NPASS Compound

Structure

NPC470502 OpenBabel07101718302D 24 27 0 0 1 0 0 0 0 0999 V2000 4.0575 2.3736 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 3.4697 1.5646 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 -0.0000 3.0000 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 -0.8660 2.5000 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 1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 4.0000 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 -0.8660 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 4.5000 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 4.5000 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 -1.7321 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 5.5000 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 10 2 0 0 0 0 4 14 2 0 0 0 0 5 6 2 0 0 0 0 5 11 1 0 0 0 0 6 21 1 0 0 0 0 7 9 2 0 0 0 0 7 12 1 0 0 0 0 8 9 1 0 0 0 0 8 13 2 0 0 0 0 9 17 1 0 0 0 0 10 11 1 0 0 0 0 10 14 1 0 0 0 0 11 15 2 0 0 0 0 12 18 2 0 0 0 0 12 19 1 0 0 0 0 13 18 1 0 0 0 0 13 20 1 0 0 0 0 14 22 1 0 0 0 0 15 16 1 0 0 0 0 15 22 1 0 0 0 0 16 17 1 0 0 0 0 16 21 2 0 0 0 0 17 23 1 0 0 0 0 18 24 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	445.93
Volume:	340.071
LogP:	4.155
LogD:	2.789
LogS:	-4.801
# Rotatable Bonds:	2
TPSA:	69.14
# H-Bond Aceptor:	4
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.403
Synthetic Accessibility Score:	3.075
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:	-5.081
MDCK Permeability:	1.2818626601074357e-05
Pgp-inhibitor:	0.007
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.24
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.003

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.165
Plasma Protein Binding (PPB):	98.18695831298828%
Volume Distribution (VD):	0.742
Pgp-substrate:	1.1339155435562134%

ADMET: Metabolism

CYP1A2-inhibitor:	0.867
CYP1A2-substrate:	0.304
CYP2C19-inhibitor:	0.521
CYP2C19-substrate:	0.274
CYP2C9-inhibitor:	0.724
CYP2C9-substrate:	0.632
CYP2D6-inhibitor:	0.82
CYP2D6-substrate:	0.785
CYP3A4-inhibitor:	0.386
CYP3A4-substrate:	0.538

ADMET: Excretion

Clearance (CL):	0.903
Half-life (T1/2):	0.375

ADMET: Toxicity

hERG Blockers:	0.072
Human Hepatotoxicity (H-HT):	0.218
Drug-inuced Liver Injury (DILI):	0.841
AMES Toxicity:	0.036
Rat Oral Acute Toxicity:	0.904
Maximum Recommended Daily Dose:	0.965
Skin Sensitization:	0.404
Carcinogencity:	0.202
Eye Corrosion:	0.003
Eye Irritation:	0.417
Respiratory Toxicity:	0.979

Download Data

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

Natural Product: NPC470502

Natural Product ID:	NPC470502
*Common Name:**	Eudistomin Y10
IUPAC Name:	2,6-dibromo-4-[hydroxy(9H-pyrido[3,4-b]indol-1-yl)methyl]phenol
Synonyms:	Eudistomin Y10
Standard InCHIKey:	FYVBQTRGGYNHNP-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C18H12Br2N2O2/c19-12-7-9(8-13(20)18(12)24)17(23)16-15-11(5-6-21-16)10-3-1-2-4-14(10)22-15/h1-8,17,22-24H
SMILES:	C1=CC=C2C(=C1)C3=C(N2)C(=NC=C3)C(C4=CC(=C(C(=C4)Br)O)Br)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2048343
PubChem CID:	70696665
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	2
MIC	10
Others	1

Activity Type	# Activity
Cell Line	1
Individual Protein	1
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	>	223200.0	nM	PMID[455175]
NPT1821	Individual Protein	Sortase	Staphylococcus aureus	IC50	>	223200.0	nM	PMID[455175]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	25.0	ug.mL-1	PMID[455175]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	=	25.0	ug.mL-1	PMID[455175]
NPT729	Organism	Micrococcus luteus	Micrococcus luteus	MIC	=	12.5	ug.mL-1	PMID[455175]
NPT566	Organism	Salmonella typhimurium	Salmonella enterica subsp. enterica serovar Typhimurium	MIC	=	12.5	ug.mL-1	PMID[455175]
NPT766	Organism	Proteus vulgaris	Proteus vulgaris	MIC	=	12.5	ug.mL-1	PMID[455175]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	100.0	ug.mL-1	PMID[455175]
NPT87	Organism	Aspergillus fumigatus	Aspergillus fumigatus	MIC	>	100.0	ug.mL-1	PMID[455175]
NPT329	Organism	Trichophyton rubrum	Trichophyton rubrum	MIC	>	100.0	ug.mL-1	PMID[455175]
NPT330	Organism	Trichophyton mentagrophytes	Trichophyton mentagrophytes	MIC	>	100.0	ug.mL-1	PMID[455175]
NPT20	Organism	Candida albicans	Candida albicans	MIC	>	100.0	ug.mL-1	PMID[455175]
NPT2	Others	Unspecified		IC50	=	122100.0	nM	PMID[455175]

☑ 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 NPC470502 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	718
0.1-0.2	4993
0.2-0.3	12687
0.3-0.4	15903
0.4-0.5	4563
0.5-0.6	2237
0.6-0.7	1418
0.7-0.8	160
0.8-0.85	12
0.85-0.9	2
0.9-0.95	1
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9899	High Similarity	NPC470503
0.9749	High Similarity	NPC470501
0.9137	High Similarity	NPC470500
0.904	High Similarity	NPC470505
0.8853	High Similarity	NPC470504
0.8544	High Similarity	NPC5145
0.8486	Intermediate Similarity	NPC174489
0.8485	Intermediate Similarity	NPC324149
0.8409	Intermediate Similarity	NPC26641
0.8333	Intermediate Similarity	NPC37152
0.8311	Intermediate Similarity	NPC200553
0.8281	Intermediate Similarity	NPC162002
0.8265	Intermediate Similarity	NPC48938
0.8145	Intermediate Similarity	NPC279189
0.8116	Intermediate Similarity	NPC473761
0.801	Intermediate Similarity	NPC192315
0.7971	Intermediate Similarity	NPC476167
0.7952	Intermediate Similarity	NPC475070
0.789	Intermediate Similarity	NPC213530
0.789	Intermediate Similarity	NPC193267
0.7838	Intermediate Similarity	NPC60006
0.783	Intermediate Similarity	NPC476124
0.783	Intermediate Similarity	NPC476121
0.7828	Intermediate Similarity	NPC167908
0.7793	Intermediate Similarity	NPC245348
0.7772	Intermediate Similarity	NPC284678
0.7767	Intermediate Similarity	NPC99666
0.7742	Intermediate Similarity	NPC477610
0.7717	Intermediate Similarity	NPC27041
0.7685	Intermediate Similarity	NPC123976
0.7685	Intermediate Similarity	NPC167860
0.7678	Intermediate Similarity	NPC19872
0.7675	Intermediate Similarity	NPC33064
0.7673	Intermediate Similarity	NPC314394
0.7671	Intermediate Similarity	NPC8022
0.7671	Intermediate Similarity	NPC470799
0.7659	Intermediate Similarity	NPC46580
0.7656	Intermediate Similarity	NPC222018
0.7647	Intermediate Similarity	NPC292958
0.7642	Intermediate Similarity	NPC232727
0.7602	Intermediate Similarity	NPC477609
0.7598	Intermediate Similarity	NPC97902
0.7557	Intermediate Similarity	NPC304926
0.7557	Intermediate Similarity	NPC476041
0.7534	Intermediate Similarity	NPC26679
0.7522	Intermediate Similarity	NPC214142
0.7511	Intermediate Similarity	NPC54803
0.7511	Intermediate Similarity	NPC321592
0.7511	Intermediate Similarity	NPC469554
0.75	Intermediate Similarity	NPC223409
0.7489	Intermediate Similarity	NPC261251
0.7488	Intermediate Similarity	NPC476138
0.7488	Intermediate Similarity	NPC245816
0.7488	Intermediate Similarity	NPC223427
0.7488	Intermediate Similarity	NPC53144
0.7477	Intermediate Similarity	NPC52909
0.7477	Intermediate Similarity	NPC94211
0.7477	Intermediate Similarity	NPC185782
0.7477	Intermediate Similarity	NPC475935
0.7476	Intermediate Similarity	NPC314002
0.7468	Intermediate Similarity	NPC477861
0.7463	Intermediate Similarity	NPC220765
0.7456	Intermediate Similarity	NPC100547
0.7456	Intermediate Similarity	NPC477607
0.7456	Intermediate Similarity	NPC477608
0.7454	Intermediate Similarity	NPC285558
0.7453	Intermediate Similarity	NPC77555
0.7432	Intermediate Similarity	NPC74969
0.743	Intermediate Similarity	NPC176538
0.743	Intermediate Similarity	NPC205254
0.743	Intermediate Similarity	NPC106771
0.743	Intermediate Similarity	NPC303820
0.743	Intermediate Similarity	NPC23420
0.7427	Intermediate Similarity	NPC204717
0.7424	Intermediate Similarity	NPC95240
0.7424	Intermediate Similarity	NPC102423
0.7424	Intermediate Similarity	NPC322135
0.7422	Intermediate Similarity	NPC310118
0.7412	Intermediate Similarity	NPC34580
0.7412	Intermediate Similarity	NPC118559
0.7412	Intermediate Similarity	NPC304307
0.7412	Intermediate Similarity	NPC124920
0.7412	Intermediate Similarity	NPC110151
0.7397	Intermediate Similarity	NPC80596
0.7391	Intermediate Similarity	NPC14288
0.7376	Intermediate Similarity	NPC471603
0.7376	Intermediate Similarity	NPC128084
0.7371	Intermediate Similarity	NPC245055
0.7371	Intermediate Similarity	NPC182222
0.7368	Intermediate Similarity	NPC24370
0.7368	Intermediate Similarity	NPC319232
0.7363	Intermediate Similarity	NPC97343
0.7362	Intermediate Similarity	NPC81175
0.7359	Intermediate Similarity	NPC101543
0.7356	Intermediate Similarity	NPC171171
0.7354	Intermediate Similarity	NPC142901
0.7353	Intermediate Similarity	NPC96890
0.7349	Intermediate Similarity	NPC249040
0.7345	Intermediate Similarity	NPC60621
0.7339	Intermediate Similarity	NPC295228
0.7336	Intermediate Similarity	NPC212213
0.7336	Intermediate Similarity	NPC6215
0.7323	Intermediate Similarity	NPC131718
0.73	Intermediate Similarity	NPC274229
0.7291	Intermediate Similarity	NPC247980
0.729	Intermediate Similarity	NPC267928
0.7289	Intermediate Similarity	NPC469594
0.7285	Intermediate Similarity	NPC85273
0.7281	Intermediate Similarity	NPC211813
0.7277	Intermediate Similarity	NPC477110
0.7273	Intermediate Similarity	NPC326363
0.7268	Intermediate Similarity	NPC184964
0.7265	Intermediate Similarity	NPC471080
0.7265	Intermediate Similarity	NPC469592
0.7253	Intermediate Similarity	NPC284888
0.7252	Intermediate Similarity	NPC246518
0.7248	Intermediate Similarity	NPC200836
0.7241	Intermediate Similarity	NPC476451
0.7233	Intermediate Similarity	NPC72980
0.7233	Intermediate Similarity	NPC42979
0.7229	Intermediate Similarity	NPC314954
0.7222	Intermediate Similarity	NPC325976
0.722	Intermediate Similarity	NPC224764
0.722	Intermediate Similarity	NPC294620
0.7212	Intermediate Similarity	NPC264285
0.721	Intermediate Similarity	NPC207686
0.7206	Intermediate Similarity	NPC313791
0.7193	Intermediate Similarity	NPC473317
0.7188	Intermediate Similarity	NPC266931
0.7188	Intermediate Similarity	NPC476287
0.7184	Intermediate Similarity	NPC151939
0.7181	Intermediate Similarity	NPC255110
0.7179	Intermediate Similarity	NPC323752
0.7176	Intermediate Similarity	NPC265576
0.7176	Intermediate Similarity	NPC239954
0.717	Intermediate Similarity	NPC95783
0.7164	Intermediate Similarity	NPC311276
0.7163	Intermediate Similarity	NPC242209
0.7163	Intermediate Similarity	NPC251090
0.7157	Intermediate Similarity	NPC325903
0.7157	Intermediate Similarity	NPC82331
0.715	Intermediate Similarity	NPC198673
0.7143	Intermediate Similarity	NPC63751
0.7143	Intermediate Similarity	NPC207020
0.7143	Intermediate Similarity	NPC15102
0.7136	Intermediate Similarity	NPC150048
0.7136	Intermediate Similarity	NPC474958
0.7136	Intermediate Similarity	NPC203754
0.7136	Intermediate Similarity	NPC469762
0.7131	Intermediate Similarity	NPC82472
0.713	Intermediate Similarity	NPC229893
0.713	Intermediate Similarity	NPC156704
0.7124	Intermediate Similarity	NPC322064
0.7119	Intermediate Similarity	NPC477549
0.7119	Intermediate Similarity	NPC272549
0.7117	Intermediate Similarity	NPC477111
0.7116	Intermediate Similarity	NPC326634
0.7114	Intermediate Similarity	NPC475746
0.711	Intermediate Similarity	NPC315491
0.711	Intermediate Similarity	NPC45459
0.7108	Intermediate Similarity	NPC473764
0.7108	Intermediate Similarity	NPC314940
0.7107	Intermediate Similarity	NPC63971
0.7107	Intermediate Similarity	NPC91868
0.7104	Intermediate Similarity	NPC477113
0.7101	Intermediate Similarity	NPC59269
0.71	Intermediate Similarity	NPC125597
0.7097	Intermediate Similarity	NPC168911
0.7095	Intermediate Similarity	NPC178858
0.7095	Intermediate Similarity	NPC190007
0.7094	Intermediate Similarity	NPC54988
0.7094	Intermediate Similarity	NPC260434
0.7089	Intermediate Similarity	NPC231536
0.7085	Intermediate Similarity	NPC216369
0.7085	Intermediate Similarity	NPC469785
0.7073	Intermediate Similarity	NPC252590
0.7072	Intermediate Similarity	NPC88008
0.707	Intermediate Similarity	NPC307963
0.7066	Intermediate Similarity	NPC471891
0.7064	Intermediate Similarity	NPC18487
0.7062	Intermediate Similarity	NPC94943
0.7059	Intermediate Similarity	NPC41679
0.7059	Intermediate Similarity	NPC118832
0.7059	Intermediate Similarity	NPC47059
0.7059	Intermediate Similarity	NPC165349
0.7059	Intermediate Similarity	NPC329708
0.7059	Intermediate Similarity	NPC264166
0.7059	Intermediate Similarity	NPC274291
0.7056	Intermediate Similarity	NPC211416
0.7056	Intermediate Similarity	NPC122436
0.7056	Intermediate Similarity	NPC130570
0.7054	Intermediate Similarity	NPC123839
0.7054	Intermediate Similarity	NPC11464
0.7048	Intermediate Similarity	NPC288349
0.7048	Intermediate Similarity	NPC212535
0.7045	Intermediate Similarity	NPC258048
0.7043	Intermediate Similarity	NPC471506
0.704	Intermediate Similarity	NPC287208
0.704	Intermediate Similarity	NPC266249
0.7039	Intermediate Similarity	NPC476492

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 NPC470502 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	354
0.1-0.2	696
0.2-0.3	860
0.3-0.4	2119
0.4-0.5	2661
0.5-0.6	1928
0.6-0.7	509
0.7-0.8	23
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
0.7874	Intermediate Similarity	NPD7948	Phase 1
0.756	Intermediate Similarity	NPD5575	Clinical (unspecified phase)
0.7512	Intermediate Similarity	NPD5065	Approved
0.7455	Intermediate Similarity	NPD3330	Phase 1
0.7445	Intermediate Similarity	NPD7603	Discontinued
0.7444	Intermediate Similarity	NPD8405	Clinical (unspecified phase)
0.7403	Intermediate Similarity	NPD7558	Phase 2
0.7354	Intermediate Similarity	NPD5612	Discontinued
0.7252	Intermediate Similarity	NPD5067	Phase 2
0.7252	Intermediate Similarity	NPD5066	Phase 2
0.7244	Intermediate Similarity	NPD7823	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD8106	Phase 2
0.7222	Intermediate Similarity	NPD2177	Approved
0.7222	Intermediate Similarity	NPD2176	Approved
0.7222	Intermediate Similarity	NPD2175	Phase 3
0.7178	Intermediate Similarity	NPD425	Approved
0.7178	Intermediate Similarity	NPD424	Approved
0.7175	Intermediate Similarity	NPD5936	Approved
0.7175	Intermediate Similarity	NPD5939	Approved
0.7149	Intermediate Similarity	NPD6290	Phase 2
0.7143	Intermediate Similarity	NPD5069	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD6803	Clinical (unspecified phase)
0.7123	Intermediate Similarity	NPD6975	Discontinued
0.7115	Intermediate Similarity	NPD6595	Phase 3
0.711	Intermediate Similarity	NPD484	Approved
0.7103	Intermediate Similarity	NPD6569	Phase 2
0.7101	Intermediate Similarity	NPD6159	Phase 2
0.7091	Intermediate Similarity	NPD6991	Approved
0.707	Intermediate Similarity	NPD1038	Approved
0.7061	Intermediate Similarity	NPD8109	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD4034	Approved
0.7059	Intermediate Similarity	NPD4033	Approved
0.7059	Intermediate Similarity	NPD4122	Approved
0.7059	Intermediate Similarity	NPD4035	Approved
0.7059	Intermediate Similarity	NPD4038	Approved
0.7059	Intermediate Similarity	NPD4039	Approved
0.7059	Intermediate Similarity	NPD32	Approved
0.7059	Intermediate Similarity	NPD4036	Approved
0.7059	Intermediate Similarity	NPD31	Approved
0.7059	Intermediate Similarity	NPD4037	Approved
0.7028	Intermediate Similarity	NPD706	Phase 1
0.7022	Intermediate Similarity	NPD4502	Phase 2
0.7008	Intermediate Similarity	NPD5482	Discontinued
0.7005	Intermediate Similarity	NPD9690	Approved
0.7	Intermediate Similarity	NPD4511	Phase 1
0.6986	Remote Similarity	NPD3825	Phase 3
0.6983	Remote Similarity	NPD5483	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD6610	Clinical (unspecified phase)
0.6976	Remote Similarity	NPD2781	Approved
0.6964	Remote Similarity	NPD7671	Approved
0.6964	Remote Similarity	NPD7672	Approved
0.6961	Remote Similarity	NPD2782	Approved
0.6961	Remote Similarity	NPD2780	Approved
0.6958	Remote Similarity	NPD2921	Clinical (unspecified phase)
0.694	Remote Similarity	NPD1856	Discontinued
0.692	Remote Similarity	NPD7222	Phase 2
0.692	Remote Similarity	NPD1392	Approved
0.6919	Remote Similarity	NPD7414	Clinical (unspecified phase)
0.6916	Remote Similarity	NPD2383	Phase 1
0.6916	Remote Similarity	NPD6141	Clinical (unspecified phase)
0.6912	Remote Similarity	NPD802	Phase 2
0.6912	Remote Similarity	NPD1304	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD4076	Approved
0.6905	Remote Similarity	NPD4079	Approved
0.6901	Remote Similarity	NPD6344	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD6473	Phase 1
0.6897	Remote Similarity	NPD112	Approved
0.6897	Remote Similarity	NPD9705	Discontinued
0.689	Remote Similarity	NPD2382	Approved
0.689	Remote Similarity	NPD2380	Approved
0.689	Remote Similarity	NPD2381	Approved
0.6889	Remote Similarity	NPD5658	Approved
0.6887	Remote Similarity	NPD5596	Phase 2
0.6883	Remote Similarity	NPD7194	Discontinued
0.688	Remote Similarity	NPD4890	Phase 2
0.6875	Remote Similarity	NPD3003	Approved
0.687	Remote Similarity	NPD5409	Clinical (unspecified phase)
0.6866	Remote Similarity	NPD3404	Approved
0.6864	Remote Similarity	NPD5559	Phase 2
0.6861	Remote Similarity	NPD4886	Phase 2
0.6857	Remote Similarity	NPD3506	Approved
0.6857	Remote Similarity	NPD3505	Approved
0.6856	Remote Similarity	NPD6140	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD3321	Discontinued
0.6844	Remote Similarity	NPD6838	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD6492	Phase 2
0.6816	Remote Similarity	NPD3931	Approved
0.6816	Remote Similarity	NPD3928	Approved
0.6814	Remote Similarity	NPD7947	Clinical (unspecified phase)
0.681	Remote Similarity	NPD3402	Phase 1
0.6784	Remote Similarity	NPD2125	Clinical (unspecified phase)
0.6783	Remote Similarity	NPD5903	Approved
0.6783	Remote Similarity	NPD5902	Approved
0.6779	Remote Similarity	NPD4184	Clinical (unspecified phase)
0.6777	Remote Similarity	NPD6203	Clinical (unspecified phase)
0.6776	Remote Similarity	NPD5083	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD8063	Discontinued
0.677	Remote Similarity	NPD7452	Approved
0.677	Remote Similarity	NPD7453	Approved
0.6769	Remote Similarity	NPD8093	Discontinued
0.6766	Remote Similarity	NPD2882	Phase 1
0.6765	Remote Similarity	NPD5255	Approved
0.676	Remote Similarity	NPD8442	Discontinued
0.6759	Remote Similarity	NPD8431	Approved
0.6757	Remote Similarity	NPD4548	Discontinued
0.6757	Remote Similarity	NPD3814	Phase 1
0.6756	Remote Similarity	NPD7712	Clinical (unspecified phase)
0.6756	Remote Similarity	NPD4795	Phase 2
0.6754	Remote Similarity	NPD8321	Discontinued
0.6753	Remote Similarity	NPD5287	Discontinued
0.675	Remote Similarity	NPD5040	Clinical (unspecified phase)
0.675	Remote Similarity	NPD6494	Phase 2
0.6745	Remote Similarity	NPD5450	Discontinued
0.6744	Remote Similarity	NPD7424	Clinical (unspecified phase)
0.6738	Remote Similarity	NPD537	Phase 2
0.6738	Remote Similarity	NPD534	Phase 2
0.6729	Remote Similarity	NPD5728	Clinical (unspecified phase)
0.6728	Remote Similarity	NPD8110	Clinical (unspecified phase)
0.6726	Remote Similarity	NPD3932	Clinical (unspecified phase)
0.6725	Remote Similarity	NPD6220	Phase 3
0.6715	Remote Similarity	NPD926	Approved
0.6715	Remote Similarity	NPD925	Approved
0.6709	Remote Similarity	NPD1996	Discontinued
0.6699	Remote Similarity	NPD1325	Approved
0.6699	Remote Similarity	NPD1326	Approved
0.6698	Remote Similarity	NPD5751	Clinical (unspecified phase)
0.6697	Remote Similarity	NPD6449	Clinical (unspecified phase)
0.6696	Remote Similarity	NPD3930	Clinical (unspecified phase)
0.6683	Remote Similarity	NPD6158	Phase 2
0.6683	Remote Similarity	NPD6476	Clinical (unspecified phase)
0.6682	Remote Similarity	NPD8396	Approved
0.6682	Remote Similarity	NPD8395	Approved
0.6682	Remote Similarity	NPD9695	Approved
0.6682	Remote Similarity	NPD7867	Phase 1
0.6681	Remote Similarity	NPD7112	Discontinued
0.6681	Remote Similarity	NPD5901	Discontinued
0.6681	Remote Similarity	NPD7726	Phase 1
0.668	Remote Similarity	NPD4080	Discontinued
0.6667	Remote Similarity	NPD4440	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4555	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1183	Approved
0.6667	Remote Similarity	NPD5140	Approved
0.6667	Remote Similarity	NPD2615	Phase 3
0.6667	Remote Similarity	NPD6501	Approved
0.6667	Remote Similarity	NPD2616	Phase 3
0.6667	Remote Similarity	NPD3254	Phase 1
0.6667	Remote Similarity	NPD4612	Discontinued
0.6667	Remote Similarity	NPD5138	Approved
0.6667	Remote Similarity	NPD3082	Discontinued
0.6667	Remote Similarity	NPD5913	Phase 3
0.6667	Remote Similarity	NPD7586	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6500	Approved
0.6667	Remote Similarity	NPD3255	Phase 1
0.6667	Remote Similarity	NPD5912	Clinical (unspecified phase)
0.6652	Remote Similarity	NPD7958	Clinical (unspecified phase)
0.6652	Remote Similarity	NPD7470	Discontinued
0.6652	Remote Similarity	NPD7957	Phase 1
0.6652	Remote Similarity	NPD4131	Phase 3
0.6652	Remote Similarity	NPD1740	Approved
0.6652	Remote Similarity	NPD3324	Clinical (unspecified phase)
0.6652	Remote Similarity	NPD4862	Clinical (unspecified phase)
0.6652	Remote Similarity	NPD5164	Discontinued
0.6652	Remote Similarity	NPD1739	Approved
0.6652	Remote Similarity	NPD8403	Phase 1
0.6651	Remote Similarity	NPD5522	Clinical (unspecified phase)
0.6651	Remote Similarity	NPD5862	Discovery
0.6651	Remote Similarity	NPD6872	Clinical (unspecified phase)
0.665	Remote Similarity	NPD9398	Clinical (unspecified phase)
0.6637	Remote Similarity	NPD2121	Clinical (unspecified phase)
0.6634	Remote Similarity	NPD4671	Clinical (unspecified phase)
0.6634	Remote Similarity	NPD4669	Clinical (unspecified phase)
0.6634	Remote Similarity	NPD4670	Clinical (unspecified phase)
0.6633	Remote Similarity	NPD9076	Clinical (unspecified phase)
0.6626	Remote Similarity	NPD4454	Phase 2
0.6625	Remote Similarity	NPD3302	Clinical (unspecified phase)
0.6624	Remote Similarity	NPD6985	Discontinued
0.6623	Remote Similarity	NPD8322	Phase 2
0.6623	Remote Similarity	NPD2794	Discontinued
0.6623	Remote Similarity	NPD8410	Clinical (unspecified phase)
0.6621	Remote Similarity	NPD6281	Approved
0.662	Remote Similarity	NPD2144	Approved
0.6611	Remote Similarity	NPD6553	Clinical (unspecified phase)
0.6611	Remote Similarity	NPD6978	Phase 2
0.6611	Remote Similarity	NPD6977	Clinical (unspecified phase)
0.6608	Remote Similarity	NPD5426	Phase 3
0.6607	Remote Similarity	NPD1768	Approved
0.6607	Remote Similarity	NPD4118	Clinical (unspecified phase)
0.6604	Remote Similarity	NPD482	Approved
0.6602	Remote Similarity	NPD604	Clinical (unspecified phase)
0.6601	Remote Similarity	NPD9706	Clinical (unspecified phase)
0.6599	Remote Similarity	NPD7067	Approved
0.6599	Remote Similarity	NPD7068	Approved
0.6597	Remote Similarity	NPD4401	Phase 2
0.6597	Remote Similarity	NPD6976	Clinical (unspecified phase)
0.6597	Remote Similarity	NPD4403	Phase 3
0.6592	Remote Similarity	NPD1229	Phase 2
0.6591	Remote Similarity	NPD4699	Discontinued
0.659	Remote Similarity	NPD2762	Phase 2
0.6589	Remote Similarity	NPD1620	Clinical (unspecified phase)
0.6587	Remote Similarity	NPD861	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