NP-MRD: Showing NP-Card for [(2r,3r,4s,5r,6s)-6-{[(1r,2r,3as,3bs,8s,9ar,9br,11ar)-1-acetyl-2-(acetyloxy)-3a,6,6,9b,11a-pentamethyl-7,10-dioxo-1h,2h,3h,3bh,4h,8h,9h,9ah,11h-cyclopenta[a]phenanthren-8-yl]oxy}-3,4,5-tris(acetyloxy)oxan-2-yl]methyl acetate (NP0273211)

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Record Information

Version

2.0

Created at

2022-09-08 20:10:32 UTC

Updated at

2022-09-08 20:10:32 UTC

NP-MRD ID

NP0273211

Secondary Accession Numbers

None

Natural Product Identification

Common Name

[(2r,3r,4s,5r,6s)-6-{[(1r,2r,3as,3bs,8s,9ar,9br,11ar)-1-acetyl-2-(acetyloxy)-3a,6,6,9b,11a-pentamethyl-7,10-dioxo-1h,2h,3h,3bh,4h,8h,9h,9ah,11h-cyclopenta[a]phenanthren-8-yl]oxy}-3,4,5-tris(acetyloxy)oxan-2-yl]methyl acetate

Description

[(2R,3R,4S,5R,6S)-6-{[(1R,2R,4S,10S,11S,13R,14R,15R)-14-acetyl-13-(acetyloxy)-1,6,6,11,15-pentamethyl-5,17-dioxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadec-7-en-4-yl]oxy}-3,4,5-tris(acetyloxy)oxan-2-yl]methyl acetate belongs to the class of organic compounds known as steroidal glycosides. These are sterol lipids containing a carbohydrate moiety glycosidically linked to the steroid skeleton. [(2r,3r,4s,5r,6s)-6-{[(1r,2r,3as,3bs,8s,9ar,9br,11ar)-1-acetyl-2-(acetyloxy)-3a,6,6,9b,11a-pentamethyl-7,10-dioxo-1h,2h,3h,3bh,4h,8h,9h,9ah,11h-cyclopenta[a]phenanthren-8-yl]oxy}-3,4,5-tris(acetyloxy)oxan-2-yl]methyl acetate is found in Picrorhiza kurrooa. Based on a literature review very few articles have been published on [(2R,3R,4S,5R,6S)-6-{[(1R,2R,4S,10S,11S,13R,14R,15R)-14-acetyl-13-(acetyloxy)-1,6,6,11,15-pentamethyl-5,17-dioxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadec-7-en-4-yl]oxy}-3,4,5-tris(acetyloxy)oxan-2-yl]methyl acetate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309082222102D          

 55 59  0  0  1  0            999 V2000
   -2.2951    0.8222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4830    0.6770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9512    1.3077    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2027   -0.0989    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3906   -0.2441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1103   -1.0201    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7018   -1.1653    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9821   -1.9412    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7942   -2.0864    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3261   -1.4557    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1382   -1.6009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6700   -0.9702    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3897   -0.1943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9215    0.4364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7336    0.2912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0139   -0.4847    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.8261   -0.6299    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.6284    0.1710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4774   -0.1236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1602   -0.5866    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.9362   -0.3063    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0814    0.5059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8573    0.7862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4507    1.0377    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9309   -1.3791    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.4373   -2.0304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1264   -2.7946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2545   -1.9175    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1064   -1.4059    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.4662   -2.1482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5745   -2.0366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7624   -1.8914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2306   -2.5221    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4821   -1.1154    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9503   -1.7461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5776   -0.0491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8616    0.7255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8641    0.3651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0458   -0.6798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2336   -0.5346    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4503   -2.5719    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7306   -3.3478    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5427   -3.4930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0745   -2.8623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8230   -4.2690    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3618   -2.4267    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8936   -3.0574    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6133   -3.8333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1988   -3.9785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1452   -4.4640    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6421   -1.6508    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4542   -1.5056    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9861   -2.1363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7058   -2.9122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7982   -1.9910    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
  4  5  1  0  0  0  0
  6  5  1  1  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  1  0  0  0
 10  9  1  6  0  0  0
 10 11  1  0  0  0  0
 12 11  1  6  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 16 15  1  1  0  0  0
 16 17  1  0  0  0  0
 17 18  1  1  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  1  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  2  0  0  0  0
 20 25  1  0  0  0  0
 25 26  1  6  0  0  0
 26 27  1  0  0  0  0
 26 28  2  0  0  0  0
 25 29  1  0  0  0  0
 17 29  1  0  0  0  0
 29 30  1  6  0  0  0
 29 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 32 34  1  0  0  0  0
 16 34  1  0  0  0  0
 12 34  1  0  0  0  0
 34 35  1  6  0  0  0
 13 36  1  0  0  0  0
 36 37  1  0  0  0  0
 36 38  1  0  0  0  0
 36 39  1  0  0  0  0
 10 39  1  0  0  0  0
 39 40  2  0  0  0  0
  8 41  1  0  0  0  0
 41 42  1  6  0  0  0
 42 43  1  0  0  0  0
 43 44  1  0  0  0  0
 43 45  2  0  0  0  0
 41 46  1  0  0  0  0
 46 47  1  1  0  0  0
 47 48  1  0  0  0  0
 48 49  1  0  0  0  0
 48 50  2  0  0  0  0
 46 51  1  0  0  0  0
  6 51  1  0  0  0  0
 51 52  1  6  0  0  0
 52 53  1  0  0  0  0
 53 54  1  0  0  0  0
 53 55  2  0  0  0  0
M  END

     RDKit          3D

109113  0  0  0  0  0  0  0  0999 V2000
   -7.9745    3.1728    3.8302 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7369    2.3733    3.7757 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.2291   -0.2411   -0.3611 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9658   -0.7140   -0.4583 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0392    0.0947   -1.0928 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0016    0.5826   -0.1295 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3711    0.7401   -0.6269 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5665    0.6279   -2.0768 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7790    0.7657   -2.5712 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8559    1.0334   -1.5456 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7478   -0.0724   -0.5194 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.8119    0.2163    0.5198 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.7745    1.6775    0.7877 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2028   -0.1224    0.0439 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9905   -0.1593    1.3546 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.8488    0.9481    1.4200 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2204    0.8084    1.4285 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2099    1.8854    1.4958 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.0941    1.7399   -3.4195 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.7350   -2.8399   -2.6399 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3670   -3.2738   -4.0221 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8745   -3.6980   -1.7367 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6659   -0.5419   -0.9540 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.4943   -1.6308   -1.3336 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2028   -1.7016   -2.5143 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.7350    2.0919    0.8816 H   0  0  0  0  0  0  0  0  0  0  0  0
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  -10.1615    1.9335    1.2463 H   0  0  0  0  0  0  0  0  0  0  0  0
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  1  2  1  0
  2  3  2  0
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  1 56  1  0
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 46102  1  6
 49103  1  0
 49104  1  0
 49105  1  0
 51106  1  1
 54107  1  0
 54108  1  0
 54109  1  0
M  END


  Mrv1652309082222102D          

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  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  6  5  1  1  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  1  0  0  0
 10  9  1  6  0  0  0
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 17 29  1  0  0  0  0
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 16 34  1  0  0  0  0
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 34 35  1  6  0  0  0
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 36 37  1  0  0  0  0
 36 38  1  0  0  0  0
 36 39  1  0  0  0  0
 10 39  1  0  0  0  0
 39 40  2  0  0  0  0
  8 41  1  0  0  0  0
 41 42  1  6  0  0  0
 42 43  1  0  0  0  0
 43 44  1  0  0  0  0
 43 45  2  0  0  0  0
 41 46  1  0  0  0  0
 46 47  1  1  0  0  0
 47 48  1  0  0  0  0
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 48 50  2  0  0  0  0
 46 51  1  0  0  0  0
  6 51  1  0  0  0  0
 51 52  1  6  0  0  0
 52 53  1  0  0  0  0
 53 54  1  0  0  0  0
 53 55  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0273211

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)OC[C@H]1O[C@@H](O[C@H]2C[C@@H]3C(=CC[C@H]4[C@]5(C)C[C@@H](OC(C)=O)[C@H](C(C)=O)[C@@]5(C)CC(=O)[C@@]34C)C(C)(C)C2=O)[C@H](OC(C)=O)[C@@H](OC(C)=O)[C@@H]1OC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C40H54O15/c1-18(41)31-27(50-20(3)43)15-38(9)29-13-12-24-25(40(29,11)30(47)16-39(31,38)10)14-26(35(48)37(24,7)8)54-36-34(53-23(6)46)33(52-22(5)45)32(51-21(4)44)28(55-36)17-49-19(2)42/h12,25-29,31-34,36H,13-17H2,1-11H3/t25-,26+,27-,28-,29+,31+,32-,33+,34-,36-,38+,39-,40+/m1/s1

> <INCHI_KEY>
ZOEQHDGEQUYKEE-LXPREJINSA-N

> <FORMULA>
C40H54O15

> <MOLECULAR_WEIGHT>
774.857

> <EXACT_MASS>
774.346271039

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
109

> <JCHEM_AVERAGE_POLARIZABILITY>
80.55714504471167

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[(2R,3R,4S,5R,6S)-6-{[(1R,2R,4S,10S,11S,13R,14R,15R)-14-acetyl-13-(acetyloxy)-1,6,6,11,15-pentamethyl-5,17-dioxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-4-yl]oxy}-3,4,5-tris(acetyloxy)oxan-2-yl]methyl acetate

> <JCHEM_LOGP>
2.8535380116666635

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
19.922825741194867

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.83227352396042

> <JCHEM_PKA_STRONGEST_BASIC>
-4.10025227942172

> <JCHEM_POLAR_SURFACE_AREA>
201.16999999999993

> <JCHEM_REFRACTIVITY>
188.15090000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
14

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
[(2R,3R,4S,5R,6S)-6-{[(1R,2R,4S,10S,11S,13R,14R,15R)-14-acetyl-13-(acetyloxy)-1,6,6,11,15-pentamethyl-5,17-dioxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-4-yl]oxy}-3,4,5-tris(acetyloxy)oxan-2-yl]methyl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 08-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-SEP-22         0                                  
HETATM    1  C   UNK     0      -4.284   1.535   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.768   1.264   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -1.776   2.441   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      -2.245  -0.185   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      -0.729  -0.456   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.206  -1.904   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       1.310  -2.175   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       1.833  -3.624   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       3.349  -3.895   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       4.342  -2.717   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.858  -2.988   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.851  -1.811   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.327  -0.363   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.320   0.815   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.836   0.544   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       9.359  -0.905   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      10.875  -1.176   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      10.506   0.319   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      12.091  -0.231   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      13.366  -1.095   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      14.814  -0.572   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      15.085   0.944   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      16.534   1.467   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      13.908   1.937   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      12.938  -2.574   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      13.883  -3.790   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      13.303  -5.217   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      15.408  -3.579   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      11.399  -2.624   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      12.070  -4.010   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      10.406  -3.802   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       8.890  -3.531   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       7.897  -4.708   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       8.367  -2.082   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       7.374  -3.259   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       4.811  -0.092   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       5.342   1.354   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       3.480   0.682   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       3.819  -1.269   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0       2.303  -0.998   0.000  0.00  0.00           O+0
HETATM   41  C   UNK     0       0.841  -4.801   0.000  0.00  0.00           C+0
HETATM   42  O   UNK     0       1.364  -6.249   0.000  0.00  0.00           O+0
HETATM   43  C   UNK     0       2.880  -6.520   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0       3.872  -5.343   0.000  0.00  0.00           C+0
HETATM   45  O   UNK     0       3.403  -7.969   0.000  0.00  0.00           O+0
HETATM   46  C   UNK     0      -0.675  -4.530   0.000  0.00  0.00           C+0
HETATM   47  O   UNK     0      -1.668  -5.707   0.000  0.00  0.00           O+0
HETATM   48  C   UNK     0      -1.145  -7.156   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0       0.371  -7.427   0.000  0.00  0.00           C+0
HETATM   50  O   UNK     0      -2.138  -8.333   0.000  0.00  0.00           O+0
HETATM   51  C   UNK     0      -1.199  -3.081   0.000  0.00  0.00           C+0
HETATM   52  O   UNK     0      -2.715  -2.810   0.000  0.00  0.00           O+0
HETATM   53  C   UNK     0      -3.707  -3.988   0.000  0.00  0.00           C+0
HETATM   54  C   UNK     0      -3.184  -5.436   0.000  0.00  0.00           C+0
HETATM   55  O   UNK     0      -5.223  -3.717   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                                                       
CONECT    6    5    7   51                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   41                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   39                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   34                                                  
CONECT   13   12   14   36                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   34                                                  
CONECT   17   16   18   19   29                                             
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   21   25                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22                                                            
CONECT   25   20   26   29                                                  
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26                                                            
CONECT   29   25   17   30   31                                             
CONECT   30   29                                                            
CONECT   31   29   32                                                       
CONECT   32   31   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32   16   12   35                                             
CONECT   35   34                                                            
CONECT   36   13   37   38   39                                             
CONECT   37   36                                                            
CONECT   38   36                                                            
CONECT   39   36   10   40                                                  
CONECT   40   39                                                            
CONECT   41    8   42   46                                                  
CONECT   42   41   43                                                       
CONECT   43   42   44   45                                                  
CONECT   44   43                                                            
CONECT   45   43                                                            
CONECT   46   41   47   51                                                  
CONECT   47   46   48                                                       
CONECT   48   47   49   50                                                  
CONECT   49   48                                                            
CONECT   50   48                                                            
CONECT   51   46    6   52                                                  
CONECT   52   51   53                                                       
CONECT   53   52   54   55                                                  
CONECT   54   53                                                            
CONECT   55   53                                                            
MASTER        0    0    0    0    0    0    0    0   55    0  118    0
END

View in JSmol

Synonyms

Value	Source
[(2R,3R,4S,5R,6S)-6-{[(1R,2R,4S,10S,11S,13R,14R,15R)-14-acetyl-13-(acetyloxy)-1,6,6,11,15-pentamethyl-5,17-dioxotetracyclo[8.7.0.0,.0,]heptadec-7-en-4-yl]oxy}-3,4,5-tris(acetyloxy)oxan-2-yl]methyl acetic acid	Generator

Chemical Formula

C₄₀H₅₄O₁₅

Average Mass

774.8570 Da

Monoisotopic Mass

774.34627 Da

IUPAC Name

[(2R,3R,4S,5R,6S)-6-{[(1R,2R,4S,10S,11S,13R,14R,15R)-14-acetyl-13-(acetyloxy)-1,6,6,11,15-pentamethyl-5,17-dioxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-4-yl]oxy}-3,4,5-tris(acetyloxy)oxan-2-yl]methyl acetate

Traditional Name

CAS Registry Number

Not Available

SMILES

CC(=O)OC[C@H]1O[C@@H](O[C@H]2C[C@@H]3C(=CC[C@H]4[C@]5(C)C[C@@H](OC(C)=O)[C@H](C(C)=O)[C@@]5(C)CC(=O)[C@@]34C)C(C)(C)C2=O)[C@H](OC(C)=O)[C@@H](OC(C)=O)[C@@H]1OC(C)=O

InChI Identifier

InChI=1S/C40H54O15/c1-18(41)31-27(50-20(3)43)15-38(9)29-13-12-24-25(40(29,11)30(47)16-39(31,38)10)14-26(35(48)37(24,7)8)54-36-34(53-23(6)46)33(52-22(5)45)32(51-21(4)44)28(55-36)17-49-19(2)42/h12,25-29,31-34,36H,13-17H2,1-11H3/t25-,26+,27-,28-,29+,31+,32-,33+,34-,36-,38+,39-,40+/m1/s1

InChI Key

ZOEQHDGEQUYKEE-LXPREJINSA-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
Picrorhiza kurrooa	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as steroidal glycosides. These are sterol lipids containing a carbohydrate moiety glycosidically linked to the steroid skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Steroidal glycosides

Direct Parent

Steroidal glycosides

Alternative Parents

Substituents

Diterpene glycoside
Steroidal glycoside
20-oxosteroid
Steroid ester
Diterpenoid
3-oxo-delta-5-steroid
3-oxosteroid
14-alpha-methylsteroid
11-oxosteroid
Oxosteroid
Delta-5-steroid
Terpene glycoside
Pentacarboxylic acid or derivatives
O-glycosyl compound
Glycosyl compound
Oxane
Monosaccharide
Cyclic ketone
Carboxylic acid ester
Ketone
Organoheterocyclic compound
Acetal
Carboxylic acid derivative
Oxacycle
Organic oxide
Carbonyl group
Organooxygen compound
Organic oxygen compound
Hydrocarbon derivative
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

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

Predicted Properties

Property	Value	Source
logP	2.85	ChemAxon
pKa (Strongest Acidic)	18.83	ChemAxon
pKa (Strongest Basic)	-4.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	201.17 Å²	ChemAxon
Rotatable Bond Count	14	ChemAxon
Refractivity	188.15 m³·mol⁻¹	ChemAxon
Polarizability	80.56 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	No	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

14447019

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for [(2r,3r,4s,5r,6s)-6-{[(1r,2r,3as,3bs,8s,9ar,9br,11ar)-1-acetyl-2-(acetyloxy)-3a,6,6,9b,11a-pentamethyl-7,10-dioxo-1h,2h,3h,3bh,4h,8h,9h,9ah,11h-cyclopenta[a]phenanthren-8-yl]oxy}-3,4,5-tris(acetyloxy)oxan-2-yl]methyl acetate (NP0273211)

MOL for NP0273211 ([(2r,3r,4s,5r,6s)-6-{[(1r,2r,3as,3bs,8s,9ar,9br,11ar)-1-acetyl-2-(acetyloxy)-3a,6,6,9b,11a-pentamethyl-7,10-dioxo-1h,2h,3h,3bh,4h,8h,9h,9ah,11h-cyclopenta[a]phenanthren-8-yl]oxy}-3,4,5-tris(acetyloxy)oxan-2-yl]methyl acetate)

3D MOL for NP0273211 ([(2r,3r,4s,5r,6s)-6-{[(1r,2r,3as,3bs,8s,9ar,9br,11ar)-1-acetyl-2-(acetyloxy)-3a,6,6,9b,11a-pentamethyl-7,10-dioxo-1h,2h,3h,3bh,4h,8h,9h,9ah,11h-cyclopenta[a]phenanthren-8-yl]oxy}-3,4,5-tris(acetyloxy)oxan-2-yl]methyl acetate)

3D SDF for NP0273211 ([(2r,3r,4s,5r,6s)-6-{[(1r,2r,3as,3bs,8s,9ar,9br,11ar)-1-acetyl-2-(acetyloxy)-3a,6,6,9b,11a-pentamethyl-7,10-dioxo-1h,2h,3h,3bh,4h,8h,9h,9ah,11h-cyclopenta[a]phenanthren-8-yl]oxy}-3,4,5-tris(acetyloxy)oxan-2-yl]methyl acetate)

3D-SDF for NP0273211 ([(2r,3r,4s,5r,6s)-6-{[(1r,2r,3as,3bs,8s,9ar,9br,11ar)-1-acetyl-2-(acetyloxy)-3a,6,6,9b,11a-pentamethyl-7,10-dioxo-1h,2h,3h,3bh,4h,8h,9h,9ah,11h-cyclopenta[a]phenanthren-8-yl]oxy}-3,4,5-tris(acetyloxy)oxan-2-yl]methyl acetate)

PDB for NP0273211 ([(2r,3r,4s,5r,6s)-6-{[(1r,2r,3as,3bs,8s,9ar,9br,11ar)-1-acetyl-2-(acetyloxy)-3a,6,6,9b,11a-pentamethyl-7,10-dioxo-1h,2h,3h,3bh,4h,8h,9h,9ah,11h-cyclopenta[a]phenanthren-8-yl]oxy}-3,4,5-tris(acetyloxy)oxan-2-yl]methyl acetate)

3D PDB for NP0273211 ([(2r,3r,4s,5r,6s)-6-{[(1r,2r,3as,3bs,8s,9ar,9br,11ar)-1-acetyl-2-(acetyloxy)-3a,6,6,9b,11a-pentamethyl-7,10-dioxo-1h,2h,3h,3bh,4h,8h,9h,9ah,11h-cyclopenta[a]phenanthren-8-yl]oxy}-3,4,5-tris(acetyloxy)oxan-2-yl]methyl acetate)

SMILES for NP0273211 ([(2r,3r,4s,5r,6s)-6-{[(1r,2r,3as,3bs,8s,9ar,9br,11ar)-1-acetyl-2-(acetyloxy)-3a,6,6,9b,11a-pentamethyl-7,10-dioxo-1h,2h,3h,3bh,4h,8h,9h,9ah,11h-cyclopenta[a]phenanthren-8-yl]oxy}-3,4,5-tris(acetyloxy)oxan-2-yl]methyl acetate)

INCHI for NP0273211 ([(2r,3r,4s,5r,6s)-6-{[(1r,2r,3as,3bs,8s,9ar,9br,11ar)-1-acetyl-2-(acetyloxy)-3a,6,6,9b,11a-pentamethyl-7,10-dioxo-1h,2h,3h,3bh,4h,8h,9h,9ah,11h-cyclopenta[a]phenanthren-8-yl]oxy}-3,4,5-tris(acetyloxy)oxan-2-yl]methyl acetate)

Structure for NP0273211 ([(2r,3r,4s,5r,6s)-6-{[(1r,2r,3as,3bs,8s,9ar,9br,11ar)-1-acetyl-2-(acetyloxy)-3a,6,6,9b,11a-pentamethyl-7,10-dioxo-1h,2h,3h,3bh,4h,8h,9h,9ah,11h-cyclopenta[a]phenanthren-8-yl]oxy}-3,4,5-tris(acetyloxy)oxan-2-yl]methyl acetate)

3D Structure for NP0273211 ([(2r,3r,4s,5r,6s)-6-{[(1r,2r,3as,3bs,8s,9ar,9br,11ar)-1-acetyl-2-(acetyloxy)-3a,6,6,9b,11a-pentamethyl-7,10-dioxo-1h,2h,3h,3bh,4h,8h,9h,9ah,11h-cyclopenta[a]phenanthren-8-yl]oxy}-3,4,5-tris(acetyloxy)oxan-2-yl]methyl acetate)