NPASS Compound

Structure

CID243998 OpenBabel06191716042D 27 30 0 0 1 0 0 0 0 0999 V2000 0.8799 -3.3693 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5862 -2.0089 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2229 2.1324 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3167 -2.2601 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0757 -3.6640 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4449 2.0125 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2999 -1.4010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8087 -2.9838 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3645 1.6195 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0077 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7870 1.2594 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.2748 -1.6235 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.0567 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.2999 0.4010 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.0567 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7643 -3.2786 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5955 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.2748 0.6235 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.2090 1.3491 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.9868 -4.2535 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.5955 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8427 -0.1996 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 -2.4974 -2.5984 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.0077 0.3090 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 8 19 1 0 0 0 0 8 25 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 21 1 1 0 0 0 13 14 1 0 0 0 0 13 26 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 27 1 0 0 0 0 17 22 2 0 0 0 0 17 26 1 0 0 0 0 18 23 2 0 0 0 0 18 27 1 0 0 0 0 19 7 1 6 0 0 0 19 25 1 0 0 0 0 20 24 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	376.15
Volume:	368.6
LogP:	0.681
LogD:	0.543
LogS:	-2.561
# Rotatable Bonds:	3
TPSA:	105.59
# H-Bond Aceptor:	7
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.318
Synthetic Accessibility Score:	5.56
Fsp3:	0.6
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	3
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.088
MDCK Permeability:	2.150528962374665e-05
Pgp-inhibitor:	0.027
Pgp-substrate:	0.052
Human Intestinal Absorption (HIA):	0.438
20% Bioavailability (F20%):	0.943
30% Bioavailability (F30%):	0.987

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.124
Plasma Protein Binding (PPB):	59.07967758178711%
Volume Distribution (VD):	2.053
Pgp-substrate:	28.64479637145996%

ADMET: Metabolism

CYP1A2-inhibitor:	0.034
CYP1A2-substrate:	0.569
CYP2C19-inhibitor:	0.148
CYP2C19-substrate:	0.634
CYP2C9-inhibitor:	0.174
CYP2C9-substrate:	0.049
CYP2D6-inhibitor:	0.008
CYP2D6-substrate:	0.087
CYP3A4-inhibitor:	0.564
CYP3A4-substrate:	0.277

ADMET: Excretion

Clearance (CL):	3.393
Half-life (T1/2):	0.754

ADMET: Toxicity

hERG Blockers:	0.031
Human Hepatotoxicity (H-HT):	0.687
Drug-inuced Liver Injury (DILI):	0.885
AMES Toxicity:	0.118
Rat Oral Acute Toxicity:	0.729
Maximum Recommended Daily Dose:	0.565
Skin Sensitization:	0.56
Carcinogencity:	0.059
Eye Corrosion:	0.004
Eye Irritation:	0.098
Respiratory Toxicity:	0.85

Download Data

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

Natural Product: NPC243998

Natural Product ID:	NPC243998
*Common Name:**	Euparotin
IUPAC Name:	[(3aR,4R,6R,6aR,7R,9aS,9bS)-7,9a-dihydroxy-9-methyl-3-methylidene-2-oxospiro[3a,4,5,6a,7,9b-hexahydroazuleno[4,5-b]furan-6,2'-oxirane]-4-yl] (E)-2-methylbut-2-enoate
Synonyms:	Euparotin
Standard InCHIKey:	ADBOAFOIAMBXJT-CZNBXQLSSA-N
Standard InCHI:	InChI=1S/C20H24O7/c1-5-9(2)17(22)26-13-7-19(8-25-19)15-12(21)6-10(3)20(15,24)16-14(13)11(4)18(23)27-16/h5-6,12-16,21,24H,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@]2(CO2)[C@@H]2[C@@H](C=C(C)[C@@]2([C@@H]2[C@@H]1C(=C)C(=O)O2)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL518194
PubChem CID:	10384889
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]
NPO21343	Eupatorium fortunei	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26385	Eupatorium rotundifolium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21343	Eupatorium fortunei	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26385	Eupatorium rotundifolium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21343	Eupatorium fortunei	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[TCM_Taiwan]
NPO21343	Eupatorium fortunei	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
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	1
Others	2

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	ED100	=	0.21	ug ml-1	PMID[532904]
NPT91	Cell Line	KB	Homo sapiens	pED50	=	6.25	n.a.	PMID[532904]
NPT91	Cell Line	KB	Homo sapiens	ED50	=	0.56	umol/L	PMID[532905]

☑ 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 NPC243998 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	243
0.1-0.2	1375
0.2-0.3	4802
0.3-0.4	9143
0.4-0.5	14411
0.5-0.6	7494
0.6-0.7	3631
0.7-0.8	1367
0.8-0.85	150
0.85-0.9	73
0.9-0.95	6
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9796	High Similarity	NPC223450
0.9293	High Similarity	NPC86077
0.9208	High Similarity	NPC54737
0.9109	High Similarity	NPC100487
0.9072	High Similarity	NPC270013
0.9072	High Similarity	NPC14961
0.9048	High Similarity	NPC35069
0.9048	High Similarity	NPC258711
0.8969	High Similarity	NPC474035
0.8969	High Similarity	NPC81386
0.8969	High Similarity	NPC477131
0.8942	High Similarity	NPC139838
0.8942	High Similarity	NPC59489
0.8878	High Similarity	NPC304886
0.8868	High Similarity	NPC95290
0.8868	High Similarity	NPC189338
0.8866	High Similarity	NPC212486
0.8866	High Similarity	NPC475912
0.8812	High Similarity	NPC150923
0.88	High Similarity	NPC473326
0.8788	High Similarity	NPC476315
0.8776	High Similarity	NPC470013
0.8776	High Similarity	NPC262133
0.8776	High Similarity	NPC198853
0.8776	High Similarity	NPC470010
0.8776	High Similarity	NPC323008
0.8763	High Similarity	NPC133698
0.8763	High Similarity	NPC131209
0.8738	High Similarity	NPC203659
0.8738	High Similarity	NPC474741
0.8713	High Similarity	NPC288876
0.8713	High Similarity	NPC186861
0.8713	High Similarity	NPC471381
0.8687	High Similarity	NPC36954
0.8687	High Similarity	NPC220221
0.8673	High Similarity	NPC179746
0.8673	High Similarity	NPC81419
0.8673	High Similarity	NPC135776
0.8641	High Similarity	NPC475945
0.8641	High Similarity	NPC475871
0.8641	High Similarity	NPC110989
0.8614	High Similarity	NPC221615
0.8614	High Similarity	NPC474213
0.86	High Similarity	NPC279621
0.8586	High Similarity	NPC57405
0.8586	High Similarity	NPC303942
0.8571	High Similarity	NPC26617
0.8571	High Similarity	NPC30515
0.8571	High Similarity	NPC12172
0.8571	High Similarity	NPC184463
0.8571	High Similarity	NPC208886
0.8544	High Similarity	NPC474747
0.8544	High Similarity	NPC225353
0.8515	High Similarity	NPC161493
0.8515	High Similarity	NPC471150
0.8505	High Similarity	NPC257240
0.85	High Similarity	NPC52044
0.85	High Similarity	NPC476053
0.85	High Similarity	NPC67584
0.8485	Intermediate Similarity	NPC476300
0.8485	Intermediate Similarity	NPC228451
0.8485	Intermediate Similarity	NPC125674
0.8485	Intermediate Similarity	NPC475838
0.8476	Intermediate Similarity	NPC166115
0.8469	Intermediate Similarity	NPC51004
0.8469	Intermediate Similarity	NPC476004
0.8469	Intermediate Similarity	NPC474761
0.8462	Intermediate Similarity	NPC124881
0.8455	Intermediate Similarity	NPC255450
0.8455	Intermediate Similarity	NPC170692
0.8454	Intermediate Similarity	NPC202672
0.8447	Intermediate Similarity	NPC474742
0.8447	Intermediate Similarity	NPC476270
0.8431	Intermediate Similarity	NPC187268
0.8416	Intermediate Similarity	NPC213078
0.8416	Intermediate Similarity	NPC473859
0.84	Intermediate Similarity	NPC474247
0.84	Intermediate Similarity	NPC473330
0.84	Intermediate Similarity	NPC473316
0.8384	Intermediate Similarity	NPC475925
0.8384	Intermediate Similarity	NPC473321
0.8367	Intermediate Similarity	NPC307411
0.8367	Intermediate Similarity	NPC295312
0.8367	Intermediate Similarity	NPC4986
0.8367	Intermediate Similarity	NPC32922
0.8364	Intermediate Similarity	NPC121816
0.8351	Intermediate Similarity	NPC231889
0.835	Intermediate Similarity	NPC70865
0.8333	Intermediate Similarity	NPC477103
0.8318	Intermediate Similarity	NPC117604
0.8317	Intermediate Similarity	NPC170120
0.8317	Intermediate Similarity	NPC475659
0.8317	Intermediate Similarity	NPC472873
0.8317	Intermediate Similarity	NPC213698
0.83	Intermediate Similarity	NPC288240
0.83	Intermediate Similarity	NPC162205
0.83	Intermediate Similarity	NPC295204
0.83	Intermediate Similarity	NPC258216
0.83	Intermediate Similarity	NPC273579
0.8283	Intermediate Similarity	NPC129419
0.8283	Intermediate Similarity	NPC473619
0.8283	Intermediate Similarity	NPC475748
0.8283	Intermediate Similarity	NPC62815
0.8273	Intermediate Similarity	NPC46269
0.8273	Intermediate Similarity	NPC273242
0.8273	Intermediate Similarity	NPC106395
0.8269	Intermediate Similarity	NPC171759
0.8265	Intermediate Similarity	NPC91248
0.8265	Intermediate Similarity	NPC153805
0.8265	Intermediate Similarity	NPC281516
0.8257	Intermediate Similarity	NPC287311
0.8252	Intermediate Similarity	NPC141191
0.8252	Intermediate Similarity	NPC45125
0.8247	Intermediate Similarity	NPC470242
0.8241	Intermediate Similarity	NPC477102
0.8235	Intermediate Similarity	NPC24956
0.8235	Intermediate Similarity	NPC230800
0.8235	Intermediate Similarity	NPC18019
0.8224	Intermediate Similarity	NPC477513
0.8218	Intermediate Similarity	NPC127019
0.8214	Intermediate Similarity	NPC471146
0.82	Intermediate Similarity	NPC155215
0.8198	Intermediate Similarity	NPC133677
0.8198	Intermediate Similarity	NPC138303
0.8198	Intermediate Similarity	NPC67290
0.8182	Intermediate Similarity	NPC123855
0.8182	Intermediate Similarity	NPC268298
0.8182	Intermediate Similarity	NPC151770
0.8182	Intermediate Similarity	NPC138757
0.8182	Intermediate Similarity	NPC474032
0.8182	Intermediate Similarity	NPC76550
0.8182	Intermediate Similarity	NPC215556
0.8182	Intermediate Similarity	NPC166919
0.8173	Intermediate Similarity	NPC475053
0.8163	Intermediate Similarity	NPC186148
0.8163	Intermediate Similarity	NPC190753
0.8163	Intermediate Similarity	NPC475703
0.8155	Intermediate Similarity	NPC474313
0.8155	Intermediate Similarity	NPC181151
0.8155	Intermediate Similarity	NPC169205
0.8155	Intermediate Similarity	NPC108475
0.8155	Intermediate Similarity	NPC213947
0.8155	Intermediate Similarity	NPC170143
0.8148	Intermediate Similarity	NPC308191
0.8144	Intermediate Similarity	NPC21469
0.8137	Intermediate Similarity	NPC163228
0.8137	Intermediate Similarity	NPC107476
0.8137	Intermediate Similarity	NPC471142
0.8137	Intermediate Similarity	NPC471141
0.8131	Intermediate Similarity	NPC314244
0.8131	Intermediate Similarity	NPC179891
0.8131	Intermediate Similarity	NPC44004
0.8113	Intermediate Similarity	NPC475873
0.81	Intermediate Similarity	NPC216284
0.81	Intermediate Similarity	NPC475855
0.81	Intermediate Similarity	NPC106510
0.81	Intermediate Similarity	NPC301969
0.81	Intermediate Similarity	NPC312042
0.81	Intermediate Similarity	NPC71533
0.81	Intermediate Similarity	NPC37607
0.81	Intermediate Similarity	NPC473448
0.8095	Intermediate Similarity	NPC110443
0.8095	Intermediate Similarity	NPC201718
0.8095	Intermediate Similarity	NPC133907
0.8095	Intermediate Similarity	NPC46998
0.8095	Intermediate Similarity	NPC474339
0.8095	Intermediate Similarity	NPC128733
0.8095	Intermediate Similarity	NPC185141
0.8095	Intermediate Similarity	NPC164598
0.8095	Intermediate Similarity	NPC473332
0.8081	Intermediate Similarity	NPC178875
0.8081	Intermediate Similarity	NPC474471
0.8081	Intermediate Similarity	NPC227379
0.8081	Intermediate Similarity	NPC177629
0.8081	Intermediate Similarity	NPC217983
0.8081	Intermediate Similarity	NPC58219
0.8081	Intermediate Similarity	NPC207114
0.8081	Intermediate Similarity	NPC473715
0.8081	Intermediate Similarity	NPC79549
0.8077	Intermediate Similarity	NPC471144
0.8077	Intermediate Similarity	NPC208233
0.8073	Intermediate Similarity	NPC273433
0.807	Intermediate Similarity	NPC477092
0.8058	Intermediate Similarity	NPC185553
0.8058	Intermediate Similarity	NPC477921
0.8058	Intermediate Similarity	NPC476009
0.8058	Intermediate Similarity	NPC98165
0.8053	Intermediate Similarity	NPC475323
0.8039	Intermediate Similarity	NPC476267
0.8039	Intermediate Similarity	NPC474338
0.8039	Intermediate Similarity	NPC140543
0.8036	Intermediate Similarity	NPC471380
0.802	Intermediate Similarity	NPC476705
0.802	Intermediate Similarity	NPC70251
0.802	Intermediate Similarity	NPC475881
0.802	Intermediate Similarity	NPC300312
0.802	Intermediate Similarity	NPC261607
0.802	Intermediate Similarity	NPC184063
0.802	Intermediate Similarity	NPC111114
0.8019	Intermediate Similarity	NPC149371

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 NPC243998 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	232
0.1-0.2	1962
0.2-0.3	3724
0.3-0.4	2194
0.4-0.5	670
0.5-0.6	293
0.6-0.7	66
0.7-0.8	5
0.8-0.85	1
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8571	High Similarity	NPD7899	Clinical (unspecified phase)
0.8505	High Similarity	NPD6371	Approved
0.8367	Intermediate Similarity	NPD1695	Approved
0.7961	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7921	Intermediate Similarity	NPD46	Approved
0.7921	Intermediate Similarity	NPD6698	Approved
0.7778	Intermediate Similarity	NPD1733	Clinical (unspecified phase)
0.7573	Intermediate Similarity	NPD7838	Discovery
0.7544	Intermediate Similarity	NPD6053	Discontinued
0.7333	Intermediate Similarity	NPD7983	Approved
0.7273	Intermediate Similarity	NPD5344	Discontinued
0.7228	Intermediate Similarity	NPD5362	Discontinued
0.7184	Intermediate Similarity	NPD4249	Approved
0.7143	Intermediate Similarity	NPD7115	Discovery
0.7115	Intermediate Similarity	NPD4251	Approved
0.7115	Intermediate Similarity	NPD4250	Approved
0.7091	Intermediate Similarity	NPD4225	Approved
0.7075	Intermediate Similarity	NPD5785	Approved
0.7043	Intermediate Similarity	NPD6686	Approved
0.7018	Intermediate Similarity	NPD6008	Approved
0.7009	Intermediate Similarity	NPD8413	Clinical (unspecified phase)
0.696	Remote Similarity	NPD7507	Approved
0.6937	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD5363	Approved
0.6923	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6893	Remote Similarity	NPD7154	Phase 3
0.6881	Remote Similarity	NPD5282	Discontinued
0.6875	Remote Similarity	NPD6648	Approved
0.6857	Remote Similarity	NPD5786	Approved
0.6838	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6797	Remote Similarity	NPD7319	Approved
0.6796	Remote Similarity	NPD6435	Approved
0.6789	Remote Similarity	NPD5779	Approved
0.6789	Remote Similarity	NPD5778	Approved
0.6774	Remote Similarity	NPD8513	Phase 3
0.6774	Remote Similarity	NPD8516	Approved
0.6774	Remote Similarity	NPD8517	Approved
0.6774	Remote Similarity	NPD8515	Approved
0.6765	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD4820	Approved
0.6765	Remote Similarity	NPD4821	Approved
0.6765	Remote Similarity	NPD4822	Approved
0.6765	Remote Similarity	NPD4819	Approved
0.675	Remote Similarity	NPD4632	Approved
0.6694	Remote Similarity	NPD6319	Approved
0.6639	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6635	Remote Similarity	NPD4270	Approved
0.6635	Remote Similarity	NPD4269	Approved
0.6614	Remote Similarity	NPD7492	Approved
0.6602	Remote Similarity	NPD5368	Approved
0.6579	Remote Similarity	NPD7639	Approved
0.6579	Remote Similarity	NPD7640	Approved
0.6571	Remote Similarity	NPD5331	Approved
0.6571	Remote Similarity	NPD5332	Approved
0.6569	Remote Similarity	NPD4271	Approved
0.6569	Remote Similarity	NPD4268	Approved
0.6562	Remote Similarity	NPD6616	Approved
0.656	Remote Similarity	NPD6054	Approved
0.6538	Remote Similarity	NPD5369	Approved
0.6538	Remote Similarity	NPD4790	Discontinued
0.6535	Remote Similarity	NPD7642	Approved
0.6529	Remote Similarity	NPD8297	Approved
0.6525	Remote Similarity	NPD5697	Approved
0.6512	Remote Similarity	NPD8074	Phase 3
0.6512	Remote Similarity	NPD7078	Approved
0.6508	Remote Similarity	NPD6015	Approved
0.6508	Remote Similarity	NPD6016	Approved
0.6491	Remote Similarity	NPD7638	Approved
0.6471	Remote Similarity	NPD6899	Approved
0.6471	Remote Similarity	NPD6881	Approved
0.6471	Remote Similarity	NPD7320	Approved
0.6462	Remote Similarity	NPD7736	Approved
0.6457	Remote Similarity	NPD5988	Approved
0.6457	Remote Similarity	NPD6370	Approved
0.6452	Remote Similarity	NPD6009	Approved
0.6446	Remote Similarity	NPD6649	Approved
0.6446	Remote Similarity	NPD6650	Approved
0.6442	Remote Similarity	NPD4252	Approved
0.6441	Remote Similarity	NPD6675	Approved
0.6441	Remote Similarity	NPD7128	Approved
0.6441	Remote Similarity	NPD6402	Approved
0.6441	Remote Similarity	NPD5739	Approved
0.6434	Remote Similarity	NPD8273	Phase 1
0.6429	Remote Similarity	NPD6059	Approved
0.6417	Remote Similarity	NPD6373	Approved
0.6417	Remote Similarity	NPD6012	Approved
0.6417	Remote Similarity	NPD6014	Approved
0.6417	Remote Similarity	NPD6013	Approved
0.6417	Remote Similarity	NPD6372	Approved
0.6408	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6406	Remote Similarity	NPD7830	Approved
0.6406	Remote Similarity	NPD7829	Approved
0.6406	Remote Similarity	NPD7604	Phase 2
0.64	Remote Similarity	NPD7328	Approved
0.64	Remote Similarity	NPD7327	Approved
0.6387	Remote Similarity	NPD5701	Approved
0.6387	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6387	Remote Similarity	NPD6412	Phase 2
0.6385	Remote Similarity	NPD8293	Discontinued
0.6378	Remote Similarity	NPD5983	Phase 2
0.6378	Remote Similarity	NPD8033	Approved
0.6364	Remote Similarity	NPD6883	Approved
0.6364	Remote Similarity	NPD7102	Approved
0.6364	Remote Similarity	NPD7290	Approved
0.6349	Remote Similarity	NPD7516	Approved
0.6333	Remote Similarity	NPD6011	Approved
0.6325	Remote Similarity	NPD5211	Phase 2
0.6324	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6321	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6321	Remote Similarity	NPD5209	Approved
0.6316	Remote Similarity	NPD7839	Suspended
0.6311	Remote Similarity	NPD6617	Approved
0.6311	Remote Similarity	NPD6847	Approved
0.6311	Remote Similarity	NPD6869	Approved
0.6311	Remote Similarity	NPD8130	Phase 1
0.6299	Remote Similarity	NPD8377	Approved
0.6299	Remote Similarity	NPD8294	Approved
0.6296	Remote Similarity	NPD1694	Approved
0.6262	Remote Similarity	NPD6110	Phase 1
0.6261	Remote Similarity	NPD6083	Phase 2
0.6261	Remote Similarity	NPD6084	Phase 2
0.626	Remote Similarity	NPD6882	Approved
0.625	Remote Similarity	NPD7503	Approved
0.625	Remote Similarity	NPD8296	Approved
0.625	Remote Similarity	NPD8380	Approved
0.625	Remote Similarity	NPD7637	Suspended
0.625	Remote Similarity	NPD8378	Approved
0.625	Remote Similarity	NPD8335	Approved
0.625	Remote Similarity	NPD8379	Approved
0.623	Remote Similarity	NPD4634	Approved
0.6228	Remote Similarity	NPD5695	Phase 3
0.6218	Remote Similarity	NPD5141	Approved
0.6216	Remote Similarity	NPD6101	Approved
0.6216	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6207	Remote Similarity	NPD5696	Approved
0.6198	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6195	Remote Similarity	NPD6399	Phase 3
0.6194	Remote Similarity	NPD7260	Phase 2
0.6186	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6183	Remote Similarity	NPD6336	Discontinued
0.6182	Remote Similarity	NPD7524	Approved
0.6168	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD4696	Approved
0.6154	Remote Similarity	NPD5285	Approved
0.6154	Remote Similarity	NPD5286	Approved
0.6148	Remote Similarity	NPD6845	Suspended
0.6142	Remote Similarity	NPD7641	Discontinued
0.6124	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6121	Remote Similarity	NPD4755	Approved
0.6111	Remote Similarity	NPD6274	Approved
0.6106	Remote Similarity	NPD6411	Approved
0.6087	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6061	Remote Similarity	NPD8451	Approved
0.6055	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.605	Remote Similarity	NPD5224	Approved
0.605	Remote Similarity	NPD7632	Discontinued
0.605	Remote Similarity	NPD5225	Approved
0.605	Remote Similarity	NPD5226	Approved
0.605	Remote Similarity	NPD4633	Approved
0.6048	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6048	Remote Similarity	NPD2204	Approved
0.6017	Remote Similarity	NPD4700	Approved
0.6015	Remote Similarity	NPD8448	Approved
0.6	Remote Similarity	NPD5174	Approved
0.6	Remote Similarity	NPD5175	Approved
0.5985	Remote Similarity	NPD8341	Approved
0.5985	Remote Similarity	NPD8340	Approved
0.5985	Remote Similarity	NPD8299	Approved
0.5985	Remote Similarity	NPD8342	Approved
0.597	Remote Similarity	NPD6033	Approved
0.5969	Remote Similarity	NPD7100	Approved
0.5969	Remote Similarity	NPD7101	Approved
0.5966	Remote Similarity	NPD5223	Approved
0.5965	Remote Similarity	NPD5693	Phase 1
0.5965	Remote Similarity	NPD5284	Approved
0.5965	Remote Similarity	NPD5281	Approved
0.5963	Remote Similarity	NPD6695	Phase 3
0.5952	Remote Similarity	NPD8133	Approved
0.5948	Remote Similarity	NPD5210	Approved
0.5948	Remote Similarity	NPD4629	Approved
0.5938	Remote Similarity	NPD6317	Approved
0.5929	Remote Similarity	NPD4753	Phase 2
0.5909	Remote Similarity	NPD8328	Phase 3
0.5909	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.5897	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.5891	Remote Similarity	NPD6313	Approved
0.5891	Remote Similarity	NPD6335	Approved
0.5891	Remote Similarity	NPD6314	Approved
0.5882	Remote Similarity	NPD5956	Approved
0.5882	Remote Similarity	NPD8392	Approved
0.5882	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.5882	Remote Similarity	NPD8390	Approved
0.5882	Remote Similarity	NPD8391	Approved
0.5878	Remote Similarity	NPD8444	Approved
0.5877	Remote Similarity	NPD5207	Approved
0.5862	Remote Similarity	NPD6001	Approved
0.5841	Remote Similarity	NPD6903	Approved
0.584	Remote Similarity	NPD6421	Discontinued
0.5833	Remote Similarity	NPD1700	Approved
0.5826	Remote Similarity	NPD6079	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