Endotoxin

ID: ALA3351088

PubChem CID: 44268108

Max Phase: Preclinical

Molecular Formula: C93H175N2O21P

Molecular Weight: 1688.39

Molecule Type: Small molecule

Associated Items:

Bioactivity Summary Target Summary Assay Summary

This compound is not in our inventory system

Names and Identifiers

Canonical SMILES: CCCCCCCCCCCCCC(=O)OC(CCCCCCCCCCC)CC(=O)OC1C(NC(=O)CC(CCCCCCCCCCC)OC(=O)CCCCCCCCCCC)C(OC2CC(OC(=O)CC(O)CCCCCCCCCCC)C(NC(=O)CC(O)CCCCCCCCCCC)C(O)O2)OC(CO)C1OP(=O)(O)O

Standard InChI: InChI=1S/C93H175N2O21P/c1-7-13-19-25-31-37-38-44-50-56-62-68-84(102)110-78(66-60-54-48-42-35-29-23-17-11-5)72-86(104)113-91-89(95-82(100)71-77(65-59-53-47-41-34-28-22-16-10-4)109-83(101)67-61-55-49-43-36-30-24-18-12-6)93(112-80(74-96)90(91)116-117(106,107)108)115-87-73-79(111-85(103)70-76(98)64-58-52-46-40-33-27-21-15-9-3)88(92(105)114-87)94-81(99)69-75(97)63-57-51-45-39-32-26-20-14-8-2/h75-80,87-93,96-98,105H,7-74H2,1-6H3,(H,94,99)(H,95,100)(H2,106,107,108)

Standard InChI Key: HSNYRLYFFRIIEC-UHFFFAOYSA-N

Molfile:

     RDKit          2D

117118  0  0  0  0  0  0  0  0999 V2000
    5.2700   -2.3339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2302   -1.3995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6762   -0.4652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2817   -1.6487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0110   -2.0225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6255    0.1246    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.1031   -0.9593    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.2418   -2.9818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0043   -2.3048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5500   -1.6736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1305   -0.9635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0815   -0.8887    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   10.6812   -0.4361    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.9636   -1.3082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4420   -2.1927    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.2726   -2.9527    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8788   -0.6770    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8564   -2.7700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9536   -3.6296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1238   -3.1811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0923   -4.5142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9378   -3.0815    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.8805   -3.7168    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0682   -3.5673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7916   -3.9369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6962   -4.5640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5068   -5.0873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6853   -5.5233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8356   -4.8755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2592   -0.8887    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.8798   -3.3805    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0591   -2.5582    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.8855   -4.7260    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6296   -2.5208    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6537   -4.7841    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8971   -4.7260    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8880   -5.7310    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3455   -4.2152    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9818   -4.0283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4827   -4.1487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8266   -2.3048    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0773   -0.0665    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0773   -1.7110    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9187   -0.1661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7186   -5.8846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3814   -5.2451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1413   -6.4702    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.3158   -4.9959    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3257    0.5482    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2584   -6.1047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5117   -5.6313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1936   -4.8215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0682   -4.7260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3041   -6.4702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1322   -6.1712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6894   -5.7227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0466   -6.8938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6080   -5.3988    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8522   -5.5233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5625  -12.7618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3099  -11.0300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5367  -13.2975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0166   -9.9711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5001  -12.4088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1255  -10.9013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7742  -11.9644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7161  -11.6156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8133   -6.8564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8598  -12.6206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2068   -9.8714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7110  -10.3199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5259  -10.2327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0882   -7.2634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1604   -8.8581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9403   -9.6471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7367   -8.2725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0606   -9.0242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8829   -9.1239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3655   -6.4827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4485   -6.5699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7807   -7.3298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8198   -6.1961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2343   -6.7775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4461   -7.5666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8688   -8.1521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6654   -7.8406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4536   -8.6380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0392   -9.2194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8274  -10.0084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4088  -10.5940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1970  -11.3872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0806   -8.9453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6197   -7.4793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4079   -8.2767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9893   -8.8581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7692   -9.6471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3506  -10.2327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1305  -11.0300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4992   -9.5226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5947   -7.4253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5641   -7.7866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2411   -8.4636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9919   -9.3980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6771  -10.0790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4279  -11.0051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1090  -11.6904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9269   -8.1770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4295   -6.1047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2177   -6.8938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7908   -7.4793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5790   -8.2767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8872  -11.6114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1480  -13.3473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2876  -14.2319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3373  -11.6904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3406  -10.7269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0774  -12.9860    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  1  1  0
  4  2  1  0
  5  8  1  0
  6 11  1  0
  7 10  1  0
  8 14  1  0
  9  7  1  0
 10 13  1  0
 11  3  1  0
 12 17  1  0
 13  4  1  0
 14 10  1  0
 15  2  1  0
 16  5  1  0
 17  3  1  0
 18 15  1  0
 19 16  1  0
 20 22  1  0
 21 23  1  0
 22  1  1  0
 23  8  1  0
 24 18  1  0
 25 20  1  0
 26 19  1  0
 27 21  1  0
 28 36  1  0
 29 35  1  0
 30 12  1  0
 31 19  2  0
 32 18  2  0
 33 21  2  0
 34 20  2  0
 35 39  1  0
 36 40  1  0
 37 28  2  0
 38 29  2  0
 39 25  1  0
 40 24  1  0
 41  9  1  0
 42 12  2  0
 43 12  1  0
 44 11  1  0
 45 27  1  0
 46 26  1  0
 47 45  1  0
 48 46  1  0
 49 44  1  0
 50 28  1  0
 51 29  1  0
 52 39  1  0
 53 40  1  0
 54 45  1  0
 55 46  1  0
 56 51  1  0
 57 50  1  0
 58 52  1  0
 59 53  1  0
 60 66  1  0
 61 72  1  0
 62 69  1  0
 63 70  1  0
 64 67  1  0
 65 71  1  0
 66 91  1  0
 67 98  1  0
 68 55  1  0
 69106  1  0
 70 78  1  0
 71 99  1  0
 72 75  1  0
 73 54  1  0
 74111  1  0
 75 74  1  0
 76107  1  0
 77 76  1  0
 78 77  1  0
 79 56  1  0
 80 79  1  0
 81 80  1  0
 82 58  1  0
 83 82  1  0
 84 83  1  0
 85 84  1  0
 86 73  1  0
 87 86  1  0
 88 87  1  0
 89 88  1  0
 90 89  1  0
 91 90  1  0
 92 85  1  0
 93 57  1  0
 94 93  1  0
 95 94  1  0
 96 95  1  0
 97 96  1  0
 98 97  1  0
 99 92  1  0
100 81  1  0
101 68  1  0
102101  1  0
103102  1  0
104103  1  0
105104  1  0
106105  1  0
107100  1  0
108 59  1  0
109108  1  0
110109  1  0
111110  1  0
112 61  1  0
113 60  1  0
114 62  1  0
115 65  1  0
116 63  1  0
117 64  1  0
  4  6  1  0
  5  9  1  0
M  END

Associated Targets(non-human)

Mus musculus (284745 Activities)

Explore this target

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Abcc1 Multidrug resistance-associated protein 1 (8 Activities)

Discover Target: Abcc1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Abcb1 Multidrug resistance protein 1 (79 Activities)

Discover Target: Abcb1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Mdr1a Multidrug resistance protein 1a (106 Activities)

Discover Target: Mdr1a

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Abcb1a P-glycoprotein 3 (492 Activities)

Discover Target: Abcb1a

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Abcb11 Bile salt export pump (36 Activities)

Discover Target: Abcb11

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Abcb11 Bile salt export pump (133 Activities)

Discover Target: Abcb11

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Abcc2 Canalicular multispecific organic anion transporter 1 (18 Activities)

Discover Target: Abcc2

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Abcc2 Canalicular multispecific organic anion transporter 1 (241 Activities)

Discover Target: Abcc2

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Abcc3 Canalicular multispecific organic anion transporter 2 (15 Activities)

Discover Target: Abcc3

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Slc10a1 Bile acid transporter (65 Activities)

Discover Target: Slc10a1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Slco1a1 Solute carrier organic anion transporter family member 1A1 (20 Activities)

Discover Target: Slco1a1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Slco1a4 Solute carrier organic anion transporter family member 1A4 (16 Activities)

Discover Target: Slco1a4

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Abcc1 Multidrug resistance-associated protein 1 (42 Activities)

Discover Target: Abcc1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Natural Product: Yes	Oral: No	Chemical Probe: No	Parenteral: No
Molecule Type: Small molecule	Topical: No	First In Class: No	Black Box: No
Chirality: No	Availability: No	Prodrug: No

Natural Product: Yes

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 1688.39	Molecular Weight (Monoisotopic): 1687.2425	AlogP: ┄	#Rotatable Bonds: ┄
Polar Surface Area: ┄	Molecular Species: ┄	HBA: ┄	HBD: ┄
#RO5 Violations: ┄	HBA (Lipinski): ┄	HBD (Lipinski): ┄	#RO5 Violations (Lipinski): ┄
CX Acidic pKa: ┄	CX Basic pKa: ┄	CX LogP: ┄	CX LogD: ┄
Aromatic Rings: ┄	Heavy Atoms: ┄	QED Weighted: ┄	Np Likeness Score: ┄

References

1. Chung S, Ban S, Kim S, Kim B, Woo S, Summers JB, Conway RG. (1995) Synthesis and bioactivities of heterocyclic lipids as PAF antagonists. 2, 5 (10): [10.1016/0960-894X(95)00174-R]
2. Vos TA, Hooiveld GJ, Koning H, Childs S, Meijer DK, Moshage H, Jansen PL, Müller M.. (1998) Up-regulation of the multidrug resistance genes, Mrp1 and Mdr1b, and down-regulation of the organic anion transporter, Mrp2, and the bile salt transporter, Spgp, in endotoxemic rat liver., 28 (1): [PMID:9828229] [10.1002/hep.510280625]
3. Zhao YL, Du J, Kanazawa H, Sugawara A, Takagi K, Kitaichi K, Tatsumi Y, Takagi K, Hasegawa T.. (2002) Effect of endotoxin on doxorubicin transport across blood-brain barrier and P-glycoprotein function in mice., 445 (1): [PMID:12065202] [10.1016/s0014-2999(02)01661-8]
4. Hartmann G, Cheung AK, Piquette-Miller M.. (2002) Inflammatory cytokines, but not bile acids, regulate expression of murine hepatic anion transporters in endotoxemia., 303 (1): [PMID:12235261] [10.1124/jpet.102.039404]
5. Trauner M, Arrese M, Lee H, Boyer JL, Karpen SJ.. (1998) Endotoxin downregulates rat hepatic ntcp gene expression via decreased activity of critical transcription factors., 101 (1): [PMID:9593765] [10.1172/jci1680]
6. Unpublished dataset,

Endotoxin

Names and Identifiers

Alternative Forms

Associated Targets(non-human)

Molecule Features

Drug Indications

Mechanisms of Action

Calculated Properties

References

Source