NPASS Compound

Structure

NPC133809 OpenBabel07101718312D 22 24 0 0 1 0 0 0 0 0999 V2000 6.0622 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5000 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 0.5000 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 3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 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 -0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 1.5000 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 2.5981 0.5000 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 -1.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.5000 0.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5000 -0.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 13 2 0 0 0 0 2 13 1 0 0 0 0 5 10 1 0 0 0 0 5 11 1 0 0 0 0 6 8 2 0 0 0 0 6 14 1 0 0 0 0 7 9 1 0 0 0 0 7 15 1 0 0 0 0 8 16 1 0 0 0 0 9 17 1 0 0 0 0 10 19 1 0 0 0 0 11 20 1 0 0 0 0 12 14 2 0 0 0 0 12 15 1 0 0 0 0 13 14 1 0 0 0 0 15 16 2 0 0 0 0 16 19 1 0 0 0 0 17 19 1 6 0 0 0 17 20 1 0 0 0 0 18 20 1 0 0 0 0 18 21 2 0 0 0 0 18 22 1 0 0 0 0 19 3 1 6 0 0 0 20 4 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	298.19
Volume:	333.205
LogP:	4.866
LogD:	3.873
LogS:	-4.537
# Rotatable Bonds:	2
TPSA:	37.3
# H-Bond Aceptor:	2
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.85
Synthetic Accessibility Score:	3.592
Fsp3:	0.55
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.898
MDCK Permeability:	2.4776563805062324e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.007

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.044
Plasma Protein Binding (PPB):	93.6103515625%
Volume Distribution (VD):	0.382
Pgp-substrate:	4.796391487121582%

ADMET: Metabolism

CYP1A2-inhibitor:	0.163
CYP1A2-substrate:	0.73
CYP2C19-inhibitor:	0.056
CYP2C19-substrate:	0.847
CYP2C9-inhibitor:	0.238
CYP2C9-substrate:	0.277
CYP2D6-inhibitor:	0.014
CYP2D6-substrate:	0.271
CYP3A4-inhibitor:	0.091
CYP3A4-substrate:	0.198

ADMET: Excretion

Clearance (CL):	1.03
Half-life (T1/2):	0.204

ADMET: Toxicity

hERG Blockers:	0.109
Human Hepatotoxicity (H-HT):	0.159
Drug-inuced Liver Injury (DILI):	0.047
AMES Toxicity:	0.008
Rat Oral Acute Toxicity:	0.096
Maximum Recommended Daily Dose:	0.278
Skin Sensitization:	0.933
Carcinogencity:	0.064
Eye Corrosion:	0.024
Eye Irritation:	0.505
Respiratory Toxicity:	0.626

Download Data

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

Natural Product: NPC133809

Natural Product ID:	NPC133809
*Common Name:**	NGBRPGLXCQJIPU-MISYRCLQSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	NGBRPGLXCQJIPU-MISYRCLQSA-N
Standard InCHI:	InChI=1S/C20H26O2/c1-13(2)14-6-8-16-15(12-14)7-9-17-19(16,3)10-5-11-20(17,4)18(21)22/h6,8,12,17H,1,5,7,9-11H2,2-4H3,(H,21,22)/t17-,19-,20-/m1/s1
SMILES:	OC(=O)[C@]1(C)CCC[C@]2([C@H]1CCc1c2ccc(c1)C(=C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3590338
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids

*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
NPO13153	Callicarpa macrophylla	Species	Lamiaceae	Eukaryota	Leaves	n.a.	n.a.	PMID[26110519]
NPO12422	Pinus massoniana	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32100544]
NPO12422	Pinus massoniana	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13153	Callicarpa macrophylla	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12422	Pinus massoniana	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12422	Pinus massoniana	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO12422	Pinus massoniana	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO13153	Callicarpa macrophylla	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO12422	Pinus massoniana	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13153	Callicarpa macrophylla	Species	Lamiaceae	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
EC50	1
IC50	1

Activity Type	# Activity
Cell Line	1
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT681	Cell Line	PC-12	Rattus norvegicus	EC50	>	30000.0	nM	PMID[568166]
NPT1464	Individual Protein	Phosphodiesterase 4D	Homo sapiens	IC50	=	3300.0	nM	PMID[568167]

☑ 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 NPC133809 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	192
0.1-0.2	1031
0.2-0.3	2089
0.3-0.4	7961
0.4-0.5	17615
0.5-0.6	11460
0.6-0.7	2007
0.7-0.8	266
0.8-0.85	51
0.85-0.9	11
0.9-0.95	11
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC136810
1.0	High Similarity	NPC128248
0.9579	High Similarity	NPC225079
0.949	High Similarity	NPC142326
0.949	High Similarity	NPC94751
0.9474	High Similarity	NPC221825
0.9263	High Similarity	NPC226041
0.9118	High Similarity	NPC475002
0.9118	High Similarity	NPC95126
0.9	High Similarity	NPC471186
0.8942	High Similarity	NPC93287
0.8824	High Similarity	NPC21929
0.8788	High Similarity	NPC264728
0.8774	High Similarity	NPC221275
0.8679	High Similarity	NPC471721
0.8611	High Similarity	NPC212891
0.8586	High Similarity	NPC120393
0.8571	High Similarity	NPC265513
0.8571	High Similarity	NPC469893
0.8558	High Similarity	NPC475006
0.8542	High Similarity	NPC220596
0.8542	High Similarity	NPC86987
0.8532	High Similarity	NPC45794
0.8526	High Similarity	NPC298115
0.8491	Intermediate Similarity	NPC280789
0.8491	Intermediate Similarity	NPC471188
0.8491	Intermediate Similarity	NPC471189
0.8485	Intermediate Similarity	NPC469890
0.8485	Intermediate Similarity	NPC469891
0.8485	Intermediate Similarity	NPC469892
0.8469	Intermediate Similarity	NPC172925
0.8438	Intermediate Similarity	NPC274455
0.8438	Intermediate Similarity	NPC86670
0.8438	Intermediate Similarity	NPC70940
0.8378	Intermediate Similarity	NPC202015
0.8365	Intermediate Similarity	NPC85560
0.8365	Intermediate Similarity	NPC244933
0.8351	Intermediate Similarity	NPC125226
0.8349	Intermediate Similarity	NPC9274
0.8304	Intermediate Similarity	NPC234337
0.8304	Intermediate Similarity	NPC133389
0.8304	Intermediate Similarity	NPC183339
0.828	Intermediate Similarity	NPC44830
0.8257	Intermediate Similarity	NPC215419
0.8252	Intermediate Similarity	NPC247976
0.8241	Intermediate Similarity	NPC470253
0.8229	Intermediate Similarity	NPC329064
0.8191	Intermediate Similarity	NPC267704
0.8173	Intermediate Similarity	NPC329282
0.8165	Intermediate Similarity	NPC294458
0.8158	Intermediate Similarity	NPC167323
0.8158	Intermediate Similarity	NPC269923
0.8158	Intermediate Similarity	NPC369
0.8158	Intermediate Similarity	NPC293831
0.8148	Intermediate Similarity	NPC66208
0.8125	Intermediate Similarity	NPC322387
0.8119	Intermediate Similarity	NPC324602
0.8108	Intermediate Similarity	NPC242764
0.8108	Intermediate Similarity	NPC105141
0.8077	Intermediate Similarity	NPC329556
0.8073	Intermediate Similarity	NPC143768
0.8053	Intermediate Similarity	NPC42657
0.802	Intermediate Similarity	NPC185208
0.802	Intermediate Similarity	NPC219573
0.8019	Intermediate Similarity	NPC100767
0.8019	Intermediate Similarity	NPC37914
0.8017	Intermediate Similarity	NPC85511
0.8	Intermediate Similarity	NPC472222
0.8	Intermediate Similarity	NPC249340
0.8	Intermediate Similarity	NPC162935
0.8	Intermediate Similarity	NPC472221
0.7965	Intermediate Similarity	NPC254233
0.7957	Intermediate Similarity	NPC127343
0.7941	Intermediate Similarity	NPC239185
0.7928	Intermediate Similarity	NPC186933
0.7913	Intermediate Similarity	NPC241001
0.7909	Intermediate Similarity	NPC477475
0.7909	Intermediate Similarity	NPC477476
0.7905	Intermediate Similarity	NPC19856
0.7895	Intermediate Similarity	NPC476645
0.7885	Intermediate Similarity	NPC476993
0.7879	Intermediate Similarity	NPC26224
0.787	Intermediate Similarity	NPC318327
0.7864	Intermediate Similarity	NPC134882
0.7863	Intermediate Similarity	NPC328107
0.7818	Intermediate Similarity	NPC218855
0.7815	Intermediate Similarity	NPC253681
0.7778	Intermediate Similarity	NPC121168
0.7767	Intermediate Similarity	NPC265220
0.7767	Intermediate Similarity	NPC477767
0.775	Intermediate Similarity	NPC51448
0.775	Intermediate Similarity	NPC115797
0.7723	Intermediate Similarity	NPC323420
0.7719	Intermediate Similarity	NPC222968
0.7719	Intermediate Similarity	NPC80605
0.7719	Intermediate Similarity	NPC323440
0.7714	Intermediate Similarity	NPC469481
0.7714	Intermediate Similarity	NPC109514
0.7708	Intermediate Similarity	NPC285773
0.7692	Intermediate Similarity	NPC271475
0.7692	Intermediate Similarity	NPC75724
0.7679	Intermediate Similarity	NPC234637
0.7679	Intermediate Similarity	NPC130591
0.7664	Intermediate Similarity	NPC56168
0.7658	Intermediate Similarity	NPC292834
0.7658	Intermediate Similarity	NPC186128
0.7642	Intermediate Similarity	NPC304873
0.7634	Intermediate Similarity	NPC249018
0.7634	Intermediate Similarity	NPC3190
0.7632	Intermediate Similarity	NPC158157
0.7632	Intermediate Similarity	NPC469843
0.7627	Intermediate Similarity	NPC182333
0.7627	Intermediate Similarity	NPC273336
0.7619	Intermediate Similarity	NPC7435
0.7615	Intermediate Similarity	NPC472979
0.7615	Intermediate Similarity	NPC112903
0.7615	Intermediate Similarity	NPC249811
0.7615	Intermediate Similarity	NPC27252
0.7611	Intermediate Similarity	NPC93181
0.7607	Intermediate Similarity	NPC32322
0.7607	Intermediate Similarity	NPC259703
0.7593	Intermediate Similarity	NPC105899
0.7593	Intermediate Similarity	NPC243601
0.7589	Intermediate Similarity	NPC471481
0.7589	Intermediate Similarity	NPC287055
0.7589	Intermediate Similarity	NPC206414
0.7589	Intermediate Similarity	NPC306977
0.7589	Intermediate Similarity	NPC242957
0.7583	Intermediate Similarity	NPC9180
0.7583	Intermediate Similarity	NPC100402
0.7573	Intermediate Similarity	NPC260233
0.757	Intermediate Similarity	NPC255676
0.7568	Intermediate Similarity	NPC474057
0.7568	Intermediate Similarity	NPC133308
0.7563	Intermediate Similarity	NPC77691
0.7563	Intermediate Similarity	NPC473938
0.7563	Intermediate Similarity	NPC307139
0.7563	Intermediate Similarity	NPC318067
0.7551	Intermediate Similarity	NPC95965
0.7549	Intermediate Similarity	NPC153885
0.7549	Intermediate Similarity	NPC59677
0.7545	Intermediate Similarity	NPC64642
0.7545	Intermediate Similarity	NPC472982
0.7545	Intermediate Similarity	NPC149455
0.7525	Intermediate Similarity	NPC84288
0.7524	Intermediate Similarity	NPC49994
0.7523	Intermediate Similarity	NPC185763
0.7523	Intermediate Similarity	NPC83409
0.7522	Intermediate Similarity	NPC326664
0.7521	Intermediate Similarity	NPC318552
0.7521	Intermediate Similarity	NPC478121
0.7521	Intermediate Similarity	NPC190501
0.75	Intermediate Similarity	NPC261947
0.75	Intermediate Similarity	NPC472698
0.75	Intermediate Similarity	NPC318173
0.75	Intermediate Similarity	NPC328694
0.75	Intermediate Similarity	NPC472697
0.748	Intermediate Similarity	NPC131684
0.7479	Intermediate Similarity	NPC176208
0.7479	Intermediate Similarity	NPC11250
0.7477	Intermediate Similarity	NPC474820
0.7477	Intermediate Similarity	NPC475978
0.7476	Intermediate Similarity	NPC238219
0.7476	Intermediate Similarity	NPC289883
0.7474	Intermediate Similarity	NPC159661
0.7458	Intermediate Similarity	NPC472981
0.7458	Intermediate Similarity	NPC164852
0.7456	Intermediate Similarity	NPC217111
0.7455	Intermediate Similarity	NPC472980
0.7453	Intermediate Similarity	NPC217621
0.7453	Intermediate Similarity	NPC54647
0.7451	Intermediate Similarity	NPC187725
0.7451	Intermediate Similarity	NPC133461
0.7451	Intermediate Similarity	NPC141607
0.7438	Intermediate Similarity	NPC470765
0.7434	Intermediate Similarity	NPC469547
0.7431	Intermediate Similarity	NPC134120
0.7431	Intermediate Similarity	NPC172483
0.7429	Intermediate Similarity	NPC251579
0.7429	Intermediate Similarity	NPC133135
0.7426	Intermediate Similarity	NPC9822
0.7423	Intermediate Similarity	NPC230068
0.7417	Intermediate Similarity	NPC471187
0.7417	Intermediate Similarity	NPC140118
0.7417	Intermediate Similarity	NPC12881
0.7414	Intermediate Similarity	NPC152812
0.7395	Intermediate Similarity	NPC253627
0.7395	Intermediate Similarity	NPC154696
0.7387	Intermediate Similarity	NPC470252
0.7383	Intermediate Similarity	NPC94487
0.7379	Intermediate Similarity	NPC155232
0.7377	Intermediate Similarity	NPC171007
0.7377	Intermediate Similarity	NPC473220
0.7377	Intermediate Similarity	NPC190849
0.7377	Intermediate Similarity	NPC5486
0.7377	Intermediate Similarity	NPC470753
0.7373	Intermediate Similarity	NPC472679
0.7373	Intermediate Similarity	NPC472680
0.7368	Intermediate Similarity	NPC196673
0.7368	Intermediate Similarity	NPC103488

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 NPC133809 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	190
0.1-0.2	815
0.2-0.3	1220
0.3-0.4	2934
0.4-0.5	2460
0.5-0.6	1186
0.6-0.7	282
0.7-0.8	50
0.8-0.85	13
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8646	High Similarity	NPD1088	Approved
0.8598	High Similarity	NPD5951	Approved
0.8469	Intermediate Similarity	NPD688	Clinical (unspecified phase)
0.8438	Intermediate Similarity	NPD1089	Approved
0.8438	Intermediate Similarity	NPD1086	Approved
0.8438	Intermediate Similarity	NPD1090	Approved
0.8333	Intermediate Similarity	NPD800	Approved
0.8317	Intermediate Similarity	NPD2066	Phase 3
0.8182	Intermediate Similarity	NPD5122	Clinical (unspecified phase)
0.8163	Intermediate Similarity	NPD1239	Approved
0.8144	Intermediate Similarity	NPD5347	Phase 2
0.8144	Intermediate Similarity	NPD5346	Phase 2
0.8142	Intermediate Similarity	NPD4199	Phase 3
0.8142	Intermediate Similarity	NPD7163	Clinical (unspecified phase)
0.8125	Intermediate Similarity	NPD1087	Approved
0.8119	Intermediate Similarity	NPD1566	Phase 3
0.8119	Intermediate Similarity	NPD1564	Approved
0.8119	Intermediate Similarity	NPD1565	Approved
0.81	Intermediate Similarity	NPD1693	Approved
0.8077	Intermediate Similarity	NPD1931	Clinical (unspecified phase)
0.8077	Intermediate Similarity	NPD1929	Approved
0.8077	Intermediate Similarity	NPD1930	Approved
0.8065	Intermediate Similarity	NPD226	Approved
0.7941	Intermediate Similarity	NPD3495	Discontinued
0.7938	Intermediate Similarity	NPD4793	Discontinued
0.7921	Intermediate Similarity	NPD6049	Phase 2
0.7921	Intermediate Similarity	NPD6048	Clinical (unspecified phase)
0.7909	Intermediate Similarity	NPD7094	Approved
0.7909	Intermediate Similarity	NPD6858	Approved
0.7843	Intermediate Similarity	NPD1989	Approved
0.7822	Intermediate Similarity	NPD1563	Approved
0.781	Intermediate Similarity	NPD1932	Approved
0.7742	Intermediate Similarity	NPD227	Approved
0.7742	Intermediate Similarity	NPD225	Approved
0.7727	Intermediate Similarity	NPD4141	Clinical (unspecified phase)
0.7719	Intermediate Similarity	NPD7610	Discontinued
0.7708	Intermediate Similarity	NPD9491	Approved
0.7706	Intermediate Similarity	NPD2329	Discontinued
0.7706	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.77	Intermediate Similarity	NPD3672	Approved
0.77	Intermediate Similarity	NPD3673	Approved
0.7664	Intermediate Similarity	NPD5909	Discontinued
0.7568	Intermediate Similarity	NPD3642	Approved
0.7568	Intermediate Similarity	NPD3643	Approved
0.7568	Intermediate Similarity	NPD3644	Approved
0.7521	Intermediate Similarity	NPD3019	Approved
0.75	Intermediate Similarity	NPD7009	Phase 2
0.75	Intermediate Similarity	NPD5206	Clinical (unspecified phase)
0.748	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.748	Intermediate Similarity	NPD7008	Discontinued
0.7456	Intermediate Similarity	NPD2629	Approved
0.7374	Intermediate Similarity	NPD5734	Clinical (unspecified phase)
0.7373	Intermediate Similarity	NPD2932	Approved
0.7368	Intermediate Similarity	NPD6010	Discontinued
0.7347	Intermediate Similarity	NPD3971	Phase 1
0.7333	Intermediate Similarity	NPD3880	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD9490	Approved
0.729	Intermediate Similarity	NPD7798	Approved
0.725	Intermediate Similarity	NPD5618	Discontinued
0.7241	Intermediate Similarity	NPD4198	Discontinued
0.7241	Intermediate Similarity	NPD3317	Approved
0.7222	Intermediate Similarity	NPD7961	Discontinued
0.7222	Intermediate Similarity	NPD6663	Approved
0.7212	Intermediate Similarity	NPD7631	Approved
0.7196	Intermediate Similarity	NPD253	Approved
0.7177	Intermediate Similarity	NPD5736	Approved
0.7168	Intermediate Similarity	NPD1317	Discontinued
0.7167	Intermediate Similarity	NPD3023	Approved
0.7167	Intermediate Similarity	NPD3881	Discontinued
0.7167	Intermediate Similarity	NPD3026	Approved
0.7143	Intermediate Similarity	NPD3024	Approved
0.7143	Intermediate Similarity	NPD3025	Approved
0.713	Intermediate Similarity	NPD3097	Clinical (unspecified phase)
0.7119	Intermediate Similarity	NPD6065	Approved
0.7115	Intermediate Similarity	NPD7609	Phase 3
0.7091	Intermediate Similarity	NPD5765	Approved
0.7091	Intermediate Similarity	NPD5700	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD1283	Approved
0.7069	Intermediate Similarity	NPD3598	Phase 3
0.7054	Intermediate Similarity	NPD6685	Approved
0.7034	Intermediate Similarity	NPD3797	Approved
0.7018	Intermediate Similarity	NPD5278	Discontinued
0.7018	Intermediate Similarity	NPD3646	Clinical (unspecified phase)
0.7009	Intermediate Similarity	NPD4766	Approved
0.7	Intermediate Similarity	NPD6994	Approved
0.7	Intermediate Similarity	NPD6993	Approved
0.7	Intermediate Similarity	NPD5981	Approved
0.6964	Remote Similarity	NPD1018	Approved
0.6964	Remote Similarity	NPD5048	Discontinued
0.6957	Remote Similarity	NPD5927	Discontinued
0.6953	Remote Similarity	NPD7715	Approved
0.6953	Remote Similarity	NPD7714	Approved
0.6942	Remote Similarity	NPD2345	Approved
0.694	Remote Similarity	NPD7003	Approved
0.6937	Remote Similarity	NPD6647	Phase 2
0.6917	Remote Similarity	NPD4479	Discontinued
0.6917	Remote Similarity	NPD3798	Phase 3
0.6893	Remote Similarity	NPD650	Approved
0.6891	Remote Similarity	NPD5162	Approved
0.6885	Remote Similarity	NPD7457	Clinical (unspecified phase)
0.6885	Remote Similarity	NPD2956	Clinical (unspecified phase)
0.6885	Remote Similarity	NPD4879	Approved
0.688	Remote Similarity	NPD6564	Approved
0.688	Remote Similarity	NPD6565	Approved
0.688	Remote Similarity	NPD6563	Approved
0.686	Remote Similarity	NPD1855	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD1281	Approved
0.6827	Remote Similarity	NPD1101	Approved
0.6822	Remote Similarity	NPD8032	Phase 2
0.6822	Remote Similarity	NPD1066	Discontinued
0.6797	Remote Similarity	NPD6966	Discovery
0.6789	Remote Similarity	NPD9566	Approved
0.6786	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.678	Remote Similarity	NPD2650	Approved
0.678	Remote Similarity	NPD2652	Approved
0.678	Remote Similarity	NPD1280	Clinical (unspecified phase)
0.6727	Remote Similarity	NPD9495	Approved
0.6724	Remote Similarity	NPD4234	Approved
0.6724	Remote Similarity	NPD1756	Approved
0.6724	Remote Similarity	NPD4233	Approved
0.6724	Remote Similarity	NPD1752	Approved
0.672	Remote Similarity	NPD182	Clinical (unspecified phase)
0.6716	Remote Similarity	NPD3935	Phase 3
0.6698	Remote Similarity	NPD9256	Approved
0.6698	Remote Similarity	NPD9258	Approved
0.6696	Remote Similarity	NPD2342	Discontinued
0.6695	Remote Similarity	NPD2607	Approved
0.6695	Remote Similarity	NPD7635	Approved
0.6667	Remote Similarity	NPD5305	Approved
0.6667	Remote Similarity	NPD4382	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1202	Approved
0.6667	Remote Similarity	NPD5306	Approved
0.6667	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6642	Remote Similarity	NPD5404	Approved
0.6642	Remote Similarity	NPD5405	Approved
0.6642	Remote Similarity	NPD5406	Approved
0.6642	Remote Similarity	NPD5408	Approved
0.6641	Remote Similarity	NPD7084	Phase 3
0.664	Remote Similarity	NPD4878	Approved
0.6639	Remote Similarity	NPD3091	Approved
0.6639	Remote Similarity	NPD4869	Clinical (unspecified phase)
0.6639	Remote Similarity	NPD2617	Discontinued
0.6638	Remote Similarity	NPD2182	Approved
0.6636	Remote Similarity	NPD1875	Phase 1
0.6615	Remote Similarity	NPD6766	Clinical (unspecified phase)
0.6615	Remote Similarity	NPD5422	Clinical (unspecified phase)
0.6612	Remote Similarity	NPD4576	Approved
0.6612	Remote Similarity	NPD4574	Approved
0.661	Remote Similarity	NPD6912	Phase 3
0.6607	Remote Similarity	NPD3135	Clinical (unspecified phase)
0.6606	Remote Similarity	NPD4814	Discontinued
0.6606	Remote Similarity	NPD3772	Phase 3
0.6606	Remote Similarity	NPD4094	Approved
0.6602	Remote Similarity	NPD4544	Approved
0.6585	Remote Similarity	NPD4105	Approved
0.6585	Remote Similarity	NPD1651	Approved
0.6585	Remote Similarity	NPD4102	Approved
0.6579	Remote Similarity	NPD164	Approved
0.6577	Remote Similarity	NPD5926	Approved
0.6574	Remote Similarity	NPD1508	Approved
0.6569	Remote Similarity	NPD8166	Discontinued
0.6567	Remote Similarity	NPD7305	Phase 1
0.656	Remote Similarity	NPD7436	Approved
0.656	Remote Similarity	NPD4807	Approved
0.656	Remote Similarity	NPD6287	Discontinued
0.656	Remote Similarity	NPD1201	Approved
0.656	Remote Similarity	NPD4806	Approved
0.656	Remote Similarity	NPD7437	Approved
0.6535	Remote Similarity	NPD1507	Clinical (unspecified phase)
0.6532	Remote Similarity	NPD3095	Discontinued
0.6532	Remote Similarity	NPD4059	Approved
0.6525	Remote Similarity	NPD188	Approved
0.6525	Remote Similarity	NPD189	Phase 3
0.6518	Remote Similarity	NPD3020	Approved
0.6518	Remote Similarity	NPD1067	Discontinued
0.6515	Remote Similarity	NPD2979	Phase 3
0.6515	Remote Similarity	NPD4140	Approved
0.6514	Remote Similarity	NPD3718	Approved
0.6514	Remote Similarity	NPD719	Approved
0.6514	Remote Similarity	NPD720	Approved
0.6514	Remote Similarity	NPD3719	Approved
0.6514	Remote Similarity	NPD1409	Phase 3
0.6504	Remote Similarity	NPD7741	Discontinued
0.6493	Remote Similarity	NPD3934	Clinical (unspecified phase)
0.6486	Remote Similarity	NPD2487	Clinical (unspecified phase)
0.6486	Remote Similarity	NPD4657	Approved
0.6486	Remote Similarity	NPD4655	Approved
0.6484	Remote Similarity	NPD2797	Approved
0.648	Remote Similarity	NPD4136	Approved
0.648	Remote Similarity	NPD4135	Approved
0.648	Remote Similarity	NPD4106	Approved
0.6476	Remote Similarity	NPD9259	Approved
0.6476	Remote Similarity	NPD9257	Approved
0.6475	Remote Similarity	NPD7325	Clinical (unspecified phase)
0.6475	Remote Similarity	NPD7236	Approved
0.6471	Remote Similarity	NPD942	Approved
0.6471	Remote Similarity	NPD2346	Discontinued
0.6466	Remote Similarity	NPD5705	Approved
0.6466	Remote Similarity	NPD467	Phase 1

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