NPASS Natural Product

Natural Product: NPC269398

Natural Product ID:	NPC269398
Common Name:	Porpoisamide A
IUPAC Name:	(3S,6S,7R,10S,13R,16S)-13-benzyl-3-[(2S)-butan-2-yl]-6,10,14-trimethyl-7-pentyl-4-oxa-1,8,11,14-tetrazabicyclo[14.3.0]nonadecane-2,5,9,12,15-pentone
Synonyms:	Porpoisamide A
Molecular Formula:	C33H50N4O6
Standard InCHIKey:	JLTRPFNFKJZRBM-BKZRQWESSA-N
Standard InCHI:	InChI=1S/C33H50N4O6/c1-7-9-11-17-25-22(4)33(42)43-28(21(3)8-2)32(41)37-19-14-18-26(37)31(40)36(6)27(20-24-15-12-10-13-16-24)30(39)34-23(5)29(38)35-25/h10,12-13,15-16,21-23,25-28H,7-9,11,14,17-20H2,1-6H3,(H,34,39)(H,35,38)/t21-,22-,23-,25+,26-,27+,28-/m0/s1
Canonical SMILES:	CCCCC[C@H]1N=C(O)[C@H](C)N=C(O)[C@@H](Cc2ccccc2)N(C)C(=O)[C@H]2N(C(=O)[C@@H](OC(=O)[C@H]1C)[C@H](CC)C)CCC2
First Find Year:
Max Developmental Stage:
Synthetic Gene Cluster:	;

Species Source

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Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO32881	lyngbya sp.	Species	Oscillatoriaceae	Bacteria		Florida		PMID[21705224]

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Biological Activity

Activity Type	# Activity
IC50	2

Activity Type	# Activity
Cell Line	2

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Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1045	Cell Line	U2OS	Homo sapiens	IC50	=	28000	nM	10.6019/CHEMBL1201861
NPT393	Cell Line	HCT-116	Homo sapiens	IC50	=	25000	nM	10.6019/CHEMBL1201861

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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 NPC269398 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	93
0.1-0.2	499
0.2-0.3	1723
0.3-0.4	9207
0.4-0.5	15863
0.5-0.6	2810
0.6-0.7	423
0.7-0.8	188
0.8-0.85	45
0.85-0.9	22
0.9-0.95	10
0.95-1	6

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Similarity Score	Similarity Level	Natural Product ID
0.7205	Intermediate Similarity	NPC73655
0.7208	Intermediate Similarity	NPC311658
0.7209	Intermediate Similarity	NPC329731
0.7212	Intermediate Similarity	NPC230611
0.7222	Intermediate Similarity	NPC477937

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Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC269398 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	93
0.1-0.2	275
0.2-0.3	611
0.3-0.4	1583
0.4-0.5	3819
0.5-0.6	2182
0.6-0.7	429
0.7-0.8	160
0.8-0.85	6
0.85-0.9	3
0.9-0.95	0
0.95-1	0

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Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.6863	Remote Similarity	NPD4214	Discontinued
0.6875	Remote Similarity	NPD7131	Phase 3
0.6879	Remote Similarity	NPD7602	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD4574	Approved
0.6879	Remote Similarity	NPD4576	Approved

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Structure

NPC269398 OpenBabel07101718192D 43 45 0 0 1 0 0 0 0 0999 V2000 -0.8126 5.4357 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5176 -0.7908 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1341 -2.1743 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3639 2.4379 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2510 1.7946 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6076 -3.0925 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5594 4.4908 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5727 -0.5376 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3855 4.2376 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.8930 -0.1135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6387 3.2926 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.0458 0.3757 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.8930 -1.0917 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2114 -4.0813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1986 -0.1135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.0458 -1.5809 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5836 3.0394 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1457 -3.7912 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6468 -3.2824 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5042 -2.0700 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8809 -1.2294 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9595 1.6618 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.4748 1.1990 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 7.1986 -1.0917 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8368 2.0945 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.1585 -2.8130 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.6570 -1.5809 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0640 -0.9762 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.7394 1.8440 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9715 -0.6545 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1347 -2.7490 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4967 -1.8535 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3145 0.9263 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9075 0.3217 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.8130 2.1585 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 4.0120 -2.3164 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.2322 -2.4986 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 4.2285 2.6912 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.9414 -0.7822 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3879 -3.6940 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2795 -2.4491 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5327 1.4155 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 7 1 0 0 0 0 2 8 1 0 0 0 0 6 36 1 0 0 0 0 7 9 1 0 0 0 0 8 21 1 0 0 0 0 9 11 1 0 0 0 0 10 12 2 0 0 0 0 10 13 1 0 0 0 0 11 17 1 0 0 0 0 12 15 1 0 0 0 0 13 16 2 0 0 0 0 14 18 1 0 0 0 0 14 19 1 0 0 0 0 15 24 2 0 0 0 0 16 24 1 0 0 0 0 19 37 1 0 0 0 0 20 24 1 0 0 0 0 21 3 1 1 0 0 0 22 4 1 1 0 0 0 22 25 1 0 0 0 0 22 33 1 0 0 0 0 23 5 1 6 0 0 0 23 29 1 0 0 0 0 23 34 1 0 0 0 0 25 17 1 1 0 0 0 25 35 1 0 0 0 0 26 18 1 6 0 0 0 26 31 1 0 0 0 0 26 37 1 0 0 0 0 27 20 1 1 0 0 0 27 30 1 0 0 0 0 27 36 1 0 0 0 0 28 21 1 6 0 0 0 28 32 1 0 0 0 0 28 43 1 0 0 0 0 29 35 2 3 0 0 0 29 38 1 0 0 0 0 30 34 2 3 0 0 0 30 39 1 0 0 0 0 31 36 1 0 0 0 0 31 40 2 0 0 0 0 32 37 1 0 0 0 0 32 41 2 0 0 0 0 33 42 2 0 0 0 0 33 43 1 0 0 0 0 M END $$$$

External Identifiers

PubChem CID	57392122
ChEMBL	CHEMBL1915490
ZINC

Physicochemical Properties

Molecular Weight:	598.37
ALogP:	-3.5724
MLogP:	3.99
XLogP:	6.991
# Rotatable Bonds:	16
Polar Surface Area:	132.1
# H-Bond Aceptor:	10
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	43

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