NP-MRD: Showing NP-Card for 6-[(1s,2s)-1,2-dihydroxy-3-methylbut-3-en-1-yl]-16-hydroxy-7-methoxy-14-methyl-2,10-dioxatricyclo[10.4.0.0³,⁸]hexadeca-1(16),3,5,7,12,14-hexaen-9-one (NP0252178)

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Record Information

Version

2.0

Created at

2022-09-07 15:36:31 UTC

Updated at

2022-09-07 15:36:31 UTC

NP-MRD ID

NP0252178

Secondary Accession Numbers

None

Natural Product Identification

Common Name

6-[(1s,2s)-1,2-dihydroxy-3-methylbut-3-en-1-yl]-16-hydroxy-7-methoxy-14-methyl-2,10-dioxatricyclo[10.4.0.0³,⁸]hexadeca-1(16),3,5,7,12,14-hexaen-9-one

Description

Pestalotiollide B belongs to the class of organic compounds known as diarylethers. These are organic compounds containing the dialkyl ether functional group, with the formula ROR', where R and R' are aryl groups. 6-[(1s,2s)-1,2-dihydroxy-3-methylbut-3-en-1-yl]-16-hydroxy-7-methoxy-14-methyl-2,10-dioxatricyclo[10.4.0.0³,⁸]hexadeca-1(16),3,5,7,12,14-hexaen-9-one is found in Rhizophora mucronata. 6-[(1s,2s)-1,2-dihydroxy-3-methylbut-3-en-1-yl]-16-hydroxy-7-methoxy-14-methyl-2,10-dioxatricyclo[10.4.0.0³,⁸]hexadeca-1(16),3,5,7,12,14-hexaen-9-one was first documented in 2017 (PMID: 29021785). Based on a literature review a small amount of articles have been published on Pestalotiollide B (PMID: 31474098) (PMID: 29625656) (PMID: 29538316) (PMID: 29364863).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309072217362D          

 28 30  0  0  1  0            999 V2000
    9.3248    1.3985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8225    0.7440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1383   -0.0182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0046    0.8516    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.6889    1.6138    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5024    0.1971    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.8181   -0.5651    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6844    0.3048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3687    1.0670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5508    1.1747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0485    0.5202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3643   -0.2420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1822   -0.3497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4979   -1.1119    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3159   -1.2196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0485   -1.0042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6319   -1.5876    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2863   -1.3199    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5241   -1.0042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2084   -0.2420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3905   -0.3497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8883    0.3048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0703    0.1971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2040    1.0670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0219    1.1747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3376    1.9369    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5241    0.5202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2863    0.8359    0.0000 O   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
  2  4  1  0  0  0  0
  4  5  1  1  0  0  0
  4  6  1  0  0  0  0
  6  7  1  1  0  0  0
  6  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
  8 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 12 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  2  0  0  0  0
 20 27  1  0  0  0  0
 27 28  1  0  0  0  0
 11 28  1  0  0  0  0
M  END

     RDKit          3D

 50 52  0  0  0  0  0  0  0  0999 V2000
   -6.4518   -0.1001   -0.7448 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6213    0.4030    0.1557 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0971    0.5877    1.5465 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2340    0.7597   -0.2282 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.1431    0.6361   -1.6340 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2813   -0.1920    0.4526 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.6342   -1.4675    0.0570 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8798    0.1599    0.3555 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4896    1.4532    0.0761 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1354    1.8353    0.0305 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8229    0.8983    0.2705 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4138   -0.4127    0.5523 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9134   -0.7714    0.5913 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2177   -2.0881    0.8674 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3462   -3.0362   -0.2146 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1667   -1.6042    0.8497 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5374   -2.3098    1.6887 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3880   -2.0948    0.4113 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3259   -1.6198   -0.5723 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8381   -0.2758   -0.2115 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2153   -0.4323   -0.1872 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0513    0.6203    0.1205 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5083    0.3386    0.1144 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5555    1.8779    0.4178 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1920    2.0469    0.3973 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6725    3.2893    0.6911 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3564    0.9956    0.0893 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0691    1.5427    0.1649 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4863   -0.3692   -0.4730 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1533   -0.2698   -1.7785 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1288    0.1752    1.6731 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4437    0.1272    2.2809 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2408    1.6943    1.7380 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0215    1.8231    0.0323 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8231    1.2605   -1.9942 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5817   -0.1276    1.5595 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8842   -2.0616    0.8051 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1750    2.2479   -0.1220 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1617    2.8461   -0.1843 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4424   -3.6537   -0.3560 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1670   -3.7571   -0.0405 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4480   -2.4800   -1.1913 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1388   -2.3214   -0.6956 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8101   -1.5164   -1.5652 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6404   -1.4180   -0.4167 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7524   -0.1856   -0.8515 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1206    1.2682    0.1240 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7888   -0.3844    0.9096 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2636    2.6564    0.6528 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6508    3.4061    0.6728 H   0  0  0  0  0  0  0  0  0  0  0  0
 15 14  1  0
 14 13  1  0
 13 12  2  0
 12 11  1  0
 11 28  1  0
 28 27  1  0
 27 25  2  0
 25 26  1  0
 25 24  1  0
 24 22  2  0
 22 23  1  0
 22 21  1  0
 21 20  2  0
 20 19  1  0
 19 18  1  0
 18 16  1  0
 16 17  2  0
 11 10  2  0
 10  9  1  0
  9  8  2  0
  8  6  1  0
  6  7  1  0
  6  4  1  0
  4  5  1  0
  4  2  1  0
  2  3  1  0
  2  1  2  3
  8 13  1  0
 16 12  1  0
 20 27  1  0
 15 40  1  0
 15 41  1  0
 15 42  1  0
 26 50  1  0
 24 49  1  0
 23 46  1  0
 23 47  1  0
 23 48  1  0
 21 45  1  0
 19 43  1  0
 19 44  1  0
 10 39  1  0
  9 38  1  0
  6 36  1  1
  7 37  1  0
  4 34  1  6
  5 35  1  0
  3 31  1  0
  3 32  1  0
  3 33  1  0
  1 29  1  0
  1 30  1  0
M  END


  Mrv1652309072217362D          

 28 30  0  0  1  0            999 V2000
    9.3248    1.3985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8225    0.7440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1383   -0.0182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0046    0.8516    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.6889    1.6138    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5024    0.1971    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.8181   -0.5651    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6844    0.3048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3687    1.0670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5508    1.1747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0485    0.5202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3643   -0.2420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1822   -0.3497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4979   -1.1119    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3159   -1.2196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0485   -1.0042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6319   -1.5876    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2863   -1.3199    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5241   -1.0042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2084   -0.2420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3905   -0.3497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8883    0.3048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0703    0.1971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2040    1.0670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0219    1.1747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3376    1.9369    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5241    0.5202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2863    0.8359    0.0000 O   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
  2  4  1  0  0  0  0
  4  5  1  1  0  0  0
  4  6  1  0  0  0  0
  6  7  1  1  0  0  0
  6  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
  8 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 12 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  2  0  0  0  0
 20 27  1  0  0  0  0
 27 28  1  0  0  0  0
 11 28  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0252178

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C2C(OC3=C(O)C=C(C)C=C3COC2=O)=CC=C1[C@H](O)[C@@H](O)C(C)=C

> <INCHI_IDENTIFIER>
InChI=1S/C21H22O7/c1-10(2)17(23)18(24)13-5-6-15-16(20(13)26-4)21(25)27-9-12-7-11(3)8-14(22)19(12)28-15/h5-8,17-18,22-24H,1,9H2,2-4H3/t17-,18-/m0/s1

> <INCHI_KEY>
HHLSDNCZICXJDV-ROUUACIJSA-N

> <FORMULA>
C21H22O7

> <MOLECULAR_WEIGHT>
386.4

> <EXACT_MASS>
386.136553048

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
50

> <JCHEM_AVERAGE_POLARIZABILITY>
39.4568670784647

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
6-[(1S,2S)-1,2-dihydroxy-3-methylbut-3-en-1-yl]-16-hydroxy-7-methoxy-14-methyl-2,10-dioxatricyclo[10.4.0.0^{3,8}]hexadeca-1(12),3(8),4,6,13,15-hexaen-9-one

> <JCHEM_LOGP>
2.717115522

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.73585691913381

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.395516681354973

> <JCHEM_PKA_STRONGEST_BASIC>
-3.461887312187618

> <JCHEM_POLAR_SURFACE_AREA>
105.45

> <JCHEM_REFRACTIVITY>
102.25729999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
6-[(1S,2S)-1,2-dihydroxy-3-methylbut-3-en-1-yl]-16-hydroxy-7-methoxy-14-methyl-2,10-dioxatricyclo[10.4.0.0^{3,8}]hexadeca-1(12),3(8),4,6,13,15-hexaen-9-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  C   UNK     0      17.406   2.610   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      16.469   1.389   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      17.058  -0.034   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      14.942   1.590   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      14.353   3.013   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      14.004   0.368   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      14.594  -1.055   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      12.478   0.569   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      11.888   1.992   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      10.361   2.193   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.424   0.971   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      10.013  -0.452   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      11.540  -0.653   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      12.129  -2.076   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      13.656  -2.277   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       9.424  -1.875   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      10.513  -2.963   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       8.001  -2.464   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       6.578  -1.875   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.989  -0.452   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.462  -0.653   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       3.525   0.569   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       1.998   0.368   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       4.114   1.992   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       5.641   2.193   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       6.230   3.616   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       6.578   0.971   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       8.001   1.560   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   13                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   28                                                  
CONECT   12   11   13   16                                                  
CONECT   13   12    8   14                                                  
CONECT   14   13   15                                                       
CONECT   15   14                                                            
CONECT   16   12   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   27                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   20   28                                                  
CONECT   28   27   11                                                       
MASTER        0    0    0    0    0    0    0    0   28    0   60    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₁H₂₂O₇

Average Mass

386.4000 Da

Monoisotopic Mass

386.13655 Da

IUPAC Name

6-[(1S,2S)-1,2-dihydroxy-3-methylbut-3-en-1-yl]-16-hydroxy-7-methoxy-14-methyl-2,10-dioxatricyclo[10.4.0.0^{3,8}]hexadeca-1(12),3(8),4,6,13,15-hexaen-9-one

Traditional Name

6-[(1S,2S)-1,2-dihydroxy-3-methylbut-3-en-1-yl]-16-hydroxy-7-methoxy-14-methyl-2,10-dioxatricyclo[10.4.0.0^{3,8}]hexadeca-1(12),3(8),4,6,13,15-hexaen-9-one

CAS Registry Number

Not Available

SMILES

COC1=C2C(OC3=C(O)C=C(C)C=C3COC2=O)=CC=C1[C@H](O)[C@@H](O)C(C)=C

InChI Identifier

InChI=1S/C21H22O7/c1-10(2)17(23)18(24)13-5-6-15-16(20(13)26-4)21(25)27-9-12-7-11(3)8-14(22)19(12)28-15/h5-8,17-18,22-24H,1,9H2,2-4H3/t17-,18-/m0/s1

InChI Key

HHLSDNCZICXJDV-ROUUACIJSA-N

Experimental Spectra

Not Available

Predicted Spectra

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

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Rhizophora mucronata	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diarylethers. These are organic compounds containing the dialkyl ether functional group, with the formula ROR', where R and R' are aryl groups.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Ethers

Direct Parent

Diarylethers

Alternative Parents

Substituents

Diaryl ether
Anisole
Phenol ether
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Phenol
Benzenoid
1,2-diol
Carboxylic acid ester
Secondary alcohol
Lactone
Oxacycle
Carboxylic acid derivative
Organoheterocyclic compound
Organic oxide
Alcohol
Hydrocarbon derivative
Aromatic alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic 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	2.72	ChemAxon
pKa (Strongest Acidic)	8.4	ChemAxon
pKa (Strongest Basic)	-3.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	105.45 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	102.26 m³·mol⁻¹	ChemAxon
Polarizability	39.46 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

27026273

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

52920650

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Liu Y, Chen L, Xie Q, Yu X, Duan A, Lin Y, Xiang B, Hao X, Chen W, Zhu X: A Gene Cluster for the Biosynthesis of Dibenzodioxocinons in the Endophyte Pestalotiopsis microspora, a Taxol Producer. J Microbiol Biotechnol. 2019 Oct 28;29(10):1570-1579. doi: 10.4014/jmb.1905.05051. [PubMed:31474098 ]
Akhberdi O, Zhang Q, Wang H, Li Y, Chen L, Wang D, Yu X, Wei D, Zhu X: Roles of phospholipid methyltransferases in pycnidia development, stress tolerance and secondary metabolism in the taxol-producing fungus Pestalotiopsis microspore. Microbiol Res. 2018 May;210:33-42. doi: 10.1016/j.micres.2018.03.001. Epub 2018 Mar 8. [PubMed:29625656 ]
Akhberdi O, Zhang Q, Wang D, Wang H, Hao X, Liu Y, Wei D, Zhu X: Distinct Roles of Velvet Complex in the Development, Stress Tolerance, and Secondary Metabolism in Pestalotiopsis microspora, a Taxol Producer. Genes (Basel). 2018 Mar 14;9(3):164. doi: 10.3390/genes9030164. [PubMed:29538316 ]
Wang D, Li Y, Wang H, Wei D, Akhberdi O, Liu Y, Xiang B, Hao X, Zhu X: The AMP-Activated Protein Kinase Homolog Snf1 Concerts Carbon Utilization, Conidia Production and the Biosynthesis of Secondary Metabolites in the Taxol-Producer Pestalotiopsis microspora. Genes (Basel). 2018 Jan 24;9(2):59. doi: 10.3390/genes9020059. [PubMed:29364863 ]
Wang D, Akhberdi O, Hao X, Yu X, Chen L, Liu Y, Zhu X: Amino Acid Sensor Kinase Gcn2 Is Required for Conidiation, Secondary Metabolism, and Cell Wall Integrity in the Taxol-Producer Pestalotiopsis microspora. Front Microbiol. 2017 Sep 27;8:1879. doi: 10.3389/fmicb.2017.01879. eCollection 2017. [PubMed:29021785 ]
LOTUS database [Link]

Showing NP-Card for 6-[(1s,2s)-1,2-dihydroxy-3-methylbut-3-en-1-yl]-16-hydroxy-7-methoxy-14-methyl-2,10-dioxatricyclo[10.4.0.0³,⁸]hexadeca-1(16),3,5,7,12,14-hexaen-9-one (NP0252178)

MOL for NP0252178 (6-[(1s,2s)-1,2-dihydroxy-3-methylbut-3-en-1-yl]-16-hydroxy-7-methoxy-14-methyl-2,10-dioxatricyclo[10.4.0.0³,⁸]hexadeca-1(16),3,5,7,12,14-hexaen-9-one)

3D MOL for NP0252178 (6-[(1s,2s)-1,2-dihydroxy-3-methylbut-3-en-1-yl]-16-hydroxy-7-methoxy-14-methyl-2,10-dioxatricyclo[10.4.0.0³,⁸]hexadeca-1(16),3,5,7,12,14-hexaen-9-one)

3D SDF for NP0252178 (6-[(1s,2s)-1,2-dihydroxy-3-methylbut-3-en-1-yl]-16-hydroxy-7-methoxy-14-methyl-2,10-dioxatricyclo[10.4.0.0³,⁸]hexadeca-1(16),3,5,7,12,14-hexaen-9-one)

3D-SDF for NP0252178 (6-[(1s,2s)-1,2-dihydroxy-3-methylbut-3-en-1-yl]-16-hydroxy-7-methoxy-14-methyl-2,10-dioxatricyclo[10.4.0.0³,⁸]hexadeca-1(16),3,5,7,12,14-hexaen-9-one)

PDB for NP0252178 (6-[(1s,2s)-1,2-dihydroxy-3-methylbut-3-en-1-yl]-16-hydroxy-7-methoxy-14-methyl-2,10-dioxatricyclo[10.4.0.0³,⁸]hexadeca-1(16),3,5,7,12,14-hexaen-9-one)

3D PDB for NP0252178 (6-[(1s,2s)-1,2-dihydroxy-3-methylbut-3-en-1-yl]-16-hydroxy-7-methoxy-14-methyl-2,10-dioxatricyclo[10.4.0.0³,⁸]hexadeca-1(16),3,5,7,12,14-hexaen-9-one)

SMILES for NP0252178 (6-[(1s,2s)-1,2-dihydroxy-3-methylbut-3-en-1-yl]-16-hydroxy-7-methoxy-14-methyl-2,10-dioxatricyclo[10.4.0.0³,⁸]hexadeca-1(16),3,5,7,12,14-hexaen-9-one)

INCHI for NP0252178 (6-[(1s,2s)-1,2-dihydroxy-3-methylbut-3-en-1-yl]-16-hydroxy-7-methoxy-14-methyl-2,10-dioxatricyclo[10.4.0.0³,⁸]hexadeca-1(16),3,5,7,12,14-hexaen-9-one)

Structure for NP0252178 (6-[(1s,2s)-1,2-dihydroxy-3-methylbut-3-en-1-yl]-16-hydroxy-7-methoxy-14-methyl-2,10-dioxatricyclo[10.4.0.0³,⁸]hexadeca-1(16),3,5,7,12,14-hexaen-9-one)

3D Structure for NP0252178 (6-[(1s,2s)-1,2-dihydroxy-3-methylbut-3-en-1-yl]-16-hydroxy-7-methoxy-14-methyl-2,10-dioxatricyclo[10.4.0.0³,⁸]hexadeca-1(16),3,5,7,12,14-hexaen-9-one)