NP-MRD: Showing NP-Card for tortuosene A (NP0042829)

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Record Information

Version

2.0

Created at

2021-06-21 00:23:57 UTC

Updated at

2021-06-30 00:18:09 UTC

NP-MRD ID

NP0042829

Secondary Accession Numbers

None

Natural Product Identification

Common Name

tortuosene A

Provided By

JEOL Database JEOL Logo

Description

Tortuosen A belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. tortuosene A is found in Sarcophyton tortuosum. tortuosene A was first documented in 2014 (Lin, K.-H., et al.). Based on a literature review very few articles have been published on Tortuosen A.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306212102233D          

 62 64  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652306212102233D          

 62 64  0  0  0  0            999 V2000
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    0.2868    1.2771    0.9782 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7872   -0.0027    2.5210 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6705    0.2168    3.6553 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7813   -0.5691    3.7188 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5751   -0.2319    4.9432 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0959   -1.4231    2.9033 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7737   -1.0902    2.9434 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1267   -1.6407    1.8329 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6644   -4.7265    1.1711 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9404   -4.8258   -0.5794 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5503   -5.6781    0.1221 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4285   -1.8964   -1.2894 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9616   -0.2214   -0.5123 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3584    2.4794   -3.0609 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8661    1.6586   -2.6680 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1354    0.5196   -4.1798 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9558   -0.4614   -2.9760 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8430    0.9145   -2.2250 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0099   -2.1580   -3.0675 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6315   -0.3140   -4.8941 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4104   -2.0541   -5.1163 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0214   -0.9862   -5.2214 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9371   -2.0449   -1.4914 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8283   -1.0269   -2.6378 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4199   -2.6955   -3.0494 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9142    3.9086    1.1433 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6158    4.3686    1.1116 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1869    1.8559    1.3513 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7277    2.7657    2.7745 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0544    2.9562    2.9746 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5753    1.3490    3.3943 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8681    2.0364    4.1746 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3818   -0.3738    1.6781 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8975    0.8114    4.8997 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4624   -0.8698    4.9869 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9723   -0.4122    5.8368 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1507   -0.7273    3.7692 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3305   -1.9270    3.3868 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8621   -0.8834    1.5492 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7291   -2.4654    2.2350 H   0  0  0  0  0  0  0  0  0  0  0  0
 30 29  1  0  0  0  0
  7  6  1  0  0  0  0
 21 24  1  0  0  0  0
 29 24  1  0  0  0  0
  6  5  2  0  0  0  0
  5  3  1  0  0  0  0
  5 30  1  0  0  0  0
 12 14  1  0  0  0  0
  8  7  1  0  0  0  0
 14 15  1  0  0  0  0
 11 12  1  0  0  0  0
 14 16  1  0  0  0  0
  8  9  2  0  0  0  0
 17 18  2  0  0  0  0
 21 22  1  1  0  0  0
  9 17  1  0  0  0  0
 12 13  1  1  0  0  0
 11 10  1  0  0  0  0
  7 35  1  1  0  0  0
 17 19  1  0  0  0  0
 24 25  1  0  0  0  0
 12  7  1  0  0  0  0
  3  4  2  0  0  0  0
 23 21  1  0  0  0  0
  3  2  1  0  0  0  0
  9 10  1  0  0  0  0
  2  1  1  0  0  0  0
 19 20  1  0  0  0  0
 25 26  1  0  0  0  0
 21 20  1  0  0  0  0
 26 27  1  0  0  0  0
  8 23  1  0  0  0  0
 26 28  2  0  0  0  0
 11 38  1  0  0  0  0
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 10 36  1  0  0  0  0
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  6 34  1  0  0  0  0
 30 61  1  0  0  0  0
 30 62  1  0  0  0  0
 19 48  1  0  0  0  0
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 20 51  1  0  0  0  0
 29 59  1  0  0  0  0
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 24 55  1  6  0  0  0
 14 41  1  6  0  0  0
 15 42  1  0  0  0  0
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 15 44  1  0  0  0  0
 16 45  1  0  0  0  0
 16 46  1  0  0  0  0
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 22 52  1  0  0  0  0
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 22 54  1  0  0  0  0
 13 40  1  0  0  0  0
  1 31  1  0  0  0  0
  1 32  1  0  0  0  0
  1 33  1  0  0  0  0
 27 56  1  0  0  0  0
 27 57  1  0  0  0  0
 27 58  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0042829

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]O[C@]1(C([H])([H])C([H])([H])C2=C3O[C@](C([H])([H])[H])(C([H])([H])C([H])([H])C2=O)[C@@]([H])(OC(=O)C([H])([H])[H])C([H])([H])C([H])([H])\C(=C([H])/[C@]13[H])C(=O)OC([H])([H])[H])C([H])(C([H])([H])[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C23H32O7/c1-13(2)23(27)11-8-16-18(25)9-10-22(4)19(29-14(3)24)7-6-15(21(26)28-5)12-17(23)20(16)30-22/h12-13,17,19,27H,6-11H2,1-5H3/b15-12+/t17-,19-,22+,23+/m0/s1

> <INCHI_KEY>
CUJMTJOOSMTWQY-RPNVNTMISA-N

> <FORMULA>
C23H32O7

> <MOLECULAR_WEIGHT>
420.502

> <EXACT_MASS>
420.21480337

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
62

> <JCHEM_AVERAGE_POLARIZABILITY>
44.67873855459272

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl (1R,2R,9R,10S,13E)-10-(acetyloxy)-2-hydroxy-9-methyl-6-oxo-2-(propan-2-yl)-16-oxatricyclo[7.5.2.0^{5,15}]hexadeca-5(15),13-diene-13-carboxylate

> <ALOGPS_LOGP>
2.37

> <JCHEM_LOGP>
2.234795559

> <ALOGPS_LOGS>
-3.87

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
16.287156110607015

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.558596416693268

> <JCHEM_PKA_STRONGEST_BASIC>
-3.175716753953049

> <JCHEM_POLAR_SURFACE_AREA>
99.13

> <JCHEM_REFRACTIVITY>
111.02049999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.61e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl (1R,2R,9R,10S,13E)-10-(acetyloxy)-2-hydroxy-2-isopropyl-9-methyl-6-oxo-16-oxatricyclo[7.5.2.0^{5,15}]hexadeca-5(15),13-diene-13-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 62 64  0  0  0  0  0  0  0  0999 V2000
    3.1704   -4.7793    0.1957 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3840   -3.6099   -0.0323 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4045   -3.4191    0.8864 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1435   -4.1710    1.8143 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6730   -2.1309    0.6506 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7745   -1.4776   -0.5267 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0551   -0.1981   -0.9272 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7414    1.0186   -0.2962 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4949    1.8642   -1.0295 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7826    1.6377   -2.4963 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2250    0.3461   -3.1017 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1321   -0.0506   -2.4883 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0387    1.0378   -2.7572 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7250   -1.3332   -3.1758 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9597   -1.1528   -4.6853 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0514   -1.7928   -2.5489 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0328    3.1719   -0.5226 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5609    3.9615   -1.3091 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9218    3.5369    0.9367 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3425    2.3772    1.8228 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1921    1.3800    2.0921 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3198    1.9587    3.2304 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2868    1.2771    0.9782 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7872   -0.0027    2.5210 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6705    0.2168    3.6553 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7813   -0.5691    3.7188 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5751   -0.2319    4.9432 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0959   -1.4231    2.9033 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7737   -1.0902    2.9434 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1267   -1.6407    1.8329 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6644   -4.7265    1.1711 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9404   -4.8258   -0.5794 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5503   -5.6781    0.1221 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4285   -1.8964   -1.2894 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9616   -0.2214   -0.5123 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3584    2.4794   -3.0609 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8661    1.6586   -2.6680 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1354    0.5196   -4.1798 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9558   -0.4614   -2.9760 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8430    0.9145   -2.2250 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0099   -2.1580   -3.0675 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6315   -0.3140   -4.8941 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4104   -2.0541   -5.1163 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0214   -0.9862   -5.2214 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9371   -2.0449   -1.4914 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8283   -1.0269   -2.6378 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4199   -2.6955   -3.0494 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9142    3.9086    1.1433 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6158    4.3686    1.1116 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1869    1.8559    1.3513 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7277    2.7657    2.7745 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0544    2.9562    2.9746 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5753    1.3490    3.3943 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8681    2.0364    4.1746 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3818   -0.3738    1.6781 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8975    0.8114    4.8997 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4624   -0.8698    4.9869 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9723   -0.4122    5.8368 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1507   -0.7273    3.7692 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3305   -1.9270    3.3868 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8621   -0.8834    1.5492 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7291   -2.4654    2.2350 H   0  0  0  0  0  0  0  0  0  0  0  0
 30 29  1  0
  7  6  1  0
 21 24  1  0
 29 24  1  0
  6  5  2  0
  5  3  1  0
  5 30  1  0
 12 14  1  0
  8  7  1  0
 14 15  1  0
 11 12  1  0
 14 16  1  0
  8  9  2  0
 17 18  2  0
 21 22  1  1
  9 17  1  0
 12 13  1  1
 11 10  1  0
  7 35  1  1
 17 19  1  0
 24 25  1  0
 12  7  1  0
  3  4  2  0
 23 21  1  0
  3  2  1  0
  9 10  1  0
  2  1  1  0
 19 20  1  0
 25 26  1  0
 21 20  1  0
 26 27  1  0
  8 23  1  0
 26 28  2  0
 11 38  1  0
 11 39  1  0
 10 36  1  0
 10 37  1  0
  6 34  1  0
 30 61  1  0
 30 62  1  0
 19 48  1  0
 19 49  1  0
 20 50  1  0
 20 51  1  0
 29 59  1  0
 29 60  1  0
 24 55  1  6
 14 41  1  6
 15 42  1  0
 15 43  1  0
 15 44  1  0
 16 45  1  0
 16 46  1  0
 16 47  1  0
 22 52  1  0
 22 53  1  0
 22 54  1  0
 13 40  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
 27 56  1  0
 27 57  1  0
 27 58  1  0
M  END

HEADER    PROTEIN                                 21-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   21-JUN-21         0                                  
HETATM    1  C   UNK     0       3.170  -4.779   0.196  0.00  0.00           C+0
HETATM    2  O   UNK     0       2.384  -3.610  -0.032  0.00  0.00           O+0
HETATM    3  C   UNK     0       1.405  -3.419   0.886  0.00  0.00           C+0
HETATM    4  O   UNK     0       1.143  -4.171   1.814  0.00  0.00           O+0
HETATM    5  C   UNK     0       0.673  -2.131   0.651  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.775  -1.478  -0.527  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.055  -0.198  -0.927  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.741   1.019  -0.296  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.495   1.864  -1.030  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.783   1.638  -2.496  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.225   0.346  -3.102  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.132  -0.051  -2.488  0.00  0.00           C+0
HETATM   13  O   UNK     0      -1.039   1.038  -2.757  0.00  0.00           O+0
HETATM   14  C   UNK     0      -0.725  -1.333  -3.176  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.960  -1.153  -4.685  0.00  0.00           C+0
HETATM   16  C   UNK     0      -2.051  -1.793  -2.549  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.033   3.172  -0.523  0.00  0.00           C+0
HETATM   18  O   UNK     0       2.561   3.962  -1.309  0.00  0.00           O+0
HETATM   19  C   UNK     0       1.922   3.537   0.937  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.342   2.377   1.823  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.192   1.380   2.092  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.320   1.959   3.230  0.00  0.00           C+0
HETATM   23  O   UNK     0       0.287   1.277   0.978  0.00  0.00           O+0
HETATM   24  C   UNK     0       1.787  -0.003   2.521  0.00  0.00           C+0
HETATM   25  O   UNK     0       2.671   0.217   3.655  0.00  0.00           O+0
HETATM   26  C   UNK     0       3.781  -0.569   3.719  0.00  0.00           C+0
HETATM   27  C   UNK     0       4.575  -0.232   4.943  0.00  0.00           C+0
HETATM   28  O   UNK     0       4.096  -1.423   2.903  0.00  0.00           O+0
HETATM   29  C   UNK     0       0.774  -1.090   2.943  0.00  0.00           C+0
HETATM   30  C   UNK     0      -0.127  -1.641   1.833  0.00  0.00           C+0
HETATM   31  H   UNK     0       3.664  -4.726   1.171  0.00  0.00           H+0
HETATM   32  H   UNK     0       3.940  -4.826  -0.579  0.00  0.00           H+0
HETATM   33  H   UNK     0       2.550  -5.678   0.122  0.00  0.00           H+0
HETATM   34  H   UNK     0       1.429  -1.896  -1.289  0.00  0.00           H+0
HETATM   35  H   UNK     0      -0.962  -0.221  -0.512  0.00  0.00           H+0
HETATM   36  H   UNK     0       1.358   2.479  -3.061  0.00  0.00           H+0
HETATM   37  H   UNK     0       2.866   1.659  -2.668  0.00  0.00           H+0
HETATM   38  H   UNK     0       1.135   0.520  -4.180  0.00  0.00           H+0
HETATM   39  H   UNK     0       1.956  -0.461  -2.976  0.00  0.00           H+0
HETATM   40  H   UNK     0      -1.843   0.915  -2.225  0.00  0.00           H+0
HETATM   41  H   UNK     0      -0.010  -2.158  -3.067  0.00  0.00           H+0
HETATM   42  H   UNK     0      -1.632  -0.314  -4.894  0.00  0.00           H+0
HETATM   43  H   UNK     0      -1.410  -2.054  -5.116  0.00  0.00           H+0
HETATM   44  H   UNK     0      -0.021  -0.986  -5.221  0.00  0.00           H+0
HETATM   45  H   UNK     0      -1.937  -2.045  -1.491  0.00  0.00           H+0
HETATM   46  H   UNK     0      -2.828  -1.027  -2.638  0.00  0.00           H+0
HETATM   47  H   UNK     0      -2.420  -2.696  -3.049  0.00  0.00           H+0
HETATM   48  H   UNK     0       0.914   3.909   1.143  0.00  0.00           H+0
HETATM   49  H   UNK     0       2.616   4.369   1.112  0.00  0.00           H+0
HETATM   50  H   UNK     0       3.187   1.856   1.351  0.00  0.00           H+0
HETATM   51  H   UNK     0       2.728   2.766   2.775  0.00  0.00           H+0
HETATM   52  H   UNK     0      -0.054   2.956   2.975  0.00  0.00           H+0
HETATM   53  H   UNK     0      -0.575   1.349   3.394  0.00  0.00           H+0
HETATM   54  H   UNK     0       0.868   2.036   4.175  0.00  0.00           H+0
HETATM   55  H   UNK     0       2.382  -0.374   1.678  0.00  0.00           H+0
HETATM   56  H   UNK     0       4.898   0.811   4.900  0.00  0.00           H+0
HETATM   57  H   UNK     0       5.462  -0.870   4.987  0.00  0.00           H+0
HETATM   58  H   UNK     0       3.972  -0.412   5.837  0.00  0.00           H+0
HETATM   59  H   UNK     0       0.151  -0.727   3.769  0.00  0.00           H+0
HETATM   60  H   UNK     0       1.331  -1.927   3.387  0.00  0.00           H+0
HETATM   61  H   UNK     0      -0.862  -0.883   1.549  0.00  0.00           H+0
HETATM   62  H   UNK     0      -0.729  -2.465   2.235  0.00  0.00           H+0
CONECT    1    2   31   32   33                                             
CONECT    2    3    1                                                       
CONECT    3    5    4    2                                                  
CONECT    4    3                                                            
CONECT    5    6    3   30                                                  
CONECT    6    7    5   34                                                  
CONECT    7    6    8   35   12                                             
CONECT    8    7    9   23                                                  
CONECT    9    8   17   10                                                  
CONECT   10   11    9   36   37                                             
CONECT   11   12   10   38   39                                             
CONECT   12   14   11   13    7                                             
CONECT   13   12   40                                                       
CONECT   14   12   15   16   41                                             
CONECT   15   14   42   43   44                                             
CONECT   16   14   45   46   47                                             
CONECT   17   18    9   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20   48   49                                             
CONECT   20   19   21   50   51                                             
CONECT   21   24   22   23   20                                             
CONECT   22   21   52   53   54                                             
CONECT   23   21    8                                                       
CONECT   24   21   29   25   55                                             
CONECT   25   24   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26   56   57   58                                             
CONECT   28   26                                                            
CONECT   29   30   24   59   60                                             
CONECT   30   29    5   61   62                                             
CONECT   31    1                                                            
CONECT   32    1                                                            
CONECT   33    1                                                            
CONECT   34    6                                                            
CONECT   35    7                                                            
CONECT   36   10                                                            
CONECT   37   10                                                            
CONECT   38   11                                                            
CONECT   39   11                                                            
CONECT   40   13                                                            
CONECT   41   14                                                            
CONECT   42   15                                                            
CONECT   43   15                                                            
CONECT   44   15                                                            
CONECT   45   16                                                            
CONECT   46   16                                                            
CONECT   47   16                                                            
CONECT   48   19                                                            
CONECT   49   19                                                            
CONECT   50   20                                                            
CONECT   51   20                                                            
CONECT   52   22                                                            
CONECT   53   22                                                            
CONECT   54   22                                                            
CONECT   55   24                                                            
CONECT   56   27                                                            
CONECT   57   27                                                            
CONECT   58   27                                                            
CONECT   59   29                                                            
CONECT   60   29                                                            
CONECT   61   30                                                            
CONECT   62   30                                                            
MASTER        0    0    0    0    0    0    0    0   62    0  128    0
END

RDKit          3D

62 64  0  0  0  0  0  0  0  0999 V2000
    3.1704   -4.7793    0.1957 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3840   -3.6099   -0.0323 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4045   -3.4191    0.8864 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1435   -4.1710    1.8143 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6730   -2.1309    0.6506 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7745   -1.4776   -0.5267 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0551   -0.1981   -0.9272 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7414    1.0186   -0.2962 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4949    1.8642   -1.0295 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7826    1.6377   -2.4963 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2250    0.3461   -3.1017 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1321   -0.0506   -2.4883 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0387    1.0378   -2.7572 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7250   -1.3332   -3.1758 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9597   -1.1528   -4.6853 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0514   -1.7928   -2.5489 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0328    3.1719   -0.5226 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5609    3.9615   -1.3091 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9218    3.5369    0.9367 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3425    2.3772    1.8228 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1921    1.3800    2.0921 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3198    1.9587    3.2304 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2868    1.2771    0.9782 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7872   -0.0027    2.5210 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6705    0.2168    3.6553 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7813   -0.5691    3.7188 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5751   -0.2319    4.9432 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0959   -1.4231    2.9033 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7737   -1.0902    2.9434 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1267   -1.6407    1.8329 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6644   -4.7265    1.1711 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9404   -4.8258   -0.5794 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5503   -5.6781    0.1221 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4285   -1.8964   -1.2894 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9616   -0.2214   -0.5123 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3584    2.4794   -3.0609 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8661    1.6586   -2.6680 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1354    0.5196   -4.1798 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9558   -0.4614   -2.9760 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8430    0.9145   -2.2250 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0099   -2.1580   -3.0675 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6315   -0.3140   -4.8941 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4104   -2.0541   -5.1163 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0214   -0.9862   -5.2214 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9371   -2.0449   -1.4914 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8283   -1.0269   -2.6378 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4199   -2.6955   -3.0494 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9142    3.9086    1.1433 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6158    4.3686    1.1116 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1869    1.8559    1.3513 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7277    2.7657    2.7745 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0544    2.9562    2.9746 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5753    1.3490    3.3943 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8681    2.0364    4.1746 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3818   -0.3738    1.6781 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8975    0.8114    4.8997 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4624   -0.8698    4.9869 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9723   -0.4122    5.8368 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1507   -0.7273    3.7692 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3305   -1.9270    3.3868 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8621   -0.8834    1.5492 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7291   -2.4654    2.2350 H   0  0  0  0  0  0  0  0  0  0  0  0
 30 29  1  0
  7  6  1  0
 21 24  1  0
 29 24  1  0
  6  5  2  0
  5  3  1  0
  5 30  1  0
 12 14  1  0
  8  7  1  0
 14 15  1  0
 11 12  1  0
 14 16  1  0
  8  9  2  0
 17 18  2  0
 21 22  1  1
  9 17  1  0
 12 13  1  1
 11 10  1  0
  7 35  1  1
 17 19  1  0
 24 25  1  0
 12  7  1  0
  3  4  2  0
 23 21  1  0
  3  2  1  0
  9 10  1  0
  2  1  1  0
 19 20  1  0
 25 26  1  0
 21 20  1  0
 26 27  1  0
  8 23  1  0
 26 28  2  0
 11 38  1  0
 11 39  1  0
 10 36  1  0
 10 37  1  0
  6 34  1  0
 30 61  1  0
 30 62  1  0
 19 48  1  0
 19 49  1  0
 20 50  1  0
 20 51  1  0
 29 59  1  0
 29 60  1  0
 24 55  1  6
 14 41  1  6
 15 42  1  0
 15 43  1  0
 15 44  1  0
 16 45  1  0
 16 46  1  0
 16 47  1  0
 22 52  1  0
 22 53  1  0
 22 54  1  0
 13 40  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
 27 56  1  0
 27 57  1  0
 27 58  1  0
M  END

View in JSmol View DFT Assignments 3D Conformers

Synonyms

Not Available

Chemical Formula

C₂₃H₃₂O₇

Average Mass

420.5020 Da

Monoisotopic Mass

420.21480 Da

IUPAC Name

methyl (1R,2R,9R,10S,13E)-10-(acetyloxy)-2-hydroxy-9-methyl-6-oxo-2-(propan-2-yl)-16-oxatricyclo[7.5.2.0^{5,15}]hexadeca-5(15),13-diene-13-carboxylate

Traditional Name

methyl (1R,2R,9R,10S,13E)-10-(acetyloxy)-2-hydroxy-2-isopropyl-9-methyl-6-oxo-16-oxatricyclo[7.5.2.0^{5,15}]hexadeca-5(15),13-diene-13-carboxylate

CAS Registry Number

Not Available

SMILES

[H]O[C@]1(C([H])([H])C([H])([H])C2=C3O[C@](C([H])([H])[H])(C([H])([H])C([H])([H])C2=O)[C@@]([H])(OC(=O)C([H])([H])[H])C([H])([H])C([H])([H])\C(=C([H])/[C@]13[H])C(=O)OC([H])([H])[H])C([H])(C([H])([H])[H])C([H])([H])[H]

InChI Identifier

InChI=1S/C23H32O7/c1-13(2)23(27)11-8-16-18(25)9-10-22(4)19(29-14(3)24)7-6-15(21(26)28-5)12-17(23)20(16)30-22/h12-13,17,19,27H,6-11H2,1-5H3/b15-12+/t17-,19-,22+,23+/m0/s1

InChI Key

CUJMTJOOSMTWQY-RPNVNTMISA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
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, 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, 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, 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

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 150 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 175 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 225 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 250 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, chcl3, 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
Sarcophyton tortuosum	JEOL database	Lin, K.-H., et al, Org. Lett. 16, 1314 (2014)

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Sesquiterpenoids

Alternative Parents

Substituents

Sesquiterpenoid
Dicarboxylic acid or derivatives
Vinylogous ester
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Methyl ester
Tertiary alcohol
Ketone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
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	2.37	ALOGPS
logP	2.23	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Acidic)	5.56	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	99.13 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	111.02 m³·mol⁻¹	ChemAxon
Polarizability	44.68 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	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

32033975

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

102232567

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Lin, K.-H., et al. (2014). Lin, K.-H., et al, Org. Lett. 16, 1314 (2014). Org. Lett..

Showing NP-Card for tortuosene A (NP0042829)

MOL for NP0042829 (tortuosene A)

3D MOL for NP0042829 (tortuosene A)

3D SDF for NP0042829 (tortuosene A)

3D-SDF for NP0042829 (tortuosene A)

PDB for NP0042829 (tortuosene A)

3D PDB for NP0042829 (tortuosene A)

SMILES for NP0042829 (tortuosene A)

INCHI for NP0042829 (tortuosene A)

Structure for NP0042829 (tortuosene A)

3D Structure for NP0042829 (tortuosene A)