NPASS Natural Product

Natural Product: NPC48323

Natural Product ID:	NPC48323
Common Name:	Bengazole A
IUPAC Name:	[(S)-1,3-oxazol-5-yl-[4-[(1S,3R,4S,5R)-1,3,4,5-tetrahydroxyhexyl]-1,3-oxazol-2-yl]methyl] tetradecanoate
Synonyms:
Molecular Formula:	C27H44N2O8
Standard InCHIKey:	XXGWNOCDEURNQA-MXNGIANISA-N
Standard InCHI:	InChI=1S/C27H44N2O8/c1-3-4-5-6-7-8-9-10-11-12-13-14-24(33)37-26(23-16-28-18-36-23)27-29-20(17-35-27)21(31)15-22(32)25(34)19(2)30/h16-19,21-22,25-26,30-32,34H,3-15H2,1-2H3/t19-,21+,22-,25+,26+/m1/s1
Canonical SMILES:	CCCCCCCCCCCCCC(=O)O[C@H](c1occ(n1)[C@H](C[C@H]([C@H]([C@H](O)C)O)O)O)c1ocnc1
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
NPO33062	dorypleres splendens	Species	NA	NA		Fiji	1996	PMID[18327911]

Biological Activity

Activity Type	# Activity
GI50	2
MIC	4
Others	17

Activity Type	# Activity
Cell Line	13
Organism	10

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20	Organism	Candida albicans	Candida albicans	IZ	=	9	mm	19273668
NPT407	Cell Line	COLO 205	Homo sapiens	GI50	=	181	nM	26331426
NPT407	Cell Line	COLO 205	Homo sapiens	TGI	=	1500	nM	21846091
NPT407	Cell Line	COLO 205	Homo sapiens	LC50	=	5250	nM	21846091
NPT373	Cell Line	SK-MEL-5	Homo sapiens	GI50	=	1130	nM	21846091
NPT168	Cell Line	P388	Mus musculus	Activity	=	0.14	ug/ml	18345641
NPT20	Organism	Candida albicans	Candida albicans	MIC	>	32	ug/ml	8158155
NPT399	Cell Line	SF-295	Homo sapiens	Activity	=	0.19	ug/ml	Open TG-GATES in vivo data: Hematology
NPT20	Organism	Candida albicans	Candida albicans	MIC	=	1	ug/ml	DrugMatrix in vitro pharmacology data
NPT373	Cell Line	SK-MEL-5	Homo sapiens	LC50	=	4830	nM	11975502
NPT20	Organism	Candida albicans	Candida albicans	IZ	=	50	mm	16180804
NPT554	Organism	Candida glabrata	Candida glabrata	IZ	=	15	mm	16180804
NPT575	Cell Line	KM-20L2	Homo sapiens	Activity	=	0.0031	ug/ml	20073490
NPT90	Cell Line	DU-145	Homo sapiens	Activity	=	0.15	ug/ml	10.1039/C4MD00086B
NPT373	Cell Line	SK-MEL-5	Homo sapiens	TGI	=	4830	nM	11975502
NPT20	Organism	Candida albicans	Candida albicans	IZ	=	50	mm	DrugMatrix in vitro pharmacology data
NPT20	Organism	Candida albicans	Candida albicans	MIC	=	1	ug/ml	9392880
NPT187	Organism	Issatchenkia orientalis	Pichia kudriavzevii	IZ	=	35	mm	10924160
NPT20	Organism	Candida albicans	Candida albicans	IZ	=	15	mm	18835721
NPT1081	Cell Line	BXPC-3	Homo sapiens	Activity	=	0.14	ug/ml	16309322
NPT20	Organism	Candida albicans	Candida albicans	MIC	=	1	ug/ml	22884991
NPT377	Cell Line	OVCAR-3	Homo sapiens	Activity	=	0.28	ug/ml	18077425
NPT397	Cell Line	NCI-H460	Homo sapiens	Activity	=	0.21	ug/ml	23268606

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 NPC48323 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	238
0.1-0.2	2221
0.2-0.3	10248
0.3-0.4	14690
0.4-0.5	3079
0.5-0.6	359
0.6-0.7	40
0.7-0.8	2
0.8-0.85	0
0.85-0.9	0
0.9-0.95	4
0.95-1	8

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC289029
0.9727	High Similarity	NPC258022
0.9663	High Similarity	NPC306300
0.9663	High Similarity	NPC58112
0.9663	High Similarity	NPC88938
0.9607	High Similarity	NPC46313
0.9607	High Similarity	NPC103452
0.9607	High Similarity	NPC199461
0.9399	High Similarity	NPC208297
0.9399	High Similarity	NPC224395
0.9344	High Similarity	NPC295653
0.9344	High Similarity	NPC107458
0.7233	Intermediate Similarity	NPC476829
0.7149	Intermediate Similarity	NPC476832
0.6982	Remote Similarity	NPC477219
0.6951	Remote Similarity	NPC37924
0.692	Remote Similarity	NPC325683
0.692	Remote Similarity	NPC476828
0.6872	Remote Similarity	NPC477218
0.683	Remote Similarity	NPC476830
0.6828	Remote Similarity	NPC299035
0.6828	Remote Similarity	NPC177432
0.6798	Remote Similarity	NPC168135
0.6798	Remote Similarity	NPC322800
0.6786	Remote Similarity	NPC476831
0.6786	Remote Similarity	NPC476827
0.6786	Remote Similarity	NPC476826
0.6585	Remote Similarity	NPC58001
0.6585	Remote Similarity	NPC314523
0.6583	Remote Similarity	NPC30527
0.62	Remote Similarity	NPC473833
0.6151	Remote Similarity	NPC471978
0.613	Remote Similarity	NPC314270
0.6128	Remote Similarity	NPC244536
0.6107	Remote Similarity	NPC314222
0.6107	Remote Similarity	NPC196449
0.6104	Remote Similarity	NPC326930
0.6104	Remote Similarity	NPC475301
0.608	Remote Similarity	NPC13603
0.6058	Remote Similarity	NPC477587
0.6058	Remote Similarity	NPC477589
0.604	Remote Similarity	NPC53255
0.604	Remote Similarity	NPC186452
0.604	Remote Similarity	NPC85879
0.6032	Remote Similarity	NPC472436
0.6024	Remote Similarity	NPC328928
0.6016	Remote Similarity	NPC471979
0.601	Remote Similarity	NPC211555
0.6008	Remote Similarity	NPC477588
0.6008	Remote Similarity	NPC477586
0.6008	Remote Similarity	NPC477585
0.6008	Remote Similarity	NPC477590
0.6	Remote Similarity	NPC153452
0.6	Remote Similarity	NPC12660
0.5991	Remote Similarity	NPC309919
0.5991	Remote Similarity	NPC49195
0.5975	Remote Similarity	NPC212766
0.5975	Remote Similarity	NPC289423
0.5971	Remote Similarity	NPC54983
0.5936	Remote Similarity	NPC471015
0.5935	Remote Similarity	NPC316224
0.5915	Remote Similarity	NPC90019
0.5913	Remote Similarity	NPC472435
0.5897	Remote Similarity	NPC313804
0.5897	Remote Similarity	NPC315804
0.5866	Remote Similarity	NPC258048
0.5863	Remote Similarity	NPC324619
0.5863	Remote Similarity	NPC475315
0.5826	Remote Similarity	NPC196718
0.5823	Remote Similarity	NPC475533
0.58	Remote Similarity	NPC161801
0.5769	Remote Similarity	NPC470042
0.5761	Remote Similarity	NPC102593
0.5726	Remote Similarity	NPC186351
0.572	Remote Similarity	NPC180668
0.572	Remote Similarity	NPC148896
0.572	Remote Similarity	NPC471013
0.5696	Remote Similarity	NPC316403
0.5672	Remote Similarity	NPC54066
0.5657	Remote Similarity	NPC472434
0.5652	Remote Similarity	NPC472287
0.5652	Remote Similarity	NPC472286
0.563	Remote Similarity	NPC10904
0.563	Remote Similarity	NPC165964
0.5615	Remote Similarity	NPC282346
0.5611	Remote Similarity	NPC75544

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC48323 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	154
0.1-0.2	825
0.2-0.3	2353
0.3-0.4	3795
0.4-0.5	1845
0.5-0.6	185
0.6-0.7	4
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
0.621	Remote Similarity	NPD7896	Approved
0.6128	Remote Similarity	NPD4086	Phase 1
0.6101	Remote Similarity	NPD6347	Phase 2
0.6	Remote Similarity	NPD7490	Discontinued
0.5985	Remote Similarity	NPD5922	Phase 3
0.5949	Remote Similarity	NPD5640	Discontinued
0.5892	Remote Similarity	NPD7031	Phase 1
0.5873	Remote Similarity	NPD5532	Phase 2
0.5873	Remote Similarity	NPD8370	Discontinued
0.583	Remote Similarity	NPD6974	Phase 3
0.5823	Remote Similarity	NPD8356	Approved
0.5809	Remote Similarity	NPD4898	Clinical (unspecified phase)
0.5794	Remote Similarity	NPD4667	Clinical (unspecified phase)
0.5738	Remote Similarity	NPD7180	Phase 3
0.5726	Remote Similarity	NPD8430	Approved
0.5709	Remote Similarity	NPD4394	Clinical (unspecified phase)
0.5703	Remote Similarity	NPD7022	Phase 2
0.5702	Remote Similarity	NPD2433	Clinical (unspecified phase)
0.5667	Remote Similarity	NPD7547	Clinical (unspecified phase)
0.566	Remote Similarity	NPD1638	Discovery
0.563	Remote Similarity	NPD6525	Clinical (unspecified phase)
0.5615	Remote Similarity	NPD1659	Phase 1
0.561	Remote Similarity	NPD4373	Phase 2

Structure

NPC48323 OpenBabel07101719252D 37 38 0 0 1 0 0 0 0 0999 V2000 -4.4529 -9.6808 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0074 3.8475 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6439 -10.2686 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7303 -9.8619 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6258 -8.8674 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7123 -8.4606 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6077 -7.4661 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6942 -7.0594 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5897 -6.0649 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3239 -5.6581 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4284 -4.6636 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3420 -4.2569 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4465 -3.2623 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3600 -2.8556 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3601 3.3122 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5396 -0.3720 0.0000 C 0 0 0 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 3.8761 1.2106 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6984 4.7985 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 1.6180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3090 2.5691 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0511 4.2633 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.6736 0.1280 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4646 -1.8611 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7202 5.0064 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7601 -0.2788 0.0000 C 0 0 1 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 4.2828 0.2971 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 1.3090 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.3675 5.5417 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2872 2.7770 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9271 4.4712 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3781 -1.4543 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.4112 5.9575 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 2.8815 1.1061 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6555 -1.2733 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 3 1 0 0 0 0 3 4 1 0 0 0 0 4 5 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 9 1 0 0 0 0 9 10 1 0 0 0 0 10 11 1 0 0 0 0 11 12 1 0 0 0 0 12 13 1 0 0 0 0 13 14 1 0 0 0 0 14 24 1 0 0 0 0 15 21 1 0 0 0 0 15 22 1 0 0 0 0 16 23 2 0 0 0 0 16 28 1 0 0 0 0 17 20 2 0 0 0 0 17 35 1 0 0 0 0 18 28 2 0 0 0 0 18 36 1 0 0 0 0 19 2 1 6 0 0 0 19 25 1 0 0 0 0 19 30 1 0 0 0 0 20 21 1 0 0 0 0 20 29 1 0 0 0 0 21 31 1 1 0 0 0 22 25 1 0 0 0 0 22 32 1 1 0 0 0 23 26 1 0 0 0 0 23 36 1 0 0 0 0 24 33 2 0 0 0 0 24 37 1 0 0 0 0 25 34 1 1 0 0 0 26 27 1 0 0 0 0 26 37 1 6 0 0 0 27 29 2 0 0 0 0 27 35 1 0 0 0 0 M END $$$$

External Identifiers

PubChem CID	10602150
ChEMBL	CHEMBL257763
ZINC

Physicochemical Properties

Molecular Weight:	524.31
ALogP:	-5.8111
MLogP:	3.33
XLogP:	4.894
# Rotatable Bonds:	27
Polar Surface Area:	159.28
# H-Bond Aceptor:	8
# H-Bond Donor:	4
# Rings:	2
# Heavy Atoms:	37

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