NP-MRD: Showing NP-Card for 2,4,10,11,15,17-hexahydroxy-5,5,10,15-tetramethyl-7-oxapentacyclo[12.2.1.0¹,¹¹.0⁴,⁹.0⁶,⁸]heptadecan-3-yl acetate (NP0187176)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-04 03:15:22 UTC

Updated at

2022-09-04 03:15:22 UTC

NP-MRD ID

NP0187176

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2,4,10,11,15,17-hexahydroxy-5,5,10,15-tetramethyl-7-oxapentacyclo[12.2.1.0¹,¹¹.0⁴,⁹.0⁶,⁸]heptadecan-3-yl acetate

Description

2,4,10,11,15,17-Hexahydroxy-5,5,10,15-tetramethyl-7-oxapentacyclo[12.2.1.0¹,¹¹.0⁴,⁹.0⁶,⁸]Heptadecan-3-yl acetate belongs to the class of organic compounds known as grayanoids. These are diterpenoids containing a skeleton based on or derived from the ent-kaurane moiety. Grayanoids usually possess either one of the grayanane, the 2,4-seco-grayanane, the 9,10-seco-grayanane, the 1,5-seco-grayanane, the kalmane, or the leucothane skeleton. Some derivatives also include the 1,5-seco-kalmane skeleton. 2,4,10,11,15,17-hexahydroxy-5,5,10,15-tetramethyl-7-oxapentacyclo[12.2.1.0¹,¹¹.0⁴,⁹.0⁶,⁸]heptadecan-3-yl acetate is found in Pieris japonica. 2,4,10,11,15,17-Hexahydroxy-5,5,10,15-tetramethyl-7-oxapentacyclo[12.2.1.0¹,¹¹.0⁴,⁹.0⁶,⁸]Heptadecan-3-yl acetate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004191519302D          

 31 35  0  0  0  0            999 V2000
    2.2056    2.0192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9682    2.3340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0769    3.1518    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6221    1.8310    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5134    1.0132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7287    0.7503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1724    1.3596    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3868   -0.0275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6253    0.4505    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9151   -0.0557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5033    0.6592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1638   -0.3965    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1946   -0.8739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6649   -1.6024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5193   -1.5657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8765   -0.7646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2882   -1.4795    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7079   -0.8534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6920   -1.6783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4067   -1.2919    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2954   -0.2682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1030   -0.4367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9280   -0.4335    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5128    0.2794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9584    0.8903    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6240    1.3778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5432    1.6032    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2060    0.5519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2739    1.3741    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8250   -0.4783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3032   -1.1506    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
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  8  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
 10 13  1  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
  8 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
 18 20  1  0  0  0  0
 18 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
 22 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
  5 28  1  0  0  0  0
 21 28  1  0  0  0  0
 28 29  1  0  0  0  0
 13 30  1  0  0  0  0
  8 30  1  0  0  0  0
 30 31  1  0  0  0  0
M  END

     RDKit          3D

 65 69  0  0  0  0  0  0  0  0999 V2000
   -2.4463    4.3830   -1.3676 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9053    3.0123   -1.5137 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7038    2.4211   -2.5998 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5711    2.2591   -0.4115 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0414    0.9167   -0.5077 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3782    1.1307   -0.1317 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3627    1.9372    1.0354 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3641    0.0829    0.0506 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5907    0.8646    0.5963 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6665    0.7777   -0.4431 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0313    0.9859    0.0394 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3484    1.6075   -1.5244 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3856   -0.6532   -0.9075 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4638   -1.5548    0.2709 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1477   -2.0938    0.7546 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1009   -1.0068    1.0116 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5149   -0.4947    2.2825 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1825   -1.6592    1.1802 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1056   -3.1874    0.8702 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -1.7753    2.6002 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4441   -1.2888    0.5959 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8613   -1.9288   -0.7134 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.1419   -2.4478   -0.8786 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0546   -1.1006   -1.1706 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.2564   -0.0893   -0.0613 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0618   -0.6923    1.0820 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0283    1.0340   -0.6167 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8549    0.1392    0.4110 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9955    0.7926    1.6662 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9151   -0.3764   -1.2773 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4659   -1.5205   -1.8069 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9982    4.7180   -2.2669 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1804    4.4230   -0.5292 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6452    5.1226   -1.0779 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1006    0.6280   -1.5637 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7935    1.8229   -0.9151 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2481    1.4185    1.8463 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4060    1.9165    0.7875 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9641    0.4442    1.5394 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0518    1.8432    0.7481 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5508    0.1113    0.4646 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6754    1.3166   -0.8282 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8795    1.3076   -2.3041 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9726   -0.9405   -1.7736 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0383   -2.4695   -0.0760 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1041   -1.1747    1.1083 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3740   -2.6246    1.7270 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8307   -2.8623    0.0598 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4990   -1.2119    2.9616 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6423   -3.6747    1.4896 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1042   -3.3906   -0.1922 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0978   -3.5842    1.2488 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5508   -0.8775    2.9804 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2575   -1.6858    1.2939 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1117   -2.1879   -1.4695 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1814   -0.8340   -2.2142 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2124   -1.7669    0.9903 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0898   -0.2444    1.0516 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5729   -0.3743    2.0221 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9695    1.1462   -1.7396 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1269    0.6846   -0.5276 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0504    1.9700   -0.0607 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5223    1.6180    1.4843 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8906    0.4281   -2.0301 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1828   -1.4902   -2.7499 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  1  1
  9 10  1  0
 10 11  1  0
 10 12  1  6
 10 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  1
 16 18  1  0
 18 19  1  0
 18 20  1  1
 18 21  1  0
 21 22  1  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
 28 29  1  1
 13 30  1  0
 30 31  1  0
 28  5  1  0
 16  8  1  0
 28 21  1  0
 30  8  1  0
 24 22  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
  5 35  1  6
  6 36  1  6
  7 37  1  0
  9 38  1  0
  9 39  1  0
 11 40  1  0
 11 41  1  0
 11 42  1  0
 12 43  1  0
 13 44  1  6
 14 45  1  0
 14 46  1  0
 15 47  1  0
 15 48  1  0
 17 49  1  0
 19 50  1  0
 19 51  1  0
 19 52  1  0
 20 53  1  0
 21 54  1  1
 22 55  1  6
 24 56  1  6
 26 57  1  0
 26 58  1  0
 26 59  1  0
 27 60  1  0
 27 61  1  0
 27 62  1  0
 29 63  1  0
 30 64  1  6
 31 65  1  0
M  END


  Mrv1533004191519302D          

 31 35  0  0  0  0            999 V2000
    2.2056    2.0192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9682    2.3340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0769    3.1518    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6221    1.8310    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5134    1.0132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7287    0.7503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1724    1.3596    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3868   -0.0275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6253    0.4505    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9151   -0.0557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5033    0.6592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1638   -0.3965    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1946   -0.8739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6649   -1.6024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5193   -1.5657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8765   -0.7646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2882   -1.4795    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7079   -0.8534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6920   -1.6783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4067   -1.2919    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2954   -0.2682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1030   -0.4367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9280   -0.4335    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5128    0.2794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9584    0.8903    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6240    1.3778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5432    1.6032    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2060    0.5519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2739    1.3741    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8250   -0.4783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3032   -1.1506    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
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  8  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
 10 13  1  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
  8 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
 18 20  1  0  0  0  0
 18 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
 22 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
  5 28  1  0  0  0  0
 21 28  1  0  0  0  0
 28 29  1  0  0  0  0
 13 30  1  0  0  0  0
  8 30  1  0  0  0  0
 30 31  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0187176

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)OC1C(O)C23CC(C)(O)C(CCC2(O)C(C)(O)C2C4OC4C(C)(C)C12O)C3O

> <INCHI_IDENTIFIER>
InChI=1S/C22H34O9/c1-9(23)30-16-14(25)20-8-18(4,26)10(13(20)24)6-7-21(20,28)19(5,27)12-11-15(31-11)17(2,3)22(12,16)29/h10-16,24-29H,6-8H2,1-5H3

> <INCHI_KEY>
XRCWCMXMUOHEKM-UHFFFAOYSA-N

> <FORMULA>
C22H34O9

> <MOLECULAR_WEIGHT>
442.505

> <EXACT_MASS>
442.220282675

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
65

> <JCHEM_AVERAGE_POLARIZABILITY>
44.460288813243274

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2,4,10,11,15,17-hexahydroxy-5,5,10,15-tetramethyl-7-oxapentacyclo[12.2.1.0¹,¹¹.0⁴,⁹.0⁶,⁸]heptadecan-3-yl acetate

> <ALOGPS_LOGP>
-0.14

> <JCHEM_LOGP>
-2.2698470146666674

> <ALOGPS_LOGS>
-1.35

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.140427037225383

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.600858409143992

> <JCHEM_PKA_STRONGEST_BASIC>
-2.940924324979144

> <JCHEM_POLAR_SURFACE_AREA>
160.21

> <JCHEM_REFRACTIVITY>
104.09929999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.96e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2,4,10,11,15,17-hexahydroxy-5,5,10,15-tetramethyl-7-oxapentacyclo[12.2.1.0¹,¹¹.0⁴,⁹.0⁶,⁸]heptadecan-3-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 19-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-APR-15         0                                  
HETATM    1  C   UNK     0       4.117   3.769   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.541   4.357   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       5.743   5.883   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       6.761   3.418   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       6.558   1.891   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.094   1.401   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       4.055   2.538   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       4.455  -0.051   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.034   0.841   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.708  -0.104   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.940   1.231   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       0.306  -0.740   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       2.230  -1.631   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.108  -2.991   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.703  -2.923   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.369  -1.427   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       6.138  -2.762   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       6.921  -1.593   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.892  -3.133   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       8.226  -2.412   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       8.018  -0.501   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       9.526  -0.815   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      11.066  -0.809   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      10.291   0.521   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       9.256   1.662   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      10.498   2.572   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       8.481   2.993   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       7.851   1.030   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       7.978   2.565   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       3.407  -0.893   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       4.299  -2.148   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   28                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   16   30                                             
CONECT    9    8   10                                                       
CONECT   10    9   11   12   13                                             
CONECT   11   10                                                            
CONECT   12   10                                                            
CONECT   13   10   14   30                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15    8   17   18                                             
CONECT   17   16                                                            
CONECT   18   16   19   20   21                                             
CONECT   19   18                                                            
CONECT   20   18                                                            
CONECT   21   18   22   28                                                  
CONECT   22   21   23   24                                                  
CONECT   23   22   24                                                       
CONECT   24   23   22   25                                                  
CONECT   25   24   26   27   28                                             
CONECT   26   25                                                            
CONECT   27   25                                                            
CONECT   28   25    5   21   29                                             
CONECT   29   28                                                            
CONECT   30   13    8   31                                                  
CONECT   31   30                                                            
MASTER        0    0    0    0    0    0    0    0   31    0   70    0
END

View in JSmol

Synonyms

Value	Source
2,4,10,11,15,17-Hexahydroxy-5,5,10,15-tetramethyl-7-oxapentacyclo[12.2.1.0,.0,.0,]heptadecan-3-yl acetic acid	Generator
2,4,10,11,15,17-Hexahydroxy-5,5,10,15-tetramethyl-7-oxapentacyclo[12.2.1.0¹,¹¹.0⁴,⁹.0⁶,⁸]heptadecan-3-yl acetic acid	Generator

Chemical Formula

C₂₂H₃₄O₉

Average Mass

442.5050 Da

Monoisotopic Mass

442.22028 Da

IUPAC Name

2,4,10,11,15,17-hexahydroxy-5,5,10,15-tetramethyl-7-oxapentacyclo[12.2.1.0¹,¹¹.0⁴,⁹.0⁶,⁸]heptadecan-3-yl acetate

Traditional Name

2,4,10,11,15,17-hexahydroxy-5,5,10,15-tetramethyl-7-oxapentacyclo[12.2.1.0¹,¹¹.0⁴,⁹.0⁶,⁸]heptadecan-3-yl acetate

CAS Registry Number

Not Available

SMILES

CC(=O)OC1C(O)C23CC(C)(O)C(CCC2(O)C(C)(O)C2C4OC4C(C)(C)C12O)C3O

InChI Identifier

InChI=1S/C22H34O9/c1-9(23)30-16-14(25)20-8-18(4,26)10(13(20)24)6-7-21(20,28)19(5,27)12-11-15(31-11)17(2,3)22(12,16)29/h10-16,24-29H,6-8H2,1-5H3

InChI Key

XRCWCMXMUOHEKM-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
Pieris japonica	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as grayanoids. These are diterpenoids containing a skeleton based on or derived from the ent-kaurane moiety. Grayanoids usually possess either one of the grayanane, the 2,4-seco-grayanane, the 9,10-seco-grayanane, the 1,5-seco-grayanane, the kalmane, or the leucothane skeleton. Some derivatives also include the 1,5-seco-kalmane skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Grayanoids

Alternative Parents

Substituents

Grayanoid
Oxane
Cyclic alcohol
Tertiary alcohol
Carboxylic acid ester
Secondary alcohol
Carboxylic acid derivative
Dialkyl ether
Oxirane
Ether
Monocarboxylic acid or derivatives
Polyol
Oxacycle
Organoheterocyclic compound
Alcohol
Organic oxygen compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Carbonyl group
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	-0.14	ALOGPS
logP	-2.3	ChemAxon
logS	-1.4	ALOGPS
pKa (Strongest Acidic)	12.6	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	160.21 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	104.1 m³·mol⁻¹	ChemAxon
Polarizability	44.46 Å³	ChemAxon
Number of Rings	5	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

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 2,4,10,11,15,17-hexahydroxy-5,5,10,15-tetramethyl-7-oxapentacyclo[12.2.1.0¹,¹¹.0⁴,⁹.0⁶,⁸]heptadecan-3-yl acetate (NP0187176)

MOL for NP0187176 (2,4,10,11,15,17-hexahydroxy-5,5,10,15-tetramethyl-7-oxapentacyclo[12.2.1.0¹,¹¹.0⁴,⁹.0⁶,⁸]heptadecan-3-yl acetate)

3D MOL for NP0187176 (2,4,10,11,15,17-hexahydroxy-5,5,10,15-tetramethyl-7-oxapentacyclo[12.2.1.0¹,¹¹.0⁴,⁹.0⁶,⁸]heptadecan-3-yl acetate)

3D SDF for NP0187176 (2,4,10,11,15,17-hexahydroxy-5,5,10,15-tetramethyl-7-oxapentacyclo[12.2.1.0¹,¹¹.0⁴,⁹.0⁶,⁸]heptadecan-3-yl acetate)

3D-SDF for NP0187176 (2,4,10,11,15,17-hexahydroxy-5,5,10,15-tetramethyl-7-oxapentacyclo[12.2.1.0¹,¹¹.0⁴,⁹.0⁶,⁸]heptadecan-3-yl acetate)

PDB for NP0187176 (2,4,10,11,15,17-hexahydroxy-5,5,10,15-tetramethyl-7-oxapentacyclo[12.2.1.0¹,¹¹.0⁴,⁹.0⁶,⁸]heptadecan-3-yl acetate)

3D PDB for NP0187176 (2,4,10,11,15,17-hexahydroxy-5,5,10,15-tetramethyl-7-oxapentacyclo[12.2.1.0¹,¹¹.0⁴,⁹.0⁶,⁸]heptadecan-3-yl acetate)

SMILES for NP0187176 (2,4,10,11,15,17-hexahydroxy-5,5,10,15-tetramethyl-7-oxapentacyclo[12.2.1.0¹,¹¹.0⁴,⁹.0⁶,⁸]heptadecan-3-yl acetate)

INCHI for NP0187176 (2,4,10,11,15,17-hexahydroxy-5,5,10,15-tetramethyl-7-oxapentacyclo[12.2.1.0¹,¹¹.0⁴,⁹.0⁶,⁸]heptadecan-3-yl acetate)

Structure for NP0187176 (2,4,10,11,15,17-hexahydroxy-5,5,10,15-tetramethyl-7-oxapentacyclo[12.2.1.0¹,¹¹.0⁴,⁹.0⁶,⁸]heptadecan-3-yl acetate)

3D Structure for NP0187176 (2,4,10,11,15,17-hexahydroxy-5,5,10,15-tetramethyl-7-oxapentacyclo[12.2.1.0¹,¹¹.0⁴,⁹.0⁶,⁸]heptadecan-3-yl acetate)