NPASS Compound

Structure

NPC470505 OpenBabel07101718302D 22 25 0 0 1 0 0 0 0 0999 V2000 3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 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 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 -3.6508 3.2872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6562 3.3917 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 -3.4697 1.5646 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 -4.0575 2.3736 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 -2.4752 1.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0685 2.5827 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 0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -5.0520 2.2691 0.0000 Br 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 -1.0739 2.4781 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 0 0 0 1 3 1 0 0 0 0 2 4 1 0 0 0 0 3 5 2 0 0 0 0 4 11 2 0 0 0 0 5 11 1 0 0 0 0 6 7 2 0 0 0 0 6 12 1 0 0 0 0 7 15 1 0 0 0 0 8 9 1 0 0 0 0 8 13 2 0 0 0 0 9 20 2 0 0 0 0 10 12 2 0 0 0 0 10 14 1 0 0 0 0 11 18 1 0 0 0 0 12 19 1 0 0 0 0 13 14 1 0 0 0 0 13 16 1 0 0 0 0 14 15 2 0 0 0 0 15 21 1 0 0 0 0 16 17 2 0 0 0 0 16 21 1 0 0 0 0 17 18 1 0 0 0 0 17 20 1 0 0 0 0 18 22 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	352.02
Volume:	311.998
LogP:	4.034
LogD:	3.259
LogS:	-4.794
# Rotatable Bonds:	2
TPSA:	48.91
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.555
Synthetic Accessibility Score:	2.773
Fsp3:	0.056
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.799
MDCK Permeability:	1.137358140113065e-05
Pgp-inhibitor:	0.003
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.007
30% Bioavailability (F30%):	0.009

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.872
Plasma Protein Binding (PPB):	95.88980102539062%
Volume Distribution (VD):	1.183
Pgp-substrate:	2.7377147674560547%

ADMET: Metabolism

CYP1A2-inhibitor:	0.928
CYP1A2-substrate:	0.572
CYP2C19-inhibitor:	0.825
CYP2C19-substrate:	0.45
CYP2C9-inhibitor:	0.755
CYP2C9-substrate:	0.86
CYP2D6-inhibitor:	0.912
CYP2D6-substrate:	0.769
CYP3A4-inhibitor:	0.432
CYP3A4-substrate:	0.694

ADMET: Excretion

Clearance (CL):	1.149
Half-life (T1/2):	0.247

ADMET: Toxicity

hERG Blockers:	0.085
Human Hepatotoxicity (H-HT):	0.216
Drug-inuced Liver Injury (DILI):	0.853
AMES Toxicity:	0.113
Rat Oral Acute Toxicity:	0.628
Maximum Recommended Daily Dose:	0.96
Skin Sensitization:	0.106
Carcinogencity:	0.09
Eye Corrosion:	0.003
Eye Irritation:	0.388
Respiratory Toxicity:	0.98

Download Data

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

Natural Product: NPC470505

Natural Product ID:	NPC470505
*Common Name:**	Eudistomin Y13
IUPAC Name:	(6-bromo-9H-pyrido[3,4-b]indol-1-yl)-phenylmethanol
Synonyms:	Eudistomin Y13
Standard InCHIKey:	FUINDJPWTVFMGF-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C18H13BrN2O/c19-12-6-7-15-14(10-12)13-8-9-20-17(16(13)21-15)18(22)11-4-2-1-3-5-11/h1-10,18,21-22H
SMILES:	Brc1ccc2c(c1)c1ccnc(c1[nH]2)C(c1ccccc1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2048346
PubChem CID:	70690409
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	=	49000.0	nM	PMID[470994]
NPT1821	Individual Protein	Sortase	Staphylococcus aureus	IC50	>	283100.0	nM	PMID[470994]
NPT1087	Individual Protein	Isocitrate lyase	Candida albicans	IC50	>	283100.0	nM	PMID[470994]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	>	100.0	ug.mL-1	PMID[470994]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	=	100.0	ug.mL-1	PMID[470994]
NPT729	Organism	Micrococcus luteus	Micrococcus luteus	MIC	=	100.0	ug.mL-1	PMID[470994]
NPT566	Organism	Salmonella typhimurium	Salmonella enterica subsp. enterica serovar Typhimurium	MIC	>	100.0	ug.mL-1	PMID[470994]
NPT766	Organism	Proteus vulgaris	Proteus vulgaris	MIC	>	100.0	ug.mL-1	PMID[470994]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	100.0	ug.mL-1	PMID[470994]
NPT87	Organism	Aspergillus fumigatus	Aspergillus fumigatus	MIC	>	100.0	ug.mL-1	PMID[470994]
NPT329	Organism	Trichophyton rubrum	Trichophyton rubrum	MIC	>	100.0	ug.mL-1	PMID[470994]
NPT330	Organism	Trichophyton mentagrophytes	Trichophyton mentagrophytes	MIC	>	100.0	ug.mL-1	PMID[470994]
NPT20	Organism	Candida albicans	Candida albicans	MIC	>	100.0	ug.mL-1	PMID[470994]
NPT2	Others	Unspecified		IC50	>	283100.0	nM	PMID[470994]

☑ 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 NPC470505 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	680
0.1-0.2	4776
0.2-0.3	14557
0.3-0.4	15894
0.4-0.5	3096
0.5-0.6	1950
0.6-0.7	1468
0.7-0.8	259
0.8-0.85	9
0.85-0.9	5
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9188	High Similarity	NPC470501
0.9141	High Similarity	NPC470503
0.904	High Similarity	NPC470502
0.895	High Similarity	NPC48938
0.875	High Similarity	NPC473761
0.866	High Similarity	NPC470500
0.8442	Intermediate Similarity	NPC5145
0.8419	Intermediate Similarity	NPC470504
0.8396	Intermediate Similarity	NPC284678
0.8281	Intermediate Similarity	NPC324149
0.8191	Intermediate Similarity	NPC314394
0.8152	Intermediate Similarity	NPC97343
0.8037	Intermediate Similarity	NPC279189
0.8033	Intermediate Similarity	NPC102423
0.799	Intermediate Similarity	NPC205254
0.799	Intermediate Similarity	NPC106771
0.799	Intermediate Similarity	NPC23420
0.799	Intermediate Similarity	NPC303820
0.798	Intermediate Similarity	NPC192315
0.795	Intermediate Similarity	NPC475935
0.795	Intermediate Similarity	NPC52909
0.795	Intermediate Similarity	NPC94211
0.794	Intermediate Similarity	NPC476167
0.7926	Intermediate Similarity	NPC162002
0.7923	Intermediate Similarity	NPC131718
0.7921	Intermediate Similarity	NPC475070
0.7892	Intermediate Similarity	NPC274229
0.789	Intermediate Similarity	NPC26641
0.787	Intermediate Similarity	NPC200553
0.7798	Intermediate Similarity	NPC174489
0.7778	Intermediate Similarity	NPC313791
0.7747	Intermediate Similarity	NPC325903
0.7725	Intermediate Similarity	NPC82331
0.7723	Intermediate Similarity	NPC19872
0.7716	Intermediate Similarity	NPC95783
0.7711	Intermediate Similarity	NPC265576
0.7711	Intermediate Similarity	NPC212213
0.7703	Intermediate Similarity	NPC477610
0.7696	Intermediate Similarity	NPC150048
0.7696	Intermediate Similarity	NPC474958
0.7696	Intermediate Similarity	NPC203754
0.7692	Intermediate Similarity	NPC15102
0.7689	Intermediate Similarity	NPC292958
0.7663	Intermediate Similarity	NPC469785
0.766	Intermediate Similarity	NPC109447
0.7658	Intermediate Similarity	NPC37152
0.7656	Intermediate Similarity	NPC151939
0.7647	Intermediate Similarity	NPC311276
0.7639	Intermediate Similarity	NPC60006
0.7628	Intermediate Similarity	NPC167908
0.7622	Intermediate Similarity	NPC469762
0.7621	Intermediate Similarity	NPC476124
0.7621	Intermediate Similarity	NPC476121
0.7619	Intermediate Similarity	NPC63751
0.7612	Intermediate Similarity	NPC179701
0.7609	Intermediate Similarity	NPC34844
0.7606	Intermediate Similarity	NPC193267
0.7606	Intermediate Similarity	NPC213530
0.7593	Intermediate Similarity	NPC245348
0.7581	Intermediate Similarity	NPC230869
0.7581	Intermediate Similarity	NPC135141
0.7581	Intermediate Similarity	NPC92796
0.7574	Intermediate Similarity	NPC262898
0.7569	Intermediate Similarity	NPC63545
0.7568	Intermediate Similarity	NPC141353
0.7566	Intermediate Similarity	NPC54988
0.7565	Intermediate Similarity	NPC59269
0.756	Intermediate Similarity	NPC167860
0.756	Intermediate Similarity	NPC123976
0.7559	Intermediate Similarity	NPC477609
0.7546	Intermediate Similarity	NPC229893
0.7538	Intermediate Similarity	NPC307191
0.7538	Intermediate Similarity	NPC231536
0.7537	Intermediate Similarity	NPC239954
0.7527	Intermediate Similarity	NPC469811
0.7527	Intermediate Similarity	NPC201380
0.7527	Intermediate Similarity	NPC179787
0.7526	Intermediate Similarity	NPC201700
0.7524	Intermediate Similarity	NPC245816
0.7524	Intermediate Similarity	NPC476138
0.7512	Intermediate Similarity	NPC304926
0.7512	Intermediate Similarity	NPC198673
0.7512	Intermediate Similarity	NPC232727
0.7512	Intermediate Similarity	NPC476041
0.7488	Intermediate Similarity	NPC207020
0.7487	Intermediate Similarity	NPC300688
0.7486	Intermediate Similarity	NPC321911
0.7476	Intermediate Similarity	NPC123839
0.7473	Intermediate Similarity	NPC316069
0.7464	Intermediate Similarity	NPC266249
0.7463	Intermediate Similarity	NPC473342
0.7463	Intermediate Similarity	NPC304187
0.7463	Intermediate Similarity	NPC176538
0.7463	Intermediate Similarity	NPC477166
0.7463	Intermediate Similarity	NPC99666
0.7463	Intermediate Similarity	NPC477167
0.746	Intermediate Similarity	NPC317105
0.746	Intermediate Similarity	NPC40779
0.7459	Intermediate Similarity	NPC469760
0.7459	Intermediate Similarity	NPC469786
0.7459	Intermediate Similarity	NPC25008
0.7459	Intermediate Similarity	NPC469763
0.7459	Intermediate Similarity	NPC73952
0.7459	Intermediate Similarity	NPC469765
0.7459	Intermediate Similarity	NPC259644
0.7452	Intermediate Similarity	NPC475288
0.7451	Intermediate Similarity	NPC474916
0.7451	Intermediate Similarity	NPC168911
0.7448	Intermediate Similarity	NPC470498
0.7447	Intermediate Similarity	NPC279918
0.744	Intermediate Similarity	NPC165599
0.7438	Intermediate Similarity	NPC222018
0.7435	Intermediate Similarity	NPC317430
0.743	Intermediate Similarity	NPC27041
0.7421	Intermediate Similarity	NPC280864
0.7419	Intermediate Similarity	NPC70922
0.7419	Intermediate Similarity	NPC80597
0.7419	Intermediate Similarity	NPC211572
0.7419	Intermediate Similarity	NPC212376
0.7419	Intermediate Similarity	NPC75540
0.7418	Intermediate Similarity	NPC159856
0.7416	Intermediate Similarity	NPC166492
0.7416	Intermediate Similarity	NPC473362
0.7413	Intermediate Similarity	NPC243716
0.7411	Intermediate Similarity	NPC220765
0.7409	Intermediate Similarity	NPC34508
0.7407	Intermediate Similarity	NPC282231
0.7391	Intermediate Similarity	NPC193761
0.7387	Intermediate Similarity	NPC62749
0.7383	Intermediate Similarity	NPC8022
0.7383	Intermediate Similarity	NPC470799
0.7382	Intermediate Similarity	NPC474561
0.7382	Intermediate Similarity	NPC49954
0.7374	Intermediate Similarity	NPC204717
0.7374	Intermediate Similarity	NPC108011
0.7351	Intermediate Similarity	NPC105818
0.7351	Intermediate Similarity	NPC24678
0.735	Intermediate Similarity	NPC46580
0.7347	Intermediate Similarity	NPC176199
0.7347	Intermediate Similarity	NPC215795
0.7346	Intermediate Similarity	NPC80596
0.734	Intermediate Similarity	NPC236711
0.7337	Intermediate Similarity	NPC314002
0.7333	Intermediate Similarity	NPC244741
0.733	Intermediate Similarity	NPC477607
0.733	Intermediate Similarity	NPC237414
0.733	Intermediate Similarity	NPC477608
0.7324	Intermediate Similarity	NPC118940
0.7324	Intermediate Similarity	NPC128084
0.7324	Intermediate Similarity	NPC26679
0.7323	Intermediate Similarity	NPC19679
0.7321	Intermediate Similarity	NPC97902
0.7321	Intermediate Similarity	NPC285558
0.732	Intermediate Similarity	NPC477611
0.732	Intermediate Similarity	NPC64055
0.732	Intermediate Similarity	NPC472123
0.7317	Intermediate Similarity	NPC77555
0.731	Intermediate Similarity	NPC24864
0.7309	Intermediate Similarity	NPC469554
0.7304	Intermediate Similarity	NPC195314
0.7302	Intermediate Similarity	NPC251936
0.73	Intermediate Similarity	NPC171171
0.7296	Intermediate Similarity	NPC68354
0.7295	Intermediate Similarity	NPC470497
0.7294	Intermediate Similarity	NPC471506
0.7292	Intermediate Similarity	NPC160105
0.7285	Intermediate Similarity	NPC476492
0.7282	Intermediate Similarity	NPC275305
0.7282	Intermediate Similarity	NPC329688
0.7282	Intermediate Similarity	NPC189812
0.7282	Intermediate Similarity	NPC37423
0.7277	Intermediate Similarity	NPC149265
0.7273	Intermediate Similarity	NPC233936
0.7273	Intermediate Similarity	NPC141926
0.7269	Intermediate Similarity	NPC477114
0.7268	Intermediate Similarity	NPC158129
0.7264	Intermediate Similarity	NPC185782
0.7263	Intermediate Similarity	NPC122141
0.7259	Intermediate Similarity	NPC270009
0.725	Intermediate Similarity	NPC163421
0.725	Intermediate Similarity	NPC188387
0.7245	Intermediate Similarity	NPC121903
0.724	Intermediate Similarity	NPC214142
0.7236	Intermediate Similarity	NPC472108
0.7236	Intermediate Similarity	NPC163055
0.7236	Intermediate Similarity	NPC139291
0.7233	Intermediate Similarity	NPC267928
0.7231	Intermediate Similarity	NPC314603
0.7228	Intermediate Similarity	NPC314372
0.7225	Intermediate Similarity	NPC57398
0.7225	Intermediate Similarity	NPC470203
0.7217	Intermediate Similarity	NPC314957
0.7215	Intermediate Similarity	NPC310118
0.7214	Intermediate Similarity	NPC94752
0.7213	Intermediate Similarity	NPC190296
0.7212	Intermediate Similarity	NPC249040
0.7208	Intermediate Similarity	NPC184964
0.7207	Intermediate Similarity	NPC261251
0.7207	Intermediate Similarity	NPC6215
0.7207	Intermediate Similarity	NPC110151

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 NPC470505 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	338
0.1-0.2	680
0.2-0.3	861
0.3-0.4	2218
0.4-0.5	2453
0.5-0.6	1899
0.6-0.7	663
0.7-0.8	38
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
0.8118	Intermediate Similarity	NPD5065	Approved
0.7619	Intermediate Similarity	NPD5069	Clinical (unspecified phase)
0.7577	Intermediate Similarity	NPD6595	Phase 3
0.7574	Intermediate Similarity	NPD7948	Phase 1
0.7563	Intermediate Similarity	NPD706	Phase 1
0.7513	Intermediate Similarity	NPD6610	Clinical (unspecified phase)
0.7512	Intermediate Similarity	NPD5575	Clinical (unspecified phase)
0.7423	Intermediate Similarity	NPD2382	Approved
0.7423	Intermediate Similarity	NPD2380	Approved
0.7423	Intermediate Similarity	NPD2381	Approved
0.7406	Intermediate Similarity	NPD3330	Phase 1
0.7391	Intermediate Similarity	NPD1183	Approved
0.7376	Intermediate Similarity	NPD3404	Approved
0.7356	Intermediate Similarity	NPD4886	Phase 2
0.735	Intermediate Similarity	NPD6141	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD4076	Approved
0.7347	Intermediate Similarity	NPD4079	Approved
0.7323	Intermediate Similarity	NPD5596	Phase 2
0.7318	Intermediate Similarity	NPD7603	Discontinued
0.7312	Intermediate Similarity	NPD2882	Phase 1
0.7302	Intermediate Similarity	NPD5255	Approved
0.7296	Intermediate Similarity	NPD6203	Clinical (unspecified phase)
0.7296	Intermediate Similarity	NPD3506	Approved
0.7296	Intermediate Similarity	NPD3505	Approved
0.7282	Intermediate Similarity	NPD6492	Phase 2
0.7273	Intermediate Similarity	NPD6991	Approved
0.7269	Intermediate Similarity	NPD5409	Clinical (unspecified phase)
0.7251	Intermediate Similarity	NPD6838	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD7424	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD6158	Phase 2
0.7219	Intermediate Similarity	NPD6476	Clinical (unspecified phase)
0.7216	Intermediate Similarity	NPD1325	Approved
0.7216	Intermediate Similarity	NPD4184	Clinical (unspecified phase)
0.7216	Intermediate Similarity	NPD1326	Approved
0.7202	Intermediate Similarity	NPD424	Approved
0.7202	Intermediate Similarity	NPD425	Approved
0.7196	Intermediate Similarity	NPD5067	Phase 2
0.7196	Intermediate Similarity	NPD5066	Phase 2
0.7192	Intermediate Similarity	NPD8063	Discontinued
0.7192	Intermediate Similarity	NPD3321	Discontinued
0.7189	Intermediate Similarity	NPD7823	Clinical (unspecified phase)
0.7183	Intermediate Similarity	NPD2125	Clinical (unspecified phase)
0.7182	Intermediate Similarity	NPD9076	Clinical (unspecified phase)
0.7178	Intermediate Similarity	NPD8431	Approved
0.7163	Intermediate Similarity	NPD8093	Discontinued
0.7156	Intermediate Similarity	NPD7712	Clinical (unspecified phase)
0.7156	Intermediate Similarity	NPD8405	Clinical (unspecified phase)
0.715	Intermediate Similarity	NPD5728	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD8110	Clinical (unspecified phase)
0.7136	Intermediate Similarity	NPD7672	Approved
0.7136	Intermediate Similarity	NPD7671	Approved
0.7136	Intermediate Similarity	NPD7947	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD7558	Phase 2
0.7101	Intermediate Similarity	NPD6449	Clinical (unspecified phase)
0.71	Intermediate Similarity	NPD7867	Phase 1
0.7098	Intermediate Similarity	NPD5140	Approved
0.7098	Intermediate Similarity	NPD5138	Approved
0.7091	Intermediate Similarity	NPD1996	Discontinued
0.709	Intermediate Similarity	NPD2837	Discontinued
0.7081	Intermediate Similarity	NPD3813	Approved
0.7079	Intermediate Similarity	NPD3082	Discontinued
0.7077	Intermediate Similarity	NPD5862	Discovery
0.7075	Intermediate Similarity	NPD5901	Discontinued
0.7073	Intermediate Similarity	NPD5912	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD5913	Phase 3
0.7068	Intermediate Similarity	NPD4669	Clinical (unspecified phase)
0.7068	Intermediate Similarity	NPD2581	Approved
0.7068	Intermediate Similarity	NPD4670	Clinical (unspecified phase)
0.7068	Intermediate Similarity	NPD2582	Approved
0.7068	Intermediate Similarity	NPD4671	Clinical (unspecified phase)
0.7065	Intermediate Similarity	NPD1722	Approved
0.7064	Intermediate Similarity	NPD5612	Discontinued
0.7056	Intermediate Similarity	NPD4612	Discontinued
0.7045	Intermediate Similarity	NPD4555	Clinical (unspecified phase)
0.7042	Intermediate Similarity	NPD4862	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD7470	Discontinued
0.7035	Intermediate Similarity	NPD2144	Approved
0.7031	Intermediate Similarity	NPD3433	Clinical (unspecified phase)
0.7028	Intermediate Similarity	NPD2121	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD6281	Approved
0.7021	Intermediate Similarity	NPD4374	Clinical (unspecified phase)
0.702	Intermediate Similarity	NPD482	Approved
0.7009	Intermediate Similarity	NPD8410	Clinical (unspecified phase)
0.7009	Intermediate Similarity	NPD8322	Phase 2
0.7005	Intermediate Similarity	NPD1038	Approved
0.7005	Intermediate Similarity	NPD5934	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD3825	Phase 3
0.6995	Remote Similarity	NPD5426	Phase 3
0.6991	Remote Similarity	NPD8321	Discontinued
0.699	Remote Similarity	NPD4640	Approved
0.699	Remote Similarity	NPD4639	Approved
0.699	Remote Similarity	NPD4699	Discontinued
0.699	Remote Similarity	NPD4638	Approved
0.6986	Remote Similarity	NPD6957	Approved
0.6986	Remote Similarity	NPD6958	Approved
0.6986	Remote Similarity	NPD6803	Clinical (unspecified phase)
0.6985	Remote Similarity	NPD749	Clinical (unspecified phase)
0.6984	Remote Similarity	NPD4463	Approved
0.6984	Remote Similarity	NPD4462	Approved
0.698	Remote Similarity	NPD2391	Clinical (unspecified phase)
0.6978	Remote Similarity	NPD6977	Clinical (unspecified phase)
0.6978	Remote Similarity	NPD6978	Phase 2
0.6978	Remote Similarity	NPD198	Clinical (unspecified phase)
0.6978	Remote Similarity	NPD2349	Phase 3
0.6976	Remote Similarity	NPD6965	Clinical (unspecified phase)
0.6971	Remote Similarity	NPD7944	Discontinued
0.6968	Remote Similarity	NPD4702	Approved
0.6968	Remote Similarity	NPD4703	Approved
0.6967	Remote Similarity	NPD484	Approved
0.6964	Remote Similarity	NPD6976	Clinical (unspecified phase)
0.6963	Remote Similarity	NPD7957	Phase 1
0.6963	Remote Similarity	NPD7958	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD1853	Clinical (unspecified phase)
0.695	Remote Similarity	NPD4181	Approved
0.695	Remote Similarity	NPD6159	Phase 2
0.6946	Remote Similarity	NPD6178	Phase 3
0.6935	Remote Similarity	NPD9690	Approved
0.6931	Remote Similarity	NPD3038	Discontinued
0.6931	Remote Similarity	NPD8408	Discontinued
0.693	Remote Similarity	NPD4865	Approved
0.6927	Remote Similarity	NPD8458	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD3002	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD5428	Discontinued
0.6923	Remote Similarity	NPD5483	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD1304	Clinical (unspecified phase)
0.6912	Remote Similarity	NPD7809	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD6711	Approved
0.6907	Remote Similarity	NPD9705	Discontinued
0.6907	Remote Similarity	NPD112	Approved
0.6905	Remote Similarity	NPD5003	Discontinued
0.69	Remote Similarity	NPD5100	Phase 3
0.69	Remote Similarity	NPD6375	Clinical (unspecified phase)
0.6898	Remote Similarity	NPD2510	Approved
0.6898	Remote Similarity	NPD2509	Approved
0.6897	Remote Similarity	NPD2094	Phase 2
0.6897	Remote Similarity	NPD2921	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD2092	Phase 2
0.6897	Remote Similarity	NPD2095	Phase 2
0.6895	Remote Similarity	NPD8094	Discontinued
0.6895	Remote Similarity	NPD8488	Clinical (unspecified phase)
0.6892	Remote Similarity	NPD3402	Phase 1
0.6888	Remote Similarity	NPD5744	Clinical (unspecified phase)
0.6884	Remote Similarity	NPD7001	Phase 3
0.6882	Remote Similarity	NPD1592	Phase 3
0.6881	Remote Similarity	NPD6452	Discontinued
0.6878	Remote Similarity	NPD7423	Phase 2
0.6875	Remote Similarity	NPD6569	Phase 2
0.6872	Remote Similarity	NPD3230	Clinical (unspecified phase)
0.6866	Remote Similarity	NPD8123	Approved
0.6866	Remote Similarity	NPD8122	Approved
0.6865	Remote Similarity	NPD786	Approved
0.6864	Remote Similarity	NPD5413	Phase 2
0.6863	Remote Similarity	NPD2096	Phase 2
0.6863	Remote Similarity	NPD2091	Phase 2
0.6853	Remote Similarity	NPD4554	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD1392	Approved
0.685	Remote Similarity	NPD4128	Approved
0.6845	Remote Similarity	NPD2383	Phase 1
0.6845	Remote Similarity	NPD3525	Discontinued
0.6842	Remote Similarity	NPD802	Phase 2
0.6837	Remote Similarity	NPD8272	Phase 2
0.6837	Remote Similarity	NPD31	Approved
0.6837	Remote Similarity	NPD3323	Discontinued
0.6837	Remote Similarity	NPD4033	Approved
0.6837	Remote Similarity	NPD32	Approved
0.6837	Remote Similarity	NPD4039	Approved
0.6837	Remote Similarity	NPD4122	Approved
0.6837	Remote Similarity	NPD4036	Approved
0.6837	Remote Similarity	NPD4038	Approved
0.6837	Remote Similarity	NPD4034	Approved
0.6837	Remote Similarity	NPD1915	Phase 1
0.6837	Remote Similarity	NPD4035	Approved
0.6837	Remote Similarity	NPD4037	Approved
0.6833	Remote Similarity	NPD3394	Approved
0.6833	Remote Similarity	NPD3393	Approved
0.6833	Remote Similarity	NPD3389	Approved
0.6822	Remote Similarity	NPD5495	Phase 2
0.6818	Remote Similarity	NPD5021	Discontinued
0.6816	Remote Similarity	NPD7194	Discontinued
0.6814	Remote Similarity	NPD4890	Phase 2
0.681	Remote Similarity	NPD4999	Phase 3
0.681	Remote Similarity	NPD7618	Phase 3
0.681	Remote Similarity	NPD7619	Phase 3
0.681	Remote Similarity	NPD4998	Phase 3
0.6807	Remote Similarity	NPD5482	Discontinued
0.6806	Remote Similarity	NPD6732	Clinical (unspecified phase)
0.6806	Remote Similarity	NPD3003	Approved
0.6798	Remote Similarity	NPD5559	Phase 2
0.6798	Remote Similarity	NPD6277	Clinical (unspecified phase)
0.6798	Remote Similarity	NPD8464	Clinical (unspecified phase)
0.6796	Remote Similarity	NPD6721	Phase 1
0.6791	Remote Similarity	NPD8072	Approved
0.6789	Remote Similarity	NPD1661	Suspended
0.6786	Remote Similarity	NPD972	Clinical (unspecified phase)
0.6784	Remote Similarity	NPD8289	Discontinued
0.6776	Remote Similarity	NPD4511	Phase 1
0.6774	Remote Similarity	NPD8493	Clinical (unspecified phase)
0.6773	Remote Similarity	NPD7594	Clinical (unspecified phase)
0.6767	Remote Similarity	NPD5891	Approved
0.6765	Remote Similarity	NPD1895	Discontinued

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