NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	264.14
Volume:	263.658
LogP:	1.957
LogD:	1.703
LogS:	-2.595
# Rotatable Bonds:	1
TPSA:	73.83
# H-Bond Aceptor:	4
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.716
Synthetic Accessibility Score:	5.053
Fsp3:	0.733
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:	-5.204
MDCK Permeability:	4.596688540914329e-06
Pgp-inhibitor:	0.001
Pgp-substrate:	0.276
Human Intestinal Absorption (HIA):	0.012
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.029

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.702
Plasma Protein Binding (PPB):	89.0708999633789%
Volume Distribution (VD):	1.054
Pgp-substrate:	15.258943557739258%

ADMET: Metabolism

CYP1A2-inhibitor:	0.062
CYP1A2-substrate:	0.538
CYP2C19-inhibitor:	0.012
CYP2C19-substrate:	0.604
CYP2C9-inhibitor:	0.023
CYP2C9-substrate:	0.2
CYP2D6-inhibitor:	0.005
CYP2D6-substrate:	0.362
CYP3A4-inhibitor:	0.04
CYP3A4-substrate:	0.154

ADMET: Excretion

Clearance (CL):	10.678
Half-life (T1/2):	0.729

ADMET: Toxicity

hERG Blockers:	0.015
Human Hepatotoxicity (H-HT):	0.559
Drug-inuced Liver Injury (DILI):	0.695
AMES Toxicity:	0.034
Rat Oral Acute Toxicity:	0.78
Maximum Recommended Daily Dose:	0.279
Skin Sensitization:	0.54
Carcinogencity:	0.195
Eye Corrosion:	0.007
Eye Irritation:	0.061
Respiratory Toxicity:	0.961

Download Data

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

Natural Product: NPC329435

Natural Product ID:	NPC329435
*Common Name:**	Chlorajapolide D
IUPAC Name:	n.a.
Synonyms:	Chlorajapolide D
Standard InCHIKey:	QKAOLXBSWUJRPA-NBVFDPJVSA-N
Standard InCHI:	InChI=1S/C15H20O4/c1-7-8-3-12-14(2,5-11(8)19-13(7)17)9-4-10(9)15(12,18)6-16/h9-12,16,18H,3-6H2,1-2H3/t9-,10+,11+,12-,14+,15-/m1/s1
SMILES:	CC1=C2CC3C(CC2OC1=O)(C4CC4C3(CO)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1669181
PubChem CID:	50993900
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]
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[21142110]
NPO6915	Chloranthus japonicus	Species	Chloranthaceae	Eukaryota	Whole plant	Suiling district, Heilongjiang Province, China	2008-AUG	PMID[21142110]
NPO6915	Chloranthus japonicus	Species	Chloranthaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21650224]
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.	Database[HerDing]
NPO6915	Chloranthus japonicus	Species	Chloranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
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	8

Activity Type	# Activity
Cell Line	8

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[483189]
NPT1997	Cell Line	OS-RC-2	Homo sapiens	IC50	<	10000.0	nM	PMID[483189]
NPT81	Cell Line	A549	Homo sapiens	IC50	<	10000.0	nM	PMID[483189]
NPT146	Cell Line	SK-OV-3	Homo sapiens	IC50	<	10000.0	nM	PMID[483189]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	<	10000.0	nM	PMID[483189]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	<	10000.0	nM	PMID[483189]
NPT515	Cell Line	SGC-7901	Homo sapiens	IC50	<	10000.0	nM	PMID[483189]
NPT114	Cell Line	LoVo	Homo sapiens	IC50	<	10000.0	nM	PMID[483189]

☑ 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 NPC329435 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	209
0.1-0.2	1589
0.2-0.3	5396
0.3-0.4	14006
0.4-0.5	8253
0.5-0.6	7648
0.6-0.7	4740
0.7-0.8	831
0.8-0.85	22
0.85-0.9	2
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8673	High Similarity	NPC472821
0.8586	High Similarity	NPC161775
0.8511	High Similarity	NPC110022
0.85	High Similarity	NPC186668
0.8469	Intermediate Similarity	NPC25177
0.8469	Intermediate Similarity	NPC247701
0.8469	Intermediate Similarity	NPC222875
0.8469	Intermediate Similarity	NPC268829
0.8469	Intermediate Similarity	NPC295110
0.8444	Intermediate Similarity	NPC32223
0.8351	Intermediate Similarity	NPC231751
0.8333	Intermediate Similarity	NPC321385
0.83	Intermediate Similarity	NPC97487
0.83	Intermediate Similarity	NPC189588
0.83	Intermediate Similarity	NPC10232
0.83	Intermediate Similarity	NPC160583
0.83	Intermediate Similarity	NPC187302
0.83	Intermediate Similarity	NPC196471
0.8211	Intermediate Similarity	NPC78594
0.82	Intermediate Similarity	NPC470972
0.8144	Intermediate Similarity	NPC111273
0.8144	Intermediate Similarity	NPC471915
0.8137	Intermediate Similarity	NPC472818
0.8137	Intermediate Similarity	NPC119855
0.8137	Intermediate Similarity	NPC470980
0.8137	Intermediate Similarity	NPC85670
0.8137	Intermediate Similarity	NPC220217
0.8119	Intermediate Similarity	NPC474822
0.8077	Intermediate Similarity	NPC257853
0.8061	Intermediate Similarity	NPC320231
0.8061	Intermediate Similarity	NPC319861
0.8058	Intermediate Similarity	NPC472820
0.8043	Intermediate Similarity	NPC37005
0.8043	Intermediate Similarity	NPC154893
0.8043	Intermediate Similarity	NPC53011
0.8043	Intermediate Similarity	NPC16887
0.8039	Intermediate Similarity	NPC200861
0.8039	Intermediate Similarity	NPC472819
0.8037	Intermediate Similarity	NPC106446
0.8	Intermediate Similarity	NPC472826
0.798	Intermediate Similarity	NPC205143
0.7963	Intermediate Similarity	NPC196931
0.7957	Intermediate Similarity	NPC253604
0.7938	Intermediate Similarity	NPC472641
0.7938	Intermediate Similarity	NPC472640
0.7925	Intermediate Similarity	NPC470076
0.7917	Intermediate Similarity	NPC472642
0.7905	Intermediate Similarity	NPC475030
0.789	Intermediate Similarity	NPC290693
0.7879	Intermediate Similarity	NPC98165
0.787	Intermediate Similarity	NPC31354
0.787	Intermediate Similarity	NPC84949
0.787	Intermediate Similarity	NPC471633
0.787	Intermediate Similarity	NPC69576
0.787	Intermediate Similarity	NPC178289
0.7864	Intermediate Similarity	NPC472822
0.7864	Intermediate Similarity	NPC473577
0.7864	Intermediate Similarity	NPC474550
0.7864	Intermediate Similarity	NPC475585
0.7857	Intermediate Similarity	NPC27335
0.7857	Intermediate Similarity	NPC105490
0.783	Intermediate Similarity	NPC179642
0.7822	Intermediate Similarity	NPC251680
0.78	Intermediate Similarity	NPC254121
0.7798	Intermediate Similarity	NPC5311
0.7798	Intermediate Similarity	NPC199428
0.7798	Intermediate Similarity	NPC310341
0.7798	Intermediate Similarity	NPC193382
0.7798	Intermediate Similarity	NPC106228
0.7798	Intermediate Similarity	NPC99620
0.7798	Intermediate Similarity	NPC138372
0.7789	Intermediate Similarity	NPC45957
0.7789	Intermediate Similarity	NPC473891
0.7789	Intermediate Similarity	NPC471657
0.7788	Intermediate Similarity	NPC84865
0.7788	Intermediate Similarity	NPC475290
0.7778	Intermediate Similarity	NPC37408
0.7755	Intermediate Similarity	NPC7349
0.7745	Intermediate Similarity	NPC475099
0.7745	Intermediate Similarity	NPC11974
0.7727	Intermediate Similarity	NPC157376
0.7727	Intermediate Similarity	NPC309034
0.7727	Intermediate Similarity	NPC34390
0.7727	Intermediate Similarity	NPC196429
0.7727	Intermediate Similarity	NPC471354
0.7727	Intermediate Similarity	NPC203862
0.7727	Intermediate Similarity	NPC77319
0.7727	Intermediate Similarity	NPC99728
0.7727	Intermediate Similarity	NPC152615
0.7727	Intermediate Similarity	NPC50305
0.7727	Intermediate Similarity	NPC471353
0.7727	Intermediate Similarity	NPC471355
0.7727	Intermediate Similarity	NPC471351
0.7727	Intermediate Similarity	NPC87250
0.7727	Intermediate Similarity	NPC93883
0.7727	Intermediate Similarity	NPC84987
0.7727	Intermediate Similarity	NPC158344
0.7727	Intermediate Similarity	NPC244402
0.7727	Intermediate Similarity	NPC473852
0.7727	Intermediate Similarity	NPC27507
0.7727	Intermediate Similarity	NPC474418
0.7727	Intermediate Similarity	NPC243196
0.7727	Intermediate Similarity	NPC142066
0.7723	Intermediate Similarity	NPC181147
0.7719	Intermediate Similarity	NPC226049
0.7706	Intermediate Similarity	NPC216665
0.77	Intermediate Similarity	NPC165632
0.77	Intermediate Similarity	NPC475304
0.7685	Intermediate Similarity	NPC470063
0.7684	Intermediate Similarity	NPC131813
0.7679	Intermediate Similarity	NPC472004
0.7677	Intermediate Similarity	NPC201725
0.767	Intermediate Similarity	NPC471914
0.767	Intermediate Similarity	NPC475038
0.767	Intermediate Similarity	NPC472552
0.767	Intermediate Similarity	NPC295791
0.767	Intermediate Similarity	NPC472815
0.767	Intermediate Similarity	NPC109195
0.7664	Intermediate Similarity	NPC103491
0.7658	Intermediate Similarity	NPC83287
0.7653	Intermediate Similarity	NPC473675
0.7652	Intermediate Similarity	NPC15095
0.7647	Intermediate Similarity	NPC38855
0.7647	Intermediate Similarity	NPC16601
0.7642	Intermediate Similarity	NPC472825
0.7642	Intermediate Similarity	NPC88701
0.7636	Intermediate Similarity	NPC72772
0.7636	Intermediate Similarity	NPC470075
0.7636	Intermediate Similarity	NPC469794
0.76	Intermediate Similarity	NPC86893
0.76	Intermediate Similarity	NPC220221
0.76	Intermediate Similarity	NPC469873
0.76	Intermediate Similarity	NPC292178
0.76	Intermediate Similarity	NPC276110
0.7596	Intermediate Similarity	NPC471938
0.7596	Intermediate Similarity	NPC297617
0.7596	Intermediate Similarity	NPC473694
0.7596	Intermediate Similarity	NPC159533
0.7596	Intermediate Similarity	NPC23584
0.7596	Intermediate Similarity	NPC475334
0.7596	Intermediate Similarity	NPC475623
0.7596	Intermediate Similarity	NPC112009
0.7596	Intermediate Similarity	NPC474775
0.7589	Intermediate Similarity	NPC19028
0.7589	Intermediate Similarity	NPC29639
0.7589	Intermediate Similarity	NPC44899
0.7589	Intermediate Similarity	NPC329905
0.7589	Intermediate Similarity	NPC32177
0.7589	Intermediate Similarity	NPC55532
0.7589	Intermediate Similarity	NPC236973
0.7589	Intermediate Similarity	NPC469756
0.7589	Intermediate Similarity	NPC9674
0.7589	Intermediate Similarity	NPC292467
0.7589	Intermediate Similarity	NPC5883
0.7589	Intermediate Similarity	NPC30483
0.7589	Intermediate Similarity	NPC470897
0.7589	Intermediate Similarity	NPC304260
0.7576	Intermediate Similarity	NPC53555
0.7573	Intermediate Similarity	NPC472554
0.7573	Intermediate Similarity	NPC471412
0.7573	Intermediate Similarity	NPC475617
0.757	Intermediate Similarity	NPC299590
0.7551	Intermediate Similarity	NPC471184
0.7549	Intermediate Similarity	NPC218107
0.7549	Intermediate Similarity	NPC222303
0.7545	Intermediate Similarity	NPC43213
0.7544	Intermediate Similarity	NPC115349
0.7525	Intermediate Similarity	NPC134072
0.7525	Intermediate Similarity	NPC7124
0.7525	Intermediate Similarity	NPC234993
0.7525	Intermediate Similarity	NPC276103
0.7525	Intermediate Similarity	NPC473153
0.7525	Intermediate Similarity	NPC54248
0.7524	Intermediate Similarity	NPC181104
0.7524	Intermediate Similarity	NPC288502
0.7524	Intermediate Similarity	NPC103298
0.7524	Intermediate Similarity	NPC471937
0.7524	Intermediate Similarity	NPC201144
0.7524	Intermediate Similarity	NPC475335
0.7524	Intermediate Similarity	NPC80809
0.7524	Intermediate Similarity	NPC475331
0.7524	Intermediate Similarity	NPC121518
0.7522	Intermediate Similarity	NPC475556
0.7522	Intermediate Similarity	NPC72260
0.7522	Intermediate Similarity	NPC475136
0.7522	Intermediate Similarity	NPC475629
0.7522	Intermediate Similarity	NPC474466
0.75	Intermediate Similarity	NPC218093
0.75	Intermediate Similarity	NPC11956
0.75	Intermediate Similarity	NPC110373
0.75	Intermediate Similarity	NPC121423
0.75	Intermediate Similarity	NPC161998
0.75	Intermediate Similarity	NPC80471
0.75	Intermediate Similarity	NPC165578
0.75	Intermediate Similarity	NPC5908
0.75	Intermediate Similarity	NPC471219
0.75	Intermediate Similarity	NPC472467
0.75	Intermediate Similarity	NPC57117
0.7478	Intermediate Similarity	NPC27363
0.7478	Intermediate Similarity	NPC129992

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 NPC329435 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	183
0.1-0.2	2043
0.2-0.3	4062
0.3-0.4	2019
0.4-0.5	459
0.5-0.6	234
0.6-0.7	137
0.7-0.8	13
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
0.79	Intermediate Similarity	NPD7638	Approved
0.7822	Intermediate Similarity	NPD7639	Approved
0.7822	Intermediate Similarity	NPD7640	Approved
0.767	Intermediate Similarity	NPD7632	Discontinued
0.7658	Intermediate Similarity	NPD7327	Approved
0.7658	Intermediate Similarity	NPD7328	Approved
0.7589	Intermediate Similarity	NPD7516	Approved
0.757	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7522	Intermediate Similarity	NPD8377	Approved
0.7522	Intermediate Similarity	NPD8294	Approved
0.7456	Intermediate Similarity	NPD8033	Approved
0.7456	Intermediate Similarity	NPD8378	Approved
0.7456	Intermediate Similarity	NPD8296	Approved
0.7456	Intermediate Similarity	NPD8335	Approved
0.7456	Intermediate Similarity	NPD8380	Approved
0.7456	Intermediate Similarity	NPD8379	Approved
0.735	Intermediate Similarity	NPD7507	Approved
0.7212	Intermediate Similarity	NPD4225	Approved
0.7182	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7167	Intermediate Similarity	NPD7319	Approved
0.7075	Intermediate Similarity	NPD5344	Discontinued
0.7009	Intermediate Similarity	NPD7503	Approved
0.6991	Remote Similarity	NPD4632	Approved
0.6972	Remote Similarity	NPD6008	Approved
0.6957	Remote Similarity	NPD7115	Discovery
0.6909	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD6371	Approved
0.6847	Remote Similarity	NPD7320	Approved
0.6847	Remote Similarity	NPD6686	Approved
0.6818	Remote Similarity	NPD5739	Approved
0.6818	Remote Similarity	NPD6402	Approved
0.6818	Remote Similarity	NPD6675	Approved
0.6818	Remote Similarity	NPD7128	Approved
0.678	Remote Similarity	NPD6319	Approved
0.6765	Remote Similarity	NPD6051	Approved
0.6762	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD5697	Approved
0.6757	Remote Similarity	NPD5701	Approved
0.6754	Remote Similarity	NPD6053	Discontinued
0.675	Remote Similarity	NPD7604	Phase 2
0.67	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6696	Remote Similarity	NPD6899	Approved
0.6696	Remote Similarity	NPD6881	Approved
0.6696	Remote Similarity	NPD6011	Approved
0.6667	Remote Similarity	NPD6009	Approved
0.6667	Remote Similarity	NPD6648	Approved
0.6637	Remote Similarity	NPD6012	Approved
0.6637	Remote Similarity	NPD6373	Approved
0.6637	Remote Similarity	NPD6372	Approved
0.6637	Remote Similarity	NPD6013	Approved
0.6637	Remote Similarity	NPD6014	Approved
0.6636	Remote Similarity	NPD6084	Phase 2
0.6636	Remote Similarity	NPD6083	Phase 2
0.6609	Remote Similarity	NPD8297	Approved
0.6606	Remote Similarity	NPD4159	Approved
0.6604	Remote Similarity	NPD5695	Phase 3
0.6583	Remote Similarity	NPD5983	Phase 2
0.6579	Remote Similarity	NPD7102	Approved
0.6579	Remote Similarity	NPD7290	Approved
0.6579	Remote Similarity	NPD6883	Approved
0.6571	Remote Similarity	NPD4202	Approved
0.6566	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6557	Remote Similarity	NPD7492	Approved
0.6538	Remote Similarity	NPD7838	Discovery
0.6538	Remote Similarity	NPD6698	Approved
0.6538	Remote Similarity	NPD46	Approved
0.6522	Remote Similarity	NPD6649	Approved
0.6522	Remote Similarity	NPD6869	Approved
0.6522	Remote Similarity	NPD8130	Phase 1
0.6522	Remote Similarity	NPD6617	Approved
0.6522	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD6650	Approved
0.6522	Remote Similarity	NPD6847	Approved
0.6509	Remote Similarity	NPD6001	Approved
0.6504	Remote Similarity	NPD6616	Approved
0.65	Remote Similarity	NPD6059	Approved
0.65	Remote Similarity	NPD6054	Approved
0.6481	Remote Similarity	NPD4755	Approved
0.6476	Remote Similarity	NPD5693	Phase 1
0.6476	Remote Similarity	NPD7637	Suspended
0.6466	Remote Similarity	NPD6882	Approved
0.646	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.646	Remote Similarity	NPD6412	Phase 2
0.6452	Remote Similarity	NPD7078	Approved
0.6452	Remote Similarity	NPD8293	Discontinued
0.6446	Remote Similarity	NPD6016	Approved
0.6446	Remote Similarity	NPD6015	Approved
0.6435	Remote Similarity	NPD4634	Approved
0.6422	Remote Similarity	NPD5696	Approved
0.641	Remote Similarity	NPD8133	Approved
0.6408	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6408	Remote Similarity	NPD7524	Approved
0.64	Remote Similarity	NPD7736	Approved
0.6396	Remote Similarity	NPD5211	Phase 2
0.6393	Remote Similarity	NPD5988	Approved
0.6393	Remote Similarity	NPD6370	Approved
0.6381	Remote Similarity	NPD5785	Approved
0.6373	Remote Similarity	NPD1694	Approved
0.6371	Remote Similarity	NPD6336	Discontinued
0.6364	Remote Similarity	NPD4748	Discontinued
0.6364	Remote Similarity	NPD5286	Approved
0.6364	Remote Similarity	NPD5285	Approved
0.6364	Remote Similarity	NPD4700	Approved
0.6364	Remote Similarity	NPD7525	Registered
0.6364	Remote Similarity	NPD4696	Approved
0.6346	Remote Similarity	NPD6903	Approved
0.6337	Remote Similarity	NPD6695	Phase 3
0.6337	Remote Similarity	NPD5362	Discontinued
0.6311	Remote Similarity	NPD4249	Approved
0.6311	Remote Similarity	NPD7521	Approved
0.6311	Remote Similarity	NPD7334	Approved
0.6311	Remote Similarity	NPD5330	Approved
0.6311	Remote Similarity	NPD7146	Approved
0.6311	Remote Similarity	NPD6409	Approved
0.6311	Remote Similarity	NPD6684	Approved
0.6311	Remote Similarity	NPD3618	Phase 1
0.6306	Remote Similarity	NPD5223	Approved
0.6303	Remote Similarity	NPD6274	Approved
0.6286	Remote Similarity	NPD4753	Phase 2
0.6286	Remote Similarity	NPD1695	Approved
0.6286	Remote Similarity	NPD5328	Approved
0.6283	Remote Similarity	NPD5141	Approved
0.6275	Remote Similarity	NPD3133	Approved
0.6275	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6275	Remote Similarity	NPD3666	Approved
0.6275	Remote Similarity	NPD3665	Phase 1
0.6262	Remote Similarity	NPD6399	Phase 3
0.625	Remote Similarity	NPD5225	Approved
0.625	Remote Similarity	NPD4250	Approved
0.625	Remote Similarity	NPD4251	Approved
0.625	Remote Similarity	NPD6317	Approved
0.625	Remote Similarity	NPD4633	Approved
0.625	Remote Similarity	NPD5224	Approved
0.625	Remote Similarity	NPD5226	Approved
0.6214	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6204	Remote Similarity	NPD7748	Approved
0.6204	Remote Similarity	NPD7625	Phase 1
0.6198	Remote Similarity	NPD6314	Approved
0.6198	Remote Similarity	NPD6335	Approved
0.6198	Remote Similarity	NPD6313	Approved
0.6195	Remote Similarity	NPD4754	Approved
0.6195	Remote Similarity	NPD5174	Approved
0.6195	Remote Similarity	NPD5175	Approved
0.619	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6179	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6176	Remote Similarity	NPD5331	Approved
0.6176	Remote Similarity	NPD5332	Approved
0.6168	Remote Similarity	NPD5284	Approved
0.6168	Remote Similarity	NPD8034	Phase 2
0.6168	Remote Similarity	NPD8035	Phase 2
0.6168	Remote Similarity	NPD6079	Approved
0.6168	Remote Similarity	NPD7515	Phase 2
0.6168	Remote Similarity	NPD5281	Approved
0.6162	Remote Similarity	NPD6114	Approved
0.6162	Remote Similarity	NPD6697	Approved
0.6162	Remote Similarity	NPD6118	Approved
0.6162	Remote Similarity	NPD6115	Approved
0.6161	Remote Similarity	NPD1700	Approved
0.6148	Remote Similarity	NPD7101	Approved
0.6148	Remote Similarity	NPD7100	Approved
0.6142	Remote Similarity	NPD6033	Approved
0.6139	Remote Similarity	NPD4790	Discontinued
0.6132	Remote Similarity	NPD6904	Approved
0.6132	Remote Similarity	NPD6080	Approved
0.6132	Remote Similarity	NPD6673	Approved
0.6122	Remote Similarity	NPD6933	Approved
0.6122	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6121	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6117	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.61	Remote Similarity	NPD4195	Approved
0.6095	Remote Similarity	NPD7750	Discontinued
0.6091	Remote Similarity	NPD5222	Approved
0.6091	Remote Similarity	NPD5221	Approved
0.6091	Remote Similarity	NPD4697	Phase 3
0.6091	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6091	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.6087	Remote Similarity	NPD4767	Approved
0.6087	Remote Similarity	NPD4768	Approved
0.608	Remote Similarity	NPD6067	Discontinued
0.6078	Remote Similarity	NPD5209	Approved
0.6078	Remote Similarity	NPD4223	Phase 3
0.6078	Remote Similarity	NPD4221	Approved
0.6075	Remote Similarity	NPD5692	Phase 3
0.6075	Remote Similarity	NPD5207	Approved
0.6068	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6058	Remote Similarity	NPD1696	Phase 3
0.6048	Remote Similarity	NPD6908	Approved
0.6048	Remote Similarity	NPD6909	Approved
0.604	Remote Similarity	NPD6930	Phase 2
0.604	Remote Similarity	NPD4822	Approved
0.604	Remote Similarity	NPD4821	Approved
0.604	Remote Similarity	NPD4819	Approved
0.604	Remote Similarity	NPD6931	Approved
0.604	Remote Similarity	NPD4820	Approved
0.604	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6038	Remote Similarity	NPD5208	Approved
0.6038	Remote Similarity	NPD5737	Approved
0.6038	Remote Similarity	NPD6672	Approved
0.6036	Remote Similarity	NPD5173	Approved
0.6036	Remote Similarity	NPD7902	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