NP-MRD: Showing NP-Card for (1s,2r,4s,7e,9s,13s,14r)-13-hydroxy-14-methyl-9-[(2r)-3-methylbut-3-en-2-yl]-6,15-dimethylidene-3,10,17-trioxatricyclo[11.3.1.0²,⁴]heptadec-7-en-11-one (NP0312013)

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Record Information

Version

2.0

Created at

2022-09-11 08:25:38 UTC

Updated at

2022-09-11 08:25:39 UTC

NP-MRD ID

NP0312013

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,2r,4s,7e,9s,13s,14r)-13-hydroxy-14-methyl-9-[(2r)-3-methylbut-3-en-2-yl]-6,15-dimethylidene-3,10,17-trioxatricyclo[11.3.1.0²,⁴]heptadec-7-en-11-one

Description

Amphidinolide p belongs to the class of organic compounds known as macrolides and analogues. These are organic compounds containing a lactone ring of at least twelve members. (1s,2r,4s,7e,9s,13s,14r)-13-hydroxy-14-methyl-9-[(2r)-3-methylbut-3-en-2-yl]-6,15-dimethylidene-3,10,17-trioxatricyclo[11.3.1.0²,⁴]heptadec-7-en-11-one was first documented in 2013 (PMID: 23790123). Based on a literature review a small amount of articles have been published on amphidinolide p (PMID: 27400333) (PMID: 27373658) (PMID: 26114894) (PMID: 23590535).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309112210252D          

 27 29  0  0  1  0            999 V2000
    2.2961    0.1480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1156    0.2427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4435    0.9998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3350    1.1421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8807    1.7609    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.7009    2.5660    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.3083    3.1243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9137    2.8129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7339    3.6181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3063    2.2546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6378    1.4330    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5599    0.6117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7606    0.4074    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0660   -0.1359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7382   -0.8929    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.5578   -0.7983    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9187   -0.9876    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5908   -1.7446    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.0826   -2.4071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9021   -2.3124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3939   -2.9749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2300   -1.5554    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.0495   -1.4607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7713   -1.8393    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9517   -1.9339    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2796   -1.1768    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6074   -0.4198    0.0000 C   0  0  0  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
  4  5  1  0  0  0  0
  5  6  1  1  0  0  0
  6  7  1  1  0  0  0
  6  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
  5 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  6  0  0  0
 15 17  1  0  0  0  0
 18 17  1  1  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
 15 22  1  0  0  0  0
 22 23  1  6  0  0  0
 18 24  1  0  0  0  0
 24 25  1  6  0  0  0
 26 25  1  1  0  0  0
 24 26  1  0  0  0  0
 26 27  1  0  0  0  0
  2 27  1  0  0  0  0
M  END

     RDKit          3D

 57 59  0  0  0  0  0  0  0  0999 V2000
    0.3902    3.8926    1.0349 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2485    2.6940    0.5073 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6832    1.5289    1.3001 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0538    0.3671    0.7921 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9356    0.1423   -0.3642 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2782   -0.4711    0.0839 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.8442    0.3495    1.2092 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1794   -0.5513   -1.0816 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6591   -1.7228   -1.4996 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5950    0.6642   -1.8427 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4748   -0.6440   -1.3830 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3360   -1.2740   -1.6913 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0747   -1.1559   -2.9042 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5386   -2.0992   -0.8401 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8478   -1.4360   -0.4982 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8080   -1.9151   -1.4051 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8330   -0.0823   -0.6447 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8955    0.6510   -0.2160 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.8398   -0.0149    0.7309 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1174   -0.9892    1.5906 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2662   -0.9873    2.8855 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2390   -1.9339    0.8595 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.9976   -3.2332    0.6909 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3474    1.9501    0.2897 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.6913    3.1852   -0.1033 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7884    2.6815   -0.9464 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3302    2.5936   -0.8331 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0804    4.7527    0.4723 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8066    4.0040    2.0066 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6724    1.7084    2.3706 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6694   -0.5195    1.2802 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2613    1.1246   -0.8300 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0294   -1.5002    0.4162 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3986    1.3704    1.1455 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5071   -0.0997    2.1808 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9393    0.3870    1.2167 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4050   -2.6615   -0.9986 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3216   -1.8157   -2.3503 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6845    1.0366   -2.3916 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4253    0.4573   -2.5194 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9342    1.4003   -1.0740 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7708   -3.0191   -1.4187 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0676   -2.4438    0.0834 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4634   -1.9582   -2.3246 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5188    0.8627   -1.1416 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3659    0.7693    1.3076 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5665   -0.6148    0.1453 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9202   -0.2737    3.3546 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7411   -1.6943    3.5035 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3623   -2.1629    1.5163 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8462   -3.0061   -0.0172 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3462   -4.0293    0.2732 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3878   -3.5836    1.6517 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7431    1.8706    1.1862 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2112    2.3587   -1.9413 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0146    1.6653   -1.3759 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1274    3.4248   -1.4485 H   0  0  0  0  0  0  0  0  0  0  0  0
  7  6  1  0
  6  5  1  0
  5 11  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  1  0
 15 16  1  6
 15 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  2  3
 20 22  1  0
 22 23  1  0
 18 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27  2  1  0
  2  1  2  0
  2  3  1  0
  3  4  2  0
  6  8  1  0
  8 10  1  0
  8  9  2  3
  4  5  1  0
 22 15  1  0
 26 24  1  0
  7 34  1  0
  7 35  1  0
  7 36  1  0
  6 33  1  1
  5 32  1  6
 14 42  1  0
 14 43  1  0
 16 44  1  0
 18 45  1  6
 19 46  1  0
 19 47  1  0
 21 48  1  0
 21 49  1  0
 22 50  1  1
 23 51  1  0
 23 52  1  0
 23 53  1  0
 24 54  1  1
 26 55  1  6
 27 56  1  0
 27 57  1  0
  1 28  1  0
  1 29  1  0
  3 30  1  0
  4 31  1  0
 10 39  1  0
 10 40  1  0
 10 41  1  0
  9 37  1  0
  9 38  1  0
M  END


  Mrv1652309112210252D          

 27 29  0  0  1  0            999 V2000
    2.2961    0.1480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1156    0.2427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4435    0.9998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3350    1.1421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8807    1.7609    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.7009    2.5660    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.3083    3.1243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9137    2.8129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7339    3.6181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3063    2.2546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6378    1.4330    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5599    0.6117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7606    0.4074    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0660   -0.1359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7382   -0.8929    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.5578   -0.7983    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9187   -0.9876    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5908   -1.7446    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.0826   -2.4071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9021   -2.3124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3939   -2.9749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2300   -1.5554    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.0495   -1.4607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7713   -1.8393    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9517   -1.9339    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2796   -1.1768    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6074   -0.4198    0.0000 C   0  0  0  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
  4  5  1  0  0  0  0
  5  6  1  1  0  0  0
  6  7  1  1  0  0  0
  6  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
  5 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  6  0  0  0
 15 17  1  0  0  0  0
 18 17  1  1  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
 15 22  1  0  0  0  0
 22 23  1  6  0  0  0
 18 24  1  0  0  0  0
 24 25  1  6  0  0  0
 26 25  1  1  0  0  0
 24 26  1  0  0  0  0
 26 27  1  0  0  0  0
  2 27  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0312013

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C22H30O5/c1-12(2)15(5)17-8-7-13(3)9-18-21(26-18)19-10-14(4)16(6)22(24,27-19)11-20(23)25-17/h7-8,15-19,21,24H,1,3-4,9-11H2,2,5-6H3/b8-7+/t15-,16-,17+,18+,19+,21-,22+/m1/s1

> <INCHI_KEY>
OHHBGABQODNLQQ-HREDAHEJSA-N

> <FORMULA>
C22H30O5

> <MOLECULAR_WEIGHT>
374.477

> <EXACT_MASS>
374.209324066

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
57

> <JCHEM_AVERAGE_POLARIZABILITY>
39.68097709687705

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,2R,4S,7E,9S,13S,14R)-13-hydroxy-14-methyl-9-[(2R)-3-methylbut-3-en-2-yl]-6,15-dimethylidene-3,10,17-trioxatricyclo[11.3.1.0^{2,4}]heptadec-7-en-11-one

> <JCHEM_LOGP>
3.5729909143333325

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.510523665391311

> <JCHEM_PKA_STRONGEST_BASIC>
-3.99583949042696

> <JCHEM_POLAR_SURFACE_AREA>
68.29

> <JCHEM_REFRACTIVITY>
103.15629999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2R,4S,7E,9S,13S,14R)-13-hydroxy-14-methyl-9-[(2R)-3-methylbut-3-en-2-yl]-6,15-dimethylidene-3,10,17-trioxatricyclo[11.3.1.0^{2,4}]heptadec-7-en-11-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 11-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-22         0                                  
HETATM    1  C   UNK     0       4.286   0.276   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.816   0.453   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.428   1.866   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.092   2.132   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.111   3.287   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.775   4.790   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.909   5.832   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.306   5.251   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.970   6.754   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.172   4.209   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      10.524   2.675   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      10.379   1.142   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       8.887   0.760   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      11.323  -0.254   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      10.711  -1.667   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      12.241  -1.490   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       9.182  -1.843   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       8.570  -3.257   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       9.487  -4.493   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      11.017  -4.317   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      11.935  -5.553   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      11.629  -2.903   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      13.159  -2.727   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       7.040  -3.433   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       5.510  -3.610   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       6.122  -2.197   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       6.734  -0.784   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   27                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   11                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11    5   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16   17   22                                             
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17   19   24                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   15   23                                                  
CONECT   23   22                                                            
CONECT   24   18   25   26                                                  
CONECT   25   24   26                                                       
CONECT   26   25   24   27                                                  
CONECT   27   26    2                                                       
MASTER        0    0    0    0    0    0    0    0   27    0   58    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₂H₃₀O₅

Average Mass

374.4770 Da

Monoisotopic Mass

374.20932 Da

IUPAC Name

(1S,2R,4S,7E,9S,13S,14R)-13-hydroxy-14-methyl-9-[(2R)-3-methylbut-3-en-2-yl]-6,15-dimethylidene-3,10,17-trioxatricyclo[11.3.1.0^{2,4}]heptadec-7-en-11-one

Traditional Name

(1S,2R,4S,7E,9S,13S,14R)-13-hydroxy-14-methyl-9-[(2R)-3-methylbut-3-en-2-yl]-6,15-dimethylidene-3,10,17-trioxatricyclo[11.3.1.0^{2,4}]heptadec-7-en-11-one

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C22H30O5/c1-12(2)15(5)17-8-7-13(3)9-18-21(26-18)19-10-14(4)16(6)22(24,27-19)11-20(23)25-17/h7-8,15-19,21,24H,1,3-4,9-11H2,2,5-6H3/b8-7+/t15-,16-,17+,18+,19+,21-,22+/m1/s1

InChI Key

OHHBGABQODNLQQ-HREDAHEJSA-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

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as macrolides and analogues. These are organic compounds containing a lactone ring of at least twelve members.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Macrolides and analogues

Sub Class

Not Available

Direct Parent

Macrolides and analogues

Alternative Parents

Substituents

Macrolide
Oxane
Carboxylic acid ester
Hemiacetal
Lactone
Carboxylic acid derivative
Dialkyl ether
Oxirane
Ether
Oxacycle
Monocarboxylic acid or derivatives
Organoheterocyclic compound
Organic oxide
Hydrocarbon derivative
Carbonyl group
Organooxygen compound
Organic oxygen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

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

Predicted Properties

Property	Value	Source
logP	3.57	ChemAxon
pKa (Strongest Acidic)	11.51	ChemAxon
pKa (Strongest Basic)	-4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	68.29 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	103.16 m³·mol⁻¹	ChemAxon
Polarizability	39.68 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

8560245

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10384803

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Nuzzo G, Gomes BA, Luongo E, Torres MC, Santos EA, Cutignano A, Pessoa OD, Costa-Lotufo LV, Fontana A: Dinoflagellate-Related Amphidinolides from the Brazilian Octocoral Stragulum bicolor. J Nat Prod. 2016 Jul 22;79(7):1881-5. doi: 10.1021/acs.jnatprod.6b00259. Epub 2016 Jul 11. [PubMed:27400333 ]
Kubota T, Sato H, Iwai T, Kobayashi J: Biosynthetic Study of Amphidinin A and Amphidinolide P. Chem Pharm Bull (Tokyo). 2016;64(7):979-81. doi: 10.1248/cpb.c16-00202. [PubMed:27373658 ]
Jecs E, Diver ST: Two Ene-Yne Metathesis Approaches to the Total Synthesis of Amphidinolide P. Org Lett. 2015 Jul 17;17(14):3510-3. doi: 10.1021/acs.orglett.5b01601. Epub 2015 Jun 26. [PubMed:26114894 ]
Hwang MH, Han SJ, Lee DH: Convergent and enantioselective total synthesis of (-)-amphidinolide O and (-)-amphidinolide P. Org Lett. 2013 Jul 5;15(13):3318-21. doi: 10.1021/ol401357k. Epub 2013 Jun 24. [PubMed:23790123 ]
Williams DR, Myers BJ, Mi L, Binder RJ: Studies for the total synthesis of amphidinolide P. J Org Chem. 2013 May 17;78(10):4762-78. doi: 10.1021/jo4002382. Epub 2013 Apr 26. [PubMed:23590535 ]
LOTUS database [Link]

Showing NP-Card for (1s,2r,4s,7e,9s,13s,14r)-13-hydroxy-14-methyl-9-[(2r)-3-methylbut-3-en-2-yl]-6,15-dimethylidene-3,10,17-trioxatricyclo[11.3.1.0²,⁴]heptadec-7-en-11-one (NP0312013)

MOL for NP0312013 ((1s,2r,4s,7e,9s,13s,14r)-13-hydroxy-14-methyl-9-[(2r)-3-methylbut-3-en-2-yl]-6,15-dimethylidene-3,10,17-trioxatricyclo[11.3.1.0²,⁴]heptadec-7-en-11-one)

3D MOL for NP0312013 ((1s,2r,4s,7e,9s,13s,14r)-13-hydroxy-14-methyl-9-[(2r)-3-methylbut-3-en-2-yl]-6,15-dimethylidene-3,10,17-trioxatricyclo[11.3.1.0²,⁴]heptadec-7-en-11-one)

3D SDF for NP0312013 ((1s,2r,4s,7e,9s,13s,14r)-13-hydroxy-14-methyl-9-[(2r)-3-methylbut-3-en-2-yl]-6,15-dimethylidene-3,10,17-trioxatricyclo[11.3.1.0²,⁴]heptadec-7-en-11-one)

3D-SDF for NP0312013 ((1s,2r,4s,7e,9s,13s,14r)-13-hydroxy-14-methyl-9-[(2r)-3-methylbut-3-en-2-yl]-6,15-dimethylidene-3,10,17-trioxatricyclo[11.3.1.0²,⁴]heptadec-7-en-11-one)

PDB for NP0312013 ((1s,2r,4s,7e,9s,13s,14r)-13-hydroxy-14-methyl-9-[(2r)-3-methylbut-3-en-2-yl]-6,15-dimethylidene-3,10,17-trioxatricyclo[11.3.1.0²,⁴]heptadec-7-en-11-one)

3D PDB for NP0312013 ((1s,2r,4s,7e,9s,13s,14r)-13-hydroxy-14-methyl-9-[(2r)-3-methylbut-3-en-2-yl]-6,15-dimethylidene-3,10,17-trioxatricyclo[11.3.1.0²,⁴]heptadec-7-en-11-one)

SMILES for NP0312013 ((1s,2r,4s,7e,9s,13s,14r)-13-hydroxy-14-methyl-9-[(2r)-3-methylbut-3-en-2-yl]-6,15-dimethylidene-3,10,17-trioxatricyclo[11.3.1.0²,⁴]heptadec-7-en-11-one)

INCHI for NP0312013 ((1s,2r,4s,7e,9s,13s,14r)-13-hydroxy-14-methyl-9-[(2r)-3-methylbut-3-en-2-yl]-6,15-dimethylidene-3,10,17-trioxatricyclo[11.3.1.0²,⁴]heptadec-7-en-11-one)

Structure for NP0312013 ((1s,2r,4s,7e,9s,13s,14r)-13-hydroxy-14-methyl-9-[(2r)-3-methylbut-3-en-2-yl]-6,15-dimethylidene-3,10,17-trioxatricyclo[11.3.1.0²,⁴]heptadec-7-en-11-one)

3D Structure for NP0312013 ((1s,2r,4s,7e,9s,13s,14r)-13-hydroxy-14-methyl-9-[(2r)-3-methylbut-3-en-2-yl]-6,15-dimethylidene-3,10,17-trioxatricyclo[11.3.1.0²,⁴]heptadec-7-en-11-one)