NPASS Compound

Structure

NPC173516 OpenBabel07101718242D 41 46 0 0 1 0 0 0 0 0999 V2000 4.4936 4.3836 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7395 3.1590 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2395 2.2930 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1761 3.2239 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3370 5.9518 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6426 3.3948 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8608 2.7713 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5686 1.9945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5468 2.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7517 3.7160 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 -4.3776 0.5933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6026 2.7272 0.0000 C 0 0 1 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 4.0098 1.7824 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9698 4.3395 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2971 1.5243 0.0000 C 0 0 1 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 2.2395 2.2930 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 2.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.9407 1.4171 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0390 3.9742 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.0140 0.0406 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.1189 5.3284 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0468 1.3364 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.2280 1.1590 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 7 1 0 0 0 0 2 27 1 0 0 0 0 3 27 1 0 0 0 0 6 37 1 0 0 0 0 7 8 2 0 0 0 0 8 20 1 0 0 0 0 9 11 1 0 0 0 0 9 17 2 0 0 0 0 10 12 2 0 0 0 0 10 16 1 0 0 0 0 11 28 1 0 0 0 0 12 38 1 0 0 0 0 13 18 1 0 0 0 0 13 21 1 0 0 0 0 14 19 1 0 0 0 0 14 22 1 0 0 0 0 15 16 2 0 0 0 0 15 38 1 0 0 0 0 16 23 1 0 0 0 0 17 29 1 0 0 0 0 18 27 1 0 0 0 0 18 29 1 1 0 0 0 19 28 1 6 0 0 0 19 31 1 0 0 0 0 20 32 2 0 0 0 0 20 40 1 0 0 0 0 21 33 2 0 0 0 0 21 37 1 0 0 0 0 22 34 2 0 0 0 0 22 39 1 0 0 0 0 23 28 1 1 0 0 0 23 39 1 0 0 0 0 24 29 1 0 0 0 0 24 30 1 0 0 0 0 24 35 2 0 0 0 0 25 27 1 0 0 0 0 25 30 1 6 0 0 0 25 40 1 0 0 0 0 26 30 1 1 0 0 0 26 31 1 0 0 0 0 26 41 1 0 0 0 0 28 4 1 1 0 0 0 29 5 1 1 0 0 0 30 36 1 1 0 0 0 31 17 1 1 0 0 0 31 41 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	568.23
Volume:	560.204
LogP:	4.176
LogD:	2.866
LogS:	-5.192
# Rotatable Bonds:	7
TPSA:	141.87
# H-Bond Aceptor:	10
# H-Bond Donor:	1
# Rings:	6
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.185
Synthetic Accessibility Score:	6.775
Fsp3:	0.613
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.412
MDCK Permeability:	4.292124503990635e-05
Pgp-inhibitor:	0.998
Pgp-substrate:	0.867
Human Intestinal Absorption (HIA):	0.14
20% Bioavailability (F20%):	0.887
30% Bioavailability (F30%):	0.972

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.97
Plasma Protein Binding (PPB):	89.13957977294922%
Volume Distribution (VD):	1.665
Pgp-substrate:	11.961433410644531%

ADMET: Metabolism

CYP1A2-inhibitor:	0.003
CYP1A2-substrate:	0.713
CYP2C19-inhibitor:	0.387
CYP2C19-substrate:	0.355
CYP2C9-inhibitor:	0.576
CYP2C9-substrate:	0.014
CYP2D6-inhibitor:	0.005
CYP2D6-substrate:	0.08
CYP3A4-inhibitor:	0.9
CYP3A4-substrate:	0.738

ADMET: Excretion

Clearance (CL):	3.573
Half-life (T1/2):	0.262

ADMET: Toxicity

hERG Blockers:	0.0
Human Hepatotoxicity (H-HT):	0.856
Drug-inuced Liver Injury (DILI):	0.354
AMES Toxicity:	0.25
Rat Oral Acute Toxicity:	0.98
Maximum Recommended Daily Dose:	0.972
Skin Sensitization:	0.542
Carcinogencity:	0.424
Eye Corrosion:	0.056
Eye Irritation:	0.079
Respiratory Toxicity:	0.994

Download Data

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

Natural Product: NPC173516

Natural Product ID:	NPC173516
*Common Name:**	Trichinenlide B
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	SGMKQRGSUCSUNU-QCDIDFPLSA-N
Standard InCHI:	InChI=1S/C31H36O10/c1-7-8-20(32)40-25-27(2,3)18(13-21(33)37-6)29(5)17-9-11-28(4)19(31(17)26(41-31)30(25,36)24(29)35)14-22(34)39-23(28)16-10-12-38-15-16/h7-10,12,15,18-19,23,25-26,36H,11,13-14H2,1-6H3/b8-7+/t18-,19+,23-,25-,26+,28+,29+,30-,31+/m0/s1
SMILES:	C/C=C/C(=O)O[C@H]1C(C)(C)[C@H](CC(=O)OC)[C@@]2(C)C3=CC[C@]4(C)[C@@H](CC(=O)O[C@H]4c4ccoc4)[C@]43[C@@H]([C@@]1(C2=O)O)O4
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2431779
PubChem CID:	72702313
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids [CHEMONTID:0002380] Limonoids

*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
NPO32744	trichilia sinensis	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24094143]

☑ 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	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	2850.0	nM	PMID[482536]

☑ 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 NPC173516 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	376
0.1-0.2	1499
0.2-0.3	3312
0.3-0.4	5743
0.4-0.5	10046
0.5-0.6	9873
0.6-0.7	8869
0.7-0.8	2514
0.8-0.85	276
0.85-0.9	108
0.9-0.95	66
0.95-1	15

Similarity Score	Similarity Level	Natural Product ID
0.9936	High Similarity	NPC471397
0.9809	High Similarity	NPC160651
0.9806	High Similarity	NPC469338
0.9806	High Similarity	NPC292389
0.9744	High Similarity	NPC276551
0.9744	High Similarity	NPC469849
0.9744	High Similarity	NPC470940
0.9682	High Similarity	NPC470875
0.962	High Similarity	NPC472282
0.9615	High Similarity	NPC69028
0.9554	High Similarity	NPC477405
0.9551	High Similarity	NPC25255
0.9497	High Similarity	NPC472774
0.9497	High Similarity	NPC472775
0.9494	High Similarity	NPC476857
0.9494	High Similarity	NPC476858
0.9494	High Similarity	NPC476856
0.949	High Similarity	NPC82851
0.949	High Similarity	NPC193798
0.949	High Similarity	NPC5079
0.949	High Similarity	NPC149896
0.949	High Similarity	NPC470939
0.9437	High Similarity	NPC271235
0.943	High Similarity	NPC39986
0.943	High Similarity	NPC51568
0.943	High Similarity	NPC134254
0.943	High Similarity	NPC472773
0.943	High Similarity	NPC234660
0.943	High Similarity	NPC302369
0.9427	High Similarity	NPC472653
0.9427	High Similarity	NPC477402
0.9423	High Similarity	NPC286722
0.9419	High Similarity	NPC264943
0.9375	High Similarity	NPC476850
0.9375	High Similarity	NPC476861
0.9375	High Similarity	NPC476853
0.9371	High Similarity	NPC476860
0.9371	High Similarity	NPC123088
0.9371	High Similarity	NPC271657
0.9367	High Similarity	NPC329938
0.9367	High Similarity	NPC263432
0.9367	High Similarity	NPC18347
0.9367	High Similarity	NPC472771
0.9363	High Similarity	NPC473473
0.9363	High Similarity	NPC477403
0.9363	High Similarity	NPC475295
0.9359	High Similarity	NPC60973
0.9359	High Similarity	NPC209364
0.9313	High Similarity	NPC23387
0.9308	High Similarity	NPC476197
0.9304	High Similarity	NPC335761
0.9299	High Similarity	NPC299038
0.9299	High Similarity	NPC249021
0.9299	High Similarity	NPC187149
0.9299	High Similarity	NPC472283
0.9295	High Similarity	NPC469850
0.9295	High Similarity	NPC469336
0.9255	High Similarity	NPC472651
0.9255	High Similarity	NPC473753
0.9255	High Similarity	NPC473766
0.925	High Similarity	NPC470182
0.9245	High Similarity	NPC96443
0.9245	High Similarity	NPC200782
0.9245	High Similarity	NPC290400
0.9241	High Similarity	NPC237155
0.9241	High Similarity	NPC475967
0.9236	High Similarity	NPC107646
0.9236	High Similarity	NPC469485
0.9231	High Similarity	NPC178932
0.9198	High Similarity	NPC472652
0.9187	High Similarity	NPC469846
0.9182	High Similarity	NPC475381
0.9182	High Similarity	NPC305016
0.9177	High Similarity	NPC261597
0.9177	High Similarity	NPC173544
0.9177	High Similarity	NPC167142
0.9177	High Similarity	NPC472772
0.9177	High Similarity	NPC36655
0.9172	High Similarity	NPC281258
0.9172	High Similarity	NPC214541
0.9172	High Similarity	NPC44675
0.9167	High Similarity	NPC476201
0.9167	High Similarity	NPC469503
0.9161	High Similarity	NPC159927
0.9161	High Similarity	NPC469335
0.9125	High Similarity	NPC117986
0.9114	High Similarity	NPC126723
0.9114	High Similarity	NPC263265
0.9108	High Similarity	NPC282445
0.9096	High Similarity	NPC478177
0.9074	High Similarity	NPC475779
0.9057	High Similarity	NPC45101
0.9051	High Similarity	NPC476262
0.9038	High Similarity	NPC196864
0.9038	High Similarity	NPC477404
0.9036	High Similarity	NPC262386
0.9024	High Similarity	NPC82602
0.9024	High Similarity	NPC470995
0.9006	High Similarity	NPC188649
0.9	High Similarity	NPC307383
0.8981	High Similarity	NPC18135
0.8976	High Similarity	NPC94763
0.8976	High Similarity	NPC236004
0.897	High Similarity	NPC160818
0.897	High Similarity	NPC169299
0.8957	High Similarity	NPC121995
0.8957	High Similarity	NPC97574
0.8957	High Similarity	NPC93172
0.8951	High Similarity	NPC663
0.8951	High Similarity	NPC288602
0.8951	High Similarity	NPC224394
0.8951	High Similarity	NPC88841
0.8941	High Similarity	NPC242068
0.8941	High Similarity	NPC247563
0.8938	High Similarity	NPC472778
0.8938	High Similarity	NPC472777
0.8938	High Similarity	NPC472776
0.8924	High Similarity	NPC44577
0.8924	High Similarity	NPC268905
0.8924	High Similarity	NPC75906
0.8917	High Similarity	NPC46551
0.8917	High Similarity	NPC476122
0.8889	High Similarity	NPC68848
0.8889	High Similarity	NPC207978
0.8889	High Similarity	NPC18986
0.8889	High Similarity	NPC211777
0.8882	High Similarity	NPC473368
0.8868	High Similarity	NPC57998
0.8868	High Similarity	NPC30222
0.8862	High Similarity	NPC471437
0.8854	High Similarity	NPC125182
0.8854	High Similarity	NPC69647
0.8848	High Similarity	NPC472766
0.8848	High Similarity	NPC296558
0.8848	High Similarity	NPC472765
0.8846	High Similarity	NPC255414
0.8841	High Similarity	NPC472141
0.8834	High Similarity	NPC419
0.8834	High Similarity	NPC198047
0.8834	High Similarity	NPC472139
0.883	High Similarity	NPC105395
0.8827	High Similarity	NPC191828
0.8827	High Similarity	NPC287559
0.882	High Similarity	NPC88007
0.8812	High Similarity	NPC35000
0.8812	High Similarity	NPC92979
0.8802	High Similarity	NPC469848
0.8795	High Similarity	NPC302392
0.8788	High Similarity	NPC270312
0.8788	High Similarity	NPC472764
0.8782	High Similarity	NPC262198
0.8773	High Similarity	NPC197596
0.8773	High Similarity	NPC471166
0.8773	High Similarity	NPC471167
0.8765	High Similarity	NPC262872
0.8757	High Similarity	NPC472665
0.875	High Similarity	NPC469576
0.8743	High Similarity	NPC159232
0.8743	High Similarity	NPC285227
0.8727	High Similarity	NPC478178
0.8727	High Similarity	NPC149945
0.8726	High Similarity	NPC221809
0.872	High Similarity	NPC285567
0.872	High Similarity	NPC471168
0.872	High Similarity	NPC165218
0.8712	High Similarity	NPC470789
0.8704	High Similarity	NPC197137
0.8704	High Similarity	NPC195954
0.8704	High Similarity	NPC194499
0.8698	High Similarity	NPC469633
0.8675	High Similarity	NPC476224
0.8675	High Similarity	NPC100333
0.8667	High Similarity	NPC56358
0.8659	High Similarity	NPC5741
0.8659	High Similarity	NPC472767
0.8659	High Similarity	NPC472668
0.8655	High Similarity	NPC470938
0.8654	High Similarity	NPC86935
0.8654	High Similarity	NPC142113
0.865	High Similarity	NPC474611
0.865	High Similarity	NPC475226
0.8642	High Similarity	NPC41880
0.8639	High Similarity	NPC471632
0.8625	High Similarity	NPC272590
0.8623	High Similarity	NPC327922
0.8608	High Similarity	NPC470941
0.8606	High Similarity	NPC472669
0.8606	High Similarity	NPC283209
0.8599	High Similarity	NPC5676
0.8598	High Similarity	NPC8389
0.859	High Similarity	NPC243577
0.8589	High Similarity	NPC470118
0.858	High Similarity	NPC75310
0.858	High Similarity	NPC141538
0.858	High Similarity	NPC296807
0.858	High Similarity	NPC155939
0.8571	High Similarity	NPC33938
0.8571	High Similarity	NPC472659
0.8563	High Similarity	NPC478179
0.8562	High Similarity	NPC470997

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 NPC173516 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	316
0.1-0.2	1053
0.2-0.3	2235
0.3-0.4	2660
0.4-0.5	1779
0.5-0.6	814
0.6-0.7	256
0.7-0.8	34
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8663	High Similarity	NPD8434	Phase 2
0.8242	Intermediate Similarity	NPD5760	Phase 2
0.8242	Intermediate Similarity	NPD5761	Phase 2
0.8155	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7753	Intermediate Similarity	NPD6764	Approved
0.7753	Intermediate Similarity	NPD6765	Approved
0.7706	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7674	Intermediate Similarity	NPD7075	Discontinued
0.7582	Intermediate Similarity	NPD6785	Approved
0.7582	Intermediate Similarity	NPD6784	Approved
0.7529	Intermediate Similarity	NPD6599	Discontinued
0.75	Intermediate Similarity	NPD7819	Suspended
0.7486	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7459	Intermediate Similarity	NPD6559	Discontinued
0.7437	Intermediate Similarity	NPD8404	Phase 2
0.7386	Intermediate Similarity	NPD5494	Approved
0.7384	Intermediate Similarity	NPD7411	Suspended
0.738	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7356	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7356	Intermediate Similarity	NPD3817	Phase 2
0.7341	Intermediate Similarity	NPD6801	Discontinued
0.7333	Intermediate Similarity	NPD3751	Discontinued
0.7314	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD4628	Phase 3
0.7278	Intermediate Similarity	NPD6799	Approved
0.7273	Intermediate Similarity	NPD3749	Approved
0.7258	Intermediate Similarity	NPD8150	Discontinued
0.7257	Intermediate Similarity	NPD5402	Approved
0.7247	Intermediate Similarity	NPD1247	Approved
0.7232	Intermediate Similarity	NPD919	Approved
0.7225	Intermediate Similarity	NPD4380	Phase 2
0.7222	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD6166	Phase 2
0.7222	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7216	Intermediate Similarity	NPD3882	Suspended
0.7207	Intermediate Similarity	NPD3787	Discontinued
0.72	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7198	Intermediate Similarity	NPD5844	Phase 1
0.7198	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7182	Intermediate Similarity	NPD7473	Discontinued
0.7175	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7168	Intermediate Similarity	NPD3226	Approved
0.7151	Intermediate Similarity	NPD5403	Approved
0.7151	Intermediate Similarity	NPD920	Approved
0.7143	Intermediate Similarity	NPD1934	Approved
0.7143	Intermediate Similarity	NPD3818	Discontinued
0.7135	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD5401	Approved
0.7127	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD1471	Phase 3
0.712	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD8312	Approved
0.7097	Intermediate Similarity	NPD8313	Approved
0.7081	Intermediate Similarity	NPD7251	Discontinued
0.7065	Intermediate Similarity	NPD7074	Phase 3
0.7059	Intermediate Similarity	NPD8407	Phase 2
0.7056	Intermediate Similarity	NPD8127	Discontinued
0.7049	Intermediate Similarity	NPD7799	Discontinued
0.7043	Intermediate Similarity	NPD7808	Phase 3
0.7041	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7035	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7035	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7035	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD6797	Phase 2
0.7024	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD7236	Approved
0.7017	Intermediate Similarity	NPD6232	Discontinued
0.7011	Intermediate Similarity	NPD7054	Approved
0.7005	Intermediate Similarity	NPD7435	Discontinued
0.6989	Remote Similarity	NPD8368	Discontinued
0.6989	Remote Similarity	NPD7685	Pre-registration
0.6978	Remote Similarity	NPD3926	Phase 2
0.6973	Remote Similarity	NPD7472	Approved
0.6961	Remote Similarity	NPD6959	Discontinued
0.6957	Remote Similarity	NPD7907	Approved
0.6942	Remote Similarity	NPD4111	Phase 1
0.6936	Remote Similarity	NPD2532	Approved
0.6936	Remote Similarity	NPD2534	Approved
0.6936	Remote Similarity	NPD2533	Approved
0.6923	Remote Similarity	NPD2346	Discontinued
0.6919	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD7239	Suspended
0.6911	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.691	Remote Similarity	NPD1465	Phase 2
0.691	Remote Similarity	NPD2801	Approved
0.6901	Remote Similarity	NPD3750	Approved
0.6897	Remote Similarity	NPD6273	Approved
0.6888	Remote Similarity	NPD8285	Discontinued
0.6885	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD1549	Phase 2
0.6875	Remote Similarity	NPD7458	Discontinued
0.6865	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6865	Remote Similarity	NPD7228	Approved
0.6864	Remote Similarity	NPD2796	Approved
0.6864	Remote Similarity	NPD6099	Approved
0.6864	Remote Similarity	NPD6100	Approved
0.686	Remote Similarity	NPD4665	Approved
0.6854	Remote Similarity	NPD37	Approved
0.6853	Remote Similarity	NPD6780	Approved
0.6853	Remote Similarity	NPD6776	Approved
0.6853	Remote Similarity	NPD6778	Approved
0.6853	Remote Similarity	NPD6782	Approved
0.6853	Remote Similarity	NPD6777	Approved
0.6853	Remote Similarity	NPD6779	Approved
0.6853	Remote Similarity	NPD6781	Approved
0.6851	Remote Similarity	NPD6234	Discontinued
0.6842	Remote Similarity	NPD2800	Approved
0.6839	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6833	Remote Similarity	NPD4965	Approved
0.6833	Remote Similarity	NPD4967	Phase 2
0.6833	Remote Similarity	NPD7768	Phase 2
0.6833	Remote Similarity	NPD4966	Approved
0.6826	Remote Similarity	NPD6355	Discontinued
0.6824	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6823	Remote Similarity	NPD8435	Approved
0.6823	Remote Similarity	NPD8360	Approved
0.6823	Remote Similarity	NPD8361	Approved
0.681	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.6805	Remote Similarity	NPD2799	Discontinued
0.6805	Remote Similarity	NPD3748	Approved
0.68	Remote Similarity	NPD1512	Approved
0.6798	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6798	Remote Similarity	NPD7874	Approved
0.678	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6776	Remote Similarity	NPD7199	Phase 2
0.6768	Remote Similarity	NPD4107	Approved
0.6765	Remote Similarity	NPD1551	Phase 2
0.6761	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD2403	Approved
0.675	Remote Similarity	NPD7697	Approved
0.675	Remote Similarity	NPD7497	Discontinued
0.675	Remote Similarity	NPD7698	Approved
0.675	Remote Similarity	NPD7696	Phase 3
0.6744	Remote Similarity	NPD1243	Approved
0.6738	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.672	Remote Similarity	NPD7240	Approved
0.6719	Remote Similarity	NPD8424	Clinical (unspecified phase)
0.6716	Remote Similarity	NPD7871	Phase 2
0.6716	Remote Similarity	NPD7870	Phase 2
0.6716	Remote Similarity	NPD8319	Approved
0.6716	Remote Similarity	NPD8320	Phase 1
0.67	Remote Similarity	NPD3057	Approved
0.67	Remote Similarity	NPD7701	Phase 2
0.6686	Remote Similarity	NPD1511	Approved
0.6686	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6683	Remote Similarity	NPD7801	Approved
0.6667	Remote Similarity	NPD6190	Approved
0.6667	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.665	Remote Similarity	NPD4482	Phase 3
0.6649	Remote Similarity	NPD7229	Phase 3
0.6647	Remote Similarity	NPD7097	Phase 1
0.6647	Remote Similarity	NPD3268	Approved
0.6647	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6647	Remote Similarity	NPD2313	Discontinued
0.663	Remote Similarity	NPD8455	Phase 2
0.6628	Remote Similarity	NPD5763	Approved
0.6628	Remote Similarity	NPD5762	Approved
0.6628	Remote Similarity	NPD2344	Approved
0.6627	Remote Similarity	NPD6832	Phase 2
0.6621	Remote Similarity	NPD7048	Phase 3
0.6617	Remote Similarity	NPD3533	Approved
0.6617	Remote Similarity	NPD2972	Approved
0.6616	Remote Similarity	NPD8485	Approved
0.6616	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.661	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6609	Remote Similarity	NPD8166	Discontinued
0.6608	Remote Similarity	NPD7033	Discontinued
0.6608	Remote Similarity	NPD1510	Phase 2
0.66	Remote Similarity	NPD4580	Approved
0.6599	Remote Similarity	NPD6534	Approved
0.6599	Remote Similarity	NPD6535	Approved
0.6587	Remote Similarity	NPD7095	Approved
0.6585	Remote Similarity	NPD8151	Discontinued
0.6583	Remote Similarity	NPD7700	Phase 2
0.6583	Remote Similarity	NPD7699	Phase 2
0.657	Remote Similarity	NPD2935	Discontinued
0.6559	Remote Similarity	NPD5711	Approved
0.6559	Remote Similarity	NPD6808	Phase 2
0.6559	Remote Similarity	NPD5710	Approved
0.6557	Remote Similarity	NPD7058	Phase 2
0.6557	Remote Similarity	NPD7057	Phase 3
0.6552	Remote Similarity	NPD4583	Approved
0.6552	Remote Similarity	NPD4582	Approved
0.6548	Remote Similarity	NPD6798	Discontinued
0.6535	Remote Similarity	NPD2491	Approved
0.6535	Remote Similarity	NPD6823	Phase 2
0.6533	Remote Similarity	NPD2974	Approved
0.6533	Remote Similarity	NPD2975	Approved
0.6533	Remote Similarity	NPD2973	Approved
0.6529	Remote Similarity	NPD447	Suspended
0.6522	Remote Similarity	NPD7783	Phase 2
0.6522	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6519	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6517	Remote Similarity	NPD8486	Clinical (unspecified phase)
0.6517	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6514	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6514	Remote Similarity	NPD4110	Phase 3
0.6514	Remote Similarity	NPD7003	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