NPASS Natural Product

Natural Product: NPC38172

Natural Product ID:	NPC38172
Common Name:	Dragonamide C
IUPAC Name:	(E)-N-[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-amino-3-methyl-1-oxobutan-2-yl]-methylamino]-3-methyl-1-oxobutan-2-yl]-methylamino]-3-methyl-1-oxobutan-2-yl]-methylamino]-3-methyl-1-oxobutan-2-yl]-3-methoxy-N-methyloct-2-en-7-ynamide
Synonyms:	Dragonamide C
Molecular Formula:	C33H57N5O6
Standard InCHIKey:	KDOGKGLXTJQXRR-USBBLSJNSA-N
Standard InCHI:	InChI=1S/C33H57N5O6/c1-15-16-17-18-24(44-14)19-25(39)35(10)27(21(4)5)31(41)37(12)29(23(8)9)33(43)38(13)28(22(6)7)32(42)36(11)26(20(2)3)30(34)40/h1,19-23,26-29H,16-18H2,2-14H3,(H2,34,40)/b24-19+/t26-,27-,28-,29-/m0/s1
Canonical SMILES:	C#CCCC/C(=CC(=O)N([C@H](C(=O)N([C@H](C(=O)N([C@H](C(=O)N([C@H](C(=N)O)C(C)C)C)C(C)C)C)C(C)C)C)C(C)C)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
NPO17326	Lyngbya polychroa	Species	Oscillatoriaceae	Bacteria				PMID[18393465]

Biological Activity

Activity Type	# Activity
GI50	3
Potency	9

Activity Type	# Activity
Cell Line	3
Individual Protein	5
Others	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT64	Individual Protein	ATPase family AAA domain-containing protein 5	Homo sapiens	Potency		29081	nM	25008455
NPT2	Others	Unspecified		Potency		20596.2	nM	Open TG-GATES in vivo data: Hematology
NPT1045	Cell Line	U2OS	Homo sapiens	GI50	=	56000	nM	18077363
NPT478	Individual Protein	Ataxin-2	Homo sapiens	Potency		31622.8	nM	9358645
NPT2	Others	Unspecified		Potency		18356.4	nM	25700232
NPT154	Individual Protein	Mothers against decapentaplegic homolog 3	Homo sapiens	Potency		25118.9	nM	12105963
NPT2	Others	Unspecified		Potency		29092.9	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency		1995.3	nM	10514299
NPT744	Cell Line	IMR-32	Homo sapiens	GI50	=	49000	nM	22444684
NPT139	Cell Line	HT-29	Homo sapiens	GI50	=	22000	nM	22444684
NPT10	Individual Protein	Geminin	Homo sapiens	Potency		5.8	nM	19572738
NPT755	Individual Protein	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	Homo sapiens	Potency		89125.1	nM	11312925

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 NPC38172 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	432
0.2-0.3	17082
0.3-0.4	11401
0.4-0.5	1568
0.5-0.6	316
0.6-0.7	41
0.7-0.8	2
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
0.7053	Intermediate Similarity	NPC235078
0.7021	Intermediate Similarity	NPC23984
0.6979	Remote Similarity	NPC472351
0.6893	Remote Similarity	NPC469739
0.6771	Remote Similarity	NPC184473
0.6759	Remote Similarity	NPC476877
0.6754	Remote Similarity	NPC472536
0.6754	Remote Similarity	NPC103391
0.67	Remote Similarity	NPC473495
0.6694	Remote Similarity	NPC22746
0.6667	Remote Similarity	NPC207820
0.6636	Remote Similarity	NPC475791
0.6636	Remote Similarity	NPC13175
0.6636	Remote Similarity	NPC476876
0.6634	Remote Similarity	NPC155230
0.6598	Remote Similarity	NPC6902
0.6598	Remote Similarity	NPC284456
0.6542	Remote Similarity	NPC475758
0.6514	Remote Similarity	NPC471097
0.6514	Remote Similarity	NPC475149
0.6491	Remote Similarity	NPC476875
0.6429	Remote Similarity	NPC53858
0.6429	Remote Similarity	NPC84128
0.6372	Remote Similarity	NPC171734
0.6303	Remote Similarity	NPC239357
0.629	Remote Similarity	NPC222466
0.625	Remote Similarity	NPC205176
0.624	Remote Similarity	NPC101719
0.6122	Remote Similarity	NPC31756
0.6121	Remote Similarity	NPC251122
0.6071	Remote Similarity	NPC5864
0.6071	Remote Similarity	NPC301148
0.6071	Remote Similarity	NPC124554
0.6064	Remote Similarity	NPC97614
0.6061	Remote Similarity	NPC476117
0.6061	Remote Similarity	NPC476243
0.6061	Remote Similarity	NPC476156
0.6061	Remote Similarity	NPC476137
0.6038	Remote Similarity	NPC47230
0.6038	Remote Similarity	NPC17143
0.6019	Remote Similarity	NPC319913
0.6	Remote Similarity	NPC476302
0.6	Remote Similarity	NPC320057
0.5965	Remote Similarity	NPC323720
0.5962	Remote Similarity	NPC322672
0.5929	Remote Similarity	NPC474244
0.5905	Remote Similarity	NPC473525
0.5888	Remote Similarity	NPC53240
0.5888	Remote Similarity	NPC474576
0.5887	Remote Similarity	NPC315188
0.5882	Remote Similarity	NPC473810
0.5877	Remote Similarity	NPC198344
0.5873	Remote Similarity	NPC36254
0.5859	Remote Similarity	NPC46268
0.5846	Remote Similarity	NPC120335
0.5841	Remote Similarity	NPC188785
0.5833	Remote Similarity	NPC62263
0.5833	Remote Similarity	NPC173763
0.5833	Remote Similarity	NPC471098
0.5826	Remote Similarity	NPC124549
0.5826	Remote Similarity	NPC469604
0.5812	Remote Similarity	NPC67009
0.5812	Remote Similarity	NPC474099
0.5794	Remote Similarity	NPC475801
0.5794	Remote Similarity	NPC474593
0.5784	Remote Similarity	NPC246005
0.5769	Remote Similarity	NPC475975
0.5755	Remote Similarity	NPC324506
0.5752	Remote Similarity	NPC233932
0.5752	Remote Similarity	NPC26597
0.5738	Remote Similarity	NPC296043
0.5729	Remote Similarity	NPC76297
0.5729	Remote Similarity	NPC196007
0.5729	Remote Similarity	NPC214532
0.5725	Remote Similarity	NPC139326
0.5714	Remote Similarity	NPC477539
0.5714	Remote Similarity	NPC469603
0.5714	Remote Similarity	NPC273185
0.5703	Remote Similarity	NPC309525
0.5691	Remote Similarity	NPC329216
0.568	Remote Similarity	NPC470652
0.568	Remote Similarity	NPC470546
0.5664	Remote Similarity	NPC220234
0.5649	Remote Similarity	NPC319766
0.5645	Remote Similarity	NPC470544
0.5636	Remote Similarity	NPC301010
0.5631	Remote Similarity	NPC277341
0.5631	Remote Similarity	NPC226982
0.5612	Remote Similarity	NPC161774
0.5612	Remote Similarity	NPC256312
0.5612	Remote Similarity	NPC209156
0.5612	Remote Similarity	NPC266888
0.5608	Remote Similarity	NPC319320
0.5608	Remote Similarity	NPC287757
0.56	Remote Similarity	NPC469899
0.56	Remote Similarity	NPC470545

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC38172 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	61
0.1-0.2	198
0.2-0.3	3656
0.3-0.4	4389
0.4-0.5	759
0.5-0.6	88
0.6-0.7	10
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
0.6441	Remote Similarity	NPD2099	Approved
0.6325	Remote Similarity	NPD2100	Approved
0.6283	Remote Similarity	NPD2147	Approved
0.617	Remote Similarity	NPD265	Phase 3
0.617	Remote Similarity	NPD266	Phase 3
0.6162	Remote Similarity	NPD7763	Phase 2
0.6162	Remote Similarity	NPD7762	Phase 2
0.6019	Remote Similarity	NPD7759	Phase 2
0.6019	Remote Similarity	NPD7760	Phase 2
0.6017	Remote Similarity	NPD2090	Approved
0.5941	Remote Similarity	NPD2683	Discontinued
0.5818	Remote Similarity	NPD7841	Clinical (unspecified phase)
0.5752	Remote Similarity	NPD3694	Phase 1
0.5607	Remote Similarity	NPD3177	Phase 3

Structure

NPC38172 OpenBabel07101718292D 44 43 0 0 1 0 0 0 0 0999 V2000 -6.0622 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 3.5000 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 2.5981 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 3.0000 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 -3.4641 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 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 -6.0622 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -1.0000 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 -3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 3.0000 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 1.7321 2.0000 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 -2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -3.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7321 2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 1 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 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -3.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 2.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -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 -2.5981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 15 3 0 0 0 0 2 20 1 0 0 0 0 3 20 1 0 0 0 0 4 21 1 0 0 0 0 5 21 1 0 0 0 0 6 22 1 0 0 0 0 7 22 1 0 0 0 0 8 23 1 0 0 0 0 9 23 1 0 0 0 0 10 35 1 0 0 0 0 11 36 1 0 0 0 0 12 37 1 0 0 0 0 13 38 1 0 0 0 0 14 44 1 0 0 0 0 15 16 1 0 0 0 0 16 17 1 0 0 0 0 17 18 1 0 0 0 0 18 24 1 0 0 0 0 19 24 2 0 0 0 0 19 25 1 0 0 0 0 24 44 1 0 0 0 0 25 35 1 0 0 0 0 25 39 2 0 0 0 0 26 20 1 1 0 0 0 26 30 1 0 0 0 0 26 36 1 0 0 0 0 27 21 1 1 0 0 0 27 31 1 0 0 0 0 27 35 1 0 0 0 0 28 22 1 1 0 0 0 28 32 1 0 0 0 0 28 38 1 0 0 0 0 29 23 1 1 0 0 0 29 33 1 0 0 0 0 29 37 1 0 0 0 0 30 34 2 0 0 0 0 30 40 1 0 0 0 0 31 37 1 0 0 0 0 31 41 2 0 0 0 0 32 36 1 0 0 0 0 32 42 2 0 0 0 0 33 38 1 0 0 0 0 33 43 2 0 0 0 0 M END $$$$

External Identifiers

PubChem CID	24878746
ChEMBL	CHEMBL446807
ZINC

Physicochemical Properties

Molecular Weight:	619.43
ALogP:	0.109
MLogP:	3.88
XLogP:	3.643
# Rotatable Bonds:	35
Polar Surface Area:	134.55
# H-Bond Aceptor:	11
# H-Bond Donor:	2
# Rings:	0
# Heavy Atoms:	44

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