NPASS Compound

Structure

NPC471168 OpenBabel07101719512D 37 42 0 0 1 0 0 0 0 0999 V2000 -1.1756 -0.2091 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2257 -4.4632 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1776 -1.3746 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6776 -2.2406 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3523 -1.3271 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2024 -2.7007 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0796 1.2594 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7057 -1.6923 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2934 -2.5013 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 -2.8116 -0.7406 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8116 -3.7406 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7546 -3.0013 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5878 -1.0181 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7688 -4.3587 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7546 -2.0013 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9456 -1.4135 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.8116 -1.7406 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.6776 -3.2406 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9456 -3.2406 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9945 -0.1045 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.9456 -0.2406 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9945 -1.9316 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.4067 -2.7406 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.5878 -2.6361 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.6776 -2.2406 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9456 -2.2406 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9945 -1.7226 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.4067 -0.9135 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.3566 -5.1677 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.5437 -3.7406 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0796 -0.7406 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.9456 0.7594 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.7057 -3.3103 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.1756 -3.4451 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9945 -3.5497 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 14 2 0 0 0 0 2 15 1 0 0 0 0 3 26 1 0 0 0 0 4 26 1 0 0 0 0 6 28 1 0 0 0 0 7 33 1 0 0 0 0 8 9 2 0 0 0 0 8 16 1 0 0 0 0 9 34 1 0 0 0 0 10 17 1 0 0 0 0 10 21 1 0 0 0 0 11 18 1 0 0 0 0 11 22 1 0 0 0 0 12 19 1 0 0 0 0 12 20 1 0 0 0 0 13 16 2 0 0 0 0 13 34 1 0 0 0 0 14 23 1 0 0 0 0 15 30 2 0 0 0 0 15 35 1 0 0 0 0 16 17 1 0 0 0 0 17 28 1 1 0 0 0 18 26 1 0 0 0 0 18 27 1 6 0 0 0 19 26 1 0 0 0 0 19 31 2 0 0 0 0 20 27 1 1 0 0 0 20 36 1 0 0 0 0 21 29 1 1 0 0 0 21 37 1 0 0 0 0 22 32 2 0 0 0 0 22 33 1 0 0 0 0 23 24 1 0 0 0 0 23 27 1 6 0 0 0 24 25 1 0 0 0 0 24 36 1 6 0 0 0 25 28 1 1 0 0 0 25 35 1 0 0 0 0 27 5 1 6 0 0 0 28 29 1 1 0 0 0 29 14 1 1 0 0 0 29 37 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	512.24
Volume:	513.304
LogP:	3.438
LogD:	2.86
LogS:	-5.088
# Rotatable Bonds:	6
TPSA:	104.57
# H-Bond Aceptor:	8
# H-Bond Donor:	0
# Rings:	6
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.339
Synthetic Accessibility Score:	5.928
Fsp3:	0.69
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:	-5.334
MDCK Permeability:	3.7619021895807236e-05
Pgp-inhibitor:	0.983
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.015
20% Bioavailability (F20%):	0.472
30% Bioavailability (F30%):	0.931

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.446
Plasma Protein Binding (PPB):	66.0136947631836%
Volume Distribution (VD):	1.936
Pgp-substrate:	27.08580207824707%

ADMET: Metabolism

CYP1A2-inhibitor:	0.018
CYP1A2-substrate:	0.107
CYP2C19-inhibitor:	0.143
CYP2C19-substrate:	0.508
CYP2C9-inhibitor:	0.633
CYP2C9-substrate:	0.013
CYP2D6-inhibitor:	0.04
CYP2D6-substrate:	0.134
CYP3A4-inhibitor:	0.825
CYP3A4-substrate:	0.623

ADMET: Excretion

Clearance (CL):	12.044
Half-life (T1/2):	0.728

ADMET: Toxicity

hERG Blockers:	0.044
Human Hepatotoxicity (H-HT):	0.507
Drug-inuced Liver Injury (DILI):	0.481
AMES Toxicity:	0.008
Rat Oral Acute Toxicity:	0.957
Maximum Recommended Daily Dose:	0.94
Skin Sensitization:	0.124
Carcinogencity:	0.15
Eye Corrosion:	0.062
Eye Irritation:	0.045
Respiratory Toxicity:	0.987

Download Data

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

Natural Product: NPC471168

Natural Product ID:	NPC471168
*Common Name:**	Turrapubin D
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	RVOBFAWYZMLHLH-FIOAHQOWSA-N
Standard InCHI:	InChI=1S/C29H36O8/c1-14-23-24(36-20-12-19(31)26(3,4)18(27(20,23)5)11-22(32)33-7)25(35-15(2)30)28(6)17(16-8-9-34-13-16)10-21-29(14,28)37-21/h8-9,13,17-18,20-21,23-25H,1,10-12H2,2-7H3/t17-,18-,20-,21+,23+,24+,25-,27+,28+,29+/m0/s1
SMILES:	COC(=O)C[C@@H]1[C@]2(C)[C@@H](O[C@@H]3[C@H]2C(=C)[C@@]24[C@]([C@H]3OC(=O)C)(C)[C@@H](C[C@H]4O2)c2cocc2)CC(=O)C1(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2386292
PubChem CID:	71725865
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids [CHEMONTID:0002380] Limonoids

*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
NPO10033	Turraea pubescens	Species	Meliaceae	Eukaryota	twig	Dongfang, Hainan Province, China	2010-Mar	PMID[23734701]
NPO10033	Turraea pubescens	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	2

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	>	20000.0	nM	PMID[507497]
NPT116	Cell Line	HL-60	Homo sapiens	IC50	<	10000.0	nM	PMID[507497]

☑ 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 NPC471168 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	442
0.1-0.2	1629
0.2-0.3	3470
0.3-0.4	6573
0.4-0.5	11717
0.5-0.6	10052
0.6-0.7	7763
0.7-0.8	744
0.8-0.85	231
0.85-0.9	54
0.9-0.95	19
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9804	High Similarity	NPC471167
0.9804	High Similarity	NPC471166
0.9548	High Similarity	NPC472668
0.9487	High Similarity	NPC472669
0.9437	High Similarity	NPC469848
0.9351	High Similarity	NPC471175
0.929	High Similarity	NPC175964
0.929	High Similarity	NPC471169
0.9156	High Similarity	NPC18135
0.9136	High Similarity	NPC285227
0.9102	High Similarity	NPC242068
0.9102	High Similarity	NPC105395
0.9102	High Similarity	NPC247563
0.9057	High Similarity	NPC5741
0.9057	High Similarity	NPC197596
0.9051	High Similarity	NPC474932
0.9045	High Similarity	NPC204663
0.9032	High Similarity	NPC116717
0.8987	High Similarity	NPC195131
0.8987	High Similarity	NPC469847
0.8974	High Similarity	NPC308205
0.8974	High Similarity	NPC322546
0.8974	High Similarity	NPC182427
0.8974	High Similarity	NPC84063
0.8974	High Similarity	NPC29695
0.8951	High Similarity	NPC472764
0.8951	High Similarity	NPC476224
0.8931	High Similarity	NPC475226
0.8896	High Similarity	NPC221809
0.8896	High Similarity	NPC472765
0.8896	High Similarity	NPC472766
0.8882	High Similarity	NPC476197
0.8875	High Similarity	NPC191828
0.8868	High Similarity	NPC167142
0.8854	High Similarity	NPC268905
0.8846	High Similarity	NPC156189
0.8834	High Similarity	NPC476861
0.8834	High Similarity	NPC476850
0.882	High Similarity	NPC472767
0.882	High Similarity	NPC470939
0.882	High Similarity	NPC6326
0.8802	High Similarity	NPC478177
0.8795	High Similarity	NPC471437
0.8795	High Similarity	NPC471632
0.879	High Similarity	NPC291150
0.8788	High Similarity	NPC159232
0.8782	High Similarity	NPC470790
0.8782	High Similarity	NPC470791
0.8782	High Similarity	NPC471001
0.878	High Similarity	NPC327922
0.8774	High Similarity	NPC255414
0.8765	High Similarity	NPC165218
0.8765	High Similarity	NPC469846
0.8758	High Similarity	NPC305016
0.875	High Similarity	NPC214495
0.875	High Similarity	NPC197137
0.875	High Similarity	NPC475066
0.875	High Similarity	NPC299038
0.875	High Similarity	NPC470119
0.875	High Similarity	NPC470118
0.8742	High Similarity	NPC476262
0.8742	High Similarity	NPC469850
0.8734	High Similarity	NPC75906
0.8734	High Similarity	NPC476201
0.8726	High Similarity	NPC5180
0.872	High Similarity	NPC173516
0.8712	High Similarity	NPC123088
0.8712	High Similarity	NPC476858
0.8712	High Similarity	NPC476857
0.8712	High Similarity	NPC476856
0.8704	High Similarity	NPC472771
0.8698	High Similarity	NPC470938
0.8696	High Similarity	NPC473473
0.8696	High Similarity	NPC472671
0.8696	High Similarity	NPC475295
0.8696	High Similarity	NPC237155
0.8683	High Similarity	NPC94763
0.8683	High Similarity	NPC236004
0.8667	High Similarity	NPC472673
0.8667	High Similarity	NPC471397
0.8667	High Similarity	NPC160651
0.8662	High Similarity	NPC69647
0.8662	High Similarity	NPC125182
0.8659	High Similarity	NPC149945
0.8659	High Similarity	NPC472141
0.8659	High Similarity	NPC478178
0.865	High Similarity	NPC472773
0.8645	High Similarity	NPC34056
0.8642	High Similarity	NPC25255
0.8634	High Similarity	NPC286722
0.8614	High Similarity	NPC470995
0.8614	High Similarity	NPC472659
0.8608	High Similarity	NPC476122
0.8608	High Similarity	NPC469335
0.8608	High Similarity	NPC159927
0.8608	High Similarity	NPC477404
0.8608	High Similarity	NPC196864
0.8606	High Similarity	NPC472774
0.8606	High Similarity	NPC472775
0.8606	High Similarity	NPC476853
0.8606	High Similarity	NPC478179
0.8598	High Similarity	NPC476860
0.859	High Similarity	NPC470999
0.8589	High Similarity	NPC193798
0.8589	High Similarity	NPC470792
0.8571	High Similarity	NPC209364
0.8571	High Similarity	NPC477824
0.8571	High Similarity	NPC107646
0.8571	High Similarity	NPC60973
0.8571	High Similarity	NPC126723
0.8571	High Similarity	NPC469576
0.8571	High Similarity	NPC263265
0.8562	High Similarity	NPC98206
0.8562	High Similarity	NPC34421
0.8562	High Similarity	NPC237259
0.8554	High Similarity	NPC271235
0.8545	High Similarity	NPC214600
0.8545	High Similarity	NPC23387
0.8544	High Similarity	NPC472654
0.8537	High Similarity	NPC472139
0.8537	High Similarity	NPC224394
0.8537	High Similarity	NPC469338
0.8537	High Similarity	NPC476035
0.8537	High Similarity	NPC14499
0.8537	High Similarity	NPC663
0.8537	High Similarity	NPC419
0.8537	High Similarity	NPC475039
0.8537	High Similarity	NPC292389
0.8528	High Similarity	NPC470789
0.8528	High Similarity	NPC472653
0.8528	High Similarity	NPC475381
0.8521	High Similarity	NPC469633
0.8521	High Similarity	NPC167340
0.8519	High Similarity	NPC195954
0.8519	High Similarity	NPC472283
0.8519	High Similarity	NPC472772
0.8509	High Similarity	NPC296807
0.8509	High Similarity	NPC92979
0.8509	High Similarity	NPC155939
0.8509	High Similarity	NPC264943
0.8509	High Similarity	NPC141538
0.85	High Similarity	NPC470996
0.85	High Similarity	NPC472672
0.85	High Similarity	NPC471002
0.8494	Intermediate Similarity	NPC270312
0.8494	Intermediate Similarity	NPC472282
0.8494	Intermediate Similarity	NPC473753
0.8494	Intermediate Similarity	NPC472651
0.8494	Intermediate Similarity	NPC473766
0.8485	Intermediate Similarity	NPC61967
0.8485	Intermediate Similarity	NPC469849
0.8485	Intermediate Similarity	NPC276551
0.8485	Intermediate Similarity	NPC126984
0.8485	Intermediate Similarity	NPC259943
0.8485	Intermediate Similarity	NPC470940
0.8485	Intermediate Similarity	NPC27541
0.8485	Intermediate Similarity	NPC62692
0.8476	Intermediate Similarity	NPC82851
0.8476	Intermediate Similarity	NPC200782
0.8476	Intermediate Similarity	NPC329938
0.8471	Intermediate Similarity	NPC470181
0.8466	Intermediate Similarity	NPC475967
0.8462	Intermediate Similarity	NPC251865
0.8452	Intermediate Similarity	NPC475237
0.8452	Intermediate Similarity	NPC475641
0.8452	Intermediate Similarity	NPC121158
0.8447	Intermediate Similarity	NPC302054
0.8447	Intermediate Similarity	NPC57998
0.8447	Intermediate Similarity	NPC253201
0.8443	Intermediate Similarity	NPC472652
0.8438	Intermediate Similarity	NPC471000
0.8434	Intermediate Similarity	NPC470875
0.8434	Intermediate Similarity	NPC472670
0.8434	Intermediate Similarity	NPC121995
0.8434	Intermediate Similarity	NPC307781
0.8428	Intermediate Similarity	NPC195325
0.8424	Intermediate Similarity	NPC39986
0.8424	Intermediate Similarity	NPC477405
0.8424	Intermediate Similarity	NPC234660
0.8424	Intermediate Similarity	NPC285567
0.8424	Intermediate Similarity	NPC51568
0.8424	Intermediate Similarity	NPC134254
0.8424	Intermediate Similarity	NPC302369
0.8408	Intermediate Similarity	NPC5676
0.8405	Intermediate Similarity	NPC472777
0.8405	Intermediate Similarity	NPC88007
0.8405	Intermediate Similarity	NPC1408
0.8405	Intermediate Similarity	NPC472776
0.8405	Intermediate Similarity	NPC472778
0.8405	Intermediate Similarity	NPC187149
0.8405	Intermediate Similarity	NPC246841
0.8397	Intermediate Similarity	NPC223415
0.8395	Intermediate Similarity	NPC469336
0.8393	Intermediate Similarity	NPC88593
0.8387	Intermediate Similarity	NPC20500
0.8373	Intermediate Similarity	NPC271657
0.8373	Intermediate Similarity	NPC276735
0.8373	Intermediate Similarity	NPC56358
0.8365	Intermediate Similarity	NPC19747
0.8364	Intermediate Similarity	NPC188649

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 NPC471168 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	366
0.1-0.2	1059
0.2-0.3	2407
0.3-0.4	2733
0.4-0.5	1739
0.5-0.6	675
0.6-0.7	162
0.7-0.8	7
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
0.8395	Intermediate Similarity	NPD5761	Phase 2
0.8395	Intermediate Similarity	NPD5760	Phase 2
0.7966	Intermediate Similarity	NPD8434	Phase 2
0.787	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7784	Intermediate Similarity	NPD6765	Approved
0.7784	Intermediate Similarity	NPD6764	Approved
0.7611	Intermediate Similarity	NPD6785	Approved
0.7611	Intermediate Similarity	NPD6784	Approved
0.7119	Intermediate Similarity	NPD5494	Approved
0.7079	Intermediate Similarity	NPD1247	Approved
0.7076	Intermediate Similarity	NPD920	Approved
0.7062	Intermediate Similarity	NPD919	Approved
0.7052	Intermediate Similarity	NPD6599	Discontinued
0.7043	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7029	Intermediate Similarity	NPD7819	Suspended
0.7024	Intermediate Similarity	NPD4628	Phase 3
0.6983	Remote Similarity	NPD8127	Discontinued
0.6978	Remote Similarity	NPD7799	Discontinued
0.6959	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6946	Remote Similarity	NPD1471	Phase 3
0.6941	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6932	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD6559	Discontinued
0.6919	Remote Similarity	NPD6273	Approved
0.691	Remote Similarity	NPD7075	Discontinued
0.6885	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD8404	Phase 2
0.6853	Remote Similarity	NPD7497	Discontinued
0.6842	Remote Similarity	NPD7236	Approved
0.6828	Remote Similarity	NPD7685	Pre-registration
0.6821	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD7411	Suspended
0.6802	Remote Similarity	NPD6799	Approved
0.68	Remote Similarity	NPD3226	Approved
0.6798	Remote Similarity	NPD3817	Phase 2
0.6798	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD2796	Approved
0.678	Remote Similarity	NPD6801	Discontinued
0.6765	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD1243	Approved
0.6757	Remote Similarity	NPD5844	Phase 1
0.6746	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6743	Remote Similarity	NPD7239	Suspended
0.6739	Remote Similarity	NPD7473	Discontinued
0.6721	Remote Similarity	NPD3926	Phase 2
0.6703	Remote Similarity	NPD7199	Phase 2
0.6686	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6648	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6647	Remote Similarity	NPD6002	Phase 3
0.6647	Remote Similarity	NPD6005	Phase 3
0.6647	Remote Similarity	NPD5763	Approved
0.6647	Remote Similarity	NPD5762	Approved
0.6647	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6647	Remote Similarity	NPD6004	Phase 3
0.6647	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD6832	Phase 2
0.663	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.663	Remote Similarity	NPD3749	Approved
0.6627	Remote Similarity	NPD8032	Phase 2
0.6613	Remote Similarity	NPD3818	Discontinued
0.6611	Remote Similarity	NPD5402	Approved
0.6598	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6595	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6592	Remote Similarity	NPD1934	Approved
0.6576	Remote Similarity	NPD6808	Phase 2
0.6576	Remote Similarity	NPD6232	Discontinued
0.6575	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6575	Remote Similarity	NPD4967	Phase 2
0.6575	Remote Similarity	NPD4966	Approved
0.6575	Remote Similarity	NPD4965	Approved
0.6575	Remote Similarity	NPD3882	Suspended
0.6573	Remote Similarity	NPD7028	Phase 2
0.6573	Remote Similarity	NPD4380	Phase 2
0.6571	Remote Similarity	NPD2532	Approved
0.6571	Remote Similarity	NPD2534	Approved
0.6571	Remote Similarity	NPD2533	Approved
0.6571	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6566	Remote Similarity	NPD8285	Discontinued
0.6538	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6532	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6529	Remote Similarity	NPD2799	Discontinued
0.6529	Remote Similarity	NPD3748	Approved
0.6517	Remote Similarity	NPD7458	Discontinued
0.6503	Remote Similarity	NPD6234	Discontinued
0.6497	Remote Similarity	NPD5403	Approved
0.6492	Remote Similarity	NPD8312	Approved
0.6492	Remote Similarity	NPD8313	Approved
0.6491	Remote Similarity	NPD1551	Phase 2
0.6477	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6477	Remote Similarity	NPD5401	Approved
0.6464	Remote Similarity	NPD2801	Approved
0.6458	Remote Similarity	NPD8407	Phase 2
0.6455	Remote Similarity	NPD7074	Phase 3
0.6453	Remote Similarity	NPD2346	Discontinued
0.645	Remote Similarity	NPD6355	Discontinued
0.6437	Remote Similarity	NPD4110	Phase 3
0.6437	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6436	Remote Similarity	NPD3751	Discontinued
0.6433	Remote Similarity	NPD7033	Discontinued
0.6432	Remote Similarity	NPD6959	Discontinued
0.6424	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6417	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6417	Remote Similarity	NPD2403	Approved
0.6417	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6417	Remote Similarity	NPD6166	Phase 2
0.6416	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6416	Remote Similarity	NPD1549	Phase 2
0.641	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6409	Remote Similarity	NPD37	Approved
0.6402	Remote Similarity	NPD7054	Approved
0.6402	Remote Similarity	NPD1876	Approved
0.6402	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.64	Remote Similarity	NPD3887	Approved
0.6398	Remote Similarity	NPD3787	Discontinued
0.6398	Remote Similarity	NPD7315	Approved
0.6398	Remote Similarity	NPD17	Approved
0.6395	Remote Similarity	NPD2438	Suspended
0.6395	Remote Similarity	NPD6100	Approved
0.6395	Remote Similarity	NPD6099	Approved
0.6395	Remote Similarity	NPD2935	Discontinued
0.6393	Remote Similarity	NPD7058	Phase 2
0.6393	Remote Similarity	NPD7768	Phase 2
0.6393	Remote Similarity	NPD7057	Phase 3
0.6392	Remote Similarity	NPD8150	Discontinued
0.6391	Remote Similarity	NPD4140	Approved
0.6387	Remote Similarity	NPD8368	Discontinued
0.6384	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.638	Remote Similarity	NPD3972	Approved
0.6379	Remote Similarity	NPD2800	Approved
0.6369	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6368	Remote Similarity	NPD7472	Approved
0.6368	Remote Similarity	NPD4107	Approved
0.6364	Remote Similarity	NPD3267	Approved
0.6364	Remote Similarity	NPD3266	Approved
0.6358	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6358	Remote Similarity	NPD2344	Approved
0.6358	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6354	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6353	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6349	Remote Similarity	NPD7228	Approved
0.6343	Remote Similarity	NPD3750	Approved
0.6341	Remote Similarity	NPD5327	Phase 3
0.6328	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6325	Remote Similarity	NPD5647	Approved
0.6316	Remote Similarity	NPD6653	Approved
0.6302	Remote Similarity	NPD7251	Discontinued
0.628	Remote Similarity	NPD1608	Approved
0.6275	Remote Similarity	NPD7435	Discontinued
0.6272	Remote Similarity	NPD3268	Approved
0.6272	Remote Similarity	NPD2313	Discontinued
0.6272	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6269	Remote Similarity	NPD7808	Phase 3
0.6264	Remote Similarity	NPD6385	Approved
0.6264	Remote Similarity	NPD6386	Approved
0.6258	Remote Similarity	NPD7457	Clinical (unspecified phase)
0.6257	Remote Similarity	NPD5735	Approved
0.6257	Remote Similarity	NPD1933	Approved
0.6256	Remote Similarity	NPD4482	Phase 3
0.625	Remote Similarity	NPD5616	Clinical (unspecified phase)
0.625	Remote Similarity	NPD5353	Approved
0.625	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.625	Remote Similarity	NPD6797	Phase 2
0.6243	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6243	Remote Similarity	NPD1510	Phase 2
0.6236	Remote Similarity	NPD1511	Approved
0.6235	Remote Similarity	NPD6663	Approved
0.6235	Remote Similarity	NPD5585	Approved
0.6223	Remote Similarity	NPD7229	Phase 3
0.6221	Remote Similarity	NPD1607	Approved
0.6221	Remote Similarity	NPD6353	Approved
0.622	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6218	Remote Similarity	NPD7240	Approved
0.6215	Remote Similarity	NPD2309	Approved
0.6209	Remote Similarity	NPD7930	Approved
0.6199	Remote Similarity	NPD4307	Phase 2
0.6199	Remote Similarity	NPD2979	Phase 3
0.6199	Remote Similarity	NPD1240	Approved
0.6196	Remote Similarity	NPD1465	Phase 2
0.619	Remote Similarity	NPD5242	Approved
0.6186	Remote Similarity	NPD7907	Approved
0.6171	Remote Similarity	NPD2353	Approved
0.6171	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6168	Remote Similarity	NPD1049	Clinical (unspecified phase)
0.6168	Remote Similarity	NPD4111	Phase 1
0.6168	Remote Similarity	NPD7319	Approved
0.6167	Remote Similarity	NPD1512	Approved
0.6166	Remote Similarity	NPD5953	Discontinued
0.6163	Remote Similarity	NPD447	Suspended
0.6162	Remote Similarity	NPD8360	Approved
0.6162	Remote Similarity	NPD8361	Approved
0.6162	Remote Similarity	NPD8435	Approved
0.6158	Remote Similarity	NPD7003	Approved
0.6158	Remote Similarity	NPD7784	Clinical (unspecified phase)
0.6146	Remote Similarity	NPD7286	Phase 2
0.6141	Remote Similarity	NPD6280	Approved
0.6141	Remote Similarity	NPD6279	Approved
0.6138	Remote Similarity	NPD5710	Approved
0.6138	Remote Similarity	NPD5711	Approved
0.6135	Remote Similarity	NPD7999	Approved
0.6131	Remote Similarity	NPD1019	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