NP-MRD: Showing NP-Card for (1s,9s)-12-(acetyloxy)-3-hydroxy-4,11-dimethoxy-17-azatetracyclo[7.5.3.0¹,¹⁰.0²,⁷]heptadeca-2,4,6,10-tetraen-13-yl acetate (NP0264681)

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Record Information

Version

2.0

Created at

2022-09-08 08:18:51 UTC

Updated at

2022-09-08 08:18:51 UTC

NP-MRD ID

NP0264681

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,9s)-12-(acetyloxy)-3-hydroxy-4,11-dimethoxy-17-azatetracyclo[7.5.3.0¹,¹⁰.0²,⁷]heptadeca-2,4,6,10-tetraen-13-yl acetate

Description

FK-3000 belongs to the class of organic compounds known as phenanthrenes and derivatives. These are polycyclic compounds containing a phenanthrene moiety, which is a tricyclic aromatic compound with three non-linearly fused benzene. (1s,9s)-12-(acetyloxy)-3-hydroxy-4,11-dimethoxy-17-azatetracyclo[7.5.3.0¹,¹⁰.0²,⁷]heptadeca-2,4,6,10-tetraen-13-yl acetate is found in Stephania cephalantha. (1s,9s)-12-(acetyloxy)-3-hydroxy-4,11-dimethoxy-17-azatetracyclo[7.5.3.0¹,¹⁰.0²,⁷]heptadeca-2,4,6,10-tetraen-13-yl acetate was first documented in 2012 (PMID: 22738786). Based on a literature review a small amount of articles have been published on FK-3000 (PMID: 25384584) (PMID: 25823424).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309082210182D          

 30 33  0  0  1  0            999 V2000
    1.2704   -1.0731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0221   -0.7331    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1092   -0.0286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4332    0.5689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8162   -0.3551    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6402   -0.3148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1944    0.2964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9281   -0.0807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6216    0.3662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5813    1.1903    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2747    1.6372    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0085    1.2601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8475    1.5673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8072    2.3914    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1540    1.1204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5146    1.3899    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7188    1.6342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1647    1.0230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2050    0.1990    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2663    1.7299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9366    1.2489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6883    1.5889    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7697    2.4099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0994    2.8908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5214    2.7499    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8552    0.4279    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5255   -0.0531    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4441   -0.8740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1144   -1.3550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6924   -1.2140    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
  5  4  1  1  0  0  0
  5  6  1  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
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 10 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  2  0  0  0  0
  7 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16  4  1  1  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
  5 19  1  0  0  0  0
 16 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
 23 24  1  0  0  0  0
 23 25  2  0  0  0  0
 21 26  1  0  0  0  0
  3 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 28 30  2  0  0  0  0
M  END

     RDKit          3D

 57 60  0  0  0  0  0  0  0  0999 V2000
   -2.7154   -2.8156   -2.1654 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9221   -2.5395   -1.0661 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4358   -1.3329   -0.6616 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2579   -0.9415   -1.0722 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5209   -1.8353   -1.9797 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8364   -2.1934   -1.3667 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3370   -1.1690   -0.4234 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5721   -1.4935    0.1592 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1895   -0.6549    1.0519 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5791    0.5237    1.3760 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1896    1.3944    2.2835 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4291    1.0567    2.8609 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3676    0.8289    0.7967 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7839    2.0206    1.1435 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7120    0.0094   -0.1080 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125    0.3390   -0.7285 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7579    1.0711   -2.0235 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3750    0.1202   -3.0257 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6585   -1.0952   -3.2208 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4279    1.2519    0.1037 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8933    1.0117   -0.1631 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7453    1.9280    0.4314 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6215    2.7248   -0.2657 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5343    3.7062    0.3685 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6327    2.5972   -1.5139 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2068   -0.4404    0.2382 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9576   -0.6337    1.5853 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9786   -0.9444    2.4622 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7309   -1.1589    3.9311 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1276   -1.0380    1.9643 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9123   -3.9283   -2.1671 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2424   -2.6115   -3.1467 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7066   -2.3380   -2.1722 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0284   -2.7984   -2.1511 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5852   -2.2359   -2.2107 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8284   -3.1700   -0.8437 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0916   -2.4148   -0.0676 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1571   -0.9121    1.5066 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7346    1.8535    3.5652 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2324    0.9261    2.1029 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3593    0.1051    3.4479 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1581    2.6911    1.7807 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5347    1.8161   -1.7584 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0842    1.5962   -2.4669 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4478   -0.0201   -2.7750 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3690    0.6709   -4.0124 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1002   -1.6225   -3.9787 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2039    2.2830   -0.1550 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2579    0.9711    1.1644 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0504    1.0466   -1.2607 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6287    3.4960    1.4723 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1219    4.7367    0.3027 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5414    3.7005   -0.0646 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2886   -0.5759    0.0445 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9945   -0.4094    4.2903 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6736   -0.9708    4.5008 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3972   -2.1827    4.0804 H   0  0  0  0  0  0  0  0  0  0  0  0
 12 11  1  0
 11 10  1  0
 10  9  2  0
  9  8  1  0
  8  7  2  0
  7  6  1  0
  6  5  1  0
  5 19  1  0
 19 18  1  0
 18 17  1  0
 16 17  1  6
 16 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 23 25  2  0
 21 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 28 30  2  0
 26  3  1  0
  3  2  1  0
  2  1  1  0
  3  4  2  0
 16 15  1  0
 15 13  2  0
 13 14  1  0
 13 10  1  0
 15  7  1  0
  4  5  1  0
  4 16  1  0
 12 39  1  0
 12 40  1  0
 12 41  1  0
  9 38  1  0
  8 37  1  0
  6 35  1  0
  6 36  1  0
  5 34  1  6
 19 47  1  0
 18 45  1  0
 18 46  1  0
 17 43  1  0
 17 44  1  0
 20 48  1  0
 20 49  1  0
 21 50  1  6
 24 51  1  0
 24 52  1  0
 24 53  1  0
 26 54  1  1
 29 55  1  0
 29 56  1  0
 29 57  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
 14 42  1  0
M  END


  Mrv1652309082210182D          

 30 33  0  0  1  0            999 V2000
    1.2704   -1.0731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0221   -0.7331    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1092   -0.0286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4332    0.5689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8162   -0.3551    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6402   -0.3148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1944    0.2964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9281   -0.0807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6216    0.3662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5813    1.1903    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2747    1.6372    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0085    1.2601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8475    1.5673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8072    2.3914    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1540    1.1204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5146    1.3899    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7188    1.6342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1647    1.0230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2050    0.1990    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2663    1.7299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9366    1.2489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6883    1.5889    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7697    2.4099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0994    2.8908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5214    2.7499    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8552    0.4279    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5255   -0.0531    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4441   -0.8740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1144   -1.3550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6924   -1.2140    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
  5  4  1  1  0  0  0
  5  6  1  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
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 10 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  2  0  0  0  0
  7 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16  4  1  1  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
  5 19  1  0  0  0  0
 16 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
 23 24  1  0  0  0  0
 23 25  2  0  0  0  0
 21 26  1  0  0  0  0
  3 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 28 30  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0264681

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC=C2C[C@@H]3NCC[C@]4(CC(OC(C)=O)C(OC(C)=O)C(OC)=C34)C2=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C22H27NO7/c1-11(24)29-16-10-22-7-8-23-14(18(22)21(28-4)20(16)30-12(2)25)9-13-5-6-15(27-3)19(26)17(13)22/h5-6,14,16,20,23,26H,7-10H2,1-4H3/t14-,16?,20?,22-/m0/s1

> <INCHI_KEY>
XAQZCUNTDGRIEM-ZOUNEDFCSA-N

> <FORMULA>
C22H27NO7

> <MOLECULAR_WEIGHT>
417.458

> <EXACT_MASS>
417.178752213

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
57

> <JCHEM_AVERAGE_POLARIZABILITY>
42.856353248399245

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,9S)-12-(acetyloxy)-3-hydroxy-4,11-dimethoxy-17-azatetracyclo[7.5.3.0^{1,10}.0^{2,7}]heptadeca-2,4,6,10-tetraen-13-yl acetate

> <JCHEM_LOGP>
0.053701487942434484

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.883910991228682

> <JCHEM_PKA_STRONGEST_BASIC>
9.016000924154067

> <JCHEM_POLAR_SURFACE_AREA>
103.32000000000002

> <JCHEM_REFRACTIVITY>
107.84589999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1S,9S)-12-(acetyloxy)-3-hydroxy-4,11-dimethoxy-17-azatetracyclo[7.5.3.0^{1,10}.0^{2,7}]heptadeca-2,4,6,10-tetraen-13-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 08-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-SEP-22         0                                  
HETATM    1  C   UNK     0       2.371  -2.003   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       3.775  -1.368   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       3.937  -0.053   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.675   1.062   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.524  -0.663   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.062  -0.588   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.096   0.553   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.466  -0.151   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.760   0.684   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.685   2.222   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       7.979   3.056   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       9.349   2.352   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.315   2.926   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       5.240   4.464   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       4.021   2.091   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.827   2.594   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.342   3.051   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.307   1.910   0.000  0.00  0.00           C+0
HETATM   19  N   UNK     0       0.383   0.372   0.000  0.00  0.00           N+0
HETATM   20  C   UNK     0       4.230   3.229   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.482   2.331   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       6.885   2.966   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       7.037   4.498   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       5.786   5.396   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       8.440   5.133   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       5.330   0.799   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       6.581  -0.099   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       6.429  -1.632   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       7.680  -2.529   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       5.026  -2.266   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   26                                                  
CONECT    4    3    5   16                                                  
CONECT    5    4    6   19                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   15                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   13                                                  
CONECT   11   10   12                                                       
CONECT   12   11                                                            
CONECT   13   10   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13    7   16                                                  
CONECT   16   15    4   17   20                                             
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18    5                                                       
CONECT   20   16   21                                                       
CONECT   21   20   22   26                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23                                                            
CONECT   26   21    3   27                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28                                                            
MASTER        0    0    0    0    0    0    0    0   30    0   66    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₂H₂₇NO₇

Average Mass

417.4580 Da

Monoisotopic Mass

417.17875 Da

IUPAC Name

(1S,9S)-12-(acetyloxy)-3-hydroxy-4,11-dimethoxy-17-azatetracyclo[7.5.3.0^{1,10}.0^{2,7}]heptadeca-2,4,6,10-tetraen-13-yl acetate

Traditional Name

(1S,9S)-12-(acetyloxy)-3-hydroxy-4,11-dimethoxy-17-azatetracyclo[7.5.3.0^{1,10}.0^{2,7}]heptadeca-2,4,6,10-tetraen-13-yl acetate

CAS Registry Number

Not Available

SMILES

COC1=CC=C2C[C@@H]3NCC[C@]4(CC(OC(C)=O)C(OC(C)=O)C(OC)=C34)C2=C1O

InChI Identifier

InChI=1S/C22H27NO7/c1-11(24)29-16-10-22-7-8-23-14(18(22)21(28-4)20(16)30-12(2)25)9-13-5-6-15(27-3)19(26)17(13)22/h5-6,14,16,20,23,26H,7-10H2,1-4H3/t14-,16?,20?,22-/m0/s1

InChI Key

XAQZCUNTDGRIEM-ZOUNEDFCSA-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

Species Name	Source	Reference
Stephania cephalantha	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenanthrenes and derivatives. These are polycyclic compounds containing a phenanthrene moiety, which is a tricyclic aromatic compound with three non-linearly fused benzene.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Phenanthrenes and derivatives

Sub Class

Not Available

Direct Parent

Phenanthrenes and derivatives

Alternative Parents

Substituents

Phenanthrene
Benzazocine
Tetralin
Anisole
1-hydroxy-4-unsubstituted benzenoid
Aralkylamine
Alkyl aryl ether
Piperidine
Dicarboxylic acid or derivatives
Carboxylic acid ester
Amino acid or derivatives
Azacycle
Organoheterocyclic compound
Secondary amine
Ether
Secondary aliphatic amine
Carboxylic acid derivative
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Carbonyl group
Amine
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

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

Predicted Properties

Property	Value	Source
logP	0.054	ChemAxon
pKa (Strongest Acidic)	9.88	ChemAxon
pKa (Strongest Basic)	9.02	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	103.32 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	107.85 m³·mol⁻¹	ChemAxon
Polarizability	42.86 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	Yes	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

34520958

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5495847

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Li YC, Kim BH, Cho SC, Bang MA, Kim S, Park DH: 6,7-di-O-acetylsinococuline (FK-3000) induces G2/M phase arrest in breast carcinomas through p38 MAPK phosphorylation and CDC25B dephosphorylation. Int J Oncol. 2015 Feb;46(2):578-86. doi: 10.3892/ijo.2014.2739. Epub 2014 Nov 7. [PubMed:25384584 ]
Xu HD, Cho SC, Bang MA, Bae CS, Choi Y, Li YC, Lim SK, Shim J, Park DH: FK-3000 isolated from Stephania delavayi Diels. inhibits MDA-MB-231 cell proliferation by decreasing NF-kappaB phosphorylation and COX-2 expression. Int J Oncol. 2015;46(6):2309-16. doi: 10.3892/ijo.2015.2940. Epub 2015 Mar 27. [PubMed:25823424 ]
Lee JH, Chae YJ, Lee KR, Ahn SH, Seo JW, Jin QR, Woo YA, Lee GW, Cho SC, Kwon SW, Park DH: Development of a LC-MS method for quantification of FK-3000 and its application to in vivo pharmacokinetic study in drug development. J Pharm Biomed Anal. 2012 Nov;70:587-91. doi: 10.1016/j.jpba.2012.05.030. Epub 2012 Jun 4. [PubMed:22738786 ]
LOTUS database [Link]

Showing NP-Card for (1s,9s)-12-(acetyloxy)-3-hydroxy-4,11-dimethoxy-17-azatetracyclo[7.5.3.0¹,¹⁰.0²,⁷]heptadeca-2,4,6,10-tetraen-13-yl acetate (NP0264681)

MOL for NP0264681 ((1s,9s)-12-(acetyloxy)-3-hydroxy-4,11-dimethoxy-17-azatetracyclo[7.5.3.0¹,¹⁰.0²,⁷]heptadeca-2,4,6,10-tetraen-13-yl acetate)

3D MOL for NP0264681 ((1s,9s)-12-(acetyloxy)-3-hydroxy-4,11-dimethoxy-17-azatetracyclo[7.5.3.0¹,¹⁰.0²,⁷]heptadeca-2,4,6,10-tetraen-13-yl acetate)

3D SDF for NP0264681 ((1s,9s)-12-(acetyloxy)-3-hydroxy-4,11-dimethoxy-17-azatetracyclo[7.5.3.0¹,¹⁰.0²,⁷]heptadeca-2,4,6,10-tetraen-13-yl acetate)

3D-SDF for NP0264681 ((1s,9s)-12-(acetyloxy)-3-hydroxy-4,11-dimethoxy-17-azatetracyclo[7.5.3.0¹,¹⁰.0²,⁷]heptadeca-2,4,6,10-tetraen-13-yl acetate)

PDB for NP0264681 ((1s,9s)-12-(acetyloxy)-3-hydroxy-4,11-dimethoxy-17-azatetracyclo[7.5.3.0¹,¹⁰.0²,⁷]heptadeca-2,4,6,10-tetraen-13-yl acetate)

3D PDB for NP0264681 ((1s,9s)-12-(acetyloxy)-3-hydroxy-4,11-dimethoxy-17-azatetracyclo[7.5.3.0¹,¹⁰.0²,⁷]heptadeca-2,4,6,10-tetraen-13-yl acetate)

SMILES for NP0264681 ((1s,9s)-12-(acetyloxy)-3-hydroxy-4,11-dimethoxy-17-azatetracyclo[7.5.3.0¹,¹⁰.0²,⁷]heptadeca-2,4,6,10-tetraen-13-yl acetate)

INCHI for NP0264681 ((1s,9s)-12-(acetyloxy)-3-hydroxy-4,11-dimethoxy-17-azatetracyclo[7.5.3.0¹,¹⁰.0²,⁷]heptadeca-2,4,6,10-tetraen-13-yl acetate)

Structure for NP0264681 ((1s,9s)-12-(acetyloxy)-3-hydroxy-4,11-dimethoxy-17-azatetracyclo[7.5.3.0¹,¹⁰.0²,⁷]heptadeca-2,4,6,10-tetraen-13-yl acetate)

3D Structure for NP0264681 ((1s,9s)-12-(acetyloxy)-3-hydroxy-4,11-dimethoxy-17-azatetracyclo[7.5.3.0¹,¹⁰.0²,⁷]heptadeca-2,4,6,10-tetraen-13-yl acetate)