NPASS Compound

Structure

CID189338 OpenBabel06191715572D 31 33 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 5.0087 -3.2853 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 4.3396 -2.5422 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 4.6486 -1.5911 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 3.3614 -2.7501 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 6 1 0 0 0 0 2 10 1 0 0 0 0 3 11 1 0 0 0 0 4 12 2 0 0 0 0 5 13 1 0 0 0 0 6 10 2 0 0 0 0 7 11 2 0 0 0 0 7 14 1 0 0 0 0 8 15 1 0 0 0 0 8 21 1 0 0 0 0 9 21 1 0 0 0 0 9 23 1 0 0 0 0 10 19 1 0 0 0 0 11 22 1 0 0 0 0 12 20 1 0 0 0 0 13 24 2 0 0 0 0 13 29 1 0 0 0 0 14 17 1 0 0 0 0 14 29 1 1 0 0 0 15 16 1 0 0 0 0 15 30 1 1 0 0 0 16 12 1 1 0 0 0 16 18 1 0 0 0 0 17 21 1 1 0 0 0 17 22 1 0 0 0 0 18 22 1 6 0 0 0 18 31 1 0 0 0 0 19 25 2 0 0 0 0 19 30 1 0 0 0 0 20 26 2 0 0 0 0 20 31 1 0 0 0 0 21 27 1 6 0 0 0 22 28 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	454.14
Volume:	433.113
LogP:	1.184
LogD:	0.786
LogS:	-2.823
# Rotatable Bonds:	6
TPSA:	119.36
# H-Bond Aceptor:	8
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.216
Synthetic Accessibility Score:	5.196
Fsp3:	0.591
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:	-5.224
MDCK Permeability:	5.422035246738233e-05
Pgp-inhibitor:	0.392
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.872
20% Bioavailability (F20%):	0.988
30% Bioavailability (F30%):	0.992

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.363
Plasma Protein Binding (PPB):	65.0608901977539%
Volume Distribution (VD):	1.679
Pgp-substrate:	23.18538475036621%

ADMET: Metabolism

CYP1A2-inhibitor:	0.042
CYP1A2-substrate:	0.181
CYP2C19-inhibitor:	0.254
CYP2C19-substrate:	0.302
CYP2C9-inhibitor:	0.345
CYP2C9-substrate:	0.061
CYP2D6-inhibitor:	0.015
CYP2D6-substrate:	0.067
CYP3A4-inhibitor:	0.598
CYP3A4-substrate:	0.267

ADMET: Excretion

Clearance (CL):	2.749
Half-life (T1/2):	0.735

ADMET: Toxicity

hERG Blockers:	0.022
Human Hepatotoxicity (H-HT):	0.902
Drug-inuced Liver Injury (DILI):	0.843
AMES Toxicity:	0.157
Rat Oral Acute Toxicity:	0.76
Maximum Recommended Daily Dose:	0.141
Skin Sensitization:	0.689
Carcinogencity:	0.071
Eye Corrosion:	0.016
Eye Irritation:	0.06
Respiratory Toxicity:	0.797

Download Data

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

Natural Product: NPC189338

Natural Product ID:	NPC189338
*Common Name:**	Eupachlorin Acetate
IUPAC Name:	[(3aR,4R,6R,6aR,7R,9aS,9bS)-7-acetyloxy-6-(chloromethyl)-6,9a-dihydroxy-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 Acetate
Standard InCHIKey:	WVTMFOWXYVFVDE-UPVVJIFBSA-N
Standard InCHI:	InChI=1S/C22H27ClO8/c1-6-10(2)19(25)30-15-8-21(27,9-23)17-14(29-13(5)24)7-11(3)22(17,28)18-16(15)12(4)20(26)31-18/h6-7,14-18,27-28H,4,8-9H2,1-3,5H3/b10-6-/t14-,15-,16-,17+,18+,21+,22-/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)OC(=O)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL250952
PubChem CID:	5281447
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	=	5.21	n.a.	PMID[566076]
NPT91	Cell Line	KB	Homo sapiens	ED50	=	0.16	ug ml-1	PMID[566076]
NPT91	Cell Line	KB	Homo sapiens	ED50	=	0.35	umol/L	PMID[566077]

☑ 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 NPC189338 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	249
0.1-0.2	1455
0.2-0.3	5280
0.3-0.4	10451
0.4-0.5	14400
0.5-0.6	7384
0.6-0.7	2771
0.7-0.8	656
0.8-0.85	37
0.85-0.9	9
0.9-0.95	1
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC95290
0.9808	High Similarity	NPC258711
0.9808	High Similarity	NPC35069
0.9231	High Similarity	NPC166115
0.9048	High Similarity	NPC223450
0.9	High Similarity	NPC255450
0.9	High Similarity	NPC170692
0.8909	High Similarity	NPC121816
0.8868	High Similarity	NPC243998
0.8818	High Similarity	NPC273242
0.8585	High Similarity	NPC86077
0.8447	Intermediate Similarity	NPC477131
0.8426	Intermediate Similarity	NPC100487
0.8364	Intermediate Similarity	NPC68248
0.8273	Intermediate Similarity	NPC26617
0.8269	Intermediate Similarity	NPC470010
0.8269	Intermediate Similarity	NPC470013
0.8269	Intermediate Similarity	NPC198853
0.8269	Intermediate Similarity	NPC262133
0.8269	Intermediate Similarity	NPC323008
0.8252	Intermediate Similarity	NPC133698
0.819	Intermediate Similarity	NPC304886
0.819	Intermediate Similarity	NPC36954
0.8182	Intermediate Similarity	NPC54737
0.8173	Intermediate Similarity	NPC475912
0.8173	Intermediate Similarity	NPC135776
0.8173	Intermediate Similarity	NPC476300
0.8148	Intermediate Similarity	NPC150923
0.8125	Intermediate Similarity	NPC115352
0.8125	Intermediate Similarity	NPC139838
0.8125	Intermediate Similarity	NPC59489
0.8091	Intermediate Similarity	NPC203659
0.8077	Intermediate Similarity	NPC131209
0.8019	Intermediate Similarity	NPC270013
0.8019	Intermediate Similarity	NPC67584
0.8019	Intermediate Similarity	NPC14961
0.8	Intermediate Similarity	NPC475945
0.8	Intermediate Similarity	NPC179746
0.8	Intermediate Similarity	NPC81419
0.8	Intermediate Similarity	NPC124881
0.8	Intermediate Similarity	NPC475871
0.8	Intermediate Similarity	NPC110989
0.7982	Intermediate Similarity	NPC474742
0.7981	Intermediate Similarity	NPC51004
0.7944	Intermediate Similarity	NPC476315
0.7944	Intermediate Similarity	NPC213078
0.7928	Intermediate Similarity	NPC474741
0.7925	Intermediate Similarity	NPC81386
0.7925	Intermediate Similarity	NPC474035
0.7909	Intermediate Similarity	NPC474747
0.7909	Intermediate Similarity	NPC225353
0.7905	Intermediate Similarity	NPC208886
0.7905	Intermediate Similarity	NPC12172
0.7905	Intermediate Similarity	NPC30515
0.7905	Intermediate Similarity	NPC184463
0.7895	Intermediate Similarity	NPC477103
0.789	Intermediate Similarity	NPC186861
0.7885	Intermediate Similarity	NPC32922
0.7885	Intermediate Similarity	NPC307411
0.787	Intermediate Similarity	NPC161493
0.787	Intermediate Similarity	NPC471150
0.7869	Intermediate Similarity	NPC470973
0.785	Intermediate Similarity	NPC52044
0.783	Intermediate Similarity	NPC212486
0.781	Intermediate Similarity	NPC474761
0.781	Intermediate Similarity	NPC476004
0.7807	Intermediate Similarity	NPC477102
0.7798	Intermediate Similarity	NPC473326
0.7798	Intermediate Similarity	NPC221615
0.7798	Intermediate Similarity	NPC187268
0.7788	Intermediate Similarity	NPC202672
0.7788	Intermediate Similarity	NPC91248
0.7778	Intermediate Similarity	NPC279621
0.7757	Intermediate Similarity	NPC127019
0.7748	Intermediate Similarity	NPC149371
0.7739	Intermediate Similarity	NPC257240
0.7736	Intermediate Similarity	NPC475925
0.7736	Intermediate Similarity	NPC473321
0.7727	Intermediate Similarity	NPC471381
0.7727	Intermediate Similarity	NPC288876
0.7727	Intermediate Similarity	NPC70865
0.7714	Intermediate Similarity	NPC295312
0.7712	Intermediate Similarity	NPC329869
0.7706	Intermediate Similarity	NPC170143
0.7706	Intermediate Similarity	NPC245521
0.7706	Intermediate Similarity	NPC213947
0.7706	Intermediate Similarity	NPC108475
0.7706	Intermediate Similarity	NPC181151
0.7692	Intermediate Similarity	NPC190753
0.7685	Intermediate Similarity	NPC220221
0.7685	Intermediate Similarity	NPC163228
0.7685	Intermediate Similarity	NPC471142
0.7685	Intermediate Similarity	NPC476053
0.7685	Intermediate Similarity	NPC472873
0.7685	Intermediate Similarity	NPC170120
0.7685	Intermediate Similarity	NPC213698
0.7679	Intermediate Similarity	NPC475873
0.7672	Intermediate Similarity	NPC287311
0.7664	Intermediate Similarity	NPC273579
0.7664	Intermediate Similarity	NPC295204
0.7664	Intermediate Similarity	NPC288240
0.7664	Intermediate Similarity	NPC162205
0.7658	Intermediate Similarity	NPC47880
0.7658	Intermediate Similarity	NPC171759
0.7652	Intermediate Similarity	NPC273433
0.7647	Intermediate Similarity	NPC471145
0.7647	Intermediate Similarity	NPC471146
0.7642	Intermediate Similarity	NPC473619
0.7642	Intermediate Similarity	NPC475748
0.7642	Intermediate Similarity	NPC37607
0.7642	Intermediate Similarity	NPC129419
0.7642	Intermediate Similarity	NPC301969
0.7636	Intermediate Similarity	NPC471144
0.7636	Intermediate Similarity	NPC474213
0.7636	Intermediate Similarity	NPC141191
0.7627	Intermediate Similarity	NPC471380
0.7619	Intermediate Similarity	NPC178875
0.7619	Intermediate Similarity	NPC79549
0.7619	Intermediate Similarity	NPC153805
0.7615	Intermediate Similarity	NPC24956
0.7615	Intermediate Similarity	NPC18019
0.7615	Intermediate Similarity	NPC476009
0.7593	Intermediate Similarity	NPC473316
0.7593	Intermediate Similarity	NPC474338
0.7593	Intermediate Similarity	NPC474247
0.7593	Intermediate Similarity	NPC303942
0.7593	Intermediate Similarity	NPC473330
0.7593	Intermediate Similarity	NPC57405
0.7586	Intermediate Similarity	NPC471884
0.757	Intermediate Similarity	NPC261607
0.757	Intermediate Similarity	NPC111114
0.757	Intermediate Similarity	NPC300312
0.7568	Intermediate Similarity	NPC280963
0.7565	Intermediate Similarity	NPC117604
0.7547	Intermediate Similarity	NPC268298
0.7547	Intermediate Similarity	NPC92974
0.7547	Intermediate Similarity	NPC474032
0.7547	Intermediate Similarity	NPC215556
0.7547	Intermediate Similarity	NPC4986
0.7545	Intermediate Similarity	NPC169205
0.7545	Intermediate Similarity	NPC474313
0.7545	Intermediate Similarity	NPC40812
0.7542	Intermediate Similarity	NPC106395
0.7542	Intermediate Similarity	NPC46269
0.7542	Intermediate Similarity	NPC209058
0.7524	Intermediate Similarity	NPC186148
0.7524	Intermediate Similarity	NPC160138
0.7524	Intermediate Similarity	NPC118601
0.7524	Intermediate Similarity	NPC231889
0.7523	Intermediate Similarity	NPC475900
0.7523	Intermediate Similarity	NPC224689
0.7523	Intermediate Similarity	NPC475659
0.7523	Intermediate Similarity	NPC471141
0.7522	Intermediate Similarity	NPC472755
0.75	Intermediate Similarity	NPC15993
0.75	Intermediate Similarity	NPC21469
0.75	Intermediate Similarity	NPC110443
0.75	Intermediate Similarity	NPC128733
0.75	Intermediate Similarity	NPC228451
0.75	Intermediate Similarity	NPC185141
0.75	Intermediate Similarity	NPC133907
0.75	Intermediate Similarity	NPC475323
0.75	Intermediate Similarity	NPC475838
0.75	Intermediate Similarity	NPC258216
0.75	Intermediate Similarity	NPC476270
0.75	Intermediate Similarity	NPC125674
0.75	Intermediate Similarity	NPC46998
0.75	Intermediate Similarity	NPC36754
0.7479	Intermediate Similarity	NPC67290
0.7479	Intermediate Similarity	NPC133677
0.7479	Intermediate Similarity	NPC138303
0.7478	Intermediate Similarity	NPC477513
0.7477	Intermediate Similarity	NPC473448
0.7477	Intermediate Similarity	NPC71533
0.7477	Intermediate Similarity	NPC106510
0.7477	Intermediate Similarity	NPC144133
0.7477	Intermediate Similarity	NPC45125
0.7477	Intermediate Similarity	NPC179394
0.7477	Intermediate Similarity	NPC62815
0.7477	Intermediate Similarity	NPC216284
0.7477	Intermediate Similarity	NPC475855
0.7459	Intermediate Similarity	NPC143755
0.7458	Intermediate Similarity	NPC123855
0.7458	Intermediate Similarity	NPC76550
0.7458	Intermediate Similarity	NPC138757
0.7455	Intermediate Similarity	NPC230800
0.7455	Intermediate Similarity	NPC185553
0.7455	Intermediate Similarity	NPC477921
0.7455	Intermediate Similarity	NPC473859
0.7453	Intermediate Similarity	NPC207114
0.7453	Intermediate Similarity	NPC177629
0.7453	Intermediate Similarity	NPC474471
0.7453	Intermediate Similarity	NPC217983
0.7453	Intermediate Similarity	NPC227379
0.7453	Intermediate Similarity	NPC58219
0.7453	Intermediate Similarity	NPC473715
0.7438	Intermediate Similarity	NPC161060
0.7436	Intermediate Similarity	NPC5103
0.7434	Intermediate Similarity	NPC324017
0.7434	Intermediate Similarity	NPC320019

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 NPC189338 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	1982
0.2-0.3	3849
0.3-0.4	2172
0.4-0.5	646
0.5-0.6	244
0.6-0.7	42
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
0.8273	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7739	Intermediate Similarity	NPD6371	Approved
0.7547	Intermediate Similarity	NPD1695	Approved
0.7364	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7156	Intermediate Similarity	NPD46	Approved
0.7156	Intermediate Similarity	NPD6698	Approved
0.7025	Intermediate Similarity	NPD6053	Discontinued
0.7009	Intermediate Similarity	NPD1733	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD7983	Approved
0.6847	Remote Similarity	NPD7838	Discovery
0.6719	Remote Similarity	NPD5983	Phase 2
0.6694	Remote Similarity	NPD4632	Approved
0.6694	Remote Similarity	NPD6686	Approved
0.6667	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5362	Discontinued
0.6641	Remote Similarity	NPD7507	Approved
0.6636	Remote Similarity	NPD4249	Approved
0.6581	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6581	Remote Similarity	NPD4225	Approved
0.6577	Remote Similarity	NPD4250	Approved
0.6577	Remote Similarity	NPD4251	Approved
0.6549	Remote Similarity	NPD5785	Approved
0.6522	Remote Similarity	NPD5282	Discontinued
0.6515	Remote Similarity	NPD6336	Discontinued
0.6493	Remote Similarity	NPD7319	Approved
0.6471	Remote Similarity	NPD5344	Discontinued
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
0.6434	Remote Similarity	NPD7100	Approved
0.6418	Remote Similarity	NPD6033	Approved
0.641	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.6406	Remote Similarity	NPD6009	Approved
0.6406	Remote Similarity	NPD7115	Discovery
0.6396	Remote Similarity	NPD5363	Approved
0.6396	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6393	Remote Similarity	NPD6008	Approved
0.6385	Remote Similarity	NPD6319	Approved
0.6364	Remote Similarity	NPD7154	Phase 3
0.6357	Remote Similarity	NPD6313	Approved
0.6357	Remote Similarity	NPD6314	Approved
0.6357	Remote Similarity	NPD6335	Approved
0.6339	Remote Similarity	NPD5786	Approved
0.6324	Remote Similarity	NPD5956	Approved
0.6308	Remote Similarity	NPD7101	Approved
0.6293	Remote Similarity	NPD5779	Approved
0.6293	Remote Similarity	NPD5778	Approved
0.6273	Remote Similarity	NPD6435	Approved
0.625	Remote Similarity	NPD6648	Approved
0.6239	Remote Similarity	NPD4821	Approved
0.6239	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6239	Remote Similarity	NPD4819	Approved
0.6239	Remote Similarity	NPD4822	Approved
0.6239	Remote Similarity	NPD4820	Approved
0.6222	Remote Similarity	NPD8074	Phase 3
0.622	Remote Similarity	NPD8297	Approved
0.6194	Remote Similarity	NPD7492	Approved
0.619	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6148	Remote Similarity	NPD6616	Approved
0.6142	Remote Similarity	NPD5215	Approved
0.6142	Remote Similarity	NPD6650	Approved
0.6142	Remote Similarity	NPD6649	Approved
0.6136	Remote Similarity	NPD6054	Approved
0.6126	Remote Similarity	NPD4270	Approved
0.6126	Remote Similarity	NPD4269	Approved
0.6116	Remote Similarity	NPD7640	Approved
0.6116	Remote Similarity	NPD7639	Approved
0.6111	Remote Similarity	NPD6372	Approved
0.6111	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD6373	Approved
0.6107	Remote Similarity	NPD7327	Approved
0.6107	Remote Similarity	NPD7328	Approved
0.6103	Remote Similarity	NPD7078	Approved
0.6091	Remote Similarity	NPD5368	Approved
0.609	Remote Similarity	NPD8033	Approved
0.609	Remote Similarity	NPD6016	Approved
0.609	Remote Similarity	NPD6015	Approved
0.608	Remote Similarity	NPD5697	Approved
0.6071	Remote Similarity	NPD5331	Approved
0.6071	Remote Similarity	NPD5332	Approved
0.6063	Remote Similarity	NPD5169	Approved
0.6061	Remote Similarity	NPD7516	Approved
0.6061	Remote Similarity	NPD4522	Approved
0.6058	Remote Similarity	NPD7736	Approved
0.6056	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6055	Remote Similarity	NPD4268	Approved
0.6055	Remote Similarity	NPD4271	Approved
0.6045	Remote Similarity	NPD6370	Approved
0.6045	Remote Similarity	NPD5988	Approved
0.6043	Remote Similarity	NPD7260	Phase 2
0.6036	Remote Similarity	NPD5369	Approved
0.6036	Remote Similarity	NPD4790	Discontinued
0.6033	Remote Similarity	NPD7638	Approved
0.6032	Remote Similarity	NPD6881	Approved
0.6032	Remote Similarity	NPD7320	Approved
0.6032	Remote Similarity	NPD6899	Approved
0.6016	Remote Similarity	NPD5216	Approved
0.6016	Remote Similarity	NPD5127	Approved
0.6016	Remote Similarity	NPD5217	Approved
0.6015	Remote Similarity	NPD8294	Approved
0.6015	Remote Similarity	NPD8377	Approved
0.6015	Remote Similarity	NPD6059	Approved
0.6	Remote Similarity	NPD5167	Approved
0.6	Remote Similarity	NPD6675	Approved
0.6	Remote Similarity	NPD7642	Approved
0.6	Remote Similarity	NPD5739	Approved
0.6	Remote Similarity	NPD7128	Approved
0.6	Remote Similarity	NPD6845	Suspended
0.6	Remote Similarity	NPD6402	Approved
0.6	Remote Similarity	NPD7839	Suspended
0.5985	Remote Similarity	NPD8293	Discontinued
0.5984	Remote Similarity	NPD6014	Approved
0.5984	Remote Similarity	NPD6012	Approved
0.5984	Remote Similarity	NPD6013	Approved
0.5982	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.597	Remote Similarity	NPD8335	Approved
0.597	Remote Similarity	NPD8378	Approved
0.597	Remote Similarity	NPD8379	Approved
0.597	Remote Similarity	NPD8380	Approved
0.597	Remote Similarity	NPD8296	Approved
0.597	Remote Similarity	NPD7503	Approved
0.5969	Remote Similarity	NPD6882	Approved
0.5965	Remote Similarity	NPD1694	Approved
0.5954	Remote Similarity	NPD6868	Approved
0.5952	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.5952	Remote Similarity	NPD5701	Approved
0.5952	Remote Similarity	NPD6412	Phase 2
0.5946	Remote Similarity	NPD4252	Approved
0.5938	Remote Similarity	NPD7290	Approved
0.5938	Remote Similarity	NPD7102	Approved
0.5938	Remote Similarity	NPD6883	Approved
0.5917	Remote Similarity	NPD5695	Phase 3
0.5912	Remote Similarity	NPD8273	Phase 1
0.5909	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.5906	Remote Similarity	NPD6011	Approved
0.5906	Remote Similarity	NPD5128	Approved
0.5902	Remote Similarity	NPD5696	Approved
0.5891	Remote Similarity	NPD8130	Phase 1
0.5891	Remote Similarity	NPD6847	Approved
0.5891	Remote Similarity	NPD6869	Approved
0.5891	Remote Similarity	NPD6617	Approved
0.5887	Remote Similarity	NPD5211	Phase 2
0.5882	Remote Similarity	NPD7829	Approved
0.5882	Remote Similarity	NPD6399	Phase 3
0.5882	Remote Similarity	NPD7604	Phase 2
0.5882	Remote Similarity	NPD7830	Approved
0.5865	Remote Similarity	NPD7641	Discontinued
0.5841	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.5841	Remote Similarity	NPD5209	Approved
0.5827	Remote Similarity	NPD6614	Approved
0.582	Remote Similarity	NPD6083	Phase 2
0.582	Remote Similarity	NPD6084	Phase 2
0.5814	Remote Similarity	NPD4634	Approved
0.5798	Remote Similarity	NPD7637	Suspended
0.5797	Remote Similarity	NPD8451	Approved
0.5794	Remote Similarity	NPD5141	Approved
0.5789	Remote Similarity	NPD6110	Phase 1
0.5781	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.5769	Remote Similarity	NPD2204	Approved
0.5769	Remote Similarity	NPD1719	Phase 1
0.5763	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.5763	Remote Similarity	NPD6101	Approved
0.576	Remote Similarity	NPD5091	Approved
0.5755	Remote Similarity	NPD8448	Approved
0.5739	Remote Similarity	NPD5766	Clinical (unspecified phase)
0.5735	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.5726	Remote Similarity	NPD5286	Approved
0.5726	Remote Similarity	NPD7524	Approved
0.5726	Remote Similarity	NPD5285	Approved
0.5726	Remote Similarity	NPD4696	Approved
0.5725	Remote Similarity	NPD8341	Approved
0.5725	Remote Similarity	NPD8299	Approved
0.5725	Remote Similarity	NPD8340	Approved
0.5725	Remote Similarity	NPD8342	Approved
0.5714	Remote Similarity	NPD6274	Approved
0.5691	Remote Similarity	NPD4755	Approved
0.5682	Remote Similarity	NPD8133	Approved
0.5676	Remote Similarity	NPD8384	Approved
0.5667	Remote Similarity	NPD5693	Phase 1
0.5667	Remote Similarity	NPD5284	Approved
0.5667	Remote Similarity	NPD6411	Approved
0.5667	Remote Similarity	NPD5281	Approved
0.5659	Remote Similarity	NPD5168	Approved
0.5656	Remote Similarity	NPD5654	Approved
0.5656	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.5652	Remote Similarity	NPD8328	Phase 3
0.5649	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5635	Remote Similarity	NPD5226	Approved
0.5635	Remote Similarity	NPD7632	Discontinued
0.5635	Remote Similarity	NPD5224	Approved
0.5635	Remote Similarity	NPD5225	Approved
0.5635	Remote Similarity	NPD3653	Clinical (unspecified phase)
0.5635	Remote Similarity	NPD4633	Approved
0.5634	Remote Similarity	NPD8391	Approved
0.5634	Remote Similarity	NPD8390	Approved
0.5634	Remote Similarity	NPD8392	Approved
0.562	Remote Similarity	NPD8444	Approved
0.5603	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.56	Remote Similarity	NPD4700	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