NP-MRD: Showing NP-Card for (1r,2r,4r,6s,7r,8s,9r,10s,11r,13s,15s,16r,17r)-6,7,8,9-tetrahydroxy-8-(hydroxymethyl)-4,17-dimethyl-5-oxo-13-phenyl-15-(prop-1-en-2-yl)-12,14,18-trioxapentacyclo[11.4.1.0¹,¹⁰.0²,⁶.0¹¹,¹⁵]octadecan-16-yl acetate (NP0235605)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-06 18:18:01 UTC

Updated at

2022-09-06 18:18:01 UTC

NP-MRD ID

NP0235605

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,2r,4r,6s,7r,8s,9r,10s,11r,13s,15s,16r,17r)-6,7,8,9-tetrahydroxy-8-(hydroxymethyl)-4,17-dimethyl-5-oxo-13-phenyl-15-(prop-1-en-2-yl)-12,14,18-trioxapentacyclo[11.4.1.0¹,¹⁰.0²,⁶.0¹¹,¹⁵]octadecan-16-yl acetate

Description

(1R,2R,4R,6S,7R,8S,9R,10S,11R,13S,15S,16R,17R)-6,7,8,9-tetrahydroxy-8-(hydroxymethyl)-4,17-dimethyl-5-oxo-13-phenyl-15-(prop-1-en-2-yl)-12,14,18-trioxapentacyclo[11.4.1.0¹,¹⁰.0²,⁶.0¹¹,¹⁵]Octadecan-16-yl acetate belongs to the class of organic compounds known as rhamnofolane and daphnane diterpenoids. These are diterpenoids with a structure based on one the rhamnofolane or daphnane skeleton. The rhamnofolane and daphnane skeletons are closely related, being formally derived from casbane by two cyclizations (6,10 and 5,14) followed by cleavage of the 1,15 (daphnane) or 2,15 (rhamnofolane) cyclopropane bonds. (1r,2r,4r,6s,7r,8s,9r,10s,11r,13s,15s,16r,17r)-6,7,8,9-tetrahydroxy-8-(hydroxymethyl)-4,17-dimethyl-5-oxo-13-phenyl-15-(prop-1-en-2-yl)-12,14,18-trioxapentacyclo[11.4.1.0¹,¹⁰.0²,⁶.0¹¹,¹⁵]octadecan-16-yl acetate is found in Daphne genkwa. Based on a literature review very few articles have been published on (1R,2R,4R,6S,7R,8S,9R,10S,11R,13S,15S,16R,17R)-6,7,8,9-tetrahydroxy-8-(hydroxymethyl)-4,17-dimethyl-5-oxo-13-phenyl-15-(prop-1-en-2-yl)-12,14,18-trioxapentacyclo[11.4.1.0¹,¹⁰.0²,⁶.0¹¹,¹⁵]Octadecan-16-yl acetate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309062220182D          

 40 45  0  0  1  0            999 V2000
    2.0899    2.4931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5884    1.7891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9274    2.3557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5008    0.7507    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3408    0.6389    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1822   -0.1804    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0991   -0.2010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4877    0.4007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4045    0.3801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8364   -0.3078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2551   -1.0410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4346   -0.9547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2513    0.2680    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8669   -0.2683    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2894   -0.8649    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6014   -1.6286    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8402   -2.0721    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3930   -1.8609    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7534   -2.7040    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9473   -2.6983    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9988   -3.5832    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0682   -1.3868    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6579   -2.2486    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1185   -0.5634    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.8390   -1.3209    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8335   -0.1517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6500   -0.7168    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6629    0.6555    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.3815    1.2964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8425    0.7427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5061   -0.0106    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6921   -0.1448    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1788   -0.8947    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6160    0.2845    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2332    0.0763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8225    1.0497    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3723    1.8383    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4519    2.0309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0161    1.4290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6910    2.8205    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  4  2  1  1  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  1  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
  7 12  1  0  0  0  0
  6 13  1  0  0  0  0
 14 13  1  1  0  0  0
  4 14  1  0  0  0  0
 15 14  1  1  0  0  0
 15 16  1  0  0  0  0
 16 17  1  6  0  0  0
 16 18  1  0  0  0  0
 18 19  1  1  0  0  0
 18 20  1  6  0  0  0
 20 21  1  0  0  0  0
 18 22  1  0  0  0  0
 22 23  1  6  0  0  0
 22 24  1  0  0  0  0
 24 25  1  6  0  0  0
 24 26  1  0  0  0  0
 26 27  2  0  0  0  0
 26 28  1  0  0  0  0
 28 29  1  1  0  0  0
 28 30  1  0  0  0  0
 31 30  1  6  0  0  0
 24 31  1  0  0  0  0
 31 32  1  0  0  0  0
 15 32  1  0  0  0  0
 32 33  1  1  0  0  0
  6 33  1  0  0  0  0
 32 34  1  0  0  0  0
 34 35  1  6  0  0  0
 34 36  1  0  0  0  0
  4 36  1  0  0  0  0
 36 37  1  1  0  0  0
 37 38  1  0  0  0  0
 38 39  1  0  0  0  0
 38 40  2  0  0  0  0
M  END

     RDKit          3D

 76 81  0  0  0  0  0  0  0  0999 V2000
   -4.2611    0.7835   -1.7330 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0596    1.3356   -1.7138 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7944    2.5301   -2.5433 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0033    0.7228   -0.8437 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.5097   -0.4741   -0.2801 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4595   -1.3481   -0.4208 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9552   -2.7512   -0.3749 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9726   -3.5618   -1.5085 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4296   -4.8593   -1.4695 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8894   -5.3991   -0.2895 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8820   -4.6079    0.8580 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4199   -3.3107    0.7969 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0878   -1.0952   -1.7420 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8330    0.2921   -1.6375 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4963    0.3633   -0.8712 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3260   -0.6716   -1.5384 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9604   -0.8601   -2.8958 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7857   -0.5760   -1.4956 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2569   -1.6883   -2.2594 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4003    0.6202   -2.1574 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9981    0.7050   -3.5140 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2637   -0.8660   -0.1165 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.6562   -1.0064   -0.0492 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7175    0.0863    0.8518 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7920    1.4305    0.5320 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5882   -0.0465    2.0911 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7424   -0.3994    2.1542 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7539    0.3413    3.2280 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5113   -0.7308    4.2319 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4442    0.8278    2.5829 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3709   -0.1730    1.4262 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1832   -0.0023    0.5625 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4576   -1.2541    0.4867 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7754    0.9255    1.2324 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5335    0.1810    2.3166 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7240    1.6297    0.2876 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2997    2.9225   -0.0404 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9830    4.0710    0.3311 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5515    5.4439   -0.0046 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0393    3.9290    0.9975 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4891   -0.0885   -1.1407 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0500    1.1972   -2.3491 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2003    2.2965   -3.5628 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3276    3.4024   -2.1425 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7154    2.7672   -2.5903 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6231   -3.1798   -2.4510 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4496   -5.5035   -2.3421 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2582   -6.4007   -0.1886 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2507   -5.0477    1.7917 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4317   -2.7343    1.7084 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7459    0.7424   -2.6296 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8962    1.3844   -0.9154 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0462   -1.6582   -1.0601 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3676   -1.7132   -3.1851 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3908   -1.4334   -3.1956 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5003    0.4826   -2.1910 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0885    1.5982   -1.7421 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6639    1.3298   -3.9349 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8547   -1.8875    0.1442 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9992   -1.3614   -0.9031 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6707    1.8330    0.7401 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2623    1.2003    3.7555 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4365   -1.3632    4.2789 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6147   -1.3406    4.0104 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4151   -0.2865    5.2545 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6785    0.7229    3.3263 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6941    1.8501    2.2383 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4120   -1.1809    1.9286 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2688    1.7781    1.7740 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7067    0.8318    3.2246 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5825   -0.0777    2.0062 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0600   -0.7650    2.6035 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6809    1.7492    0.8732 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9097    6.1287    0.7870 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1106    5.7402   -0.9383 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4566    5.5279   -0.1531 H   0  0  0  0  0  0  0  0  0  0  0  0
 29 28  1  0
 28 30  1  0
 30 31  1  0
 31 24  1  0
 24 25  1  6
 24 22  1  0
 22 23  1  0
 22 18  1  0
 18 19  1  6
 18 20  1  0
 20 21  1  0
 18 16  1  0
 16 17  1  0
 16 15  1  0
 15 14  1  0
 14 13  1  0
 13  6  1  0
  6  5  1  0
  5  4  1  0
  4 36  1  0
 36 37  1  0
 37 38  1  0
 38 39  1  0
 38 40  2  0
 36 34  1  0
 34 35  1  0
 34 32  1  0
 32 33  1  6
  4  2  1  6
  2  3  1  0
  2  1  2  3
  6  7  1  6
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 24 26  1  0
 26 27  2  0
 26 28  1  0
 32 31  1  0
 12  7  1  0
 32 15  1  0
  4 14  1  0
 33  6  1  0
 29 63  1  0
 29 64  1  0
 29 65  1  0
 28 62  1  1
 30 66  1  0
 30 67  1  0
 31 68  1  1
 25 61  1  0
 22 59  1  1
 23 60  1  0
 19 55  1  0
 20 56  1  0
 20 57  1  0
 21 58  1  0
 16 53  1  1
 17 54  1  0
 15 52  1  1
 14 51  1  6
 36 73  1  1
 39 74  1  0
 39 75  1  0
 39 76  1  0
 34 69  1  1
 35 70  1  0
 35 71  1  0
 35 72  1  0
  3 43  1  0
  3 44  1  0
  3 45  1  0
  1 41  1  0
  1 42  1  0
  8 46  1  0
  9 47  1  0
 10 48  1  0
 11 49  1  0
 12 50  1  0
M  END


  Mrv1652309062220182D          

 40 45  0  0  1  0            999 V2000
    2.0899    2.4931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5884    1.7891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9274    2.3557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5008    0.7507    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3408    0.6389    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1822   -0.1804    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0991   -0.2010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4877    0.4007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4045    0.3801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8364   -0.3078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2551   -1.0410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4346   -0.9547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2513    0.2680    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8669   -0.2683    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2894   -0.8649    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6014   -1.6286    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8402   -2.0721    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3930   -1.8609    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7534   -2.7040    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9473   -2.6983    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9988   -3.5832    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0682   -1.3868    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6579   -2.2486    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1185   -0.5634    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.8390   -1.3209    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8335   -0.1517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6500   -0.7168    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6629    0.6555    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.3815    1.2964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8425    0.7427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5061   -0.0106    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6921   -0.1448    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1788   -0.8947    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6160    0.2845    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2332    0.0763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8225    1.0497    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3723    1.8383    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4519    2.0309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0161    1.4290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6910    2.8205    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  4  2  1  1  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  1  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
  7 12  1  0  0  0  0
  6 13  1  0  0  0  0
 14 13  1  1  0  0  0
  4 14  1  0  0  0  0
 15 14  1  1  0  0  0
 15 16  1  0  0  0  0
 16 17  1  6  0  0  0
 16 18  1  0  0  0  0
 18 19  1  1  0  0  0
 18 20  1  6  0  0  0
 20 21  1  0  0  0  0
 18 22  1  0  0  0  0
 22 23  1  6  0  0  0
 22 24  1  0  0  0  0
 24 25  1  6  0  0  0
 24 26  1  0  0  0  0
 26 27  2  0  0  0  0
 26 28  1  0  0  0  0
 28 29  1  1  0  0  0
 28 30  1  0  0  0  0
 31 30  1  6  0  0  0
 24 31  1  0  0  0  0
 31 32  1  0  0  0  0
 15 32  1  0  0  0  0
 32 33  1  1  0  0  0
  6 33  1  0  0  0  0
 32 34  1  0  0  0  0
 34 35  1  6  0  0  0
 34 36  1  0  0  0  0
  4 36  1  0  0  0  0
 36 37  1  1  0  0  0
 37 38  1  0  0  0  0
 38 39  1  0  0  0  0
 38 40  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0235605

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]1C[C@@H]2[C@](O)([C@H](O)[C@](O)(CO)[C@H](O)[C@H]3[C@H]4O[C@@]5(O[C@]4([C@H](OC(C)=O)[C@@H](C)[C@]23O5)C(C)=C)C2=CC=CC=C2)C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C29H36O11/c1-13(2)27-22(37-16(5)31)15(4)28-18-11-14(3)20(32)26(18,36)24(34)25(35,12-30)21(33)19(28)23(27)38-29(39-27,40-28)17-9-7-6-8-10-17/h6-10,14-15,18-19,21-24,30,33-36H,1,11-12H2,2-5H3/t14-,15-,18-,19+,21-,22-,23-,24-,25+,26-,27+,28+,29-/m1/s1

> <INCHI_KEY>
SEXUAJFNRBNIBX-ZBZOBOIWSA-N

> <FORMULA>
C29H36O11

> <MOLECULAR_WEIGHT>
560.596

> <EXACT_MASS>
560.225761979

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
76

> <JCHEM_AVERAGE_POLARIZABILITY>
56.62379745778515

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,2R,4R,6S,7R,8S,9R,10S,11R,13S,15S,16R,17R)-6,7,8,9-tetrahydroxy-8-(hydroxymethyl)-4,17-dimethyl-5-oxo-13-phenyl-15-(prop-1-en-2-yl)-12,14,18-trioxapentacyclo[11.4.1.0^{1,10}.0^{2,6}.0^{11,15}]octadecan-16-yl acetate

> <JCHEM_LOGP>
0.7310984936666669

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.33184202303294

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.553254314663866

> <JCHEM_PKA_STRONGEST_BASIC>
-3.1449505187138014

> <JCHEM_POLAR_SURFACE_AREA>
172.20999999999998

> <JCHEM_REFRACTIVITY>
135.6063

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2R,4R,6S,7R,8S,9R,10S,11R,13S,15S,16R,17R)-6,7,8,9-tetrahydroxy-8-(hydroxymethyl)-4,17-dimethyl-5-oxo-13-phenyl-15-(prop-1-en-2-yl)-12,14,18-trioxapentacyclo[11.4.1.0^{1,10}.0^{2,6}.0^{11,15}]octadecan-16-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-22         0                                  
HETATM    1  C   UNK     0       3.901   4.654   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.965   3.340   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.731   4.397   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.801   1.401   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       4.370   1.193   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       4.073  -0.337   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.785  -0.375   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.510   0.748   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.222   0.710   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.028  -0.575   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.943  -1.943   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.411  -1.782   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       2.336   0.500   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       1.618  -0.501   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.407  -1.614   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.989  -3.040   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       1.568  -3.868   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       4.467  -3.474   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       5.140  -5.047   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       3.635  -5.037   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       3.731  -6.689   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       5.727  -2.589   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       6.828  -4.197   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       5.821  -1.052   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       7.166  -2.466   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       7.156  -0.283   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       8.680  -1.338   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       6.837   1.224   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       8.179   2.420   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       5.306   1.386   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       4.678  -0.020   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       3.159  -0.270   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       4.067  -1.670   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       1.150   0.531   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -0.435   0.143   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       1.535   1.959   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0       0.695   3.431   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0      -0.844   3.791   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      -1.897   2.667   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0      -1.290   5.265   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   14   36                                             
CONECT    5    4    6                                                       
CONECT    6    5    7   13   33                                             
CONECT    7    6    8   12                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11    7                                                       
CONECT   13    6   14                                                       
CONECT   14   13    4   15                                                  
CONECT   15   14   16   32                                                  
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19   20   22                                             
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20                                                            
CONECT   22   18   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25   26   31                                             
CONECT   25   24                                                            
CONECT   26   24   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31                                                       
CONECT   31   30   24   32                                                  
CONECT   32   31   15   33   34                                             
CONECT   33   32    6                                                       
CONECT   34   32   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34    4   37                                                  
CONECT   37   36   38                                                       
CONECT   38   37   39   40                                                  
CONECT   39   38                                                            
CONECT   40   38                                                            
MASTER        0    0    0    0    0    0    0    0   40    0   90    0
END

View in JSmol

Synonyms

Value	Source
(1R,2R,4R,6S,7R,8S,9R,10S,11R,13S,15S,16R,17R)-6,7,8,9-Tetrahydroxy-8-(hydroxymethyl)-4,17-dimethyl-5-oxo-13-phenyl-15-(prop-1-en-2-yl)-12,14,18-trioxapentacyclo[11.4.1.0,.0,.0,]octadecan-16-yl acetic acid	Generator

Chemical Formula

C₂₉H₃₆O₁₁

Average Mass

560.5960 Da

Monoisotopic Mass

560.22576 Da

IUPAC Name

Traditional Name

CAS Registry Number

Not Available

SMILES

C[C@@H]1C[C@@H]2[C@](O)([C@H](O)[C@](O)(CO)[C@H](O)[C@H]3[C@H]4O[C@@]5(O[C@]4([C@H](OC(C)=O)[C@@H](C)[C@]23O5)C(C)=C)C2=CC=CC=C2)C1=O

InChI Identifier

InChI=1S/C29H36O11/c1-13(2)27-22(37-16(5)31)15(4)28-18-11-14(3)20(32)26(18,36)24(34)25(35,12-30)21(33)19(28)23(27)38-29(39-27,40-28)17-9-7-6-8-10-17/h6-10,14-15,18-19,21-24,30,33-36H,1,11-12H2,2-5H3/t14-,15-,18-,19+,21-,22-,23-,24-,25+,26-,27+,28+,29-/m1/s1

InChI Key

SEXUAJFNRBNIBX-ZBZOBOIWSA-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
Daphne genkwa	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as rhamnofolane and daphnane diterpenoids. These are diterpenoids with a structure based on one the rhamnofolane or daphnane skeleton. The rhamnofolane and daphnane skeletons are closely related, being formally derived from casbane by two cyclizations (6,10 and 5,14) followed by cleavage of the 1,15 (daphnane) or 2,15 (rhamnofolane) cyclopropane bonds.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Rhamnofolane and daphnane diterpenoids

Alternative Parents

Substituents

Daphnane diterpenoid
1,3-dioxepane
Carboxylic acid orthoester
Ortho ester
Dioxepane
Meta-dioxane
Monocyclic benzene moiety
Benzenoid
Meta-dioxolane
Tertiary alcohol
Cyclic alcohol
Carboxylic acid ester
Secondary alcohol
Orthocarboxylic acid derivative
Ketone
Oxacycle
Carboxylic acid derivative
Organoheterocyclic compound
Polyol
Monocarboxylic acid or derivatives
Organic oxide
Carbonyl group
Organic oxygen compound
Hydrocarbon derivative
Primary alcohol
Alcohol
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

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

Predicted Properties

Property	Value	Source
logP	0.73	ChemAxon
pKa (Strongest Acidic)	11.55	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	172.21 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	135.61 m³·mol⁻¹	ChemAxon
Polarizability	56.62 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	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

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

162943851

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1r,2r,4r,6s,7r,8s,9r,10s,11r,13s,15s,16r,17r)-6,7,8,9-tetrahydroxy-8-(hydroxymethyl)-4,17-dimethyl-5-oxo-13-phenyl-15-(prop-1-en-2-yl)-12,14,18-trioxapentacyclo[11.4.1.0¹,¹⁰.0²,⁶.0¹¹,¹⁵]octadecan-16-yl acetate (NP0235605)

MOL for NP0235605 ((1r,2r,4r,6s,7r,8s,9r,10s,11r,13s,15s,16r,17r)-6,7,8,9-tetrahydroxy-8-(hydroxymethyl)-4,17-dimethyl-5-oxo-13-phenyl-15-(prop-1-en-2-yl)-12,14,18-trioxapentacyclo[11.4.1.0¹,¹⁰.0²,⁶.0¹¹,¹⁵]octadecan-16-yl acetate)

3D MOL for NP0235605 ((1r,2r,4r,6s,7r,8s,9r,10s,11r,13s,15s,16r,17r)-6,7,8,9-tetrahydroxy-8-(hydroxymethyl)-4,17-dimethyl-5-oxo-13-phenyl-15-(prop-1-en-2-yl)-12,14,18-trioxapentacyclo[11.4.1.0¹,¹⁰.0²,⁶.0¹¹,¹⁵]octadecan-16-yl acetate)

3D SDF for NP0235605 ((1r,2r,4r,6s,7r,8s,9r,10s,11r,13s,15s,16r,17r)-6,7,8,9-tetrahydroxy-8-(hydroxymethyl)-4,17-dimethyl-5-oxo-13-phenyl-15-(prop-1-en-2-yl)-12,14,18-trioxapentacyclo[11.4.1.0¹,¹⁰.0²,⁶.0¹¹,¹⁵]octadecan-16-yl acetate)

3D-SDF for NP0235605 ((1r,2r,4r,6s,7r,8s,9r,10s,11r,13s,15s,16r,17r)-6,7,8,9-tetrahydroxy-8-(hydroxymethyl)-4,17-dimethyl-5-oxo-13-phenyl-15-(prop-1-en-2-yl)-12,14,18-trioxapentacyclo[11.4.1.0¹,¹⁰.0²,⁶.0¹¹,¹⁵]octadecan-16-yl acetate)

PDB for NP0235605 ((1r,2r,4r,6s,7r,8s,9r,10s,11r,13s,15s,16r,17r)-6,7,8,9-tetrahydroxy-8-(hydroxymethyl)-4,17-dimethyl-5-oxo-13-phenyl-15-(prop-1-en-2-yl)-12,14,18-trioxapentacyclo[11.4.1.0¹,¹⁰.0²,⁶.0¹¹,¹⁵]octadecan-16-yl acetate)

3D PDB for NP0235605 ((1r,2r,4r,6s,7r,8s,9r,10s,11r,13s,15s,16r,17r)-6,7,8,9-tetrahydroxy-8-(hydroxymethyl)-4,17-dimethyl-5-oxo-13-phenyl-15-(prop-1-en-2-yl)-12,14,18-trioxapentacyclo[11.4.1.0¹,¹⁰.0²,⁶.0¹¹,¹⁵]octadecan-16-yl acetate)

SMILES for NP0235605 ((1r,2r,4r,6s,7r,8s,9r,10s,11r,13s,15s,16r,17r)-6,7,8,9-tetrahydroxy-8-(hydroxymethyl)-4,17-dimethyl-5-oxo-13-phenyl-15-(prop-1-en-2-yl)-12,14,18-trioxapentacyclo[11.4.1.0¹,¹⁰.0²,⁶.0¹¹,¹⁵]octadecan-16-yl acetate)

INCHI for NP0235605 ((1r,2r,4r,6s,7r,8s,9r,10s,11r,13s,15s,16r,17r)-6,7,8,9-tetrahydroxy-8-(hydroxymethyl)-4,17-dimethyl-5-oxo-13-phenyl-15-(prop-1-en-2-yl)-12,14,18-trioxapentacyclo[11.4.1.0¹,¹⁰.0²,⁶.0¹¹,¹⁵]octadecan-16-yl acetate)

Structure for NP0235605 ((1r,2r,4r,6s,7r,8s,9r,10s,11r,13s,15s,16r,17r)-6,7,8,9-tetrahydroxy-8-(hydroxymethyl)-4,17-dimethyl-5-oxo-13-phenyl-15-(prop-1-en-2-yl)-12,14,18-trioxapentacyclo[11.4.1.0¹,¹⁰.0²,⁶.0¹¹,¹⁵]octadecan-16-yl acetate)

3D Structure for NP0235605 ((1r,2r,4r,6s,7r,8s,9r,10s,11r,13s,15s,16r,17r)-6,7,8,9-tetrahydroxy-8-(hydroxymethyl)-4,17-dimethyl-5-oxo-13-phenyl-15-(prop-1-en-2-yl)-12,14,18-trioxapentacyclo[11.4.1.0¹,¹⁰.0²,⁶.0¹¹,¹⁵]octadecan-16-yl acetate)