NPASS Compound

Structure

NPC471397 OpenBabel07101718292D 42 47 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 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 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 1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7517 -3.7160 0.0000 C 0 0 3 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 2.5981 -0.5000 0.0000 C 0 0 1 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 -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 1.7321 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6825 -4.0814 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 -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 38 1 0 0 0 0 7 8 2 0 0 0 0 8 18 1 0 0 0 0 9 11 1 0 0 0 0 9 16 2 0 0 0 0 10 12 2 0 0 0 0 10 15 1 0 0 0 0 11 28 1 0 0 0 0 12 39 1 0 0 0 0 13 17 1 0 0 0 0 13 19 1 0 0 0 0 14 15 2 0 0 0 0 14 39 1 0 0 0 0 15 22 1 0 0 0 0 16 29 1 0 0 0 0 17 28 1 6 0 0 0 17 31 1 0 0 0 0 18 32 2 0 0 0 0 18 41 1 0 0 0 0 19 33 2 0 0 0 0 19 40 1 0 0 0 0 20 21 1 0 0 0 0 20 23 1 0 0 0 0 20 34 1 0 0 0 0 21 27 1 0 0 0 0 21 29 1 1 0 0 0 22 28 1 1 0 0 0 22 40 1 0 0 0 0 23 35 2 0 0 0 0 23 38 1 0 0 0 0 24 29 1 0 0 0 0 24 30 1 0 0 0 0 24 36 2 0 0 0 0 25 27 1 0 0 0 0 25 30 1 6 0 0 0 25 41 1 0 0 0 0 26 30 1 1 0 0 0 26 31 1 0 0 0 0 26 42 1 0 0 0 0 28 4 1 1 0 0 0 29 5 1 1 0 0 0 30 37 1 1 0 0 0 31 16 1 1 0 0 0 31 42 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	584.23
Volume:	568.994
LogP:	3.417
LogD:	1.223
LogS:	-4.01
# Rotatable Bonds:	7
TPSA:	162.1
# H-Bond Aceptor:	11
# H-Bond Donor:	2
# Rings:	6
# Heavy Atoms:	11

MedChem Properties

QED Drug-Likeness Score:	0.166
Synthetic Accessibility Score:	7.043
Fsp3:	0.613
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.436
MDCK Permeability:	4.805729986401275e-05
Pgp-inhibitor:	0.974
Pgp-substrate:	0.997
Human Intestinal Absorption (HIA):	0.041
20% Bioavailability (F20%):	0.179
30% Bioavailability (F30%):	0.733

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.617
Plasma Protein Binding (PPB):	92.6318588256836%
Volume Distribution (VD):	1.79
Pgp-substrate:	12.008977890014648%

ADMET: Metabolism

CYP1A2-inhibitor:	0.001
CYP1A2-substrate:	0.921
CYP2C19-inhibitor:	0.022
CYP2C19-substrate:	0.41
CYP2C9-inhibitor:	0.12
CYP2C9-substrate:	0.012
CYP2D6-inhibitor:	0.005
CYP2D6-substrate:	0.078
CYP3A4-inhibitor:	0.784
CYP3A4-substrate:	0.65

ADMET: Excretion

Clearance (CL):	2.286
Half-life (T1/2):	0.149

ADMET: Toxicity

hERG Blockers:	0.0
Human Hepatotoxicity (H-HT):	0.743
Drug-inuced Liver Injury (DILI):	0.822
AMES Toxicity:	0.584
Rat Oral Acute Toxicity:	0.964
Maximum Recommended Daily Dose:	0.957
Skin Sensitization:	0.643
Carcinogencity:	0.297
Eye Corrosion:	0.042
Eye Irritation:	0.161
Respiratory Toxicity:	0.991

Download Data

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

Natural Product: NPC471397

Natural Product ID:	NPC471397
*Common Name:**	Trichinenlide C
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	UCHPUEMCYMPXDX-UYQGBQFOSA-N
Standard InCHI:	InChI=1S/C31H36O11/c1-7-8-18(32)41-25-27(2,3)21(20(34)23(35)38-6)29(5)16-9-11-28(4)17(31(16)26(42-31)30(25,37)24(29)36)13-19(33)40-22(28)15-10-12-39-14-15/h7-10,12,14,17,20-22,25-26,34,37H,11,13H2,1-6H3/b8-7+/t17-,20?,21+,22+,25+,26-,28-,29-,30+,31-/m1/s1
SMILES:	C/C=C/C(=O)O[C@H]1C(C)(C)[C@H](C(C(=O)OC)O)[C@@]2(C(=O)[C@@]1(O)[C@H]1O[C@]31C2=CC[C@@]1([C@H]3CC(=O)O[C@H]1c1ccoc1)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2431778
PubChem CID:	72702314
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	=	1880.0	nM	PMID[509004]

☑ 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 NPC471397 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	1475
0.2-0.3	3309
0.3-0.4	5631
0.4-0.5	9975
0.5-0.6	9959
0.6-0.7	8758
0.7-0.8	2745
0.8-0.85	269
0.85-0.9	117
0.9-0.95	63
0.95-1	20

Similarity Score	Similarity Level	Natural Product ID
0.9936	High Similarity	NPC173516
0.9808	High Similarity	NPC276551
0.9747	High Similarity	NPC160651
0.9745	High Similarity	NPC470875
0.9744	High Similarity	NPC469338
0.9744	High Similarity	NPC292389
0.9684	High Similarity	NPC472282
0.9682	High Similarity	NPC469849
0.9682	High Similarity	NPC470940
0.9679	High Similarity	NPC69028
0.9618	High Similarity	NPC477405
0.956	High Similarity	NPC472775
0.956	High Similarity	NPC472774
0.9557	High Similarity	NPC476857
0.9557	High Similarity	NPC476856
0.9557	High Similarity	NPC476858
0.9554	High Similarity	NPC5079
0.95	High Similarity	NPC271235
0.9494	High Similarity	NPC302369
0.9494	High Similarity	NPC51568
0.9494	High Similarity	NPC134254
0.9494	High Similarity	NPC39986
0.9494	High Similarity	NPC472773
0.9494	High Similarity	NPC234660
0.949	High Similarity	NPC25255
0.949	High Similarity	NPC477402
0.9437	High Similarity	NPC476850
0.9437	High Similarity	NPC476861
0.9437	High Similarity	NPC476853
0.9434	High Similarity	NPC271657
0.9434	High Similarity	NPC123088
0.943	High Similarity	NPC82851
0.943	High Similarity	NPC193798
0.943	High Similarity	NPC149896
0.943	High Similarity	NPC263432
0.943	High Similarity	NPC470939
0.943	High Similarity	NPC472771
0.9375	High Similarity	NPC23387
0.9367	High Similarity	NPC472653
0.9367	High Similarity	NPC335761
0.9363	High Similarity	NPC286722
0.9359	High Similarity	NPC264943
0.9359	High Similarity	NPC469336
0.9317	High Similarity	NPC472651
0.9313	High Similarity	NPC476860
0.9308	High Similarity	NPC200782
0.9308	High Similarity	NPC329938
0.9308	High Similarity	NPC290400
0.9308	High Similarity	NPC18347
0.9308	High Similarity	NPC96443
0.9304	High Similarity	NPC473473
0.9304	High Similarity	NPC475295
0.9304	High Similarity	NPC477403
0.9304	High Similarity	NPC475967
0.9299	High Similarity	NPC209364
0.9299	High Similarity	NPC60973
0.9295	High Similarity	NPC178932
0.9259	High Similarity	NPC472652
0.925	High Similarity	NPC476197
0.9241	High Similarity	NPC187149
0.9241	High Similarity	NPC299038
0.9241	High Similarity	NPC249021
0.9241	High Similarity	NPC472772
0.9241	High Similarity	NPC472283
0.9236	High Similarity	NPC281258
0.9236	High Similarity	NPC469850
0.9231	High Similarity	NPC469503
0.9198	High Similarity	NPC473753
0.9198	High Similarity	NPC473766
0.9193	High Similarity	NPC470182
0.9187	High Similarity	NPC117986
0.9182	High Similarity	NPC237155
0.9177	High Similarity	NPC469485
0.9177	High Similarity	NPC107646
0.9136	High Similarity	NPC475779
0.913	High Similarity	NPC469846
0.9125	High Similarity	NPC305016
0.9125	High Similarity	NPC475381
0.9119	High Similarity	NPC45101
0.9119	High Similarity	NPC173544
0.9119	High Similarity	NPC261597
0.9119	High Similarity	NPC167142
0.9119	High Similarity	NPC36655
0.9114	High Similarity	NPC214541
0.9114	High Similarity	NPC44675
0.9108	High Similarity	NPC476201
0.9103	High Similarity	NPC159927
0.9103	High Similarity	NPC469335
0.9096	High Similarity	NPC262386
0.9085	High Similarity	NPC470995
0.9085	High Similarity	NPC82602
0.9062	High Similarity	NPC307383
0.9057	High Similarity	NPC126723
0.9057	High Similarity	NPC263265
0.9051	High Similarity	NPC282445
0.9042	High Similarity	NPC478177
0.903	High Similarity	NPC169299
0.903	High Similarity	NPC160818
0.9018	High Similarity	NPC97574
0.9018	High Similarity	NPC93172
0.9018	High Similarity	NPC121995
0.9	High Similarity	NPC472777
0.9	High Similarity	NPC472778
0.9	High Similarity	NPC247563
0.9	High Similarity	NPC472776
0.9	High Similarity	NPC242068
0.8994	High Similarity	NPC476262
0.8987	High Similarity	NPC75906
0.8981	High Similarity	NPC477404
0.8981	High Similarity	NPC196864
0.8951	High Similarity	NPC188649
0.8951	High Similarity	NPC211777
0.8951	High Similarity	NPC18986
0.8951	High Similarity	NPC207978
0.8931	High Similarity	NPC57998
0.8924	High Similarity	NPC18135
0.8922	High Similarity	NPC471437
0.8922	High Similarity	NPC94763
0.8922	High Similarity	NPC236004
0.8917	High Similarity	NPC69647
0.8917	High Similarity	NPC125182
0.8909	High Similarity	NPC472766
0.8909	High Similarity	NPC472765
0.8896	High Similarity	NPC288602
0.8896	High Similarity	NPC663
0.8896	High Similarity	NPC88841
0.8896	High Similarity	NPC198047
0.8896	High Similarity	NPC224394
0.8889	High Similarity	NPC105395
0.8875	High Similarity	NPC35000
0.8875	High Similarity	NPC92979
0.8868	High Similarity	NPC44577
0.8868	High Similarity	NPC268905
0.8861	High Similarity	NPC46551
0.8861	High Similarity	NPC476122
0.8848	High Similarity	NPC472764
0.8834	High Similarity	NPC68848
0.8827	High Similarity	NPC262872
0.8827	High Similarity	NPC473368
0.8812	High Similarity	NPC30222
0.8802	High Similarity	NPC285227
0.8795	High Similarity	NPC296558
0.879	High Similarity	NPC255414
0.8788	High Similarity	NPC472141
0.878	High Similarity	NPC419
0.878	High Similarity	NPC472139
0.8773	High Similarity	NPC470789
0.8773	High Similarity	NPC287559
0.8773	High Similarity	NPC191828
0.8765	High Similarity	NPC197137
0.8765	High Similarity	NPC88007
0.8765	High Similarity	NPC194499
0.875	High Similarity	NPC469848
0.8743	High Similarity	NPC302392
0.8735	High Similarity	NPC270312
0.8735	High Similarity	NPC100333
0.8726	High Similarity	NPC262198
0.872	High Similarity	NPC471167
0.872	High Similarity	NPC197596
0.872	High Similarity	NPC472767
0.872	High Similarity	NPC471166
0.872	High Similarity	NPC5741
0.8713	High Similarity	NPC470938
0.8712	High Similarity	NPC475226
0.8712	High Similarity	NPC474611
0.8706	High Similarity	NPC472665
0.8698	High Similarity	NPC471632
0.8698	High Similarity	NPC469576
0.869	High Similarity	NPC159232
0.8675	High Similarity	NPC149945
0.8675	High Similarity	NPC478178
0.8671	High Similarity	NPC221809
0.8667	High Similarity	NPC283209
0.8667	High Similarity	NPC285567
0.8667	High Similarity	NPC165218
0.8667	High Similarity	NPC471168
0.8662	High Similarity	NPC5676
0.8654	High Similarity	NPC243577
0.865	High Similarity	NPC195954
0.8647	High Similarity	NPC469633
0.8642	High Similarity	NPC75310
0.8642	High Similarity	NPC155939
0.8642	High Similarity	NPC141538
0.8642	High Similarity	NPC296807
0.8634	High Similarity	NPC33938
0.8631	High Similarity	NPC472659
0.8625	High Similarity	NPC470997
0.8623	High Similarity	NPC476224
0.8614	High Similarity	NPC56358
0.8614	High Similarity	NPC146991
0.8606	High Similarity	NPC79571
0.8606	High Similarity	NPC470792
0.8606	High Similarity	NPC472668
0.8599	High Similarity	NPC137295
0.8599	High Similarity	NPC476944
0.8599	High Similarity	NPC142113
0.8599	High Similarity	NPC86935
0.8589	High Similarity	NPC41880
0.858	High Similarity	NPC114880
0.858	High Similarity	NPC302054

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 NPC471397 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	317
0.1-0.2	1056
0.2-0.3	2246
0.3-0.4	2636
0.4-0.5	1784
0.5-0.6	814
0.6-0.7	253
0.7-0.8	41
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
0.8721	High Similarity	NPD8434	Phase 2
0.8303	Intermediate Similarity	NPD5760	Phase 2
0.8303	Intermediate Similarity	NPD5761	Phase 2
0.8107	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7809	Intermediate Similarity	NPD6764	Approved
0.7809	Intermediate Similarity	NPD6765	Approved
0.7661	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7637	Intermediate Similarity	NPD6784	Approved
0.7637	Intermediate Similarity	NPD6785	Approved
0.763	Intermediate Similarity	NPD7075	Discontinued
0.7514	Intermediate Similarity	NPD6559	Discontinued
0.7487	Intermediate Similarity	NPD8404	Phase 2
0.7485	Intermediate Similarity	NPD6599	Discontinued
0.7457	Intermediate Similarity	NPD7819	Suspended
0.7446	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7433	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7399	Intermediate Similarity	NPD6801	Discontinued
0.7389	Intermediate Similarity	NPD3751	Discontinued
0.7365	Intermediate Similarity	NPD4628	Phase 3
0.7345	Intermediate Similarity	NPD5494	Approved
0.7341	Intermediate Similarity	NPD7411	Suspended
0.7314	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7314	Intermediate Similarity	NPD3817	Phase 2
0.7314	Intermediate Similarity	NPD5402	Approved
0.7312	Intermediate Similarity	NPD8150	Discontinued
0.7283	Intermediate Similarity	NPD4380	Phase 2
0.7278	Intermediate Similarity	NPD6166	Phase 2
0.7278	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7263	Intermediate Similarity	NPD3787	Discontinued
0.7253	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7253	Intermediate Similarity	NPD5844	Phase 1
0.7235	Intermediate Similarity	NPD6799	Approved
0.7232	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7232	Intermediate Similarity	NPD3749	Approved
0.7209	Intermediate Similarity	NPD5403	Approved
0.7207	Intermediate Similarity	NPD1247	Approved
0.7198	Intermediate Similarity	NPD3818	Discontinued
0.7193	Intermediate Similarity	NPD5401	Approved
0.7191	Intermediate Similarity	NPD919	Approved
0.7189	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7175	Intermediate Similarity	NPD3882	Suspended
0.7174	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7159	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD8313	Approved
0.7151	Intermediate Similarity	NPD8312	Approved
0.7143	Intermediate Similarity	NPD7473	Discontinued
0.7135	Intermediate Similarity	NPD7251	Discontinued
0.7126	Intermediate Similarity	NPD3226	Approved
0.712	Intermediate Similarity	NPD7074	Phase 3
0.7112	Intermediate Similarity	NPD8407	Phase 2
0.7111	Intermediate Similarity	NPD8127	Discontinued
0.711	Intermediate Similarity	NPD920	Approved
0.7104	Intermediate Similarity	NPD7799	Discontinued
0.7102	Intermediate Similarity	NPD1934	Approved
0.7097	Intermediate Similarity	NPD7808	Phase 3
0.7093	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7088	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD1471	Phase 3
0.7081	Intermediate Similarity	NPD6797	Phase 2
0.7076	Intermediate Similarity	NPD7236	Approved
0.7065	Intermediate Similarity	NPD7054	Approved
0.7059	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7056	Intermediate Similarity	NPD7435	Discontinued
0.7043	Intermediate Similarity	NPD7685	Pre-registration
0.7043	Intermediate Similarity	NPD8368	Discontinued
0.7027	Intermediate Similarity	NPD7472	Approved
0.7	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD642	Clinical (unspecified phase)
0.699	Remote Similarity	NPD4111	Phase 1
0.6982	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6978	Remote Similarity	NPD6232	Discontinued
0.6971	Remote Similarity	NPD7239	Suspended
0.6954	Remote Similarity	NPD6273	Approved
0.694	Remote Similarity	NPD3926	Phase 2
0.6923	Remote Similarity	NPD7907	Approved
0.6923	Remote Similarity	NPD6959	Discontinued
0.6919	Remote Similarity	NPD7228	Approved
0.691	Remote Similarity	NPD37	Approved
0.6908	Remote Similarity	NPD4665	Approved
0.6904	Remote Similarity	NPD6781	Approved
0.6904	Remote Similarity	NPD6778	Approved
0.6904	Remote Similarity	NPD6782	Approved
0.6904	Remote Similarity	NPD6780	Approved
0.6904	Remote Similarity	NPD6777	Approved
0.6904	Remote Similarity	NPD6779	Approved
0.6904	Remote Similarity	NPD6776	Approved
0.6897	Remote Similarity	NPD2532	Approved
0.6897	Remote Similarity	NPD2534	Approved
0.6897	Remote Similarity	NPD2533	Approved
0.6889	Remote Similarity	NPD4967	Phase 2
0.6889	Remote Similarity	NPD4966	Approved
0.6889	Remote Similarity	NPD4965	Approved
0.6882	Remote Similarity	NPD2346	Discontinued
0.6879	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD8361	Approved
0.6875	Remote Similarity	NPD8360	Approved
0.6875	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD8435	Approved
0.6872	Remote Similarity	NPD2801	Approved
0.6872	Remote Similarity	NPD1465	Phase 2
0.686	Remote Similarity	NPD3750	Approved
0.6857	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.6853	Remote Similarity	NPD8285	Discontinued
0.6848	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6847	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6847	Remote Similarity	NPD7874	Approved
0.6842	Remote Similarity	NPD1549	Phase 2
0.6836	Remote Similarity	NPD7458	Discontinued
0.6836	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6831	Remote Similarity	NPD7199	Phase 2
0.6828	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD6100	Approved
0.6824	Remote Similarity	NPD6099	Approved
0.6824	Remote Similarity	NPD2796	Approved
0.6813	Remote Similarity	NPD6234	Discontinued
0.6802	Remote Similarity	NPD2800	Approved
0.68	Remote Similarity	NPD7696	Phase 3
0.68	Remote Similarity	NPD7698	Approved
0.68	Remote Similarity	NPD7697	Approved
0.68	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6796	Remote Similarity	NPD7768	Phase 2
0.6791	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD6355	Discontinued
0.6784	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6784	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD7240	Approved
0.6771	Remote Similarity	NPD8424	Clinical (unspecified phase)
0.6766	Remote Similarity	NPD7870	Phase 2
0.6766	Remote Similarity	NPD7871	Phase 2
0.6766	Remote Similarity	NPD8320	Phase 1
0.6766	Remote Similarity	NPD8319	Approved
0.6765	Remote Similarity	NPD3748	Approved
0.6765	Remote Similarity	NPD2799	Discontinued
0.6761	Remote Similarity	NPD1512	Approved
0.675	Remote Similarity	NPD3057	Approved
0.6749	Remote Similarity	NPD7701	Phase 2
0.6734	Remote Similarity	NPD4107	Approved
0.6732	Remote Similarity	NPD7801	Approved
0.6726	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6725	Remote Similarity	NPD1551	Phase 2
0.6724	Remote Similarity	NPD6190	Approved
0.6723	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.672	Remote Similarity	NPD2403	Approved
0.6716	Remote Similarity	NPD7497	Discontinued
0.6705	Remote Similarity	NPD1243	Approved
0.6686	Remote Similarity	NPD5763	Approved
0.6686	Remote Similarity	NPD5762	Approved
0.6685	Remote Similarity	NPD8455	Phase 2
0.6667	Remote Similarity	NPD3533	Approved
0.6667	Remote Similarity	NPD7033	Discontinued
0.6667	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD8485	Approved
0.6667	Remote Similarity	NPD2972	Approved
0.665	Remote Similarity	NPD6535	Approved
0.665	Remote Similarity	NPD6534	Approved
0.6648	Remote Similarity	NPD1511	Approved
0.6647	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6634	Remote Similarity	NPD8151	Discontinued
0.6633	Remote Similarity	NPD7700	Phase 2
0.6633	Remote Similarity	NPD7699	Phase 2
0.6617	Remote Similarity	NPD4482	Phase 3
0.6613	Remote Similarity	NPD7229	Phase 3
0.6612	Remote Similarity	NPD7057	Phase 3
0.6612	Remote Similarity	NPD7058	Phase 2
0.6608	Remote Similarity	NPD7097	Phase 1
0.6607	Remote Similarity	NPD3268	Approved
0.6607	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6607	Remote Similarity	NPD2313	Discontinued
0.6591	Remote Similarity	NPD7048	Phase 3
0.659	Remote Similarity	NPD2344	Approved
0.6587	Remote Similarity	NPD6832	Phase 2
0.6584	Remote Similarity	NPD2491	Approved
0.6584	Remote Similarity	NPD6823	Phase 2
0.6573	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD8166	Discontinued
0.657	Remote Similarity	NPD1510	Phase 2
0.657	Remote Similarity	NPD7783	Phase 2
0.657	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6567	Remote Similarity	NPD8486	Clinical (unspecified phase)
0.6567	Remote Similarity	NPD4580	Approved
0.6548	Remote Similarity	NPD7095	Approved
0.6532	Remote Similarity	NPD2935	Discontinued
0.6526	Remote Similarity	NPD8155	Clinical (unspecified phase)
0.6524	Remote Similarity	NPD5710	Approved
0.6524	Remote Similarity	NPD6808	Phase 2
0.6524	Remote Similarity	NPD5711	Approved
0.652	Remote Similarity	NPD4582	Approved
0.652	Remote Similarity	NPD4583	Approved
0.6509	Remote Similarity	NPD6798	Discontinued
0.6502	Remote Similarity	NPD3448	Approved
0.65	Remote Similarity	NPD2973	Approved
0.65	Remote Similarity	NPD2975	Approved
0.65	Remote Similarity	NPD2974	Approved
0.6491	Remote Similarity	NPD447	Suspended
0.649	Remote Similarity	NPD5676	Approved
0.6485	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6484	Remote Similarity	NPD7615	Clinical (unspecified phase)

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