NPASS Natural Product

Natural Product: NPC311369

Natural Product ID:	NPC311369
Common Name:	Curacin A
IUPAC Name:	(4R)-4-[(1Z,5E,7E,11R)-11-methoxy-8-methyltetradeca-1,5,7,13-tetraenyl]-2-[(1R,2S)-2-methylcyclopropyl]-4,5-dihydro-1,3-thiazole
Synonyms:	Curacin A
Molecular Formula:	C23H35NOS
Standard InCHIKey:	LUEYTMPPCOCKBX-KWYHTCOPSA-N
Standard InCHI:	InChI=1S/C23H35NOS/c1-5-11-21(25-4)15-14-18(2)12-9-7-6-8-10-13-20-17-26-23(24-20)22-16-19(22)3/h5,7,9-10,12-13,19-22H,1,6,8,11,14-17H2,2-4H3/b9-7+,13-10-,18-12+/t19-,20+,21-,22+/m0/s1
Canonical SMILES:	C=CC[C@@H](CC/C(=C/C=C/CC/C=C[C@@H]1CSC(=N1)[C@@H]1C[C@@H]1C)/C)OC
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		Caribbean		PMID[8699186]

Biological Activity

Activity Type	# Activity
EC50	1
GI50	4
IC50	7
LD50	1
Others	5

Activity Type	# Activity
Cell Line	10
Individual Protein	2
Organism	2
Others	3
Protein Complex	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT176	Organism	Artemia salina	Artemia salina	LC50	=	0.0025	ug/ml	19391605
NPT140	Organism	Artemia	Artemia	LD50	=	8	nM	19193025
NPT1719	Cell Line	2008	Homo sapiens	GI50	=	35	nM	Open TG-GATES in vivo data: Organ Weight
NPT82	Cell Line	MDA-MB-231	Homo sapiens	GI50	=	96	nM	Open TG-GATES in vivo data: Organ Weight
NPT179	Cell Line	A2780	Homo sapiens	Inhibition	=	78	%	Open TG-GATES in vivo data: Organ Weight
NPT306	Cell Line	PC-3	Homo sapiens	GI50	=	50	nM	Open TG-GATES in vivo data: Organ Weight
NPT83	Cell Line	MCF7	Homo sapiens	GI50	=	40	nM	Open TG-GATES in vivo data: Organ Weight
NPT518	Protein Complex	Tubulin	Homo sapiens	IC50	=	720	nM	Open TG-GATES in vivo data: Organ Weight
NPT1396	Cell Line	NCI-H69	Homo sapiens	IC50	=	0.89	ug/ml	16570920
NPT179	Cell Line	A2780	Homo sapiens	Inhibition	=	94	%	8691203
NPT781	Individual Protein	Tubulin alpha chain	Sus scrofa	IC50	=	2500	nM	20020916
NPT2	Others	Unspecified		EC50	=	510	nM	17993275
NPT76	Cell Line	C6	Rattus norvegicus	LC50	=	11	nM	16792412
NPT3377	Cell Line	PC-9		IC50	=	19.6	ug/ml	25710081
NPT1183	Cell Line	WiDr	Homo sapiens	IC50	<	0.2	ug/ml	25710081
NPT781	Individual Protein	Tubulin alpha chain	Sus scrofa	IC50	=	2500	nM	25710081
NPT2	Others	Unspecified		IC50	=	1400	nM	26425784
NPT2	Others	Unspecified		Inhibition	=	96	%	19056262

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 NPC311369 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	47
0.1-0.2	549
0.2-0.3	17711
0.3-0.4	10886
0.4-0.5	1575
0.5-0.6	115
0.6-0.7	6
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	Natural Product ID
0.6224	Remote Similarity	NPC319473
0.6058	Remote Similarity	NPC474873
0.6023	Remote Similarity	NPC314678
0.6019	Remote Similarity	NPC471636
0.6019	Remote Similarity	NPC287572
0.6019	Remote Similarity	NPC132931
0.5963	Remote Similarity	NPC474891
0.5882	Remote Similarity	NPC129995
0.5882	Remote Similarity	NPC315141
0.5877	Remote Similarity	NPC201968
0.5872	Remote Similarity	NPC474969
0.5872	Remote Similarity	NPC476034
0.5849	Remote Similarity	NPC72401
0.5849	Remote Similarity	NPC325339
0.5841	Remote Similarity	NPC50694
0.5833	Remote Similarity	NPC477199
0.5833	Remote Similarity	NPC101106
0.5833	Remote Similarity	NPC135216
0.5804	Remote Similarity	NPC279383
0.5804	Remote Similarity	NPC273215
0.5804	Remote Similarity	NPC268327
0.5804	Remote Similarity	NPC295444
0.5789	Remote Similarity	NPC477554
0.578	Remote Similarity	NPC250187
0.5765	Remote Similarity	NPC477525
0.5758	Remote Similarity	NPC316186
0.5752	Remote Similarity	NPC475988
0.5739	Remote Similarity	NPC477553
0.569	Remote Similarity	NPC477555
0.5682	Remote Similarity	NPC291196
0.5682	Remote Similarity	NPC103712
0.5625	Remote Similarity	NPC242930
0.5625	Remote Similarity	NPC297020
0.5625	Remote Similarity	NPC127578
0.561	Remote Similarity	NPC321030
0.56	Remote Similarity	NPC34754

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC311369 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	74
0.1-0.2	345
0.2-0.3	4853
0.3-0.4	3461
0.4-0.5	416
0.5-0.6	12
0.6-0.7	0
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
0.5833	Remote Similarity	NPD4211	Phase 1

Structure

NPC311369 OpenBabel07101719512D 26 27 0 0 1 0 0 0 0 0999 V2000 -7.0595 7.0985 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5369 2.1259 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9538 0.5570 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1279 5.2905 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.8685 6.5107 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6917 -0.0888 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7962 0.9057 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7781 -0.4955 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7098 1.3125 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6736 -1.4901 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7640 5.5162 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8143 2.3070 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7601 -1.8968 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8324 3.7082 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7459 4.1150 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4538 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7278 2.7137 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4538 -0.3090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9511 -1.3090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.8504 5.1095 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.5878 -0.8090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.5878 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.6180 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -6.0414 5.6973 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 1 5 2 0 0 0 0 2 18 1 0 0 0 0 4 25 1 0 0 0 0 5 11 1 0 0 0 0 6 7 1 0 0 0 0 6 8 1 0 0 0 0 7 9 2 0 0 0 0 8 10 1 0 0 0 0 9 12 1 0 0 0 0 10 13 2 0 0 0 0 12 18 2 0 0 0 0 14 15 1 0 0 0 0 14 18 1 0 0 0 0 15 21 1 0 0 0 0 16 19 1 0 0 0 0 16 22 1 0 0 0 0 17 20 1 0 0 0 0 17 26 1 0 0 0 0 19 3 1 1 0 0 0 19 22 1 0 0 0 0 20 13 1 6 0 0 0 20 24 1 0 0 0 0 21 11 1 6 0 0 0 21 25 1 0 0 0 0 22 23 1 1 0 0 0 23 24 2 0 0 0 0 23 26 1 0 0 0 0 M END $$$$

External Identifiers

PubChem CID	5281967
ChEMBL	CHEMBL89138
ZINC

Physicochemical Properties

Molecular Weight:	373.24
ALogP:	3.5218
MLogP:	3.66
XLogP:	5.676
# Rotatable Bonds:	15
Polar Surface Area:	46.89
# H-Bond Aceptor:	2
# H-Bond Donor:	0
# Rings:	2
# Heavy Atoms:	26

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