NP-MRD: Showing NP-Card for (1r,4s,6s,9e,13s,14r)-13-hydroxy-4,9,13-trimethyl-17-methylidene-5,15-dioxatricyclo[12.3.1.0⁴,⁶]octadec-9-en-16-one (NP0282963)

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Record Information

Version

2.0

Created at

2022-09-09 10:00:41 UTC

Updated at

2022-09-09 10:00:41 UTC

NP-MRD ID

NP0282963

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,4s,6s,9e,13s,14r)-13-hydroxy-4,9,13-trimethyl-17-methylidene-5,15-dioxatricyclo[12.3.1.0⁴,⁶]octadec-9-en-16-one

Description

Flexibilide 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. (1r,4s,6s,9e,13s,14r)-13-hydroxy-4,9,13-trimethyl-17-methylidene-5,15-dioxatricyclo[12.3.1.0⁴,⁶]octadec-9-en-16-one is found in Sinularia capillosa and Sinularia flexibilis. (1r,4s,6s,9e,13s,14r)-13-hydroxy-4,9,13-trimethyl-17-methylidene-5,15-dioxatricyclo[12.3.1.0⁴,⁶]octadec-9-en-16-one was first documented in 2008 (PMID: 18553926). Based on a literature review a small amount of articles have been published on Flexibilide (PMID: 26859520) (PMID: 24979268) (PMID: 23118718) (PMID: 19048343).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 54 56  0  0  0  0  0  0  0  0999 V2000
   -3.4331    1.5564   -1.5924 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2191    0.7757   -0.5731 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7801   -0.5893   -0.6016 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5364   -0.9703   -1.5495 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4305   -1.4107    0.4586 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0960   -1.3564    0.9245 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5529    0.0138    1.1025 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4573    1.1272    0.6303 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6766    2.4166    0.4981 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5685    2.3635   -0.4910 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7975    2.6815    0.0529 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0075    2.6262    1.5285 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5693    3.6769   -0.5479 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8112    2.4007   -0.9468 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8866    1.5312   -0.4338 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2530    0.2280   -0.0098 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1383   -0.9447   -0.0959 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6124   -0.7829   -0.1624 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5679   -2.1451   -0.1116 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1969   -2.4126   -0.5561 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1638   -2.3617    0.5537 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2337   -2.2422    0.0149 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9201   -3.6156    0.0545 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2904   -1.8378   -1.3051 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0048    1.2333   -2.4496 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0514    2.5676   -1.6359 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1124   -1.9230    1.9036 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3695    0.1778    2.2038 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5493    0.0864    0.6379 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2017    1.3049    1.4495 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3746    2.7071    1.5273 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4134    3.2065    0.1923 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5689    1.3575   -0.9580 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7233    3.0728   -1.3549 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4093    1.9098    2.0833 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7214    3.6439    1.9315 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1096    2.5611    1.7597 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4755    2.1666   -1.9781 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5171    1.9756    0.3575 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5950    1.2828   -1.2777 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4166    0.0360   -0.7342 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8133    0.3043    1.0045 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8926    0.2664   -0.0745 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1149   -1.3862    0.6483 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9368   -1.2454   -1.1392 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2038   -2.9773    0.2423 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8518   -1.7994   -1.4048 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1499   -3.4757   -0.9409 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2106   -3.3326    1.1304 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3874   -1.5895    1.3182 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4346   -4.2612    0.8126 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8324   -4.1326   -0.9217 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9853   -3.5286    0.3141 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9939   -0.9375   -1.4886 H   0  0  0  0  0  0  0  0  0  0  0  0
 18 17  1  0
 17 19  2  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 22 24  1  6
 22  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  1
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
  8  2  1  0
  2  1  2  3
  2  3  1  0
  3  4  2  0
  3  5  1  0
 16 17  1  0
  5  6  1  0
 14 11  1  0
 18 43  1  0
 18 44  1  0
 18 45  1  0
 19 46  1  0
 20 47  1  0
 20 48  1  0
 21 49  1  0
 21 50  1  0
 23 51  1  0
 23 52  1  0
 23 53  1  0
 24 54  1  0
  6 27  1  1
  7 28  1  0
  7 29  1  0
  8 30  1  1
  9 31  1  0
  9 32  1  0
 10 33  1  0
 10 34  1  0
 12 35  1  0
 12 36  1  0
 12 37  1  0
 14 38  1  6
 15 39  1  0
 15 40  1  0
 16 41  1  0
 16 42  1  0
  1 25  1  0
  1 26  1  0
M  END


  Mrv1652304282223452D          

 24 26  0  0  1  0            999 V2000
    4.5631    2.3574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1576    2.9295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9503    2.7006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1484    1.8998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9411    1.6710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1392    0.8701    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.5447    0.2981    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.7521    0.5269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1576   -0.0451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3650    0.1837    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.1668    0.9845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3742    1.2133    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1760    2.0142    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7705    2.5862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3688    1.8441    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5836    2.5883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7797    0.6413    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9779   -0.1595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3834   -0.7316    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7705   -0.3883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9687   -1.1892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3374    0.0693    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3159   -0.4945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5447    3.2727    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  1  0  0  0
 12 11  1  1  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
  1 14  1  0  0  0  0
 13 15  1  1  0  0  0
 13 16  1  6  0  0  0
 12 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
 10 20  1  0  0  0  0
 20 21  2  0  0  0  0
  7 22  1  0  0  0  0
  6 22  1  6  0  0  0
  7 23  1  6  0  0  0
  3 24  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0282963

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C\C1=C\CC[C@](C)(O)[C@H]2C[C@@H](CC[C@]3(C)O[C@H]3CC1)C(=C)C(=O)O2

> <INCHI_IDENTIFIER>
InChI=1S/C20H30O4/c1-13-6-5-10-19(3,22)17-12-15(14(2)18(21)23-17)9-11-20(4)16(24-20)8-7-13/h6,15-17,22H,2,5,7-12H2,1,3-4H3/b13-6-/t15-,16+,17-,19+,20+/m1/s1

> <INCHI_KEY>
YKKJETNBRNDYKN-ALZFIODESA-N

> <FORMULA>
C20H30O4

> <MOLECULAR_WEIGHT>
334.456

> <EXACT_MASS>
334.214409446

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
54

> <JCHEM_AVERAGE_POLARIZABILITY>
37.501186761868695

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,4S,6S,9Z,13S,14R)-13-hydroxy-4,9,13-trimethyl-17-methylidene-5,15-dioxatricyclo[12.3.1.0^{4,6}]octadec-9-en-16-one

> <ALOGPS_LOGP>
3.57

> <JCHEM_LOGP>
3.665471669666667

> <ALOGPS_LOGS>
-4.04

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.02152368176137

> <JCHEM_PKA_STRONGEST_BASIC>
-3.2267855415975752

> <JCHEM_POLAR_SURFACE_AREA>
59.06

> <JCHEM_REFRACTIVITY>
93.34159999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.07e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,4S,6S,9Z,13S,14R)-13-hydroxy-4,9,13-trimethyl-17-methylidene-5,15-dioxatricyclo[12.3.1.0^{4,6}]octadec-9-en-16-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0       8.518   4.401   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.628   5.468   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      11.107   5.041   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      11.477   3.546   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      12.957   3.119   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      13.327   1.624   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      12.217   0.556   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      10.737   0.984   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.628  -0.084   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.148   0.343   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.778   1.838   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.298   2.265   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.929   3.760   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.038   4.828   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       4.422   3.442   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       4.823   4.832   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       5.189   1.197   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       5.559  -0.298   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       4.449  -1.366   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       7.038  -0.725   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       7.408  -2.220   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      13.696   0.129   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      11.790  -0.923   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      12.217   6.109   0.000  0.00  0.00           C+0
CONECT    1    2   14                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4   24                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   22                                                  
CONECT    7    6    8   22   23                                             
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   20                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   17                                                  
CONECT   13   12   14   15   16                                             
CONECT   14   13    1                                                       
CONECT   15   13                                                            
CONECT   16   13                                                            
CONECT   17   12   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   10   21                                                  
CONECT   21   20                                                            
CONECT   22    7    6                                                       
CONECT   23    7                                                            
CONECT   24    3                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   52    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₃₀O₄

Average Mass

334.4560 Da

Monoisotopic Mass

334.21441 Da

IUPAC Name

(1R,4S,6S,9Z,13S,14R)-13-hydroxy-4,9,13-trimethyl-17-methylidene-5,15-dioxatricyclo[12.3.1.0^{4,6}]octadec-9-en-16-one

Traditional Name

(1R,4S,6S,9Z,13S,14R)-13-hydroxy-4,9,13-trimethyl-17-methylidene-5,15-dioxatricyclo[12.3.1.0^{4,6}]octadec-9-en-16-one

CAS Registry Number

Not Available

SMILES

C\C1=C\CC[C@](C)(O)[C@H]2C[C@@H](CC[C@]3(C)O[C@H]3CC1)C(=C)C(=O)O2

InChI Identifier

InChI=1S/C20H30O4/c1-13-6-5-10-19(3,22)17-12-15(14(2)18(21)23-17)9-11-20(4)16(24-20)8-7-13/h6,15-17,22H,2,5,7-12H2,1,3-4H3/b13-6-/t15-,16+,17-,19+,20+/m1/s1

InChI Key

YKKJETNBRNDYKN-ALZFIODESA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Sinularia capillosa	LOTUS Database	35616633
Sinularia flexibilis	LOTUS Database	35616633

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
Delta valerolactone
Delta_valerolactone
Oxane
Tertiary alcohol
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Carboxylic acid ester
Lactone
Monocarboxylic acid or derivatives
Ether
Oxirane
Dialkyl ether
Carboxylic acid derivative
Oxacycle
Organoheterocyclic compound
Organooxygen compound
Organic oxygen compound
Hydrocarbon derivative
Alcohol
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	3.57	ALOGPS
logP	3.67	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	14.02	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	59.06 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	93.34 m³·mol⁻¹	ChemAxon
Polarizability	37.5 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

C00039030

Chemspider ID

57260755

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

92029063

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Gao D, Wang Y, Xie W, Yang T, Jiang Y, Guo Y, Guan J, Liu H: Metabolomics study on the antitumor effect of marine natural compound flexibilide in HCT-116 colon cancer cell line. J Chromatogr B Analyt Technol Biomed Life Sci. 2016 Mar 1;1014:17-23. doi: 10.1016/j.jchromb.2016.01.003. Epub 2016 Jan 8. [PubMed:26859520 ]
Chen NF, Huang SY, Lu CH, Chen CL, Feng CW, Chen CH, Hung HC, Lin YY, Sung PJ, Sung CS, Yang SN, Wang HM, Chang YC, Sheu JH, Chen WF, Wen ZH: Flexibilide obtained from cultured soft coral has anti-neuroinflammatory and analgesic effects through the upregulation of spinal transforming growth factor-beta1 in neuropathic rats. Mar Drugs. 2014 Jun 27;12(7):3792-817. doi: 10.3390/md12073792. [PubMed:24979268 ]
Yang B, Zhou X, Huang H, Yang XW, Liu J, Lin X, Li X, Peng Y, Liu Y: New cembrane diterpenoids from a Hainan soft coral Sinularia sp. Mar Drugs. 2012 Sep;10(9):2023-2032. doi: 10.3390/md10092023. Epub 2012 Sep 18. [PubMed:23118718 ]
Khalesi MK, Beeftink HH, Wijffels RH: Light-dependency of growth and secondary metabolite production in the captive zooxanthellate soft coral Sinularia flexibilis. Mar Biotechnol (NY). 2009 Jul-Aug;11(4):488-94. doi: 10.1007/s10126-008-9164-z. Epub 2008 Dec 2. [PubMed:19048343 ]
Wen T, Ding Y, Deng Z, van Ofwegen L, Proksch P, Lin W: Sinulaflexiolides A-K, cembrane-type diterpenoids from the chinese soft coral Sinularia flexibilis. J Nat Prod. 2008 Jul;71(7):1133-40. doi: 10.1021/np070640g. Epub 2008 Jun 14. [PubMed:18553926 ]
LOTUS database [Link]

Showing NP-Card for (1r,4s,6s,9e,13s,14r)-13-hydroxy-4,9,13-trimethyl-17-methylidene-5,15-dioxatricyclo[12.3.1.0⁴,⁶]octadec-9-en-16-one (NP0282963)

MOL for NP0282963 ((1r,4s,6s,9e,13s,14r)-13-hydroxy-4,9,13-trimethyl-17-methylidene-5,15-dioxatricyclo[12.3.1.0⁴,⁶]octadec-9-en-16-one)

3D MOL for NP0282963 ((1r,4s,6s,9e,13s,14r)-13-hydroxy-4,9,13-trimethyl-17-methylidene-5,15-dioxatricyclo[12.3.1.0⁴,⁶]octadec-9-en-16-one)

3D SDF for NP0282963 ((1r,4s,6s,9e,13s,14r)-13-hydroxy-4,9,13-trimethyl-17-methylidene-5,15-dioxatricyclo[12.3.1.0⁴,⁶]octadec-9-en-16-one)

3D-SDF for NP0282963 ((1r,4s,6s,9e,13s,14r)-13-hydroxy-4,9,13-trimethyl-17-methylidene-5,15-dioxatricyclo[12.3.1.0⁴,⁶]octadec-9-en-16-one)

PDB for NP0282963 ((1r,4s,6s,9e,13s,14r)-13-hydroxy-4,9,13-trimethyl-17-methylidene-5,15-dioxatricyclo[12.3.1.0⁴,⁶]octadec-9-en-16-one)

3D PDB for NP0282963 ((1r,4s,6s,9e,13s,14r)-13-hydroxy-4,9,13-trimethyl-17-methylidene-5,15-dioxatricyclo[12.3.1.0⁴,⁶]octadec-9-en-16-one)

SMILES for NP0282963 ((1r,4s,6s,9e,13s,14r)-13-hydroxy-4,9,13-trimethyl-17-methylidene-5,15-dioxatricyclo[12.3.1.0⁴,⁶]octadec-9-en-16-one)

INCHI for NP0282963 ((1r,4s,6s,9e,13s,14r)-13-hydroxy-4,9,13-trimethyl-17-methylidene-5,15-dioxatricyclo[12.3.1.0⁴,⁶]octadec-9-en-16-one)

Structure for NP0282963 ((1r,4s,6s,9e,13s,14r)-13-hydroxy-4,9,13-trimethyl-17-methylidene-5,15-dioxatricyclo[12.3.1.0⁴,⁶]octadec-9-en-16-one)

3D Structure for NP0282963 ((1r,4s,6s,9e,13s,14r)-13-hydroxy-4,9,13-trimethyl-17-methylidene-5,15-dioxatricyclo[12.3.1.0⁴,⁶]octadec-9-en-16-one)