NPASS Compound

Structure

CID150923 OpenBabel06191715522D 27 29 0 0 1 0 0 0 0 0999 V2000 -1.3763 -6.0290 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0024 -4.8707 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3272 -2.2213 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9445 1.5248 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3835 -5.9096 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7782 -2.6635 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3288 -0.4417 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4546 -2.4237 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0096 -4.9901 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6581 -1.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5410 -2.0169 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5111 -1.0174 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7971 -2.4703 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.0341 0.5138 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.3364 -1.5827 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7110 -0.4175 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.7431 -0.6691 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.5903 -4.1899 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0342 0.5288 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.5591 -3.4182 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.6339 1.3140 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5831 -4.3093 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7796 -0.0933 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1268 0.9491 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1972 -3.2704 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 2 0 0 0 0 5 9 2 0 0 0 0 6 11 1 0 0 0 0 6 13 1 0 0 0 0 7 12 1 0 0 0 0 7 14 1 0 0 0 0 8 11 1 0 0 0 0 8 21 1 0 0 0 0 9 18 1 0 0 0 0 10 19 1 0 0 0 0 11 12 2 0 0 0 0 12 16 1 0 0 0 0 13 15 1 0 0 0 0 13 26 1 6 0 0 0 14 20 1 6 0 0 0 14 22 1 0 0 0 0 15 10 1 6 0 0 0 15 17 1 0 0 0 0 16 17 1 0 0 0 0 16 20 1 6 0 0 0 17 27 1 1 0 0 0 18 23 2 0 0 0 0 18 26 1 0 0 0 0 19 24 2 0 0 0 0 19 27 1 0 0 0 0 20 4 1 1 0 0 0 20 25 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	378.17
Volume:	377.156
LogP:	0.943
LogD:	0.731
LogS:	-2.652
# Rotatable Bonds:	4
TPSA:	113.29
# H-Bond Aceptor:	7
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.378
Synthetic Accessibility Score:	4.992
Fsp3:	0.6
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	2
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.892
MDCK Permeability:	5.4671265388606116e-05
Pgp-inhibitor:	0.002
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.756
20% Bioavailability (F20%):	0.02
30% Bioavailability (F30%):	0.9

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.276
Plasma Protein Binding (PPB):	51.51201629638672%
Volume Distribution (VD):	1.189
Pgp-substrate:	33.87967300415039%

ADMET: Metabolism

CYP1A2-inhibitor:	0.044
CYP1A2-substrate:	0.059
CYP2C19-inhibitor:	0.027
CYP2C19-substrate:	0.189
CYP2C9-inhibitor:	0.062
CYP2C9-substrate:	0.045
CYP2D6-inhibitor:	0.006
CYP2D6-substrate:	0.063
CYP3A4-inhibitor:	0.167
CYP3A4-substrate:	0.237

ADMET: Excretion

Clearance (CL):	4.856
Half-life (T1/2):	0.84

ADMET: Toxicity

hERG Blockers:	0.038
Human Hepatotoxicity (H-HT):	0.326
Drug-inuced Liver Injury (DILI):	0.555
AMES Toxicity:	0.05
Rat Oral Acute Toxicity:	0.963
Maximum Recommended Daily Dose:	0.868
Skin Sensitization:	0.561
Carcinogencity:	0.339
Eye Corrosion:	0.088
Eye Irritation:	0.142
Respiratory Toxicity:	0.982

Download Data

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

Natural Product: NPC150923

Natural Product ID:	NPC150923
*Common Name:**	Eupachinilide A
IUPAC Name:	[(3aR,4R,8S,9R,9aS,9bS)-8,9-dihydroxy-6-(hydroxymethyl)-9-methyl-3-methylidene-2-oxo-4,5,7,8,9a,9b-hexahydro-3aH-azuleno[4,5-b]furan-4-yl] (Z)-2-methylbut-2-enoate
Synonyms:
Standard InCHIKey:	CITDRWAOOHPFCD-XFTYBKLESA-N
Standard InCHI:	InChI=1S/C20H26O7/c1-5-9(2)18(23)26-13-6-11(8-21)12-7-14(22)20(4,25)16(12)17-15(13)10(3)19(24)27-17/h5,13-17,21-22,25H,3,6-8H2,1-2,4H3/b9-5-/t13-,14+,15-,16+,17+,20+/m1/s1
SMILES:	C/C=C(C(=O)O[C@@H]1CC(=C2[C@@H]([C@@H]3[C@@H]1C(=C)C(=O)O3)[C@@]([C@H](C2)O)(C)O)CO)/C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL516684
PubChem CID:	21578008
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:0001771] Germacranolides 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	=	10.8	ug.mL-1	PMID[506415]
NPT181	Cell Line	Bel-7402	Homo sapiens	IC50	=	72.2	ug.mL-1	PMID[506415]

☑ 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 NPC150923 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	235
0.1-0.2	1239
0.2-0.3	4718
0.3-0.4	10198
0.4-0.5	13194
0.5-0.6	7587
0.6-0.7	4076
0.7-0.8	1285
0.8-0.85	132
0.85-0.9	24
0.9-0.95	7
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9263	High Similarity	NPC161493
0.9255	High Similarity	NPC170120
0.9255	High Similarity	NPC52044
0.9255	High Similarity	NPC67584
0.9255	High Similarity	NPC213698
0.9158	High Similarity	NPC213078
0.9149	High Similarity	NPC127019
0.9072	High Similarity	NPC70865
0.899	High Similarity	NPC124881
0.8969	High Similarity	NPC221615
0.8936	High Similarity	NPC475925
0.89	High Similarity	NPC100487
0.8889	High Similarity	NPC86077
0.8854	High Similarity	NPC304886
0.8854	High Similarity	NPC472873
0.883	High Similarity	NPC37607
0.883	High Similarity	NPC301969
0.8812	High Similarity	NPC54737
0.8812	High Similarity	NPC243998
0.8763	High Similarity	NPC24956
0.8763	High Similarity	NPC18019
0.875	High Similarity	NPC262133
0.875	High Similarity	NPC477131
0.875	High Similarity	NPC470013
0.875	High Similarity	NPC470010
0.875	High Similarity	NPC323008
0.875	High Similarity	NPC198853
0.8673	High Similarity	NPC471150
0.866	High Similarity	NPC224689
0.8646	High Similarity	NPC475912
0.8627	High Similarity	NPC223450
0.8617	High Similarity	NPC217983
0.8617	High Similarity	NPC207114
0.8602	High Similarity	NPC67493
0.8586	High Similarity	NPC187268
0.8558	High Similarity	NPC139838
0.8558	High Similarity	NPC59489
0.8544	High Similarity	NPC26617
0.8542	High Similarity	NPC184063
0.8542	High Similarity	NPC131209
0.8542	High Similarity	NPC133698
0.8526	High Similarity	NPC215556
0.8495	Intermediate Similarity	NPC235792
0.8485	Intermediate Similarity	NPC311904
0.8485	Intermediate Similarity	NPC474313
0.8469	Intermediate Similarity	NPC14961
0.8469	Intermediate Similarity	NPC270013
0.8469	Intermediate Similarity	NPC36954
0.8454	Intermediate Similarity	NPC228451
0.8454	Intermediate Similarity	NPC475838
0.8454	Intermediate Similarity	NPC179746
0.8454	Intermediate Similarity	NPC81419
0.8454	Intermediate Similarity	NPC125674
0.8438	Intermediate Similarity	NPC297474
0.8438	Intermediate Similarity	NPC54065
0.8438	Intermediate Similarity	NPC216284
0.8438	Intermediate Similarity	NPC475855
0.8438	Intermediate Similarity	NPC19087
0.8438	Intermediate Similarity	NPC473448
0.8438	Intermediate Similarity	NPC129419
0.8421	Intermediate Similarity	NPC79549
0.8421	Intermediate Similarity	NPC202672
0.8421	Intermediate Similarity	NPC224652
0.8416	Intermediate Similarity	NPC171759
0.8404	Intermediate Similarity	NPC187661
0.8404	Intermediate Similarity	NPC64153
0.8387	Intermediate Similarity	NPC156485
0.8384	Intermediate Similarity	NPC279621
0.8367	Intermediate Similarity	NPC81386
0.8367	Intermediate Similarity	NPC474338
0.8367	Intermediate Similarity	NPC474247
0.8367	Intermediate Similarity	NPC474035
0.8351	Intermediate Similarity	NPC171360
0.8351	Intermediate Similarity	NPC12172
0.8351	Intermediate Similarity	NPC184463
0.8351	Intermediate Similarity	NPC29821
0.8351	Intermediate Similarity	NPC57304
0.8351	Intermediate Similarity	NPC35959
0.8351	Intermediate Similarity	NPC30515
0.8351	Intermediate Similarity	NPC63193
0.8351	Intermediate Similarity	NPC293001
0.8351	Intermediate Similarity	NPC208886
0.8351	Intermediate Similarity	NPC133888
0.8333	Intermediate Similarity	NPC295312
0.8333	Intermediate Similarity	NPC38392
0.8333	Intermediate Similarity	NPC268298
0.8333	Intermediate Similarity	NPC121816
0.8333	Intermediate Similarity	NPC155935
0.8318	Intermediate Similarity	NPC258711
0.8318	Intermediate Similarity	NPC35069
0.8317	Intermediate Similarity	NPC471381
0.8317	Intermediate Similarity	NPC186861
0.8316	Intermediate Similarity	NPC160138
0.8302	Intermediate Similarity	NPC257240
0.83	Intermediate Similarity	NPC170143
0.83	Intermediate Similarity	NPC181151
0.83	Intermediate Similarity	NPC108475
0.83	Intermediate Similarity	NPC213947
0.8298	Intermediate Similarity	NPC165162
0.8286	Intermediate Similarity	NPC117604
0.8283	Intermediate Similarity	NPC469873
0.8283	Intermediate Similarity	NPC476053
0.8269	Intermediate Similarity	NPC166115
0.8265	Intermediate Similarity	NPC212486
0.8265	Intermediate Similarity	NPC476300
0.8265	Intermediate Similarity	NPC258216
0.8265	Intermediate Similarity	NPC135776
0.8252	Intermediate Similarity	NPC475871
0.8252	Intermediate Similarity	NPC474775
0.8252	Intermediate Similarity	NPC475945
0.8247	Intermediate Similarity	NPC476004
0.8247	Intermediate Similarity	NPC474761
0.8247	Intermediate Similarity	NPC51004
0.8247	Intermediate Similarity	NPC144133
0.8247	Intermediate Similarity	NPC35809
0.8247	Intermediate Similarity	NPC179394
0.8241	Intermediate Similarity	NPC273242
0.8229	Intermediate Similarity	NPC91248
0.8218	Intermediate Similarity	NPC473326
0.8218	Intermediate Similarity	NPC45125
0.8211	Intermediate Similarity	NPC475461
0.8211	Intermediate Similarity	NPC305475
0.8211	Intermediate Similarity	NPC107787
0.82	Intermediate Similarity	NPC476315
0.82	Intermediate Similarity	NPC230800
0.8191	Intermediate Similarity	NPC224386
0.8191	Intermediate Similarity	NPC194859
0.8173	Intermediate Similarity	NPC203659
0.8172	Intermediate Similarity	NPC89555
0.8163	Intermediate Similarity	NPC155215
0.8163	Intermediate Similarity	NPC473321
0.8155	Intermediate Similarity	NPC474747
0.8148	Intermediate Similarity	NPC123855
0.8148	Intermediate Similarity	NPC76550
0.8148	Intermediate Similarity	NPC189338
0.8148	Intermediate Similarity	NPC95290
0.8144	Intermediate Similarity	NPC212664
0.8144	Intermediate Similarity	NPC473564
0.8144	Intermediate Similarity	NPC307411
0.8137	Intermediate Similarity	NPC288876
0.8125	Intermediate Similarity	NPC237540
0.8119	Intermediate Similarity	NPC477949
0.8105	Intermediate Similarity	NPC78089
0.8105	Intermediate Similarity	NPC284534
0.8105	Intermediate Similarity	NPC255307
0.8105	Intermediate Similarity	NPC300082
0.8105	Intermediate Similarity	NPC204105
0.81	Intermediate Similarity	NPC163228
0.81	Intermediate Similarity	NPC37408
0.81	Intermediate Similarity	NPC220221
0.81	Intermediate Similarity	NPC471141
0.8095	Intermediate Similarity	NPC179891
0.8095	Intermediate Similarity	NPC44004
0.8091	Intermediate Similarity	NPC255450
0.8091	Intermediate Similarity	NPC170692
0.8085	Intermediate Similarity	NPC250315
0.8085	Intermediate Similarity	NPC128246
0.8081	Intermediate Similarity	NPC288240
0.8081	Intermediate Similarity	NPC273579
0.8081	Intermediate Similarity	NPC295204
0.8081	Intermediate Similarity	NPC162205
0.8081	Intermediate Similarity	NPC475788
0.8077	Intermediate Similarity	NPC110989
0.8073	Intermediate Similarity	NPC46269
0.8073	Intermediate Similarity	NPC106395
0.8061	Intermediate Similarity	NPC473619
0.8058	Intermediate Similarity	NPC474742
0.8056	Intermediate Similarity	NPC474750
0.8041	Intermediate Similarity	NPC473715
0.8041	Intermediate Similarity	NPC153805
0.8041	Intermediate Similarity	NPC476803
0.8039	Intermediate Similarity	NPC474213
0.8037	Intermediate Similarity	NPC477102
0.8021	Intermediate Similarity	NPC56593
0.802	Intermediate Similarity	NPC126156
0.802	Intermediate Similarity	NPC142529
0.802	Intermediate Similarity	NPC91771
0.8	Intermediate Similarity	NPC115786
0.8	Intermediate Similarity	NPC303942
0.8	Intermediate Similarity	NPC57405
0.8	Intermediate Similarity	NPC114979
0.8	Intermediate Similarity	NPC472957
0.8	Intermediate Similarity	NPC138303
0.8	Intermediate Similarity	NPC191476
0.8	Intermediate Similarity	NPC309190
0.8	Intermediate Similarity	NPC476804
0.8	Intermediate Similarity	NPC165287
0.8	Intermediate Similarity	NPC472958
0.8	Intermediate Similarity	NPC133677
0.8	Intermediate Similarity	NPC67290
0.8	Intermediate Similarity	NPC474741
0.7982	Intermediate Similarity	NPC138757
0.7982	Intermediate Similarity	NPC126691
0.7981	Intermediate Similarity	NPC140591
0.7981	Intermediate Similarity	NPC197835
0.7981	Intermediate Similarity	NPC291500
0.7981	Intermediate Similarity	NPC189609
0.7981	Intermediate Similarity	NPC303653
0.7981	Intermediate Similarity	NPC225353
0.7979	Intermediate Similarity	NPC246076

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 NPC150923 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	217
0.1-0.2	1879
0.2-0.3	3757
0.3-0.4	2266
0.4-0.5	636
0.5-0.6	262
0.6-0.7	109
0.7-0.8	23
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
0.8544	High Similarity	NPD7899	Clinical (unspecified phase)
0.8302	Intermediate Similarity	NPD6371	Approved
0.7959	Intermediate Similarity	NPD1695	Approved
0.7835	Intermediate Similarity	NPD4249	Approved
0.7755	Intermediate Similarity	NPD4250	Approved
0.7755	Intermediate Similarity	NPD4251	Approved
0.77	Intermediate Similarity	NPD5785	Approved
0.77	Intermediate Similarity	NPD6698	Approved
0.77	Intermediate Similarity	NPD46	Approved
0.7658	Intermediate Similarity	NPD6053	Discontinued
0.7573	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7551	Intermediate Similarity	NPD5363	Approved
0.7526	Intermediate Similarity	NPD5362	Discontinued
0.7396	Intermediate Similarity	NPD4819	Approved
0.7396	Intermediate Similarity	NPD5790	Clinical (unspecified phase)
0.7396	Intermediate Similarity	NPD4822	Approved
0.7396	Intermediate Similarity	NPD4820	Approved
0.7396	Intermediate Similarity	NPD4821	Approved
0.7374	Intermediate Similarity	NPD6082	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD7838	Discovery
0.7245	Intermediate Similarity	NPD4269	Approved
0.7245	Intermediate Similarity	NPD4270	Approved
0.72	Intermediate Similarity	NPD1733	Clinical (unspecified phase)
0.7196	Intermediate Similarity	NPD4225	Approved
0.7188	Intermediate Similarity	NPD4268	Approved
0.7188	Intermediate Similarity	NPD4271	Approved
0.7172	Intermediate Similarity	NPD7154	Phase 3
0.7143	Intermediate Similarity	NPD6686	Approved
0.7143	Intermediate Similarity	NPD5369	Approved
0.713	Intermediate Similarity	NPD7640	Approved
0.713	Intermediate Similarity	NPD7639	Approved
0.7129	Intermediate Similarity	NPD5786	Approved
0.7115	Intermediate Similarity	NPD7983	Approved
0.7105	Intermediate Similarity	NPD8413	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD6435	Approved
0.7064	Intermediate Similarity	NPD5344	Discontinued
0.7041	Intermediate Similarity	NPD4252	Approved
0.7037	Intermediate Similarity	NPD7638	Approved
0.7037	Intermediate Similarity	NPD8029	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD5332	Approved
0.7	Intermediate Similarity	NPD5331	Approved
0.6981	Remote Similarity	NPD5282	Discontinued
0.697	Remote Similarity	NPD4790	Discontinued
0.6949	Remote Similarity	NPD7115	Discovery
0.6911	Remote Similarity	NPD7507	Approved
0.6869	Remote Similarity	NPD5368	Approved
0.6814	Remote Similarity	NPD6008	Approved
0.6777	Remote Similarity	NPD6319	Approved
0.6754	Remote Similarity	NPD6412	Phase 2
0.6746	Remote Similarity	NPD7319	Approved
0.6729	Remote Similarity	NPD5778	Approved
0.6729	Remote Similarity	NPD5779	Approved
0.6695	Remote Similarity	NPD4632	Approved
0.6694	Remote Similarity	NPD7492	Approved
0.6667	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6648	Approved
0.664	Remote Similarity	NPD6616	Approved
0.6639	Remote Similarity	NPD6054	Approved
0.6638	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6636	Remote Similarity	NPD6084	Phase 2
0.6636	Remote Similarity	NPD6083	Phase 2
0.6612	Remote Similarity	NPD7328	Approved
0.6612	Remote Similarity	NPD7327	Approved
0.6609	Remote Similarity	NPD5697	Approved
0.6606	Remote Similarity	NPD5695	Phase 3
0.6587	Remote Similarity	NPD7078	Approved
0.6585	Remote Similarity	NPD8515	Approved
0.6585	Remote Similarity	NPD8513	Phase 3
0.6585	Remote Similarity	NPD6016	Approved
0.6585	Remote Similarity	NPD8517	Approved
0.6585	Remote Similarity	NPD8516	Approved
0.6585	Remote Similarity	NPD6015	Approved
0.6585	Remote Similarity	NPD8033	Approved
0.6577	Remote Similarity	NPD5696	Approved
0.6569	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6557	Remote Similarity	NPD7516	Approved
0.6552	Remote Similarity	NPD7320	Approved
0.6552	Remote Similarity	NPD6899	Approved
0.6552	Remote Similarity	NPD6881	Approved
0.6549	Remote Similarity	NPD7632	Discontinued
0.6538	Remote Similarity	NPD1694	Approved
0.6535	Remote Similarity	NPD7736	Approved
0.6532	Remote Similarity	NPD6370	Approved
0.6532	Remote Similarity	NPD5988	Approved
0.6525	Remote Similarity	NPD6649	Approved
0.6525	Remote Similarity	NPD6650	Approved
0.6522	Remote Similarity	NPD6402	Approved
0.6522	Remote Similarity	NPD5739	Approved
0.6522	Remote Similarity	NPD7128	Approved
0.6522	Remote Similarity	NPD6675	Approved
0.6504	Remote Similarity	NPD6059	Approved
0.6504	Remote Similarity	NPD8377	Approved
0.6504	Remote Similarity	NPD8294	Approved
0.6496	Remote Similarity	NPD6373	Approved
0.6496	Remote Similarity	NPD6012	Approved
0.6496	Remote Similarity	NPD6372	Approved
0.6496	Remote Similarity	NPD6013	Approved
0.6496	Remote Similarity	NPD6014	Approved
0.6481	Remote Similarity	NPD7637	Suspended
0.6471	Remote Similarity	NPD8297	Approved
0.6466	Remote Similarity	NPD5701	Approved
0.6457	Remote Similarity	NPD8293	Discontinued
0.6452	Remote Similarity	NPD8379	Approved
0.6452	Remote Similarity	NPD8380	Approved
0.6452	Remote Similarity	NPD8296	Approved
0.6452	Remote Similarity	NPD8335	Approved
0.6452	Remote Similarity	NPD8378	Approved
0.6452	Remote Similarity	NPD7503	Approved
0.6441	Remote Similarity	NPD6883	Approved
0.6441	Remote Similarity	NPD7290	Approved
0.6441	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6441	Remote Similarity	NPD4634	Approved
0.6441	Remote Similarity	NPD7102	Approved
0.6422	Remote Similarity	NPD6399	Phase 3
0.641	Remote Similarity	NPD6011	Approved
0.6404	Remote Similarity	NPD5211	Phase 2
0.6393	Remote Similarity	NPD6009	Approved
0.6387	Remote Similarity	NPD6847	Approved
0.6387	Remote Similarity	NPD8130	Phase 1
0.6387	Remote Similarity	NPD6869	Approved
0.6387	Remote Similarity	NPD6617	Approved
0.6355	Remote Similarity	NPD6903	Approved
0.6333	Remote Similarity	NPD6882	Approved
0.633	Remote Similarity	NPD5281	Approved
0.633	Remote Similarity	NPD5284	Approved
0.633	Remote Similarity	NPD5693	Phase 1
0.6328	Remote Similarity	NPD8074	Phase 3
0.6321	Remote Similarity	NPD7521	Approved
0.6321	Remote Similarity	NPD5330	Approved
0.6321	Remote Similarity	NPD7334	Approved
0.6321	Remote Similarity	NPD7146	Approved
0.6321	Remote Similarity	NPD6409	Approved
0.6321	Remote Similarity	NPD6684	Approved
0.632	Remote Similarity	NPD5983	Phase 2
0.6308	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6306	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6306	Remote Similarity	NPD4629	Approved
0.6306	Remote Similarity	NPD5210	Approved
0.6296	Remote Similarity	NPD4753	Phase 2
0.6293	Remote Similarity	NPD5141	Approved
0.6286	Remote Similarity	NPD3665	Phase 1
0.6286	Remote Similarity	NPD3666	Approved
0.6286	Remote Similarity	NPD3133	Approved
0.6286	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6262	Remote Similarity	NPD7524	Approved
0.625	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.625	Remote Similarity	NPD7839	Suspended
0.625	Remote Similarity	NPD5209	Approved
0.6239	Remote Similarity	NPD5207	Approved
0.6228	Remote Similarity	NPD5286	Approved
0.6228	Remote Similarity	NPD5285	Approved
0.6228	Remote Similarity	NPD4696	Approved
0.622	Remote Similarity	NPD7604	Phase 2
0.6204	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6195	Remote Similarity	NPD4755	Approved
0.619	Remote Similarity	NPD6110	Phase 1
0.619	Remote Similarity	NPD6695	Phase 3
0.619	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6186	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6183	Remote Similarity	NPD5956	Approved
0.6179	Remote Similarity	NPD6274	Approved
0.6148	Remote Similarity	NPD8133	Approved
0.6148	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6147	Remote Similarity	NPD6101	Approved
0.6147	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6147	Remote Similarity	NPD5370	Suspended
0.6136	Remote Similarity	NPD7260	Phase 2
0.6132	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6126	Remote Similarity	NPD4202	Approved
0.6124	Remote Similarity	NPD6336	Discontinued
0.6124	Remote Similarity	NPD8273	Phase 1
0.6121	Remote Similarity	NPD5224	Approved
0.6121	Remote Similarity	NPD4633	Approved
0.6121	Remote Similarity	NPD5226	Approved
0.6121	Remote Similarity	NPD5225	Approved
0.6116	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6105	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6094	Remote Similarity	NPD6067	Discontinued
0.6094	Remote Similarity	NPD7642	Approved
0.609	Remote Similarity	NPD6845	Suspended
0.6087	Remote Similarity	NPD4700	Approved
0.6071	Remote Similarity	NPD6001	Approved
0.6068	Remote Similarity	NPD5174	Approved
0.6068	Remote Similarity	NPD5175	Approved
0.605	Remote Similarity	NPD6685	Approved
0.6036	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.6036	Remote Similarity	NPD6411	Approved
0.6034	Remote Similarity	NPD5223	Approved
0.6033	Remote Similarity	NPD6420	Discontinued
0.6032	Remote Similarity	NPD4522	Approved
0.6032	Remote Similarity	NPD7100	Approved
0.6032	Remote Similarity	NPD7101	Approved
0.6031	Remote Similarity	NPD6033	Approved
0.6019	Remote Similarity	NPD3618	Phase 1
0.6	Remote Similarity	NPD6080	Approved
0.6	Remote Similarity	NPD6904	Approved
0.6	Remote Similarity	NPD6673	Approved
0.6	Remote Similarity	NPD6051	Approved
0.6	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6	Remote Similarity	NPD6317	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