NPASS Compound

Structure

NPC470418 OpenBabel07101719512D 32 37 0 0 1 0 0 0 0 0999 V2000 3.2210 -1.8031 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7210 -2.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1229 -3.1691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1970 -1.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1229 -0.1691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7431 -2.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8549 -4.1691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9889 -3.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6092 -2.1691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7372 -1.6215 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9456 0.4135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8549 -1.1691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3305 -0.7079 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3523 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.1229 -2.1691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8549 -2.1691 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.7210 -3.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9889 -0.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 0.3090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.7317 -1.5169 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0736 -0.0388 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 2.7210 -2.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9889 -2.6691 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6092 -1.1691 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.1229 -1.1691 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.7431 -0.6691 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.5870 -4.1691 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9889 0.3309 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.4009 -2.2601 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.9691 0.9557 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.9396 -0.5388 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 22 1 0 0 0 0 2 22 1 0 0 0 0 4 24 1 0 0 0 0 5 25 1 0 0 0 0 6 9 1 0 0 0 0 6 15 2 0 0 0 0 7 8 2 0 0 0 0 7 17 1 0 0 0 0 8 23 1 0 0 0 0 9 24 1 0 0 0 0 10 13 2 0 0 0 0 10 20 1 0 0 0 0 11 14 1 0 0 0 0 11 19 1 0 0 0 0 12 16 1 0 0 0 0 12 18 1 0 0 0 0 13 14 1 0 0 0 0 13 21 1 0 0 0 0 14 24 1 6 0 0 0 15 23 1 0 0 0 0 15 25 1 0 0 0 0 16 22 1 0 0 0 0 16 23 1 1 0 0 0 17 22 1 0 0 0 0 17 27 2 0 0 0 0 18 25 1 0 0 0 0 18 28 2 0 0 0 0 19 26 1 6 0 0 0 19 32 1 0 0 0 0 20 29 2 0 0 0 0 20 31 1 0 0 0 0 21 30 1 0 0 0 0 21 31 1 0 0 0 0 23 3 1 1 0 0 0 24 26 1 6 0 0 0 25 26 1 6 0 0 0 26 32 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	438.2
Volume:	443.836
LogP:	3.13
LogD:	2.63
LogS:	-4.421
# Rotatable Bonds:	1
TPSA:	100.27
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	6
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.497
Synthetic Accessibility Score:	5.967
Fsp3:	0.615
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-5.557
MDCK Permeability:	1.542803511256352e-05
Pgp-inhibitor:	0.002
Pgp-substrate:	0.008
Human Intestinal Absorption (HIA):	0.013
20% Bioavailability (F20%):	0.01
30% Bioavailability (F30%):	0.282

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.729
Plasma Protein Binding (PPB):	88.86774444580078%
Volume Distribution (VD):	1.089
Pgp-substrate:	11.801883697509766%

ADMET: Metabolism

CYP1A2-inhibitor:	0.007
CYP1A2-substrate:	0.865
CYP2C19-inhibitor:	0.019
CYP2C19-substrate:	0.476
CYP2C9-inhibitor:	0.183
CYP2C9-substrate:	0.132
CYP2D6-inhibitor:	0.011
CYP2D6-substrate:	0.047
CYP3A4-inhibitor:	0.612
CYP3A4-substrate:	0.811

ADMET: Excretion

Clearance (CL):	11.144
Half-life (T1/2):	0.658

ADMET: Toxicity

hERG Blockers:	0.015
Human Hepatotoxicity (H-HT):	0.273
Drug-inuced Liver Injury (DILI):	0.148
AMES Toxicity:	0.012
Rat Oral Acute Toxicity:	0.909
Maximum Recommended Daily Dose:	0.939
Skin Sensitization:	0.159
Carcinogencity:	0.915
Eye Corrosion:	0.003
Eye Irritation:	0.158
Respiratory Toxicity:	0.964

Download Data

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

Natural Product: NPC470418

Natural Product ID:	NPC470418
*Common Name:**	Toonaciliatavarin F
IUPAC Name:	n.a.
Synonyms:	Toonaciliatavarin F
Standard InCHIKey:	SDYQIAAYGZKFQX-HOEPTORSSA-N
Standard InCHI:	InChI=1S/C26H30O6/c1-22(2)16-12-18(28)25(5)15(23(16,3)8-7-17(22)27)6-9-24(4)14(11-19-26(24,25)32-19)13-10-20(29)31-21(13)30/h6-8,10,14,16,19,21,30H,9,11-12H2,1-5H3/t14-,16-,19+,21?,23+,24-,25-,26+/m0/s1
SMILES:	O=C1OC(C(=C1)[C@@H]1C[C@@H]2[C@]3([C@@]1(C)CC=C1[C@@]3(C)C(=O)C[C@@H]3[C@]1(C)C=CC(=O)C3(C)C)O2)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2035086
PubChem CID:	57409855
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001125] Steroid lactones

*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
NPO13083	Toona ciliata	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19275174]
NPO13083	Toona ciliata	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22537362]
NPO13083	Toona ciliata	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31503490]
NPO13083	Toona ciliata	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13083	Toona ciliata	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13083	Toona ciliata	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO13083	Toona ciliata	Species	Meliaceae	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
IC50	7

Activity Type	# Activity
Cell Line	5
NON-MOLECULAR	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	50000.0	nM	PMID[498367]
NPT91	Cell Line	KB	Homo sapiens	IC50	>	50000.0	nM	PMID[498367]
NPT659	Cell Line	SMMC-7721	Homo sapiens	IC50	>	50000.0	nM	PMID[498367]
NPT111	Cell Line	K562	Homo sapiens	IC50	>	50000.0	nM	PMID[498367]
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	28800.0	nM	PMID[498367]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	50000.0	nM	PMID[498367]
NPT2	Others	Unspecified		IC50	>	50000	nM	PMID[20521785]

☑ 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 NPC470418 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	231
0.1-0.2	1401
0.2-0.3	4668
0.3-0.4	8996
0.4-0.5	12541
0.5-0.6	7589
0.6-0.7	5765
0.7-0.8	1454
0.8-0.85	47
0.85-0.9	2
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9735	High Similarity	NPC470419
0.864	High Similarity	NPC478072
0.8618	High Similarity	NPC104382
0.8559	High Similarity	NPC475913
0.8487	Intermediate Similarity	NPC475834
0.8487	Intermediate Similarity	NPC474179
0.8468	Intermediate Similarity	NPC175186
0.8468	Intermediate Similarity	NPC473593
0.8455	Intermediate Similarity	NPC287423
0.8403	Intermediate Similarity	NPC470420
0.84	Intermediate Similarity	NPC471170
0.8361	Intermediate Similarity	NPC472768
0.8361	Intermediate Similarity	NPC204812
0.8347	Intermediate Similarity	NPC473256
0.8347	Intermediate Similarity	NPC470878
0.8293	Intermediate Similarity	NPC241456
0.8293	Intermediate Similarity	NPC32868
0.824	Intermediate Similarity	NPC473620
0.822	Intermediate Similarity	NPC122056
0.8203	Intermediate Similarity	NPC471234
0.8197	Intermediate Similarity	NPC67569
0.8197	Intermediate Similarity	NPC46570
0.8189	Intermediate Similarity	NPC231240
0.8182	Intermediate Similarity	NPC264954
0.8182	Intermediate Similarity	NPC473274
0.8182	Intermediate Similarity	NPC473270
0.8175	Intermediate Similarity	NPC472770
0.8174	Intermediate Similarity	NPC91034
0.8167	Intermediate Similarity	NPC239273
0.816	Intermediate Similarity	NPC42399
0.8151	Intermediate Similarity	NPC474181
0.8145	Intermediate Similarity	NPC8369
0.8145	Intermediate Similarity	NPC8374
0.8136	Intermediate Similarity	NPC191620
0.8136	Intermediate Similarity	NPC236217
0.813	Intermediate Similarity	NPC23786
0.813	Intermediate Similarity	NPC470265
0.813	Intermediate Similarity	NPC107493
0.8125	Intermediate Similarity	NPC316915
0.812	Intermediate Similarity	NPC179642
0.8115	Intermediate Similarity	NPC474370
0.8095	Intermediate Similarity	NPC470850
0.8095	Intermediate Similarity	NPC311534
0.8083	Intermediate Similarity	NPC148458
0.8067	Intermediate Similarity	NPC9848
0.8067	Intermediate Similarity	NPC312017
0.8065	Intermediate Similarity	NPC469789
0.8065	Intermediate Similarity	NPC120724
0.8053	Intermediate Similarity	NPC475099
0.8047	Intermediate Similarity	NPC472769
0.8033	Intermediate Similarity	NPC476960
0.8033	Intermediate Similarity	NPC472933
0.8017	Intermediate Similarity	NPC472934
0.8017	Intermediate Similarity	NPC286528
0.8017	Intermediate Similarity	NPC20302
0.8017	Intermediate Similarity	NPC167606
0.8017	Intermediate Similarity	NPC140055
0.8017	Intermediate Similarity	NPC470492
0.8017	Intermediate Similarity	NPC472927
0.8	Intermediate Similarity	NPC172154
0.8	Intermediate Similarity	NPC3381
0.8	Intermediate Similarity	NPC81736
0.7984	Intermediate Similarity	NPC153700
0.7984	Intermediate Similarity	NPC469674
0.7984	Intermediate Similarity	NPC88326
0.7982	Intermediate Similarity	NPC293753
0.7969	Intermediate Similarity	NPC196921
0.7969	Intermediate Similarity	NPC220757
0.7969	Intermediate Similarity	NPC476852
0.7969	Intermediate Similarity	NPC476862
0.7969	Intermediate Similarity	NPC476863
0.7966	Intermediate Similarity	NPC235014
0.7953	Intermediate Similarity	NPC476859
0.7951	Intermediate Similarity	NPC50774
0.7951	Intermediate Similarity	NPC709
0.7951	Intermediate Similarity	NPC186525
0.7949	Intermediate Similarity	NPC472825
0.7949	Intermediate Similarity	NPC220155
0.7937	Intermediate Similarity	NPC293112
0.7934	Intermediate Similarity	NPC190286
0.7931	Intermediate Similarity	NPC470309
0.792	Intermediate Similarity	NPC11895
0.7903	Intermediate Similarity	NPC471999
0.7903	Intermediate Similarity	NPC472000
0.7903	Intermediate Similarity	NPC310511
0.7903	Intermediate Similarity	NPC472001
0.7899	Intermediate Similarity	NPC472928
0.7899	Intermediate Similarity	NPC474315
0.7899	Intermediate Similarity	NPC470961
0.7899	Intermediate Similarity	NPC324683
0.7891	Intermediate Similarity	NPC471407
0.7891	Intermediate Similarity	NPC476966
0.7891	Intermediate Similarity	NPC35109
0.7891	Intermediate Similarity	NPC476851
0.7891	Intermediate Similarity	NPC470851
0.7891	Intermediate Similarity	NPC231529
0.7881	Intermediate Similarity	NPC474901
0.7881	Intermediate Similarity	NPC475941
0.7874	Intermediate Similarity	NPC298841
0.7874	Intermediate Similarity	NPC473253
0.7869	Intermediate Similarity	NPC470493
0.7869	Intermediate Similarity	NPC183580
0.7869	Intermediate Similarity	NPC312824
0.7869	Intermediate Similarity	NPC243065
0.7851	Intermediate Similarity	NPC238667
0.7851	Intermediate Similarity	NPC470953
0.7851	Intermediate Similarity	NPC67259
0.7851	Intermediate Similarity	NPC147912
0.7846	Intermediate Similarity	NPC469673
0.784	Intermediate Similarity	NPC170538
0.784	Intermediate Similarity	NPC269642
0.7833	Intermediate Similarity	NPC100267
0.7833	Intermediate Similarity	NPC475524
0.7833	Intermediate Similarity	NPC475970
0.7833	Intermediate Similarity	NPC221144
0.7829	Intermediate Similarity	NPC213634
0.7829	Intermediate Similarity	NPC476855
0.7826	Intermediate Similarity	NPC234892
0.7823	Intermediate Similarity	NPC79579
0.7823	Intermediate Similarity	NPC474585
0.7823	Intermediate Similarity	NPC476962
0.7815	Intermediate Similarity	NPC42776
0.7815	Intermediate Similarity	NPC206595
0.7815	Intermediate Similarity	NPC37116
0.7815	Intermediate Similarity	NPC29133
0.7812	Intermediate Similarity	NPC245094
0.7807	Intermediate Similarity	NPC307954
0.7807	Intermediate Similarity	NPC54705
0.7805	Intermediate Similarity	NPC153440
0.7805	Intermediate Similarity	NPC329736
0.7805	Intermediate Similarity	NPC113448
0.7797	Intermediate Similarity	NPC476765
0.7797	Intermediate Similarity	NPC322903
0.7797	Intermediate Similarity	NPC61411
0.7795	Intermediate Similarity	NPC15095
0.7788	Intermediate Similarity	NPC475709
0.7788	Intermediate Similarity	NPC476253
0.7787	Intermediate Similarity	NPC469794
0.7787	Intermediate Similarity	NPC64318
0.7787	Intermediate Similarity	NPC176840
0.7787	Intermediate Similarity	NPC72772
0.7787	Intermediate Similarity	NPC268213
0.7786	Intermediate Similarity	NPC476823
0.7778	Intermediate Similarity	NPC472935
0.7778	Intermediate Similarity	NPC473979
0.7769	Intermediate Similarity	NPC472926
0.7769	Intermediate Similarity	NPC472929
0.7769	Intermediate Similarity	NPC471855
0.7769	Intermediate Similarity	NPC34963
0.7768	Intermediate Similarity	NPC476488
0.7768	Intermediate Similarity	NPC476487
0.7759	Intermediate Similarity	NPC159442
0.7759	Intermediate Similarity	NPC36688
0.7752	Intermediate Similarity	NPC476854
0.7752	Intermediate Similarity	NPC470880
0.775	Intermediate Similarity	NPC207689
0.7742	Intermediate Similarity	NPC61520
0.7742	Intermediate Similarity	NPC475041
0.7742	Intermediate Similarity	NPC5292
0.7742	Intermediate Similarity	NPC475520
0.7739	Intermediate Similarity	NPC472924
0.7739	Intermediate Similarity	NPC99411
0.7734	Intermediate Similarity	NPC305496
0.7734	Intermediate Similarity	NPC469757
0.7734	Intermediate Similarity	NPC471357
0.7734	Intermediate Similarity	NPC146456
0.7734	Intermediate Similarity	NPC117702
0.7731	Intermediate Similarity	NPC31522
0.7724	Intermediate Similarity	NPC469684
0.7724	Intermediate Similarity	NPC474518
0.7719	Intermediate Similarity	NPC197386
0.7719	Intermediate Similarity	NPC166745
0.7719	Intermediate Similarity	NPC316598
0.7719	Intermediate Similarity	NPC235464
0.7712	Intermediate Similarity	NPC472925
0.7712	Intermediate Similarity	NPC475294
0.7712	Intermediate Similarity	NPC473037
0.771	Intermediate Similarity	NPC476097
0.771	Intermediate Similarity	NPC470427
0.771	Intermediate Similarity	NPC327664
0.771	Intermediate Similarity	NPC58029
0.7704	Intermediate Similarity	NPC25887
0.7699	Intermediate Similarity	NPC472941
0.7699	Intermediate Similarity	NPC456
0.7698	Intermediate Similarity	NPC287236
0.7692	Intermediate Similarity	NPC96268
0.7692	Intermediate Similarity	NPC241935
0.7692	Intermediate Similarity	NPC279478
0.7692	Intermediate Similarity	NPC173347
0.7686	Intermediate Similarity	NPC12046
0.7686	Intermediate Similarity	NPC194951
0.7686	Intermediate Similarity	NPC69291
0.768	Intermediate Similarity	NPC109973
0.768	Intermediate Similarity	NPC17938
0.768	Intermediate Similarity	NPC476961
0.768	Intermediate Similarity	NPC281840
0.7679	Intermediate Similarity	NPC53685
0.7672	Intermediate Similarity	NPC475320
0.7672	Intermediate Similarity	NPC58329
0.7672	Intermediate Similarity	NPC281702

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 NPC470418 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	205
0.1-0.2	1648
0.2-0.3	3806
0.3-0.4	2365
0.4-0.5	641
0.5-0.6	232
0.6-0.7	227
0.7-0.8	26
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
0.8017	Intermediate Similarity	NPD7115	Discovery
0.7627	Intermediate Similarity	NPD6008	Approved
0.7615	Intermediate Similarity	NPD7319	Approved
0.7559	Intermediate Similarity	NPD6370	Approved
0.7538	Intermediate Similarity	NPD7736	Approved
0.7519	Intermediate Similarity	NPD7507	Approved
0.75	Intermediate Similarity	NPD7640	Approved
0.75	Intermediate Similarity	NPD7639	Approved
0.7442	Intermediate Similarity	NPD7492	Approved
0.7414	Intermediate Similarity	NPD7638	Approved
0.7414	Intermediate Similarity	NPD5696	Approved
0.7411	Intermediate Similarity	NPD5785	Approved
0.7402	Intermediate Similarity	NPD6054	Approved
0.7385	Intermediate Similarity	NPD6616	Approved
0.7355	Intermediate Similarity	NPD6686	Approved
0.7344	Intermediate Similarity	NPD6015	Approved
0.7344	Intermediate Similarity	NPD6016	Approved
0.7328	Intermediate Similarity	NPD8293	Discontinued
0.7328	Intermediate Similarity	NPD7078	Approved
0.7304	Intermediate Similarity	NPD5210	Approved
0.7304	Intermediate Similarity	NPD5695	Phase 3
0.7304	Intermediate Similarity	NPD4629	Approved
0.7302	Intermediate Similarity	NPD6009	Approved
0.7287	Intermediate Similarity	NPD5988	Approved
0.7273	Intermediate Similarity	NPD5697	Approved
0.7273	Intermediate Similarity	NPD6412	Phase 2
0.7266	Intermediate Similarity	NPD6319	Approved
0.7258	Intermediate Similarity	NPD6053	Discontinued
0.7258	Intermediate Similarity	NPD6882	Approved
0.7244	Intermediate Similarity	NPD7328	Approved
0.7244	Intermediate Similarity	NPD7327	Approved
0.7236	Intermediate Similarity	NPD6371	Approved
0.7213	Intermediate Similarity	NPD6011	Approved
0.7213	Intermediate Similarity	NPD6899	Approved
0.7213	Intermediate Similarity	NPD6881	Approved
0.7209	Intermediate Similarity	NPD7503	Approved
0.7209	Intermediate Similarity	NPD8033	Approved
0.72	Intermediate Similarity	NPD4632	Approved
0.7193	Intermediate Similarity	NPD5281	Approved
0.7193	Intermediate Similarity	NPD5284	Approved
0.7188	Intermediate Similarity	NPD7516	Approved
0.7179	Intermediate Similarity	NPD6084	Phase 2
0.7179	Intermediate Similarity	NPD6083	Phase 2
0.7177	Intermediate Similarity	NPD6649	Approved
0.7177	Intermediate Similarity	NPD6650	Approved
0.7155	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7154	Intermediate Similarity	NPD6012	Approved
0.7154	Intermediate Similarity	NPD6013	Approved
0.7154	Intermediate Similarity	NPD6014	Approved
0.7132	Intermediate Similarity	NPD8377	Approved
0.7132	Intermediate Similarity	NPD8294	Approved
0.7132	Intermediate Similarity	NPD6059	Approved
0.7105	Intermediate Similarity	NPD5207	Approved
0.7097	Intermediate Similarity	NPD6883	Approved
0.7097	Intermediate Similarity	NPD7102	Approved
0.7097	Intermediate Similarity	NPD7290	Approved
0.7083	Intermediate Similarity	NPD5211	Phase 2
0.7077	Intermediate Similarity	NPD8379	Approved
0.7077	Intermediate Similarity	NPD8296	Approved
0.7077	Intermediate Similarity	NPD8378	Approved
0.7077	Intermediate Similarity	NPD8380	Approved
0.7077	Intermediate Similarity	NPD8335	Approved
0.7073	Intermediate Similarity	NPD7320	Approved
0.7049	Intermediate Similarity	NPD6675	Approved
0.7049	Intermediate Similarity	NPD6402	Approved
0.7049	Intermediate Similarity	NPD7128	Approved
0.7049	Intermediate Similarity	NPD5739	Approved
0.7043	Intermediate Similarity	NPD5693	Phase 1
0.704	Intermediate Similarity	NPD6617	Approved
0.704	Intermediate Similarity	NPD8130	Phase 1
0.704	Intermediate Similarity	NPD6847	Approved
0.704	Intermediate Similarity	NPD6869	Approved
0.7016	Intermediate Similarity	NPD6373	Approved
0.7016	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7016	Intermediate Similarity	NPD6372	Approved
0.6992	Remote Similarity	NPD5701	Approved
0.6984	Remote Similarity	NPD8297	Approved
0.6983	Remote Similarity	NPD6399	Phase 3
0.6975	Remote Similarity	NPD4225	Approved
0.697	Remote Similarity	NPD7604	Phase 2
0.6967	Remote Similarity	NPD5141	Approved
0.6964	Remote Similarity	NPD5363	Approved
0.696	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.696	Remote Similarity	NPD4634	Approved
0.6947	Remote Similarity	NPD5983	Phase 2
0.6942	Remote Similarity	NPD7632	Discontinued
0.693	Remote Similarity	NPD6903	Approved
0.6923	Remote Similarity	NPD6001	Approved
0.6917	Remote Similarity	NPD5285	Approved
0.6917	Remote Similarity	NPD5286	Approved
0.6917	Remote Similarity	NPD4696	Approved
0.6903	Remote Similarity	NPD7146	Approved
0.6903	Remote Similarity	NPD6684	Approved
0.6903	Remote Similarity	NPD7334	Approved
0.6903	Remote Similarity	NPD6409	Approved
0.6903	Remote Similarity	NPD5690	Phase 2
0.6903	Remote Similarity	NPD7521	Approved
0.6903	Remote Similarity	NPD5330	Approved
0.6903	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD5694	Approved
0.6875	Remote Similarity	NPD3133	Approved
0.6875	Remote Similarity	NPD3666	Approved
0.6875	Remote Similarity	NPD3665	Phase 1
0.687	Remote Similarity	NPD4753	Phase 2
0.686	Remote Similarity	NPD5223	Approved
0.6838	Remote Similarity	NPD5779	Approved
0.6838	Remote Similarity	NPD4202	Approved
0.6838	Remote Similarity	NPD5778	Approved
0.6818	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6814	Remote Similarity	NPD1694	Approved
0.681	Remote Similarity	NPD5692	Phase 3
0.6803	Remote Similarity	NPD4633	Approved
0.6803	Remote Similarity	NPD5226	Approved
0.6803	Remote Similarity	NPD5225	Approved
0.6803	Remote Similarity	NPD5224	Approved
0.6788	Remote Similarity	NPD5956	Approved
0.6783	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6769	Remote Similarity	NPD6317	Approved
0.6765	Remote Similarity	NPD6033	Approved
0.6754	Remote Similarity	NPD3618	Phase 1
0.6752	Remote Similarity	NPD6079	Approved
0.6752	Remote Similarity	NPD7637	Suspended
0.6752	Remote Similarity	NPD6050	Approved
0.675	Remote Similarity	NPD4755	Approved
0.6748	Remote Similarity	NPD5174	Approved
0.6748	Remote Similarity	NPD5175	Approved
0.6741	Remote Similarity	NPD6336	Discontinued
0.6739	Remote Similarity	NPD7260	Phase 2
0.6724	Remote Similarity	NPD6673	Approved
0.6724	Remote Similarity	NPD6080	Approved
0.6724	Remote Similarity	NPD6904	Approved
0.6723	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.672	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.672	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6718	Remote Similarity	NPD6314	Approved
0.6718	Remote Similarity	NPD6335	Approved
0.6718	Remote Similarity	NPD6313	Approved
0.6716	Remote Similarity	NPD6067	Discontinued
0.6696	Remote Similarity	NPD4223	Phase 3
0.6696	Remote Similarity	NPD4270	Approved
0.6696	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6696	Remote Similarity	NPD4269	Approved
0.6696	Remote Similarity	NPD4221	Approved
0.6692	Remote Similarity	NPD8515	Approved
0.6692	Remote Similarity	NPD8513	Phase 3
0.6692	Remote Similarity	NPD8517	Approved
0.6692	Remote Similarity	NPD8516	Approved
0.6692	Remote Similarity	NPD6274	Approved
0.6667	Remote Similarity	NPD7100	Approved
0.6667	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5221	Approved
0.6667	Remote Similarity	NPD7101	Approved
0.6667	Remote Similarity	NPD8133	Approved
0.6667	Remote Similarity	NPD5222	Approved
0.6639	Remote Similarity	NPD4700	Approved
0.6638	Remote Similarity	NPD5737	Approved
0.6638	Remote Similarity	NPD5208	Approved
0.6638	Remote Similarity	NPD6672	Approved
0.6637	Remote Similarity	NPD5362	Discontinued
0.6612	Remote Similarity	NPD5173	Approved
0.661	Remote Similarity	NPD6411	Approved
0.6609	Remote Similarity	NPD4694	Approved
0.6609	Remote Similarity	NPD5280	Approved
0.6609	Remote Similarity	NPD5786	Approved
0.6609	Remote Similarity	NPD5279	Phase 3
0.6607	Remote Similarity	NPD5369	Approved
0.6593	Remote Similarity	NPD8328	Phase 3
0.6587	Remote Similarity	NPD6614	Approved
0.6581	Remote Similarity	NPD1695	Approved
0.6581	Remote Similarity	NPD6051	Approved
0.6581	Remote Similarity	NPD5328	Approved
0.6579	Remote Similarity	NPD4197	Approved
0.6579	Remote Similarity	NPD4786	Approved
0.6579	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6573	Remote Similarity	NPD6334	Approved
0.6573	Remote Similarity	NPD6333	Approved
0.6549	Remote Similarity	NPD3667	Approved
0.6535	Remote Similarity	NPD4729	Approved
0.6535	Remote Similarity	NPD4730	Approved
0.6532	Remote Similarity	NPD5091	Approved
0.6529	Remote Similarity	NPD4697	Phase 3
0.6522	Remote Similarity	NPD5329	Approved
0.6518	Remote Similarity	NPD4252	Approved
0.65	Remote Similarity	NPD7748	Approved
0.65	Remote Similarity	NPD5282	Discontinued
0.6484	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.648	Remote Similarity	NPD4754	Approved
0.6475	Remote Similarity	NPD5959	Approved
0.6475	Remote Similarity	NPD7902	Approved
0.6471	Remote Similarity	NPD7515	Phase 2
0.6466	Remote Similarity	NPD4688	Approved
0.6466	Remote Similarity	NPD4690	Approved
0.6466	Remote Similarity	NPD4689	Approved
0.6466	Remote Similarity	NPD4693	Phase 3
0.6466	Remote Similarity	NPD5205	Approved
0.6466	Remote Similarity	NPD6098	Approved
0.6466	Remote Similarity	NPD4138	Approved
0.6454	Remote Similarity	NPD6845	Suspended
0.6452	Remote Similarity	NPD5344	Discontinued

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