NP-MRD: Showing NP-Card for (1s,9s,10s,11s,12s,13s,14r)-11,12,14-trihydroxy-7,9-dimethoxy-13-methyl-12-[(2r,3s)-3-methyloxirane-2-carbonyl]-15-oxatetracyclo[8.4.1.0¹,¹⁰.0³,⁸]pentadeca-3(8),4,6-trien-2-one (NP0280375)

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Record Information

Version

2.0

Created at

2022-09-09 06:07:45 UTC

Updated at

2022-09-09 06:07:45 UTC

NP-MRD ID

NP0280375

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,9s,10s,11s,12s,13s,14r)-11,12,14-trihydroxy-7,9-dimethoxy-13-methyl-12-[(2r,3s)-3-methyloxirane-2-carbonyl]-15-oxatetracyclo[8.4.1.0¹,¹⁰.0³,⁸]pentadeca-3(8),4,6-trien-2-one

Description

Mensacarcin belongs to the class of organic compounds known as tetralins. These are polycyclic aromatic compounds containing a tetralin moiety, which consists of a benzene fused to a cyclohexane. (1s,9s,10s,11s,12s,13s,14r)-11,12,14-trihydroxy-7,9-dimethoxy-13-methyl-12-[(2r,3s)-3-methyloxirane-2-carbonyl]-15-oxatetracyclo[8.4.1.0¹,¹⁰.0³,⁸]pentadeca-3(8),4,6-trien-2-one was first documented in 2014 (PMID: 24554499). Based on a literature review a small amount of articles have been published on Mensacarcin (PMID: 33763824) (PMID: 34285967) (PMID: 29074620) (PMID: 25907804).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309092208072D          

 30 34  0  0  1  0            999 V2000
    5.0013   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8579   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4289    1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4289    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0980    1.3808    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4323    0.4623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3802    0.3190    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9626   -0.1697    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7379   -0.4519    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1059   -0.9822    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8237   -1.7574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  3  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  6  0  0  0
 10 11  1  0  0  0  0
  9 12  1  0  0  0  0
 12 13  1  6  0  0  0
 14 13  1  6  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
  7 15  1  0  0  0  0
 15 16  2  0  0  0  0
 14 17  1  0  0  0  0
 17 18  1  1  0  0  0
 17 19  1  0  0  0  0
 19 20  1  1  0  0  0
 19 21  1  0  0  0  0
 21 22  1  1  0  0  0
 21 23  1  6  0  0  0
 23 24  2  0  0  0  0
 25 23  1  6  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 25 27  1  0  0  0  0
 27 28  1  1  0  0  0
 21 29  1  0  0  0  0
 12 29  1  0  0  0  0
 29 30  1  1  0  0  0
M  END

     RDKit          3D

 54 58  0  0  0  0  0  0  0  0999 V2000
   -4.7784    3.2693    0.0577 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7407    2.3299   -0.0227 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9842    0.9652   -0.0007 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2562    0.4456    0.1012 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4512   -0.9264    0.1194 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4204   -1.8114    0.0388 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1381   -1.2590   -0.0647 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9110    0.1011   -0.0840 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4934    0.5356   -0.1568 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3858    1.9184   -0.2614 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8782    2.5205    0.8841 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6424   -0.2367   -1.1043 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1157   -1.0149   -2.1265 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7569   -1.6329   -0.9272 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9537   -2.0897   -0.1811 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9473   -3.2105    0.3586 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4492   -2.4877   -0.8205 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3729   -3.1589    0.4209 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7697   -1.8182   -0.8841 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7451   -2.5560    0.0103 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7194   -0.3530   -0.4531 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2371   -0.3073    0.8305 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0320    0.2785   -0.6335 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5199    0.2725   -1.7511 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7959    0.9199    0.4574 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.6294    1.9657    0.0591 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3139    0.8197    0.4250 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.0642    0.9086    1.7219 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7444    0.3029   -1.4003 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7574    1.6702   -1.3999 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3042    3.3568   -0.9274 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3508    4.2577    0.3326 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4681    2.9589    0.8664 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0797    1.1430    0.1651 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4627   -1.3393    0.2010 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4883   -2.8861    0.0479 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0666    0.3133    0.8800 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1258    2.1821    1.1803 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8306    3.6122    0.6895 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5354    2.3560    1.7678 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4352   -3.3049   -1.5974 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2038   -4.1232    0.3158 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1477   -1.8815   -1.9319 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7929   -2.2213   -0.1887 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4666   -2.4434    1.0759 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7144   -3.6425   -0.2040 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9530   -0.5071    1.4559 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3856    0.9435    1.4793 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7016    0.1254   -0.3438 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7638    0.0352    1.8236 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3545    0.8341    2.5871 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6337    1.8504    1.8426 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1019   -0.0049   -2.4277 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5090    2.0249   -2.3031 H   0  0  0  0  0  0  0  0  0  0  0  0
 11 10  1  0
 10  9  1  0
  9  8  1  0
  8  7  2  0
  7  6  1  0
  6  5  2  0
  5  4  1  0
  4  3  2  0
  3  2  1  0
  2  1  1  0
  7 15  1  0
 15 16  2  0
 15 14  1  0
 14 13  1  6
 12 13  1  6
 12 29  1  0
 29 30  1  0
 29 21  1  0
 21 22  1  1
 21 19  1  0
 19 20  1  0
 19 17  1  0
 17 18  1  0
 21 23  1  0
 23 24  2  0
 23 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 12  9  1  0
 27 25  1  0
  3  8  1  0
 12 14  1  0
 17 14  1  0
 11 38  1  0
 11 39  1  0
 11 40  1  0
  9 37  1  1
  6 36  1  0
  5 35  1  0
  4 34  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
 29 53  1  6
 30 54  1  0
 22 47  1  0
 19 43  1  6
 20 44  1  0
 20 45  1  0
 20 46  1  0
 17 41  1  6
 18 42  1  0
 25 48  1  1
 27 49  1  6
 28 50  1  0
 28 51  1  0
 28 52  1  0
M  END


  Mrv1652309092208072D          

 30 34  0  0  1  0            999 V2000
    5.0013   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8579   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4289    1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4289    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0980    1.3808    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4323    0.4623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3802    0.3190    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9626   -0.1697    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7379   -0.4519    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1059   -0.9822    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8237   -1.7574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  3  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  6  0  0  0
 10 11  1  0  0  0  0
  9 12  1  0  0  0  0
 12 13  1  6  0  0  0
 14 13  1  6  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
  7 15  1  0  0  0  0
 15 16  2  0  0  0  0
 14 17  1  0  0  0  0
 17 18  1  1  0  0  0
 17 19  1  0  0  0  0
 19 20  1  1  0  0  0
 19 21  1  0  0  0  0
 21 22  1  1  0  0  0
 21 23  1  6  0  0  0
 23 24  2  0  0  0  0
 25 23  1  6  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 25 27  1  0  0  0  0
 27 28  1  1  0  0  0
 21 29  1  0  0  0  0
 12 29  1  0  0  0  0
 29 30  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0280375

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CO[C@H]1C2=C(C=CC=C2OC)C(=O)[C@@]23O[C@@]12[C@@H](O)[C@@](O)([C@@H](C)[C@H]3O)C(=O)[C@@H]1O[C@H]1C

> <INCHI_IDENTIFIER>
InChI=1S/C21H24O9/c1-8-14(22)20-15(23)10-6-5-7-11(27-3)12(10)17(28-4)21(20,30-20)18(25)19(8,26)16(24)13-9(2)29-13/h5-9,13-14,17-18,22,25-26H,1-4H3/t8-,9-,13+,14+,17-,18-,19+,20+,21+/m0/s1

> <INCHI_KEY>
WWNXYRCJJRRWAQ-ALCXHWRFSA-N

> <FORMULA>
C21H24O9

> <MOLECULAR_WEIGHT>
420.414

> <EXACT_MASS>
420.142032353

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
54

> <JCHEM_AVERAGE_POLARIZABILITY>
41.03521859411613

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,9S,10S,11S,12S,13S,14R)-11,12,14-trihydroxy-7,9-dimethoxy-13-methyl-12-[(2R,3S)-3-methyloxirane-2-carbonyl]-15-oxatetracyclo[8.4.1.0^{1,10}.0^{3,8}]pentadeca-3(8),4,6-trien-2-one

> <JCHEM_LOGP>
-0.1415612153333324

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.119964267812488

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.646695662558503

> <JCHEM_PKA_STRONGEST_BASIC>
-3.502156341481154

> <JCHEM_POLAR_SURFACE_AREA>
138.35

> <JCHEM_REFRACTIVITY>
99.47079999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1S,9S,10S,11S,12S,13S,14R)-11,12,14-trihydroxy-7,9-dimethoxy-13-methyl-12-[(2R,3S)-3-methyloxirane-2-carbonyl]-15-oxatetracyclo[8.4.1.0^{1,10}.0^{3,8}]pentadeca-3(8),4,6-trien-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 09-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-SEP-22         0                                  
HETATM    1  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       8.002  -0.000   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.336   2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.336   3.850   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.002   4.620   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       5.335  -0.000   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       2.667   3.080   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       5.335   6.160   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       2.667   6.160   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -0.183   2.577   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       0.807   0.863   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      -0.710   0.595   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       1.797  -0.317   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       3.244  -0.844   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       2.064  -1.833   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       1.538  -3.281   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       2.667  -0.000   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    8                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   15                                                  
CONECT    8    7    3    9                                                  
CONECT    9    8   10   12                                                  
CONECT   10    9   11                                                       
CONECT   11   10                                                            
CONECT   12    9   13   14   29                                             
CONECT   13   12   14                                                       
CONECT   14   13   12   15   17                                             
CONECT   15   14    7   16                                                  
CONECT   16   15                                                            
CONECT   17   14   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22   23   29                                             
CONECT   22   21                                                            
CONECT   23   21   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26   27                                                  
CONECT   26   25   27                                                       
CONECT   27   26   25   28                                                  
CONECT   28   27                                                            
CONECT   29   21   12   30                                                  
CONECT   30   29                                                            
MASTER        0    0    0    0    0    0    0    0   30    0   68    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₁H₂₄O₉

Average Mass

420.4140 Da

Monoisotopic Mass

420.14203 Da

IUPAC Name

(1S,9S,10S,11S,12S,13S,14R)-11,12,14-trihydroxy-7,9-dimethoxy-13-methyl-12-[(2R,3S)-3-methyloxirane-2-carbonyl]-15-oxatetracyclo[8.4.1.0^{1,10}.0^{3,8}]pentadeca-3(8),4,6-trien-2-one

Traditional Name

(1S,9S,10S,11S,12S,13S,14R)-11,12,14-trihydroxy-7,9-dimethoxy-13-methyl-12-[(2R,3S)-3-methyloxirane-2-carbonyl]-15-oxatetracyclo[8.4.1.0^{1,10}.0^{3,8}]pentadeca-3(8),4,6-trien-2-one

CAS Registry Number

Not Available

SMILES

CO[C@H]1C2=C(C=CC=C2OC)C(=O)[C@@]23O[C@@]12[C@@H](O)[C@@](O)([C@@H](C)[C@H]3O)C(=O)[C@@H]1O[C@H]1C

InChI Identifier

InChI=1S/C21H24O9/c1-8-14(22)20-15(23)10-6-5-7-11(27-3)12(10)17(28-4)21(20,30-20)18(25)19(8,26)16(24)13-9(2)29-13/h5-9,13-14,17-18,22,25-26H,1-4H3/t8-,9-,13+,14+,17-,18-,19+,20+,21+/m0/s1

InChI Key

WWNXYRCJJRRWAQ-ALCXHWRFSA-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, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as tetralins. These are polycyclic aromatic compounds containing a tetralin moiety, which consists of a benzene fused to a cyclohexane.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Tetralins

Sub Class

Not Available

Direct Parent

Tetralins

Alternative Parents

Substituents

Tetralin
Anisole
Aryl alkyl ketone
Aryl ketone
Alkyl aryl ether
Oxepane
Cyclitol or derivatives
Alpha-hydroxy ketone
Cyclic alcohol
Tertiary alcohol
Ketone
Secondary alcohol
Organoheterocyclic compound
Oxacycle
Ether
Oxirane
Dialkyl ether
Polyol
Alcohol
Carbonyl group
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

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

Predicted Properties

Property	Value	Source
logP	-0.14	ChemAxon
pKa (Strongest Acidic)	11.65	ChemAxon
pKa (Strongest Basic)	-3.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	138.35 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	99.47 m³·mol⁻¹	ChemAxon
Polarizability	41.04 Å³	ChemAxon
Number of Rings	5	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

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

357559

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Mensacarcin

METLIN ID

Not Available

PubChem Compound

403671

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Alali A, Zhang L, Li J, Zuo C, Wassouf D, Yan X, Schwarzer P, Gunther S, Einsle O, Bechthold A: Biosynthesis of the Tricyclic Aromatic Type II Polyketide Rishirilide: New Potential Third Ring Oxygenation after Three Cyclization Steps. Mol Biotechnol. 2021 Jun;63(6):502-514. doi: 10.1007/s12033-021-00314-x. Epub 2021 Mar 24. [PubMed:33763824 ]
Plitzko B, Loesgen S: Measurement of Oxygen Consumption Rate (OCR) and Extracellular Acidification Rate (ECAR) in Culture Cells for Assessment of the Energy Metabolism. Bio Protoc. 2018 May 20;8(10):e2850. doi: 10.21769/BioProtoc.2850. eCollection 2018 May 20. [PubMed:34285967 ]
Plitzko B, Kaweesa EN, Loesgen S: The natural product mensacarcin induces mitochondrial toxicity and apoptosis in melanoma cells. J Biol Chem. 2017 Dec 22;292(51):21102-21116. doi: 10.1074/jbc.M116.774836. Epub 2017 Oct 26. [PubMed:29074620 ]
Maier S, Heitzler T, Asmus K, Brotz E, Hardter U, Hesselbach K, Paululat T, Bechthold A: Functional characterization of different ORFs including luciferase-like monooxygenase genes from the mensacarcin gene cluster. Chembiochem. 2015 May 26;16(8):1175-82. doi: 10.1002/cbic.201500048. Epub 2015 Apr 23. [PubMed:25907804 ]
Maier S, Pfluger T, Loesgen S, Asmus K, Brotz E, Paululat T, Zeeck A, Andrade S, Bechthold A: Insights into the bioactivity of mensacarcin and epoxide formation by MsnO8. Chembiochem. 2014 Mar 21;15(5):749-56. doi: 10.1002/cbic.201300704. Epub 2014 Feb 19. [PubMed:24554499 ]
LOTUS database [Link]

Showing NP-Card for (1s,9s,10s,11s,12s,13s,14r)-11,12,14-trihydroxy-7,9-dimethoxy-13-methyl-12-[(2r,3s)-3-methyloxirane-2-carbonyl]-15-oxatetracyclo[8.4.1.0¹,¹⁰.0³,⁸]pentadeca-3(8),4,6-trien-2-one (NP0280375)

MOL for NP0280375 ((1s,9s,10s,11s,12s,13s,14r)-11,12,14-trihydroxy-7,9-dimethoxy-13-methyl-12-[(2r,3s)-3-methyloxirane-2-carbonyl]-15-oxatetracyclo[8.4.1.0¹,¹⁰.0³,⁸]pentadeca-3(8),4,6-trien-2-one)

3D MOL for NP0280375 ((1s,9s,10s,11s,12s,13s,14r)-11,12,14-trihydroxy-7,9-dimethoxy-13-methyl-12-[(2r,3s)-3-methyloxirane-2-carbonyl]-15-oxatetracyclo[8.4.1.0¹,¹⁰.0³,⁸]pentadeca-3(8),4,6-trien-2-one)

3D SDF for NP0280375 ((1s,9s,10s,11s,12s,13s,14r)-11,12,14-trihydroxy-7,9-dimethoxy-13-methyl-12-[(2r,3s)-3-methyloxirane-2-carbonyl]-15-oxatetracyclo[8.4.1.0¹,¹⁰.0³,⁸]pentadeca-3(8),4,6-trien-2-one)

3D-SDF for NP0280375 ((1s,9s,10s,11s,12s,13s,14r)-11,12,14-trihydroxy-7,9-dimethoxy-13-methyl-12-[(2r,3s)-3-methyloxirane-2-carbonyl]-15-oxatetracyclo[8.4.1.0¹,¹⁰.0³,⁸]pentadeca-3(8),4,6-trien-2-one)

PDB for NP0280375 ((1s,9s,10s,11s,12s,13s,14r)-11,12,14-trihydroxy-7,9-dimethoxy-13-methyl-12-[(2r,3s)-3-methyloxirane-2-carbonyl]-15-oxatetracyclo[8.4.1.0¹,¹⁰.0³,⁸]pentadeca-3(8),4,6-trien-2-one)

3D PDB for NP0280375 ((1s,9s,10s,11s,12s,13s,14r)-11,12,14-trihydroxy-7,9-dimethoxy-13-methyl-12-[(2r,3s)-3-methyloxirane-2-carbonyl]-15-oxatetracyclo[8.4.1.0¹,¹⁰.0³,⁸]pentadeca-3(8),4,6-trien-2-one)

SMILES for NP0280375 ((1s,9s,10s,11s,12s,13s,14r)-11,12,14-trihydroxy-7,9-dimethoxy-13-methyl-12-[(2r,3s)-3-methyloxirane-2-carbonyl]-15-oxatetracyclo[8.4.1.0¹,¹⁰.0³,⁸]pentadeca-3(8),4,6-trien-2-one)

INCHI for NP0280375 ((1s,9s,10s,11s,12s,13s,14r)-11,12,14-trihydroxy-7,9-dimethoxy-13-methyl-12-[(2r,3s)-3-methyloxirane-2-carbonyl]-15-oxatetracyclo[8.4.1.0¹,¹⁰.0³,⁸]pentadeca-3(8),4,6-trien-2-one)

Structure for NP0280375 ((1s,9s,10s,11s,12s,13s,14r)-11,12,14-trihydroxy-7,9-dimethoxy-13-methyl-12-[(2r,3s)-3-methyloxirane-2-carbonyl]-15-oxatetracyclo[8.4.1.0¹,¹⁰.0³,⁸]pentadeca-3(8),4,6-trien-2-one)

3D Structure for NP0280375 ((1s,9s,10s,11s,12s,13s,14r)-11,12,14-trihydroxy-7,9-dimethoxy-13-methyl-12-[(2r,3s)-3-methyloxirane-2-carbonyl]-15-oxatetracyclo[8.4.1.0¹,¹⁰.0³,⁸]pentadeca-3(8),4,6-trien-2-one)