Compound Detail

CHEMBL118218

IROFULVEN

🧪 Phase III

Enter ChEMBL ID:

Free Research Context This compound will appear in recent viewed items on the research home for this browser.

Research home View demo workspace

🧪 Phase III

CC1=C(CO)C2=C(C)C3(CC3)[C@@](C)(O)C(=O)C2=C1

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL118218
Name	IROFULVEN
Phase	Phase III
Structure Type	MOL
InChI Key	NICJCIQSJJKZAH-AWEZNQCLSA-N

Known Names

(hydroxymethyl)acylfulvene 6-hydroxymethylacylfulvene Irofulven Irofulvene Irofulveno LP-100 MGI 114 MGI-114 MGI114 NSC-683863

Targets

Activities

Assay Types

PK Parameters

Publications

Known Names

Indications

Mechanisms

Molecular Properties

246.3

MW (Da)

1.67

ALogP

HBA

HBD

57.5

PSA (Å²)

0.74

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Small molecule
Chirality	Single Enantiomer

Flags

Natural Product

USAN Stem	-fulven
USAN Year	1998

Extended Properties

Molecular Formula	C15H18O3
MW	246.31
Aromatic Rings	0
Heavy Atoms	18
NP-Likeness	3.07

Mechanism of Action

Mechanism	Action Type	Target	Direct	Efficacy
DNA inhibitor	INHIBITOR	DNA	✓	✓

Indications

Pancreatic Neoplasms Breast Neoplasms Colorectal Neoplasms Endometrial Neoplasms Fallopian Tube Neoplasms Kidney Neoplasms Lung Neoplasms Melanoma Ovarian Neoplasms Peritoneal Neoplasms Prostatic Neoplasms, Castration-Resistant Stomach Neoplasms Thyroid Neoplasms Uterine Cervical Neoplasms Central Nervous System Neoplasms Leukemia Liver Neoplasms Myelodysplastic Syndromes Neoplasms

Activity Summary

IC50 63 meas. best 8.4

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
ADMET CHEMBL612558	IC50	8.4	7.3533	4.0	3
NON-PROTEIN TARGET CHEMBL3879801	IC50	7.3	6.6894	50.1	33
NCI-H460 CHEMBL396	IC50	7.3	7.3	50.1	1
Prostaglandin reductase 1 CHEMBL4166	IC50	7.26	7.26	55.0	1
HL-60 CHEMBL383	IC50	7.14	7.14	73.0	2
NCI-H23 CHEMBL614997	IC50	7.1	7.1	79.4	1
A549 CHEMBL392	IC50	6.9	6.9	125.9	1
SK-MEL-5 CHEMBL614922	IC50	6.8	6.8	158.5	1
NCI-H522 CHEMBL614387	IC50	6.8	6.8	158.5	1
NCI-H226 CHEMBL614740	IC50	6.7	6.7	199.5	1
A498 CHEMBL614516	IC50	6.7	6.7	199.5	1
EKVX CHEMBL614487	IC50	6.7	6.7	199.5	1
T47D CHEMBL614361	IC50	6.7	6.7	199.5	1
SK-MEL-2 CHEMBL614917	IC50	6.7	6.7	199.5	1
Malme-3M CHEMBL614021	IC50	6.7	6.7	199.5	1
786-0 CHEMBL613102	IC50	6.7	6.7	199.5	1
NCI-H322M CHEMBL614803	IC50	6.6	6.6	251.2	1
HT-29 CHEMBL384	IC50	6.6	6.6	251.2	1
ACHN CHEMBL614519	IC50	6.6	6.6	251.2	1
M14 CHEMBL614317	IC50	6.6	6.6	251.2	1
MCF7 CHEMBL387	IC50	6.6	6.6	251.2	1
MDA-MB-231 CHEMBL400	IC50	6.5	6.5	316.2	1
U-251 CHEMBL615022	IC50	6.5	6.5	316.2	1
SN12C CHEMBL614054	IC50	6.4	6.4	398.1	1
KM12 CHEMBL614709	IC50	6.2	6.2	631.0	1
SK-MEL-28 CHEMBL614919	IC50	6.2	6.2	631.0	1
HEK293 CHEMBL614818	IC50	5.92	5.92	1200.0	1
MDA-MB-435 CHEMBL614697	IC50	5.8	5.8	1584.9	1

Pharmacokinetic Data

Parameter	Value	Units	Species
CL	140.0	mL.min-1.kg-1	Homo sapiens
MRT	0.4	hr	Homo sapiens
T1/2	0.3	hr	Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
ADMET	IC50	=	4.0	nM	8.4	Concentration required for 50% toxicity in metastatic lung carcinoma (MV522) cel...	11000013
NCI-H460	IC50	=	50.12	nM	7.3	Cytotoxicity against human NCI-H460 cells after 48 hrs by sulforhodamine B assay	26922141
NON-PROTEIN TARGET	IC50	=	50.12	nM	7.3	Cytotoxicity against human RXF393 cells after 48 hrs by sulforhodamine B assay	26922141
Prostaglandin reductase 1	IC50	=	55.0	nM	7.26	Cytotoxicity against HEK293 cells transfected with recombinant AOR by MTT assay	16610802
NON-PROTEIN TARGET	IC50	=	70.0	nM	7.16	Antitumor activity in MV522 cells assessed as cell survival after 48 hrs	17977722
NON-PROTEIN TARGET	IC50	=	70.0	nM	7.16	Cytotoxicity against human MV522 cells after 48 hrs by trypan blue exclusion ass...	26922141
HL-60	IC50	=	73.0	nM	7.14	Cytotoxicity against human HL60 cells after 48 hrs by trypan blue exclusion meth...	8864242
HL-60	IC50	=	73.0	nM	7.14	Cytotoxicity against human HL60 cells after 48 hrs by trypan blue exclusion assa...	12608875
ADMET	IC50	=	76.0	nM	7.12	Cytotoxicity against human 8392B cells after 48 hrs by trypan blue exclusion ass...	20067264
NCI-H23	IC50	=	79.43	nM	7.1	Cytotoxicity against human NCI-H23 cells after 48 hrs by sulforhodamine B assay	26922141
NON-PROTEIN TARGET	IC50	=	100.0	nM	7.0	Cytotoxicity against human DU145 cells after 48 hrs by sulforhodamine B assay	26922141
NON-PROTEIN TARGET	IC50	=	110.0	nM	6.96	Antitumor activity in MV522 cells assessed as inhibition of DNA synthesis after ...	17977722
A549	IC50	=	125.89	nM	6.9	Cytotoxicity against human A549 cells after 48 hrs by sulforhodamine B assay	26922141
NON-PROTEIN TARGET	IC50	=	158.49	nM	6.8	Cytotoxicity against human HOP62 cells after 48 hrs by sulforhodamine B assay	26922141
NON-PROTEIN TARGET	IC50	=	158.49	nM	6.8	Cytotoxicity against human OVCAR5 cells after 48 hrs by sulforhodamine B assay	26922141
NON-PROTEIN TARGET	IC50	=	158.49	nM	6.8	Cytotoxicity against human IGROV1 cells after 48 hrs by sulforhodamine B assay	26922141
SK-MEL-5	IC50	=	158.49	nM	6.8	Cytotoxicity against human SK-MEL-5 cells after 48 hrs by sulforhodamine B assay	26922141
NON-PROTEIN TARGET	IC50	=	158.49	nM	6.8	Cytotoxicity against human HCC2998 cells after 48 hrs by sulforhodamine B assay	26922141
NON-PROTEIN TARGET	IC50	=	158.49	nM	6.8	Cytotoxicity against human SF539 cells after 48 hrs by sulforhodamine B assay	26922141
NCI-H522	IC50	=	158.49	nM	6.8	Cytotoxicity against human NCI-H522 cells after 48 hrs by sulforhodamine B assay	26922141

Literature References

PubMed	DOI	Target Context	# Activities
26922141	10.1016/j.bmcl.2016.02.028	NON-PROTEIN TARGET	31
18426954	10.1124/dmd.108.020479	ADMET	4
16610802	10.1021/jm051104t	Prostaglandin reductase 1	2
17977722	10.1016/j.bmcl.2007.10.040	NON-PROTEIN TARGET	2
8864242	10.1021/np960450y	NON-PROTEIN TARGET	2
20067264	10.1021/jm901384s	NON-PROTEIN TARGET	1
26922141	10.1016/j.bmcl.2016.02.028	Unchecked	1
26922141	10.1016/j.bmcl.2016.02.028	NCI-H460	1
26922141	10.1016/j.bmcl.2016.02.028	NCI-H322M	1
26922141	10.1016/j.bmcl.2016.02.028	NCI-H23	1
26922141	10.1016/j.bmcl.2016.02.028	NCI-H226	1
26922141	10.1016/j.bmcl.2016.02.028	EKVX	1
26922141	10.1016/j.bmcl.2016.02.028	A549	1
20067264	10.1021/jm901384s	Unchecked	1
11000013	10.1021/jm0000315	ADMET	1
20067264	10.1021/jm901384s	ADMET	1
12608875	10.1021/np0204085	HL-60	1
18715789	10.1016/j.bmc.2008.08.015	MDA-MB-231	1
18715789	10.1016/j.bmc.2008.08.015	MCF7	1
8864242	10.1021/np960450y	HL-60	1

Data from ChEMBL 36 via Core Engine