glucuronidated SN-38

ID: ALA1743143

PubChem CID: 54580698

Max Phase: Preclinical

Molecular Formula: C29H30N2O11

Molecular Weight: 582.56

Molecule Type: Small molecule

This compound is available for customization.

Associated Items:

Bioactivity Summary Target Summary Assay Summary

Names and Identifiers

Synonyms: Glucuronidated Sn-38 | Glucuronidated Sn-38|CHEMBL1743143|BDBM50485569

Canonical SMILES: CCc1c2c(nc3ccc(OC[C@@H]4O[C@H](C(=O)O)[C@@H](O)[C@H](O)[C@H]4O)cc13)-c1cc3c(c(=O)n1C2)COC(=O)[C@]3(O)CC

Standard InChI: InChI=1S/C29H30N2O11/c1-3-13-14-7-12(40-11-20-22(32)23(33)24(34)25(42-20)27(36)37)5-6-18(14)30-21-15(13)9-31-19(21)8-17-16(26(31)35)10-41-28(38)29(17,39)4-2/h5-8,20,22-25,32-34,39H,3-4,9-11H2,1-2H3,(H,36,37)/t20-,22-,23+,24-,25-,29-/m0/s1

Standard InChI Key: TYRCRLNOGKXTCN-PUAAHTLNSA-N

Molfile:

     RDKit          2D

 42 47  0  0  0  0  0  0  0  0999 V2000
   14.4736  -24.6291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4724  -25.4565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1872  -25.8694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1854  -24.2164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9050  -24.6255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9059  -25.4527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6193  -25.8638    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.6136  -24.2110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3317  -24.6146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3392  -25.4458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1154  -24.3543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6094  -25.0166    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.1279  -25.6899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4274  -25.0939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7702  -25.8389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2945  -26.5118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6336  -27.2558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4535  -27.3368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9292  -26.6638    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.5891  -25.9141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9018  -24.4189    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.7938  -28.0859    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.0417  -27.9667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.8095  -27.2149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4335  -26.4811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3615  -27.9077    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6065  -23.3861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3174  -22.9674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7590  -24.2168    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.9621  -24.4303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5496  -25.1448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7246  -25.1448    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.3121  -25.8593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7246  -26.5738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5496  -26.5738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9621  -25.8593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4871  -25.8593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0746  -26.5738    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0746  -25.1448    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.3121  -27.2882    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.9621  -27.2882    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.7871  -25.8593    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 13 25  2  0
 25 16  1  0
  3  6  2  0
 15 14  1  0
 14 12  1  0
 15 16  2  0
  6  7  1  0
  7 10  2  0
  1  2  2  0
  9  8  2  0
  8  5  1  0
  9 10  1  0
 15 20  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
  5  4  2  0
 14 21  2  0
  4  1  1  0
 18 22  2  0
 17 23  1  1
 10 13  1  0
 17 24  1  0
 12 11  1  0
 11  9  1  0
 24 26  1  0
  2  3  1  0
  8 27  1  0
  5  6  1  0
 27 28  1  0
 12 13  1  0
  1 29  1  0
 29 30  1  0
 31 30  1  1
 31 32  1  0
 36 31  1  0
 32 33  1  0
 33 34  1  0
 34 35  1  0
 35 36  1  0
 33 37  1  1
 37 38  1  0
 37 39  2  0
 34 40  1  6
 35 41  1  1
 36 42  1  6
M  END

Associated Targets(Human)

ABCC2 Tchem Canalicular multispecific organic anion transporter 1 (1191 Activities)

Discover Target: ABCC2

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

SLCO1B1 Tchem Solute carrier organic anion transporter family member 1B1 (2672 Activities)

Discover Target: SLCO1B1

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

ABCG2 Tchem ATP-binding cassette sub-family G member 2 (4927 Activities)

Discover Target: ABCG2

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

Associated Targets(non-human)

Abcb1a P-glycoprotein 3 (492 Activities)

Discover Target: Abcb1a

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

Natural Product: No	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: No

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: 582.56	Molecular Weight (Monoisotopic): 582.1850	AlogP: -0.04	#Rotatable Bonds: 6
Polar Surface Area: 197.87	Molecular Species: ACID	HBA: 12	HBD: 5
#RO5 Violations: 2	HBA (Lipinski): 13	HBD (Lipinski): 5	#RO5 Violations (Lipinski): 2
CX Acidic pKa: 3.39	CX Basic pKa: 4.02	CX LogP: -1.28	CX LogD: -3.74
Aromatic Rings: 3	Heavy Atoms: 42	QED Weighted: 0.19	Np Likeness Score: 1.28

References

1. International Transporter Consortium, Giacomini KM, Huang SM, Tweedie DJ, Benet LZ, Brouwer KL, Chu X, Dahlin A, Evers R, Fischer V, Hillgren KM, Hoffmaster KA, Ishikawa T, Keppler D, Kim RB, Lee CA, Niemi M, Polli JW, Sugiyama Y, Swaan PW, Ware JA, Wright SH, Yee SW, Zamek-Gliszczynski MJ, Zhang L.. (2010) Membrane transporters in drug development., 9 (3): [PMID:20190787] [10.1038/nrd3028]
2. Arimori K, Kuroki N, Hidaka M, Iwakiri T, Yamsaki K, Okumura M, Ono H, Takamura N, Kikuchi M, Nakano M.. (2003) Effect of P-glycoprotein modulator, cyclosporin A, on the gastrointestinal excretion of irinotecan and its metabolite SN-38 in rats., 20 (1): [PMID:12817897] [10.1023/a:1023847521767]
3. Nozawa T, Minami H, Sugiura S, Tsuji A, Tamai I.. (2005) Role of organic anion transporter OATP1B1 (OATP-C) in hepatic uptake of irinotecan and its active metabolite, 7-ethyl-10-hydroxycamptothecin: in vitro evidence and effect of single nucleotide polymorphisms., 33 (1): [PMID:15608127] [10.1124/dmd.104.001909]
4. Nakatomi K, Yoshikawa M, Oka M, Ikegami Y, Hayasaka S, Sano K, Shiozawa K, Kawabata S, Soda H, Ishikawa T, Tanabe S, Kohno S.. (2001) Transport of 7-ethyl-10-hydroxycamptothecin (SN-38) by breast cancer resistance protein ABCG2 in human lung cancer cells., 288 (1): [PMID:11688982] [10.1006/bbrc.2001.5850]
5. Chu XY, Kato Y, Niinuma K, Sudo KI, Hakusui H, Sugiyama Y.. (1997) Multispecific organic anion transporter is responsible for the biliary excretion of the camptothecin derivative irinotecan and its metabolites in rats., 281 (1): [PMID:9103511]
6. Jedlitschky, G G and 5 more authors. 1997-10-01 ATP-dependent transport of bilirubin glucuronides by the multidrug resistance protein MRP1 and its hepatocyte canalicular isoform MRP2. [PMID:9355767]

glucuronidated SN-38

Names and Identifiers

Alternative Forms

Associated Targets(Human)

Associated Targets(non-human)

Molecule Features

Drug Indications

Mechanisms of Action

Biocomponents

Calculated Properties

References

Source