NPASS Compound

Structure

NPC135950 OpenBabel07101719242D 22 23 0 0 0 0 0 0 0 0999 V2000 -3.4641 3.0000 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 1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 2.5000 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 -2.5981 -1.5000 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 -4.3301 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 -1.5000 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 -0.8660 -0.5000 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 -0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 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 1.7321 -0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -3.0000 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 -3.4641 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 4 1 0 0 0 0 2 8 1 0 0 0 0 3 9 1 0 0 0 0 4 8 2 0 0 0 0 5 6 2 0 0 0 0 5 10 1 0 0 0 0 6 18 1 0 0 0 0 7 11 1 0 0 0 0 7 22 1 0 0 0 0 8 16 1 0 0 0 0 9 13 2 0 0 0 0 9 14 1 0 0 0 0 10 12 2 0 0 0 0 10 14 1 0 0 0 0 11 12 1 0 0 0 0 11 18 2 0 0 0 0 12 15 1 0 0 0 0 13 15 1 0 0 0 0 13 17 1 0 0 0 0 14 19 2 0 0 0 0 15 20 2 0 0 0 0 16 21 2 0 0 0 0 16 22 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	300.11
Volume:	304.242
LogP:	1.017
LogD:	0.964
LogS:	-2.535
# Rotatable Bonds:	4
TPSA:	97.18
# H-Bond Aceptor:	6
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.681
Synthetic Accessibility Score:	3.735
Fsp3:	0.312
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.741
MDCK Permeability:	3.1758441764395684e-05
Pgp-inhibitor:	0.015
Pgp-substrate:	0.006
Human Intestinal Absorption (HIA):	0.016
20% Bioavailability (F20%):	0.02
30% Bioavailability (F30%):	0.023

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.642
Plasma Protein Binding (PPB):	83.66899108886719%
Volume Distribution (VD):	1.367
Pgp-substrate:	12.443379402160645%

ADMET: Metabolism

CYP1A2-inhibitor:	0.894
CYP1A2-substrate:	0.625
CYP2C19-inhibitor:	0.462
CYP2C19-substrate:	0.184
CYP2C9-inhibitor:	0.77
CYP2C9-substrate:	0.108
CYP2D6-inhibitor:	0.717
CYP2D6-substrate:	0.161
CYP3A4-inhibitor:	0.444
CYP3A4-substrate:	0.188

ADMET: Excretion

Clearance (CL):	2.224
Half-life (T1/2):	0.438

ADMET: Toxicity

hERG Blockers:	0.038
Human Hepatotoxicity (H-HT):	0.436
Drug-inuced Liver Injury (DILI):	0.966
AMES Toxicity:	0.92
Rat Oral Acute Toxicity:	0.093
Maximum Recommended Daily Dose:	0.681
Skin Sensitization:	0.408
Carcinogencity:	0.313
Eye Corrosion:	0.004
Eye Irritation:	0.028
Respiratory Toxicity:	0.883

Download Data

Data Type	Select
General Info & Identifiers & Properties
Structure MOL file
Source Organisms
Biological Activities
Similar NPs/Drugs

Natural Product: NPC135950

Natural Product ID:	NPC135950
*Common Name:**	Cribrostatin 3
IUPAC Name:	(7-amino-6-methyl-5,8-dioxoisoquinolin-1-yl)methyl (Z)-2-methylbut-2-enoate
Synonyms:	Cribrostatin 3
Standard InCHIKey:	OOVHJUXBXNVAER-YWEYNIOJSA-N
Standard InCHI:	InChI=1S/C16H16N2O4/c1-4-8(2)16(21)22-7-11-12-10(5-6-18-11)14(19)9(3)13(17)15(12)20/h4-6H,7,17H2,1-3H3/b8-4-
SMILES:	C/C=C(C(=O)OCc1nccc2c1C(=O)C(=C(C2=O)C)N)/C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL500613
PubChem CID:	9926342
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0002566] Isoquinolines and derivatives [CHEMONTID:0002567] Isoquinoline quinones

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO33225	cribrochalina sp.	Species	Niphatidae	Eukaryota	n.a.	republic of maldives	n.a.	PMID[10869203]
NPO33225	cribrochalina sp.	Species	Niphatidae	Eukaryota	n.a.	n.a.	n.a.	PMID[12713412]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
ED50	1
GI50	46
MIC	2

Activity Type	# Activity
Cell Line	46
NON-MOLECULAR	1
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT374	Cell Line	SF-539	Homo sapiens	GI50	=	4786.3	nM	PMID[558156]
NPT399	Cell Line	SF-295	Homo sapiens	GI50	=	3630.78	nM	PMID[558156]
NPT395	Cell Line	SF-268	Homo sapiens	GI50	=	6309.57	nM	PMID[558156]
NPT396	Cell Line	T47D	Homo sapiens	GI50	=	6456.54	nM	PMID[558156]
NPT367	Cell Line	MDA-N	Homo sapiens	GI50	=	1905.46	nM	PMID[558156]
NPT400	Cell Line	MDA-MB-435	Homo sapiens	GI50	=	1819.7	nM	PMID[558156]
NPT402	Cell Line	Hs-578T	Homo sapiens	GI50	=	6309.57	nM	PMID[558156]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	GI50	=	8709.64	nM	PMID[558156]
NPT83	Cell Line	MCF7	Homo sapiens	GI50	=	4570.88	nM	PMID[558156]
NPT83	Cell Line	MCF7	Homo sapiens	GI50	=	4677.35	nM	PMID[558156]
NPT306	Cell Line	PC-3	Homo sapiens	GI50	=	1995.26	nM	PMID[558156]
NPT368	Cell Line	SN12C	Homo sapiens	GI50	=	6165.95	nM	PMID[558156]
NPT406	Cell Line	RXF 393	Homo sapiens	GI50	=	4897.79	nM	PMID[558156]
NPT369	Cell Line	ACHN	Homo sapiens	GI50	=	9549.93	nM	PMID[558156]
NPT401	Cell Line	786-0	Homo sapiens	GI50	=	5888.44	nM	PMID[558156]
NPT381	Cell Line	OVCAR-8	Homo sapiens	GI50	=	8709.64	nM	PMID[558156]
NPT456	Cell Line	OVCAR-4	Homo sapiens	GI50	=	5248.07	nM	PMID[558156]
NPT458	Cell Line	IGROV-1	Homo sapiens	GI50	=	1819.7	nM	PMID[558156]
NPT398	Cell Line	UACC-62	Homo sapiens	GI50	=	2511.89	nM	PMID[558156]
NPT373	Cell Line	SK-MEL-5	Homo sapiens	GI50	=	1096.48	nM	PMID[558156]
NPT375	Cell Line	Malme-3M	Homo sapiens	GI50	=	616.6	nM	PMID[558156]
NPT390	Cell Line	LOX IMVI	Homo sapiens	GI50	=	4073.8	nM	PMID[558156]
NPT380	Cell Line	U-251	Homo sapiens	GI50	=	3235.94	nM	PMID[558156]
NPT392	Cell Line	SNB-75	Homo sapiens	GI50	=	4786.3	nM	PMID[558156]
NPT323	Cell Line	SW-620	Homo sapiens	GI50	=	3630.78	nM	PMID[558156]
NPT386	Cell Line	KM12	Homo sapiens	GI50	=	4897.79	nM	PMID[558156]
NPT407	Cell Line	COLO 205	Homo sapiens	GI50	=	5888.44	nM	PMID[558156]
NPT455	Cell Line	NCI-H522	Homo sapiens	GI50	=	3890.45	nM	PMID[558156]
NPT397	Cell Line	NCI-H460	Homo sapiens	GI50	=	3019.95	nM	PMID[558156]
NPT405	Cell Line	NCI-H226	Homo sapiens	GI50	=	7079.46	nM	PMID[558156]
NPT372	Cell Line	HOP-92	Homo sapiens	GI50	=	9549.93	nM	PMID[558156]
NPT379	Cell Line	HOP-62	Homo sapiens	GI50	=	5370.32	nM	PMID[558156]
NPT81	Cell Line	A549	Homo sapiens	GI50	=	3467.37	nM	PMID[558156]
NPT385	Cell Line	SR	Homo sapiens	GI50	=	3388.44	nM	PMID[558156]
NPT389	Cell Line	RPMI-8226	Homo sapiens	GI50	=	8511.38	nM	PMID[558156]
NPT112	Cell Line	MOLT-4	Homo sapiens	GI50	=	4897.79	nM	PMID[558156]
NPT111	Cell Line	K562	Homo sapiens	GI50	=	7413.1	nM	PMID[558156]
NPT404	Cell Line	CCRF-CEM	Homo sapiens	GI50	=	4265.8	nM	PMID[558156]
NPT1081	Cell Line	BXPC-3	Homo sapiens	GI50	>	1.0	ug.mL-1	PMID[558156]
NPT377	Cell Line	OVCAR-3	Homo sapiens	GI50	=	0.77	ug.mL-1	PMID[558156]
NPT399	Cell Line	SF-295	Homo sapiens	GI50	>	1.0	ug.mL-1	PMID[558156]
NPT397	Cell Line	NCI-H460	Homo sapiens	GI50	>	1.0	ug.mL-1	PMID[558156]
NPT575	Cell Line	KM-20L2	Homo sapiens	GI50	>	1.0	ug.mL-1	PMID[558156]
NPT90	Cell Line	DU-145	Homo sapiens	GI50	>	1.0	ug.mL-1	PMID[558156]
NPT168	Cell Line	P388	Mus musculus	GI50	=	2.49	ug.mL-1	PMID[558156]
NPT168	Cell Line	P388	Mus musculus	ED50	=	2.5	ug ml-1	PMID[558156]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	GI50	=	3090.3	nM	PMID[558156]
NPT1522	Organism	Neisseria gonorrhoeae	Neisseria gonorrhoeae	MIC	=	0.39	ug	PMID[558156]
NPT1522	Organism	Neisseria gonorrhoeae	Neisseria gonorrhoeae	MIC	=	0.0975	ug	PMID[558156]

☑ Note for Activity Records:
☉ The quantitative biological activities were primarily integrated from ChEMBL (Version-30) database and were also directly collected from PubMed literature. PubMed PMID was provided as the reference link for each activity record.

Chemically structural similarity: I. Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes 4,3285 NPs with experimentally-derived bioactivity available 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 NPC135950 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	283
0.1-0.2	2593
0.2-0.3	10684
0.3-0.4	12870
0.4-0.5	11313
0.5-0.6	3156
0.6-0.7	1549
0.7-0.8	233
0.8-0.85	11
0.85-0.9	1
0.9-0.95	2
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9773	High Similarity	NPC103361
0.9061	High Similarity	NPC109922
0.8994	High Similarity	NPC469489
0.8432	Intermediate Similarity	NPC114974
0.8418	Intermediate Similarity	NPC249614
0.822	Intermediate Similarity	NPC123395
0.8202	Intermediate Similarity	NPC470894
0.8198	Intermediate Similarity	NPC70406
0.8046	Intermediate Similarity	NPC107287
0.8011	Intermediate Similarity	NPC273532
0.7845	Intermediate Similarity	NPC41717
0.7841	Intermediate Similarity	NPC251391
0.7829	Intermediate Similarity	NPC313889
0.7816	Intermediate Similarity	NPC112741
0.7811	Intermediate Similarity	NPC123839
0.7734	Intermediate Similarity	NPC118940
0.7725	Intermediate Similarity	NPC207851
0.7714	Intermediate Similarity	NPC105811
0.7711	Intermediate Similarity	NPC266249
0.7709	Intermediate Similarity	NPC213914
0.7697	Intermediate Similarity	NPC209362
0.7684	Intermediate Similarity	NPC282103
0.7676	Intermediate Similarity	NPC191310
0.767	Intermediate Similarity	NPC123906
0.7668	Intermediate Similarity	NPC138370
0.765	Intermediate Similarity	NPC473239
0.765	Intermediate Similarity	NPC289086
0.7647	Intermediate Similarity	NPC318299
0.7626	Intermediate Similarity	NPC470279
0.7624	Intermediate Similarity	NPC63041
0.7624	Intermediate Similarity	NPC470190
0.761	Intermediate Similarity	NPC317752
0.76	Intermediate Similarity	NPC467188
0.7598	Intermediate Similarity	NPC263455
0.7586	Intermediate Similarity	NPC472550
0.7586	Intermediate Similarity	NPC304179
0.7586	Intermediate Similarity	NPC48042
0.7573	Intermediate Similarity	NPC264674
0.7546	Intermediate Similarity	NPC475426
0.7542	Intermediate Similarity	NPC312860
0.7536	Intermediate Similarity	NPC76565
0.7536	Intermediate Similarity	NPC207531
0.7536	Intermediate Similarity	NPC193361
0.7536	Intermediate Similarity	NPC62844
0.7512	Intermediate Similarity	NPC40919
0.7512	Intermediate Similarity	NPC470189
0.75	Intermediate Similarity	NPC103230
0.75	Intermediate Similarity	NPC475137
0.75	Intermediate Similarity	NPC475498
0.75	Intermediate Similarity	NPC472752
0.75	Intermediate Similarity	NPC472070
0.75	Intermediate Similarity	NPC84347
0.7488	Intermediate Similarity	NPC477979
0.7488	Intermediate Similarity	NPC477788
0.7488	Intermediate Similarity	NPC228331
0.7476	Intermediate Similarity	NPC472553
0.7476	Intermediate Similarity	NPC477901
0.7475	Intermediate Similarity	NPC327592
0.7465	Intermediate Similarity	NPC473506
0.7465	Intermediate Similarity	NPC35208
0.7464	Intermediate Similarity	NPC319556
0.7453	Intermediate Similarity	NPC250807
0.7453	Intermediate Similarity	NPC57797
0.7452	Intermediate Similarity	NPC477909
0.7452	Intermediate Similarity	NPC36405
0.7452	Intermediate Similarity	NPC42678
0.7452	Intermediate Similarity	NPC477907
0.7448	Intermediate Similarity	NPC46895
0.7443	Intermediate Similarity	NPC230085
0.7443	Intermediate Similarity	NPC159630
0.7438	Intermediate Similarity	NPC317373
0.743	Intermediate Similarity	NPC475631
0.743	Intermediate Similarity	NPC87152
0.743	Intermediate Similarity	NPC475600
0.743	Intermediate Similarity	NPC476110
0.7424	Intermediate Similarity	NPC77061
0.7418	Intermediate Similarity	NPC473850
0.7418	Intermediate Similarity	NPC26881
0.7416	Intermediate Similarity	NPC206343
0.7416	Intermediate Similarity	NPC477908
0.7409	Intermediate Similarity	NPC311282
0.7406	Intermediate Similarity	NPC235364
0.7404	Intermediate Similarity	NPC319128
0.7404	Intermediate Similarity	NPC4421
0.7403	Intermediate Similarity	NPC229055
0.7395	Intermediate Similarity	NPC471977
0.7395	Intermediate Similarity	NPC471190
0.7395	Intermediate Similarity	NPC475644
0.7395	Intermediate Similarity	NPC470486
0.7391	Intermediate Similarity	NPC280473
0.7391	Intermediate Similarity	NPC323551
0.7389	Intermediate Similarity	NPC132539
0.7385	Intermediate Similarity	NPC44354
0.7381	Intermediate Similarity	NPC62367
0.7381	Intermediate Similarity	NPC187494
0.7373	Intermediate Similarity	NPC49547
0.7368	Intermediate Similarity	NPC470306
0.7368	Intermediate Similarity	NPC477910
0.7363	Intermediate Similarity	NPC74357
0.7363	Intermediate Similarity	NPC79223
0.736	Intermediate Similarity	NPC302159
0.7358	Intermediate Similarity	NPC477903
0.7356	Intermediate Similarity	NPC165837
0.7356	Intermediate Similarity	NPC51008
0.7356	Intermediate Similarity	NPC41724
0.7353	Intermediate Similarity	NPC309498
0.7349	Intermediate Similarity	NPC477787
0.7349	Intermediate Similarity	NPC146824
0.7349	Intermediate Similarity	NPC122968
0.7349	Intermediate Similarity	NPC328186
0.7349	Intermediate Similarity	NPC74575
0.7349	Intermediate Similarity	NPC228377
0.7346	Intermediate Similarity	NPC216428
0.7346	Intermediate Similarity	NPC472555
0.7336	Intermediate Similarity	NPC477900
0.7336	Intermediate Similarity	NPC477899
0.7333	Intermediate Similarity	NPC471014
0.7333	Intermediate Similarity	NPC471016
0.7333	Intermediate Similarity	NPC475408
0.7327	Intermediate Similarity	NPC475303
0.7327	Intermediate Similarity	NPC475596
0.7326	Intermediate Similarity	NPC70949
0.7317	Intermediate Similarity	NPC156044
0.7315	Intermediate Similarity	NPC475362
0.7308	Intermediate Similarity	NPC476467
0.7306	Intermediate Similarity	NPC327769
0.7306	Intermediate Similarity	NPC170751
0.7303	Intermediate Similarity	NPC167400
0.7299	Intermediate Similarity	NPC158020
0.7299	Intermediate Similarity	NPC473089
0.7299	Intermediate Similarity	NPC75600
0.7299	Intermediate Similarity	NPC6576
0.7299	Intermediate Similarity	NPC212768
0.7299	Intermediate Similarity	NPC473115
0.7294	Intermediate Similarity	NPC30456
0.7292	Intermediate Similarity	NPC61011
0.7292	Intermediate Similarity	NPC317010
0.7292	Intermediate Similarity	NPC471997
0.7282	Intermediate Similarity	NPC118084
0.7281	Intermediate Similarity	NPC91125
0.7277	Intermediate Similarity	NPC477912
0.7269	Intermediate Similarity	NPC14116
0.7269	Intermediate Similarity	NPC285411
0.7269	Intermediate Similarity	NPC475601
0.7269	Intermediate Similarity	NPC124029
0.7264	Intermediate Similarity	NPC320748
0.7264	Intermediate Similarity	NPC324245
0.7264	Intermediate Similarity	NPC301368
0.7264	Intermediate Similarity	NPC84815
0.7264	Intermediate Similarity	NPC248782
0.7256	Intermediate Similarity	NPC477902
0.7252	Intermediate Similarity	NPC253482
0.7251	Intermediate Similarity	NPC6981
0.7248	Intermediate Similarity	NPC477906
0.7248	Intermediate Similarity	NPC473689
0.7248	Intermediate Similarity	NPC316841
0.7248	Intermediate Similarity	NPC292416
0.7243	Intermediate Similarity	NPC216612
0.7243	Intermediate Similarity	NPC477911
0.7241	Intermediate Similarity	NPC32451
0.7241	Intermediate Similarity	NPC328559
0.7235	Intermediate Similarity	NPC311196
0.7235	Intermediate Similarity	NPC134384
0.7222	Intermediate Similarity	NPC470018
0.722	Intermediate Similarity	NPC12944
0.722	Intermediate Similarity	NPC25442
0.7217	Intermediate Similarity	NPC144779
0.7217	Intermediate Similarity	NPC294579
0.7215	Intermediate Similarity	NPC320324
0.7215	Intermediate Similarity	NPC244839
0.7215	Intermediate Similarity	NPC469748
0.7215	Intermediate Similarity	NPC319880
0.7214	Intermediate Similarity	NPC106824
0.7212	Intermediate Similarity	NPC470020
0.7209	Intermediate Similarity	NPC229893
0.7206	Intermediate Similarity	NPC57398
0.7206	Intermediate Similarity	NPC472063
0.7206	Intermediate Similarity	NPC328596
0.7206	Intermediate Similarity	NPC328318
0.7206	Intermediate Similarity	NPC472062
0.7206	Intermediate Similarity	NPC472069
0.7198	Intermediate Similarity	NPC470280
0.7189	Intermediate Similarity	NPC211920
0.7188	Intermediate Similarity	NPC83774
0.7184	Intermediate Similarity	NPC82053
0.7182	Intermediate Similarity	NPC237702
0.7178	Intermediate Similarity	NPC59033
0.7176	Intermediate Similarity	NPC233727
0.7176	Intermediate Similarity	NPC328154
0.7171	Intermediate Similarity	NPC317572
0.7169	Intermediate Similarity	NPC260434
0.7169	Intermediate Similarity	NPC96801
0.7169	Intermediate Similarity	NPC150698
0.7164	Intermediate Similarity	NPC472116
0.7163	Intermediate Similarity	NPC127026
0.7163	Intermediate Similarity	NPC127720
0.7157	Intermediate Similarity	NPC278434
0.7157	Intermediate Similarity	NPC98864
0.7156	Intermediate Similarity	NPC475648
0.7156	Intermediate Similarity	NPC146976

Chemically structural similarity: II. Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC135950 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	178
0.1-0.2	555
0.2-0.3	889
0.3-0.4	1321
0.4-0.5	2892
0.5-0.6	2403
0.6-0.7	850
0.7-0.8	57
0.8-0.85	5
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8187	Intermediate Similarity	NPD8304	Clinical (unspecified phase)
0.8144	Intermediate Similarity	NPD2121	Clinical (unspecified phase)
0.8103	Intermediate Similarity	NPD3947	Discontinued
0.8011	Intermediate Similarity	NPD820	Phase 3
0.7889	Intermediate Similarity	NPD2509	Approved
0.7889	Intermediate Similarity	NPD2510	Approved
0.7816	Intermediate Similarity	NPD9271	Approved
0.7809	Intermediate Similarity	NPD2582	Approved
0.7809	Intermediate Similarity	NPD2581	Approved
0.7772	Intermediate Similarity	NPD5475	Discontinued
0.7725	Intermediate Similarity	NPD1096	Discontinued
0.7707	Intermediate Similarity	NPD3394	Approved
0.7707	Intermediate Similarity	NPD3389	Approved
0.7707	Intermediate Similarity	NPD3393	Approved
0.77	Intermediate Similarity	NPD7010	Phase 3
0.7641	Intermediate Similarity	NPD5975	Clinical (unspecified phase)
0.7622	Intermediate Similarity	NPD485	Clinical (unspecified phase)
0.761	Intermediate Similarity	NPD3794	Approved
0.761	Intermediate Similarity	NPD3795	Approved
0.7574	Intermediate Similarity	NPD3371	Approved
0.7526	Intermediate Similarity	NPD3178	Discontinued
0.7526	Intermediate Similarity	NPD1783	Clinical (unspecified phase)
0.7512	Intermediate Similarity	NPD4417	Approved
0.7512	Intermediate Similarity	NPD7404	Approved
0.7476	Intermediate Similarity	NPD1996	Discontinued
0.7471	Intermediate Similarity	NPD107	Approved
0.7459	Intermediate Similarity	NPD4174	Clinical (unspecified phase)
0.7446	Intermediate Similarity	NPD5088	Discontinued
0.7444	Intermediate Similarity	NPD180	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD6770	Approved
0.7411	Intermediate Similarity	NPD4529	Approved
0.7411	Intermediate Similarity	NPD4526	Approved
0.7411	Intermediate Similarity	NPD4528	Approved
0.7381	Intermediate Similarity	NPD4429	Discontinued
0.736	Intermediate Similarity	NPD4376	Phase 3
0.7353	Intermediate Similarity	NPD4862	Clinical (unspecified phase)
0.735	Intermediate Similarity	NPD4987	Clinical (unspecified phase)
0.733	Intermediate Similarity	NPD6529	Discontinued
0.7311	Intermediate Similarity	NPD3280	Approved
0.7303	Intermediate Similarity	NPD9074	Approved
0.7303	Intermediate Similarity	NPD9075	Approved
0.7302	Intermediate Similarity	NPD2076	Approved
0.7302	Intermediate Similarity	NPD2077	Approved
0.7292	Intermediate Similarity	NPD1643	Phase 3
0.7277	Intermediate Similarity	NPD4301	Approved
0.7273	Intermediate Similarity	NPD5891	Approved
0.7273	Intermediate Similarity	NPD3006	Discontinued
0.7246	Intermediate Similarity	NPD4506	Discontinued
0.7225	Intermediate Similarity	NPD6657	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD1270	Approved
0.7222	Intermediate Similarity	NPD2336	Approved
0.7202	Intermediate Similarity	NPD5022	Discontinued
0.7164	Intermediate Similarity	NPD7061	Clinical (unspecified phase)
0.7136	Intermediate Similarity	NPD2831	Approved
0.7136	Intermediate Similarity	NPD7396	Approved
0.7124	Intermediate Similarity	NPD5483	Clinical (unspecified phase)
0.7119	Intermediate Similarity	NPD4804	Approved
0.7115	Intermediate Similarity	NPD7467	Discontinued
0.7113	Intermediate Similarity	NPD2481	Approved
0.7113	Intermediate Similarity	NPD2479	Phase 3
0.71	Intermediate Similarity	NPD6665	Discontinued
0.7098	Intermediate Similarity	NPD2921	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD7470	Discontinued
0.7092	Intermediate Similarity	NPD3569	Discontinued
0.7085	Intermediate Similarity	NPD8063	Discontinued
0.7085	Intermediate Similarity	NPD4958	Clinical (unspecified phase)
0.7079	Intermediate Similarity	NPD2307	Discontinued
0.7056	Intermediate Similarity	NPD1623	Approved
0.7056	Intermediate Similarity	NPD4889	Approved
0.7053	Intermediate Similarity	NPD6987	Phase 1
0.7045	Intermediate Similarity	NPD4952	Phase 3
0.7039	Intermediate Similarity	NPD4805	Approved
0.7035	Intermediate Similarity	NPD7234	Approved
0.7035	Intermediate Similarity	NPD7233	Approved
0.7019	Intermediate Similarity	NPD7289	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD8468	Phase 2
0.7014	Intermediate Similarity	NPD5416	Discontinued
0.7009	Intermediate Similarity	NPD3326	Clinical (unspecified phase)
0.7005	Intermediate Similarity	NPD5255	Approved
0.7005	Intermediate Similarity	NPD5513	Phase 2
0.7005	Intermediate Similarity	NPD8356	Approved
0.7005	Intermediate Similarity	NPD1630	Approved
0.7	Intermediate Similarity	NPD5482	Discontinued
0.6995	Remote Similarity	NPD5417	Clinical (unspecified phase)
0.6995	Remote Similarity	NPD6226	Phase 3
0.6986	Remote Similarity	NPD8289	Discontinued
0.6985	Remote Similarity	NPD4948	Discontinued
0.6981	Remote Similarity	NPD5866	Approved
0.698	Remote Similarity	NPD1173	Approved
0.6977	Remote Similarity	NPD6578	Clinical (unspecified phase)
0.6971	Remote Similarity	NPD5901	Discontinued
0.6971	Remote Similarity	NPD1627	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD1659	Phase 1
0.6955	Remote Similarity	NPD7994	Phase 2
0.6951	Remote Similarity	NPD4373	Phase 2
0.6942	Remote Similarity	NPD6479	Discontinued
0.6942	Remote Similarity	NPD4491	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD7688	Phase 1
0.6923	Remote Similarity	NPD2753	Discontinued
0.6915	Remote Similarity	NPD2565	Phase 2
0.6915	Remote Similarity	NPD2564	Approved
0.6907	Remote Similarity	NPD4736	Clinical (unspecified phase)
0.6904	Remote Similarity	NPD9362	Approved
0.6898	Remote Similarity	NPD7395	Discontinued
0.6895	Remote Similarity	NPD6173	Approved
0.6895	Remote Similarity	NPD1631	Approved
0.6895	Remote Similarity	NPD7547	Clinical (unspecified phase)
0.6895	Remote Similarity	NPD6635	Approved
0.6892	Remote Similarity	NPD5801	Clinical (unspecified phase)
0.689	Remote Similarity	NPD3946	Clinical (unspecified phase)
0.6878	Remote Similarity	NPD5003	Discontinued
0.6878	Remote Similarity	NPD687	Clinical (unspecified phase)
0.6878	Remote Similarity	NPD8430	Approved
0.6872	Remote Similarity	NPD203	Clinical (unspecified phase)
0.6872	Remote Similarity	NPD3238	Discontinued
0.6872	Remote Similarity	NPD7885	Phase 2
0.6872	Remote Similarity	NPD2896	Discontinued
0.6872	Remote Similarity	NPD7886	Phase 2
0.6869	Remote Similarity	NPD2823	Clinical (unspecified phase)
0.6869	Remote Similarity	NPD5888	Phase 2
0.6868	Remote Similarity	NPD751	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD4427	Phase 2
0.686	Remote Similarity	NPD4396	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD7001	Phase 3
0.6854	Remote Similarity	NPD7927	Clinical (unspecified phase)
0.6853	Remote Similarity	NPD9510	Approved
0.6849	Remote Similarity	NPD6160	Clinical (unspecified phase)
0.6845	Remote Similarity	NPD2809	Approved
0.6842	Remote Similarity	NPD6176	Phase 1
0.6842	Remote Similarity	NPD6790	Phase 1
0.6837	Remote Similarity	NPD7538	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD8479	Phase 2
0.6835	Remote Similarity	NPD6242	Discontinued
0.6834	Remote Similarity	NPD2091	Phase 2
0.6834	Remote Similarity	NPD2096	Phase 2
0.6834	Remote Similarity	NPD721	Approved
0.6833	Remote Similarity	NPD5887	Clinical (unspecified phase)
0.6833	Remote Similarity	NPD5640	Discontinued
0.6832	Remote Similarity	NPD3321	Discontinued
0.6825	Remote Similarity	NPD2214	Approved
0.6825	Remote Similarity	NPD2213	Approved
0.6822	Remote Similarity	NPD7069	Discontinued
0.6818	Remote Similarity	NPD6752	Phase 1
0.6818	Remote Similarity	NPD6753	Phase 1
0.6816	Remote Similarity	NPD8052	Clinical (unspecified phase)
0.6814	Remote Similarity	NPD7853	Phase 2
0.6812	Remote Similarity	NPD6661	Clinical (unspecified phase)
0.6808	Remote Similarity	NPD7998	Clinical (unspecified phase)
0.6798	Remote Similarity	NPD272	Approved
0.6793	Remote Similarity	NPD1801	Approved
0.6793	Remote Similarity	NPD1802	Approved
0.6789	Remote Similarity	NPD2511	Approved
0.6784	Remote Similarity	NPD2092	Phase 2
0.6784	Remote Similarity	NPD2094	Phase 2
0.6784	Remote Similarity	NPD2095	Phase 2
0.6784	Remote Similarity	NPD5728	Clinical (unspecified phase)
0.6784	Remote Similarity	NPD946	Discontinued
0.6779	Remote Similarity	NPD8248	Clinical (unspecified phase)
0.6776	Remote Similarity	NPD7703	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD8325	Phase 3
0.6774	Remote Similarity	NPD8327	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD8326	Phase 3
0.6769	Remote Similarity	NPD750	Phase 2
0.6768	Remote Similarity	NPD1291	Clinical (unspecified phase)
0.6766	Remote Similarity	NPD3315	Phase 3
0.6765	Remote Similarity	NPD6569	Phase 2
0.6759	Remote Similarity	NPD5149	Phase 2
0.6759	Remote Similarity	NPD5148	Clinical (unspecified phase)
0.6759	Remote Similarity	NPD5293	Phase 2
0.6758	Remote Similarity	NPD7180	Phase 3
0.6757	Remote Similarity	NPD4702	Approved
0.6757	Remote Similarity	NPD4703	Approved
0.6755	Remote Similarity	NPD5257	Clinical (unspecified phase)
0.6753	Remote Similarity	NPD1575	Approved
0.6753	Remote Similarity	NPD1573	Approved
0.6751	Remote Similarity	NPD4072	Approved
0.6751	Remote Similarity	NPD6642	Approved
0.6751	Remote Similarity	NPD6641	Approved
0.6751	Remote Similarity	NPD4071	Approved
0.6751	Remote Similarity	NPD5751	Clinical (unspecified phase)
0.6749	Remote Similarity	NPD6281	Approved
0.6748	Remote Similarity	NPD3478	Clinical (unspecified phase)
0.6748	Remote Similarity	NPD3477	Phase 2
0.6743	Remote Similarity	NPD6568	Discontinued
0.6743	Remote Similarity	NPD5632	Approved
0.6738	Remote Similarity	NPD5965	Clinical (unspecified phase)
0.6735	Remote Similarity	NPD5322	Clinical (unspecified phase)
0.6734	Remote Similarity	NPD4011	Clinical (unspecified phase)
0.6733	Remote Similarity	NPD9364	Phase 2
0.6733	Remote Similarity	NPD9363	Approved
0.673	Remote Similarity	NPD944	Approved
0.6729	Remote Similarity	NPD5072	Discontinued
0.6726	Remote Similarity	NPD4086	Phase 1
0.6726	Remote Similarity	NPD3259	Approved
0.6726	Remote Similarity	NPD6741	Clinical (unspecified phase)
0.672	Remote Similarity	NPD2737	Clinical (unspecified phase)
0.6714	Remote Similarity	NPD5721	Clinical (unspecified phase)
0.6714	Remote Similarity	NPD6477	Clinical (unspecified phase)
0.6713	Remote Similarity	NPD3945	Discontinued
0.6701	Remote Similarity	NPD1343	Approved

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data