NP-MRD: Showing NP-Card for (2s,3s,4s,5r,6r)-3,4,5-trihydroxy-6-[(5r,8s)-2,10,10-trimethyltricyclo[6.3.0.0¹,⁵]undec-6-ene-6-carbonyloxy]oxane-2-carboxylic acid (NP0316222)

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Record Information

Version

2.0

Created at

2022-09-11 15:16:22 UTC

Updated at

2022-09-11 15:16:23 UTC

NP-MRD ID

NP0316222

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2s,3s,4s,5r,6r)-3,4,5-trihydroxy-6-[(5r,8s)-2,10,10-trimethyltricyclo[6.3.0.0¹,⁵]undec-6-ene-6-carbonyloxy]oxane-2-carboxylic acid

Description

Deoxypentalenylglucuron belongs to the class of organic compounds known as terpene glycosides. These are prenol lipids containing a carbohydrate moiety glycosidically bound to a terpene backbone. (2s,3s,4s,5r,6r)-3,4,5-trihydroxy-6-[(5r,8s)-2,10,10-trimethyltricyclo[6.3.0.0¹,⁵]undec-6-ene-6-carbonyloxy]oxane-2-carboxylic acid is found in Streptomyces omiyaensis. (2s,3s,4s,5r,6r)-3,4,5-trihydroxy-6-[(5r,8s)-2,10,10-trimethyltricyclo[6.3.0.0¹,⁵]undec-6-ene-6-carbonyloxy]oxane-2-carboxylic acid was first documented in 1983 (PMID: 6833143). Based on a literature review very few articles have been published on Deoxypentalenylglucuron.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309112217162D          

 29 32  0  0  1  0            999 V2000
    2.3838   -1.4901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8989   -0.8227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0739   -0.8227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8190   -0.0381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4864    0.4468    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7413    1.2315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2564    1.8989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5920    2.6526    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4359    1.8127    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0490    2.4801    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8695    2.3939    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3544    3.0613    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1749    2.9751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6598    3.6425    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5104    2.2214    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0188    3.8150    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5037    4.4824    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1983    3.9012    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1372    4.6549    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2866    3.2338    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1071    3.3200    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5663    1.2315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8213    0.4468    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4887   -0.0381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2338   -0.8227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0408   -0.9942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1476   -1.6432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4088   -0.8227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1538   -0.0381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  5  4  1  1  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
 10  9  1  1  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  6  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 12 16  1  0  0  0  0
 16 17  1  1  0  0  0
 16 18  1  0  0  0  0
 18 19  1  6  0  0  0
 18 20  1  0  0  0  0
 10 20  1  0  0  0  0
 20 21  1  1  0  0  0
  6 22  2  0  0  0  0
 23 22  1  6  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 25 28  1  0  0  0  0
 28 29  1  0  0  0  0
  2 29  1  0  0  0  0
 23 29  1  0  0  0  0
  5 29  1  0  0  0  0
M  END

     RDKit          3D

 59 62  0  0  0  0  0  0  0  0999 V2000
   -3.3451   -1.2876   -2.9188 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4056   -1.3447   -1.7454 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5284   -2.6898   -1.0291 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9281   -2.3972    0.3066 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8845   -0.9133    0.4910 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5725   -0.3139    0.2362 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7548   -0.7596    0.6882 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9032   -1.7868    1.3980 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8975   -0.0588    0.3456 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2051   -0.4718    0.7732 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9287   -0.7271   -0.3676 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9901    0.1272   -0.5630 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.7437   -0.3015   -1.7660 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3885   -1.2965   -2.4292 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8824    0.4049   -2.1919 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9190   -0.0075    0.6196 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.0663    0.7313    0.3200 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2290    0.5897    1.8200 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.6039   -0.1666    2.9319 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7520    0.6252    1.6211 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2832    1.8429    1.1311 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7410    0.7659   -0.5114 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1558    0.9874   -0.8230 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8062    1.7052    0.3404 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2273    1.1759    0.2621 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9735    2.1214   -0.6833 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9051    1.1715    1.6050 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1529   -0.2183   -0.3202 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7159   -0.3982   -0.6593 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.5351   -0.2306   -3.1560 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2305   -1.8885   -2.7119 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7894   -1.7216   -3.7942 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3494   -1.2363   -2.0364 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6297   -2.8924   -0.9691 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0134   -3.4955   -1.5732 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9634   -2.9030    0.4591 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6171   -2.8079    1.1018 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3199   -0.5947    1.4764 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1034   -1.4020    1.3891 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6824    1.1916   -0.6241 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9101    1.4093   -1.9846 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1713   -1.0720    0.7813 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8501    0.2675    0.7025 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5802    1.6504    1.9200 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0044   -0.9178    3.0941 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2815    0.5156    2.6418 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1536    2.4727    1.8963 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0533    1.4332   -0.8704 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3508    1.4503   -1.7838 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7510    2.7993    0.2312 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3075    1.4390    1.2908 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2526    2.6294   -1.3713 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7320    1.5828   -1.2719 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4850    2.8799   -0.0446 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0072    1.3748    1.4784 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5327    1.9897    2.2608 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8203    0.1857    2.1247 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5459   -0.9807    0.3977 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7632   -0.2376   -1.2498 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6 22  2  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 25 27  1  0
 25 28  1  0
 29 28  1  1
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 12 13  1  0
 13 15  1  0
 13 14  2  0
 29  2  1  0
 20 10  1  0
 29  5  1  0
 29 23  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  2 33  1  6
  3 34  1  0
  3 35  1  0
  4 36  1  0
  4 37  1  0
  5 38  1  1
 22 48  1  0
 23 49  1  6
 24 50  1  0
 24 51  1  0
 26 52  1  0
 26 53  1  0
 26 54  1  0
 27 55  1  0
 27 56  1  0
 27 57  1  0
 28 58  1  0
 28 59  1  0
 10 39  1  1
 12 40  1  6
 16 42  1  1
 17 43  1  0
 18 44  1  1
 19 45  1  0
 20 46  1  1
 21 47  1  0
 15 41  1  0
M  END


  Mrv1652309112217162D          

 29 32  0  0  1  0            999 V2000
    2.3838   -1.4901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8989   -0.8227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0739   -0.8227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8190   -0.0381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4864    0.4468    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7413    1.2315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2564    1.8989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5920    2.6526    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4359    1.8127    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0490    2.4801    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8695    2.3939    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3544    3.0613    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1749    2.9751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6598    3.6425    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5104    2.2214    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0188    3.8150    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5037    4.4824    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1983    3.9012    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1372    4.6549    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2866    3.2338    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1071    3.3200    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5663    1.2315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8213    0.4468    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4887   -0.0381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2338   -0.8227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0408   -0.9942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1476   -1.6432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4088   -0.8227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1538   -0.0381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  5  4  1  1  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
 10  9  1  1  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  6  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 12 16  1  0  0  0  0
 16 17  1  1  0  0  0
 16 18  1  0  0  0  0
 18 19  1  6  0  0  0
 18 20  1  0  0  0  0
 10 20  1  0  0  0  0
 20 21  1  1  0  0  0
  6 22  2  0  0  0  0
 23 22  1  6  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 25 28  1  0  0  0  0
 28 29  1  0  0  0  0
  2 29  1  0  0  0  0
 23 29  1  0  0  0  0
  5 29  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0316222

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1CC[C@H]2C(=C[C@@H]3CC(C)(C)CC123)C(=O)O[C@H]1O[C@@H]([C@@H](O)[C@H](O)[C@H]1O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C21H30O8/c1-9-4-5-12-11(6-10-7-20(2,3)8-21(9,10)12)18(27)29-19-15(24)13(22)14(23)16(28-19)17(25)26/h6,9-10,12-16,19,22-24H,4-5,7-8H2,1-3H3,(H,25,26)/t9?,10-,12+,13+,14+,15-,16+,19-,21?/m1/s1

> <INCHI_KEY>
BFYOGFPGIVIQCC-PLCONXLHSA-N

> <FORMULA>
C21H30O8

> <MOLECULAR_WEIGHT>
410.463

> <EXACT_MASS>
410.194067926

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
59

> <JCHEM_AVERAGE_POLARIZABILITY>
42.67994419673023

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S,3S,4S,5R,6R)-3,4,5-trihydroxy-6-[(5R,8S)-2,10,10-trimethyltricyclo[6.3.0.0^{1,5}]undec-6-ene-6-carbonyloxy]oxane-2-carboxylic acid

> <JCHEM_LOGP>
1.578390563333333

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
12.212240288393827

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.2144137639692865

> <JCHEM_PKA_STRONGEST_BASIC>
-3.686906431163913

> <JCHEM_POLAR_SURFACE_AREA>
133.52

> <JCHEM_REFRACTIVITY>
99.71019999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3S,4S,5R,6R)-3,4,5-trihydroxy-6-[(5R,8S)-2,10,10-trimethyltricyclo[6.3.0.0^{1,5}]undec-6-ene-6-carbonyloxy]oxane-2-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 11-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-22         0                                  
HETATM    1  C   UNK     0       4.450  -2.782   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.545  -1.536   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.005  -1.536   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.529  -0.071   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.775   0.834   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.251   2.299   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.345   3.545   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       2.972   4.951   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0       0.814   3.384   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      -0.091   4.630   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -1.623   4.469   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -2.528   5.714   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -4.060   5.553   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -4.965   6.799   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0      -4.686   4.147   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      -1.902   7.121   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -2.807   8.367   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      -0.370   7.282   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       0.256   8.689   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       0.535   6.036   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       2.067   6.197   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       4.791   2.299   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       5.266   0.834   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       6.512  -0.071   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       6.036  -1.536   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       7.543  -1.856   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       5.875  -3.067   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       4.496  -1.536   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       4.021  -0.071   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   29                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   29                                                  
CONECT    6    5    7   22                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11   20                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   16                                                  
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13                                                            
CONECT   16   12   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   10   21                                                  
CONECT   21   20                                                            
CONECT   22    6   23                                                       
CONECT   23   22   24   29                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26   27   28                                             
CONECT   26   25                                                            
CONECT   27   25                                                            
CONECT   28   25   29                                                       
CONECT   29   28    2   23    5                                             
MASTER        0    0    0    0    0    0    0    0   29    0   64    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₁H₃₀O₈

Average Mass

410.4630 Da

Monoisotopic Mass

410.19407 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

CC1CC[C@H]2C(=C[C@@H]3CC(C)(C)CC123)C(=O)O[C@H]1O[C@@H]([C@@H](O)[C@H](O)[C@H]1O)C(O)=O

InChI Identifier

InChI=1S/C21H30O8/c1-9-4-5-12-11(6-10-7-20(2,3)8-21(9,10)12)18(27)29-19-15(24)13(22)14(23)16(28-19)17(25)26/h6,9-10,12-16,19,22-24H,4-5,7-8H2,1-3H3,(H,25,26)/t9?,10-,12+,13+,14+,15-,16+,19-,21?/m1/s1

InChI Key

BFYOGFPGIVIQCC-PLCONXLHSA-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
Streptomyces omiyaensis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as terpene glycosides. These are prenol lipids containing a carbohydrate moiety glycosidically bound to a terpene backbone.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene glycosides

Direct Parent

Terpene glycosides

Alternative Parents

Substituents

Terpene glycoside
Angular triquinane sesquiterpenoid
Sesquiterpenoid
O-glucuronide
1-o-glucuronide
Glucuronic acid or derivatives
Beta-hydroxy acid
Pyran
Oxane
Monosaccharide
Hydroxy acid
Dicarboxylic acid or derivatives
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Secondary alcohol
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Polyol
Carboxylic acid
Carboxylic acid derivative
Acetal
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
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

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00018493

Chemspider ID

114080

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

128725

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Takahashi S, Takeuchi M, Arai M, Seto H, Otake N: Studies on biosynthesis of pentalenolactone. V isolation of deoxypentalenylglucuron. J Antibiot (Tokyo). 1983 Mar;36(3):226-8. doi: 10.7164/antibiotics.36.226. [PubMed:6833143 ]
LOTUS database [Link]

Showing NP-Card for (2s,3s,4s,5r,6r)-3,4,5-trihydroxy-6-[(5r,8s)-2,10,10-trimethyltricyclo[6.3.0.0¹,⁵]undec-6-ene-6-carbonyloxy]oxane-2-carboxylic acid (NP0316222)

MOL for NP0316222 ((2s,3s,4s,5r,6r)-3,4,5-trihydroxy-6-[(5r,8s)-2,10,10-trimethyltricyclo[6.3.0.0¹,⁵]undec-6-ene-6-carbonyloxy]oxane-2-carboxylic acid)

3D MOL for NP0316222 ((2s,3s,4s,5r,6r)-3,4,5-trihydroxy-6-[(5r,8s)-2,10,10-trimethyltricyclo[6.3.0.0¹,⁵]undec-6-ene-6-carbonyloxy]oxane-2-carboxylic acid)

3D SDF for NP0316222 ((2s,3s,4s,5r,6r)-3,4,5-trihydroxy-6-[(5r,8s)-2,10,10-trimethyltricyclo[6.3.0.0¹,⁵]undec-6-ene-6-carbonyloxy]oxane-2-carboxylic acid)

3D-SDF for NP0316222 ((2s,3s,4s,5r,6r)-3,4,5-trihydroxy-6-[(5r,8s)-2,10,10-trimethyltricyclo[6.3.0.0¹,⁵]undec-6-ene-6-carbonyloxy]oxane-2-carboxylic acid)

PDB for NP0316222 ((2s,3s,4s,5r,6r)-3,4,5-trihydroxy-6-[(5r,8s)-2,10,10-trimethyltricyclo[6.3.0.0¹,⁵]undec-6-ene-6-carbonyloxy]oxane-2-carboxylic acid)

3D PDB for NP0316222 ((2s,3s,4s,5r,6r)-3,4,5-trihydroxy-6-[(5r,8s)-2,10,10-trimethyltricyclo[6.3.0.0¹,⁵]undec-6-ene-6-carbonyloxy]oxane-2-carboxylic acid)

SMILES for NP0316222 ((2s,3s,4s,5r,6r)-3,4,5-trihydroxy-6-[(5r,8s)-2,10,10-trimethyltricyclo[6.3.0.0¹,⁵]undec-6-ene-6-carbonyloxy]oxane-2-carboxylic acid)

INCHI for NP0316222 ((2s,3s,4s,5r,6r)-3,4,5-trihydroxy-6-[(5r,8s)-2,10,10-trimethyltricyclo[6.3.0.0¹,⁵]undec-6-ene-6-carbonyloxy]oxane-2-carboxylic acid)

Structure for NP0316222 ((2s,3s,4s,5r,6r)-3,4,5-trihydroxy-6-[(5r,8s)-2,10,10-trimethyltricyclo[6.3.0.0¹,⁵]undec-6-ene-6-carbonyloxy]oxane-2-carboxylic acid)

3D Structure for NP0316222 ((2s,3s,4s,5r,6r)-3,4,5-trihydroxy-6-[(5r,8s)-2,10,10-trimethyltricyclo[6.3.0.0¹,⁵]undec-6-ene-6-carbonyloxy]oxane-2-carboxylic acid)