NP-MRD: Showing NP-Card for Luisol B (NP0001614)

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Record Information

Version

1.0

Created at

2020-09-23 01:58:40 UTC

Updated at

2021-08-10 02:55:42 UTC

NP-MRD ID

NP0001614

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Luisol B

Provided By

NPAtlas

Description

(1R,2S,9R,10S,13R)-13-methyl-12,14-dioxatetracyclo[8.3.1.0¹,¹⁰.0³,⁸]Tetradeca-3(8),4,6-triene-2,4,9,13-tetrol belongs to the class of organic compounds known as naphthofurans. Naphthofurans are compounds containing a furan ring fused to a naphthalene moiety. Furan is a 5 membered- ring aromatic ring with four carbon and one oxygen atoms. Naphthalene is a polycyclic aromatic hydrocarbon made up of two fused benzene rings. Luisol B is found in Streptomyces sp. It was first documented in 1999 (PMID: 10217720). Based on a literature review very few articles have been published on (1R,2S,9R,10S,13R)-13-methyl-12,14-dioxatetracyclo[8.3.1.0¹,¹⁰.0³,⁸]Tetradeca-3(8),4,6-triene-2,4,9,13-tetrol (PMID: 26389497) (PMID: 26389486) (PMID: 26389480) (PMID: 26389479).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242117433D          

 33 36  0  0  0  0            999 V2000
    3.4340   -1.0345   -0.2669 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5034   -0.0398    0.4004 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4536   -0.1988    1.7678 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9258    1.2194    0.0731 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8713    1.9482   -0.4257 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8244    0.9456   -0.8707 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1973   -0.1410   -1.6253 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1236   -0.2382   -0.2382 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1451   -1.1254    0.4145 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3213   -1.0642    1.8176 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2466   -0.7104    0.1640 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2853   -1.5367    0.6377 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9206   -2.6831    1.3095 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5977   -1.1906    0.4257 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9174   -0.0388   -0.2482 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9081    0.7753   -0.7146 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5725    0.4260   -0.5007 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5921    1.3886   -1.0508 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8127    2.6767   -0.5958 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9876   -1.4585   -1.1997 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7044   -1.8749    0.3953 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3746   -0.5344   -0.5979 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2555    0.2493    2.1441 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4293    2.5174    0.4208 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1433    2.6685   -1.2007 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2219   -2.1986    0.0708 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2739   -0.3743    2.1863 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9753   -2.9634    1.4839 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3789   -1.8608    0.8101 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9610    0.2329   -0.4148 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1843    1.6860   -1.2475 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7841    1.4179   -2.1637 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5059    3.1145   -1.1607 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  1  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  6  0  0  0
  8  7  1  6  0  0  0
  8  9  1  0  0  0  0
  9 10  1  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
 12 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
  8  2  1  0  0  0  0
 17 11  1  0  0  0  0
  8  6  1  0  0  0  0
 18  6  1  0  0  0  0
  1 20  1  0  0  0  0
  1 21  1  0  0  0  0
  1 22  1  0  0  0  0
  3 23  1  0  0  0  0
  5 24  1  0  0  0  0
  5 25  1  0  0  0  0
  9 26  1  6  0  0  0
 10 27  1  0  0  0  0
 13 28  1  0  0  0  0
 14 29  1  0  0  0  0
 15 30  1  0  0  0  0
 16 31  1  0  0  0  0
 18 32  1  6  0  0  0
 19 33  1  0  0  0  0
M  END

     RDKit          3D

 33 36  0  0  0  0  0  0  0  0999 V2000
    3.4340   -1.0345   -0.2669 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5034   -0.0398    0.4004 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4536   -0.1988    1.7678 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9258    1.2194    0.0731 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8713    1.9482   -0.4257 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8244    0.9456   -0.8707 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1973   -0.1410   -1.6253 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1236   -0.2382   -0.2382 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1451   -1.1254    0.4145 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3213   -1.0642    1.8176 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2466   -0.7104    0.1640 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2853   -1.5367    0.6377 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9206   -2.6831    1.3095 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5977   -1.1906    0.4257 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9174   -0.0388   -0.2482 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9081    0.7753   -0.7146 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5725    0.4260   -0.5007 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5921    1.3886   -1.0508 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8127    2.6767   -0.5958 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9876   -1.4585   -1.1997 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7044   -1.8749    0.3953 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3746   -0.5344   -0.5979 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2555    0.2493    2.1441 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4293    2.5174    0.4208 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1433    2.6685   -1.2007 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2219   -2.1986    0.0708 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2739   -0.3743    2.1863 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9753   -2.9634    1.4839 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3789   -1.8608    0.8101 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9610    0.2329   -0.4148 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1843    1.6860   -1.2475 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7841    1.4179   -2.1637 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5059    3.1145   -1.1607 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  1
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  6
  8  7  1  6
  8  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 12 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
  8  2  1  0
 17 11  1  0
  8  6  1  0
 18  6  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  3 23  1  0
  5 24  1  0
  5 25  1  0
  9 26  1  6
 10 27  1  0
 13 28  1  0
 14 29  1  0
 15 30  1  0
 16 31  1  0
 18 32  1  6
 19 33  1  0
M  END


  Mrv1652306242117433D          

 33 36  0  0  0  0            999 V2000
    3.4340   -1.0345   -0.2669 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5034   -0.0398    0.4004 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4536   -0.1988    1.7678 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9258    1.2194    0.0731 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8713    1.9482   -0.4257 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8244    0.9456   -0.8707 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1973   -0.1410   -1.6253 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1236   -0.2382   -0.2382 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1451   -1.1254    0.4145 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3213   -1.0642    1.8176 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2466   -0.7104    0.1640 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2853   -1.5367    0.6377 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9206   -2.6831    1.3095 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5977   -1.1906    0.4257 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9174   -0.0388   -0.2482 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9081    0.7753   -0.7146 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5725    0.4260   -0.5007 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5921    1.3886   -1.0508 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8127    2.6767   -0.5958 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9876   -1.4585   -1.1997 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7044   -1.8749    0.3953 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3746   -0.5344   -0.5979 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2555    0.2493    2.1441 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4293    2.5174    0.4208 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1433    2.6685   -1.2007 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2219   -2.1986    0.0708 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2739   -0.3743    2.1863 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9753   -2.9634    1.4839 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3789   -1.8608    0.8101 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9610    0.2329   -0.4148 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1843    1.6860   -1.2475 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7841    1.4179   -2.1637 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5059    3.1145   -1.1607 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  1  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  6  0  0  0
  8  7  1  6  0  0  0
  8  9  1  0  0  0  0
  9 10  1  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
 12 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
  8  2  1  0  0  0  0
 17 11  1  0  0  0  0
  8  6  1  0  0  0  0
 18  6  1  0  0  0  0
  1 20  1  0  0  0  0
  1 21  1  0  0  0  0
  1 22  1  0  0  0  0
  3 23  1  0  0  0  0
  5 24  1  0  0  0  0
  5 25  1  0  0  0  0
  9 26  1  6  0  0  0
 10 27  1  0  0  0  0
 13 28  1  0  0  0  0
 14 29  1  0  0  0  0
 15 30  1  0  0  0  0
 16 31  1  0  0  0  0
 18 32  1  6  0  0  0
 19 33  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0001614

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C2C(=C([H])C([H])=C1[H])[C@@]([H])(O[H])[C@]13O[C@@]1([C@@]2([H])O[H])[C@](O[H])(OC3([H])[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C13H14O6/c1-11(17)13-10(16)8-6(3-2-4-7(8)14)9(15)12(13,19-13)5-18-11/h2-4,9-10,14-17H,5H2,1H3/t9-,10+,11-,12+,13+/m1/s1

> <INCHI_KEY>
FFOFXXVVSZUIAV-FHUSYTEZSA-N

> <FORMULA>
C13H14O6

> <MOLECULAR_WEIGHT>
266.249

> <EXACT_MASS>
266.079038171

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
33

> <JCHEM_AVERAGE_POLARIZABILITY>
25.084051908904186

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,2S,9R,10S,13R)-13-methyl-12,14-dioxatetracyclo[8.3.1.0^{1,10}.0^{3,8}]tetradeca-3,5,7-triene-2,4,9,13-tetrol

> <ALOGPS_LOGP>
-0.43

> <JCHEM_LOGP>
-0.5031003956666663

> <ALOGPS_LOGS>
-0.63

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.9955008294638

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.656846553011267

> <JCHEM_PKA_STRONGEST_BASIC>
-3.668791355211301

> <JCHEM_POLAR_SURFACE_AREA>
102.68

> <JCHEM_REFRACTIVITY>
62.36240000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.26e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2S,9R,10S,13R)-13-methyl-12,14-dioxatetracyclo[8.3.1.0^{1,10}.0^{3,8}]tetradeca-3,5,7-triene-2,4,9,13-tetrol

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 33 36  0  0  0  0  0  0  0  0999 V2000
    3.4340   -1.0345   -0.2669 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5034   -0.0398    0.4004 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4536   -0.1988    1.7678 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9258    1.2194    0.0731 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8713    1.9482   -0.4257 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8244    0.9456   -0.8707 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1973   -0.1410   -1.6253 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1236   -0.2382   -0.2382 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1451   -1.1254    0.4145 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3213   -1.0642    1.8176 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2466   -0.7104    0.1640 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2853   -1.5367    0.6377 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9206   -2.6831    1.3095 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5977   -1.1906    0.4257 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9174   -0.0388   -0.2482 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9081    0.7753   -0.7146 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5725    0.4260   -0.5007 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5921    1.3886   -1.0508 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8127    2.6767   -0.5958 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9876   -1.4585   -1.1997 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7044   -1.8749    0.3953 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3746   -0.5344   -0.5979 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2555    0.2493    2.1441 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4293    2.5174    0.4208 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1433    2.6685   -1.2007 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2219   -2.1986    0.0708 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2739   -0.3743    2.1863 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9753   -2.9634    1.4839 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3789   -1.8608    0.8101 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9610    0.2329   -0.4148 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1843    1.6860   -1.2475 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7841    1.4179   -2.1637 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5059    3.1145   -1.1607 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  1
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  6
  8  7  1  6
  8  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 12 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
  8  2  1  0
 17 11  1  0
  8  6  1  0
 18  6  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  3 23  1  0
  5 24  1  0
  5 25  1  0
  9 26  1  6
 10 27  1  0
 13 28  1  0
 14 29  1  0
 15 30  1  0
 16 31  1  0
 18 32  1  6
 19 33  1  0
M  END

HEADER    PROTEIN                                 24-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-JUN-21         0                                  
HETATM    1  C   UNK     0       3.434  -1.034  -0.267  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.503  -0.040   0.400  0.00  0.00           C+0
HETATM    3  O   UNK     0       2.454  -0.199   1.768  0.00  0.00           O+0
HETATM    4  O   UNK     0       2.926   1.219   0.073  0.00  0.00           O+0
HETATM    5  C   UNK     0       1.871   1.948  -0.426  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.824   0.946  -0.871  0.00  0.00           C+0
HETATM    7  O   UNK     0       1.197  -0.141  -1.625  0.00  0.00           O+0
HETATM    8  C   UNK     0       1.124  -0.238  -0.238  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.145  -1.125   0.415  0.00  0.00           C+0
HETATM   10  O   UNK     0       0.321  -1.064   1.818  0.00  0.00           O+0
HETATM   11  C   UNK     0      -1.247  -0.710   0.164  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.285  -1.537   0.638  0.00  0.00           C+0
HETATM   13  O   UNK     0      -1.921  -2.683   1.310  0.00  0.00           O+0
HETATM   14  C   UNK     0      -3.598  -1.191   0.426  0.00  0.00           C+0
HETATM   15  C   UNK     0      -3.917  -0.039  -0.248  0.00  0.00           C+0
HETATM   16  C   UNK     0      -2.908   0.775  -0.715  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.573   0.426  -0.501  0.00  0.00           C+0
HETATM   18  C   UNK     0      -0.592   1.389  -1.051  0.00  0.00           C+0
HETATM   19  O   UNK     0      -0.813   2.677  -0.596  0.00  0.00           O+0
HETATM   20  H   UNK     0       2.988  -1.458  -1.200  0.00  0.00           H+0
HETATM   21  H   UNK     0       3.704  -1.875   0.395  0.00  0.00           H+0
HETATM   22  H   UNK     0       4.375  -0.534  -0.598  0.00  0.00           H+0
HETATM   23  H   UNK     0       3.256   0.249   2.144  0.00  0.00           H+0
HETATM   24  H   UNK     0       1.429   2.517   0.421  0.00  0.00           H+0
HETATM   25  H   UNK     0       2.143   2.668  -1.201  0.00  0.00           H+0
HETATM   26  H   UNK     0       0.222  -2.199   0.071  0.00  0.00           H+0
HETATM   27  H   UNK     0      -0.274  -0.374   2.186  0.00  0.00           H+0
HETATM   28  H   UNK     0      -0.975  -2.963   1.484  0.00  0.00           H+0
HETATM   29  H   UNK     0      -4.379  -1.861   0.810  0.00  0.00           H+0
HETATM   30  H   UNK     0      -4.961   0.233  -0.415  0.00  0.00           H+0
HETATM   31  H   UNK     0      -3.184   1.686  -1.248  0.00  0.00           H+0
HETATM   32  H   UNK     0      -0.784   1.418  -2.164  0.00  0.00           H+0
HETATM   33  H   UNK     0      -1.506   3.115  -1.161  0.00  0.00           H+0
CONECT    1    2   20   21   22                                             
CONECT    2    1    3    4    8                                             
CONECT    3    2   23                                                       
CONECT    4    2    5                                                       
CONECT    5    4    6   24   25                                             
CONECT    6    5    7    8   18                                             
CONECT    7    6    8                                                       
CONECT    8    7    9    2    6                                             
CONECT    9    8   10   11   26                                             
CONECT   10    9   27                                                       
CONECT   11    9   12   17                                                  
CONECT   12   11   13   14                                                  
CONECT   13   12   28                                                       
CONECT   14   12   15   29                                                  
CONECT   15   14   16   30                                                  
CONECT   16   15   17   31                                                  
CONECT   17   16   18   11                                                  
CONECT   18   17   19    6   32                                             
CONECT   19   18   33                                                       
CONECT   20    1                                                            
CONECT   21    1                                                            
CONECT   22    1                                                            
CONECT   23    3                                                            
CONECT   24    5                                                            
CONECT   25    5                                                            
CONECT   26    9                                                            
CONECT   27   10                                                            
CONECT   28   13                                                            
CONECT   29   14                                                            
CONECT   30   15                                                            
CONECT   31   16                                                            
CONECT   32   18                                                            
CONECT   33   19                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   72    0
END

RDKit          3D

33 36  0  0  0  0  0  0  0  0999 V2000
    3.4340   -1.0345   -0.2669 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5034   -0.0398    0.4004 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4536   -0.1988    1.7678 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9258    1.2194    0.0731 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8713    1.9482   -0.4257 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8244    0.9456   -0.8707 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1973   -0.1410   -1.6253 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1236   -0.2382   -0.2382 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1451   -1.1254    0.4145 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3213   -1.0642    1.8176 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2466   -0.7104    0.1640 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2853   -1.5367    0.6377 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9206   -2.6831    1.3095 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5977   -1.1906    0.4257 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9174   -0.0388   -0.2482 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9081    0.7753   -0.7146 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5725    0.4260   -0.5007 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5921    1.3886   -1.0508 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8127    2.6767   -0.5958 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9876   -1.4585   -1.1997 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7044   -1.8749    0.3953 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3746   -0.5344   -0.5979 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2555    0.2493    2.1441 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4293    2.5174    0.4208 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1433    2.6685   -1.2007 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2219   -2.1986    0.0708 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2739   -0.3743    2.1863 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9753   -2.9634    1.4839 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3789   -1.8608    0.8101 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9610    0.2329   -0.4148 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1843    1.6860   -1.2475 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7841    1.4179   -2.1637 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5059    3.1145   -1.1607 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  1
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  6
  8  7  1  6
  8  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 12 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
  8  2  1  0
 17 11  1  0
  8  6  1  0
 18  6  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  3 23  1  0
  5 24  1  0
  5 25  1  0
  9 26  1  6
 10 27  1  0
 13 28  1  0
 14 29  1  0
 15 30  1  0
 16 31  1  0
 18 32  1  6
 19 33  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Value	Source
Luisol-b	MeSH

Chemical Formula

C₁₃H₁₄O₆

Average Mass

266.2490 Da

Monoisotopic Mass

266.07904 Da

IUPAC Name

(1R,2S,9R,10S,13R)-13-methyl-12,14-dioxatetracyclo[8.3.1.0^{1,10}.0^{3,8}]tetradeca-3,5,7-triene-2,4,9,13-tetrol

Traditional Name

(1R,2S,9R,10S,13R)-13-methyl-12,14-dioxatetracyclo[8.3.1.0^{1,10}.0^{3,8}]tetradeca-3,5,7-triene-2,4,9,13-tetrol

CAS Registry Number

Not Available

SMILES

[H]OC1=C2C(=C([H])C([H])=C1[H])[C@@]([H])(O[H])[C@]13O[C@@]1([C@@]2([H])O[H])[C@](O[H])(OC3([H])[H])C([H])([H])[H]

InChI Identifier

InChI=1S/C13H14O6/c1-11(17)13-10(16)8-6(3-2-4-7(8)14)9(15)12(13,19-13)5-18-11/h2-4,9-10,14-17H,5H2,1H3/t9-,10+,11-,12+,13+/m1/s1

InChI Key

FFOFXXVVSZUIAV-FHUSYTEZSA-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
Streptomyces sp.	NPAtlas	10217720

Species Where Detected

Species Name	Source	Reference
Streptomyces sp. CNH370	KNApSAcK Database	22123792

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as naphthofurans. Naphthofurans are compounds containing a furan ring fused to a naphthalene moiety. Furan is a 5 membered- ring aromatic ring with four carbon and one oxygen atoms. Naphthalene is a polycyclic aromatic hydrocarbon made up of two fused benzene rings.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Naphthofurans

Sub Class

Not Available

Direct Parent

Naphthofurans

Alternative Parents

Substituents

Naphthofuran
Tetralin
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Para-dioxane
Benzenoid
Oxolane
Hemiacetal
Secondary alcohol
Dialkyl ether
Oxirane
Ether
Oxacycle
Polyol
Hydrocarbon derivative
Organic oxygen compound
Organooxygen compound
Alcohol
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	-0.43	ALOGPS
logP	-0.5	ChemAxon
logS	-0.63	ALOGPS
pKa (Strongest Acidic)	9.66	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	102.68 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	62.36 m³·mol⁻¹	ChemAxon
Polarizability	25.08 Å³	ChemAxon
Number of Rings	4	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

NPA007993

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

8834731

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10659377

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Cheng XC, Jensen PR, Fenical W: Luisols A and B, new aromatic tetraols produced by an estuarine marine bacterium of the genus Streptomyces (Actinomycetales). J Nat Prod. 1999 Apr;62(4):608-10. doi: 10.1021/np980415m. [PubMed:10217720 ]
Authors unspecified: Lung Cancer Prevention (PDQ(R)): Patient Version. 2002. [PubMed:26389497 ]
Authors unspecified: Endometrial Cancer Screening (PDQ(R)): Patient Version. 2002. [PubMed:26389486 ]
Authors unspecified: Ewing Sarcoma and Undifferentiated Small Round Cell Sarcomas of Bone and Soft Tissue Treatment (PDQ(R)): Health Professional Version. 2002. [PubMed:26389480 ]
Authors unspecified: Bladder Cancer Treatment (PDQ(R)): Patient Version. 2002. [PubMed:26389479 ]

Showing NP-Card for Luisol B (NP0001614)

MOL for NP0001614 (Luisol B)

3D MOL for NP0001614 (Luisol B)

3D SDF for NP0001614 (Luisol B)

3D-SDF for NP0001614 (Luisol B)

PDB for NP0001614 (Luisol B)

3D PDB for NP0001614 (Luisol B)

SMILES for NP0001614 (Luisol B)

INCHI for NP0001614 (Luisol B)

Structure for NP0001614 (Luisol B)

3D Structure for NP0001614 (Luisol B)