NPASS Compound

Structure

CID121816 OpenBabel06191715472D 29 32 0 0 1 0 0 0 0 0999 V2000 2.7636 -4.0583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1595 -1.1879 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6932 0.0857 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8025 -5.4442 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0024 -6.0440 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6913 -3.1236 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6028 -3.9396 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6831 -4.4514 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2085 -0.8789 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4443 -2.4657 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.3995 -1.4667 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.2335 -2.0645 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6265 -1.1449 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.2375 -1.9748 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5904 -0.8789 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0150 -0.9999 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.4832 -3.8515 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8995 0.0722 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8734 -0.4870 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7073 -2.9451 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.4118 -4.5274 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0 3.1218 -7.0369 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.4205 -2.7279 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.4028 -4.2446 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.4872 0.8812 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7938 -3.3518 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3639 -2.8587 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.8995 0.0722 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 1 8 1 0 0 0 0 2 9 2 0 0 0 0 4 5 1 0 0 0 0 4 8 2 0 0 0 0 5 22 1 0 0 0 0 6 10 1 0 0 0 0 6 20 1 0 0 0 0 7 20 1 0 0 0 0 7 21 1 0 0 0 0 8 17 1 0 0 0 0 9 18 1 0 0 0 0 10 11 1 0 0 0 0 10 27 1 6 0 0 0 11 9 1 6 0 0 0 11 15 1 0 0 0 0 12 13 1 0 0 0 0 12 14 1 0 0 0 0 12 20 1 6 0 0 0 13 15 1 0 0 0 0 13 19 1 6 0 0 0 14 16 1 0 0 0 0 14 23 1 6 0 0 0 15 28 1 1 0 0 0 16 19 1 6 0 0 0 16 29 1 0 0 0 0 17 24 2 0 0 0 0 17 27 1 0 0 0 0 18 25 2 0 0 0 0 18 28 1 0 0 0 0 19 3 1 6 0 0 0 19 29 1 0 0 0 0 20 26 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	428.12
Volume:	395.237
LogP:	0.61
LogD:	0.65
LogS:	-2.677
# Rotatable Bonds:	6
TPSA:	122.66
# H-Bond Aceptor:	8
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.211
Synthetic Accessibility Score:	5.533
Fsp3:	0.75
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	4
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.292
MDCK Permeability:	0.00011307669046800584
Pgp-inhibitor:	0.001
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.677
20% Bioavailability (F20%):	0.905
30% Bioavailability (F30%):	0.989

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.929
Plasma Protein Binding (PPB):	44.674949645996094%
Volume Distribution (VD):	0.644
Pgp-substrate:	64.21556091308594%

ADMET: Metabolism

CYP1A2-inhibitor:	0.03
CYP1A2-substrate:	0.273
CYP2C19-inhibitor:	0.02
CYP2C19-substrate:	0.153
CYP2C9-inhibitor:	0.007
CYP2C9-substrate:	0.033
CYP2D6-inhibitor:	0.007
CYP2D6-substrate:	0.087
CYP3A4-inhibitor:	0.192
CYP3A4-substrate:	0.243

ADMET: Excretion

Clearance (CL):	8.477
Half-life (T1/2):	0.735

ADMET: Toxicity

hERG Blockers:	0.063
Human Hepatotoxicity (H-HT):	0.703
Drug-inuced Liver Injury (DILI):	0.554
AMES Toxicity:	0.065
Rat Oral Acute Toxicity:	0.558
Maximum Recommended Daily Dose:	0.045
Skin Sensitization:	0.771
Carcinogencity:	0.216
Eye Corrosion:	0.713
Eye Irritation:	0.106
Respiratory Toxicity:	0.978

Download Data

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

Natural Product: NPC121816

Natural Product ID:	NPC121816
*Common Name:**	Eupachinilide E
IUPAC Name:	n.a.
Synonyms:	eupachinilide E
Standard InCHIKey:	JNLCQVGOEVZPLZ-GQEGKNDZSA-N
Standard InCHI:	InChI=1S/C20H25ClO8/c1-8(4-5-22)17(24)27-10-6-20(26,7-21)12-13(19(3)16(29-19)14(12)23)15-11(10)9(2)18(25)28-15/h4,10-16,22-23,26H,2,5-7H2,1,3H3/b8-4+/t10-,11-,12+,13+,14+,15+,16-,19+,20+/m1/s1
SMILES:	OC/C=C(/C(=O)O[C@@H]1C[C@](O)(CCl)[C@H]2[C@@H]([C@@H]3[C@@H]1C(=C)C(=O)O3)[C@]1([C@@H]([C@H]2O)O1)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL462890
PubChem CID:	21578012
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:0001770] Guaianolides 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
NPO24212	Eupatorium chinense	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15104494]
NPO851	Eupatorium lindleyanum	Species	Asteraceae	Eukaryota	Whole plant	Songyang County, Zhejiang Province, China	n.a.	PMID[15387644]
NPO24212	Eupatorium chinense	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19318257]
NPO24212	Eupatorium chinense	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[29280632]
NPO851	Eupatorium lindleyanum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24212	Eupatorium chinense	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24212	Eupatorium chinense	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO851	Eupatorium lindleyanum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO851	Eupatorium lindleyanum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO851	Eupatorium lindleyanum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO851	Eupatorium lindleyanum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24212	Eupatorium chinense	Species	Asteraceae	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	2

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT116	Cell Line	HL-60	Homo sapiens	IC50	=	1.3	ug.mL-1	PMID[548564]
NPT181	Cell Line	Bel-7402	Homo sapiens	IC50	=	18.0	ug.mL-1	PMID[548564]

☑ 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 NPC121816 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	299
0.1-0.2	1945
0.2-0.3	6716
0.3-0.4	15543
0.4-0.5	10194
0.5-0.6	5745
0.6-0.7	1937
0.7-0.8	278
0.8-0.85	23
0.85-0.9	12
0.9-0.95	1
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9905	High Similarity	NPC273242
0.972	High Similarity	NPC170692
0.972	High Similarity	NPC255450
0.8909	High Similarity	NPC189338
0.8909	High Similarity	NPC95290
0.8909	High Similarity	NPC35069
0.8909	High Similarity	NPC258711
0.8889	High Similarity	NPC68248
0.8879	High Similarity	NPC54737
0.8807	High Similarity	NPC59489
0.8807	High Similarity	NPC139838
0.8807	High Similarity	NPC115352
0.8704	High Similarity	NPC166115
0.8411	Intermediate Similarity	NPC471381
0.8411	Intermediate Similarity	NPC186861
0.8381	Intermediate Similarity	NPC472873
0.8364	Intermediate Similarity	NPC243998
0.8364	Intermediate Similarity	NPC223450
0.8333	Intermediate Similarity	NPC150923
0.8318	Intermediate Similarity	NPC45125
0.8224	Intermediate Similarity	NPC471150
0.819	Intermediate Similarity	NPC258216
0.8148	Intermediate Similarity	NPC221615
0.8131	Intermediate Similarity	NPC24956
0.8131	Intermediate Similarity	NPC18019
0.8095	Intermediate Similarity	NPC155215
0.8095	Intermediate Similarity	NPC475925
0.8091	Intermediate Similarity	NPC86077
0.8056	Intermediate Similarity	NPC161493
0.8056	Intermediate Similarity	NPC181151
0.8037	Intermediate Similarity	NPC476053
0.8036	Intermediate Similarity	NPC44004
0.8018	Intermediate Similarity	NPC124881
0.8	Intermediate Similarity	NPC216284
0.7963	Intermediate Similarity	NPC213078
0.7905	Intermediate Similarity	NPC472872
0.7905	Intermediate Similarity	NPC215556
0.789	Intermediate Similarity	NPC474313
0.787	Intermediate Similarity	NPC52044
0.787	Intermediate Similarity	NPC67584
0.787	Intermediate Similarity	NPC213698
0.787	Intermediate Similarity	NPC170120
0.781	Intermediate Similarity	NPC79549
0.781	Intermediate Similarity	NPC217983
0.781	Intermediate Similarity	NPC207114
0.7807	Intermediate Similarity	NPC26617
0.7798	Intermediate Similarity	NPC279621
0.7778	Intermediate Similarity	NPC323008
0.7778	Intermediate Similarity	NPC198853
0.7778	Intermediate Similarity	NPC127019
0.7778	Intermediate Similarity	NPC470010
0.7778	Intermediate Similarity	NPC262133
0.7778	Intermediate Similarity	NPC477131
0.7778	Intermediate Similarity	NPC470013
0.7757	Intermediate Similarity	NPC133888
0.7757	Intermediate Similarity	NPC57304
0.7757	Intermediate Similarity	NPC63193
0.7757	Intermediate Similarity	NPC29821
0.7757	Intermediate Similarity	NPC184063
0.7757	Intermediate Similarity	NPC171360
0.7757	Intermediate Similarity	NPC35959
0.7757	Intermediate Similarity	NPC293001
0.7748	Intermediate Similarity	NPC70865
0.7742	Intermediate Similarity	NPC470973
0.7739	Intermediate Similarity	NPC117604
0.7727	Intermediate Similarity	NPC311904
0.7706	Intermediate Similarity	NPC14961
0.7706	Intermediate Similarity	NPC304886
0.7706	Intermediate Similarity	NPC220221
0.7706	Intermediate Similarity	NPC270013
0.7686	Intermediate Similarity	NPC477092
0.7685	Intermediate Similarity	NPC472874
0.7679	Intermediate Similarity	NPC171759
0.7664	Intermediate Similarity	NPC19087
0.7664	Intermediate Similarity	NPC297474
0.7664	Intermediate Similarity	NPC35809
0.7664	Intermediate Similarity	NPC54065
0.7658	Intermediate Similarity	NPC474213
0.7636	Intermediate Similarity	NPC476315
0.7636	Intermediate Similarity	NPC98165
0.7632	Intermediate Similarity	NPC100487
0.7619	Intermediate Similarity	NPC187661
0.7619	Intermediate Similarity	NPC64153
0.7615	Intermediate Similarity	NPC81386
0.7615	Intermediate Similarity	NPC474247
0.7615	Intermediate Similarity	NPC474035
0.7607	Intermediate Similarity	NPC257240
0.7607	Intermediate Similarity	NPC50223
0.7603	Intermediate Similarity	NPC475401
0.7593	Intermediate Similarity	NPC131209
0.7593	Intermediate Similarity	NPC133698
0.757	Intermediate Similarity	NPC155935
0.757	Intermediate Similarity	NPC38392
0.7568	Intermediate Similarity	NPC170143
0.7568	Intermediate Similarity	NPC108475
0.7568	Intermediate Similarity	NPC213947
0.7559	Intermediate Similarity	NPC475371
0.7545	Intermediate Similarity	NPC163228
0.7545	Intermediate Similarity	NPC36954
0.7524	Intermediate Similarity	NPC204105
0.7524	Intermediate Similarity	NPC300082
0.7524	Intermediate Similarity	NPC284534
0.7523	Intermediate Similarity	NPC212486
0.7523	Intermediate Similarity	NPC475788
0.7523	Intermediate Similarity	NPC125674
0.7523	Intermediate Similarity	NPC228451
0.7523	Intermediate Similarity	NPC475912
0.7523	Intermediate Similarity	NPC475838
0.7521	Intermediate Similarity	NPC475305
0.7521	Intermediate Similarity	NPC477102
0.75	Intermediate Similarity	NPC37607
0.75	Intermediate Similarity	NPC49833
0.75	Intermediate Similarity	NPC305044
0.75	Intermediate Similarity	NPC187268
0.75	Intermediate Similarity	NPC265290
0.75	Intermediate Similarity	NPC473326
0.75	Intermediate Similarity	NPC301969
0.75	Intermediate Similarity	NPC249171
0.7478	Intermediate Similarity	NPC474741
0.7477	Intermediate Similarity	NPC230800
0.7477	Intermediate Similarity	NPC471149
0.7458	Intermediate Similarity	NPC477103
0.7458	Intermediate Similarity	NPC41551
0.7458	Intermediate Similarity	NPC193741
0.7456	Intermediate Similarity	NPC80144
0.7434	Intermediate Similarity	NPC288876
0.7429	Intermediate Similarity	NPC224386
0.7429	Intermediate Similarity	NPC194859
0.7417	Intermediate Similarity	NPC46269
0.7417	Intermediate Similarity	NPC106395
0.7414	Intermediate Similarity	NPC470980
0.7411	Intermediate Similarity	NPC304445
0.7411	Intermediate Similarity	NPC236580
0.7407	Intermediate Similarity	NPC283409
0.7407	Intermediate Similarity	NPC4986
0.7391	Intermediate Similarity	NPC475945
0.7391	Intermediate Similarity	NPC475871
0.7391	Intermediate Similarity	NPC473148
0.7387	Intermediate Similarity	NPC471141
0.7387	Intermediate Similarity	NPC224689
0.7383	Intermediate Similarity	NPC270270
0.7383	Intermediate Similarity	NPC24728
0.7373	Intermediate Similarity	NPC208307
0.7368	Intermediate Similarity	NPC67296
0.7364	Intermediate Similarity	NPC81419
0.7364	Intermediate Similarity	NPC476300
0.7364	Intermediate Similarity	NPC179746
0.7355	Intermediate Similarity	NPC138303
0.7355	Intermediate Similarity	NPC133677
0.7355	Intermediate Similarity	NPC67290
0.7339	Intermediate Similarity	NPC143755
0.7333	Intermediate Similarity	NPC475851
0.7333	Intermediate Similarity	NPC245665
0.7333	Intermediate Similarity	NPC111409
0.7333	Intermediate Similarity	NPC76550
0.7333	Intermediate Similarity	NPC128246
0.7333	Intermediate Similarity	NPC123855
0.7333	Intermediate Similarity	NPC138757
0.7333	Intermediate Similarity	NPC475924
0.7328	Intermediate Similarity	NPC203659
0.7321	Intermediate Similarity	NPC476009
0.7321	Intermediate Similarity	NPC142529
0.7321	Intermediate Similarity	NPC126156
0.7321	Intermediate Similarity	NPC474297
0.7321	Intermediate Similarity	NPC91771
0.7315	Intermediate Similarity	NPC91248
0.7315	Intermediate Similarity	NPC224652
0.7315	Intermediate Similarity	NPC178875
0.7304	Intermediate Similarity	NPC474747
0.7302	Intermediate Similarity	NPC129992
0.7297	Intermediate Similarity	NPC57405
0.7297	Intermediate Similarity	NPC303942
0.729	Intermediate Similarity	NPC470242
0.729	Intermediate Similarity	NPC304558
0.729	Intermediate Similarity	NPC56593
0.7288	Intermediate Similarity	NPC308191
0.7273	Intermediate Similarity	NPC30515
0.7273	Intermediate Similarity	NPC208886
0.7273	Intermediate Similarity	NPC101965
0.7273	Intermediate Similarity	NPC184463
0.7273	Intermediate Similarity	NPC101400
0.7273	Intermediate Similarity	NPC12172
0.7265	Intermediate Similarity	NPC179891
0.7257	Intermediate Similarity	NPC261372
0.7257	Intermediate Similarity	NPC477949
0.7257	Intermediate Similarity	NPC58267
0.7257	Intermediate Similarity	NPC263674
0.725	Intermediate Similarity	NPC474750
0.725	Intermediate Similarity	NPC475495
0.725	Intermediate Similarity	NPC287311
0.7248	Intermediate Similarity	NPC92974
0.7241	Intermediate Similarity	NPC474783
0.7241	Intermediate Similarity	NPC110989
0.7241	Intermediate Similarity	NPC260809
0.7238	Intermediate Similarity	NPC246076
0.7236	Intermediate Similarity	NPC471146
0.7222	Intermediate Similarity	NPC186148
0.7222	Intermediate Similarity	NPC190753
0.7222	Intermediate Similarity	NPC118601
0.7217	Intermediate Similarity	NPC201718

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 NPC121816 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	285
0.1-0.2	2544
0.2-0.3	4003
0.3-0.4	1695
0.4-0.5	414
0.5-0.6	181
0.6-0.7	24
0.7-0.8	4
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
0.7807	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7607	Intermediate Similarity	NPD6371	Approved
0.7407	Intermediate Similarity	NPD1695	Approved
0.7182	Intermediate Similarity	NPD6698	Approved
0.7182	Intermediate Similarity	NPD46	Approved
0.6911	Remote Similarity	NPD6053	Discontinued
0.6875	Remote Similarity	NPD7838	Discovery
0.6818	Remote Similarity	NPD4249	Approved
0.6757	Remote Similarity	NPD4251	Approved
0.6757	Remote Similarity	NPD4250	Approved
0.6638	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6579	Remote Similarity	NPD5785	Approved
0.6577	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD7115	Discovery
0.6545	Remote Similarity	NPD5362	Discontinued
0.65	Remote Similarity	NPD5344	Discontinued
0.6489	Remote Similarity	NPD5983	Phase 2
0.6471	Remote Similarity	NPD5956	Approved
0.6457	Remote Similarity	NPD4632	Approved
0.6452	Remote Similarity	NPD6686	Approved
0.6441	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD5363	Approved
0.6429	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6422	Remote Similarity	NPD4822	Approved
0.6422	Remote Similarity	NPD4820	Approved
0.6422	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6422	Remote Similarity	NPD4821	Approved
0.6422	Remote Similarity	NPD4819	Approved
0.6418	Remote Similarity	NPD7507	Approved
0.6379	Remote Similarity	NPD7983	Approved
0.6333	Remote Similarity	NPD4225	Approved
0.6333	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6324	Remote Similarity	NPD6033	Approved
0.6296	Remote Similarity	NPD6336	Discontinued
0.629	Remote Similarity	NPD6008	Approved
0.6288	Remote Similarity	NPD6319	Approved
0.6277	Remote Similarity	NPD7319	Approved
0.625	Remote Similarity	NPD7154	Phase 3
0.6241	Remote Similarity	NPD8033	Approved
0.6239	Remote Similarity	NPD4271	Approved
0.6239	Remote Similarity	NPD4268	Approved
0.6212	Remote Similarity	NPD4522	Approved
0.6212	Remote Similarity	NPD7100	Approved
0.6183	Remote Similarity	NPD6009	Approved
0.6161	Remote Similarity	NPD4270	Approved
0.6161	Remote Similarity	NPD6435	Approved
0.6161	Remote Similarity	NPD4269	Approved
0.6148	Remote Similarity	NPD7639	Approved
0.6148	Remote Similarity	NPD6648	Approved
0.6148	Remote Similarity	NPD7640	Approved
0.6142	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6136	Remote Similarity	NPD7327	Approved
0.6136	Remote Similarity	NPD6314	Approved
0.6136	Remote Similarity	NPD6313	Approved
0.6136	Remote Similarity	NPD6335	Approved
0.6136	Remote Similarity	NPD7328	Approved
0.6106	Remote Similarity	NPD5332	Approved
0.6106	Remote Similarity	NPD5331	Approved
0.6103	Remote Similarity	NPD7492	Approved
0.6094	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.609	Remote Similarity	NPD7516	Approved
0.609	Remote Similarity	NPD7101	Approved
0.6087	Remote Similarity	NPD5786	Approved
0.6071	Remote Similarity	NPD4790	Discontinued
0.6071	Remote Similarity	NPD5369	Approved
0.6066	Remote Similarity	NPD7638	Approved
0.6058	Remote Similarity	NPD6616	Approved
0.6045	Remote Similarity	NPD8377	Approved
0.6045	Remote Similarity	NPD6054	Approved
0.6045	Remote Similarity	NPD8294	Approved
0.6014	Remote Similarity	NPD7078	Approved
0.6	Remote Similarity	NPD8296	Approved
0.6	Remote Similarity	NPD6015	Approved
0.6	Remote Similarity	NPD8378	Approved
0.6	Remote Similarity	NPD8516	Approved
0.6	Remote Similarity	NPD6016	Approved
0.6	Remote Similarity	NPD8515	Approved
0.6	Remote Similarity	NPD8379	Approved
0.6	Remote Similarity	NPD8335	Approved
0.6	Remote Similarity	NPD7503	Approved
0.6	Remote Similarity	NPD5282	Discontinued
0.6	Remote Similarity	NPD8517	Approved
0.6	Remote Similarity	NPD8380	Approved
0.6	Remote Similarity	NPD8297	Approved
0.6	Remote Similarity	NPD8513	Phase 3
0.5984	Remote Similarity	NPD6412	Phase 2
0.5982	Remote Similarity	NPD5368	Approved
0.5982	Remote Similarity	NPD4252	Approved
0.5971	Remote Similarity	NPD7736	Approved
0.5956	Remote Similarity	NPD5988	Approved
0.5956	Remote Similarity	NPD6370	Approved
0.5954	Remote Similarity	NPD8133	Approved
0.5942	Remote Similarity	NPD8273	Phase 1
0.5926	Remote Similarity	NPD6059	Approved
0.5923	Remote Similarity	NPD6649	Approved
0.5923	Remote Similarity	NPD5215	Approved
0.5923	Remote Similarity	NPD6650	Approved
0.5899	Remote Similarity	NPD8293	Discontinued
0.5891	Remote Similarity	NPD6373	Approved
0.5891	Remote Similarity	NPD6372	Approved
0.5859	Remote Similarity	NPD5697	Approved
0.5859	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.5854	Remote Similarity	NPD6084	Phase 2
0.5854	Remote Similarity	NPD6083	Phase 2
0.5846	Remote Similarity	NPD5169	Approved
0.5827	Remote Similarity	NPD4057	Clinical (unspecified phase)
0.5827	Remote Similarity	NPD4056	Clinical (unspecified phase)
0.582	Remote Similarity	NPD5695	Phase 3
0.5814	Remote Similarity	NPD6881	Approved
0.5814	Remote Similarity	NPD7320	Approved
0.5814	Remote Similarity	NPD6899	Approved
0.5806	Remote Similarity	NPD5696	Approved
0.5804	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.5802	Remote Similarity	NPD5217	Approved
0.5802	Remote Similarity	NPD5216	Approved
0.5802	Remote Similarity	NPD5127	Approved
0.5797	Remote Similarity	NPD7642	Approved
0.5797	Remote Similarity	NPD7604	Phase 2
0.5789	Remote Similarity	NPD5167	Approved
0.5786	Remote Similarity	NPD8074	Phase 3
0.5785	Remote Similarity	NPD5779	Approved
0.5785	Remote Similarity	NPD5778	Approved
0.5781	Remote Similarity	NPD6402	Approved
0.5781	Remote Similarity	NPD6675	Approved
0.5781	Remote Similarity	NPD7128	Approved
0.5781	Remote Similarity	NPD5739	Approved
0.5776	Remote Similarity	NPD5766	Clinical (unspecified phase)
0.5769	Remote Similarity	NPD6013	Approved
0.5769	Remote Similarity	NPD6012	Approved
0.5769	Remote Similarity	NPD6014	Approved
0.5758	Remote Similarity	NPD6882	Approved
0.5736	Remote Similarity	NPD5701	Approved
0.5736	Remote Similarity	NPD6614	Approved
0.5725	Remote Similarity	NPD7102	Approved
0.5725	Remote Similarity	NPD7290	Approved
0.5725	Remote Similarity	NPD6883	Approved
0.5725	Remote Similarity	NPD4634	Approved
0.5702	Remote Similarity	NPD7637	Suspended
0.5692	Remote Similarity	NPD5128	Approved
0.5692	Remote Similarity	NPD6011	Approved
0.5691	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.5683	Remote Similarity	NPD7829	Approved
0.5683	Remote Similarity	NPD7830	Approved
0.5682	Remote Similarity	NPD6847	Approved
0.5682	Remote Similarity	NPD6869	Approved
0.5682	Remote Similarity	NPD8130	Phase 1
0.5682	Remote Similarity	NPD6617	Approved
0.5669	Remote Similarity	NPD5211	Phase 2
0.5669	Remote Similarity	NPD7632	Discontinued
0.5669	Remote Similarity	NPD5091	Approved
0.5664	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.5656	Remote Similarity	NPD6399	Phase 3
0.5646	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.563	Remote Similarity	NPD6868	Approved
0.563	Remote Similarity	NPD7524	Approved
0.5625	Remote Similarity	NPD7260	Phase 2
0.5603	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.56	Remote Similarity	NPD5959	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