NP-MRD: Showing NP-Card for (1's,3r,3ar,4s,5r,6's,7'r,7ar,9's)-5,7'-dihydroxy-7a-methyl-10'-methylidene-2',11'-dioxo-hexahydro-3'-oxaspiro[2-benzofuran-4,5'-tricyclo[7.2.1.0¹,⁶]dodecan]-3-yl acetate (NP0210262)

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Record Information

Version

2.0

Created at

2022-09-05 07:59:45 UTC

Updated at

2022-09-05 07:59:46 UTC

NP-MRD ID

NP0210262

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1's,3r,3ar,4s,5r,6's,7'r,7ar,9's)-5,7'-dihydroxy-7a-methyl-10'-methylidene-2',11'-dioxo-hexahydro-3'-oxaspiro[2-benzofuran-4,5'-tricyclo[7.2.1.0¹,⁶]dodecan]-3-yl acetate

Description

Oreskaurin A belongs to the class of organic compounds known as diterpene lactones. These are diterpenoids containing a lactone moiety. (1's,3r,3ar,4s,5r,6's,7'r,7ar,9's)-5,7'-dihydroxy-7a-methyl-10'-methylidene-2',11'-dioxo-hexahydro-3'-oxaspiro[2-benzofuran-4,5'-tricyclo[7.2.1.0¹,⁶]dodecan]-3-yl acetate is found in Isodon oresbius. Based on a literature review very few articles have been published on Oreskaurin A.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309052209592D          

 30 34  0  0  1  0            999 V2000
   -1.6361   -0.2489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7836   -0.2606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1441   -0.8497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6400   -1.5336    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6548   -0.4444    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1647    0.0749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4243    0.5243    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1172    1.1987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7755    1.1971    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7110    2.0602    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2355    0.2260    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0597    0.0533    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3324   -0.7324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7956   -1.3666    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9819   -1.2223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7129   -2.0461    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8045    0.8378    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6813    1.6984    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3564    1.4511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1634    1.2798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4186    0.4953    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0924    1.0659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1724    0.1600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0864   -0.6605    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2795   -0.8323    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6707   -1.6211    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3900   -2.0483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1095   -1.6447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3798   -2.8733    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8668   -0.1180    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  1  0  0  0
  7  6  1  1  0  0  0
  2  7  1  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
  9 11  1  0  0  0  0
 11  5  1  1  0  0  0
 11 12  1  0  0  0  0
 12 13  1  1  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
  5 15  1  0  0  0  0
 15 16  2  0  0  0  0
 12 17  1  0  0  0  0
 17 18  1  6  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  6  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  6  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 29  2  0  0  0  0
 30 25  1  1  0  0  0
 12 30  1  0  0  0  0
 21 30  1  0  0  0  0
M  END

     RDKit          3D

 58 62  0  0  0  0  0  0  0  0999 V2000
    3.0104    1.8109   -2.8397 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7527    1.4752   -1.6021 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5536    1.8582   -0.8608 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6911    2.7151   -1.1318 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5820    0.9523    0.3624 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0783    1.0872    0.6265 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6063    0.6514   -0.7085 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3374   -0.8126   -0.9283 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2767   -1.3686    0.0367 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8897   -1.5769    1.2350 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1398   -0.4155   -0.0011 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1356   -0.8720    0.6848 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0070   -0.5530    2.1788 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3076    0.7726    2.4308 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9407    1.5655    1.5214 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9865    2.8159    1.6571 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2819   -2.3710    0.6676 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7136   -3.0509    1.3484 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5144   -2.8108   -0.7344 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9990   -2.5040   -0.9827 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3352   -1.1374   -0.5906 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8878   -0.4406   -1.8524 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5128   -1.1729    0.3601 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5227    0.0701    0.8988 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2096    0.5598    0.9826 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3560    1.9201    0.5373 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2322    3.0125    1.3424 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4081    4.3885    0.7529 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9766    2.8590    2.5492 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3507   -0.2629    0.0763 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9296    1.4713   -3.2897 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3605    2.4140   -3.4580 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2552    2.2016    0.6854 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4589    0.6489    1.5095 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6791    0.8333   -0.8464 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2475   -1.4408   -0.8405 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9412   -0.9858   -1.9542 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0714   -2.3755   -0.4022 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8402   -1.7203    1.1073 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8290   -0.3881   -1.0953 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9077   -1.1589    2.4998 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8323   -0.9734    2.7615 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2077   -2.5761    1.2903 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8585   -3.9464    0.9595 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0092   -2.1949   -1.5183 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3185   -3.8657   -0.9338 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2197   -2.7603   -2.0561 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5519   -3.2654   -0.3880 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5156    0.4122   -1.5763 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4997   -1.1742   -2.4010 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0311   -0.1827   -2.4891 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4668   -1.2862   -0.2373 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5147   -2.0049    1.0576 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9750    0.5513    2.0389 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9515    5.1557    1.4046 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5256    4.5242    0.6751 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9338    4.4609   -0.2358 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9761    0.4609   -0.7147 H   0  0  0  0  0  0  0  0  0  0  0  0
 28 27  1  0
 27 29  2  0
 27 26  1  0
 26 25  1  0
 25 24  1  0
 24 23  1  0
 23 21  1  0
 21 22  1  6
 21 20  1  0
 20 19  1  0
 19 17  1  0
 17 18  1  0
 17 12  1  0
 12 13  1  1
 13 14  1  0
 14 15  1  0
 15 16  2  0
  5 15  1  1
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  1  0
  7  2  1  0
  2  1  2  3
  2  3  1  0
  3  4  2  0
 12 30  1  0
 30 25  1  0
 30 21  1  0
 11 12  1  0
 11  5  1  0
  3  5  1  0
 28 55  1  0
 28 56  1  0
 28 57  1  0
 25 54  1  1
 23 52  1  0
 23 53  1  0
 22 49  1  0
 22 50  1  0
 22 51  1  0
 20 47  1  0
 20 48  1  0
 19 45  1  0
 19 46  1  0
 17 43  1  1
 18 44  1  0
 13 41  1  0
 13 42  1  0
  6 33  1  0
  6 34  1  0
  7 35  1  1
  8 36  1  0
  8 37  1  0
  9 38  1  6
 10 39  1  0
 11 40  1  6
  1 31  1  0
  1 32  1  0
 30 58  1  6
M  END


  Mrv1652309052209592D          

 30 34  0  0  1  0            999 V2000
   -1.6361   -0.2489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7836   -0.2606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1441   -0.8497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6400   -1.5336    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6548   -0.4444    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1647    0.0749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4243    0.5243    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1172    1.1987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7755    1.1971    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7110    2.0602    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2355    0.2260    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0597    0.0533    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3324   -0.7324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7956   -1.3666    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9819   -1.2223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7129   -2.0461    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8045    0.8378    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6813    1.6984    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3564    1.4511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1634    1.2798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4186    0.4953    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0924    1.0659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1724    0.1600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0864   -0.6605    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2795   -0.8323    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6707   -1.6211    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3900   -2.0483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1095   -1.6447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3798   -2.8733    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8668   -0.1180    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  1  0  0  0
  7  6  1  1  0  0  0
  2  7  1  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
  9 11  1  0  0  0  0
 11  5  1  1  0  0  0
 11 12  1  0  0  0  0
 12 13  1  1  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
  5 15  1  0  0  0  0
 15 16  2  0  0  0  0
 12 17  1  0  0  0  0
 17 18  1  6  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  6  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  6  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 29  2  0  0  0  0
 30 25  1  1  0  0  0
 12 30  1  0  0  0  0
 21 30  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0210262

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)O[C@H]1OC[C@]2(C)CC[C@@H](O)[C@]3(COC(=O)[C@@]45C[C@@H](C[C@@H](O)[C@@H]34)C(=C)C5=O)[C@H]12

> <INCHI_IDENTIFIER>
InChI=1S/C22H28O8/c1-10-12-6-13(24)15-21(7-12,17(10)26)19(27)29-9-22(15)14(25)4-5-20(3)8-28-18(16(20)22)30-11(2)23/h12-16,18,24-25H,1,4-9H2,2-3H3/t12-,13-,14-,15-,16-,18-,20+,21+,22+/m1/s1

> <INCHI_KEY>
XESCNAZYJNKEGK-WSNWWDQLSA-N

> <FORMULA>
C22H28O8

> <MOLECULAR_WEIGHT>
420.458

> <EXACT_MASS>
420.178417862

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
58

> <JCHEM_AVERAGE_POLARIZABILITY>
42.1644088632722

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1'S,3R,3aR,4S,5R,6'S,7'R,7aR,9'S)-5,7'-dihydroxy-7a-methyl-10'-methylidene-2',11'-dioxo-hexahydro-1H-3'-oxaspiro[2-benzofuran-4,5'-tricyclo[7.2.1.0^{1,6}]dodecane]-3-yl acetate

> <JCHEM_LOGP>
0.44509003833333294

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.047267444582989

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.403522364903022

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8655390989426746

> <JCHEM_POLAR_SURFACE_AREA>
119.36000000000001

> <JCHEM_REFRACTIVITY>
101.6542

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1'S,3R,3aR,4S,5R,6'S,7'R,7aR,9'S)-5,7'-dihydroxy-7a-methyl-10'-methylidene-2',11'-dioxo-hexahydro-3'-oxaspiro[2-benzofuran-4,5'-tricyclo[7.2.1.0^{1,6}]dodecane]-3-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-22         0                                  
HETATM    1  C   UNK     0      -3.054  -0.465   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.463  -0.486   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.269  -1.586   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -1.195  -2.863   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       1.222  -0.830   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.307   0.140   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.792   0.979   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.219   2.238   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.448   2.235   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       1.327   3.846   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       2.306   0.422   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.845   0.099   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.354  -1.367   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       3.352  -2.551   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       1.833  -2.282   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       1.331  -3.819   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       3.368   1.564   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       3.138   3.170   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       4.399   2.709   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.905   2.389   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.381   0.925   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       7.639   1.990   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       7.788   0.299   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       7.628  -1.233   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       6.122  -1.554   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       6.852  -3.026   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       8.195  -3.824   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       9.538  -3.070   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       8.176  -5.363   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       5.351  -0.220   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    7                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   11   15                                             
CONECT    6    5    7                                                       
CONECT    7    6    2    8                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9    5   12                                                  
CONECT   12   11   13   17   30                                             
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14    5   16                                                  
CONECT   16   15                                                            
CONECT   17   12   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   23   30                                             
CONECT   22   21                                                            
CONECT   23   21   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26   30                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27                                                            
CONECT   30   25   12   21                                                  
MASTER        0    0    0    0    0    0    0    0   30    0   68    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₂H₂₈O₈

Average Mass

420.4580 Da

Monoisotopic Mass

420.17842 Da

IUPAC Name

(1'S,3R,3aR,4S,5R,6'S,7'R,7aR,9'S)-5,7'-dihydroxy-7a-methyl-10'-methylidene-2',11'-dioxo-hexahydro-1H-3'-oxaspiro[2-benzofuran-4,5'-tricyclo[7.2.1.0^{1,6}]dodecane]-3-yl acetate

Traditional Name

(1'S,3R,3aR,4S,5R,6'S,7'R,7aR,9'S)-5,7'-dihydroxy-7a-methyl-10'-methylidene-2',11'-dioxo-hexahydro-3'-oxaspiro[2-benzofuran-4,5'-tricyclo[7.2.1.0^{1,6}]dodecane]-3-yl acetate

CAS Registry Number

Not Available

SMILES

CC(=O)O[C@H]1OC[C@]2(C)CC[C@@H](O)[C@]3(COC(=O)[C@@]45C[C@@H](C[C@@H](O)[C@@H]34)C(=C)C5=O)[C@H]12

InChI Identifier

InChI=1S/C22H28O8/c1-10-12-6-13(24)15-21(7-12,17(10)26)19(27)29-9-22(15)14(25)4-5-20(3)8-28-18(16(20)22)30-11(2)23/h12-16,18,24-25H,1,4-9H2,2-3H3/t12-,13-,14-,15-,16-,18-,20+,21+,22+/m1/s1

InChI Key

XESCNAZYJNKEGK-WSNWWDQLSA-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
Isodon oresbius	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diterpene lactones. These are diterpenoids containing a lactone moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Diterpene lactones

Alternative Parents

Substituents

Diterpene lactone
Diterpenoid
Kaurane diterpenoid
Isobenzofuran
Delta valerolactone
Delta_valerolactone
Oxane
Dicarboxylic acid or derivatives
Tetrahydrofuran
Cyclic alcohol
Carboxylic acid ester
Secondary alcohol
Lactone
Ketone
Oxacycle
Organoheterocyclic compound
Carboxylic acid derivative
Acetal
Organooxygen compound
Hydrocarbon derivative
Carbonyl group
Alcohol
Organic oxygen compound
Organic oxide
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	0.45	ChemAxon
pKa (Strongest Acidic)	14.4	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	119.36 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	101.65 m³·mol⁻¹	ChemAxon
Polarizability	42.16 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

C00035709

Chemspider ID

558690

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

643551

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1's,3r,3ar,4s,5r,6's,7'r,7ar,9's)-5,7'-dihydroxy-7a-methyl-10'-methylidene-2',11'-dioxo-hexahydro-3'-oxaspiro[2-benzofuran-4,5'-tricyclo[7.2.1.0¹,⁶]dodecan]-3-yl acetate (NP0210262)

MOL for NP0210262 ((1's,3r,3ar,4s,5r,6's,7'r,7ar,9's)-5,7'-dihydroxy-7a-methyl-10'-methylidene-2',11'-dioxo-hexahydro-3'-oxaspiro[2-benzofuran-4,5'-tricyclo[7.2.1.0¹,⁶]dodecan]-3-yl acetate)

3D MOL for NP0210262 ((1's,3r,3ar,4s,5r,6's,7'r,7ar,9's)-5,7'-dihydroxy-7a-methyl-10'-methylidene-2',11'-dioxo-hexahydro-3'-oxaspiro[2-benzofuran-4,5'-tricyclo[7.2.1.0¹,⁶]dodecan]-3-yl acetate)

3D SDF for NP0210262 ((1's,3r,3ar,4s,5r,6's,7'r,7ar,9's)-5,7'-dihydroxy-7a-methyl-10'-methylidene-2',11'-dioxo-hexahydro-3'-oxaspiro[2-benzofuran-4,5'-tricyclo[7.2.1.0¹,⁶]dodecan]-3-yl acetate)

3D-SDF for NP0210262 ((1's,3r,3ar,4s,5r,6's,7'r,7ar,9's)-5,7'-dihydroxy-7a-methyl-10'-methylidene-2',11'-dioxo-hexahydro-3'-oxaspiro[2-benzofuran-4,5'-tricyclo[7.2.1.0¹,⁶]dodecan]-3-yl acetate)

PDB for NP0210262 ((1's,3r,3ar,4s,5r,6's,7'r,7ar,9's)-5,7'-dihydroxy-7a-methyl-10'-methylidene-2',11'-dioxo-hexahydro-3'-oxaspiro[2-benzofuran-4,5'-tricyclo[7.2.1.0¹,⁶]dodecan]-3-yl acetate)

3D PDB for NP0210262 ((1's,3r,3ar,4s,5r,6's,7'r,7ar,9's)-5,7'-dihydroxy-7a-methyl-10'-methylidene-2',11'-dioxo-hexahydro-3'-oxaspiro[2-benzofuran-4,5'-tricyclo[7.2.1.0¹,⁶]dodecan]-3-yl acetate)

SMILES for NP0210262 ((1's,3r,3ar,4s,5r,6's,7'r,7ar,9's)-5,7'-dihydroxy-7a-methyl-10'-methylidene-2',11'-dioxo-hexahydro-3'-oxaspiro[2-benzofuran-4,5'-tricyclo[7.2.1.0¹,⁶]dodecan]-3-yl acetate)

INCHI for NP0210262 ((1's,3r,3ar,4s,5r,6's,7'r,7ar,9's)-5,7'-dihydroxy-7a-methyl-10'-methylidene-2',11'-dioxo-hexahydro-3'-oxaspiro[2-benzofuran-4,5'-tricyclo[7.2.1.0¹,⁶]dodecan]-3-yl acetate)

Structure for NP0210262 ((1's,3r,3ar,4s,5r,6's,7'r,7ar,9's)-5,7'-dihydroxy-7a-methyl-10'-methylidene-2',11'-dioxo-hexahydro-3'-oxaspiro[2-benzofuran-4,5'-tricyclo[7.2.1.0¹,⁶]dodecan]-3-yl acetate)

3D Structure for NP0210262 ((1's,3r,3ar,4s,5r,6's,7'r,7ar,9's)-5,7'-dihydroxy-7a-methyl-10'-methylidene-2',11'-dioxo-hexahydro-3'-oxaspiro[2-benzofuran-4,5'-tricyclo[7.2.1.0¹,⁶]dodecan]-3-yl acetate)