NP-MRD: Showing NP-Card for (1s,3ar,3br,4r,5ar,9ar,9br,11s,11as)-11-hydroxy-1-[(2s,3s,5r)-2-hydroxy-5-(hydroxymethyl)oxolan-3-yl]-3b,6,6,9a,11a-pentamethyl-7-oxo-1h,2h,3h,3ah,4h,5h,5ah,9bh,10h,11h-cyclopenta[a]phenanthren-4-yl (2e)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate (NP0152591)

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Record Information

Version

2.0

Created at

2022-09-02 09:06:24 UTC

Updated at

2022-09-02 09:06:24 UTC

NP-MRD ID

NP0152591

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,3ar,3br,4r,5ar,9ar,9br,11s,11as)-11-hydroxy-1-[(2s,3s,5r)-2-hydroxy-5-(hydroxymethyl)oxolan-3-yl]-3b,6,6,9a,11a-pentamethyl-7-oxo-1h,2h,3h,3ah,4h,5h,5ah,9bh,10h,11h-cyclopenta[a]phenanthren-4-yl (2e)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate

Description

(1R,2R,7R,9R,10R,11R,14S,15S,16S)-16-hydroxy-14-[(2S,3S,5R)-2-hydroxy-5-(hydroxymethyl)oxolan-3-yl]-2,6,6,10,15-pentamethyl-5-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadec-3-en-9-yl (2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate belongs to the class of organic compounds known as limonoids. These are highly oxygenated, modified terpenoids with a prototypical structure either containing or derived from a precursor with a 4,4,8-trimethyl-17-furanylsteroid skeleton. All naturally occurring citrus limonoids contain a furan ring attached to the D-ring, at C-17, as well as oxygen containing functional groups at C-3, C-4, C-7, C-16 and C-17. (1s,3ar,3br,4r,5ar,9ar,9br,11s,11as)-11-hydroxy-1-[(2s,3s,5r)-2-hydroxy-5-(hydroxymethyl)oxolan-3-yl]-3b,6,6,9a,11a-pentamethyl-7-oxo-1h,2h,3h,3ah,4h,5h,5ah,9bh,10h,11h-cyclopenta[a]phenanthren-4-yl (2e)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate is found in Azadirachta indica. Based on a literature review very few articles have been published on (1R,2R,7R,9R,10R,11R,14S,15S,16S)-16-hydroxy-14-[(2S,3S,5R)-2-hydroxy-5-(hydroxymethyl)oxolan-3-yl]-2,6,6,10,15-pentamethyl-5-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadec-3-en-9-yl (2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022211062D          

 46 51  0  0  1  0            999 V2000
    4.1281   -9.4359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5963   -8.8052    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8766   -8.0293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3448   -7.3986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6251   -6.6227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0933   -5.9920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3736   -5.2160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8417   -4.5853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0296   -4.7305    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1220   -3.8094    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5902   -3.1787    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7781   -3.3239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2463   -2.6932    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4342   -2.8384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7182   -3.6130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2793   -3.2526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0976   -2.2077    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9098   -2.3529    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1827   -1.4318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9948   -1.2866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5266   -1.9173    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8069   -1.1414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3387   -1.7721    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6190   -0.9961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4311   -0.8509    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7114   -0.0750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9629   -1.4816    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.3228   -0.7393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7875   -1.5084    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.2939   -0.8571    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0646   -0.0646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7474    0.3984    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.7742    1.2229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0735    1.6584    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3987   -0.1080    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1184   -0.8839    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.5814   -1.5668    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0168   -2.3009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3340   -2.7639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6826   -2.2576    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8705   -2.4028    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4023   -3.0335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4372   -6.4775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9690   -7.1082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6887   -7.8841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2205   -8.5148    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  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 11 10  1  6  0  0  0
 11 12  1  0  0  0  0
 13 12  1  1  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 14 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 13 21  1  0  0  0  0
 21 22  1  1  0  0  0
 21 23  1  0  0  0  0
 23 24  1  1  0  0  0
 24 25  1  0  0  0  0
 25 26  1  6  0  0  0
 25 27  1  0  0  0  0
 27 28  1  6  0  0  0
 27 29  1  0  0  0  0
 29 30  1  6  0  0  0
 30 31  1  6  0  0  0
 31 32  1  0  0  0  0
 32 33  1  6  0  0  0
 33 34  1  0  0  0  0
 32 35  1  0  0  0  0
 35 36  1  0  0  0  0
 30 36  1  0  0  0  0
 36 37  1  6  0  0  0
 29 38  1  0  0  0  0
 38 39  1  0  0  0  0
 40 39  1  1  0  0  0
 27 40  1  0  0  0  0
 40 41  1  0  0  0  0
 11 41  1  0  0  0  0
 23 41  1  0  0  0  0
 41 42  1  1  0  0  0
  5 43  2  0  0  0  0
 43 44  1  0  0  0  0
 44 45  2  0  0  0  0
  3 45  1  0  0  0  0
 45 46  1  0  0  0  0
M  END

     RDKit          3D

 96101  0  0  0  0  0  0  0  0999 V2000
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    5.0121    1.9264   -0.5913 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.1067    0.4993   -0.0120 C   0  0  0  0  0  0  0  0  0  0  0  0
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  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
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 41 42  1  1
 29 30  1  0
 30 31  1  0
 31 32  1  0
 32 33  1  0
 33 34  1  0
 32 35  1  0
 35 36  1  0
 36 37  1  0
  5 43  2  0
 43 44  1  0
 44 45  2  0
 45 46  1  0
 45  3  1  0
 41 11  1  0
 36 30  1  0
 21 13  1  0
 41 23  1  0
 40 27  1  0
  1 47  1  0
  1 48  1  0
  1 49  1  0
  4 50  1  0
  6 51  1  0
  7 52  1  0
 11 53  1  1
 12 54  1  0
 12 55  1  0
 13 56  1  6
 15 57  1  0
 15 58  1  0
 15 59  1  0
 16 60  1  0
 16 61  1  0
 16 62  1  0
 19 63  1  0
 20 64  1  0
 22 65  1  0
 22 66  1  0
 22 67  1  0
 23 68  1  6
 24 69  1  0
 24 70  1  0
 25 71  1  1
 26 72  1  0
 28 73  1  0
 28 74  1  0
 28 75  1  0
 29 76  1  1
 38 86  1  0
 38 87  1  0
 39 88  1  0
 39 89  1  0
 40 90  1  6
 42 91  1  0
 42 92  1  0
 42 93  1  0
 30 77  1  6
 31 78  1  0
 31 79  1  0
 32 80  1  6
 33 81  1  0
 33 82  1  0
 34 83  1  0
 36 84  1  6
 37 85  1  0
 43 94  1  0
 44 95  1  0
 46 96  1  0
M  END


  Mrv1652309022211062D          

 46 51  0  0  1  0            999 V2000
    4.1281   -9.4359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5963   -8.8052    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8766   -8.0293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3448   -7.3986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6251   -6.6227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0933   -5.9920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3736   -5.2160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8417   -4.5853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0296   -4.7305    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1220   -3.8094    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5902   -3.1787    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7781   -3.3239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2463   -2.6932    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4342   -2.8384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7182   -3.6130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2793   -3.2526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0976   -2.2077    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9098   -2.3529    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1827   -1.4318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9948   -1.2866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5266   -1.9173    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8069   -1.1414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3387   -1.7721    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6190   -0.9961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4311   -0.8509    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7114   -0.0750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9629   -1.4816    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.3228   -0.7393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7875   -1.5084    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.2939   -0.8571    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0646   -0.0646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7474    0.3984    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.7742    1.2229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0735    1.6584    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3987   -0.1080    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1184   -0.8839    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.5814   -1.5668    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0168   -2.3009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3340   -2.7639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6826   -2.2576    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8705   -2.4028    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4023   -3.0335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4372   -6.4775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9690   -7.1082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6887   -7.8841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2205   -8.5148    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  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 11 10  1  6  0  0  0
 11 12  1  0  0  0  0
 13 12  1  1  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 14 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 13 21  1  0  0  0  0
 21 22  1  1  0  0  0
 21 23  1  0  0  0  0
 23 24  1  1  0  0  0
 24 25  1  0  0  0  0
 25 26  1  6  0  0  0
 25 27  1  0  0  0  0
 27 28  1  6  0  0  0
 27 29  1  0  0  0  0
 29 30  1  6  0  0  0
 30 31  1  6  0  0  0
 31 32  1  0  0  0  0
 32 33  1  6  0  0  0
 33 34  1  0  0  0  0
 32 35  1  0  0  0  0
 35 36  1  0  0  0  0
 30 36  1  0  0  0  0
 36 37  1  6  0  0  0
 29 38  1  0  0  0  0
 38 39  1  0  0  0  0
 40 39  1  1  0  0  0
 27 40  1  0  0  0  0
 40 41  1  0  0  0  0
 11 41  1  0  0  0  0
 23 41  1  0  0  0  0
 41 42  1  1  0  0  0
  5 43  2  0  0  0  0
 43 44  1  0  0  0  0
 44 45  2  0  0  0  0
  3 45  1  0  0  0  0
 45 46  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0152591

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(\C=C\C(=O)O[C@@H]2C[C@H]3C(C)(C)C(=O)C=C[C@]3(C)[C@H]3C[C@H](O)[C@@]4(C)[C@@H](CC[C@H]4[C@]23C)[C@@H]2C[C@H](CO)O[C@@H]2O)=CC=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C37H50O9/c1-34(2)27-18-31(46-32(42)12-8-20-7-10-24(39)25(15-20)44-6)37(5)26-11-9-23(22-16-21(19-38)45-33(22)43)36(26,4)30(41)17-28(37)35(27,3)14-13-29(34)40/h7-8,10,12-15,21-23,26-28,30-31,33,38-39,41,43H,9,11,16-19H2,1-6H3/b12-8+/t21-,22+,23+,26-,27+,28-,30+,31-,33+,35+,36+,37+/m1/s1

> <INCHI_KEY>
JBNMGQJPHZENKR-BTWMYXJXSA-N

> <FORMULA>
C37H50O9

> <MOLECULAR_WEIGHT>
638.798

> <EXACT_MASS>
638.34548319

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
96

> <JCHEM_AVERAGE_POLARIZABILITY>
69.73272279525105

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,2R,7R,9R,10R,11R,14S,15S,16S)-16-hydroxy-14-[(2S,3S,5R)-2-hydroxy-5-(hydroxymethyl)oxolan-3-yl]-2,6,6,10,15-pentamethyl-5-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-3-en-9-yl (2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate

> <ALOGPS_LOGP>
4.19

> <JCHEM_LOGP>
4.870537861333333

> <ALOGPS_LOGS>
-5.35

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.166299880104813

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.865571399159343

> <JCHEM_PKA_STRONGEST_BASIC>
-0.3496760324048115

> <JCHEM_POLAR_SURFACE_AREA>
142.75

> <JCHEM_REFRACTIVITY>
173.3914

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.83e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2R,7R,9R,10R,11R,14S,15S,16S)-16-hydroxy-14-[(2S,3S,5R)-2-hydroxy-5-(hydroxymethyl)oxolan-3-yl]-2,6,6,10,15-pentamethyl-5-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-3-en-9-yl (2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  C   UNK     0       7.706 -17.614   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       6.713 -16.436   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       7.236 -14.988   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.244 -13.811   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.767 -12.362   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.774 -11.185   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.297  -9.737   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.305  -8.559   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       3.789  -8.830   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0       5.828  -7.111   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       4.835  -5.934   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.319  -6.205   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.326  -5.027   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.810  -5.298   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.341  -6.744   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.521  -6.072   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.182  -4.121   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -1.698  -4.392   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       0.341  -2.673   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.857  -2.402   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.850  -3.579   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       3.373  -2.131   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.366  -3.308   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       4.889  -1.859   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       6.405  -1.588   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       6.928  -0.140   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       7.398  -2.766   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       8.069  -1.380   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       8.937  -2.816   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       9.882  -1.600   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       9.454  -0.121   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      10.728   0.744   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      10.779   2.283   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       9.471   3.096   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0      11.944  -0.202   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0      11.421  -1.650   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0      12.285  -2.925   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0       9.365  -4.295   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       8.090  -5.159   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       6.874  -4.214   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0       5.358  -4.485   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0       6.351  -5.663   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0       8.283 -12.091   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0       9.276 -13.269   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0       8.752 -14.717   0.000  0.00  0.00           C+0
HETATM   46  O   UNK     0       9.745 -15.894   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   45                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   43                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12   41                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   21                                                  
CONECT   14   13   15   16   17                                             
CONECT   15   14                                                            
CONECT   16   14                                                            
CONECT   17   14   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   13   22   23                                             
CONECT   22   21                                                            
CONECT   23   21   24   41                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28   29   40                                             
CONECT   28   27                                                            
CONECT   29   27   30   38                                                  
CONECT   30   29   31   36                                                  
CONECT   31   30   32                                                       
CONECT   32   31   33   35                                                  
CONECT   33   32   34                                                       
CONECT   34   33                                                            
CONECT   35   32   36                                                       
CONECT   36   35   30   37                                                  
CONECT   37   36                                                            
CONECT   38   29   39                                                       
CONECT   39   38   40                                                       
CONECT   40   39   27   41                                                  
CONECT   41   40   11   23   42                                             
CONECT   42   41                                                            
CONECT   43    5   44                                                       
CONECT   44   43   45                                                       
CONECT   45   44    3   46                                                  
CONECT   46   45                                                            
MASTER        0    0    0    0    0    0    0    0   46    0  102    0
END

View in JSmol

Synonyms

Value	Source
(1R,2R,7R,9R,10R,11R,14S,15S,16S)-16-Hydroxy-14-[(2S,3S,5R)-2-hydroxy-5-(hydroxymethyl)oxolan-3-yl]-2,6,6,10,15-pentamethyl-5-oxotetracyclo[8.7.0.0,.0,]heptadec-3-en-9-yl (2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoic acid	Generator

Chemical Formula

C₃₇H₅₀O₉

Average Mass

638.7980 Da

Monoisotopic Mass

638.34548 Da

IUPAC Name

(1R,2R,7R,9R,10R,11R,14S,15S,16S)-16-hydroxy-14-[(2S,3S,5R)-2-hydroxy-5-(hydroxymethyl)oxolan-3-yl]-2,6,6,10,15-pentamethyl-5-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-3-en-9-yl (2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate

Traditional Name

CAS Registry Number

Not Available

SMILES

COC1=CC(\C=C\C(=O)O[C@@H]2C[C@H]3C(C)(C)C(=O)C=C[C@]3(C)[C@H]3C[C@H](O)[C@@]4(C)[C@@H](CC[C@H]4[C@]23C)[C@@H]2C[C@H](CO)O[C@@H]2O)=CC=C1O

InChI Identifier

InChI=1S/C37H50O9/c1-34(2)27-18-31(46-32(42)12-8-20-7-10-24(39)25(15-20)44-6)37(5)26-11-9-23(22-16-21(19-38)45-33(22)43)36(26,4)30(41)17-28(37)35(27,3)14-13-29(34)40/h7-8,10,12-15,21-23,26-28,30-31,33,38-39,41,43H,9,11,16-19H2,1-6H3/b12-8+/t21-,22+,23+,26-,27+,28-,30+,31-,33+,35+,36+,37+/m1/s1

InChI Key

JBNMGQJPHZENKR-BTWMYXJXSA-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
Azadirachta indica	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as limonoids. These are highly oxygenated, modified terpenoids with a prototypical structure either containing or derived from a precursor with a 4,4,8-trimethyl-17-furanylsteroid skeleton. All naturally occurring citrus limonoids contain a furan ring attached to the D-ring, at C-17, as well as oxygen containing functional groups at C-3, C-4, C-7, C-16 and C-17.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Triterpenoids

Direct Parent

Limonoids

Alternative Parents

Substituents

Limonoid skeleton
24-hydroxysteroid
Steroid ester
Androgen-skeleton
Androstane-skeleton
3-oxo-delta-1-steroid
3-oxosteroid
12-hydroxysteroid
Hydroxysteroid
Oxosteroid
3-oxo-5-alpha-steroid
Delta-1-steroid
Steroid
Cinnamic acid or derivatives
Coumaric acid or derivatives
Hydroxycinnamic acid or derivatives
Cinnamic acid ester
Methoxyphenol
Phenol ether
Styrene
Anisole
Phenoxy compound
Methoxybenzene
Alkyl aryl ether
Phenol
1-hydroxy-2-unsubstituted benzenoid
Cyclohexenone
Benzenoid
Monocyclic benzene moiety
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Tetrahydrofuran
Cyclic alcohol
Secondary alcohol
Cyclic ketone
Carboxylic acid ester
Ketone
Hemiacetal
Carboxylic acid derivative
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Oxacycle
Ether
Organooxygen compound
Primary alcohol
Carbonyl group
Organic oxide
Hydrocarbon derivative
Alcohol
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	4.19	ALOGPS
logP	4.87	ChemAxon
logS	-5.4	ALOGPS
pKa (Strongest Acidic)	9.87	ChemAxon
pKa (Strongest Basic)	-0.35	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	142.75 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	173.39 m³·mol⁻¹	ChemAxon
Polarizability	69.73 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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

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

163194738

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1s,3ar,3br,4r,5ar,9ar,9br,11s,11as)-11-hydroxy-1-[(2s,3s,5r)-2-hydroxy-5-(hydroxymethyl)oxolan-3-yl]-3b,6,6,9a,11a-pentamethyl-7-oxo-1h,2h,3h,3ah,4h,5h,5ah,9bh,10h,11h-cyclopenta[a]phenanthren-4-yl (2e)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate (NP0152591)

MOL for NP0152591 ((1s,3ar,3br,4r,5ar,9ar,9br,11s,11as)-11-hydroxy-1-[(2s,3s,5r)-2-hydroxy-5-(hydroxymethyl)oxolan-3-yl]-3b,6,6,9a,11a-pentamethyl-7-oxo-1h,2h,3h,3ah,4h,5h,5ah,9bh,10h,11h-cyclopenta[a]phenanthren-4-yl (2e)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate)

3D MOL for NP0152591 ((1s,3ar,3br,4r,5ar,9ar,9br,11s,11as)-11-hydroxy-1-[(2s,3s,5r)-2-hydroxy-5-(hydroxymethyl)oxolan-3-yl]-3b,6,6,9a,11a-pentamethyl-7-oxo-1h,2h,3h,3ah,4h,5h,5ah,9bh,10h,11h-cyclopenta[a]phenanthren-4-yl (2e)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate)

3D SDF for NP0152591 ((1s,3ar,3br,4r,5ar,9ar,9br,11s,11as)-11-hydroxy-1-[(2s,3s,5r)-2-hydroxy-5-(hydroxymethyl)oxolan-3-yl]-3b,6,6,9a,11a-pentamethyl-7-oxo-1h,2h,3h,3ah,4h,5h,5ah,9bh,10h,11h-cyclopenta[a]phenanthren-4-yl (2e)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate)

3D-SDF for NP0152591 ((1s,3ar,3br,4r,5ar,9ar,9br,11s,11as)-11-hydroxy-1-[(2s,3s,5r)-2-hydroxy-5-(hydroxymethyl)oxolan-3-yl]-3b,6,6,9a,11a-pentamethyl-7-oxo-1h,2h,3h,3ah,4h,5h,5ah,9bh,10h,11h-cyclopenta[a]phenanthren-4-yl (2e)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate)

PDB for NP0152591 ((1s,3ar,3br,4r,5ar,9ar,9br,11s,11as)-11-hydroxy-1-[(2s,3s,5r)-2-hydroxy-5-(hydroxymethyl)oxolan-3-yl]-3b,6,6,9a,11a-pentamethyl-7-oxo-1h,2h,3h,3ah,4h,5h,5ah,9bh,10h,11h-cyclopenta[a]phenanthren-4-yl (2e)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate)

3D PDB for NP0152591 ((1s,3ar,3br,4r,5ar,9ar,9br,11s,11as)-11-hydroxy-1-[(2s,3s,5r)-2-hydroxy-5-(hydroxymethyl)oxolan-3-yl]-3b,6,6,9a,11a-pentamethyl-7-oxo-1h,2h,3h,3ah,4h,5h,5ah,9bh,10h,11h-cyclopenta[a]phenanthren-4-yl (2e)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate)

SMILES for NP0152591 ((1s,3ar,3br,4r,5ar,9ar,9br,11s,11as)-11-hydroxy-1-[(2s,3s,5r)-2-hydroxy-5-(hydroxymethyl)oxolan-3-yl]-3b,6,6,9a,11a-pentamethyl-7-oxo-1h,2h,3h,3ah,4h,5h,5ah,9bh,10h,11h-cyclopenta[a]phenanthren-4-yl (2e)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate)

INCHI for NP0152591 ((1s,3ar,3br,4r,5ar,9ar,9br,11s,11as)-11-hydroxy-1-[(2s,3s,5r)-2-hydroxy-5-(hydroxymethyl)oxolan-3-yl]-3b,6,6,9a,11a-pentamethyl-7-oxo-1h,2h,3h,3ah,4h,5h,5ah,9bh,10h,11h-cyclopenta[a]phenanthren-4-yl (2e)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate)

Structure for NP0152591 ((1s,3ar,3br,4r,5ar,9ar,9br,11s,11as)-11-hydroxy-1-[(2s,3s,5r)-2-hydroxy-5-(hydroxymethyl)oxolan-3-yl]-3b,6,6,9a,11a-pentamethyl-7-oxo-1h,2h,3h,3ah,4h,5h,5ah,9bh,10h,11h-cyclopenta[a]phenanthren-4-yl (2e)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate)

3D Structure for NP0152591 ((1s,3ar,3br,4r,5ar,9ar,9br,11s,11as)-11-hydroxy-1-[(2s,3s,5r)-2-hydroxy-5-(hydroxymethyl)oxolan-3-yl]-3b,6,6,9a,11a-pentamethyl-7-oxo-1h,2h,3h,3ah,4h,5h,5ah,9bh,10h,11h-cyclopenta[a]phenanthren-4-yl (2e)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate)