NPASS Compound

Structure

NPC198205 OpenBabel07101719252D 37 41 0 0 1 0 0 0 0 0999 V2000 4.1123 1.1828 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5663 -3.9874 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 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 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9227 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5139 0.6235 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4242 -2.6195 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4888 0.4010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3438 -3.0125 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4888 -1.4010 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5139 -1.6235 0.0000 C 0 0 2 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 -2.5981 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0017 -2.2594 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 -0.0000 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 -2.5000 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 1.7321 -1.0000 0.0000 C 0 0 2 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 -2.5981 -1.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.9977 -2.3491 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2954 -0.1738 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 15 1 0 0 0 0 2 16 1 0 0 0 0 3 17 1 0 0 0 0 4 18 1 0 0 0 0 5 28 1 0 0 0 0 6 28 1 0 0 0 0 7 31 1 0 0 0 0 8 9 2 0 0 0 0 8 10 1 0 0 0 0 9 11 1 0 0 0 0 10 19 2 0 0 0 0 11 23 2 0 0 0 0 12 15 1 0 0 0 0 13 15 2 0 0 0 0 13 22 1 0 0 0 0 14 16 2 0 0 0 0 14 21 1 0 0 0 0 16 24 1 0 0 0 0 17 26 1 0 0 0 0 17 29 1 6 0 0 0 18 32 2 0 0 0 0 18 37 1 0 0 0 0 19 23 1 0 0 0 0 19 27 1 0 0 0 0 20 12 1 1 0 0 0 20 21 1 0 0 0 0 20 24 1 0 0 0 0 21 29 1 1 0 0 0 22 25 1 0 0 0 0 22 29 1 6 0 0 0 23 31 1 0 0 0 0 24 33 2 0 0 0 0 25 28 1 0 0 0 0 25 30 1 1 0 0 0 26 30 1 1 0 0 0 26 36 1 0 0 0 0 27 34 2 0 0 0 0 27 36 1 0 0 0 0 28 30 1 0 0 0 0 29 35 1 6 0 0 0 30 37 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	507.26
Volume:	527.3
LogP:	4.917
LogD:	3.114
LogS:	-4.94
# Rotatable Bonds:	6
TPSA:	101.93
# H-Bond Aceptor:	7
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.462
Synthetic Accessibility Score:	4.918
Fsp3:	0.567
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:	-5.128
MDCK Permeability:	2.7473066438687965e-05
Pgp-inhibitor:	0.997
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.094
20% Bioavailability (F20%):	0.032
30% Bioavailability (F30%):	0.866

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.096
Plasma Protein Binding (PPB):	77.64827728271484%
Volume Distribution (VD):	1.709
Pgp-substrate:	18.5292911529541%

ADMET: Metabolism

CYP1A2-inhibitor:	0.263
CYP1A2-substrate:	0.104
CYP2C19-inhibitor:	0.859
CYP2C19-substrate:	0.448
CYP2C9-inhibitor:	0.925
CYP2C9-substrate:	0.077
CYP2D6-inhibitor:	0.485
CYP2D6-substrate:	0.173
CYP3A4-inhibitor:	0.909
CYP3A4-substrate:	0.253

ADMET: Excretion

Clearance (CL):	6.803
Half-life (T1/2):	0.3

ADMET: Toxicity

hERG Blockers:	0.891
Human Hepatotoxicity (H-HT):	0.99
Drug-inuced Liver Injury (DILI):	0.58
AMES Toxicity:	0.036
Rat Oral Acute Toxicity:	0.72
Maximum Recommended Daily Dose:	0.89
Skin Sensitization:	0.323
Carcinogencity:	0.014
Eye Corrosion:	0.003
Eye Irritation:	0.01
Respiratory Toxicity:	0.956

Download Data

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

Natural Product: NPC198205

Natural Product ID:	NPC198205
*Common Name:**	RVVIYIWBNNSAIQ-UFOUZLIMSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	RVVIYIWBNNSAIQ-UFOUZLIMSA-N
Standard InCHI:	InChI=1S/C30H37NO6/c1-15-12-20-21(14-16(2)24(20)33)29(35)17(3)26(36-27(34)19-10-8-9-11-23(19)31-7)30(37-18(4)32)25(22(29)13-15)28(30,5)6/h8-11,13-14,17,20-22,25-26,31,35H,12H2,1-7H3/t17-,20-,21-,22+,25-,26-,29+,30-/m1/s1
SMILES:	CNc1ccccc1C(=O)O[C@@H]1[C@@H](C)[C@]2(O)[C@@H]3C=C(C(=O)[C@@H]3CC(=C[C@H]2[C@H]2[C@]1(OC(=O)C)C2(C)C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL503125
PubChem CID:	10907317
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0002875] Tigliane and ingenane 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
NPO25366	Sapium indicum	Species	Euphorbiaceae	Eukaryota	Fruits	n.a.	n.a.	PMID[12713411]
NPO25366	Sapium indicum	Species	Euphorbiaceae	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
MIC	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT88	Organism	Mycobacterium tuberculosis	Mycobacterium tuberculosis	MIC	=	200.0	ug.mL-1	PMID[541490]

☑ 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 NPC198205 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	250
0.1-0.2	1125
0.2-0.3	2879
0.3-0.4	7964
0.4-0.5	15331
0.5-0.6	13447
0.6-0.7	1613
0.7-0.8	68
0.8-0.85	11
0.85-0.9	0
0.9-0.95	0
0.95-1	9

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC21483
0.9885	High Similarity	NPC198390
0.9829	High Similarity	NPC311054
0.9829	High Similarity	NPC112752
0.9773	High Similarity	NPC107828
0.9773	High Similarity	NPC90358
0.9663	High Similarity	NPC136573
0.9663	High Similarity	NPC176371
0.877	High Similarity	NPC475223
0.8723	High Similarity	NPC475448
0.8723	High Similarity	NPC246983
0.8105	Intermediate Similarity	NPC476205
0.8105	Intermediate Similarity	NPC476257
0.8105	Intermediate Similarity	NPC476207
0.8105	Intermediate Similarity	NPC476129
0.8105	Intermediate Similarity	NPC259791
0.8105	Intermediate Similarity	NPC476206
0.8105	Intermediate Similarity	NPC476256
0.8105	Intermediate Similarity	NPC476212
0.8063	Intermediate Similarity	NPC476218
0.8063	Intermediate Similarity	NPC108804
0.7756	Intermediate Similarity	NPC473837
0.7614	Intermediate Similarity	NPC132652
0.7596	Intermediate Similarity	NPC223590
0.7444	Intermediate Similarity	NPC22571
0.7444	Intermediate Similarity	NPC469648
0.7444	Intermediate Similarity	NPC138641
0.7444	Intermediate Similarity	NPC145649
0.7444	Intermediate Similarity	NPC233581
0.7444	Intermediate Similarity	NPC283875
0.7444	Intermediate Similarity	NPC469647
0.7393	Intermediate Similarity	NPC140311
0.7371	Intermediate Similarity	NPC473667
0.7333	Intermediate Similarity	NPC471016
0.733	Intermediate Similarity	NPC183540
0.733	Intermediate Similarity	NPC140021
0.7327	Intermediate Similarity	NPC35390
0.7327	Intermediate Similarity	NPC470631
0.7327	Intermediate Similarity	NPC473781
0.7326	Intermediate Similarity	NPC470971
0.7326	Intermediate Similarity	NPC173295
0.7324	Intermediate Similarity	NPC106593
0.7322	Intermediate Similarity	NPC11410
0.7294	Intermediate Similarity	NPC475316
0.7294	Intermediate Similarity	NPC473486
0.7293	Intermediate Similarity	NPC472398
0.729	Intermediate Similarity	NPC250807
0.729	Intermediate Similarity	NPC57797
0.729	Intermediate Similarity	NPC76565
0.7286	Intermediate Similarity	NPC470306
0.7264	Intermediate Similarity	NPC301368
0.7264	Intermediate Similarity	NPC84815
0.7256	Intermediate Similarity	NPC475137
0.7256	Intermediate Similarity	NPC475498
0.7256	Intermediate Similarity	NPC473850
0.7251	Intermediate Similarity	NPC475408
0.7251	Intermediate Similarity	NPC471014
0.7219	Intermediate Similarity	NPC253738
0.7217	Intermediate Similarity	NPC62367
0.7213	Intermediate Similarity	NPC114808
0.7204	Intermediate Similarity	NPC477909
0.7204	Intermediate Similarity	NPC42678
0.7204	Intermediate Similarity	NPC477907
0.7189	Intermediate Similarity	NPC328186
0.7189	Intermediate Similarity	NPC475600
0.7189	Intermediate Similarity	NPC122968
0.7189	Intermediate Similarity	NPC476110
0.7189	Intermediate Similarity	NPC146824
0.7189	Intermediate Similarity	NPC477787
0.7189	Intermediate Similarity	NPC87152
0.7189	Intermediate Similarity	NPC475631
0.7189	Intermediate Similarity	NPC475601
0.7189	Intermediate Similarity	NPC228377
0.7183	Intermediate Similarity	NPC216428
0.717	Intermediate Similarity	NPC6981
0.7168	Intermediate Similarity	NPC253476
0.7163	Intermediate Similarity	NPC304179
0.7163	Intermediate Similarity	NPC127026
0.7163	Intermediate Similarity	NPC48042
0.7163	Intermediate Similarity	NPC127720
0.7163	Intermediate Similarity	NPC472550
0.7156	Intermediate Similarity	NPC4421
0.7156	Intermediate Similarity	NPC475362
0.7156	Intermediate Similarity	NPC471190
0.7156	Intermediate Similarity	NPC470486
0.7156	Intermediate Similarity	NPC471977
0.7156	Intermediate Similarity	NPC475644
0.7149	Intermediate Similarity	NPC35208
0.7149	Intermediate Similarity	NPC475426
0.7143	Intermediate Similarity	NPC472553
0.7136	Intermediate Similarity	NPC144779
0.7136	Intermediate Similarity	NPC294579
0.713	Intermediate Similarity	NPC471980
0.7129	Intermediate Similarity	NPC36607
0.7121	Intermediate Similarity	NPC477998
0.7119	Intermediate Similarity	NPC90614
0.7119	Intermediate Similarity	NPC100913
0.7119	Intermediate Similarity	NPC97667
0.7119	Intermediate Similarity	NPC171207
0.7119	Intermediate Similarity	NPC275592
0.7116	Intermediate Similarity	NPC477912
0.711	Intermediate Similarity	NPC14116
0.711	Intermediate Similarity	NPC285411
0.7105	Intermediate Similarity	NPC30171
0.7097	Intermediate Similarity	NPC328154
0.7097	Intermediate Similarity	NPC477902
0.7091	Intermediate Similarity	NPC292416
0.7091	Intermediate Similarity	NPC475596
0.7091	Intermediate Similarity	NPC96801
0.7091	Intermediate Similarity	NPC316841
0.7091	Intermediate Similarity	NPC150698
0.7091	Intermediate Similarity	NPC475303
0.7091	Intermediate Similarity	NPC473689
0.7085	Intermediate Similarity	NPC471623
0.7083	Intermediate Similarity	NPC477788
0.7079	Intermediate Similarity	NPC291599
0.7079	Intermediate Similarity	NPC41481
0.7079	Intermediate Similarity	NPC97947
0.7079	Intermediate Similarity	NPC87448
0.7079	Intermediate Similarity	NPC118080
0.7079	Intermediate Similarity	NPC16912
0.7079	Intermediate Similarity	NPC27377
0.7079	Intermediate Similarity	NPC472576
0.7078	Intermediate Similarity	NPC134384
0.7078	Intermediate Similarity	NPC311196
0.7075	Intermediate Similarity	NPC264674
0.7075	Intermediate Similarity	NPC228331
0.7064	Intermediate Similarity	NPC473506
0.7059	Intermediate Similarity	NPC319880
0.7059	Intermediate Similarity	NPC320324
0.7059	Intermediate Similarity	NPC469748
0.7059	Intermediate Similarity	NPC244839
0.7059	Intermediate Similarity	NPC30456
0.7056	Intermediate Similarity	NPC158020
0.7056	Intermediate Similarity	NPC212768
0.7056	Intermediate Similarity	NPC6576
0.7056	Intermediate Similarity	NPC473089
0.7056	Intermediate Similarity	NPC473115
0.7056	Intermediate Similarity	NPC49184
0.7056	Intermediate Similarity	NPC75600
0.7056	Intermediate Similarity	NPC34943
0.705	Intermediate Similarity	NPC275170
0.705	Intermediate Similarity	NPC473300
0.705	Intermediate Similarity	NPC453583
0.705	Intermediate Similarity	NPC206211
0.705	Intermediate Similarity	NPC306001
0.705	Intermediate Similarity	NPC471754
0.705	Intermediate Similarity	NPC475336
0.705	Intermediate Similarity	NPC473400
0.705	Intermediate Similarity	NPC471629
0.705	Intermediate Similarity	NPC317882
0.705	Intermediate Similarity	NPC324251
0.7048	Intermediate Similarity	NPC25961
0.7045	Intermediate Similarity	NPC472551
0.7045	Intermediate Similarity	NPC472545
0.7042	Intermediate Similarity	NPC477910
0.7035	Intermediate Similarity	NPC316405
0.7033	Intermediate Similarity	NPC63041
0.7032	Intermediate Similarity	NPC124029
0.7032	Intermediate Similarity	NPC211920
0.7029	Intermediate Similarity	NPC474608
0.7027	Intermediate Similarity	NPC237702
0.7022	Intermediate Similarity	NPC472547
0.7022	Intermediate Similarity	NPC253482
0.7017	Intermediate Similarity	NPC125882
0.7017	Intermediate Similarity	NPC311825
0.7017	Intermediate Similarity	NPC92867
0.7017	Intermediate Similarity	NPC473541
0.7015	Intermediate Similarity	NPC33372
0.7015	Intermediate Similarity	NPC67246
0.7006	Intermediate Similarity	NPC39549
0.7005	Intermediate Similarity	NPC97584
0.7	Intermediate Similarity	NPC477894
0.7	Intermediate Similarity	NPC95449
0.7	Intermediate Similarity	NPC163087
0.6996	Remote Similarity	NPC170751
0.6996	Remote Similarity	NPC327769
0.6996	Remote Similarity	NPC475406
0.6995	Remote Similarity	NPC319128
0.6989	Remote Similarity	NPC66761
0.6989	Remote Similarity	NPC195647
0.6989	Remote Similarity	NPC251139
0.6989	Remote Similarity	NPC472577
0.6989	Remote Similarity	NPC17877
0.6989	Remote Similarity	NPC291638
0.6986	Remote Similarity	NPC148860
0.6978	Remote Similarity	NPC94602
0.6978	Remote Similarity	NPC473602
0.6978	Remote Similarity	NPC209592
0.6978	Remote Similarity	NPC48599
0.6978	Remote Similarity	NPC20255
0.6978	Remote Similarity	NPC478263
0.6978	Remote Similarity	NPC240115
0.6977	Remote Similarity	NPC122235
0.6966	Remote Similarity	NPC9905
0.6965	Remote Similarity	NPC25401
0.6964	Remote Similarity	NPC327904
0.6964	Remote Similarity	NPC38959
0.6961	Remote Similarity	NPC476974
0.6961	Remote Similarity	NPC188865

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 NPC198205 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	169
0.1-0.2	543
0.2-0.3	817
0.3-0.4	1664
0.4-0.5	3637
0.5-0.6	2092
0.6-0.7	225
0.7-0.8	3
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
0.7374	Intermediate Similarity	NPD2737	Clinical (unspecified phase)
0.7268	Intermediate Similarity	NPD2836	Approved
0.7157	Intermediate Similarity	NPD8424	Clinical (unspecified phase)
0.7085	Intermediate Similarity	NPD8360	Approved
0.7085	Intermediate Similarity	NPD8435	Approved
0.7085	Intermediate Similarity	NPD8361	Approved
0.7081	Intermediate Similarity	NPD2672	Discontinued
0.7039	Intermediate Similarity	NPD1625	Approved
0.7033	Intermediate Similarity	NPD7528	Approved
0.7033	Intermediate Similarity	NPD4888	Discontinued
0.6961	Remote Similarity	NPD7238	Clinical (unspecified phase)
0.6915	Remote Similarity	NPD5928	Phase 1
0.691	Remote Similarity	NPD1626	Approved
0.6884	Remote Similarity	NPD8407	Phase 2
0.6882	Remote Similarity	NPD5086	Approved
0.6878	Remote Similarity	NPD8485	Approved
0.6845	Remote Similarity	NPD4668	Phase 2
0.6842	Remote Similarity	NPD7597	Clinical (unspecified phase)
0.6837	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD5466	Approved
0.6818	Remote Similarity	NPD8368	Discontinued
0.6784	Remote Similarity	NPD8658	Clinical (unspecified phase)
0.6784	Remote Similarity	NPD7962	Phase 2
0.6779	Remote Similarity	NPD8486	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD7606	Phase 3
0.6771	Remote Similarity	NPD5430	Discontinued
0.6769	Remote Similarity	NPD5997	Discontinued
0.6735	Remote Similarity	NPD5919	Clinical (unspecified phase)
0.6731	Remote Similarity	NPD6874	Approved
0.6703	Remote Similarity	NPD6414	Clinical (unspecified phase)
0.6703	Remote Similarity	NPD1189	Approved
0.6685	Remote Similarity	NPD7295	Approved
0.6667	Remote Similarity	NPD7880	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2670	Approved
0.6615	Remote Similarity	NPD2821	Approved
0.6613	Remote Similarity	NPD1802	Approved
0.6613	Remote Similarity	NPD7478	Approved
0.6613	Remote Similarity	NPD1801	Approved
0.6606	Remote Similarity	NPD5433	Clinical (unspecified phase)
0.6603	Remote Similarity	NPD5196	Approved
0.6603	Remote Similarity	NPD5197	Approved
0.6603	Remote Similarity	NPD5194	Approved
0.6602	Remote Similarity	NPD5937	Approved
0.6541	Remote Similarity	NPD7487	Discontinued
0.6538	Remote Similarity	NPD3170	Approved
0.6526	Remote Similarity	NPD7497	Discontinued
0.6522	Remote Similarity	NPD7569	Approved
0.6522	Remote Similarity	NPD8146	Phase 2
0.6522	Remote Similarity	NPD7570	Approved
0.6519	Remote Similarity	NPD3528	Clinical (unspecified phase)
0.6514	Remote Similarity	NPD6657	Clinical (unspecified phase)
0.6514	Remote Similarity	NPD8462	Phase 1
0.6508	Remote Similarity	NPD1230	Approved
0.65	Remote Similarity	NPD5498	Phase 2
0.6486	Remote Similarity	NPD7082	Approved
0.6484	Remote Similarity	NPD3795	Approved
0.6484	Remote Similarity	NPD3794	Approved
0.6481	Remote Similarity	NPD7302	Phase 3
0.6481	Remote Similarity	NPD7300	Phase 3
0.6471	Remote Similarity	NPD6021	Clinical (unspecified phase)
0.6456	Remote Similarity	NPD7693	Approved
0.6452	Remote Similarity	NPD7259	Approved
0.6452	Remote Similarity	NPD2387	Approved
0.6452	Remote Similarity	NPD4506	Discontinued
0.6441	Remote Similarity	NPD8468	Phase 2
0.6435	Remote Similarity	NPD7922	Phase 1
0.6429	Remote Similarity	NPD5411	Discontinued
0.6429	Remote Similarity	NPD8155	Clinical (unspecified phase)
0.6422	Remote Similarity	NPD7546	Discontinued
0.642	Remote Similarity	NPD1574	Approved
0.6417	Remote Similarity	NPD7274	Clinical (unspecified phase)
0.6415	Remote Similarity	NPD5608	Approved
0.6415	Remote Similarity	NPD5609	Approved
0.6406	Remote Similarity	NPD4082	Approved
0.6398	Remote Similarity	NPD5195	Discontinued
0.6398	Remote Similarity	NPD2820	Phase 3
0.6396	Remote Similarity	NPD8404	Phase 2
0.6393	Remote Similarity	NPD1945	Phase 1
0.6393	Remote Similarity	NPD4493	Discontinued
0.6383	Remote Similarity	NPD4607	Approved
0.6383	Remote Similarity	NPD7236	Approved
0.6382	Remote Similarity	NPD5242	Approved
0.6381	Remote Similarity	NPD7256	Discontinued
0.6378	Remote Similarity	NPD7702	Clinical (unspecified phase)
0.6368	Remote Similarity	NPD4513	Discontinued
0.6364	Remote Similarity	NPD6723	Discontinued
0.6359	Remote Similarity	NPD7244	Discontinued
0.6355	Remote Similarity	NPD7476	Discontinued
0.6354	Remote Similarity	NPD6591	Clinical (unspecified phase)
0.635	Remote Similarity	NPD3451	Clinical (unspecified phase)
0.6344	Remote Similarity	NPD2365	Approved
0.6339	Remote Similarity	NPD2899	Discontinued
0.6329	Remote Similarity	NPD6793	Clinical (unspecified phase)
0.6321	Remote Similarity	NPD3684	Discontinued
0.6316	Remote Similarity	NPD5042	Phase 1
0.6308	Remote Similarity	NPD7599	Phase 2
0.6308	Remote Similarity	NPD6519	Phase 2
0.6304	Remote Similarity	NPD4981	Phase 2
0.6302	Remote Similarity	NPD7239	Suspended
0.63	Remote Similarity	NPD1913	Phase 1
0.6296	Remote Similarity	NPD6176	Phase 1
0.6292	Remote Similarity	NPD9567	Approved
0.6292	Remote Similarity	NPD552	Approved
0.6292	Remote Similarity	NPD553	Approved
0.6289	Remote Similarity	NPD7105	Phase 1
0.6284	Remote Similarity	NPD6973	Clinical (unspecified phase)
0.6284	Remote Similarity	NPD4596	Phase 1
0.6276	Remote Similarity	NPD7600	Phase 2
0.6275	Remote Similarity	NPD6496	Clinical (unspecified phase)
0.6273	Remote Similarity	NPD3893	Discontinued
0.627	Remote Similarity	NPD1110	Approved
0.627	Remote Similarity	NPD1109	Approved
0.6269	Remote Similarity	NPD7997	Clinical (unspecified phase)
0.6263	Remote Similarity	NPD6758	Approved
0.6256	Remote Similarity	NPD5610	Approved
0.6256	Remote Similarity	NPD2510	Approved
0.6256	Remote Similarity	NPD2509	Approved
0.625	Remote Similarity	NPD5186	Approved
0.625	Remote Similarity	NPD2369	Discontinued
0.625	Remote Similarity	NPD956	Clinical (unspecified phase)
0.625	Remote Similarity	NPD5183	Approved
0.6244	Remote Similarity	NPD7039	Approved
0.6244	Remote Similarity	NPD7038	Approved
0.6244	Remote Similarity	NPD1210	Approved
0.6239	Remote Similarity	NPD7858	Clinical (unspecified phase)
0.6239	Remote Similarity	NPD7999	Approved
0.6236	Remote Similarity	NPD2198	Approved
0.6236	Remote Similarity	NPD2199	Approved
0.6233	Remote Similarity	NPD4562	Clinical (unspecified phase)
0.6232	Remote Similarity	NPD8167	Discontinued
0.6231	Remote Similarity	NPD8002	Clinical (unspecified phase)
0.6231	Remote Similarity	NPD8003	Clinical (unspecified phase)
0.623	Remote Similarity	NPD4161	Discontinued
0.623	Remote Similarity	NPD5942	Approved
0.623	Remote Similarity	NPD5941	Approved
0.6224	Remote Similarity	NPD7114	Clinical (unspecified phase)
0.6223	Remote Similarity	NPD6625	Approved
0.6218	Remote Similarity	NPD3399	Approved
0.6216	Remote Similarity	NPD3888	Discontinued
0.6216	Remote Similarity	NPD4492	Approved
0.6216	Remote Similarity	NPD7301	Phase 3
0.6216	Remote Similarity	NPD4494	Approved
0.6214	Remote Similarity	NPD3253	Clinical (unspecified phase)
0.6211	Remote Similarity	NPD4041	Approved
0.621	Remote Similarity	NPD5143	Clinical (unspecified phase)
0.6207	Remote Similarity	NPD7799	Discontinued
0.6205	Remote Similarity	NPD6571	Approved
0.6205	Remote Similarity	NPD3389	Approved
0.6205	Remote Similarity	NPD3394	Approved
0.6205	Remote Similarity	NPD3393	Approved
0.6205	Remote Similarity	NPD6570	Approved
0.6204	Remote Similarity	NPD6238	Discontinued
0.6202	Remote Similarity	NPD3154	Approved
0.6202	Remote Similarity	NPD3153	Approved
0.62	Remote Similarity	NPD6457	Approved
0.6193	Remote Similarity	NPD7891	Discontinued
0.6193	Remote Similarity	NPD1294	Discontinued
0.619	Remote Similarity	NPD5896	Clinical (unspecified phase)
0.619	Remote Similarity	NPD7235	Clinical (unspecified phase)
0.6188	Remote Similarity	NPD4455	Discontinued
0.6184	Remote Similarity	NPD4412	Phase 2
0.6182	Remote Similarity	NPD4859	Phase 1
0.6182	Remote Similarity	NPD3472	Approved
0.6182	Remote Similarity	NPD4022	Approved
0.6181	Remote Similarity	NPD7036	Phase 3
0.6181	Remote Similarity	NPD7035	Approved
0.6178	Remote Similarity	NPD3949	Clinical (unspecified phase)
0.6178	Remote Similarity	NPD3352	Approved
0.6176	Remote Similarity	NPD5334	Clinical (unspecified phase)
0.6175	Remote Similarity	NPD5848	Clinical (unspecified phase)
0.6172	Remote Similarity	NPD6891	Phase 2
0.6172	Remote Similarity	NPD6484	Approved
0.6172	Remote Similarity	NPD6483	Approved
0.6172	Remote Similarity	NPD3863	Clinical (unspecified phase)
0.6172	Remote Similarity	NPD4948	Discontinued
0.617	Remote Similarity	NPD2923	Approved
0.6169	Remote Similarity	NPD7795	Phase 2
0.6168	Remote Similarity	NPD6621	Clinical (unspecified phase)
0.6167	Remote Similarity	NPD3437	Discontinued
0.6167	Remote Similarity	NPD3280	Approved
0.6165	Remote Similarity	NPD3471	Approved
0.6165	Remote Similarity	NPD3470	Approved
0.6164	Remote Similarity	NPD7010	Phase 3
0.6158	Remote Similarity	NPD6185	Discontinued
0.6154	Remote Similarity	NPD7708	Approved
0.6154	Remote Similarity	NPD6163	Clinical (unspecified phase)
0.615	Remote Similarity	NPD6534	Approved
0.615	Remote Similarity	NPD7292	Approved
0.615	Remote Similarity	NPD6535	Approved
0.6147	Remote Similarity	NPD7064	Clinical (unspecified phase)
0.6147	Remote Similarity	NPD2121	Clinical (unspecified phase)
0.6146	Remote Similarity	NPD7479	Phase 2
0.6146	Remote Similarity	NPD8304	Clinical (unspecified phase)
0.6146	Remote Similarity	NPD2869	Clinical (unspecified phase)
0.6141	Remote Similarity	NPD5182	Approved
0.6141	Remote Similarity	NPD5184	Approved
0.6141	Remote Similarity	NPD5185	Approved
0.6141	Remote Similarity	NPD3373	Approved
0.614	Remote Similarity	NPD7700	Phase 2
0.614	Remote Similarity	NPD7699	Phase 2

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