NPASS Natural Product

Natural Product: NPC469492

Natural Product ID:	NPC469492
Common Name:	Grenadamide B
IUPAC Name:	(5E)-5-(chloromethylidene)-N-(4,6-dimethyl-5-oxodec-9-en-2-yl)octanamide
Synonyms:
Molecular Formula:	C21H36ClNO2
Standard InCHIKey:	MTSIKQYOKFAJKC-XDJHFCHBSA-N
Standard InCHI:	InChI=1S/C21H36ClNO2/c1-6-8-11-16(3)21(25)17(4)14-18(5)23-20(24)13-9-12-19(15-22)10-7-2/h6,15-18H,1,7-14H2,2-5H3,(H,23,24)/b19-15+
Canonical SMILES:	CCC/C(=CCl)/CCCC(=NC(CC(C(=O)C(CCC=C)C)C)C)O
First Find Year:
Max Developmental Stage:
Synthetic Gene Cluster:	;

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria		Eastern Caribbean		PMID[19739598]

Biological Activity

Activity Type	# Activity
IC50	1
Others	1

Activity Type	# Activity
Cell Line	1
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2779	Organism	Spodoptera exigua	Spodoptera exigua	Activity	=	38	%	23623680
NPT71	Cell Line	HEK293	Homo sapiens	IC50	>=	100000	nM	18474583

Similar Natural Products in NPASS

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules. Tc lies between [0, 1] where '1' indicates the highest similarity. What is Tanimoto coefficient

● The left chart: Distribution of similarity level between NPC469492 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	32
0.1-0.2	337
0.2-0.3	10932
0.3-0.4	11891
0.4-0.5	6846
0.5-0.6	817
0.6-0.7	33
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9863	High Similarity	NPC469517
0.68	Remote Similarity	NPC210999
0.6796	Remote Similarity	NPC46764
0.6535	Remote Similarity	NPC474563
0.6484	Remote Similarity	NPC477199
0.6463	Remote Similarity	NPC474812
0.64	Remote Similarity	NPC233932
0.6354	Remote Similarity	NPC314500
0.6289	Remote Similarity	NPC472613
0.6286	Remote Similarity	NPC307903
0.6286	Remote Similarity	NPC140251
0.6264	Remote Similarity	NPC39966
0.625	Remote Similarity	NPC316674
0.6211	Remote Similarity	NPC316186
0.6196	Remote Similarity	NPC471595
0.619	Remote Similarity	NPC475800
0.617	Remote Similarity	NPC322672
0.6161	Remote Similarity	NPC323532
0.6154	Remote Similarity	NPC259476
0.6105	Remote Similarity	NPC473525
0.6105	Remote Similarity	NPC472614
0.6087	Remote Similarity	NPC16709
0.6087	Remote Similarity	NPC224072
0.6076	Remote Similarity	NPC329003
0.6076	Remote Similarity	NPC326524
0.6076	Remote Similarity	NPC325550
0.6075	Remote Similarity	NPC474725
0.6064	Remote Similarity	NPC319913
0.6061	Remote Similarity	NPC477290
0.6024	Remote Similarity	NPC187315
0.6023	Remote Similarity	NPC217095
0.6023	Remote Similarity	NPC264417
0.6	Remote Similarity	NPC103712
0.6	Remote Similarity	NPC291196
0.5981	Remote Similarity	NPC207820
0.5977	Remote Similarity	NPC43219
0.5962	Remote Similarity	NPC128501
0.5952	Remote Similarity	NPC470110
0.5952	Remote Similarity	NPC278895
0.5949	Remote Similarity	NPC321030
0.5941	Remote Similarity	NPC123141
0.5926	Remote Similarity	NPC473578
0.5909	Remote Similarity	NPC7797
0.5909	Remote Similarity	NPC86064
0.5905	Remote Similarity	NPC471317
0.59	Remote Similarity	NPC116930
0.5889	Remote Similarity	NPC316242
0.5876	Remote Similarity	NPC34754
0.5849	Remote Similarity	NPC119329
0.5833	Remote Similarity	NPC197089
0.5833	Remote Similarity	NPC475150
0.5833	Remote Similarity	NPC168733
0.5833	Remote Similarity	NPC171734
0.5833	Remote Similarity	NPC470109
0.5825	Remote Similarity	NPC234542
0.5824	Remote Similarity	NPC315535
0.5824	Remote Similarity	NPC474833
0.5824	Remote Similarity	NPC315131
0.5824	Remote Similarity	NPC478017
0.5818	Remote Similarity	NPC12270
0.5816	Remote Similarity	NPC39290
0.5816	Remote Similarity	NPC159369
0.5814	Remote Similarity	NPC469914
0.5812	Remote Similarity	NPC280498
0.5804	Remote Similarity	NPC471645
0.5802	Remote Similarity	NPC6795
0.5802	Remote Similarity	NPC40206
0.5794	Remote Similarity	NPC271269
0.5794	Remote Similarity	NPC154601
0.5794	Remote Similarity	NPC472615
0.5784	Remote Similarity	NPC476449
0.5773	Remote Similarity	NPC324506
0.5769	Remote Similarity	NPC473224
0.5766	Remote Similarity	NPC469865
0.5765	Remote Similarity	NPC195165
0.5763	Remote Similarity	NPC204639
0.5761	Remote Similarity	NPC471597
0.5755	Remote Similarity	NPC202613
0.5755	Remote Similarity	NPC476877
0.5752	Remote Similarity	NPC471318
0.575	Remote Similarity	NPC325734
0.5747	Remote Similarity	NPC477200
0.5745	Remote Similarity	NPC474312
0.5745	Remote Similarity	NPC473810
0.5741	Remote Similarity	NPC251330
0.5732	Remote Similarity	NPC21848
0.5732	Remote Similarity	NPC124849
0.5732	Remote Similarity	NPC125312
0.5732	Remote Similarity	NPC174560
0.573	Remote Similarity	NPC288086
0.573	Remote Similarity	NPC469835
0.5728	Remote Similarity	NPC4834
0.5727	Remote Similarity	NPC92829
0.5714	Remote Similarity	NPC470108
0.5702	Remote Similarity	NPC188010
0.5702	Remote Similarity	NPC216335
0.5701	Remote Similarity	NPC472616
0.5698	Remote Similarity	NPC476614
0.5664	Remote Similarity	NPC50694
0.5664	Remote Similarity	NPC476813
0.5664	Remote Similarity	NPC476814
0.566	Remote Similarity	NPC152718
0.566	Remote Similarity	NPC226509
0.566	Remote Similarity	NPC469598
0.5657	Remote Similarity	NPC249312
0.5648	Remote Similarity	NPC476876
0.5645	Remote Similarity	NPC78189
0.5636	Remote Similarity	NPC329305
0.5632	Remote Similarity	NPC478256
0.5631	Remote Similarity	NPC25565
0.5631	Remote Similarity	NPC475503
0.5625	Remote Similarity	NPC227051
0.5619	Remote Similarity	NPC275686
0.561	Remote Similarity	NPC96425
0.56	Remote Similarity	NPC474964
0.56	Remote Similarity	NPC477288
0.56	Remote Similarity	NPC17143
0.56	Remote Similarity	NPC47230

Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

● The left chart: Distribution of similarity level between NPC469492 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	52
0.1-0.2	275
0.2-0.3	3628
0.3-0.4	3920
0.4-0.5	1157
0.5-0.6	128
0.6-0.7	1
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.6289	Remote Similarity	NPD5781	Clinical (unspecified phase)
0.5872	Remote Similarity	NPD6420	Discontinued
0.5833	Remote Similarity	NPD7331	Phase 2
0.5824	Remote Similarity	NPD7917	Clinical (unspecified phase)
0.5824	Remote Similarity	NPD7918	Clinical (unspecified phase)
0.5818	Remote Similarity	NPD1719	Phase 1
0.5806	Remote Similarity	NPD857	Phase 3
0.578	Remote Similarity	NPD6413	Approved
0.5743	Remote Similarity	NPD5769	Clinical (unspecified phase)
0.5732	Remote Similarity	NPD835	Approved
0.5732	Remote Similarity	NPD834	Approved
0.5676	Remote Similarity	NPD3643	Approved
0.5676	Remote Similarity	NPD3642	Approved
0.5676	Remote Similarity	NPD3644	Approved
0.5652	Remote Similarity	NPD3732	Approved
0.5632	Remote Similarity	NPD1082	Approved
0.5632	Remote Similarity	NPD791	Approved
0.5632	Remote Similarity	NPD15	Approved
0.5631	Remote Similarity	NPD4228	Discovery

Structure

NPC469492 OpenBabel07101719522D 25 24 0 0 1 0 0 0 0 0999 V2000 3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.6603 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -6.9282 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.6603 3.0000 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 1.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 6 2 0 0 0 0 2 7 1 0 0 0 0 3 16 1 0 0 0 0 4 17 1 0 0 0 0 5 18 1 0 0 0 0 6 8 1 0 0 0 0 7 10 1 0 0 0 0 8 11 1 0 0 0 0 9 12 1 0 0 0 0 9 13 1 0 0 0 0 10 19 1 0 0 0 0 11 16 1 0 0 0 0 12 19 1 0 0 0 0 13 20 1 0 0 0 0 14 17 1 0 0 0 0 14 18 1 0 0 0 0 15 19 2 0 0 0 0 15 22 1 0 0 0 0 16 21 1 0 0 0 0 17 21 1 0 0 0 0 18 23 1 0 0 0 0 20 23 2 3 0 0 0 20 24 1 0 0 0 0 21 25 2 0 0 0 0 M END $$$$

External Identifiers

PubChem CID	44479217
ChEMBL	CHEMBL1080777
ZINC

Physicochemical Properties

Molecular Weight:	369.24
ALogP:	1.8089
MLogP:	3.33
XLogP:	5.551
# Rotatable Bonds:	20
Polar Surface Area:	49.66
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	0
# Heavy Atoms:	25

Download Data

Data Type	Select
General Info & Identifiers & Properties
Structure MOL file
Source Organisms
Biological Activities
Similar NPs/Drugs