NP-MRD: Showing NP-Card for sarcrassin A (NP0032455)

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Record Information

Version

2.0

Created at

2021-06-19 23:15:16 UTC

Updated at

2021-06-30 00:01:39 UTC

NP-MRD ID

NP0032455

Secondary Accession Numbers

None

Natural Product Identification

Common Name

sarcrassin A

Provided By

JEOL Database JEOL Logo

Description

Sarcophytonolide B belongs to the class of organic compounds known as cembrane diterpenoids. These are diterpenoids with a structure based a cembrane skeleton, which is characterized by the presence of an isopropyl group at C-1 and by three symmetrically disposed methyl groups a the t C-4, -8 and -12 positions. sarcrassin A is found in Sarcophyton crassocaule and Sarcophyton tortuosum. sarcrassin A was first documented in 2006 (Zhang, C., et al.). Based on a literature review very few articles have been published on Sarcophytonolide B.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202101153D          

 59 60  0  0  0  0            999 V2000
    4.4707   -0.8921    1.0925 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5042    0.1554    1.0174 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3220   -0.1406    1.6150 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0615   -1.1971    2.1736 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3370    0.9835    1.4936 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7087    2.1832    0.9972 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8035    3.3681    0.7948 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3940    4.4784   -0.0835 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6254    4.0861   -1.5289 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9723    3.5166   -1.8706 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2139    5.1224   -2.4380 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4332    3.9188   -2.4728 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4878    3.2365   -3.8100 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2138    1.8732   -3.8238 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4353    0.8431   -2.9251 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7409    0.3185   -3.4425 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1399    0.5305   -4.5790 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4232   -0.3733   -2.4947 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6905   -0.8637   -2.9316 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0656    0.3755   -1.7621 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3200    0.7665   -1.1482 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7133    0.5096    0.1176 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0663    0.9899    0.6590 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.5364    2.3461    0.1171 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1433   -0.0723    0.4223 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8797   -0.2566    1.1366 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0403    0.6650    2.0381 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.7342   -1.0959    2.1350 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0973   -1.7966    0.6020 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3702   -0.5609    0.5663 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7463    2.3377    0.7092 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5892    3.8027    1.7790 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1487    3.0473    0.3624 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3309    4.8426    0.3565 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7010    5.3299   -0.0479 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7562    3.9652   -1.2516 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2500    3.7017   -2.9130 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9855    2.4364   -1.7042 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5709    3.9778   -2.0714 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0224    3.8839   -4.5347 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5156    3.1370   -4.1724 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2245    1.4913   -4.8532 H   0  0  0  0  0  0  0  0  0  0  0  0
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 20 15  2  0  0  0  0
  6  7  1  0  0  0  0
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  7  8  1  0  0  0  0
 14 13  1  0  0  0  0
  8  9  1  0  0  0  0
 13 12  1  0  0  0  0
  9 12  1  0  0  0  0
  3  4  2  0  0  0  0
 22 23  1  0  0  0  0
  2  1  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
  3  2  1  0  0  0  0
 15 16  1  0  0  0  0
 26 22  1  0  0  0  0
 16 17  2  0  0  0  0
 26 27  1  0  0  0  0
 16 18  1  0  0  0  0
 22 21  2  0  0  0  0
 18 19  1  0  0  0  0
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 12 11  1  0  0  0  0
 11  9  1  0  0  0  0
 21 20  1  0  0  0  0
  9 10  1  1  0  0  0
  5  6  2  0  0  0  0
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  5  3  1  0  0  0  0
  1 28  1  0  0  0  0
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 10 38  1  0  0  0  0
M  END

     RDKit          3D

 59 60  0  0  0  0  0  0  0  0999 V2000
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    1.3370    0.9835    1.4936 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7087    2.1832    0.9972 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8035    3.3681    0.7948 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3940    4.4784   -0.0835 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.4332    3.9188   -2.4728 C   0  0  1  0  0  0  0  0  0  0  0  0
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   -0.2138    1.8732   -3.8238 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1652306202101153D          

 59 60  0  0  0  0            999 V2000
    4.4707   -0.8921    1.0925 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5042    0.1554    1.0174 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3220   -0.1406    1.6150 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.8035    3.3681    0.7948 C   0  0  2  0  0  0  0  0  0  0  0  0
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    4.0973   -1.7966    0.6020 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3702   -0.5609    0.5663 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7463    2.3377    0.7092 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5892    3.8027    1.7790 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1487    3.0473    0.3624 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3309    4.8426    0.3565 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7010    5.3299   -0.0479 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7562    3.9652   -1.2516 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2500    3.7017   -2.9130 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9855    2.4364   -1.7042 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5709    3.9778   -2.0714 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0224    3.8839   -4.5347 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5156    3.1370   -4.1724 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2245    1.4913   -4.8532 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2690    2.0215   -3.5763 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3541   -0.0318   -3.1874 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1398   -1.4235   -2.1070 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5694   -1.5410   -3.7829 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5061   -0.3677   -1.2124 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0035    1.3185   -1.7852 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9639    1.1257    1.7441 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8309    2.2916   -0.9362 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4099    2.6957    0.6790 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7530    3.1047    0.2192 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0944    0.2347    0.8709 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3143   -0.2366   -0.6476 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8618   -1.0320    0.8689 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2597   -1.0219    0.6585 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5657   -0.8293    1.7752 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5928    1.5847    2.2652 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0840    0.1749    3.0134 H   0  0  0  0  0  0  0  0  0  0  0  0
 20 15  2  0  0  0  0
  6  7  1  0  0  0  0
 15 14  1  0  0  0  0
  7  8  1  0  0  0  0
 14 13  1  0  0  0  0
  8  9  1  0  0  0  0
 13 12  1  0  0  0  0
  9 12  1  0  0  0  0
  3  4  2  0  0  0  0
 22 23  1  0  0  0  0
  2  1  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
  3  2  1  0  0  0  0
 15 16  1  0  0  0  0
 26 22  1  0  0  0  0
 16 17  2  0  0  0  0
 26 27  1  0  0  0  0
 16 18  1  0  0  0  0
 22 21  2  0  0  0  0
 18 19  1  0  0  0  0
 27  5  1  0  0  0  0
 12 11  1  0  0  0  0
 11  9  1  0  0  0  0
 21 20  1  0  0  0  0
  9 10  1  1  0  0  0
  5  6  2  0  0  0  0
 12 39  1  1  0  0  0
  5  3  1  0  0  0  0
  1 28  1  0  0  0  0
  1 29  1  0  0  0  0
  1 30  1  0  0  0  0
 26 56  1  0  0  0  0
 26 57  1  0  0  0  0
 27 58  1  0  0  0  0
 27 59  1  0  0  0  0
 21 48  1  0  0  0  0
 20 47  1  0  0  0  0
  6 31  1  0  0  0  0
  7 32  1  0  0  0  0
  7 33  1  0  0  0  0
 14 42  1  0  0  0  0
 14 43  1  0  0  0  0
  8 34  1  0  0  0  0
  8 35  1  0  0  0  0
 13 40  1  0  0  0  0
 13 41  1  0  0  0  0
 23 49  1  1  0  0  0
 24 50  1  0  0  0  0
 24 51  1  0  0  0  0
 24 52  1  0  0  0  0
 25 53  1  0  0  0  0
 25 54  1  0  0  0  0
 25 55  1  0  0  0  0
 19 44  1  0  0  0  0
 19 45  1  0  0  0  0
 19 46  1  0  0  0  0
 10 36  1  0  0  0  0
 10 37  1  0  0  0  0
 10 38  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0032455

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]/C1=C(C(=O)OC([H])([H])[H])/C([H])([H])C([H])([H])[C@]2([H])O[C@@]2(C([H])([H])[H])C([H])([H])C([H])([H])\C([H])=C(C(=O)OC([H])([H])[H])/C([H])([H])C([H])([H])/C(=C\1/[H])C([H])(C([H])([H])[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C22H32O5/c1-15(2)16-8-10-17(20(23)25-4)7-6-14-22(3)19(27-22)13-12-18(11-9-16)21(24)26-5/h7,9,11,15,19H,6,8,10,12-14H2,1-5H3/b16-9+,17-7+,18-11+/t19-,22-/m0/s1

> <INCHI_KEY>
OQZOTIXASJTXOV-VIMFUQNDSA-N

> <FORMULA>
C22H32O5

> <MOLECULAR_WEIGHT>
376.493

> <EXACT_MASS>
376.22497413

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
59

> <JCHEM_AVERAGE_POLARIZABILITY>
41.163000974136175

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4,10-dimethyl (1S,4E,6E,10E,14S)-14-methyl-7-(propan-2-yl)-15-oxabicyclo[12.1.0]pentadeca-4,6,10-triene-4,10-dicarboxylate

> <ALOGPS_LOGP>
5.19

> <JCHEM_LOGP>
4.722365999666668

> <ALOGPS_LOGS>
-4.98

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.222487881926377

> <JCHEM_POLAR_SURFACE_AREA>
65.13

> <JCHEM_REFRACTIVITY>
106.89110000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.90e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4,10-dimethyl (1S,4E,6E,10E,14S)-7-isopropyl-14-methyl-15-oxabicyclo[12.1.0]pentadeca-4,6,10-triene-4,10-dicarboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 59 60  0  0  0  0  0  0  0  0999 V2000
    4.4707   -0.8921    1.0925 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5042    0.1554    1.0174 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3220   -0.1406    1.6150 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0615   -1.1971    2.1736 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3370    0.9835    1.4936 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7087    2.1832    0.9972 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8035    3.3681    0.7948 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3940    4.4784   -0.0835 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6254    4.0861   -1.5289 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9723    3.5166   -1.8706 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2139    5.1224   -2.4380 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4332    3.9188   -2.4728 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4878    3.2365   -3.8100 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2138    1.8732   -3.8238 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4353    0.8431   -2.9251 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7409    0.3185   -3.4425 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1399    0.5305   -4.5790 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4232   -0.3733   -2.4947 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6905   -0.8637   -2.9316 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0656    0.3755   -1.7621 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3200    0.7665   -1.1482 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7133    0.5096    0.1176 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0663    0.9899    0.6590 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.5364    2.3461    0.1171 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1433   -0.0723    0.4223 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8797   -0.2566    1.1366 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0403    0.6650    2.0381 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7342   -1.0959    2.1350 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0973   -1.7966    0.6020 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3702   -0.5609    0.5663 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7463    2.3377    0.7092 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5892    3.8027    1.7790 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1487    3.0473    0.3624 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3309    4.8426    0.3565 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7010    5.3299   -0.0479 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7562    3.9652   -1.2516 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2500    3.7017   -2.9130 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9855    2.4364   -1.7042 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5709    3.9778   -2.0714 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0224    3.8839   -4.5347 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5156    3.1370   -4.1724 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2245    1.4913   -4.8532 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2690    2.0215   -3.5763 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3541   -0.0318   -3.1874 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1398   -1.4235   -2.1070 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5694   -1.5410   -3.7829 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5061   -0.3677   -1.2124 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0035    1.3185   -1.7852 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9639    1.1257    1.7441 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8309    2.2916   -0.9362 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4099    2.6957    0.6790 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7530    3.1047    0.2192 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0944    0.2347    0.8709 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3143   -0.2366   -0.6476 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8618   -1.0320    0.8689 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2597   -1.0219    0.6585 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5657   -0.8293    1.7752 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5928    1.5847    2.2652 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0840    0.1749    3.0134 H   0  0  0  0  0  0  0  0  0  0  0  0
 20 15  2  0
  6  7  1  0
 15 14  1  0
  7  8  1  0
 14 13  1  0
  8  9  1  0
 13 12  1  0
  9 12  1  0
  3  4  2  0
 22 23  1  0
  2  1  1  0
 23 24  1  0
 23 25  1  0
  3  2  1  0
 15 16  1  0
 26 22  1  0
 16 17  2  0
 26 27  1  0
 16 18  1  0
 22 21  2  0
 18 19  1  0
 27  5  1  0
 12 11  1  0
 11  9  1  0
 21 20  1  0
  9 10  1  1
  5  6  2  0
 12 39  1  1
  5  3  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
 26 56  1  0
 26 57  1  0
 27 58  1  0
 27 59  1  0
 21 48  1  0
 20 47  1  0
  6 31  1  0
  7 32  1  0
  7 33  1  0
 14 42  1  0
 14 43  1  0
  8 34  1  0
  8 35  1  0
 13 40  1  0
 13 41  1  0
 23 49  1  1
 24 50  1  0
 24 51  1  0
 24 52  1  0
 25 53  1  0
 25 54  1  0
 25 55  1  0
 19 44  1  0
 19 45  1  0
 19 46  1  0
 10 36  1  0
 10 37  1  0
 10 38  1  0
M  END

HEADER    PROTEIN                                 20-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-JUN-21         0                                  
HETATM    1  C   UNK     0       4.471  -0.892   1.093  0.00  0.00           C+0
HETATM    2  O   UNK     0       3.504   0.155   1.017  0.00  0.00           O+0
HETATM    3  C   UNK     0       2.322  -0.141   1.615  0.00  0.00           C+0
HETATM    4  O   UNK     0       2.062  -1.197   2.174  0.00  0.00           O+0
HETATM    5  C   UNK     0       1.337   0.984   1.494  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.709   2.183   0.997  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.804   3.368   0.795  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.394   4.478  -0.084  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.625   4.086  -1.529  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.972   3.517  -1.871  0.00  0.00           C+0
HETATM   11  O   UNK     0       1.214   5.122  -2.438  0.00  0.00           O+0
HETATM   12  C   UNK     0       0.433   3.919  -2.473  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.488   3.236  -3.810  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.214   1.873  -3.824  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.435   0.843  -2.925  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.741   0.319  -3.442  0.00  0.00           C+0
HETATM   17  O   UNK     0       2.140   0.531  -4.579  0.00  0.00           O+0
HETATM   18  O   UNK     0       2.423  -0.373  -2.495  0.00  0.00           O+0
HETATM   19  C   UNK     0       3.691  -0.864  -2.932  0.00  0.00           C+0
HETATM   20  C   UNK     0      -0.066   0.376  -1.762  0.00  0.00           C+0
HETATM   21  C   UNK     0      -1.320   0.767  -1.148  0.00  0.00           C+0
HETATM   22  C   UNK     0      -1.713   0.510   0.118  0.00  0.00           C+0
HETATM   23  C   UNK     0      -3.066   0.990   0.659  0.00  0.00           C+0
HETATM   24  C   UNK     0      -3.536   2.346   0.117  0.00  0.00           C+0
HETATM   25  C   UNK     0      -4.143  -0.072   0.422  0.00  0.00           C+0
HETATM   26  C   UNK     0      -0.880  -0.257   1.137  0.00  0.00           C+0
HETATM   27  C   UNK     0      -0.040   0.665   2.038  0.00  0.00           C+0
HETATM   28  H   UNK     0       4.734  -1.096   2.135  0.00  0.00           H+0
HETATM   29  H   UNK     0       4.097  -1.797   0.602  0.00  0.00           H+0
HETATM   30  H   UNK     0       5.370  -0.561   0.566  0.00  0.00           H+0
HETATM   31  H   UNK     0       2.746   2.338   0.709  0.00  0.00           H+0
HETATM   32  H   UNK     0       0.589   3.803   1.779  0.00  0.00           H+0
HETATM   33  H   UNK     0      -0.149   3.047   0.362  0.00  0.00           H+0
HETATM   34  H   UNK     0       2.331   4.843   0.357  0.00  0.00           H+0
HETATM   35  H   UNK     0       0.701   5.330  -0.048  0.00  0.00           H+0
HETATM   36  H   UNK     0       3.756   3.965  -1.252  0.00  0.00           H+0
HETATM   37  H   UNK     0       3.250   3.702  -2.913  0.00  0.00           H+0
HETATM   38  H   UNK     0       2.986   2.436  -1.704  0.00  0.00           H+0
HETATM   39  H   UNK     0      -0.571   3.978  -2.071  0.00  0.00           H+0
HETATM   40  H   UNK     0      -0.022   3.884  -4.535  0.00  0.00           H+0
HETATM   41  H   UNK     0       1.516   3.137  -4.172  0.00  0.00           H+0
HETATM   42  H   UNK     0      -0.225   1.491  -4.853  0.00  0.00           H+0
HETATM   43  H   UNK     0      -1.269   2.022  -3.576  0.00  0.00           H+0
HETATM   44  H   UNK     0       4.354  -0.032  -3.187  0.00  0.00           H+0
HETATM   45  H   UNK     0       4.140  -1.424  -2.107  0.00  0.00           H+0
HETATM   46  H   UNK     0       3.569  -1.541  -3.783  0.00  0.00           H+0
HETATM   47  H   UNK     0       0.506  -0.368  -1.212  0.00  0.00           H+0
HETATM   48  H   UNK     0      -2.003   1.319  -1.785  0.00  0.00           H+0
HETATM   49  H   UNK     0      -2.964   1.126   1.744  0.00  0.00           H+0
HETATM   50  H   UNK     0      -3.831   2.292  -0.936  0.00  0.00           H+0
HETATM   51  H   UNK     0      -4.410   2.696   0.679  0.00  0.00           H+0
HETATM   52  H   UNK     0      -2.753   3.105   0.219  0.00  0.00           H+0
HETATM   53  H   UNK     0      -5.094   0.235   0.871  0.00  0.00           H+0
HETATM   54  H   UNK     0      -4.314  -0.237  -0.648  0.00  0.00           H+0
HETATM   55  H   UNK     0      -3.862  -1.032   0.869  0.00  0.00           H+0
HETATM   56  H   UNK     0      -0.260  -1.022   0.659  0.00  0.00           H+0
HETATM   57  H   UNK     0      -1.566  -0.829   1.775  0.00  0.00           H+0
HETATM   58  H   UNK     0      -0.593   1.585   2.265  0.00  0.00           H+0
HETATM   59  H   UNK     0       0.084   0.175   3.013  0.00  0.00           H+0
CONECT    1    2   28   29   30                                             
CONECT    2    1    3                                                       
CONECT    3    4    2    5                                                  
CONECT    4    3                                                            
CONECT    5   27    6    3                                                  
CONECT    6    7    5   31                                                  
CONECT    7    6    8   32   33                                             
CONECT    8    7    9   34   35                                             
CONECT    9    8   12   11   10                                             
CONECT   10    9   36   37   38                                             
CONECT   11   12    9                                                       
CONECT   12   13    9   11   39                                             
CONECT   13   14   12   40   41                                             
CONECT   14   15   13   42   43                                             
CONECT   15   20   14   16                                                  
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18   44   45   46                                             
CONECT   20   15   21   47                                                  
CONECT   21   22   20   48                                                  
CONECT   22   23   26   21                                                  
CONECT   23   22   24   25   49                                             
CONECT   24   23   50   51   52                                             
CONECT   25   23   53   54   55                                             
CONECT   26   22   27   56   57                                             
CONECT   27   26    5   58   59                                             
CONECT   28    1                                                            
CONECT   29    1                                                            
CONECT   30    1                                                            
CONECT   31    6                                                            
CONECT   32    7                                                            
CONECT   33    7                                                            
CONECT   34    8                                                            
CONECT   35    8                                                            
CONECT   36   10                                                            
CONECT   37   10                                                            
CONECT   38   10                                                            
CONECT   39   12                                                            
CONECT   40   13                                                            
CONECT   41   13                                                            
CONECT   42   14                                                            
CONECT   43   14                                                            
CONECT   44   19                                                            
CONECT   45   19                                                            
CONECT   46   19                                                            
CONECT   47   20                                                            
CONECT   48   21                                                            
CONECT   49   23                                                            
CONECT   50   24                                                            
CONECT   51   24                                                            
CONECT   52   24                                                            
CONECT   53   25                                                            
CONECT   54   25                                                            
CONECT   55   25                                                            
CONECT   56   26                                                            
CONECT   57   26                                                            
CONECT   58   27                                                            
CONECT   59   27                                                            
MASTER        0    0    0    0    0    0    0    0   59    0  120    0
END

RDKit          3D

59 60  0  0  0  0  0  0  0  0999 V2000
    4.4707   -0.8921    1.0925 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5042    0.1554    1.0174 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3220   -0.1406    1.6150 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0615   -1.1971    2.1736 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3370    0.9835    1.4936 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7087    2.1832    0.9972 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8035    3.3681    0.7948 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3940    4.4784   -0.0835 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6254    4.0861   -1.5289 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9723    3.5166   -1.8706 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2139    5.1224   -2.4380 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4332    3.9188   -2.4728 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4878    3.2365   -3.8100 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2138    1.8732   -3.8238 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4353    0.8431   -2.9251 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7409    0.3185   -3.4425 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1399    0.5305   -4.5790 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4232   -0.3733   -2.4947 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6905   -0.8637   -2.9316 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0656    0.3755   -1.7621 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3200    0.7665   -1.1482 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7133    0.5096    0.1176 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0663    0.9899    0.6590 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.5364    2.3461    0.1171 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1433   -0.0723    0.4223 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8797   -0.2566    1.1366 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0403    0.6650    2.0381 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7342   -1.0959    2.1350 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0973   -1.7966    0.6020 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3702   -0.5609    0.5663 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7463    2.3377    0.7092 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5892    3.8027    1.7790 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1487    3.0473    0.3624 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3309    4.8426    0.3565 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7010    5.3299   -0.0479 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7562    3.9652   -1.2516 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2500    3.7017   -2.9130 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9855    2.4364   -1.7042 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5709    3.9778   -2.0714 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0224    3.8839   -4.5347 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5156    3.1370   -4.1724 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2245    1.4913   -4.8532 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2690    2.0215   -3.5763 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3541   -0.0318   -3.1874 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1398   -1.4235   -2.1070 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5694   -1.5410   -3.7829 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5061   -0.3677   -1.2124 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0035    1.3185   -1.7852 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9639    1.1257    1.7441 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8309    2.2916   -0.9362 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4099    2.6957    0.6790 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7530    3.1047    0.2192 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0944    0.2347    0.8709 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3143   -0.2366   -0.6476 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8618   -1.0320    0.8689 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2597   -1.0219    0.6585 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5657   -0.8293    1.7752 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5928    1.5847    2.2652 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0840    0.1749    3.0134 H   0  0  0  0  0  0  0  0  0  0  0  0
 20 15  2  0
  6  7  1  0
 15 14  1  0
  7  8  1  0
 14 13  1  0
  8  9  1  0
 13 12  1  0
  9 12  1  0
  3  4  2  0
 22 23  1  0
  2  1  1  0
 23 24  1  0
 23 25  1  0
  3  2  1  0
 15 16  1  0
 26 22  1  0
 16 17  2  0
 26 27  1  0
 16 18  1  0
 22 21  2  0
 18 19  1  0
 27  5  1  0
 12 11  1  0
 11  9  1  0
 21 20  1  0
  9 10  1  1
  5  6  2  0
 12 39  1  1
  5  3  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
 26 56  1  0
 26 57  1  0
 27 58  1  0
 27 59  1  0
 21 48  1  0
 20 47  1  0
  6 31  1  0
  7 32  1  0
  7 33  1  0
 14 42  1  0
 14 43  1  0
  8 34  1  0
  8 35  1  0
 13 40  1  0
 13 41  1  0
 23 49  1  1
 24 50  1  0
 24 51  1  0
 24 52  1  0
 25 53  1  0
 25 54  1  0
 25 55  1  0
 19 44  1  0
 19 45  1  0
 19 46  1  0
 10 36  1  0
 10 37  1  0
 10 38  1  0
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₂H₃₂O₅

Average Mass

376.4930 Da

Monoisotopic Mass

376.22497 Da

IUPAC Name

4,10-dimethyl (1S,4E,6E,10E,14S)-14-methyl-7-(propan-2-yl)-15-oxabicyclo[12.1.0]pentadeca-4,6,10-triene-4,10-dicarboxylate

Traditional Name

4,10-dimethyl (1S,4E,6E,10E,14S)-7-isopropyl-14-methyl-15-oxabicyclo[12.1.0]pentadeca-4,6,10-triene-4,10-dicarboxylate

CAS Registry Number

Not Available

SMILES

[H]/C1=C(C(=O)OC([H])([H])[H])/C([H])([H])C([H])([H])[C@]2([H])O[C@@]2(C([H])([H])[H])C([H])([H])C([H])([H])\C([H])=C(C(=O)OC([H])([H])[H])/C([H])([H])C([H])([H])/C(=C\1/[H])C([H])(C([H])([H])[H])C([H])([H])[H]

InChI Identifier

InChI=1S/C22H32O5/c1-15(2)16-8-10-17(20(23)25-4)7-6-14-22(3)19(27-22)13-12-18(11-9-16)21(24)26-5/h7,9,11,15,19H,6,8,10,12-14H2,1-5H3/b16-9+,17-7+,18-11+/t19-,22-/m0/s1

InChI Key

OQZOTIXASJTXOV-VIMFUQNDSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Sarcophyton crassocaule	JEOL database	Zhang, C., et al, J. Nat. Prod. 69, 1476 (2006)
Sarcophyton tortuosum	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cembrane diterpenoids. These are diterpenoids with a structure based a cembrane skeleton, which is characterized by the presence of an isopropyl group at C-1 and by three symmetrically disposed methyl groups a the t C-4, -8 and -12 positions.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Cembrane diterpenoids

Alternative Parents

Substituents

Cembrane diterpenoid
Dicarboxylic acid or derivatives
Methyl ester
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Carboxylic acid ester
Carboxylic acid derivative
Dialkyl ether
Oxirane
Ether
Oxacycle
Organoheterocyclic compound
Hydrocarbon derivative
Organic oxygen compound
Organooxygen compound
Organic oxide
Carbonyl group
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	5.19	ALOGPS
logP	4.72	ChemAxon
logS	-5	ALOGPS
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	65.13 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	106.89 m³·mol⁻¹	ChemAxon
Polarizability	41.16 Å³	ChemAxon
Number of Rings	2	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

101720914

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Zhang, C., et al. (2006). Zhang, C., et al, J. Nat. Prod. 69, 1476 (2006) . J. Nat. Prod..

Showing NP-Card for sarcrassin A (NP0032455)

MOL for NP0032455 (sarcrassin A)

3D MOL for NP0032455 (sarcrassin A)

3D SDF for NP0032455 (sarcrassin A)

3D-SDF for NP0032455 (sarcrassin A)

PDB for NP0032455 (sarcrassin A)

3D PDB for NP0032455 (sarcrassin A)

SMILES for NP0032455 (sarcrassin A)

INCHI for NP0032455 (sarcrassin A)

Structure for NP0032455 (sarcrassin A)

3D Structure for NP0032455 (sarcrassin A)