NP-MRD: Showing NP-Card for Terrecoumarin B (NP0014767)

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Record Information

Version

2.0

Created at

2021-01-05 23:50:50 UTC

Updated at

2026-02-11 04:01:52 UTC

NP-MRD ID

NP0014767

Natural Product DOI

https://doi.org/10.57994/6258

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Terrecoumarin B

Provided By

NPAtlas

Description

Terrecoumarin B is found in Penicillium oxalicum. Terrecoumarin B was first documented in 2015 (PMID: 26411648). Based on a literature review very few articles have been published on 6-methoxy-3-methyl-5-(3-methylbut-2-en-1-yl)-1H-isochromen-1-one.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242120063D          

 37 38  0  0  0  0            999 V2000
   -1.6489    3.8395   -0.5040 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1744    2.6959    0.1224 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0881    1.9464   -0.2968 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6001    2.3620   -1.4228 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7062    1.6600   -1.8904 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1148    0.5303   -1.2112 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2053   -0.2425   -1.6152 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8309    0.1314   -2.6315 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5825   -1.3188   -0.9752 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9883   -1.7833    0.0946 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4328   -3.0151    0.8065 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8956   -1.0457    0.5366 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4527    0.0919   -0.0908 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3454    0.8181    0.3520 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3624    0.2489    1.4951 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2786   -0.8387    1.3106 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3613   -1.0347    0.6367 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0360   -2.4362    0.7488 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1225   -0.1533   -0.2622 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3343    4.3452    0.2429 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8905    4.5888   -0.7751 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2478    3.5771   -1.3902 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3162    3.2411   -1.9820 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2612    1.9606   -2.7618 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5393   -3.1382    0.7491 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2090   -2.9285    1.9141 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9430   -3.9208    0.4468 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3924   -1.4172    1.4111 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4080    0.0802    2.2968 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9747    1.1201    1.9312 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9748   -1.7722    1.9150 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8386   -2.3055    1.4959 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4372   -2.7199   -0.2238 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2623   -3.1730    1.0500 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4164   -0.7783   -1.1668 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6603    0.7560   -0.5969 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1146    0.0286    0.2406 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  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 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  2  3  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 14  3  1  0  0  0  0
 13  6  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
  5 24  1  0  0  0  0
 11 25  1  0  0  0  0
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 12 28  1  0  0  0  0
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 18 32  1  0  0  0  0
 18 33  1  0  0  0  0
 18 34  1  0  0  0  0
 19 35  1  0  0  0  0
 19 36  1  0  0  0  0
 19 37  1  0  0  0  0
M  END

     RDKit          3D

 37 38  0  0  0  0  0  0  0  0999 V2000
   -1.6489    3.8395   -0.5040 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1744    2.6959    0.1224 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0881    1.9464   -0.2968 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6001    2.3620   -1.4228 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7062    1.6600   -1.8904 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1148    0.5303   -1.2112 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2053   -0.2425   -1.6152 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8309    0.1314   -2.6315 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5825   -1.3188   -0.9752 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9883   -1.7833    0.0946 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4328   -3.0151    0.8065 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8956   -1.0457    0.5366 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4527    0.0919   -0.0908 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3454    0.8181    0.3520 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3624    0.2489    1.4951 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2786   -0.8387    1.3106 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3613   -1.0347    0.6367 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0360   -2.4362    0.7488 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1225   -0.1533   -0.2622 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3343    4.3452    0.2429 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8905    4.5888   -0.7751 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2478    3.5771   -1.3902 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3162    3.2411   -1.9820 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2612    1.9606   -2.7618 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5393   -3.1382    0.7491 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2090   -2.9285    1.9141 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9430   -3.9208    0.4468 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3924   -1.4172    1.4111 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4080    0.0802    2.2968 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9747    1.1201    1.9312 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9748   -1.7722    1.9150 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8386   -2.3055    1.4959 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4372   -2.7199   -0.2238 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2623   -3.1730    1.0500 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4164   -0.7783   -1.1668 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6603    0.7560   -0.5969 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1146    0.0286    0.2406 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
  7  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  2  3
 17 18  1  0
 17 19  1  0
 14  3  1  0
 13  6  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  4 23  1  0
  5 24  1  0
 11 25  1  0
 11 26  1  0
 11 27  1  0
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 15 29  1  0
 15 30  1  0
 16 31  1  0
 18 32  1  0
 18 33  1  0
 18 34  1  0
 19 35  1  0
 19 36  1  0
 19 37  1  0
M  END


  Mrv1652306242120063D          

 37 38  0  0  0  0            999 V2000
   -1.6489    3.8395   -0.5040 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1744    2.6959    0.1224 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0881    1.9464   -0.2968 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6001    2.3620   -1.4228 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7062    1.6600   -1.8904 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1148    0.5303   -1.2112 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2053   -0.2425   -1.6152 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8309    0.1314   -2.6315 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5825   -1.3188   -0.9752 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9883   -1.7833    0.0946 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4328   -3.0151    0.8065 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8956   -1.0457    0.5366 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4527    0.0919   -0.0908 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3454    0.8181    0.3520 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3624    0.2489    1.4951 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2786   -0.8387    1.3106 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3613   -1.0347    0.6367 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0360   -2.4362    0.7488 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1225   -0.1533   -0.2622 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3343    4.3452    0.2429 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8905    4.5888   -0.7751 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2478    3.5771   -1.3902 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3162    3.2411   -1.9820 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2612    1.9606   -2.7618 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5393   -3.1382    0.7491 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2090   -2.9285    1.9141 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9430   -3.9208    0.4468 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3924   -1.4172    1.4111 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4080    0.0802    2.2968 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9747    1.1201    1.9312 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9748   -1.7722    1.9150 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8386   -2.3055    1.4959 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4372   -2.7199   -0.2238 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2623   -3.1730    1.0500 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4164   -0.7783   -1.1668 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6603    0.7560   -0.5969 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1146    0.0286    0.2406 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  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
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 16 17  2  3  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 14  3  1  0  0  0  0
 13  6  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
  5 24  1  0  0  0  0
 11 25  1  0  0  0  0
 11 26  1  0  0  0  0
 11 27  1  0  0  0  0
 12 28  1  0  0  0  0
 15 29  1  0  0  0  0
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 16 31  1  0  0  0  0
 18 32  1  0  0  0  0
 18 33  1  0  0  0  0
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 19 35  1  0  0  0  0
 19 36  1  0  0  0  0
 19 37  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0014767

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]C(=C(C([H])([H])[H])C([H])([H])[H])C([H])([H])C1=C2C([H])=C(OC(=O)C2=C([H])C([H])=C1OC([H])([H])[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C16H18O3/c1-10(2)5-6-12-14-9-11(3)19-16(17)13(14)7-8-15(12)18-4/h5,7-9H,6H2,1-4H3

> <INCHI_KEY>
YFKIIPGXPUGSGV-UHFFFAOYSA-N

> <FORMULA>
C16H18O3

> <MOLECULAR_WEIGHT>
258.317

> <EXACT_MASS>
258.12559444

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
37

> <JCHEM_AVERAGE_POLARIZABILITY>
28.75211947762971

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
6-methoxy-3-methyl-5-(3-methylbut-2-en-1-yl)-1H-isochromen-1-one

> <ALOGPS_LOGP>
3.85

> <JCHEM_LOGP>
3.8263587750000005

> <ALOGPS_LOGS>
-4.56

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.85679270793723

> <JCHEM_POLAR_SURFACE_AREA>
35.53

> <JCHEM_REFRACTIVITY>
78.01110000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.05e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6-methoxy-3-methyl-5-(3-methylbut-2-en-1-yl)isochromen-1-one

> <JCHEM_VEBER_RULE>
1

$$$$

     RDKit          3D

 37 38  0  0  0  0  0  0  0  0999 V2000
   -1.6489    3.8395   -0.5040 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1744    2.6959    0.1224 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0881    1.9464   -0.2968 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6001    2.3620   -1.4228 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7062    1.6600   -1.8904 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1148    0.5303   -1.2112 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2053   -0.2425   -1.6152 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8309    0.1314   -2.6315 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5825   -1.3188   -0.9752 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9883   -1.7833    0.0946 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4328   -3.0151    0.8065 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8956   -1.0457    0.5366 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4527    0.0919   -0.0908 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3454    0.8181    0.3520 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3624    0.2489    1.4951 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2786   -0.8387    1.3106 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3613   -1.0347    0.6367 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0360   -2.4362    0.7488 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1225   -0.1533   -0.2622 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3343    4.3452    0.2429 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8905    4.5888   -0.7751 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2478    3.5771   -1.3902 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3162    3.2411   -1.9820 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2612    1.9606   -2.7618 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5393   -3.1382    0.7491 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2090   -2.9285    1.9141 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9430   -3.9208    0.4468 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3924   -1.4172    1.4111 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4080    0.0802    2.2968 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9747    1.1201    1.9312 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9748   -1.7722    1.9150 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8386   -2.3055    1.4959 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4372   -2.7199   -0.2238 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2623   -3.1730    1.0500 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4164   -0.7783   -1.1668 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6603    0.7560   -0.5969 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1146    0.0286    0.2406 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
  7  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  2  3
 17 18  1  0
 17 19  1  0
 14  3  1  0
 13  6  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  4 23  1  0
  5 24  1  0
 11 25  1  0
 11 26  1  0
 11 27  1  0
 12 28  1  0
 15 29  1  0
 15 30  1  0
 16 31  1  0
 18 32  1  0
 18 33  1  0
 18 34  1  0
 19 35  1  0
 19 36  1  0
 19 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      -1.649   3.840  -0.504  0.00  0.00           C+0
HETATM    2  O   UNK     0      -1.174   2.696   0.122  0.00  0.00           O+0
HETATM    3  C   UNK     0      -0.088   1.946  -0.297  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.600   2.362  -1.423  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.706   1.660  -1.890  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.115   0.530  -1.211  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.205  -0.243  -1.615  0.00  0.00           C+0
HETATM    8  O   UNK     0       3.831   0.131  -2.632  0.00  0.00           O+0
HETATM    9  O   UNK     0       3.583  -1.319  -0.975  0.00  0.00           O+0
HETATM   10  C   UNK     0       2.988  -1.783   0.095  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.433  -3.015   0.807  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.896  -1.046   0.537  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.453   0.092  -0.091  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.345   0.818   0.352  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.362   0.249   1.495  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.279  -0.839   1.311  0.00  0.00           C+0
HETATM   17  C   UNK     0      -2.361  -1.035   0.637  0.00  0.00           C+0
HETATM   18  C   UNK     0      -3.036  -2.436   0.749  0.00  0.00           C+0
HETATM   19  C   UNK     0      -3.123  -0.153  -0.262  0.00  0.00           C+0
HETATM   20  H   UNK     0      -2.334   4.345   0.243  0.00  0.00           H+0
HETATM   21  H   UNK     0      -0.891   4.589  -0.775  0.00  0.00           H+0
HETATM   22  H   UNK     0      -2.248   3.577  -1.390  0.00  0.00           H+0
HETATM   23  H   UNK     0       0.316   3.241  -1.982  0.00  0.00           H+0
HETATM   24  H   UNK     0       2.261   1.961  -2.762  0.00  0.00           H+0
HETATM   25  H   UNK     0       4.539  -3.138   0.749  0.00  0.00           H+0
HETATM   26  H   UNK     0       3.209  -2.929   1.914  0.00  0.00           H+0
HETATM   27  H   UNK     0       2.943  -3.921   0.447  0.00  0.00           H+0
HETATM   28  H   UNK     0       1.392  -1.417   1.411  0.00  0.00           H+0
HETATM   29  H   UNK     0       0.408   0.080   2.297  0.00  0.00           H+0
HETATM   30  H   UNK     0      -0.975   1.120   1.931  0.00  0.00           H+0
HETATM   31  H   UNK     0      -0.975  -1.772   1.915  0.00  0.00           H+0
HETATM   32  H   UNK     0      -3.839  -2.305   1.496  0.00  0.00           H+0
HETATM   33  H   UNK     0      -3.437  -2.720  -0.224  0.00  0.00           H+0
HETATM   34  H   UNK     0      -2.262  -3.173   1.050  0.00  0.00           H+0
HETATM   35  H   UNK     0      -3.416  -0.778  -1.167  0.00  0.00           H+0
HETATM   36  H   UNK     0      -2.660   0.756  -0.597  0.00  0.00           H+0
HETATM   37  H   UNK     0      -4.115   0.029   0.241  0.00  0.00           H+0
CONECT    1    2   20   21   22                                             
CONECT    2    1    3                                                       
CONECT    3    2    4   14                                                  
CONECT    4    3    5   23                                                  
CONECT    5    4    6   24                                                  
CONECT    6    5    7   13                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10   25   26   27                                             
CONECT   12   10   13   28                                                  
CONECT   13   12   14    6                                                  
CONECT   14   13   15    3                                                  
CONECT   15   14   16   29   30                                             
CONECT   16   15   17   31                                                  
CONECT   17   16   18   19                                                  
CONECT   18   17   32   33   34                                             
CONECT   19   17   35   36   37                                             
CONECT   20    1                                                            
CONECT   21    1                                                            
CONECT   22    1                                                            
CONECT   23    4                                                            
CONECT   24    5                                                            
CONECT   25   11                                                            
CONECT   26   11                                                            
CONECT   27   11                                                            
CONECT   28   12                                                            
CONECT   29   15                                                            
CONECT   30   15                                                            
CONECT   31   16                                                            
CONECT   32   18                                                            
CONECT   33   18                                                            
CONECT   34   18                                                            
CONECT   35   19                                                            
CONECT   36   19                                                            
CONECT   37   19                                                            
MASTER        0    0    0    0    0    0    0    0   37    0   76    0
END

RDKit          3D

37 38  0  0  0  0  0  0  0  0999 V2000
   -1.6489    3.8395   -0.5040 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1744    2.6959    0.1224 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0881    1.9464   -0.2968 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6001    2.3620   -1.4228 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7062    1.6600   -1.8904 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1148    0.5303   -1.2112 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2053   -0.2425   -1.6152 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8309    0.1314   -2.6315 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5825   -1.3188   -0.9752 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9883   -1.7833    0.0946 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4328   -3.0151    0.8065 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8956   -1.0457    0.5366 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4527    0.0919   -0.0908 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3454    0.8181    0.3520 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3624    0.2489    1.4951 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2786   -0.8387    1.3106 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3613   -1.0347    0.6367 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0360   -2.4362    0.7488 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1225   -0.1533   -0.2622 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3343    4.3452    0.2429 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8905    4.5888   -0.7751 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2478    3.5771   -1.3902 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3162    3.2411   -1.9820 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2612    1.9606   -2.7618 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5393   -3.1382    0.7491 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2090   -2.9285    1.9141 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9430   -3.9208    0.4468 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3924   -1.4172    1.4111 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4080    0.0802    2.2968 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9747    1.1201    1.9312 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9748   -1.7722    1.9150 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8386   -2.3055    1.4959 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4372   -2.7199   -0.2238 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2623   -3.1730    1.0500 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4164   -0.7783   -1.1668 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6603    0.7560   -0.5969 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1146    0.0286    0.2406 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
  7  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  2  3
 17 18  1  0
 17 19  1  0
 14  3  1  0
 13  6  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  4 23  1  0
  5 24  1  0
 11 25  1  0
 11 26  1  0
 11 27  1  0
 12 28  1  0
 15 29  1  0
 15 30  1  0
 16 31  1  0
 18 32  1  0
 18 33  1  0
 18 34  1  0
 19 35  1  0
 19 36  1  0
 19 37  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Not Available

Chemical Formula

C₁₆H₁₈O₃

Average Mass

258.3170 Da

Monoisotopic Mass

258.12559 Da

IUPAC Name

6-methoxy-3-methyl-5-(3-methylbut-2-en-1-yl)-1H-isochromen-1-one

Traditional Name

6-methoxy-3-methyl-5-(3-methylbut-2-en-1-yl)isochromen-1-one

CAS Registry Number

Not Available

SMILES

COC1=C(CC=C(C)C)C2=C(C=C1)C(=O)OC(C)=C2

InChI Identifier

InChI=1S/C16H18O3/c1-10(2)5-6-12-14-9-11(3)19-16(17)13(14)7-8-15(12)18-4/h5,7-9H,6H2,1-4H3

InChI Key

YFKIIPGXPUGSGV-UHFFFAOYSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 150 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 250 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 175 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 225 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

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

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 400.0, Chloroform-d, simulated)	[email protected]	Not Available	Not Available	2026-02-11	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100.0, Chloroform-d, simulated)	[email protected]	Not Available	Not Available	2026-02-11	View Spectrum

Species

Species of Origin

Species Name	Source	Reference
Penicillium oxalicum	NPAtlas	26411648
Penicillium oxalicum 0403		Not Available

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	3.85	ALOGPS
logP	3.83	ChemAxon
logS	-4.6	ALOGPS
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	35.53 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	78.01 m³·mol⁻¹	ChemAxon
Polarizability	28.75 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

NPAtlas ID

NPA010739

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

78435660

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

139586078

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Li QQ, Dang LZ, Zhang YP, Jiang JX, Zhang CM, Xiang NJ, Yang HY, Du G, Duan YQ: Isocoumarins from the fermentation products of a plant entophytic fungus Penicillium oxalicum. J Asian Nat Prod Res. 2015;17(9):876-81. doi: 10.1080/10286020.2015.1039997. [PubMed:26411648 ]
DOI: 10.1080/10286020.2015.1039997
PMID: 26411648

Showing NP-Card for Terrecoumarin B (NP0014767)

MOL for NP0014767 (Terrecoumarin B)

3D MOL for NP0014767 (Terrecoumarin B)

3D SDF for NP0014767 (Terrecoumarin B)

3D-SDF for NP0014767 (Terrecoumarin B)

PDB for NP0014767 (Terrecoumarin B)

3D PDB for NP0014767 (Terrecoumarin B)

SMILES for NP0014767 (Terrecoumarin B)

INCHI for NP0014767 (Terrecoumarin B)

Structure for NP0014767 (Terrecoumarin B)

3D Structure for NP0014767 (Terrecoumarin B)