NPASS Compound

Structure

CID258711 OpenBabel06191716062D 28 30 0 0 1 0 0 0 0 0999 V2000 -3.1429 -2.7714 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5430 -5.3482 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9297 0.4657 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2410 -1.2937 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2475 -3.7659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9002 -1.0288 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2560 -3.1923 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3565 -3.9919 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4385 -4.3537 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0342 -0.5288 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2946 -0.9705 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6923 -2.0069 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.5068 -2.5457 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.4769 -1.5461 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6978 -2.1115 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.3232 -0.9463 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.5249 -3.9470 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9999 -0.0150 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2371 -2.9990 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.2910 -1.1979 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.2761 -4.3849 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0 3.3614 -2.7501 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7159 -4.5347 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5997 0.7852 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1567 -3.3921 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2918 -1.2373 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4204 -2.9524 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 5 1 0 0 0 0 2 9 1 0 0 0 0 3 10 1 0 0 0 0 4 11 2 0 0 0 0 5 9 2 0 0 0 0 6 10 2 0 0 0 0 6 12 1 0 0 0 0 7 13 1 0 0 0 0 7 19 1 0 0 0 0 8 19 1 0 0 0 0 8 21 1 0 0 0 0 9 17 1 0 0 0 0 10 20 1 0 0 0 0 11 18 1 0 0 0 0 12 15 1 0 0 0 0 12 22 1 1 0 0 0 13 14 1 0 0 0 0 13 27 1 1 0 0 0 14 11 1 1 0 0 0 14 16 1 0 0 0 0 15 19 1 1 0 0 0 15 20 1 0 0 0 0 16 20 1 6 0 0 0 16 28 1 0 0 0 0 17 23 2 0 0 0 0 17 27 1 0 0 0 0 18 24 2 0 0 0 0 18 28 1 0 0 0 0 19 25 1 6 0 0 0 20 26 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	412.13
Volume:	392.367
LogP:	0.883
LogD:	0.599
LogS:	-2.565
# Rotatable Bonds:	4
TPSA:	113.29
# H-Bond Aceptor:	7
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.274
Synthetic Accessibility Score:	5.231
Fsp3:	0.6
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	3
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.245
MDCK Permeability:	3.0105562473181635e-05
Pgp-inhibitor:	0.005
Pgp-substrate:	0.007
Human Intestinal Absorption (HIA):	0.85
20% Bioavailability (F20%):	0.975
30% Bioavailability (F30%):	0.987

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.357
Plasma Protein Binding (PPB):	70.40473937988281%
Volume Distribution (VD):	1.458
Pgp-substrate:	21.06414222717285%

ADMET: Metabolism

CYP1A2-inhibitor:	0.037
CYP1A2-substrate:	0.533
CYP2C19-inhibitor:	0.151
CYP2C19-substrate:	0.527
CYP2C9-inhibitor:	0.174
CYP2C9-substrate:	0.087
CYP2D6-inhibitor:	0.009
CYP2D6-substrate:	0.07
CYP3A4-inhibitor:	0.516
CYP3A4-substrate:	0.253

ADMET: Excretion

Clearance (CL):	3.037
Half-life (T1/2):	0.714

ADMET: Toxicity

hERG Blockers:	0.034
Human Hepatotoxicity (H-HT):	0.758
Drug-inuced Liver Injury (DILI):	0.546
AMES Toxicity:	0.136
Rat Oral Acute Toxicity:	0.811
Maximum Recommended Daily Dose:	0.312
Skin Sensitization:	0.571
Carcinogencity:	0.075
Eye Corrosion:	0.013
Eye Irritation:	0.109
Respiratory Toxicity:	0.848

Download Data

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

Natural Product: NPC258711

Natural Product ID:	NPC258711
*Common Name:**	Eupachlorin
IUPAC Name:	[(3aR,4R,6R,6aR,7R,9aS,9bS)-6-(chloromethyl)-6,7,9a-trihydroxy-9-methyl-3-methylidene-2-oxo-3a,4,5,6a,7,9b-hexahydroazuleno[4,5-b]furan-4-yl] (Z)-2-methylbut-2-enoate
Synonyms:	Eupachlorin
Standard InCHIKey:	VCAKAFVZYNRGKS-WBNZXOOCSA-N
Standard InCHI:	InChI=1S/C20H25ClO7/c1-5-9(2)17(23)27-13-7-19(25,8-21)15-12(22)6-10(3)20(15,26)16-14(13)11(4)18(24)28-16/h5-6,12-16,22,25-26H,4,7-8H2,1-3H3/b9-5-/t12-,13-,14-,15+,16+,19+,20-/m1/s1
SMILES:	C/C=C(/C)C(=O)O[C@@H]1C[C@](CCl)([C@@H]2[C@@H](C=C(C)[C@@]2([C@@H]2[C@@H]1C(=C)C(=O)O2)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL437014
PubChem CID:	5281446
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
NPO33469	Asteraceae	Family	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18329753]
NPO26385	Eupatorium rotundifolium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26385	Eupatorium rotundifolium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26385	Eupatorium rotundifolium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO26385	Eupatorium rotundifolium	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
ED50	2
Others	1

Activity Type	# Activity
Cell Line	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	pED50	=	6.29	n.a.	PMID[536376]
NPT91	Cell Line	KB	Homo sapiens	ED50	=	0.21	ug ml-1	PMID[536376]
NPT91	Cell Line	KB	Homo sapiens	ED50	=	0.51	umol/L	PMID[536377]

☑ 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 NPC258711 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	246
0.1-0.2	1437
0.2-0.3	5222
0.3-0.4	10366
0.4-0.5	14248
0.5-0.6	7464
0.6-0.7	2937
0.7-0.8	714
0.8-0.85	46
0.85-0.9	12
0.9-0.95	0
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC35069
0.9808	High Similarity	NPC95290
0.9808	High Similarity	NPC189338
0.9417	High Similarity	NPC166115
0.9048	High Similarity	NPC243998
0.9	High Similarity	NPC255450
0.9	High Similarity	NPC170692
0.8909	High Similarity	NPC121816
0.8868	High Similarity	NPC223450
0.8818	High Similarity	NPC273242
0.8762	High Similarity	NPC86077
0.8598	High Similarity	NPC100487
0.8532	High Similarity	NPC68248
0.8447	Intermediate Similarity	NPC477131
0.8365	Intermediate Similarity	NPC304886
0.835	Intermediate Similarity	NPC475912
0.8349	Intermediate Similarity	NPC54737
0.8318	Intermediate Similarity	NPC150923
0.8269	Intermediate Similarity	NPC262133
0.8269	Intermediate Similarity	NPC470010
0.8269	Intermediate Similarity	NPC323008
0.8269	Intermediate Similarity	NPC470013
0.8269	Intermediate Similarity	NPC198853
0.8257	Intermediate Similarity	NPC203659
0.8252	Intermediate Similarity	NPC133698
0.8252	Intermediate Similarity	NPC131209
0.819	Intermediate Similarity	NPC14961
0.819	Intermediate Similarity	NPC270013
0.819	Intermediate Similarity	NPC36954
0.8173	Intermediate Similarity	NPC135776
0.8173	Intermediate Similarity	NPC81419
0.8173	Intermediate Similarity	NPC179746
0.8165	Intermediate Similarity	NPC475945
0.8165	Intermediate Similarity	NPC110989
0.8165	Intermediate Similarity	NPC475871
0.8125	Intermediate Similarity	NPC59489
0.8125	Intermediate Similarity	NPC115352
0.8125	Intermediate Similarity	NPC139838
0.8108	Intermediate Similarity	NPC26617
0.8095	Intermediate Similarity	NPC81386
0.8095	Intermediate Similarity	NPC474035
0.8077	Intermediate Similarity	NPC30515
0.8077	Intermediate Similarity	NPC12172
0.8077	Intermediate Similarity	NPC184463
0.8077	Intermediate Similarity	NPC208886
0.8073	Intermediate Similarity	NPC474747
0.8073	Intermediate Similarity	NPC225353
0.8037	Intermediate Similarity	NPC471150
0.8037	Intermediate Similarity	NPC161493
0.8019	Intermediate Similarity	NPC52044
0.8019	Intermediate Similarity	NPC67584
0.8	Intermediate Similarity	NPC124881
0.8	Intermediate Similarity	NPC212486
0.8	Intermediate Similarity	NPC476300
0.7982	Intermediate Similarity	NPC474742
0.7981	Intermediate Similarity	NPC51004
0.7981	Intermediate Similarity	NPC474761
0.7981	Intermediate Similarity	NPC476004
0.7963	Intermediate Similarity	NPC473326
0.7963	Intermediate Similarity	NPC187268
0.7961	Intermediate Similarity	NPC202672
0.7944	Intermediate Similarity	NPC476315
0.7944	Intermediate Similarity	NPC213078
0.7928	Intermediate Similarity	NPC474741
0.7905	Intermediate Similarity	NPC475925
0.7905	Intermediate Similarity	NPC473321
0.7895	Intermediate Similarity	NPC257240
0.789	Intermediate Similarity	NPC288876
0.789	Intermediate Similarity	NPC70865
0.789	Intermediate Similarity	NPC471381
0.789	Intermediate Similarity	NPC186861
0.7885	Intermediate Similarity	NPC32922
0.7885	Intermediate Similarity	NPC307411
0.7885	Intermediate Similarity	NPC295312
0.785	Intermediate Similarity	NPC213698
0.785	Intermediate Similarity	NPC472873
0.785	Intermediate Similarity	NPC220221
0.785	Intermediate Similarity	NPC170120
0.783	Intermediate Similarity	NPC295204
0.783	Intermediate Similarity	NPC288240
0.783	Intermediate Similarity	NPC273579
0.783	Intermediate Similarity	NPC162205
0.7818	Intermediate Similarity	NPC171759
0.781	Intermediate Similarity	NPC473619
0.781	Intermediate Similarity	NPC129419
0.7798	Intermediate Similarity	NPC474213
0.7798	Intermediate Similarity	NPC141191
0.7798	Intermediate Similarity	NPC221615
0.7788	Intermediate Similarity	NPC91248
0.7788	Intermediate Similarity	NPC153805
0.7778	Intermediate Similarity	NPC18019
0.7778	Intermediate Similarity	NPC279621
0.7778	Intermediate Similarity	NPC24956
0.7757	Intermediate Similarity	NPC127019
0.7757	Intermediate Similarity	NPC303942
0.7757	Intermediate Similarity	NPC57405
0.7739	Intermediate Similarity	NPC477103
0.7724	Intermediate Similarity	NPC470973
0.7714	Intermediate Similarity	NPC215556
0.7714	Intermediate Similarity	NPC268298
0.7714	Intermediate Similarity	NPC474032
0.7706	Intermediate Similarity	NPC169205
0.7706	Intermediate Similarity	NPC108475
0.7706	Intermediate Similarity	NPC181151
0.7706	Intermediate Similarity	NPC170143
0.7706	Intermediate Similarity	NPC474313
0.7706	Intermediate Similarity	NPC213947
0.7692	Intermediate Similarity	NPC46269
0.7692	Intermediate Similarity	NPC190753
0.7692	Intermediate Similarity	NPC186148
0.7692	Intermediate Similarity	NPC106395
0.7685	Intermediate Similarity	NPC163228
0.7685	Intermediate Similarity	NPC476053
0.7685	Intermediate Similarity	NPC471142
0.7679	Intermediate Similarity	NPC475873
0.7672	Intermediate Similarity	NPC287311
0.767	Intermediate Similarity	NPC21469
0.7664	Intermediate Similarity	NPC475838
0.7664	Intermediate Similarity	NPC125674
0.7664	Intermediate Similarity	NPC228451
0.7658	Intermediate Similarity	NPC185141
0.7658	Intermediate Similarity	NPC46998
0.7658	Intermediate Similarity	NPC133907
0.7658	Intermediate Similarity	NPC110443
0.7658	Intermediate Similarity	NPC476270
0.7658	Intermediate Similarity	NPC128733
0.7652	Intermediate Similarity	NPC477102
0.7652	Intermediate Similarity	NPC273433
0.7647	Intermediate Similarity	NPC475323
0.7642	Intermediate Similarity	NPC301969
0.7642	Intermediate Similarity	NPC475855
0.7642	Intermediate Similarity	NPC216284
0.7642	Intermediate Similarity	NPC473448
0.7642	Intermediate Similarity	NPC71533
0.7642	Intermediate Similarity	NPC106510
0.7642	Intermediate Similarity	NPC37607
0.7636	Intermediate Similarity	NPC471144
0.7627	Intermediate Similarity	NPC138303
0.7627	Intermediate Similarity	NPC67290
0.7627	Intermediate Similarity	NPC133677
0.7627	Intermediate Similarity	NPC471380
0.7619	Intermediate Similarity	NPC178875
0.7619	Intermediate Similarity	NPC227379
0.7619	Intermediate Similarity	NPC79549
0.7619	Intermediate Similarity	NPC177629
0.7619	Intermediate Similarity	NPC474471
0.7619	Intermediate Similarity	NPC58219
0.7619	Intermediate Similarity	NPC473715
0.7619	Intermediate Similarity	NPC217983
0.7619	Intermediate Similarity	NPC207114
0.7615	Intermediate Similarity	NPC473859
0.7615	Intermediate Similarity	NPC477921
0.7615	Intermediate Similarity	NPC476009
0.7615	Intermediate Similarity	NPC185553
0.7607	Intermediate Similarity	NPC123855
0.7607	Intermediate Similarity	NPC138757
0.7607	Intermediate Similarity	NPC76550
0.7593	Intermediate Similarity	NPC474247
0.7593	Intermediate Similarity	NPC473316
0.7593	Intermediate Similarity	NPC474338
0.7593	Intermediate Similarity	NPC473330
0.7589	Intermediate Similarity	NPC149371
0.7586	Intermediate Similarity	NPC5103
0.757	Intermediate Similarity	NPC261607
0.757	Intermediate Similarity	NPC300312
0.757	Intermediate Similarity	NPC111114
0.757	Intermediate Similarity	NPC184063
0.7565	Intermediate Similarity	NPC475960
0.7565	Intermediate Similarity	NPC117604
0.7565	Intermediate Similarity	NPC308191
0.7563	Intermediate Similarity	NPC329869
0.7547	Intermediate Similarity	NPC473564
0.7547	Intermediate Similarity	NPC4986
0.7547	Intermediate Similarity	NPC92974
0.7545	Intermediate Similarity	NPC245521
0.7545	Intermediate Similarity	NPC40812
0.7544	Intermediate Similarity	NPC179891
0.7542	Intermediate Similarity	NPC209058
0.7524	Intermediate Similarity	NPC231889
0.7524	Intermediate Similarity	NPC248602
0.7524	Intermediate Similarity	NPC118601
0.7524	Intermediate Similarity	NPC237540
0.7524	Intermediate Similarity	NPC160138
0.7523	Intermediate Similarity	NPC477922
0.7523	Intermediate Similarity	NPC475900
0.7523	Intermediate Similarity	NPC224689
0.7523	Intermediate Similarity	NPC193645
0.7523	Intermediate Similarity	NPC90121
0.7523	Intermediate Similarity	NPC475659
0.7523	Intermediate Similarity	NPC275960
0.7523	Intermediate Similarity	NPC48803
0.7522	Intermediate Similarity	NPC474775
0.7522	Intermediate Similarity	NPC472755
0.75	Intermediate Similarity	NPC471145
0.75	Intermediate Similarity	NPC477950
0.75	Intermediate Similarity	NPC38154
0.75	Intermediate Similarity	NPC258216
0.75	Intermediate Similarity	NPC137033
0.75	Intermediate Similarity	NPC471146
0.75	Intermediate Similarity	NPC47880

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 NPC258711 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	210
0.1-0.2	1958
0.2-0.3	3840
0.3-0.4	2201
0.4-0.5	637
0.5-0.6	247
0.6-0.7	52
0.7-0.8	4
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8108	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7895	Intermediate Similarity	NPD6371	Approved
0.7547	Intermediate Similarity	NPD1695	Approved
0.7523	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7167	Intermediate Similarity	NPD6053	Discontinued
0.7156	Intermediate Similarity	NPD46	Approved
0.7156	Intermediate Similarity	NPD6698	Approved
0.7009	Intermediate Similarity	NPD1733	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD7983	Approved
0.685	Remote Similarity	NPD5983	Phase 2
0.6847	Remote Similarity	NPD7838	Discovery
0.6829	Remote Similarity	NPD4632	Approved
0.6822	Remote Similarity	NPD5362	Discontinued
0.6789	Remote Similarity	NPD4249	Approved
0.6727	Remote Similarity	NPD4250	Approved
0.6727	Remote Similarity	NPD4251	Approved
0.6724	Remote Similarity	NPD4225	Approved
0.6696	Remote Similarity	NPD5785	Approved
0.6694	Remote Similarity	NPD6686	Approved
0.6667	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6641	Remote Similarity	NPD6336	Discontinued
0.6641	Remote Similarity	NPD7507	Approved
0.661	Remote Similarity	NPD5344	Discontinued
0.6581	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD7100	Approved
0.6552	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.6545	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6545	Remote Similarity	NPD5363	Approved
0.6541	Remote Similarity	NPD6033	Approved
0.6535	Remote Similarity	NPD6009	Approved
0.6535	Remote Similarity	NPD7115	Discovery
0.6522	Remote Similarity	NPD5282	Discontinued
0.6514	Remote Similarity	NPD7154	Phase 3
0.6493	Remote Similarity	NPD7319	Approved
0.6486	Remote Similarity	NPD5786	Approved
0.6484	Remote Similarity	NPD6313	Approved
0.6484	Remote Similarity	NPD6335	Approved
0.6484	Remote Similarity	NPD6314	Approved
0.6462	Remote Similarity	NPD8513	Phase 3
0.6462	Remote Similarity	NPD8517	Approved
0.6462	Remote Similarity	NPD8516	Approved
0.6462	Remote Similarity	NPD8515	Approved
0.6444	Remote Similarity	NPD5956	Approved
0.6435	Remote Similarity	NPD5779	Approved
0.6435	Remote Similarity	NPD5778	Approved
0.6434	Remote Similarity	NPD7101	Approved
0.6422	Remote Similarity	NPD6435	Approved
0.6393	Remote Similarity	NPD6008	Approved
0.6389	Remote Similarity	NPD4821	Approved
0.6389	Remote Similarity	NPD4820	Approved
0.6389	Remote Similarity	NPD4819	Approved
0.6389	Remote Similarity	NPD4822	Approved
0.6389	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6385	Remote Similarity	NPD6319	Approved
0.6316	Remote Similarity	NPD7492	Approved
0.6273	Remote Similarity	NPD4270	Approved
0.6273	Remote Similarity	NPD4269	Approved
0.627	Remote Similarity	NPD5215	Approved
0.6269	Remote Similarity	NPD6616	Approved
0.626	Remote Similarity	NPD6054	Approved
0.625	Remote Similarity	NPD7640	Approved
0.625	Remote Similarity	NPD6648	Approved
0.625	Remote Similarity	NPD7639	Approved
0.624	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6239	Remote Similarity	NPD5368	Approved
0.6222	Remote Similarity	NPD7078	Approved
0.6222	Remote Similarity	NPD8074	Phase 3
0.622	Remote Similarity	NPD8297	Approved
0.6216	Remote Similarity	NPD5332	Approved
0.6216	Remote Similarity	NPD5331	Approved
0.6212	Remote Similarity	NPD6015	Approved
0.6212	Remote Similarity	NPD6016	Approved
0.621	Remote Similarity	NPD5697	Approved
0.6204	Remote Similarity	NPD4268	Approved
0.6204	Remote Similarity	NPD4271	Approved
0.619	Remote Similarity	NPD5169	Approved
0.6183	Remote Similarity	NPD4522	Approved
0.6182	Remote Similarity	NPD5369	Approved
0.6182	Remote Similarity	NPD4790	Discontinued
0.6176	Remote Similarity	NPD7736	Approved
0.6167	Remote Similarity	NPD7638	Approved
0.6165	Remote Similarity	NPD5988	Approved
0.6165	Remote Similarity	NPD6370	Approved
0.616	Remote Similarity	NPD7320	Approved
0.616	Remote Similarity	NPD6881	Approved
0.616	Remote Similarity	NPD6899	Approved
0.6142	Remote Similarity	NPD5216	Approved
0.6142	Remote Similarity	NPD6650	Approved
0.6142	Remote Similarity	NPD5127	Approved
0.6142	Remote Similarity	NPD6649	Approved
0.6142	Remote Similarity	NPD5217	Approved
0.6136	Remote Similarity	NPD6059	Approved
0.6129	Remote Similarity	NPD7128	Approved
0.6129	Remote Similarity	NPD5739	Approved
0.6129	Remote Similarity	NPD6402	Approved
0.6129	Remote Similarity	NPD6675	Approved
0.6124	Remote Similarity	NPD5167	Approved
0.6111	Remote Similarity	NPD6372	Approved
0.6111	Remote Similarity	NPD6014	Approved
0.6111	Remote Similarity	NPD6373	Approved
0.6111	Remote Similarity	NPD6013	Approved
0.6111	Remote Similarity	NPD6012	Approved
0.6107	Remote Similarity	NPD7327	Approved
0.6107	Remote Similarity	NPD7328	Approved
0.6103	Remote Similarity	NPD8293	Discontinued
0.6091	Remote Similarity	NPD4252	Approved
0.609	Remote Similarity	NPD8033	Approved
0.608	Remote Similarity	NPD5701	Approved
0.608	Remote Similarity	NPD6412	Phase 2
0.6077	Remote Similarity	NPD6868	Approved
0.6063	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6063	Remote Similarity	NPD6883	Approved
0.6063	Remote Similarity	NPD7102	Approved
0.6063	Remote Similarity	NPD7290	Approved
0.6061	Remote Similarity	NPD7516	Approved
0.6056	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6055	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6032	Remote Similarity	NPD6011	Approved
0.6032	Remote Similarity	NPD5128	Approved
0.6016	Remote Similarity	NPD6617	Approved
0.6016	Remote Similarity	NPD8130	Phase 1
0.6016	Remote Similarity	NPD6847	Approved
0.6016	Remote Similarity	NPD6869	Approved
0.6016	Remote Similarity	NPD5211	Phase 2
0.6015	Remote Similarity	NPD8294	Approved
0.6015	Remote Similarity	NPD8377	Approved
0.6	Remote Similarity	NPD7604	Phase 2
0.6	Remote Similarity	NPD7839	Suspended
0.6	Remote Similarity	NPD7642	Approved
0.5982	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.597	Remote Similarity	NPD8378	Approved
0.597	Remote Similarity	NPD8379	Approved
0.597	Remote Similarity	NPD8335	Approved
0.597	Remote Similarity	NPD7503	Approved
0.597	Remote Similarity	NPD8296	Approved
0.597	Remote Similarity	NPD8380	Approved
0.5969	Remote Similarity	NPD6882	Approved
0.5965	Remote Similarity	NPD1694	Approved
0.595	Remote Similarity	NPD6083	Phase 2
0.595	Remote Similarity	NPD6084	Phase 2
0.5938	Remote Similarity	NPD4634	Approved
0.5932	Remote Similarity	NPD7637	Suspended
0.5929	Remote Similarity	NPD7260	Phase 2
0.5929	Remote Similarity	NPD6110	Phase 1
0.592	Remote Similarity	NPD5141	Approved
0.5917	Remote Similarity	NPD5695	Phase 3
0.5912	Remote Similarity	NPD8273	Phase 1
0.5906	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.5902	Remote Similarity	NPD5696	Approved
0.5897	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.5897	Remote Similarity	NPD6101	Approved
0.5891	Remote Similarity	NPD1719	Phase 1
0.5887	Remote Similarity	NPD6845	Suspended
0.5882	Remote Similarity	NPD7829	Approved
0.5882	Remote Similarity	NPD7830	Approved
0.5882	Remote Similarity	NPD6399	Phase 3
0.5877	Remote Similarity	NPD5766	Clinical (unspecified phase)
0.5865	Remote Similarity	NPD7641	Discontinued
0.5862	Remote Similarity	NPD7524	Approved
0.5854	Remote Similarity	NPD5285	Approved
0.5854	Remote Similarity	NPD5286	Approved
0.5854	Remote Similarity	NPD4696	Approved
0.5852	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.5841	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.5841	Remote Similarity	NPD5209	Approved
0.5833	Remote Similarity	NPD6274	Approved
0.5827	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.5827	Remote Similarity	NPD6614	Approved
0.582	Remote Similarity	NPD4755	Approved
0.5798	Remote Similarity	NPD6411	Approved
0.5797	Remote Similarity	NPD8451	Approved
0.5781	Remote Similarity	NPD5168	Approved
0.5769	Remote Similarity	NPD2204	Approved
0.5769	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.576	Remote Similarity	NPD5224	Approved
0.576	Remote Similarity	NPD4633	Approved
0.576	Remote Similarity	NPD5225	Approved
0.576	Remote Similarity	NPD5226	Approved
0.576	Remote Similarity	NPD5091	Approved
0.576	Remote Similarity	NPD7632	Discontinued
0.5755	Remote Similarity	NPD8448	Approved
0.5739	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.5726	Remote Similarity	NPD4700	Approved
0.5725	Remote Similarity	NPD8340	Approved
0.5725	Remote Similarity	NPD8341	Approved
0.5725	Remote Similarity	NPD8299	Approved
0.5725	Remote Similarity	NPD8342	Approved
0.5714	Remote Similarity	NPD5175	Approved
0.5714	Remote Similarity	NPD5174	Approved
0.5682	Remote Similarity	NPD8133	Approved
0.568	Remote Similarity	NPD5223	Approved
0.5676	Remote Similarity	NPD8384	Approved
0.5672	Remote Similarity	NPD6317	Approved
0.5667	Remote Similarity	NPD5693	Phase 1
0.5667	Remote Similarity	NPD5284	Approved
0.5667	Remote Similarity	NPD5281	Approved
0.5656	Remote Similarity	NPD4629	Approved
0.5656	Remote Similarity	NPD5210	Approved
0.5656	Remote Similarity	NPD5654	Approved
0.5656	Remote Similarity	NPD6356	Clinical (unspecified phase)

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