NPASS Compound

Structure

CID195507 OpenBabel06191715582D 26 30 0 0 1 0 0 0 0 0999 V2000 -0.8533 -0.4925 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6740 2.8647 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9537 -1.5762 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -0.7768 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0062 -1.5338 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0270 0.0649 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5692 -0.6921 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1085 2.3710 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2873 2.8454 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6431 -0.0003 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8217 -0.4744 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6425 0.9489 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2869 0.9479 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0006 2.8460 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0796 0.1072 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1084 1.4219 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6433 0.9482 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4652 1.4223 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4654 2.3713 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8210 1.4229 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8221 1.4226 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0002 0.9485 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.9527 0.9343 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 -0.8208 2.3719 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.8223 2.3716 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1 24 1 0 0 0 0 2 25 1 0 0 0 0 3 4 2 0 0 0 0 3 5 1 0 0 0 0 4 6 1 0 0 0 0 5 7 2 0 0 0 0 6 15 2 0 0 0 0 7 15 1 0 0 0 0 8 9 2 0 0 0 0 8 16 1 0 0 0 0 9 19 1 0 0 0 0 10 11 1 0 0 0 0 10 17 1 0 0 0 0 11 24 1 0 0 0 0 12 15 1 0 0 0 0 13 16 2 0 0 0 0 13 18 1 0 0 0 0 14 25 1 0 0 0 0 14 26 1 0 0 0 0 16 23 1 0 0 0 0 17 18 1 0 0 0 0 17 21 2 0 0 0 0 18 19 2 0 0 0 0 19 26 1 0 0 0 0 20 12 1 6 0 0 0 20 22 1 0 0 0 0 20 25 1 0 0 0 0 21 26 1 0 0 0 0 22 21 1 6 0 0 0 22 24 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	409.12
Volume:	380.105
LogP:	4.649
LogD:	4.0
LogS:	-4.283
# Rotatable Bonds:	2
TPSA:	11.41
# H-Bond Aceptor:	3
# H-Bond Donor:	0
# Rings:	5
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.619
Synthetic Accessibility Score:	3.589
Fsp3:	0.364
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.818
MDCK Permeability:	2.3557771783089265e-05
Pgp-inhibitor:	1.0
Pgp-substrate:	0.146
Human Intestinal Absorption (HIA):	0.011
20% Bioavailability (F20%):	0.026
30% Bioavailability (F30%):	0.948

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.998
Plasma Protein Binding (PPB):	93.37178802490234%
Volume Distribution (VD):	2.842
Pgp-substrate:	3.273179292678833%

ADMET: Metabolism

CYP1A2-inhibitor:	0.634
CYP1A2-substrate:	0.693
CYP2C19-inhibitor:	0.504
CYP2C19-substrate:	0.966
CYP2C9-inhibitor:	0.075
CYP2C9-substrate:	0.305
CYP2D6-inhibitor:	0.988
CYP2D6-substrate:	0.91
CYP3A4-inhibitor:	0.12
CYP3A4-substrate:	0.905

ADMET: Excretion

Clearance (CL):	7.548
Half-life (T1/2):	0.135

ADMET: Toxicity

hERG Blockers:	0.916
Human Hepatotoxicity (H-HT):	0.626
Drug-inuced Liver Injury (DILI):	0.442
AMES Toxicity:	0.22
Rat Oral Acute Toxicity:	0.655
Maximum Recommended Daily Dose:	0.978
Skin Sensitization:	0.063
Carcinogencity:	0.325
Eye Corrosion:	0.003
Eye Irritation:	0.01
Respiratory Toxicity:	0.577

Download Data

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

Natural Product: NPC195507

Natural Product ID:	NPC195507
*Common Name:**	Eudistomidin I
IUPAC Name:	n.a.
Synonyms:	Eudistomidin I
Standard InCHIKey:	DJAYVOJDCFDUFD-RBBKRZOGSA-N
Standard InCHI:	InChI=1S/C22H24BrN3/c1-24-11-10-17-18-13-16(23)8-9-19(18)26-14-25(2)20(22(24)21(17)26)12-15-6-4-3-5-7-15/h3-9,13,20,22H,10-12,14H2,1-2H3/t20-,22+/m0/s1
SMILES:	Brc1ccc2c(c1)c1CCN([C@H]3c1n2CN([C@H]3Cc1ccccc1)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1800681
PubChem CID:	56683231
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000211] Indoles and derivatives [CHEMONTID:0001213] Pyridoindoles [CHEMONTID:0001914] Beta carbolines

*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
NPO3258	Parmelia glabra	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8196	Leucanthemum aligulatum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2552	Shorea acuminata	Species	Dipterocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4412	Vepris stolzii	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7903	Ascochyta fabae	Species	Didymellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ 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

Activity Type	# Activity
Cell Line	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT168	Cell Line	P388	Mus musculus	IC50	>	10.0	ug.mL-1	PMID[513983]
NPT137	Cell Line	L1210	Mus musculus	IC50	>	10.0	ug.mL-1	PMID[513983]
NPT91	Cell Line	KB	Homo sapiens	IC50	>	10.0	ug.mL-1	PMID[513983]

☑ 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 NPC195507 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	1157
0.1-0.2	14397
0.2-0.3	17784
0.3-0.4	4213
0.4-0.5	2546
0.5-0.6	1838
0.6-0.7	637
0.7-0.8	120
0.8-0.85	3
0.85-0.9	0
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9481	High Similarity	NPC2165
0.8428	Intermediate Similarity	NPC476219
0.8323	Intermediate Similarity	NPC20144
0.8125	Intermediate Similarity	NPC40070
0.8086	Intermediate Similarity	NPC476297
0.7939	Intermediate Similarity	NPC6436
0.7904	Intermediate Similarity	NPC247987
0.7898	Intermediate Similarity	NPC88097
0.7866	Intermediate Similarity	NPC34844
0.7824	Intermediate Similarity	NPC97343
0.7778	Intermediate Similarity	NPC82331
0.7765	Intermediate Similarity	NPC231536
0.7746	Intermediate Similarity	NPC121903
0.7746	Intermediate Similarity	NPC474958
0.7725	Intermediate Similarity	NPC221786
0.7725	Intermediate Similarity	NPC475990
0.7725	Intermediate Similarity	NPC474880
0.7697	Intermediate Similarity	NPC232798
0.7679	Intermediate Similarity	NPC229173
0.7679	Intermediate Similarity	NPC255229
0.7679	Intermediate Similarity	NPC81229
0.7673	Intermediate Similarity	NPC104483
0.7673	Intermediate Similarity	NPC316811
0.7669	Intermediate Similarity	NPC21605
0.7658	Intermediate Similarity	NPC314102
0.7658	Intermediate Similarity	NPC251722
0.7647	Intermediate Similarity	NPC280864
0.7643	Intermediate Similarity	NPC198988
0.7622	Intermediate Similarity	NPC2272
0.7602	Intermediate Similarity	NPC109447
0.7595	Intermediate Similarity	NPC325252
0.7578	Intermediate Similarity	NPC63157
0.7578	Intermediate Similarity	NPC473868
0.7571	Intermediate Similarity	NPC307191
0.7546	Intermediate Similarity	NPC204141
0.7544	Intermediate Similarity	NPC274229
0.7529	Intermediate Similarity	NPC288074
0.7529	Intermediate Similarity	NPC194881
0.7516	Intermediate Similarity	NPC59084
0.75	Intermediate Similarity	NPC316069
0.7486	Intermediate Similarity	NPC108011
0.7485	Intermediate Similarity	NPC149265
0.7438	Intermediate Similarity	NPC150259
0.7414	Intermediate Similarity	NPC474897
0.7407	Intermediate Similarity	NPC2949
0.7407	Intermediate Similarity	NPC115611
0.7403	Intermediate Similarity	NPC135601
0.7403	Intermediate Similarity	NPC141612
0.7403	Intermediate Similarity	NPC17273
0.74	Intermediate Similarity	NPC54102
0.74	Intermediate Similarity	NPC162689
0.7381	Intermediate Similarity	NPC141926
0.7365	Intermediate Similarity	NPC33421
0.7349	Intermediate Similarity	NPC470111
0.7345	Intermediate Similarity	NPC280852
0.7338	Intermediate Similarity	NPC122718
0.7333	Intermediate Similarity	NPC469525
0.7333	Intermediate Similarity	NPC81561
0.733	Intermediate Similarity	NPC477611
0.7321	Intermediate Similarity	NPC470233
0.7299	Intermediate Similarity	NPC478183
0.7288	Intermediate Similarity	NPC280297
0.7283	Intermediate Similarity	NPC271797
0.7283	Intermediate Similarity	NPC21174
0.7283	Intermediate Similarity	NPC478182
0.7278	Intermediate Similarity	NPC325903
0.7267	Intermediate Similarity	NPC218268
0.7267	Intermediate Similarity	NPC148140
0.7247	Intermediate Similarity	NPC472122
0.7247	Intermediate Similarity	NPC24594
0.7246	Intermediate Similarity	NPC201380
0.7246	Intermediate Similarity	NPC179787
0.7241	Intermediate Similarity	NPC17751
0.7233	Intermediate Similarity	NPC475450
0.7232	Intermediate Similarity	NPC64055
0.7229	Intermediate Similarity	NPC470440
0.7225	Intermediate Similarity	NPC470203
0.7209	Intermediate Similarity	NPC56765
0.7207	Intermediate Similarity	NPC326575
0.7202	Intermediate Similarity	NPC321911
0.7195	Intermediate Similarity	NPC284635
0.7186	Intermediate Similarity	NPC63545
0.7186	Intermediate Similarity	NPC478186
0.717	Intermediate Similarity	NPC22079
0.7168	Intermediate Similarity	NPC470204
0.7167	Intermediate Similarity	NPC133261
0.7152	Intermediate Similarity	NPC476566
0.7143	Intermediate Similarity	NPC469811
0.7135	Intermediate Similarity	NPC472123
0.7134	Intermediate Similarity	NPC250361
0.7134	Intermediate Similarity	NPC73767
0.7134	Intermediate Similarity	NPC110126
0.7127	Intermediate Similarity	NPC187827
0.7127	Intermediate Similarity	NPC472105
0.711	Intermediate Similarity	NPC293487
0.711	Intermediate Similarity	NPC477591
0.7107	Intermediate Similarity	NPC473587
0.7102	Intermediate Similarity	NPC56233
0.7093	Intermediate Similarity	NPC51054
0.7091	Intermediate Similarity	NPC469784
0.7091	Intermediate Similarity	NPC469761
0.7091	Intermediate Similarity	NPC469767
0.7091	Intermediate Similarity	NPC469768
0.7091	Intermediate Similarity	NPC469780
0.7091	Intermediate Similarity	NPC469783
0.7091	Intermediate Similarity	NPC469779
0.7086	Intermediate Similarity	NPC478184
0.7086	Intermediate Similarity	NPC317105
0.7081	Intermediate Similarity	NPC473930
0.7078	Intermediate Similarity	NPC215519
0.7073	Intermediate Similarity	NPC169433
0.7069	Intermediate Similarity	NPC122141
0.7063	Intermediate Similarity	NPC475428
0.7062	Intermediate Similarity	NPC317430
0.7059	Intermediate Similarity	NPC53947
0.7051	Intermediate Similarity	NPC46358
0.7049	Intermediate Similarity	NPC472104
0.7049	Intermediate Similarity	NPC472110
0.7049	Intermediate Similarity	NPC472109
0.7049	Intermediate Similarity	NPC143533
0.7048	Intermediate Similarity	NPC469766
0.7044	Intermediate Similarity	NPC473762
0.7039	Intermediate Similarity	NPC161861
0.7033	Intermediate Similarity	NPC15840
0.7029	Intermediate Similarity	NPC225018
0.7024	Intermediate Similarity	NPC86288
0.7019	Intermediate Similarity	NPC179365
0.7012	Intermediate Similarity	NPC105127
0.7012	Intermediate Similarity	NPC84911
0.7011	Intermediate Similarity	NPC206819
0.7011	Intermediate Similarity	NPC258480
0.7011	Intermediate Similarity	NPC472294
0.7011	Intermediate Similarity	NPC318065
0.7	Intermediate Similarity	NPC317054
0.6989	Remote Similarity	NPC469541
0.6982	Remote Similarity	NPC288838
0.6977	Remote Similarity	NPC281094
0.6974	Remote Similarity	NPC470505
0.6973	Remote Similarity	NPC472107
0.6973	Remote Similarity	NPC79062
0.6971	Remote Similarity	NPC44773
0.6971	Remote Similarity	NPC215584
0.6954	Remote Similarity	NPC129721
0.6954	Remote Similarity	NPC236711
0.6951	Remote Similarity	NPC96102
0.6951	Remote Similarity	NPC261195
0.6951	Remote Similarity	NPC29886
0.6935	Remote Similarity	NPC66210
0.6932	Remote Similarity	NPC478185
0.6927	Remote Similarity	NPC91895
0.6923	Remote Similarity	NPC48564
0.6923	Remote Similarity	NPC182570
0.6923	Remote Similarity	NPC265605
0.6919	Remote Similarity	NPC472119
0.6914	Remote Similarity	NPC41257
0.6909	Remote Similarity	NPC125746
0.6906	Remote Similarity	NPC471579
0.6895	Remote Similarity	NPC474180
0.6895	Remote Similarity	NPC188821
0.6886	Remote Similarity	NPC238499
0.6882	Remote Similarity	NPC143872
0.6879	Remote Similarity	NPC41174
0.6865	Remote Similarity	NPC472108
0.6865	Remote Similarity	NPC139291
0.6857	Remote Similarity	NPC216643
0.6857	Remote Similarity	NPC286427
0.6856	Remote Similarity	NPC303820
0.6856	Remote Similarity	NPC106771
0.6856	Remote Similarity	NPC23420
0.6856	Remote Similarity	NPC205254
0.6852	Remote Similarity	NPC69914
0.6845	Remote Similarity	NPC478077
0.6842	Remote Similarity	NPC477166
0.6842	Remote Similarity	NPC473342
0.6842	Remote Similarity	NPC304187
0.6842	Remote Similarity	NPC471386
0.6842	Remote Similarity	NPC477167
0.6839	Remote Similarity	NPC474389
0.6833	Remote Similarity	NPC32534
0.6831	Remote Similarity	NPC234987
0.6826	Remote Similarity	NPC312092
0.6824	Remote Similarity	NPC285731
0.6824	Remote Similarity	NPC314372
0.6821	Remote Similarity	NPC52909
0.6821	Remote Similarity	NPC475935
0.6821	Remote Similarity	NPC94211
0.6813	Remote Similarity	NPC329688
0.6813	Remote Similarity	NPC189812
0.6813	Remote Similarity	NPC297034
0.6809	Remote Similarity	NPC472323
0.6805	Remote Similarity	NPC190296
0.6804	Remote Similarity	NPC220797
0.6804	Remote Similarity	NPC201266
0.6804	Remote Similarity	NPC474318
0.6804	Remote Similarity	NPC153123
0.6804	Remote Similarity	NPC268744
0.6804	Remote Similarity	NPC475914
0.6802	Remote Similarity	NPC37548
0.6798	Remote Similarity	NPC90723
0.6792	Remote Similarity	NPC476322

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 NPC195507 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	453
0.1-0.2	910
0.2-0.3	1072
0.3-0.4	2183
0.4-0.5	2289
0.5-0.6	1734
0.6-0.7	469
0.7-0.8	38
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.84	Intermediate Similarity	NPD3385	Approved
0.8323	Intermediate Similarity	NPD4637	Clinical (unspecified phase)
0.7895	Intermediate Similarity	NPD3654	Approved
0.7888	Intermediate Similarity	NPD4547	Phase 3
0.7826	Intermediate Similarity	NPD1683	Approved
0.7771	Intermediate Similarity	NPD45	Approved
0.7771	Intermediate Similarity	NPD6554	Approved
0.7711	Intermediate Similarity	NPD2150	Discontinued
0.7701	Intermediate Similarity	NPD7111	Discontinued
0.7673	Intermediate Similarity	NPD2068	Approved
0.7673	Intermediate Similarity	NPD2070	Approved
0.7673	Intermediate Similarity	NPD2071	Approved
0.7673	Intermediate Similarity	NPD2069	Approved
0.764	Intermediate Similarity	NPD4047	Discontinued
0.7545	Intermediate Similarity	NPD6285	Phase 2
0.7515	Intermediate Similarity	NPD5538	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD1183	Approved
0.75	Intermediate Similarity	NPD6794	Approved
0.7485	Intermediate Similarity	NPD5671	Approved
0.7485	Intermediate Similarity	NPD2837	Discontinued
0.7484	Intermediate Similarity	NPD1254	Approved
0.7484	Intermediate Similarity	NPD1256	Approved
0.7484	Intermediate Similarity	NPD1253	Approved
0.7484	Intermediate Similarity	NPD1255	Approved
0.7471	Intermediate Similarity	NPD6827	Clinical (unspecified phase)
0.7471	Intermediate Similarity	NPD6828	Phase 2
0.7459	Intermediate Similarity	NPD7394	Phase 2
0.7407	Intermediate Similarity	NPD3943	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD1993	Approved
0.7405	Intermediate Similarity	NPD1994	Approved
0.7405	Intermediate Similarity	NPD1995	Approved
0.7386	Intermediate Similarity	NPD7006	Approved
0.736	Intermediate Similarity	NPD3341	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD4326	Phase 2
0.7341	Intermediate Similarity	NPD4550	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD2006	Phase 2
0.7305	Intermediate Similarity	NPD2430	Phase 2
0.7294	Intermediate Similarity	NPD2927	Phase 3
0.7289	Intermediate Similarity	NPD7469	Discontinued
0.7283	Intermediate Similarity	NPD3323	Discontinued
0.7278	Intermediate Similarity	NPD3475	Approved
0.7278	Intermediate Similarity	NPD3476	Approved
0.7273	Intermediate Similarity	NPD5254	Discontinued
0.7273	Intermediate Similarity	NPD3401	Clinical (unspecified phase)
0.7257	Intermediate Similarity	NPD4779	Clinical (unspecified phase)
0.7257	Intermediate Similarity	NPD7287	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD3942	Approved
0.725	Intermediate Similarity	NPD3944	Approved
0.7225	Intermediate Similarity	NPD5315	Discontinued
0.7208	Intermediate Similarity	NPD4341	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD2118	Approved
0.7197	Intermediate Similarity	NPD2119	Approved
0.7173	Intermediate Similarity	NPD4142	Discontinued
0.7169	Intermediate Similarity	NPD4509	Discontinued
0.7168	Intermediate Similarity	NPD6074	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD2466	Phase 3
0.716	Intermediate Similarity	NPD2465	Approved
0.716	Intermediate Similarity	NPD2462	Phase 3
0.7152	Intermediate Similarity	NPD1722	Approved
0.7151	Intermediate Similarity	NPD5104	Approved
0.7143	Intermediate Similarity	NPD5744	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD1313	Approved
0.7143	Intermediate Similarity	NPD2915	Discontinued
0.7135	Intermediate Similarity	NPD4872	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD786	Approved
0.712	Intermediate Similarity	NPD3378	Clinical (unspecified phase)
0.7118	Intermediate Similarity	NPD2882	Phase 1
0.7107	Intermediate Similarity	NPD947	Approved
0.7101	Intermediate Similarity	NPD4374	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD3799	Suspended
0.7079	Intermediate Similarity	NPD5934	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD2323	Clinical (unspecified phase)
0.7066	Intermediate Similarity	NPD1918	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD715	Phase 3
0.7062	Intermediate Similarity	NPD2333	Discontinued
0.7062	Intermediate Similarity	NPD2390	Clinical (unspecified phase)
0.7056	Intermediate Similarity	NPD2406	Clinical (unspecified phase)
0.7056	Intermediate Similarity	NPD2367	Phase 2
0.7045	Intermediate Similarity	NPD509	Phase 3
0.7045	Intermediate Similarity	NPD3889	Approved
0.7037	Intermediate Similarity	NPD4029	Approved
0.7037	Intermediate Similarity	NPD4030	Approved
0.7037	Intermediate Similarity	NPD4028	Approved
0.7033	Intermediate Similarity	NPD6277	Clinical (unspecified phase)
0.7029	Intermediate Similarity	NPD2149	Clinical (unspecified phase)
0.7029	Intermediate Similarity	NPD1853	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD4902	Discontinued
0.7022	Intermediate Similarity	NPD2875	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD4615	Phase 2
0.7018	Intermediate Similarity	NPD6476	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD6158	Phase 2
0.7017	Intermediate Similarity	NPD4181	Approved
0.7	Intermediate Similarity	NPD3100	Discontinued
0.7	Intermediate Similarity	NPD7023	Clinical (unspecified phase)
0.6978	Remote Similarity	NPD3409	Phase 1
0.6971	Remote Similarity	NPD6454	Clinical (unspecified phase)
0.6961	Remote Similarity	NPD6375	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD4463	Approved
0.6959	Remote Similarity	NPD4462	Approved
0.6951	Remote Similarity	NPD198	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD4112	Clinical (unspecified phase)
0.6932	Remote Similarity	NPD6771	Discontinued
0.6927	Remote Similarity	NPD6468	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD6469	Phase 3
0.6923	Remote Similarity	NPD271	Approved
0.6923	Remote Similarity	NPD270	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD3629	Approved
0.6923	Remote Similarity	NPD3630	Approved
0.6923	Remote Similarity	NPD268	Approved
0.6919	Remote Similarity	NPD4520	Approved
0.6915	Remote Similarity	NPD5145	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD1251	Discontinued
0.6911	Remote Similarity	NPD7935	Phase 2
0.6909	Remote Similarity	NPD1262	Discovery
0.6906	Remote Similarity	NPD4128	Approved
0.6906	Remote Similarity	NPD5065	Approved
0.6902	Remote Similarity	NPD5806	Clinical (unspecified phase)
0.6902	Remote Similarity	NPD4649	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD2580	Discontinued
0.689	Remote Similarity	NPD2141	Approved
0.689	Remote Similarity	NPD2140	Approved
0.689	Remote Similarity	NPD2142	Approved
0.6889	Remote Similarity	NPD3609	Approved
0.6889	Remote Similarity	NPD3610	Approved
0.6882	Remote Similarity	NPD5075	Discontinued
0.6878	Remote Similarity	NPD6761	Discontinued
0.6875	Remote Similarity	NPD991	Phase 2
0.6875	Remote Similarity	NPD5462	Discontinued
0.6875	Remote Similarity	NPD992	Clinical (unspecified phase)
0.6872	Remote Similarity	NPD4640	Approved
0.6872	Remote Similarity	NPD4638	Approved
0.6872	Remote Similarity	NPD5021	Discontinued
0.6872	Remote Similarity	NPD4639	Approved
0.6857	Remote Similarity	NPD5300	Clinical (unspecified phase)
0.6854	Remote Similarity	NPD1002	Clinical (unspecified phase)
0.6851	Remote Similarity	NPD7217	Approved
0.6851	Remote Similarity	NPD7216	Approved
0.6848	Remote Similarity	NPD5962	Phase 2
0.6845	Remote Similarity	NPD6721	Phase 1
0.6837	Remote Similarity	NPD6991	Approved
0.6833	Remote Similarity	NPD5436	Phase 1
0.6828	Remote Similarity	NPD5892	Approved
0.6828	Remote Similarity	NPD4957	Phase 2
0.6818	Remote Similarity	NPD5418	Discontinued
0.6816	Remote Similarity	NPD1215	Discontinued
0.6809	Remote Similarity	NPD3486	Clinical (unspecified phase)
0.6805	Remote Similarity	NPD2007	Clinical (unspecified phase)
0.6793	Remote Similarity	NPD2930	Clinical (unspecified phase)
0.6791	Remote Similarity	NPD4298	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD3830	Phase 1
0.6772	Remote Similarity	NPD6965	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD5787	Discontinued
0.6769	Remote Similarity	NPD6816	Phase 3
0.6763	Remote Similarity	NPD2172	Phase 1
0.6761	Remote Similarity	NPD6497	Approved
0.6758	Remote Similarity	NPD5996	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD1873	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD5473	Discontinued
0.6755	Remote Similarity	NPD2591	Phase 2
0.6754	Remote Similarity	NPD7722	Suspended
0.6746	Remote Similarity	NPD5020	Approved
0.6738	Remote Similarity	NPD5463	Clinical (unspecified phase)
0.6738	Remote Similarity	NPD7564	Discontinued
0.6737	Remote Similarity	NPD6281	Approved
0.6736	Remote Similarity	NPD2960	Clinical (unspecified phase)
0.6736	Remote Similarity	NPD6278	Clinical (unspecified phase)
0.6726	Remote Similarity	NPD2072	Approved
0.6726	Remote Similarity	NPD2075	Approved
0.6726	Remote Similarity	NPD2074	Approved
0.6726	Remote Similarity	NPD2073	Approved
0.6724	Remote Similarity	NPD2524	Discontinued
0.6724	Remote Similarity	NPD2128	Phase 1
0.6722	Remote Similarity	NPD3361	Phase 1
0.6721	Remote Similarity	NPD3859	Clinical (unspecified phase)
0.672	Remote Similarity	NPD1895	Discontinued
0.6705	Remote Similarity	NPD3112	Approved
0.6705	Remote Similarity	NPD3113	Approved
0.6705	Remote Similarity	NPD3115	Approved
0.6705	Remote Similarity	NPD3114	Approved
0.6705	Remote Similarity	NPD473	Clinical (unspecified phase)
0.6703	Remote Similarity	NPD1567	Clinical (unspecified phase)
0.6702	Remote Similarity	NPD6610	Clinical (unspecified phase)
0.6701	Remote Similarity	NPD6129	Phase 2
0.67	Remote Similarity	NPD7672	Approved
0.67	Remote Similarity	NPD7671	Approved
0.6687	Remote Similarity	NPD4880	Discontinued
0.6685	Remote Similarity	NPD4075	Phase 2
0.6685	Remote Similarity	NPD2640	Approved
0.6685	Remote Similarity	NPD2641	Approved
0.6684	Remote Similarity	NPD2730	Approved
0.6684	Remote Similarity	NPD2729	Approved
0.6684	Remote Similarity	NPD5016	Approved
0.6684	Remote Similarity	NPD4441	Phase 2
0.6684	Remote Similarity	NPD2728	Approved
0.6683	Remote Similarity	NPD6271	Approved
0.6683	Remote Similarity	NPD4023	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2719	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5809	Phase 3
0.6667	Remote Similarity	NPD1333	Phase 3
0.6667	Remote Similarity	NPD7127	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