NPASS Compound

Structure

NPC262386 OpenBabel07101718292D 38 44 0 0 1 0 0 0 0 0999 V2000 -2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3660 -1.3660 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 -3.5686 3.9945 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 -4.5468 4.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7481 -2.2252 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3776 2.5933 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 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 2.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.1619 -1.4151 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.5704 -0.5023 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.9842 0.3079 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.9894 0.2052 0.0000 C 0 0 2 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 -0.8660 1.5000 0.0000 C 0 0 1 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 0.0000 1.0000 0.0000 C 0 0 1 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 1.5810 -0.7075 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.1327 0.8801 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.7429 -2.1226 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.5651 -0.3997 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3927 1.2206 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4032 1.0154 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 0.6936 1.4435 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0468 3.3364 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1672 -1.5177 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9035 1.3252 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5862 -0.8101 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3 5 1 0 0 0 0 3 11 2 0 0 0 0 4 6 2 0 0 0 0 4 10 1 0 0 0 0 5 25 1 0 0 0 0 6 33 1 0 0 0 0 7 12 1 0 0 0 0 7 24 1 0 0 0 0 8 27 1 0 0 0 0 9 10 2 0 0 0 0 9 33 1 0 0 0 0 11 21 1 0 0 0 0 11 24 1 0 0 0 0 12 10 1 6 0 0 0 12 34 1 0 0 0 0 13 8 1 1 0 0 0 13 14 1 0 0 0 0 13 35 1 0 0 0 0 14 15 1 0 0 0 0 14 28 1 6 0 0 0 15 16 1 0 0 0 0 15 29 1 1 0 0 0 16 22 1 0 0 0 0 16 30 1 6 0 0 0 17 18 1 0 0 0 0 17 19 1 0 0 0 0 17 37 1 6 0 0 0 18 20 1 0 0 0 0 18 36 1 6 0 0 0 19 24 1 0 0 0 0 19 25 1 6 0 0 0 20 26 1 6 0 0 0 20 36 1 0 0 0 0 21 31 2 0 0 0 0 21 34 1 0 0 0 0 22 35 1 0 0 0 0 22 38 1 1 0 0 0 23 26 1 0 0 0 0 23 32 2 0 0 0 0 23 37 1 0 0 0 0 24 1 1 1 0 0 0 25 2 1 6 0 0 0 26 25 1 1 0 0 0 26 38 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	534.17
Volume:	490.657
LogP:	1.07
LogD:	0.628
LogS:	-3.781
# Rotatable Bonds:	4
TPSA:	177.65
# H-Bond Aceptor:	12
# H-Bond Donor:	4
# Rings:	8
# Heavy Atoms:	12

MedChem Properties

QED Drug-Likeness Score:	0.288
Synthetic Accessibility Score:	6.41
Fsp3:	0.692
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:	-5.991
MDCK Permeability:	7.288753113243729e-05
Pgp-inhibitor:	0.541
Pgp-substrate:	0.96
Human Intestinal Absorption (HIA):	0.9
20% Bioavailability (F20%):	0.19
30% Bioavailability (F30%):	0.996

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.115
Plasma Protein Binding (PPB):	82.45178985595703%
Volume Distribution (VD):	1.038
Pgp-substrate:	15.896764755249023%

ADMET: Metabolism

CYP1A2-inhibitor:	0.012
CYP1A2-substrate:	0.702
CYP2C19-inhibitor:	0.016
CYP2C19-substrate:	0.435
CYP2C9-inhibitor:	0.015
CYP2C9-substrate:	0.017
CYP2D6-inhibitor:	0.005
CYP2D6-substrate:	0.097
CYP3A4-inhibitor:	0.536
CYP3A4-substrate:	0.239

ADMET: Excretion

Clearance (CL):	3.538
Half-life (T1/2):	0.611

ADMET: Toxicity

hERG Blockers:	0.117
Human Hepatotoxicity (H-HT):	0.148
Drug-inuced Liver Injury (DILI):	0.256
AMES Toxicity:	0.228
Rat Oral Acute Toxicity:	0.604
Maximum Recommended Daily Dose:	0.455
Skin Sensitization:	0.155
Carcinogencity:	0.868
Eye Corrosion:	0.004
Eye Irritation:	0.024
Respiratory Toxicity:	0.951

Download Data

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

Natural Product: NPC262386

Natural Product ID:	NPC262386
*Common Name:**	Fibraurinoside
IUPAC Name:	n.a.
Synonyms:	Fibraurinoside
Standard InCHIKey:	PPILOQQTEQXAMT-HSWSLHEESA-N
Standard InCHI:	InChI=1S/C26H30O12/c1-24-7-12(10-4-6-33-9-10)34-21(31)11(24)3-5-25(2)19(24)17-18-20(36-18)26(25,23(32)37-17)38-22-16(30)15(29)14(28)13(8-27)35-22/h3-4,6,9,12-20,22,27-30H,5,7-8H2,1-2H3/t12-,13-,14-,15+,16-,17-,18+,19+,20+,22+,24-,25-,26+/m1/s1
SMILES:	C[C@@]12C[C@H](c3ccoc3)OC(=O)C1=CC[C@]1(C)[C@H]2[C@H]2[C@H]3[C@@H]([C@@]1(C(=O)O2)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O)O3
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL399731
PubChem CID:	44445724
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0003909] Fatty Acyls [CHEMONTID:0001766] Fatty acyl glycosides [CHEMONTID:0003861] Fatty acyl glycosides of mono- and disaccharides

*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
NPO10715	Fibraurea tinctoria	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17994701]
NPO10715	Fibraurea tinctoria	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18829331]
NPO10715	Fibraurea tinctoria	Species	Menispermaceae	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	1
Others	12

Activity Type	# Activity
Individual Protein	1
Organism	12

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT109	Individual Protein	Cytochrome P450 3A4	Homo sapiens	IC50	>	100000.0	nM	PMID[556259]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	25.07	%	PMID[556260]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	23.03	%	PMID[556260]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	18.67	%	PMID[556260]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	18.48	%	PMID[556260]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	20.89	%	PMID[556260]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	20.36	%	PMID[556260]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	18.99	%	PMID[556260]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	18.18	%	PMID[556260]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	17.12	%	PMID[556260]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	25.03	%	PMID[556260]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	25.25	%	PMID[556260]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	24.8	%	PMID[556260]

☑ 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 NPC262386 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	415
0.1-0.2	1697
0.2-0.3	3645
0.3-0.4	6735
0.4-0.5	9920
0.5-0.6	9676
0.6-0.7	8288
0.7-0.8	2116
0.8-0.85	112
0.85-0.9	71
0.9-0.95	21
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9503	High Similarity	NPC271657
0.9451	High Similarity	NPC169299
0.9451	High Similarity	NPC160818
0.9383	High Similarity	NPC146991
0.9379	High Similarity	NPC18347
0.9379	High Similarity	NPC149896
0.9325	High Similarity	NPC93172
0.9325	High Similarity	NPC97574
0.9273	High Similarity	NPC82602
0.9259	High Similarity	NPC211777
0.9202	High Similarity	NPC198047
0.9146	High Similarity	NPC470182
0.9096	High Similarity	NPC471397
0.9096	High Similarity	NPC271235
0.9085	High Similarity	NPC134254
0.9085	High Similarity	NPC51568
0.9085	High Similarity	NPC234660
0.9085	High Similarity	NPC302369
0.9085	High Similarity	NPC39986
0.9036	High Similarity	NPC100333
0.9036	High Similarity	NPC173516
0.9024	High Similarity	NPC200782
0.9024	High Similarity	NPC207978
0.9024	High Similarity	NPC5079
0.9018	High Similarity	NPC262872
0.8963	High Similarity	NPC335761
0.8963	High Similarity	NPC472653
0.8957	High Similarity	NPC187149
0.8922	High Similarity	NPC472651
0.8916	High Similarity	NPC476856
0.8916	High Similarity	NPC476857
0.8916	High Similarity	NPC276551
0.8916	High Similarity	NPC476858
0.8909	High Similarity	NPC290400
0.8909	High Similarity	NPC117986
0.8909	High Similarity	NPC82851
0.8909	High Similarity	NPC96443
0.8902	High Similarity	NPC475967
0.8902	High Similarity	NPC475295
0.8902	High Similarity	NPC473473
0.8869	High Similarity	NPC472652
0.8869	High Similarity	NPC160651
0.8862	High Similarity	NPC470875
0.8862	High Similarity	NPC23387
0.8855	High Similarity	NPC477405
0.8855	High Similarity	NPC292389
0.8855	High Similarity	NPC469338
0.8841	High Similarity	NPC36655
0.8841	High Similarity	NPC45101
0.8841	High Similarity	NPC261597
0.8841	High Similarity	NPC299038
0.8841	High Similarity	NPC286722
0.8834	High Similarity	NPC214541
0.8834	High Similarity	NPC44675
0.8827	High Similarity	NPC147168
0.881	High Similarity	NPC472282
0.881	High Similarity	NPC476853
0.881	High Similarity	NPC476850
0.881	High Similarity	NPC476861
0.881	High Similarity	NPC472775
0.881	High Similarity	NPC472774
0.8802	High Similarity	NPC469849
0.8802	High Similarity	NPC476860
0.8802	High Similarity	NPC470940
0.8795	High Similarity	NPC69028
0.8788	High Similarity	NPC307383
0.878	High Similarity	NPC209364
0.8773	High Similarity	NPC57998
0.8743	High Similarity	NPC247563
0.8743	High Similarity	NPC242068
0.8743	High Similarity	NPC469846
0.8735	High Similarity	NPC477402
0.8735	High Similarity	NPC25255
0.8727	High Similarity	NPC249021
0.872	High Similarity	NPC476262
0.8712	High Similarity	NPC476201
0.8712	High Similarity	NPC476939
0.8712	High Similarity	NPC44577
0.8712	High Similarity	NPC469503
0.8712	High Similarity	NPC476940
0.869	High Similarity	NPC123088
0.8683	High Similarity	NPC470939
0.8683	High Similarity	NPC193798
0.8678	High Similarity	NPC470938
0.8675	High Similarity	NPC477403
0.8667	High Similarity	NPC60973
0.8667	High Similarity	NPC107646
0.8667	High Similarity	NPC126723
0.8659	High Similarity	NPC282445
0.8639	High Similarity	NPC472141
0.8636	High Similarity	NPC105395
0.8631	High Similarity	NPC472139
0.8631	High Similarity	NPC472773
0.8623	High Similarity	NPC305016
0.8623	High Similarity	NPC475381
0.8614	High Similarity	NPC472776
0.8614	High Similarity	NPC472778
0.8614	High Similarity	NPC472777
0.8606	High Similarity	NPC264943
0.8598	High Similarity	NPC268905
0.8596	High Similarity	NPC470995
0.8589	High Similarity	NPC476122
0.8571	High Similarity	NPC472771
0.8571	High Similarity	NPC263432
0.8555	High Similarity	NPC236004
0.8547	High Similarity	NPC159232
0.8528	High Similarity	NPC125182
0.8528	High Similarity	NPC69647
0.8521	High Similarity	NPC419
0.8503	High Similarity	NPC472283
0.8494	Intermediate Similarity	NPC469336
0.8494	Intermediate Similarity	NPC35000
0.848	Intermediate Similarity	NPC473753
0.848	Intermediate Similarity	NPC473766
0.8466	Intermediate Similarity	NPC476942
0.8466	Intermediate Similarity	NPC476941
0.8466	Intermediate Similarity	NPC7388
0.8462	Intermediate Similarity	NPC329938
0.8457	Intermediate Similarity	NPC478177
0.8452	Intermediate Similarity	NPC237155
0.8448	Intermediate Similarity	NPC94763
0.8447	Intermediate Similarity	NPC86935
0.8443	Intermediate Similarity	NPC469485
0.8443	Intermediate Similarity	NPC263265
0.8434	Intermediate Similarity	NPC178932
0.8434	Intermediate Similarity	NPC30222
0.843	Intermediate Similarity	NPC242334
0.8424	Intermediate Similarity	NPC18135
0.8421	Intermediate Similarity	NPC475779
0.8421	Intermediate Similarity	NPC478178
0.8412	Intermediate Similarity	NPC476197
0.8405	Intermediate Similarity	NPC476938
0.8405	Intermediate Similarity	NPC476937
0.8405	Intermediate Similarity	NPC255414
0.8393	Intermediate Similarity	NPC472772
0.8393	Intermediate Similarity	NPC173544
0.8383	Intermediate Similarity	NPC469850
0.8383	Intermediate Similarity	NPC281258
0.8382	Intermediate Similarity	NPC302392
0.8353	Intermediate Similarity	NPC188649
0.8352	Intermediate Similarity	NPC472665
0.8352	Intermediate Similarity	NPC470181
0.8333	Intermediate Similarity	NPC137295
0.8324	Intermediate Similarity	NPC327922
0.8314	Intermediate Similarity	NPC472670
0.8314	Intermediate Similarity	NPC121995
0.8314	Intermediate Similarity	NPC307781
0.8304	Intermediate Similarity	NPC88841
0.8304	Intermediate Similarity	NPC288602
0.8294	Intermediate Similarity	NPC470789
0.8293	Intermediate Similarity	NPC221809
0.8293	Intermediate Similarity	NPC470941
0.8293	Intermediate Similarity	NPC250228
0.8284	Intermediate Similarity	NPC167142
0.8282	Intermediate Similarity	NPC5676
0.8276	Intermediate Similarity	NPC472659
0.8266	Intermediate Similarity	NPC478179
0.8263	Intermediate Similarity	NPC75906
0.8256	Intermediate Similarity	NPC259943
0.8253	Intermediate Similarity	NPC159927
0.8253	Intermediate Similarity	NPC196864
0.8253	Intermediate Similarity	NPC477404
0.8253	Intermediate Similarity	NPC469335
0.8253	Intermediate Similarity	NPC476936
0.8246	Intermediate Similarity	NPC18986
0.8239	Intermediate Similarity	NPC469576
0.8239	Intermediate Similarity	NPC471632
0.8235	Intermediate Similarity	NPC475226
0.8235	Intermediate Similarity	NPC473368
0.8232	Intermediate Similarity	NPC346
0.8221	Intermediate Similarity	NPC476944
0.8218	Intermediate Similarity	NPC472765
0.8218	Intermediate Similarity	NPC296558
0.8218	Intermediate Similarity	NPC472766
0.8218	Intermediate Similarity	NPC472673
0.8208	Intermediate Similarity	NPC120012
0.8208	Intermediate Similarity	NPC214600
0.8198	Intermediate Similarity	NPC165218
0.8193	Intermediate Similarity	NPC195325
0.8192	Intermediate Similarity	NPC124828
0.8192	Intermediate Similarity	NPC469633
0.8176	Intermediate Similarity	NPC195954
0.8176	Intermediate Similarity	NPC88007
0.8176	Intermediate Similarity	NPC194499
0.8171	Intermediate Similarity	NPC472650
0.8161	Intermediate Similarity	NPC472764
0.8161	Intermediate Similarity	NPC102465
0.816	Intermediate Similarity	NPC243577
0.8144	Intermediate Similarity	NPC46551
0.814	Intermediate Similarity	NPC68848
0.814	Intermediate Similarity	NPC470792
0.814	Intermediate Similarity	NPC472668
0.814	Intermediate Similarity	NPC5741
0.8136	Intermediate Similarity	NPC471437
0.8136	Intermediate Similarity	NPC477824
0.8129	Intermediate Similarity	NPC472779
0.8129	Intermediate Similarity	NPC474611
0.8121	Intermediate Similarity	NPC262198
0.8111	Intermediate Similarity	NPC254588
0.811	Intermediate Similarity	NPC251865

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 NPC262386 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	350
0.1-0.2	1168
0.2-0.3	2406
0.3-0.4	2809
0.4-0.5	1603
0.5-0.6	599
0.6-0.7	188
0.7-0.8	26
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
0.8167	Intermediate Similarity	NPD8434	Phase 2
0.7849	Intermediate Similarity	NPD5760	Phase 2
0.7849	Intermediate Similarity	NPD5761	Phase 2
0.7701	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.767	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7596	Intermediate Similarity	NPD6559	Discontinued
0.7569	Intermediate Similarity	NPD3751	Discontinued
0.7527	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7459	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7446	Intermediate Similarity	NPD6797	Phase 2
0.7444	Intermediate Similarity	NPD3787	Discontinued
0.7405	Intermediate Similarity	NPD6764	Approved
0.7405	Intermediate Similarity	NPD7251	Discontinued
0.7405	Intermediate Similarity	NPD6765	Approved
0.7391	Intermediate Similarity	NPD7074	Phase 3
0.7366	Intermediate Similarity	NPD7808	Phase 3
0.734	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7326	Intermediate Similarity	NPD8312	Approved
0.7326	Intermediate Similarity	NPD8313	Approved
0.7318	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD7435	Discontinued
0.7304	Intermediate Similarity	NPD8404	Phase 2
0.7283	Intermediate Similarity	NPD3818	Discontinued
0.726	Intermediate Similarity	NPD5619	Clinical (unspecified phase)
0.7249	Intermediate Similarity	NPD6784	Approved
0.7249	Intermediate Similarity	NPD6785	Approved
0.7247	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7243	Intermediate Similarity	NPD7054	Approved
0.7222	Intermediate Similarity	NPD7075	Discontinued
0.7204	Intermediate Similarity	NPD7472	Approved
0.7189	Intermediate Similarity	NPD7228	Approved
0.7189	Intermediate Similarity	NPD7799	Discontinued
0.7175	Intermediate Similarity	NPD6599	Discontinued
0.7157	Intermediate Similarity	NPD6778	Approved
0.7157	Intermediate Similarity	NPD6781	Approved
0.7157	Intermediate Similarity	NPD6782	Approved
0.7157	Intermediate Similarity	NPD6780	Approved
0.7157	Intermediate Similarity	NPD6779	Approved
0.7157	Intermediate Similarity	NPD6777	Approved
0.7157	Intermediate Similarity	NPD6776	Approved
0.7143	Intermediate Similarity	NPD5494	Approved
0.7128	Intermediate Similarity	NPD7685	Pre-registration
0.7111	Intermediate Similarity	NPD5402	Approved
0.7105	Intermediate Similarity	NPD8407	Phase 2
0.71	Intermediate Similarity	NPD8319	Approved
0.71	Intermediate Similarity	NPD8320	Phase 1
0.7095	Intermediate Similarity	NPD6801	Discontinued
0.7094	Intermediate Similarity	NPD7874	Approved
0.7094	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD6166	Phase 2
0.7059	Intermediate Similarity	NPD5844	Phase 1
0.7052	Intermediate Similarity	NPD4628	Phase 3
0.705	Intermediate Similarity	NPD7696	Phase 3
0.705	Intermediate Similarity	NPD7698	Approved
0.705	Intermediate Similarity	NPD7697	Approved
0.7037	Intermediate Similarity	NPD7240	Approved
0.7037	Intermediate Similarity	NPD8368	Discontinued
0.7031	Intermediate Similarity	NPD8150	Discontinued
0.7027	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7017	Intermediate Similarity	NPD3817	Phase 2
0.7	Intermediate Similarity	NPD37	Approved
0.6995	Remote Similarity	NPD919	Approved
0.6995	Remote Similarity	NPD7701	Phase 2
0.6984	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6978	Remote Similarity	NPD4965	Approved
0.6978	Remote Similarity	NPD4967	Phase 2
0.6978	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6978	Remote Similarity	NPD4966	Approved
0.6976	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6976	Remote Similarity	NPD7783	Phase 2
0.6968	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.6961	Remote Similarity	NPD8455	Phase 2
0.6961	Remote Similarity	NPD7819	Suspended
0.6932	Remote Similarity	NPD6799	Approved
0.6931	Remote Similarity	NPD7871	Phase 2
0.6931	Remote Similarity	NPD7870	Phase 2
0.6919	Remote Similarity	NPD7199	Phase 2
0.6919	Remote Similarity	NPD1247	Approved
0.691	Remote Similarity	NPD5403	Approved
0.6904	Remote Similarity	NPD6534	Approved
0.6904	Remote Similarity	NPD6535	Approved
0.6902	Remote Similarity	NPD6234	Discontinued
0.6893	Remote Similarity	NPD5401	Approved
0.6893	Remote Similarity	NPD7801	Approved
0.6889	Remote Similarity	NPD4380	Phase 2
0.6885	Remote Similarity	NPD3882	Suspended
0.6884	Remote Similarity	NPD7700	Phase 2
0.6884	Remote Similarity	NPD7699	Phase 2
0.6872	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD3749	Approved
0.6833	Remote Similarity	NPD7458	Discontinued
0.6825	Remote Similarity	NPD4111	Phase 1
0.6816	Remote Similarity	NPD920	Approved
0.6798	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6796	Remote Similarity	NPD8151	Discontinued
0.6786	Remote Similarity	NPD8435	Approved
0.6776	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6761	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6761	Remote Similarity	NPD8155	Clinical (unspecified phase)
0.6761	Remote Similarity	NPD7907	Approved
0.6758	Remote Similarity	NPD7411	Suspended
0.6749	Remote Similarity	NPD6823	Phase 2
0.6745	Remote Similarity	NPD4665	Approved
0.6738	Remote Similarity	NPD6959	Discontinued
0.6738	Remote Similarity	NPD8127	Discontinued
0.6725	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6722	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6721	Remote Similarity	NPD1934	Approved
0.6707	Remote Similarity	NPD1049	Clinical (unspecified phase)
0.6704	Remote Similarity	NPD2532	Approved
0.6704	Remote Similarity	NPD2534	Approved
0.6704	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6704	Remote Similarity	NPD2533	Approved
0.6702	Remote Similarity	NPD6232	Discontinued
0.6701	Remote Similarity	NPD8361	Approved
0.6701	Remote Similarity	NPD8360	Approved
0.6685	Remote Similarity	NPD1465	Phase 2
0.6685	Remote Similarity	NPD7236	Approved
0.6684	Remote Similarity	NPD7473	Discontinued
0.6667	Remote Similarity	NPD6273	Approved
0.665	Remote Similarity	NPD8486	Clinical (unspecified phase)
0.6649	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6632	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6629	Remote Similarity	NPD6190	Approved
0.6611	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6599	Remote Similarity	NPD8424	Clinical (unspecified phase)
0.6595	Remote Similarity	NPD2801	Approved
0.6593	Remote Similarity	NPD1653	Approved
0.6593	Remote Similarity	NPD7239	Suspended
0.6592	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6591	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6591	Remote Similarity	NPD1471	Phase 3
0.6585	Remote Similarity	NPD3057	Approved
0.6579	Remote Similarity	NPD3926	Phase 2
0.657	Remote Similarity	NPD7211	Clinical (unspecified phase)
0.6569	Remote Similarity	NPD4107	Approved
0.6557	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6557	Remote Similarity	NPD7930	Approved
0.6557	Remote Similarity	NPD3226	Approved
0.6556	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6553	Remote Similarity	NPD7680	Approved
0.6553	Remote Similarity	NPD7497	Discontinued
0.652	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6517	Remote Similarity	NPD2800	Approved
0.6514	Remote Similarity	NPD7097	Phase 1
0.6505	Remote Similarity	NPD3533	Approved
0.6505	Remote Similarity	NPD2972	Approved
0.6502	Remote Similarity	NPD8485	Approved
0.6497	Remote Similarity	NPD2346	Discontinued
0.6494	Remote Similarity	NPD6355	Discontinued
0.6493	Remote Similarity	NPD5676	Approved
0.649	Remote Similarity	NPD7999	Approved
0.648	Remote Similarity	NPD3750	Approved
0.648	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6461	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6461	Remote Similarity	NPD1549	Phase 2
0.6456	Remote Similarity	NPD4482	Phase 3
0.6441	Remote Similarity	NPD2796	Approved
0.6441	Remote Similarity	NPD1551	Phase 2
0.6436	Remote Similarity	NPD6213	Phase 3
0.6436	Remote Similarity	NPD6212	Phase 3
0.6436	Remote Similarity	NPD7768	Phase 2
0.6436	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.6432	Remote Similarity	NPD7028	Phase 2
0.6429	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6425	Remote Similarity	NPD1243	Approved
0.6425	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6404	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6404	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6404	Remote Similarity	NPD5762	Approved
0.6404	Remote Similarity	NPD5763	Approved
0.6404	Remote Similarity	NPD7266	Discontinued
0.64	Remote Similarity	NPD1933	Approved
0.6393	Remote Similarity	NPD1512	Approved
0.6386	Remote Similarity	NPD8517	Approved
0.6386	Remote Similarity	NPD8513	Phase 3
0.6386	Remote Similarity	NPD8515	Approved
0.6386	Remote Similarity	NPD8516	Approved
0.6384	Remote Similarity	NPD2799	Discontinued
0.6384	Remote Similarity	NPD3748	Approved
0.6384	Remote Similarity	NPD7033	Discontinued
0.6381	Remote Similarity	NPD7583	Approved
0.6381	Remote Similarity	NPD7584	Approved
0.6379	Remote Similarity	NPD6233	Phase 2
0.6373	Remote Similarity	NPD2403	Approved
0.6359	Remote Similarity	NPD8285	Discontinued
0.6354	Remote Similarity	NPD5710	Approved
0.6354	Remote Similarity	NPD5711	Approved
0.6351	Remote Similarity	NPD7585	Approved
0.6349	Remote Similarity	NPD7057	Phase 3
0.6349	Remote Similarity	NPD7058	Phase 2
0.6348	Remote Similarity	NPD2935	Discontinued
0.6348	Remote Similarity	NPD6100	Approved
0.6348	Remote Similarity	NPD6099	Approved
0.6346	Remote Similarity	NPD2491	Approved
0.6341	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6333	Remote Similarity	NPD6674	Discontinued
0.6329	Remote Similarity	NPD4580	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