NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	244.11
Volume:	261.435
LogP:	4.114
LogD:	3.615
LogS:	-3.68
# Rotatable Bonds:	0
TPSA:	53.6
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.739
Synthetic Accessibility Score:	2.851
Fsp3:	0.2
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:	-4.765
MDCK Permeability:	1.7800042769522406e-05
Pgp-inhibitor:	0.006
Pgp-substrate:	0.179
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.097
30% Bioavailability (F30%):	0.182

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.058
Plasma Protein Binding (PPB):	99.81571197509766%
Volume Distribution (VD):	0.563
Pgp-substrate:	1.1892019510269165%

ADMET: Metabolism

CYP1A2-inhibitor:	0.966
CYP1A2-substrate:	0.938
CYP2C19-inhibitor:	0.803
CYP2C19-substrate:	0.109
CYP2C9-inhibitor:	0.801
CYP2C9-substrate:	0.811
CYP2D6-inhibitor:	0.813
CYP2D6-substrate:	0.858
CYP3A4-inhibitor:	0.312
CYP3A4-substrate:	0.311

ADMET: Excretion

Clearance (CL):	13.24
Half-life (T1/2):	0.807

ADMET: Toxicity

hERG Blockers:	0.013
Human Hepatotoxicity (H-HT):	0.067
Drug-inuced Liver Injury (DILI):	0.649
AMES Toxicity:	0.049
Rat Oral Acute Toxicity:	0.639
Maximum Recommended Daily Dose:	0.345
Skin Sensitization:	0.8
Carcinogencity:	0.658
Eye Corrosion:	0.176
Eye Irritation:	0.941
Respiratory Toxicity:	0.488

Download Data

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

Natural Product: NPC184391

Natural Product ID:	NPC184391
*Common Name:**	Chlorantene E
IUPAC Name:	n.a.
Synonyms:	Chlorantene E
Standard InCHIKey:	KELZYRMOEAISJM-UXBLZVDNSA-N
Standard InCHI:	InChI=1S/C15H16O3/c1-9-5-4-6-10(2)14(17)15-13(12(16)7-9)11(3)8-18-15/h6,8H,1,4-5,7H2,2-3H3/b10-6+
SMILES:	C=C1CC/C=C(C)/C(=O)c2c(C(=O)C1)c(C)co2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL516311
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001550] Sesquiterpenoids [CHEMONTID:0002456] Germacrane sesquiterpenoids

*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
NPO21178	Chloranthus serratus	Species	Chloranthaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19053511]
NPO21178	Chloranthus serratus	Species	Chloranthaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22372956]
NPO21178	Chloranthus serratus	Species	Chloranthaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27588583]
NPO21178	Chloranthus serratus	Species	Chloranthaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[30724564]
NPO21178	Chloranthus serratus	Species	Chloranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21178	Chloranthus serratus	Species	Chloranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21178	Chloranthus serratus	Species	Chloranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO21178	Chloranthus serratus	Species	Chloranthaceae	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
MIC	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT452	Organism	Helicobacter pylori SS1	Helicobacter pylori SS1	MIC	=	25.0	ug.mL-1	PMID[513935]

☑ 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 NPC184391 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	344
0.1-0.2	2088
0.2-0.3	5717
0.3-0.4	11655
0.4-0.5	8501
0.5-0.6	7290
0.6-0.7	6465
0.7-0.8	600
0.8-0.85	27
0.85-0.9	9
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8992	High Similarity	NPC200718
0.8739	High Similarity	NPC22678
0.8722	High Similarity	NPC177262
0.8538	High Similarity	NPC45947
0.8537	High Similarity	NPC227660
0.8516	High Similarity	NPC216810
0.8455	Intermediate Similarity	NPC45536
0.8226	Intermediate Similarity	NPC205523
0.8129	Intermediate Similarity	NPC248795
0.8125	Intermediate Similarity	NPC79557
0.8116	Intermediate Similarity	NPC265181
0.8102	Intermediate Similarity	NPC286130
0.8095	Intermediate Similarity	NPC312525
0.8095	Intermediate Similarity	NPC217180
0.8077	Intermediate Similarity	NPC118853
0.806	Intermediate Similarity	NPC136340
0.8058	Intermediate Similarity	NPC18904
0.8058	Intermediate Similarity	NPC473681
0.8058	Intermediate Similarity	NPC61157
0.8058	Intermediate Similarity	NPC218204
0.8028	Intermediate Similarity	NPC195920
0.8016	Intermediate Similarity	NPC59035
0.8016	Intermediate Similarity	NPC79202
0.7984	Intermediate Similarity	NPC97566
0.7972	Intermediate Similarity	NPC475864
0.7958	Intermediate Similarity	NPC117674
0.7931	Intermediate Similarity	NPC192069
0.7931	Intermediate Similarity	NPC475904
0.7931	Intermediate Similarity	NPC474270
0.7917	Intermediate Similarity	NPC281398
0.7905	Intermediate Similarity	NPC88958
0.7902	Intermediate Similarity	NPC27798
0.7902	Intermediate Similarity	NPC93241
0.7883	Intermediate Similarity	NPC106247
0.7879	Intermediate Similarity	NPC473885
0.7879	Intermediate Similarity	NPC471074
0.7868	Intermediate Similarity	NPC471817
0.7862	Intermediate Similarity	NPC474255
0.7862	Intermediate Similarity	NPC474220
0.7862	Intermediate Similarity	NPC471618
0.7857	Intermediate Similarity	NPC474615
0.7847	Intermediate Similarity	NPC233763
0.7842	Intermediate Similarity	NPC42400
0.7829	Intermediate Similarity	NPC137710
0.7829	Intermediate Similarity	NPC67345
0.7829	Intermediate Similarity	NPC244862
0.7826	Intermediate Similarity	NPC159786
0.781	Intermediate Similarity	NPC470740
0.7801	Intermediate Similarity	NPC282973
0.7795	Intermediate Similarity	NPC28054
0.7793	Intermediate Similarity	NPC224418
0.7787	Intermediate Similarity	NPC42471
0.7786	Intermediate Similarity	NPC323118
0.7778	Intermediate Similarity	NPC245522
0.7778	Intermediate Similarity	NPC37488
0.7778	Intermediate Similarity	NPC114513
0.7762	Intermediate Similarity	NPC110305
0.7761	Intermediate Similarity	NPC141059
0.7737	Intermediate Similarity	NPC473982
0.7724	Intermediate Similarity	NPC219969
0.7724	Intermediate Similarity	NPC140688
0.7714	Intermediate Similarity	NPC473268
0.771	Intermediate Similarity	NPC115859
0.7704	Intermediate Similarity	NPC329707
0.7703	Intermediate Similarity	NPC144010
0.7692	Intermediate Similarity	NPC473152
0.7687	Intermediate Similarity	NPC83301
0.7671	Intermediate Similarity	NPC474317
0.7669	Intermediate Similarity	NPC188377
0.7669	Intermediate Similarity	NPC65735
0.7669	Intermediate Similarity	NPC178382
0.7667	Intermediate Similarity	NPC472786
0.7664	Intermediate Similarity	NPC477645
0.766	Intermediate Similarity	NPC472376
0.7652	Intermediate Similarity	NPC174915
0.7652	Intermediate Similarity	NPC270807
0.7651	Intermediate Similarity	NPC474378
0.7651	Intermediate Similarity	NPC474219
0.7651	Intermediate Similarity	NPC471613
0.7651	Intermediate Similarity	NPC145830
0.7647	Intermediate Similarity	NPC50583
0.7647	Intermediate Similarity	NPC59502
0.7643	Intermediate Similarity	NPC217914
0.7642	Intermediate Similarity	NPC298087
0.7619	Intermediate Similarity	NPC252208
0.7615	Intermediate Similarity	NPC243704
0.7615	Intermediate Similarity	NPC206007
0.7615	Intermediate Similarity	NPC21831
0.7615	Intermediate Similarity	NPC187547
0.7603	Intermediate Similarity	NPC478166
0.7568	Intermediate Similarity	NPC280025
0.7557	Intermediate Similarity	NPC473969
0.7556	Intermediate Similarity	NPC52035
0.7554	Intermediate Similarity	NPC474425
0.7554	Intermediate Similarity	NPC474426
0.7554	Intermediate Similarity	NPC474407
0.7554	Intermediate Similarity	NPC293253
0.7551	Intermediate Similarity	NPC250331
0.755	Intermediate Similarity	NPC75310
0.755	Intermediate Similarity	NPC179170
0.7537	Intermediate Similarity	NPC243269
0.7536	Intermediate Similarity	NPC475092
0.7519	Intermediate Similarity	NPC150895
0.7518	Intermediate Similarity	NPC146872
0.7517	Intermediate Similarity	NPC254198
0.7517	Intermediate Similarity	NPC226578
0.75	Intermediate Similarity	NPC53953
0.7483	Intermediate Similarity	NPC474261
0.7483	Intermediate Similarity	NPC62799
0.7483	Intermediate Similarity	NPC107571
0.7483	Intermediate Similarity	NPC233707
0.7481	Intermediate Similarity	NPC474829
0.7468	Intermediate Similarity	NPC333139
0.7467	Intermediate Similarity	NPC472406
0.7467	Intermediate Similarity	NPC472787
0.7466	Intermediate Similarity	NPC84479
0.7466	Intermediate Similarity	NPC218712
0.7466	Intermediate Similarity	NPC261733
0.7466	Intermediate Similarity	NPC267004
0.7466	Intermediate Similarity	NPC307346
0.7465	Intermediate Similarity	NPC232996
0.7462	Intermediate Similarity	NPC476031
0.7462	Intermediate Similarity	NPC476014
0.7459	Intermediate Similarity	NPC217226
0.7451	Intermediate Similarity	NPC221992
0.7447	Intermediate Similarity	NPC209858
0.7444	Intermediate Similarity	NPC1848
0.7442	Intermediate Similarity	NPC292036
0.7442	Intermediate Similarity	NPC252004
0.7434	Intermediate Similarity	NPC41719
0.7434	Intermediate Similarity	NPC290927
0.7432	Intermediate Similarity	NPC190572
0.7431	Intermediate Similarity	NPC148374
0.7426	Intermediate Similarity	NPC470858
0.7417	Intermediate Similarity	NPC475777
0.7413	Intermediate Similarity	NPC29638
0.7413	Intermediate Similarity	NPC236532
0.7407	Intermediate Similarity	NPC11799
0.7407	Intermediate Similarity	NPC141252
0.7405	Intermediate Similarity	NPC472895
0.7405	Intermediate Similarity	NPC131801
0.7405	Intermediate Similarity	NPC144745
0.7405	Intermediate Similarity	NPC208906
0.7403	Intermediate Similarity	NPC10051
0.7403	Intermediate Similarity	NPC294300
0.7403	Intermediate Similarity	NPC473282
0.7403	Intermediate Similarity	NPC104380
0.7403	Intermediate Similarity	NPC299094
0.7403	Intermediate Similarity	NPC476404
0.7403	Intermediate Similarity	NPC217602
0.7403	Intermediate Similarity	NPC317900
0.7397	Intermediate Similarity	NPC22248
0.7394	Intermediate Similarity	NPC303217
0.7391	Intermediate Similarity	NPC208389
0.7388	Intermediate Similarity	NPC314329
0.7388	Intermediate Similarity	NPC263870
0.7385	Intermediate Similarity	NPC11821
0.7383	Intermediate Similarity	NPC198427
0.7379	Intermediate Similarity	NPC477537
0.7377	Intermediate Similarity	NPC156768
0.7376	Intermediate Similarity	NPC477536
0.7372	Intermediate Similarity	NPC474830
0.7372	Intermediate Similarity	NPC319140
0.7372	Intermediate Similarity	NPC95567
0.7372	Intermediate Similarity	NPC237868
0.7372	Intermediate Similarity	NPC246392
0.7368	Intermediate Similarity	NPC246214
0.7365	Intermediate Similarity	NPC262198
0.7365	Intermediate Similarity	NPC104924
0.7357	Intermediate Similarity	NPC324488
0.7344	Intermediate Similarity	NPC105249
0.7343	Intermediate Similarity	NPC307401
0.7338	Intermediate Similarity	NPC21460
0.7338	Intermediate Similarity	NPC81405
0.7328	Intermediate Similarity	NPC76844
0.7328	Intermediate Similarity	NPC474987
0.7324	Intermediate Similarity	NPC247743
0.7324	Intermediate Similarity	NPC265793
0.7324	Intermediate Similarity	NPC324117
0.732	Intermediate Similarity	NPC472785
0.7319	Intermediate Similarity	NPC26532
0.7315	Intermediate Similarity	NPC471346
0.731	Intermediate Similarity	NPC201370
0.731	Intermediate Similarity	NPC473983
0.7308	Intermediate Similarity	NPC472781
0.7308	Intermediate Similarity	NPC472782
0.7303	Intermediate Similarity	NPC156244
0.7299	Intermediate Similarity	NPC224657
0.7297	Intermediate Similarity	NPC469385
0.7293	Intermediate Similarity	NPC35744
0.7292	Intermediate Similarity	NPC301341
0.7292	Intermediate Similarity	NPC477534
0.7292	Intermediate Similarity	NPC284184
0.729	Intermediate Similarity	NPC140952
0.7285	Intermediate Similarity	NPC46551
0.7279	Intermediate Similarity	NPC64568
0.7279	Intermediate Similarity	NPC27220
0.7279	Intermediate Similarity	NPC205071
0.7279	Intermediate Similarity	NPC267632
0.7267	Intermediate Similarity	NPC19747

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 NPC184391 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	339
0.1-0.2	1092
0.2-0.3	1921
0.3-0.4	2972
0.4-0.5	1862
0.5-0.6	769
0.6-0.7	174
0.7-0.8	20
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8116	Intermediate Similarity	NPD1471	Phase 3
0.7483	Intermediate Similarity	NPD2344	Approved
0.7468	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7388	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7361	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7279	Intermediate Similarity	NPD2309	Approved
0.7231	Intermediate Similarity	NPD1241	Discontinued
0.7152	Intermediate Similarity	NPD1247	Approved
0.7143	Intermediate Similarity	NPD6280	Approved
0.7143	Intermediate Similarity	NPD9092	Discovery
0.7143	Intermediate Similarity	NPD6279	Approved
0.708	Intermediate Similarity	NPD3972	Approved
0.705	Intermediate Similarity	NPD1049	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD920	Approved
0.7021	Intermediate Similarity	NPD6832	Phase 2
0.702	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6808	Phase 2
0.7	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.6978	Remote Similarity	NPD1876	Approved
0.6939	Remote Similarity	NPD2796	Approved
0.6918	Remote Similarity	NPD919	Approved
0.6913	Remote Similarity	NPD1243	Approved
0.6879	Remote Similarity	NPD2798	Approved
0.6879	Remote Similarity	NPD1019	Discontinued
0.6871	Remote Similarity	NPD2799	Discontinued
0.687	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD3926	Phase 2
0.6842	Remote Similarity	NPD6799	Approved
0.6835	Remote Similarity	NPD9717	Approved
0.6829	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6806	Remote Similarity	NPD2313	Discontinued
0.6795	Remote Similarity	NPD6599	Discontinued
0.679	Remote Similarity	NPD5668	Clinical (unspecified phase)
0.673	Remote Similarity	NPD2296	Approved
0.6712	Remote Similarity	NPD3142	Approved
0.6712	Remote Similarity	NPD3140	Approved
0.6711	Remote Similarity	NPD3887	Approved
0.6692	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.669	Remote Similarity	NPD3267	Approved
0.669	Remote Similarity	NPD3266	Approved
0.6689	Remote Similarity	NPD2800	Approved
0.6689	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD3882	Suspended
0.6667	Remote Similarity	NPD2346	Discontinued
0.6624	Remote Similarity	NPD3226	Approved
0.6623	Remote Similarity	NPD1549	Phase 2
0.6599	Remote Similarity	NPD1240	Approved
0.6591	Remote Similarity	NPD2182	Approved
0.6581	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6575	Remote Similarity	NPD3268	Approved
0.6573	Remote Similarity	NPD1203	Approved
0.657	Remote Similarity	NPD8434	Phase 2
0.6562	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6556	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6556	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6556	Remote Similarity	NPD2353	Approved
0.6556	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6554	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6544	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6541	Remote Similarity	NPD5889	Approved
0.6541	Remote Similarity	NPD7411	Suspended
0.6541	Remote Similarity	NPD5890	Approved
0.6522	Remote Similarity	NPD5616	Clinical (unspecified phase)
0.651	Remote Similarity	NPD1607	Approved
0.6506	Remote Similarity	NPD2403	Approved
0.65	Remote Similarity	NPD17	Approved
0.65	Remote Similarity	NPD6801	Discontinued
0.65	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6497	Remote Similarity	NPD5403	Approved
0.649	Remote Similarity	NPD1551	Phase 2
0.6483	Remote Similarity	NPD9494	Approved
0.6474	Remote Similarity	NPD2532	Approved
0.6474	Remote Similarity	NPD2534	Approved
0.6474	Remote Similarity	NPD2533	Approved
0.6474	Remote Similarity	NPD5401	Approved
0.6474	Remote Similarity	NPD4661	Approved
0.6474	Remote Similarity	NPD4662	Approved
0.6463	Remote Similarity	NPD5494	Approved
0.6449	Remote Similarity	NPD9493	Approved
0.6443	Remote Similarity	NPD1933	Approved
0.6443	Remote Similarity	NPD447	Suspended
0.6443	Remote Similarity	NPD6355	Discontinued
0.6442	Remote Similarity	NPD7075	Discontinued
0.6429	Remote Similarity	NPD4628	Phase 3
0.6424	Remote Similarity	NPD1510	Phase 2
0.642	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6418	Remote Similarity	NPD2067	Discontinued
0.6414	Remote Similarity	NPD5647	Approved
0.6412	Remote Similarity	NPD164	Approved
0.6392	Remote Similarity	NPD3873	Phase 3
0.6392	Remote Similarity	NPD3869	Phase 3
0.6387	Remote Similarity	NPD3295	Clinical (unspecified phase)
0.6387	Remote Similarity	NPD2354	Approved
0.6375	Remote Similarity	NPD6585	Discontinued
0.6374	Remote Similarity	NPD6765	Approved
0.6374	Remote Similarity	NPD6764	Approved
0.6369	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD2654	Approved
0.6364	Remote Similarity	NPD1608	Approved
0.6358	Remote Similarity	NPD5761	Phase 2
0.6358	Remote Similarity	NPD7819	Suspended
0.6358	Remote Similarity	NPD5760	Phase 2
0.6357	Remote Similarity	NPD9545	Approved
0.6351	Remote Similarity	NPD411	Approved
0.6351	Remote Similarity	NPD6798	Discontinued
0.6345	Remote Similarity	NPD2797	Approved
0.6341	Remote Similarity	NPD3749	Approved
0.6331	Remote Similarity	NPD2163	Approved
0.6323	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6319	Remote Similarity	NPD5402	Approved
0.6319	Remote Similarity	NPD3817	Phase 2
0.6316	Remote Similarity	NPD3134	Approved
0.6312	Remote Similarity	NPD1651	Approved
0.631	Remote Similarity	NPD4575	Clinical (unspecified phase)
0.6284	Remote Similarity	NPD2598	Clinical (unspecified phase)
0.6275	Remote Similarity	NPD2935	Discontinued
0.6269	Remote Similarity	NPD1358	Approved
0.6267	Remote Similarity	NPD4307	Phase 2
0.625	Remote Similarity	NPD957	Approved
0.6241	Remote Similarity	NPD1894	Discontinued
0.6231	Remote Similarity	NPD1238	Approved
0.6229	Remote Similarity	NPD6784	Approved
0.6229	Remote Similarity	NPD6785	Approved
0.6226	Remote Similarity	NPD5049	Phase 3
0.6226	Remote Similarity	NPD6273	Approved
0.6225	Remote Similarity	NPD4622	Approved
0.6225	Remote Similarity	NPD4618	Approved
0.6222	Remote Similarity	NPD2684	Approved
0.6214	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6213	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6209	Remote Similarity	NPD3748	Approved
0.62	Remote Similarity	NPD4062	Phase 3
0.62	Remote Similarity	NPD6233	Phase 2
0.6197	Remote Similarity	NPD5585	Approved
0.6196	Remote Similarity	NPD6844	Discontinued
0.6194	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6194	Remote Similarity	NPD2897	Discontinued
0.6188	Remote Similarity	NPD5586	Clinical (unspecified phase)
0.6185	Remote Similarity	NPD6559	Discontinued
0.6184	Remote Similarity	NPD6651	Approved
0.6165	Remote Similarity	NPD1237	Approved
0.6159	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD1778	Approved
0.6144	Remote Similarity	NPD5689	Approved
0.6144	Remote Similarity	NPD5688	Approved
0.6135	Remote Similarity	NPD958	Approved
0.6133	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6125	Remote Similarity	NPD1512	Approved
0.6119	Remote Similarity	NPD9697	Approved
0.6111	Remote Similarity	NPD2649	Approved
0.6111	Remote Similarity	NPD2651	Approved
0.6104	Remote Similarity	NPD7033	Discontinued
0.6104	Remote Similarity	NPD4308	Phase 3
0.6098	Remote Similarity	NPD7577	Discontinued
0.6098	Remote Similarity	NPD1934	Approved
0.6093	Remote Similarity	NPD8032	Phase 2
0.609	Remote Similarity	NPD4534	Discontinued
0.609	Remote Similarity	NPD9261	Approved
0.609	Remote Similarity	NPD5958	Discontinued
0.6084	Remote Similarity	NPD7768	Phase 2
0.6084	Remote Similarity	NPD5691	Approved
0.6084	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6074	Remote Similarity	NPD4380	Phase 2
0.6069	Remote Similarity	NPD1281	Approved
0.6061	Remote Similarity	NPD2801	Approved
0.6056	Remote Similarity	NPD5536	Phase 2
0.6048	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6047	Remote Similarity	NPD3818	Discontinued
0.6043	Remote Similarity	NPD7843	Approved
0.6043	Remote Similarity	NPD5535	Approved
0.6028	Remote Similarity	NPD7157	Approved
0.6026	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6026	Remote Similarity	NPD6004	Phase 3
0.6026	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6026	Remote Similarity	NPD3764	Approved
0.6026	Remote Similarity	NPD6002	Phase 3
0.6026	Remote Similarity	NPD6005	Phase 3
0.6026	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6023	Remote Similarity	NPD6166	Phase 2
0.6023	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6023	Remote Similarity	NPD7784	Clinical (unspecified phase)
0.6023	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6014	Remote Similarity	NPD1470	Approved
0.6013	Remote Similarity	NPD3750	Approved
0.6012	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6012	Remote Similarity	NPD3050	Clinical (unspecified phase)
0.6	Remote Similarity	NPD1511	Approved
0.6	Remote Similarity	NPD7317	Phase 3
0.6	Remote Similarity	NPD3496	Discontinued
0.5988	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.5988	Remote Similarity	NPD4947	Clinical (unspecified phase)
0.5986	Remote Similarity	NPD4359	Approved
0.5978	Remote Similarity	NPD6040	Clinical (unspecified phase)
0.5977	Remote Similarity	NPD1729	Discontinued
0.5967	Remote Similarity	NPD3269	Clinical (unspecified phase)
0.5964	Remote Similarity	NPD7972	Discontinued
0.5962	Remote Similarity	NPD5712	Approved
0.5962	Remote Similarity	NPD4476	Approved
0.5962	Remote Similarity	NPD4477	Approved
0.596	Remote Similarity	NPD7095	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