NPASS Compound

Structure

NPC273242 OpenBabel07101719252D 32 35 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 -2.0595 -3.2877 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 -1.4016 -2.5346 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 1.6265 -1.1449 0.0000 C 0 0 1 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 2.5904 -0.8789 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 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 -1.7248 -1.5883 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 -0.4205 -2.7279 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 9 1 0 0 0 0 2 10 2 0 0 0 0 3 11 1 0 0 0 0 5 6 1 0 0 0 0 5 9 2 0 0 0 0 6 24 1 0 0 0 0 7 12 1 0 0 0 0 7 22 1 0 0 0 0 8 22 1 0 0 0 0 8 23 1 0 0 0 0 9 19 1 0 0 0 0 10 20 1 0 0 0 0 11 25 2 0 0 0 0 11 29 1 0 0 0 0 12 13 1 0 0 0 0 12 30 1 6 0 0 0 13 10 1 6 0 0 0 13 16 1 0 0 0 0 14 15 1 0 0 0 0 14 16 1 0 0 0 0 14 21 1 6 0 0 0 15 17 1 0 0 0 0 15 22 1 6 0 0 0 16 31 1 1 0 0 0 17 18 1 0 0 0 0 17 29 1 6 0 0 0 18 21 1 6 0 0 0 18 32 1 0 0 0 0 19 26 2 0 0 0 0 19 30 1 0 0 0 0 20 27 2 0 0 0 0 20 31 1 0 0 0 0 21 4 1 6 0 0 0 21 32 1 0 0 0 0 22 28 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	470.13
Volume:	435.983
LogP:	0.918
LogD:	0.776
LogS:	-3.222
# Rotatable Bonds:	8
TPSA:	128.73
# H-Bond Aceptor:	9
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.15
Synthetic Accessibility Score:	5.488
Fsp3:	0.727
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:	-5.274
MDCK Permeability:	8.817615162115544e-05
Pgp-inhibitor:	0.226
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.74
20% Bioavailability (F20%):	0.947
30% Bioavailability (F30%):	0.995

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.92
Plasma Protein Binding (PPB):	42.18827438354492%
Volume Distribution (VD):	1.013
Pgp-substrate:	60.97801971435547%

ADMET: Metabolism

CYP1A2-inhibitor:	0.041
CYP1A2-substrate:	0.078
CYP2C19-inhibitor:	0.018
CYP2C19-substrate:	0.072
CYP2C9-inhibitor:	0.009
CYP2C9-substrate:	0.025
CYP2D6-inhibitor:	0.027
CYP2D6-substrate:	0.074
CYP3A4-inhibitor:	0.347
CYP3A4-substrate:	0.243

ADMET: Excretion

Clearance (CL):	7.081
Half-life (T1/2):	0.738

ADMET: Toxicity

hERG Blockers:	0.089
Human Hepatotoxicity (H-HT):	0.925
Drug-inuced Liver Injury (DILI):	0.864
AMES Toxicity:	0.076
Rat Oral Acute Toxicity:	0.502
Maximum Recommended Daily Dose:	0.033
Skin Sensitization:	0.842
Carcinogencity:	0.137
Eye Corrosion:	0.634
Eye Irritation:	0.066
Respiratory Toxicity:	0.98

Download Data

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

Natural Product: NPC273242

Natural Product ID:	NPC273242
*Common Name:**	Eupachnilide F
IUPAC Name:	n.a.
Synonyms:	eupachnilide F
Standard InCHIKey:	CXXLXCCCYXUUOP-ROZFHUFVSA-N
Standard InCHI:	InChI=1S/C22H27ClO9/c1-9(5-6-24)19(26)30-12-7-22(28,8-23)15-14(16-13(12)10(2)20(27)31-16)21(4)18(32-21)17(15)29-11(3)25/h5,12-18,24,28H,2,6-8H2,1,3-4H3/b9-5+/t12-,13-,14+,15+,16+,17+,18-,21+,22+/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]2OC(=O)C)O1)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL464954
PubChem CID:	21578013
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]
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]
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]
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	=	0.87	ug.mL-1	PMID[452685]
NPT181	Cell Line	Bel-7402	Homo sapiens	IC50	=	3.7	ug.mL-1	PMID[452685]

☑ 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 NPC273242 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	290
0.1-0.2	1942
0.2-0.3	6765
0.3-0.4	15835
0.4-0.5	9990
0.5-0.6	5639
0.6-0.7	1933
0.7-0.8	266
0.8-0.85	25
0.85-0.9	8
0.9-0.95	0
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9905	High Similarity	NPC121816
0.9626	High Similarity	NPC255450
0.9626	High Similarity	NPC170692
0.8818	High Similarity	NPC35069
0.8818	High Similarity	NPC258711
0.8818	High Similarity	NPC95290
0.8818	High Similarity	NPC189338
0.8796	High Similarity	NPC68248
0.8785	High Similarity	NPC166115
0.8785	High Similarity	NPC54737
0.8716	High Similarity	NPC59489
0.8716	High Similarity	NPC139838
0.8716	High Similarity	NPC115352
0.8318	Intermediate Similarity	NPC471381
0.8318	Intermediate Similarity	NPC186861
0.8286	Intermediate Similarity	NPC472873
0.8273	Intermediate Similarity	NPC243998
0.8273	Intermediate Similarity	NPC223450
0.8269	Intermediate Similarity	NPC258216
0.8241	Intermediate Similarity	NPC150923
0.8224	Intermediate Similarity	NPC221615
0.8224	Intermediate Similarity	NPC45125
0.8208	Intermediate Similarity	NPC18019
0.8208	Intermediate Similarity	NPC24956
0.8173	Intermediate Similarity	NPC475925
0.8173	Intermediate Similarity	NPC155215
0.8131	Intermediate Similarity	NPC161493
0.8131	Intermediate Similarity	NPC471150
0.8113	Intermediate Similarity	NPC476053
0.8077	Intermediate Similarity	NPC216284
0.8037	Intermediate Similarity	NPC213078
0.8	Intermediate Similarity	NPC86077
0.7981	Intermediate Similarity	NPC472872
0.7981	Intermediate Similarity	NPC215556
0.7963	Intermediate Similarity	NPC181151
0.7946	Intermediate Similarity	NPC44004
0.7944	Intermediate Similarity	NPC67584
0.7944	Intermediate Similarity	NPC52044
0.7944	Intermediate Similarity	NPC170120
0.7944	Intermediate Similarity	NPC213698
0.7928	Intermediate Similarity	NPC124881
0.7885	Intermediate Similarity	NPC217983
0.7885	Intermediate Similarity	NPC207114
0.7885	Intermediate Similarity	NPC79549
0.787	Intermediate Similarity	NPC279621
0.785	Intermediate Similarity	NPC470010
0.785	Intermediate Similarity	NPC127019
0.785	Intermediate Similarity	NPC262133
0.785	Intermediate Similarity	NPC198853
0.785	Intermediate Similarity	NPC470013
0.785	Intermediate Similarity	NPC477131
0.785	Intermediate Similarity	NPC323008
0.783	Intermediate Similarity	NPC184063
0.783	Intermediate Similarity	NPC57304
0.783	Intermediate Similarity	NPC63193
0.783	Intermediate Similarity	NPC171360
0.783	Intermediate Similarity	NPC35959
0.783	Intermediate Similarity	NPC293001
0.783	Intermediate Similarity	NPC133888
0.783	Intermediate Similarity	NPC29821
0.7798	Intermediate Similarity	NPC474313
0.7778	Intermediate Similarity	NPC304886
0.7757	Intermediate Similarity	NPC472874
0.7748	Intermediate Similarity	NPC171759
0.7736	Intermediate Similarity	NPC54065
0.7736	Intermediate Similarity	NPC35809
0.7736	Intermediate Similarity	NPC19087
0.7736	Intermediate Similarity	NPC297474
0.7719	Intermediate Similarity	NPC26617
0.7706	Intermediate Similarity	NPC476315
0.7692	Intermediate Similarity	NPC64153
0.7692	Intermediate Similarity	NPC187661
0.7685	Intermediate Similarity	NPC474247
0.7664	Intermediate Similarity	NPC131209
0.7664	Intermediate Similarity	NPC133698
0.7661	Intermediate Similarity	NPC470973
0.7658	Intermediate Similarity	NPC70865
0.7652	Intermediate Similarity	NPC117604
0.7642	Intermediate Similarity	NPC155935
0.7642	Intermediate Similarity	NPC38392
0.7636	Intermediate Similarity	NPC311904
0.7636	Intermediate Similarity	NPC108475
0.7636	Intermediate Similarity	NPC170143
0.7636	Intermediate Similarity	NPC213947
0.7615	Intermediate Similarity	NPC220221
0.7615	Intermediate Similarity	NPC270013
0.7615	Intermediate Similarity	NPC14961
0.7615	Intermediate Similarity	NPC163228
0.7603	Intermediate Similarity	NPC477092
0.7596	Intermediate Similarity	NPC300082
0.7596	Intermediate Similarity	NPC204105
0.7596	Intermediate Similarity	NPC284534
0.7593	Intermediate Similarity	NPC125674
0.7593	Intermediate Similarity	NPC475838
0.7593	Intermediate Similarity	NPC228451
0.7583	Intermediate Similarity	NPC475305
0.757	Intermediate Similarity	NPC301969
0.757	Intermediate Similarity	NPC37607
0.7568	Intermediate Similarity	NPC474213
0.7547	Intermediate Similarity	NPC471149
0.7545	Intermediate Similarity	NPC230800
0.7545	Intermediate Similarity	NPC98165
0.7544	Intermediate Similarity	NPC100487
0.7523	Intermediate Similarity	NPC474035
0.7523	Intermediate Similarity	NPC81386
0.7521	Intermediate Similarity	NPC50223
0.7521	Intermediate Similarity	NPC257240
0.7521	Intermediate Similarity	NPC475401
0.75	Intermediate Similarity	NPC224386
0.75	Intermediate Similarity	NPC288876
0.75	Intermediate Similarity	NPC194859
0.748	Intermediate Similarity	NPC475371
0.7477	Intermediate Similarity	NPC4986
0.7477	Intermediate Similarity	NPC283409
0.7455	Intermediate Similarity	NPC224689
0.7455	Intermediate Similarity	NPC36954
0.7453	Intermediate Similarity	NPC270270
0.7453	Intermediate Similarity	NPC24728
0.7436	Intermediate Similarity	NPC477102
0.7431	Intermediate Similarity	NPC475788
0.7431	Intermediate Similarity	NPC475912
0.7431	Intermediate Similarity	NPC212486
0.7417	Intermediate Similarity	NPC265290
0.7417	Intermediate Similarity	NPC305044
0.7411	Intermediate Similarity	NPC187268
0.7411	Intermediate Similarity	NPC473326
0.7411	Intermediate Similarity	NPC249171
0.7411	Intermediate Similarity	NPC49833
0.7404	Intermediate Similarity	NPC128246
0.7404	Intermediate Similarity	NPC111409
0.7404	Intermediate Similarity	NPC245665
0.7398	Intermediate Similarity	NPC143755
0.7391	Intermediate Similarity	NPC474741
0.7387	Intermediate Similarity	NPC126156
0.7387	Intermediate Similarity	NPC91771
0.7387	Intermediate Similarity	NPC142529
0.7383	Intermediate Similarity	NPC91248
0.7383	Intermediate Similarity	NPC224652
0.7383	Intermediate Similarity	NPC178875
0.7373	Intermediate Similarity	NPC477103
0.7373	Intermediate Similarity	NPC41551
0.7373	Intermediate Similarity	NPC193741
0.7368	Intermediate Similarity	NPC80144
0.7364	Intermediate Similarity	NPC57405
0.7364	Intermediate Similarity	NPC303942
0.7358	Intermediate Similarity	NPC470242
0.7358	Intermediate Similarity	NPC304558
0.7358	Intermediate Similarity	NPC56593
0.7333	Intermediate Similarity	NPC106395
0.7333	Intermediate Similarity	NPC46269
0.7328	Intermediate Similarity	NPC470980
0.7321	Intermediate Similarity	NPC477949
0.7321	Intermediate Similarity	NPC236580
0.7321	Intermediate Similarity	NPC304445
0.7311	Intermediate Similarity	NPC475495
0.7311	Intermediate Similarity	NPC474750
0.7308	Intermediate Similarity	NPC246076
0.7304	Intermediate Similarity	NPC475871
0.7304	Intermediate Similarity	NPC473148
0.7304	Intermediate Similarity	NPC475945
0.7297	Intermediate Similarity	NPC471141
0.729	Intermediate Similarity	NPC118601
0.7288	Intermediate Similarity	NPC208307
0.7281	Intermediate Similarity	NPC201718
0.7281	Intermediate Similarity	NPC67296
0.7281	Intermediate Similarity	NPC477950
0.7273	Intermediate Similarity	NPC133677
0.7273	Intermediate Similarity	NPC67290
0.7273	Intermediate Similarity	NPC135776
0.7273	Intermediate Similarity	NPC179746
0.7273	Intermediate Similarity	NPC308656
0.7273	Intermediate Similarity	NPC60386
0.7273	Intermediate Similarity	NPC473263
0.7273	Intermediate Similarity	NPC138303
0.7273	Intermediate Similarity	NPC471380
0.7273	Intermediate Similarity	NPC476300
0.7273	Intermediate Similarity	NPC473234
0.7273	Intermediate Similarity	NPC81419
0.7273	Intermediate Similarity	NPC473273
0.7266	Intermediate Similarity	NPC470850
0.7257	Intermediate Similarity	NPC469918
0.7257	Intermediate Similarity	NPC223700
0.7257	Intermediate Similarity	NPC117066
0.7257	Intermediate Similarity	NPC96399
0.7257	Intermediate Similarity	NPC469919
0.725	Intermediate Similarity	NPC138757
0.725	Intermediate Similarity	NPC475851
0.725	Intermediate Similarity	NPC475924
0.725	Intermediate Similarity	NPC76550
0.725	Intermediate Similarity	NPC477093
0.725	Intermediate Similarity	NPC123855
0.725	Intermediate Similarity	NPC473522
0.725	Intermediate Similarity	NPC475277
0.7248	Intermediate Similarity	NPC475748
0.7248	Intermediate Similarity	NPC475855
0.7241	Intermediate Similarity	NPC203659
0.7236	Intermediate Similarity	NPC475372
0.7236	Intermediate Similarity	NPC161060
0.7232	Intermediate Similarity	NPC476009
0.7232	Intermediate Similarity	NPC473859

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 NPC273242 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	277
0.1-0.2	2519
0.2-0.3	4059
0.3-0.4	1689
0.4-0.5	387
0.5-0.6	192
0.6-0.7	23
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
0.7719	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7521	Intermediate Similarity	NPD6371	Approved
0.7477	Intermediate Similarity	NPD1695	Approved
0.7091	Intermediate Similarity	NPD46	Approved
0.7091	Intermediate Similarity	NPD6698	Approved
0.6967	Remote Similarity	NPD6053	Discontinued
0.6881	Remote Similarity	NPD4249	Approved
0.6818	Remote Similarity	NPD4251	Approved
0.6818	Remote Similarity	NPD4250	Approved
0.6786	Remote Similarity	NPD7838	Discovery
0.6696	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6637	Remote Similarity	NPD5785	Approved
0.6636	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6606	Remote Similarity	NPD5362	Discontinued
0.6538	Remote Similarity	NPD5983	Phase 2
0.6519	Remote Similarity	NPD5956	Approved
0.6486	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6486	Remote Similarity	NPD5363	Approved
0.6484	Remote Similarity	NPD7115	Discovery
0.6481	Remote Similarity	NPD4820	Approved
0.6481	Remote Similarity	NPD4821	Approved
0.6481	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6481	Remote Similarity	NPD4819	Approved
0.6481	Remote Similarity	NPD4822	Approved
0.6417	Remote Similarity	NPD5344	Discontinued
0.6387	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6378	Remote Similarity	NPD4632	Approved
0.6371	Remote Similarity	NPD6686	Approved
0.637	Remote Similarity	NPD6033	Approved
0.6356	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.6349	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6343	Remote Similarity	NPD7507	Approved
0.6343	Remote Similarity	NPD6336	Discontinued
0.6341	Remote Similarity	NPD6008	Approved
0.6306	Remote Similarity	NPD7154	Phase 3
0.6296	Remote Similarity	NPD4271	Approved
0.6296	Remote Similarity	NPD4268	Approved
0.6293	Remote Similarity	NPD7983	Approved
0.626	Remote Similarity	NPD7100	Approved
0.625	Remote Similarity	NPD4225	Approved
0.6231	Remote Similarity	NPD6009	Approved
0.6216	Remote Similarity	NPD6435	Approved
0.6216	Remote Similarity	NPD4269	Approved
0.6216	Remote Similarity	NPD4270	Approved
0.6212	Remote Similarity	NPD6319	Approved
0.6204	Remote Similarity	NPD7319	Approved
0.6198	Remote Similarity	NPD7640	Approved
0.6198	Remote Similarity	NPD7639	Approved
0.6198	Remote Similarity	NPD6648	Approved
0.6183	Remote Similarity	NPD6314	Approved
0.6183	Remote Similarity	NPD6335	Approved
0.6183	Remote Similarity	NPD6313	Approved
0.6165	Remote Similarity	NPD8033	Approved
0.6161	Remote Similarity	NPD5331	Approved
0.6161	Remote Similarity	NPD5332	Approved
0.6148	Remote Similarity	NPD7492	Approved
0.6142	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.614	Remote Similarity	NPD5786	Approved
0.6136	Remote Similarity	NPD4522	Approved
0.6136	Remote Similarity	NPD7101	Approved
0.6126	Remote Similarity	NPD5369	Approved
0.6126	Remote Similarity	NPD4790	Discontinued
0.6116	Remote Similarity	NPD7638	Approved
0.6103	Remote Similarity	NPD6616	Approved
0.609	Remote Similarity	NPD6054	Approved
0.6063	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6061	Remote Similarity	NPD7328	Approved
0.6061	Remote Similarity	NPD7327	Approved
0.6058	Remote Similarity	NPD7078	Approved
0.605	Remote Similarity	NPD5282	Discontinued
0.6047	Remote Similarity	NPD8297	Approved
0.6045	Remote Similarity	NPD6015	Approved
0.6045	Remote Similarity	NPD6016	Approved
0.6036	Remote Similarity	NPD4252	Approved
0.6036	Remote Similarity	NPD5368	Approved
0.6015	Remote Similarity	NPD7516	Approved
0.6014	Remote Similarity	NPD7736	Approved
0.6	Remote Similarity	NPD6370	Approved
0.6	Remote Similarity	NPD5988	Approved
0.597	Remote Similarity	NPD8294	Approved
0.597	Remote Similarity	NPD6059	Approved
0.597	Remote Similarity	NPD8377	Approved
0.5969	Remote Similarity	NPD6650	Approved
0.5969	Remote Similarity	NPD6649	Approved
0.5969	Remote Similarity	NPD5215	Approved
0.5942	Remote Similarity	NPD8293	Discontinued
0.5938	Remote Similarity	NPD6372	Approved
0.5938	Remote Similarity	NPD6373	Approved
0.5926	Remote Similarity	NPD8378	Approved
0.5926	Remote Similarity	NPD8515	Approved
0.5926	Remote Similarity	NPD8516	Approved
0.5926	Remote Similarity	NPD8296	Approved
0.5926	Remote Similarity	NPD8335	Approved
0.5926	Remote Similarity	NPD8517	Approved
0.5926	Remote Similarity	NPD8379	Approved
0.5926	Remote Similarity	NPD8380	Approved
0.5926	Remote Similarity	NPD8513	Phase 3
0.5926	Remote Similarity	NPD7503	Approved
0.5906	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.5906	Remote Similarity	NPD6412	Phase 2
0.5906	Remote Similarity	NPD5697	Approved
0.5902	Remote Similarity	NPD6084	Phase 2
0.5902	Remote Similarity	NPD6083	Phase 2
0.5891	Remote Similarity	NPD5169	Approved
0.5878	Remote Similarity	NPD8133	Approved
0.587	Remote Similarity	NPD8273	Phase 1
0.5868	Remote Similarity	NPD5695	Phase 3
0.5859	Remote Similarity	NPD6881	Approved
0.5859	Remote Similarity	NPD6899	Approved
0.5859	Remote Similarity	NPD7320	Approved
0.5856	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.5854	Remote Similarity	NPD5696	Approved
0.5846	Remote Similarity	NPD5217	Approved
0.5846	Remote Similarity	NPD5216	Approved
0.5846	Remote Similarity	NPD5127	Approved
0.5839	Remote Similarity	NPD7604	Phase 2
0.5833	Remote Similarity	NPD5167	Approved
0.5833	Remote Similarity	NPD5779	Approved
0.5833	Remote Similarity	NPD5778	Approved
0.5827	Remote Similarity	NPD5739	Approved
0.5827	Remote Similarity	NPD7128	Approved
0.5827	Remote Similarity	NPD6402	Approved
0.5827	Remote Similarity	NPD6675	Approved
0.5826	Remote Similarity	NPD5766	Clinical (unspecified phase)
0.5814	Remote Similarity	NPD6013	Approved
0.5814	Remote Similarity	NPD6012	Approved
0.5814	Remote Similarity	NPD6014	Approved
0.5802	Remote Similarity	NPD6882	Approved
0.5781	Remote Similarity	NPD6614	Approved
0.5781	Remote Similarity	NPD5701	Approved
0.5769	Remote Similarity	NPD7102	Approved
0.5769	Remote Similarity	NPD6883	Approved
0.5769	Remote Similarity	NPD7290	Approved
0.575	Remote Similarity	NPD7637	Suspended
0.5748	Remote Similarity	NPD4056	Clinical (unspecified phase)
0.5748	Remote Similarity	NPD4057	Clinical (unspecified phase)
0.5738	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.5736	Remote Similarity	NPD6011	Approved
0.5736	Remote Similarity	NPD5128	Approved
0.5725	Remote Similarity	NPD8130	Phase 1
0.5725	Remote Similarity	NPD6869	Approved
0.5725	Remote Similarity	NPD6617	Approved
0.5725	Remote Similarity	NPD6847	Approved
0.5725	Remote Similarity	NPD7642	Approved
0.5714	Remote Similarity	NPD8074	Phase 3
0.5714	Remote Similarity	NPD5091	Approved
0.5714	Remote Similarity	NPD7632	Discontinued
0.5714	Remote Similarity	NPD5211	Phase 2
0.5704	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.5702	Remote Similarity	NPD6399	Phase 3
0.5672	Remote Similarity	NPD6868	Approved
0.5664	Remote Similarity	NPD7260	Phase 2
0.5652	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.5649	Remote Similarity	NPD4634	Approved
0.5645	Remote Similarity	NPD5959	Approved
0.5641	Remote Similarity	NPD1694	Approved
0.5635	Remote Similarity	NPD1700	Approved
0.5625	Remote Similarity	NPD6845	Suspended
0.5625	Remote Similarity	NPD5141	Approved
0.562	Remote Similarity	NPD5693	Phase 1
0.562	Remote Similarity	NPD5281	Approved
0.562	Remote Similarity	NPD5284	Approved
0.5612	Remote Similarity	NPD7829	Approved
0.5612	Remote Similarity	NPD7830	Approved
0.561	Remote Similarity	NPD4629	Approved
0.561	Remote Similarity	NPD5654	Approved
0.561	Remote Similarity	NPD5210	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