NP-MRD: Showing NP-Card for (1s)-2-[(1'r,2r,6's,7's,8'r,11'r,13's)-8',11'-dihydroxy-13'-methyl-12'-oxo-9'-oxaspiro[oxirane-2,2'-tricyclo[5.3.3.0¹,⁶]tridecan]-7'-yl]-1-(furan-3-yl)ethyl acetate (NP0167832)

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Record Information

Version

2.0

Created at

2022-09-03 03:30:22 UTC

Updated at

2022-09-03 03:30:22 UTC

NP-MRD ID

NP0167832

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s)-2-[(1'r,2r,6's,7's,8'r,11'r,13's)-8',11'-dihydroxy-13'-methyl-12'-oxo-9'-oxaspiro[oxirane-2,2'-tricyclo[5.3.3.0¹,⁶]tridecan]-7'-yl]-1-(furan-3-yl)ethyl acetate

Description

(1S)-2-[(1'R,2R,6'S,7'S,8'R,11'R,13'S)-8',11'-dihydroxy-13'-methyl-12'-oxo-9'-oxaspiro[oxirane-2,2'-tricyclo[5.3.3.0¹,⁶]Tridecane]-7'-yl]-1-(furan-3-yl)ethyl acetate belongs to the class of organic compounds known as oxanes. Oxanes are compounds containing an oxane (tetrahydropyran) ring, which is a six-member saturated aliphatic heterocycle with one oxygen atom and five carbon atoms. (1s)-2-[(1'r,2r,6's,7's,8'r,11'r,13's)-8',11'-dihydroxy-13'-methyl-12'-oxo-9'-oxaspiro[oxirane-2,2'-tricyclo[5.3.3.0¹,⁶]tridecan]-7'-yl]-1-(furan-3-yl)ethyl acetate is found in Teucrium montanum. Based on a literature review very few articles have been published on (1S)-2-[(1'R,2R,6'S,7'S,8'R,11'R,13'S)-8',11'-dihydroxy-13'-methyl-12'-oxo-9'-oxaspiro[oxirane-2,2'-tricyclo[5.3.3.0¹,⁶]Tridecane]-7'-yl]-1-(furan-3-yl)ethyl acetate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309032205302D          

 30 34  0  0  1  0            999 V2000
    0.6714    3.8212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0124    3.3249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7469    3.6474    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1128    2.5060    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5461    2.0096    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4458    1.1908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3136    0.8683    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3062    0.0433    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4587   -0.2656    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8844   -0.5452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5619   -1.3046    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7094   -0.5526    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0183   -1.3176    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2979    0.0255    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3052    0.8505    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7292    1.6724    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9021    1.4464    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5932    2.2114    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6394    0.5226    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7406    1.3413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5003    1.6631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1588    1.1660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0576    0.3473    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.8763    0.2461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3793   -0.4124    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3055    2.3321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4909    3.1360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3128    3.2081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6353    2.4487    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0127    1.9074    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
  5  4  1  1  0  0  0
  5  6  1  0  0  0  0
  7  6  1  6  0  0  0
  7  8  1  0  0  0  0
  8  9  1  1  0  0  0
  8 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  1  0  0  0
 12 14  1  0  0  0  0
 14 15  1  1  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
  7 17  1  0  0  0  0
 17 18  1  6  0  0  0
 14 19  1  0  0  0  0
  7 19  1  0  0  0  0
 19 20  1  1  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 14 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 23 25  1  1  0  0  0
  5 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 26 30  2  0  0  0  0
M  END

     RDKit          3D

 58 62  0  0  0  0  0  0  0  0999 V2000
    4.0599   -2.4995    1.8103 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6043   -1.6728    0.6389 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8673   -2.1550   -0.4955 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9443   -0.4699    0.8111 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5481    0.2489   -0.3204 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1505    0.6968   -0.2584 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0281   -0.2494   -0.1571 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1008   -1.0670    1.0800 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1523   -2.5619    0.8831 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0849   -0.8130    1.9870 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9285   -0.5160    3.1459 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4079   -0.9478    1.3820 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7764   -2.3057    1.3305 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4358   -0.2939    0.0294 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4713   -1.3188   -1.0369 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3070   -1.7308   -1.5613 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1326   -1.1576   -1.3494 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2477   -0.4666   -2.5294 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2436    0.6261   -0.2136 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4683    1.1948   -1.5721 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6141    2.2149   -1.4316 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8641    1.3426   -1.2429 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6487    0.6169    0.0363 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.6703    1.5508    1.2557 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5691    0.5422    1.0328 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4986    1.4392   -0.3385 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8936    2.2415    0.6903 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7601    3.1828    0.1895 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8842    2.9541   -1.1067 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1375    1.9103   -1.4585 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0515   -2.0950    2.1179 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3471   -2.2355    2.6384 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0646   -3.5653    1.5755 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8165   -0.3379   -1.2222 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0185    1.4204    0.6239 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0323    1.4435   -1.1098 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9695   -0.8313    1.7297 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0826   -2.9368    0.4239 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7414   -3.0162    0.4649 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2048   -2.9714    1.9432 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1557   -0.5080    2.1033 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7766   -2.3431    1.2965 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9701   -2.2343   -0.5833 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1834   -1.0752   -1.8822 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6544   -1.9432   -1.2600 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0328   -0.9890   -3.3152 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1958    1.4378    0.5234 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6353    1.6369   -2.0953 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8914    0.4311   -2.2923 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4558    2.7267   -0.4649 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6897    2.8686   -2.2966 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6922    2.0683   -1.0778 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0858    0.7350   -2.1169 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0935    2.5687    1.1325 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8641    1.5015    1.9826 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5887    2.1597    1.7062 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2778    3.9874    0.7058 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1009    1.5604   -2.4816 H   0  0  0  0  0  0  0  0  0  0  0  0
  9  8  1  0
  8 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  1  6
 15 16  1  0
 16 17  1  0
 17 18  1  0
 17  7  1  0
  7  6  1  6
  6  5  1  0
  5  4  1  0
  4  2  1  0
  2  1  1  0
  2  3  2  0
  5 26  1  0
 26 30  2  0
 30 29  1  0
 29 28  1  0
 28 27  2  0
  7 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
  7  8  1  0
 27 26  1  0
 23 25  1  1
 19 14  1  0
 23 14  1  0
  9 38  1  0
  9 39  1  0
  9 40  1  0
  8 37  1  1
 12 41  1  1
 13 42  1  0
 15 43  1  0
 15 44  1  0
 17 45  1  1
 18 46  1  0
  6 35  1  0
  6 36  1  0
  5 34  1  6
  1 31  1  0
  1 32  1  0
  1 33  1  0
 30 58  1  0
 28 57  1  0
 27 56  1  0
 19 47  1  1
 20 48  1  0
 20 49  1  0
 21 50  1  0
 21 51  1  0
 22 52  1  0
 22 53  1  0
 24 54  1  0
 24 55  1  0
M  END


  Mrv1652309032205302D          

 30 34  0  0  1  0            999 V2000
    0.6714    3.8212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0124    3.3249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7469    3.6474    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1128    2.5060    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5461    2.0096    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4458    1.1908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3136    0.8683    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3062    0.0433    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4587   -0.2656    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8844   -0.5452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5619   -1.3046    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7094   -0.5526    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0183   -1.3176    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2979    0.0255    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3052    0.8505    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7292    1.6724    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9021    1.4464    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5932    2.2114    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6394    0.5226    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7406    1.3413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5003    1.6631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1588    1.1660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0576    0.3473    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.8763    0.2461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3793   -0.4124    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3055    2.3321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4909    3.1360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3128    3.2081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6353    2.4487    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0127    1.9074    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
  5  4  1  1  0  0  0
  5  6  1  0  0  0  0
  7  6  1  6  0  0  0
  7  8  1  0  0  0  0
  8  9  1  1  0  0  0
  8 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  1  0  0  0
 12 14  1  0  0  0  0
 14 15  1  1  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
  7 17  1  0  0  0  0
 17 18  1  6  0  0  0
 14 19  1  0  0  0  0
  7 19  1  0  0  0  0
 19 20  1  1  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 14 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 23 25  1  1  0  0  0
  5 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 26 30  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0167832

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]1C(=O)[C@H](O)[C@]23CO[C@@H](O)[C@@]1(C[C@H](OC(C)=O)C1=COC=C1)[C@H]2CCC[C@]31CO1

> <INCHI_IDENTIFIER>
InChI=1S/C22H28O8/c1-12-17(24)18(25)22-11-28-19(26)21(12,16(22)4-3-6-20(22)10-29-20)8-15(30-13(2)23)14-5-7-27-9-14/h5,7,9,12,15-16,18-19,25-26H,3-4,6,8,10-11H2,1-2H3/t12-,15+,16-,18+,19-,20+,21-,22+/m1/s1

> <INCHI_KEY>
ZOVARCOHEIZNCO-BZQJATGJSA-N

> <FORMULA>
C22H28O8

> <MOLECULAR_WEIGHT>
420.458

> <EXACT_MASS>
420.178417862

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
58

> <JCHEM_AVERAGE_POLARIZABILITY>
42.361794563139235

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S)-2-[(1'R,2R,6'S,7'S,8'R,11'R,13'S)-8',11'-dihydroxy-13'-methyl-12'-oxo-9'-oxaspiro[oxirane-2,2'-tricyclo[5.3.3.0^{1,6}]tridecane]-7'-yl]-1-(furan-3-yl)ethyl acetate

> <ALOGPS_LOGP>
0.93

> <JCHEM_LOGP>
0.9765827293333332

> <ALOGPS_LOGS>
-3.01

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.83817948703986

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.866784569341627

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8533702880924916

> <JCHEM_POLAR_SURFACE_AREA>
118.73000000000002

> <JCHEM_REFRACTIVITY>
101.88980000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.15e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S)-2-[(1'R,2R,6'S,7'S,8'R,11'R,13'S)-8',11'-dihydroxy-13'-methyl-12'-oxo-9'-oxaspiro[oxirane-2,2'-tricyclo[5.3.3.0^{1,6}]tridecane]-7'-yl]-1-(furan-3-yl)ethyl acetate

> <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       1.253   7.133   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.023   6.206   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -1.394   6.808   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       0.211   4.678   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      -1.019   3.751   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.832   2.223   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.585   1.621   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.572   0.081   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.856  -0.496   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.651  -1.018   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       1.049  -2.435   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       3.191  -1.032   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       3.767  -2.459   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       4.289   0.048   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.303   1.588   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       3.228   3.122   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       1.684   2.700   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       1.107   4.128   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       3.060   0.975   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.249   2.504   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.667   3.104   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.896   2.177   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       5.707   0.648   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       7.236   0.459   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       6.308  -0.770   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      -2.437   4.353   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -2.783   5.854   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -4.317   5.988   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      -4.919   4.571   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      -3.757   3.560   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   26                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   17   19                                             
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   19   23                                             
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16    7   18                                                  
CONECT   18   17                                                            
CONECT   19   14    7   20                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   14   24   25                                             
CONECT   24   23   25                                                       
CONECT   25   24   23                                                       
CONECT   26    5   27   30                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   26                                                       
MASTER        0    0    0    0    0    0    0    0   30    0   68    0
END

View in JSmol

Synonyms

Value	Source
(1S)-2-[(1'r,2R,6's,7's,8'r,11'r,13's)-8',11'-Dihydroxy-13'-methyl-12'-oxo-9'-oxaspiro[oxirane-2,2'-tricyclo[5.3.3.0,]tridecane]-7'-yl]-1-(furan-3-yl)ethyl acetic acid	Generator

Chemical Formula

C₂₂H₂₈O₈

Average Mass

420.4580 Da

Monoisotopic Mass

420.17842 Da

IUPAC Name

(1S)-2-[(1'R,2R,6'S,7'S,8'R,11'R,13'S)-8',11'-dihydroxy-13'-methyl-12'-oxo-9'-oxaspiro[oxirane-2,2'-tricyclo[5.3.3.0^{1,6}]tridecane]-7'-yl]-1-(furan-3-yl)ethyl acetate

Traditional Name

(1S)-2-[(1'R,2R,6'S,7'S,8'R,11'R,13'S)-8',11'-dihydroxy-13'-methyl-12'-oxo-9'-oxaspiro[oxirane-2,2'-tricyclo[5.3.3.0^{1,6}]tridecane]-7'-yl]-1-(furan-3-yl)ethyl acetate

CAS Registry Number

Not Available

SMILES

C[C@@H]1C(=O)[C@H](O)[C@]23CO[C@@H](O)[C@@]1(C[C@H](OC(C)=O)C1=COC=C1)[C@H]2CCC[C@]31CO1

InChI Identifier

InChI=1S/C22H28O8/c1-12-17(24)18(25)22-11-28-19(26)21(12,16(22)4-3-6-20(22)10-29-20)8-15(30-13(2)23)14-5-7-27-9-14/h5,7,9,12,15-16,18-19,25-26H,3-4,6,8,10-11H2,1-2H3/t12-,15+,16-,18+,19-,20+,21-,22+/m1/s1

InChI Key

ZOVARCOHEIZNCO-BZQJATGJSA-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
Teucrium montanum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as oxanes. Oxanes are compounds containing an oxane (tetrahydropyran) ring, which is a six-member saturated aliphatic heterocycle with one oxygen atom and five carbon atoms.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Oxanes

Sub Class

Not Available

Direct Parent

Oxanes

Alternative Parents

Substituents

Oxane
Cyclic alcohol
Furan
Heteroaromatic compound
Carboxylic acid ester
Hemiacetal
Ketone
Secondary alcohol
Cyclic ketone
Monocarboxylic acid or derivatives
Ether
Oxirane
Dialkyl ether
Carboxylic acid derivative
Oxacycle
Carbonyl group
Organic oxide
Organic oxygen compound
Organooxygen compound
Hydrocarbon derivative
Alcohol
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	0.93	ALOGPS
logP	0.98	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	11.87	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	118.73 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	101.89 m³·mol⁻¹	ChemAxon
Polarizability	42.36 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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

162915275

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1s)-2-[(1'r,2r,6's,7's,8'r,11'r,13's)-8',11'-dihydroxy-13'-methyl-12'-oxo-9'-oxaspiro[oxirane-2,2'-tricyclo[5.3.3.0¹,⁶]tridecan]-7'-yl]-1-(furan-3-yl)ethyl acetate (NP0167832)

MOL for NP0167832 ((1s)-2-[(1'r,2r,6's,7's,8'r,11'r,13's)-8',11'-dihydroxy-13'-methyl-12'-oxo-9'-oxaspiro[oxirane-2,2'-tricyclo[5.3.3.0¹,⁶]tridecan]-7'-yl]-1-(furan-3-yl)ethyl acetate)

3D MOL for NP0167832 ((1s)-2-[(1'r,2r,6's,7's,8'r,11'r,13's)-8',11'-dihydroxy-13'-methyl-12'-oxo-9'-oxaspiro[oxirane-2,2'-tricyclo[5.3.3.0¹,⁶]tridecan]-7'-yl]-1-(furan-3-yl)ethyl acetate)

3D SDF for NP0167832 ((1s)-2-[(1'r,2r,6's,7's,8'r,11'r,13's)-8',11'-dihydroxy-13'-methyl-12'-oxo-9'-oxaspiro[oxirane-2,2'-tricyclo[5.3.3.0¹,⁶]tridecan]-7'-yl]-1-(furan-3-yl)ethyl acetate)

3D-SDF for NP0167832 ((1s)-2-[(1'r,2r,6's,7's,8'r,11'r,13's)-8',11'-dihydroxy-13'-methyl-12'-oxo-9'-oxaspiro[oxirane-2,2'-tricyclo[5.3.3.0¹,⁶]tridecan]-7'-yl]-1-(furan-3-yl)ethyl acetate)

PDB for NP0167832 ((1s)-2-[(1'r,2r,6's,7's,8'r,11'r,13's)-8',11'-dihydroxy-13'-methyl-12'-oxo-9'-oxaspiro[oxirane-2,2'-tricyclo[5.3.3.0¹,⁶]tridecan]-7'-yl]-1-(furan-3-yl)ethyl acetate)

3D PDB for NP0167832 ((1s)-2-[(1'r,2r,6's,7's,8'r,11'r,13's)-8',11'-dihydroxy-13'-methyl-12'-oxo-9'-oxaspiro[oxirane-2,2'-tricyclo[5.3.3.0¹,⁶]tridecan]-7'-yl]-1-(furan-3-yl)ethyl acetate)

SMILES for NP0167832 ((1s)-2-[(1'r,2r,6's,7's,8'r,11'r,13's)-8',11'-dihydroxy-13'-methyl-12'-oxo-9'-oxaspiro[oxirane-2,2'-tricyclo[5.3.3.0¹,⁶]tridecan]-7'-yl]-1-(furan-3-yl)ethyl acetate)

INCHI for NP0167832 ((1s)-2-[(1'r,2r,6's,7's,8'r,11'r,13's)-8',11'-dihydroxy-13'-methyl-12'-oxo-9'-oxaspiro[oxirane-2,2'-tricyclo[5.3.3.0¹,⁶]tridecan]-7'-yl]-1-(furan-3-yl)ethyl acetate)

Structure for NP0167832 ((1s)-2-[(1'r,2r,6's,7's,8'r,11'r,13's)-8',11'-dihydroxy-13'-methyl-12'-oxo-9'-oxaspiro[oxirane-2,2'-tricyclo[5.3.3.0¹,⁶]tridecan]-7'-yl]-1-(furan-3-yl)ethyl acetate)

3D Structure for NP0167832 ((1s)-2-[(1'r,2r,6's,7's,8'r,11'r,13's)-8',11'-dihydroxy-13'-methyl-12'-oxo-9'-oxaspiro[oxirane-2,2'-tricyclo[5.3.3.0¹,⁶]tridecan]-7'-yl]-1-(furan-3-yl)ethyl acetate)