NP-MRD: Showing NP-Card for Sanguinone B (NP0007190)

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Record Information

Version

2.0

Created at

2020-12-09 04:03:06 UTC

Updated at

2021-07-15 16:56:55 UTC

NP-MRD ID

NP0007190

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Sanguinone B

Provided By

NPAtlas

Description

Sanguinone B belongs to the class of organic compounds known as quinoline carboxylic acids. These are quinolines in which the quinoline ring system is substituted by a carboxyl group at one or more positions. Sanguinone B is found in Mycena sanguinolenta. Sanguinone B was first documented in 2007 (PMID: 17658856). Based on a literature review very few articles have been published on Sanguinone B.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242118383D          

 39 43  0  0  0  0            999 V2000
    4.9284   -0.2383    0.0024 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4862   -0.5909   -0.2918 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8660    0.2995   -1.2257 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5963    0.5227   -1.1929 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9790    1.3764   -2.0826 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6979    2.0242   -3.0723 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3984    1.6386   -2.0414 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0806    0.9835   -1.0513 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5237    0.1304   -0.1435 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8254   -0.0998   -0.2207 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4316   -1.0398    0.7505 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6728   -1.0304    2.0500 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7754   -1.4388    1.7606 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3302   -0.4470    0.8821 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6736    0.0168    1.0151 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.5172   -1.1767    1.3966 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0329   -2.3235    1.5074 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8670   -1.0058    1.6325 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2818    0.6768   -0.1573 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3440    1.2929   -1.1122 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5165    2.2449   -2.2416 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3258    2.4283   -2.7759 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7955   -0.6287    0.9932 N   0  0  2  0  0  0  0  0  0  0  0  0
    4.9389    0.4330    0.8690 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4171    0.2314   -0.8748 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4447   -1.2032    0.2328 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4265   -1.6375   -0.6996 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6787    1.9077   -3.1883 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4026   -2.0701    0.3373 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6562    0.0117    2.4601 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1463   -1.7319    2.7380 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7342   -2.4250    1.2521 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2517   -1.5150    2.7448 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6544    0.7294    1.9004 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4451   -0.7455    0.8260 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9337   -0.0871   -0.6785 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0038    1.4527    0.2537 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4608    2.6735   -2.5256 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7607    0.3609    1.3355 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
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 15 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 11 23  1  0  0  0  0
 23  2  1  0  0  0  0
 10  4  1  0  0  0  0
 22  7  1  0  0  0  0
 20  8  2  0  0  0  0
 14  9  1  0  0  0  0
  1 24  1  0  0  0  0
  1 25  1  0  0  0  0
  1 26  1  0  0  0  0
  2 27  1  6  0  0  0
  6 28  1  0  0  0  0
 11 29  1  6  0  0  0
 12 30  1  0  0  0  0
 12 31  1  0  0  0  0
 13 32  1  0  0  0  0
 13 33  1  0  0  0  0
 15 34  1  1  0  0  0
 18 35  1  0  0  0  0
 19 36  1  0  0  0  0
 19 37  1  0  0  0  0
 21 38  1  0  0  0  0
 23 39  1  0  0  0  0
M  END

     RDKit          3D

 39 43  0  0  0  0  0  0  0  0999 V2000
    4.9284   -0.2383    0.0024 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4862   -0.5909   -0.2918 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8660    0.2995   -1.2257 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5963    0.5227   -1.1929 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9790    1.3764   -2.0826 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6979    2.0242   -3.0723 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3984    1.6386   -2.0414 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0806    0.9835   -1.0513 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5237    0.1304   -0.1435 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8254   -0.0998   -0.2207 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4316   -1.0398    0.7505 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6728   -1.0304    2.0500 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7754   -1.4388    1.7606 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3302   -0.4470    0.8821 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6736    0.0168    1.0151 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.5172   -1.1767    1.3966 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0329   -2.3235    1.5074 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8670   -1.0058    1.6325 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2818    0.6768   -0.1573 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3440    1.2929   -1.1122 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5165    2.2449   -2.2416 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3258    2.4283   -2.7759 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7955   -0.6287    0.9932 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9389    0.4330    0.8690 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4171    0.2314   -0.8748 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4447   -1.2032    0.2328 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4265   -1.6375   -0.6996 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6787    1.9077   -3.1883 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4026   -2.0701    0.3373 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6562    0.0117    2.4601 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1463   -1.7319    2.7380 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7342   -2.4250    1.2521 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2517   -1.5150    2.7448 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6544    0.7294    1.9004 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4451   -0.7455    0.8260 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9337   -0.0871   -0.6785 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0038    1.4527    0.2537 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4608    2.6735   -2.5256 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7607    0.3609    1.3355 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
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 15 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 11 23  1  0
 23  2  1  0
 10  4  1  0
 22  7  1  0
 20  8  2  0
 14  9  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  2 27  1  6
  6 28  1  0
 11 29  1  6
 12 30  1  0
 12 31  1  0
 13 32  1  0
 13 33  1  0
 15 34  1  1
 18 35  1  0
 19 36  1  0
 19 37  1  0
 21 38  1  0
 23 39  1  0
M  END


  Mrv1652306242118383D          

 39 43  0  0  0  0            999 V2000
    4.9284   -0.2383    0.0024 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4862   -0.5909   -0.2918 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8660    0.2995   -1.2257 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5963    0.5227   -1.1929 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9790    1.3764   -2.0826 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6979    2.0242   -3.0723 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3984    1.6386   -2.0414 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0806    0.9835   -1.0513 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5237    0.1304   -0.1435 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8254   -0.0998   -0.2207 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4316   -1.0398    0.7505 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6728   -1.0304    2.0500 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7754   -1.4388    1.7606 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3302   -0.4470    0.8821 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6736    0.0168    1.0151 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.5172   -1.1767    1.3966 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0329   -2.3235    1.5074 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8670   -1.0058    1.6325 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2818    0.6768   -0.1573 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3440    1.2929   -1.1122 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5165    2.2449   -2.2416 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3258    2.4283   -2.7759 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7955   -0.6287    0.9932 N   0  0  2  0  0  0  0  0  0  0  0  0
    4.9389    0.4330    0.8690 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4171    0.2314   -0.8748 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4447   -1.2032    0.2328 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4265   -1.6375   -0.6996 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6787    1.9077   -3.1883 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4026   -2.0701    0.3373 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6562    0.0117    2.4601 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1463   -1.7319    2.7380 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7342   -2.4250    1.2521 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2517   -1.5150    2.7448 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6544    0.7294    1.9004 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4451   -0.7455    0.8260 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9337   -0.0871   -0.6785 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0038    1.4527    0.2537 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4608    2.6735   -2.5256 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7607    0.3609    1.3355 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
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 15 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 11 23  1  0  0  0  0
 23  2  1  0  0  0  0
 10  4  1  0  0  0  0
 22  7  1  0  0  0  0
 20  8  2  0  0  0  0
 14  9  1  0  0  0  0
  1 24  1  0  0  0  0
  1 25  1  0  0  0  0
  1 26  1  0  0  0  0
  2 27  1  6  0  0  0
  6 28  1  0  0  0  0
 11 29  1  6  0  0  0
 12 30  1  0  0  0  0
 12 31  1  0  0  0  0
 13 32  1  0  0  0  0
 13 33  1  0  0  0  0
 15 34  1  1  0  0  0
 18 35  1  0  0  0  0
 19 36  1  0  0  0  0
 19 37  1  0  0  0  0
 21 38  1  0  0  0  0
 23 39  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0007190

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC(=O)[C@@]1([H])N2C3=C4C(=N[C@]([H])(N([H])[C@@]4([H])C([H])([H])C2([H])[H])C([H])([H])[H])C(O[H])=C2N=C([H])C(=C32)C1([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C16H16N4O3/c1-6-18-8-2-3-20-9(16(22)23)4-7-5-17-12-10(7)14(20)11(8)13(19-6)15(12)21/h5-6,8-9,18,21H,2-4H2,1H3,(H,22,23)/t6-,8-,9-/m0/s1

> <INCHI_KEY>
KJCDJSBKHGBMGO-XVYDVKMFSA-N

> <FORMULA>
C16H16N4O3

> <MOLECULAR_WEIGHT>
312.329

> <EXACT_MASS>
312.122240391

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
39

> <JCHEM_AVERAGE_POLARIZABILITY>
31.85109249996669

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(6S,10S,12S)-18-hydroxy-12-methyl-2,7,11,13-tetraazapentacyclo[12.3.1.0^{4,17}.0^{7,16}.0^{10,15}]octadeca-1(18),2,4(17),13,15-pentaene-6-carboxylic acid

> <ALOGPS_LOGP>
-0.71

> <JCHEM_LOGP>
-5.38694560503992

> <ALOGPS_LOGS>
-2.63

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
3.610204422871498

> <JCHEM_PKA_STRONGEST_ACIDIC>
-2.374898642130387

> <JCHEM_PKA_STRONGEST_BASIC>
13.945090135910492

> <JCHEM_POLAR_SURFACE_AREA>
97.52

> <JCHEM_REFRACTIVITY>
85.5441

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.31e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(6S,10S,12S)-18-hydroxy-12-methyl-2,7,11,13-tetraazapentacyclo[12.3.1.0^{4,17}.0^{7,16}.0^{10,15}]octadeca-1(18),2,4(17),13,15-pentaene-6-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 39 43  0  0  0  0  0  0  0  0999 V2000
    4.9284   -0.2383    0.0024 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4862   -0.5909   -0.2918 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8660    0.2995   -1.2257 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5963    0.5227   -1.1929 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9790    1.3764   -2.0826 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6979    2.0242   -3.0723 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3984    1.6386   -2.0414 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0806    0.9835   -1.0513 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5237    0.1304   -0.1435 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8254   -0.0998   -0.2207 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4316   -1.0398    0.7505 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6728   -1.0304    2.0500 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7754   -1.4388    1.7606 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3302   -0.4470    0.8821 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6736    0.0168    1.0151 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.5172   -1.1767    1.3966 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0329   -2.3235    1.5074 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8670   -1.0058    1.6325 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2818    0.6768   -0.1573 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3440    1.2929   -1.1122 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5165    2.2449   -2.2416 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3258    2.4283   -2.7759 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7955   -0.6287    0.9932 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9389    0.4330    0.8690 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4171    0.2314   -0.8748 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4447   -1.2032    0.2328 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4265   -1.6375   -0.6996 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6787    1.9077   -3.1883 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4026   -2.0701    0.3373 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6562    0.0117    2.4601 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1463   -1.7319    2.7380 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7342   -2.4250    1.2521 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2517   -1.5150    2.7448 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6544    0.7294    1.9004 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4451   -0.7455    0.8260 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9337   -0.0871   -0.6785 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0038    1.4527    0.2537 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4608    2.6735   -2.5256 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7607    0.3609    1.3355 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
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 15 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 11 23  1  0
 23  2  1  0
 10  4  1  0
 22  7  1  0
 20  8  2  0
 14  9  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  2 27  1  6
  6 28  1  0
 11 29  1  6
 12 30  1  0
 12 31  1  0
 13 32  1  0
 13 33  1  0
 15 34  1  1
 18 35  1  0
 19 36  1  0
 19 37  1  0
 21 38  1  0
 23 39  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       4.928  -0.238   0.002  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.486  -0.591  -0.292  0.00  0.00           C+0
HETATM    3  N   UNK     0       2.866   0.300  -1.226  0.00  0.00           N+0
HETATM    4  C   UNK     0       1.596   0.523  -1.193  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.979   1.376  -2.083  0.00  0.00           C+0
HETATM    6  O   UNK     0       1.698   2.024  -3.072  0.00  0.00           O+0
HETATM    7  C   UNK     0      -0.398   1.639  -2.041  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.081   0.984  -1.051  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.524   0.130  -0.144  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.825  -0.100  -0.221  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.432  -1.040   0.751  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.673  -1.030   2.050  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.775  -1.439   1.761  0.00  0.00           C+0
HETATM   14  N   UNK     0      -1.330  -0.447   0.882  0.00  0.00           N+0
HETATM   15  C   UNK     0      -2.674   0.017   1.015  0.00  0.00           C+0
HETATM   16  C   UNK     0      -3.517  -1.177   1.397  0.00  0.00           C+0
HETATM   17  O   UNK     0      -3.033  -2.324   1.507  0.00  0.00           O+0
HETATM   18  O   UNK     0      -4.867  -1.006   1.633  0.00  0.00           O+0
HETATM   19  C   UNK     0      -3.282   0.677  -0.157  0.00  0.00           C+0
HETATM   20  C   UNK     0      -2.344   1.293  -1.112  0.00  0.00           C+0
HETATM   21  C   UNK     0      -2.517   2.245  -2.242  0.00  0.00           C+0
HETATM   22  N   UNK     0      -1.326   2.428  -2.776  0.00  0.00           N+0
HETATM   23  N   UNK     0       2.796  -0.629   0.993  0.00  0.00           N+0
HETATM   24  H   UNK     0       4.939   0.433   0.869  0.00  0.00           H+0
HETATM   25  H   UNK     0       5.417   0.231  -0.875  0.00  0.00           H+0
HETATM   26  H   UNK     0       5.445  -1.203   0.233  0.00  0.00           H+0
HETATM   27  H   UNK     0       3.426  -1.638  -0.700  0.00  0.00           H+0
HETATM   28  H   UNK     0       2.679   1.908  -3.188  0.00  0.00           H+0
HETATM   29  H   UNK     0       1.403  -2.070   0.337  0.00  0.00           H+0
HETATM   30  H   UNK     0       0.656   0.012   2.460  0.00  0.00           H+0
HETATM   31  H   UNK     0       1.146  -1.732   2.738  0.00  0.00           H+0
HETATM   32  H   UNK     0      -0.734  -2.425   1.252  0.00  0.00           H+0
HETATM   33  H   UNK     0      -1.252  -1.515   2.745  0.00  0.00           H+0
HETATM   34  H   UNK     0      -2.654   0.729   1.900  0.00  0.00           H+0
HETATM   35  H   UNK     0      -5.445  -0.746   0.826  0.00  0.00           H+0
HETATM   36  H   UNK     0      -3.934  -0.087  -0.679  0.00  0.00           H+0
HETATM   37  H   UNK     0      -4.004   1.453   0.254  0.00  0.00           H+0
HETATM   38  H   UNK     0      -3.461   2.674  -2.526  0.00  0.00           H+0
HETATM   39  H   UNK     0       2.761   0.361   1.335  0.00  0.00           H+0
CONECT    1    2   24   25   26                                             
CONECT    2    1    3   23   27                                             
CONECT    3    2    4                                                       
CONECT    4    3    5   10                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5   28                                                       
CONECT    7    5    8   22                                                  
CONECT    8    7    9   20                                                  
CONECT    9    8   10   14                                                  
CONECT   10    9   11    4                                                  
CONECT   11   10   12   23   29                                             
CONECT   12   11   13   30   31                                             
CONECT   13   12   14   32   33                                             
CONECT   14   13   15    9                                                  
CONECT   15   14   16   19   34                                             
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   35                                                       
CONECT   19   15   20   36   37                                             
CONECT   20   19   21    8                                                  
CONECT   21   20   22   38                                                  
CONECT   22   21    7                                                       
CONECT   23   11    2   39                                                  
CONECT   24    1                                                            
CONECT   25    1                                                            
CONECT   26    1                                                            
CONECT   27    2                                                            
CONECT   28    6                                                            
CONECT   29   11                                                            
CONECT   30   12                                                            
CONECT   31   12                                                            
CONECT   32   13                                                            
CONECT   33   13                                                            
CONECT   34   15                                                            
CONECT   35   18                                                            
CONECT   36   19                                                            
CONECT   37   19                                                            
CONECT   38   21                                                            
CONECT   39   23                                                            
MASTER        0    0    0    0    0    0    0    0   39    0   86    0
END

RDKit          3D

39 43  0  0  0  0  0  0  0  0999 V2000
    4.9284   -0.2383    0.0024 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4862   -0.5909   -0.2918 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8660    0.2995   -1.2257 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5963    0.5227   -1.1929 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9790    1.3764   -2.0826 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6979    2.0242   -3.0723 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3984    1.6386   -2.0414 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0806    0.9835   -1.0513 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5237    0.1304   -0.1435 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8254   -0.0998   -0.2207 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4316   -1.0398    0.7505 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6728   -1.0304    2.0500 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7754   -1.4388    1.7606 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3302   -0.4470    0.8821 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6736    0.0168    1.0151 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.5172   -1.1767    1.3966 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0329   -2.3235    1.5074 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8670   -1.0058    1.6325 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2818    0.6768   -0.1573 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3440    1.2929   -1.1122 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5165    2.2449   -2.2416 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3258    2.4283   -2.7759 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7955   -0.6287    0.9932 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9389    0.4330    0.8690 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4171    0.2314   -0.8748 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4447   -1.2032    0.2328 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4265   -1.6375   -0.6996 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6787    1.9077   -3.1883 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4026   -2.0701    0.3373 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6562    0.0117    2.4601 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1463   -1.7319    2.7380 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7342   -2.4250    1.2521 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2517   -1.5150    2.7448 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6544    0.7294    1.9004 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4451   -0.7455    0.8260 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9337   -0.0871   -0.6785 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0038    1.4527    0.2537 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4608    2.6735   -2.5256 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7607    0.3609    1.3355 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
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 15 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 11 23  1  0
 23  2  1  0
 10  4  1  0
 22  7  1  0
 20  8  2  0
 14  9  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  2 27  1  6
  6 28  1  0
 11 29  1  6
 12 30  1  0
 12 31  1  0
 13 32  1  0
 13 33  1  0
 15 34  1  1
 18 35  1  0
 19 36  1  0
 19 37  1  0
 21 38  1  0
 23 39  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Value	Source
(6S,10S,12S)-18-Hydroxy-12-methyl-2,7,11,13-tetraazapentacyclo[12.3.1.0,.0,.0,]octadeca-1(18),2,4(17),13,15-pentaene-6-carboxylate	Generator

Chemical Formula

C₁₆H₁₆N₄O₃

Average Mass

312.3290 Da

Monoisotopic Mass

312.12224 Da

IUPAC Name

(6S,10S,12S)-18-hydroxy-12-methyl-2,7,11,13-tetraazapentacyclo[12.3.1.0^{4,17}.0^{7,16}.0^{10,15}]octadeca-1(18),2,4(17),13,15-pentaene-6-carboxylic acid

Traditional Name

(6S,10S,12S)-18-hydroxy-12-methyl-2,7,11,13-tetraazapentacyclo[12.3.1.0^{4,17}.0^{7,16}.0^{10,15}]octadeca-1(18),2,4(17),13,15-pentaene-6-carboxylic acid

CAS Registry Number

Not Available

SMILES

C[C@H]1N[C@H]2CCN3[C@@H](CC4=C5C(N=C4)=C(O)C(=N1)C2=C35)C(O)=O

InChI Identifier

InChI=1S/C16H16N4O3/c1-6-18-8-2-3-20-9(16(22)23)4-7-5-17-12-10(7)14(20)11(8)13(19-6)15(12)21/h5-6,8-9,18,21H,2-4H2,1H3,(H,22,23)/t6-,8-,9-/m0/s1

InChI Key

KJCDJSBKHGBMGO-XVYDVKMFSA-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
Mycena sanguinolenta	NPAtlas	17658856

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as quinoline carboxylic acids. These are quinolines in which the quinoline ring system is substituted by a carboxyl group at one or more positions.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Quinolines and derivatives

Sub Class

Quinoline carboxylic acids

Direct Parent

Quinoline carboxylic acids

Alternative Parents

Substituents

Quinoline-2-carboxylic acid
L-alpha-amino acid
Tetrahydroquinoline
Alpha-amino acid or derivatives
Alpha-amino acid
Indole or derivatives
Dialkylarylamine
Tertiary aliphatic/aromatic amine
Aralkylamine
Benzenoid
Amino acid
Tertiary amine
Amino acid or derivatives
Azacycle
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Secondary amine
Monocarboxylic acid or derivatives
Secondary aliphatic amine
Carboxylic acid
Carboxylic acid derivative
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Imine
Carbonyl group
Amine
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	-0.71	ALOGPS
logP	-5.4	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	-2.4	ChemAxon
pKa (Strongest Basic)	13.95	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	97.52 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	85.54 m³·mol⁻¹	ChemAxon
Polarizability	31.85 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

NPAtlas ID

NPA013828

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00057686

Chemspider ID

78437925

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Mycena sanguinolenta

METLIN ID

Not Available

PubChem Compound

135796735

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Peters S, Spiteller P: Sanguinones A and B, blue pyrroloquinoline alkaloids from the fruiting bodies of the mushroom Mycena sanguinolenta. J Nat Prod. 2007 Aug;70(8):1274-7. doi: 10.1021/np070179s. Epub 2007 Jul 21. [PubMed:17658856 ]

Showing NP-Card for Sanguinone B (NP0007190)

MOL for NP0007190 (Sanguinone B)

3D MOL for NP0007190 (Sanguinone B)

3D SDF for NP0007190 (Sanguinone B)

3D-SDF for NP0007190 (Sanguinone B)

PDB for NP0007190 (Sanguinone B)

3D PDB for NP0007190 (Sanguinone B)

SMILES for NP0007190 (Sanguinone B)

INCHI for NP0007190 (Sanguinone B)

Structure for NP0007190 (Sanguinone B)

3D Structure for NP0007190 (Sanguinone B)