NPASS Compound

Structure

NPC329938 OpenBabel07101718192D 46 49 0 0 1 0 0 0 0 0999 V2000 -4.4100 0.8487 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4300 -0.8487 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4500 0.8487 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9600 5.0922 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8487 -0.4900 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.9800 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5061 2.9048 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9200 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4300 0.8487 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8087 1.9248 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2501 3.7934 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6574 2.4148 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9058 3.0651 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4700 -0.8487 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8087 4.8648 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4573 2.4202 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9400 -0.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 1.4700 0.8487 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9800 5.0922 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3548 3.3948 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9800 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.8087 3.8848 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9600 2.4148 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4500 -0.8487 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6574 5.3548 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.6974 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 0.9800 1.6974 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5061 3.8848 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.4900 0.8487 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9800 3.3948 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.9600 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6574 3.3948 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.9600 3.3948 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.4900 5.9409 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1113 1.9248 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.9400 -1.6974 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.6574 6.3348 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4700 2.5461 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4700 -0.8487 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4700 4.2435 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.9400 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.4158 2.2164 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.4900 4.2435 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.5061 4.8648 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4700 0.8487 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 9 1 0 0 0 0 2 17 1 0 0 0 0 4 19 1 0 0 0 0 5 32 1 0 0 0 0 6 32 1 0 0 0 0 8 42 1 0 0 0 0 9 17 1 0 0 0 0 10 12 1 0 0 0 0 10 23 1 0 0 0 0 11 13 2 0 0 0 0 11 20 1 0 0 0 0 12 33 1 0 0 0 0 13 43 1 0 0 0 0 14 24 1 0 0 0 0 15 22 2 0 0 0 0 15 25 1 0 0 0 0 16 20 2 0 0 0 0 16 43 1 0 0 0 0 17 31 1 0 0 0 0 18 3 1 6 0 0 0 18 21 1 0 0 0 0 18 27 1 0 0 0 0 19 35 2 0 0 0 0 19 44 1 0 0 0 0 20 28 1 0 0 0 0 21 14 1 1 0 0 0 21 32 1 0 0 0 0 22 33 1 0 0 0 0 22 34 1 0 0 0 0 23 34 1 0 0 0 0 23 36 2 0 0 0 0 24 37 2 0 0 0 0 24 42 1 0 0 0 0 25 38 2 0 0 0 0 25 45 1 0 0 0 0 26 27 1 0 0 0 0 26 29 1 0 0 0 0 26 30 1 0 0 0 0 27 39 2 0 0 0 0 28 33 1 6 0 0 0 28 45 1 0 0 0 0 29 32 1 0 0 0 0 29 46 1 6 0 0 0 30 34 1 0 0 0 0 30 44 1 6 0 0 0 31 40 2 0 0 0 0 31 46 1 0 0 0 0 33 7 1 6 0 0 0 34 41 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	644.28
Volume:	644.149
LogP:	3.745
LogD:	1.317
LogS:	-3.959
# Rotatable Bonds:	12
TPSA:	172.71
# H-Bond Aceptor:	12
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	12

MedChem Properties

QED Drug-Likeness Score:	0.305
Synthetic Accessibility Score:	5.568
Fsp3:	0.647
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:	-5.17
MDCK Permeability:	3.3059201086871326e-05
Pgp-inhibitor:	1.0
Pgp-substrate:	0.017
Human Intestinal Absorption (HIA):	0.043
20% Bioavailability (F20%):	0.081
30% Bioavailability (F30%):	0.705

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.069
Plasma Protein Binding (PPB):	86.4183120727539%
Volume Distribution (VD):	1.545
Pgp-substrate:	8.669456481933594%

ADMET: Metabolism

CYP1A2-inhibitor:	0.009
CYP1A2-substrate:	0.079
CYP2C19-inhibitor:	0.597
CYP2C19-substrate:	0.256
CYP2C9-inhibitor:	0.927
CYP2C9-substrate:	0.02
CYP2D6-inhibitor:	0.019
CYP2D6-substrate:	0.026
CYP3A4-inhibitor:	0.894
CYP3A4-substrate:	0.879

ADMET: Excretion

Clearance (CL):	3.904
Half-life (T1/2):	0.932

ADMET: Toxicity

hERG Blockers:	0.206
Human Hepatotoxicity (H-HT):	0.633
Drug-inuced Liver Injury (DILI):	0.901
AMES Toxicity:	0.046
Rat Oral Acute Toxicity:	0.991
Maximum Recommended Daily Dose:	0.212
Skin Sensitization:	0.066
Carcinogencity:	0.079
Eye Corrosion:	0.007
Eye Irritation:	0.031
Respiratory Toxicity:	0.76

Download Data

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

Natural Product: NPC329938

Natural Product ID:	NPC329938
*Common Name:**	Granaxylocarpin A
IUPAC Name:	[(1R,3R,4R)-6-[(R)-acetyloxy-[(1R,5R,8aR)-1-(furan-3-yl)-5-hydroxy-8a-methyl-3,6-dioxo-7,8-dihydro-1H-isochromen-5-yl]methyl]-3-(2-methoxy-2-oxoethyl)-2,2,4-trimethyl-5-oxocyclohexyl] 2-methylbutanoate
Synonyms:
Standard InCHIKey:	WLGITUVANAQCQM-CZXGELTISA-N
Standard InCHI:	InChI=1S/C34H44O12/c1-9-17(2)31(40)46-29-26(27(39)18(3)21(32(29,5)6)14-24(37)42-8)30(44-19(4)35)34(41)22-15-25(38)45-28(20-11-13-43-16-20)33(22,7)12-10-23(34)36/h11,13,15-18,21,26,28-30,41H,9-10,12,14H2,1-8H3/t17?,18-,21-,26?,28+,29-,30-,33-,34+/m1/s1
SMILES:	CCC(C)C(=O)OC1C(C(=O)C(C(C1(C)C)CC(=O)OC)C)C(C2(C(=O)CCC3(C2=CC(=O)OC3C4=COC=C4)C)O)OC(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL389681
PubChem CID:	44421657
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO28813	Xylocarpus granatum	Species	Meliaceae	Eukaryota	n.a.	rind	n.a.	DOI[10.1002/hlca.200800177]
NPO28813	Xylocarpus granatum	Species	Meliaceae	Eukaryota	seeds	n.a.	n.a.	PMID[17323995]
NPO28813	Xylocarpus granatum	Species	Meliaceae	Eukaryota	n.a.	bark	n.a.	PMID[17450509]
NPO28813	Xylocarpus granatum	Species	Meliaceae	Eukaryota	seed kernels	n.a.	n.a.	PMID[19908853]
NPO28813	Xylocarpus granatum	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20411928]
NPO28813	Xylocarpus granatum	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31895570]
NPO28813	Xylocarpus granatum	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
NPT168	Cell Line	P388	Mus musculus	IC50	=	9300.0	nM	PMID[512668]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	10000.0	nM	PMID[512668]

☑ 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 NPC329938 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	343
0.1-0.2	1307
0.2-0.3	3020
0.3-0.4	5310
0.4-0.5	9962
0.5-0.6	9716
0.6-0.7	7838
0.7-0.8	4693
0.8-0.85	245
0.85-0.9	204
0.9-0.95	55
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9671	High Similarity	NPC173544
0.9613	High Similarity	NPC469849
0.9613	High Similarity	NPC470940
0.9605	High Similarity	NPC469485
0.9551	High Similarity	NPC470875
0.9548	High Similarity	NPC292389
0.9548	High Similarity	NPC477405
0.9548	High Similarity	NPC469338
0.9545	High Similarity	NPC477402
0.949	High Similarity	NPC472282
0.9487	High Similarity	NPC276551
0.9484	High Similarity	NPC69028
0.9484	High Similarity	NPC193798
0.9481	High Similarity	NPC477403
0.943	High Similarity	NPC160651
0.9419	High Similarity	NPC25255
0.9367	High Similarity	NPC173516
0.9367	High Similarity	NPC472775
0.9367	High Similarity	NPC472774
0.9363	High Similarity	NPC476858
0.9363	High Similarity	NPC476856
0.9363	High Similarity	NPC476857
0.9359	High Similarity	NPC263432
0.9359	High Similarity	NPC82851
0.9308	High Similarity	NPC471397
0.9299	High Similarity	NPC472773
0.9295	High Similarity	NPC472653
0.929	High Similarity	NPC249021
0.929	High Similarity	NPC472283
0.9286	High Similarity	NPC264943
0.9245	High Similarity	NPC476850
0.9245	High Similarity	NPC476861
0.9245	High Similarity	NPC476853
0.9241	High Similarity	NPC123088
0.9241	High Similarity	NPC476860
0.9236	High Similarity	NPC472771
0.9198	High Similarity	NPC471437
0.9182	High Similarity	NPC23387
0.9177	High Similarity	NPC224394
0.9177	High Similarity	NPC663
0.9172	High Similarity	NPC191828
0.9167	High Similarity	NPC36655
0.9167	High Similarity	NPC167142
0.9167	High Similarity	NPC472772
0.9167	High Similarity	NPC261597
0.9167	High Similarity	NPC45101
0.9161	High Similarity	NPC469336
0.9161	High Similarity	NPC44675
0.9161	High Similarity	NPC214541
0.9114	High Similarity	NPC5079
0.9114	High Similarity	NPC200782
0.9114	High Similarity	NPC470939
0.9108	High Similarity	NPC475967
0.9108	High Similarity	NPC237155
0.9108	High Similarity	NPC307383
0.9097	High Similarity	NPC178932
0.9097	High Similarity	NPC282445
0.9097	High Similarity	NPC30222
0.9068	High Similarity	NPC472652
0.9062	High Similarity	NPC472141
0.9057	High Similarity	NPC134254
0.9057	High Similarity	NPC288602
0.9057	High Similarity	NPC39986
0.9057	High Similarity	NPC234660
0.9057	High Similarity	NPC302369
0.9057	High Similarity	NPC88841
0.9057	High Similarity	NPC51568
0.9051	High Similarity	NPC335761
0.9051	High Similarity	NPC470789
0.9045	High Similarity	NPC286722
0.9038	High Similarity	NPC35000
0.9038	High Similarity	NPC281258
0.9038	High Similarity	NPC469850
0.9026	High Similarity	NPC159927
0.9026	High Similarity	NPC469335
0.9026	High Similarity	NPC477404
0.9026	High Similarity	NPC196864
0.9006	High Similarity	NPC472651
0.9	High Similarity	NPC470182
0.8994	High Similarity	NPC188649
0.8987	High Similarity	NPC473473
0.8987	High Similarity	NPC475295
0.8981	High Similarity	NPC107646
0.8981	High Similarity	NPC126723
0.8981	High Similarity	NPC209364
0.8981	High Similarity	NPC263265
0.8981	High Similarity	NPC60973
0.897	High Similarity	NPC478177
0.8951	High Similarity	NPC271235
0.8944	High Similarity	NPC121995
0.8944	High Similarity	NPC475779
0.8938	High Similarity	NPC476197
0.8931	High Similarity	NPC305016
0.8931	High Similarity	NPC287559
0.8931	High Similarity	NPC475381
0.8924	High Similarity	NPC472776
0.8924	High Similarity	NPC472777
0.8924	High Similarity	NPC472778
0.8924	High Similarity	NPC187149
0.8924	High Similarity	NPC299038
0.8917	High Similarity	NPC476262
0.891	High Similarity	NPC44577
0.891	High Similarity	NPC75906
0.891	High Similarity	NPC476201
0.891	High Similarity	NPC469503
0.8896	High Similarity	NPC82602
0.8889	High Similarity	NPC473766
0.8889	High Similarity	NPC473753
0.8889	High Similarity	NPC262198
0.8882	High Similarity	NPC271657
0.8875	High Similarity	NPC18986
0.8875	High Similarity	NPC68848
0.8875	High Similarity	NPC96443
0.8875	High Similarity	NPC149896
0.8875	High Similarity	NPC207978
0.8875	High Similarity	NPC290400
0.8875	High Similarity	NPC18347
0.8875	High Similarity	NPC117986
0.8848	High Similarity	NPC471632
0.8848	High Similarity	NPC94763
0.8846	High Similarity	NPC18135
0.8841	High Similarity	NPC285227
0.8839	High Similarity	NPC125182
0.8839	High Similarity	NPC69647
0.8834	High Similarity	NPC296558
0.8831	High Similarity	NPC255414
0.8827	High Similarity	NPC149945
0.882	High Similarity	NPC469846
0.882	High Similarity	NPC198047
0.882	High Similarity	NPC419
0.882	High Similarity	NPC472139
0.8805	High Similarity	NPC88007
0.8797	High Similarity	NPC92979
0.8795	High Similarity	NPC469633
0.8782	High Similarity	NPC476122
0.8782	High Similarity	NPC46551
0.878	High Similarity	NPC470995
0.8773	High Similarity	NPC270312
0.8773	High Similarity	NPC478179
0.8758	High Similarity	NPC470792
0.8758	High Similarity	NPC476944
0.8758	High Similarity	NPC211777
0.875	High Similarity	NPC475226
0.875	High Similarity	NPC121158
0.8742	High Similarity	NPC41880
0.8735	High Similarity	NPC469576
0.8735	High Similarity	NPC236004
0.8727	High Similarity	NPC169299
0.8727	High Similarity	NPC160818
0.8726	High Similarity	NPC272590
0.872	High Similarity	NPC472765
0.872	High Similarity	NPC472766
0.8718	High Similarity	NPC472654
0.8718	High Similarity	NPC195325
0.8712	High Similarity	NPC478178
0.8712	High Similarity	NPC93172
0.8712	High Similarity	NPC97574
0.871	High Similarity	NPC470941
0.871	High Similarity	NPC221809
0.8706	High Similarity	NPC247563
0.8706	High Similarity	NPC105395
0.8706	High Similarity	NPC242068
0.8704	High Similarity	NPC285567
0.8693	High Similarity	NPC243577
0.8693	High Similarity	NPC476946
0.8688	High Similarity	NPC194499
0.8688	High Similarity	NPC195954
0.8688	High Similarity	NPC197137
0.8688	High Similarity	NPC470118
0.8679	High Similarity	NPC75310
0.8675	High Similarity	NPC469848
0.8671	High Similarity	NPC33938
0.8671	High Similarity	NPC147168
0.8671	High Similarity	NPC268905
0.8662	High Similarity	NPC156189
0.8659	High Similarity	NPC472764
0.8659	High Similarity	NPC476224
0.8659	High Similarity	NPC100333
0.865	High Similarity	NPC56358
0.8645	High Similarity	NPC346
0.8642	High Similarity	NPC471167
0.8642	High Similarity	NPC197596
0.8642	High Similarity	NPC471166
0.8642	High Similarity	NPC472767
0.8636	High Similarity	NPC137295
0.8636	High Similarity	NPC251865
0.8634	High Similarity	NPC474611
0.8634	High Similarity	NPC262872
0.8634	High Similarity	NPC472779
0.8631	High Similarity	NPC472665
0.8618	High Similarity	NPC90296
0.8616	High Similarity	NPC302054
0.8616	High Similarity	NPC57998
0.8616	High Similarity	NPC253201
0.8614	High Similarity	NPC159232
0.8599	High Similarity	NPC470790
0.8599	High Similarity	NPC211625
0.8599	High Similarity	NPC470791
0.859	High Similarity	NPC250228
0.8589	High Similarity	NPC283209

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 NPC329938 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	287
0.1-0.2	975
0.2-0.3	2077
0.3-0.4	2576
0.4-0.5	1885
0.5-0.6	986
0.6-0.7	300
0.7-0.8	61
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8757	High Similarity	NPD8434	Phase 2
0.8562	High Similarity	NPD5760	Phase 2
0.8562	High Similarity	NPD5761	Phase 2
0.8133	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7829	Intermediate Similarity	NPD6765	Approved
0.7829	Intermediate Similarity	NPD6764	Approved
0.7751	Intermediate Similarity	NPD7075	Discontinued
0.7679	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7654	Intermediate Similarity	NPD6784	Approved
0.7654	Intermediate Similarity	NPD6785	Approved
0.7619	Intermediate Similarity	NPD6801	Discontinued
0.7605	Intermediate Similarity	NPD6599	Discontinued
0.7593	Intermediate Similarity	NPD4628	Phase 3
0.7574	Intermediate Similarity	NPD7819	Suspended
0.7528	Intermediate Similarity	NPD6559	Discontinued
0.75	Intermediate Similarity	NPD8404	Phase 2
0.7459	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7446	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.744	Intermediate Similarity	NPD3226	Approved
0.7427	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7427	Intermediate Similarity	NPD5402	Approved
0.7427	Intermediate Similarity	NPD3817	Phase 2
0.736	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD7411	Suspended
0.7349	Intermediate Similarity	NPD6799	Approved
0.7321	Intermediate Similarity	NPD920	Approved
0.7321	Intermediate Similarity	NPD5403	Approved
0.7317	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7314	Intermediate Similarity	NPD1247	Approved
0.7305	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD3818	Discontinued
0.7301	Intermediate Similarity	NPD1471	Phase 3
0.7299	Intermediate Similarity	NPD919	Approved
0.7294	Intermediate Similarity	NPD4380	Phase 2
0.7283	Intermediate Similarity	NPD3882	Suspended
0.7253	Intermediate Similarity	NPD8312	Approved
0.7253	Intermediate Similarity	NPD8313	Approved
0.7247	Intermediate Similarity	NPD7473	Discontinued
0.7241	Intermediate Similarity	NPD3749	Approved
0.7241	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7228	Intermediate Similarity	NPD8150	Discontinued
0.7202	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD5401	Approved
0.7195	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7191	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7184	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7168	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7159	Intermediate Similarity	NPD5494	Approved
0.7119	Intermediate Similarity	NPD8127	Discontinued
0.7111	Intermediate Similarity	NPD7799	Discontinued
0.7111	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.711	Intermediate Similarity	NPD1934	Approved
0.7104	Intermediate Similarity	NPD7808	Phase 3
0.7104	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD2533	Approved
0.7101	Intermediate Similarity	NPD2532	Approved
0.7101	Intermediate Similarity	NPD2534	Approved
0.7095	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD6166	Phase 2
0.7088	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7079	Intermediate Similarity	NPD6232	Discontinued
0.7072	Intermediate Similarity	NPD5844	Phase 1
0.7069	Intermediate Similarity	NPD2801	Approved
0.7066	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7049	Intermediate Similarity	NPD7251	Discontinued
0.7035	Intermediate Similarity	NPD7458	Discontinued
0.703	Intermediate Similarity	NPD2796	Approved
0.7027	Intermediate Similarity	NPD8407	Phase 2
0.7019	Intermediate Similarity	NPD3268	Approved
0.7	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.6995	Remote Similarity	NPD6797	Phase 2
0.6994	Remote Similarity	NPD6355	Discontinued
0.6989	Remote Similarity	NPD7768	Phase 2
0.6988	Remote Similarity	NPD2346	Discontinued
0.6982	Remote Similarity	NPD7236	Approved
0.6978	Remote Similarity	NPD7054	Approved
0.6974	Remote Similarity	NPD7435	Discontinued
0.697	Remote Similarity	NPD7033	Discontinued
0.697	Remote Similarity	NPD2799	Discontinued
0.6968	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD3750	Approved
0.6959	Remote Similarity	NPD1512	Approved
0.6959	Remote Similarity	NPD6273	Approved
0.6957	Remote Similarity	NPD8368	Discontinued
0.6957	Remote Similarity	NPD7685	Pre-registration
0.6946	Remote Similarity	NPD1549	Phase 2
0.6946	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD3926	Phase 2
0.694	Remote Similarity	NPD7472	Approved
0.694	Remote Similarity	NPD7074	Phase 3
0.6928	Remote Similarity	NPD6100	Approved
0.6928	Remote Similarity	NPD1551	Phase 2
0.6928	Remote Similarity	NPD6099	Approved
0.6927	Remote Similarity	NPD6959	Discontinued
0.6923	Remote Similarity	NPD3751	Discontinued
0.6914	Remote Similarity	NPD2313	Discontinued
0.6914	Remote Similarity	NPD37	Approved
0.691	Remote Similarity	NPD6234	Discontinued
0.6905	Remote Similarity	NPD1243	Approved
0.6905	Remote Similarity	NPD2800	Approved
0.6893	Remote Similarity	NPD4967	Phase 2
0.6893	Remote Similarity	NPD4965	Approved
0.6893	Remote Similarity	NPD4966	Approved
0.6886	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6886	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6886	Remote Similarity	NPD2344	Approved
0.6879	Remote Similarity	NPD7239	Suspended
0.6867	Remote Similarity	NPD1510	Phase 2
0.6856	Remote Similarity	NPD8285	Discontinued
0.6851	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.685	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.685	Remote Similarity	NPD7874	Approved
0.6845	Remote Similarity	NPD7907	Approved
0.6842	Remote Similarity	NPD1511	Approved
0.6839	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6826	Remote Similarity	NPD2935	Discontinued
0.6821	Remote Similarity	NPD6782	Approved
0.6821	Remote Similarity	NPD6777	Approved
0.6821	Remote Similarity	NPD6781	Approved
0.6821	Remote Similarity	NPD6780	Approved
0.6821	Remote Similarity	NPD6778	Approved
0.6821	Remote Similarity	NPD6779	Approved
0.6821	Remote Similarity	NPD6776	Approved
0.6802	Remote Similarity	NPD7697	Approved
0.6802	Remote Similarity	NPD7696	Phase 3
0.6802	Remote Similarity	NPD7698	Approved
0.6796	Remote Similarity	NPD3787	Discontinued
0.679	Remote Similarity	NPD6832	Phase 2
0.6789	Remote Similarity	NPD8360	Approved
0.6789	Remote Similarity	NPD8361	Approved
0.6786	Remote Similarity	NPD5762	Approved
0.6786	Remote Similarity	NPD5763	Approved
0.678	Remote Similarity	NPD1465	Phase 2
0.6768	Remote Similarity	NPD7870	Phase 2
0.6768	Remote Similarity	NPD7871	Phase 2
0.6768	Remote Similarity	NPD8320	Phase 1
0.6768	Remote Similarity	NPD8319	Approved
0.6766	Remote Similarity	NPD4308	Phase 3
0.6766	Remote Similarity	NPD3748	Approved
0.675	Remote Similarity	NPD7701	Phase 2
0.6748	Remote Similarity	NPD7095	Approved
0.674	Remote Similarity	NPD7199	Phase 2
0.6739	Remote Similarity	NPD7228	Approved
0.6733	Remote Similarity	NPD7801	Approved
0.6725	Remote Similarity	NPD6190	Approved
0.6725	Remote Similarity	NPD2309	Approved
0.6724	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6708	Remote Similarity	NPD3267	Approved
0.6708	Remote Similarity	NPD3266	Approved
0.6708	Remote Similarity	NPD2797	Approved
0.6707	Remote Similarity	NPD6798	Discontinued
0.6707	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD3764	Approved
0.6703	Remote Similarity	NPD6808	Phase 2
0.6703	Remote Similarity	NPD7229	Phase 3
0.6702	Remote Similarity	NPD8435	Approved
0.6699	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD447	Suspended
0.6685	Remote Similarity	NPD8455	Phase 2
0.6667	Remote Similarity	NPD8032	Phase 2
0.6667	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4111	Phase 1
0.6667	Remote Similarity	NPD7003	Approved
0.6667	Remote Similarity	NPD6233	Phase 2
0.6667	Remote Similarity	NPD4665	Approved
0.6667	Remote Similarity	NPD8166	Discontinued
0.665	Remote Similarity	NPD7783	Phase 2
0.665	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6647	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6647	Remote Similarity	NPD1607	Approved
0.6633	Remote Similarity	NPD7700	Phase 2
0.6633	Remote Similarity	NPD7699	Phase 2
0.6631	Remote Similarity	NPD5953	Discontinued
0.663	Remote Similarity	NPD4575	Clinical (unspecified phase)
0.663	Remote Similarity	NPD7784	Clinical (unspecified phase)
0.663	Remote Similarity	NPD2403	Approved
0.6628	Remote Similarity	NPD2354	Approved
0.6628	Remote Similarity	NPD3887	Approved
0.6627	Remote Similarity	NPD1240	Approved
0.6627	Remote Similarity	NPD4060	Phase 1
0.6625	Remote Similarity	NPD1608	Approved
0.6613	Remote Similarity	NPD7286	Phase 2
0.6612	Remote Similarity	NPD5711	Approved
0.6612	Remote Similarity	NPD5710	Approved
0.6607	Remote Similarity	NPD7097	Phase 1
0.6597	Remote Similarity	NPD8424	Clinical (unspecified phase)
0.6588	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6588	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6588	Remote Similarity	NPD6004	Phase 3
0.6588	Remote Similarity	NPD6005	Phase 3
0.6588	Remote Similarity	NPD6002	Phase 3
0.6583	Remote Similarity	NPD3057	Approved
0.6582	Remote Similarity	NPD8485	Approved
0.657	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.657	Remote Similarity	NPD4110	Phase 3

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