NP-MRD: Showing NP-Card for (1s,6s,7as)-4-[(acetyloxy)methyl]-1-[(3-methylbutanoyl)oxy]-6,7a-dihydro-1h-spiro[cyclopenta[c]pyran-7,2'-oxiran]-6-yl 3-methylbutanoate (NP0182109)

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Record Information

Version

2.0

Created at

2022-09-03 20:44:08 UTC

Updated at

2022-09-03 20:44:08 UTC

NP-MRD ID

NP0182109

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,6s,7as)-4-[(acetyloxy)methyl]-1-[(3-methylbutanoyl)oxy]-6,7a-dihydro-1h-spiro[cyclopenta[c]pyran-7,2'-oxiran]-6-yl 3-methylbutanoate

Description

(1S,6S,7aS)-4-[(acetyloxy)methyl]-1-[(3-methylbutanoyl)oxy]-6,7a-dihydro-1H-spiro[cyclopenta[c]pyran-7,2'-oxirane]-6-yl 3-methylbutanoate belongs to the class of organic compounds known as iridoids and derivatives. These are monoterpenes containing a skeleton structurally characterized by the presence of a cylopentane fused to a pyran ( forming a 4,7-dimethylcyclopenta[c]pyran), or a derivative where the pentane moiety is open. (1s,6s,7as)-4-[(acetyloxy)methyl]-1-[(3-methylbutanoyl)oxy]-6,7a-dihydro-1h-spiro[cyclopenta[c]pyran-7,2'-oxiran]-6-yl 3-methylbutanoate is found in Valeriana jatamansi. Based on a literature review very few articles have been published on (1S,6S,7aS)-4-[(acetyloxy)methyl]-1-[(3-methylbutanoyl)oxy]-6,7a-dihydro-1H-spiro[cyclopenta[c]pyran-7,2'-oxirane]-6-yl 3-methylbutanoate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309032222442D          

 30 32  0  0  1  0            999 V2000
    3.6763   -3.4374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8513   -3.4374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4388   -4.1519    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4388   -2.7229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6138   -2.7229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2013   -2.0084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3763   -2.0084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0362   -1.2940    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3763   -0.5795    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0362    0.1350    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8612    0.1350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2737   -0.5795    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2737    0.8494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0987    0.8494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5112    1.5639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5112    0.1350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2013   -0.5795    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6138   -1.2940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4208   -1.1225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5070   -0.3020    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2215    0.1105    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9360   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9360   -1.1270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6505    0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3649   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0794    0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3649   -1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7534    0.0336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2013    0.6467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0083    0.8182    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  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  1  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
  9 17  1  0  0  0  0
 17 18  1  6  0  0  0
  6 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  1  0  0  0
 21 22  1  0  0  0  0
 22 23  2  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
 20 28  1  0  0  0  0
 17 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 28 30  1  0  0  0  0
M  END

     RDKit          3D

 60 62  0  0  0  0  0  0  0  0999 V2000
    1.2325    7.4556   -1.0442 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5852    6.1275   -0.8688 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3014    5.7848    0.3006 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2946    5.2849   -1.9136 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2946    4.0372   -1.8289 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4778    2.9937   -1.1185 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6737    3.1688   -0.5785 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2659    2.1107    0.0715 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8436    0.7653   -0.0342 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4439   -0.0501    0.9450 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2813   -1.1000    0.5826 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5126   -1.3319   -0.6452 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9139   -1.9605    1.6182 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7617   -3.0121    0.9643 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4112   -3.8944    1.9932 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8659   -2.3602    0.1403 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3354    0.7893    0.0760 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1630    1.6737   -1.0006 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1266    1.0985   -1.6805 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4149   -0.2595   -1.1555 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.6920   -0.1893   -0.5142 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7517   -0.9950   -0.9505 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4945   -1.7590   -1.9201 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0928   -0.9548   -0.3149 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3227   -2.0974    0.6352 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2090   -3.4095   -0.0993 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7642   -1.9561    1.1367 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3028   -0.5199   -0.2110 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3286   -1.5099    0.8466 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4547   -1.6794   -0.3007 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3404    7.4017   -0.9906 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9573    7.9040   -2.0287 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8732    8.1671   -0.2781 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5322    3.7051   -2.8798 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3115    4.1404   -1.3490 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1484    4.1396   -0.6673 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1398    0.4350   -1.0576 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1720   -2.4560    2.2595 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6191   -1.3182    2.2208 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1635   -3.6364    0.2642 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7526   -3.3438    2.8811 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3252   -4.3666    1.5443 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7286   -4.7375    2.2182 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0762   -1.3527    0.5368 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6038   -2.3311   -0.9448 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8079   -2.9490    0.1998 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0797    1.1788    1.0882 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6281    1.5824   -2.5151 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4753   -1.0227   -1.9848 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2995    0.0240    0.1624 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8472   -1.0588   -1.1379 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6711   -2.0527    1.5242 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6301   -3.3265   -1.1043 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1128   -3.6207   -0.2211 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7053   -4.2102    0.4866 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8975   -2.4253    2.1278 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0085   -0.8668    1.1721 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4097   -2.4112    0.3518 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2441   -2.1174    0.9656 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2876   -1.3258    1.7570 H   0  0  0  0  0  0  0  0  0  0  0  0
 26 25  1  0
 25 27  1  0
 25 24  1  0
 24 22  1  0
 22 23  2  0
 22 21  1  0
 21 20  1  0
 20 19  1  0
 19 18  2  0
 18 17  1  0
 17  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
  9  8  1  0
  8  7  1  0
  7  6  2  0
  6  5  1  0
  5  4  1  0
  4  2  1  0
  2  1  1  0
  2  3  2  0
 17 28  1  0
 28 29  1  0
 29 30  1  0
 28 20  1  0
 28 30  1  6
  6 18  1  0
 26 53  1  0
 26 54  1  0
 26 55  1  0
 25 52  1  0
 27 56  1  0
 27 57  1  0
 27 58  1  0
 24 50  1  0
 24 51  1  0
 20 49  1  6
 19 48  1  0
 17 47  1  1
  9 37  1  6
 13 38  1  0
 13 39  1  0
 14 40  1  0
 15 41  1  0
 15 42  1  0
 15 43  1  0
 16 44  1  0
 16 45  1  0
 16 46  1  0
  7 36  1  0
  5 34  1  0
  5 35  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
 29 59  1  0
 29 60  1  0
M  END


  Mrv1652309032222442D          

 30 32  0  0  1  0            999 V2000
    3.6763   -3.4374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8513   -3.4374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4388   -4.1519    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4388   -2.7229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6138   -2.7229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2013   -2.0084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3763   -2.0084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0362   -1.2940    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3763   -0.5795    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0362    0.1350    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8612    0.1350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2737   -0.5795    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2737    0.8494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0987    0.8494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5112    1.5639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5112    0.1350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2013   -0.5795    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6138   -1.2940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4208   -1.1225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5070   -0.3020    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2215    0.1105    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9360   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9360   -1.1270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6505    0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3649   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0794    0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3649   -1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7534    0.0336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2013    0.6467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0083    0.8182    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  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  1  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
  9 17  1  0  0  0  0
 17 18  1  6  0  0  0
  6 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  1  0  0  0
 21 22  1  0  0  0  0
 22 23  2  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
 20 28  1  0  0  0  0
 17 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 28 30  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0182109

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)CC(=O)O[C@H]1C=C2[C@H]([C@H](OC(=O)CC(C)C)OC=C2COC(C)=O)C11CO1

> <INCHI_IDENTIFIER>
InChI=1S/C22H30O8/c1-12(2)6-18(24)29-17-8-16-15(9-26-14(5)23)10-27-21(20(16)22(17)11-28-22)30-19(25)7-13(3)4/h8,10,12-13,17,20-21H,6-7,9,11H2,1-5H3/t17-,20+,21-,22?/m0/s1

> <INCHI_KEY>
BDIAUFOIMFAIPU-LFNVVQRMSA-N

> <FORMULA>
C22H30O8

> <MOLECULAR_WEIGHT>
422.474

> <EXACT_MASS>
422.194067926

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
60

> <JCHEM_AVERAGE_POLARIZABILITY>
44.456776318027956

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,6S,7aS)-4-[(acetyloxy)methyl]-1-[(3-methylbutanoyl)oxy]-6,7a-dihydro-1H-spiro[cyclopenta[c]pyran-7,2'-oxirane]-6-yl 3-methylbutanoate

> <JCHEM_LOGP>
2.236523454333333

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.236658611948695

> <JCHEM_PKA_STRONGEST_BASIC>
-4.145751632836598

> <JCHEM_POLAR_SURFACE_AREA>
100.66

> <JCHEM_REFRACTIVITY>
105.25389999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1S,6S,7aS)-4-[(acetyloxy)methyl]-1-[(3-methylbutanoyl)oxy]-6,7a-dihydro-1H-spiro[cyclopenta[c]pyran-7,2'-oxirane]-6-yl 3-methylbutanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 03-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-SEP-22         0                                  
HETATM    1  C   UNK     0       6.862  -6.416   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.322  -6.416   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       4.552  -7.750   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       4.552  -5.083   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       3.012  -5.083   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.242  -3.749   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.702  -3.749   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -0.068  -2.415   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       0.702  -1.082   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -0.068   0.252   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      -1.608   0.252   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -2.378  -1.082   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      -2.378   1.586   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -3.918   1.586   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -4.688   2.919   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -4.688   0.252   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.242  -1.082   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.012  -2.415   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.519  -2.095   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.680  -0.564   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       6.013   0.206   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       7.347  -0.564   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       7.347  -2.104   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       8.681   0.206   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      10.015  -0.564   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      11.348   0.206   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      10.015  -2.104   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       3.273   0.063   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       2.242   1.207   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       3.749   1.527   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                                                       
CONECT    6    5    7   18                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   17                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14                                                            
CONECT   17    9   18   28                                                  
CONECT   18   17    6   19                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   28                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25                                                            
CONECT   28   20   17   29   30                                             
CONECT   29   28   30                                                       
CONECT   30   29   28                                                       
MASTER        0    0    0    0    0    0    0    0   30    0   64    0
END

View in JSmol

Synonyms

Value	Source
(1S,6S,7AS)-4-[(acetyloxy)methyl]-1-[(3-methylbutanoyl)oxy]-6,7a-dihydro-1H-spiro[cyclopenta[c]pyran-7,2'-oxirane]-6-yl 3-methylbutanoic acid	Generator

Chemical Formula

C₂₂H₃₀O₈

Average Mass

422.4740 Da

Monoisotopic Mass

422.19407 Da

IUPAC Name

(1S,6S,7aS)-4-[(acetyloxy)methyl]-1-[(3-methylbutanoyl)oxy]-6,7a-dihydro-1H-spiro[cyclopenta[c]pyran-7,2'-oxirane]-6-yl 3-methylbutanoate

Traditional Name

(1S,6S,7aS)-4-[(acetyloxy)methyl]-1-[(3-methylbutanoyl)oxy]-6,7a-dihydro-1H-spiro[cyclopenta[c]pyran-7,2'-oxirane]-6-yl 3-methylbutanoate

CAS Registry Number

Not Available

SMILES

CC(C)CC(=O)O[C@H]1C=C2[C@H]([C@H](OC(=O)CC(C)C)OC=C2COC(C)=O)C11CO1

InChI Identifier

InChI=1S/C22H30O8/c1-12(2)6-18(24)29-17-8-16-15(9-26-14(5)23)10-27-21(20(16)22(17)11-28-22)30-19(25)7-13(3)4/h8,10,12-13,17,20-21H,6-7,9,11H2,1-5H3/t17-,20+,21-,22?/m0/s1

InChI Key

BDIAUFOIMFAIPU-LFNVVQRMSA-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
Valeriana jatamansi	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as iridoids and derivatives. These are monoterpenes containing a skeleton structurally characterized by the presence of a cylopentane fused to a pyran ( forming a 4,7-dimethylcyclopenta[c]pyran), or a derivative where the pentane moiety is open.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Monoterpenoids

Direct Parent

Iridoids and derivatives

Alternative Parents

Substituents

Iridoid-skeleton
Bicyclic monoterpenoid
Tricarboxylic acid or derivatives
Fatty acid ester
Fatty acyl
Carboxylic acid ester
Acetal
Carboxylic acid derivative
Dialkyl ether
Oxirane
Ether
Oxacycle
Organoheterocyclic compound
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organooxygen compound
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	2.24	ChemAxon
pKa (Strongest Acidic)	18.24	ChemAxon
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	11	ChemAxon
Refractivity	105.25 m³·mol⁻¹	ChemAxon
Polarizability	44.46 Å³	ChemAxon
Number of Rings	3	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

2298519

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

3033955

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1s,6s,7as)-4-[(acetyloxy)methyl]-1-[(3-methylbutanoyl)oxy]-6,7a-dihydro-1h-spiro[cyclopenta[c]pyran-7,2'-oxiran]-6-yl 3-methylbutanoate (NP0182109)

MOL for NP0182109 ((1s,6s,7as)-4-[(acetyloxy)methyl]-1-[(3-methylbutanoyl)oxy]-6,7a-dihydro-1h-spiro[cyclopenta[c]pyran-7,2'-oxiran]-6-yl 3-methylbutanoate)

3D MOL for NP0182109 ((1s,6s,7as)-4-[(acetyloxy)methyl]-1-[(3-methylbutanoyl)oxy]-6,7a-dihydro-1h-spiro[cyclopenta[c]pyran-7,2'-oxiran]-6-yl 3-methylbutanoate)

3D SDF for NP0182109 ((1s,6s,7as)-4-[(acetyloxy)methyl]-1-[(3-methylbutanoyl)oxy]-6,7a-dihydro-1h-spiro[cyclopenta[c]pyran-7,2'-oxiran]-6-yl 3-methylbutanoate)

3D-SDF for NP0182109 ((1s,6s,7as)-4-[(acetyloxy)methyl]-1-[(3-methylbutanoyl)oxy]-6,7a-dihydro-1h-spiro[cyclopenta[c]pyran-7,2'-oxiran]-6-yl 3-methylbutanoate)

PDB for NP0182109 ((1s,6s,7as)-4-[(acetyloxy)methyl]-1-[(3-methylbutanoyl)oxy]-6,7a-dihydro-1h-spiro[cyclopenta[c]pyran-7,2'-oxiran]-6-yl 3-methylbutanoate)

3D PDB for NP0182109 ((1s,6s,7as)-4-[(acetyloxy)methyl]-1-[(3-methylbutanoyl)oxy]-6,7a-dihydro-1h-spiro[cyclopenta[c]pyran-7,2'-oxiran]-6-yl 3-methylbutanoate)

SMILES for NP0182109 ((1s,6s,7as)-4-[(acetyloxy)methyl]-1-[(3-methylbutanoyl)oxy]-6,7a-dihydro-1h-spiro[cyclopenta[c]pyran-7,2'-oxiran]-6-yl 3-methylbutanoate)

INCHI for NP0182109 ((1s,6s,7as)-4-[(acetyloxy)methyl]-1-[(3-methylbutanoyl)oxy]-6,7a-dihydro-1h-spiro[cyclopenta[c]pyran-7,2'-oxiran]-6-yl 3-methylbutanoate)

Structure for NP0182109 ((1s,6s,7as)-4-[(acetyloxy)methyl]-1-[(3-methylbutanoyl)oxy]-6,7a-dihydro-1h-spiro[cyclopenta[c]pyran-7,2'-oxiran]-6-yl 3-methylbutanoate)

3D Structure for NP0182109 ((1s,6s,7as)-4-[(acetyloxy)methyl]-1-[(3-methylbutanoyl)oxy]-6,7a-dihydro-1h-spiro[cyclopenta[c]pyran-7,2'-oxiran]-6-yl 3-methylbutanoate)