NPASS Compound

Structure

CID85670 OpenBabel06191715422D 29 33 0 0 1 0 0 0 0 0999 V2000 -4.6472 -0.7431 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7626 -2.4727 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8337 1.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1860 1.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3958 -0.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4696 1.1045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5823 0.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9781 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6581 -1.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1860 0.9781 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.9836 -0.1045 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.4013 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3200 1.4781 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6036 1.6045 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6036 2.6045 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.7375 3.1045 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.1285 2.6045 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.2079 -0.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1285 1.6045 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5768 0.8090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9945 0.1045 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.3356 1.6045 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4696 3.1045 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7375 4.1045 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9945 3.1045 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.1215 -1.3849 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7375 1.1045 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9945 1.1045 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 8 2 0 0 0 0 2 9 1 0 0 0 0 4 13 1 0 0 0 0 5 11 1 0 0 0 0 5 12 1 0 0 0 0 6 22 1 0 0 0 0 7 20 1 0 0 0 0 7 21 1 0 0 0 0 8 10 1 0 0 0 0 8 11 1 0 0 0 0 9 12 2 0 0 0 0 9 18 1 0 0 0 0 10 4 1 1 0 0 0 10 13 1 0 0 0 0 11 20 1 1 0 0 0 12 21 1 0 0 0 0 13 20 1 1 0 0 0 14 6 1 1 0 0 0 14 15 1 0 0 0 0 14 27 1 0 0 0 0 15 16 1 0 0 0 0 15 23 1 6 0 0 0 16 17 1 0 0 0 0 16 24 1 1 0 0 0 17 19 1 0 0 0 0 17 25 1 6 0 0 0 18 26 2 0 0 0 0 18 28 1 0 0 0 0 19 27 1 0 0 0 0 19 29 1 1 0 0 0 20 3 1 1 0 0 0 21 28 1 0 0 0 0 21 29 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	408.18
Volume:	391.402
LogP:	1.096
LogD:	1.759
LogS:	-2.838
# Rotatable Bonds:	3
TPSA:	125.68
# H-Bond Aceptor:	8
# H-Bond Donor:	4
# Rings:	5
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.292
Synthetic Accessibility Score:	5.39
Fsp3:	0.762
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-5.938
MDCK Permeability:	7.410016405628994e-05
Pgp-inhibitor:	0.009
Pgp-substrate:	0.992
Human Intestinal Absorption (HIA):	0.055
20% Bioavailability (F20%):	0.012
30% Bioavailability (F30%):	0.971

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.139
Plasma Protein Binding (PPB):	55.8877067565918%
Volume Distribution (VD):	0.513
Pgp-substrate:	39.04694747924805%

ADMET: Metabolism

CYP1A2-inhibitor:	0.021
CYP1A2-substrate:	0.96
CYP2C19-inhibitor:	0.014
CYP2C19-substrate:	0.679
CYP2C9-inhibitor:	0.009
CYP2C9-substrate:	0.025
CYP2D6-inhibitor:	0.003
CYP2D6-substrate:	0.08
CYP3A4-inhibitor:	0.211
CYP3A4-substrate:	0.16

ADMET: Excretion

Clearance (CL):	3.175
Half-life (T1/2):	0.611

ADMET: Toxicity

hERG Blockers:	0.039
Human Hepatotoxicity (H-HT):	0.258
Drug-inuced Liver Injury (DILI):	0.238
AMES Toxicity:	0.346
Rat Oral Acute Toxicity:	0.628
Maximum Recommended Daily Dose:	0.105
Skin Sensitization:	0.064
Carcinogencity:	0.218
Eye Corrosion:	0.004
Eye Irritation:	0.013
Respiratory Toxicity:	0.97

Download Data

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

Natural Product: NPC85670

Natural Product ID:	NPC85670
*Common Name:**	Chlorajaposide
IUPAC Name:	n.a.
Synonyms:	Chlorajaposide
Standard InCHIKey:	DIHJSNVGGKCCRW-IFIACUTQSA-N
Standard InCHI:	InChI=1S/C21H28O8/c1-8-10-4-13(10)20(3)7-21(12(5-11(8)20)9(2)18(26)28-21)29-19-17(25)16(24)15(23)14(6-22)27-19/h10-11,13-17,19,22-25H,1,4-7H2,2-3H3/t10-,11+,13-,14-,15-,16+,17-,19+,20-,21-/m1/s1
SMILES:	C=C1[C@H]2C[C@H]2[C@]2(C)C[C@]3(C(=C(C)C(=O)O3)C[C@@H]12)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1669183
PubChem CID:	53316475
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 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[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]
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[551378]
NPT1997	Cell Line	OS-RC-2	Homo sapiens	IC50	<	10000.0	nM	PMID[551378]
NPT81	Cell Line	A549	Homo sapiens	IC50	<	10000.0	nM	PMID[551378]
NPT146	Cell Line	SK-OV-3	Homo sapiens	IC50	<	10000.0	nM	PMID[551378]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	<	10000.0	nM	PMID[551378]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	<	10000.0	nM	PMID[551378]
NPT515	Cell Line	SGC-7901	Homo sapiens	IC50	<	10000.0	nM	PMID[551378]
NPT114	Cell Line	LoVo	Homo sapiens	IC50	<	10000.0	nM	PMID[551378]

☑ 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 NPC85670 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	214
0.1-0.2	1445
0.2-0.3	4895
0.3-0.4	11444
0.4-0.5	9833
0.5-0.6	7053
0.6-0.7	5842
0.7-0.8	1862
0.8-0.85	96
0.85-0.9	10
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.97	High Similarity	NPC257853
0.9192	High Similarity	NPC198992
0.91	High Similarity	NPC121423
0.902	High Similarity	NPC239961
0.8835	High Similarity	NPC82251
0.8704	High Similarity	NPC106446
0.8624	High Similarity	NPC99620
0.8624	High Similarity	NPC193382
0.8624	High Similarity	NPC5311
0.8624	High Similarity	NPC199428
0.8624	High Similarity	NPC310341
0.8558	High Similarity	NPC161775
0.8545	High Similarity	NPC309034
0.8545	High Similarity	NPC203862
0.8545	High Similarity	NPC34390
0.8545	High Similarity	NPC474418
0.8545	High Similarity	NPC471351
0.8545	High Similarity	NPC84987
0.8545	High Similarity	NPC93883
0.8545	High Similarity	NPC471355
0.8545	High Similarity	NPC471354
0.8545	High Similarity	NPC244402
0.8545	High Similarity	NPC77319
0.8545	High Similarity	NPC99728
0.8545	High Similarity	NPC142066
0.8545	High Similarity	NPC50305
0.8545	High Similarity	NPC152615
0.8545	High Similarity	NPC158344
0.8545	High Similarity	NPC290693
0.8545	High Similarity	NPC471353
0.8545	High Similarity	NPC473852
0.8545	High Similarity	NPC27507
0.8545	High Similarity	NPC243196
0.8545	High Similarity	NPC157376
0.8545	High Similarity	NPC87250
0.8545	High Similarity	NPC196429
0.8532	High Similarity	NPC471633
0.8532	High Similarity	NPC31354
0.8532	High Similarity	NPC84949
0.8532	High Similarity	NPC69576
0.8529	High Similarity	NPC130792
0.8482	Intermediate Similarity	NPC470312
0.8468	Intermediate Similarity	NPC83287
0.8393	Intermediate Similarity	NPC469756
0.8393	Intermediate Similarity	NPC30483
0.8393	Intermediate Similarity	NPC29639
0.8393	Intermediate Similarity	NPC32177
0.8393	Intermediate Similarity	NPC292467
0.8393	Intermediate Similarity	NPC55532
0.8393	Intermediate Similarity	NPC44899
0.8393	Intermediate Similarity	NPC470897
0.8393	Intermediate Similarity	NPC329905
0.8393	Intermediate Similarity	NPC236973
0.8393	Intermediate Similarity	NPC5883
0.8393	Intermediate Similarity	NPC304260
0.8333	Intermediate Similarity	NPC115349
0.8319	Intermediate Similarity	NPC475629
0.8319	Intermediate Similarity	NPC72260
0.8319	Intermediate Similarity	NPC475136
0.8319	Intermediate Similarity	NPC474466
0.8319	Intermediate Similarity	NPC475556
0.8318	Intermediate Similarity	NPC177524
0.8318	Intermediate Similarity	NPC392
0.8318	Intermediate Similarity	NPC219900
0.8304	Intermediate Similarity	NPC218093
0.8288	Intermediate Similarity	NPC207637
0.8261	Intermediate Similarity	NPC27363
0.8246	Intermediate Similarity	NPC120390
0.8246	Intermediate Similarity	NPC475590
0.8246	Intermediate Similarity	NPC475419
0.8246	Intermediate Similarity	NPC474908
0.8246	Intermediate Similarity	NPC314535
0.8246	Intermediate Similarity	NPC231518
0.8246	Intermediate Similarity	NPC40749
0.8246	Intermediate Similarity	NPC173555
0.8246	Intermediate Similarity	NPC475219
0.8241	Intermediate Similarity	NPC206618
0.8235	Intermediate Similarity	NPC319861
0.823	Intermediate Similarity	NPC153085
0.823	Intermediate Similarity	NPC268326
0.823	Intermediate Similarity	NPC291820
0.823	Intermediate Similarity	NPC81222
0.819	Intermediate Similarity	NPC201191
0.819	Intermediate Similarity	NPC472815
0.8174	Intermediate Similarity	NPC74259
0.8174	Intermediate Similarity	NPC474423
0.8174	Intermediate Similarity	NPC193893
0.8174	Intermediate Similarity	NPC264336
0.8158	Intermediate Similarity	NPC107607
0.8155	Intermediate Similarity	NPC474182
0.8148	Intermediate Similarity	NPC38948
0.8137	Intermediate Similarity	NPC329435
0.8125	Intermediate Similarity	NPC106228
0.8125	Intermediate Similarity	NPC138372
0.812	Intermediate Similarity	NPC250556
0.812	Intermediate Similarity	NPC469750
0.8113	Intermediate Similarity	NPC281378
0.8108	Intermediate Similarity	NPC264153
0.8103	Intermediate Similarity	NPC117445
0.8103	Intermediate Similarity	NPC308262
0.8103	Intermediate Similarity	NPC208193
0.807	Intermediate Similarity	NPC9674
0.807	Intermediate Similarity	NPC19028
0.8056	Intermediate Similarity	NPC472820
0.8053	Intermediate Similarity	NPC474483
0.8051	Intermediate Similarity	NPC329784
0.8051	Intermediate Similarity	NPC240070
0.8051	Intermediate Similarity	NPC179412
0.8051	Intermediate Similarity	NPC469757
0.8051	Intermediate Similarity	NPC146456
0.8051	Intermediate Similarity	NPC117702
0.8051	Intermediate Similarity	NPC471357
0.8051	Intermediate Similarity	NPC471356
0.8036	Intermediate Similarity	NPC178289
0.8	Intermediate Similarity	NPC135369
0.7983	Intermediate Similarity	NPC311534
0.7982	Intermediate Similarity	NPC291564
0.7982	Intermediate Similarity	NPC128795
0.7982	Intermediate Similarity	NPC48548
0.7982	Intermediate Similarity	NPC473828
0.7982	Intermediate Similarity	NPC239293
0.7982	Intermediate Similarity	NPC135015
0.7982	Intermediate Similarity	NPC181994
0.7982	Intermediate Similarity	NPC217921
0.7982	Intermediate Similarity	NPC473617
0.7981	Intermediate Similarity	NPC205143
0.7963	Intermediate Similarity	NPC472818
0.7963	Intermediate Similarity	NPC218158
0.7963	Intermediate Similarity	NPC473199
0.7963	Intermediate Similarity	NPC165405
0.7944	Intermediate Similarity	NPC120009
0.7944	Intermediate Similarity	NPC472821
0.7941	Intermediate Similarity	NPC472641
0.7941	Intermediate Similarity	NPC472640
0.7931	Intermediate Similarity	NPC233500
0.7928	Intermediate Similarity	NPC470076
0.7925	Intermediate Similarity	NPC477717
0.7925	Intermediate Similarity	NPC11974
0.7917	Intermediate Similarity	NPC469755
0.7917	Intermediate Similarity	NPC471361
0.7917	Intermediate Similarity	NPC469754
0.7917	Intermediate Similarity	NPC180079
0.7917	Intermediate Similarity	NPC284406
0.7917	Intermediate Similarity	NPC219085
0.7917	Intermediate Similarity	NPC89514
0.7917	Intermediate Similarity	NPC17896
0.7917	Intermediate Similarity	NPC10823
0.7917	Intermediate Similarity	NPC469753
0.7917	Intermediate Similarity	NPC276838
0.7917	Intermediate Similarity	NPC197707
0.7917	Intermediate Similarity	NPC9499
0.7917	Intermediate Similarity	NPC232785
0.7917	Intermediate Similarity	NPC86159
0.7917	Intermediate Similarity	NPC6108
0.7917	Intermediate Similarity	NPC469752
0.7917	Intermediate Similarity	NPC140092
0.7917	Intermediate Similarity	NPC188234
0.7917	Intermediate Similarity	NPC471360
0.7917	Intermediate Similarity	NPC471352
0.7917	Intermediate Similarity	NPC329986
0.7917	Intermediate Similarity	NPC70542
0.7917	Intermediate Similarity	NPC125077
0.7917	Intermediate Similarity	NPC469751
0.7917	Intermediate Similarity	NPC471359
0.7917	Intermediate Similarity	NPC251866
0.7917	Intermediate Similarity	NPC471358
0.7913	Intermediate Similarity	NPC477071
0.7913	Intermediate Similarity	NPC232258
0.7913	Intermediate Similarity	NPC219656
0.7909	Intermediate Similarity	NPC40728
0.7909	Intermediate Similarity	NPC316974
0.7909	Intermediate Similarity	NPC472901
0.7909	Intermediate Similarity	NPC250089
0.7909	Intermediate Similarity	NPC14630
0.7909	Intermediate Similarity	NPC475030
0.7909	Intermediate Similarity	NPC157530
0.789	Intermediate Similarity	NPC88013
0.789	Intermediate Similarity	NPC472390
0.789	Intermediate Similarity	NPC125423
0.789	Intermediate Similarity	NPC234160
0.7885	Intermediate Similarity	NPC165632
0.7881	Intermediate Similarity	NPC471090
0.787	Intermediate Similarity	NPC472819
0.787	Intermediate Similarity	NPC93352
0.787	Intermediate Similarity	NPC85593
0.787	Intermediate Similarity	NPC31430
0.787	Intermediate Similarity	NPC471937
0.7863	Intermediate Similarity	NPC196130
0.7863	Intermediate Similarity	NPC27335
0.7863	Intermediate Similarity	NPC471082
0.7857	Intermediate Similarity	NPC328074
0.7857	Intermediate Similarity	NPC321272
0.7857	Intermediate Similarity	NPC317460
0.7857	Intermediate Similarity	NPC470025
0.7851	Intermediate Similarity	NPC159338
0.7851	Intermediate Similarity	NPC253456
0.7851	Intermediate Similarity	NPC16569
0.785	Intermediate Similarity	NPC470972
0.785	Intermediate Similarity	NPC471914
0.785	Intermediate Similarity	NPC472552

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 NPC85670 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	174
0.1-0.2	1700
0.2-0.3	4065
0.3-0.4	2174
0.4-0.5	585
0.5-0.6	275
0.6-0.7	152
0.7-0.8	22
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8468	Intermediate Similarity	NPD7327	Approved
0.8468	Intermediate Similarity	NPD7328	Approved
0.8393	Intermediate Similarity	NPD7516	Approved
0.8319	Intermediate Similarity	NPD8377	Approved
0.8319	Intermediate Similarity	NPD8294	Approved
0.8318	Intermediate Similarity	NPD6686	Approved
0.8246	Intermediate Similarity	NPD8033	Approved
0.8246	Intermediate Similarity	NPD8335	Approved
0.8246	Intermediate Similarity	NPD8379	Approved
0.8246	Intermediate Similarity	NPD8380	Approved
0.8246	Intermediate Similarity	NPD8296	Approved
0.8246	Intermediate Similarity	NPD8378	Approved
0.812	Intermediate Similarity	NPD7507	Approved
0.7917	Intermediate Similarity	NPD7319	Approved
0.7778	Intermediate Similarity	NPD7503	Approved
0.7478	Intermediate Similarity	NPD8133	Approved
0.7411	Intermediate Similarity	NPD6412	Phase 2
0.7407	Intermediate Similarity	NPD7638	Approved
0.7339	Intermediate Similarity	NPD7640	Approved
0.7339	Intermediate Similarity	NPD7639	Approved
0.7281	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD4225	Approved
0.7238	Intermediate Similarity	NPD46	Approved
0.7238	Intermediate Similarity	NPD6698	Approved
0.7117	Intermediate Similarity	NPD5344	Discontinued
0.7075	Intermediate Similarity	NPD7838	Discovery
0.7069	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.699	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6983	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD8293	Discontinued
0.6903	Remote Similarity	NPD7632	Discontinued
0.686	Remote Similarity	NPD7115	Discovery
0.6855	Remote Similarity	NPD6370	Approved
0.685	Remote Similarity	NPD7736	Approved
0.681	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.68	Remote Similarity	NPD8328	Phase 3
0.678	Remote Similarity	NPD6371	Approved
0.6746	Remote Similarity	NPD7492	Approved
0.6739	Remote Similarity	NPD7625	Phase 1
0.6726	Remote Similarity	NPD6648	Approved
0.6721	Remote Similarity	NPD6009	Approved
0.6697	Remote Similarity	NPD7637	Suspended
0.6694	Remote Similarity	NPD6319	Approved
0.6694	Remote Similarity	NPD6054	Approved
0.6694	Remote Similarity	NPD6059	Approved
0.6693	Remote Similarity	NPD6616	Approved
0.6667	Remote Similarity	NPD6882	Approved
0.6641	Remote Similarity	NPD7078	Approved
0.664	Remote Similarity	NPD6015	Approved
0.664	Remote Similarity	NPD8517	Approved
0.664	Remote Similarity	NPD8516	Approved
0.664	Remote Similarity	NPD8513	Phase 3
0.664	Remote Similarity	NPD8515	Approved
0.664	Remote Similarity	NPD6016	Approved
0.6636	Remote Similarity	NPD7524	Approved
0.6612	Remote Similarity	NPD4632	Approved
0.6587	Remote Similarity	NPD5988	Approved
0.6585	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6583	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6535	Remote Similarity	NPD6067	Discontinued
0.6529	Remote Similarity	NPD6053	Discontinued
0.6529	Remote Similarity	NPD8297	Approved
0.6525	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6509	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6486	Remote Similarity	NPD8171	Discontinued
0.6476	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD7320	Approved
0.6449	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6441	Remote Similarity	NPD6675	Approved
0.6441	Remote Similarity	NPD6008	Approved
0.6441	Remote Similarity	NPD5739	Approved
0.6441	Remote Similarity	NPD6402	Approved
0.6441	Remote Similarity	NPD7128	Approved
0.6417	Remote Similarity	NPD6373	Approved
0.6417	Remote Similarity	NPD6372	Approved
0.6415	Remote Similarity	NPD6695	Phase 3
0.6406	Remote Similarity	NPD7604	Phase 2
0.6387	Remote Similarity	NPD5701	Approved
0.6387	Remote Similarity	NPD5697	Approved
0.6356	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6339	Remote Similarity	NPD6399	Phase 3
0.6333	Remote Similarity	NPD6899	Approved
0.6333	Remote Similarity	NPD6881	Approved
0.6311	Remote Similarity	NPD6650	Approved
0.6311	Remote Similarity	NPD6649	Approved
0.6281	Remote Similarity	NPD6014	Approved
0.6281	Remote Similarity	NPD6013	Approved
0.6281	Remote Similarity	NPD6012	Approved
0.6279	Remote Similarity	NPD7829	Approved
0.6279	Remote Similarity	NPD7830	Approved
0.6261	Remote Similarity	NPD6083	Phase 2
0.6261	Remote Similarity	NPD6084	Phase 2
0.625	Remote Similarity	NPD5983	Phase 2
0.6239	Remote Similarity	NPD4249	Approved
0.623	Remote Similarity	NPD7102	Approved
0.623	Remote Similarity	NPD6883	Approved
0.623	Remote Similarity	NPD7290	Approved
0.6228	Remote Similarity	NPD5695	Phase 3
0.6226	Remote Similarity	NPD6902	Approved
0.6216	Remote Similarity	NPD6051	Approved
0.6212	Remote Similarity	NPD6033	Approved
0.6198	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6198	Remote Similarity	NPD6011	Approved
0.619	Remote Similarity	NPD6929	Approved
0.6182	Remote Similarity	NPD4251	Approved
0.6182	Remote Similarity	NPD7750	Discontinued
0.6182	Remote Similarity	NPD4250	Approved
0.6179	Remote Similarity	NPD8130	Phase 1
0.6179	Remote Similarity	NPD6869	Approved
0.6179	Remote Similarity	NPD6847	Approved
0.6179	Remote Similarity	NPD6617	Approved
0.6136	Remote Similarity	NPD8074	Phase 3
0.6132	Remote Similarity	NPD6930	Phase 2
0.6132	Remote Similarity	NPD6931	Approved
0.6132	Remote Similarity	NPD7525	Registered
0.6121	Remote Similarity	NPD4755	Approved
0.6106	Remote Similarity	NPD8034	Phase 2
0.6106	Remote Similarity	NPD8035	Phase 2
0.6106	Remote Similarity	NPD7983	Approved
0.6098	Remote Similarity	NPD4634	Approved
0.6091	Remote Similarity	NPD3618	Phase 1
0.6087	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6087	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6071	Remote Similarity	NPD1695	Approved
0.6071	Remote Similarity	NPD5328	Approved
0.6068	Remote Similarity	NPD5696	Approved
0.6061	Remote Similarity	NPD6336	Discontinued
0.6058	Remote Similarity	NPD6933	Approved
0.6053	Remote Similarity	NPD5778	Approved
0.6053	Remote Similarity	NPD5779	Approved
0.6053	Remote Similarity	NPD4202	Approved
0.605	Remote Similarity	NPD5211	Phase 2
0.6048	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6031	Remote Similarity	NPD7642	Approved
0.6029	Remote Similarity	NPD8449	Approved
0.6029	Remote Similarity	NPD8338	Approved
0.6018	Remote Similarity	NPD3168	Discontinued
0.6018	Remote Similarity	NPD5785	Approved
0.6017	Remote Similarity	NPD4700	Approved
0.6017	Remote Similarity	NPD5285	Approved
0.6017	Remote Similarity	NPD4696	Approved
0.6017	Remote Similarity	NPD5286	Approved
0.6	Remote Similarity	NPD1694	Approved
0.6	Remote Similarity	NPD7748	Approved
0.6	Remote Similarity	NPD5776	Phase 2
0.6	Remote Similarity	NPD6925	Approved
0.6	Remote Similarity	NPD5282	Discontinued
0.6	Remote Similarity	NPD5956	Approved
0.6	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.5985	Remote Similarity	NPD8450	Suspended
0.5984	Remote Similarity	NPD6274	Approved
0.5983	Remote Similarity	NPD7902	Approved
0.5982	Remote Similarity	NPD6903	Approved
0.5982	Remote Similarity	NPD5737	Approved
0.5982	Remote Similarity	NPD6672	Approved
0.5981	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.5981	Remote Similarity	NPD6928	Phase 2
0.5981	Remote Similarity	NPD7514	Phase 3
0.5971	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.597	Remote Similarity	NPD8336	Approved
0.597	Remote Similarity	NPD8337	Approved
0.5966	Remote Similarity	NPD4159	Approved
0.5965	Remote Similarity	NPD5693	Phase 1
0.5965	Remote Similarity	NPD6411	Approved
0.5965	Remote Similarity	NPD6079	Approved
0.5965	Remote Similarity	NPD7087	Discontinued
0.5965	Remote Similarity	NPD7515	Phase 2
0.5963	Remote Similarity	NPD5362	Discontinued
0.5963	Remote Similarity	NPD3669	Approved
0.5963	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.5956	Remote Similarity	NPD7260	Phase 2
0.5954	Remote Similarity	NPD8080	Discontinued
0.595	Remote Similarity	NPD5141	Approved
0.5946	Remote Similarity	NPD7334	Approved
0.5946	Remote Similarity	NPD6409	Approved
0.5946	Remote Similarity	NPD5330	Approved
0.5946	Remote Similarity	NPD6684	Approved
0.5946	Remote Similarity	NPD5279	Phase 3
0.5946	Remote Similarity	NPD7521	Approved
0.5946	Remote Similarity	NPD7146	Approved
0.5943	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.5943	Remote Similarity	NPD7145	Approved
0.594	Remote Similarity	NPD8451	Approved
0.5938	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.5929	Remote Similarity	NPD4753	Phase 2
0.5917	Remote Similarity	NPD5226	Approved
0.5917	Remote Similarity	NPD4633	Approved
0.5917	Remote Similarity	NPD5224	Approved
0.5917	Remote Similarity	NPD5225	Approved
0.5912	Remote Similarity	NPD6845	Suspended
0.5909	Remote Similarity	NPD3666	Approved
0.5909	Remote Similarity	NPD4786	Approved
0.5909	Remote Similarity	NPD3665	Phase 1
0.5909	Remote Similarity	NPD3133	Approved
0.5902	Remote Similarity	NPD4768	Approved
0.5902	Remote Similarity	NPD6640	Phase 3
0.5902	Remote Similarity	NPD4767	Approved
0.5897	Remote Similarity	NPD4697	Phase 3
0.5897	Remote Similarity	NPD5222	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