NPASS Compound

Structure

NPC473321 OpenBabel07101718182D 29 30 0 0 1 0 0 0 0 0999 V2000 -3.3022 -5.0924 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5279 -2.4563 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5493 -2.0255 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0594 2.2872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2319 -2.5772 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0862 2.8225 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7089 -4.1789 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2129 -0.4428 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0050 0.5354 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4013 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1211 -3.3698 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8061 -1.3563 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2673 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3364 -1.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0808 2.9271 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2618 1.2045 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9945 -0.1045 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.2024 -1.0827 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.9401 -1.8563 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -1.9456 -1.7518 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.1266 -3.4744 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4067 -0.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4875 3.8406 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.1480 -2.8345 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7199 -4.3879 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3849 -1.1215 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.6685 2.1180 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 -1.5388 -2.6654 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 7 1 0 0 0 0 2 11 1 0 0 0 0 3 12 1 0 0 0 0 4 13 1 0 0 0 0 5 14 2 0 0 0 0 6 15 1 0 0 0 0 7 11 2 0 0 0 0 8 9 1 0 0 0 0 8 12 2 0 0 0 0 9 16 1 0 0 0 0 10 13 2 0 0 0 0 11 21 1 0 0 0 0 12 19 1 0 0 0 0 13 16 1 0 0 0 0 14 22 1 0 0 0 0 15 23 2 0 0 0 0 15 27 1 0 0 0 0 16 27 1 6 0 0 0 17 10 1 1 0 0 0 17 18 1 0 0 0 0 17 28 1 0 0 0 0 18 14 1 6 0 0 0 18 20 1 0 0 0 0 19 20 1 0 0 0 0 19 24 1 0 0 0 0 20 29 1 6 0 0 0 21 25 2 0 0 0 0 21 29 1 0 0 0 0 22 26 2 0 0 0 0 22 28 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	404.18
Volume:	415.032
LogP:	1.686
LogD:	1.462
LogS:	-2.848
# Rotatable Bonds:	5
TPSA:	99.13
# H-Bond Aceptor:	7
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.334
Synthetic Accessibility Score:	5.059
Fsp3:	0.5
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	2
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.822
MDCK Permeability:	7.507675036322325e-05
Pgp-inhibitor:	0.113
Pgp-substrate:	0.006
Human Intestinal Absorption (HIA):	0.966
20% Bioavailability (F20%):	0.768
30% Bioavailability (F30%):	0.988

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.44
Plasma Protein Binding (PPB):	85.61215209960938%
Volume Distribution (VD):	1.339
Pgp-substrate:	11.980562210083008%

ADMET: Metabolism

CYP1A2-inhibitor:	0.073
CYP1A2-substrate:	0.088
CYP2C19-inhibitor:	0.5
CYP2C19-substrate:	0.223
CYP2C9-inhibitor:	0.477
CYP2C9-substrate:	0.066
CYP2D6-inhibitor:	0.086
CYP2D6-substrate:	0.137
CYP3A4-inhibitor:	0.645
CYP3A4-substrate:	0.215

ADMET: Excretion

Clearance (CL):	7.155
Half-life (T1/2):	0.618

ADMET: Toxicity

hERG Blockers:	0.018
Human Hepatotoxicity (H-HT):	0.895
Drug-inuced Liver Injury (DILI):	0.558
AMES Toxicity:	0.197
Rat Oral Acute Toxicity:	0.838
Maximum Recommended Daily Dose:	0.953
Skin Sensitization:	0.347
Carcinogencity:	0.071
Eye Corrosion:	0.006
Eye Irritation:	0.011
Respiratory Toxicity:	0.953

Download Data

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

Natural Product: NPC473321

Natural Product ID:	NPC473321
*Common Name:**	Eupatocunin
IUPAC Name:	n.a.
Synonyms:	Eupatocunin
Standard InCHIKey:	JWMHJIFDEKQJQY-GKUOJRQYSA-N
Standard InCHI:	InChI=1S/C22H28O7/c1-7-11(2)21(25)29-20-18-14(5)22(26)28-17(18)10-13(4)16(27-15(6)23)9-8-12(3)19(20)24/h7-8,10,16-20,24H,5,9H2,1-4,6H3/b11-7-,12-8-,13-10+/t16-,17+,18-,19?,20-/m0/s1
SMILES:	C/C=C(C(=O)O[C@@H]1C(O)/C(=CC[C@@H](/C(=C/[C@@H]2[C@@H]1C(=C)C(=O)O2)/C)OC(=O)C)/C)/C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL400238
PubChem CID:	n.a.
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
NPO33469	Asteraceae	Family	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18329753]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
ED50	2
Others	1

Activity Type	# Activity
Cell Line	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	ED50	=	0.11	ug ml-1	PMID[492530]
NPT91	Cell Line	KB	Homo sapiens	pED50	=	6.57	n.a.	PMID[492530]
NPT91	Cell Line	KB	Homo sapiens	ED50	=	0.27	umol/L	PMID[492531]

☑ 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 NPC473321 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	195
0.1-0.2	1277
0.2-0.3	4848
0.3-0.4	8878
0.4-0.5	14929
0.5-0.6	7452
0.6-0.7	3781
0.7-0.8	1006
0.8-0.85	212
0.85-0.9	95
0.9-0.95	14
0.95-1	10

Similarity Score	Similarity Level	Natural Product ID
0.9882	High Similarity	NPC473619
0.9655	High Similarity	NPC288240
0.9655	High Similarity	NPC162205
0.9655	High Similarity	NPC295204
0.9655	High Similarity	NPC273579
0.9647	High Similarity	NPC473715
0.9551	High Similarity	NPC477921
0.9438	High Similarity	NPC471142
0.9438	High Similarity	NPC477922
0.931	High Similarity	NPC474032
0.9294	High Similarity	NPC21469
0.9213	High Similarity	NPC475912
0.913	High Similarity	NPC471144
0.9111	High Similarity	NPC303942
0.9111	High Similarity	NPC57405
0.9059	High Similarity	NPC40746
0.9059	High Similarity	NPC169575
0.9032	High Similarity	NPC288876
0.9011	High Similarity	NPC14961
0.9011	High Similarity	NPC270013
0.9011	High Similarity	NPC36954
0.8989	High Similarity	NPC474232
0.8989	High Similarity	NPC475855
0.8966	High Similarity	NPC469910
0.8925	High Similarity	NPC473326
0.8913	High Similarity	NPC473859
0.8913	High Similarity	NPC279621
0.8901	High Similarity	NPC81386
0.8901	High Similarity	NPC474035
0.8889	High Similarity	NPC184463
0.8889	High Similarity	NPC30515
0.8851	High Similarity	NPC470755
0.8837	High Similarity	NPC116543
0.8837	High Similarity	NPC473390
0.8837	High Similarity	NPC131669
0.883	High Similarity	NPC475949
0.8824	High Similarity	NPC24417
0.8804	High Similarity	NPC475659
0.8791	High Similarity	NPC179746
0.8791	High Similarity	NPC475838
0.8791	High Similarity	NPC476300
0.8791	High Similarity	NPC81419
0.8791	High Similarity	NPC212486
0.8791	High Similarity	NPC228451
0.8791	High Similarity	NPC125674
0.8778	High Similarity	NPC474761
0.8778	High Similarity	NPC179394
0.8778	High Similarity	NPC51004
0.8778	High Similarity	NPC476004
0.8778	High Similarity	NPC144133
0.8764	High Similarity	NPC476803
0.8764	High Similarity	NPC475819
0.8764	High Similarity	NPC202672
0.875	High Similarity	NPC305475
0.875	High Similarity	NPC475461
0.8736	High Similarity	NPC158756
0.8736	High Similarity	NPC476804
0.8723	High Similarity	NPC474213
0.8721	High Similarity	NPC229825
0.871	High Similarity	NPC476315
0.871	High Similarity	NPC306041
0.8696	High Similarity	NPC474247
0.8681	High Similarity	NPC12172
0.8681	High Similarity	NPC208886
0.8667	High Similarity	NPC295312
0.8667	High Similarity	NPC307411
0.8646	High Similarity	NPC149371
0.8636	High Similarity	NPC255307
0.8621	High Similarity	NPC59097
0.8602	High Similarity	NPC471141
0.8588	High Similarity	NPC167881
0.8588	High Similarity	NPC98557
0.8556	High Similarity	NPC476805
0.8542	High Similarity	NPC47880
0.8539	High Similarity	NPC112685
0.8526	High Similarity	NPC187268
0.8523	High Similarity	NPC96259
0.8523	High Similarity	NPC191476
0.8523	High Similarity	NPC114979
0.8523	High Similarity	NPC141193
0.8511	High Similarity	NPC230800
0.8495	Intermediate Similarity	NPC473316
0.8495	Intermediate Similarity	NPC473330
0.8485	Intermediate Similarity	NPC477513
0.8471	Intermediate Similarity	NPC93763
0.8471	Intermediate Similarity	NPC471465
0.8471	Intermediate Similarity	NPC108816
0.8471	Intermediate Similarity	NPC196653
0.8469	Intermediate Similarity	NPC100487
0.8462	Intermediate Similarity	NPC477011
0.8462	Intermediate Similarity	NPC166919
0.8462	Intermediate Similarity	NPC151770
0.8391	Intermediate Similarity	NPC52861
0.8384	Intermediate Similarity	NPC243998
0.8372	Intermediate Similarity	NPC270126
0.8367	Intermediate Similarity	NPC475945
0.8367	Intermediate Similarity	NPC475871
0.8353	Intermediate Similarity	NPC476028
0.8353	Intermediate Similarity	NPC7563
0.8353	Intermediate Similarity	NPC141789
0.8353	Intermediate Similarity	NPC320630
0.8353	Intermediate Similarity	NPC171204
0.8353	Intermediate Similarity	NPC116177
0.8352	Intermediate Similarity	NPC20339
0.8352	Intermediate Similarity	NPC153805
0.8352	Intermediate Similarity	NPC40376
0.8352	Intermediate Similarity	NPC48338
0.8352	Intermediate Similarity	NPC89001
0.8352	Intermediate Similarity	NPC21208
0.8352	Intermediate Similarity	NPC233551
0.8352	Intermediate Similarity	NPC280621
0.8351	Intermediate Similarity	NPC164598
0.8351	Intermediate Similarity	NPC474339
0.8351	Intermediate Similarity	NPC476270
0.8333	Intermediate Similarity	NPC240695
0.8333	Intermediate Similarity	NPC114694
0.8333	Intermediate Similarity	NPC150755
0.8333	Intermediate Similarity	NPC142117
0.8333	Intermediate Similarity	NPC62118
0.8333	Intermediate Similarity	NPC107717
0.8333	Intermediate Similarity	NPC475581
0.8333	Intermediate Similarity	NPC171174
0.8333	Intermediate Similarity	NPC231096
0.8333	Intermediate Similarity	NPC232555
0.8316	Intermediate Similarity	NPC17585
0.8298	Intermediate Similarity	NPC471147
0.8283	Intermediate Similarity	NPC203659
0.8276	Intermediate Similarity	NPC281132
0.8265	Intermediate Similarity	NPC474747
0.8265	Intermediate Similarity	NPC320019
0.8265	Intermediate Similarity	NPC324017
0.8265	Intermediate Similarity	NPC86077
0.8265	Intermediate Similarity	NPC471148
0.8261	Intermediate Similarity	NPC477017
0.8261	Intermediate Similarity	NPC280612
0.8261	Intermediate Similarity	NPC477016
0.8242	Intermediate Similarity	NPC178215
0.8242	Intermediate Similarity	NPC231889
0.8242	Intermediate Similarity	NPC186148
0.8242	Intermediate Similarity	NPC160138
0.8235	Intermediate Similarity	NPC68819
0.8229	Intermediate Similarity	NPC40812
0.8222	Intermediate Similarity	NPC137033
0.8222	Intermediate Similarity	NPC100921
0.8222	Intermediate Similarity	NPC82795
0.8222	Intermediate Similarity	NPC120398
0.8222	Intermediate Similarity	NPC1083
0.8222	Intermediate Similarity	NPC223871
0.8222	Intermediate Similarity	NPC132496
0.8222	Intermediate Similarity	NPC66346
0.8222	Intermediate Similarity	NPC473478
0.8222	Intermediate Similarity	NPC107986
0.8222	Intermediate Similarity	NPC473669
0.8222	Intermediate Similarity	NPC231009
0.8222	Intermediate Similarity	NPC477018
0.8222	Intermediate Similarity	NPC283085
0.8222	Intermediate Similarity	NPC103284
0.8222	Intermediate Similarity	NPC50362
0.8222	Intermediate Similarity	NPC471567
0.8222	Intermediate Similarity	NPC319795
0.8222	Intermediate Similarity	NPC286338
0.8222	Intermediate Similarity	NPC38468
0.8222	Intermediate Similarity	NPC110710
0.8222	Intermediate Similarity	NPC473651
0.8211	Intermediate Similarity	NPC304886
0.8202	Intermediate Similarity	NPC250315
0.82	Intermediate Similarity	NPC223450
0.8191	Intermediate Similarity	NPC11456
0.8191	Intermediate Similarity	NPC469645
0.8191	Intermediate Similarity	NPC469692
0.8182	Intermediate Similarity	NPC472755
0.8182	Intermediate Similarity	NPC110989
0.8172	Intermediate Similarity	NPC473904
0.8172	Intermediate Similarity	NPC473448
0.8172	Intermediate Similarity	NPC469368
0.8172	Intermediate Similarity	NPC71533
0.8172	Intermediate Similarity	NPC80875
0.8172	Intermediate Similarity	NPC49342
0.8172	Intermediate Similarity	NPC475748
0.8172	Intermediate Similarity	NPC251385
0.8172	Intermediate Similarity	NPC239517
0.8172	Intermediate Similarity	NPC106510
0.8163	Intermediate Similarity	NPC46998
0.8163	Intermediate Similarity	NPC128733
0.8163	Intermediate Similarity	NPC185141
0.8163	Intermediate Similarity	NPC133907
0.8163	Intermediate Similarity	NPC110443
0.8163	Intermediate Similarity	NPC150923
0.8163	Intermediate Similarity	NPC473332
0.8163	Intermediate Similarity	NPC201718
0.8163	Intermediate Similarity	NPC474742
0.8163	Intermediate Similarity	NPC15993
0.8152	Intermediate Similarity	NPC151403
0.8152	Intermediate Similarity	NPC169511
0.8152	Intermediate Similarity	NPC172821
0.8152	Intermediate Similarity	NPC133730
0.8152	Intermediate Similarity	NPC61257
0.8152	Intermediate Similarity	NPC227379
0.8152	Intermediate Similarity	NPC191929
0.8152	Intermediate Similarity	NPC274446

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 NPC473321 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	182
0.1-0.2	1901
0.2-0.3	3696
0.3-0.4	2242
0.4-0.5	759
0.5-0.6	288
0.6-0.7	68
0.7-0.8	13
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
0.8222	Intermediate Similarity	NPD1733	Clinical (unspecified phase)
0.8172	Intermediate Similarity	NPD46	Approved
0.8172	Intermediate Similarity	NPD6698	Approved
0.7895	Intermediate Similarity	NPD7983	Approved
0.7604	Intermediate Similarity	NPD7838	Discovery
0.7596	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7547	Intermediate Similarity	NPD6371	Approved
0.7475	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD4225	Approved
0.7255	Intermediate Similarity	NPD8029	Clinical (unspecified phase)
0.7196	Intermediate Similarity	NPD6686	Approved
0.7188	Intermediate Similarity	NPD4249	Approved
0.7156	Intermediate Similarity	NPD8413	Clinical (unspecified phase)
0.7113	Intermediate Similarity	NPD4251	Approved
0.7113	Intermediate Similarity	NPD4250	Approved
0.7071	Intermediate Similarity	NPD5785	Approved
0.7053	Intermediate Similarity	NPD7154	Phase 3
0.697	Remote Similarity	NPD1695	Approved
0.6952	Remote Similarity	NPD5344	Discontinued
0.6931	Remote Similarity	NPD5779	Approved
0.6931	Remote Similarity	NPD5778	Approved
0.6915	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6907	Remote Similarity	NPD5363	Approved
0.6897	Remote Similarity	NPD8516	Approved
0.6897	Remote Similarity	NPD8513	Phase 3
0.6897	Remote Similarity	NPD8515	Approved
0.6897	Remote Similarity	NPD8517	Approved
0.6875	Remote Similarity	NPD6110	Phase 1
0.6837	Remote Similarity	NPD5786	Approved
0.6786	Remote Similarity	NPD6053	Discontinued
0.6771	Remote Similarity	NPD6435	Approved
0.6731	Remote Similarity	NPD7839	Suspended
0.6702	Remote Similarity	NPD4268	Approved
0.6702	Remote Similarity	NPD4271	Approved
0.6701	Remote Similarity	NPD5362	Discontinued
0.6612	Remote Similarity	NPD8074	Phase 3
0.6598	Remote Similarity	NPD4269	Approved
0.6598	Remote Similarity	NPD4270	Approved
0.6566	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD4819	Approved
0.6562	Remote Similarity	NPD4821	Approved
0.6562	Remote Similarity	NPD4252	Approved
0.6562	Remote Similarity	NPD4820	Approved
0.6562	Remote Similarity	NPD4822	Approved
0.6562	Remote Similarity	NPD5368	Approved
0.6552	Remote Similarity	NPD7115	Discovery
0.6542	Remote Similarity	NPD6648	Approved
0.6542	Remote Similarity	NPD7639	Approved
0.6542	Remote Similarity	NPD7640	Approved
0.6538	Remote Similarity	NPD5282	Discontinued
0.6518	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6517	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.65	Remote Similarity	NPD7829	Approved
0.65	Remote Similarity	NPD7642	Approved
0.65	Remote Similarity	NPD7830	Approved
0.6496	Remote Similarity	NPD7641	Discontinued
0.6449	Remote Similarity	NPD7638	Approved
0.6429	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.64	Remote Similarity	NPD1694	Approved
0.6393	Remote Similarity	NPD7507	Approved
0.6354	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6327	Remote Similarity	NPD5369	Approved
0.6316	Remote Similarity	NPD6421	Discontinued
0.6316	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6311	Remote Similarity	NPD6101	Approved
0.6311	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.63	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6293	Remote Similarity	NPD4632	Approved
0.6279	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6263	Remote Similarity	NPD5209	Approved
0.6261	Remote Similarity	NPD2204	Approved
0.625	Remote Similarity	NPD6319	Approved
0.625	Remote Similarity	NPD4756	Discovery
0.624	Remote Similarity	NPD7319	Approved
0.62	Remote Similarity	NPD5331	Approved
0.62	Remote Similarity	NPD5332	Approved
0.6198	Remote Similarity	NPD8444	Approved
0.6195	Remote Similarity	NPD6412	Phase 2
0.619	Remote Similarity	NPD7637	Suspended
0.619	Remote Similarity	NPD6411	Approved
0.6162	Remote Similarity	NPD4790	Discontinued
0.6154	Remote Similarity	NPD5370	Suspended
0.6142	Remote Similarity	NPD7260	Phase 2
0.614	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6129	Remote Similarity	NPD8451	Approved
0.6111	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6106	Remote Similarity	NPD6008	Approved
0.608	Remote Similarity	NPD8448	Approved
0.6068	Remote Similarity	NPD8297	Approved
0.6053	Remote Similarity	NPD5697	Approved
0.6053	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6048	Remote Similarity	NPD8341	Approved
0.6048	Remote Similarity	NPD7492	Approved
0.6048	Remote Similarity	NPD8340	Approved
0.6048	Remote Similarity	NPD8342	Approved
0.6048	Remote Similarity	NPD8299	Approved
0.6038	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.6019	Remote Similarity	NPD6422	Discontinued
0.6	Remote Similarity	NPD6881	Approved
0.6	Remote Similarity	NPD6009	Approved
0.6	Remote Similarity	NPD7500	Approved
0.6	Remote Similarity	NPD6899	Approved
0.6	Remote Similarity	NPD8273	Phase 1
0.6	Remote Similarity	NPD6616	Approved
0.6	Remote Similarity	NPD3197	Phase 1
0.5984	Remote Similarity	NPD6054	Approved
0.5983	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.5983	Remote Similarity	NPD6650	Approved
0.5983	Remote Similarity	NPD6649	Approved
0.5982	Remote Similarity	NPD7632	Discontinued
0.5981	Remote Similarity	NPD6399	Phase 3
0.5969	Remote Similarity	NPD6845	Suspended
0.5968	Remote Similarity	NPD8328	Phase 3
0.5965	Remote Similarity	NPD7128	Approved
0.5965	Remote Similarity	NPD6402	Approved
0.5965	Remote Similarity	NPD6675	Approved
0.5965	Remote Similarity	NPD5739	Approved
0.5963	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.5952	Remote Similarity	NPD7078	Approved
0.5948	Remote Similarity	NPD6012	Approved
0.5948	Remote Similarity	NPD6373	Approved
0.5948	Remote Similarity	NPD6013	Approved
0.5948	Remote Similarity	NPD6014	Approved
0.5948	Remote Similarity	NPD6372	Approved
0.5938	Remote Similarity	NPD8391	Approved
0.5938	Remote Similarity	NPD8392	Approved
0.5938	Remote Similarity	NPD8390	Approved
0.5935	Remote Similarity	NPD5983	Phase 2
0.5935	Remote Similarity	NPD6015	Approved
0.5935	Remote Similarity	NPD6016	Approved
0.5913	Remote Similarity	NPD5701	Approved
0.5906	Remote Similarity	NPD7736	Approved
0.5897	Remote Similarity	NPD7102	Approved
0.5897	Remote Similarity	NPD7290	Approved
0.5897	Remote Similarity	NPD6883	Approved
0.5887	Remote Similarity	NPD6370	Approved
0.5887	Remote Similarity	NPD5988	Approved
0.5876	Remote Similarity	NPD8039	Approved
0.587	Remote Similarity	NPD7331	Phase 2
0.5862	Remote Similarity	NPD7320	Approved
0.5862	Remote Similarity	NPD6011	Approved
0.5854	Remote Similarity	NPD6059	Approved
0.5847	Remote Similarity	NPD6847	Approved
0.5847	Remote Similarity	NPD6869	Approved
0.5847	Remote Similarity	NPD6617	Approved
0.5847	Remote Similarity	NPD8130	Phase 1
0.5843	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.5841	Remote Similarity	NPD5211	Phase 2
0.584	Remote Similarity	NPD7604	Phase 2
0.5827	Remote Similarity	NPD8293	Discontinued
0.582	Remote Similarity	NPD7328	Approved
0.582	Remote Similarity	NPD7327	Approved
0.581	Remote Similarity	NPD7524	Approved
0.5806	Remote Similarity	NPD7503	Approved
0.5806	Remote Similarity	NPD8033	Approved
0.5798	Remote Similarity	NPD6882	Approved
0.5789	Remote Similarity	NPD6647	Phase 2
0.5784	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.5772	Remote Similarity	NPD7516	Approved
0.5766	Remote Similarity	NPD6084	Phase 2
0.5766	Remote Similarity	NPD6083	Phase 2
0.5766	Remote Similarity	NPD7902	Approved
0.5763	Remote Similarity	NPD4634	Approved
0.5763	Remote Similarity	NPD2067	Discontinued
0.576	Remote Similarity	NPD8080	Discontinued
0.575	Remote Similarity	NPD8133	Approved
0.5748	Remote Similarity	NPD6336	Discontinued
0.5739	Remote Similarity	NPD5141	Approved
0.5738	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.5738	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.5738	Remote Similarity	NPD7505	Discontinued
0.5727	Remote Similarity	NPD5695	Phase 3
0.5726	Remote Similarity	NPD8294	Approved
0.5726	Remote Similarity	NPD8377	Approved
0.5714	Remote Similarity	NPD8387	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD5696	Approved
0.5692	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.569	Remote Similarity	NPD5048	Discontinued
0.568	Remote Similarity	NPD8296	Approved
0.568	Remote Similarity	NPD8267	Approved
0.568	Remote Similarity	NPD8335	Approved
0.568	Remote Similarity	NPD8380	Approved
0.568	Remote Similarity	NPD8269	Approved
0.568	Remote Similarity	NPD8379	Approved
0.568	Remote Similarity	NPD8266	Approved
0.568	Remote Similarity	NPD8268	Approved
0.568	Remote Similarity	NPD8378	Approved
0.5678	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.5673	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.5664	Remote Similarity	NPD5286	Approved
0.5664	Remote Similarity	NPD4696	Approved
0.5664	Remote Similarity	NPD5285	Approved
0.5656	Remote Similarity	NPD6274	Approved
0.5636	Remote Similarity	NPD7748	Approved
0.5625	Remote Similarity	NPD4755	Approved
0.5618	Remote Similarity	NPD9119	Approved
0.5618	Remote Similarity	NPD69	Approved
0.5603	Remote Similarity	NPD6190	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