NPASS Natural Product

Natural Product: NPC258022

Natural Product ID:	NPC258022
Common Name:	Bengazole B
IUPAC Name:	[(S)-1,3-oxazol-5-yl-[4-[(1S,3R,4S,5R)-1,3,4,5-tetrahydroxyhexyl]-1,3-oxazol-2-yl]methyl] 13-methyltetradecanoate
Synonyms:
Molecular Formula:	C28H46N2O8
Standard InCHIKey:	PMKUFDGLMYDGTM-OTUXKISRSA-N
Standard InCHI:	InChI=1S/C28H46N2O8/c1-19(2)13-11-9-7-5-4-6-8-10-12-14-25(34)38-27(24-16-29-18-37-24)28-30-21(17-36-28)22(32)15-23(33)26(35)20(3)31/h16-20,22-23,26-27,31-33,35H,4-15H2,1-3H3/t20-,22+,23-,26+,27+/m1/s1
Canonical SMILES:	CC(CCCCCCCCCCCC(=O)O[C@H](c1occ(n1)[C@H](C[C@H]([C@H]([C@H](O)C)O)O)O)c1ocnc1)C
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
Others	9

Activity Type	# Activity
Cell Line	7
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT399	Cell Line	SF-295	Homo sapiens	Activity	=	0.19	ug/ml	PubChem BioAssay data set
NPT168	Cell Line	P388	Mus musculus	Activity	=	0.053	ug/ml	23819871
NPT575	Cell Line	KM-20L2	Homo sapiens	Activity	=	0.33	ug/ml	24720452
NPT90	Cell Line	DU-145	Homo sapiens	Activity	=	0.15	ug/ml	24720452
NPT1081	Cell Line	BXPC-3	Homo sapiens	Activity	=	0.18	ug/ml	24468633
NPT20	Organism	Candida albicans	Candida albicans	Activity	=	50	%	16792412
NPT20	Organism	Candida albicans	Candida albicans	IZ	=	9	mm	16792412
NPT377	Cell Line	OVCAR-3	Homo sapiens	Activity	=	0.37	ug/ml	23265253
NPT397	Cell Line	NCI-H460	Homo sapiens	Activity	=	0.2	ug/ml	20231393

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 NPC258022 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	225
0.1-0.2	1625
0.2-0.3	8167
0.3-0.4	15857
0.4-0.5	4369
0.5-0.6	581
0.6-0.7	38
0.7-0.8	15
0.8-0.85	0
0.85-0.9	0
0.9-0.95	6
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
0.9727	High Similarity	NPC48323
0.9727	High Similarity	NPC289029
0.9672	High Similarity	NPC208297
0.9672	High Similarity	NPC224395
0.9617	High Similarity	NPC295653
0.9617	High Similarity	NPC107458
0.9399	High Similarity	NPC88938
0.9399	High Similarity	NPC306300
0.9399	High Similarity	NPC58112
0.9344	High Similarity	NPC103452
0.9344	High Similarity	NPC199461
0.9344	High Similarity	NPC46313
0.7476	Intermediate Similarity	NPC476829
0.7376	Intermediate Similarity	NPC476832
0.7207	Intermediate Similarity	NPC477219
0.7175	Intermediate Similarity	NPC37924
0.7143	Intermediate Similarity	NPC325683
0.7143	Intermediate Similarity	NPC476828
0.7093	Intermediate Similarity	NPC477218
0.7054	Intermediate Similarity	NPC476830
0.7048	Intermediate Similarity	NPC299035
0.7048	Intermediate Similarity	NPC177432
0.7018	Intermediate Similarity	NPC322800
0.7018	Intermediate Similarity	NPC168135
0.7009	Intermediate Similarity	NPC476827
0.7009	Intermediate Similarity	NPC476826
0.7009	Intermediate Similarity	NPC476831
0.6834	Remote Similarity	NPC30527
0.6748	Remote Similarity	NPC58001
0.6748	Remote Similarity	NPC314523
0.64	Remote Similarity	NPC473833
0.6349	Remote Similarity	NPC471978
0.6348	Remote Similarity	NPC314270
0.634	Remote Similarity	NPC244536
0.6305	Remote Similarity	NPC326930
0.6305	Remote Similarity	NPC475301
0.6298	Remote Similarity	NPC314222
0.6298	Remote Similarity	NPC196449
0.6287	Remote Similarity	NPC186452
0.628	Remote Similarity	NPC13603
0.6266	Remote Similarity	NPC477589
0.6266	Remote Similarity	NPC477587
0.6256	Remote Similarity	NPC211555
0.6244	Remote Similarity	NPC12660
0.624	Remote Similarity	NPC53255
0.624	Remote Similarity	NPC85879
0.622	Remote Similarity	NPC328928
0.6214	Remote Similarity	NPC477588
0.6214	Remote Similarity	NPC477586
0.6214	Remote Similarity	NPC477590
0.6214	Remote Similarity	NPC54983
0.6214	Remote Similarity	NPC477585
0.6211	Remote Similarity	NPC471979
0.6166	Remote Similarity	NPC472436
0.6138	Remote Similarity	NPC316224
0.6137	Remote Similarity	NPC49195
0.6137	Remote Similarity	NPC309919
0.6135	Remote Similarity	NPC471015
0.6064	Remote Similarity	NPC475315
0.6064	Remote Similarity	NPC324619
0.6047	Remote Similarity	NPC472435
0.6043	Remote Similarity	NPC315804
0.6043	Remote Similarity	NPC313804
0.6024	Remote Similarity	NPC475533
0.6	Remote Similarity	NPC258048
0.5967	Remote Similarity	NPC196718
0.5967	Remote Similarity	NPC102593
0.5962	Remote Similarity	NPC470042
0.592	Remote Similarity	NPC148896
0.592	Remote Similarity	NPC180668
0.592	Remote Similarity	NPC471013
0.5873	Remote Similarity	NPC161801
0.5872	Remote Similarity	NPC153452
0.5851	Remote Similarity	NPC289423
0.5851	Remote Similarity	NPC212766
0.5844	Remote Similarity	NPC316403
0.5827	Remote Similarity	NPC10904
0.5808	Remote Similarity	NPC282346
0.5802	Remote Similarity	NPC186351
0.5794	Remote Similarity	NPC472434
0.5792	Remote Similarity	NPC90019
0.5785	Remote Similarity	NPC209981
0.5765	Remote Similarity	NPC165964
0.575	Remote Similarity	NPC54066
0.5749	Remote Similarity	NPC323752
0.5741	Remote Similarity	NPC475455
0.5733	Remote Similarity	NPC472287
0.5733	Remote Similarity	NPC472286
0.5726	Remote Similarity	NPC35208
0.572	Remote Similarity	NPC474183
0.5709	Remote Similarity	NPC58209
0.5697	Remote Similarity	NPC253482
0.5695	Remote Similarity	NPC75544
0.566	Remote Similarity	NPC472752
0.5656	Remote Similarity	NPC233727
0.5647	Remote Similarity	NPC72715
0.5645	Remote Similarity	NPC471004
0.563	Remote Similarity	NPC475648
0.563	Remote Similarity	NPC75179
0.5622	Remote Similarity	NPC220852
0.5618	Remote Similarity	NPC184680
0.5611	Remote Similarity	NPC470903
0.5611	Remote Similarity	NPC470112
0.5611	Remote Similarity	NPC167763

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC258022 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	163
0.1-0.2	648
0.2-0.3	2109
0.3-0.4	3774
0.4-0.5	2167
0.5-0.6	292
0.6-0.7	8
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
0.6364	Remote Similarity	NPD7896	Approved
0.634	Remote Similarity	NPD4086	Phase 1
0.633	Remote Similarity	NPD6347	Phase 2
0.6227	Remote Similarity	NPD7490	Discontinued
0.6071	Remote Similarity	NPD8370	Discontinued
0.6054	Remote Similarity	NPD5922	Phase 3
0.6025	Remote Similarity	NPD5640	Discontinued
0.6009	Remote Similarity	NPD4667	Clinical (unspecified phase)
0.5967	Remote Similarity	NPD7031	Phase 1
0.5945	Remote Similarity	NPD5532	Phase 2
0.5907	Remote Similarity	NPD6974	Phase 3
0.59	Remote Similarity	NPD8356	Approved
0.5885	Remote Similarity	NPD4898	Clinical (unspecified phase)
0.5847	Remote Similarity	NPD2433	Clinical (unspecified phase)
0.5816	Remote Similarity	NPD7180	Phase 3
0.5802	Remote Similarity	NPD8430	Approved
0.5796	Remote Similarity	NPD7284	Clinical (unspecified phase)
0.5783	Remote Similarity	NPD4394	Clinical (unspecified phase)
0.5777	Remote Similarity	NPD7022	Phase 2
0.5765	Remote Similarity	NPD6525	Clinical (unspecified phase)
0.5755	Remote Similarity	NPD1659	Phase 1
0.5749	Remote Similarity	NPD4373	Phase 2
0.5744	Remote Similarity	NPD7547	Clinical (unspecified phase)
0.5738	Remote Similarity	NPD1638	Discovery
0.5703	Remote Similarity	NPD7853	Phase 2
0.5697	Remote Similarity	NPD7885	Phase 2
0.5697	Remote Similarity	NPD7886	Phase 2
0.5692	Remote Similarity	NPD6495	Clinical (unspecified phase)
0.5663	Remote Similarity	NPD8329	Phase 3
0.564	Remote Similarity	NPD3006	Discontinued
0.5637	Remote Similarity	NPD6252	Clinical (unspecified phase)
0.5628	Remote Similarity	NPD4952	Phase 3
0.5625	Remote Similarity	NPD8326	Phase 3
0.5625	Remote Similarity	NPD8327	Clinical (unspecified phase)
0.5625	Remote Similarity	NPD8325	Phase 3
0.5611	Remote Similarity	NPD3801	Clinical (unspecified phase)
0.561	Remote Similarity	NPD6553	Clinical (unspecified phase)
0.5609	Remote Similarity	NPD6857	Phase 3
0.5607	Remote Similarity	NPD6169	Phase 1
0.5603	Remote Similarity	NPD2779	Approved

Structure

NPC258022 OpenBabel07101718242D 38 39 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 -3.7484 -11.2631 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 -0.5897 -6.0649 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 0.3239 -5.6581 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 0.4284 -4.6636 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 1.3420 -4.2569 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 1.4465 -3.2623 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 2.3600 -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 -3.6439 -10.2686 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 19 1 0 0 0 0 2 19 1 0 0 0 0 4 5 1 0 0 0 0 4 6 1 0 0 0 0 5 7 1 0 0 0 0 6 8 1 0 0 0 0 7 9 1 0 0 0 0 8 10 1 0 0 0 0 9 11 1 0 0 0 0 10 12 1 0 0 0 0 11 13 1 0 0 0 0 12 14 1 0 0 0 0 13 19 1 0 0 0 0 14 25 1 0 0 0 0 15 22 1 0 0 0 0 15 23 1 0 0 0 0 16 24 2 0 0 0 0 16 29 1 0 0 0 0 17 21 2 0 0 0 0 17 36 1 0 0 0 0 18 29 2 0 0 0 0 18 37 1 0 0 0 0 20 3 1 6 0 0 0 20 26 1 0 0 0 0 20 31 1 0 0 0 0 21 22 1 0 0 0 0 21 30 1 0 0 0 0 22 32 1 1 0 0 0 23 26 1 0 0 0 0 23 33 1 1 0 0 0 24 27 1 0 0 0 0 24 37 1 0 0 0 0 25 34 2 0 0 0 0 25 38 1 0 0 0 0 26 35 1 1 0 0 0 27 28 1 0 0 0 0 27 38 1 6 0 0 0 28 30 2 0 0 0 0 28 36 1 0 0 0 0 M END $$$$

External Identifiers

PubChem CID	16753227
ChEMBL	CHEMBL402899
ZINC

Physicochemical Properties

Molecular Weight:	538.33
ALogP:	-4.4579
MLogP:	3.44
XLogP:	5.402
# Rotatable Bonds:	28
Polar Surface Area:	159.28
# H-Bond Aceptor:	8
# H-Bond Donor:	4
# Rings:	2
# Heavy Atoms:	38

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General Info & Identifiers & Properties
Structure MOL file
Source Organisms
Biological Activities
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