NPASS Compound

Structure

CID316411 OpenBabel06191716132D 34 38 0 0 0 0 0 0 0 0999 V2000 0.3090 0.9511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5878 0.9230 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4826 0.4598 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9921 -3.8781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1759 -4.8531 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1261 -4.3781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9190 -4.1840 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1261 -2.3781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0169 -3.5659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2788 -3.3781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7111 -1.5878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9921 -2.8781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2248 -4.5441 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2601 -2.8781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7601 -2.8968 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3090 -2.5691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7601 -1.8968 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2601 -3.8781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7111 -3.2058 0.0000 C 0 0 0 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 -0.9511 -1.3090 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 -0.9511 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5878 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7601 0.2788 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8581 -2.3781 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0 -0.4817 -5.2132 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0 0.3090 -4.1871 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -3.2989 -2.3968 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 2.0878 -1.6750 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 2.0878 0.0570 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6736 -0.1280 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 30 1 0 0 0 0 2 33 1 0 0 0 0 3 34 1 0 0 0 0 4 6 2 0 0 0 0 4 12 1 0 0 0 0 5 7 2 0 0 0 0 5 13 1 0 0 0 0 6 18 1 0 0 0 0 7 19 1 0 0 0 0 8 12 2 0 0 0 0 8 14 1 0 0 0 0 9 13 2 0 0 0 0 9 15 1 0 0 0 0 10 16 2 0 0 0 0 10 28 1 0 0 0 0 11 17 2 0 0 0 0 11 29 1 0 0 0 0 12 26 1 0 0 0 0 13 27 1 0 0 0 0 14 16 1 0 0 0 0 14 18 2 0 0 0 0 15 17 1 0 0 0 0 15 19 2 0 0 0 0 16 20 1 0 0 0 0 17 21 1 0 0 0 0 18 28 1 0 0 0 0 19 29 1 0 0 0 0 20 21 1 0 0 0 0 20 22 2 0 0 0 0 21 23 2 0 0 0 0 22 24 1 0 0 0 0 22 30 1 0 0 0 0 23 25 1 0 0 0 0 23 30 1 0 0 0 0 24 31 2 0 0 0 0 24 33 1 0 0 0 0 25 32 2 0 0 0 0 25 34 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	495.08
Volume:	465.11
LogP:	5.842
LogD:	4.081
LogS:	-6.762
# Rotatable Bonds:	6
TPSA:	89.11
# H-Bond Aceptor:	7
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.29
Synthetic Accessibility Score:	2.829
Fsp3:	0.12
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.238
MDCK Permeability:	9.978886737371795e-06
Pgp-inhibitor:	0.99
Pgp-substrate:	0.567
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.005

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.023
Plasma Protein Binding (PPB):	98.66764068603516%
Volume Distribution (VD):	0.971
Pgp-substrate:	0.8412638902664185%

ADMET: Metabolism

CYP1A2-inhibitor:	0.927
CYP1A2-substrate:	0.606
CYP2C19-inhibitor:	0.945
CYP2C19-substrate:	0.066
CYP2C9-inhibitor:	0.906
CYP2C9-substrate:	0.928
CYP2D6-inhibitor:	0.463
CYP2D6-substrate:	0.823
CYP3A4-inhibitor:	0.83
CYP3A4-substrate:	0.173

ADMET: Excretion

Clearance (CL):	7.021
Half-life (T1/2):	0.058

ADMET: Toxicity

hERG Blockers:	0.408
Human Hepatotoxicity (H-HT):	0.955
Drug-inuced Liver Injury (DILI):	0.971
AMES Toxicity:	0.058
Rat Oral Acute Toxicity:	0.12
Maximum Recommended Daily Dose:	0.973
Skin Sensitization:	0.056
Carcinogencity:	0.037
Eye Corrosion:	0.003
Eye Irritation:	0.017
Respiratory Toxicity:	0.068

Download Data

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

Natural Product: NPC316411

Natural Product ID:	NPC316411
*Common Name:**	HDSWTZRUKHSYDF-UHFFFAOYSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	HDSWTZRUKHSYDF-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C25H19Cl2N3O4/c1-30-22(24(31)33-2)20(16-10-28-18-6-4-12(26)8-14(16)18)21(23(30)25(32)34-3)17-11-29-19-7-5-13(27)9-15(17)19/h4-11,28-29H,1-3H3
SMILES:	Cn1c(c(c2c[nH]c3ccc(cc23)Cl)c(c2c[nH]c3ccc(cc23)Cl)c1C(=O)OC)C(=O)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3327032
PubChem CID:	NA
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000211] Indoles and derivatives [CHEMONTID:0002497] Indoles

*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
NPO40641	Streptomyces sp. SCSIO 03032	Strain	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[24547685]
NPO40641	Streptomyces sp. SCSIO 03032	Strain	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[25069084]

☑ 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
IC50	1
MIC	5

Activity Type	# Activity
Cell Line	1
Organism	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	10000.0	nM	PMID[542483]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	128.0	ug.mL-1	PMID[542483]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	>	128.0	ug.mL-1	PMID[542483]
NPT1261	Organism	Bacillus thuringiensis	Bacillus thuringiensis	MIC	>	128.0	ug.mL-1	PMID[542483]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	>	128.0	ug.mL-1	PMID[542483]
NPT20	Organism	Candida albicans	Candida albicans	MIC	>	128.0	ug.mL-1	PMID[542483]

☑ 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 NPC316411 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	563
0.1-0.2	4274
0.2-0.3	13280
0.3-0.4	17206
0.4-0.5	3353
0.5-0.6	2168
0.6-0.7	1670
0.7-0.8	171
0.8-0.85	4
0.85-0.9	1
0.9-0.95	2
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.9903	High Similarity	NPC244897
0.9855	High Similarity	NPC315062
0.9855	High Similarity	NPC267853
0.971	High Similarity	NPC192712
0.9349	High Similarity	NPC104712
0.9227	High Similarity	NPC36405
0.8673	High Similarity	NPC82370
0.8489	Intermediate Similarity	NPC15801
0.8203	Intermediate Similarity	NPC118940
0.8104	Intermediate Similarity	NPC67288
0.7936	Intermediate Similarity	NPC266249
0.792	Intermediate Similarity	NPC229893
0.7892	Intermediate Similarity	NPC472285
0.7864	Intermediate Similarity	NPC123839
0.7723	Intermediate Similarity	NPC477979
0.765	Intermediate Similarity	NPC74413
0.7644	Intermediate Similarity	NPC474412
0.7642	Intermediate Similarity	NPC321708
0.7636	Intermediate Similarity	NPC132539
0.7626	Intermediate Similarity	NPC260900
0.7626	Intermediate Similarity	NPC57398
0.7604	Intermediate Similarity	NPC131887
0.757	Intermediate Similarity	NPC138370
0.756	Intermediate Similarity	NPC314919
0.7548	Intermediate Similarity	NPC84827
0.7548	Intermediate Similarity	NPC145885
0.7548	Intermediate Similarity	NPC14113
0.7547	Intermediate Similarity	NPC160381
0.75	Intermediate Similarity	NPC312645
0.7489	Intermediate Similarity	NPC478157
0.7489	Intermediate Similarity	NPC260434
0.7477	Intermediate Similarity	NPC227582
0.7448	Intermediate Similarity	NPC101350
0.7445	Intermediate Similarity	NPC89508
0.7422	Intermediate Similarity	NPC478158
0.7406	Intermediate Similarity	NPC240384
0.7406	Intermediate Similarity	NPC235685
0.7397	Intermediate Similarity	NPC141454
0.7376	Intermediate Similarity	NPC252338
0.7361	Intermediate Similarity	NPC83111
0.7346	Intermediate Similarity	NPC126709
0.7346	Intermediate Similarity	NPC248041
0.7346	Intermediate Similarity	NPC283219
0.7339	Intermediate Similarity	NPC304203
0.733	Intermediate Similarity	NPC123395
0.7322	Intermediate Similarity	NPC39370
0.7311	Intermediate Similarity	NPC473186
0.7311	Intermediate Similarity	NPC469896
0.7309	Intermediate Similarity	NPC53534
0.7309	Intermediate Similarity	NPC193761
0.7302	Intermediate Similarity	NPC235684
0.7277	Intermediate Similarity	NPC165599
0.7273	Intermediate Similarity	NPC152620
0.7257	Intermediate Similarity	NPC54420
0.7253	Intermediate Similarity	NPC276657
0.7251	Intermediate Similarity	NPC267885
0.7248	Intermediate Similarity	NPC476460
0.7246	Intermediate Similarity	NPC472762
0.7241	Intermediate Similarity	NPC264285
0.7232	Intermediate Similarity	NPC476073
0.7217	Intermediate Similarity	NPC111275
0.7208	Intermediate Similarity	NPC70155
0.7207	Intermediate Similarity	NPC171317
0.7204	Intermediate Similarity	NPC203468
0.7204	Intermediate Similarity	NPC110500
0.7204	Intermediate Similarity	NPC149155
0.7193	Intermediate Similarity	NPC162860
0.7191	Intermediate Similarity	NPC16352
0.7185	Intermediate Similarity	NPC194740
0.7182	Intermediate Similarity	NPC472295
0.7182	Intermediate Similarity	NPC269886
0.7182	Intermediate Similarity	NPC472210
0.7182	Intermediate Similarity	NPC247735
0.7182	Intermediate Similarity	NPC81802
0.7181	Intermediate Similarity	NPC244741
0.7178	Intermediate Similarity	NPC182222
0.7167	Intermediate Similarity	NPC196718
0.7161	Intermediate Similarity	NPC122436
0.7156	Intermediate Similarity	NPC476874
0.7143	Intermediate Similarity	NPC214428
0.7137	Intermediate Similarity	NPC82053
0.7136	Intermediate Similarity	NPC314058
0.7136	Intermediate Similarity	NPC316359
0.7136	Intermediate Similarity	NPC315617
0.7136	Intermediate Similarity	NPC284775
0.7136	Intermediate Similarity	NPC316018
0.7136	Intermediate Similarity	NPC472292
0.7131	Intermediate Similarity	NPC476818
0.713	Intermediate Similarity	NPC284678
0.7124	Intermediate Similarity	NPC317701
0.7117	Intermediate Similarity	NPC472293
0.7113	Intermediate Similarity	NPC33949
0.7111	Intermediate Similarity	NPC471944
0.711	Intermediate Similarity	NPC278434
0.7102	Intermediate Similarity	NPC148889
0.7101	Intermediate Similarity	NPC24370
0.7101	Intermediate Similarity	NPC319232
0.71	Intermediate Similarity	NPC75634
0.71	Intermediate Similarity	NPC318299
0.71	Intermediate Similarity	NPC473493
0.71	Intermediate Similarity	NPC207020
0.7098	Intermediate Similarity	NPC103361
0.7097	Intermediate Similarity	NPC282103
0.7095	Intermediate Similarity	NPC78020
0.7095	Intermediate Similarity	NPC207686
0.7095	Intermediate Similarity	NPC102593
0.7093	Intermediate Similarity	NPC473376
0.7083	Intermediate Similarity	NPC472844
0.7083	Intermediate Similarity	NPC83381
0.7075	Intermediate Similarity	NPC258048
0.7069	Intermediate Similarity	NPC234078
0.7069	Intermediate Similarity	NPC39500
0.7069	Intermediate Similarity	NPC54744
0.7069	Intermediate Similarity	NPC229348
0.7069	Intermediate Similarity	NPC317752
0.7069	Intermediate Similarity	NPC221100
0.7068	Intermediate Similarity	NPC91868
0.7068	Intermediate Similarity	NPC63971
0.7061	Intermediate Similarity	NPC277350
0.7059	Intermediate Similarity	NPC55493
0.7047	Intermediate Similarity	NPC74619
0.7043	Intermediate Similarity	NPC61038
0.704	Intermediate Similarity	NPC102592
0.704	Intermediate Similarity	NPC79356
0.704	Intermediate Similarity	NPC245916
0.7037	Intermediate Similarity	NPC325976
0.7034	Intermediate Similarity	NPC14686
0.7032	Intermediate Similarity	NPC17059
0.7031	Intermediate Similarity	NPC1203
0.7031	Intermediate Similarity	NPC321428
0.7027	Intermediate Similarity	NPC88315
0.7027	Intermediate Similarity	NPC326422
0.7026	Intermediate Similarity	NPC110182
0.7023	Intermediate Similarity	NPC219336
0.7023	Intermediate Similarity	NPC213468
0.7023	Intermediate Similarity	NPC55772
0.7022	Intermediate Similarity	NPC472296
0.7022	Intermediate Similarity	NPC472297
0.7021	Intermediate Similarity	NPC477714
0.7021	Intermediate Similarity	NPC281049
0.7018	Intermediate Similarity	NPC280290
0.7018	Intermediate Similarity	NPC327592
0.7009	Intermediate Similarity	NPC85702
0.7009	Intermediate Similarity	NPC262898
0.7004	Intermediate Similarity	NPC60621
0.7	Intermediate Similarity	NPC196251
0.7	Intermediate Similarity	NPC111602
0.7	Intermediate Similarity	NPC102338
0.7	Intermediate Similarity	NPC213629
0.7	Intermediate Similarity	NPC63199
0.6996	Remote Similarity	NPC472291
0.6996	Remote Similarity	NPC19692
0.6996	Remote Similarity	NPC323198
0.6996	Remote Similarity	NPC220151
0.6996	Remote Similarity	NPC323752
0.6992	Remote Similarity	NPC269270
0.6992	Remote Similarity	NPC74360
0.6991	Remote Similarity	NPC213308
0.6991	Remote Similarity	NPC315491
0.6991	Remote Similarity	NPC45459
0.6988	Remote Similarity	NPC178858
0.6987	Remote Similarity	NPC300156
0.6987	Remote Similarity	NPC317373
0.6986	Remote Similarity	NPC315555
0.6986	Remote Similarity	NPC62749
0.6979	Remote Similarity	NPC477715
0.6978	Remote Similarity	NPC474916
0.6977	Remote Similarity	NPC217372
0.6977	Remote Similarity	NPC15573
0.6977	Remote Similarity	NPC183662
0.6977	Remote Similarity	NPC59269
0.6975	Remote Similarity	NPC144452
0.6974	Remote Similarity	NPC475774
0.6968	Remote Similarity	NPC469489
0.6966	Remote Similarity	NPC118228
0.6964	Remote Similarity	NPC179701
0.6959	Remote Similarity	NPC71037
0.6957	Remote Similarity	NPC4687
0.6952	Remote Similarity	NPC8104
0.6949	Remote Similarity	NPC184408
0.6948	Remote Similarity	NPC78609
0.6947	Remote Similarity	NPC293917
0.6941	Remote Similarity	NPC15102
0.6926	Remote Similarity	NPC39679
0.6923	Remote Similarity	NPC207866
0.692	Remote Similarity	NPC202812
0.692	Remote Similarity	NPC135950
0.6917	Remote Similarity	NPC125597
0.6914	Remote Similarity	NPC475859
0.6914	Remote Similarity	NPC474877
0.6914	Remote Similarity	NPC472842
0.6914	Remote Similarity	NPC475969
0.6913	Remote Similarity	NPC175602
0.6909	Remote Similarity	NPC94752
0.6905	Remote Similarity	NPC26543
0.6903	Remote Similarity	NPC470499
0.6901	Remote Similarity	NPC274640
0.6901	Remote Similarity	NPC314954
0.6895	Remote Similarity	NPC207851
0.6892	Remote Similarity	NPC154339

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 NPC316411 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	281
0.1-0.2	689
0.2-0.3	866
0.3-0.4	2050
0.4-0.5	2606
0.5-0.6	1976
0.6-0.7	630
0.7-0.8	52
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
0.7991	Intermediate Similarity	NPD7470	Discontinued
0.7964	Intermediate Similarity	NPD3757	Clinical (unspecified phase)
0.7805	Intermediate Similarity	NPD5450	Discontinued
0.7763	Intermediate Similarity	NPD4862	Clinical (unspecified phase)
0.7752	Intermediate Similarity	NPD2121	Clinical (unspecified phase)
0.7717	Intermediate Similarity	NPD5901	Discontinued
0.7717	Intermediate Similarity	NPD2721	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD2509	Approved
0.7692	Intermediate Similarity	NPD2510	Approved
0.7682	Intermediate Similarity	NPD2715	Clinical (unspecified phase)
0.7657	Intermediate Similarity	NPD5483	Clinical (unspecified phase)
0.7564	Intermediate Similarity	NPD7688	Phase 1
0.7563	Intermediate Similarity	NPD2921	Clinical (unspecified phase)
0.7531	Intermediate Similarity	NPD5482	Discontinued
0.7477	Intermediate Similarity	NPD3947	Discontinued
0.7444	Intermediate Similarity	NPD7001	Phase 3
0.7399	Intermediate Similarity	NPD5426	Phase 3
0.7395	Intermediate Similarity	NPD1534	Approved
0.7389	Intermediate Similarity	NPD7998	Clinical (unspecified phase)
0.7384	Intermediate Similarity	NPD6263	Clinical (unspecified phase)
0.738	Intermediate Similarity	NPD3389	Approved
0.738	Intermediate Similarity	NPD3393	Approved
0.738	Intermediate Similarity	NPD3394	Approved
0.7362	Intermediate Similarity	NPD3259	Approved
0.7358	Intermediate Similarity	NPD3178	Discontinued
0.7357	Intermediate Similarity	NPD8013	Clinical (unspecified phase)
0.7281	Intermediate Similarity	NPD5475	Discontinued
0.7255	Intermediate Similarity	NPD7393	Clinical (unspecified phase)
0.7253	Intermediate Similarity	NPD1996	Discontinued
0.7253	Intermediate Similarity	NPD6242	Discontinued
0.7252	Intermediate Similarity	NPD6999	Discontinued
0.7252	Intermediate Similarity	NPD7000	Clinical (unspecified phase)
0.7251	Intermediate Similarity	NPD749	Clinical (unspecified phase)
0.7243	Intermediate Similarity	NPD2094	Phase 2
0.7243	Intermediate Similarity	NPD7576	Discontinued
0.7243	Intermediate Similarity	NPD2095	Phase 2
0.7243	Intermediate Similarity	NPD2092	Phase 2
0.7217	Intermediate Similarity	NPD3243	Approved
0.7212	Intermediate Similarity	NPD6732	Clinical (unspecified phase)
0.7209	Intermediate Similarity	NPD2096	Phase 2
0.7209	Intermediate Similarity	NPD2091	Phase 2
0.7204	Intermediate Similarity	NPD482	Approved
0.7195	Intermediate Similarity	NPD4848	Phase 1
0.7191	Intermediate Similarity	NPD6160	Clinical (unspecified phase)
0.7186	Intermediate Similarity	NPD3257	Approved
0.7179	Intermediate Similarity	NPD3280	Approved
0.7162	Intermediate Similarity	NPD5003	Discontinued
0.7156	Intermediate Similarity	NPD750	Phase 2
0.7149	Intermediate Similarity	NPD4454	Phase 2
0.7137	Intermediate Similarity	NPD3258	Approved
0.7137	Intermediate Similarity	NPD6770	Approved
0.713	Intermediate Similarity	NPD4987	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD8238	Clinical (unspecified phase)
0.7119	Intermediate Similarity	NPD6995	Phase 1
0.7093	Intermediate Similarity	NPD6288	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD5728	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD3006	Discontinued
0.7074	Intermediate Similarity	NPD7665	Phase 2
0.7074	Intermediate Similarity	NPD7666	Phase 3
0.707	Intermediate Similarity	NPD6595	Phase 3
0.7026	Intermediate Similarity	NPD8349	Phase 1
0.7026	Intermediate Similarity	NPD8097	Phase 3
0.7026	Intermediate Similarity	NPD8096	Phase 3
0.7021	Intermediate Similarity	NPD5632	Approved
0.6996	Remote Similarity	NPD2823	Clinical (unspecified phase)
0.6991	Remote Similarity	NPD484	Approved
0.6974	Remote Similarity	NPD6176	Phase 1
0.6963	Remote Similarity	NPD1586	Approved
0.6957	Remote Similarity	NPD8463	Approved
0.6955	Remote Similarity	NPD4948	Discontinued
0.6953	Remote Similarity	NPD4852	Phase 2
0.6949	Remote Similarity	NPD8405	Clinical (unspecified phase)
0.6948	Remote Similarity	NPD5472	Clinical (unspecified phase)
0.6947	Remote Similarity	NPD7621	Clinical (unspecified phase)
0.6946	Remote Similarity	NPD3222	Phase 2
0.6943	Remote Similarity	NPD8098	Approved
0.6939	Remote Similarity	NPD6735	Approved
0.6936	Remote Similarity	NPD6803	Clinical (unspecified phase)
0.6936	Remote Similarity	NPD8160	Phase 2
0.6929	Remote Similarity	NPD7994	Phase 2
0.6929	Remote Similarity	NPD4845	Discontinued
0.6929	Remote Similarity	NPD4328	Approved
0.692	Remote Similarity	NPD7404	Approved
0.692	Remote Similarity	NPD3791	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD6217	Discontinued
0.6907	Remote Similarity	NPD6710	Phase 3
0.6907	Remote Similarity	NPD5818	Discontinued
0.6895	Remote Similarity	NPD3607	Clinical (unspecified phase)
0.6892	Remote Similarity	NPD2565	Phase 2
0.6892	Remote Similarity	NPD2564	Approved
0.6888	Remote Similarity	NPD8289	Discontinued
0.6883	Remote Similarity	NPD8493	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD8279	Clinical (unspecified phase)
0.6878	Remote Similarity	NPD4429	Discontinued
0.6875	Remote Similarity	NPD4529	Approved
0.6875	Remote Similarity	NPD4528	Approved
0.6875	Remote Similarity	NPD4526	Approved
0.6872	Remote Similarity	NPD5801	Clinical (unspecified phase)
0.6872	Remote Similarity	NPD5479	Discontinued
0.687	Remote Similarity	NPD6987	Phase 1
0.687	Remote Similarity	NPD8282	Approved
0.687	Remote Similarity	NPD5891	Approved
0.687	Remote Similarity	NPD8283	Approved
0.687	Remote Similarity	NPD56	Approved
0.6867	Remote Similarity	NPD3914	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD7825	Clinical (unspecified phase)
0.6866	Remote Similarity	NPD1587	Approved
0.6865	Remote Similarity	NPD4558	Phase 2
0.6864	Remote Similarity	NPD6610	Clinical (unspecified phase)
0.6861	Remote Similarity	NPD6180	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD7953	Approved
0.6857	Remote Similarity	NPD7789	Approved
0.6857	Remote Similarity	NPD7950	Approved
0.6857	Remote Similarity	NPD7791	Approved
0.6857	Remote Similarity	NPD7951	Approved
0.6857	Remote Similarity	NPD7952	Approved
0.6857	Remote Similarity	NPD5040	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD7790	Approved
0.6852	Remote Similarity	NPD5471	Phase 3
0.6844	Remote Similarity	NPD1867	Approved
0.6842	Remote Similarity	NPD2305	Discontinued
0.684	Remote Similarity	NPD7010	Phase 3
0.6837	Remote Similarity	NPD2076	Approved
0.6837	Remote Similarity	NPD2077	Approved
0.6835	Remote Similarity	NPD8464	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD6452	Discontinued
0.6824	Remote Similarity	NPD4506	Discontinued
0.6824	Remote Similarity	NPD7704	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD7603	Discontinued
0.6816	Remote Similarity	NPD4499	Approved
0.6815	Remote Similarity	NPD6154	Approved
0.681	Remote Similarity	NPD6838	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD8093	Discontinued
0.6806	Remote Similarity	NPD5065	Approved
0.6804	Remote Similarity	NPD4383	Clinical (unspecified phase)
0.6798	Remote Similarity	NPD8102	Discontinued
0.6795	Remote Similarity	NPD7809	Clinical (unspecified phase)
0.679	Remote Similarity	NPD6165	Phase 2
0.679	Remote Similarity	NPD7731	Approved
0.679	Remote Similarity	NPD7730	Approved
0.679	Remote Similarity	NPD6164	Phase 2
0.6786	Remote Similarity	NPD5912	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD5913	Phase 3
0.6781	Remote Similarity	NPD7947	Clinical (unspecified phase)
0.678	Remote Similarity	NPD1322	Clinical (unspecified phase)
0.678	Remote Similarity	NPD3794	Approved
0.678	Remote Similarity	NPD3795	Approved
0.6777	Remote Similarity	NPD7271	Approved
0.6776	Remote Similarity	NPD2844	Phase 3
0.6762	Remote Similarity	NPD7781	Approved
0.6762	Remote Similarity	NPD1580	Clinical (unspecified phase)
0.6762	Remote Similarity	NPD7780	Approved
0.6757	Remote Similarity	NPD4426	Clinical (unspecified phase)
0.6756	Remote Similarity	NPD6665	Discontinued
0.6754	Remote Similarity	NPD7946	Pre-registration
0.6753	Remote Similarity	NPD8072	Approved
0.6752	Remote Similarity	NPD2125	Clinical (unspecified phase)
0.6751	Remote Similarity	NPD6745	Discontinued
0.6743	Remote Similarity	NPD6203	Clinical (unspecified phase)
0.674	Remote Similarity	NPD1851	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD7903	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD5017	Discontinued
0.6737	Remote Similarity	NPD6657	Clinical (unspecified phase)
0.6735	Remote Similarity	NPD7824	Approved
0.6735	Remote Similarity	NPD4952	Phase 3
0.6726	Remote Similarity	NPD1038	Approved
0.6726	Remote Similarity	NPD1304	Clinical (unspecified phase)
0.6711	Remote Similarity	NPD4699	Discontinued
0.6711	Remote Similarity	NPD7948	Phase 1
0.671	Remote Similarity	NPD8073	Approved
0.6707	Remote Similarity	NPD4958	Clinical (unspecified phase)
0.6697	Remote Similarity	NPD4345	Clinical (unspecified phase)
0.6696	Remote Similarity	NPD4501	Approved
0.6696	Remote Similarity	NPD8248	Clinical (unspecified phase)
0.6696	Remote Similarity	NPD4500	Approved
0.6695	Remote Similarity	NPD7958	Clinical (unspecified phase)
0.6695	Remote Similarity	NPD7957	Phase 1
0.6694	Remote Similarity	NPD6130	Phase 1
0.6693	Remote Similarity	NPD6790	Phase 1
0.6692	Remote Similarity	NPD6531	Approved
0.6692	Remote Similarity	NPD6530	Approved
0.6681	Remote Similarity	NPD3230	Clinical (unspecified phase)
0.6681	Remote Similarity	NPD8112	Clinical (unspecified phase)
0.668	Remote Similarity	NPD7772	Phase 3
0.668	Remote Similarity	NPD4885	Approved
0.668	Remote Similarity	NPD7711	Discontinued
0.6667	Remote Similarity	NPD5866	Approved
0.6667	Remote Similarity	NPD7548	Discontinued
0.6667	Remote Similarity	NPD5449	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4184	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD972	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7818	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2144	Approved
0.6654	Remote Similarity	NPD8284	Discontinued
0.6654	Remote Similarity	NPD8100	Phase 3
0.6653	Remote Similarity	NPD4373	Phase 2
0.6653	Remote Similarity	NPD6615	Clinical (unspecified phase)
0.6652	Remote Similarity	NPD6141	Clinical (unspecified phase)
0.6652	Remote Similarity	NPD6661	Clinical (unspecified phase)
0.6652	Remote Similarity	NPD4348	Clinical (unspecified phase)

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