NP-MRD: Showing NP-Card for [(3r,14r,16s)-12-hydroxy-3-[(1s)-1-hydroxyethyl]-14-methyl-10-oxo-15-oxa-2-azapentacyclo[9.7.1.0²,⁶.0⁷,¹⁹.0¹³,¹⁸]nonadeca-6,8,11(19),12-tetraen-16-yl]acetic acid (NP0169508)

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Record Information

Version

2.0

Created at

2022-09-03 05:28:23 UTC

Updated at

2022-09-03 05:28:23 UTC

NP-MRD ID

NP0169508

Secondary Accession Numbers

None

Natural Product Identification

Common Name

[(3r,14r,16s)-12-hydroxy-3-[(1s)-1-hydroxyethyl]-14-methyl-10-oxo-15-oxa-2-azapentacyclo[9.7.1.0²,⁶.0⁷,¹⁹.0¹³,¹⁸]nonadeca-6,8,11(19),12-tetraen-16-yl]acetic acid

Description

2-[(3R,14R,16S)-12-hydroxy-3-[(1S)-1-hydroxyethyl]-14-methyl-10-oxo-15-oxa-2-azapentacyclo[9.7.1.0²,⁶.0⁷,¹⁹.0¹³,¹⁸]Nonadeca-6,8,11(19),12-tetraen-16-yl]acetic acid belongs to the class of organic compounds known as naphthopyrans. Naphthopyrans are compounds containing a pyran ring fused to a naphthalene moiety. Furan is a 6 membered-ring non-aromatic ring with five carbon and one oxygen atoms. Naphthalene is a polycyclic aromatic hydrocarbon made up of two fused benzene rings. Based on a literature review very few articles have been published on 2-[(3R,14R,16S)-12-hydroxy-3-[(1S)-1-hydroxyethyl]-14-methyl-10-oxo-15-oxa-2-azapentacyclo[9.7.1.0²,⁶.0⁷,¹⁹.0¹³,¹⁸]Nonadeca-6,8,11(19),12-tetraen-16-yl]acetic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309032207282D          

 29 33  0  0  1  0            999 V2000
    1.8040   -2.2971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2281   -1.5895    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0530   -1.6029    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8273   -0.8684    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0084   -0.7687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8500    0.0409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5712    0.4417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9190    1.1898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5958    1.9489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0915    2.6083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9105    2.5087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4063    3.1681    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2337    1.7496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7379    1.0902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8963    0.2805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6766    0.0128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8349   -0.7969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6153   -1.0646    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.7736   -1.8743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1516   -2.4162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3099   -3.2259    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3712   -2.1485    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2373   -0.5227    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0790    0.2870    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.7010    0.8289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2987    0.5547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1403    1.3644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7813    1.8838    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1752   -0.1203    0.0000 N   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
  4  2  1  1  0  0  0
  4  5  1  0  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  2  0  0  0  0
 11 13  1  0  0  0  0
 13 14  2  0  0  0  0
  8 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  6  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
 18 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  1  0  0  0
 24 26  1  0  0  0  0
 16 26  1  0  0  0  0
 26 27  2  0  0  0  0
 13 27  1  0  0  0  0
 27 28  1  0  0  0  0
 15 29  1  0  0  0  0
  7 29  1  0  0  0  0
  4 29  1  0  0  0  0
M  END

     RDKit          3D

 54 58  0  0  0  0  0  0  0  0999 V2000
   -1.6756   -2.7865    1.3826 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4667   -2.3216    0.2280 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9325   -2.6827   -0.9898 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9789   -0.9294    0.2506 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.5517   -0.5578    1.6027 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8531    0.9267    1.3015 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5775    1.3107    0.6368 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7490    2.3207    0.4887 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6498    3.7254    0.9510 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5999    4.4845    0.6115 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4815    3.9199   -0.2310 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4836    4.5954   -0.5723 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4096    2.5468   -0.6923 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6496    1.8790   -0.3271 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9518    0.5590   -0.8514 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1853   -0.2654   -1.1419 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8364   -1.0316   -0.0092 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3500   -0.9748   -0.1481 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0681   -1.9184    0.7613 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8430   -1.7023    2.1996 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1209   -0.7621    2.5937 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4176   -2.5242    3.1393 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8008   -1.2003   -1.4376 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3565   -0.2583   -2.3710 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4572    0.5189   -2.9704 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3516    0.5523   -1.6579 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4851    1.8293   -1.4162 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5828    2.5646   -1.7989 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0899    0.1410   -0.0721 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2907   -3.3823    2.1240 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1986   -1.9969    1.9955 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8916   -3.5334    1.0650 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4351   -2.9764    0.2639 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5423   -2.6082   -1.7421 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8884   -0.8720   -0.4438 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7998   -0.5436    2.4049 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4732   -1.0971    1.8345 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0187    1.4920    2.2360 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7064    1.0381    0.6329 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4496    4.1045    1.5646 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5218    5.5106    0.9412 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4261    0.8052   -1.9110 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0212   -1.0032   -1.9682 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5055   -0.6917    0.9728 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5839   -2.0982   -0.1388 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6375    0.0616    0.1194 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8580   -2.9889    0.4800 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1831   -1.8364    0.6152 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9665   -3.3937    3.4282 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8591   -0.8485   -3.1770 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0178    1.2595   -3.6817 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0427   -0.1773   -3.6414 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1914    0.9435   -2.2790 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3137    2.8739   -1.1556 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 22  1  0
 20 21  2  0
 18 23  1  0
 23 24  1  0
 24 25  1  0
 24 26  1  0
 26 27  2  0
 27 28  1  0
 15 29  1  0
 29  4  1  0
 29  7  1  0
 14  8  1  0
 26 16  1  0
 27 13  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  2 33  1  1
  3 34  1  0
  4 35  1  6
  5 36  1  0
  5 37  1  0
  6 38  1  0
  6 39  1  0
  9 40  1  0
 10 41  1  0
 15 42  1  6
 16 43  1  6
 17 44  1  0
 17 45  1  0
 18 46  1  1
 19 47  1  0
 19 48  1  0
 22 49  1  0
 24 50  1  6
 25 51  1  0
 25 52  1  0
 25 53  1  0
 28 54  1  0
M  END


  Mrv1652309032207282D          

 29 33  0  0  1  0            999 V2000
    1.8040   -2.2971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2281   -1.5895    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0530   -1.6029    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8273   -0.8684    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0084   -0.7687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8500    0.0409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5712    0.4417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9190    1.1898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5958    1.9489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0915    2.6083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9105    2.5087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4063    3.1681    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2337    1.7496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7379    1.0902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8963    0.2805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6766    0.0128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8349   -0.7969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6153   -1.0646    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.7736   -1.8743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1516   -2.4162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3099   -3.2259    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3712   -2.1485    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2373   -0.5227    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0790    0.2870    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.7010    0.8289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2987    0.5547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1403    1.3644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7813    1.8838    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1752   -0.1203    0.0000 N   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
  4  2  1  1  0  0  0
  4  5  1  0  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  2  0  0  0  0
 11 13  1  0  0  0  0
 13 14  2  0  0  0  0
  8 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  6  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
 18 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  1  0  0  0
 24 26  1  0  0  0  0
 16 26  1  0  0  0  0
 26 27  2  0  0  0  0
 13 27  1  0  0  0  0
 27 28  1  0  0  0  0
 15 29  1  0  0  0  0
  7 29  1  0  0  0  0
  4 29  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0169508

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H](O)[C@H]1CCC2=C3C=CC(=O)C4=C3C(C3C[C@@H](CC(O)=O)O[C@H](C)C3=C4O)N12

> <INCHI_IDENTIFIER>
InChI=1S/C22H25NO6/c1-9(24)14-4-5-15-12-3-6-16(25)20-19(12)21(23(14)15)13-7-11(8-17(26)27)29-10(2)18(13)22(20)28/h3,6,9-11,13-14,21,24,28H,4-5,7-8H2,1-2H3,(H,26,27)/t9-,10+,11-,13?,14+,21?/m0/s1

> <INCHI_KEY>
VUWWFEJXASWGTA-ONRPBGGJSA-N

> <FORMULA>
C22H25NO6

> <MOLECULAR_WEIGHT>
399.443

> <EXACT_MASS>
399.168187529

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
54

> <JCHEM_AVERAGE_POLARIZABILITY>
42.135503405660636

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-[(3R,14R,16S)-12-hydroxy-3-[(1S)-1-hydroxyethyl]-14-methyl-10-oxo-15-oxa-2-azapentacyclo[9.7.1.0^{2,6}.0^{7,19}.0^{13,18}]nonadeca-6,8,11(19),12-tetraen-16-yl]acetic acid

> <ALOGPS_LOGP>
0.89

> <JCHEM_LOGP>
-2.8251204434128203

> <ALOGPS_LOGS>
-2.74

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
7.159659048870359

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.791450514042227

> <JCHEM_PKA_STRONGEST_BASIC>
9.143568740069393

> <JCHEM_POLAR_SURFACE_AREA>
107.3

> <JCHEM_REFRACTIVITY>
108.18029999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.31e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[(3R,14R,16S)-12-hydroxy-3-[(1S)-1-hydroxyethyl]-14-methyl-10-oxo-15-oxa-2-azapentacyclo[9.7.1.0^{2,6}.0^{7,19}.0^{13,18}]nonadeca-6,8,11(19),12-tetraen-16-yl]acetic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 03-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-SEP-22         0                                  
HETATM    1  C   UNK     0       3.367  -4.288   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.159  -2.967   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       5.699  -2.992   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       3.411  -1.621   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.882  -1.435   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.587   0.076   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.933   0.825   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.582   2.221   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.979   3.638   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.904   4.869   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.433   4.683   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       6.358   5.914   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       6.036   3.266   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.111   2.035   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.406   0.524   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.863   0.024   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.159  -1.488   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.615  -1.987   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.911  -3.499   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       7.750  -4.510   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       8.045  -6.022   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       6.293  -4.011   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       9.776  -0.976   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       9.481   0.536   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      10.642   1.547   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       8.024   1.035   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       7.729   2.547   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       8.925   3.516   0.000  0.00  0.00           O+0
HETATM   29  N   UNK     0       4.060  -0.224   0.000  0.00  0.00           N+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   29                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   29                                                  
CONECT    8    7    9   14                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   27                                                  
CONECT   14   13    8   15                                                  
CONECT   15   14   16   29                                                  
CONECT   16   15   17   26                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   23                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20                                                            
CONECT   23   18   24                                                       
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   16   27                                                  
CONECT   27   26   13   28                                                  
CONECT   28   27                                                            
CONECT   29   15    7    4                                                  
MASTER        0    0    0    0    0    0    0    0   29    0   66    0
END

View in JSmol

Synonyms

Value	Source
2-[(3R,14R,16S)-12-Hydroxy-3-[(1S)-1-hydroxyethyl]-14-methyl-10-oxo-15-oxa-2-azapentacyclo[9.7.1.0,.0,.0,]nonadeca-6,8,11(19),12-tetraen-16-yl]acetate	Generator

Chemical Formula

C₂₂H₂₅NO₆

Average Mass

399.4430 Da

Monoisotopic Mass

399.16819 Da

IUPAC Name

2-[(3R,14R,16S)-12-hydroxy-3-[(1S)-1-hydroxyethyl]-14-methyl-10-oxo-15-oxa-2-azapentacyclo[9.7.1.0^{2,6}.0^{7,19}.0^{13,18}]nonadeca-6,8,11(19),12-tetraen-16-yl]acetic acid

Traditional Name

[(3R,14R,16S)-12-hydroxy-3-[(1S)-1-hydroxyethyl]-14-methyl-10-oxo-15-oxa-2-azapentacyclo[9.7.1.0^{2,6}.0^{7,19}.0^{13,18}]nonadeca-6,8,11(19),12-tetraen-16-yl]acetic acid

CAS Registry Number

Not Available

SMILES

C[C@H](O)[C@H]1CCC2=C3C=CC(=O)C4=C3C(C3C[C@@H](CC(O)=O)O[C@H](C)C3=C4O)N12

InChI Identifier

InChI=1S/C22H25NO6/c1-9(24)14-4-5-15-12-3-6-16(25)20-19(12)21(23(14)15)13-7-11(8-17(26)27)29-10(2)18(13)22(20)28/h3,6,9-11,13-14,21,24,28H,4-5,7-8H2,1-2H3,(H,26,27)/t9-,10+,11-,13?,14+,21?/m0/s1

InChI Key

VUWWFEJXASWGTA-ONRPBGGJSA-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 naphthopyrans. Naphthopyrans are compounds containing a pyran ring fused to a naphthalene moiety. Furan is a 6 membered-ring non-aromatic ring with five 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

Naphthopyrans

Sub Class

Not Available

Direct Parent

Naphthopyrans

Alternative Parents

Substituents

Naphthopyran
Naphthalene
Isoindole or derivatives
Indole or derivatives
N-alkylpyrrolidine
Pyran
Oxane
Pyrroline
Pyrrolidine
Amino acid
Tertiary aliphatic amine
Tertiary amine
Secondary alcohol
Ketone
Amino acid or derivatives
1,2-aminoalcohol
Oxacycle
Azacycle
Monocarboxylic acid or derivatives
Ether
Enol
Enamine
Dialkyl ether
Carboxylic acid
Carboxylic acid derivative
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Carbonyl group
Amine
Alcohol
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic 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	0.89	ALOGPS
logP	-2.8	ChemAxon
logS	-2.7	ALOGPS
pKa (Strongest Acidic)	3.79	ChemAxon
pKa (Strongest Basic)	9.14	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	107.3 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	108.18 m³·mol⁻¹	ChemAxon
Polarizability	42.14 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

163114627

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for [(3r,14r,16s)-12-hydroxy-3-[(1s)-1-hydroxyethyl]-14-methyl-10-oxo-15-oxa-2-azapentacyclo[9.7.1.0²,⁶.0⁷,¹⁹.0¹³,¹⁸]nonadeca-6,8,11(19),12-tetraen-16-yl]acetic acid (NP0169508)

MOL for NP0169508 ([(3r,14r,16s)-12-hydroxy-3-[(1s)-1-hydroxyethyl]-14-methyl-10-oxo-15-oxa-2-azapentacyclo[9.7.1.0²,⁶.0⁷,¹⁹.0¹³,¹⁸]nonadeca-6,8,11(19),12-tetraen-16-yl]acetic acid)

3D MOL for NP0169508 ([(3r,14r,16s)-12-hydroxy-3-[(1s)-1-hydroxyethyl]-14-methyl-10-oxo-15-oxa-2-azapentacyclo[9.7.1.0²,⁶.0⁷,¹⁹.0¹³,¹⁸]nonadeca-6,8,11(19),12-tetraen-16-yl]acetic acid)

3D SDF for NP0169508 ([(3r,14r,16s)-12-hydroxy-3-[(1s)-1-hydroxyethyl]-14-methyl-10-oxo-15-oxa-2-azapentacyclo[9.7.1.0²,⁶.0⁷,¹⁹.0¹³,¹⁸]nonadeca-6,8,11(19),12-tetraen-16-yl]acetic acid)

3D-SDF for NP0169508 ([(3r,14r,16s)-12-hydroxy-3-[(1s)-1-hydroxyethyl]-14-methyl-10-oxo-15-oxa-2-azapentacyclo[9.7.1.0²,⁶.0⁷,¹⁹.0¹³,¹⁸]nonadeca-6,8,11(19),12-tetraen-16-yl]acetic acid)

PDB for NP0169508 ([(3r,14r,16s)-12-hydroxy-3-[(1s)-1-hydroxyethyl]-14-methyl-10-oxo-15-oxa-2-azapentacyclo[9.7.1.0²,⁶.0⁷,¹⁹.0¹³,¹⁸]nonadeca-6,8,11(19),12-tetraen-16-yl]acetic acid)

3D PDB for NP0169508 ([(3r,14r,16s)-12-hydroxy-3-[(1s)-1-hydroxyethyl]-14-methyl-10-oxo-15-oxa-2-azapentacyclo[9.7.1.0²,⁶.0⁷,¹⁹.0¹³,¹⁸]nonadeca-6,8,11(19),12-tetraen-16-yl]acetic acid)

SMILES for NP0169508 ([(3r,14r,16s)-12-hydroxy-3-[(1s)-1-hydroxyethyl]-14-methyl-10-oxo-15-oxa-2-azapentacyclo[9.7.1.0²,⁶.0⁷,¹⁹.0¹³,¹⁸]nonadeca-6,8,11(19),12-tetraen-16-yl]acetic acid)

INCHI for NP0169508 ([(3r,14r,16s)-12-hydroxy-3-[(1s)-1-hydroxyethyl]-14-methyl-10-oxo-15-oxa-2-azapentacyclo[9.7.1.0²,⁶.0⁷,¹⁹.0¹³,¹⁸]nonadeca-6,8,11(19),12-tetraen-16-yl]acetic acid)

Structure for NP0169508 ([(3r,14r,16s)-12-hydroxy-3-[(1s)-1-hydroxyethyl]-14-methyl-10-oxo-15-oxa-2-azapentacyclo[9.7.1.0²,⁶.0⁷,¹⁹.0¹³,¹⁸]nonadeca-6,8,11(19),12-tetraen-16-yl]acetic acid)

3D Structure for NP0169508 ([(3r,14r,16s)-12-hydroxy-3-[(1s)-1-hydroxyethyl]-14-methyl-10-oxo-15-oxa-2-azapentacyclo[9.7.1.0²,⁶.0⁷,¹⁹.0¹³,¹⁸]nonadeca-6,8,11(19),12-tetraen-16-yl]acetic acid)