NP-MRD: Showing NP-Card for Crocin I (NP0140457)

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Record Information

Version

2.0

Created at

2022-06-29 21:35:19 UTC

Updated at

2022-06-29 21:35:19 UTC

NP-MRD ID

NP0140457

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Crocin I

Description

Crocin, also known as alpha-crocin or saffron, belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units. Crocin is an extremely weak basic (essentially neutral) compound (based on its pKa). Note that in India, the term 'Crocin' is also used by GlaxoSmithKline as a brand-name for paracetamol. A diester that is crocetin in which both of the carboxy groups have been converted to their gentiobiosyl esters. Crocin I is found in Buddleja officinalis, Crocus sativus and Gardenia jasminoides. Crocin I was first documented in 2003 (PMID: 14514073). It is one of the water-soluble yellow-red pigments of Crocin and is used as a spice for flavouring and colouring food (PMID: 17215084) (PMID: 16448211) (PMID: 17704979) (PMID: 21398065).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652301212022263D          

 68 71  0  0  0  0            999 V2000
   -3.1923    3.3913   -1.1276 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5475   -1.2278    0.0676 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1287   -2.1026   -0.8499 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4747   -2.6780    0.9518 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9374    1.8081   -0.7759 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0083    0.8923   -0.5356 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5491    0.5108   -0.8819 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5088   -0.7211    0.2412 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2943    1.4624   -0.7665 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4234    1.0895   -0.5032 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8945    1.7139   -0.9040 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6728    0.2577   -0.0681 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9282    0.2085   -0.9340 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9206   -0.4192    0.3568 C   0  0  0  0  0  0  0  0  0  0  0  0
  -14.7810    4.2526   -0.1400 C   0  0  0  0  0  0  0  0  0  0  0  0
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    6.8813   -1.2610    0.6800 C   0  0  0  0  0  0  0  0  0  0  0  0
  -15.4523    2.9003   -0.3690 C   0  0  2  0  0  0  0  0  0  0  0  0
   16.0876    1.9312   -0.5754 C   0  0  2  0  0  0  0  0  0  0  0  0
  -13.0869   -2.0027   -1.8239 C   0  0  2  0  0  0  0  0  0  0  0  0
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   16.9168   -0.7306   -1.2075 C   0  0  2  0  0  0  0  0  0  0  0  0
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  -15.1553    0.6222   -0.3610 C   0  0  2  0  0  0  0  0  0  0  0  0
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  -11.0169   -1.7216   -0.9260 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.6429   -1.0336    1.1390 C   0  0  1  0  0  0  0  0  0  0  0  0
  -14.2338    4.3177    1.1370 O   0  0  0  0  0  0  0  0  0  0  0  0
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  -17.7904    2.5099   -0.1451 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.4995    1.5100    1.3215 O   0  0  0  0  0  0  0  0  0  0  0  0
  -12.7723   -4.3308   -1.2887 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.3011    0.7411    1.8906 O   0  0  0  0  0  0  0  0  0  0  0  0
  -15.3520    2.0110    2.4714 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.9783    0.4288   -1.5941 O   0  0  0  0  0  0  0  0  0  0  0  0
  -13.6197   -2.5512    1.4991 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -8.6896   -2.8953   -0.9221 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5440    0.3587    0.3958 O   0  0  0  0  0  0  0  0  0  0  0  0
  -14.1965   -0.3301   -0.5425 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.6153   -1.0811   -1.2322 O   0  0  0  0  0  0  0  0  0  0  0  0
  -14.5300    1.8885   -0.2226 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.4369    1.0401   -1.4031 O   0  0  0  0  0  0  0  0  0  0  0  0
  -11.9631   -1.2394   -1.7460 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.5873   -1.8121    0.5271 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.8060   -0.9614   -0.9316 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.3615   -1.5916    1.1383 O   0  0  0  0  0  0  0  0  0  0  0  0
  1 19  1  0  0  0  0
  2 20  1  0  0  0  0
  3 21  1  0  0  0  0
  4 22  1  0  0  0  0
  5  6  2  0  0  0  0
  5  9  1  0  0  0  0
  6 10  1  0  0  0  0
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  7 13  1  0  0  0  0
  8 12  2  0  0  0  0
  8 14  1  0  0  0  0
  9 19  2  0  0  0  0
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 11 19  1  0  0  0  0
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 26 18  1  6  0  0  0
 18 62  1  0  0  0  0
 21 39  1  0  0  0  0
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 29 33  1  0  0  0  0
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 34 38  1  0  0  0  0
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 43 65  1  0  0  0  0
 43 67  1  1  0  0  0
 44 66  1  0  0  0  0
 44 68  1  1  0  0  0
M  END

     RDKit          3D

132135  0  0  0  0  0  0  0  0999 V2000
    2.6054   -0.9965   -0.0759 C   0  0  0  0  0  0  0  0  0  0  0  0
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    8.8013   -1.1599    0.2567 C   0  0  0  0  0  0  0  0  0  0  0  0
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   17.1753    1.4912   -0.4847 H   0  0  0  0  0  0  0  0  0  0  0  0
   14.0240    3.0733    0.3156 H   0  0  0  0  0  0  0  0  0  0  0  0
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    9.9393    1.5703   -4.8294 H   0  0  0  0  0  0  0  0  0  0  0  0
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    1.9635   -1.4585    3.2008 H   0  0  0  0  0  0  0  0  0  0  0  0
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  -11.2259   -0.3468    2.4479 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.4833    1.4411   -0.2051 H   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1652301212022263D          

 68 71  0  0  0  0            999 V2000
   -3.1923    3.3913   -1.1276 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5475   -1.2278    0.0676 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1287   -2.1026   -0.8499 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4747   -2.6780    0.9518 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9374    1.8081   -0.7759 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0083    0.8923   -0.5356 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5491    0.5108   -0.8819 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5088   -0.7211    0.2412 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2943    1.4624   -0.7665 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4234    1.0895   -0.5032 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8945    1.7139   -0.9040 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6728    0.2577   -0.0681 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9282    0.2085   -0.9340 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9206   -0.4192    0.3568 C   0  0  0  0  0  0  0  0  0  0  0  0
  -14.7810    4.2526   -0.1400 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1270    3.2555   -1.3333 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -8.5884   -1.6096   -0.9240 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2661   -0.8467    0.7410 C   0  0  0  0  0  0  0  0  0  0  0  0
  -15.1553    0.6222   -0.3610 C   0  0  2  0  0  0  0  0  0  0  0  0
   15.5264   -0.2559   -0.7658 C   0  0  2  0  0  0  0  0  0  0  0  0
  -11.0169   -1.7216   -0.9260 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.6429   -1.0336    1.1390 C   0  0  1  0  0  0  0  0  0  0  0  0
  -14.2338    4.3177    1.1370 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.7850    4.1912   -0.5379 O   0  0  0  0  0  0  0  0  0  0  0  0
  -17.7904    2.5099   -0.1451 O   0  0  0  0  0  0  0  0  0  0  0  0
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  -12.7723   -4.3308   -1.2887 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.3011    0.7411    1.8906 O   0  0  0  0  0  0  0  0  0  0  0  0
  -15.3520    2.0110    2.4714 O   0  0  0  0  0  0  0  0  0  0  0  0
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  -13.6197   -2.5512    1.4991 O   0  0  0  0  0  0  0  0  0  0  0  0
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  -10.4868   -2.1559    1.3857 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.8777    0.5804    2.9264 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6896   -2.8953   -0.9221 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5440    0.3587    0.3958 O   0  0  0  0  0  0  0  0  0  0  0  0
  -14.1965   -0.3301   -0.5425 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.6153   -1.0811   -1.2322 O   0  0  0  0  0  0  0  0  0  0  0  0
  -14.5300    1.8885   -0.2226 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.4369    1.0401   -1.4031 O   0  0  0  0  0  0  0  0  0  0  0  0
  -11.9631   -1.2394   -1.7460 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.5873   -1.8121    0.5271 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.8060   -0.9614   -0.9316 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.3615   -1.5916    1.1383 O   0  0  0  0  0  0  0  0  0  0  0  0
  1 19  1  0  0  0  0
  2 20  1  0  0  0  0
  3 21  1  0  0  0  0
  4 22  1  0  0  0  0
  5  6  2  0  0  0  0
  5  9  1  0  0  0  0
  6 10  1  0  0  0  0
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  7 13  1  0  0  0  0
  8 12  2  0  0  0  0
  8 14  1  0  0  0  0
  9 19  2  0  0  0  0
 10 20  2  0  0  0  0
 11 19  1  0  0  0  0
 12 20  1  0  0  0  0
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 23 15  1  1  0  0  0
 15 45  1  0  0  0  0
 24 16  1  6  0  0  0
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 25 17  1  1  0  0  0
 17 61  1  0  0  0  0
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 29 33  1  0  0  0  0
 29 49  1  6  0  0  0
 30 34  1  0  0  0  0
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 31 35  1  0  0  0  0
 31 51  1  1  0  0  0
 32 36  1  0  0  0  0
 32 52  1  6  0  0  0
 33 37  1  0  0  0  0
 33 53  1  1  0  0  0
 34 38  1  0  0  0  0
 34 54  1  6  0  0  0
 35 41  1  0  0  0  0
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 36 42  1  0  0  0  0
 36 56  1  1  0  0  0
 37 43  1  0  0  0  0
 37 57  1  1  0  0  0
 38 44  1  0  0  0  0
 38 58  1  6  0  0  0
 39 59  2  0  0  0  0
 39 67  1  0  0  0  0
 40 60  2  0  0  0  0
 40 68  1  0  0  0  0
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 41 63  1  0  0  0  0
 42 62  1  6  0  0  0
 42 64  1  0  0  0  0
 43 65  1  0  0  0  0
 43 67  1  1  0  0  0
 44 66  1  0  0  0  0
 44 68  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0140457

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C\C(\C=C\C=C(/C)C(=O)O[C@@H]1O[C@H](CO[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)[C@@H](O)[C@H](O)[C@H]1O)=C/C=C/C=C(\C)/C=C/C=C(\C)C(=O)O[C@@H]1O[C@H](CO[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)[C@@H](O)[C@H](O)[C@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C44H64O24/c1-19(11-7-13-21(3)39(59)67-43-37(57)33(53)29(49)25(65-43)17-61-41-35(55)31(51)27(47)23(15-45)63-41)9-5-6-10-20(2)12-8-14-22(4)40(60)68-44-38(58)34(54)30(50)26(66-44)18-62-42-36(56)32(52)28(48)24(16-46)64-42/h5-14,23-38,41-58H,15-18H2,1-4H3/b6-5+,11-7+,12-8+,19-9+,20-10+,21-13+,22-14+/t23-,24-,25-,26-,27-,28-,29-,30-,31+,32+,33+,34+,35-,36-,37-,38-,41-,42-,43+,44+/m1/s1

> <INCHI_KEY>
SEBIKDIMAPSUBY-RTJKDTQDSA-N

> <FORMULA>
C44H64O24

> <MOLECULAR_WEIGHT>
976.972

> <EXACT_MASS>
976.378752941

> <JCHEM_ACCEPTOR_COUNT>
22

> <JCHEM_ATOM_COUNT>
132

> <JCHEM_AVERAGE_POLARIZABILITY>
100.06898038130447

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
14

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
bis[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-({[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl] (2E,4E,6E,8E,10E,12E,14E)-2,6,11,15-tetramethylhexadeca-2,4,6,8,10,12,14-heptaenedioate

> <ALOGPS_LOGP>
-0.02

> <JCHEM_LOGP>
-3.210937580666667

> <ALOGPS_LOGS>
-3.24

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.088030392139236

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.668685014311508

> <JCHEM_PKA_STRONGEST_BASIC>
-3.678613072130494

> <JCHEM_POLAR_SURFACE_AREA>
391.20000000000005

> <JCHEM_REFRACTIVITY>
233.48580000000015

> <JCHEM_ROTATABLE_BOND_COUNT>
20

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.67e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
saffron

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 21-JAN-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   21-JAN-20         0                                  
HETATM    1  C   UNK     0      -3.192   3.391  -1.128  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.548  -1.228   0.068  0.00  0.00           C+0
HETATM    3  C   UNK     0      -6.129  -2.103  -0.850  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.475  -2.678   0.952  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.937   1.808  -0.776  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.008   0.892  -0.536  0.00  0.00           C+0
HETATM    7  C   UNK     0      -5.549   0.511  -0.882  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.509  -0.721   0.241  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.294   1.462  -0.767  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.423   1.089  -0.503  0.00  0.00           C+0
HETATM   11  C   UNK     0      -4.894   1.714  -0.904  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.673   0.258  -0.068  0.00  0.00           C+0
HETATM   13  C   UNK     0      -6.928   0.209  -0.934  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.921  -0.419   0.357  0.00  0.00           C+0
HETATM   15  C   UNK     0     -14.781   4.253  -0.140  0.00  0.00           C+0
HETATM   16  C   UNK     0      16.127   3.256  -1.333  0.00  0.00           C+0
HETATM   17  C   UNK     0     -14.269  -1.011  -1.738  0.00  0.00           C+0
HETATM   18  C   UNK     0      13.665  -1.745  -0.580  0.00  0.00           C+0
HETATM   19  C   UNK     0      -3.476   1.575  -0.829  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.247   0.059  -0.199  0.00  0.00           C+0
HETATM   21  C   UNK     0      -7.260  -1.091  -0.916  0.00  0.00           C+0
HETATM   22  C   UNK     0       6.881  -1.261   0.680  0.00  0.00           C+0
HETATM   23  C   UNK     0     -15.452   2.900  -0.369  0.00  0.00           C+0
HETATM   24  C   UNK     0      16.088   1.931  -0.575  0.00  0.00           C+0
HETATM   25  C   UNK     0     -13.087  -2.003  -1.824  0.00  0.00           C+0
HETATM   26  C   UNK     0      12.704  -0.934   0.245  0.00  0.00           C+0
HETATM   27  C   UNK     0     -16.607   2.699   0.589  0.00  0.00           C+0
HETATM   28  C   UNK     0      17.425   1.481  -0.086  0.00  0.00           C+0
HETATM   29  C   UNK     0     -13.229  -3.081  -0.825  0.00  0.00           C+0
HETATM   30  C   UNK     0      13.288  -0.608   1.633  0.00  0.00           C+0
HETATM   31  C   UNK     0     -16.359   1.610   1.589  0.00  0.00           C+0
HETATM   32  C   UNK     0      17.930   0.199  -0.657  0.00  0.00           C+0
HETATM   33  C   UNK     0     -12.649  -2.771   0.535  0.00  0.00           C+0
HETATM   34  C   UNK     0      12.445  -1.248   2.732  0.00  0.00           C+0
HETATM   35  C   UNK     0     -15.931   0.340   0.913  0.00  0.00           C+0
HETATM   36  C   UNK     0      16.917  -0.731  -1.208  0.00  0.00           C+0
HETATM   37  C   UNK     0     -11.535  -1.783   0.518  0.00  0.00           C+0
HETATM   38  C   UNK     0      11.028  -0.778   2.618  0.00  0.00           C+0
HETATM   39  C   UNK     0      -8.588  -1.610  -0.924  0.00  0.00           C+0
HETATM   40  C   UNK     0       8.266  -0.847   0.741  0.00  0.00           C+0
HETATM   41  C   UNK     0     -15.155   0.622  -0.361  0.00  0.00           C+0
HETATM   42  C   UNK     0      15.526  -0.256  -0.766  0.00  0.00           C+0
HETATM   43  C   UNK     0     -11.017  -1.722  -0.926  0.00  0.00           C+0
HETATM   44  C   UNK     0      10.643  -1.034   1.139  0.00  0.00           C+0
HETATM   45  O   UNK     0     -14.234   4.318   1.137  0.00  0.00           O+0
HETATM   46  O   UNK     0      16.785   4.191  -0.538  0.00  0.00           O+0
HETATM   47  O   UNK     0     -17.790   2.510  -0.145  0.00  0.00           O+0
HETATM   48  O   UNK     0      17.500   1.510   1.321  0.00  0.00           O+0
HETATM   49  O   UNK     0     -12.772  -4.331  -1.289  0.00  0.00           O+0
HETATM   50  O   UNK     0      13.301   0.741   1.891  0.00  0.00           O+0
HETATM   51  O   UNK     0     -15.352   2.011   2.471  0.00  0.00           O+0
HETATM   52  O   UNK     0      18.978   0.429  -1.594  0.00  0.00           O+0
HETATM   53  O   UNK     0     -13.620  -2.551   1.499  0.00  0.00           O+0
HETATM   54  O   UNK     0      12.490  -2.631   2.587  0.00  0.00           O+0
HETATM   55  O   UNK     0     -17.014  -0.479   0.682  0.00  0.00           O+0
HETATM   56  O   UNK     0      17.127  -2.068  -0.992  0.00  0.00           O+0
HETATM   57  O   UNK     0     -10.487  -2.156   1.386  0.00  0.00           O+0
HETATM   58  O   UNK     0      10.878   0.580   2.926  0.00  0.00           O+0
HETATM   59  O   UNK     0      -8.690  -2.895  -0.922  0.00  0.00           O+0
HETATM   60  O   UNK     0       8.544   0.359   0.396  0.00  0.00           O+0
HETATM   61  O   UNK     0     -14.197  -0.330  -0.543  0.00  0.00           O+0
HETATM   62  O   UNK     0      14.615  -1.081  -1.232  0.00  0.00           O+0
HETATM   63  O   UNK     0     -14.530   1.889  -0.223  0.00  0.00           O+0
HETATM   64  O   UNK     0      15.437   1.040  -1.403  0.00  0.00           O+0
HETATM   65  O   UNK     0     -11.963  -1.239  -1.746  0.00  0.00           O+0
HETATM   66  O   UNK     0      11.587  -1.812   0.527  0.00  0.00           O+0
HETATM   67  O   UNK     0      -9.806  -0.961  -0.932  0.00  0.00           O+0
HETATM   68  O   UNK     0       9.361  -1.592   1.138  0.00  0.00           O+0
CONECT    1   19                                                            
CONECT    2   20                                                            
CONECT    3   21                                                            
CONECT    4   22                                                            
CONECT    5    6    9                                                       
CONECT    6    5   10                                                       
CONECT    7   11   13                                                       
CONECT    8   12   14                                                       
CONECT    9    5   19                                                       
CONECT   10    6   20                                                       
CONECT   11    7   19                                                       
CONECT   12    8   20                                                       
CONECT   13    7   21                                                       
CONECT   14    8   22                                                       
CONECT   15   23   45                                                       
CONECT   16   24   46                                                       
CONECT   17   25   61                                                       
CONECT   18   26   62                                                       
CONECT   19    1    9   11                                                  
CONECT   20    2   10   12                                                  
CONECT   21    3   13   39                                                  
CONECT   22    4   14   40                                                  
CONECT   23   15   27   63                                                  
CONECT   24   16   28   64                                                  
CONECT   25   17   29   65                                                  
CONECT   26   18   30   66                                                  
CONECT   27   23   31   47                                                  
CONECT   28   24   32   48                                                  
CONECT   29   25   33   49                                                  
CONECT   30   26   34   50                                                  
CONECT   31   27   35   51                                                  
CONECT   32   28   36   52                                                  
CONECT   33   29   37   53                                                  
CONECT   34   30   38   54                                                  
CONECT   35   31   41   55                                                  
CONECT   36   32   42   56                                                  
CONECT   37   33   43   57                                                  
CONECT   38   34   44   58                                                  
CONECT   39   21   59   67                                                  
CONECT   40   22   60   68                                                  
CONECT   41   35   61   63                                                  
CONECT   42   36   62   64                                                  
CONECT   43   37   65   67                                                  
CONECT   44   38   66   68                                                  
CONECT   45   15                                                            
CONECT   46   16                                                            
CONECT   47   27                                                            
CONECT   48   28                                                            
CONECT   49   29                                                            
CONECT   50   30                                                            
CONECT   51   31                                                            
CONECT   52   32                                                            
CONECT   53   33                                                            
CONECT   54   34                                                            
CONECT   55   35                                                            
CONECT   56   36                                                            
CONECT   57   37                                                            
CONECT   58   38                                                            
CONECT   59   39                                                            
CONECT   60   40                                                            
CONECT   61   17   41                                                       
CONECT   62   18   42                                                       
CONECT   63   23   41                                                       
CONECT   64   24   42                                                       
CONECT   65   25   43                                                       
CONECT   66   26   44                                                       
CONECT   67   39   43                                                       
CONECT   68   40   44                                                       
MASTER        0    0    0    0    0    0    0    0   68    0  142    0
END

View in JSmol

Synonyms

Value	Source
alpha-Crocin	ChEBI
Bis(beta-D-gentiobiosyl) crocetin	ChEBI
C.I. 75100	ChEBI
Crocetin di-beta-D-gentiobiose ester	ChEBI
Crocetin di-gentiobiose ester	ChEBI
Crocetin digentiobioside	ChEBI
Crocine	ChEBI
Natural red 1	ChEBI
Natural yellow 19	ChEBI
Natural yellow 6	ChEBI
Saffron	ChEBI
trans-Crocetin bis(beta-D-gentiobiosyl) ester	ChEBI
a-Crocin	Generator
Α-crocin	Generator
Bis(b-D-gentiobiosyl) crocetin	Generator
Bis(β-D-gentiobiosyl) crocetin	Generator
Crocetin di-b-D-gentiobiose ester	Generator
Crocetin di-β-D-gentiobiose ester	Generator
trans-Crocetin bis(b-D-gentiobiosyl) ester	Generator
trans-Crocetin bis(β-D-gentiobiosyl) ester	Generator
all-trans-Crocetin di-beta-D-gentiobiosyl ester	HMDB
all-trans-Crocetin di-beta-delta-gentiobiosyl ester	HMDB
Crocetin bis(gentiobiosyl) ester	HMDB
Crocetin digentiobiose ester	HMDB
Crocin 1	HMDB
Gardenia yellow	HMDB
Saffron (JP15)	HMDB
Crocin	MeSH

Chemical Formula

C₄₄H₆₄O₂₄

Average Mass

976.9720 Da

Monoisotopic Mass

976.37875 Da

IUPAC Name

bis[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-({[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl] (2E,4E,6E,8E,10E,12E,14E)-2,6,11,15-tetramethylhexadeca-2,4,6,8,10,12,14-heptaenedioate

Traditional Name

saffron

CAS Registry Number

Not Available

SMILES

C\C(\C=C\C=C(/C)C(=O)O[C@@H]1O[C@H](CO[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)[C@@H](O)[C@H](O)[C@H]1O)=C/C=C/C=C(\C)/C=C/C=C(\C)C(=O)O[C@@H]1O[C@H](CO[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)[C@@H](O)[C@H](O)[C@H]1O

InChI Identifier

InChI=1S/C44H64O24/c1-19(11-7-13-21(3)39(59)67-43-37(57)33(53)29(49)25(65-43)17-61-41-35(55)31(51)27(47)23(15-45)63-41)9-5-6-10-20(2)12-8-14-22(4)40(60)68-44-38(58)34(54)30(50)26(66-44)18-62-42-36(56)32(52)28(48)24(16-46)64-42/h5-14,23-38,41-58H,15-18H2,1-4H3/b6-5+,11-7+,12-8+,19-9+,20-10+,21-13+,22-14+/t23-,24-,25-,26-,27-,28-,29-,30-,31+,32+,33+,34+,35-,36-,37-,38-,41-,42-,43+,44+/m1/s1

InChI Key

SEBIKDIMAPSUBY-RTJKDTQDSA-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
Buddleja officinalis	LOTUS Database	35616633
Crocus sativus	LOTUS Database	35616633
Gardenia jasminoides	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Diterpenoids

Alternative Parents

Substituents

Diterpenoid
Disaccharide
Glycosyl compound
O-glycosyl compound
Fatty acid ester
Dicarboxylic acid or derivatives
Fatty acyl
Oxane
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Carboxylic acid ester
Secondary alcohol
Polyol
Acetal
Organoheterocyclic compound
Oxacycle
Carboxylic acid derivative
Alcohol
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
Primary alcohol
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

diester (CHEBI:79068 )
disaccharide derivative (CHEBI:79068 )
diterpenoid (CHEBI:79068 )

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	-0.02	ALOGPS
logP	-3.2	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	11.67	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	22	ChemAxon
Hydrogen Donor Count	14	ChemAxon
Polar Surface Area	391.2 Å²	ChemAxon
Rotatable Bond Count	20	ChemAxon
Refractivity	233.49 m³·mol⁻¹	ChemAxon
Polarizability	100.07 Å³	ChemAxon
Number of Rings	4	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

HMDB0002398

DrugBank ID

DB11874

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Crocin

METLIN ID

Not Available

PubChem Compound

5281233

PDB ID

Not Available

ChEBI ID

79068

Good Scents ID

Not Available

References

General References

Ochiai T, Shimeno H, Mishima K, Iwasaki K, Fujiwara M, Tanaka H, Shoyama Y, Toda A, Eyanagi R, Soeda S: Protective effects of carotenoids from saffron on neuronal injury in vitro and in vivo. Biochim Biophys Acta. 2007 Apr;1770(4):578-84. doi: 10.1016/j.bbagen.2006.11.012. Epub 2006 Dec 5. [PubMed:17215084 ]
Carmona M, Zalacain A, Sanchez AM, Novella JL, Alonso GL: Crocetin esters, picrocrocin and its related compounds present in Crocus sativus stigmas and Gardenia jasminoides fruits. Tentative identification of seven new compounds by LC-ESI-MS. J Agric Food Chem. 2006 Feb 8;54(3):973-9. doi: 10.1021/jf052297w. [PubMed:16448211 ]
Chen SA, Wang X, Zhao B, Yuan X, Wang Y: Production of crocin using Crocus sativus callus by two-stage culture system. Biotechnol Lett. 2003 Aug;25(15):1235-8. doi: 10.1023/a:1025036729160. [PubMed:14514073 ]
Schmidt M, Betti G, Hensel A: Saffron in phytotherapy: pharmacology and clinical uses. Wien Med Wochenschr. 2007;157(13-14):315-9. doi: 10.1007/s10354-007-0428-4. [PubMed:17704979 ]
Chryssanthi DG, Lamari FN, Georgakopoulos CD, Cordopatis P: A new validated SPE-HPLC method for monitoring crocetin in human plasma--application after saffron tea consumption. J Pharm Biomed Anal. 2011 Jun 1;55(3):563-8. doi: 10.1016/j.jpba.2011.02.018. Epub 2011 Feb 21. [PubMed:21398065 ]

Showing NP-Card for Crocin I (NP0140457)

MOL for NP0140457 (Crocin I)

3D MOL for NP0140457 (Crocin I)

3D SDF for NP0140457 (Crocin I)

3D-SDF for NP0140457 (Crocin I)

PDB for NP0140457 (Crocin I)

3D PDB for NP0140457 (Crocin I)

SMILES for NP0140457 (Crocin I)

INCHI for NP0140457 (Crocin I)

Structure for NP0140457 (Crocin I)

3D Structure for NP0140457 (Crocin I)