NPASS Compound

Structure

NPC473166 OpenBabel07101718292D 37 40 0 0 1 0 0 0 0 0999 V2000 -5.5401 -5.1570 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4214 -3.4178 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0225 2.3083 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0469 2.3083 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8650 -2.9998 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6621 -3.9541 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6898 -0.9756 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4481 0.4035 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6898 0.9756 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5858 -4.9542 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3462 -0.9756 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8449 1.4634 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3796 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5347 -0.4878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7728 -0.1863 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.9756 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0285 -2.8956 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.9512 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0742 -2.6928 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7728 -1.7649 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8449 -1.4634 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8449 -1.4634 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.6813 -2.1706 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6898 0.9756 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.3796 0.9756 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8449 -0.4878 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.6356 -2.3734 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5347 1.4634 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9371 -3.3013 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6898 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8449 -0.4878 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6898 -1.9512 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3799 -1.2427 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2245 1.4634 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.2884 -1.6484 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2843 -4.0263 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 10 1 0 0 0 0 3 28 1 0 0 0 0 4 28 1 0 0 0 0 5 29 1 0 0 0 0 6 29 1 0 0 0 0 8 31 1 0 0 0 0 10 37 1 0 0 0 0 11 15 1 0 0 0 0 11 20 1 0 0 0 0 12 16 1 0 0 0 0 12 24 1 0 0 0 0 13 14 1 0 0 0 0 13 25 1 0 0 0 0 14 30 1 0 0 0 0 15 31 1 0 0 0 0 16 32 1 0 0 0 0 17 19 1 0 0 0 0 17 23 1 0 0 0 0 18 21 1 0 0 0 0 18 22 1 0 0 0 0 19 2 1 6 0 0 0 19 20 1 0 0 0 0 20 21 2 0 0 0 0 21 31 1 0 0 0 0 22 26 1 0 0 0 0 22 33 1 1 0 0 0 23 27 1 0 0 0 0 23 34 1 1 0 0 0 24 28 1 0 0 0 0 24 30 1 1 0 0 0 25 28 1 0 0 0 0 25 35 2 0 0 0 0 26 30 1 6 0 0 0 26 32 1 0 0 0 0 27 29 1 0 0 0 0 27 36 1 6 0 0 0 29 37 1 0 0 0 0 30 7 1 1 0 0 0 31 32 1 6 0 0 0 32 9 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	518.4
Volume:	566.48
LogP:	4.653
LogD:	3.928
LogS:	-4.779
# Rotatable Bonds:	7
TPSA:	86.99
# H-Bond Aceptor:	5
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.369
Synthetic Accessibility Score:	5.255
Fsp3:	0.906
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:	-5.234
MDCK Permeability:	1.2851179235440213e-05
Pgp-inhibitor:	0.991
Pgp-substrate:	0.094
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.962
30% Bioavailability (F30%):	0.935

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.257
Plasma Protein Binding (PPB):	92.4027328491211%
Volume Distribution (VD):	1.002
Pgp-substrate:	2.2002480030059814%

ADMET: Metabolism

CYP1A2-inhibitor:	0.005
CYP1A2-substrate:	0.589
CYP2C19-inhibitor:	0.026
CYP2C19-substrate:	0.942
CYP2C9-inhibitor:	0.094
CYP2C9-substrate:	0.204
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.101
CYP3A4-inhibitor:	0.781
CYP3A4-substrate:	0.756

ADMET: Excretion

Clearance (CL):	6.975
Half-life (T1/2):	0.214

ADMET: Toxicity

hERG Blockers:	0.032
Human Hepatotoxicity (H-HT):	0.278
Drug-inuced Liver Injury (DILI):	0.037
AMES Toxicity:	0.02
Rat Oral Acute Toxicity:	0.55
Maximum Recommended Daily Dose:	0.714
Skin Sensitization:	0.09
Carcinogencity:	0.399
Eye Corrosion:	0.003
Eye Irritation:	0.01
Respiratory Toxicity:	0.978

Download Data

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

Natural Product: NPC473166

Natural Product ID:	NPC473166
*Common Name:**	QVVRXENOONWNGX-IPAXGOGQSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	QVVRXENOONWNGX-IPAXGOGQSA-N
Standard InCHI:	InChI=1S/C32H54O5/c1-10-37-29(5,6)27(36)23(34)17-19(2)20-11-15-31(8)21(20)18-22(33)26-30(7)14-13-25(35)28(3,4)24(30)12-16-32(26,31)9/h19,22-24,26-27,33-34,36H,10-18H2,1-9H3/t19-,22+,23+,24+,26+,27-,30+,31+,32+/m1/s1
SMILES:	CCOC(C)(C)C(C(CC(C)C1=C2CC(C3C4(CCC(=O)C(C4CCC3(C2(CC1)C)C)(C)C)C)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3632946
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

*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
NPO30648	Alisma orientale	Species	Alismataceae	Eukaryota	rhizome	n.a.	n.a.	PMID[10560729]
NPO30648	Alisma orientale	Species	Alismataceae	Eukaryota	n.a.	rhizome	n.a.	PMID[17541191]
NPO30648	Alisma orientale	Species	Alismataceae	Eukaryota	Rhizome	n.a.	n.a.	PMID[26425784]
NPO30648	Alisma orientale	Species	Alismataceae	Eukaryota	n.a.	tuber	n.a.	PMID[26666273]
NPO30648	Alisma orientale	Species	Alismataceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]

☑ 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
EC50	1
IC50	1

Activity Type	# Activity
Individual Protein	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT203	Individual Protein	Carboxylesterase 2	Homo sapiens	IC50	=	4720.0	nM	PMID[528444]
NPT540	Individual Protein	Bile acid receptor FXR	Homo sapiens	EC50	=	940.0	nM	PMID[528445]

☑ 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 NPC473166 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	221
0.1-0.2	1506
0.2-0.3	4891
0.3-0.4	13022
0.4-0.5	9684
0.5-0.6	5516
0.6-0.7	5623
0.7-0.8	2148
0.8-0.85	49
0.85-0.9	17
0.9-0.95	11
0.95-1	9

Similarity Score	Similarity Level	Natural Product ID
0.9659	High Similarity	NPC37787
0.9659	High Similarity	NPC180557
0.9659	High Similarity	NPC473415
0.9659	High Similarity	NPC469329
0.9659	High Similarity	NPC30677
0.9655	High Similarity	NPC274046
0.9655	High Similarity	NPC198074
0.9529	High Similarity	NPC469314
0.9529	High Similarity	NPC469317
0.9529	High Similarity	NPC241875
0.9333	High Similarity	NPC471777
0.913	High Similarity	NPC303777
0.913	High Similarity	NPC471784
0.908	High Similarity	NPC469322
0.9059	High Similarity	NPC86370
0.9043	High Similarity	NPC469316
0.8947	High Similarity	NPC324001
0.8936	High Similarity	NPC469327
0.8901	High Similarity	NPC240617
0.8889	High Similarity	NPC473167
0.8876	High Similarity	NPC229871
0.8876	High Similarity	NPC469319
0.8737	High Similarity	NPC476897
0.871	High Similarity	NPC471822
0.8673	High Similarity	NPC471783
0.8673	High Similarity	NPC469318
0.8673	High Similarity	NPC9457
0.8673	High Similarity	NPC473173
0.8632	High Similarity	NPC473176
0.8602	High Similarity	NPC473170
0.8571	High Similarity	NPC470587
0.8485	Intermediate Similarity	NPC473165
0.8462	Intermediate Similarity	NPC250592
0.8462	Intermediate Similarity	NPC77263
0.8462	Intermediate Similarity	NPC32830
0.8444	Intermediate Similarity	NPC138756
0.8387	Intermediate Similarity	NPC469315
0.8384	Intermediate Similarity	NPC472655
0.8367	Intermediate Similarity	NPC471005
0.8333	Intermediate Similarity	NPC471737
0.8317	Intermediate Similarity	NPC41405
0.8315	Intermediate Similarity	NPC473157
0.8298	Intermediate Similarity	NPC67831
0.8298	Intermediate Similarity	NPC174051
0.828	Intermediate Similarity	NPC155304
0.828	Intermediate Similarity	NPC262870
0.8242	Intermediate Similarity	NPC90652
0.8235	Intermediate Similarity	NPC470065
0.8235	Intermediate Similarity	NPC5284
0.8229	Intermediate Similarity	NPC272451
0.8222	Intermediate Similarity	NPC197823
0.8211	Intermediate Similarity	NPC279974
0.8182	Intermediate Similarity	NPC239716
0.8182	Intermediate Similarity	NPC264048
0.8172	Intermediate Similarity	NPC136801
0.8163	Intermediate Similarity	NPC233012
0.8163	Intermediate Similarity	NPC54909
0.8152	Intermediate Similarity	NPC474677
0.8152	Intermediate Similarity	NPC470417
0.8152	Intermediate Similarity	NPC193360
0.8144	Intermediate Similarity	NPC470067
0.8144	Intermediate Similarity	NPC470068
0.8144	Intermediate Similarity	NPC470066
0.8144	Intermediate Similarity	NPC119036
0.8137	Intermediate Similarity	NPC218853
0.8125	Intermediate Similarity	NPC230151
0.8125	Intermediate Similarity	NPC91439
0.8105	Intermediate Similarity	NPC159410
0.8105	Intermediate Similarity	NPC318332
0.81	Intermediate Similarity	NPC75531
0.81	Intermediate Similarity	NPC149124
0.8085	Intermediate Similarity	NPC235704
0.8081	Intermediate Similarity	NPC473163
0.8077	Intermediate Similarity	NPC234042
0.8077	Intermediate Similarity	NPC470063
0.8077	Intermediate Similarity	NPC152117
0.8065	Intermediate Similarity	NPC122116
0.8065	Intermediate Similarity	NPC474245
0.8065	Intermediate Similarity	NPC31985
0.8065	Intermediate Similarity	NPC1015
0.8061	Intermediate Similarity	NPC167974
0.8058	Intermediate Similarity	NPC250956
0.8041	Intermediate Similarity	NPC474785
0.8041	Intermediate Similarity	NPC474938
0.8021	Intermediate Similarity	NPC200702
0.802	Intermediate Similarity	NPC475414
0.802	Intermediate Similarity	NPC173172
0.8	Intermediate Similarity	NPC107674
0.8	Intermediate Similarity	NPC141497
0.8	Intermediate Similarity	NPC170220
0.8	Intermediate Similarity	NPC255017
0.8	Intermediate Similarity	NPC86368
0.798	Intermediate Similarity	NPC473174
0.798	Intermediate Similarity	NPC470054
0.7979	Intermediate Similarity	NPC473269
0.7979	Intermediate Similarity	NPC471896
0.7979	Intermediate Similarity	NPC126993
0.7979	Intermediate Similarity	NPC85173
0.7961	Intermediate Similarity	NPC475065
0.7961	Intermediate Similarity	NPC472216
0.7961	Intermediate Similarity	NPC5475
0.7961	Intermediate Similarity	NPC284828
0.7961	Intermediate Similarity	NPC173905
0.7957	Intermediate Similarity	NPC44181
0.7957	Intermediate Similarity	NPC230387
0.7941	Intermediate Similarity	NPC144459
0.7941	Intermediate Similarity	NPC475176
0.7941	Intermediate Similarity	NPC473284
0.7941	Intermediate Similarity	NPC255387
0.7941	Intermediate Similarity	NPC131665
0.7938	Intermediate Similarity	NPC327179
0.7938	Intermediate Similarity	NPC120708
0.7938	Intermediate Similarity	NPC327788
0.7935	Intermediate Similarity	NPC325594
0.7935	Intermediate Similarity	NPC73038
0.7935	Intermediate Similarity	NPC56588
0.7935	Intermediate Similarity	NPC213412
0.7921	Intermediate Similarity	NPC471293
0.7917	Intermediate Similarity	NPC473172
0.7917	Intermediate Similarity	NPC296164
0.7912	Intermediate Similarity	NPC59453
0.7912	Intermediate Similarity	NPC221758
0.79	Intermediate Similarity	NPC470053
0.79	Intermediate Similarity	NPC473928
0.79	Intermediate Similarity	NPC296879
0.79	Intermediate Similarity	NPC477054
0.79	Intermediate Similarity	NPC471119
0.7895	Intermediate Similarity	NPC285184
0.7895	Intermediate Similarity	NPC86266
0.7895	Intermediate Similarity	NPC26888
0.7895	Intermediate Similarity	NPC77099
0.7895	Intermediate Similarity	NPC212301
0.7895	Intermediate Similarity	NPC470590
0.7895	Intermediate Similarity	NPC110657
0.7895	Intermediate Similarity	NPC60755
0.7895	Intermediate Similarity	NPC189520
0.7889	Intermediate Similarity	NPC151519
0.7889	Intermediate Similarity	NPC212083
0.7885	Intermediate Similarity	NPC154856
0.7885	Intermediate Similarity	NPC475317
0.7885	Intermediate Similarity	NPC52241
0.7879	Intermediate Similarity	NPC83709
0.7872	Intermediate Similarity	NPC474889
0.7872	Intermediate Similarity	NPC469323
0.7872	Intermediate Similarity	NPC475921
0.7872	Intermediate Similarity	NPC30522
0.7872	Intermediate Similarity	NPC119416
0.7872	Intermediate Similarity	NPC474704
0.7864	Intermediate Similarity	NPC472218
0.7864	Intermediate Similarity	NPC473482
0.7864	Intermediate Similarity	NPC318363
0.7864	Intermediate Similarity	NPC475418
0.7864	Intermediate Similarity	NPC472217
0.7864	Intermediate Similarity	NPC258323
0.7864	Intermediate Similarity	NPC472219
0.7857	Intermediate Similarity	NPC9613
0.7857	Intermediate Similarity	NPC259788
0.7857	Intermediate Similarity	NPC247139
0.7857	Intermediate Similarity	NPC255589
0.7857	Intermediate Similarity	NPC170978
0.7849	Intermediate Similarity	NPC475740
0.7849	Intermediate Similarity	NPC251808
0.7849	Intermediate Similarity	NPC99909
0.7849	Intermediate Similarity	NPC474174
0.7849	Intermediate Similarity	NPC73064
0.7843	Intermediate Similarity	NPC477877
0.7843	Intermediate Similarity	NPC475494
0.7835	Intermediate Similarity	NPC195715
0.7835	Intermediate Similarity	NPC473648
0.7835	Intermediate Similarity	NPC32118
0.7826	Intermediate Similarity	NPC470574
0.7826	Intermediate Similarity	NPC133954
0.7822	Intermediate Similarity	NPC191892
0.7822	Intermediate Similarity	NPC55954
0.7822	Intermediate Similarity	NPC222153
0.7822	Intermediate Similarity	NPC218513
0.7812	Intermediate Similarity	NPC477436
0.7812	Intermediate Similarity	NPC477435
0.7812	Intermediate Similarity	NPC307335
0.7812	Intermediate Similarity	NPC474806
0.7812	Intermediate Similarity	NPC136313
0.7812	Intermediate Similarity	NPC287118
0.7812	Intermediate Similarity	NPC74855
0.7812	Intermediate Similarity	NPC473690
0.7812	Intermediate Similarity	NPC275809
0.7812	Intermediate Similarity	NPC133579
0.7812	Intermediate Similarity	NPC12722
0.7812	Intermediate Similarity	NPC471902
0.7802	Intermediate Similarity	NPC472743
0.7802	Intermediate Similarity	NPC475726
0.7802	Intermediate Similarity	NPC132635
0.78	Intermediate Similarity	NPC115899
0.78	Intermediate Similarity	NPC289670
0.78	Intermediate Similarity	NPC477051
0.78	Intermediate Similarity	NPC477053
0.78	Intermediate Similarity	NPC477052
0.7789	Intermediate Similarity	NPC148414
0.7789	Intermediate Similarity	NPC111585
0.7789	Intermediate Similarity	NPC120840
0.7789	Intermediate Similarity	NPC111110

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 NPC473166 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	193
0.1-0.2	1878
0.2-0.3	3861
0.3-0.4	2164
0.4-0.5	598
0.5-0.6	200
0.6-0.7	205
0.7-0.8	51
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
0.7912	Intermediate Similarity	NPD4786	Approved
0.7889	Intermediate Similarity	NPD3667	Approved
0.7742	Intermediate Similarity	NPD3618	Phase 1
0.7732	Intermediate Similarity	NPD7748	Approved
0.7684	Intermediate Similarity	NPD5328	Approved
0.7629	Intermediate Similarity	NPD6399	Phase 3
0.757	Intermediate Similarity	NPD8297	Approved
0.7526	Intermediate Similarity	NPD8034	Phase 2
0.7526	Intermediate Similarity	NPD6079	Approved
0.7526	Intermediate Similarity	NPD7515	Phase 2
0.7526	Intermediate Similarity	NPD8035	Phase 2
0.75	Intermediate Similarity	NPD5739	Approved
0.75	Intermediate Similarity	NPD7128	Approved
0.75	Intermediate Similarity	NPD7902	Approved
0.75	Intermediate Similarity	NPD6675	Approved
0.75	Intermediate Similarity	NPD4755	Approved
0.75	Intermediate Similarity	NPD6402	Approved
0.7473	Intermediate Similarity	NPD7525	Registered
0.7455	Intermediate Similarity	NPD7115	Discovery
0.7453	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7449	Intermediate Similarity	NPD4202	Approved
0.7447	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD7320	Approved
0.7358	Intermediate Similarity	NPD6899	Approved
0.7358	Intermediate Similarity	NPD6881	Approved
0.7356	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.7356	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD5286	Approved
0.7353	Intermediate Similarity	NPD5285	Approved
0.7353	Intermediate Similarity	NPD4700	Approved
0.7353	Intermediate Similarity	NPD4696	Approved
0.734	Intermediate Similarity	NPD3665	Phase 1
0.734	Intermediate Similarity	NPD3666	Approved
0.734	Intermediate Similarity	NPD3133	Approved
0.734	Intermediate Similarity	NPD3668	Phase 3
0.7327	Intermediate Similarity	NPD6084	Phase 2
0.7327	Intermediate Similarity	NPD6083	Phase 2
0.7326	Intermediate Similarity	NPD3699	Clinical (unspecified phase)
0.7326	Intermediate Similarity	NPD3700	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD4753	Phase 2
0.7315	Intermediate Similarity	NPD8130	Phase 1
0.729	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD6373	Approved
0.729	Intermediate Similarity	NPD6372	Approved
0.7264	Intermediate Similarity	NPD6412	Phase 2
0.7264	Intermediate Similarity	NPD5701	Approved
0.7264	Intermediate Similarity	NPD5697	Approved
0.7255	Intermediate Similarity	NPD7638	Approved
0.7234	Intermediate Similarity	NPD4788	Approved
0.7228	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7228	Intermediate Similarity	NPD5222	Approved
0.7228	Intermediate Similarity	NPD5221	Approved
0.7228	Intermediate Similarity	NPD4697	Phase 3
0.7222	Intermediate Similarity	NPD6883	Approved
0.7222	Intermediate Similarity	NPD6117	Approved
0.7222	Intermediate Similarity	NPD7102	Approved
0.7222	Intermediate Similarity	NPD7290	Approved
0.7212	Intermediate Similarity	NPD5211	Phase 2
0.7212	Intermediate Similarity	NPD5224	Approved
0.7212	Intermediate Similarity	NPD5225	Approved
0.7212	Intermediate Similarity	NPD4633	Approved
0.7212	Intermediate Similarity	NPD5226	Approved
0.72	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD7900	Approved
0.7188	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7184	Intermediate Similarity	NPD7640	Approved
0.7184	Intermediate Similarity	NPD7639	Approved
0.7174	Intermediate Similarity	NPD7645	Phase 2
0.7157	Intermediate Similarity	NPD5173	Approved
0.7156	Intermediate Similarity	NPD6650	Approved
0.7156	Intermediate Similarity	NPD6617	Approved
0.7156	Intermediate Similarity	NPD6869	Approved
0.7156	Intermediate Similarity	NPD6649	Approved
0.7156	Intermediate Similarity	NPD6847	Approved
0.7143	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD5175	Approved
0.7143	Intermediate Similarity	NPD6116	Phase 1
0.7143	Intermediate Similarity	NPD5174	Approved
0.713	Intermediate Similarity	NPD6013	Approved
0.713	Intermediate Similarity	NPD6014	Approved
0.713	Intermediate Similarity	NPD6012	Approved
0.7126	Intermediate Similarity	NPD4267	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD5223	Approved
0.7111	Intermediate Similarity	NPD3703	Phase 2
0.7091	Intermediate Similarity	NPD6882	Approved
0.7087	Intermediate Similarity	NPD4225	Approved
0.7075	Intermediate Similarity	NPD5141	Approved
0.7065	Intermediate Similarity	NPD3617	Approved
0.7065	Intermediate Similarity	NPD6115	Approved
0.7065	Intermediate Similarity	NPD6697	Approved
0.7065	Intermediate Similarity	NPD6118	Approved
0.7065	Intermediate Similarity	NPD6114	Approved
0.7064	Intermediate Similarity	NPD4634	Approved
0.7048	Intermediate Similarity	NPD7632	Discontinued
0.7045	Intermediate Similarity	NPD4245	Approved
0.7045	Intermediate Similarity	NPD4244	Approved
0.7041	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD6011	Approved
0.7027	Intermediate Similarity	NPD4632	Approved
0.7011	Intermediate Similarity	NPD5360	Phase 3
0.7011	Intermediate Similarity	NPD5361	Clinical (unspecified phase)
0.701	Intermediate Similarity	NPD7146	Approved
0.701	Intermediate Similarity	NPD7334	Approved
0.701	Intermediate Similarity	NPD5330	Approved
0.701	Intermediate Similarity	NPD6684	Approved
0.701	Intermediate Similarity	NPD7521	Approved
0.701	Intermediate Similarity	NPD6409	Approved
0.7009	Intermediate Similarity	NPD4768	Approved
0.7009	Intermediate Similarity	NPD4767	Approved
0.7	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD4754	Approved
0.6961	Remote Similarity	NPD5695	Phase 3
0.6961	Remote Similarity	NPD5210	Approved
0.6961	Remote Similarity	NPD4629	Approved
0.6957	Remote Similarity	NPD6054	Approved
0.6957	Remote Similarity	NPD6319	Approved
0.6957	Remote Similarity	NPD6059	Approved
0.6947	Remote Similarity	NPD4223	Phase 3
0.6947	Remote Similarity	NPD4221	Approved
0.6939	Remote Similarity	NPD7524	Approved
0.6932	Remote Similarity	NPD3698	Phase 2
0.6923	Remote Similarity	NPD5696	Approved
0.6923	Remote Similarity	NPD7339	Approved
0.6923	Remote Similarity	NPD6942	Approved
0.6909	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6907	Remote Similarity	NPD5329	Approved
0.6881	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6881	Remote Similarity	NPD4729	Approved
0.6881	Remote Similarity	NPD5128	Approved
0.6881	Remote Similarity	NPD4730	Approved
0.6875	Remote Similarity	NPD8133	Approved
0.6869	Remote Similarity	NPD5737	Approved
0.6869	Remote Similarity	NPD6672	Approved
0.6869	Remote Similarity	NPD6903	Approved
0.6854	Remote Similarity	NPD4789	Approved
0.6848	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD6933	Approved
0.6842	Remote Similarity	NPD4692	Approved
0.6842	Remote Similarity	NPD4139	Approved
0.6838	Remote Similarity	NPD6370	Approved
0.6837	Remote Similarity	NPD5279	Phase 3
0.6833	Remote Similarity	NPD7736	Approved
0.6832	Remote Similarity	NPD6411	Approved
0.6807	Remote Similarity	NPD7507	Approved
0.6804	Remote Similarity	NPD4197	Approved
0.6796	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD4159	Approved
0.678	Remote Similarity	NPD8328	Phase 3
0.6757	Remote Similarity	NPD5249	Phase 3
0.6757	Remote Similarity	NPD5251	Approved
0.6757	Remote Similarity	NPD5250	Approved
0.6757	Remote Similarity	NPD5247	Approved
0.6757	Remote Similarity	NPD5248	Approved
0.6754	Remote Similarity	NPD6274	Approved
0.6752	Remote Similarity	NPD6015	Approved
0.6752	Remote Similarity	NPD6016	Approved
0.675	Remote Similarity	NPD8293	Discontinued
0.6737	Remote Similarity	NPD4748	Discontinued
0.6737	Remote Similarity	NPD4695	Discontinued
0.6727	Remote Similarity	NPD6686	Approved
0.6724	Remote Similarity	NPD7100	Approved
0.6724	Remote Similarity	NPD7101	Approved
0.6723	Remote Similarity	NPD7492	Approved
0.6702	Remote Similarity	NPD3671	Phase 1
0.6701	Remote Similarity	NPD6695	Phase 3
0.6697	Remote Similarity	NPD6008	Approved
0.6696	Remote Similarity	NPD5217	Approved
0.6696	Remote Similarity	NPD5215	Approved
0.6696	Remote Similarity	NPD5216	Approved
0.6696	Remote Similarity	NPD6009	Approved
0.6695	Remote Similarity	NPD5988	Approved
0.6667	Remote Similarity	NPD4690	Approved
0.6667	Remote Similarity	NPD6616	Approved
0.6667	Remote Similarity	NPD5205	Approved
0.6667	Remote Similarity	NPD4138	Approved
0.6667	Remote Similarity	NPD4623	Approved
0.6667	Remote Similarity	NPD4688	Approved
0.6667	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4519	Discontinued
0.6667	Remote Similarity	NPD4689	Approved
0.6667	Remote Similarity	NPD4693	Phase 3
0.6667	Remote Similarity	NPD6098	Approved
0.6639	Remote Similarity	NPD7319	Approved
0.6639	Remote Similarity	NPD7604	Phase 2
0.6638	Remote Similarity	NPD6335	Approved
0.6636	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6634	Remote Similarity	NPD6080	Approved
0.6634	Remote Similarity	NPD6904	Approved
0.6634	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6634	Remote Similarity	NPD6101	Approved
0.6634	Remote Similarity	NPD6673	Approved
0.6634	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6633	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.663	Remote Similarity	NPD6926	Approved
0.663	Remote Similarity	NPD6924	Approved
0.6612	Remote Similarity	NPD7078	Approved
0.661	Remote Similarity	NPD8033	Approved
0.661	Remote Similarity	NPD5983	Phase 2
0.661	Remote Similarity	NPD6909	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