NPASS Natural Product

Natural Product: NPC469388

Natural Product ID:	NPC469388
Common Name:	Norbatzelladine L
IUPAC Name:
Synonyms:	Nor-Batzelladine L
Molecular Formula:	C38H66N6O2
Standard InCHIKey:	HGZBYTYKEVODQE-LZBHNGPDSA-N
Standard InCHI:	InChI=1S/C38H66N6O2/c1-5-6-7-8-11-14-18-30-25-33-21-22-34-35(28(4)40-38(42-30)44(33)34)36(45)46-27(3)16-13-10-9-12-15-17-29-24-32-20-19-31-23-26(2)39-37(41-29)43(31)32/h26-35H,5-25H2,1-4H3,(H,39,41)(H,40,42)/t26-,27?,28+,29+,30+,31+,32-,33-,34-,35-/m0/s1
Canonical SMILES:	CCCCCCCC[C@@H]1C[C@@H]2CC[C@@H]3N2C(=N[C@@H]([C@@H]3C(=O)OC(CCCCCCC[C@@H]2C[C@@H]3CC[C@H]4N3C(=N[C@H](C4)C)N2)C)C)N1
First Find Year:
Max Developmental Stage:
Synthetic Gene Cluster:	;

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Collection Location	Reference
NPO8412	Monanchora arbuscula	Species	Crambeidae	Eukaryota	Caribbean	PMID[19743809]
NPO33489	clathria calla	Species	Microcionidae	Eukaryota	Caribbean	PMID[19743809]
NPO8412	Monanchora arbuscula	Species	Crambeidae	Eukaryota		PMID[25924111]

Biological Activity

Activity Type	# Activity
GI50	3
IC50	4
Others	11

Activity Type	# Activity
Cell Line	10
Organism	7
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1021	Organism	Leishmania infantum	Leishmania infantum	Activity	=	65	%	Open TG-GATES in vivo data: Biochemistry
NPT139	Cell Line	HT-29	Homo sapiens	GI50	=	1200	nM	17803266
NPT82	Cell Line	MDA-MB-231	Homo sapiens	GI50	=	700	nM	24387683
NPT82	Cell Line	MDA-MB-231	Homo sapiens	TGI	=	1900	nM	15043407
NPT1021	Organism	Leishmania infantum	Leishmania infantum	Activity	=	82	%	15568769
NPT580	Organism	Trypanosoma cruzi	Trypanosoma cruzi	Ratio IC50	=	54		15332833
NPT1225	Organism	Plasmodium falciparum (isolate FcB1 / Columbia)	Plasmodium falciparum FcB1/Columbia	IC50	=	400	nM	18183025
NPT81	Cell Line	A549	Homo sapiens	GI50	=	1100	nM	21067924
NPT1021	Organism	Leishmania infantum	Leishmania infantum	Activity	=	30	%	15387645
NPT2	Others	Unspecified		Ratio IC50	=	12		15387645
NPT81	Cell Line	A549	Homo sapiens	LC50	=	4200	nM	22472691
NPT81	Cell Line	A549	Homo sapiens	TGI	=	2100	nM	10.1007/s00044-013-0780-4
NPT139	Cell Line	HT-29	Homo sapiens	TGI	=	2200	nM	10.1007/s00044-013-0780-4
NPT1021	Organism	Leishmania infantum	Leishmania infantum	IC50	=	2000	nM	26331426
NPT139	Cell Line	HT-29	Homo sapiens	LC50	=	4000	nM	7903980
NPT82	Cell Line	MDA-MB-231	Homo sapiens	LC50	=	4800	nM	11520237
NPT580	Organism	Trypanosoma cruzi	Trypanosoma cruzi	IC50	=	7000	nM	23558238
NPT2679	Cell Line	LLC-MK2	Macaca mulatta	IC50	=	85000	nM	22209731

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 NPC469388 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	98
0.1-0.2	2469
0.2-0.3	15611
0.3-0.4	11249
0.4-0.5	1305
0.5-0.6	138
0.6-0.7	11
0.7-0.8	5
0.8-0.85	0
0.85-0.9	1
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC472737
1.0	High Similarity	NPC469389
0.8627	High Similarity	NPC472736
0.7724	Intermediate Similarity	NPC311244
0.7724	Intermediate Similarity	NPC324722
0.7724	Intermediate Similarity	NPC198644
0.7686	Intermediate Similarity	NPC477518
0.7007	Intermediate Similarity	NPC477519
0.6923	Remote Similarity	NPC261730
0.6739	Remote Similarity	NPC142761
0.6599	Remote Similarity	NPC327517
0.6599	Remote Similarity	NPC322372
0.6599	Remote Similarity	NPC319334
0.6515	Remote Similarity	NPC469387
0.6455	Remote Similarity	NPC304454
0.64	Remote Similarity	NPC469423
0.6376	Remote Similarity	NPC321485
0.6376	Remote Similarity	NPC317377
0.6019	Remote Similarity	NPC216090
0.5935	Remote Similarity	NPC87919
0.5905	Remote Similarity	NPC208657
0.5893	Remote Similarity	NPC277918
0.5882	Remote Similarity	NPC476449
0.584	Remote Similarity	NPC467022
0.5667	Remote Similarity	NPC476261
0.5667	Remote Similarity	NPC471635
0.5667	Remote Similarity	NPC25033
0.5667	Remote Similarity	NPC119225
0.5667	Remote Similarity	NPC470382
0.5655	Remote Similarity	NPC473955
0.563	Remote Similarity	NPC469998
0.562	Remote Similarity	NPC3604

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC469388 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	79
0.1-0.2	485
0.2-0.3	4405
0.3-0.4	3558
0.4-0.5	560
0.5-0.6	69
0.6-0.7	5
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
0.64	Remote Similarity	NPD2696	Approved
0.64	Remote Similarity	NPD2694	Approved
0.64	Remote Similarity	NPD2695	Approved
0.64	Remote Similarity	NPD2697	Approved
0.605	Remote Similarity	NPD4825	Clinical (unspecified phase)
0.5948	Remote Similarity	NPD6699	Clinical (unspecified phase)
0.5929	Remote Similarity	NPD3176	Clinical (unspecified phase)
0.584	Remote Similarity	NPD1829	Clinical (unspecified phase)
0.584	Remote Similarity	NPD1828	Approved
0.584	Remote Similarity	NPD1827	Clinical (unspecified phase)
0.5726	Remote Similarity	NPD6122	Discontinued
0.5714	Remote Similarity	NPD8175	Discontinued
0.562	Remote Similarity	NPD5349	Clinical (unspecified phase)

Structure

NPC469388 OpenBabel07101719512D 46 51 0 0 1 0 0 0 0 0999 V2000 -7.7942 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 14.9908 -0.0331 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0565 -1.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3316 1.0381 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 1.0000 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 7.4723 -0.4089 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5847 0.0517 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 8.3150 0.1294 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7420 -0.4866 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 9.2026 -0.3312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8544 -0.0260 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.0453 0.2071 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 13.1151 -2.7408 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.1169 -2.6810 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6581 -1.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3364 -1.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 14.1085 -1.2935 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.9777 -1.2525 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 14.0964 -0.4804 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.0117 -0.5643 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 1.4181 0.6314 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 10.9329 -0.2535 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 13.4805 -1.8099 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 11.8653 -1.7131 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.7431 -0.6691 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.3938 -0.1814 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.2813 -0.6420 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.6632 -0.1758 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 13.4531 0.0170 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.7978 1.1571 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 11.7756 0.2849 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 12.7081 -1.1748 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.3262 -1.6410 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.1241 -0.1037 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 5 1 0 0 0 0 3 27 1 0 0 0 0 5 6 1 0 0 0 0 6 7 1 0 0 0 0 7 8 1 0 0 0 0 8 11 1 0 0 0 0 9 10 1 0 0 0 0 9 12 1 0 0 0 0 10 13 1 0 0 0 0 11 14 1 0 0 0 0 12 15 1 0 0 0 0 13 16 1 0 0 0 0 14 18 1 0 0 0 0 15 17 1 0 0 0 0 16 27 1 0 0 0 0 19 20 1 0 0 0 0 21 22 1 0 0 0 0 23 26 1 0 0 0 0 23 31 1 0 0 0 0 24 29 1 0 0 0 0 24 32 1 0 0 0 0 25 30 1 0 0 0 0 25 33 1 0 0 0 0 26 2 1 1 0 0 0 26 39 1 0 0 0 0 27 46 1 0 0 0 0 28 4 1 6 0 0 0 28 35 1 0 0 0 0 28 40 1 0 0 0 0 29 17 1 1 0 0 0 29 41 1 0 0 0 0 30 18 1 1 0 0 0 30 42 1 0 0 0 0 31 19 1 1 0 0 0 31 43 1 0 0 0 0 32 20 1 1 0 0 0 32 43 1 0 0 0 0 33 21 1 1 0 0 0 33 44 1 0 0 0 0 34 22 1 6 0 0 0 34 35 1 0 0 0 0 34 44 1 0 0 0 0 35 36 1 6 0 0 0 36 45 2 0 0 0 0 36 46 1 0 0 0 0 37 39 2 0 0 0 0 37 41 1 0 0 0 0 37 43 1 0 0 0 0 38 40 2 0 0 0 0 38 42 1 0 0 0 0 38 44 1 0 0 0 0 M END $$$$

External Identifiers

PubChem CID	44631992
ChEMBL	CHEMBL1077542
ZINC

Physicochemical Properties

Molecular Weight:	638.52
ALogP:	-7.6954
MLogP:	4.76
XLogP:	11.365
# Rotatable Bonds:	22
Polar Surface Area:	81.56
# H-Bond Aceptor:	8
# H-Bond Donor:	2
# Rings:	6
# Heavy Atoms:	46

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