NP-MRD: Showing NP-Card for Orthosiphol Y (NP0026371)

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Record Information

Version

2.0

Created at

2021-06-19 18:15:50 UTC

Updated at

2021-06-29 23:51:52 UTC

NP-MRD ID

NP0026371

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Orthosiphol Y

Provided By

JEOL Database JEOL Logo

Description

Orthosiphol Y is found in Orthosiphon aristatus and Orthosiphon stamineus. Orthosiphol Y was first documented in 2003 (Awale, S., et al.). Based on a literature review very few articles have been published on ORTHOSIPHOL Y.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306192120153D          

 64 66  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652306192120153D          

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   -2.7784    2.0499    2.2714 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.2639    1.6488    2.3253 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7183    3.5180    1.7768 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9012    1.1545    1.3278 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5723    0.8621   -0.0288 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5722    0.2775   -1.0319 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5181    1.2367   -1.2743 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7847    2.2047   -2.1942 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4067    3.0981   -2.3523 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8391    2.3406   -2.7963 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9447   -1.0213   -0.4822 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9478   -2.0495   -0.3929 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0429   -1.5529   -1.5373 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2918   -1.5968   -2.7270 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2454   -1.0944    0.9159 H   0  0  0  0  0  0  0  0  0  0  0  0
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    2.3847   -0.2760   -1.9160 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9156   -3.4912   -1.7819 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2669   -3.8787   -2.3030 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1461   -2.5628   -3.0772 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5629   -3.7558   -0.0242 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1111   -3.2639    0.6211 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3686   -2.8405    1.7249 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5557   -2.7817    2.7790 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5114   -0.0712    0.8020 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9538   -0.7552    3.2926 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9410   -2.0792    2.8252 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0904   -1.4061    1.6658 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3107   -0.2322    3.5530 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0095    3.2321    7.1941 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1048    4.3812    6.4065 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6533    2.7121    6.6855 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8228    2.2941    3.0140 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4131    0.6263    2.6746 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7454    1.7426    1.3463 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1323    3.6293    0.7700 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6870    3.8897    1.7616 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2859    4.1856    2.4364 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0229    1.7805    1.0967 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9791    1.7899   -0.4433 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4181    0.1769    0.0912 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1049    0.0604   -1.9676 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2718    2.5097   -2.6687 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6130    3.6095   -1.4088 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1979    3.8485   -3.1201 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3116   -2.1726   -1.2937 H   0  0  0  0  0  0  0  0  0  0  0  0
  9  8  1  0  0  0  0
  6  7  1  0  0  0  0
 22 23  1  0  0  0  0
 12 13  1  0  0  0  0
 23 24  1  0  0  0  0
 17 18  2  0  0  0  0
 24 29  1  0  0  0  0
 19 20  1  1  0  0  0
  8 29  1  0  0  0  0
 24 25  1  0  0  0  0
 19 22  1  0  0  0  0
 22 57  1  6  0  0  0
  9 11  1  0  0  0  0
  3  4  1  0  0  0  0
  9 22  1  0  0  0  0
 29 30  1  1  0  0  0
  9 10  1  1  0  0  0
 12 17  1  0  0  0  0
 19 21  1  0  0  0  0
 12 11  2  0  0  0  0
  2  1  2  3  0  0  0
  8  6  1  0  0  0  0
 31 32  2  0  0  0  0
 29 31  1  0  0  0  0
 13 14  1  0  0  0  0
 31  3  1  0  0  0  0
 14 15  1  0  0  0  0
  3  5  1  0  0  0  0
 14 16  2  0  0  0  0
  5  6  1  0  0  0  0
 25 26  1  0  0  0  0
 17 19  1  0  0  0  0
 26 27  1  0  0  0  0
  3  2  1  1  0  0  0
 26 28  2  0  0  0  0
 11 47  1  0  0  0  0
 23 58  1  0  0  0  0
 23 59  1  0  0  0  0
 24 60  1  6  0  0  0
  8 43  1  6  0  0  0
  5 39  1  0  0  0  0
  5 40  1  0  0  0  0
  6 41  1  1  0  0  0
  2 35  1  0  0  0  0
  7 42  1  0  0  0  0
 20 51  1  0  0  0  0
 20 52  1  0  0  0  0
 20 53  1  0  0  0  0
  4 36  1  0  0  0  0
  4 37  1  0  0  0  0
  4 38  1  0  0  0  0
 30 64  1  0  0  0  0
 10 44  1  0  0  0  0
 10 45  1  0  0  0  0
 10 46  1  0  0  0  0
 21 54  1  0  0  0  0
 21 55  1  0  0  0  0
 21 56  1  0  0  0  0
  1 33  1  0  0  0  0
  1 34  1  0  0  0  0
 15 48  1  0  0  0  0
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 15 50  1  0  0  0  0
 27 61  1  0  0  0  0
 27 62  1  0  0  0  0
 27 63  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0026371

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]O[C@]1([H])C([H])([H])[C@](C([H])=C([H])[H])(C(=O)[C@]2(O[H])[C@]([H])(OC(=O)C([H])([H])[H])C([H])([H])[C@]3([H])[C@@](C([H])=C(OC(=O)C([H])([H])[H])C(=O)C3(C([H])([H])[H])C([H])([H])[H])(C([H])([H])[H])[C@@]12[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C24H32O8/c1-8-22(6)10-14(27)18-23(7)11-15(31-12(2)25)19(28)21(4,5)16(23)9-17(32-13(3)26)24(18,30)20(22)29/h8,11,14,16-18,27,30H,1,9-10H2,2-7H3/t14-,16+,17-,18-,22+,23+,24+/m1/s1

> <INCHI_KEY>
HPYXDZBUORPUPP-FBZJSPOMSA-N

> <FORMULA>
C24H32O8

> <MOLECULAR_WEIGHT>
448.512

> <EXACT_MASS>
448.20971799

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
64

> <JCHEM_AVERAGE_POLARIZABILITY>
46.238641089717774

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(4aR,4bS,5R,7R,8aR,9R,10aR)-3-(acetyloxy)-7-ethenyl-5,8a-dihydroxy-1,1,4a,7-tetramethyl-2,8-dioxo-1,2,4a,4b,5,6,7,8,8a,9,10,10a-dodecahydrophenanthren-9-yl acetate

> <ALOGPS_LOGP>
1.99

> <JCHEM_LOGP>
1.7881451753333333

> <ALOGPS_LOGS>
-3.74

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.864999185484493

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.813267104232485

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9013968144223554

> <JCHEM_POLAR_SURFACE_AREA>
127.20000000000002

> <JCHEM_REFRACTIVITY>
114.95279999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.14e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(4aR,4bS,5R,7R,8aR,9R,10aR)-3-(acetyloxy)-7-ethenyl-5,8a-dihydroxy-1,1,4a,7-tetramethyl-2,8-dioxo-4b,5,6,9,10,10a-hexahydrophenanthren-9-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 64 66  0  0  0  0  0  0  0  0999 V2000
    3.1803   -0.5426   -0.0157 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3587   -0.8925   -1.0145 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4038   -2.0738   -1.0613 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9657   -3.0551   -2.1134 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1607   -2.8697    0.2374 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3832   -2.1400    1.3499 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2881   -1.9128    2.4290 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2931   -0.8115    0.9105 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2966   -0.1516    1.9735 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3757   -1.1483    2.4499 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5708    0.3105    3.2296 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9584    1.3370    3.9992 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2529    1.6654    5.1643 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2515    2.9398    5.0935 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7903    3.3341    6.4359 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3079    3.6510    4.0969 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2191    2.0801    3.6992 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7704    2.7058    4.6079 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7784    2.0499    2.2714 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.2639    1.6488    2.3253 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7183    3.5180    1.7768 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9012    1.1545    1.3278 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5723    0.8621   -0.0288 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5722    0.2775   -1.0319 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5181    1.2367   -1.2743 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7847    2.2047   -2.1942 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4067    3.0981   -2.3523 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8391    2.3406   -2.7963 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9447   -1.0213   -0.4822 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9478   -2.0495   -0.3929 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0429   -1.5529   -1.5373 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2918   -1.5968   -2.7270 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2454   -1.0944    0.9159 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8256    0.3266   -0.1113 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3847   -0.2760   -1.9160 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9156   -3.4912   -1.7819 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2669   -3.8787   -2.3030 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1461   -2.5628   -3.0772 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5629   -3.7558   -0.0242 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1111   -3.2639    0.6211 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3686   -2.8405    1.7249 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5557   -2.7817    2.7790 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5114   -0.0712    0.8020 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9538   -0.7552    3.2926 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9410   -2.0792    2.8252 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0904   -1.4061    1.6658 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3107   -0.2322    3.5530 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0095    3.2321    7.1941 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1048    4.3812    6.4065 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6533    2.7121    6.6855 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8228    2.2941    3.0140 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4131    0.6263    2.6746 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7454    1.7426    1.3463 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1323    3.6293    0.7700 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6870    3.8897    1.7616 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2859    4.1856    2.4364 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0229    1.7805    1.0967 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9791    1.7899   -0.4433 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4181    0.1769    0.0912 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1049    0.0604   -1.9676 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2718    2.5097   -2.6687 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6130    3.6095   -1.4088 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1979    3.8485   -3.1201 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3116   -2.1726   -1.2937 H   0  0  0  0  0  0  0  0  0  0  0  0
  9  8  1  0
  6  7  1  0
 22 23  1  0
 12 13  1  0
 23 24  1  0
 17 18  2  0
 24 29  1  0
 19 20  1  1
  8 29  1  0
 24 25  1  0
 19 22  1  0
 22 57  1  6
  9 11  1  0
  3  4  1  0
  9 22  1  0
 29 30  1  1
  9 10  1  1
 12 17  1  0
 19 21  1  0
 12 11  2  0
  2  1  2  3
  8  6  1  0
 31 32  2  0
 29 31  1  0
 13 14  1  0
 31  3  1  0
 14 15  1  0
  3  5  1  0
 14 16  2  0
  5  6  1  0
 25 26  1  0
 17 19  1  0
 26 27  1  0
  3  2  1  1
 26 28  2  0
 11 47  1  0
 23 58  1  0
 23 59  1  0
 24 60  1  6
  8 43  1  6
  5 39  1  0
  5 40  1  0
  6 41  1  1
  2 35  1  0
  7 42  1  0
 20 51  1  0
 20 52  1  0
 20 53  1  0
  4 36  1  0
  4 37  1  0
  4 38  1  0
 30 64  1  0
 10 44  1  0
 10 45  1  0
 10 46  1  0
 21 54  1  0
 21 55  1  0
 21 56  1  0
  1 33  1  0
  1 34  1  0
 15 48  1  0
 15 49  1  0
 15 50  1  0
 27 61  1  0
 27 62  1  0
 27 63  1  0
M  END

HEADER    PROTEIN                                 19-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-JUN-21         0                                  
HETATM    1  C   UNK     0       3.180  -0.543  -0.016  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.359  -0.893  -1.014  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.404  -2.074  -1.061  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.966  -3.055  -2.113  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.161  -2.870   0.237  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.383  -2.140   1.350  0.00  0.00           C+0
HETATM    7  O   UNK     0       1.288  -1.913   2.429  0.00  0.00           O+0
HETATM    8  C   UNK     0      -0.293  -0.812   0.911  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.297  -0.152   1.974  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.376  -1.148   2.450  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.571   0.311   3.230  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.958   1.337   3.999  0.00  0.00           C+0
HETATM   13  O   UNK     0      -0.253   1.665   5.164  0.00  0.00           O+0
HETATM   14  C   UNK     0       0.252   2.940   5.093  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.790   3.334   6.436  0.00  0.00           C+0
HETATM   16  O   UNK     0       0.308   3.651   4.097  0.00  0.00           O+0
HETATM   17  C   UNK     0      -2.219   2.080   3.699  0.00  0.00           C+0
HETATM   18  O   UNK     0      -2.770   2.706   4.608  0.00  0.00           O+0
HETATM   19  C   UNK     0      -2.778   2.050   2.271  0.00  0.00           C+0
HETATM   20  C   UNK     0      -4.264   1.649   2.325  0.00  0.00           C+0
HETATM   21  C   UNK     0      -2.718   3.518   1.777  0.00  0.00           C+0
HETATM   22  C   UNK     0      -1.901   1.155   1.328  0.00  0.00           C+0
HETATM   23  C   UNK     0      -2.572   0.862  -0.029  0.00  0.00           C+0
HETATM   24  C   UNK     0      -1.572   0.278  -1.032  0.00  0.00           C+0
HETATM   25  O   UNK     0      -0.518   1.237  -1.274  0.00  0.00           O+0
HETATM   26  C   UNK     0      -0.785   2.205  -2.194  0.00  0.00           C+0
HETATM   27  C   UNK     0       0.407   3.098  -2.352  0.00  0.00           C+0
HETATM   28  O   UNK     0      -1.839   2.341  -2.796  0.00  0.00           O+0
HETATM   29  C   UNK     0      -0.945  -1.021  -0.482  0.00  0.00           C+0
HETATM   30  O   UNK     0      -1.948  -2.050  -0.393  0.00  0.00           O+0
HETATM   31  C   UNK     0       0.043  -1.553  -1.537  0.00  0.00           C+0
HETATM   32  O   UNK     0      -0.292  -1.597  -2.727  0.00  0.00           O+0
HETATM   33  H   UNK     0       3.245  -1.094   0.916  0.00  0.00           H+0
HETATM   34  H   UNK     0       3.826   0.327  -0.111  0.00  0.00           H+0
HETATM   35  H   UNK     0       2.385  -0.276  -1.916  0.00  0.00           H+0
HETATM   36  H   UNK     0       2.916  -3.491  -1.782  0.00  0.00           H+0
HETATM   37  H   UNK     0       1.267  -3.879  -2.303  0.00  0.00           H+0
HETATM   38  H   UNK     0       2.146  -2.563  -3.077  0.00  0.00           H+0
HETATM   39  H   UNK     0       0.563  -3.756  -0.024  0.00  0.00           H+0
HETATM   40  H   UNK     0       2.111  -3.264   0.621  0.00  0.00           H+0
HETATM   41  H   UNK     0      -0.369  -2.841   1.725  0.00  0.00           H+0
HETATM   42  H   UNK     0       1.556  -2.782   2.779  0.00  0.00           H+0
HETATM   43  H   UNK     0       0.511  -0.071   0.802  0.00  0.00           H+0
HETATM   44  H   UNK     0      -2.954  -0.755   3.293  0.00  0.00           H+0
HETATM   45  H   UNK     0      -1.941  -2.079   2.825  0.00  0.00           H+0
HETATM   46  H   UNK     0      -3.090  -1.406   1.666  0.00  0.00           H+0
HETATM   47  H   UNK     0       0.311  -0.232   3.553  0.00  0.00           H+0
HETATM   48  H   UNK     0       0.010   3.232   7.194  0.00  0.00           H+0
HETATM   49  H   UNK     0       1.105   4.381   6.407  0.00  0.00           H+0
HETATM   50  H   UNK     0       1.653   2.712   6.686  0.00  0.00           H+0
HETATM   51  H   UNK     0      -4.823   2.294   3.014  0.00  0.00           H+0
HETATM   52  H   UNK     0      -4.413   0.626   2.675  0.00  0.00           H+0
HETATM   53  H   UNK     0      -4.745   1.743   1.346  0.00  0.00           H+0
HETATM   54  H   UNK     0      -3.132   3.629   0.770  0.00  0.00           H+0
HETATM   55  H   UNK     0      -1.687   3.890   1.762  0.00  0.00           H+0
HETATM   56  H   UNK     0      -3.286   4.186   2.436  0.00  0.00           H+0
HETATM   57  H   UNK     0      -1.023   1.781   1.097  0.00  0.00           H+0
HETATM   58  H   UNK     0      -2.979   1.790  -0.443  0.00  0.00           H+0
HETATM   59  H   UNK     0      -3.418   0.177   0.091  0.00  0.00           H+0
HETATM   60  H   UNK     0      -2.105   0.060  -1.968  0.00  0.00           H+0
HETATM   61  H   UNK     0       1.272   2.510  -2.669  0.00  0.00           H+0
HETATM   62  H   UNK     0       0.613   3.610  -1.409  0.00  0.00           H+0
HETATM   63  H   UNK     0       0.198   3.849  -3.120  0.00  0.00           H+0
HETATM   64  H   UNK     0      -2.312  -2.173  -1.294  0.00  0.00           H+0
CONECT    1    2   33   34                                                  
CONECT    2    1    3   35                                                  
CONECT    3    4   31    5    2                                             
CONECT    4    3   36   37   38                                             
CONECT    5    3    6   39   40                                             
CONECT    6    7    8    5   41                                             
CONECT    7    6   42                                                       
CONECT    8    9   29    6   43                                             
CONECT    9    8   11   22   10                                             
CONECT   10    9   44   45   46                                             
CONECT   11    9   12   47                                                  
CONECT   12   13   17   11                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14   48   49   50                                             
CONECT   16   14                                                            
CONECT   17   18   12   19                                                  
CONECT   18   17                                                            
CONECT   19   20   22   21   17                                             
CONECT   20   19   51   52   53                                             
CONECT   21   19   54   55   56                                             
CONECT   22   23   19   57    9                                             
CONECT   23   22   24   58   59                                             
CONECT   24   23   29   25   60                                             
CONECT   25   24   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26   61   62   63                                             
CONECT   28   26                                                            
CONECT   29   24    8   30   31                                             
CONECT   30   29   64                                                       
CONECT   31   32   29    3                                                  
CONECT   32   31                                                            
CONECT   33    1                                                            
CONECT   34    1                                                            
CONECT   35    2                                                            
CONECT   36    4                                                            
CONECT   37    4                                                            
CONECT   38    4                                                            
CONECT   39    5                                                            
CONECT   40    5                                                            
CONECT   41    6                                                            
CONECT   42    7                                                            
CONECT   43    8                                                            
CONECT   44   10                                                            
CONECT   45   10                                                            
CONECT   46   10                                                            
CONECT   47   11                                                            
CONECT   48   15                                                            
CONECT   49   15                                                            
CONECT   50   15                                                            
CONECT   51   20                                                            
CONECT   52   20                                                            
CONECT   53   20                                                            
CONECT   54   21                                                            
CONECT   55   21                                                            
CONECT   56   21                                                            
CONECT   57   22                                                            
CONECT   58   23                                                            
CONECT   59   23                                                            
CONECT   60   24                                                            
CONECT   61   27                                                            
CONECT   62   27                                                            
CONECT   63   27                                                            
CONECT   64   30                                                            
MASTER        0    0    0    0    0    0    0    0   64    0  132    0
END

RDKit          3D

64 66  0  0  0  0  0  0  0  0999 V2000
    3.1803   -0.5426   -0.0157 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3587   -0.8925   -1.0145 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4038   -2.0738   -1.0613 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9657   -3.0551   -2.1134 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1607   -2.8697    0.2374 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3832   -2.1400    1.3499 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2881   -1.9128    2.4290 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2931   -0.8115    0.9105 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2966   -0.1516    1.9735 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3757   -1.1483    2.4499 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5708    0.3105    3.2296 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9584    1.3370    3.9992 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2529    1.6654    5.1643 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2515    2.9398    5.0935 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7903    3.3341    6.4359 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3079    3.6510    4.0969 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2191    2.0801    3.6992 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7704    2.7058    4.6079 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7784    2.0499    2.2714 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.2639    1.6488    2.3253 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7183    3.5180    1.7768 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9012    1.1545    1.3278 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5723    0.8621   -0.0288 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5722    0.2775   -1.0319 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5181    1.2367   -1.2743 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7847    2.2047   -2.1942 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4067    3.0981   -2.3523 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8391    2.3406   -2.7963 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9447   -1.0213   -0.4822 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9478   -2.0495   -0.3929 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0429   -1.5529   -1.5373 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2918   -1.5968   -2.7270 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2454   -1.0944    0.9159 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8256    0.3266   -0.1113 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3847   -0.2760   -1.9160 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9156   -3.4912   -1.7819 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2669   -3.8787   -2.3030 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1461   -2.5628   -3.0772 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5629   -3.7558   -0.0242 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1111   -3.2639    0.6211 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3686   -2.8405    1.7249 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5557   -2.7817    2.7790 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5114   -0.0712    0.8020 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9538   -0.7552    3.2926 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9410   -2.0792    2.8252 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0904   -1.4061    1.6658 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3107   -0.2322    3.5530 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0095    3.2321    7.1941 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1048    4.3812    6.4065 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6533    2.7121    6.6855 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8228    2.2941    3.0140 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4131    0.6263    2.6746 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7454    1.7426    1.3463 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1323    3.6293    0.7700 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6870    3.8897    1.7616 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2859    4.1856    2.4364 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0229    1.7805    1.0967 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9791    1.7899   -0.4433 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4181    0.1769    0.0912 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1049    0.0604   -1.9676 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2718    2.5097   -2.6687 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6130    3.6095   -1.4088 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1979    3.8485   -3.1201 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3116   -2.1726   -1.2937 H   0  0  0  0  0  0  0  0  0  0  0  0
  9  8  1  0
  6  7  1  0
 22 23  1  0
 12 13  1  0
 23 24  1  0
 17 18  2  0
 24 29  1  0
 19 20  1  1
  8 29  1  0
 24 25  1  0
 19 22  1  0
 22 57  1  6
  9 11  1  0
  3  4  1  0
  9 22  1  0
 29 30  1  1
  9 10  1  1
 12 17  1  0
 19 21  1  0
 12 11  2  0
  2  1  2  3
  8  6  1  0
 31 32  2  0
 29 31  1  0
 13 14  1  0
 31  3  1  0
 14 15  1  0
  3  5  1  0
 14 16  2  0
  5  6  1  0
 25 26  1  0
 17 19  1  0
 26 27  1  0
  3  2  1  1
 26 28  2  0
 11 47  1  0
 23 58  1  0
 23 59  1  0
 24 60  1  6
  8 43  1  6
  5 39  1  0
  5 40  1  0
  6 41  1  1
  2 35  1  0
  7 42  1  0
 20 51  1  0
 20 52  1  0
 20 53  1  0
  4 36  1  0
  4 37  1  0
  4 38  1  0
 30 64  1  0
 10 44  1  0
 10 45  1  0
 10 46  1  0
 21 54  1  0
 21 55  1  0
 21 56  1  0
  1 33  1  0
  1 34  1  0
 15 48  1  0
 15 49  1  0
 15 50  1  0
 27 61  1  0
 27 62  1  0
 27 63  1  0
M  END

View in JSmol

Synonyms

Value	Source
(4AR,4BS,5R,7R,8ar,9R,10ar)-3-(acetyloxy)-7-ethenyl-5,8a-dihydroxy-1,1,4a,7-tetramethyl-2,8-dioxo-1,2,4a,4b,5,6,7,8,8a,9,10,10a-dodecahydrophenanthren-9-yl acetic acid	Generator

Chemical Formula

C₂₄H₃₂O₈

Average Mass

448.5120 Da

Monoisotopic Mass

448.20972 Da

IUPAC Name

(4aR,4bS,5R,7R,8aR,9R,10aR)-3-(acetyloxy)-7-ethenyl-5,8a-dihydroxy-1,1,4a,7-tetramethyl-2,8-dioxo-1,2,4a,4b,5,6,7,8,8a,9,10,10a-dodecahydrophenanthren-9-yl acetate

Traditional Name

(4aR,4bS,5R,7R,8aR,9R,10aR)-3-(acetyloxy)-7-ethenyl-5,8a-dihydroxy-1,1,4a,7-tetramethyl-2,8-dioxo-4b,5,6,9,10,10a-hexahydrophenanthren-9-yl acetate

CAS Registry Number

Not Available

SMILES

[H]O[C@]1([H])C([H])([H])[C@](C([H])=C([H])[H])(C(=O)[C@]2(O[H])[C@]([H])(OC(=O)C([H])([H])[H])C([H])([H])[C@]3([H])[C@@](C([H])=C(OC(=O)C([H])([H])[H])C(=O)C3(C([H])([H])[H])C([H])([H])[H])(C([H])([H])[H])[C@@]12[H])C([H])([H])[H]

InChI Identifier

InChI=1S/C24H32O8/c1-8-22(6)10-14(27)18-23(7)11-15(31-12(2)25)19(28)21(4,5)16(23)9-17(32-13(3)26)24(18,30)20(22)29/h8,11,14,16-18,27,30H,1,9-10H2,2-7H3/t14-,16+,17-,18-,22+,23+,24+/m1/s1

InChI Key

HPYXDZBUORPUPP-FBZJSPOMSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Orthosiphon aristatus	LOTUS Database	35616633
Orthosiphon stamineus	JEOL database	Awale, S., et al, J. Nat. Prod. 66, 255 (2003)

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Diterpenoids

Alternative Parents

Substituents

Diterpenoid
Pimarane diterpenoid
Hydrophenanthrene
Phenanthrene
Cyclohexenone
Dicarboxylic acid or derivatives
Cyclic alcohol
Enol ester
Tertiary alcohol
Ketone
Cyclic ketone
Carboxylic acid ester
Secondary alcohol
Carboxylic acid derivative
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Alcohol
Organooxygen compound
Carbonyl group
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic 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	1.99	ALOGPS
logP	1.79	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	11.81	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	127.2 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	114.95 m³·mol⁻¹	ChemAxon
Polarizability	46.24 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

9319917

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11144807

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Awale, S., et al. (2003). Awale, S., et al, J. Nat. Prod. 66, 255 (2003). J. Nat. Prod..

Showing NP-Card for Orthosiphol Y (NP0026371)

MOL for NP0026371 (Orthosiphol Y)

3D MOL for NP0026371 (Orthosiphol Y)

3D SDF for NP0026371 (Orthosiphol Y)

3D-SDF for NP0026371 (Orthosiphol Y)

PDB for NP0026371 (Orthosiphol Y)

3D PDB for NP0026371 (Orthosiphol Y)

SMILES for NP0026371 (Orthosiphol Y)

INCHI for NP0026371 (Orthosiphol Y)

Structure for NP0026371 (Orthosiphol Y)

3D Structure for NP0026371 (Orthosiphol Y)