NP-MRD: Showing NP-Card for (3s)-6-[(1e,3e,5e,7e,9e,11e,13e,15e,17e)-18-[(4r)-4-hydroxy-2,6,6-trimethylcyclohex-1-en-1-yl]-3,7,12,16-tetramethyloctadeca-1,3,5,7,9,11,13,15,17-nonaen-1-yl]-1,5,5-trimethyl-7-oxabicyclo[4.1.0]heptan-3-ol (NP0285035)

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Record Information

Version

2.0

Created at

2022-09-09 13:01:06 UTC

Updated at

2022-09-09 13:01:06 UTC

NP-MRD ID

NP0285035

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(3s)-6-[(1e,3e,5e,7e,9e,11e,13e,15e,17e)-18-[(4r)-4-hydroxy-2,6,6-trimethylcyclohex-1-en-1-yl]-3,7,12,16-tetramethyloctadeca-1,3,5,7,9,11,13,15,17-nonaen-1-yl]-1,5,5-trimethyl-7-oxabicyclo[4.1.0]heptan-3-ol

Description

Antheraxanthin belongs to the class of organic compounds known as xanthophylls. These are carotenoids containing an oxygenated carotene backbone. Carotenes are characterized by the presence of two end-groups (mostly cyclohexene rings, but also cyclopentene rings or acyclic groups) linked by a long branched alkyl chain. Carotenes belonging form a subgroup of the carotenoids family. Xanthophylls arise by oxygenation of the carotene backbone. (3s)-6-[(1e,3e,5e,7e,9e,11e,13e,15e,17e)-18-[(4r)-4-hydroxy-2,6,6-trimethylcyclohex-1-en-1-yl]-3,7,12,16-tetramethyloctadeca-1,3,5,7,9,11,13,15,17-nonaen-1-yl]-1,5,5-trimethyl-7-oxabicyclo[4.1.0]heptan-3-ol is found in Ceramium rubrum, Chara tomentosa, Citrus reticulata, Euglena gracilis, Mantoniella squamata, Nannochloropsis oculata, Olisthodiscus luteus, Tetraselmis subcordiformis and Wittrockiella paradoxa. Antheraxanthin is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652303082006222D          

 59 61  0  0  1  0            999 V2000
   -5.1710   -3.4618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0460   -3.4618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.4289   -2.0328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4085   -8.4631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2463   -7.4664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3277   -6.9361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6737   -0.2194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6131   -0.2194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0164    2.3644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5210   -3.4618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6960   -3.4618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9960   -4.8907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2210   -2.0328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -7.2335   -7.0341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -7.6460   -9.1775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -7.2335   -8.4631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4710   -9.1775    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
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   -7.6460   -7.7486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.1434    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -8.8835   -9.8920    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -6.4085   -4.1762    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.4585   -1.3184    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9960   -6.3197    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -9.2960   -9.1775    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8578    2.4750    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 12 11  2  0  0  0  0
 15 11  1  0  0  0  0
 16 12  1  0  0  0  0
 17 13  2  0  0  0  0
 18 14  2  0  0  0  0
 19 13  1  0  0  0  0
 20 14  1  0  0  0  0
 22 21  2  0  0  0  0
 24 23  2  0  0  0  0
 29  1  1  0  0  0  0
 29 15  2  0  0  0  0
 29 17  1  0  0  0  0
 30  2  1  0  0  0  0
 30 16  2  0  0  0  0
 30 18  1  0  0  0  0
 31  3  1  0  0  0  0
 31 19  2  0  0  0  0
 31 21  1  0  0  0  0
 32  4  1  0  0  0  0
 32 20  2  0  0  0  0
 32 23  1  0  0  0  0
 33  5  1  0  0  0  0
 33 25  1  0  0  0  0
 34 25  1  0  0  0  0
 34 26  1  0  0  0  0
 35 27  1  0  0  0  0
 35 28  1  0  0  0  0
 36 22  1  0  0  0  0
 36 33  2  0  0  0  0
 37  6  1  0  0  0  0
 37  7  1  0  0  0  0
 37 26  1  0  0  0  0
 37 36  1  0  0  0  0
 38  8  1  0  0  0  0
 38  9  1  0  0  0  0
 38 27  1  0  0  0  0
 39 10  1  0  0  0  0
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 40 24  1  0  0  0  0
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 56 23  1  0  0  0  0
 57 24  1  0  0  0  0
 34 58  1  6  0  0  0
 35 59  1  6  0  0  0
M  END

     RDKit          3D

 99101  0  0  0  0  0  0  0  0999 V2000
  -12.0006   -1.2456    1.7586 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.4188    0.0469    1.1404 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.4807    0.8360    0.5495 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.1221    0.3700    0.5496 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0542    0.9041    0.0438 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7525    0.2127    0.1910 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6529   -1.0491    0.9496 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6542    0.7467   -0.3069 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3076    0.2077   -0.1743 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2509    0.7827   -0.7005 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9364    0.2036   -0.5280 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6298   -0.9808    0.2959 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8580    0.8082   -1.0834 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5244    0.2687   -0.8284 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5743    0.8108   -1.3389 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8837    0.2449   -1.0558 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0333    0.7182   -1.5051 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9781    1.9152   -2.3685 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2766    0.0745   -1.0830 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4623    0.4692   -1.4758 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6380   -0.2255   -1.0010 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8919    0.0345   -1.2999 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1945    1.1438   -2.2263 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9837   -0.7025   -0.6879 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2633   -0.5128   -0.9175 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3155   -1.2837   -0.2660 C   0  0  2  0  0  0  0  0  0  0  0  0
   12.6518   -0.9983   -0.8438 O   0  0  0  0  0  0  0  0  0  0  0  0
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   13.3866   -2.6775    1.2564 C   0  0  1  0  0  0  0  0  0  0  0  0
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   11.4027   -1.1268    1.2459 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0124    0.2980    1.5697 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4412   -2.0483    1.9417 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.0007    2.0922    0.0384 C   0  0  0  0  0  0  0  0  0  0  0  0
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  -11.0645    3.1723   -0.3529 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.8105    2.7295    1.2242 C   0  0  0  0  0  0  0  0  0  0  0  0
  -13.9990    1.9044    1.5779 C   0  0  2  0  0  0  0  0  0  0  0  0
  -14.1899    1.8714    2.9873 O   0  0  0  0  0  0  0  0  0  0  0  0
  -13.8224    0.4668    1.1409 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.6153   -1.9143    1.0004 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.2540   -1.0587    2.5710 H   0  0  0  0  0  0  0  0  0  0  0  0
  -12.8967   -1.6674    2.2611 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.9836   -0.6230    1.0858 H   0  0  0  0  0  0  0  0  0  0  0  0
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    2.1955    1.7705   -3.1482 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7292    2.8034   -1.7240 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9607    2.1348   -2.8080 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2441   -0.7886   -0.3962 H   0  0  0  0  0  0  0  0  0  0  0  0
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    6.5030   -1.0755   -0.3118 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4623    2.0821   -1.7182 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3637    1.2971   -2.9680 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.0760    0.9039   -2.8886 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7503   -1.5042    0.0421 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.5017    0.2746   -1.6463 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.4734   -2.6262   -2.9220 H   0  0  0  0  0  0  0  0  0  0  0  0
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 39 93  1  0
M  END


  Mrv1652303082006222D          

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   -8.8835   -9.8920    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.4585   -1.3184    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
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 22 21  2  0  0  0  0
 24 23  2  0  0  0  0
 29  1  1  0  0  0  0
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 30  2  1  0  0  0  0
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 33  5  1  0  0  0  0
 33 25  1  0  0  0  0
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 36 22  1  0  0  0  0
 36 33  2  0  0  0  0
 37  6  1  0  0  0  0
 37  7  1  0  0  0  0
 37 26  1  0  0  0  0
 37 36  1  0  0  0  0
 38  8  1  0  0  0  0
 38  9  1  0  0  0  0
 38 27  1  0  0  0  0
 39 10  1  0  0  0  0
 39 28  1  0  0  0  0
 40 24  1  0  0  0  0
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 44 11  1  0  0  0  0
 45 12  1  0  0  0  0
 46 13  1  0  0  0  0
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 49 16  1  0  0  0  0
 50 17  1  0  0  0  0
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 53 20  1  0  0  0  0
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 57 24  1  0  0  0  0
 34 58  1  6  0  0  0
 35 59  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0285035

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]/C(=C(/[H])\C(\[H])=C(/C)\C(\[H])=C(/[H])\C(\[H])=C(/C)\C(\[H])=C(/[H])C12OC1(C)C[C@@]([H])(O)CC2(C)C)/C(/[H])=C(\C)/C(/[H])=C(\[H])/C(/[H])=C(\C)/C(/[H])=C(\[H])C1=C(C)C[C@@]([H])(O)CC1(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C40H56O3/c1-29(17-13-19-31(3)21-22-36-33(5)25-34(41)26-37(36,6)7)15-11-12-16-30(2)18-14-20-32(4)23-24-40-38(8,9)27-35(42)28-39(40,10)43-40/h11-24,34-35,41-42H,25-28H2,1-10H3/b12-11+,17-13+,18-14+,22-21+,24-23+,29-15+,30-16+,31-19+,32-20+/t34-,35+,39?,40?/m1/s1

> <INCHI_KEY>
OFNSUWBAQRCHAV-UKGDUWIJSA-N

> <FORMULA>
C40H56O3

> <MOLECULAR_WEIGHT>
584.885

> <EXACT_MASS>
584.422945663

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
99

> <JCHEM_AVERAGE_POLARIZABILITY>
75.05836481225077

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3S)-6-[(1E,3E,5E,7E,9E,11E,13E,15E,17E)-18-[(4R)-4-hydroxy-2,6,6-trimethylcyclohex-1-en-1-yl]-3,7,12,16-tetramethyloctadeca-1,3,5,7,9,11,13,15,17-nonaen-1-yl]-1,5,5-trimethyl-7-oxabicyclo[4.1.0]heptan-3-ol

> <ALOGPS_LOGP>
8.37

> <JCHEM_LOGP>
7.804052578333334

> <ALOGPS_LOGS>
-5.95

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
18.907213404525137

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.139684034106125

> <JCHEM_PKA_STRONGEST_BASIC>
-1.089506579901021

> <JCHEM_POLAR_SURFACE_AREA>
52.99

> <JCHEM_REFRACTIVITY>
193.6389

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
6.58e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3S)-6-[(1E,3E,5E,7E,9E,11E,13E,15E,17E)-18-[(4R)-4-hydroxy-2,6,6-trimethylcyclohex-1-en-1-yl]-3,7,12,16-tetramethyloctadeca-1,3,5,7,9,11,13,15,17-nonaen-1-yl]-1,5,5-trimethyl-7-oxabicyclo[4.1.0]heptan-3-ol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 08-MAR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-MAR-20         0                                  
HETATM    1  C   UNK     0      -9.653  -6.462   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.953  -6.462   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0     -14.273  -9.129   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667  -3.795   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0     -11.963 -15.798   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0     -17.260 -13.937   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0     -15.545 -12.947   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.991  -0.410   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.011  -0.410   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.897   4.414   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -6.573  -6.462   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -5.033  -6.462   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0     -11.193  -9.129   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.413  -3.795   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -7.343  -7.796   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -4.263  -5.128   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -9.653  -9.129   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.953  -3.795   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0     -11.963 -10.463   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.357  -2.461   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0     -14.273 -11.797   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0     -13.503 -13.130   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.667  -1.127   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       1.897   0.206   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0     -14.273 -17.131   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0     -16.583 -15.798   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -8.883  -7.796   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -2.723  -5.128   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0     -13.503 -10.463   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       1.897  -2.461   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0     -13.503 -15.798   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0     -15.813 -17.131   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       5.335   3.080   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0     -14.273 -14.464   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0     -15.813 -14.464   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       4.001   0.770   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       2.667   3.080   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0     -16.583 -18.465   0.000  0.00  0.00           O+0
HETATM   42  O   UNK     0       6.668   3.850   0.000  0.00  0.00           O+0
HETATM   43  O   UNK     0       1.334   2.310   0.000  0.00  0.00           O+0
HETATM   44  H   UNK     0      -7.343  -5.128   0.000  0.00  0.00           H+0
HETATM   45  H   UNK     0      -4.263  -7.796   0.000  0.00  0.00           H+0
HETATM   46  H   UNK     0     -11.963  -7.796   0.000  0.00  0.00           H+0
HETATM   47  H   UNK     0       0.357  -5.128   0.000  0.00  0.00           H+0
HETATM   48  H   UNK     0      -6.573  -9.129   0.000  0.00  0.00           H+0
HETATM   49  H   UNK     0      -5.033  -3.795   0.000  0.00  0.00           H+0
HETATM   50  H   UNK     0      -8.883 -10.463   0.000  0.00  0.00           H+0
HETATM   51  H   UNK     0      -2.723  -2.461   0.000  0.00  0.00           H+0
HETATM   52  H   UNK     0     -11.193 -11.797   0.000  0.00  0.00           H+0
HETATM   53  H   UNK     0      -0.413  -1.127   0.000  0.00  0.00           H+0
HETATM   54  H   UNK     0     -15.470 -10.829   0.000  0.00  0.00           H+0
HETATM   55  H   UNK     0     -11.963 -13.130   0.000  0.00  0.00           H+0
HETATM   56  H   UNK     0       4.030  -1.845   0.000  0.00  0.00           H+0
HETATM   57  H   UNK     0       0.357   0.206   0.000  0.00  0.00           H+0
HETATM   58  H   UNK     0     -17.353 -17.131   0.000  0.00  0.00           H+0
HETATM   59  H   UNK     0       5.335   4.620   0.000  0.00  0.00           H+0
CONECT    1   29                                                            
CONECT    2   30                                                            
CONECT    3   31                                                            
CONECT    4   32                                                            
CONECT    5   33                                                            
CONECT    6   37                                                            
CONECT    7   37                                                            
CONECT    8   38                                                            
CONECT    9   38                                                            
CONECT   10   39                                                            
CONECT   11   12   15   44                                                  
CONECT   12   11   16   45                                                  
CONECT   13   17   19   46                                                  
CONECT   14   18   20   47                                                  
CONECT   15   11   29   48                                                  
CONECT   16   12   30   49                                                  
CONECT   17   13   29   50                                                  
CONECT   18   14   30   51                                                  
CONECT   19   13   31   52                                                  
CONECT   20   14   32   53                                                  
CONECT   21   22   31   54                                                  
CONECT   22   21   36   55                                                  
CONECT   23   24   32   56                                                  
CONECT   24   23   40   57                                                  
CONECT   25   33   34                                                       
CONECT   26   34   37                                                       
CONECT   27   35   38                                                       
CONECT   28   35   39                                                       
CONECT   29    1   15   17                                                  
CONECT   30    2   16   18                                                  
CONECT   31    3   19   21                                                  
CONECT   32    4   20   23                                                  
CONECT   33    5   25   36                                                  
CONECT   34   25   26   41   58                                             
CONECT   35   27   28   42   59                                             
CONECT   36   22   33   37                                                  
CONECT   37    6    7   26   36                                             
CONECT   38    8    9   27   40                                             
CONECT   39   10   28   40   43                                             
CONECT   40   24   38   39   43                                             
CONECT   41   34                                                            
CONECT   42   35                                                            
CONECT   43   39   40                                                       
CONECT   44   11                                                            
CONECT   45   12                                                            
CONECT   46   13                                                            
CONECT   47   14                                                            
CONECT   48   15                                                            
CONECT   49   16                                                            
CONECT   50   17                                                            
CONECT   51   18                                                            
CONECT   52   19                                                            
CONECT   53   20                                                            
CONECT   54   21                                                            
CONECT   55   22                                                            
CONECT   56   23                                                            
CONECT   57   24                                                            
CONECT   58   34                                                            
CONECT   59   35                                                            
MASTER        0    0    0    0    0    0    0    0   59    0  122    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₄₀H₅₆O₃

Average Mass

584.8850 Da

Monoisotopic Mass

584.42295 Da

IUPAC Name

(3S)-6-[(1E,3E,5E,7E,9E,11E,13E,15E,17E)-18-[(4R)-4-hydroxy-2,6,6-trimethylcyclohex-1-en-1-yl]-3,7,12,16-tetramethyloctadeca-1,3,5,7,9,11,13,15,17-nonaen-1-yl]-1,5,5-trimethyl-7-oxabicyclo[4.1.0]heptan-3-ol

Traditional Name

CAS Registry Number

Not Available

SMILES

[H]/C(=C(/[H])\C(\[H])=C(/C)\C(\[H])=C(/[H])\C(\[H])=C(/C)\C(\[H])=C(/[H])C12OC1(C)C[C@@]([H])(O)CC2(C)C)/C(/[H])=C(\C)/C(/[H])=C(\[H])/C(/[H])=C(\C)/C(/[H])=C(\[H])C1=C(C)C[C@@]([H])(O)CC1(C)C

InChI Identifier

InChI=1S/C40H56O3/c1-29(17-13-19-31(3)21-22-36-33(5)25-34(41)26-37(36,6)7)15-11-12-16-30(2)18-14-20-32(4)23-24-40-38(8,9)27-35(42)28-39(40,10)43-40/h11-24,34-35,41-42H,25-28H2,1-10H3/b12-11+,17-13+,18-14+,22-21+,24-23+,29-15+,30-16+,31-19+,32-20+/t34-,35+,39?,40?/m1/s1

InChI Key

OFNSUWBAQRCHAV-UKGDUWIJSA-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
Ceramium rubrum	LOTUS Database	35616633
Chara tomentosa	LOTUS Database	35616633
Citrus reticulata	LOTUS Database	35616633
Euglena gracilis	LOTUS Database	35616633
Mantoniella squamata	LOTUS Database	35616633
Nannochloropsis oculata	LOTUS Database	35616633
Olisthodiscus luteus	LOTUS Database	35616633
Tetraselmis subcordiformis	LOTUS Database	35616633
Wittrockiella paradoxa	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as xanthophylls. These are carotenoids containing an oxygenated carotene backbone. Carotenes are characterized by the presence of two end-groups (mostly cyclohexene rings, but also cyclopentene rings or acyclic groups) linked by a long branched alkyl chain. Carotenes belonging form a subgroup of the carotenoids family. Xanthophylls arise by oxygenation of the carotene backbone.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Tetraterpenoids

Direct Parent

Xanthophylls

Alternative Parents

Substituents

Xanthophyll
Oxepane
Cyclic alcohol
Secondary alcohol
Oxacycle
Organoheterocyclic compound
Ether
Oxirane
Dialkyl ether
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
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	8.37	ALOGPS
logP	7.8	ChemAxon
logS	-6	ALOGPS
pKa (Strongest Acidic)	15.14	ChemAxon
pKa (Strongest Basic)	-1.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	52.99 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	193.64 m³·mol⁻¹	ChemAxon
Polarizability	75.06 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Antheraxanthin

METLIN ID

Not Available

PubChem Compound

25244322

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (3s)-6-[(1e,3e,5e,7e,9e,11e,13e,15e,17e)-18-[(4r)-4-hydroxy-2,6,6-trimethylcyclohex-1-en-1-yl]-3,7,12,16-tetramethyloctadeca-1,3,5,7,9,11,13,15,17-nonaen-1-yl]-1,5,5-trimethyl-7-oxabicyclo[4.1.0]heptan-3-ol (NP0285035)

MOL for NP0285035 ((3s)-6-[(1e,3e,5e,7e,9e,11e,13e,15e,17e)-18-[(4r)-4-hydroxy-2,6,6-trimethylcyclohex-1-en-1-yl]-3,7,12,16-tetramethyloctadeca-1,3,5,7,9,11,13,15,17-nonaen-1-yl]-1,5,5-trimethyl-7-oxabicyclo[4.1.0]heptan-3-ol)

3D MOL for NP0285035 ((3s)-6-[(1e,3e,5e,7e,9e,11e,13e,15e,17e)-18-[(4r)-4-hydroxy-2,6,6-trimethylcyclohex-1-en-1-yl]-3,7,12,16-tetramethyloctadeca-1,3,5,7,9,11,13,15,17-nonaen-1-yl]-1,5,5-trimethyl-7-oxabicyclo[4.1.0]heptan-3-ol)

3D SDF for NP0285035 ((3s)-6-[(1e,3e,5e,7e,9e,11e,13e,15e,17e)-18-[(4r)-4-hydroxy-2,6,6-trimethylcyclohex-1-en-1-yl]-3,7,12,16-tetramethyloctadeca-1,3,5,7,9,11,13,15,17-nonaen-1-yl]-1,5,5-trimethyl-7-oxabicyclo[4.1.0]heptan-3-ol)

3D-SDF for NP0285035 ((3s)-6-[(1e,3e,5e,7e,9e,11e,13e,15e,17e)-18-[(4r)-4-hydroxy-2,6,6-trimethylcyclohex-1-en-1-yl]-3,7,12,16-tetramethyloctadeca-1,3,5,7,9,11,13,15,17-nonaen-1-yl]-1,5,5-trimethyl-7-oxabicyclo[4.1.0]heptan-3-ol)

PDB for NP0285035 ((3s)-6-[(1e,3e,5e,7e,9e,11e,13e,15e,17e)-18-[(4r)-4-hydroxy-2,6,6-trimethylcyclohex-1-en-1-yl]-3,7,12,16-tetramethyloctadeca-1,3,5,7,9,11,13,15,17-nonaen-1-yl]-1,5,5-trimethyl-7-oxabicyclo[4.1.0]heptan-3-ol)

3D PDB for NP0285035 ((3s)-6-[(1e,3e,5e,7e,9e,11e,13e,15e,17e)-18-[(4r)-4-hydroxy-2,6,6-trimethylcyclohex-1-en-1-yl]-3,7,12,16-tetramethyloctadeca-1,3,5,7,9,11,13,15,17-nonaen-1-yl]-1,5,5-trimethyl-7-oxabicyclo[4.1.0]heptan-3-ol)

SMILES for NP0285035 ((3s)-6-[(1e,3e,5e,7e,9e,11e,13e,15e,17e)-18-[(4r)-4-hydroxy-2,6,6-trimethylcyclohex-1-en-1-yl]-3,7,12,16-tetramethyloctadeca-1,3,5,7,9,11,13,15,17-nonaen-1-yl]-1,5,5-trimethyl-7-oxabicyclo[4.1.0]heptan-3-ol)

INCHI for NP0285035 ((3s)-6-[(1e,3e,5e,7e,9e,11e,13e,15e,17e)-18-[(4r)-4-hydroxy-2,6,6-trimethylcyclohex-1-en-1-yl]-3,7,12,16-tetramethyloctadeca-1,3,5,7,9,11,13,15,17-nonaen-1-yl]-1,5,5-trimethyl-7-oxabicyclo[4.1.0]heptan-3-ol)

Structure for NP0285035 ((3s)-6-[(1e,3e,5e,7e,9e,11e,13e,15e,17e)-18-[(4r)-4-hydroxy-2,6,6-trimethylcyclohex-1-en-1-yl]-3,7,12,16-tetramethyloctadeca-1,3,5,7,9,11,13,15,17-nonaen-1-yl]-1,5,5-trimethyl-7-oxabicyclo[4.1.0]heptan-3-ol)

3D Structure for NP0285035 ((3s)-6-[(1e,3e,5e,7e,9e,11e,13e,15e,17e)-18-[(4r)-4-hydroxy-2,6,6-trimethylcyclohex-1-en-1-yl]-3,7,12,16-tetramethyloctadeca-1,3,5,7,9,11,13,15,17-nonaen-1-yl]-1,5,5-trimethyl-7-oxabicyclo[4.1.0]heptan-3-ol)