NPASS Compound

Structure

NPC174489 OpenBabel07101718242D 24 27 0 0 0 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 0 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 2 0 0 0 0 18 24 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	443.91
Volume:	337.435
LogP:	4.656
LogD:	3.344
LogS:	-5.278
# Rotatable Bonds:	2
TPSA:	65.98
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.418
Synthetic Accessibility Score:	2.474
Fsp3:	0.0
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.164
MDCK Permeability:	1.3748946912528481e-05
Pgp-inhibitor:	0.998
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.062
20% Bioavailability (F20%):	0.001
30% Bioavailability (F30%):	0.006

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.188
Plasma Protein Binding (PPB):	99.59056091308594%
Volume Distribution (VD):	0.512
Pgp-substrate:	0.9429454803466797%

ADMET: Metabolism

CYP1A2-inhibitor:	0.973
CYP1A2-substrate:	0.167
CYP2C19-inhibitor:	0.686
CYP2C19-substrate:	0.065
CYP2C9-inhibitor:	0.639
CYP2C9-substrate:	0.35
CYP2D6-inhibitor:	0.706
CYP2D6-substrate:	0.554
CYP3A4-inhibitor:	0.421
CYP3A4-substrate:	0.114

ADMET: Excretion

Clearance (CL):	0.578
Half-life (T1/2):	0.297

ADMET: Toxicity

hERG Blockers:	0.046
Human Hepatotoxicity (H-HT):	0.544
Drug-inuced Liver Injury (DILI):	0.964
AMES Toxicity:	0.185
Rat Oral Acute Toxicity:	0.779
Maximum Recommended Daily Dose:	0.908
Skin Sensitization:	0.137
Carcinogencity:	0.714
Eye Corrosion:	0.004
Eye Irritation:	0.525
Respiratory Toxicity:	0.955

Download Data

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

Natural Product: NPC174489

Natural Product ID:	NPC174489
*Common Name:**	Eudistomin Y5
IUPAC Name:	(3,5-dibromo-4-hydroxyphenyl)-(9H-pyrido[3,4-b]indol-1-yl)methanone
Synonyms:	Eudistomin Y5
Standard InCHIKey:	LDRUYDYVJKQZJS-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C18H10Br2N2O2/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/h1-8,22,24H
SMILES:	c1ccc2c(c1)c1ccnc(c1[nH]2)C(=O)c1cc(c(c(c1)Br)O)Br
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2048339
PubChem CID:	24800707
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	=	85400.0	nM	PMID[573982]
NPT1821	Individual Protein	Sortase	Staphylococcus aureus	IC50	=	146400.0	nM	PMID[573982]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	6.25	ug.mL-1	PMID[573982]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	=	3.125	ug.mL-1	PMID[573982]
NPT729	Organism	Micrococcus luteus	Micrococcus luteus	MIC	=	3.125	ug.mL-1	PMID[573982]
NPT566	Organism	Salmonella typhimurium	Salmonella enterica subsp. enterica serovar Typhimurium	MIC	=	0.78	ug.mL-1	PMID[573982]
NPT766	Organism	Proteus vulgaris	Proteus vulgaris	MIC	=	1.56	ug.mL-1	PMID[573982]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	=	100.0	ug.mL-1	PMID[573982]
NPT87	Organism	Aspergillus fumigatus	Aspergillus fumigatus	MIC	>	100.0	ug.mL-1	PMID[573982]
NPT329	Organism	Trichophyton rubrum	Trichophyton rubrum	MIC	>	100.0	ug.mL-1	PMID[573982]
NPT330	Organism	Trichophyton mentagrophytes	Trichophyton mentagrophytes	MIC	>	100.0	ug.mL-1	PMID[573982]
NPT20	Organism	Candida albicans	Candida albicans	MIC	>	100.0	ug.mL-1	PMID[573982]
NPT2	Others	Unspecified		IC50	=	19800.0	nM	PMID[573982]

☑ 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 NPC174489 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	740
0.1-0.2	5256
0.2-0.3	12231
0.3-0.4	13605
0.4-0.5	6973
0.5-0.6	2265
0.6-0.7	1420
0.7-0.8	192
0.8-0.85	7
0.85-0.9	1
0.9-0.95	1
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
0.9904	High Similarity	NPC26641
0.981	High Similarity	NPC37152
0.9808	High Similarity	NPC200553
0.9762	High Similarity	NPC162002
0.9619	High Similarity	NPC279189
0.9183	High Similarity	NPC27041
0.8649	High Similarity	NPC97902
0.8486	Intermediate Similarity	NPC470502
0.8475	Intermediate Similarity	NPC207686
0.8409	Intermediate Similarity	NPC470503
0.8341	Intermediate Similarity	NPC322064
0.8281	Intermediate Similarity	NPC470501
0.8038	Intermediate Similarity	NPC324149
0.8	Intermediate Similarity	NPC229893
0.7981	Intermediate Similarity	NPC237414
0.7946	Intermediate Similarity	NPC276657
0.7932	Intermediate Similarity	NPC63971
0.7932	Intermediate Similarity	NPC91868
0.7931	Intermediate Similarity	NPC235685
0.7922	Intermediate Similarity	NPC182222
0.792	Intermediate Similarity	NPC122436
0.7897	Intermediate Similarity	NPC101350
0.785	Intermediate Similarity	NPC474916
0.78	Intermediate Similarity	NPC77101
0.7798	Intermediate Similarity	NPC470505
0.7788	Intermediate Similarity	NPC323969
0.7773	Intermediate Similarity	NPC178858
0.7746	Intermediate Similarity	NPC326422
0.7746	Intermediate Similarity	NPC216369
0.7717	Intermediate Similarity	NPC470500
0.7713	Intermediate Similarity	NPC110182
0.7692	Intermediate Similarity	NPC191415
0.7682	Intermediate Similarity	NPC175602
0.7639	Intermediate Similarity	NPC74153
0.7639	Intermediate Similarity	NPC260434
0.7636	Intermediate Similarity	NPC472259
0.7634	Intermediate Similarity	NPC219087
0.7613	Intermediate Similarity	NPC171787
0.7613	Intermediate Similarity	NPC266249
0.7585	Intermediate Similarity	NPC477549
0.7583	Intermediate Similarity	NPC470504
0.7581	Intermediate Similarity	NPC473821
0.7578	Intermediate Similarity	NPC61038
0.7568	Intermediate Similarity	NPC183777
0.7565	Intermediate Similarity	NPC220851
0.7561	Intermediate Similarity	NPC63109
0.7545	Intermediate Similarity	NPC123839
0.7511	Intermediate Similarity	NPC317701
0.75	Intermediate Similarity	NPC471944
0.749	Intermediate Similarity	NPC258048
0.7489	Intermediate Similarity	NPC243633
0.7489	Intermediate Similarity	NPC175150
0.7488	Intermediate Similarity	NPC102755
0.7477	Intermediate Similarity	NPC475070
0.7468	Intermediate Similarity	NPC33064
0.7468	Intermediate Similarity	NPC475635
0.7467	Intermediate Similarity	NPC264285
0.746	Intermediate Similarity	NPC74619
0.7445	Intermediate Similarity	NPC207866
0.7435	Intermediate Similarity	NPC269270
0.743	Intermediate Similarity	NPC278434
0.7411	Intermediate Similarity	NPC270918
0.7403	Intermediate Similarity	NPC14686
0.7397	Intermediate Similarity	NPC78767
0.7397	Intermediate Similarity	NPC473814
0.7393	Intermediate Similarity	NPC60006
0.7389	Intermediate Similarity	NPC5145
0.7387	Intermediate Similarity	NPC57398
0.7368	Intermediate Similarity	NPC470703
0.7366	Intermediate Similarity	NPC476121
0.7366	Intermediate Similarity	NPC476124
0.7366	Intermediate Similarity	NPC82053
0.7361	Intermediate Similarity	NPC324091
0.7359	Intermediate Similarity	NPC74360
0.7354	Intermediate Similarity	NPC53144
0.7353	Intermediate Similarity	NPC284888
0.735	Intermediate Similarity	NPC245348
0.7336	Intermediate Similarity	NPC237740
0.733	Intermediate Similarity	NPC81535
0.7325	Intermediate Similarity	NPC118940
0.7325	Intermediate Similarity	NPC473218
0.7325	Intermediate Similarity	NPC470702
0.7318	Intermediate Similarity	NPC141454
0.7314	Intermediate Similarity	NPC148889
0.7306	Intermediate Similarity	NPC93390
0.7299	Intermediate Similarity	NPC284775
0.7296	Intermediate Similarity	NPC60621
0.7294	Intermediate Similarity	NPC99666
0.7293	Intermediate Similarity	NPC477610
0.7285	Intermediate Similarity	NPC192315
0.7284	Intermediate Similarity	NPC193267
0.7284	Intermediate Similarity	NPC213530
0.7281	Intermediate Similarity	NPC82370
0.7273	Intermediate Similarity	NPC469727
0.7265	Intermediate Similarity	NPC16352
0.7252	Intermediate Similarity	NPC476167
0.7252	Intermediate Similarity	NPC477004
0.7246	Intermediate Similarity	NPC214142
0.724	Intermediate Similarity	NPC53534
0.7232	Intermediate Similarity	NPC211813
0.7229	Intermediate Similarity	NPC74969
0.722	Intermediate Similarity	NPC315491
0.722	Intermediate Similarity	NPC45459
0.7218	Intermediate Similarity	NPC181081
0.7215	Intermediate Similarity	NPC124920
0.7215	Intermediate Similarity	NPC34580
0.7215	Intermediate Similarity	NPC261251
0.7215	Intermediate Similarity	NPC118559
0.7215	Intermediate Similarity	NPC304307
0.7202	Intermediate Similarity	NPC154339
0.72	Intermediate Similarity	NPC165599
0.72	Intermediate Similarity	NPC200836
0.7195	Intermediate Similarity	NPC222018
0.719	Intermediate Similarity	NPC15801
0.7189	Intermediate Similarity	NPC471536
0.7185	Intermediate Similarity	NPC100547
0.7178	Intermediate Similarity	NPC245055
0.7173	Intermediate Similarity	NPC319232
0.7173	Intermediate Similarity	NPC24370
0.717	Intermediate Similarity	NPC151635
0.7169	Intermediate Similarity	NPC476460
0.7168	Intermediate Similarity	NPC132539
0.7167	Intermediate Similarity	NPC477609
0.7163	Intermediate Similarity	NPC48938
0.7162	Intermediate Similarity	NPC90229
0.7162	Intermediate Similarity	NPC85273
0.7162	Intermediate Similarity	NPC227582
0.7162	Intermediate Similarity	NPC167710
0.7162	Intermediate Similarity	NPC309845
0.7161	Intermediate Similarity	NPC167908
0.7155	Intermediate Similarity	NPC322135
0.7155	Intermediate Similarity	NPC326363
0.7155	Intermediate Similarity	NPC67658
0.7155	Intermediate Similarity	NPC223409
0.7155	Intermediate Similarity	NPC95240
0.7149	Intermediate Similarity	NPC202812
0.7143	Intermediate Similarity	NPC213308
0.7143	Intermediate Similarity	NPC62749
0.7137	Intermediate Similarity	NPC168209
0.7137	Intermediate Similarity	NPC474357
0.713	Intermediate Similarity	NPC131887
0.7125	Intermediate Similarity	NPC14288
0.7124	Intermediate Similarity	NPC304926
0.7124	Intermediate Similarity	NPC476041
0.7117	Intermediate Similarity	NPC102592
0.7117	Intermediate Similarity	NPC179701
0.7117	Intermediate Similarity	NPC79356
0.711	Intermediate Similarity	NPC46580
0.7107	Intermediate Similarity	NPC325976
0.7105	Intermediate Similarity	NPC244741
0.7104	Intermediate Similarity	NPC267343
0.7104	Intermediate Similarity	NPC304203
0.71	Intermediate Similarity	NPC207020
0.7097	Intermediate Similarity	NPC295158
0.7095	Intermediate Similarity	NPC54803
0.7095	Intermediate Similarity	NPC267078
0.7095	Intermediate Similarity	NPC935
0.7095	Intermediate Similarity	NPC321592
0.7091	Intermediate Similarity	NPC138370
0.709	Intermediate Similarity	NPC41679
0.7087	Intermediate Similarity	NPC167860
0.7087	Intermediate Similarity	NPC123976
0.7085	Intermediate Similarity	NPC262898
0.708	Intermediate Similarity	NPC473761
0.7075	Intermediate Similarity	NPC475746
0.7075	Intermediate Similarity	NPC252572
0.7074	Intermediate Similarity	NPC116555
0.707	Intermediate Similarity	NPC152620
0.7067	Intermediate Similarity	NPC252338
0.7054	Intermediate Similarity	NPC477112
0.7051	Intermediate Similarity	NPC472285
0.7051	Intermediate Similarity	NPC110158
0.7048	Intermediate Similarity	NPC134848
0.7048	Intermediate Similarity	NPC476098
0.7045	Intermediate Similarity	NPC83111
0.7042	Intermediate Similarity	NPC477607
0.7042	Intermediate Similarity	NPC66777
0.7042	Intermediate Similarity	NPC477608
0.7039	Intermediate Similarity	NPC477979
0.7035	Intermediate Similarity	NPC232727
0.7026	Intermediate Similarity	NPC471194
0.7026	Intermediate Similarity	NPC471603
0.7026	Intermediate Similarity	NPC471193
0.7025	Intermediate Similarity	NPC196718
0.7018	Intermediate Similarity	NPC314002
0.7016	Intermediate Similarity	NPC208522
0.7009	Intermediate Similarity	NPC156704
0.7009	Intermediate Similarity	NPC77555
0.7005	Intermediate Similarity	NPC220765
0.7004	Intermediate Similarity	NPC171393
0.7004	Intermediate Similarity	NPC295452
0.7	Intermediate Similarity	NPC221873
0.6996	Remote Similarity	NPC323752
0.6987	Remote Similarity	NPC476818
0.6983	Remote Similarity	NPC119006
0.6983	Remote Similarity	NPC470323
0.6982	Remote Similarity	NPC47190
0.6981	Remote Similarity	NPC97343
0.698	Remote Similarity	NPC184225
0.6974	Remote Similarity	NPC223427

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 NPC174489 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	378
0.1-0.2	717
0.2-0.3	874
0.3-0.4	2281
0.4-0.5	2486
0.5-0.6	1914
0.6-0.7	489
0.7-0.8	11
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
0.7467	Intermediate Similarity	NPD8405	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD4845	Discontinued
0.7426	Intermediate Similarity	NPD5040	Clinical (unspecified phase)
0.7342	Intermediate Similarity	NPD8106	Phase 2
0.7319	Intermediate Similarity	NPD7603	Discontinued
0.7318	Intermediate Similarity	NPD7948	Phase 1
0.7244	Intermediate Similarity	NPD5901	Discontinued
0.7224	Intermediate Similarity	NPD5483	Clinical (unspecified phase)
0.722	Intermediate Similarity	NPD484	Approved
0.7179	Intermediate Similarity	NPD1996	Discontinued
0.7155	Intermediate Similarity	NPD3393	Approved
0.7155	Intermediate Similarity	NPD3389	Approved
0.7155	Intermediate Similarity	NPD3394	Approved
0.7131	Intermediate Similarity	NPD2921	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD2121	Clinical (unspecified phase)
0.7123	Intermediate Similarity	NPD5065	Approved
0.7108	Intermediate Similarity	NPD5482	Discontinued
0.7106	Intermediate Similarity	NPD6242	Discontinued
0.7105	Intermediate Similarity	NPD6838	Clinical (unspecified phase)
0.7104	Intermediate Similarity	NPD5575	Clinical (unspecified phase)
0.7074	Intermediate Similarity	NPD2509	Approved
0.7074	Intermediate Similarity	NPD6376	Discontinued
0.7074	Intermediate Similarity	NPD2510	Approved
0.7016	Intermediate Similarity	NPD3959	Phase 2
0.7016	Intermediate Similarity	NPD3962	Phase 2
0.698	Remote Similarity	NPD4958	Clinical (unspecified phase)
0.6953	Remote Similarity	NPD6530	Approved
0.6953	Remote Similarity	NPD6531	Approved
0.6949	Remote Similarity	NPD4429	Discontinued
0.6946	Remote Similarity	NPD2803	Discontinued
0.6942	Remote Similarity	NPD5801	Clinical (unspecified phase)
0.691	Remote Similarity	NPD7927	Clinical (unspecified phase)
0.6881	Remote Similarity	NPD3178	Discontinued
0.6878	Remote Similarity	NPD4948	Discontinued
0.6865	Remote Similarity	NPD4558	Phase 2
0.686	Remote Similarity	NPD7994	Phase 2
0.6851	Remote Similarity	NPD3794	Approved
0.6851	Remote Similarity	NPD3795	Approved
0.6849	Remote Similarity	NPD5728	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD8248	Clinical (unspecified phase)
0.6838	Remote Similarity	NPD5475	Discontinued
0.682	Remote Similarity	NPD5827	Discontinued
0.6809	Remote Similarity	NPD8093	Discontinued
0.6803	Remote Similarity	NPD5022	Discontinued
0.6798	Remote Similarity	NPD7000	Clinical (unspecified phase)
0.6798	Remote Similarity	NPD6999	Discontinued
0.6797	Remote Similarity	NPD5426	Phase 3
0.679	Remote Similarity	NPD6165	Phase 2
0.679	Remote Similarity	NPD6164	Phase 2
0.6782	Remote Similarity	NPD5450	Discontinued
0.678	Remote Similarity	NPD3243	Approved
0.6765	Remote Similarity	NPD7823	Clinical (unspecified phase)
0.676	Remote Similarity	NPD6790	Phase 1
0.6757	Remote Similarity	NPD4426	Clinical (unspecified phase)
0.6749	Remote Similarity	NPD8289	Discontinued
0.6748	Remote Similarity	NPD3960	Clinical (unspecified phase)
0.6744	Remote Similarity	NPD8091	Phase 3
0.6742	Remote Similarity	NPD6178	Phase 3
0.6734	Remote Similarity	NPD5891	Approved
0.6734	Remote Similarity	NPD7853	Phase 2
0.673	Remote Similarity	NPD7393	Clinical (unspecified phase)
0.6728	Remote Similarity	NPD482	Approved
0.6726	Remote Similarity	NPD460	Discontinued
0.6725	Remote Similarity	NPD6137	Clinical (unspecified phase)
0.6724	Remote Similarity	NPD6987	Phase 1
0.6723	Remote Similarity	NPD7998	Clinical (unspecified phase)
0.6723	Remote Similarity	NPD6803	Clinical (unspecified phase)
0.6711	Remote Similarity	NPD5592	Clinical (unspecified phase)
0.6709	Remote Similarity	NPD7666	Phase 3
0.6709	Remote Similarity	NPD7665	Phase 2
0.6709	Remote Similarity	NPD8094	Discontinued
0.6708	Remote Similarity	NPD7586	Clinical (unspecified phase)
0.6706	Remote Similarity	NPD6525	Clinical (unspecified phase)
0.6705	Remote Similarity	NPD6458	Discontinued
0.6697	Remote Similarity	NPD749	Clinical (unspecified phase)
0.6697	Remote Similarity	NPD2092	Phase 2
0.6697	Remote Similarity	NPD2095	Phase 2
0.6697	Remote Similarity	NPD2094	Phase 2
0.6696	Remote Similarity	NPD7619	Phase 3
0.6696	Remote Similarity	NPD7618	Phase 3
0.6695	Remote Similarity	NPD4989	Phase 2
0.6695	Remote Similarity	NPD5416	Discontinued
0.6695	Remote Similarity	NPD2008	Discontinued
0.6694	Remote Similarity	NPD2951	Discontinued
0.6681	Remote Similarity	NPD4922	Phase 2
0.668	Remote Similarity	NPD5050	Approved
0.6667	Remote Similarity	NPD3006	Discontinued
0.6667	Remote Similarity	NPD2411	Approved
0.6667	Remote Similarity	NPD3330	Phase 1
0.6667	Remote Similarity	NPD3607	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2096	Phase 2
0.6667	Remote Similarity	NPD5479	Discontinued
0.6667	Remote Similarity	NPD2091	Phase 2
0.6653	Remote Similarity	NPD5612	Discontinued
0.6653	Remote Similarity	NPD4850	Phase 1
0.6653	Remote Similarity	NPD4051	Discontinued
0.6652	Remote Similarity	NPD6288	Clinical (unspecified phase)
0.6651	Remote Similarity	NPD424	Approved
0.6651	Remote Similarity	NPD425	Approved
0.6639	Remote Similarity	NPD7203	Clinical (unspecified phase)
0.6639	Remote Similarity	NPD7404	Approved
0.6638	Remote Similarity	NPD7187	Phase 2
0.6638	Remote Similarity	NPD6975	Discontinued
0.6637	Remote Similarity	NPD2336	Approved
0.6625	Remote Similarity	NPD3326	Clinical (unspecified phase)
0.6624	Remote Similarity	NPD4862	Clinical (unspecified phase)
0.6624	Remote Similarity	NPD4614	Clinical (unspecified phase)
0.6624	Remote Similarity	NPD6567	Clinical (unspecified phase)
0.6623	Remote Similarity	NPD5975	Clinical (unspecified phase)
0.6612	Remote Similarity	NPD3280	Approved
0.6611	Remote Similarity	NPD5417	Clinical (unspecified phase)
0.661	Remote Similarity	NPD1600	Suspended
0.6609	Remote Similarity	NPD4987	Clinical (unspecified phase)
0.6606	Remote Similarity	NPD2479	Phase 3
0.6606	Remote Similarity	NPD2481	Approved
0.6598	Remote Similarity	NPD6173	Approved
0.6598	Remote Similarity	NPD3222	Phase 2
0.6595	Remote Similarity	NPD4511	Phase 1
0.6595	Remote Similarity	NPD5017	Discontinued
0.6594	Remote Similarity	NPD4848	Phase 1
0.6592	Remote Similarity	NPD7689	Approved
0.6583	Remote Similarity	NPD2412	Clinical (unspecified phase)
0.6581	Remote Similarity	NPD3947	Discontinued
0.6579	Remote Similarity	NPD1038	Approved
0.6578	Remote Similarity	NPD6141	Clinical (unspecified phase)
0.6577	Remote Similarity	NPD1783	Clinical (unspecified phase)
0.6575	Remote Similarity	NPD4883	Approved
0.6564	Remote Similarity	NPD6180	Clinical (unspecified phase)
0.6557	Remote Similarity	NPD6824	Clinical (unspecified phase)
0.6557	Remote Similarity	NPD8356	Approved
0.6555	Remote Similarity	NPD7470	Discontinued
0.6546	Remote Similarity	NPD3746	Discontinued
0.6544	Remote Similarity	NPD2781	Approved
0.6542	Remote Similarity	NPD5293	Phase 2
0.6538	Remote Similarity	NPD6991	Approved
0.6535	Remote Similarity	NPD4376	Phase 3
0.6532	Remote Similarity	NPD5473	Discontinued
0.6531	Remote Similarity	NPD6752	Phase 1
0.6531	Remote Similarity	NPD7547	Clinical (unspecified phase)
0.6531	Remote Similarity	NPD6753	Phase 1
0.6529	Remote Similarity	NPD7878	Phase 2
0.6528	Remote Similarity	NPD2782	Approved
0.6528	Remote Similarity	NPD2780	Approved
0.6527	Remote Similarity	NPD7594	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD2307	Discontinued
0.6522	Remote Similarity	NPD2290	Phase 3
0.6522	Remote Similarity	NPD2289	Phase 3
0.652	Remote Similarity	NPD7558	Phase 2
0.652	Remote Similarity	NPD7415	Suspended
0.6518	Remote Similarity	NPD3259	Approved
0.6518	Remote Similarity	NPD1096	Discontinued
0.6518	Remote Similarity	NPD8430	Approved
0.6511	Remote Similarity	NPD6138	Clinical (unspecified phase)
0.6511	Remote Similarity	NPD2721	Clinical (unspecified phase)
0.6507	Remote Similarity	NPD802	Phase 2
0.6498	Remote Similarity	NPD7947	Clinical (unspecified phase)
0.6498	Remote Similarity	NPD2916	Discontinued
0.6494	Remote Similarity	NPD6153	Approved
0.6489	Remote Similarity	NPD6344	Clinical (unspecified phase)
0.6489	Remote Similarity	NPD6610	Clinical (unspecified phase)
0.6488	Remote Similarity	NPD5409	Clinical (unspecified phase)
0.6486	Remote Similarity	NPD5398	Clinical (unspecified phase)
0.6483	Remote Similarity	NPD6732	Clinical (unspecified phase)
0.6483	Remote Similarity	NPD7001	Phase 3
0.6483	Remote Similarity	NPD2715	Clinical (unspecified phase)
0.648	Remote Similarity	NPD5151	Clinical (unspecified phase)
0.6479	Remote Similarity	NPD7925	Phase 2
0.6479	Remote Similarity	NPD7924	Phase 2
0.6475	Remote Similarity	NPD8349	Phase 1
0.6475	Remote Similarity	NPD5850	Phase 3
0.6471	Remote Similarity	NPD3914	Clinical (unspecified phase)
0.6468	Remote Similarity	NPD4886	Phase 2
0.6468	Remote Similarity	NPD6176	Phase 1
0.6463	Remote Similarity	NPD3404	Approved
0.6461	Remote Similarity	NPD7395	Discontinued
0.6457	Remote Similarity	NPD6595	Phase 3
0.6457	Remote Similarity	NPD1291	Clinical (unspecified phase)
0.6456	Remote Similarity	NPD3905	Phase 3
0.6456	Remote Similarity	NPD1506	Discontinued
0.6455	Remote Similarity	NPD750	Phase 2
0.6454	Remote Similarity	NPD4373	Phase 2
0.6454	Remote Similarity	NPD6741	Clinical (unspecified phase)
0.6446	Remote Similarity	NPD2433	Clinical (unspecified phase)
0.6444	Remote Similarity	NPD7564	Discontinued
0.6441	Remote Similarity	NPD7712	Clinical (unspecified phase)
0.6441	Remote Similarity	NPD6159	Phase 2
0.6438	Remote Similarity	NPD3814	Phase 1
0.6438	Remote Similarity	NPD3825	Phase 3
0.6437	Remote Similarity	NPD2311	Clinical (unspecified phase)
0.6437	Remote Similarity	NPD4926	Clinical (unspecified phase)
0.6437	Remote Similarity	NPD7269	Clinical (unspecified phase)
0.6435	Remote Similarity	NPD1304	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD7672	Approved
0.6429	Remote Similarity	NPD7414	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD4011	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD2443	Approved
0.6429	Remote Similarity	NPD7671	Approved
0.6429	Remote Similarity	NPD2442	Approved
0.6426	Remote Similarity	NPD3928	Approved
0.6426	Remote Similarity	NPD3931	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