NP-MRD: Showing NP-Card for Chaetoatrosin A (NP0003288)

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Record Information

Version

1.0

Created at

2020-12-09 00:32:45 UTC

Updated at

2021-07-15 16:46:02 UTC

NP-MRD ID

NP0003288

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Chaetoatrosin A

Provided By

NPAtlas

Description

Chaetoatrosin A is found in Amesia atrobrunnea and Chaetomium. It was first documented in 2000 (PMID: 10819295). Based on a literature review very few articles have been published on 1-(4,5-dihydroxy-7-methoxynaphthalen-2-yl)-2-hydroxypropan-1-one.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242117463D          

 33 34  0  0  0  0            999 V2000
    4.7274    2.1093   -0.2130 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7026    0.7835    0.2351 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4796    0.0915    0.2901 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4153   -1.2065    0.7229 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1849   -1.8934    0.7751 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1997   -3.1733    1.2134 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0297   -1.2381    0.3811 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2043   -1.8532    0.4084 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3522   -3.1442    0.8264 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3414   -1.1594    0.0040 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3230    0.1314   -0.4331 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4792    0.8946   -0.8640 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2611    2.1164   -1.2480 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8740    0.4884   -0.9317 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.7000    1.4381   -0.0401 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1499   -0.7896   -0.5373 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0520    0.7330   -0.4503 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0915    0.0879   -0.0615 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3284    0.7097   -0.0906 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2139    2.2739   -1.1665 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2406    2.7796    0.5391 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7931    2.4168   -0.3760 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3043   -1.7268    1.0315 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5516   -3.8589    1.3512 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1997   -3.6620    0.8776 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2554   -1.6909    0.0500 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2530    0.7069   -1.9637 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0636    1.6868    0.8475 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9128    2.3603   -0.5801 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6128    0.9328    0.2940 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6503   -0.8429    0.2988 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0373    1.7541   -0.7850 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3846    1.7440   -0.4347 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
  5  6  1  0  0  0  0
  5  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  2  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
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 11 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19  3  1  0  0  0  0
 18  7  1  0  0  0  0
  1 20  1  0  0  0  0
  1 21  1  0  0  0  0
  1 22  1  0  0  0  0
  4 23  1  0  0  0  0
  6 24  1  0  0  0  0
  9 25  1  0  0  0  0
 10 26  1  0  0  0  0
 14 27  1  6  0  0  0
 15 28  1  0  0  0  0
 15 29  1  0  0  0  0
 15 30  1  0  0  0  0
 16 31  1  0  0  0  0
 17 32  1  0  0  0  0
 19 33  1  0  0  0  0
M  END

     RDKit          3D

 33 34  0  0  0  0  0  0  0  0999 V2000
    4.7274    2.1093   -0.2130 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7026    0.7835    0.2351 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4796    0.0915    0.2901 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4153   -1.2065    0.7229 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1849   -1.8934    0.7751 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1997   -3.1733    1.2134 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0297   -1.2381    0.3811 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2043   -1.8532    0.4084 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3522   -3.1442    0.8264 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3414   -1.1594    0.0040 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3230    0.1314   -0.4331 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4792    0.8946   -0.8640 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2611    2.1164   -1.2480 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8740    0.4884   -0.9317 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.7000    1.4381   -0.0401 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1499   -0.7896   -0.5373 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0520    0.7330   -0.4503 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0915    0.0879   -0.0615 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3284    0.7097   -0.0906 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2139    2.2739   -1.1665 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2406    2.7796    0.5391 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7931    2.4168   -0.3760 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3043   -1.7268    1.0315 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5516   -3.8589    1.3512 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1997   -3.6620    0.8776 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2554   -1.6909    0.0500 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2530    0.7069   -1.9637 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0636    1.6868    0.8475 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9128    2.3603   -0.5801 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6128    0.9328    0.2940 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6503   -0.8429    0.2988 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0373    1.7541   -0.7850 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3846    1.7440   -0.4347 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  5  7  2  0
  7  8  1  0
  8  9  1  0
  8 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  1  0
 14 16  1  0
 11 17  2  0
 17 18  1  0
 18 19  2  0
 19  3  1  0
 18  7  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  4 23  1  0
  6 24  1  0
  9 25  1  0
 10 26  1  0
 14 27  1  6
 15 28  1  0
 15 29  1  0
 15 30  1  0
 16 31  1  0
 17 32  1  0
 19 33  1  0
M  END


  Mrv1652306242117463D          

 33 34  0  0  0  0            999 V2000
    4.7274    2.1093   -0.2130 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7026    0.7835    0.2351 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4796    0.0915    0.2901 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4153   -1.2065    0.7229 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1849   -1.8934    0.7751 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1997   -3.1733    1.2134 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0297   -1.2381    0.3811 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2043   -1.8532    0.4084 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3522   -3.1442    0.8264 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3414   -1.1594    0.0040 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3230    0.1314   -0.4331 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4792    0.8946   -0.8640 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2611    2.1164   -1.2480 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8740    0.4884   -0.9317 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.7000    1.4381   -0.0401 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1499   -0.7896   -0.5373 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0520    0.7330   -0.4503 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0915    0.0879   -0.0615 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3284    0.7097   -0.0906 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2139    2.2739   -1.1665 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2406    2.7796    0.5391 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7931    2.4168   -0.3760 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3043   -1.7268    1.0315 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5516   -3.8589    1.3512 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1997   -3.6620    0.8776 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2554   -1.6909    0.0500 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2530    0.7069   -1.9637 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0636    1.6868    0.8475 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9128    2.3603   -0.5801 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6128    0.9328    0.2940 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6503   -0.8429    0.2988 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0373    1.7541   -0.7850 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3846    1.7440   -0.4347 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
  5  6  1  0  0  0  0
  5  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  2  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
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 11 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19  3  1  0  0  0  0
 18  7  1  0  0  0  0
  1 20  1  0  0  0  0
  1 21  1  0  0  0  0
  1 22  1  0  0  0  0
  4 23  1  0  0  0  0
  6 24  1  0  0  0  0
  9 25  1  0  0  0  0
 10 26  1  0  0  0  0
 14 27  1  6  0  0  0
 15 28  1  0  0  0  0
 15 29  1  0  0  0  0
 15 30  1  0  0  0  0
 16 31  1  0  0  0  0
 17 32  1  0  0  0  0
 19 33  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0003288

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C([H])C(=C([H])C2=C([H])C(OC([H])([H])[H])=C([H])C(O[H])=C12)C(=O)[C@@]([H])(O[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C14H14O5/c1-7(15)14(18)9-3-8-4-10(19-2)6-12(17)13(8)11(16)5-9/h3-7,15-17H,1-2H3/t7-/m0/s1

> <INCHI_KEY>
XPOXRISVRJOBAH-UHFFFAOYSA-N

> <FORMULA>
C14H14O5

> <MOLECULAR_WEIGHT>
262.261

> <EXACT_MASS>
262.084123551

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
33

> <JCHEM_AVERAGE_POLARIZABILITY>
26.89220075232345

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S)-1-(4,5-dihydroxy-7-methoxynaphthalen-2-yl)-2-hydroxypropan-1-one

> <ALOGPS_LOGP>
1.56

> <JCHEM_LOGP>
1.5070843786666668

> <ALOGPS_LOGS>
-2.89

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.250066685754774

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.042401710977488

> <JCHEM_PKA_STRONGEST_BASIC>
-3.4062296000026944

> <JCHEM_POLAR_SURFACE_AREA>
86.99

> <JCHEM_REFRACTIVITY>
69.5321

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.36e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-1-(4,5-dihydroxy-7-methoxynaphthalen-2-yl)-2-hydroxypropan-1-one

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 33 34  0  0  0  0  0  0  0  0999 V2000
    4.7274    2.1093   -0.2130 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7026    0.7835    0.2351 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4796    0.0915    0.2901 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4153   -1.2065    0.7229 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1849   -1.8934    0.7751 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1997   -3.1733    1.2134 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0297   -1.2381    0.3811 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2043   -1.8532    0.4084 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3522   -3.1442    0.8264 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3414   -1.1594    0.0040 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3230    0.1314   -0.4331 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4792    0.8946   -0.8640 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2611    2.1164   -1.2480 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8740    0.4884   -0.9317 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.7000    1.4381   -0.0401 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1499   -0.7896   -0.5373 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0520    0.7330   -0.4503 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0915    0.0879   -0.0615 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3284    0.7097   -0.0906 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2139    2.2739   -1.1665 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2406    2.7796    0.5391 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7931    2.4168   -0.3760 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3043   -1.7268    1.0315 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5516   -3.8589    1.3512 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1997   -3.6620    0.8776 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2554   -1.6909    0.0500 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2530    0.7069   -1.9637 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0636    1.6868    0.8475 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9128    2.3603   -0.5801 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6128    0.9328    0.2940 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6503   -0.8429    0.2988 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0373    1.7541   -0.7850 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3846    1.7440   -0.4347 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  5  7  2  0
  7  8  1  0
  8  9  1  0
  8 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  1  0
 14 16  1  0
 11 17  2  0
 17 18  1  0
 18 19  2  0
 19  3  1  0
 18  7  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  4 23  1  0
  6 24  1  0
  9 25  1  0
 10 26  1  0
 14 27  1  6
 15 28  1  0
 15 29  1  0
 15 30  1  0
 16 31  1  0
 17 32  1  0
 19 33  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       4.727   2.109  -0.213  0.00  0.00           C+0
HETATM    2  O   UNK     0       4.703   0.784   0.235  0.00  0.00           O+0
HETATM    3  C   UNK     0       3.480   0.092   0.290  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.415  -1.206   0.723  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.185  -1.893   0.775  0.00  0.00           C+0
HETATM    6  O   UNK     0       2.200  -3.173   1.213  0.00  0.00           O+0
HETATM    7  C   UNK     0       1.030  -1.238   0.381  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.204  -1.853   0.408  0.00  0.00           C+0
HETATM    9  O   UNK     0      -0.352  -3.144   0.826  0.00  0.00           O+0
HETATM   10  C   UNK     0      -1.341  -1.159   0.004  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.323   0.131  -0.433  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.479   0.895  -0.864  0.00  0.00           C+0
HETATM   13  O   UNK     0      -2.261   2.116  -1.248  0.00  0.00           O+0
HETATM   14  C   UNK     0      -3.874   0.488  -0.932  0.00  0.00           C+0
HETATM   15  C   UNK     0      -4.700   1.438  -0.040  0.00  0.00           C+0
HETATM   16  O   UNK     0      -4.150  -0.790  -0.537  0.00  0.00           O+0
HETATM   17  C   UNK     0      -0.052   0.733  -0.450  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.091   0.088  -0.062  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.328   0.710  -0.091  0.00  0.00           C+0
HETATM   20  H   UNK     0       4.214   2.274  -1.167  0.00  0.00           H+0
HETATM   21  H   UNK     0       4.241   2.780   0.539  0.00  0.00           H+0
HETATM   22  H   UNK     0       5.793   2.417  -0.376  0.00  0.00           H+0
HETATM   23  H   UNK     0       4.304  -1.727   1.032  0.00  0.00           H+0
HETATM   24  H   UNK     0       1.552  -3.859   1.351  0.00  0.00           H+0
HETATM   25  H   UNK     0      -1.200  -3.662   0.878  0.00  0.00           H+0
HETATM   26  H   UNK     0      -2.255  -1.691   0.050  0.00  0.00           H+0
HETATM   27  H   UNK     0      -4.253   0.707  -1.964  0.00  0.00           H+0
HETATM   28  H   UNK     0      -4.064   1.687   0.848  0.00  0.00           H+0
HETATM   29  H   UNK     0      -4.913   2.360  -0.580  0.00  0.00           H+0
HETATM   30  H   UNK     0      -5.613   0.933   0.294  0.00  0.00           H+0
HETATM   31  H   UNK     0      -4.650  -0.843   0.299  0.00  0.00           H+0
HETATM   32  H   UNK     0       0.037   1.754  -0.785  0.00  0.00           H+0
HETATM   33  H   UNK     0       2.385   1.744  -0.435  0.00  0.00           H+0
CONECT    1    2   20   21   22                                             
CONECT    2    1    3                                                       
CONECT    3    2    4   19                                                  
CONECT    4    3    5   23                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5   24                                                       
CONECT    7    5    8   18                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8   25                                                       
CONECT   10    8   11   26                                                  
CONECT   11   10   12   17                                                  
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   16   27                                             
CONECT   15   14   28   29   30                                             
CONECT   16   14   31                                                       
CONECT   17   11   18   32                                                  
CONECT   18   17   19    7                                                  
CONECT   19   18    3   33                                                  
CONECT   20    1                                                            
CONECT   21    1                                                            
CONECT   22    1                                                            
CONECT   23    4                                                            
CONECT   24    6                                                            
CONECT   25    9                                                            
CONECT   26   10                                                            
CONECT   27   14                                                            
CONECT   28   15                                                            
CONECT   29   15                                                            
CONECT   30   15                                                            
CONECT   31   16                                                            
CONECT   32   17                                                            
CONECT   33   19                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   68    0
END

RDKit          3D

33 34  0  0  0  0  0  0  0  0999 V2000
    4.7274    2.1093   -0.2130 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7026    0.7835    0.2351 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4796    0.0915    0.2901 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4153   -1.2065    0.7229 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1849   -1.8934    0.7751 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1997   -3.1733    1.2134 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0297   -1.2381    0.3811 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2043   -1.8532    0.4084 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3522   -3.1442    0.8264 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3414   -1.1594    0.0040 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3230    0.1314   -0.4331 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4792    0.8946   -0.8640 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2611    2.1164   -1.2480 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8740    0.4884   -0.9317 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.7000    1.4381   -0.0401 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1499   -0.7896   -0.5373 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0520    0.7330   -0.4503 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0915    0.0879   -0.0615 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3284    0.7097   -0.0906 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2139    2.2739   -1.1665 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2406    2.7796    0.5391 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7931    2.4168   -0.3760 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3043   -1.7268    1.0315 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5516   -3.8589    1.3512 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1997   -3.6620    0.8776 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2554   -1.6909    0.0500 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2530    0.7069   -1.9637 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0636    1.6868    0.8475 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9128    2.3603   -0.5801 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6128    0.9328    0.2940 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6503   -0.8429    0.2988 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0373    1.7541   -0.7850 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3846    1.7440   -0.4347 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  5  7  2  0
  7  8  1  0
  8  9  1  0
  8 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  1  0
 14 16  1  0
 11 17  2  0
 17 18  1  0
 18 19  2  0
 19  3  1  0
 18  7  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  4 23  1  0
  6 24  1  0
  9 25  1  0
 10 26  1  0
 14 27  1  6
 15 28  1  0
 15 29  1  0
 15 30  1  0
 16 31  1  0
 17 32  1  0
 19 33  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Value	Source
Chaetoatrosin a	MeSH

Chemical Formula

C₁₄H₁₄O₅

Average Mass

262.2610 Da

Monoisotopic Mass

262.08412 Da

IUPAC Name

(2S)-1-(4,5-dihydroxy-7-methoxynaphthalen-2-yl)-2-hydroxypropan-1-one

Traditional Name

(2S)-1-(4,5-dihydroxy-7-methoxynaphthalen-2-yl)-2-hydroxypropan-1-one

CAS Registry Number

Not Available

SMILES

COC1=CC2=CC(=CC(O)=C2C(O)=C1)C(=O)C(C)O

InChI Identifier

InChI=1S/C14H14O5/c1-7(15)14(18)9-3-8-4-10(19-2)6-12(17)13(8)11(16)5-9/h3-7,15-17H,1-2H3

InChI Key

XPOXRISVRJOBAH-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
Amesia atrobrunnea	LOTUS Database	35616633
Chaetomium	NPAtlas	10819295

Species Where Detected

Species Name	Source	Reference
Chaetomium atrobrunneum F449	KNApSAcK Database	22123792

Chemical Taxonomy

Description

This compound belongs to the class of organic compounds known as naphthols and derivatives. These are naphthalene derivatives carrying one or more hydroxyl (-OH) groups at any ring position.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Naphthalenes

Sub Class

Naphthols and derivatives

Direct Parent

Naphthols and derivatives

Alternative Parents

Substituents

1-naphthol
Aryl alkyl ketone
Aryl ketone
Anisole
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Acyloin
Alpha-hydroxy ketone
Secondary alcohol
Ketone
Ether
Organic oxygen compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Alcohol
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	1.56	ALOGPS
logP	1.51	ChemAxon
logS	-2.9	ALOGPS
pKa (Strongest Acidic)	8.04	ChemAxon
pKa (Strongest Basic)	-3.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	86.99 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	69.53 m³·mol⁻¹	ChemAxon
Polarizability	26.89 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

NPA012972

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

8168434

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

9992852

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Hwang EI, Yun BS, Kim YK, Kwon BM, Kim HG, Lee HB, Bae KS, Kim SU: Chaetoatrosin A, a novel chitin synthase II inhibitor produced by Chaetomium atrobrunneum F449. J Antibiot (Tokyo). 2000 Mar;53(3):248-55. doi: 10.7164/antibiotics.53.248. [PubMed:10819295 ]

Showing NP-Card for Chaetoatrosin A (NP0003288)

MOL for NP0003288 (Chaetoatrosin A)

3D MOL for NP0003288 (Chaetoatrosin A)

3D SDF for NP0003288 (Chaetoatrosin A)

3D-SDF for NP0003288 (Chaetoatrosin A)

PDB for NP0003288 (Chaetoatrosin A)

3D PDB for NP0003288 (Chaetoatrosin A)

SMILES for NP0003288 (Chaetoatrosin A)

INCHI for NP0003288 (Chaetoatrosin A)

Structure for NP0003288 (Chaetoatrosin A)

3D Structure for NP0003288 (Chaetoatrosin A)