NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	246.13
Volume:	252.232
LogP:	2.701
LogD:	2.803
LogS:	-3.121
# Rotatable Bonds:	1
TPSA:	53.6
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.8
Synthetic Accessibility Score:	4.985
Fsp3:	0.6
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.859
MDCK Permeability:	8.50292417453602e-06
Pgp-inhibitor:	0.001
Pgp-substrate:	0.148
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.01

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.268
Plasma Protein Binding (PPB):	91.75843048095703%
Volume Distribution (VD):	1.088
Pgp-substrate:	13.734464645385742%

ADMET: Metabolism

CYP1A2-inhibitor:	0.176
CYP1A2-substrate:	0.725
CYP2C19-inhibitor:	0.023
CYP2C19-substrate:	0.825
CYP2C9-inhibitor:	0.032
CYP2C9-substrate:	0.344
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.229
CYP3A4-inhibitor:	0.179
CYP3A4-substrate:	0.472

ADMET: Excretion

Clearance (CL):	16.876
Half-life (T1/2):	0.556

ADMET: Toxicity

hERG Blockers:	0.019
Human Hepatotoxicity (H-HT):	0.749
Drug-inuced Liver Injury (DILI):	0.893
AMES Toxicity:	0.131
Rat Oral Acute Toxicity:	0.921
Maximum Recommended Daily Dose:	0.488
Skin Sensitization:	0.581
Carcinogencity:	0.926
Eye Corrosion:	0.004
Eye Irritation:	0.017
Respiratory Toxicity:	0.977

Download Data

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

Natural Product: NPC321385

Natural Product ID:	NPC321385
*Common Name:**	Chlorajapolide C
IUPAC Name:	n.a.
Synonyms:	Chlorajapolide C
Standard InCHIKey:	MTQDWDRXGBDENC-RNKJKDHYSA-N
Standard InCHI:	InChI=1S/C15H18O3/c1-7-8-3-12-10(6-16)9-4-11(9)15(12,2)5-13(8)18-14(7)17/h9,11,13,16H,3-6H2,1-2H3/t9-,11-,13+,15+/m1/s1
SMILES:	OCC1=C2CC3=C(C)C(=O)O[C@H]3C[C@]2([C@H]2[C@@H]1C2)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1669180
PubChem CID:	50993899
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones [CHEMONTID:0001543] Sesquiterpene lactones [CHEMONTID:0001772] Eudesmanolides, secoeudesmanolides, and derivatives

*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
NPO6915	Chloranthus japonicus	Species	Chloranthaceae	Eukaryota	n.a.	whole plant	n.a.	DOI[10.1016/j.phytol.2016.01.005]
NPO6915	Chloranthus japonicus	Species	Chloranthaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[18451544]
NPO21178	Chloranthus serratus	Species	Chloranthaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19053511]
NPO6915	Chloranthus japonicus	Species	Chloranthaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[21142110]
NPO6915	Chloranthus japonicus	Species	Chloranthaceae	Eukaryota	Whole plant	Suiling district, Heilongjiang Province, China	2008-AUG	PMID[21142110]
NPO6915	Chloranthus japonicus	Species	Chloranthaceae	Eukaryota	whole plants	Suiling district, Heilongjiang Province, China	2008-AUG	PMID[21142110]
NPO6915	Chloranthus japonicus	Species	Chloranthaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[21650224]
NPO6915	Chloranthus japonicus	Species	Chloranthaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21650224]
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]
NPO6915	Chloranthus japonicus	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]
NPO6915	Chloranthus japonicus	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]
NPO6915	Chloranthus japonicus	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
IC50	9

Activity Type	# Activity
Cell Line	8
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT65	Cell Line	HepG2	Homo sapiens	IC50	<	10000.0	nM	PMID[520069]
NPT1997	Cell Line	OS-RC-2	Homo sapiens	IC50	<	10000.0	nM	PMID[520069]
NPT81	Cell Line	A549	Homo sapiens	IC50	<	10000.0	nM	PMID[520069]
NPT146	Cell Line	SK-OV-3	Homo sapiens	IC50	<	10000.0	nM	PMID[520069]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	<	10000.0	nM	PMID[520069]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	<	10000.0	nM	PMID[520069]
NPT515	Cell Line	SGC-7901	Homo sapiens	IC50	<	10000.0	nM	PMID[520069]
NPT114	Cell Line	LoVo	Homo sapiens	IC50	<	10000.0	nM	PMID[520069]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	50000.0	nM	PMID[520070]

☑ 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 NPC321385 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	176
0.1-0.2	1294
0.2-0.3	5837
0.3-0.4	16102
0.4-0.5	8978
0.5-0.6	7333
0.6-0.7	2711
0.7-0.8	259
0.8-0.85	3
0.85-0.9	2
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8652	High Similarity	NPC319861
0.8652	High Similarity	NPC320231
0.8333	Intermediate Similarity	NPC329435
0.8315	Intermediate Similarity	NPC472954
0.8202	Intermediate Similarity	NPC2882
0.8118	Intermediate Similarity	NPC311070
0.8049	Intermediate Similarity	NPC189206
0.8023	Intermediate Similarity	NPC32223
0.8023	Intermediate Similarity	NPC474693
0.7976	Intermediate Similarity	NPC10636
0.7955	Intermediate Similarity	NPC471657
0.7955	Intermediate Similarity	NPC45957
0.7955	Intermediate Similarity	NPC473891
0.7952	Intermediate Similarity	NPC184737
0.7931	Intermediate Similarity	NPC475860
0.7931	Intermediate Similarity	NPC473659
0.7931	Intermediate Similarity	NPC474694
0.7907	Intermediate Similarity	NPC472377
0.7889	Intermediate Similarity	NPC182136
0.7889	Intermediate Similarity	NPC472642
0.7841	Intermediate Similarity	NPC131813
0.7835	Intermediate Similarity	NPC161775
0.7802	Intermediate Similarity	NPC78594
0.7802	Intermediate Similarity	NPC472953
0.7778	Intermediate Similarity	NPC50488
0.7778	Intermediate Similarity	NPC474396
0.7778	Intermediate Similarity	NPC212664
0.7753	Intermediate Similarity	NPC312561
0.7742	Intermediate Similarity	NPC111273
0.7742	Intermediate Similarity	NPC471915
0.7727	Intermediate Similarity	NPC245434
0.7727	Intermediate Similarity	NPC471795
0.7717	Intermediate Similarity	NPC472640
0.7717	Intermediate Similarity	NPC472641
0.7692	Intermediate Similarity	NPC221111
0.7692	Intermediate Similarity	NPC78973
0.7692	Intermediate Similarity	NPC310479
0.7692	Intermediate Similarity	NPC280149
0.7667	Intermediate Similarity	NPC472809
0.7667	Intermediate Similarity	NPC472810
0.766	Intermediate Similarity	NPC470801
0.766	Intermediate Similarity	NPC190713
0.764	Intermediate Similarity	NPC329692
0.764	Intermediate Similarity	NPC474062
0.7634	Intermediate Similarity	NPC201725
0.7614	Intermediate Similarity	NPC475100
0.7609	Intermediate Similarity	NPC472814
0.7609	Intermediate Similarity	NPC110923
0.7609	Intermediate Similarity	NPC74296
0.7609	Intermediate Similarity	NPC177037
0.7609	Intermediate Similarity	NPC472811
0.7604	Intermediate Similarity	NPC201406
0.7582	Intermediate Similarity	NPC470734
0.7579	Intermediate Similarity	NPC231751
0.7579	Intermediate Similarity	NPC205143
0.7576	Intermediate Similarity	NPC85670
0.7558	Intermediate Similarity	NPC268827
0.7556	Intermediate Similarity	NPC471796
0.7553	Intermediate Similarity	NPC472441
0.7551	Intermediate Similarity	NPC476237
0.7529	Intermediate Similarity	NPC172066
0.7528	Intermediate Similarity	NPC86316
0.7528	Intermediate Similarity	NPC106416
0.7528	Intermediate Similarity	NPC42586
0.7528	Intermediate Similarity	NPC473251
0.7528	Intermediate Similarity	NPC253604
0.7527	Intermediate Similarity	NPC115021
0.7527	Intermediate Similarity	NPC472812
0.7527	Intermediate Similarity	NPC110022
0.7527	Intermediate Similarity	NPC205034
0.7527	Intermediate Similarity	NPC152778
0.7527	Intermediate Similarity	NPC162615
0.7527	Intermediate Similarity	NPC476304
0.7527	Intermediate Similarity	NPC139692
0.7527	Intermediate Similarity	NPC53555
0.75	Intermediate Similarity	NPC218107
0.75	Intermediate Similarity	NPC30502
0.75	Intermediate Similarity	NPC42476
0.75	Intermediate Similarity	NPC209816
0.75	Intermediate Similarity	NPC474809
0.75	Intermediate Similarity	NPC92275
0.75	Intermediate Similarity	NPC281942
0.75	Intermediate Similarity	NPC232426
0.7474	Intermediate Similarity	NPC242848
0.7474	Intermediate Similarity	NPC162346
0.7474	Intermediate Similarity	NPC165632
0.7474	Intermediate Similarity	NPC473153
0.7474	Intermediate Similarity	NPC134072
0.7474	Intermediate Similarity	NPC234993
0.7473	Intermediate Similarity	NPC472378
0.7473	Intermediate Similarity	NPC471956
0.7471	Intermediate Similarity	NPC475944
0.7447	Intermediate Similarity	NPC470255
0.7447	Intermediate Similarity	NPC476186
0.7447	Intermediate Similarity	NPC474554
0.7447	Intermediate Similarity	NPC57117
0.7447	Intermediate Similarity	NPC96541
0.7447	Intermediate Similarity	NPC474555
0.7447	Intermediate Similarity	NPC471720
0.7447	Intermediate Similarity	NPC53685
0.7444	Intermediate Similarity	NPC250981
0.7444	Intermediate Similarity	NPC471219
0.7442	Intermediate Similarity	NPC80471
0.7442	Intermediate Similarity	NPC242767
0.7442	Intermediate Similarity	NPC5908
0.7442	Intermediate Similarity	NPC110373
0.7423	Intermediate Similarity	NPC472826
0.7419	Intermediate Similarity	NPC329842
0.7419	Intermediate Similarity	NPC72845
0.7419	Intermediate Similarity	NPC141831
0.7419	Intermediate Similarity	NPC249034
0.7416	Intermediate Similarity	NPC16887
0.7416	Intermediate Similarity	NPC53011
0.7416	Intermediate Similarity	NPC82297
0.7416	Intermediate Similarity	NPC471302
0.7416	Intermediate Similarity	NPC154893
0.7416	Intermediate Similarity	NPC96055
0.7416	Intermediate Similarity	NPC37005
0.7412	Intermediate Similarity	NPC316500
0.7412	Intermediate Similarity	NPC262747
0.7391	Intermediate Similarity	NPC472240
0.7391	Intermediate Similarity	NPC262858
0.7391	Intermediate Similarity	NPC5509
0.7386	Intermediate Similarity	NPC471298
0.7374	Intermediate Similarity	NPC297617
0.7374	Intermediate Similarity	NPC474822
0.7374	Intermediate Similarity	NPC112009
0.7368	Intermediate Similarity	NPC220221
0.7368	Intermediate Similarity	NPC469873
0.7368	Intermediate Similarity	NPC293052
0.7356	Intermediate Similarity	NPC281880
0.7353	Intermediate Similarity	NPC257853
0.7347	Intermediate Similarity	NPC222875
0.7347	Intermediate Similarity	NPC247701
0.7347	Intermediate Similarity	NPC295110
0.7347	Intermediate Similarity	NPC268829
0.7347	Intermediate Similarity	NPC118174
0.7347	Intermediate Similarity	NPC25177
0.734	Intermediate Similarity	NPC38232
0.734	Intermediate Similarity	NPC472871
0.734	Intermediate Similarity	NPC156553
0.7333	Intermediate Similarity	NPC65661
0.7333	Intermediate Similarity	NPC30984
0.7333	Intermediate Similarity	NPC52628
0.7326	Intermediate Similarity	NPC474816
0.7326	Intermediate Similarity	NPC209135
0.732	Intermediate Similarity	NPC98868
0.7312	Intermediate Similarity	NPC51486
0.7312	Intermediate Similarity	NPC477782
0.7303	Intermediate Similarity	NPC471297
0.7303	Intermediate Similarity	NPC472473
0.7294	Intermediate Similarity	NPC476317
0.7292	Intermediate Similarity	NPC472362
0.7292	Intermediate Similarity	NPC17578
0.7292	Intermediate Similarity	NPC195366
0.7292	Intermediate Similarity	NPC114743
0.7292	Intermediate Similarity	NPC154526
0.7292	Intermediate Similarity	NPC7124
0.7292	Intermediate Similarity	NPC240673
0.7292	Intermediate Similarity	NPC472363
0.7292	Intermediate Similarity	NPC476797
0.7292	Intermediate Similarity	NPC16967
0.7273	Intermediate Similarity	NPC471914
0.7273	Intermediate Similarity	NPC475038
0.7273	Intermediate Similarity	NPC282293
0.7273	Intermediate Similarity	NPC109195
0.7273	Intermediate Similarity	NPC170303
0.7273	Intermediate Similarity	NPC159148
0.7263	Intermediate Similarity	NPC191521
0.7263	Intermediate Similarity	NPC184870
0.7263	Intermediate Similarity	NPC105490
0.7263	Intermediate Similarity	NPC298973
0.7263	Intermediate Similarity	NPC104925
0.7263	Intermediate Similarity	NPC469697
0.7253	Intermediate Similarity	NPC477920
0.7245	Intermediate Similarity	NPC251680
0.7245	Intermediate Similarity	NPC472644
0.7245	Intermediate Similarity	NPC470074
0.7245	Intermediate Similarity	NPC476303
0.7245	Intermediate Similarity	NPC16601
0.7234	Intermediate Similarity	NPC470113
0.7234	Intermediate Similarity	NPC477783
0.7234	Intermediate Similarity	NPC212948
0.7234	Intermediate Similarity	NPC473675
0.7228	Intermediate Similarity	NPC472818
0.7222	Intermediate Similarity	NPC222634
0.7222	Intermediate Similarity	NPC472326
0.7222	Intermediate Similarity	NPC306951
0.7222	Intermediate Similarity	NPC471301
0.7216	Intermediate Similarity	NPC121402
0.7216	Intermediate Similarity	NPC475709
0.7216	Intermediate Similarity	NPC175351
0.7216	Intermediate Similarity	NPC141401
0.7216	Intermediate Similarity	NPC151681
0.7216	Intermediate Similarity	NPC476253
0.7216	Intermediate Similarity	NPC474343
0.7216	Intermediate Similarity	NPC253826
0.7216	Intermediate Similarity	NPC132753
0.7216	Intermediate Similarity	NPC224356
0.7209	Intermediate Similarity	NPC54996

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 NPC321385 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	158
0.1-0.2	1832
0.2-0.3	4133
0.3-0.4	2203
0.4-0.5	518
0.5-0.6	276
0.6-0.7	30
0.7-0.8	0
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
0.7245	Intermediate Similarity	NPD7640	Approved
0.7245	Intermediate Similarity	NPD7639	Approved
0.7143	Intermediate Similarity	NPD4225	Approved
0.7143	Intermediate Similarity	NPD7638	Approved
0.71	Intermediate Similarity	NPD7632	Discontinued
0.7	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD1694	Approved
0.6848	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD5362	Discontinued
0.6701	Remote Similarity	NPD7637	Suspended
0.6698	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.663	Remote Similarity	NPD5209	Approved
0.6598	Remote Similarity	NPD5785	Approved
0.6596	Remote Similarity	NPD1696	Phase 3
0.6577	Remote Similarity	NPD7115	Discovery
0.6556	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6506	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6505	Remote Similarity	NPD5344	Discontinued
0.6495	Remote Similarity	NPD6051	Approved
0.6481	Remote Similarity	NPD6371	Approved
0.6481	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6449	Remote Similarity	NPD6686	Approved
0.6392	Remote Similarity	NPD6903	Approved
0.6383	Remote Similarity	NPD7154	Phase 3
0.6383	Remote Similarity	NPD6695	Phase 3
0.6383	Remote Similarity	NPD5331	Approved
0.6383	Remote Similarity	NPD5332	Approved
0.6374	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6373	Remote Similarity	NPD6083	Phase 2
0.6373	Remote Similarity	NPD6084	Phase 2
0.6372	Remote Similarity	NPD7328	Approved
0.6372	Remote Similarity	NPD7327	Approved
0.6354	Remote Similarity	NPD6409	Approved
0.6354	Remote Similarity	NPD5330	Approved
0.6354	Remote Similarity	NPD7334	Approved
0.6354	Remote Similarity	NPD6684	Approved
0.6354	Remote Similarity	NPD3618	Phase 1
0.6354	Remote Similarity	NPD7521	Approved
0.6354	Remote Similarity	NPD7146	Approved
0.6354	Remote Similarity	NPD5279	Phase 3
0.6344	Remote Similarity	NPD6902	Approved
0.6344	Remote Similarity	NPD4790	Discontinued
0.6337	Remote Similarity	NPD5695	Phase 3
0.6337	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6327	Remote Similarity	NPD1695	Approved
0.6327	Remote Similarity	NPD5328	Approved
0.6316	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD7516	Approved
0.6316	Remote Similarity	NPD3665	Phase 1
0.6316	Remote Similarity	NPD3666	Approved
0.6316	Remote Similarity	NPD3133	Approved
0.6304	Remote Similarity	NPD6929	Approved
0.63	Remote Similarity	NPD6399	Phase 3
0.6296	Remote Similarity	NPD7320	Approved
0.6292	Remote Similarity	NPD6924	Approved
0.6292	Remote Similarity	NPD6926	Approved
0.6263	Remote Similarity	NPD7838	Discovery
0.6263	Remote Similarity	NPD46	Approved
0.6263	Remote Similarity	NPD6698	Approved
0.6262	Remote Similarity	NPD5739	Approved
0.6262	Remote Similarity	NPD6402	Approved
0.6262	Remote Similarity	NPD7128	Approved
0.6262	Remote Similarity	NPD6675	Approved
0.6261	Remote Similarity	NPD8377	Approved
0.6261	Remote Similarity	NPD8294	Approved
0.625	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.625	Remote Similarity	NPD6648	Approved
0.6238	Remote Similarity	NPD7748	Approved
0.6238	Remote Similarity	NPD6001	Approved
0.6237	Remote Similarity	NPD7509	Discontinued
0.6237	Remote Similarity	NPD6931	Approved
0.6237	Remote Similarity	NPD6930	Phase 2
0.6237	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6237	Remote Similarity	NPD7332	Phase 2
0.6224	Remote Similarity	NPD5737	Approved
0.6224	Remote Similarity	NPD6672	Approved
0.6224	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6207	Remote Similarity	NPD8378	Approved
0.6207	Remote Similarity	NPD8335	Approved
0.6207	Remote Similarity	NPD8033	Approved
0.6207	Remote Similarity	NPD8296	Approved
0.6207	Remote Similarity	NPD8380	Approved
0.6207	Remote Similarity	NPD8379	Approved
0.6204	Remote Similarity	NPD5697	Approved
0.6204	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6204	Remote Similarity	NPD5701	Approved
0.62	Remote Similarity	NPD5693	Phase 1
0.62	Remote Similarity	NPD6079	Approved
0.62	Remote Similarity	NPD7515	Phase 2
0.6154	Remote Similarity	NPD6933	Approved
0.6154	Remote Similarity	NPD5696	Approved
0.6147	Remote Similarity	NPD6881	Approved
0.6147	Remote Similarity	NPD6899	Approved
0.6147	Remote Similarity	NPD6011	Approved
0.6146	Remote Similarity	NPD4786	Approved
0.6139	Remote Similarity	NPD5779	Approved
0.6139	Remote Similarity	NPD5778	Approved
0.6139	Remote Similarity	NPD4202	Approved
0.6134	Remote Similarity	NPD7507	Approved
0.6122	Remote Similarity	NPD7750	Discontinued
0.6122	Remote Similarity	NPD7524	Approved
0.6105	Remote Similarity	NPD3667	Approved
0.6091	Remote Similarity	NPD6373	Approved
0.6091	Remote Similarity	NPD6012	Approved
0.6091	Remote Similarity	NPD6372	Approved
0.6091	Remote Similarity	NPD6013	Approved
0.6091	Remote Similarity	NPD6014	Approved
0.6087	Remote Similarity	NPD6925	Approved
0.6087	Remote Similarity	NPD5776	Phase 2
0.6082	Remote Similarity	NPD5363	Approved
0.6071	Remote Similarity	NPD6053	Discontinued
0.6064	Remote Similarity	NPD4819	Approved
0.6064	Remote Similarity	NPD4822	Approved
0.6064	Remote Similarity	NPD7525	Registered
0.6064	Remote Similarity	NPD4821	Approved
0.6064	Remote Similarity	NPD4820	Approved
0.6064	Remote Similarity	NPD7514	Phase 3
0.6064	Remote Similarity	NPD4748	Discontinued
0.6058	Remote Similarity	NPD7902	Approved
0.6044	Remote Similarity	NPD8039	Approved
0.6044	Remote Similarity	NPD6942	Approved
0.6044	Remote Similarity	NPD7339	Approved
0.604	Remote Similarity	NPD8034	Phase 2
0.604	Remote Similarity	NPD8035	Phase 2
0.604	Remote Similarity	NPD6411	Approved
0.6036	Remote Similarity	NPD6883	Approved
0.6036	Remote Similarity	NPD7290	Approved
0.6036	Remote Similarity	NPD7102	Approved
0.6023	Remote Similarity	NPD6922	Approved
0.6023	Remote Similarity	NPD6923	Approved
0.6022	Remote Similarity	NPD3617	Approved
0.6022	Remote Similarity	NPD4268	Approved
0.6022	Remote Similarity	NPD7145	Approved
0.6022	Remote Similarity	NPD4271	Approved
0.602	Remote Similarity	NPD4249	Approved
0.602	Remote Similarity	NPD4519	Discontinued
0.602	Remote Similarity	NPD4623	Approved
0.6	Remote Similarity	NPD4753	Phase 2
0.6	Remote Similarity	NPD6898	Phase 1
0.5984	Remote Similarity	NPD7319	Approved
0.5982	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5982	Remote Similarity	NPD8130	Phase 1
0.5982	Remote Similarity	NPD6650	Approved
0.5982	Remote Similarity	NPD6617	Approved
0.5982	Remote Similarity	NPD6847	Approved
0.5982	Remote Similarity	NPD6649	Approved
0.5982	Remote Similarity	NPD6869	Approved
0.5981	Remote Similarity	NPD5211	Phase 2
0.5978	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.5963	Remote Similarity	NPD6008	Approved
0.5962	Remote Similarity	NPD5221	Approved
0.5962	Remote Similarity	NPD5222	Approved
0.5962	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.5962	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.5962	Remote Similarity	NPD4697	Phase 3
0.596	Remote Similarity	NPD4250	Approved
0.596	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.596	Remote Similarity	NPD4251	Approved
0.5957	Remote Similarity	NPD4195	Approved
0.5955	Remote Similarity	NPD7143	Approved
0.5955	Remote Similarity	NPD7144	Approved
0.5941	Remote Similarity	NPD5207	Approved
0.5938	Remote Similarity	NPD4270	Approved
0.5938	Remote Similarity	NPD4221	Approved
0.5938	Remote Similarity	NPD4223	Phase 3
0.5938	Remote Similarity	NPD4269	Approved
0.5934	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.5932	Remote Similarity	NPD7503	Approved
0.5929	Remote Similarity	NPD8297	Approved
0.5929	Remote Similarity	NPD6882	Approved
0.5918	Remote Similarity	NPD6893	Approved
0.5909	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.5905	Remote Similarity	NPD4755	Approved
0.5905	Remote Similarity	NPD5173	Approved
0.59	Remote Similarity	NPD5208	Approved
0.5889	Remote Similarity	NPD7152	Approved
0.5889	Remote Similarity	NPD7150	Approved
0.5889	Remote Similarity	NPD7151	Approved
0.5888	Remote Similarity	NPD4159	Approved
0.5882	Remote Similarity	NPD5284	Approved
0.5882	Remote Similarity	NPD5281	Approved
0.5882	Remote Similarity	NPD7087	Discontinued
0.5872	Remote Similarity	NPD5141	Approved
0.587	Remote Similarity	NPD8264	Approved
0.5859	Remote Similarity	NPD5786	Approved
0.5849	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.5842	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.5842	Remote Similarity	NPD6080	Approved
0.5842	Remote Similarity	NPD6673	Approved
0.5842	Remote Similarity	NPD6101	Approved
0.5842	Remote Similarity	NPD6904	Approved
0.5816	Remote Similarity	NPD4197	Approved
0.5814	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.5806	Remote Similarity	NPD6117	Approved
0.5794	Remote Similarity	NPD4700	Approved
0.5794	Remote Similarity	NPD6404	Discontinued
0.5794	Remote Similarity	NPD5286	Approved
0.5794	Remote Similarity	NPD4696	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