NP-MRD: Showing NP-Card for (2s,3r,6s,8s,9r,12s,15s,22r)-12-hydroxy-8-(2-hydroxypropan-2-yl)-2,3,23,23,25,25-hexamethyl-7,24-dioxa-31-azaoctacyclo[15.14.0.0²,¹⁵.0³,¹².0⁶,¹¹.0¹⁸,³⁰.0²⁰,²⁸.0²²,²⁷]hentriaconta-1(17),10,18,20(28),26,29-hexaen-9-yl acetate (NP0223600)

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Record Information

Version

2.0

Created at

2022-09-06 01:44:30 UTC

Updated at

2022-09-06 01:44:30 UTC

NP-MRD ID

NP0223600

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2s,3r,6s,8s,9r,12s,15s,22r)-12-hydroxy-8-(2-hydroxypropan-2-yl)-2,3,23,23,25,25-hexamethyl-7,24-dioxa-31-azaoctacyclo[15.14.0.0²,¹⁵.0³,¹².0⁶,¹¹.0¹⁸,³⁰.0²⁰,²⁸.0²²,²⁷]hentriaconta-1(17),10,18,20(28),26,29-hexaen-9-yl acetate

Description

(2S,3R,6S,8S,9R,12S,15S,22R)-12-hydroxy-8-(2-hydroxypropan-2-yl)-2,3,23,23,25,25-hexamethyl-7,24-dioxa-31-azaoctacyclo[15.14.0.0²,¹⁵.0³,¹².0⁶,¹¹.0¹⁸,³⁰.0²⁰,²⁸.0²²,²⁷]Hentriaconta-1(17),10,18(30),19,26,28-hexaen-9-yl acetate 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. (2s,3r,6s,8s,9r,12s,15s,22r)-12-hydroxy-8-(2-hydroxypropan-2-yl)-2,3,23,23,25,25-hexamethyl-7,24-dioxa-31-azaoctacyclo[15.14.0.0²,¹⁵.0³,¹².0⁶,¹¹.0¹⁸,³⁰.0²⁰,²⁸.0²²,²⁷]hentriaconta-1(17),10,18,20(28),26,29-hexaen-9-yl acetate is found in Penicillium janthinellum. Based on a literature review very few articles have been published on (2S,3R,6S,8S,9R,12S,15S,22R)-12-hydroxy-8-(2-hydroxypropan-2-yl)-2,3,23,23,25,25-hexamethyl-7,24-dioxa-31-azaoctacyclo[15.14.0.0²,¹⁵.0³,¹².0⁶,¹¹.0¹⁸,³⁰.0²⁰,²⁸.0²²,²⁷]Hentriaconta-1(17),10,18(30),19,26,28-hexaen-9-yl acetate.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309062203442D          

 46 53  0  0  1  0            999 V2000
   -7.2319   -5.0327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9366   -4.6038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6605   -4.9996    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9176   -3.7790    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1938   -3.3831    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.4890   -3.8120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7652   -3.4161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7462   -2.5913    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.0223   -2.1954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3176   -2.6243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3367   -3.4491    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.6128   -3.0532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0605   -3.8450    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.7843   -4.2409    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0795   -4.6698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3748   -5.0987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6510   -4.7028    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8724   -4.9758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3722   -4.3197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8416   -3.6413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3414   -2.9852    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5629   -3.2582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8391   -2.8623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1343   -3.2912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1534   -4.1160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8772   -4.5119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5819   -4.0830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6252   -4.3890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1254   -3.7329    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6560   -3.0545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0089   -2.3087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8311   -2.2415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6221   -1.4434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5808   -1.8971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3005   -2.9199    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9476   -3.6657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6806   -4.0444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0435   -4.4851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6319   -3.8780    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.2790   -3.1323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4509   -2.1624    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1747   -2.5583    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -7.8795   -2.1294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5842   -1.7005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3084   -2.8342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4506   -1.4247    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  5  4  1  1  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  1  0  0  0
 11 13  1  0  0  0  0
  7 13  1  0  0  0  0
 13 14  1  6  0  0  0
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 17 18  1  6  0  0  0
 18 19  1  0  0  0  0
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 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
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 26 27  2  0  0  0  0
 19 27  1  0  0  0  0
 22 27  1  0  0  0  0
 25 28  1  0  0  0  0
 29 28  1  6  0  0  0
 29 30  1  0  0  0  0
 24 30  1  0  0  0  0
 30 31  2  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 32 34  1  0  0  0  0
 32 35  1  0  0  0  0
 35 36  1  0  0  0  0
 29 36  1  0  0  0  0
 36 37  1  0  0  0  0
 36 38  1  0  0  0  0
 20 39  1  0  0  0  0
 17 39  1  0  0  0  0
 11 39  1  0  0  0  0
 39 40  1  6  0  0  0
  8 41  1  1  0  0  0
 41 42  1  0  0  0  0
  5 42  1  0  0  0  0
 42 43  1  1  0  0  0
 43 44  1  0  0  0  0
 43 45  1  0  0  0  0
 43 46  1  0  0  0  0
M  END


  Mrv1652309062203442D          

 46 53  0  0  1  0            999 V2000
   -7.2319   -5.0327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9366   -4.6038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6605   -4.9996    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9176   -3.7790    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1938   -3.3831    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.4890   -3.8120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7652   -3.4161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7462   -2.5913    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.0223   -2.1954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3176   -2.6243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3367   -3.4491    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.6128   -3.0532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0605   -3.8450    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.7843   -4.2409    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0795   -4.6698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3748   -5.0987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6510   -4.7028    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8724   -4.9758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3722   -4.3197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8416   -3.6413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3414   -2.9852    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5629   -3.2582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8391   -2.8623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1343   -3.2912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1534   -4.1160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8772   -4.5119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5819   -4.0830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6252   -4.3890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1254   -3.7329    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6560   -3.0545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0089   -2.3087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8311   -2.2415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6221   -1.4434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5808   -1.8971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3005   -2.9199    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9476   -3.6657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6806   -4.0444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0435   -4.4851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6319   -3.8780    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.2790   -3.1323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4509   -2.1624    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1747   -2.5583    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -7.8795   -2.1294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5842   -1.7005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3084   -2.8342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4506   -1.4247    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  5  4  1  1  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  1  0  0  0
 11 13  1  0  0  0  0
  7 13  1  0  0  0  0
 13 14  1  6  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  6  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 19 27  1  0  0  0  0
 22 27  1  0  0  0  0
 25 28  1  0  0  0  0
 29 28  1  6  0  0  0
 29 30  1  0  0  0  0
 24 30  1  0  0  0  0
 30 31  2  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 32 34  1  0  0  0  0
 32 35  1  0  0  0  0
 35 36  1  0  0  0  0
 29 36  1  0  0  0  0
 36 37  1  0  0  0  0
 36 38  1  0  0  0  0
 20 39  1  0  0  0  0
 17 39  1  0  0  0  0
 11 39  1  0  0  0  0
 39 40  1  6  0  0  0
  8 41  1  1  0  0  0
 41 42  1  0  0  0  0
  5 42  1  0  0  0  0
 42 43  1  1  0  0  0
 43 44  1  0  0  0  0
 43 45  1  0  0  0  0
 43 46  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0223600

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)O[C@@H]1C=C2[C@H](CC[C@]3(C)[C@]4(C)[C@H](CC5=C4NC4=CC6=C(C[C@@H]7C6=CC(C)(C)OC7(C)C)C=C54)CC[C@@]23O)O[C@@H]1C(C)(C)O

> <INCHI_IDENTIFIER>
InChI=1S/C39H51NO6/c1-20(41)44-31-18-28-30(45-33(31)35(4,5)42)11-12-37(8)38(9)22(10-13-39(28,37)43)16-25-24-14-21-15-27-26(19-34(2,3)46-36(27,6)7)23(21)17-29(24)40-32(25)38/h14,17-19,22,27,30-31,33,40,42-43H,10-13,15-16H2,1-9H3/t22-,27+,30-,31+,33-,37+,38+,39+/m0/s1

> <INCHI_KEY>
PGYSJEQVCATFBQ-YQENVTARSA-N

> <FORMULA>
C39H51NO6

> <MOLECULAR_WEIGHT>
629.838

> <EXACT_MASS>
629.371638366

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
97

> <JCHEM_AVERAGE_POLARIZABILITY>
74.95771602729619

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,3R,6S,8S,9R,12S,15S,22R)-12-hydroxy-8-(2-hydroxypropan-2-yl)-2,3,23,23,25,25-hexamethyl-7,24-dioxa-31-azaoctacyclo[15.14.0.0^{2,15}.0^{3,12}.0^{6,11}.0^{18,30}.0^{20,28}.0^{22,27}]hentriaconta-1(17),10,18,20(28),26,29-hexaen-9-yl acetate

> <JCHEM_LOGP>
5.1249896623333315

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
8

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.348608728093065

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.611570040393485

> <JCHEM_PKA_STRONGEST_BASIC>
-3.1357150032455516

> <JCHEM_POLAR_SURFACE_AREA>
101.01

> <JCHEM_REFRACTIVITY>
178.79440000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3R,6S,8S,9R,12S,15S,22R)-12-hydroxy-8-(2-hydroxypropan-2-yl)-2,3,23,23,25,25-hexamethyl-7,24-dioxa-31-azaoctacyclo[15.14.0.0^{2,15}.0^{3,12}.0^{6,11}.0^{18,30}.0^{20,28}.0^{22,27}]hentriaconta-1(17),10,18,20(28),26,29-hexaen-9-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-22         0                                  
HETATM    1  C   UNK     0     -13.500  -9.394   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0     -14.815  -8.594   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0     -16.166  -9.333   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0     -14.779  -7.054   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0     -13.428  -6.315   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0     -12.113  -7.116   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0     -10.762  -6.377   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0     -10.726  -4.837   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -9.375  -4.098   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -8.060  -4.899   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -8.095  -6.438   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -6.744  -5.699   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -9.446  -7.177   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0     -10.797  -7.916   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      -9.482  -8.717   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -8.166  -9.518   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -6.815  -8.779   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -5.362  -9.288   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -4.428  -8.063   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -5.304  -6.797   0.000  0.00  0.00           C+0
HETATM   21  N   UNK     0      -4.371  -5.572   0.000  0.00  0.00           N+0
HETATM   22  C   UNK     0      -2.917  -6.082   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -1.566  -5.343   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -0.251  -6.144   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -0.286  -7.683   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -1.637  -8.422   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -2.953  -7.622   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       1.167  -8.193   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       2.101  -6.968   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       1.225  -5.702   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       1.883  -4.310   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       3.418  -4.184   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       3.028  -2.694   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       4.817  -3.541   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       4.294  -5.451   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0       3.636  -6.843   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       5.004  -7.549   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       3.815  -8.372   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      -6.780  -7.239   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      -6.121  -5.847   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0     -12.042  -4.037   0.000  0.00  0.00           O+0
HETATM   42  C   UNK     0     -13.393  -4.776   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0     -14.708  -3.975   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0     -16.024  -3.174   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0     -15.509  -5.290   0.000  0.00  0.00           C+0
HETATM   46  O   UNK     0     -13.908  -2.659   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   42                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   13                                                  
CONECT    8    7    9   41                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   13   39                                             
CONECT   12   11                                                            
CONECT   13   11    7   14   15                                             
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   39                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   27                                                  
CONECT   20   19   21   39                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23   27                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25   30                                                  
CONECT   25   24   26   28                                                  
CONECT   26   25   27                                                       
CONECT   27   26   19   22                                                  
CONECT   28   25   29                                                       
CONECT   29   28   30   36                                                  
CONECT   30   29   24   31                                                  
CONECT   31   30   32                                                       
CONECT   32   31   33   34   35                                             
CONECT   33   32                                                            
CONECT   34   32                                                            
CONECT   35   32   36                                                       
CONECT   36   35   29   37   38                                             
CONECT   37   36                                                            
CONECT   38   36                                                            
CONECT   39   20   17   11   40                                             
CONECT   40   39                                                            
CONECT   41    8   42                                                       
CONECT   42   41    5   43                                                  
CONECT   43   42   44   45   46                                             
CONECT   44   43                                                            
CONECT   45   43                                                            
CONECT   46   43                                                            
MASTER        0    0    0    0    0    0    0    0   46    0  106    0
END

View in JSmol

Synonyms

Value	Source
(2S,3R,6S,8S,9R,12S,15S,22R)-12-Hydroxy-8-(2-hydroxypropan-2-yl)-2,3,23,23,25,25-hexamethyl-7,24-dioxa-31-azaoctacyclo[15.14.0.0,.0,.0,.0,.0,.0,]hentriaconta-1(17),10,18(30),19,26,28-hexaen-9-yl acetic acid	Generator

Chemical Formula

C₃₉H₅₁NO₆

Average Mass

629.8380 Da

Monoisotopic Mass

629.37164 Da

IUPAC Name

(2S,3R,6S,8S,9R,12S,15S,22R)-12-hydroxy-8-(2-hydroxypropan-2-yl)-2,3,23,23,25,25-hexamethyl-7,24-dioxa-31-azaoctacyclo[15.14.0.0^{2,15}.0^{3,12}.0^{6,11}.0^{18,30}.0^{20,28}.0^{22,27}]hentriaconta-1(17),10,18,20(28),26,29-hexaen-9-yl acetate

Traditional Name

CAS Registry Number

Not Available

SMILES

CC(=O)O[C@@H]1C=C2[C@H](CC[C@]3(C)[C@]4(C)[C@H](CC5=C4NC4=CC6=C(C[C@@H]7C6=CC(C)(C)OC7(C)C)C=C54)CC[C@@]23O)O[C@@H]1C(C)(C)O

InChI Identifier

InChI=1S/C39H51NO6/c1-20(41)44-31-18-28-30(45-33(31)35(4,5)42)11-12-37(8)38(9)22(10-13-39(28,37)43)16-25-24-14-21-15-27-26(19-34(2,3)46-36(27,6)7)23(21)17-29(24)40-32(25)38/h14,17-19,22,27,30-31,33,40,42-43H,10-13,15-16H2,1-9H3/t22-,27+,30-,31+,33-,37+,38+,39+/m0/s1

InChI Key

PGYSJEQVCATFBQ-YQENVTARSA-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
Penicillium janthinellum	LOTUS Database	35616633

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
3-alkylindole
Indane
Indole
Indole or derivatives
Benzenoid
Pyran
Cyclic alcohol
Heteroaromatic compound
Tertiary alcohol
Pyrrole
Carboxylic acid ester
Carboxylic acid derivative
Dialkyl ether
Ether
Monocarboxylic acid or derivatives
Oxacycle
Azacycle
Organic oxide
Organopnictogen compound
Carbonyl group
Hydrocarbon derivative
Alcohol
Organic nitrogen compound
Organic oxygen compound
Organonitrogen compound
Organooxygen 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	5.12	ChemAxon
pKa (Strongest Acidic)	13.61	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	101.01 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	178.79 m³·mol⁻¹	ChemAxon
Polarizability	74.96 Å³	ChemAxon
Number of Rings	8	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	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

163185744

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2s,3r,6s,8s,9r,12s,15s,22r)-12-hydroxy-8-(2-hydroxypropan-2-yl)-2,3,23,23,25,25-hexamethyl-7,24-dioxa-31-azaoctacyclo[15.14.0.0²,¹⁵.0³,¹².0⁶,¹¹.0¹⁸,³⁰.0²⁰,²⁸.0²²,²⁷]hentriaconta-1(17),10,18,20(28),26,29-hexaen-9-yl acetate (NP0223600)

MOL for NP0223600 ((2s,3r,6s,8s,9r,12s,15s,22r)-12-hydroxy-8-(2-hydroxypropan-2-yl)-2,3,23,23,25,25-hexamethyl-7,24-dioxa-31-azaoctacyclo[15.14.0.0²,¹⁵.0³,¹².0⁶,¹¹.0¹⁸,³⁰.0²⁰,²⁸.0²²,²⁷]hentriaconta-1(17),10,18,20(28),26,29-hexaen-9-yl acetate)

3D MOL for NP0223600 ((2s,3r,6s,8s,9r,12s,15s,22r)-12-hydroxy-8-(2-hydroxypropan-2-yl)-2,3,23,23,25,25-hexamethyl-7,24-dioxa-31-azaoctacyclo[15.14.0.0²,¹⁵.0³,¹².0⁶,¹¹.0¹⁸,³⁰.0²⁰,²⁸.0²²,²⁷]hentriaconta-1(17),10,18,20(28),26,29-hexaen-9-yl acetate)

3D SDF for NP0223600 ((2s,3r,6s,8s,9r,12s,15s,22r)-12-hydroxy-8-(2-hydroxypropan-2-yl)-2,3,23,23,25,25-hexamethyl-7,24-dioxa-31-azaoctacyclo[15.14.0.0²,¹⁵.0³,¹².0⁶,¹¹.0¹⁸,³⁰.0²⁰,²⁸.0²²,²⁷]hentriaconta-1(17),10,18,20(28),26,29-hexaen-9-yl acetate)

3D-SDF for NP0223600 ((2s,3r,6s,8s,9r,12s,15s,22r)-12-hydroxy-8-(2-hydroxypropan-2-yl)-2,3,23,23,25,25-hexamethyl-7,24-dioxa-31-azaoctacyclo[15.14.0.0²,¹⁵.0³,¹².0⁶,¹¹.0¹⁸,³⁰.0²⁰,²⁸.0²²,²⁷]hentriaconta-1(17),10,18,20(28),26,29-hexaen-9-yl acetate)

PDB for NP0223600 ((2s,3r,6s,8s,9r,12s,15s,22r)-12-hydroxy-8-(2-hydroxypropan-2-yl)-2,3,23,23,25,25-hexamethyl-7,24-dioxa-31-azaoctacyclo[15.14.0.0²,¹⁵.0³,¹².0⁶,¹¹.0¹⁸,³⁰.0²⁰,²⁸.0²²,²⁷]hentriaconta-1(17),10,18,20(28),26,29-hexaen-9-yl acetate)

3D PDB for NP0223600 ((2s,3r,6s,8s,9r,12s,15s,22r)-12-hydroxy-8-(2-hydroxypropan-2-yl)-2,3,23,23,25,25-hexamethyl-7,24-dioxa-31-azaoctacyclo[15.14.0.0²,¹⁵.0³,¹².0⁶,¹¹.0¹⁸,³⁰.0²⁰,²⁸.0²²,²⁷]hentriaconta-1(17),10,18,20(28),26,29-hexaen-9-yl acetate)

SMILES for NP0223600 ((2s,3r,6s,8s,9r,12s,15s,22r)-12-hydroxy-8-(2-hydroxypropan-2-yl)-2,3,23,23,25,25-hexamethyl-7,24-dioxa-31-azaoctacyclo[15.14.0.0²,¹⁵.0³,¹².0⁶,¹¹.0¹⁸,³⁰.0²⁰,²⁸.0²²,²⁷]hentriaconta-1(17),10,18,20(28),26,29-hexaen-9-yl acetate)

INCHI for NP0223600 ((2s,3r,6s,8s,9r,12s,15s,22r)-12-hydroxy-8-(2-hydroxypropan-2-yl)-2,3,23,23,25,25-hexamethyl-7,24-dioxa-31-azaoctacyclo[15.14.0.0²,¹⁵.0³,¹².0⁶,¹¹.0¹⁸,³⁰.0²⁰,²⁸.0²²,²⁷]hentriaconta-1(17),10,18,20(28),26,29-hexaen-9-yl acetate)

Structure for NP0223600 ((2s,3r,6s,8s,9r,12s,15s,22r)-12-hydroxy-8-(2-hydroxypropan-2-yl)-2,3,23,23,25,25-hexamethyl-7,24-dioxa-31-azaoctacyclo[15.14.0.0²,¹⁵.0³,¹².0⁶,¹¹.0¹⁸,³⁰.0²⁰,²⁸.0²²,²⁷]hentriaconta-1(17),10,18,20(28),26,29-hexaen-9-yl acetate)

3D Structure for NP0223600 ((2s,3r,6s,8s,9r,12s,15s,22r)-12-hydroxy-8-(2-hydroxypropan-2-yl)-2,3,23,23,25,25-hexamethyl-7,24-dioxa-31-azaoctacyclo[15.14.0.0²,¹⁵.0³,¹².0⁶,¹¹.0¹⁸,³⁰.0²⁰,²⁸.0²²,²⁷]hentriaconta-1(17),10,18,20(28),26,29-hexaen-9-yl acetate)