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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:38:43 UTC

Update Date

2022-03-07 02:52:40 UTC

HMDB ID

HMDB0030735

Secondary Accession Numbers

HMDB30735

Metabolite Identification

Common Name

Aurantiumal

Description

Aurantiumal belongs to the class of organic compounds known as psoralens. These are organic compounds containing a psoralen moiety, which consists of a furan fused to a chromenone to for 7H-furo[3,2-g]chromen-7-one. Based on a literature review very few articles have been published on Aurantiumal.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI


  Mrv0541 05061305282D          

 26 28  0  0  0  0            999 V2000
    3.5724    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7474    7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3974    7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9280    2.3174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4130    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    8.2500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9280    0.9826    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  2  0  0  0  0
  9  6  1  0  0  0  0
 10  7  1  0  0  0  0
 11  8  2  0  0  0  0
 14  1  1  0  0  0  0
 14  6  1  0  0  0  0
 14  7  2  0  0  0  0
 15  4  1  0  0  0  0
 16  8  1  0  0  0  0
 17 12  2  0  0  0  0
 17 16  1  0  0  0  0
 18 12  1  0  0  0  0
 18 15  2  0  0  0  0
 19  5  1  0  0  0  0
 20 15  1  0  0  0  0
 20 16  2  0  0  0  0
 21  2  1  0  0  0  0
 21  3  1  0  0  0  0
 21  9  1  0  0  0  0
 21 13  1  0  0  0  0
 22 13  2  0  0  0  0
 23 19  2  0  0  0  0
 24 11  1  0  0  0  0
 24 17  1  0  0  0  0
 25 10  1  0  0  0  0
 25 20  1  0  0  0  0
 26 18  1  0  0  0  0
 26 19  1  0  0  0  0
M  END

HMDB0030735
     RDKit          3D
Aurantiumal
 48 50  0  0  0  0  0  0  0  0999 V2000
   -0.7457    1.7134   -0.4318 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2517    0.3762   -0.0138 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4117   -0.6452   -0.1506 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9701   -0.4739   -0.6936 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8823   -0.9087    0.3227 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2285   -0.8458    0.0504 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8773   -1.9084   -0.5272 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4603   -3.1738   -0.9517 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5637   -3.8184   -1.4593 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5837   -3.0140   -1.3566 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2265   -1.8746   -0.8122 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9043   -0.7043   -0.4843 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2833    0.3634    0.0893 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9266    1.4660    0.3972 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3338    2.4977    0.9500 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0215    3.5251    1.2174 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9928    2.4873    1.2429 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2498    1.3441    0.9404 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9278    0.2934    0.3608 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5886    0.1318    0.5253 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6870    0.5195   -0.4366 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0334    0.2508    0.1601 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2368    1.0415    1.4452 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2810   -1.2027    0.4444 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0630    0.7034   -0.8106 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8751    0.7341   -2.0108 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4005    1.7334   -1.4858 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5263    2.4974   -0.3516 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1009    1.9666    0.2249 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7123   -1.6683    0.1369 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1873    0.5849   -0.9269 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1191   -1.0529   -1.6298 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4348   -3.5099   -0.8618 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5564   -4.8361   -1.8733 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9717   -0.6845   -0.7126 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5292    3.3558    1.7004 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2087    1.3244    1.1636 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7938    0.7114    1.4690 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6942   -0.9254    0.8022 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6007   -0.0591   -1.3663 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6061    1.6124   -0.6030 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6711    0.5743    2.2553 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3093    1.0475    1.7193 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8913    2.0948    1.3271 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7863   -1.5330    1.3630 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9657   -1.7870   -0.4491 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3892   -1.3427    0.5151 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0197    1.0179   -0.4235 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
 17 18  2  0
 18 19  1  0
  2 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 22 24  1  0
 22 25  1  0
 25 26  2  0
 19  6  1  0
 11  7  1  0
 19 13  2  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  3 30  1  0
  4 31  1  0
  4 32  1  0
  8 33  1  0
  9 34  1  0
 12 35  1  0
 17 36  1  0
 18 37  1  0
 20 38  1  0
 20 39  1  0
 21 40  1  0
 21 41  1  0
 23 42  1  0
 23 43  1  0
 23 44  1  0
 24 45  1  0
 24 46  1  0
 24 47  1  0
 25 48  1  0
M  END


  Mrv0541 05061305282D          

 26 28  0  0  0  0            999 V2000
    3.5724    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7474    7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3974    7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9280    2.3174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4130    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    8.2500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9280    0.9826    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  2  0  0  0  0
  9  6  1  0  0  0  0
 10  7  1  0  0  0  0
 11  8  2  0  0  0  0
 14  1  1  0  0  0  0
 14  6  1  0  0  0  0
 14  7  2  0  0  0  0
 15  4  1  0  0  0  0
 16  8  1  0  0  0  0
 17 12  2  0  0  0  0
 17 16  1  0  0  0  0
 18 12  1  0  0  0  0
 18 15  2  0  0  0  0
 19  5  1  0  0  0  0
 20 15  1  0  0  0  0
 20 16  2  0  0  0  0
 21  2  1  0  0  0  0
 21  3  1  0  0  0  0
 21  9  1  0  0  0  0
 21 13  1  0  0  0  0
 22 13  2  0  0  0  0
 23 19  2  0  0  0  0
 24 11  1  0  0  0  0
 24 17  1  0  0  0  0
 25 10  1  0  0  0  0
 25 20  1  0  0  0  0
 26 18  1  0  0  0  0
 26 19  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0030735

> <DATABASE_NAME>
hmdb

> <SMILES>
C\C(CCC(C)(C)C=O)=C/COC1=C2C=COC2=CC2=C1C=CC(=O)O2

> <INCHI_IDENTIFIER>
InChI=1S/C21H22O5/c1-14(6-9-21(2,3)13-22)7-10-25-20-15-4-5-19(23)26-18(15)12-17-16(20)8-11-24-17/h4-5,7-8,11-13H,6,9-10H2,1-3H3/b14-7+

> <INCHI_KEY>
JBBNVKWFZYFPIG-VGOFMYFVSA-N

> <FORMULA>
C21H22O5

> <MOLECULAR_WEIGHT>
354.3964

> <EXACT_MASS>
354.146723814

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
38.1429151102089

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(5E)-2,2,5-trimethyl-7-({7-oxo-7H-furo[3,2-g]chromen-4-yl}oxy)hept-5-enal

> <ALOGPS_LOGP>
4.73

> <JCHEM_LOGP>
4.099906398000001

> <ALOGPS_LOGS>
-4.55

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8253961643655354

> <JCHEM_POLAR_SURFACE_AREA>
65.74000000000001

> <JCHEM_REFRACTIVITY>
99.58959999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.00e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(5E)-2,2,5-trimethyl-7-({7-oxofuro[3,2-g]chromen-4-yl}oxy)hept-5-enal

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0030735
     RDKit          3D
Aurantiumal
 48 50  0  0  0  0  0  0  0  0999 V2000
   -0.7457    1.7134   -0.4318 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2517    0.3762   -0.0138 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4117   -0.6452   -0.1506 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9701   -0.4739   -0.6936 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8823   -0.9087    0.3227 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2285   -0.8458    0.0504 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8773   -1.9084   -0.5272 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4603   -3.1738   -0.9517 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5637   -3.8184   -1.4593 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5837   -3.0140   -1.3566 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2265   -1.8746   -0.8122 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9043   -0.7043   -0.4843 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2833    0.3634    0.0893 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9266    1.4660    0.3972 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3338    2.4977    0.9500 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0215    3.5251    1.2174 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9928    2.4873    1.2429 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2498    1.3441    0.9404 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9278    0.2934    0.3608 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5886    0.1318    0.5253 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6870    0.5195   -0.4366 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0334    0.2508    0.1601 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2368    1.0415    1.4452 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2810   -1.2027    0.4444 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0630    0.7034   -0.8106 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8751    0.7341   -2.0108 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4005    1.7334   -1.4858 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5263    2.4974   -0.3516 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1009    1.9666    0.2249 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7123   -1.6683    0.1369 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1873    0.5849   -0.9269 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1191   -1.0529   -1.6298 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4348   -3.5099   -0.8618 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5564   -4.8361   -1.8733 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9717   -0.6845   -0.7126 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5292    3.3558    1.7004 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2087    1.3244    1.1636 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7938    0.7114    1.4690 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6942   -0.9254    0.8022 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6007   -0.0591   -1.3663 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6061    1.6124   -0.6030 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6711    0.5743    2.2553 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3093    1.0475    1.7193 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8913    2.0948    1.3271 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7863   -1.5330    1.3630 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9657   -1.7870   -0.4491 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3892   -1.3427    0.5151 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0197    1.0179   -0.4235 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
 17 18  2  0
 18 19  1  0
  2 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 22 24  1  0
 22 25  1  0
 25 26  2  0
 19  6  1  0
 11  7  1  0
 19 13  2  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  3 30  1  0
  4 31  1  0
  4 32  1  0
  8 33  1  0
  9 34  1  0
 12 35  1  0
 17 36  1  0
 18 37  1  0
 20 38  1  0
 20 39  1  0
 21 40  1  0
 21 41  1  0
 23 42  1  0
 23 43  1  0
 23 44  1  0
 24 45  1  0
 24 46  1  0
 24 47  1  0
 25 48  1  0
M  END

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       6.668   8.470   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.128  13.090   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.208  13.090   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.335  10.780   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.001   8.470   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.466   4.326   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.668  11.550   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.001   6.930   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.371   3.080   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.668  14.630   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.335   9.240   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.668  13.090   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       8.002  15.400   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      -2.667   1.540   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       5.466   1.834   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       2.667   6.160   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       0.000   1.540   0.000  0.00  0.00           O+0
CONECT    1   14                                                            
CONECT    2   21                                                            
CONECT    3   21                                                            
CONECT    4    5   15                                                       
CONECT    5    4   19                                                       
CONECT    6    9   14                                                       
CONECT    7   10   14                                                       
CONECT    8   11   16                                                       
CONECT    9    6   21                                                       
CONECT   10    7   25                                                       
CONECT   11    8   24                                                       
CONECT   12   17   18                                                       
CONECT   13   21   22                                                       
CONECT   14    1    6    7                                                  
CONECT   15    4   18   20                                                  
CONECT   16    8   17   20                                                  
CONECT   17   12   16   24                                                  
CONECT   18   12   15   26                                                  
CONECT   19    5   23   26                                                  
CONECT   20   15   16   25                                                  
CONECT   21    2    3    9   13                                             
CONECT   22   13                                                            
CONECT   23   19                                                            
CONECT   24   11   17                                                       
CONECT   25   10   20                                                       
CONECT   26   18   19                                                       
MASTER        0    0    0    0    0    0    0    0   26    0   56    0
END

COMPND    HMDB0030735
HETATM    1  C1  UNL     1      -0.746   1.713  -0.432  1.00  0.00           C  
HETATM    2  C2  UNL     1      -1.252   0.376  -0.014  1.00  0.00           C  
HETATM    3  C3  UNL     1      -0.412  -0.645  -0.151  1.00  0.00           C  
HETATM    4  C4  UNL     1       0.970  -0.474  -0.694  1.00  0.00           C  
HETATM    5  O1  UNL     1       1.882  -0.909   0.323  1.00  0.00           O  
HETATM    6  C5  UNL     1       3.229  -0.846   0.050  1.00  0.00           C  
HETATM    7  C6  UNL     1       3.877  -1.908  -0.527  1.00  0.00           C  
HETATM    8  C7  UNL     1       3.460  -3.174  -0.952  1.00  0.00           C  
HETATM    9  C8  UNL     1       4.564  -3.818  -1.459  1.00  0.00           C  
HETATM   10  O2  UNL     1       5.584  -3.014  -1.357  1.00  0.00           O  
HETATM   11  C9  UNL     1       5.226  -1.875  -0.812  1.00  0.00           C  
HETATM   12  C10 UNL     1       5.904  -0.704  -0.484  1.00  0.00           C  
HETATM   13  C11 UNL     1       5.283   0.363   0.089  1.00  0.00           C  
HETATM   14  O3  UNL     1       5.927   1.466   0.397  1.00  0.00           O  
HETATM   15  C12 UNL     1       5.334   2.498   0.950  1.00  0.00           C  
HETATM   16  O4  UNL     1       6.021   3.525   1.217  1.00  0.00           O  
HETATM   17  C13 UNL     1       3.993   2.487   1.243  1.00  0.00           C  
HETATM   18  C14 UNL     1       3.250   1.344   0.940  1.00  0.00           C  
HETATM   19  C15 UNL     1       3.928   0.293   0.361  1.00  0.00           C  
HETATM   20  C16 UNL     1      -2.589   0.132   0.525  1.00  0.00           C  
HETATM   21  C17 UNL     1      -3.687   0.520  -0.437  1.00  0.00           C  
HETATM   22  C18 UNL     1      -5.033   0.251   0.160  1.00  0.00           C  
HETATM   23  C19 UNL     1      -5.237   1.042   1.445  1.00  0.00           C  
HETATM   24  C20 UNL     1      -5.281  -1.203   0.444  1.00  0.00           C  
HETATM   25  C21 UNL     1      -6.063   0.703  -0.811  1.00  0.00           C  
HETATM   26  O5  UNL     1      -5.875   0.734  -2.011  1.00  0.00           O  
HETATM   27  H1  UNL     1      -0.401   1.733  -1.486  1.00  0.00           H  
HETATM   28  H2  UNL     1      -1.526   2.497  -0.352  1.00  0.00           H  
HETATM   29  H3  UNL     1       0.101   1.967   0.225  1.00  0.00           H  
HETATM   30  H4  UNL     1      -0.712  -1.668   0.137  1.00  0.00           H  
HETATM   31  H5  UNL     1       1.187   0.585  -0.927  1.00  0.00           H  
HETATM   32  H6  UNL     1       1.119  -1.053  -1.630  1.00  0.00           H  
HETATM   33  H7  UNL     1       2.435  -3.510  -0.862  1.00  0.00           H  
HETATM   34  H8  UNL     1       4.556  -4.836  -1.873  1.00  0.00           H  
HETATM   35  H9  UNL     1       6.972  -0.684  -0.713  1.00  0.00           H  
HETATM   36  H10 UNL     1       3.529   3.356   1.700  1.00  0.00           H  
HETATM   37  H11 UNL     1       2.209   1.324   1.164  1.00  0.00           H  
HETATM   38  H12 UNL     1      -2.794   0.711   1.469  1.00  0.00           H  
HETATM   39  H13 UNL     1      -2.694  -0.925   0.802  1.00  0.00           H  
HETATM   40  H14 UNL     1      -3.601  -0.059  -1.366  1.00  0.00           H  
HETATM   41  H15 UNL     1      -3.606   1.612  -0.603  1.00  0.00           H  
HETATM   42  H16 UNL     1      -4.671   0.574   2.255  1.00  0.00           H  
HETATM   43  H17 UNL     1      -6.309   1.047   1.719  1.00  0.00           H  
HETATM   44  H18 UNL     1      -4.891   2.095   1.327  1.00  0.00           H  
HETATM   45  H19 UNL     1      -4.786  -1.533   1.363  1.00  0.00           H  
HETATM   46  H20 UNL     1      -4.966  -1.787  -0.449  1.00  0.00           H  
HETATM   47  H21 UNL     1      -6.389  -1.343   0.515  1.00  0.00           H  
HETATM   48  H22 UNL     1      -7.020   1.018  -0.424  1.00  0.00           H  
CONECT    1    2   27   28   29
CONECT    2    3    3   20
CONECT    3    4   30
CONECT    4    5   31   32
CONECT    5    6
CONECT    6    7    7   19
CONECT    7    8   11
CONECT    8    9    9   33
CONECT    9   10   34
CONECT   10   11
CONECT   11   12   12
CONECT   12   13   35
CONECT   13   14   19   19
CONECT   14   15
CONECT   15   16   16   17
CONECT   17   18   18   36
CONECT   18   19   37
CONECT   20   21   38   39
CONECT   21   22   40   41
CONECT   22   23   24   25
CONECT   23   42   43   44
CONECT   24   45   46   47
CONECT   25   26   26   48
END

HMDB0030735
     RDKit          3D
Aurantiumal
 48 50  0  0  0  0  0  0  0  0999 V2000
   -0.7457    1.7134   -0.4318 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2517    0.3762   -0.0138 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4117   -0.6452   -0.1506 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9701   -0.4739   -0.6936 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8823   -0.9087    0.3227 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2285   -0.8458    0.0504 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8773   -1.9084   -0.5272 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4603   -3.1738   -0.9517 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5637   -3.8184   -1.4593 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5837   -3.0140   -1.3566 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2265   -1.8746   -0.8122 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9043   -0.7043   -0.4843 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2833    0.3634    0.0893 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9266    1.4660    0.3972 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3338    2.4977    0.9500 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0215    3.5251    1.2174 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9928    2.4873    1.2429 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2498    1.3441    0.9404 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9278    0.2934    0.3608 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5886    0.1318    0.5253 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6870    0.5195   -0.4366 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0334    0.2508    0.1601 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2368    1.0415    1.4452 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2810   -1.2027    0.4444 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0630    0.7034   -0.8106 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8751    0.7341   -2.0108 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4005    1.7334   -1.4858 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5263    2.4974   -0.3516 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1009    1.9666    0.2249 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7123   -1.6683    0.1369 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1873    0.5849   -0.9269 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1191   -1.0529   -1.6298 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4348   -3.5099   -0.8618 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5564   -4.8361   -1.8733 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9717   -0.6845   -0.7126 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5292    3.3558    1.7004 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2087    1.3244    1.1636 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7938    0.7114    1.4690 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6942   -0.9254    0.8022 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6007   -0.0591   -1.3663 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6061    1.6124   -0.6030 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6711    0.5743    2.2553 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3093    1.0475    1.7193 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8913    2.0948    1.3271 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7863   -1.5330    1.3630 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9657   -1.7870   -0.4491 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3892   -1.3427    0.5151 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0197    1.0179   -0.4235 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
 17 18  2  0
 18 19  1  0
  2 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 22 24  1  0
 22 25  1  0
 25 26  2  0
 19  6  1  0
 11  7  1  0
 19 13  2  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  3 30  1  0
  4 31  1  0
  4 32  1  0
  8 33  1  0
  9 34  1  0
 12 35  1  0
 17 36  1  0
 18 37  1  0
 20 38  1  0
 20 39  1  0
 21 40  1  0
 21 41  1  0
 23 42  1  0
 23 43  1  0
 23 44  1  0
 24 45  1  0
 24 46  1  0
 24 47  1  0
 25 48  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
5-[(3,6-Dimethyl-6-formyl-2-heptenyl)oxy]psoralen	HMDB

Chemical Formula

C₂₁H₂₂O₅

Average Molecular Weight

354.3964

Monoisotopic Molecular Weight

354.146723814

IUPAC Name

(5E)-2,2,5-trimethyl-7-({7-oxo-7H-furo[3,2-g]chromen-4-yl}oxy)hept-5-enal

Traditional Name

(5E)-2,2,5-trimethyl-7-({7-oxofuro[3,2-g]chromen-4-yl}oxy)hept-5-enal

CAS Registry Number

Not Available

SMILES

C\C(CCC(C)(C)C=O)=C/COC1=C2C=COC2=CC2=C1C=CC(=O)O2

InChI Identifier

InChI=1S/C21H22O5/c1-14(6-9-21(2,3)13-22)7-10-25-20-15-4-5-19(23)26-18(15)12-17-16(20)8-11-24-17/h4-5,7-8,11-13H,6,9-10H2,1-3H3/b14-7+

InChI Key

JBBNVKWFZYFPIG-VGOFMYFVSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as psoralens. These are organic compounds containing a psoralen moiety, which consists of a furan fused to a chromenone to for 7H-furo[3,2-g]chromen-7-one.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Coumarins and derivatives

Sub Class

Furanocoumarins

Direct Parent

Psoralens

Alternative Parents

Substituents

Psoralen
Benzopyran
1-benzopyran
Benzofuran
Alkyl aryl ether
Pyranone
Benzenoid
Pyran
Heteroaromatic compound
Furan
Lactone
Ether
Oxacycle
Organoheterocyclic compound
Aldehyde
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cell membrane (HMDB: HMDB0030735)

Cellular substructure

Membrane (HMDB: HMDB0030735)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0030735)

Source

Endogenous

Endogenous (HMDB: HMDB0030735)

Plant

Plant (HMDB: HMDB0030735)

Exogenous

Food

Food (HMDB: HMDB0030735)

Fruit

Citrus

Citrus (FooDB: FOOD00859)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	134 - 136 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.01 g/L	ALOGPS
logP	4.73	ALOGPS
logP	4.1	ChemAxon
logS	-4.6	ALOGPS
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	65.74 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	99.59 m³·mol⁻¹	ChemAxon
Polarizability	38.14 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	Yes	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	184.975	31661259
DarkChem	[M-H]-	183.972	31661259
DeepCCS	[M+H]+	192.401	30932474
DeepCCS	[M-H]-	189.908	30932474
DeepCCS	[M-2H]-	224.335	30932474
DeepCCS	[M+Na]+	200.178	30932474
AllCCS	[M+H]+	185.2	32859911
AllCCS	[M+H-H2O]+	182.3	32859911
AllCCS	[M+NH4]+	187.8	32859911
AllCCS	[M+Na]+	188.5	32859911
AllCCS	[M-H]-	189.3	32859911
AllCCS	[M+Na-2H]-	189.0	32859911
AllCCS	[M+HCOO]-	188.7	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Aurantiumal	C\C(CCC(C)(C)C=O)=C/COC1=C2C=COC2=CC2=C1C=CC(=O)O2	3726.9	Standard polar	33892256
Aurantiumal	C\C(CCC(C)(C)C=O)=C/COC1=C2C=COC2=CC2=C1C=CC(=O)O2	2901.8	Standard non polar	33892256
Aurantiumal	C\C(CCC(C)(C)C=O)=C/COC1=C2C=COC2=CC2=C1C=CC(=O)O2	2958.4	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Aurantiumal GC-MS (Non-derivatized) - 70eV, Positive	splash10-0fi0-4569000000-18a7a96accf2ad0d4300	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Aurantiumal GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Aurantiumal 10V, Positive-QTOF	splash10-0a4i-0329000000-3ba30c824120dddd5cb8	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Aurantiumal 20V, Positive-QTOF	splash10-0uxr-5795000000-f44ed3b5b7097fd2e440	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Aurantiumal 40V, Positive-QTOF	splash10-0udi-9640000000-f522d76819173300aed8	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Aurantiumal 10V, Negative-QTOF	splash10-0udi-0039000000-7a12ac609e967bb30c8d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Aurantiumal 20V, Negative-QTOF	splash10-0udi-0494000000-58d184a896d50bc7e900	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Aurantiumal 40V, Negative-QTOF	splash10-0a4i-1910000000-f16468f2722290f6f4ff	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Aurantiumal 10V, Positive-QTOF	splash10-0udi-0198000000-7da23b8a6046a154588b	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Aurantiumal 20V, Positive-QTOF	splash10-0udi-3696000000-d0729de9efec49c7b2cd	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Aurantiumal 40V, Positive-QTOF	splash10-0kxr-3972000000-96957b4a02c2059fe29d	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Aurantiumal 10V, Negative-QTOF	splash10-0fb9-0059000000-240036c4fb670a837be4	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Aurantiumal 20V, Negative-QTOF	splash10-0udi-0398000000-7db2b7ffa0d354d734ad	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Aurantiumal 40V, Negative-QTOF	splash10-0zfr-0890000000-d66a954f8c5efe2e2fdd	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB002661

KNApSAcK ID

Not Available

Chemspider ID

30776846

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

122201415

PDB ID

Not Available

ChEBI ID

171795

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for Aurantiumal (HMDB0030735)

MOL for HMDB0030735 (Aurantiumal)

3D MOL for HMDB0030735 (Aurantiumal)

3D SDF for HMDB0030735 (Aurantiumal)

3D-SDF for HMDB0030735 (Aurantiumal)

PDB for HMDB0030735 (Aurantiumal)

3D PDB for HMDB0030735 (Aurantiumal)

SMILES for HMDB0030735 (Aurantiumal)

INCHI for HMDB0030735 (Aurantiumal)

Structure for HMDB0030735 (Aurantiumal)

3D Structure for HMDB0030735 (Aurantiumal)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra