NPASS Compound

Structure

CID86077 OpenBabel06191715422D 27 30 0 0 1 0 0 0 0 0999 V2000 0.5246 3.8331 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0540 -0.7657 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8796 1.4332 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5927 5.3081 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2589 5.9532 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9055 0.7114 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3883 2.7032 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0523 3.1872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4598 4.2481 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0601 0.2223 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9307 0.9423 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9116 1.6993 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.1940 2.1280 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.1947 0.7220 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.1991 1.3094 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.2008 1.7099 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.3761 0.7270 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.3114 3.6030 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8077 0.1330 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2069 2.6981 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.1260 7.0133 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2959 4.0179 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5678 -0.6177 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2130 3.6862 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.9177 2.6876 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1785 2.5429 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 1 0 0 0 0 3 11 2 0 0 0 0 4 5 1 0 0 0 0 4 9 2 0 0 0 0 5 21 1 0 0 0 0 6 10 2 0 0 0 0 7 13 1 0 0 0 0 7 20 1 0 0 0 0 8 20 1 0 0 0 0 8 25 1 0 0 0 0 9 18 1 0 0 0 0 11 19 1 0 0 0 0 12 6 1 6 0 0 0 12 16 1 0 0 0 0 12 25 1 0 0 0 0 13 15 1 0 0 0 0 13 26 1 6 0 0 0 14 10 1 6 0 0 0 14 16 1 0 0 0 0 14 17 1 0 0 0 0 15 11 1 6 0 0 0 15 17 1 0 0 0 0 16 20 1 6 0 0 0 17 27 1 1 0 0 0 18 22 2 0 0 0 0 18 26 1 0 0 0 0 19 23 2 0 0 0 0 19 27 1 0 0 0 0 20 24 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	376.15
Volume:	368.6
LogP:	-0.007
LogD:	0.883
LogS:	-2.485
# Rotatable Bonds:	5
TPSA:	99.13
# H-Bond Aceptor:	7
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.337
Synthetic Accessibility Score:	5.357
Fsp3:	0.65
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:	-4.946
MDCK Permeability:	6.72125315759331e-05
Pgp-inhibitor:	0.03
Pgp-substrate:	0.006
Human Intestinal Absorption (HIA):	0.468
20% Bioavailability (F20%):	0.373
30% Bioavailability (F30%):	0.967

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.405
Plasma Protein Binding (PPB):	48.11909484863281%
Volume Distribution (VD):	1.514
Pgp-substrate:	51.123748779296875%

ADMET: Metabolism

CYP1A2-inhibitor:	0.063
CYP1A2-substrate:	0.107
CYP2C19-inhibitor:	0.034
CYP2C19-substrate:	0.165
CYP2C9-inhibitor:	0.029
CYP2C9-substrate:	0.03
CYP2D6-inhibitor:	0.012
CYP2D6-substrate:	0.073
CYP3A4-inhibitor:	0.548
CYP3A4-substrate:	0.214

ADMET: Excretion

Clearance (CL):	4.651
Half-life (T1/2):	0.501

ADMET: Toxicity

hERG Blockers:	0.035
Human Hepatotoxicity (H-HT):	0.941
Drug-inuced Liver Injury (DILI):	0.874
AMES Toxicity:	0.095
Rat Oral Acute Toxicity:	0.195
Maximum Recommended Daily Dose:	0.186
Skin Sensitization:	0.676
Carcinogencity:	0.06
Eye Corrosion:	0.093
Eye Irritation:	0.068
Respiratory Toxicity:	0.712

Download Data

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

Natural Product: NPC86077

Natural Product ID:	NPC86077
*Common Name:**	Eupalinilide C
IUPAC Name:	n.a.
Synonyms:	Eupalinilide C
Standard InCHIKey:	QWNQZWRFKIHTPL-NPUYJLKLSA-N
Standard InCHI:	InChI=1S/C20H24O7/c1-9(4-5-21)18(22)26-13-7-20(24)8-25-12-6-10(2)14(16(12)20)17-15(13)11(3)19(23)27-17/h4,6,12-17,21,24H,3,5,7-8H2,1-2H3/b9-4+/t12-,13-,14+,15-,16-,17-,20+/m1/s1
SMILES:	C/C(=CCO)/C(=O)O[C@@H]1C[C@@]2(CO[C@@H]3C=C(C)[C@@H]([C@H]23)[C@@H]2[C@@H]1C(=C)C(=O)O2)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL518078
PubChem CID:	11417523
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
NPO851	Eupatorium lindleyanum	Species	Asteraceae	Eukaryota	Whole plant	Songyang County, Zhejiang Province, China	n.a.	PMID[15387644]
NPO851	Eupatorium lindleyanum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO851	Eupatorium lindleyanum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO851	Eupatorium lindleyanum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO851	Eupatorium lindleyanum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO851	Eupatorium lindleyanum	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
NPT168	Cell Line	P388	Mus musculus	IC50	=	1.2	ug.mL-1	PMID[533056]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	11.0	ug.mL-1	PMID[533056]

☑ 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 NPC86077 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	1229
0.2-0.3	4675
0.3-0.4	9945
0.4-0.5	13736
0.5-0.6	7871
0.6-0.7	3713
0.7-0.8	1070
0.8-0.85	176
0.85-0.9	37
0.9-0.95	9
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9293	High Similarity	NPC243998
0.9255	High Similarity	NPC477131
0.9158	High Similarity	NPC304886
0.91	High Similarity	NPC223450
0.9053	High Similarity	NPC470010
0.9053	High Similarity	NPC323008
0.9053	High Similarity	NPC262133
0.9053	High Similarity	NPC470013
0.9053	High Similarity	NPC198853
0.9043	High Similarity	NPC131209
0.9043	High Similarity	NPC133698
0.8889	High Similarity	NPC150923
0.8878	High Similarity	NPC187268
0.8812	High Similarity	NPC100487
0.8762	High Similarity	NPC35069
0.8762	High Similarity	NPC258711
0.875	High Similarity	NPC179746
0.875	High Similarity	NPC81419
0.875	High Similarity	NPC475912
0.8725	High Similarity	NPC166115
0.8713	High Similarity	NPC124881
0.8646	High Similarity	NPC475925
0.8646	High Similarity	NPC208886
0.8646	High Similarity	NPC12172
0.8641	High Similarity	NPC26617
0.8627	High Similarity	NPC203659
0.8611	High Similarity	NPC475323
0.86	High Similarity	NPC70865
0.8586	High Similarity	NPC161493
0.8585	High Similarity	NPC189338
0.8585	High Similarity	NPC95290
0.8571	High Similarity	NPC270013
0.8571	High Similarity	NPC36954
0.8571	High Similarity	NPC67584
0.8571	High Similarity	NPC220221
0.8571	High Similarity	NPC14961
0.8571	High Similarity	NPC52044
0.8557	High Similarity	NPC135776
0.8544	High Similarity	NPC54737
0.8529	High Similarity	NPC110989
0.8529	High Similarity	NPC475871
0.8529	High Similarity	NPC475945
0.8526	High Similarity	NPC91248
0.8485	Intermediate Similarity	NPC213078
0.8485	Intermediate Similarity	NPC279621
0.8469	Intermediate Similarity	NPC81386
0.8469	Intermediate Similarity	NPC474338
0.8469	Intermediate Similarity	NPC474035
0.8454	Intermediate Similarity	NPC30515
0.8454	Intermediate Similarity	NPC184463
0.8438	Intermediate Similarity	NPC473564
0.8431	Intermediate Similarity	NPC474747
0.8431	Intermediate Similarity	NPC225353
0.84	Intermediate Similarity	NPC181151
0.84	Intermediate Similarity	NPC474313
0.8396	Intermediate Similarity	NPC257240
0.8384	Intermediate Similarity	NPC213698
0.8384	Intermediate Similarity	NPC170120
0.8384	Intermediate Similarity	NPC472873
0.8367	Intermediate Similarity	NPC475838
0.8367	Intermediate Similarity	NPC228451
0.8367	Intermediate Similarity	NPC476300
0.8367	Intermediate Similarity	NPC212486
0.8367	Intermediate Similarity	NPC125674
0.8351	Intermediate Similarity	NPC474761
0.8351	Intermediate Similarity	NPC475855
0.8351	Intermediate Similarity	NPC51004
0.8351	Intermediate Similarity	NPC129419
0.8351	Intermediate Similarity	NPC476004
0.8351	Intermediate Similarity	NPC473448
0.8333	Intermediate Similarity	NPC474742
0.8333	Intermediate Similarity	NPC207114
0.8333	Intermediate Similarity	NPC202672
0.8333	Intermediate Similarity	NPC217983
0.8317	Intermediate Similarity	NPC473326
0.8317	Intermediate Similarity	NPC221615
0.8302	Intermediate Similarity	NPC139838
0.8302	Intermediate Similarity	NPC59489
0.83	Intermediate Similarity	NPC476315
0.83	Intermediate Similarity	NPC18019
0.83	Intermediate Similarity	NPC24956
0.8283	Intermediate Similarity	NPC127019
0.8283	Intermediate Similarity	NPC474247
0.8273	Intermediate Similarity	NPC473656
0.8269	Intermediate Similarity	NPC474741
0.8269	Intermediate Similarity	NPC474917
0.8265	Intermediate Similarity	NPC184063
0.8265	Intermediate Similarity	NPC473321
0.8247	Intermediate Similarity	NPC32922
0.8247	Intermediate Similarity	NPC307411
0.8247	Intermediate Similarity	NPC4986
0.8247	Intermediate Similarity	NPC215556
0.8247	Intermediate Similarity	NPC268298
0.8247	Intermediate Similarity	NPC295312
0.8235	Intermediate Similarity	NPC288876
0.8229	Intermediate Similarity	NPC190753
0.8229	Intermediate Similarity	NPC186148
0.8229	Intermediate Similarity	NPC160138
0.8218	Intermediate Similarity	NPC471150
0.8208	Intermediate Similarity	NPC475960
0.82	Intermediate Similarity	NPC224689
0.8182	Intermediate Similarity	NPC273579
0.8182	Intermediate Similarity	NPC162205
0.8182	Intermediate Similarity	NPC295204
0.8182	Intermediate Similarity	NPC288240
0.8165	Intermediate Similarity	NPC106395
0.8165	Intermediate Similarity	NPC46269
0.8165	Intermediate Similarity	NPC209058
0.8163	Intermediate Similarity	NPC179394
0.8163	Intermediate Similarity	NPC206614
0.8163	Intermediate Similarity	NPC216284
0.8163	Intermediate Similarity	NPC37607
0.8163	Intermediate Similarity	NPC473619
0.8163	Intermediate Similarity	NPC301969
0.8163	Intermediate Similarity	NPC144133
0.8163	Intermediate Similarity	NPC239517
0.8163	Intermediate Similarity	NPC19087
0.8163	Intermediate Similarity	NPC474323
0.8158	Intermediate Similarity	NPC469352
0.8155	Intermediate Similarity	NPC185141
0.8155	Intermediate Similarity	NPC128733
0.8155	Intermediate Similarity	NPC46998
0.8155	Intermediate Similarity	NPC133907
0.8155	Intermediate Similarity	NPC110443
0.8144	Intermediate Similarity	NPC191929
0.8144	Intermediate Similarity	NPC274446
0.8144	Intermediate Similarity	NPC39754
0.8144	Intermediate Similarity	NPC242364
0.8144	Intermediate Similarity	NPC320569
0.8144	Intermediate Similarity	NPC261952
0.8144	Intermediate Similarity	NPC79549
0.8144	Intermediate Similarity	NPC153805
0.8144	Intermediate Similarity	NPC81045
0.8144	Intermediate Similarity	NPC100454
0.8144	Intermediate Similarity	NPC287164
0.8144	Intermediate Similarity	NPC234077
0.8144	Intermediate Similarity	NPC151403
0.8144	Intermediate Similarity	NPC169511
0.8144	Intermediate Similarity	NPC172821
0.8144	Intermediate Similarity	NPC133730
0.8144	Intermediate Similarity	NPC61257
0.8144	Intermediate Similarity	NPC58219
0.8144	Intermediate Similarity	NPC177629
0.8144	Intermediate Similarity	NPC171135
0.8137	Intermediate Similarity	NPC141191
0.8137	Intermediate Similarity	NPC474213
0.8131	Intermediate Similarity	NPC477102
0.8125	Intermediate Similarity	NPC64153
0.8125	Intermediate Similarity	NPC305475
0.8125	Intermediate Similarity	NPC187661
0.8125	Intermediate Similarity	NPC475461
0.8125	Intermediate Similarity	NPC107787
0.8119	Intermediate Similarity	NPC230800
0.81	Intermediate Similarity	NPC167219
0.81	Intermediate Similarity	NPC303942
0.81	Intermediate Similarity	NPC57405
0.8091	Intermediate Similarity	NPC67290
0.8091	Intermediate Similarity	NPC133677
0.8091	Intermediate Similarity	NPC138303
0.8091	Intermediate Similarity	NPC471380
0.8091	Intermediate Similarity	NPC121816
0.8073	Intermediate Similarity	NPC123855
0.8073	Intermediate Similarity	NPC138757
0.8073	Intermediate Similarity	NPC76550
0.8061	Intermediate Similarity	NPC40066
0.8061	Intermediate Similarity	NPC92974
0.8061	Intermediate Similarity	NPC81778
0.8061	Intermediate Similarity	NPC42598
0.8061	Intermediate Similarity	NPC20621
0.8061	Intermediate Similarity	NPC474032
0.8061	Intermediate Similarity	NPC93794
0.8061	Intermediate Similarity	NPC473504
0.8061	Intermediate Similarity	NPC318963
0.8061	Intermediate Similarity	NPC91067
0.8061	Intermediate Similarity	NPC38392
0.8058	Intermediate Similarity	NPC186861
0.8058	Intermediate Similarity	NPC471381
0.8056	Intermediate Similarity	NPC471884
0.8056	Intermediate Similarity	NPC477103
0.8041	Intermediate Similarity	NPC237540
0.8039	Intermediate Similarity	NPC170143
0.8039	Intermediate Similarity	NPC169205
0.8039	Intermediate Similarity	NPC108475
0.8039	Intermediate Similarity	NPC213947
0.8037	Intermediate Similarity	NPC308191
0.8036	Intermediate Similarity	NPC475372
0.8021	Intermediate Similarity	NPC21469
0.8021	Intermediate Similarity	NPC78089
0.8021	Intermediate Similarity	NPC165162
0.8021	Intermediate Similarity	NPC255307
0.802	Intermediate Similarity	NPC471142
0.802	Intermediate Similarity	NPC471141
0.8019	Intermediate Similarity	NPC179891
0.8019	Intermediate Similarity	NPC475217
0.8	Intermediate Similarity	NPC273242
0.8	Intermediate Similarity	NPC472874
0.8	Intermediate Similarity	NPC469645
0.8	Intermediate Similarity	NPC258216
0.8	Intermediate Similarity	NPC475788
0.8	Intermediate Similarity	NPC475873

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 NPC86077 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	221
0.1-0.2	1878
0.2-0.3	3754
0.3-0.4	2284
0.4-0.5	652
0.5-0.6	291
0.6-0.7	57
0.7-0.8	11
0.8-0.85	1
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8641	High Similarity	NPD7899	Clinical (unspecified phase)
0.8396	Intermediate Similarity	NPD6371	Approved
0.8247	Intermediate Similarity	NPD1695	Approved
0.7843	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.78	Intermediate Similarity	NPD46	Approved
0.78	Intermediate Similarity	NPD6698	Approved
0.7451	Intermediate Similarity	NPD7838	Discovery
0.73	Intermediate Similarity	NPD1733	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD4225	Approved
0.7281	Intermediate Similarity	NPD6053	Discontinued
0.7273	Intermediate Similarity	NPD5362	Discontinued
0.7232	Intermediate Similarity	NPD6686	Approved
0.7228	Intermediate Similarity	NPD4249	Approved
0.7212	Intermediate Similarity	NPD7983	Approved
0.7193	Intermediate Similarity	NPD8413	Clinical (unspecified phase)
0.7157	Intermediate Similarity	NPD4250	Approved
0.7157	Intermediate Similarity	NPD4251	Approved
0.7156	Intermediate Similarity	NPD5344	Discontinued
0.713	Intermediate Similarity	NPD8029	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD5785	Approved
0.71	Intermediate Similarity	NPD7154	Phase 3
0.7075	Intermediate Similarity	NPD5282	Discontinued
0.7034	Intermediate Similarity	NPD7115	Discovery
0.6961	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6961	Remote Similarity	NPD5363	Approved
0.68	Remote Similarity	NPD4819	Approved
0.68	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.68	Remote Similarity	NPD4822	Approved
0.68	Remote Similarity	NPD4820	Approved
0.68	Remote Similarity	NPD4821	Approved
0.6757	Remote Similarity	NPD7640	Approved
0.6757	Remote Similarity	NPD7639	Approved
0.6757	Remote Similarity	NPD6648	Approved
0.6733	Remote Similarity	NPD4790	Discontinued
0.6724	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.672	Remote Similarity	NPD7507	Approved
0.6667	Remote Similarity	NPD8515	Approved
0.6667	Remote Similarity	NPD8513	Phase 3
0.6667	Remote Similarity	NPD5778	Approved
0.6667	Remote Similarity	NPD4270	Approved
0.6667	Remote Similarity	NPD8517	Approved
0.6667	Remote Similarity	NPD5779	Approved
0.6667	Remote Similarity	NPD8516	Approved
0.6667	Remote Similarity	NPD4269	Approved
0.6667	Remote Similarity	NPD7638	Approved
0.6602	Remote Similarity	NPD5332	Approved
0.6602	Remote Similarity	NPD5331	Approved
0.66	Remote Similarity	NPD4268	Approved
0.66	Remote Similarity	NPD4271	Approved
0.66	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD5786	Approved
0.6569	Remote Similarity	NPD5369	Approved
0.6562	Remote Similarity	NPD7319	Approved
0.6525	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6505	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6505	Remote Similarity	NPD6435	Approved
0.65	Remote Similarity	NPD4632	Approved
0.6476	Remote Similarity	NPD1694	Approved
0.6471	Remote Similarity	NPD4252	Approved
0.6466	Remote Similarity	NPD6008	Approved
0.6452	Remote Similarity	NPD6319	Approved
0.6423	Remote Similarity	NPD7327	Approved
0.6423	Remote Similarity	NPD7328	Approved
0.6422	Remote Similarity	NPD7637	Suspended
0.641	Remote Similarity	NPD6412	Phase 2
0.6406	Remote Similarity	NPD8074	Phase 3
0.6406	Remote Similarity	NPD7078	Approved
0.64	Remote Similarity	NPD8033	Approved
0.6378	Remote Similarity	NPD7492	Approved
0.6371	Remote Similarity	NPD7516	Approved
0.6364	Remote Similarity	NPD6399	Phase 3
0.6355	Remote Similarity	NPD7524	Approved
0.6328	Remote Similarity	NPD6616	Approved
0.6328	Remote Similarity	NPD8273	Phase 1
0.632	Remote Similarity	NPD8377	Approved
0.632	Remote Similarity	NPD6054	Approved
0.632	Remote Similarity	NPD8294	Approved
0.6311	Remote Similarity	NPD5368	Approved
0.6286	Remote Similarity	NPD6110	Phase 1
0.6283	Remote Similarity	NPD6084	Phase 2
0.6283	Remote Similarity	NPD6083	Phase 2
0.6281	Remote Similarity	NPD8297	Approved
0.6271	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6271	Remote Similarity	NPD5697	Approved
0.627	Remote Similarity	NPD8335	Approved
0.627	Remote Similarity	NPD6016	Approved
0.627	Remote Similarity	NPD6015	Approved
0.627	Remote Similarity	NPD8296	Approved
0.627	Remote Similarity	NPD8380	Approved
0.627	Remote Similarity	NPD8378	Approved
0.627	Remote Similarity	NPD7503	Approved
0.627	Remote Similarity	NPD8379	Approved
0.625	Remote Similarity	NPD5695	Phase 3
0.6231	Remote Similarity	NPD7736	Approved
0.6228	Remote Similarity	NPD5696	Approved
0.6226	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6222	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.622	Remote Similarity	NPD5988	Approved
0.622	Remote Similarity	NPD6370	Approved
0.6218	Remote Similarity	NPD6881	Approved
0.6218	Remote Similarity	NPD6899	Approved
0.6218	Remote Similarity	NPD7320	Approved
0.621	Remote Similarity	NPD6009	Approved
0.6207	Remote Similarity	NPD7632	Discontinued
0.6198	Remote Similarity	NPD6649	Approved
0.6198	Remote Similarity	NPD6650	Approved
0.6195	Remote Similarity	NPD7839	Suspended
0.619	Remote Similarity	NPD6059	Approved
0.619	Remote Similarity	NPD5209	Approved
0.6186	Remote Similarity	NPD6675	Approved
0.6186	Remote Similarity	NPD7128	Approved
0.6186	Remote Similarity	NPD5739	Approved
0.6186	Remote Similarity	NPD6402	Approved
0.6172	Remote Similarity	NPD7642	Approved
0.6167	Remote Similarity	NPD6014	Approved
0.6167	Remote Similarity	NPD6012	Approved
0.6167	Remote Similarity	NPD6373	Approved
0.6167	Remote Similarity	NPD6372	Approved
0.6167	Remote Similarity	NPD6013	Approved
0.6154	Remote Similarity	NPD8293	Discontinued
0.6142	Remote Similarity	NPD5983	Phase 2
0.6134	Remote Similarity	NPD5701	Approved
0.6132	Remote Similarity	NPD6695	Phase 3
0.6116	Remote Similarity	NPD7290	Approved
0.6116	Remote Similarity	NPD6883	Approved
0.6116	Remote Similarity	NPD7102	Approved
0.6098	Remote Similarity	NPD8133	Approved
0.6091	Remote Similarity	NPD6101	Approved
0.6091	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.609	Remote Similarity	NPD7260	Phase 2
0.6083	Remote Similarity	NPD6011	Approved
0.6083	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6075	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6068	Remote Similarity	NPD5211	Phase 2
0.6066	Remote Similarity	NPD2204	Approved
0.6066	Remote Similarity	NPD6869	Approved
0.6066	Remote Similarity	NPD8130	Phase 1
0.6066	Remote Similarity	NPD6847	Approved
0.6066	Remote Similarity	NPD6617	Approved
0.6047	Remote Similarity	NPD7830	Approved
0.6047	Remote Similarity	NPD7604	Phase 2
0.6047	Remote Similarity	NPD7829	Approved
0.6045	Remote Similarity	NPD6845	Suspended
0.6042	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6038	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.6032	Remote Similarity	NPD7641	Discontinued
0.6016	Remote Similarity	NPD6882	Approved
0.5984	Remote Similarity	NPD4634	Approved
0.5984	Remote Similarity	NPD6421	Discontinued
0.5982	Remote Similarity	NPD5281	Approved
0.5982	Remote Similarity	NPD6411	Approved
0.5982	Remote Similarity	NPD5284	Approved
0.5982	Remote Similarity	NPD5693	Phase 1
0.5966	Remote Similarity	NPD5141	Approved
0.5965	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.5965	Remote Similarity	NPD5210	Approved
0.5965	Remote Similarity	NPD4629	Approved
0.5954	Remote Similarity	NPD8451	Approved
0.5954	Remote Similarity	NPD6336	Discontinued
0.5946	Remote Similarity	NPD4753	Phase 2
0.5913	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.5909	Remote Similarity	NPD8448	Approved
0.5909	Remote Similarity	NPD7750	Discontinued
0.5897	Remote Similarity	NPD5285	Approved
0.5897	Remote Similarity	NPD4696	Approved
0.5897	Remote Similarity	NPD5286	Approved
0.5896	Remote Similarity	NPD5956	Approved
0.5896	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.5893	Remote Similarity	NPD5207	Approved
0.5891	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.5891	Remote Similarity	NPD8266	Approved
0.5891	Remote Similarity	NPD8267	Approved
0.5891	Remote Similarity	NPD8268	Approved
0.5891	Remote Similarity	NPD8269	Approved
0.5878	Remote Similarity	NPD8341	Approved
0.5878	Remote Similarity	NPD8299	Approved
0.5878	Remote Similarity	NPD8340	Approved
0.5878	Remote Similarity	NPD8342	Approved
0.5873	Remote Similarity	NPD6274	Approved
0.5865	Remote Similarity	NPD4756	Discovery
0.5862	Remote Similarity	NPD7902	Approved
0.5862	Remote Similarity	NPD4755	Approved
0.5856	Remote Similarity	NPD5737	Approved
0.5856	Remote Similarity	NPD6903	Approved
0.5856	Remote Similarity	NPD6672	Approved
0.5849	Remote Similarity	NPD6931	Approved
0.5849	Remote Similarity	NPD6930	Phase 2
0.5849	Remote Similarity	NPD7332	Phase 2
0.5833	Remote Similarity	NPD4056	Clinical (unspecified phase)
0.5833	Remote Similarity	NPD4057	Clinical (unspecified phase)
0.5827	Remote Similarity	NPD7505	Discontinued
0.5827	Remote Similarity	NPD7500	Approved
0.5818	Remote Similarity	NPD3618	Phase 1
0.5818	Remote Similarity	NPD7334	Approved
0.5818	Remote Similarity	NPD6684	Approved
0.5818	Remote Similarity	NPD7146	Approved
0.5818	Remote Similarity	NPD5330	Approved
0.5818	Remote Similarity	NPD7521	Approved
0.5818	Remote Similarity	NPD5279	Phase 3
0.5818	Remote Similarity	NPD6409	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