NPASS Compound

Structure

NPC470778 OpenBabel07101718332D 37 41 0 0 1 0 0 0 0 0999 V2000 -5.2248 -1.2934 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7508 -2.8480 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0423 2.8454 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3936 -1.0114 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1713 -2.9921 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1415 -2.5261 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8464 1.9156 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0077 0.5335 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2928 0.9011 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0390 -2.2225 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0281 1.8979 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.4322 1.5657 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.6036 0.8658 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2505 1.5834 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.4298 -1.9006 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6138 1.5480 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.9176 -0.1249 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.1921 0.2794 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.8260 0.5512 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.5331 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.4461 -0.6181 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.3845 0.9689 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2527 -1.3530 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4219 0.8835 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.2403 0.9011 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.7666 -0.5569 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.4170 0.3798 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5322 -2.2043 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.4414 2.0094 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8187 -0.4177 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7790 -1.5052 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3173 1.1353 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6937 -1.3060 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6851 -2.1960 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 -1.9655 1.5492 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.6156 -0.9715 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 10 1 0 0 0 0 2 10 1 0 0 0 0 5 34 1 0 0 0 0 6 10 2 0 0 0 0 6 15 1 0 0 0 0 7 12 1 0 0 0 0 7 14 1 0 0 0 0 8 13 1 0 0 0 0 8 24 1 0 0 0 0 9 35 1 0 0 0 0 11 3 1 1 0 0 0 11 12 1 0 0 0 0 11 16 1 0 0 0 0 12 24 1 6 0 0 0 13 16 1 0 0 0 0 13 27 2 0 0 0 0 14 25 1 6 0 0 0 14 36 1 0 0 0 0 15 28 2 0 0 0 0 15 37 1 0 0 0 0 16 29 1 6 0 0 0 17 19 1 0 0 0 0 17 21 1 0 0 0 0 17 30 1 6 0 0 0 18 20 1 0 0 0 0 18 22 1 0 0 0 0 18 37 1 1 0 0 0 19 24 1 6 0 0 0 19 25 1 0 0 0 0 20 25 1 6 0 0 0 20 26 1 0 0 0 0 21 26 1 1 0 0 0 21 31 1 0 0 0 0 22 32 2 0 0 0 0 22 36 1 0 0 0 0 23 33 2 0 0 0 0 23 34 1 0 0 0 0 24 4 1 6 0 0 0 25 9 1 6 0 0 0 26 23 1 6 0 0 0 26 35 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	522.21
Volume:	498.98
LogP:	1.255
LogD:	-0.038
LogS:	-2.362
# Rotatable Bonds:	5
TPSA:	165.89
# H-Bond Aceptor:	11
# H-Bond Donor:	3
# Rings:	5
# Heavy Atoms:	11

MedChem Properties

QED Drug-Likeness Score:	0.253
Synthetic Accessibility Score:	6.643
Fsp3:	0.769
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:	-5.387
MDCK Permeability:	0.00012406830501277
Pgp-inhibitor:	0.845
Pgp-substrate:	0.998
Human Intestinal Absorption (HIA):	0.499
20% Bioavailability (F20%):	0.091
30% Bioavailability (F30%):	0.968

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.126
Plasma Protein Binding (PPB):	43.54277801513672%
Volume Distribution (VD):	0.666
Pgp-substrate:	57.66356658935547%

ADMET: Metabolism

CYP1A2-inhibitor:	0.006
CYP1A2-substrate:	0.867
CYP2C19-inhibitor:	0.02
CYP2C19-substrate:	0.711
CYP2C9-inhibitor:	0.01
CYP2C9-substrate:	0.022
CYP2D6-inhibitor:	0.008
CYP2D6-substrate:	0.11
CYP3A4-inhibitor:	0.234
CYP3A4-substrate:	0.15

ADMET: Excretion

Clearance (CL):	2.338
Half-life (T1/2):	0.74

ADMET: Toxicity

hERG Blockers:	0.066
Human Hepatotoxicity (H-HT):	0.682
Drug-inuced Liver Injury (DILI):	0.918
AMES Toxicity:	0.013
Rat Oral Acute Toxicity:	0.425
Maximum Recommended Daily Dose:	0.954
Skin Sensitization:	0.252
Carcinogencity:	0.089
Eye Corrosion:	0.004
Eye Irritation:	0.015
Respiratory Toxicity:	0.935

Download Data

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

Natural Product: NPC470778

Natural Product ID:	NPC470778
*Common Name:**	Javanicolides E
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	BVRDRHRMMWTKQW-ZBGSOLQASA-N
Standard InCHI:	InChI=1S/C26H34O11/c1-10(2)6-15(28)37-18-20-25-9-35-26(20,23(33)34-5)21(31)17(30)19(25)24(4)8-13(27)16(29)11(3)12(24)7-14(25)36-22(18)32/h6,11-12,14,16-21,29-31H,7-9H2,1-5H3/t11-,12-,14+,16+,17+,18+,19+,20+,21-,24-,25+,26+/m0/s1
SMILES:	COC(=O)[C@]12OC[C@]34[C@H]2[C@@H](OC(=O)C=C(C)C)C(=O)O[C@@H]4C[C@@H]2[C@]([C@H]3[C@H]([C@@H]1O)O)(C)CC(=O)[C@@H]([C@H]2C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2228448
PubChem CID:	46182897
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones [CHEMONTID:0002119] Quassinoids

*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
NPO14948	Brucea javanica	Species	Simaroubaceae	Eukaryota	n.a.	seed	n.a.	DOI[10.1016/0031-9422(96)00258-0]
NPO14948	Brucea javanica	Species	Simaroubaceae	Eukaryota	n.a.	fruit	n.a.	DOI[10.1016/S1383-5769(99)00023-9]
NPO14948	Brucea javanica	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10086989]
NPO14948	Brucea javanica	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1512598]
NPO14948	Brucea javanica	Species	Simaroubaceae	Eukaryota	Seeds	n.a.	n.a.	PMID[15165151]
NPO14948	Brucea javanica	Species	Simaroubaceae	Eukaryota	fruit	Indonesia	n.a.	PMID[17896817]
NPO14948	Brucea javanica	Species	Simaroubaceae	Eukaryota	n.a.	Vietnam	n.a.	PMID[19026551]
NPO14948	Brucea javanica	Species	Simaroubaceae	Eukaryota	seeds	n.a.	n.a.	PMID[20050684]
NPO14948	Brucea javanica	Species	Simaroubaceae	Eukaryota	Seeds	n.a.	n.a.	PMID[22506620]
NPO14948	Brucea javanica	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[6481366]
NPO14948	Brucea javanica	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7561896]
NPO14948	Brucea javanica	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14948	Brucea javanica	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14948	Brucea javanica	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO14948	Brucea javanica	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO14948	Brucea javanica	Species	Simaroubaceae	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
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT786	Organism	Tobacco mosaic virus	Tobacco mosaic virus	Inhibition	=	52.0	%	PMID[463214]

☑ 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 NPC470778 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	301
0.1-0.2	1977
0.2-0.3	5440
0.3-0.4	8479
0.4-0.5	11689
0.5-0.6	7149
0.6-0.7	5142
0.7-0.8	2274
0.8-0.85	173
0.85-0.9	44
0.9-0.95	16
0.95-1	13

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC146432
0.9907	High Similarity	NPC89929
0.9722	High Similarity	NPC213084
0.9722	High Similarity	NPC190185
0.972	High Similarity	NPC94509
0.964	High Similarity	NPC470779
0.963	High Similarity	NPC299849
0.9298	High Similarity	NPC265557
0.9298	High Similarity	NPC91693
0.9298	High Similarity	NPC105926
0.9298	High Similarity	NPC18945
0.9217	High Similarity	NPC476729
0.9211	High Similarity	NPC312833
0.913	High Similarity	NPC67251
0.9052	High Similarity	NPC24651
0.886	High Similarity	NPC17772
0.8772	High Similarity	NPC473590
0.8739	High Similarity	NPC476008
0.8729	High Similarity	NPC470922
0.8696	High Similarity	NPC470776
0.8684	High Similarity	NPC16081
0.8684	High Similarity	NPC251236
0.8684	High Similarity	NPC96312
0.8684	High Similarity	NPC40632
0.8684	High Similarity	NPC328374
0.8684	High Similarity	NPC173686
0.8655	High Similarity	NPC477745
0.8621	High Similarity	NPC470777
0.8609	High Similarity	NPC470854
0.8609	High Similarity	NPC287343
0.8609	High Similarity	NPC97908
0.8609	High Similarity	NPC474654
0.8609	High Similarity	NPC122033
0.8596	High Similarity	NPC143268
0.8596	High Similarity	NPC268238
0.8596	High Similarity	NPC45218
0.8596	High Similarity	NPC473798
0.8596	High Similarity	NPC323821
0.8548	High Similarity	NPC262813
0.8547	High Similarity	NPC109607
0.8547	High Similarity	NPC107338
0.8534	High Similarity	NPC251310
0.8534	High Similarity	NPC297179
0.8522	High Similarity	NPC474734
0.8509	High Similarity	NPC49451
0.8509	High Similarity	NPC477126
0.848	Intermediate Similarity	NPC251998
0.848	Intermediate Similarity	NPC471089
0.848	Intermediate Similarity	NPC190065
0.848	Intermediate Similarity	NPC141215
0.8462	Intermediate Similarity	NPC476529
0.8462	Intermediate Similarity	NPC475775
0.8448	Intermediate Similarity	NPC470775
0.8448	Intermediate Similarity	NPC176513
0.8413	Intermediate Similarity	NPC596
0.8413	Intermediate Similarity	NPC140045
0.8413	Intermediate Similarity	NPC295885
0.8407	Intermediate Similarity	NPC100908
0.8393	Intermediate Similarity	NPC289702
0.8393	Intermediate Similarity	NPC208461
0.839	Intermediate Similarity	NPC112038
0.8387	Intermediate Similarity	NPC168879
0.8376	Intermediate Similarity	NPC204552
0.8376	Intermediate Similarity	NPC188667
0.8362	Intermediate Similarity	NPC134869
0.8362	Intermediate Similarity	NPC152199
0.8362	Intermediate Similarity	NPC235539
0.8348	Intermediate Similarity	NPC7921
0.8348	Intermediate Similarity	NPC208998
0.8333	Intermediate Similarity	NPC157476
0.8319	Intermediate Similarity	NPC102822
0.8319	Intermediate Similarity	NPC477046
0.8306	Intermediate Similarity	NPC478154
0.8306	Intermediate Similarity	NPC102316
0.8293	Intermediate Similarity	NPC476851
0.8279	Intermediate Similarity	NPC470780
0.8276	Intermediate Similarity	NPC18547
0.8276	Intermediate Similarity	NPC474906
0.824	Intermediate Similarity	NPC478151
0.8235	Intermediate Similarity	NPC251226
0.8226	Intermediate Similarity	NPC301639
0.8226	Intermediate Similarity	NPC172374
0.8226	Intermediate Similarity	NPC264566
0.8226	Intermediate Similarity	NPC475167
0.8226	Intermediate Similarity	NPC173435
0.8226	Intermediate Similarity	NPC262796
0.8226	Intermediate Similarity	NPC45346
0.8226	Intermediate Similarity	NPC478064
0.8226	Intermediate Similarity	NPC25998
0.8226	Intermediate Similarity	NPC478155
0.8226	Intermediate Similarity	NPC476074
0.8226	Intermediate Similarity	NPC476852
0.8226	Intermediate Similarity	NPC329993
0.8226	Intermediate Similarity	NPC475377
0.8226	Intermediate Similarity	NPC134914
0.8226	Intermediate Similarity	NPC478065
0.8211	Intermediate Similarity	NPC476859
0.8205	Intermediate Similarity	NPC474046
0.8205	Intermediate Similarity	NPC470628
0.8205	Intermediate Similarity	NPC259306
0.8205	Intermediate Similarity	NPC207217
0.8197	Intermediate Similarity	NPC181999
0.8174	Intermediate Similarity	NPC146945
0.8174	Intermediate Similarity	NPC171888
0.8167	Intermediate Similarity	NPC159456
0.8167	Intermediate Similarity	NPC4021
0.816	Intermediate Similarity	NPC478152
0.816	Intermediate Similarity	NPC478150
0.816	Intermediate Similarity	NPC478153
0.8151	Intermediate Similarity	NPC473839
0.8151	Intermediate Similarity	NPC211093
0.8151	Intermediate Similarity	NPC469488
0.8151	Intermediate Similarity	NPC473636
0.8151	Intermediate Similarity	NPC230513
0.8151	Intermediate Similarity	NPC77689
0.8145	Intermediate Similarity	NPC477196
0.8145	Intermediate Similarity	NPC231529
0.8145	Intermediate Similarity	NPC476854
0.8142	Intermediate Similarity	NPC166993
0.8136	Intermediate Similarity	NPC58662
0.8136	Intermediate Similarity	NPC55296
0.8136	Intermediate Similarity	NPC134430
0.8136	Intermediate Similarity	NPC473968
0.8136	Intermediate Similarity	NPC475809
0.812	Intermediate Similarity	NPC469877
0.812	Intermediate Similarity	NPC470919
0.8103	Intermediate Similarity	NPC269530
0.8103	Intermediate Similarity	NPC11252
0.8103	Intermediate Similarity	NPC289312
0.8103	Intermediate Similarity	NPC474516
0.8099	Intermediate Similarity	NPC269642
0.8083	Intermediate Similarity	NPC268530
0.8083	Intermediate Similarity	NPC154491
0.8083	Intermediate Similarity	NPC472004
0.8083	Intermediate Similarity	NPC478051
0.808	Intermediate Similarity	NPC476855
0.808	Intermediate Similarity	NPC477197
0.807	Intermediate Similarity	NPC293850
0.807	Intermediate Similarity	NPC273155
0.8065	Intermediate Similarity	NPC114306
0.8065	Intermediate Similarity	NPC475281
0.8065	Intermediate Similarity	NPC477075
0.8065	Intermediate Similarity	NPC188291
0.8065	Intermediate Similarity	NPC477078
0.8065	Intermediate Similarity	NPC475636
0.8065	Intermediate Similarity	NPC477490
0.8065	Intermediate Similarity	NPC477191
0.8065	Intermediate Similarity	NPC329923
0.8065	Intermediate Similarity	NPC477192
0.8065	Intermediate Similarity	NPC477193
0.8065	Intermediate Similarity	NPC295220
0.8065	Intermediate Similarity	NPC477194
0.8053	Intermediate Similarity	NPC138908
0.8053	Intermediate Similarity	NPC200957
0.8049	Intermediate Similarity	NPC87662
0.8049	Intermediate Similarity	NPC293112
0.8049	Intermediate Similarity	NPC285091
0.8049	Intermediate Similarity	NPC473635
0.8047	Intermediate Similarity	NPC243014
0.8034	Intermediate Similarity	NPC51978
0.8034	Intermediate Similarity	NPC198539
0.8033	Intermediate Similarity	NPC11895
0.8017	Intermediate Similarity	NPC469655
0.8017	Intermediate Similarity	NPC474846
0.8017	Intermediate Similarity	NPC469656
0.8017	Intermediate Similarity	NPC201992
0.8016	Intermediate Similarity	NPC254614
0.8016	Intermediate Similarity	NPC100390
0.8016	Intermediate Similarity	NPC476776
0.8016	Intermediate Similarity	NPC477195
0.8	Intermediate Similarity	NPC477076
0.8	Intermediate Similarity	NPC470913
0.8	Intermediate Similarity	NPC472267
0.8	Intermediate Similarity	NPC269484
0.8	Intermediate Similarity	NPC477077
0.8	Intermediate Similarity	NPC42673
0.8	Intermediate Similarity	NPC88311
0.8	Intermediate Similarity	NPC42662
0.8	Intermediate Similarity	NPC474243
0.8	Intermediate Similarity	NPC470912
0.8	Intermediate Similarity	NPC107536
0.8	Intermediate Similarity	NPC470518
0.8	Intermediate Similarity	NPC273878
0.8	Intermediate Similarity	NPC280029
0.8	Intermediate Similarity	NPC11577
0.8	Intermediate Similarity	NPC244296
0.8	Intermediate Similarity	NPC97918
0.8	Intermediate Similarity	NPC477079
0.8	Intermediate Similarity	NPC252657
0.8	Intermediate Similarity	NPC9470
0.8	Intermediate Similarity	NPC141600
0.8	Intermediate Similarity	NPC309096
0.8	Intermediate Similarity	NPC252289
0.8	Intermediate Similarity	NPC115656
0.8	Intermediate Similarity	NPC1314
0.8	Intermediate Similarity	NPC82380
0.8	Intermediate Similarity	NPC305793
0.8	Intermediate Similarity	NPC54614
0.7984	Intermediate Similarity	NPC117702
0.7984	Intermediate Similarity	NPC469757

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 NPC470778 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	306
0.1-0.2	2311
0.2-0.3	3809
0.3-0.4	1675
0.4-0.5	599
0.5-0.6	263
0.6-0.7	130
0.7-0.8	55
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8393	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7886	Intermediate Similarity	NPD8328	Phase 3
0.7857	Intermediate Similarity	NPD7319	Approved
0.7724	Intermediate Similarity	NPD6921	Approved
0.7642	Intermediate Similarity	NPD6319	Approved
0.7619	Intermediate Similarity	NPD7507	Approved
0.75	Intermediate Similarity	NPD7736	Approved
0.7402	Intermediate Similarity	NPD7492	Approved
0.7398	Intermediate Similarity	NPD7115	Discovery
0.7398	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7395	Intermediate Similarity	NPD6373	Approved
0.7395	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7395	Intermediate Similarity	NPD6372	Approved
0.736	Intermediate Similarity	NPD6054	Approved
0.736	Intermediate Similarity	NPD6059	Approved
0.7355	Intermediate Similarity	NPD8297	Approved
0.7344	Intermediate Similarity	NPD6616	Approved
0.7333	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7311	Intermediate Similarity	NPD6686	Approved
0.7288	Intermediate Similarity	NPD6675	Approved
0.7288	Intermediate Similarity	NPD7128	Approved
0.7288	Intermediate Similarity	NPD5739	Approved
0.7288	Intermediate Similarity	NPD6402	Approved
0.7287	Intermediate Similarity	NPD8293	Discontinued
0.7287	Intermediate Similarity	NPD7078	Approved
0.728	Intermediate Similarity	NPD7516	Approved
0.7273	Intermediate Similarity	NPD6650	Approved
0.7273	Intermediate Similarity	NPD6649	Approved
0.7244	Intermediate Similarity	NPD6370	Approved
0.7217	Intermediate Similarity	NPD4225	Approved
0.7217	Intermediate Similarity	NPD7638	Approved
0.72	Intermediate Similarity	NPD7327	Approved
0.72	Intermediate Similarity	NPD7328	Approved
0.7167	Intermediate Similarity	NPD6899	Approved
0.7167	Intermediate Similarity	NPD7320	Approved
0.7167	Intermediate Similarity	NPD6881	Approved
0.7165	Intermediate Similarity	NPD6016	Approved
0.7165	Intermediate Similarity	NPD6015	Approved
0.7155	Intermediate Similarity	NPD7640	Approved
0.7155	Intermediate Similarity	NPD7639	Approved
0.7154	Intermediate Similarity	NPD8133	Approved
0.7154	Intermediate Similarity	NPD4632	Approved
0.7109	Intermediate Similarity	NPD5988	Approved
0.7083	Intermediate Similarity	NPD5701	Approved
0.7083	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD5697	Approved
0.7073	Intermediate Similarity	NPD6882	Approved
0.7049	Intermediate Similarity	NPD7290	Approved
0.7049	Intermediate Similarity	NPD7102	Approved
0.7049	Intermediate Similarity	NPD6883	Approved
0.7031	Intermediate Similarity	NPD8515	Approved
0.7031	Intermediate Similarity	NPD8379	Approved
0.7031	Intermediate Similarity	NPD8378	Approved
0.7031	Intermediate Similarity	NPD8516	Approved
0.7031	Intermediate Similarity	NPD8296	Approved
0.7031	Intermediate Similarity	NPD8517	Approved
0.7031	Intermediate Similarity	NPD8380	Approved
0.7031	Intermediate Similarity	NPD8335	Approved
0.7031	Intermediate Similarity	NPD8513	Phase 3
0.6992	Remote Similarity	NPD6617	Approved
0.6992	Remote Similarity	NPD6847	Approved
0.6992	Remote Similarity	NPD6869	Approved
0.6992	Remote Similarity	NPD8130	Phase 1
0.6984	Remote Similarity	NPD6009	Approved
0.6967	Remote Similarity	NPD6014	Approved
0.6967	Remote Similarity	NPD6013	Approved
0.6967	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6967	Remote Similarity	NPD6012	Approved
0.6953	Remote Similarity	NPD8377	Approved
0.6953	Remote Similarity	NPD8294	Approved
0.6923	Remote Similarity	NPD7604	Phase 2
0.6911	Remote Similarity	NPD4634	Approved
0.6899	Remote Similarity	NPD8033	Approved
0.6899	Remote Similarity	NPD5983	Phase 2
0.6885	Remote Similarity	NPD6011	Approved
0.6855	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD6033	Approved
0.6838	Remote Similarity	NPD7902	Approved
0.6818	Remote Similarity	NPD6336	Discontinued
0.6807	Remote Similarity	NPD1700	Approved
0.6803	Remote Similarity	NPD6412	Phase 2
0.6803	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6724	Remote Similarity	NPD7748	Approved
0.6721	Remote Similarity	NPD6008	Approved
0.672	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6696	Remote Similarity	NPD7515	Phase 2
0.6695	Remote Similarity	NPD6084	Phase 2
0.6695	Remote Similarity	NPD4755	Approved
0.6695	Remote Similarity	NPD6083	Phase 2
0.6691	Remote Similarity	NPD7260	Phase 2
0.6642	Remote Similarity	NPD8074	Phase 3
0.6641	Remote Similarity	NPD6274	Approved
0.6641	Remote Similarity	NPD7503	Approved
0.664	Remote Similarity	NPD6371	Approved
0.6639	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6639	Remote Similarity	NPD5696	Approved
0.6615	Remote Similarity	NPD7101	Approved
0.6615	Remote Similarity	NPD7100	Approved
0.6612	Remote Similarity	NPD5211	Phase 2
0.6612	Remote Similarity	NPD7632	Discontinued
0.6609	Remote Similarity	NPD6698	Approved
0.6609	Remote Similarity	NPD46	Approved
0.6583	Remote Similarity	NPD5285	Approved
0.6583	Remote Similarity	NPD4700	Approved
0.6583	Remote Similarity	NPD5286	Approved
0.6583	Remote Similarity	NPD4696	Approved
0.6581	Remote Similarity	NPD7900	Approved
0.6581	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD8035	Phase 2
0.6552	Remote Similarity	NPD8034	Phase 2
0.6538	Remote Similarity	NPD6335	Approved
0.6529	Remote Similarity	NPD5344	Discontinued
0.6522	Remote Similarity	NPD6845	Suspended
0.6515	Remote Similarity	NPD6908	Approved
0.6515	Remote Similarity	NPD6909	Approved
0.6504	Remote Similarity	NPD5141	Approved
0.6475	Remote Similarity	NPD4633	Approved
0.6475	Remote Similarity	NPD5225	Approved
0.6475	Remote Similarity	NPD5226	Approved
0.6475	Remote Similarity	NPD5224	Approved
0.6471	Remote Similarity	NPD4697	Phase 3
0.6462	Remote Similarity	NPD6317	Approved
0.6452	Remote Similarity	NPD4767	Approved
0.6452	Remote Similarity	NPD4768	Approved
0.6441	Remote Similarity	NPD5282	Discontinued
0.6423	Remote Similarity	NPD5174	Approved
0.6423	Remote Similarity	NPD5175	Approved
0.6412	Remote Similarity	NPD6313	Approved
0.6412	Remote Similarity	NPD6314	Approved
0.6406	Remote Similarity	NPD6053	Discontinued
0.6393	Remote Similarity	NPD5223	Approved
0.6391	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6387	Remote Similarity	NPD5695	Phase 3
0.6387	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6385	Remote Similarity	NPD6868	Approved
0.6379	Remote Similarity	NPD5328	Approved
0.6356	Remote Similarity	NPD6399	Phase 3
0.6349	Remote Similarity	NPD4730	Approved
0.6349	Remote Similarity	NPD4729	Approved
0.6348	Remote Similarity	NPD3573	Approved
0.6333	Remote Similarity	NPD5221	Approved
0.6333	Remote Similarity	NPD5222	Approved
0.6333	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6293	Remote Similarity	NPD6672	Approved
0.6293	Remote Similarity	NPD5737	Approved
0.629	Remote Similarity	NPD4754	Approved
0.6281	Remote Similarity	NPD5173	Approved
0.6273	Remote Similarity	NPD6118	Approved
0.6273	Remote Similarity	NPD6114	Approved
0.6273	Remote Similarity	NPD6697	Approved
0.6273	Remote Similarity	NPD6115	Approved
0.6271	Remote Similarity	NPD6411	Approved
0.6271	Remote Similarity	NPD5693	Phase 1
0.6271	Remote Similarity	NPD7983	Approved
0.6271	Remote Similarity	NPD6079	Approved
0.6268	Remote Similarity	NPD8387	Clinical (unspecified phase)
0.6261	Remote Similarity	NPD3618	Phase 1
0.625	Remote Similarity	NPD5250	Approved
0.625	Remote Similarity	NPD5248	Approved
0.625	Remote Similarity	NPD5247	Approved
0.625	Remote Similarity	NPD5249	Phase 3
0.625	Remote Similarity	NPD5251	Approved
0.622	Remote Similarity	NPD5128	Approved
0.6218	Remote Similarity	NPD5778	Approved
0.6218	Remote Similarity	NPD5779	Approved
0.6197	Remote Similarity	NPD8415	Approved
0.6196	Remote Similarity	NPD7799	Discontinued
0.6182	Remote Similarity	NPD6116	Phase 1
0.6179	Remote Similarity	NPD6648	Approved
0.6174	Remote Similarity	NPD1694	Approved
0.6154	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6147	Remote Similarity	NPD3703	Phase 2
0.6143	Remote Similarity	NPD5956	Approved
0.6131	Remote Similarity	NPD8407	Phase 2
0.6116	Remote Similarity	NPD5210	Approved
0.6116	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6116	Remote Similarity	NPD4629	Approved
0.6102	Remote Similarity	NPD6904	Approved
0.6102	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6102	Remote Similarity	NPD6080	Approved
0.6102	Remote Similarity	NPD4753	Phase 2
0.6102	Remote Similarity	NPD6101	Approved
0.6102	Remote Similarity	NPD6673	Approved
0.6093	Remote Similarity	NPD7236	Approved
0.6091	Remote Similarity	NPD6117	Approved
0.6083	Remote Similarity	NPD4202	Approved
0.6077	Remote Similarity	NPD5216	Approved
0.6077	Remote Similarity	NPD5215	Approved
0.6077	Remote Similarity	NPD5217	Approved
0.6069	Remote Similarity	NPD6333	Approved
0.6069	Remote Similarity	NPD6334	Approved
0.6059	Remote Similarity	NPD8434	Phase 2
0.6058	Remote Similarity	NPD6067	Discontinued
0.6053	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6048	Remote Similarity	NPD8368	Discontinued
0.6	Remote Similarity	NPD7239	Suspended
0.6	Remote Similarity	NPD5135	Approved
0.6	Remote Similarity	NPD7637	Suspended

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