Compound Information

General Information of the Compound

Compound ID

CP0041451

Compound Name

CAS_75921-69-6

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Synonyms

Afamelanotide

NDP-MSH

NDP-alpha-MSH

[Nle4,dPhe7]alpha-MSH

alpha-NDP-MSH

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Structure

Formula

C78H111N21O19

Molecular Weight

1646.874

Canonical SMILES

CCCC[C@H](NC(=O)[C@H](CO)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@H](CO)NC(C)=O)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](Cc1cnc[nH]1)C(=O)N[C@H](Cc1ccccc1)C(=O)N[C@@H](CCCN=C(N)N)C(=O)N[C@@H](Cc1c[nH]c2ccccc12)C(=O)NCC(=O)N[C@@H](CCCCN)C(=O)N1CCC[C@H]1C(=O)N[C@@H](C(C)C)C(N)=O

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InChI

InChI=1S/C78H111N21O19/c1-5-6-19-52(91-75(116)61(41-101)97-72(113)57(34-46-24-26-49(103)27-25-46)94-74(115)60(40-100)88-44(4)102)68(109)92-54(28-29-64(105)106)70(111)96-59(36-48-38-83-42-87-48)73(114)93-56(33-45-16-8-7-9-17-45)71(112)90-53(22-14-31-84-78(81)82)69(110)95-58(35-47-37-85-51-20-11-10-18-50(47)51)67(108)86-39-63(104)89-55(21-12-13-30-79)77(118)99-32-15-23-62(99)76(117)98-65(43(2)3)66(80)107/h7-11,16-18,20,24-27,37-38,42-43,52-62,65,85,100-101,103H,5-6,12-15,19,21-23,28-36,39-41,79H2,1-4H3,(H2,80,107)(H,83,87)(H,86,108)(H,88,102)(H,89,104)(H,90,112)(H,91,116)(H,92,109)(H,93,114)(H,94,115)(H,95,110)(H,96,111)(H,97,113)(H,98,117)(H,105,106)(H4,81,82,84)/t52-,53-,54-,55-,56+,57-,58-,59-,60-,61-,62-,65-/m0/s1

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InChIKey

UAHFGYDRQSXQEB-LEBBXHLNSA-N

CAS

75921-69-6

Physicochemical Property

logP	-4.3094
Rotatable Bonds	50
Heavy Atom Count	118
Polar Areas	645.48
Hydrogen Bond Donor Count	22
Hydrogen Bond Acceptor Count	21
Complexity	118

"RO5" indicates the cutoff set by lipinski's rule of five:

(1) Molecular weight less than 500 Dalton;

(2) xlogp less than 5;

(3) No more than 5 hbonddonor (Hydrogen Bond Donor Count);

(4) No more than 10 hbondacc (Hydrogen Bond Acceptor Count);

(5) No more than 10 rotbonds (Rotatable Bond Count).

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PubChem ID

CID: 91898441

SID: 16544557

ChEMBL ID

CHEMBL441738

DrugBank ID

DB04931

Map of Molecular Bioactivity Related to the Compound

Map of Molecular Bioactivity Related to the Compound Compound Cell Line Protein Bioactivity Value: <= 0.1 μM > 0.1 μM and <= 10 μM > 10 μM Imprecise Activity

Table of Molecular Bioactivities Related to the Compound

Protein ID: PT02450, Melanocortin receptor 3

Protein Info

Cell-based Assay

Cell Line ID	Cell Line Name	Cell Line Organism
CL000006	HEK293 Cell Line Info	Homo sapiens (Human)	18
1	EC50 = 0.063 nM Bioactivity Info	TI LI LO TS
2	EC50 = 0.07 nM Bioactivity Info	TI LI LO TS
3	EC50 = 0.074 nM Bioactivity Info	TI LI LO TS
4	EC50 = 0.085 nM Bioactivity Info	TI LI LO TS
5	EC50 = 0.09 nM Bioactivity Info	TI LI LO TS
6	EC50 = 0.098 nM Bioactivity Info	TI LI LO TS
7	EC50 = 0.14 nM Bioactivity Info	TI LI LO TS
8	EC50 = 0.19 nM Bioactivity Info	TI LI LO TS
9	EC50 = 0.23 nM Bioactivity Info	TI LI LO TS
10	EC50 = 0.24 nM Bioactivity Info	TI LI LO TS
11	EC50 = 0.33 nM Bioactivity Info	TI LI LO TS
12	EC50 = 0.36 nM Bioactivity Info	TI LI LO TS
13	EC50 = 0.414 nM Bioactivity Info	TI LI LO TS
14	EC50 = 0.81 nM Bioactivity Info	TI LI LO TS
15	EC50 = 75 nM Bioactivity Info	TI LI LO TS
16	IC50 = 4.18 nM Bioactivity Info	TI LI LO TS
17	IC50 = 5.3 nM Bioactivity Info	TI LI LO TS
18	IC50 = 8.2 nM Bioactivity Info	TI LI LO TS

Biochemical Assays

1	EC50 = 0.089 nM
2	EC50 = 0.098 nM

Protein ID: PT01325, Melanocortin receptor 3

Protein Info

Cell-based Assay

Cell Line ID	Cell Line Name	Cell Line Organism
CL000006	HEK293 Cell Line Info	Homo sapiens (Human)	5
1	EC50 = 0.3 nM Bioactivity Info	TI LI LO TS
2	EC50 = 0.36 nM Bioactivity Info	TI LI LO TS
3	EC50 = 0.8 nM Bioactivity Info	TI LI LO TS
4	EC50 = 6.8 nM Bioactivity Info	TI LI LO TS
5	IC50 = 3.3 nM Bioactivity Info	TI LI LO TS
CL000309	NCTC clone 929 Cell Line Info	Mus musculus (Mouse)	2
1	EC50 = 4.1 nM Bioactivity Info	TI LI LO TS
2	IC50 = 2.9 nM Bioactivity Info	TI LI LO TS
CL000404	BHK570 Cell Line Info	Mesocricetus auratus (Golden hamster)	1
1	Ki = 0.78 nM Bioactivity Info	TI LI LO TS

Biochemical Assays

1	EC50 = 0.13 nM
2	IC50 = 1.17 nM
3	IC50 = 3.3 nM
4	IC50 = 3.8 nM
5	Ki = 0.68 nM

Protein ID: PT01431, Melanocortin receptor 4

Protein Info

Cell-based Assay

Cell Line ID	Cell Line Name	Cell Line Organism
CL000006	HEK293 Cell Line Info	Homo sapiens (Human)	17
1	EC50 = 0.097 nM Bioactivity Info	TI LI LO TS
2	EC50 = 0.12 nM Bioactivity Info	TI LI LO TS
3	EC50 = 0.13 nM Bioactivity Info	TI LI LO TS
4	EC50 = 0.2 nM Bioactivity Info	TI LI LO TS
5	EC50 = 0.21 nM Bioactivity Info	TI LI LO TS
6	EC50 = 0.279 nM Bioactivity Info	TI LI LO TS
7	EC50 = 0.3 nM Bioactivity Info	TI LI LO TS
8	EC50 = 0.39 nM Bioactivity Info	TI LI LO TS
9	EC50 = 0.41 nM Bioactivity Info	TI LI LO TS
10	EC50 = 0.46 nM Bioactivity Info	TI LI LO TS
11	EC50 = 0.8 nM Bioactivity Info	TI LI LO TS
12	EC50 = 0.87 nM Bioactivity Info	TI LI LO TS
13	EC50 = 0.9 nM Bioactivity Info	TI LI LO TS
14	EC50 = 1.1 nM Bioactivity Info	TI LI LO TS
15	IC50 = 1.09 nM Bioactivity Info	TI LI LO TS
16	IC50 = 1.3 nM Bioactivity Info	TI LI LO TS
17	IC50 = 2 nM Bioactivity Info	TI LI LO TS

Biochemical Assays

1	EC50 = 0.16 nM
2	EC50 = 0.21 nM
3	IC50 = 4.22 nM

Protein ID: PT00914, Melanocortin receptor 4

Protein Info

Cell-based Assay

Cell Line ID	Cell Line Name	Cell Line Organism
CL000006	HEK293 Cell Line Info	Homo sapiens (Human)	26
1	EC50 = 0.13 nM Bioactivity Info	TI LI LO TS
2	EC50 = 0.2 nM Bioactivity Info	TI LI LO TS
3	EC50 = 0.4 nM Bioactivity Info	TI LI LO TS
4	EC50 = 0.51 nM Bioactivity Info	TI LI LO TS
5	EC50 = 1 nM Bioactivity Info	TI LI LO TS
6	EC50 = 1.1 nM Bioactivity Info	TI LI LO TS
7	EC50 = 1.2 nM Bioactivity Info	TI LI LO TS
8	EC50 = 1.4 nM Bioactivity Info	TI LI LO TS
9	EC50 = 1.5 nM Bioactivity Info	TI LI LO TS
10	EC50 = 2 nM Bioactivity Info	TI LI LO TS
11	EC50 = 5.1 nM Bioactivity Info	TI LI LO TS
12	EC50 = 6.4 nM Bioactivity Info	TI LI LO TS
13	EC50 = 9 nM Bioactivity Info	TI LI LO TS
14	IC50 = 0.4 nM Bioactivity Info	TI LI LO TS
15	IC50 = 9 nM Bioactivity Info	TI LI LO TS
16	IC50 = 10 nM Bioactivity Info	TI LI LO TS
17	IC50 = 14 nM Bioactivity Info	TI LI LO TS
18	Ki = 0.56 nM Bioactivity Info	TI LI LO TS
19	Ki = 0.57 nM Bioactivity Info	TI LI LO TS
20	Ki = 0.63 nM Bioactivity Info	TI LI LO TS
21	Ki = 0.82 nM Bioactivity Info	TI LI LO TS
22	Ki = 0.97 nM Bioactivity Info	TI LI LO TS
23	Ki = 1.2 nM Bioactivity Info	TI LI LO TS
24	Ki = 1.3 nM Bioactivity Info	TI LI LO TS
25	Ki = 9 nM Bioactivity Info	TI LI LO TS
26	Ki = 19 nM Bioactivity Info	TI LI LO TS
CL000404	BHK570 Cell Line Info	Mesocricetus auratus (Golden hamster)	1
1	EC50 = 0.14 nM Bioactivity Info	TI LI LO TS
CL000309	NCTC clone 929 Cell Line Info	Mus musculus (Mouse)	2
1	EC50 = 0.72 nM Bioactivity Info	TI LI LO TS
2	IC50 = 3.3 nM Bioactivity Info	TI LI LO TS
CL000011	CHO Cell Line Info	Cricetulus griseus (Chinese hamster)	1
1	IC50 = 0.15 nM Bioactivity Info	TI LI LO TS

Biochemical Assays

1	EC50 = 0.017 nM
2	IC50 = 0.2 nM
3	IC50 = 0.4 nM
4	IC50 = 0.48 nM
5	IC50 = 0.52 nM
6	IC50 = 1.16 nM
7	IC50 = 3.6 nM
8	Ki = 0.3 nM
9	Ki = 0.44 nM
10	Ki = 0.47 nM
11	Ki = 0.95 nM

Protein ID: PT01528, Melanocortin receptor 5

Protein Info

Cell-based Assay

Cell Line ID	Cell Line Name	Cell Line Organism
CL000006	HEK293 Cell Line Info	Homo sapiens (Human)	18
1	EC50 = 0.03 nM Bioactivity Info	TI LI LO TS
2	EC50 = 0.062 nM Bioactivity Info	TI LI LO TS
3	EC50 = 0.071 nM Bioactivity Info	TI LI LO TS
4	EC50 = 0.078 nM Bioactivity Info	TI LI LO TS
5	EC50 = 0.08 nM Bioactivity Info	TI LI LO TS
6	EC50 = 0.11 nM Bioactivity Info	TI LI LO TS
7	EC50 = 0.13 nM Bioactivity Info	TI LI LO TS
8	EC50 = 0.14 nM Bioactivity Info	TI LI LO TS
9	EC50 = 0.18 nM Bioactivity Info	TI LI LO TS
10	EC50 = 0.21 nM Bioactivity Info	TI LI LO TS
11	EC50 = 0.26 nM Bioactivity Info	TI LI LO TS
12	EC50 = 0.28 nM Bioactivity Info	TI LI LO TS
13	EC50 = 0.3 nM Bioactivity Info	TI LI LO TS
14	EC50 = 0.31 nM Bioactivity Info	TI LI LO TS
15	EC50 = 0.41 nM Bioactivity Info	TI LI LO TS
16	EC50 = 1.98 nM Bioactivity Info	TI LI LO TS
17	EC50 = 2.6 nM Bioactivity Info	TI LI LO TS
18	IC50 = 140 nM Bioactivity Info	TI LI LO TS

Biochemical Assays

1	EC50 = 0.071 nM
2	EC50 = 0.095 nM

Protein ID: PT01804, Melanocortin receptor 5

Protein Info

Cell-based Assay

Cell Line ID	Cell Line Name	Cell Line Organism
CL000006	HEK293 Cell Line Info	Homo sapiens (Human)	5
1	EC50 = 0.4 nM Bioactivity Info	TI LI LO TS
2	EC50 = 1 nM Bioactivity Info	TI LI LO TS
3	EC50 = 1.1 nM Bioactivity Info	TI LI LO TS
4	IC50 = 2.2 nM Bioactivity Info	TI LI LO TS
5	Ki = 9.9 nM Bioactivity Info	TI LI LO TS
CL000309	NCTC clone 929 Cell Line Info	Mus musculus (Mouse)	2
1	EC50 = 0.58 nM Bioactivity Info	TI LI LO TS
2	IC50 = 0.89 nM Bioactivity Info	TI LI LO TS
CL000404	BHK570 Cell Line Info	Mesocricetus auratus (Golden hamster)	1
1	Ki = 0.48 nM Bioactivity Info	TI LI LO TS

Biochemical Assays

1	IC50 = 0.86 nM
2	IC50 = 2.2 nM

Protein ID: PT01440, Melanocyte-stimulating hormone receptor

Protein Info

Cell-based Assay

Cell Line ID	Cell Line Name	Cell Line Organism
CL000006	HEK293 Cell Line Info	Homo sapiens (Human)	17
1	EC50 = 0.01 nM Bioactivity Info	TI LI LO TS
2	EC50 = 0.012 nM Bioactivity Info	TI LI LO TS
3	EC50 = 0.015 nM Bioactivity Info	TI LI LO TS
4	EC50 = 0.018 nM Bioactivity Info	TI LI LO TS
5	EC50 = 0.02 nM Bioactivity Info	TI LI LO TS
6	EC50 = 0.021 nM Bioactivity Info	TI LI LO TS
7	EC50 = 0.023 nM Bioactivity Info	TI LI LO TS
8	EC50 = 0.03 nM Bioactivity Info	TI LI LO TS
9	EC50 = 0.038 nM Bioactivity Info	TI LI LO TS
10	EC50 = 0.04 nM Bioactivity Info	TI LI LO TS
11	EC50 = 0.05 nM Bioactivity Info	TI LI LO TS
12	EC50 = 0.051 nM Bioactivity Info	TI LI LO TS
13	EC50 = 0.088 nM Bioactivity Info	TI LI LO TS
14	EC50 = 0.09 nM Bioactivity Info	TI LI LO TS
15	EC50 = 0.092 nM Bioactivity Info	TI LI LO TS
16	IC50 = 0.29 nM Bioactivity Info	TI LI LO TS
17	IC50 = 0.31 nM Bioactivity Info	TI LI LO TS

Biochemical Assays

1	EC50 = 0.018 nM
2	EC50 = 0.038 nM

Protein ID: PT00911, Melanocyte-stimulating hormone receptor

Protein Info

Cell-based Assay

Cell Line ID	Cell Line Name	Cell Line Organism
CL000006	HEK293 Cell Line Info	Homo sapiens (Human)	1
1	EC50 = 0.07 nM Bioactivity Info	TI LI LO TS
CL000309	NCTC clone 929 Cell Line Info	Mus musculus (Mouse)	1
1	EC50 = 0.19 nM Bioactivity Info	TI LI LO TS
CL000404	BHK570 Cell Line Info	Mesocricetus auratus (Golden hamster)	1
1	Ki = 0.046 nM Bioactivity Info	TI LI LO TS
CL000067	HCT 116 Cell Line Info	Homo sapiens (Human)	1
1	Ki = 1.8 nM Bioactivity Info	TI LI LO TS

Biochemical Assays

1	EC50 = 0.023 nM
2	IC50 = 0.51 nM
3	Ki = 0.5 nM

Clinical Information about the Compound

Drug 1 ( NDP-alpha-MSH )

Drug Name	NDP-alpha-MSH
Target(s)	Melanocortin receptor 4 (MC4R) Target Info Inhibitor

Drug 2 ( Afamelanotide )

Drug Name	Afamelanotide
Indication	Erythropoietic porphyrias Approved Vitiligo Phase 2
Target(s)	Melanocortin receptor 1 (MC1R) Target Info Modulator

Cite

About MolBiC

Correspondence

Prof. Feng ZHU

Prof. Leo, Lianyi Han