NP-MRD: Showing NP-Card for 9'-(acetyloxy)-12'-[(acetyloxy)methyl]-3'-methyl-10'-oxaspiro[oxirane-2,7'-tricyclo[6.4.0.0²,⁴]dodecan]-11'-en-3'-ylmethyl acetate (NP0237739)

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Record Information

Version

2.0

Created at

2022-09-06 20:58:25 UTC

Updated at

2022-09-06 20:58:26 UTC

NP-MRD ID

NP0237739

Secondary Accession Numbers

None

Natural Product Identification

Common Name

9'-(acetyloxy)-12'-[(acetyloxy)methyl]-3'-methyl-10'-oxaspiro[oxirane-2,7'-tricyclo[6.4.0.0²,⁴]dodecan]-11'-en-3'-ylmethyl acetate

Description

[9'-(Acetyloxy)-12'-[(acetyloxy)methyl]-3'-methyl-10'-oxaspiro[oxirane-2,7'-tricyclo[6.4.0.0²,⁴]Dodecan]-11'-en-3'-yl]methyl acetate belongs to the class of organic compounds known as aromadendrane sesquiterpenoids. These are sesquiterpenoids with a structure based on an aromadendrane (a cyclopropa[e]azulene derivative) skeleton. Some aromadendrane sesquiterpenoids are found in essential oils. Certain aromadendrane Sesquiterpenoids from the Leaves of Xylopia brasiliensis were found to possess antifungal activities. 9'-(acetyloxy)-12'-[(acetyloxy)methyl]-3'-methyl-10'-oxaspiro[oxirane-2,7'-tricyclo[6.4.0.0²,⁴]dodecan]-11'-en-3'-ylmethyl acetate is found in Plagiochila semidecurrens. [9'-(Acetyloxy)-12'-[(acetyloxy)methyl]-3'-methyl-10'-oxaspiro[oxirane-2,7'-tricyclo[6.4.0.0²,⁴]Dodecan]-11'-en-3'-yl]methyl acetate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004161513512D          

 29 32  0  0  0  0            999 V2000
    4.3576    3.3771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1144    2.5887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3101    2.4051    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6755    1.9840    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4324    1.1956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6281    1.0120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0669    1.6168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2626    1.4332    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0194    0.6449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2151    0.4613    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6540    1.0661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1503    0.8825    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8971    1.8544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5806    0.0401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3849    0.2237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0299   -0.2907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0299   -1.1157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3849   -1.6301    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5806   -1.4465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2226   -0.7032    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5081   -1.1157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5081   -0.2907    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7444   -0.7032    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4202   -1.1764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4202   -0.2300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3483    0.5919    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0241    1.0651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9522    1.8869    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7718    0.7164    0.0000 C   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  2  0  0  0  0
  7  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
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
  9 14  1  0  0  0  0
 14 15  1  0  0  0  0
  6 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 14 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 20 22  1  0  0  0  0
 17 23  1  0  0  0  0
 16 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 27 29  1  0  0  0  0
M  END

     RDKit          3D

 57 60  0  0  0  0  0  0  0  0999 V2000
    0.2786   -4.3366    2.3363 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8712   -3.5986    1.7877 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8999   -4.2844    1.4840 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8726   -2.2068    1.5940 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0497   -1.6551    1.0619 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9546   -0.1621    0.8971 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8102    0.6175    1.5414 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7593    1.9929    1.4188 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2674    2.4830    0.1670 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.1526    2.1734   -0.8919 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7697    3.1493   -1.6655 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6991    2.8071   -2.7769 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5196    4.3542   -1.3996 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8829    1.8726   -0.0990 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9048    0.3845    0.0104 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4399   -0.1151    0.4354 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4180    0.4657   -0.6314 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2479    1.4528    0.1064 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4663    2.7759    0.0301 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1610    2.5388    0.7475 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2319    3.6443    1.6891 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2645    2.3012    2.0891 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3233   -0.9598   -0.3376 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7630   -1.8536   -1.4246 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4580   -1.6512    0.4317 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2473   -2.4401   -0.4096 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9535   -1.9839   -1.4916 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7813   -2.8919   -2.3510 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8965   -0.7530   -1.7635 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9185   -3.6815    2.9760 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1026   -5.1782    2.9496 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8891   -4.7761    1.5245 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2443   -2.0365    0.0171 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9194   -1.9422    1.6527 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5602    0.1218    2.1761 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1846    3.5673    0.2345 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5952    3.5307   -3.6309 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3599    1.8197   -3.1978 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7382    2.7523   -2.4272 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6554    2.1334   -1.1571 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1009   -0.0939   -0.9976 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6674    0.0455    1.4939 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0120    0.8149   -1.5805 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2719    1.5804   -0.2989 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3057    1.2309    1.2102 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0361    3.6142    0.4261 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2110    2.9021   -1.0610 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2611    3.7173    2.0680 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4888    4.4434    1.9420 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5661   -2.4981   -1.8217 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0971   -2.4230   -1.0346 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3925   -1.2158   -2.2776 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9703   -2.2959    1.1892 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0466   -0.9039    1.0049 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1288   -3.6403   -2.8533 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3767   -2.3022   -3.0563 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4839   -3.4074   -1.6514 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  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  2  0
  9 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 17 23  1  0
 23 24  1  6
 23 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 27 29  2  0
 15  6  1  0
 23 16  1  0
 20 14  1  0
 20 22  1  1
  1 30  1  0
  1 31  1  0
  1 32  1  0
  5 33  1  0
  5 34  1  0
  7 35  1  0
  9 36  1  1
 12 37  1  0
 12 38  1  0
 12 39  1  0
 14 40  1  6
 15 41  1  6
 16 42  1  1
 17 43  1  6
 18 44  1  0
 18 45  1  0
 19 46  1  0
 19 47  1  0
 21 48  1  0
 21 49  1  0
 24 50  1  0
 24 51  1  0
 24 52  1  0
 25 53  1  0
 25 54  1  0
 28 55  1  0
 28 56  1  0
 28 57  1  0
M  END


  Mrv1533004161513512D          

 29 32  0  0  0  0            999 V2000
    4.3576    3.3771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1144    2.5887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3101    2.4051    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6755    1.9840    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4324    1.1956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6281    1.0120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0669    1.6168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2626    1.4332    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0194    0.6449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2151    0.4613    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6540    1.0661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1503    0.8825    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8971    1.8544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5806    0.0401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3849    0.2237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0299   -0.2907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0299   -1.1157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3849   -1.6301    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5806   -1.4465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2226   -0.7032    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5081   -1.1157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5081   -0.2907    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7444   -0.7032    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4202   -1.1764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4202   -0.2300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3483    0.5919    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0241    1.0651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9522    1.8869    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7718    0.7164    0.0000 C   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  2  0  0  0  0
  7  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
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
  9 14  1  0  0  0  0
 14 15  1  0  0  0  0
  6 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 14 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 20 22  1  0  0  0  0
 17 23  1  0  0  0  0
 16 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 27 29  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0237739

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)OCC1=COC(OC(C)=O)C2C1C1C(CCC22CO2)C1(C)COC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C21H28O8/c1-11(22)25-7-14-8-26-19(29-13(3)24)18-16(14)17-15(5-6-21(18)10-28-21)20(17,4)9-27-12(2)23/h8,15-19H,5-7,9-10H2,1-4H3

> <INCHI_KEY>
JHVOFEZRFCOCHL-UHFFFAOYSA-N

> <FORMULA>
C21H28O8

> <MOLECULAR_WEIGHT>
408.447

> <EXACT_MASS>
408.178417862

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
57

> <JCHEM_AVERAGE_POLARIZABILITY>
42.143879202467964

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
[9'-(acetyloxy)-12'-[(acetyloxy)methyl]-3'-methyl-10'-oxaspiro[oxirane-2,7'-tricyclo[6.4.0.0²,⁴]dodecan]-11'-en-3'-yl]methyl acetate

> <ALOGPS_LOGP>
1.69

> <JCHEM_LOGP>
0.5580278806666656

> <ALOGPS_LOGS>
-4.12

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.123456316326767

> <JCHEM_POLAR_SURFACE_AREA>
100.66

> <JCHEM_REFRACTIVITY>
98.33779999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.09e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
9'-(acetyloxy)-12'-[(acetyloxy)methyl]-3'-methyl-10'-oxaspiro[oxirane-2,7'-tricyclo[6.4.0.0²,⁴]dodecan]-11'-en-3'-ylmethyl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 16-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   16-APR-15         0                                  
HETATM    1  C   UNK     0       8.134   6.304   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.680   4.832   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       6.179   4.490   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       8.728   3.703   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       8.274   2.232   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.772   1.889   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.725   3.018   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       4.224   2.675   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       3.770   1.204   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       2.268   0.861   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       1.221   1.990   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -0.281   1.647   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       1.675   3.462   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.817   0.075   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.318   0.418   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.522  -0.543   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.522  -2.083   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.318  -3.043   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.817  -2.700   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.149  -1.313   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.815  -2.083   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       2.815  -0.543   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       8.856  -1.313   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      10.118  -2.196   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      10.118  -0.429   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       9.983   1.105   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      11.245   1.988   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      11.111   3.522   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      12.641   1.337   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   15                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   14                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11                                                            
CONECT   14    9   15   20                                                  
CONECT   15   14    6   16                                                  
CONECT   16   15   17   23                                                  
CONECT   17   16   18   23                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   14   21   22                                             
CONECT   21   20   22                                                       
CONECT   22   21   20                                                       
CONECT   23   17   16   24   25                                             
CONECT   24   23                                                            
CONECT   25   23   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27                                                            
MASTER        0    0    0    0    0    0    0    0   29    0   64    0
END

View in JSmol

Synonyms

Value	Source
[9'-(Acetyloxy)-12'-[(acetyloxy)methyl]-3'-methyl-10'-oxaspiro[oxirane-2,7'-tricyclo[6.4.0.0,]dodecan]-11'-en-3'-yl]methyl acetic acid	Generator
[9'-(Acetyloxy)-12'-[(acetyloxy)methyl]-3'-methyl-10'-oxaspiro[oxirane-2,7'-tricyclo[6.4.0.0²,⁴]dodecan]-11'-en-3'-yl]methyl acetic acid	Generator

Chemical Formula

C₂₁H₂₈O₈

Average Mass

408.4470 Da

Monoisotopic Mass

408.17842 Da

IUPAC Name

[9'-(acetyloxy)-12'-[(acetyloxy)methyl]-3'-methyl-10'-oxaspiro[oxirane-2,7'-tricyclo[6.4.0.0²,⁴]dodecan]-11'-en-3'-yl]methyl acetate

Traditional Name

9'-(acetyloxy)-12'-[(acetyloxy)methyl]-3'-methyl-10'-oxaspiro[oxirane-2,7'-tricyclo[6.4.0.0²,⁴]dodecan]-11'-en-3'-ylmethyl acetate

CAS Registry Number

Not Available

SMILES

CC(=O)OCC1=COC(OC(C)=O)C2C1C1C(CCC22CO2)C1(C)COC(C)=O

InChI Identifier

InChI=1S/C21H28O8/c1-11(22)25-7-14-8-26-19(29-13(3)24)18-16(14)17-15(5-6-21(18)10-28-21)20(17,4)9-27-12(2)23/h8,15-19H,5-7,9-10H2,1-4H3

InChI Key

JHVOFEZRFCOCHL-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
Plagiochila semidecurrens	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as aromadendrane sesquiterpenoids. These are sesquiterpenoids with a structure based on an aromadendrane (a cyclopropa[e]azulene derivative) skeleton. Some aromadendrane sesquiterpenoids are found in essential oils. Certain aromadendrane Sesquiterpenoids from the Leaves of Xylopia brasiliensis were found to possess antifungal activities.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Aromadendrane sesquiterpenoids

Alternative Parents

Substituents

Aromadendrane sesquiterpenoid
Tricarboxylic acid or derivatives
Carboxylic acid ester
Acetal
Carboxylic acid derivative
Dialkyl ether
Oxirane
Ether
Organoheterocyclic compound
Oxacycle
Carbonyl group
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
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	1.69	ALOGPS
logP	0.56	ChemAxon
logS	-4.1	ALOGPS
pKa (Strongest Basic)	-4.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	100.66 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	98.34 m³·mol⁻¹	ChemAxon
Polarizability	42.14 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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

14037347

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 9'-(acetyloxy)-12'-[(acetyloxy)methyl]-3'-methyl-10'-oxaspiro[oxirane-2,7'-tricyclo[6.4.0.0²,⁴]dodecan]-11'-en-3'-ylmethyl acetate (NP0237739)

MOL for NP0237739 (9'-(acetyloxy)-12'-[(acetyloxy)methyl]-3'-methyl-10'-oxaspiro[oxirane-2,7'-tricyclo[6.4.0.0²,⁴]dodecan]-11'-en-3'-ylmethyl acetate)

3D MOL for NP0237739 (9'-(acetyloxy)-12'-[(acetyloxy)methyl]-3'-methyl-10'-oxaspiro[oxirane-2,7'-tricyclo[6.4.0.0²,⁴]dodecan]-11'-en-3'-ylmethyl acetate)

3D SDF for NP0237739 (9'-(acetyloxy)-12'-[(acetyloxy)methyl]-3'-methyl-10'-oxaspiro[oxirane-2,7'-tricyclo[6.4.0.0²,⁴]dodecan]-11'-en-3'-ylmethyl acetate)

3D-SDF for NP0237739 (9'-(acetyloxy)-12'-[(acetyloxy)methyl]-3'-methyl-10'-oxaspiro[oxirane-2,7'-tricyclo[6.4.0.0²,⁴]dodecan]-11'-en-3'-ylmethyl acetate)

PDB for NP0237739 (9'-(acetyloxy)-12'-[(acetyloxy)methyl]-3'-methyl-10'-oxaspiro[oxirane-2,7'-tricyclo[6.4.0.0²,⁴]dodecan]-11'-en-3'-ylmethyl acetate)

3D PDB for NP0237739 (9'-(acetyloxy)-12'-[(acetyloxy)methyl]-3'-methyl-10'-oxaspiro[oxirane-2,7'-tricyclo[6.4.0.0²,⁴]dodecan]-11'-en-3'-ylmethyl acetate)

SMILES for NP0237739 (9'-(acetyloxy)-12'-[(acetyloxy)methyl]-3'-methyl-10'-oxaspiro[oxirane-2,7'-tricyclo[6.4.0.0²,⁴]dodecan]-11'-en-3'-ylmethyl acetate)

INCHI for NP0237739 (9'-(acetyloxy)-12'-[(acetyloxy)methyl]-3'-methyl-10'-oxaspiro[oxirane-2,7'-tricyclo[6.4.0.0²,⁴]dodecan]-11'-en-3'-ylmethyl acetate)

Structure for NP0237739 (9'-(acetyloxy)-12'-[(acetyloxy)methyl]-3'-methyl-10'-oxaspiro[oxirane-2,7'-tricyclo[6.4.0.0²,⁴]dodecan]-11'-en-3'-ylmethyl acetate)

3D Structure for NP0237739 (9'-(acetyloxy)-12'-[(acetyloxy)methyl]-3'-methyl-10'-oxaspiro[oxirane-2,7'-tricyclo[6.4.0.0²,⁴]dodecan]-11'-en-3'-ylmethyl acetate)