MiMeDB: Showing metabocard for Phytosphingosine (MMDBc0000605)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2020-12-10 18:50:57 UTC

Update Date

2024-04-30 19:33:15 UTC

Metabolite ID

MMDBc0000605

Metabolite Identification

Common Name

Phytosphingosine

Description

Phytosphingosine is a phospholipid. Phospholipids are a class of lipids and a major component of all biological membranes; sphingolipid metabolites, such as sphingosine and ceramide, are highly bioactive compounds and are involved in diverse cell processes, including cell-cell interaction, cell proliferation, differentiation, and apoptosis. Phytosphingosine is also one of the most widely distributed natural sphingoid bases, which is abundant in fungi and plants, and also found in animals including humans. Phytosphingosine is structurally similar to sphingosine; phytosphingosine possesses a hydroxyl group at C-4 of the sphingoid long-chain base. The physiological roles of phytosphingosine are largely unknown. Phytosphingosine induces apoptosis in human T-cell lymphoma and non-small cell lung cancer cells, and induces caspase-independent cytochrome c release from mitochondria. In the presence of caspase inhibitors, phytosphingosine-induced apoptosis is almost completely suppressed, suggesting that phytosphingosine-induced apoptosis is largely dependent on caspase activities. (PMID: 12576463 , 12531554 , 8046331 , 8048941 ,8706124 ).

Structure

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

HMDB0004610
     RDKit          3D
Phytosphingosine
 61 60  0  0  0  0  0  0  0  0999 V2000
    7.8720    1.8626   -1.5700 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6181    1.4573   -0.8262 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9689    0.8967    0.5327 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7594    0.4790    1.3122 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9716   -0.5915    0.5907 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7591   -0.9896    1.4040 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0289   -2.0555    0.6217 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7976   -2.5465    1.3142 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7834   -1.4609    1.5650 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3691   -0.8735    0.2517 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6477    0.2272    0.3742 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9209   -0.1772    1.0142 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6806   -1.2591    0.3348 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1089   -0.9877   -1.0510 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0056    0.1975   -1.2546 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.2571    0.2275   -2.6543 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3619    0.0663   -0.6041 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.1986    0.0466    0.7606 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2125    1.2783   -0.9428 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.4228    1.3550   -2.3851 N   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5753    1.1984   -0.2991 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5362    1.1203    1.0700 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2533    2.8644   -1.2292 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6646    1.0880   -1.4631 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6838    1.9615   -2.6571 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9919    2.3767   -0.7432 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0728    0.7447   -1.4553 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7017    0.0909    0.3961 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4701    1.7135    1.0947 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1129    0.1288    2.3066 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0760    1.3264    1.5129 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5643   -1.4991    0.4029 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5767   -0.1250   -0.3449 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0530   -0.1323    1.5069 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0319   -1.3406    2.4046 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7361   -2.9350    0.5777 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8861   -1.7344   -0.4079 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3203   -3.3009    0.6707 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1008   -3.0665    2.2450 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1824   -0.6796    2.2569 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0655   -1.9498    2.1033 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0139   -1.7112   -0.3926 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2848   -0.4842   -0.2397 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7781    0.6733   -0.6364 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1877    1.0255    0.9958 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6995   -0.5010    2.0550 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5592    0.7258    1.1112 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0608   -2.2091    0.3124 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5541   -1.5549    0.9445 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7041   -1.8824   -1.4068 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2836   -0.9084   -1.7869 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5426    1.1627   -1.0264 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4184    0.4906   -3.1422 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9236   -0.8128   -0.9909 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7527   -0.6299    1.2208 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6720    2.1816   -0.6521 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2618    1.9844   -2.5123 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6644    0.4367   -2.7931 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1077    2.1401   -0.5801 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1757    0.3637   -0.6980 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3662    1.4563    1.4813 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  2 26  1  0
  2 27  1  0
  3 28  1  0
  3 29  1  0
  4 30  1  0
  4 31  1  0
  5 32  1  0
  5 33  1  0
  6 34  1  0
  6 35  1  0
  7 36  1  0
  7 37  1  0
  8 38  1  0
  8 39  1  0
  9 40  1  0
  9 41  1  0
 10 42  1  0
 10 43  1  0
 11 44  1  0
 11 45  1  0
 12 46  1  0
 12 47  1  0
 13 48  1  0
 13 49  1  0
 14 50  1  0
 14 51  1  0
 15 52  1  1
 16 53  1  0
 17 54  1  6
 18 55  1  0
 19 56  1  1
 20 57  1  0
 20 58  1  0
 21 59  1  0
 21 60  1  0
 22 61  1  0
M  END


  Mrv1652309042000312D          

 22 21  0  0  0  0            999 V2000
10018.988210015.2073    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10018.272710015.6194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10017.557510015.2073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10016.844010015.6194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10016.128510015.2073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10015.413110015.6194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10014.697610015.2073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10013.982910015.6194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10013.268010015.2073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10012.553510015.6194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10011.839010015.2073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10011.124210015.6194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10010.409510015.2073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10009.694910015.6194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10008.980410015.2073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10019.701510015.6194    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10020.417010015.2073    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10021.130310015.6194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10021.845710015.2073    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10020.417010014.3821    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
10019.701510016.4439    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10018.988810014.3817    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1 16  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 16 17  1  0  0  0  0
 16 21  1  1  0  0  0
 17 18  1  0  0  0  0
 17 20  1  6  0  0  0
 18 19  1  0  0  0  0
  1 22  1  6  0  0  0
M  END
> <DATABASE_ID>
MMDBc0000605

> <DATABASE_NAME>
MIME

> <SMILES>
CCCCCCCCCCCCCC[C@@H](O)[C@@H](O)[C@@H](N)CO

> <INCHI_IDENTIFIER>
InChI=1S/C18H39NO3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-17(21)18(22)16(19)15-20/h16-18,20-22H,2-15,19H2,1H3/t16-,17+,18-/m0/s1

> <INCHI_KEY>
AERBNCYCJBRYDG-KSZLIROESA-N

> <FORMULA>
C18H39NO3

> <MOLECULAR_WEIGHT>
317.5072

> <EXACT_MASS>
317.292994119

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
61

> <JCHEM_AVERAGE_POLARIZABILITY>
41.04821545288787

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S,3S,4R)-2-aminooctadecane-1,3,4-triol

> <ALOGPS_LOGP>
3.96

> <JCHEM_LOGP>
3.6976906383333326

> <ALOGPS_LOGS>
-3.85

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
14.815152200058375

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.447718983386185

> <JCHEM_PKA_STRONGEST_BASIC>
8.908333300303687

> <JCHEM_POLAR_SURFACE_AREA>
86.71

> <JCHEM_REFRACTIVITY>
92.2909

> <JCHEM_ROTATABLE_BOND_COUNT>
16

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.46e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
phytosphingosine

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0004610
     RDKit          3D
Phytosphingosine
 61 60  0  0  0  0  0  0  0  0999 V2000
    7.8720    1.8626   -1.5700 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6181    1.4573   -0.8262 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9689    0.8967    0.5327 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7594    0.4790    1.3122 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9716   -0.5915    0.5907 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7591   -0.9896    1.4040 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0289   -2.0555    0.6217 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7976   -2.5465    1.3142 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7834   -1.4609    1.5650 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3691   -0.8735    0.2517 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6477    0.2272    0.3742 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9209   -0.1772    1.0142 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6806   -1.2591    0.3348 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1089   -0.9877   -1.0510 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0056    0.1975   -1.2546 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.2571    0.2275   -2.6543 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3619    0.0663   -0.6041 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.1986    0.0466    0.7606 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2125    1.2783   -0.9428 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.4228    1.3550   -2.3851 N   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5753    1.1984   -0.2991 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5362    1.1203    1.0700 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2533    2.8644   -1.2292 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6646    1.0880   -1.4631 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6838    1.9615   -2.6571 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9919    2.3767   -0.7432 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0728    0.7447   -1.4553 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7017    0.0909    0.3961 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4701    1.7135    1.0947 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1129    0.1288    2.3066 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0760    1.3264    1.5129 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5643   -1.4991    0.4029 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5767   -0.1250   -0.3449 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0530   -0.1323    1.5069 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0319   -1.3406    2.4046 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7361   -2.9350    0.5777 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8861   -1.7344   -0.4079 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3203   -3.3009    0.6707 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1008   -3.0665    2.2450 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1824   -0.6796    2.2569 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0655   -1.9498    2.1033 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0139   -1.7112   -0.3926 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2848   -0.4842   -0.2397 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7781    0.6733   -0.6364 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1877    1.0255    0.9958 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6995   -0.5010    2.0550 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5592    0.7258    1.1112 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0608   -2.2091    0.3124 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5541   -1.5549    0.9445 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7041   -1.8824   -1.4068 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2836   -0.9084   -1.7869 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5426    1.1627   -1.0264 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4184    0.4906   -3.1422 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9236   -0.8128   -0.9909 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7527   -0.6299    1.2208 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6720    2.1816   -0.6521 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2618    1.9844   -2.5123 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6644    0.4367   -2.7931 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1077    2.1401   -0.5801 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1757    0.3637   -0.6980 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3662    1.4563    1.4813 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  2 26  1  0
  2 27  1  0
  3 28  1  0
  3 29  1  0
  4 30  1  0
  4 31  1  0
  5 32  1  0
  5 33  1  0
  6 34  1  0
  6 35  1  0
  7 36  1  0
  7 37  1  0
  8 38  1  0
  8 39  1  0
  9 40  1  0
  9 41  1  0
 10 42  1  0
 10 43  1  0
 11 44  1  0
 11 45  1  0
 12 46  1  0
 12 47  1  0
 13 48  1  0
 13 49  1  0
 14 50  1  0
 14 51  1  0
 15 52  1  1
 16 53  1  0
 17 54  1  6
 18 55  1  0
 19 56  1  1
 20 57  1  0
 20 58  1  0
 21 59  1  0
 21 60  1  0
 22 61  1  0
M  END

HEADER    PROTEIN                                 04-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-20         0                                  
HETATM    1  C   UNK     0    8702.1118695.054   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8700.7768695.823   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8699.4418695.054   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    8698.1098695.823   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0    8696.7738695.054   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    8695.4388695.823   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    8694.1028695.054   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8692.7688695.823   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8691.4348695.054   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8690.1008695.823   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8688.7668695.054   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8687.4328695.823   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8686.0988695.054   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8684.7648695.823   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8683.4308695.054   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8703.4438695.823   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8704.7788695.054   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    8706.1108695.823   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0    8707.4458695.054   0.000  0.00  0.00           O+0
HETATM   20  N   UNK     0    8704.7788693.513   0.000  0.00  0.00           N+0
HETATM   21  O   UNK     0    8703.4438697.362   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0    8702.1128693.513   0.000  0.00  0.00           O+0
CONECT    1    2   16   22                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14                                                            
CONECT   16    1   17   21                                                  
CONECT   17   16   18   20                                                  
CONECT   18   17   19                                                       
CONECT   19   18                                                            
CONECT   20   17                                                            
CONECT   21   16                                                            
CONECT   22    1                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   42    0
END

COMPND    HMDB0004610
HETATM    1  C1  UNL     1       7.872   1.863  -1.570  1.00  0.00           C  
HETATM    2  C2  UNL     1       6.618   1.457  -0.826  1.00  0.00           C  
HETATM    3  C3  UNL     1       6.969   0.897   0.533  1.00  0.00           C  
HETATM    4  C4  UNL     1       5.759   0.479   1.312  1.00  0.00           C  
HETATM    5  C5  UNL     1       4.972  -0.591   0.591  1.00  0.00           C  
HETATM    6  C6  UNL     1       3.759  -0.990   1.404  1.00  0.00           C  
HETATM    7  C7  UNL     1       3.029  -2.056   0.622  1.00  0.00           C  
HETATM    8  C8  UNL     1       1.798  -2.547   1.314  1.00  0.00           C  
HETATM    9  C9  UNL     1       0.783  -1.461   1.565  1.00  0.00           C  
HETATM   10  C10 UNL     1       0.369  -0.874   0.252  1.00  0.00           C  
HETATM   11  C11 UNL     1      -0.648   0.227   0.374  1.00  0.00           C  
HETATM   12  C12 UNL     1      -1.921  -0.177   1.014  1.00  0.00           C  
HETATM   13  C13 UNL     1      -2.681  -1.259   0.335  1.00  0.00           C  
HETATM   14  C14 UNL     1      -3.109  -0.988  -1.051  1.00  0.00           C  
HETATM   15  C15 UNL     1      -4.006   0.197  -1.255  1.00  0.00           C  
HETATM   16  O1  UNL     1      -4.257   0.228  -2.654  1.00  0.00           O  
HETATM   17  C16 UNL     1      -5.362   0.066  -0.604  1.00  0.00           C  
HETATM   18  O2  UNL     1      -5.199   0.047   0.761  1.00  0.00           O  
HETATM   19  C17 UNL     1      -6.213   1.278  -0.943  1.00  0.00           C  
HETATM   20  N1  UNL     1      -6.423   1.355  -2.385  1.00  0.00           N  
HETATM   21  C18 UNL     1      -7.575   1.198  -0.299  1.00  0.00           C  
HETATM   22  O3  UNL     1      -7.536   1.120   1.070  1.00  0.00           O  
HETATM   23  H1  UNL     1       8.253   2.864  -1.229  1.00  0.00           H  
HETATM   24  H2  UNL     1       8.665   1.088  -1.463  1.00  0.00           H  
HETATM   25  H3  UNL     1       7.684   1.961  -2.657  1.00  0.00           H  
HETATM   26  H4  UNL     1       5.992   2.377  -0.743  1.00  0.00           H  
HETATM   27  H5  UNL     1       6.073   0.745  -1.455  1.00  0.00           H  
HETATM   28  H6  UNL     1       7.702   0.091   0.396  1.00  0.00           H  
HETATM   29  H7  UNL     1       7.470   1.714   1.095  1.00  0.00           H  
HETATM   30  H8  UNL     1       6.113   0.129   2.307  1.00  0.00           H  
HETATM   31  H9  UNL     1       5.076   1.326   1.513  1.00  0.00           H  
HETATM   32  H10 UNL     1       5.564  -1.499   0.403  1.00  0.00           H  
HETATM   33  H11 UNL     1       4.577  -0.125  -0.345  1.00  0.00           H  
HETATM   34  H12 UNL     1       3.053  -0.132   1.507  1.00  0.00           H  
HETATM   35  H13 UNL     1       4.032  -1.341   2.405  1.00  0.00           H  
HETATM   36  H14 UNL     1       3.736  -2.935   0.578  1.00  0.00           H  
HETATM   37  H15 UNL     1       2.886  -1.734  -0.408  1.00  0.00           H  
HETATM   38  H16 UNL     1       1.320  -3.301   0.671  1.00  0.00           H  
HETATM   39  H17 UNL     1       2.101  -3.066   2.245  1.00  0.00           H  
HETATM   40  H18 UNL     1       1.182  -0.680   2.257  1.00  0.00           H  
HETATM   41  H19 UNL     1      -0.065  -1.950   2.103  1.00  0.00           H  
HETATM   42  H20 UNL     1       0.014  -1.711  -0.393  1.00  0.00           H  
HETATM   43  H21 UNL     1       1.285  -0.484  -0.240  1.00  0.00           H  
HETATM   44  H22 UNL     1      -0.778   0.673  -0.636  1.00  0.00           H  
HETATM   45  H23 UNL     1      -0.188   1.026   0.996  1.00  0.00           H  
HETATM   46  H24 UNL     1      -1.700  -0.501   2.055  1.00  0.00           H  
HETATM   47  H25 UNL     1      -2.559   0.726   1.111  1.00  0.00           H  
HETATM   48  H26 UNL     1      -2.061  -2.209   0.312  1.00  0.00           H  
HETATM   49  H27 UNL     1      -3.554  -1.555   0.945  1.00  0.00           H  
HETATM   50  H28 UNL     1      -3.704  -1.882  -1.407  1.00  0.00           H  
HETATM   51  H29 UNL     1      -2.284  -0.908  -1.787  1.00  0.00           H  
HETATM   52  H30 UNL     1      -3.543   1.163  -1.026  1.00  0.00           H  
HETATM   53  H31 UNL     1      -3.418   0.491  -3.142  1.00  0.00           H  
HETATM   54  H32 UNL     1      -5.924  -0.813  -0.991  1.00  0.00           H  
HETATM   55  H33 UNL     1      -5.753  -0.630   1.221  1.00  0.00           H  
HETATM   56  H34 UNL     1      -5.672   2.182  -0.652  1.00  0.00           H  
HETATM   57  H35 UNL     1      -7.262   1.984  -2.512  1.00  0.00           H  
HETATM   58  H36 UNL     1      -6.664   0.437  -2.793  1.00  0.00           H  
HETATM   59  H37 UNL     1      -8.108   2.140  -0.580  1.00  0.00           H  
HETATM   60  H38 UNL     1      -8.176   0.364  -0.698  1.00  0.00           H  
HETATM   61  H39 UNL     1      -8.366   1.456   1.481  1.00  0.00           H  
CONECT    1    2   23   24   25
CONECT    2    3   26   27
CONECT    3    4   28   29
CONECT    4    5   30   31
CONECT    5    6   32   33
CONECT    6    7   34   35
CONECT    7    8   36   37
CONECT    8    9   38   39
CONECT    9   10   40   41
CONECT   10   11   42   43
CONECT   11   12   44   45
CONECT   12   13   46   47
CONECT   13   14   48   49
CONECT   14   15   50   51
CONECT   15   16   17   52
CONECT   16   53
CONECT   17   18   19   54
CONECT   18   55
CONECT   19   20   21   56
CONECT   20   57   58
CONECT   21   22   59   60
CONECT   22   61
END

HMDB0004610
     RDKit          3D
Phytosphingosine
 61 60  0  0  0  0  0  0  0  0999 V2000
    7.8720    1.8626   -1.5700 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6181    1.4573   -0.8262 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9689    0.8967    0.5327 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7594    0.4790    1.3122 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9716   -0.5915    0.5907 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7591   -0.9896    1.4040 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0289   -2.0555    0.6217 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7976   -2.5465    1.3142 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7834   -1.4609    1.5650 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3691   -0.8735    0.2517 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6477    0.2272    0.3742 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9209   -0.1772    1.0142 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6806   -1.2591    0.3348 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1089   -0.9877   -1.0510 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0056    0.1975   -1.2546 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.2571    0.2275   -2.6543 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3619    0.0663   -0.6041 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.1986    0.0466    0.7606 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2125    1.2783   -0.9428 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.4228    1.3550   -2.3851 N   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5753    1.1984   -0.2991 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5362    1.1203    1.0700 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2533    2.8644   -1.2292 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6646    1.0880   -1.4631 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6838    1.9615   -2.6571 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9919    2.3767   -0.7432 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0728    0.7447   -1.4553 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7017    0.0909    0.3961 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4701    1.7135    1.0947 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1129    0.1288    2.3066 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0760    1.3264    1.5129 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5643   -1.4991    0.4029 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5767   -0.1250   -0.3449 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0530   -0.1323    1.5069 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0319   -1.3406    2.4046 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7361   -2.9350    0.5777 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8861   -1.7344   -0.4079 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3203   -3.3009    0.6707 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1008   -3.0665    2.2450 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1824   -0.6796    2.2569 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0655   -1.9498    2.1033 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0139   -1.7112   -0.3926 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2848   -0.4842   -0.2397 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7781    0.6733   -0.6364 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1877    1.0255    0.9958 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6995   -0.5010    2.0550 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5592    0.7258    1.1112 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0608   -2.2091    0.3124 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5541   -1.5549    0.9445 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7041   -1.8824   -1.4068 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2836   -0.9084   -1.7869 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5426    1.1627   -1.0264 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4184    0.4906   -3.1422 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9236   -0.8128   -0.9909 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7527   -0.6299    1.2208 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6720    2.1816   -0.6521 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2618    1.9844   -2.5123 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6644    0.4367   -2.7931 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1077    2.1401   -0.5801 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1757    0.3637   -0.6980 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3662    1.4563    1.4813 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  2 26  1  0
  2 27  1  0
  3 28  1  0
  3 29  1  0
  4 30  1  0
  4 31  1  0
  5 32  1  0
  5 33  1  0
  6 34  1  0
  6 35  1  0
  7 36  1  0
  7 37  1  0
  8 38  1  0
  8 39  1  0
  9 40  1  0
  9 41  1  0
 10 42  1  0
 10 43  1  0
 11 44  1  0
 11 45  1  0
 12 46  1  0
 12 47  1  0
 13 48  1  0
 13 49  1  0
 14 50  1  0
 14 51  1  0
 15 52  1  1
 16 53  1  0
 17 54  1  6
 18 55  1  0
 19 56  1  1
 20 57  1  0
 20 58  1  0
 21 59  1  0
 21 60  1  0
 22 61  1  0
M  END

Synonyms

Value	Source
4-D-Hydroxysphinganine	ChEBI
4-R-Hydroxyoctadecasphinganine	ChEBI
(+)-D-Ribo-phytosphingosine	HMDB
4-D-Hydroxy-sphinganine	HMDB
4D-Hydroxysphinganine	HMDB
C18-Phytosphingosine	HMDB
D-Ribo-1,3,4-trihydroxy-2-aminooctadecane	HMDB
D-Ribo-2-amino-1,3,4-octadecanetriol	HMDB
[2S-(2R,3R,4S*)]-2-amino-1,3,4-octadecanetriol	HMDB
8-(Z-e)-C18-Phytosphingenine	HMDB
(2S,3S,4R)-2-Amino-1,3,4-octadecanetriol	HMDB
(2S,3S,4R)-2-Amino-1,3,4-trihydroxyoctadecane	HMDB
D-Ribo-phytosphingosine	HMDB
SP(t18:0)	HMDB
Phytosphingosine	HMDB

Molecular Formula

C₁₈H₃₉NO₃

Average Mass

317.5072

Monoisotopic Mass

317.292994119

IUPAC Name

(2S,3S,4R)-2-aminooctadecane-1,3,4-triol

Traditional Name

phytosphingosine

CAS Registry Number

Not Available

SMILES

CCCCCCCCCCCCCC[C@@H](O)[C@@H](O)[C@@H](N)CO

InChI Identifier

InChI=1S/C18H39NO3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-17(21)18(22)16(19)15-20/h16-18,20-22H,2-15,19H2,1H3/t16-,17+,18-/m0/s1

InChI Key

AERBNCYCJBRYDG-KSZLIROESA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 1,3-aminoalcohols. These are organic compounds containing an alkyl chain with an amine group bound to the C1 atom and an alcohol group bound to the C3 atom.

Kingdom

Organic compounds

Super Class

Organic nitrogen compounds

Class

Organonitrogen compounds

Sub Class

Amines

Direct Parent

1,3-aminoalcohols

Alternative Parents

Substituents

1,3-aminoalcohol
Secondary alcohol
1,2-aminoalcohol
Polyol
Organic oxygen compound
Organopnictogen compound
Hydrocarbon derivative
Primary amine
Primary alcohol
Organooxygen compound
Primary aliphatic amine
Alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

sphingoid (CHEBI:46961 )
amino alcohol (CHEBI:46961 )
triol (CHEBI:46961 )
4-Hydroxysphinganines (Phytosphingosines) (C12144 )
4-Hydroxysphinganines (Phytosphingosines) (LMSP01030001 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.045 g/L	ALOGPS
logP	3.96	ALOGPS
logP	3.7	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	13.45	ChemAxon
pKa (Strongest Basic)	8.91	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	86.71 Å²	ChemAxon
Rotatable Bond Count	16	ChemAxon
Refractivity	92.29 m³·mol⁻¹	ChemAxon
Polarizability	41.05 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-001i-1910000000-6a156f8b67eb8d2e2af8	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0udi-0590000000-55f1259ff17447451d03	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-001i-1910000000-6a156f8b67eb8d2e2af8	2018-05-18	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0udi-0590000000-55f1259ff17447451d03	2018-05-18	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-08fu-9240000000-f0c822bc0197665bc676	2016-09-22	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positive	splash10-0pxr-8498250000-59c3446ba7cde2700251	2017-10-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-03di-9025000000-41591a03203ebe6783ab	2020-07-21	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF 35V, positive	splash10-03yi-9055000000-c534f58f04d1f008079f	2020-07-21	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 5V, positive	splash10-014i-0009000000-2467642b22875f4e99a1	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 7V, positive	splash10-014i-0009000000-94b30bf1ae7ab25e566e	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 12V, positive	splash10-03xr-9037000000-2e7ea43f8d534e10f1d4	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 15V, positive	splash10-03di-9020000000-ac9c04a9082abb540f22	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 19V, positive	splash10-03di-9010000000-e1fe657c8693bf3f19e7	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 26V, positive	splash10-03di-9000000000-f71f3038d0b8478d679c	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 31V, positive	splash10-03di-9000000000-795a4947f722e8f61620	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 38V, positive	splash10-03di-9000000000-e62d8c5bcb55aa166603	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 44V, positive	splash10-03di-9000000000-cb05f289ecdcd16de4e7	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 52V, positive	splash10-03di-9000000000-e898ac84341e318b5862	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 60V, positive	splash10-08fr-9000000000-b048fe168eacee259394	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 72V, positive	splash10-0900-9000000000-d72ddb3ba2da45266fab	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - n/a 22V, positive	splash10-0udi-0039000000-33d42068332d814a2c83	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - n/a 22V, positive	splash10-06yt-6940000000-fdeb46044349d9fcc996	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - n/a 22V, positive	splash10-0006-9000000000-981a59d4f1dd5e03c5ac	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - n/a 22V, positive	splash10-0ik9-0190000000-d31bcfd06b73972a4300	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - n/a 22V, positive	splash10-03di-2290000000-b7855c3c2203ca25bab3	2020-07-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0uxr-1029000000-ea43e68bb4fffc9657b1	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03dl-9121000000-cce64d1dcf28012d72f8	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9520000000-d95a37794c98d95dd2b0	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-2097000000-1f5b8c8eefe1a491d0c9	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0bt9-9060000000-7550c32b4e1dfcbc4593	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-052f-9020000000-5cbe1fbb421cacd42e98	2016-09-12	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-21	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Epidermis
Feces
Placenta
Thyroid Gland

Tissue Locations

Epidermis
Placenta
Thyroid Gland

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species
MMDBp0192100	Globoside alpha-1,3-N-acetylgalactosaminyltransferase 1	Unknown	Q8N5D6	Homo sapiens
MMDBp0192203	N-acetylglucosaminyl-phosphatidylinositol de-N-acetylase	Enzyme	Q9Y2B2	Homo sapiens
MMDBp0192558	Phosphatidylinositol N-acetylglucosaminyltransferase subunit Q	Enzyme	Q9BRB3	Homo sapiens
MMDBp0192559	Phosphatidylinositol N-acetylglucosaminyltransferase subunit A	Enzyme	P37287	Homo sapiens
MMDBp0192560	Phosphatidylinositol N-acetylglucosaminyltransferase subunit H	Enzyme	Q14442	Homo sapiens
MMDBp0192561	Phosphatidylinositol N-acetylglucosaminyltransferase subunit P	Enzyme	P57054	Homo sapiens
MMDBp0192562	Phosphatidylinositol N-acetylglucosaminyltransferase subunit C	Enzyme	Q92535	Homo sapiens
MMDBp0192690	Acid ceramidase	Enzyme	Q13510	Homo sapiens
MMDBp0193223	Ganglioside GM2 activator	Enzyme	P17900	Homo sapiens
MMDBp0193531	T-cell surface glycoprotein CD1e, membrane-associated	Enzyme	P15812	Homo sapiens
MMDBp0193636	Epididymal secretory protein E1	Enzyme	P61916	Homo sapiens
MMDBp0193673	Antigen-presenting glycoprotein CD1d	Enzyme	P15813	Homo sapiens
MMDBp0193742	GPI mannosyltransferase 1	Enzyme	Q9H3S5	Homo sapiens
MMDBp0193755	Phosphatidylinositol-glycan biosynthesis class W protein	Enzyme	Q7Z7B1	Homo sapiens
MMDBp0193805	Phosphatidylinositol-glycan biosynthesis class X protein	Enzyme	Q8TBF5	Homo sapiens
MMDBp0193806	GPI mannosyltransferase 4	Enzyme	Q86VD9	Homo sapiens
MMDBp0194033	Lactosylceramide 1,3-N-acetyl-beta-D-glucosaminyltransferase	Enzyme	Q9BYG0	Homo sapiens
MMDBp0194044	Beta-1,3-galactosyltransferase 5	Enzyme	Q9Y2C3	Homo sapiens
MMDBp0194119	GPI mannosyltransferase 3	Enzyme	Q92521	Homo sapiens
MMDBp0194120	Phosphatidylinositol-glycan biosynthesis class F protein	Enzyme	Q07326	Homo sapiens
MMDBp0194121	GPI ethanolamine phosphate transferase 2	Enzyme	Q5H8A4	Homo sapiens
MMDBp0194122	GPI ethanolamine phosphate transferase 1	Enzyme	O95427	Homo sapiens
MMDBp0194123	GPI ethanolamine phosphate transferase 3	Enzyme	Q8TEQ8	Homo sapiens
MMDBp0194124	GPI transamidase component PIG-S	Enzyme	Q96S52	Homo sapiens
MMDBp0194125	GPI transamidase component PIG-T	Enzyme	Q969N2	Homo sapiens
MMDBp0194126	Phosphatidylinositol glycan anchor biosynthesis class U protein	Enzyme	Q9H490	Homo sapiens
MMDBp0194127	GPI mannosyltransferase 2	Enzyme	Q9NUD9	Homo sapiens
MMDBp0194128	Phosphatidylinositol N-acetylglucosaminyltransferase subunit Y	Enzyme	Q3MUY2	Homo sapiens
MMDBp0194133	Pleckstrin homology domain-containing family A member 8	Unknown	Q96JA3	Homo sapiens
MMDBp0195880	Alkaline ceramidase 2	Enzyme	Q5QJU3	Homo sapiens
MMDBp0195885	Non-lysosomal glucosylceramidase	Enzyme	Q9HCG7	Homo sapiens
MMDBp0196227	Alkaline ceramidase 1	Enzyme	Q8TDN7	Homo sapiens
MMDBp0196528	GPI-anchor transamidase	Enzyme	Q92643	Homo sapiens
MMDBp0196556	Glycosylphosphatidylinositol anchor attachment 1 protein	Unknown	O43292	Homo sapiens
MMDBp0196557	Protein PLEKHA9	Unknown	O95397	Homo sapiens
MMDBp0196558	Glycolipid transfer protein domain-containing protein 2	Unknown	A6NH11	Homo sapiens
MMDBp0196559	Putative uncharacterized protein PLEKHA8	Unknown	B5MDU3	Homo sapiens
MMDBp0196560	T-cell surface glycoprotein CD1a	Unknown	P06126	Homo sapiens
MMDBp0196561	Glycolipid transfer protein domain-containing protein 1	Unknown	Q5TA50	Homo sapiens
MMDBp0196562	T-cell surface glycoprotein CD1c	Unknown	P29017	Homo sapiens
MMDBp0196563	Lipopolysaccharide-binding protein	Unknown	P18428	Homo sapiens
MMDBp0196564	Putative uncharacterized protein DKFZp434L0435	Unknown	Q9UFH6	Homo sapiens
MMDBp0196565	T-cell surface glycoprotein CD1b	Unknown	P29016	Homo sapiens
MMDBp0196566	Glycolipid transfer protein	Unknown	Q9NZD2	Homo sapiens

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference
MMDBr0009101	Adenosine triphosphate	ADP	Sphingosine kinase 1	Sphingosine Kinase 1	VMH	30371894
MMDBr0009125	Phytosphingosine	Phytosphingosine	Not Available	Phytosphingosine Transport, from Golgi to Cytosol (Flippase?)	VMH	30371894
MMDBr0009126	Phytosphingosine	Phytosphingosine	Not Available	Phytosphingosine Transport, from Er to Cytosol (Flippase?)	VMH	30371894
MMDBr0019535	Hydrogen Ion	Phytosphingosine	Sphingolipid C4-hydroxylase SUR2	Hydroxylation	PathBank	31602464
MMDBr0019538	Phytosphingosine	Hydrogen Ion	Ceramide synthase subunit LIP1	Synthesis	PathBank	31602464
MMDBr0019541	Phytosphingosine	Hydrogen Ion	Ceramide synthase subunit LIP1	Synthesis	PathBank	31602464
MMDBr0019553	Phytosphingosine	Hydrogen Ion	Ceramide synthase subunit LIP1	Synthesis	PathBank	31602464
MMDBr0019620	Phytosphingosine	Hydrogen Ion	Ceramide synthase subunit LIP1	Synthesis	PathBank	31602464
MMDBr0019621	Phytosphingosine	Hydrogen Ion	Ceramide synthase subunit LIP1	Synthesis	PathBank	31602464
MMDBr0019878	Hydrogen Ion	Phytosphingosine	Sphingolipid C4-hydroxylase SUR2	Hydroxylation	PathBank	31602464

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Verrucomicrobia	1	Human feces; Human stool; Human ; Human urine	Indirect association between microbiota composition and metabolites measured in host biospecimen
Bacteria	Firmicutes	4	Human feces; Human stool; Human ; Human urine; Human sputum	Indirect association between microbiota composition and metabolites measured in host biospecimen
Archaea	Euryarchaeota	1	Human feces; Human	Indirect association between microbiota composition and metabolites measured in host biospecimen
Eukaryota/Fungi	Ascomycota	1	Human feces; Human saliva	Unknown

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Age	Sex	Health Condition	Data Source	Reference
Human Feces	Detected but not Quantified				HMDB
Human Epidermis	Detected but not Quantified	Not Specified	Not Specified	Normal	HMDB	34986597
Human Placenta	Detected but not Quantified	Not Specified	Not Specified	Normal	HMDB	34986597
Human Thyroid gland	Detected but not Quantified	Not Specified	Not Specified	Normal	HMDB	34986597
Human Feces	Detected but not Quantified	Adult (>18 years old)	Both	Normal	HMDB	27543620
Human Feces	Detected but not Quantified	Adult (>18 years old)	Both	Normal	HMDB	25037050
Human Feces	Detected but not Quantified	Adult (>18 years old)	Both	Normal	HMDB	29808030

External Links

HMDB ID

HMDB0004610

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB023381

KNApSAcK ID

Not Available

Chemspider ID

108921

KEGG Compound ID

C12144

BioCyc ID

PHYTOSPINGOSINE

BiGG ID

Not Available

Wikipedia Link

Phytosphingosine

METLIN ID

7066

PubChem Compound

122121

PDB ID

Not Available

ChEBI ID

46961

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Madison KC, Swartzendruber DC, Wertz PW, Downing DT: Sphingolipid metabolism in organotypic mouse keratinocyte cultures. J Invest Dermatol. 1990 Dec;95(6):657-64. doi: 10.1111/1523-1747.ep12514333. [PubMed:2123494 ]
Bouchon B, Portoukalian J, Orgiazzi J, Bornet H: Selective enrichment of phytosphingosine in glycosphingolipids of isolated human thyrocytes as compared to the whole thyroid. Biochem Biophys Res Commun. 1987 Mar 30;143(3):827-31. doi: 10.1016/0006-291x(87)90323-8. [PubMed:3566758 ]
Flamand N, Justine P, Bernaud F, Rougier A, Gaetani Q: In vivo distribution of free long-chain sphingoid bases in the human stratum corneum by high-performance liquid chromatographic analysis of strippings. J Chromatogr B Biomed Appl. 1994 Jun 3;656(1):65-71. doi: 10.1016/0378-4347(94)80021-9. [PubMed:7952048 ]
Haimovitz-Friedman A, Kan CC, Ehleiter D, Persaud RS, McLoughlin M, Fuks Z, Kolesnick RN: Ionizing radiation acts on cellular membranes to generate ceramide and initiate apoptosis. J Exp Med. 1994 Aug 1;180(2):525-35. doi: 10.1084/jem.180.2.525. [PubMed:8046331 ]
Quintans J, Kilkus J, McShan CL, Gottschalk AR, Dawson G: Ceramide mediates the apoptotic response of WEHI 231 cells to anti-immunoglobulin, corticosteroids and irradiation. Biochem Biophys Res Commun. 1994 Jul 29;202(2):710-4. doi: 10.1006/bbrc.1994.1988. [PubMed:8048941 ]
Santana P, Pena LA, Haimovitz-Friedman A, Martin S, Green D, McLoughlin M, Cordon-Cardo C, Schuchman EH, Fuks Z, Kolesnick R: Acid sphingomyelinase-deficient human lymphoblasts and mice are defective in radiation-induced apoptosis. Cell. 1996 Jul 26;86(2):189-99. doi: 10.1016/s0092-8674(00)80091-4. [PubMed:8706124 ]
Nenoff P, Haustein UF: In vitro activity of phytosphingosines against Malassezia furfur and Candida albicans. Acta Derm Venereol. 2002;82(3):170-3. doi: 10.1080/00015550260132433. [PubMed:12353705 ]
Maceyka M, Payne SG, Milstien S, Spiegel S: Sphingosine kinase, sphingosine-1-phosphate, and apoptosis. Biochim Biophys Acta. 2002 Dec 30;1585(2-3):193-201. doi: 10.1016/s1388-1981(02)00341-4. [PubMed:12531554 ]
Park MT, Kang JA, Choi JA, Kang CM, Kim TH, Bae S, Kang S, Kim S, Choi WI, Cho CK, Chung HY, Lee YS, Lee SJ: Phytosphingosine induces apoptotic cell death via caspase 8 activation and Bax translocation in human cancer cells. Clin Cancer Res. 2003 Feb;9(2):878-85. [PubMed:12576463 ]
Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]

Showing metabocard for Phytosphingosine (MMDBc0000605)

MOL for #<Metabolite:0x00007fa5084f9868>

3D MOL for #<Metabolite:0x00007fa5084f9868>

3D SDF for #<Metabolite:0x00007fa5084f9868>

3D-SDF for #<Metabolite:0x00007fa5084f9868>

PDB for #<Metabolite:0x00007fa5084f9868>

3D PDB for #<Metabolite:0x00007fa5084f9868>

SMILES for #<Metabolite:0x00007fa5084f9868>

INCHI for #<Metabolite:0x00007fa5084f9868>

Structure for #<Metabolite:0x00007fa5084f9868>

3D Structure for #<Metabolite:0x00007fa5084f9868>