NP-MRD: Showing NP-Card for 6-{[8a-carboxy-8-hydroxy-4-(hydroxymethyl)-4,6a,6b,11,11,14b-hexamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy}-4,5-dihydroxy-3-[(3,4,5-trihydroxyoxan-2-yl)oxy]oxane-2-carboxylic acid (NP0255515)

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Record Information

Version

2.0

Created at

2022-09-07 20:02:56 UTC

Updated at

2022-09-07 20:02:56 UTC

NP-MRD ID

NP0255515

Secondary Accession Numbers

None

Natural Product Identification

Common Name

6-{[8a-carboxy-8-hydroxy-4-(hydroxymethyl)-4,6a,6b,11,11,14b-hexamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy}-4,5-dihydroxy-3-[(3,4,5-trihydroxyoxan-2-yl)oxy]oxane-2-carboxylic acid

Description

6-{[8A-carboxy-8-hydroxy-4-(hydroxymethyl)-4,6a,6b,11,11,14b-hexamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b-icosahydropicen-3-yl]oxy}-4,5-dihydroxy-3-[(3,4,5-trihydroxyoxan-2-yl)oxy]oxane-2-carboxylic acid belongs to the class of organic compounds known as alpha amino acids. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon). 6-{[8a-carboxy-8-hydroxy-4-(hydroxymethyl)-4,6a,6b,11,11,14b-hexamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy}-4,5-dihydroxy-3-[(3,4,5-trihydroxyoxan-2-yl)oxy]oxane-2-carboxylic acid is found in Prunella vulgaris. 6-{[8A-carboxy-8-hydroxy-4-(hydroxymethyl)-4,6a,6b,11,11,14b-hexamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b-icosahydropicen-3-yl]oxy}-4,5-dihydroxy-3-[(3,4,5-trihydroxyoxan-2-yl)oxy]oxane-2-carboxylic acid is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004241500052D          

 56 62  0  0  0  0            999 V2000
   -0.4733   -3.5409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -3.8230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4452   -3.0106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105   -4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -5.2520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270   -5.2520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395   -5.9664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270   -6.6809    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -5.9664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770   -5.2520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1895   -5.9664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770   -3.8230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020   -3.8230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0145   -4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8395   -4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4270   -3.8230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2520   -3.8230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0770   -3.8230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4895   -4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3145   -4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7270   -3.8230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3145   -3.1086    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7270   -2.3941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5520   -2.3941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9645   -1.6796    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.7895   -1.6796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2020   -2.3941    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.0270   -2.3941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4395   -1.6796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2645   -1.6796    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.0270   -0.9651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4395   -0.2507    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.2020   -0.9651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7895   -0.2507    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9645   -3.1086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7895   -3.1086    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5520   -3.8230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9645   -4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3145   -1.6796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7270   -0.9651    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4895   -1.6796    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0770   -5.2520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9337   -6.0644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8522   -5.5341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9955   -6.3466    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2520   -5.2520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8395   -5.9664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0145   -5.9664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020   -5.2520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6882   -6.0725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395   -4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270   -3.8230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -5.9664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6282   -6.7869    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105   -5.9664    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
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 30 32  1  0  0  0  0
 32 33  1  0  0  0  0
 32 34  1  0  0  0  0
 27 34  1  0  0  0  0
 34 35  1  0  0  0  0
 25 36  1  0  0  0  0
 36 37  1  0  0  0  0
 36 38  1  0  0  0  0
 22 38  1  0  0  0  0
 38 39  1  0  0  0  0
 24 40  1  0  0  0  0
 40 41  2  0  0  0  0
 40 42  1  0  0  0  0
 20 43  1  0  0  0  0
 43 44  1  0  0  0  0
 43 45  1  0  0  0  0
 45 46  1  0  0  0  0
 43 47  1  0  0  0  0
 16 47  1  0  0  0  0
 47 48  1  0  0  0  0
 48 49  1  0  0  0  0
 49 50  1  0  0  0  0
 10 50  1  0  0  0  0
 15 50  1  0  0  0  0
 50 51  1  0  0  0  0
 12 52  1  0  0  0  0
  6 52  1  0  0  0  0
 52 53  1  0  0  0  0
  2 53  1  0  0  0  0
  6 54  1  0  0  0  0
 54 55  2  0  0  0  0
 54 56  1  0  0  0  0
M  END

     RDKit          3D

120126  0  0  0  0  0  0  0  0999 V2000
   -9.0047    1.2235   -1.9281 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8360    0.2616   -1.9782 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5772   -0.2134   -3.3983 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2495   -0.9642   -1.1850 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4332   -0.5973    0.2425 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2063    0.0274    0.8812 C   0  0  1  0  0  0  0  0  0  0  0  0
   -7.7867    0.7721    2.0633 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4837    0.4132    3.2092 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6542    1.8492    1.8486 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3740   -1.0979    1.3994 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.1758   -2.0928    0.4132 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1193   -0.7275    2.1000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3460    0.4026    1.4715 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.1716    1.4699    2.5675 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0169    1.0570    0.3656 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2554    1.7845   -0.4267 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7996    1.9511   -0.2386 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1200    1.0241    0.6920 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.9533   -0.1362    1.1330 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.5212   -0.7948    2.4134 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1259   -1.0789   -0.0102 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9705   -1.0791   -0.9972 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7163   -0.7777   -0.2490 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5411   -1.3568   -0.7416 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8471   -1.2062   -2.1945 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3851   -2.8909   -0.5689 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6364   -3.4744   -0.9150 O   0  0  0  0  0  0  0  0  0  0  0  0
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    2.6300   -0.1654   -0.3055 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9324   -0.6566   -0.1129 C   0  0  2  0  0  0  0  0  0  0  0  0
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    6.3243    2.8162   -0.8606 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6653   -0.1738   -0.2053 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.9248    0.4023   -0.3294 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8658   -0.3382    0.3824 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.8786   -0.8197   -0.4388 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.1307   -0.7599    0.1315 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5593    0.6956    0.1857 C   0  0  1  0  0  0  0  0  0  0  0  0
   11.5607    1.1797   -1.1135 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.5220    1.4430    0.9727 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.8934    2.4227    0.1758 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.4301    0.5409    1.4889 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.7940   -0.1813    2.6072 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0516   -0.5358   -1.5140 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.7926   -1.5954   -2.0871 O   0  0  0  0  0  0  0  0  0  0  0  0
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    3.9383   -0.2892   -2.4267 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -7.1427    0.5822   -4.0326 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9350   -1.1144   -3.3216 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2780   -1.2234   -1.5773 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6355   -1.8405   -1.3855 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3130    0.0737    0.3506 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6741   -1.5077    0.8260 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3098    2.7648    2.1628 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0376   -1.6333    2.1488 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8988   -2.9204    0.8773 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3560   -0.5427    3.1744 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5023   -1.6778    2.1280 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9723    1.4184    3.3297 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1827    2.4935    2.1130 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2381    1.3778    3.1176 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6928    2.3151   -1.2786 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6860    3.0246    0.1107 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4065    1.8765   -1.2995 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.2209   -0.6388    3.2832 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3361   -2.1223    0.3294 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0076   -0.7723   -0.6105 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9105   -2.0958   -1.4169 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1556   -0.4183   -1.8692 H   0  0  0  0  0  0  0  0  0  0  0  0
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    1.2149   -0.1802   -2.3935 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6900   -1.8687   -2.4965 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0092   -1.4951   -2.8546 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1827   -3.1734    0.4586 H   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


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M  END
> <DATABASE_ID>
NP0255515

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1(C)CCC2(C(O)CC3(C)C(=CCC4C5(C)CCC(OC6OC(C(OC7OCC(O)C(O)C7O)C(O)C6O)C(O)=O)C(C)(CO)C5CCC34C)C2C1)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C41H64O15/c1-36(2)13-14-41(35(51)52)20(15-36)19-7-8-23-37(3)11-10-25(38(4,18-42)22(37)9-12-39(23,5)40(19,6)16-24(41)44)54-34-29(48)27(46)30(31(56-34)32(49)50)55-33-28(47)26(45)21(43)17-53-33/h7,20-31,33-34,42-48H,8-18H2,1-6H3,(H,49,50)(H,51,52)

> <INCHI_KEY>
XZFHCYYKRRBNBJ-UHFFFAOYSA-N

> <FORMULA>
C41H64O15

> <MOLECULAR_WEIGHT>
796.948

> <EXACT_MASS>
796.424521361

> <JCHEM_ACCEPTOR_COUNT>
15

> <JCHEM_ATOM_COUNT>
120

> <JCHEM_AVERAGE_POLARIZABILITY>
85.73258611847797

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
9

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
6-{[8a-carboxy-8-hydroxy-4-(hydroxymethyl)-4,6a,6b,11,11,14b-hexamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b-icosahydropicen-3-yl]oxy}-4,5-dihydroxy-3-[(3,4,5-trihydroxyoxan-2-yl)oxy]oxane-2-carboxylic acid

> <ALOGPS_LOGP>
2.05

> <JCHEM_LOGP>
1.492189398333333

> <ALOGPS_LOGS>
-3.68

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
4.638307530078826

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.428172562214883

> <JCHEM_PKA_STRONGEST_BASIC>
-3.5265806647778204

> <JCHEM_POLAR_SURFACE_AREA>
253.12999999999997

> <JCHEM_REFRACTIVITY>
195.64620000000014

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.65e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6-{[8a-carboxy-8-hydroxy-4-(hydroxymethyl)-4,6a,6b,11,11,14b-hexamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy}-4,5-dihydroxy-3-[(3,4,5-trihydroxyoxan-2-yl)oxy]oxane-2-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-APR-15         0                                  
HETATM    1  C   UNK     0      -0.883  -6.610   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.564  -7.136   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.831  -5.620   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.206  -8.470   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.564  -9.804   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.104  -9.804   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.874 -11.137   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       2.104 -12.471   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       4.414 -11.137   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.184  -9.804   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.954 -11.137   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.414  -8.470   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.184  -7.136   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.724  -7.136   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.494  -8.470   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       9.034  -8.470   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.264  -7.136   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       9.804  -7.136   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      11.344  -7.136   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      12.114  -8.470   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      13.654  -8.470   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      14.424  -7.136   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      13.654  -5.803   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      14.424  -4.469   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      15.964  -4.469   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      16.734  -3.135   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      18.274  -3.135   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      19.044  -4.469   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      20.584  -4.469   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      21.354  -3.135   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      22.894  -3.135   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      20.584  -1.802   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      21.354  -0.468   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      19.044  -1.802   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      18.274  -0.468   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0      16.734  -5.803   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0      18.274  -5.803   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0      15.964  -7.136   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0      16.734  -8.470   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0      13.654  -3.135   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0      14.424  -1.802   0.000  0.00  0.00           O+0
HETATM   42  O   UNK     0      12.114  -3.135   0.000  0.00  0.00           O+0
HETATM   43  C   UNK     0      11.344  -9.804   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0      11.076 -11.320   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0      12.791 -10.330   0.000  0.00  0.00           C+0
HETATM   46  O   UNK     0      13.058 -11.847   0.000  0.00  0.00           O+0
HETATM   47  C   UNK     0       9.804  -9.804   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0       9.034 -11.137   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0       7.494 -11.137   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0       6.724  -9.804   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0       6.885 -11.335   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0       2.874  -8.470   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0       2.104  -7.136   0.000  0.00  0.00           C+0
HETATM   54  C   UNK     0       1.334 -11.137   0.000  0.00  0.00           C+0
HETATM   55  O   UNK     0       1.173 -12.669   0.000  0.00  0.00           O+0
HETATM   56  O   UNK     0      -0.206 -11.137   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4   53                                             
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   52   54                                             
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11   12   50                                             
CONECT   11   10                                                            
CONECT   12   10   13   52                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   50                                                  
CONECT   16   15   17   18   47                                             
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   43                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23   38                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25   40                                                  
CONECT   25   24   26   36                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28   34                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32   27   35                                                  
CONECT   35   34                                                            
CONECT   36   25   37   38                                                  
CONECT   37   36                                                            
CONECT   38   36   22   39                                                  
CONECT   39   38                                                            
CONECT   40   24   41   42                                                  
CONECT   41   40                                                            
CONECT   42   40                                                            
CONECT   43   20   44   45   47                                             
CONECT   44   43                                                            
CONECT   45   43   46                                                       
CONECT   46   45                                                            
CONECT   47   43   16   48                                                  
CONECT   48   47   49                                                       
CONECT   49   48   50                                                       
CONECT   50   49   10   15   51                                             
CONECT   51   50                                                            
CONECT   52   12    6   53                                                  
CONECT   53   52    2                                                       
CONECT   54    6   55   56                                                  
CONECT   55   54                                                            
CONECT   56   54                                                            
MASTER        0    0    0    0    0    0    0    0   56    0  124    0
END

View in JSmol

Synonyms

Value	Source
6-{[8a-carboxy-8-hydroxy-4-(hydroxymethyl)-4,6a,6b,11,11,14b-hexamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b-icosahydropicen-3-yl]oxy}-4,5-dihydroxy-3-[(3,4,5-trihydroxyoxan-2-yl)oxy]oxane-2-carboxylate	Generator

Chemical Formula

C₄₁H₆₄O₁₅

Average Mass

796.9480 Da

Monoisotopic Mass

796.42452 Da

IUPAC Name

6-{[8a-carboxy-8-hydroxy-4-(hydroxymethyl)-4,6a,6b,11,11,14b-hexamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b-icosahydropicen-3-yl]oxy}-4,5-dihydroxy-3-[(3,4,5-trihydroxyoxan-2-yl)oxy]oxane-2-carboxylic acid

Traditional Name

CAS Registry Number

Not Available

SMILES

CC1(C)CCC2(C(O)CC3(C)C(=CCC4C5(C)CCC(OC6OC(C(OC7OCC(O)C(O)C7O)C(O)C6O)C(O)=O)C(C)(CO)C5CCC34C)C2C1)C(O)=O

InChI Identifier

InChI=1S/C41H64O15/c1-36(2)13-14-41(35(51)52)20(15-36)19-7-8-23-37(3)11-10-25(38(4,18-42)22(37)9-12-39(23,5)40(19,6)16-24(41)44)54-34-29(48)27(46)30(31(56-34)32(49)50)55-33-28(47)26(45)21(43)17-53-33/h7,20-31,33-34,42-48H,8-18H2,1-6H3,(H,49,50)(H,51,52)

InChI Key

XZFHCYYKRRBNBJ-UHFFFAOYSA-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
Prunella vulgaris	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as alpha amino acids. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon).

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Alpha amino acids

Alternative Parents

Substituents

Alpha-amino acid
Phosphoethanolamine
Monoalkyl phosphate
Organic phosphoric acid derivative
Phosphoric acid ester
Fatty acid
Alkyl phosphate
Amino acid
Carboxylic acid
Monocarboxylic acid or derivatives
Organic nitrogen compound
Primary amine
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Organic oxide
Organopnictogen compound
Primary aliphatic amine
Organic oxygen compound
Carbonyl group
Amine
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

alpha-amino acid (CHEBI:86913 )

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	2.05	ALOGPS
logP	1.49	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	3.43	ChemAxon
pKa (Strongest Basic)	-3.5	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	15	ChemAxon
Hydrogen Donor Count	9	ChemAxon
Polar Surface Area	253.13 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	195.65 m³·mol⁻¹	ChemAxon
Polarizability	85.73 Å³	ChemAxon
Number of Rings	7	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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 6-{[8a-carboxy-8-hydroxy-4-(hydroxymethyl)-4,6a,6b,11,11,14b-hexamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy}-4,5-dihydroxy-3-[(3,4,5-trihydroxyoxan-2-yl)oxy]oxane-2-carboxylic acid (NP0255515)

MOL for NP0255515 (6-{[8a-carboxy-8-hydroxy-4-(hydroxymethyl)-4,6a,6b,11,11,14b-hexamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy}-4,5-dihydroxy-3-[(3,4,5-trihydroxyoxan-2-yl)oxy]oxane-2-carboxylic acid)

3D MOL for NP0255515 (6-{[8a-carboxy-8-hydroxy-4-(hydroxymethyl)-4,6a,6b,11,11,14b-hexamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy}-4,5-dihydroxy-3-[(3,4,5-trihydroxyoxan-2-yl)oxy]oxane-2-carboxylic acid)

3D SDF for NP0255515 (6-{[8a-carboxy-8-hydroxy-4-(hydroxymethyl)-4,6a,6b,11,11,14b-hexamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy}-4,5-dihydroxy-3-[(3,4,5-trihydroxyoxan-2-yl)oxy]oxane-2-carboxylic acid)

3D-SDF for NP0255515 (6-{[8a-carboxy-8-hydroxy-4-(hydroxymethyl)-4,6a,6b,11,11,14b-hexamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy}-4,5-dihydroxy-3-[(3,4,5-trihydroxyoxan-2-yl)oxy]oxane-2-carboxylic acid)

PDB for NP0255515 (6-{[8a-carboxy-8-hydroxy-4-(hydroxymethyl)-4,6a,6b,11,11,14b-hexamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy}-4,5-dihydroxy-3-[(3,4,5-trihydroxyoxan-2-yl)oxy]oxane-2-carboxylic acid)

3D PDB for NP0255515 (6-{[8a-carboxy-8-hydroxy-4-(hydroxymethyl)-4,6a,6b,11,11,14b-hexamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy}-4,5-dihydroxy-3-[(3,4,5-trihydroxyoxan-2-yl)oxy]oxane-2-carboxylic acid)

SMILES for NP0255515 (6-{[8a-carboxy-8-hydroxy-4-(hydroxymethyl)-4,6a,6b,11,11,14b-hexamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy}-4,5-dihydroxy-3-[(3,4,5-trihydroxyoxan-2-yl)oxy]oxane-2-carboxylic acid)

INCHI for NP0255515 (6-{[8a-carboxy-8-hydroxy-4-(hydroxymethyl)-4,6a,6b,11,11,14b-hexamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy}-4,5-dihydroxy-3-[(3,4,5-trihydroxyoxan-2-yl)oxy]oxane-2-carboxylic acid)

Structure for NP0255515 (6-{[8a-carboxy-8-hydroxy-4-(hydroxymethyl)-4,6a,6b,11,11,14b-hexamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy}-4,5-dihydroxy-3-[(3,4,5-trihydroxyoxan-2-yl)oxy]oxane-2-carboxylic acid)

3D Structure for NP0255515 (6-{[8a-carboxy-8-hydroxy-4-(hydroxymethyl)-4,6a,6b,11,11,14b-hexamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy}-4,5-dihydroxy-3-[(3,4,5-trihydroxyoxan-2-yl)oxy]oxane-2-carboxylic acid)