NPASS Compound

Structure

NPC473111 OpenBabel07101719252D 46 50 0 0 1 0 0 0 0 0999 V2000 0.9431 -0.6899 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1785 -0.0853 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6737 -3.7186 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9438 1.5796 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0209 1.3978 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6365 -0.3127 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6147 -0.7652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.8805 -6.6705 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8002 -0.2950 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6147 -1.7058 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9817 -6.9477 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.0898 -5.7535 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9856 -0.7652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8002 -2.1761 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2922 -6.3080 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.4003 -5.1137 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1711 -2.1761 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8120 -4.7512 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1711 -3.1167 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0213 -3.8342 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1285 -1.8375 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8747 -0.2655 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1285 -1.1602 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.9692 -1.0022 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8592 -3.2483 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9856 -1.7058 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5015 -5.3910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4932 0.2941 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.4580 -2.1761 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6751 -0.9127 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.3565 -3.5870 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3318 -3.1945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3809 -0.6397 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.0446 -1.8375 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.6398 0.6895 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0446 -1.1602 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.4580 -0.8215 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.6586 -1.6420 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0446 -3.7186 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3565 -4.5275 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.5411 -2.2775 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.0704 -1.2795 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8592 -2.3077 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.4580 -3.1167 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.4330 -3.4717 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 23 1 0 0 0 0 2 24 1 0 0 0 0 3 25 1 0 0 0 0 4 35 1 0 0 0 0 5 35 1 0 0 0 0 6 36 1 0 0 0 0 7 9 2 0 0 0 0 7 10 1 0 0 0 0 8 11 2 0 0 0 0 8 12 1 0 0 0 0 9 13 1 0 0 0 0 10 14 2 0 0 0 0 11 15 1 0 0 0 0 12 16 2 0 0 0 0 13 26 2 0 0 0 0 14 26 1 0 0 0 0 15 27 2 0 0 0 0 16 27 1 0 0 0 0 17 19 2 0 0 0 0 17 26 1 0 0 0 0 18 20 2 0 0 0 0 18 27 1 0 0 0 0 19 31 1 0 0 0 0 20 32 1 0 0 0 0 21 23 1 0 0 0 0 21 29 1 0 0 0 0 22 30 1 0 0 0 0 23 37 1 6 0 0 0 24 38 2 0 0 0 0 24 42 1 0 0 0 0 25 39 2 0 0 0 0 25 43 1 0 0 0 0 28 22 1 1 0 0 0 28 33 1 0 0 0 0 28 35 1 0 0 0 0 29 34 1 0 0 0 0 29 44 1 6 0 0 0 30 36 1 1 0 0 0 30 45 1 0 0 0 0 31 40 2 0 0 0 0 31 44 1 0 0 0 0 32 41 2 0 0 0 0 32 45 1 0 0 0 0 33 37 1 6 0 0 0 33 42 1 0 0 0 0 34 36 1 1 0 0 0 34 43 1 0 0 0 0 35 46 1 0 0 0 0 36 37 1 1 0 0 0 37 46 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	630.28
Volume:	653.2
LogP:	5.146
LogD:	3.687
LogS:	-5.454
# Rotatable Bonds:	12
TPSA:	114.43
# H-Bond Aceptor:	9
# H-Bond Donor:	0
# Rings:	5
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.205
Synthetic Accessibility Score:	5.873
Fsp3:	0.459
Lipinski Rule-of-5:	Rejected
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:	-5.034
MDCK Permeability:	3.032841232197825e-05
Pgp-inhibitor:	1.0
Pgp-substrate:	0.316
Human Intestinal Absorption (HIA):	0.023
20% Bioavailability (F20%):	0.945
30% Bioavailability (F30%):	0.982

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.976
Plasma Protein Binding (PPB):	92.8052749633789%
Volume Distribution (VD):	1.855
Pgp-substrate:	6.806664943695068%

ADMET: Metabolism

CYP1A2-inhibitor:	0.144
CYP1A2-substrate:	0.025
CYP2C19-inhibitor:	0.208
CYP2C19-substrate:	0.063
CYP2C9-inhibitor:	0.662
CYP2C9-substrate:	0.205
CYP2D6-inhibitor:	0.747
CYP2D6-substrate:	0.124
CYP3A4-inhibitor:	0.829
CYP3A4-substrate:	0.41

ADMET: Excretion

Clearance (CL):	3.377
Half-life (T1/2):	0.118

ADMET: Toxicity

hERG Blockers:	0.212
Human Hepatotoxicity (H-HT):	0.98
Drug-inuced Liver Injury (DILI):	0.986
AMES Toxicity:	0.027
Rat Oral Acute Toxicity:	0.073
Maximum Recommended Daily Dose:	0.854
Skin Sensitization:	0.961
Carcinogencity:	0.143
Eye Corrosion:	0.022
Eye Irritation:	0.642
Respiratory Toxicity:	0.952

Download Data

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

Natural Product: NPC473111

Natural Product ID:	NPC473111
*Common Name:**	JUCKRBRETJEQNN-IQBZRUAFSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	JUCKRBRETJEQNN-IQBZRUAFSA-N
Standard InCHI:	InChI=1S/C37H42O9/c1-23-21-29(44-31(40)19-17-26-13-9-7-10-14-26)34(43-25(3)39)36(6)30(45-32(41)20-18-27-15-11-8-12-16-27)22-28-33(42-24(2)38)37(23,36)46-35(28,4)5/h7-20,23,28-30,33-34H,21-22H2,1-6H3/b19-17+,20-18+/t23-,28-,29+,30+,33-,34-,36-,37-/m1/s1
SMILES:	O=C(O[C@H]1C[C@@H](C)[C@@]23[C@]([C@@H]1OC(=O)C)(C)[C@@H](OC(=O)/C=C/c1ccccc1)C[C@H]([C@H]3OC(=O)C)C(O2)(C)C)/C=C/c1ccccc1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3609768
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001550] Sesquiterpenoids [CHEMONTID:0002051] Agarofurans

*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
NPO11250	Celastrus flagellaris	Species	Celastraceae	Eukaryota	seeds	Jilin, China	n.a.	PMID[26295746]
NPO11250	Celastrus flagellaris	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11250	Celastrus flagellaris	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11250	Celastrus flagellaris	Species	Celastraceae	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
Others	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT519	Cell Line	SH-SY5Y	Homo sapiens	Activity	=	84.5	%	PMID[545393]

☑ 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 NPC473111 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	276
0.1-0.2	1158
0.2-0.3	2207
0.3-0.4	5391
0.4-0.5	9738
0.5-0.6	17769
0.6-0.7	5376
0.7-0.8	558
0.8-0.85	74
0.85-0.9	101
0.9-0.95	40
0.95-1	9

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC473110
0.9915	High Similarity	NPC114927
0.9661	High Similarity	NPC70973
0.9583	High Similarity	NPC473083
0.9576	High Similarity	NPC311175
0.9576	High Similarity	NPC37641
0.9344	High Similarity	NPC476970
0.9344	High Similarity	NPC473082
0.9322	High Similarity	NPC473860
0.9268	High Similarity	NPC476971
0.9268	High Similarity	NPC476972
0.9237	High Similarity	NPC84129
0.9187	High Similarity	NPC470158
0.9187	High Similarity	NPC475933
0.9127	High Similarity	NPC476977
0.9055	High Similarity	NPC476976
0.9016	High Similarity	NPC473889
0.9016	High Similarity	NPC473749
0.9008	High Similarity	NPC473085
0.9008	High Similarity	NPC184747
0.9008	High Similarity	NPC4341
0.9008	High Similarity	NPC473112
0.9008	High Similarity	NPC473081
0.9008	High Similarity	NPC48017
0.9008	High Similarity	NPC200592
0.9008	High Similarity	NPC476094
0.9008	High Similarity	NPC473613
0.9008	High Similarity	NPC147880
0.9008	High Similarity	NPC473109
0.9008	High Similarity	NPC43241
0.9008	High Similarity	NPC473758
0.9008	High Similarity	NPC473060
0.9008	High Similarity	NPC211137
0.8983	High Similarity	NPC473869
0.8943	High Similarity	NPC473870
0.8943	High Similarity	NPC473871
0.8934	High Similarity	NPC473439
0.8934	High Similarity	NPC300827
0.8931	High Similarity	NPC210591
0.8931	High Similarity	NPC475652
0.8931	High Similarity	NPC214550
0.8855	High Similarity	NPC183122
0.8855	High Similarity	NPC283375
0.8806	High Similarity	NPC270498
0.8806	High Similarity	NPC473673
0.8806	High Similarity	NPC246480
0.8806	High Similarity	NPC147217
0.8806	High Similarity	NPC177340
0.8806	High Similarity	NPC191082
0.8806	High Similarity	NPC475429
0.8806	High Similarity	NPC139067
0.8741	High Similarity	NPC188865
0.8741	High Similarity	NPC476974
0.8741	High Similarity	NPC472569
0.8741	High Similarity	NPC25768
0.8741	High Similarity	NPC472570
0.8741	High Similarity	NPC95810
0.8741	High Similarity	NPC163719
0.8741	High Similarity	NPC57628
0.8741	High Similarity	NPC95265
0.8741	High Similarity	NPC70716
0.8741	High Similarity	NPC11685
0.8741	High Similarity	NPC125106
0.8741	High Similarity	NPC51314
0.8741	High Similarity	NPC67777
0.8741	High Similarity	NPC470231
0.8741	High Similarity	NPC472573
0.8702	High Similarity	NPC66761
0.8702	High Similarity	NPC291638
0.8702	High Similarity	NPC472577
0.8702	High Similarity	NPC195647
0.8702	High Similarity	NPC17877
0.8689	High Similarity	NPC89324
0.8676	High Similarity	NPC470157
0.8676	High Similarity	NPC469349
0.8676	High Similarity	NPC472575
0.8676	High Similarity	NPC473088
0.8676	High Similarity	NPC158663
0.8676	High Similarity	NPC171525
0.8676	High Similarity	NPC471104
0.8676	High Similarity	NPC174982
0.8676	High Similarity	NPC472572
0.8676	High Similarity	NPC184817
0.8676	High Similarity	NPC472568
0.8676	High Similarity	NPC470159
0.8676	High Similarity	NPC29704
0.8676	High Similarity	NPC472571
0.8676	High Similarity	NPC96903
0.8676	High Similarity	NPC70403
0.8676	High Similarity	NPC200471
0.8676	High Similarity	NPC177940
0.8676	High Similarity	NPC476973
0.8667	High Similarity	NPC163087
0.8651	High Similarity	NPC471758
0.8626	High Similarity	NPC474608
0.8603	High Similarity	NPC475122
0.8603	High Similarity	NPC475759
0.8603	High Similarity	NPC470152
0.8603	High Similarity	NPC241951
0.8583	High Similarity	NPC45821
0.8551	High Similarity	NPC281717
0.8527	High Similarity	NPC93632
0.8519	High Similarity	NPC16912
0.8504	High Similarity	NPC284022
0.8492	Intermediate Similarity	NPC12016
0.8489	Intermediate Similarity	NPC92293
0.8489	Intermediate Similarity	NPC266265
0.8489	Intermediate Similarity	NPC301556
0.8489	Intermediate Similarity	NPC476975
0.8489	Intermediate Similarity	NPC471101
0.8489	Intermediate Similarity	NPC270590
0.8478	Intermediate Similarity	NPC474935
0.845	Intermediate Similarity	NPC195224
0.8444	Intermediate Similarity	NPC97667
0.8444	Intermediate Similarity	NPC90614
0.8444	Intermediate Similarity	NPC171207
0.8443	Intermediate Similarity	NPC476476
0.8429	Intermediate Similarity	NPC254558
0.8429	Intermediate Similarity	NPC470245
0.8429	Intermediate Similarity	NPC473214
0.8425	Intermediate Similarity	NPC472373
0.8406	Intermediate Similarity	NPC472556
0.8397	Intermediate Similarity	NPC472418
0.8397	Intermediate Similarity	NPC472361
0.8382	Intermediate Similarity	NPC472576
0.8382	Intermediate Similarity	NPC291599
0.8382	Intermediate Similarity	NPC87448
0.8382	Intermediate Similarity	NPC27377
0.8382	Intermediate Similarity	NPC118080
0.8382	Intermediate Similarity	NPC97947
0.8382	Intermediate Similarity	NPC41481
0.8369	Intermediate Similarity	NPC470153
0.8357	Intermediate Similarity	NPC473215
0.8333	Intermediate Similarity	NPC475493
0.8321	Intermediate Similarity	NPC475513
0.8321	Intermediate Similarity	NPC147561
0.8321	Intermediate Similarity	NPC473755
0.832	Intermediate Similarity	NPC470814
0.8309	Intermediate Similarity	NPC477904
0.8309	Intermediate Similarity	NPC100913
0.8309	Intermediate Similarity	NPC275592
0.8309	Intermediate Similarity	NPC183270
0.8308	Intermediate Similarity	NPC58061
0.8308	Intermediate Similarity	NPC230331
0.8271	Intermediate Similarity	NPC472437
0.8248	Intermediate Similarity	NPC224491
0.8231	Intermediate Similarity	NPC473423
0.8201	Intermediate Similarity	NPC80895
0.8201	Intermediate Similarity	NPC471912
0.8194	Intermediate Similarity	NPC282239
0.8182	Intermediate Similarity	NPC477905
0.8169	Intermediate Similarity	NPC31829
0.8162	Intermediate Similarity	NPC475373
0.8143	Intermediate Similarity	NPC471100
0.8143	Intermediate Similarity	NPC277053
0.8143	Intermediate Similarity	NPC471107
0.8143	Intermediate Similarity	NPC301946
0.814	Intermediate Similarity	NPC469742
0.8138	Intermediate Similarity	NPC106895
0.8125	Intermediate Similarity	NPC475328
0.8099	Intermediate Similarity	NPC474564
0.8092	Intermediate Similarity	NPC190849
0.8092	Intermediate Similarity	NPC171007
0.8085	Intermediate Similarity	NPC473602
0.8085	Intermediate Similarity	NPC48599
0.8085	Intermediate Similarity	NPC209592
0.8082	Intermediate Similarity	NPC472393
0.808	Intermediate Similarity	NPC470820
0.806	Intermediate Similarity	NPC80599
0.8058	Intermediate Similarity	NPC34012
0.8056	Intermediate Similarity	NPC472548
0.8045	Intermediate Similarity	NPC475138
0.8043	Intermediate Similarity	NPC472547
0.8042	Intermediate Similarity	NPC475447
0.8042	Intermediate Similarity	NPC70236
0.8042	Intermediate Similarity	NPC476092
0.8042	Intermediate Similarity	NPC475218
0.8029	Intermediate Similarity	NPC184109
0.8028	Intermediate Similarity	NPC473760
0.8027	Intermediate Similarity	NPC471102
0.8014	Intermediate Similarity	NPC217091
0.8	Intermediate Similarity	NPC91703
0.8	Intermediate Similarity	NPC470815
0.7986	Intermediate Similarity	NPC51602
0.7986	Intermediate Similarity	NPC266374
0.7971	Intermediate Similarity	NPC472395
0.7971	Intermediate Similarity	NPC472371
0.797	Intermediate Similarity	NPC225103
0.7956	Intermediate Similarity	NPC472551
0.7956	Intermediate Similarity	NPC472545
0.7945	Intermediate Similarity	NPC34066
0.7945	Intermediate Similarity	NPC228204
0.7945	Intermediate Similarity	NPC26033
0.7945	Intermediate Similarity	NPC472549
0.7943	Intermediate Similarity	NPC471139
0.7941	Intermediate Similarity	NPC4242
0.7941	Intermediate Similarity	NPC471911
0.7929	Intermediate Similarity	NPC140021
0.7929	Intermediate Similarity	NPC472546
0.7926	Intermediate Similarity	NPC209851

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 NPC473111 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	240
0.1-0.2	747
0.2-0.3	1286
0.3-0.4	3340
0.4-0.5	2253
0.5-0.6	1146
0.6-0.7	129
0.7-0.8	9
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7273	Intermediate Similarity	NPD7741	Discontinued
0.7211	Intermediate Similarity	NPD7274	Clinical (unspecified phase)
0.7209	Intermediate Similarity	NPD6858	Approved
0.7209	Intermediate Similarity	NPD7094	Approved
0.7113	Intermediate Similarity	NPD7966	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD7236	Approved
0.7045	Intermediate Similarity	NPD4198	Discontinued
0.7042	Intermediate Similarity	NPD7961	Discontinued
0.7037	Intermediate Similarity	NPD5125	Phase 3
0.7037	Intermediate Similarity	NPD5126	Approved
0.7021	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD8127	Discontinued
0.6975	Remote Similarity	NPD7799	Discontinued
0.6935	Remote Similarity	NPD7798	Approved
0.6933	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD7239	Suspended
0.6913	Remote Similarity	NPD8166	Discontinued
0.6908	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6861	Remote Similarity	NPD7457	Clinical (unspecified phase)
0.6845	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD7266	Discontinued
0.6805	Remote Similarity	NPD8434	Phase 2
0.6786	Remote Similarity	NPD8407	Phase 2
0.6725	Remote Similarity	NPD8360	Approved
0.6725	Remote Similarity	NPD8435	Approved
0.6725	Remote Similarity	NPD8361	Approved
0.6707	Remote Similarity	NPD8368	Discontinued
0.6691	Remote Similarity	NPD7516	Approved
0.6667	Remote Similarity	NPD6648	Approved
0.6667	Remote Similarity	NPD7008	Discontinued
0.6646	Remote Similarity	NPD37	Approved
0.6645	Remote Similarity	NPD6190	Approved
0.6641	Remote Similarity	NPD6647	Phase 2
0.6625	Remote Similarity	NPD4966	Approved
0.6625	Remote Similarity	NPD4967	Phase 2
0.6625	Remote Similarity	NPD4965	Approved
0.6618	Remote Similarity	NPD7328	Approved
0.6618	Remote Similarity	NPD7327	Approved
0.6615	Remote Similarity	NPD6685	Approved
0.6608	Remote Similarity	NPD8424	Clinical (unspecified phase)
0.6591	Remote Similarity	NPD2067	Discontinued
0.6591	Remote Similarity	NPD8485	Approved
0.6589	Remote Similarity	NPD5909	Discontinued
0.6587	Remote Similarity	NPD5926	Approved
0.6569	Remote Similarity	NPD7610	Discontinued
0.6543	Remote Similarity	NPD6234	Discontinued
0.6541	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6528	Remote Similarity	NPD5736	Approved
0.6525	Remote Similarity	NPD6637	Approved
0.6522	Remote Similarity	NPD7058	Phase 2
0.6522	Remote Similarity	NPD7057	Phase 3
0.6519	Remote Similarity	NPD4869	Clinical (unspecified phase)
0.651	Remote Similarity	NPD7097	Phase 1
0.6489	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.648	Remote Similarity	NPD8486	Clinical (unspecified phase)
0.6475	Remote Similarity	NPD8296	Approved
0.6475	Remote Similarity	NPD8379	Approved
0.6475	Remote Similarity	NPD8378	Approved
0.6475	Remote Similarity	NPD8380	Approved
0.6475	Remote Similarity	NPD8335	Approved
0.6475	Remote Similarity	NPD7503	Approved
0.6474	Remote Similarity	NPD6273	Approved
0.6471	Remote Similarity	NPD2629	Approved
0.6467	Remote Similarity	NPD7228	Approved
0.6458	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD5844	Phase 1
0.6419	Remote Similarity	NPD4140	Approved
0.6416	Remote Similarity	NPD8150	Discontinued
0.6412	Remote Similarity	NPD5048	Discontinued
0.6403	Remote Similarity	NPD8377	Approved
0.6403	Remote Similarity	NPD8294	Approved
0.6402	Remote Similarity	NPD5494	Approved
0.6397	Remote Similarity	NPD6010	Discontinued
0.6395	Remote Similarity	NPD3764	Approved
0.6385	Remote Similarity	NPD5765	Approved
0.6382	Remote Similarity	NPD5763	Approved
0.6382	Remote Similarity	NPD5762	Approved
0.637	Remote Similarity	NPD6912	Phase 3
0.637	Remote Similarity	NPD7055	Discontinued
0.6364	Remote Similarity	NPD4628	Phase 3
0.6364	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD5327	Phase 3
0.6357	Remote Similarity	NPD8033	Approved
0.6357	Remote Similarity	NPD5691	Approved
0.6357	Remote Similarity	NPD5344	Discontinued
0.6352	Remote Similarity	NPD7458	Discontinued
0.6351	Remote Similarity	NPD8032	Phase 2
0.6351	Remote Similarity	NPD6663	Approved
0.635	Remote Similarity	NPD5951	Approved
0.6349	Remote Similarity	NPD6048	Clinical (unspecified phase)
0.6349	Remote Similarity	NPD6049	Phase 2
0.6343	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6331	Remote Similarity	NPD6065	Approved
0.6329	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6328	Remote Similarity	NPD7638	Approved
0.6327	Remote Similarity	NPD7095	Approved
0.6316	Remote Similarity	NPD2438	Suspended
0.6316	Remote Similarity	NPD7240	Approved
0.6312	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6311	Remote Similarity	NPD1282	Approved
0.6306	Remote Similarity	NPD7446	Clinical (unspecified phase)
0.6306	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6296	Remote Similarity	NPD7819	Suspended
0.6296	Remote Similarity	NPD8455	Phase 2
0.6279	Remote Similarity	NPD7639	Approved
0.6279	Remote Similarity	NPD7640	Approved
0.6276	Remote Similarity	NPD3094	Phase 2
0.6275	Remote Similarity	NPD7702	Clinical (unspecified phase)
0.6269	Remote Similarity	NPD2182	Approved
0.6269	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6267	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6267	Remote Similarity	NPD5124	Phase 1
0.6258	Remote Similarity	NPD7003	Approved
0.625	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6243	Remote Similarity	NPD8312	Approved
0.6243	Remote Similarity	NPD8313	Approved
0.6224	Remote Similarity	NPD6287	Discontinued
0.622	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.622	Remote Similarity	NPD7768	Phase 2
0.6213	Remote Similarity	NPD7473	Discontinued
0.62	Remote Similarity	NPD4060	Phase 1
0.6197	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.6196	Remote Similarity	NPD7497	Discontinued
0.6194	Remote Similarity	NPD6674	Discontinued
0.619	Remote Similarity	NPD7084	Phase 3
0.6187	Remote Similarity	NPD3317	Approved
0.6176	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6174	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6172	Remote Similarity	NPD1989	Approved
0.6168	Remote Similarity	NPD7199	Phase 2
0.6159	Remote Similarity	NPD5735	Approved
0.6159	Remote Similarity	NPD6355	Discontinued
0.6154	Remote Similarity	NPD4481	Phase 3
0.6154	Remote Similarity	NPD7982	Clinical (unspecified phase)
0.6149	Remote Similarity	NPD4908	Phase 1
0.6148	Remote Similarity	NPD5734	Clinical (unspecified phase)
0.6144	Remote Similarity	NPD3748	Approved
0.6139	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6138	Remote Similarity	NPD7876	Discontinued
0.6136	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.6133	Remote Similarity	NPD7713	Phase 3
0.6133	Remote Similarity	NPD7715	Approved
0.6133	Remote Similarity	NPD7714	Approved
0.6131	Remote Similarity	NPD6232	Discontinued
0.6131	Remote Similarity	NPD969	Suspended
0.6127	Remote Similarity	NPD5585	Approved
0.6119	Remote Similarity	NPD5704	Approved
0.6119	Remote Similarity	NPD5705	Approved
0.6119	Remote Similarity	NPD5706	Approved
0.6111	Remote Similarity	NPD1611	Approved
0.6111	Remote Similarity	NPD3705	Approved
0.6111	Remote Similarity	NPD3092	Approved
0.6111	Remote Similarity	NPD6599	Discontinued
0.6104	Remote Similarity	NPD5408	Approved
0.6104	Remote Similarity	NPD5406	Approved
0.6104	Remote Similarity	NPD5404	Approved
0.6104	Remote Similarity	NPD5405	Approved
0.6103	Remote Similarity	NPD5239	Approved
0.6103	Remote Similarity	NPD5240	Approved
0.6103	Remote Similarity	NPD5237	Approved
0.6103	Remote Similarity	NPD5235	Approved
0.6103	Remote Similarity	NPD5236	Approved
0.6098	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6096	Remote Similarity	NPD8651	Approved
0.6095	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6093	Remote Similarity	NPD2979	Phase 3
0.6092	Remote Similarity	NPD7549	Discontinued
0.6087	Remote Similarity	NPD5535	Approved
0.6084	Remote Similarity	NPD7075	Discontinued
0.6084	Remote Similarity	NPD3095	Discontinued
0.6084	Remote Similarity	NPD4626	Approved
0.6081	Remote Similarity	NPD2861	Phase 2
0.6078	Remote Similarity	NPD5886	Approved
0.6078	Remote Similarity	NPD41	Approved
0.6077	Remote Similarity	NPD4225	Approved
0.6074	Remote Similarity	NPD1358	Approved
0.6074	Remote Similarity	NPD6686	Approved
0.6069	Remote Similarity	NPD7507	Approved
0.6067	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6061	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6061	Remote Similarity	NPD5402	Approved
0.6056	Remote Similarity	NPD3091	Approved
0.6054	Remote Similarity	NPD7319	Approved
0.6053	Remote Similarity	NPD3657	Discovery
0.6051	Remote Similarity	NPD4110	Phase 3
0.6051	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6049	Remote Similarity	NPD6591	Clinical (unspecified phase)
0.6049	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6048	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6043	Remote Similarity	NPD5283	Phase 1
0.6042	Remote Similarity	NPD7815	Approved
0.6042	Remote Similarity	NPD7813	Approved
0.6042	Remote Similarity	NPD3496	Discontinued
0.6036	Remote Similarity	NPD7229	Phase 3
0.6034	Remote Similarity	NPD7685	Pre-registration
0.6032	Remote Similarity	NPD3672	Approved
0.6032	Remote Similarity	NPD3673	Approved
0.6031	Remote Similarity	NPD1238	Approved
0.6031	Remote Similarity	NPD2066	Phase 3

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