037   -0.2859 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9802   -2.6201   -0.5356 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2236   -0.3336   -0.1504 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1087   -0.7005   -0.2739 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4250   -1.8882   -0.5110 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0680    0.2845   -0.1321 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1717   -4.4234    0.6954 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5372   -4.3802   -1.0040 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1556   -3.6103   -0.5491 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3646    0.7863   -0.1985 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8839    2.9559    0.7847 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5550    4.2237    0.8457 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2122    3.7387   -0.7514 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3411    3.6382    0.4556 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1567    0.3307    0.5465 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4131   -0.3887   -0.9230 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0007   -1.0244    0.6907 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2916   -1.6154   -0.2515 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1953   -3.1436   -0.6653 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
  3  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
  7  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 15 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  5  1  0  0  0  0
 24 10  2  0  0  0  0
 21 12  1  0  0  0  0
  1 25  1  0  0  0  0
  1 26  1  0  0  0  0
  1 27  1  0  0  0  0
  6 28  1  0  0  0  0
  8 29  1  0  0  0  0
  8 30  1  0  0  0  0
  8 31  1  0  0  0  0
  9 32  1  0  0  0  0
 17 33  1  0  0  0  0
 17 34  1  0  0  0  0
 17 35  1  0  0  0  0
 18 36  1  0  0  0  0
 20 37  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0016532

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C2C(=O)C3=C(OC2=C(Cl)C(OC([H])([H])[H])=C1[H])C([H])=C(C([H])=C3C(=O)OC([H])([H])[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C17H13ClO6/c1-7-4-8(17(21)23-3)12-10(5-7)24-16-13(15(12)20)9(19)6-11(22-2)14(16)18/h4-6,19H,1-3H3

> <INCHI_KEY>
MYRRQAHCRTWRND-UHFFFAOYSA-N

> <FORMULA>
C17H13ClO6

> <MOLECULAR_WEIGHT>
348.74

> <EXACT_MASS>
348.0400658

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
37

> <JCHEM_AVERAGE_POLARIZABILITY>
34.62379137057101

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl 5-chloro-8-hydroxy-6-methoxy-3-methyl-9-oxo-9H-xanthene-1-carboxylate

> <ALOGPS_LOGP>
3.65

> <JCHEM_LOGP>
4.269346662666666

> <ALOGPS_LOGS>
-4.18

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.993082335293247

> <JCHEM_PKA_STRONGEST_BASIC>
-3.7752648513602094

> <JCHEM_POLAR_SURFACE_AREA>
82.06

> <JCHEM_REFRACTIVITY>
87.1317

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.30e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl 5-chloro-8-hydroxy-6-methoxy-3-methyl-9-oxoxanthene-1-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 37 39  0  0  0  0  0  0  0  0999 V2000
   -3.1092   -3.7889   -0.2301 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4380   -2.5764    0.0152 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9374   -1.3840   -0.4208 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0672   -1.3940   -1.0795 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3922   -0.0482   -0.2522 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3133    1.0202   -0.1067 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9608    2.3119    0.1404 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0080    3.3924    0.2826 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6340    2.6232    0.2595 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7024    1.6152    0.1229 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5681    1.8833    0.2266 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5136    0.9927    0.1049 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8475    1.3943    0.2365 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2618    3.0492    0.5574 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.8330    0.4559    0.1077 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1658    0.8504    0.2378 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2272   -0.0802    0.1139 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5200   -0.8428   -0.1436 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1873   -1.3037   -0.2859 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9802   -2.6201   -0.5356 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2236   -0.3336   -0.1504 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1087   -0.7005   -0.2739 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4250   -1.8882   -0.5110 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0680    0.2845   -0.1321 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1717   -4.4234    0.6954 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5372   -4.3802   -1.0040 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1556   -3.6103   -0.5491 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3646    0.7863   -0.1985 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8839    2.9559    0.7847 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5550    4.2237    0.8457 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2122    3.7387   -0.7514 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3411    3.6382    0.4556 H   0  0  0  0  0  0  0  0  0  0  0  0
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    6.4131   -0.3887   -0.9230 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0007   -1.0244    0.6907 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2916   -1.6154   -0.2515 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1953   -3.1436   -0.6653 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
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 17 33  1  0
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 17 35  1  0
 18 36  1  0
 20 37  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      -3.109  -3.789  -0.230  0.00  0.00           C+0
HETATM    2  O   UNK     0      -2.438  -2.576   0.015  0.00  0.00           O+0
HETATM    3  C   UNK     0      -2.937  -1.384  -0.421  0.00  0.00           C+0
HETATM    4  O   UNK     0      -4.067  -1.394  -1.079  0.00  0.00           O+0
HETATM    5  C   UNK     0      -2.392  -0.048  -0.252  0.00  0.00           C+0
HETATM    6  C   UNK     0      -3.313   1.020  -0.107  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.961   2.312   0.140  0.00  0.00           C+0
HETATM    8  C   UNK     0      -4.008   3.392   0.283  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.634   2.623   0.260  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.702   1.615   0.123  0.00  0.00           C+0
HETATM   11  O   UNK     0       0.568   1.883   0.227  0.00  0.00           O+0
HETATM   12  C   UNK     0       1.514   0.993   0.105  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.848   1.394   0.237  0.00  0.00           C+0
HETATM   14 Cl   UNK     0       3.262   3.049   0.557  0.00  0.00          Cl+0
HETATM   15  C   UNK     0       3.833   0.456   0.108  0.00  0.00           C+0
HETATM   16  O   UNK     0       5.166   0.850   0.238  0.00  0.00           O+0
HETATM   17  C   UNK     0       6.227  -0.080   0.114  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.520  -0.843  -0.144  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.187  -1.304  -0.286  0.00  0.00           C+0
HETATM   20  O   UNK     0       1.980  -2.620  -0.536  0.00  0.00           O+0
HETATM   21  C   UNK     0       1.224  -0.334  -0.150  0.00  0.00           C+0
HETATM   22  C   UNK     0      -0.109  -0.701  -0.274  0.00  0.00           C+0
HETATM   23  O   UNK     0      -0.425  -1.888  -0.511  0.00  0.00           O+0
HETATM   24  C   UNK     0      -1.068   0.285  -0.132  0.00  0.00           C+0
HETATM   25  H   UNK     0      -3.172  -4.423   0.695  0.00  0.00           H+0
HETATM   26  H   UNK     0      -2.537  -4.380  -1.004  0.00  0.00           H+0
HETATM   27  H   UNK     0      -4.156  -3.610  -0.549  0.00  0.00           H+0
HETATM   28  H   UNK     0      -4.365   0.786  -0.199  0.00  0.00           H+0
HETATM   29  H   UNK     0      -4.884   2.956   0.785  0.00  0.00           H+0
HETATM   30  H   UNK     0      -3.555   4.224   0.846  0.00  0.00           H+0
HETATM   31  H   UNK     0      -4.212   3.739  -0.751  0.00  0.00           H+0
HETATM   32  H   UNK     0      -1.341   3.638   0.456  0.00  0.00           H+0
HETATM   33  H   UNK     0       7.157   0.331   0.547  0.00  0.00           H+0
HETATM   34  H   UNK     0       6.413  -0.389  -0.923  0.00  0.00           H+0
HETATM   35  H   UNK     0       6.001  -1.024   0.691  0.00  0.00           H+0
HETATM   36  H   UNK     0       4.292  -1.615  -0.252  0.00  0.00           H+0
HETATM   37  H   UNK     0       1.195  -3.144  -0.665  0.00  0.00           H+0
CONECT    1    2   25   26   27                                             
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   24                                                  
CONECT    6    5    7   28                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7   29   30   31                                             
CONECT    9    7   10   32                                                  
CONECT   10    9   11   24                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   21                                                  
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   18                                                  
CONECT   16   15   17                                                       
CONECT   17   16   33   34   35                                             
CONECT   18   15   19   36                                                  
CONECT   19   18   20   21                                                  
CONECT   20   19   37                                                       
CONECT   21   19   22   12                                                  
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22    5   10                                                  
CONECT   25    1                                                            
CONECT   26    1                                                            
CONECT   27    1                                                            
CONECT   28    6                                                            
CONECT   29    8                                                            
CONECT   30    8                                                            
CONECT   31    8                                                            
CONECT   32    9                                                            
CONECT   33   17                                                            
CONECT   34   17                                                            
CONECT   35   17                                                            
CONECT   36   18                                                            
CONECT   37   20                                                            
MASTER        0    0    0    0    0    0    0    0   37    0   78    0
END

RDKit          3D

37 39  0  0  0  0  0  0  0  0999 V2000
   -3.1092   -3.7889   -0.2301 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4380   -2.5764    0.0152 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9374   -1.3840   -0.4208 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0672   -1.3940   -1.0795 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3922   -0.0482   -0.2522 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3133    1.0202   -0.1067 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9608    2.3119    0.1404 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0080    3.3924    0.2826 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6340    2.6232    0.2595 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7024    1.6152    0.1229 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5681    1.8833    0.2266 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5136    0.9927    0.1049 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8475    1.3943    0.2365 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2618    3.0492    0.5574 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.8330    0.4559    0.1077 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1658    0.8504    0.2378 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2272   -0.0802    0.1139 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5200   -0.8428   -0.1436 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1873   -1.3037   -0.2859 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9802   -2.6201   -0.5356 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2236   -0.3336   -0.1504 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1087   -0.7005   -0.2739 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4250   -1.8882   -0.5110 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0680    0.2845   -0.1321 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1717   -4.4234    0.6954 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5372   -4.3802   -1.0040 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1556   -3.6103   -0.5491 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3646    0.7863   -0.1985 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8839    2.9559    0.7847 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5550    4.2237    0.8457 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2122    3.7387   -0.7514 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3411    3.6382    0.4556 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1567    0.3307    0.5465 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4131   -0.3887   -0.9230 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0007   -1.0244    0.6907 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2916   -1.6154   -0.2515 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1953   -3.1436   -0.6653 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
  3  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  7  9  2  0
  9 10  1  0
 10 11  1  0
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 17 33  1  0
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 17 35  1  0
 18 36  1  0
 20 37  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Value	Source
Methyl 5-chloro-8-hydroxy-6-methoxy-3-methyl-9-oxo-9H-xanthene-1-carboxylic acid	Generator

Chemical Formula

C₁₇H₁₃ClO₆

Average Mass

348.7400 Da

Monoisotopic Mass

348.04007 Da

IUPAC Name

methyl 5-chloro-8-hydroxy-6-methoxy-3-methyl-9-oxo-9H-xanthene-1-carboxylate

Traditional Name

methyl 5-chloro-8-hydroxy-6-methoxy-3-methyl-9-oxoxanthene-1-carboxylate

CAS Registry Number

Not Available

SMILES

COC(=O)C1=CC(C)=CC2=C1C(=O)C1=C(O2)C(Cl)=C(OC)C=C1O

InChI Identifier

InChI=1S/C17H13ClO6/c1-7-4-8(17(21)23-3)12-10(5-7)24-16-13(15(12)20)9(19)6-11(22-2)14(16)18/h4-6,19H,1-3H3

InChI Key

MYRRQAHCRTWRND-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
Penicillium	NPAtlas	28465625
Penicillium citrinum	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	3.65	ALOGPS
logP	4.27	ChemAxon
logS	-4.2	ALOGPS
pKa (Strongest Acidic)	7.99	ChemAxon
pKa (Strongest Basic)	-3.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	82.06 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	87.13 m³·mol⁻¹	ChemAxon
Polarizability	34.62 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

NPAtlas ID

NPA021660

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

59718422

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

139589443

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

He KY, Zhang C, Duan YR, Huang GL, Yang CY, Lu XR, Zheng CJ, Chen GY: New chlorinated xanthone and anthraquinone produced by a mangrove-derived fungus Penicillium citrinum HL-5126. J Antibiot (Tokyo). 2017 Jul;70(7):823-827. doi: 10.1038/ja.2017.52. Epub 2017 May 3. [PubMed:28465625 ]

Showing NP-Card for 4-chloro-1-hydroxy-3-methoxy-6-methyl-8-methoxycarbonyl-xanthen-9-one (NP0016532)

MOL for NP0016532 (4-chloro-1-hydroxy-3-methoxy-6-methyl-8-methoxycarbonyl-xanthen-9-one)

3D MOL for NP0016532 (4-chloro-1-hydroxy-3-methoxy-6-methyl-8-methoxycarbonyl-xanthen-9-one)

3D SDF for NP0016532 (4-chloro-1-hydroxy-3-methoxy-6-methyl-8-methoxycarbonyl-xanthen-9-one)

3D-SDF for NP0016532 (4-chloro-1-hydroxy-3-methoxy-6-methyl-8-methoxycarbonyl-xanthen-9-one)

PDB for NP0016532 (4-chloro-1-hydroxy-3-methoxy-6-methyl-8-methoxycarbonyl-xanthen-9-one)

3D PDB for NP0016532 (4-chloro-1-hydroxy-3-methoxy-6-methyl-8-methoxycarbonyl-xanthen-9-one)

SMILES for NP0016532 (4-chloro-1-hydroxy-3-methoxy-6-methyl-8-methoxycarbonyl-xanthen-9-one)

INCHI for NP0016532 (4-chloro-1-hydroxy-3-methoxy-6-methyl-8-methoxycarbonyl-xanthen-9-one)

Structure for NP0016532 (4-chloro-1-hydroxy-3-methoxy-6-methyl-8-methoxycarbonyl-xanthen-9-one)

3D Structure for NP0016532 (4-chloro-1-hydroxy-3-methoxy-6-methyl-8-methoxycarbonyl-xanthen-9-one)