NPASS Compound

Structure

NPC473766 OpenBabel07101719132D 38 43 0 0 1 0 0 0 0 0999 V2000 -3.7551 1.0301 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6927 1.9545 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0277 -1.5968 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5163 -2.4432 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -2.9318 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5390 -1.4659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.9773 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8463 -2.4432 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6927 -3.9091 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4875 -1.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8463 -3.4205 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6927 -1.9545 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4434 -2.1524 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6927 -0.9773 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4813 0.3761 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6927 0.9773 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3854 -0.9773 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.9545 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6927 -1.9545 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5390 -3.4205 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8463 -0.4886 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.2782 -0.5798 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5390 -0.4886 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8463 0.4886 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6927 0.9773 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5390 -2.4432 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8463 -2.4432 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6927 -0.9773 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -0.9773 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8463 -0.4886 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.4108 0.6781 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5390 0.4886 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3854 -3.9091 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6927 1.9545 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.9321 -1.3060 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8463 0.4886 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5390 0.4886 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 15 1 0 0 0 0 2 16 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 29 1 0 0 0 0 8 12 1 0 0 0 0 8 18 1 0 0 0 0 9 11 2 0 0 0 0 9 20 1 0 0 0 0 10 13 2 0 0 0 0 10 17 1 0 0 0 0 11 27 1 0 0 0 0 12 28 1 0 0 0 0 13 35 1 0 0 0 0 14 19 1 0 0 0 0 14 21 1 0 0 0 0 15 22 1 0 0 0 0 15 31 2 0 0 0 0 16 32 2 0 0 0 0 16 36 1 0 0 0 0 17 22 2 0 0 0 0 17 23 1 0 0 0 0 18 27 1 1 0 0 0 18 29 1 0 0 0 0 19 26 1 0 0 0 0 19 27 1 1 0 0 0 20 26 1 0 0 0 0 20 33 2 0 0 0 0 21 29 1 6 0 0 0 21 36 1 0 0 0 0 22 35 1 0 0 0 0 23 28 1 6 0 0 0 23 37 1 0 0 0 0 24 25 1 0 0 0 0 24 30 1 6 0 0 0 24 38 1 0 0 0 0 25 34 2 0 0 0 0 25 37 1 0 0 0 0 27 5 1 1 0 0 0 28 30 1 6 0 0 0 29 30 1 6 0 0 0 30 38 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	524.24
Volume:	527.964
LogP:	3.484
LogD:	2.442
LogS:	-4.878
# Rotatable Bonds:	4
TPSA:	112.41
# H-Bond Aceptor:	8
# H-Bond Donor:	0
# Rings:	6
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.316
Synthetic Accessibility Score:	5.691
Fsp3:	0.667
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:	-5.354
MDCK Permeability:	1.33342036860995e-05
Pgp-inhibitor:	1.0
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.703
30% Bioavailability (F30%):	0.946

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.033
Plasma Protein Binding (PPB):	81.63573455810547%
Volume Distribution (VD):	2.317
Pgp-substrate:	11.0173921585083%

ADMET: Metabolism

CYP1A2-inhibitor:	0.088
CYP1A2-substrate:	0.198
CYP2C19-inhibitor:	0.365
CYP2C19-substrate:	0.588
CYP2C9-inhibitor:	0.812
CYP2C9-substrate:	0.032
CYP2D6-inhibitor:	0.11
CYP2D6-substrate:	0.063
CYP3A4-inhibitor:	0.77
CYP3A4-substrate:	0.779

ADMET: Excretion

Clearance (CL):	3.36
Half-life (T1/2):	0.286

ADMET: Toxicity

hERG Blockers:	0.18
Human Hepatotoxicity (H-HT):	0.633
Drug-inuced Liver Injury (DILI):	0.54
AMES Toxicity:	0.226
Rat Oral Acute Toxicity:	0.818
Maximum Recommended Daily Dose:	0.885
Skin Sensitization:	0.419
Carcinogencity:	0.117
Eye Corrosion:	0.097
Eye Irritation:	0.085
Respiratory Toxicity:	0.945

Download Data

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

Natural Product: NPC473766

Natural Product ID:	NPC473766
*Common Name:**	DWKWCVXACCMPGW-KCOSXCBVSA-N
IUPAC Name:	n.a.
Synonyms:	21-Acetylgedunin
Standard InCHIKey:	DWKWCVXACCMPGW-KCOSXCBVSA-N
Standard InCHI:	InChI=1S/C30H36O8/c1-15(31)22-17(10-13-35-22)23-28(6)12-8-18-27(5)11-9-20(33)26(3,4)19(27)14-21(36-16(2)32)29(18,7)30(28)24(38-30)25(34)37-23/h9-11,13,18-19,21,23-24H,8,12,14H2,1-7H3/t18-,19+,21-,23+,24-,27-,28+,29+,30-/m1/s1
SMILES:	CC(=O)O[C@@H]1C[C@@H]2[C@]([C@@H]3[C@]1(C)[C@@]14O[C@@H]1C(=O)O[C@H]([C@@]4(CC3)C)c1ccoc1C(=O)C)(C)C=CC(=O)C2(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL451271
PubChem CID:	10506255
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
NPO20413	Meliaceae spp.	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9134742]
NPO20413	Meliaceae spp.	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]

☑ 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	3
Others	3

Activity Type	# Activity
Cell Line	2
Organism	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	Activity	=	31.0	%	PMID[558806]
NPT91	Cell Line	KB	Homo sapiens	IC50	=	9.4	ug.mL-1	PMID[558806]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	0.133	ug.mL-1	PMID[558806]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	0.039	ug.mL-1	PMID[558806]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Activity	=	29.38	%	PMID[558806]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Activity	=	51.3	%	PMID[558806]

☑ 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 NPC473766 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	453
0.1-0.2	1565
0.2-0.3	3170
0.3-0.4	6436
0.4-0.5	10575
0.5-0.6	8753
0.6-0.7	8299
0.7-0.8	3033
0.8-0.85	271
0.85-0.9	98
0.9-0.95	36
0.95-1	8

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC473753
0.9613	High Similarity	NPC473368
0.9548	High Similarity	NPC286722
0.95	High Similarity	NPC302392
0.949	High Similarity	NPC470939
0.9487	High Similarity	NPC475295
0.9487	High Similarity	NPC473473
0.9484	High Similarity	NPC209364
0.9484	High Similarity	NPC60973
0.9423	High Similarity	NPC472283
0.9363	High Similarity	NPC237155
0.9359	High Similarity	NPC107646
0.9313	High Similarity	NPC475779
0.9304	High Similarity	NPC25255
0.9304	High Similarity	NPC305016
0.9304	High Similarity	NPC475381
0.9295	High Similarity	NPC469850
0.9255	High Similarity	NPC173516
0.925	High Similarity	NPC476856
0.925	High Similarity	NPC476857
0.925	High Similarity	NPC476858
0.9245	High Similarity	NPC193798
0.9245	High Similarity	NPC5079
0.9236	High Similarity	NPC263265
0.9236	High Similarity	NPC126723
0.9198	High Similarity	NPC471397
0.9187	High Similarity	NPC469338
0.9187	High Similarity	NPC51568
0.9187	High Similarity	NPC292389
0.9187	High Similarity	NPC234660
0.9161	High Similarity	NPC159927
0.9161	High Similarity	NPC469335
0.9136	High Similarity	NPC476853
0.9136	High Similarity	NPC476850
0.9136	High Similarity	NPC476861
0.9136	High Similarity	NPC472282
0.913	High Similarity	NPC123088
0.913	High Similarity	NPC476860
0.913	High Similarity	NPC470940
0.913	High Similarity	NPC276551
0.913	High Similarity	NPC469849
0.9125	High Similarity	NPC69028
0.9119	High Similarity	NPC477403
0.908	High Similarity	NPC160651
0.9074	High Similarity	NPC23387
0.9074	High Similarity	NPC470875
0.9068	High Similarity	NPC302369
0.9068	High Similarity	NPC476197
0.9068	High Similarity	NPC469846
0.9068	High Similarity	NPC477405
0.9068	High Similarity	NPC134254
0.9068	High Similarity	NPC39986
0.9062	High Similarity	NPC335761
0.9062	High Similarity	NPC472653
0.9038	High Similarity	NPC46551
0.9038	High Similarity	NPC196864
0.9038	High Similarity	NPC477404
0.9036	High Similarity	NPC167340
0.9006	High Similarity	NPC96443
0.9006	High Similarity	NPC290400
0.8944	High Similarity	NPC191828
0.8944	High Similarity	NPC477402
0.8938	High Similarity	NPC167142
0.8931	High Similarity	NPC469336
0.8924	High Similarity	NPC476201
0.891	High Similarity	NPC19747
0.8903	High Similarity	NPC262198
0.8889	High Similarity	NPC197596
0.8889	High Similarity	NPC263432
0.8889	High Similarity	NPC329938
0.8889	High Similarity	NPC117986
0.8889	High Similarity	NPC82851
0.8889	High Similarity	NPC188649
0.8868	High Similarity	NPC178932
0.8861	High Similarity	NPC18135
0.8848	High Similarity	NPC271235
0.8841	High Similarity	NPC121995
0.8834	High Similarity	NPC14499
0.8834	High Similarity	NPC475039
0.8834	High Similarity	NPC88841
0.8834	High Similarity	NPC288602
0.8834	High Similarity	NPC476035
0.8827	High Similarity	NPC287559
0.8827	High Similarity	NPC333139
0.882	High Similarity	NPC249021
0.8812	High Similarity	NPC264943
0.8812	High Similarity	NPC476262
0.8812	High Similarity	NPC75310
0.8797	High Similarity	NPC476122
0.8788	High Similarity	NPC472651
0.8788	High Similarity	NPC270312
0.8788	High Similarity	NPC472774
0.8788	High Similarity	NPC472775
0.8774	High Similarity	NPC86935
0.8773	High Similarity	NPC68848
0.8773	High Similarity	NPC18986
0.8773	High Similarity	NPC149896
0.8773	High Similarity	NPC472771
0.8765	High Similarity	NPC474611
0.8758	High Similarity	NPC41880
0.8758	High Similarity	NPC469485
0.8735	High Similarity	NPC472652
0.8735	High Similarity	NPC296558
0.8726	High Similarity	NPC221809
0.8726	High Similarity	NPC71821
0.872	High Similarity	NPC472773
0.8704	High Similarity	NPC195954
0.8704	High Similarity	NPC187149
0.8704	High Similarity	NPC88007
0.8704	High Similarity	NPC472772
0.8704	High Similarity	NPC173544
0.8696	High Similarity	NPC281258
0.8696	High Similarity	NPC214541
0.8696	High Similarity	NPC44675
0.869	High Similarity	NPC469848
0.8688	High Similarity	NPC469503
0.8688	High Similarity	NPC475777
0.8667	High Similarity	NPC271657
0.8667	High Similarity	NPC56358
0.8662	High Similarity	NPC62799
0.8659	High Similarity	NPC18347
0.8654	High Similarity	NPC142113
0.865	High Similarity	NPC307383
0.8647	High Similarity	NPC472665
0.8634	High Similarity	NPC114880
0.8634	High Similarity	NPC282445
0.8616	High Similarity	NPC211625
0.8608	High Similarity	NPC470941
0.8606	High Similarity	NPC224394
0.8606	High Similarity	NPC285567
0.8606	High Similarity	NPC663
0.8589	High Similarity	NPC36655
0.8589	High Similarity	NPC194499
0.8589	High Similarity	NPC299038
0.8589	High Similarity	NPC45101
0.8589	High Similarity	NPC261597
0.8589	High Similarity	NPC81405
0.8571	High Similarity	NPC75906
0.8571	High Similarity	NPC88593
0.8563	High Similarity	NPC476224
0.8562	High Similarity	NPC212257
0.8554	High Similarity	NPC276735
0.8554	High Similarity	NPC472664
0.8554	High Similarity	NPC470182
0.8554	High Similarity	NPC261184
0.8545	High Similarity	NPC200782
0.8545	High Similarity	NPC471166
0.8545	High Similarity	NPC471167
0.8545	High Similarity	NPC6326
0.8538	High Similarity	NPC478177
0.8537	High Similarity	NPC475967
0.8537	High Similarity	NPC140952
0.8528	High Similarity	NPC104736
0.8521	High Similarity	NPC160818
0.8521	High Similarity	NPC169299
0.8519	High Similarity	NPC30222
0.8519	High Similarity	NPC57998
0.8516	High Similarity	NPC282973
0.8512	High Similarity	NPC327922
0.8512	High Similarity	NPC475109
0.8503	High Similarity	NPC478178
0.8494	Intermediate Similarity	NPC283209
0.8494	Intermediate Similarity	NPC419
0.8494	Intermediate Similarity	NPC471168
0.8485	Intermediate Similarity	NPC8389
0.848	Intermediate Similarity	NPC262386
0.8476	Intermediate Similarity	NPC304692
0.8476	Intermediate Similarity	NPC1408
0.8476	Intermediate Similarity	NPC246841
0.8476	Intermediate Similarity	NPC7059
0.8471	Intermediate Similarity	NPC110305
0.8466	Intermediate Similarity	NPC35000
0.8462	Intermediate Similarity	NPC82602
0.8462	Intermediate Similarity	NPC470995
0.8457	Intermediate Similarity	NPC246164
0.8457	Intermediate Similarity	NPC294511
0.8457	Intermediate Similarity	NPC44577
0.8457	Intermediate Similarity	NPC121615
0.8452	Intermediate Similarity	NPC478179
0.8447	Intermediate Similarity	NPC228842
0.8447	Intermediate Similarity	NPC156189
0.8434	Intermediate Similarity	NPC472668
0.8434	Intermediate Similarity	NPC207978
0.8434	Intermediate Similarity	NPC79571
0.8434	Intermediate Similarity	NPC211777
0.8434	Intermediate Similarity	NPC471003
0.8428	Intermediate Similarity	NPC233763
0.8424	Intermediate Similarity	NPC474932
0.8421	Intermediate Similarity	NPC236004
0.8418	Intermediate Similarity	NPC84479
0.8415	Intermediate Similarity	NPC204663
0.8412	Intermediate Similarity	NPC159232
0.84	Intermediate Similarity	NPC247563
0.84	Intermediate Similarity	NPC242068
0.8395	Intermediate Similarity	NPC116717
0.8387	Intermediate Similarity	NPC476943
0.8383	Intermediate Similarity	NPC472669
0.8383	Intermediate Similarity	NPC198047
0.8364	Intermediate Similarity	NPC472776
0.8364	Intermediate Similarity	NPC472778

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 NPC473766 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	380
0.1-0.2	930
0.2-0.3	1824
0.3-0.4	2765
0.4-0.5	1958
0.5-0.6	926
0.6-0.7	311
0.7-0.8	55
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8827	High Similarity	NPD5537	Clinical (unspecified phase)
0.8555	High Similarity	NPD8434	Phase 2
0.8057	Intermediate Similarity	NPD6765	Approved
0.8057	Intermediate Similarity	NPD6764	Approved
0.7917	Intermediate Similarity	NPD5761	Phase 2
0.7917	Intermediate Similarity	NPD5760	Phase 2
0.7877	Intermediate Similarity	NPD6785	Approved
0.7877	Intermediate Similarity	NPD6784	Approved
0.7811	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD7075	Discontinued
0.7764	Intermediate Similarity	NPD1471	Phase 3
0.7738	Intermediate Similarity	NPD6599	Discontinued
0.7688	Intermediate Similarity	NPD5494	Approved
0.7644	Intermediate Similarity	NPD1247	Approved
0.763	Intermediate Similarity	NPD919	Approved
0.7602	Intermediate Similarity	NPD7819	Suspended
0.756	Intermediate Similarity	NPD920	Approved
0.7544	Intermediate Similarity	NPD6801	Discontinued
0.7485	Intermediate Similarity	NPD6799	Approved
0.7485	Intermediate Similarity	NPD7411	Suspended
0.7473	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7459	Intermediate Similarity	NPD6559	Discontinued
0.7457	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7457	Intermediate Similarity	NPD5402	Approved
0.7457	Intermediate Similarity	NPD3817	Phase 2
0.744	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD4628	Phase 3
0.7391	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7371	Intermediate Similarity	NPD3749	Approved
0.7368	Intermediate Similarity	NPD3226	Approved
0.7353	Intermediate Similarity	NPD5403	Approved
0.735	Intermediate Similarity	NPD8404	Phase 2
0.7337	Intermediate Similarity	NPD5401	Approved
0.7333	Intermediate Similarity	NPD7799	Discontinued
0.7333	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD3751	Discontinued
0.733	Intermediate Similarity	NPD8285	Discontinued
0.7321	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD7236	Approved
0.7293	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD2796	Approved
0.7263	Intermediate Similarity	NPD3926	Phase 2
0.7258	Intermediate Similarity	NPD8150	Discontinued
0.7246	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7235	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7229	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD4380	Phase 2
0.7222	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7216	Intermediate Similarity	NPD3882	Suspended
0.7216	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD3748	Approved
0.7209	Intermediate Similarity	NPD7239	Suspended
0.7207	Intermediate Similarity	NPD3787	Discontinued
0.7202	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD4107	Approved
0.7198	Intermediate Similarity	NPD5844	Phase 1
0.7189	Intermediate Similarity	NPD8313	Approved
0.7189	Intermediate Similarity	NPD8312	Approved
0.7182	Intermediate Similarity	NPD7473	Discontinued
0.7175	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD8127	Discontinued
0.7143	Intermediate Similarity	NPD6832	Phase 2
0.7143	Intermediate Similarity	NPD1243	Approved
0.7135	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7127	Intermediate Similarity	NPD6166	Phase 2
0.7127	Intermediate Similarity	NPD2403	Approved
0.7127	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7127	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD2346	Discontinued
0.7102	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7093	Intermediate Similarity	NPD6273	Approved
0.7092	Intermediate Similarity	NPD7435	Discontinued
0.7081	Intermediate Similarity	NPD7251	Discontinued
0.7077	Intermediate Similarity	NPD4482	Phase 3
0.7069	Intermediate Similarity	NPD7458	Discontinued
0.7063	Intermediate Similarity	NPD1049	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD3887	Approved
0.7059	Intermediate Similarity	NPD8407	Phase 2
0.7056	Intermediate Similarity	NPD6959	Discontinued
0.7052	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7049	Intermediate Similarity	NPD3818	Discontinued
0.7045	Intermediate Similarity	NPD1934	Approved
0.7043	Intermediate Similarity	NPD7808	Phase 3
0.7035	Intermediate Similarity	NPD2533	Approved
0.7035	Intermediate Similarity	NPD2532	Approved
0.7035	Intermediate Similarity	NPD2534	Approved
0.703	Intermediate Similarity	NPD6355	Discontinued
0.7027	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD6797	Phase 2
0.7017	Intermediate Similarity	NPD6808	Phase 2
0.7017	Intermediate Similarity	NPD6232	Discontinued
0.7006	Intermediate Similarity	NPD2799	Discontinued
0.7	Intermediate Similarity	NPD3750	Approved
0.6989	Remote Similarity	NPD8368	Discontinued
0.6989	Remote Similarity	NPD7685	Pre-registration
0.6982	Remote Similarity	NPD1549	Phase 2
0.6973	Remote Similarity	NPD7074	Phase 3
0.6971	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD6099	Approved
0.6964	Remote Similarity	NPD6100	Approved
0.6957	Remote Similarity	NPD3266	Approved
0.6957	Remote Similarity	NPD3267	Approved
0.6957	Remote Similarity	NPD7907	Approved
0.6941	Remote Similarity	NPD2800	Approved
0.694	Remote Similarity	NPD7784	Clinical (unspecified phase)
0.6936	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD7768	Phase 2
0.6923	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD7054	Approved
0.6911	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD8032	Phase 2
0.6897	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.689	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.6885	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD7472	Approved
0.6881	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6881	Remote Similarity	NPD7874	Approved
0.6867	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD1551	Phase 2
0.686	Remote Similarity	NPD4111	Phase 1
0.6854	Remote Similarity	NPD37	Approved
0.6853	Remote Similarity	NPD6780	Approved
0.6853	Remote Similarity	NPD6782	Approved
0.6853	Remote Similarity	NPD6779	Approved
0.6853	Remote Similarity	NPD6777	Approved
0.6853	Remote Similarity	NPD6778	Approved
0.6853	Remote Similarity	NPD6776	Approved
0.6853	Remote Similarity	NPD6781	Approved
0.6848	Remote Similarity	NPD2313	Discontinued
0.6848	Remote Similarity	NPD3268	Approved
0.6845	Remote Similarity	NPD7097	Phase 1
0.6834	Remote Similarity	NPD7696	Phase 3
0.6834	Remote Similarity	NPD7697	Approved
0.6834	Remote Similarity	NPD7698	Approved
0.6833	Remote Similarity	NPD4965	Approved
0.6833	Remote Similarity	NPD7057	Phase 3
0.6833	Remote Similarity	NPD4967	Phase 2
0.6833	Remote Similarity	NPD4966	Approved
0.6833	Remote Similarity	NPD7058	Phase 2
0.6826	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6826	Remote Similarity	NPD1933	Approved
0.6824	Remote Similarity	NPD2344	Approved
0.6824	Remote Similarity	NPD2353	Approved
0.6824	Remote Similarity	NPD5763	Approved
0.6824	Remote Similarity	NPD5762	Approved
0.6824	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6823	Remote Similarity	NPD8435	Approved
0.6816	Remote Similarity	NPD1465	Phase 2
0.6816	Remote Similarity	NPD2801	Approved
0.6813	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6806	Remote Similarity	NPD8424	Clinical (unspecified phase)
0.6805	Remote Similarity	NPD7033	Discontinued
0.68	Remote Similarity	NPD8319	Approved
0.68	Remote Similarity	NPD7870	Phase 2
0.68	Remote Similarity	NPD8320	Phase 1
0.68	Remote Similarity	NPD7871	Phase 2
0.6798	Remote Similarity	NPD5890	Approved
0.6798	Remote Similarity	NPD5889	Approved
0.6792	Remote Similarity	NPD17	Approved
0.6788	Remote Similarity	NPD7095	Approved
0.6784	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6784	Remote Similarity	NPD3057	Approved
0.6779	Remote Similarity	NPD4665	Approved
0.6774	Remote Similarity	NPD7228	Approved
0.677	Remote Similarity	NPD3972	Approved
0.6766	Remote Similarity	NPD4307	Phase 2
0.6765	Remote Similarity	NPD2438	Suspended
0.6765	Remote Similarity	NPD2935	Discontinued
0.6763	Remote Similarity	NPD5980	Discovery
0.6758	Remote Similarity	NPD6234	Discontinued
0.6747	Remote Similarity	NPD6798	Discontinued
0.6747	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6742	Remote Similarity	NPD6585	Discontinued
0.6739	Remote Similarity	NPD7229	Phase 3
0.6736	Remote Similarity	NPD8360	Approved
0.6736	Remote Similarity	NPD8361	Approved
0.6722	Remote Similarity	NPD8455	Phase 2
0.6707	Remote Similarity	NPD6233	Phase 2
0.6706	Remote Similarity	NPD1510	Phase 2
0.6705	Remote Similarity	NPD7003	Approved
0.6705	Remote Similarity	NPD1512	Approved
0.6701	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.67	Remote Similarity	NPD3533	Approved
0.67	Remote Similarity	NPD7701	Phase 2
0.67	Remote Similarity	NPD2972	Approved
0.6687	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD2897	Discontinued
0.6685	Remote Similarity	NPD5353	Approved
0.6685	Remote Similarity	NPD5616	Clinical (unspecified phase)
0.6685	Remote Similarity	NPD7199	Phase 2
0.6683	Remote Similarity	NPD7801	Approved
0.6683	Remote Similarity	NPD4580	Approved
0.6667	Remote Similarity	NPD1608	Approved
0.6667	Remote Similarity	NPD2309	Approved
0.6667	Remote Similarity	NPD7497	Discontinued
0.6667	Remote Similarity	NPD2354	Approved
0.6667	Remote Similarity	NPD6190	Approved
0.6649	Remote Similarity	NPD2968	Approved

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