NPASS Compound

Structure

NPC470504 OpenBabel07101718302D 34 38 0 0 1 0 0 0 0 0999 V2000 4.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5000 -0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5000 0.8660 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 -7.2702 -6.0181 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5000 -0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5000 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8635 -5.1045 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 -3.4641 -6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6879 -6.7226 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6824 -6.8271 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2812 -5.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8690 -5.0000 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 -4.3301 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -3.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -7.0892 -7.7406 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -3.0000 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -4.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -5.2812 -4.1910 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -2.5000 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 -1.0000 0.0000 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 -0.0000 -0.0000 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 1 14 1 0 0 0 0 2 6 1 0 0 0 0 2 14 2 0 0 0 0 3 7 2 0 0 0 0 3 14 1 0 0 0 0 4 9 2 0 0 0 0 4 15 1 0 0 0 0 5 8 2 0 0 0 0 5 16 1 0 0 0 0 6 17 2 0 0 0 0 7 17 1 0 0 0 0 8 21 1 0 0 0 0 9 22 1 0 0 0 0 10 11 1 0 0 0 0 10 18 2 0 0 0 0 11 28 2 0 0 0 0 12 15 2 0 0 0 0 12 20 1 0 0 0 0 13 16 2 0 0 0 0 13 19 1 0 0 0 0 15 25 1 0 0 0 0 16 26 1 0 0 0 0 17 34 1 0 0 0 0 18 19 1 0 0 0 0 18 23 1 0 0 0 0 19 21 2 0 0 0 0 20 22 2 0 0 0 0 20 27 1 0 0 0 0 21 29 1 0 0 0 0 22 33 1 0 0 0 0 23 24 2 0 0 0 0 23 29 1 0 0 0 0 24 25 1 0 0 0 0 24 28 1 0 0 0 0 25 30 1 0 0 0 0 31 34 2 0 0 0 0 32 34 2 0 0 0 0 33 34 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	599.94
Volume:	480.767
LogP:	5.691
LogD:	3.562
LogS:	-5.233
# Rotatable Bonds:	5
TPSA:	92.28
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.227
Synthetic Accessibility Score:	3.16
Fsp3:	0.08
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.156
MDCK Permeability:	1.2855300155933946e-05
Pgp-inhibitor:	0.818
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.385
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.002

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.046
Plasma Protein Binding (PPB):	100.23802947998047%
Volume Distribution (VD):	0.522
Pgp-substrate:	0.8943918347358704%

ADMET: Metabolism

CYP1A2-inhibitor:	0.651
CYP1A2-substrate:	0.646
CYP2C19-inhibitor:	0.943
CYP2C19-substrate:	0.515
CYP2C9-inhibitor:	0.93
CYP2C9-substrate:	0.922
CYP2D6-inhibitor:	0.899
CYP2D6-substrate:	0.869
CYP3A4-inhibitor:	0.678
CYP3A4-substrate:	0.926

ADMET: Excretion

Clearance (CL):	0.8
Half-life (T1/2):	0.036

ADMET: Toxicity

hERG Blockers:	0.136
Human Hepatotoxicity (H-HT):	0.376
Drug-inuced Liver Injury (DILI):	0.984
AMES Toxicity:	0.01
Rat Oral Acute Toxicity:	0.862
Maximum Recommended Daily Dose:	0.973
Skin Sensitization:	0.037
Carcinogencity:	0.469
Eye Corrosion:	0.003
Eye Irritation:	0.059
Respiratory Toxicity:	0.952

Download Data

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

Natural Product: NPC470504

Natural Product ID:	NPC470504
*Common Name:**	Eudistomin Y12
IUPAC Name:	[2-bromo-4-[(6-bromo-9H-pyrido[3,4-b]indol-1-yl)-hydroxymethyl]phenyl] 4-methylbenzenesulfonate
Synonyms:	Eudistomin Y12
Standard InCHIKey:	YWBMOWQMJIWLMG-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C25H18Br2N2O4S/c1-14-2-6-17(7-3-14)34(31,32)33-22-9-4-15(12-20(22)27)25(30)24-23-18(10-11-28-24)19-13-16(26)5-8-21(19)29-23/h2-13,25,29-30H,1H3
SMILES:	CC1=CC=C(C=C1)S(=O)(=O)OC2=C(C=C(C=C2)C(C3=NC=CC4=C3NC5=C4C=C(C=C5)Br)O)Br
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2048345
PubChem CID:	70684125
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0001140] Harmala alkaloids

*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
NPO33080	synoicum sp.	Species	Polyclinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[22652254]
NPO33080	synoicum sp.	Species	Polyclinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[23145909]
NPO33080	synoicum sp.	Species	Polyclinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[23747224]

☑ 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	3
MIC	10
Others	1

Activity Type	# Activity
Cell Line	1
Individual Protein	2
Organism	10
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	LC50	=	63300.0	nM	PMID[497639]
NPT1821	Individual Protein	Sortase	Staphylococcus aureus	IC50	>	166000.0	nM	PMID[497639]
NPT1087	Individual Protein	Isocitrate lyase	Candida albicans	IC50	>	166000.0	nM	PMID[497639]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	>	100.0	ug.mL-1	PMID[497639]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	>	100.0	ug.mL-1	PMID[497639]
NPT729	Organism	Micrococcus luteus	Micrococcus luteus	MIC	>	100.0	ug.mL-1	PMID[497639]
NPT566	Organism	Salmonella typhimurium	Salmonella enterica subsp. enterica serovar Typhimurium	MIC	>	100.0	ug.mL-1	PMID[497639]
NPT766	Organism	Proteus vulgaris	Proteus vulgaris	MIC	>	100.0	ug.mL-1	PMID[497639]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	100.0	ug.mL-1	PMID[497639]
NPT87	Organism	Aspergillus fumigatus	Aspergillus fumigatus	MIC	>	100.0	ug.mL-1	PMID[497639]
NPT329	Organism	Trichophyton rubrum	Trichophyton rubrum	MIC	>	100.0	ug.mL-1	PMID[497639]
NPT330	Organism	Trichophyton mentagrophytes	Trichophyton mentagrophytes	MIC	>	100.0	ug.mL-1	PMID[497639]
NPT20	Organism	Candida albicans	Candida albicans	MIC	>	100.0	ug.mL-1	PMID[497639]
NPT2	Others	Unspecified		IC50	>	166000.0	nM	PMID[497639]

☑ 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 NPC470504 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	668
0.1-0.2	5164
0.2-0.3	12887
0.3-0.4	16670
0.4-0.5	3914
0.5-0.6	2454
0.6-0.7	884
0.7-0.8	50
0.8-0.85	2
0.85-0.9	2
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9074	High Similarity	NPC470501
0.8945	High Similarity	NPC470503
0.8853	High Similarity	NPC470502
0.8419	Intermediate Similarity	NPC470505
0.8333	Intermediate Similarity	NPC470500
0.7902	Intermediate Similarity	NPC5145
0.7773	Intermediate Similarity	NPC162002
0.7742	Intermediate Similarity	NPC324149
0.7667	Intermediate Similarity	NPC26641
0.7647	Intermediate Similarity	NPC200553
0.7647	Intermediate Similarity	NPC279189
0.7585	Intermediate Similarity	NPC60006
0.7583	Intermediate Similarity	NPC174489
0.7542	Intermediate Similarity	NPC245348
0.7535	Intermediate Similarity	NPC48938
0.7511	Intermediate Similarity	NPC473761
0.7459	Intermediate Similarity	NPC37152
0.7445	Intermediate Similarity	NPC475070
0.7426	Intermediate Similarity	NPC167908
0.7404	Intermediate Similarity	NPC213530
0.7404	Intermediate Similarity	NPC193267
0.7378	Intermediate Similarity	NPC476167
0.7333	Intermediate Similarity	NPC192315
0.7295	Intermediate Similarity	NPC33064
0.7284	Intermediate Similarity	NPC167860
0.7284	Intermediate Similarity	NPC123976
0.7261	Intermediate Similarity	NPC476121
0.7261	Intermediate Similarity	NPC476124
0.7213	Intermediate Similarity	NPC469554
0.7193	Intermediate Similarity	NPC19872
0.7191	Intermediate Similarity	NPC477610
0.7188	Intermediate Similarity	NPC99666
0.7185	Intermediate Similarity	NPC292958
0.7182	Intermediate Similarity	NPC284678
0.7173	Intermediate Similarity	NPC476041
0.7173	Intermediate Similarity	NPC304926
0.7162	Intermediate Similarity	NPC232727
0.7149	Intermediate Similarity	NPC214142
0.7149	Intermediate Similarity	NPC26679
0.7143	Intermediate Similarity	NPC54803
0.7143	Intermediate Similarity	NPC285558
0.7143	Intermediate Similarity	NPC321592
0.7131	Intermediate Similarity	NPC8022
0.7131	Intermediate Similarity	NPC223409
0.7131	Intermediate Similarity	NPC470799
0.7119	Intermediate Similarity	NPC110151
0.7119	Intermediate Similarity	NPC261251
0.7108	Intermediate Similarity	NPC477861
0.7101	Intermediate Similarity	NPC27041
0.709	Intermediate Similarity	NPC100547
0.7085	Intermediate Similarity	NPC97902
0.7073	Intermediate Similarity	NPC101543
0.7071	Intermediate Similarity	NPC477609
0.7061	Intermediate Similarity	NPC95240
0.7061	Intermediate Similarity	NPC326363
0.7061	Intermediate Similarity	NPC322135
0.7059	Intermediate Similarity	NPC74969
0.7054	Intermediate Similarity	NPC310118
0.7049	Intermediate Similarity	NPC124920
0.7049	Intermediate Similarity	NPC304307
0.7049	Intermediate Similarity	NPC118559
0.7049	Intermediate Similarity	NPC34580
0.7033	Intermediate Similarity	NPC14288
0.7026	Intermediate Similarity	NPC476138
0.7026	Intermediate Similarity	NPC245816
0.7026	Intermediate Similarity	NPC223427
0.7021	Intermediate Similarity	NPC185782
0.702	Intermediate Similarity	NPC477608
0.702	Intermediate Similarity	NPC477607
0.7018	Intermediate Similarity	NPC222018
0.7016	Intermediate Similarity	NPC245055
0.7016	Intermediate Similarity	NPC325976
0.7014	Intermediate Similarity	NPC314394
0.7009	Intermediate Similarity	NPC46580
0.7008	Intermediate Similarity	NPC24370
0.7008	Intermediate Similarity	NPC319232
0.7	Intermediate Similarity	NPC42979
0.7	Intermediate Similarity	NPC469594
0.6988	Remote Similarity	NPC295228
0.6986	Remote Similarity	NPC224764
0.697	Remote Similarity	NPC176538
0.697	Remote Similarity	NPC249040
0.6951	Remote Similarity	NPC314954
0.6944	Remote Similarity	NPC81175
0.694	Remote Similarity	NPC475935
0.694	Remote Similarity	NPC94211
0.694	Remote Similarity	NPC52909
0.692	Remote Similarity	NPC314002
0.6914	Remote Similarity	NPC60621
0.6911	Remote Similarity	NPC6215
0.6908	Remote Similarity	NPC284888
0.6904	Remote Similarity	NPC469592
0.6904	Remote Similarity	NPC471080
0.6901	Remote Similarity	NPC255110
0.6897	Remote Similarity	NPC303820
0.6897	Remote Similarity	NPC23420
0.6897	Remote Similarity	NPC205254
0.6897	Remote Similarity	NPC106771
0.6889	Remote Similarity	NPC171171
0.6881	Remote Similarity	NPC97343
0.688	Remote Similarity	NPC53144
0.688	Remote Similarity	NPC182222
0.6875	Remote Similarity	NPC204717
0.6844	Remote Similarity	NPC473317
0.684	Remote Similarity	NPC323752
0.684	Remote Similarity	NPC77555
0.684	Remote Similarity	NPC267928
0.6834	Remote Similarity	NPC153400
0.6833	Remote Similarity	NPC266931
0.683	Remote Similarity	NPC220765
0.6827	Remote Similarity	NPC476451
0.6816	Remote Similarity	NPC16352
0.681	Remote Similarity	NPC212213
0.6807	Remote Similarity	NPC80596
0.6798	Remote Similarity	NPC82472
0.6792	Remote Similarity	NPC207020
0.6792	Remote Similarity	NPC471603
0.6792	Remote Similarity	NPC128084
0.6786	Remote Similarity	NPC477549
0.6786	Remote Similarity	NPC272549
0.678	Remote Similarity	NPC264166
0.678	Remote Similarity	NPC118832
0.678	Remote Similarity	NPC329708
0.678	Remote Similarity	NPC47059
0.678	Remote Similarity	NPC165349
0.678	Remote Similarity	NPC274291
0.6777	Remote Similarity	NPC142901
0.6777	Remote Similarity	NPC477110
0.6774	Remote Similarity	NPC102423
0.6765	Remote Similarity	NPC477111
0.6763	Remote Similarity	NPC476287
0.6761	Remote Similarity	NPC125597
0.6742	Remote Similarity	NPC313791
0.6738	Remote Similarity	NPC265576
0.6735	Remote Similarity	NPC132642
0.673	Remote Similarity	NPC475746
0.6726	Remote Similarity	NPC151939
0.6726	Remote Similarity	NPC96890
0.6725	Remote Similarity	NPC231536
0.6725	Remote Similarity	NPC95783
0.6724	Remote Similarity	NPC251090
0.6723	Remote Similarity	NPC323927
0.6722	Remote Similarity	NPC294620
0.6719	Remote Similarity	NPC39092
0.6712	Remote Similarity	NPC109447
0.671	Remote Similarity	NPC307963
0.6708	Remote Similarity	NPC322064
0.6708	Remote Similarity	NPC85273
0.6708	Remote Similarity	NPC288349
0.6697	Remote Similarity	NPC311276
0.6697	Remote Similarity	NPC82331
0.6696	Remote Similarity	NPC72980
0.6695	Remote Similarity	NPC156704
0.6695	Remote Similarity	NPC193761
0.6695	Remote Similarity	NPC262898
0.6695	Remote Similarity	NPC211813
0.6693	Remote Similarity	NPC184225
0.6693	Remote Similarity	NPC260434
0.6692	Remote Similarity	NPC26543
0.6682	Remote Similarity	NPC474958
0.6682	Remote Similarity	NPC203754
0.6682	Remote Similarity	NPC150048
0.6682	Remote Similarity	NPC131718
0.668	Remote Similarity	NPC471891
0.668	Remote Similarity	NPC175150
0.668	Remote Similarity	NPC208284
0.668	Remote Similarity	NPC243633
0.6667	Remote Similarity	NPC300688
0.6667	Remote Similarity	NPC475774
0.6667	Remote Similarity	NPC41679
0.6667	Remote Similarity	NPC101350
0.6667	Remote Similarity	NPC239954
0.6667	Remote Similarity	NPC207686
0.6667	Remote Similarity	NPC200836
0.6667	Remote Similarity	NPC274229
0.6654	Remote Similarity	NPC321939
0.6654	Remote Similarity	NPC63971
0.6654	Remote Similarity	NPC91868
0.6653	Remote Similarity	NPC122436
0.6653	Remote Similarity	NPC264285
0.6652	Remote Similarity	NPC179701
0.6652	Remote Similarity	NPC184964
0.6642	Remote Similarity	NPC216369
0.6641	Remote Similarity	NPC178858
0.664	Remote Similarity	NPC476492
0.664	Remote Similarity	NPC471506
0.664	Remote Similarity	NPC473185
0.6639	Remote Similarity	NPC11464
0.6639	Remote Similarity	NPC170114
0.6638	Remote Similarity	NPC106937
0.6638	Remote Similarity	NPC198673
0.6638	Remote Similarity	NPC18487
0.663	Remote Similarity	NPC117980
0.6627	Remote Similarity	NPC235685
0.6627	Remote Similarity	NPC28945
0.6625	Remote Similarity	NPC475910
0.6625	Remote Similarity	NPC287208
0.6623	Remote Similarity	NPC94943
0.6623	Remote Similarity	NPC243716
0.6623	Remote Similarity	NPC15102

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 NPC470504 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	313
0.1-0.2	731
0.2-0.3	895
0.3-0.4	2270
0.4-0.5	2711
0.5-0.6	1902
0.6-0.7	324
0.7-0.8	4
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
0.7444	Intermediate Similarity	NPD7948	Phase 1
0.7319	Intermediate Similarity	NPD5409	Clinical (unspecified phase)
0.7254	Intermediate Similarity	NPD7558	Phase 2
0.7143	Intermediate Similarity	NPD8405	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD7603	Discontinued
0.7049	Intermediate Similarity	NPD6553	Clinical (unspecified phase)
0.7004	Intermediate Similarity	NPD5575	Clinical (unspecified phase)
0.6958	Remote Similarity	NPD7823	Clinical (unspecified phase)
0.6953	Remote Similarity	NPD6991	Approved
0.6941	Remote Similarity	NPD5065	Approved
0.6941	Remote Similarity	NPD6492	Phase 2
0.6917	Remote Similarity	NPD5612	Discontinued
0.6891	Remote Similarity	NPD5067	Phase 2
0.6891	Remote Similarity	NPD5066	Phase 2
0.687	Remote Similarity	NPD7540	Clinical (unspecified phase)
0.6862	Remote Similarity	NPD3330	Phase 1
0.6855	Remote Similarity	NPD7567	Approved
0.6835	Remote Similarity	NPD7671	Approved
0.6835	Remote Similarity	NPD7672	Approved
0.679	Remote Similarity	NPD8109	Clinical (unspecified phase)
0.6781	Remote Similarity	NPD2175	Phase 3
0.6781	Remote Similarity	NPD2176	Approved
0.6781	Remote Similarity	NPD2177	Approved
0.678	Remote Similarity	NPD31	Approved
0.678	Remote Similarity	NPD4038	Approved
0.678	Remote Similarity	NPD4036	Approved
0.678	Remote Similarity	NPD4033	Approved
0.678	Remote Similarity	NPD4034	Approved
0.678	Remote Similarity	NPD4037	Approved
0.678	Remote Similarity	NPD3397	Phase 2
0.678	Remote Similarity	NPD32	Approved
0.678	Remote Similarity	NPD4122	Approved
0.678	Remote Similarity	NPD4039	Approved
0.678	Remote Similarity	NPD4035	Approved
0.6766	Remote Similarity	NPD6975	Discontinued
0.6758	Remote Similarity	NPD2781	Approved
0.6757	Remote Similarity	NPD5482	Discontinued
0.675	Remote Similarity	NPD5939	Approved
0.675	Remote Similarity	NPD5936	Approved
0.6747	Remote Similarity	NPD7555	Discontinued
0.6743	Remote Similarity	NPD2780	Approved
0.6743	Remote Similarity	NPD2782	Approved
0.6739	Remote Similarity	NPD6569	Phase 2
0.6732	Remote Similarity	NPD5483	Clinical (unspecified phase)
0.6726	Remote Similarity	NPD6159	Phase 2
0.6723	Remote Similarity	NPD6290	Phase 2
0.6718	Remote Similarity	NPD8247	Approved
0.6718	Remote Similarity	NPD8246	Approved
0.6711	Remote Similarity	NPD7414	Clinical (unspecified phase)
0.671	Remote Similarity	NPD1038	Approved
0.6695	Remote Similarity	NPD4473	Clinical (unspecified phase)
0.6693	Remote Similarity	NPD8106	Phase 2
0.6693	Remote Similarity	NPD6131	Phase 1
0.6681	Remote Similarity	NPD6590	Discontinued
0.668	Remote Similarity	NPD4502	Phase 2
0.6667	Remote Similarity	NPD6595	Phase 3
0.6654	Remote Similarity	NPD6473	Phase 1
0.6654	Remote Similarity	NPD8442	Discontinued
0.6653	Remote Similarity	NPD7222	Phase 2
0.6653	Remote Similarity	NPD3354	Phase 2
0.6653	Remote Similarity	NPD4865	Approved
0.6641	Remote Similarity	NPD2921	Clinical (unspecified phase)
0.664	Remote Similarity	NPD6494	Phase 2
0.6639	Remote Similarity	NPD6803	Clinical (unspecified phase)
0.6638	Remote Similarity	NPD5590	Clinical (unspecified phase)
0.6638	Remote Similarity	NPD802	Phase 2
0.6627	Remote Similarity	NPD8004	Discontinued
0.6626	Remote Similarity	NPD7194	Discontinued
0.6625	Remote Similarity	NPD7947	Clinical (unspecified phase)
0.6624	Remote Similarity	NPD6769	Clinical (unspecified phase)
0.6623	Remote Similarity	NPD3082	Discontinued
0.6609	Remote Similarity	NPD8110	Clinical (unspecified phase)
0.6606	Remote Similarity	NPD5069	Clinical (unspecified phase)
0.6598	Remote Similarity	NPD2125	Clinical (unspecified phase)
0.6598	Remote Similarity	NPD6140	Clinical (unspecified phase)
0.6598	Remote Similarity	NPD5903	Approved
0.6598	Remote Similarity	NPD5902	Approved
0.6588	Remote Similarity	NPD1259	Discontinued
0.6583	Remote Similarity	NPD1392	Approved
0.6582	Remote Similarity	NPD4511	Phase 1
0.6568	Remote Similarity	NPD3825	Phase 3
0.6567	Remote Similarity	NPD1304	Clinical (unspecified phase)
0.6565	Remote Similarity	NPD6141	Clinical (unspecified phase)
0.6565	Remote Similarity	NPD8431	Approved
0.656	Remote Similarity	NPD4890	Phase 2
0.6556	Remote Similarity	NPD5658	Approved
0.655	Remote Similarity	NPD6610	Clinical (unspecified phase)
0.6546	Remote Similarity	NPD1856	Discontinued
0.6542	Remote Similarity	NPD3003	Approved
0.654	Remote Similarity	NPD484	Approved
0.6535	Remote Similarity	NPD5596	Phase 2
0.6529	Remote Similarity	NPD7409	Clinical (unspecified phase)
0.6519	Remote Similarity	NPD5450	Discontinued
0.6516	Remote Similarity	NPD8093	Discontinued
0.6515	Remote Similarity	NPD6838	Clinical (unspecified phase)
0.6509	Remote Similarity	NPD3321	Discontinued
0.6509	Remote Similarity	NPD8063	Discontinued
0.6507	Remote Similarity	NPD3254	Phase 1
0.6507	Remote Similarity	NPD3255	Phase 1
0.6502	Remote Similarity	NPD4650	Approved
0.6494	Remote Similarity	NPD2383	Phase 1
0.6492	Remote Similarity	NPD3402	Phase 1
0.6486	Remote Similarity	NPD424	Approved
0.6486	Remote Similarity	NPD425	Approved
0.6482	Remote Similarity	NPD5559	Phase 2
0.6478	Remote Similarity	NPD6344	Clinical (unspecified phase)
0.6476	Remote Similarity	NPD4079	Approved
0.6476	Remote Similarity	NPD4076	Approved
0.6473	Remote Similarity	NPD7957	Phase 1
0.6473	Remote Similarity	NPD7958	Clinical (unspecified phase)
0.6458	Remote Similarity	NPD4886	Phase 2
0.6458	Remote Similarity	NPD8284	Discontinued
0.645	Remote Similarity	NPD706	Phase 1
0.6446	Remote Similarity	NPD7453	Approved
0.6446	Remote Similarity	NPD7452	Approved
0.6443	Remote Similarity	NPD6978	Phase 2
0.6443	Remote Similarity	NPD6977	Clinical (unspecified phase)
0.6439	Remote Similarity	NPD4303	Clinical (unspecified phase)
0.6435	Remote Similarity	NPD5083	Clinical (unspecified phase)
0.6434	Remote Similarity	NPD8321	Discontinued
0.6432	Remote Similarity	NPD4795	Phase 2
0.6432	Remote Similarity	NPD7712	Clinical (unspecified phase)
0.6432	Remote Similarity	NPD3505	Approved
0.6432	Remote Similarity	NPD3506	Approved
0.6429	Remote Similarity	NPD8396	Approved
0.6429	Remote Similarity	NPD4548	Discontinued
0.6429	Remote Similarity	NPD8395	Approved
0.6429	Remote Similarity	NPD7719	Discontinued
0.6429	Remote Similarity	NPD4184	Clinical (unspecified phase)
0.6426	Remote Similarity	NPD6276	Discontinued
0.6426	Remote Similarity	NPD6501	Approved
0.6426	Remote Similarity	NPD6500	Approved
0.6419	Remote Similarity	NPD7867	Phase 1
0.6417	Remote Similarity	NPD3928	Approved
0.6417	Remote Similarity	NPD3931	Approved
0.6414	Remote Similarity	NPD4899	Clinical (unspecified phase)
0.6414	Remote Similarity	NPD4945	Discontinued
0.641	Remote Similarity	NPD5912	Clinical (unspecified phase)
0.641	Remote Similarity	NPD5913	Phase 3
0.6408	Remote Similarity	NPD4131	Phase 3
0.6407	Remote Similarity	NPD7424	Clinical (unspecified phase)
0.6406	Remote Similarity	NPD6476	Clinical (unspecified phase)
0.6406	Remote Similarity	NPD6158	Phase 2
0.6405	Remote Similarity	NPD5530	Phase 1
0.6403	Remote Similarity	NPD7002	Clinical (unspecified phase)
0.6398	Remote Similarity	NPD3395	Approved
0.6398	Remote Similarity	NPD3396	Approved
0.6398	Remote Similarity	NPD6491	Clinical (unspecified phase)
0.6395	Remote Similarity	NPD4454	Phase 2
0.6391	Remote Similarity	NPD5522	Clinical (unspecified phase)
0.6388	Remote Similarity	NPD2381	Approved
0.6388	Remote Similarity	NPD2382	Approved
0.6388	Remote Similarity	NPD2380	Approved
0.6387	Remote Similarity	NPD3231	Approved
0.6383	Remote Similarity	NPD3404	Approved
0.6381	Remote Similarity	NPD5040	Clinical (unspecified phase)
0.638	Remote Similarity	NPD112	Approved
0.638	Remote Similarity	NPD9705	Discontinued
0.6379	Remote Similarity	NPD3039	Clinical (unspecified phase)
0.6377	Remote Similarity	NPD8101	Phase 3
0.6375	Remote Similarity	NPD7726	Phase 1
0.6374	Remote Similarity	NPD4440	Clinical (unspecified phase)
0.6371	Remote Similarity	NPD7112	Discontinued
0.6371	Remote Similarity	NPD6550	Discontinued
0.6368	Remote Similarity	NPD6281	Approved
0.6364	Remote Similarity	NPD8272	Phase 2
0.6364	Remote Similarity	NPD6976	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD1258	Discontinued
0.636	Remote Similarity	NPD6203	Clinical (unspecified phase)
0.636	Remote Similarity	NPD3814	Phase 1
0.6352	Remote Similarity	NPD2816	Clinical (unspecified phase)
0.6349	Remote Similarity	NPD6824	Clinical (unspecified phase)
0.6345	Remote Similarity	NPD6988	Phase 1
0.6345	Remote Similarity	NPD5164	Discontinued
0.6344	Remote Similarity	NPD9690	Approved
0.6341	Remote Similarity	NPD7470	Discontinued
0.6341	Remote Similarity	NPD6220	Phase 3
0.6339	Remote Similarity	NPD7675	Phase 3
0.6339	Remote Similarity	NPD7674	Phase 3
0.6339	Remote Similarity	NPD7676	Clinical (unspecified phase)
0.6339	Remote Similarity	NPD7426	Phase 1
0.6337	Remote Similarity	NPD3932	Clinical (unspecified phase)
0.6337	Remote Similarity	NPD8403	Phase 1
0.6335	Remote Similarity	NPD5255	Approved
0.6335	Remote Similarity	NPD1996	Discontinued
0.6333	Remote Similarity	NPD1739	Approved
0.6333	Remote Similarity	NPD1740	Approved
0.6332	Remote Similarity	NPD7052	Phase 1
0.633	Remote Similarity	NPD2882	Phase 1
0.6329	Remote Similarity	NPD7944	Discontinued
0.6328	Remote Similarity	NPD8512	Phase 3
0.6328	Remote Similarity	NPD6969	Phase 2
0.6328	Remote Similarity	NPD6968	Phase 2
0.6325	Remote Similarity	NPD6965	Clinical (unspecified phase)
0.6322	Remote Similarity	NPD8072	Approved
0.632	Remote Similarity	NPD6985	Discontinued
0.632	Remote Similarity	NPD5728	Clinical (unspecified phase)
0.6318	Remote Similarity	NPD4296	Phase 2
0.6318	Remote Similarity	NPD4080	Discontinued
0.6316	Remote Similarity	NPD6525	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