NP-MRD: Showing NP-Card for YM-181741 (NP0004105)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2020-12-09 01:36:16 UTC

Updated at

2021-07-15 16:48:14 UTC

NP-MRD ID

NP0004105

Secondary Accession Numbers

None

Natural Product Identification

Common Name

YM-181741

Provided By

NPAtlas

Description

YM-181741 belongs to the class of organic compounds known as angucyclines. These are polyketides with a structure based on then benz[a]anthracene skeleton, with the particularity that the central ring of the anthracene moiety is a para-quinone. YM-181741 is found in Streptomyces sp. YM-181741 was first documented in 2002 (PMID: 11918062). Based on a literature review very few articles have been published on YM-181741.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242118043D          

 38 41  0  0  0  0            999 V2000
    2.7133   -2.4540    1.1886 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2688   -1.3686    0.7005 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8662   -1.0559    0.8705 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0211   -1.9060    1.5367 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3185   -1.6150    1.6987 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8137   -0.4643    1.1917 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9652    0.4291    0.5024 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3660    0.1420    0.3345 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2214    1.0513   -0.3773 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8506    2.1063   -0.8781 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6340    0.7258   -0.5414 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4783    1.5981   -1.2248 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8138    1.3632   -1.4174 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3126    0.2034   -0.8995 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4907   -0.7162   -0.1956 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0623   -1.8485    0.2899 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1484   -0.4613   -0.0124 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5251    1.6901    0.0545 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8770    2.7324    0.1762 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8726    1.6688   -0.5333 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.7344    0.6056    0.0478 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.8676   -0.5120   -0.9968 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.6786   -1.5216   -0.4606 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2092   -0.0626    1.2948 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4514   -2.8321    1.9389 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9321   -2.3220    2.2297 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0562    2.5045   -1.6217 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4523    2.0539   -1.9514 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3512   -0.0582   -1.0059 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7566   -2.5928    0.7732 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7776    1.5702   -1.6553 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3452    2.6622   -0.3137 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7572    1.0069    0.1915 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8848   -0.9810   -1.2091 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3003   -0.1301   -1.9354 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3169   -1.0597    0.1415 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8687   -0.8731    1.6206 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2705    0.7212    2.1071 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  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
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 11 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
 15 17  2  0  0  0  0
  7 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 21 24  1  0  0  0  0
 17  2  1  0  0  0  0
  8  3  1  0  0  0  0
 17 11  1  0  0  0  0
 24  6  1  0  0  0  0
  4 25  1  0  0  0  0
  5 26  1  0  0  0  0
 12 27  1  0  0  0  0
 13 28  1  0  0  0  0
 14 29  1  0  0  0  0
 16 30  1  0  0  0  0
 20 31  1  0  0  0  0
 20 32  1  0  0  0  0
 21 33  1  1  0  0  0
 22 34  1  0  0  0  0
 22 35  1  0  0  0  0
 23 36  1  0  0  0  0
 24 37  1  0  0  0  0
 24 38  1  0  0  0  0
M  END

     RDKit          3D

 38 41  0  0  0  0  0  0  0  0999 V2000
    2.7133   -2.4540    1.1886 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2688   -1.3686    0.7005 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8662   -1.0559    0.8705 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0211   -1.9060    1.5367 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3185   -1.6150    1.6987 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8137   -0.4643    1.1917 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9652    0.4291    0.5024 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3660    0.1420    0.3345 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2214    1.0513   -0.3773 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8506    2.1063   -0.8781 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6340    0.7258   -0.5414 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4783    1.5981   -1.2248 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8138    1.3632   -1.4174 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3126    0.2034   -0.8995 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4907   -0.7162   -0.1956 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0623   -1.8485    0.2899 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1484   -0.4613   -0.0124 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5251    1.6901    0.0545 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8770    2.7324    0.1762 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8726    1.6688   -0.5333 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7344    0.6056    0.0478 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.8676   -0.5120   -0.9968 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6786   -1.5216   -0.4606 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2092   -0.0626    1.2948 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4514   -2.8321    1.9389 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9321   -2.3220    2.2297 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0562    2.5045   -1.6217 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4523    2.0539   -1.9514 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3512   -0.0582   -1.0059 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7566   -2.5928    0.7732 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7776    1.5702   -1.6553 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3452    2.6622   -0.3137 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7572    1.0069    0.1915 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8848   -0.9810   -1.2091 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3003   -0.1301   -1.9354 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3169   -1.0597    0.1415 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8687   -0.8731    1.6206 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2705    0.7212    2.1071 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  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
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 15 17  2  0
  7 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 21 24  1  0
 17  2  1  0
  8  3  1  0
 17 11  1  0
 24  6  1  0
  4 25  1  0
  5 26  1  0
 12 27  1  0
 13 28  1  0
 14 29  1  0
 16 30  1  0
 20 31  1  0
 20 32  1  0
 21 33  1  1
 22 34  1  0
 22 35  1  0
 23 36  1  0
 24 37  1  0
 24 38  1  0
M  END


  Mrv1652306242118043D          

 38 41  0  0  0  0            999 V2000
    2.7133   -2.4540    1.1886 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2688   -1.3686    0.7005 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8662   -1.0559    0.8705 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0211   -1.9060    1.5367 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3185   -1.6150    1.6987 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8137   -0.4643    1.1917 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9652    0.4291    0.5024 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3660    0.1420    0.3345 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2214    1.0513   -0.3773 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8506    2.1063   -0.8781 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6340    0.7258   -0.5414 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4783    1.5981   -1.2248 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8138    1.3632   -1.4174 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3126    0.2034   -0.8995 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4907   -0.7162   -0.1956 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0623   -1.8485    0.2899 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1484   -0.4613   -0.0124 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5251    1.6901    0.0545 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8770    2.7324    0.1762 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8726    1.6688   -0.5333 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.7344    0.6056    0.0478 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.8676   -0.5120   -0.9968 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.6786   -1.5216   -0.4606 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2092   -0.0626    1.2948 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4514   -2.8321    1.9389 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9321   -2.3220    2.2297 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0562    2.5045   -1.6217 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4523    2.0539   -1.9514 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3512   -0.0582   -1.0059 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7566   -2.5928    0.7732 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7776    1.5702   -1.6553 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3452    2.6622   -0.3137 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7572    1.0069    0.1915 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8848   -0.9810   -1.2091 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3003   -0.1301   -1.9354 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3169   -1.0597    0.1415 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8687   -0.8731    1.6206 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2705    0.7212    2.1071 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  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
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 11 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
 15 17  2  0  0  0  0
  7 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 21 24  1  0  0  0  0
 17  2  1  0  0  0  0
  8  3  1  0  0  0  0
 17 11  1  0  0  0  0
 24  6  1  0  0  0  0
  4 25  1  0  0  0  0
  5 26  1  0  0  0  0
 12 27  1  0  0  0  0
 13 28  1  0  0  0  0
 14 29  1  0  0  0  0
 16 30  1  0  0  0  0
 20 31  1  0  0  0  0
 20 32  1  0  0  0  0
 21 33  1  1  0  0  0
 22 34  1  0  0  0  0
 22 35  1  0  0  0  0
 23 36  1  0  0  0  0
 24 37  1  0  0  0  0
 24 38  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0004105

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C2C(=O)C3=C([H])C([H])=C4C(C(=O)C([H])([H])[C@@]([H])(C([H])([H])O[H])C4([H])[H])=C3C(=O)C2=C([H])C([H])=C1[H]

> <INCHI_IDENTIFIER>
InChI=1S/C19H14O5/c20-8-9-6-10-4-5-12-17(15(10)14(22)7-9)19(24)11-2-1-3-13(21)16(11)18(12)23/h1-5,9,20-21H,6-8H2/t9-/m0/s1

> <INCHI_KEY>
UXSDRWXYYLSCOY-VIFPVBQESA-N

> <FORMULA>
C19H14O5

> <MOLECULAR_WEIGHT>
322.316

> <EXACT_MASS>
322.084123551

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
38

> <JCHEM_AVERAGE_POLARIZABILITY>
32.54274270704783

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3S)-8-hydroxy-3-(hydroxymethyl)-1,2,3,4,7,12-hexahydrotetraphene-1,7,12-trione

> <ALOGPS_LOGP>
2.62

> <JCHEM_LOGP>
2.5013138149999996

> <ALOGPS_LOGS>
-3.82

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.721547128131913

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.823063797549772

> <JCHEM_PKA_STRONGEST_BASIC>
-2.604783861794683

> <JCHEM_POLAR_SURFACE_AREA>
91.67

> <JCHEM_REFRACTIVITY>
87.8009

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.90e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3S)-8-hydroxy-3-(hydroxymethyl)-3,4-dihydro-2H-tetraphene-1,7,12-trione

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 38 41  0  0  0  0  0  0  0  0999 V2000
    2.7133   -2.4540    1.1886 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2688   -1.3686    0.7005 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8662   -1.0559    0.8705 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0211   -1.9060    1.5367 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3185   -1.6150    1.6987 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8137   -0.4643    1.1917 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9652    0.4291    0.5024 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3660    0.1420    0.3345 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2214    1.0513   -0.3773 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8506    2.1063   -0.8781 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6340    0.7258   -0.5414 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4783    1.5981   -1.2248 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8138    1.3632   -1.4174 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3126    0.2034   -0.8995 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4907   -0.7162   -0.1956 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0623   -1.8485    0.2899 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1484   -0.4613   -0.0124 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5251    1.6901    0.0545 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8770    2.7324    0.1762 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8726    1.6688   -0.5333 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7344    0.6056    0.0478 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.8676   -0.5120   -0.9968 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6786   -1.5216   -0.4606 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2092   -0.0626    1.2948 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4514   -2.8321    1.9389 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9321   -2.3220    2.2297 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0562    2.5045   -1.6217 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4523    2.0539   -1.9514 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3512   -0.0582   -1.0059 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7566   -2.5928    0.7732 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7776    1.5702   -1.6553 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3452    2.6622   -0.3137 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7572    1.0069    0.1915 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8848   -0.9810   -1.2091 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3003   -0.1301   -1.9354 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3169   -1.0597    0.1415 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8687   -0.8731    1.6206 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2705    0.7212    2.1071 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  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
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 15 17  2  0
  7 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 21 24  1  0
 17  2  1  0
  8  3  1  0
 17 11  1  0
 24  6  1  0
  4 25  1  0
  5 26  1  0
 12 27  1  0
 13 28  1  0
 14 29  1  0
 16 30  1  0
 20 31  1  0
 20 32  1  0
 21 33  1  1
 22 34  1  0
 22 35  1  0
 23 36  1  0
 24 37  1  0
 24 38  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  O   UNK     0       2.713  -2.454   1.189  0.00  0.00           O+0
HETATM    2  C   UNK     0       2.269  -1.369   0.701  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.866  -1.056   0.871  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.021  -1.906   1.537  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.319  -1.615   1.699  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.814  -0.464   1.192  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.965   0.429   0.502  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.366   0.142   0.335  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.221   1.051  -0.377  0.00  0.00           C+0
HETATM   10  O   UNK     0       0.851   2.106  -0.878  0.00  0.00           O+0
HETATM   11  C   UNK     0       2.634   0.726  -0.541  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.478   1.598  -1.225  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.814   1.363  -1.417  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.313   0.203  -0.900  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.491  -0.716  -0.196  0.00  0.00           C+0
HETATM   16  O   UNK     0       5.062  -1.849   0.290  0.00  0.00           O+0
HETATM   17  C   UNK     0       3.148  -0.461  -0.012  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.525   1.690   0.055  0.00  0.00           C+0
HETATM   19  O   UNK     0      -0.877   2.732   0.176  0.00  0.00           O+0
HETATM   20  C   UNK     0      -2.873   1.669  -0.533  0.00  0.00           C+0
HETATM   21  C   UNK     0      -3.734   0.606   0.048  0.00  0.00           C+0
HETATM   22  C   UNK     0      -3.868  -0.512  -0.997  0.00  0.00           C+0
HETATM   23  O   UNK     0      -4.679  -1.522  -0.461  0.00  0.00           O+0
HETATM   24  C   UNK     0      -3.209  -0.063   1.295  0.00  0.00           C+0
HETATM   25  H   UNK     0       0.451  -2.832   1.939  0.00  0.00           H+0
HETATM   26  H   UNK     0      -1.932  -2.322   2.230  0.00  0.00           H+0
HETATM   27  H   UNK     0       3.056   2.505  -1.622  0.00  0.00           H+0
HETATM   28  H   UNK     0       5.452   2.054  -1.951  0.00  0.00           H+0
HETATM   29  H   UNK     0       6.351  -0.058  -1.006  0.00  0.00           H+0
HETATM   30  H   UNK     0       4.757  -2.593   0.773  0.00  0.00           H+0
HETATM   31  H   UNK     0      -2.778   1.570  -1.655  0.00  0.00           H+0
HETATM   32  H   UNK     0      -3.345   2.662  -0.314  0.00  0.00           H+0
HETATM   33  H   UNK     0      -4.757   1.007   0.192  0.00  0.00           H+0
HETATM   34  H   UNK     0      -2.885  -0.981  -1.209  0.00  0.00           H+0
HETATM   35  H   UNK     0      -4.300  -0.130  -1.935  0.00  0.00           H+0
HETATM   36  H   UNK     0      -5.317  -1.060   0.142  0.00  0.00           H+0
HETATM   37  H   UNK     0      -3.869  -0.873   1.621  0.00  0.00           H+0
HETATM   38  H   UNK     0      -3.271   0.721   2.107  0.00  0.00           H+0
CONECT    1    2                                                            
CONECT    2    1    3   17                                                  
CONECT    3    2    4    8                                                  
CONECT    4    3    5   25                                                  
CONECT    5    4    6   26                                                  
CONECT    6    5    7   24                                                  
CONECT    7    6    8   18                                                  
CONECT    8    7    9    3                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   17                                                  
CONECT   12   11   13   27                                                  
CONECT   13   12   14   28                                                  
CONECT   14   13   15   29                                                  
CONECT   15   14   16   17                                                  
CONECT   16   15   30                                                       
CONECT   17   15    2   11                                                  
CONECT   18    7   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21   31   32                                             
CONECT   21   20   22   24   33                                             
CONECT   22   21   23   34   35                                             
CONECT   23   22   36                                                       
CONECT   24   21    6   37   38                                             
CONECT   25    4                                                            
CONECT   26    5                                                            
CONECT   27   12                                                            
CONECT   28   13                                                            
CONECT   29   14                                                            
CONECT   30   16                                                            
CONECT   31   20                                                            
CONECT   32   20                                                            
CONECT   33   21                                                            
CONECT   34   22                                                            
CONECT   35   22                                                            
CONECT   36   23                                                            
CONECT   37   24                                                            
CONECT   38   24                                                            
MASTER        0    0    0    0    0    0    0    0   38    0   82    0
END

RDKit          3D

38 41  0  0  0  0  0  0  0  0999 V2000
    2.7133   -2.4540    1.1886 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2688   -1.3686    0.7005 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8662   -1.0559    0.8705 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0211   -1.9060    1.5367 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3185   -1.6150    1.6987 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8137   -0.4643    1.1917 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9652    0.4291    0.5024 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3660    0.1420    0.3345 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2214    1.0513   -0.3773 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8506    2.1063   -0.8781 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6340    0.7258   -0.5414 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4783    1.5981   -1.2248 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8138    1.3632   -1.4174 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3126    0.2034   -0.8995 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4907   -0.7162   -0.1956 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0623   -1.8485    0.2899 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1484   -0.4613   -0.0124 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5251    1.6901    0.0545 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8770    2.7324    0.1762 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8726    1.6688   -0.5333 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7344    0.6056    0.0478 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.8676   -0.5120   -0.9968 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6786   -1.5216   -0.4606 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2092   -0.0626    1.2948 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4514   -2.8321    1.9389 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9321   -2.3220    2.2297 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0562    2.5045   -1.6217 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4523    2.0539   -1.9514 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3512   -0.0582   -1.0059 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7566   -2.5928    0.7732 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7776    1.5702   -1.6553 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3452    2.6622   -0.3137 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7572    1.0069    0.1915 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8848   -0.9810   -1.2091 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3003   -0.1301   -1.9354 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3169   -1.0597    0.1415 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8687   -0.8731    1.6206 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2705    0.7212    2.1071 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  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
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 15 17  2  0
  7 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 21 24  1  0
 17  2  1  0
  8  3  1  0
 17 11  1  0
 24  6  1  0
  4 25  1  0
  5 26  1  0
 12 27  1  0
 13 28  1  0
 14 29  1  0
 16 30  1  0
 20 31  1  0
 20 32  1  0
 21 33  1  1
 22 34  1  0
 22 35  1  0
 23 36  1  0
 24 37  1  0
 24 38  1  0
M  END

View in JSmol View NMR Assignments View DFT Assignments 3D Conformers

Synonyms

Not Available

Chemical Formula

C₁₉H₁₄O₅

Average Mass

322.3160 Da

Monoisotopic Mass

322.08412 Da

IUPAC Name

(3S)-8-hydroxy-3-(hydroxymethyl)-1,2,3,4,7,12-hexahydrotetraphene-1,7,12-trione

Traditional Name

(3S)-8-hydroxy-3-(hydroxymethyl)-3,4-dihydro-2H-tetraphene-1,7,12-trione

CAS Registry Number

Not Available

SMILES

OC[C@@H]1CC(=O)C2=C(C1)C=CC1=C2C(=O)C2=C(C(O)=CC=C2)C1=O

InChI Identifier

InChI=1S/C19H14O5/c20-8-9-6-10-4-5-12-17(15(10)14(22)7-9)19(24)11-2-1-3-13(21)16(11)18(12)23/h1-5,9,20-21H,6-8H2/t9-/m0/s1

InChI Key

UXSDRWXYYLSCOY-VIFPVBQESA-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
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 150 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 175 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 225 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 250 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, chcl3, 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
Streptomyces sp.	NPAtlas	11918062

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as angucyclines. These are polyketides with a structure based on then benz[a]anthracene skeleton, with the particularity that the central ring of the anthracene moiety is a para-quinone.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Angucyclines

Sub Class

Not Available

Direct Parent

Angucyclines

Alternative Parents

Substituents

Angucycline core
9,10-anthraquinone
Anthraquinone
Anthracene
Phenanthrene
Tetralin
Aryl alkyl ketone
Aryl ketone
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Benzenoid
Vinylogous acid
Ketone
Alcohol
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Primary alcohol
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

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

Predicted Properties

Property	Value	Source
logP	2.62	ALOGPS
logP	2.5	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	7.82	ChemAxon
pKa (Strongest Basic)	-2.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	91.67 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	87.8 m³·mol⁻¹	ChemAxon
Polarizability	32.54 Å³	ChemAxon
Number of Rings	4	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

NPA010790

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

8511692

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10336233

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Taniguchi M, Nagai K, Watanabe M, Nimura N, Suzuki K, Tanaka A: YM-181741, a novel benz[a]anthraquinone antibiotic with anti-Helicobacter pylori activity from Streptomyces sp. J Antibiot (Tokyo). 2002 Jan;55(1):30-5. doi: 10.7164/antibiotics.55.30. [PubMed:11918062 ]

Showing NP-Card for YM-181741 (NP0004105)

MOL for NP0004105 (YM-181741)

3D MOL for NP0004105 (YM-181741)

3D SDF for NP0004105 (YM-181741)

3D-SDF for NP0004105 (YM-181741)

PDB for NP0004105 (YM-181741)

3D PDB for NP0004105 (YM-181741)

SMILES for NP0004105 (YM-181741)

INCHI for NP0004105 (YM-181741)

Structure for NP0004105 (YM-181741)

3D Structure for NP0004105 (YM-181741)