NP-MRD: Showing NP-Card for Botryorhodine A (NP0008852)

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Record Information

Version

2.0

Created at

2020-12-09 06:21:00 UTC

Updated at

2021-07-15 17:01:36 UTC

NP-MRD ID

NP0008852

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Botryorhodine A

Provided By

NPAtlas

Description

Botryorhodine A is found in Botryosphaeria and Lasiodiplodia theobromae. Botryorhodine A was first documented in 2010 (PMID: 19913264). Based on a literature review very few articles have been published on 6,14-dihydroxy-4,12-dimethyl-10-oxo-2,9-dioxatricyclo[9.4.0.0³,⁸]Pentadeca-1(11),3(8),4,6,12,14-hexaene-15-carbaldehyde.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242106303D          

 34 36  0  0  0  0            999 V2000
    2.7746   -2.2242    0.0307 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7141   -0.7513    0.1091 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9009   -0.0301    0.2683 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9558    1.3313    0.3640 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1819    1.9604    0.5204 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7847    2.0167    0.3001 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5882    1.3508    0.1437 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5494   -0.0273    0.0474 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4232   -0.8503   -0.1159 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9410   -0.5254   -0.1548 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7473   -1.5908   -0.4563 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2373   -2.9143   -0.7211 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0568   -3.2877   -0.7145 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1200   -1.4043   -0.5245 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0155   -2.3926   -0.8150 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6389   -0.1524   -0.2885 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8713    0.9623    0.0198 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4469    2.2894    0.2604 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5140    0.7227    0.0756 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7998    1.9476    0.3934 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4573    2.8075    0.9948 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5220    2.2735    0.1085 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5257   -2.5643   -0.9819 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8332   -2.5357    0.2253 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1003   -2.6707    0.7699 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8364   -0.5791    0.3196 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2900    2.9582    0.5969 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7555    3.1063    0.3697 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9571   -3.7034   -0.9593 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8641   -3.3412   -1.0129 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7137   -0.0095   -0.3424 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6723    2.5676    1.2926 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5282    2.1648   -0.1070 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1545    3.0952   -0.4384 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 11 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
  8  2  1  0  0  0  0
 19 10  1  0  0  0  0
 22  7  1  0  0  0  0
  1 23  1  0  0  0  0
  1 24  1  0  0  0  0
  1 25  1  0  0  0  0
  3 26  1  0  0  0  0
  5 27  1  0  0  0  0
  6 28  1  0  0  0  0
 12 29  1  0  0  0  0
 15 30  1  0  0  0  0
 16 31  1  0  0  0  0
 18 32  1  0  0  0  0
 18 33  1  0  0  0  0
 18 34  1  0  0  0  0
M  END

     RDKit          3D

 34 36  0  0  0  0  0  0  0  0999 V2000
    2.7746   -2.2242    0.0307 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7141   -0.7513    0.1091 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9009   -0.0301    0.2683 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9558    1.3313    0.3640 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1819    1.9604    0.5204 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7847    2.0167    0.3001 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5882    1.3508    0.1437 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5494   -0.0273    0.0474 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4232   -0.8503   -0.1159 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9410   -0.5254   -0.1548 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7473   -1.5908   -0.4563 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2373   -2.9143   -0.7211 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0568   -3.2877   -0.7145 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1200   -1.4043   -0.5245 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0155   -2.3926   -0.8150 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6389   -0.1524   -0.2885 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8713    0.9623    0.0198 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4469    2.2894    0.2604 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5140    0.7227    0.0756 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7998    1.9476    0.3934 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4573    2.8075    0.9948 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5220    2.2735    0.1085 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5257   -2.5643   -0.9819 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8332   -2.5357    0.2253 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1003   -2.6707    0.7699 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8364   -0.5791    0.3196 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2900    2.9582    0.5969 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7555    3.1063    0.3697 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9571   -3.7034   -0.9593 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8641   -3.3412   -1.0129 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7137   -0.0095   -0.3424 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6723    2.5676    1.2926 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5282    2.1648   -0.1070 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1545    3.0952   -0.4384 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  4  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 11 14  1  0
 14 15  1  0
 14 16  2  0
 16 17  1  0
 17 18  1  0
 17 19  2  0
 19 20  1  0
 20 21  2  0
 20 22  1  0
  8  2  1  0
 19 10  1  0
 22  7  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  3 26  1  0
  5 27  1  0
  6 28  1  0
 12 29  1  0
 15 30  1  0
 16 31  1  0
 18 32  1  0
 18 33  1  0
 18 34  1  0
M  END


  Mrv1652306242106303D          

 34 36  0  0  0  0            999 V2000
    2.7746   -2.2242    0.0307 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7141   -0.7513    0.1091 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9009   -0.0301    0.2683 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9558    1.3313    0.3640 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1819    1.9604    0.5204 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7847    2.0167    0.3001 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5882    1.3508    0.1437 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5494   -0.0273    0.0474 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4232   -0.8503   -0.1159 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9410   -0.5254   -0.1548 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7473   -1.5908   -0.4563 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2373   -2.9143   -0.7211 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0568   -3.2877   -0.7145 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1200   -1.4043   -0.5245 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0155   -2.3926   -0.8150 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6389   -0.1524   -0.2885 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8713    0.9623    0.0198 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4469    2.2894    0.2604 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5140    0.7227    0.0756 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7998    1.9476    0.3934 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4573    2.8075    0.9948 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5220    2.2735    0.1085 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5257   -2.5643   -0.9819 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8332   -2.5357    0.2253 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1003   -2.6707    0.7699 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8364   -0.5791    0.3196 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2900    2.9582    0.5969 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7555    3.1063    0.3697 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9571   -3.7034   -0.9593 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8641   -3.3412   -1.0129 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7137   -0.0095   -0.3424 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6723    2.5676    1.2926 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5282    2.1648   -0.1070 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1545    3.0952   -0.4384 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 11 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
  8  2  1  0  0  0  0
 19 10  1  0  0  0  0
 22  7  1  0  0  0  0
  1 23  1  0  0  0  0
  1 24  1  0  0  0  0
  1 25  1  0  0  0  0
  3 26  1  0  0  0  0
  5 27  1  0  0  0  0
  6 28  1  0  0  0  0
 12 29  1  0  0  0  0
 15 30  1  0  0  0  0
 16 31  1  0  0  0  0
 18 32  1  0  0  0  0
 18 33  1  0  0  0  0
 18 34  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0008852

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C([H])C2=C(OC3=C(C([H])=O)C(O[H])=C([H])C(=C3C(=O)O2)C([H])([H])[H])C(=C1[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C16H12O6/c1-7-4-11(19)10(6-17)15-13(7)16(20)21-12-5-9(18)3-8(2)14(12)22-15/h3-6,18-19H,1-2H3

> <INCHI_KEY>
QQDBQWUHQOGQCJ-UHFFFAOYSA-N

> <FORMULA>
C16H12O6

> <MOLECULAR_WEIGHT>
300.266

> <EXACT_MASS>
300.063388106

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
34

> <JCHEM_AVERAGE_POLARIZABILITY>
29.6809724927435

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
6,14-dihydroxy-4,12-dimethyl-10-oxo-2,9-dioxatricyclo[9.4.0.0^{3,8}]pentadeca-1(15),3(8),4,6,11,13-hexaene-15-carbaldehyde

> <ALOGPS_LOGP>
3.00

> <JCHEM_LOGP>
3.7439370756666666

> <ALOGPS_LOGS>
-3.65

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.368446166130083

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.259428429122023

> <JCHEM_PKA_STRONGEST_BASIC>
-3.803339556151663

> <JCHEM_POLAR_SURFACE_AREA>
93.06000000000002

> <JCHEM_REFRACTIVITY>
78.6719

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.74e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6,14-dihydroxy-4,12-dimethyl-10-oxo-2,9-dioxatricyclo[9.4.0.0^{3,8}]pentadeca-1(15),3(8),4,6,11,13-hexaene-15-carbaldehyde

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 34 36  0  0  0  0  0  0  0  0999 V2000
    2.7746   -2.2242    0.0307 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7141   -0.7513    0.1091 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9009   -0.0301    0.2683 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9558    1.3313    0.3640 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1819    1.9604    0.5204 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7847    2.0167    0.3001 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5882    1.3508    0.1437 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5494   -0.0273    0.0474 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4232   -0.8503   -0.1159 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9410   -0.5254   -0.1548 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7473   -1.5908   -0.4563 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2373   -2.9143   -0.7211 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0568   -3.2877   -0.7145 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1200   -1.4043   -0.5245 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0155   -2.3926   -0.8150 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6389   -0.1524   -0.2885 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8713    0.9623    0.0198 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4469    2.2894    0.2604 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5140    0.7227    0.0756 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7998    1.9476    0.3934 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4573    2.8075    0.9948 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5220    2.2735    0.1085 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5257   -2.5643   -0.9819 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8332   -2.5357    0.2253 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1003   -2.6707    0.7699 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8364   -0.5791    0.3196 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2900    2.9582    0.5969 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7555    3.1063    0.3697 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9571   -3.7034   -0.9593 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8641   -3.3412   -1.0129 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7137   -0.0095   -0.3424 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6723    2.5676    1.2926 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5282    2.1648   -0.1070 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1545    3.0952   -0.4384 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  4  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 11 14  1  0
 14 15  1  0
 14 16  2  0
 16 17  1  0
 17 18  1  0
 17 19  2  0
 19 20  1  0
 20 21  2  0
 20 22  1  0
  8  2  1  0
 19 10  1  0
 22  7  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  3 26  1  0
  5 27  1  0
  6 28  1  0
 12 29  1  0
 15 30  1  0
 16 31  1  0
 18 32  1  0
 18 33  1  0
 18 34  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       2.775  -2.224   0.031  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.714  -0.751   0.109  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.901  -0.030   0.268  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.956   1.331   0.364  0.00  0.00           C+0
HETATM    5  O   UNK     0       5.182   1.960   0.520  0.00  0.00           O+0
HETATM    6  C   UNK     0       2.785   2.017   0.300  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.588   1.351   0.144  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.549  -0.027   0.047  0.00  0.00           C+0
HETATM    9  O   UNK     0       0.423  -0.850  -0.116  0.00  0.00           O+0
HETATM   10  C   UNK     0      -0.941  -0.525  -0.155  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.747  -1.591  -0.456  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.237  -2.914  -0.721  0.00  0.00           C+0
HETATM   13  O   UNK     0      -0.057  -3.288  -0.715  0.00  0.00           O+0
HETATM   14  C   UNK     0      -3.120  -1.404  -0.525  0.00  0.00           C+0
HETATM   15  O   UNK     0      -4.016  -2.393  -0.815  0.00  0.00           O+0
HETATM   16  C   UNK     0      -3.639  -0.152  -0.289  0.00  0.00           C+0
HETATM   17  C   UNK     0      -2.871   0.962   0.020  0.00  0.00           C+0
HETATM   18  C   UNK     0      -3.447   2.289   0.260  0.00  0.00           C+0
HETATM   19  C   UNK     0      -1.514   0.723   0.076  0.00  0.00           C+0
HETATM   20  C   UNK     0      -0.800   1.948   0.393  0.00  0.00           C+0
HETATM   21  O   UNK     0      -1.457   2.808   0.995  0.00  0.00           O+0
HETATM   22  O   UNK     0       0.522   2.273   0.109  0.00  0.00           O+0
HETATM   23  H   UNK     0       2.526  -2.564  -0.982  0.00  0.00           H+0
HETATM   24  H   UNK     0       3.833  -2.536   0.225  0.00  0.00           H+0
HETATM   25  H   UNK     0       2.100  -2.671   0.770  0.00  0.00           H+0
HETATM   26  H   UNK     0       4.836  -0.579   0.320  0.00  0.00           H+0
HETATM   27  H   UNK     0       5.290   2.958   0.597  0.00  0.00           H+0
HETATM   28  H   UNK     0       2.756   3.106   0.370  0.00  0.00           H+0
HETATM   29  H   UNK     0      -1.957  -3.703  -0.959  0.00  0.00           H+0
HETATM   30  H   UNK     0      -3.864  -3.341  -1.013  0.00  0.00           H+0
HETATM   31  H   UNK     0      -4.714  -0.010  -0.342  0.00  0.00           H+0
HETATM   32  H   UNK     0      -3.672   2.568   1.293  0.00  0.00           H+0
HETATM   33  H   UNK     0      -4.528   2.165  -0.107  0.00  0.00           H+0
HETATM   34  H   UNK     0      -3.155   3.095  -0.438  0.00  0.00           H+0
CONECT    1    2   23   24   25                                             
CONECT    2    1    3    8                                                  
CONECT    3    2    4   26                                                  
CONECT    4    3    5    6                                                  
CONECT    5    4   27                                                       
CONECT    6    4    7   28                                                  
CONECT    7    6    8   22                                                  
CONECT    8    7    9    2                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   19                                                  
CONECT   11   10   12   14                                                  
CONECT   12   11   13   29                                                  
CONECT   13   12                                                            
CONECT   14   11   15   16                                                  
CONECT   15   14   30                                                       
CONECT   16   14   17   31                                                  
CONECT   17   16   18   19                                                  
CONECT   18   17   32   33   34                                             
CONECT   19   17   20   10                                                  
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20    7                                                       
CONECT   23    1                                                            
CONECT   24    1                                                            
CONECT   25    1                                                            
CONECT   26    3                                                            
CONECT   27    5                                                            
CONECT   28    6                                                            
CONECT   29   12                                                            
CONECT   30   15                                                            
CONECT   31   16                                                            
CONECT   32   18                                                            
CONECT   33   18                                                            
CONECT   34   18                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   72    0
END

RDKit          3D

34 36  0  0  0  0  0  0  0  0999 V2000
    2.7746   -2.2242    0.0307 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7141   -0.7513    0.1091 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9009   -0.0301    0.2683 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9558    1.3313    0.3640 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1819    1.9604    0.5204 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7847    2.0167    0.3001 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5882    1.3508    0.1437 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5494   -0.0273    0.0474 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4232   -0.8503   -0.1159 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9410   -0.5254   -0.1548 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7473   -1.5908   -0.4563 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2373   -2.9143   -0.7211 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0568   -3.2877   -0.7145 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1200   -1.4043   -0.5245 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0155   -2.3926   -0.8150 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6389   -0.1524   -0.2885 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8713    0.9623    0.0198 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4469    2.2894    0.2604 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5140    0.7227    0.0756 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7998    1.9476    0.3934 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4573    2.8075    0.9948 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5220    2.2735    0.1085 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5257   -2.5643   -0.9819 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8332   -2.5357    0.2253 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1003   -2.6707    0.7699 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8364   -0.5791    0.3196 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2900    2.9582    0.5969 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7555    3.1063    0.3697 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9571   -3.7034   -0.9593 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8641   -3.3412   -1.0129 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7137   -0.0095   -0.3424 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6723    2.5676    1.2926 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5282    2.1648   -0.1070 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1545    3.0952   -0.4384 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  4  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 11 14  1  0
 14 15  1  0
 14 16  2  0
 16 17  1  0
 17 18  1  0
 17 19  2  0
 19 20  1  0
 20 21  2  0
 20 22  1  0
  8  2  1  0
 19 10  1  0
 22  7  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  3 26  1  0
  5 27  1  0
  6 28  1  0
 12 29  1  0
 15 30  1  0
 16 31  1  0
 18 32  1  0
 18 33  1  0
 18 34  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Not Available

Chemical Formula

C₁₆H₁₂O₆

Average Mass

300.2660 Da

Monoisotopic Mass

300.06339 Da

IUPAC Name

6,14-dihydroxy-4,12-dimethyl-10-oxo-2,9-dioxatricyclo[9.4.0.0^{3,8}]pentadeca-1(15),3(8),4,6,11,13-hexaene-15-carbaldehyde

Traditional Name

6,14-dihydroxy-4,12-dimethyl-10-oxo-2,9-dioxatricyclo[9.4.0.0^{3,8}]pentadeca-1(15),3(8),4,6,11,13-hexaene-15-carbaldehyde

CAS Registry Number

Not Available

SMILES

CC1=CC(O)=CC2=C1OC1=C(C(C)=CC(O)=C1C=O)C(=O)O2

InChI Identifier

InChI=1S/C16H12O6/c1-7-4-11(19)10(6-17)15-13(7)16(20)21-12-5-9(18)3-8(2)14(12)22-15/h3-6,18-19H,1-2H3

InChI Key

QQDBQWUHQOGQCJ-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
Botryosphaeria	NPAtlas	19913264
Lasiodiplodia theobromae	LOTUS Database	35616633

Chemical Taxonomy

Description

This compound belongs to the class of organic compounds known as depsides and depsidones. These are polycyclic compounds that is either a polyphenolic compound composed of two or more monocyclic aromatic units linked by an ester bond (depside), or a compound containing the depsidone structure (depsidone).

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Depsides and depsidones

Sub Class

Not Available

Direct Parent

Depsides and depsidones

Alternative Parents

Substituents

Depsidone
Diaryl ether
1-hydroxy-2-unsubstituted benzenoid
1,4-dioxepine
Dioxepine
Aryl-aldehyde
Phenol
Benzenoid
Vinylogous acid
Carboxylic acid ester
Lactone
Carboxylic acid derivative
Oxacycle
Organoheterocyclic compound
Ether
Hydrocarbon derivative
Organic oxide
Aldehyde
Organic oxygen compound
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic 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	3	ALOGPS
logP	3.74	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	7.26	ChemAxon
pKa (Strongest Basic)	-3.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	93.06 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	78.67 m³·mol⁻¹	ChemAxon
Polarizability	29.68 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

NPA008300

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

28287129

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

46178006

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Abdou R, Scherlach K, Dahse HM, Sattler I, Hertweck C: Botryorhodines A-D, antifungal and cytotoxic depsidones from Botryosphaeria rhodina, an endophyte of the medicinal plant Bidens pilosa. Phytochemistry. 2010 Jan;71(1):110-6. doi: 10.1016/j.phytochem.2009.09.024. Epub 2009 Nov 11. [PubMed:19913264 ]

Showing NP-Card for Botryorhodine A (NP0008852)

MOL for NP0008852 (Botryorhodine A)

3D MOL for NP0008852 (Botryorhodine A)

3D SDF for NP0008852 (Botryorhodine A)

3D-SDF for NP0008852 (Botryorhodine A)

PDB for NP0008852 (Botryorhodine A)

3D PDB for NP0008852 (Botryorhodine A)

SMILES for NP0008852 (Botryorhodine A)

INCHI for NP0008852 (Botryorhodine A)

Structure for NP0008852 (Botryorhodine A)

3D Structure for NP0008852 (Botryorhodine A)