NPASS Compound

Structure

CID25255 OpenBabel06191715352D 38 42 0 0 1 0 0 0 0 0999 V2000 -2.2585 4.8663 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7839 3.6903 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8294 3.6903 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4800 1.4318 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3039 3.2130 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.9545 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8267 2.3864 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1787 0.5663 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6533 1.9091 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8174 1.2757 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6533 0.9545 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6052 3.2130 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4064 1.9039 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7812 4.0397 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3066 0.9545 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.9091 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6533 1.9091 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8267 0.4773 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3494 3.2130 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.0824 4.0397 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4800 0.4773 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8267 -0.4773 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6533 -0.9545 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3066 2.8636 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6533 0.9545 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8267 2.3864 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 0.9545 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8267 0.4773 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.2585 3.2130 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8267 -0.4773 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6052 4.8663 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.0370 4.0397 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6533 -1.9091 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1333 2.3864 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3401 2.1023 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8267 4.0397 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4800 -0.4773 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 1 0 0 0 0 2 24 1 0 0 0 0 3 24 1 0 0 0 0 4 25 1 0 0 0 0 6 27 1 0 0 0 0 7 9 1 0 0 0 0 7 16 1 0 0 0 0 8 10 2 0 0 0 0 8 15 1 0 0 0 0 9 25 1 0 0 0 0 10 35 1 0 0 0 0 11 17 1 0 0 0 0 11 18 1 0 0 0 0 12 20 1 0 0 0 0 13 15 2 0 0 0 0 13 35 1 0 0 0 0 14 29 2 0 0 0 0 14 36 1 0 0 0 0 15 21 1 0 0 0 0 16 26 1 1 0 0 0 16 27 1 0 0 0 0 17 24 1 0 0 0 0 17 26 1 1 0 0 0 18 27 1 0 0 0 0 18 30 2 0 0 0 0 19 12 1 6 0 0 0 19 26 1 0 0 0 0 19 36 1 0 0 0 0 20 31 2 0 0 0 0 20 32 1 0 0 0 0 21 25 1 1 0 0 0 21 37 1 0 0 0 0 22 23 1 0 0 0 0 22 28 1 1 0 0 0 22 38 1 0 0 0 0 23 33 2 0 0 0 0 23 37 1 0 0 0 0 24 34 1 0 0 0 0 25 28 1 6 0 0 0 26 5 1 1 0 0 0 27 28 1 6 0 0 0 28 38 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	532.23
Volume:	522.145
LogP:	1.646
LogD:	0.83
LogS:	-3.788
# Rotatable Bonds:	7
TPSA:	152.87
# H-Bond Aceptor:	10
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.412
Synthetic Accessibility Score:	5.773
Fsp3:	0.714
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:	-5.491
MDCK Permeability:	2.1746147467638366e-05
Pgp-inhibitor:	0.306
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.019
20% Bioavailability (F20%):	0.812
30% Bioavailability (F30%):	0.848

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.427
Plasma Protein Binding (PPB):	72.04100036621094%
Volume Distribution (VD):	0.379
Pgp-substrate:	20.7698917388916%

ADMET: Metabolism

CYP1A2-inhibitor:	0.004
CYP1A2-substrate:	0.079
CYP2C19-inhibitor:	0.013
CYP2C19-substrate:	0.251
CYP2C9-inhibitor:	0.041
CYP2C9-substrate:	0.066
CYP2D6-inhibitor:	0.026
CYP2D6-substrate:	0.086
CYP3A4-inhibitor:	0.077
CYP3A4-substrate:	0.217

ADMET: Excretion

Clearance (CL):	4.46
Half-life (T1/2):	0.876

ADMET: Toxicity

hERG Blockers:	0.003
Human Hepatotoxicity (H-HT):	0.578
Drug-inuced Liver Injury (DILI):	0.924
AMES Toxicity:	0.112
Rat Oral Acute Toxicity:	0.957
Maximum Recommended Daily Dose:	0.575
Skin Sensitization:	0.211
Carcinogencity:	0.163
Eye Corrosion:	0.234
Eye Irritation:	0.327
Respiratory Toxicity:	0.949

Download Data

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

Natural Product: NPC25255

Natural Product ID:	NPC25255
*Common Name:**	Nomilinic Acid
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	ZIKZPLSIAVHITA-GBCWXVSRSA-N
Standard InCHI:	InChI=1S/C28H36O10/c1-14(29)36-19(12-20(31)32)26(5)16-7-9-25(4)21(15-8-10-35-13-15)37-23(33)22-28(25,38-22)27(16,6)18(30)11-17(26)24(2,3)34/h8,10,13,16-17,19,21-22,34H,7,9,11-12H2,1-6H3,(H,31,32)/t16-,17+,19-,21-,22-,25+,26-,27+,28-/m1/s1
SMILES:	OC(=O)C[C@H]([C@@]1(C)[C@@H](CC(=O)[C@@]2([C@@H]1CC[C@@]1([C@]32O[C@@H]3C(=O)O[C@@H]1c1ccoc1)C)C)C(O)(C)C)OC(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2269933
PubChem CID:	76315917
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001125] Steroid 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
NPO27288	Citrus maxima	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/S0031-9422(99)00119-3]
NPO27288	Citrus maxima	Species	Rutaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO27288	Citrus maxima	Species	Rutaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO27288	Citrus maxima	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27288	Citrus maxima	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO27288	Citrus maxima	Species	Rutaceae	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
Others	2

Activity Type	# Activity
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1848	Organism	Puccinia arachidis	Puccinia arachidis	Inhibition	=	34.2	%	PMID[502556]
NPT1848	Organism	Puccinia arachidis	Puccinia arachidis	Inhibition	=	28.5	%	PMID[502556]

☑ 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 NPC25255 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	356
0.1-0.2	1445
0.2-0.3	3154
0.3-0.4	5758
0.4-0.5	10494
0.5-0.6	10271
0.6-0.7	9096
0.7-0.8	1709
0.8-0.85	245
0.85-0.9	100
0.9-0.95	49
0.95-1	20

Similarity Score	Similarity Level	Natural Product ID
0.9934	High Similarity	NPC193798
0.9804	High Similarity	NPC123088
0.9804	High Similarity	NPC476858
0.9804	High Similarity	NPC476857
0.9804	High Similarity	NPC476856
0.9677	High Similarity	NPC476850
0.9677	High Similarity	NPC476861
0.9677	High Similarity	NPC476853
0.9675	High Similarity	NPC476860
0.9671	High Similarity	NPC477403
0.9671	High Similarity	NPC237155
0.9613	High Similarity	NPC23387
0.9608	High Similarity	NPC472653
0.9551	High Similarity	NPC472282
0.9551	High Similarity	NPC173516
0.9545	High Similarity	NPC5079
0.9545	High Similarity	NPC470939
0.9539	High Similarity	NPC60973
0.9539	High Similarity	NPC263265
0.949	High Similarity	NPC160651
0.949	High Similarity	NPC471397
0.9484	High Similarity	NPC39986
0.9484	High Similarity	NPC292389
0.9484	High Similarity	NPC234660
0.9484	High Similarity	NPC302369
0.9484	High Similarity	NPC469338
0.9484	High Similarity	NPC477405
0.9484	High Similarity	NPC51568
0.9484	High Similarity	NPC134254
0.9481	High Similarity	NPC477402
0.9481	High Similarity	NPC305016
0.9481	High Similarity	NPC335761
0.9477	High Similarity	NPC286722
0.9423	High Similarity	NPC469849
0.9423	High Similarity	NPC470940
0.9423	High Similarity	NPC276551
0.9419	High Similarity	NPC69028
0.9419	High Similarity	NPC329938
0.9419	High Similarity	NPC263432
0.9416	High Similarity	NPC473473
0.9416	High Similarity	NPC475295
0.9412	High Similarity	NPC126723
0.9412	High Similarity	NPC107646
0.9412	High Similarity	NPC209364
0.9363	High Similarity	NPC470875
0.9355	High Similarity	NPC475381
0.9351	High Similarity	NPC472283
0.9346	High Similarity	NPC264943
0.9304	High Similarity	NPC472651
0.9304	High Similarity	NPC473753
0.9304	High Similarity	NPC472774
0.9304	High Similarity	NPC473766
0.9304	High Similarity	NPC472775
0.9295	High Similarity	NPC290400
0.9295	High Similarity	NPC117986
0.9295	High Similarity	NPC96443
0.9295	High Similarity	NPC82851
0.9295	High Similarity	NPC472771
0.9286	High Similarity	NPC469485
0.9245	High Similarity	NPC271235
0.9245	High Similarity	NPC472652
0.9236	High Similarity	NPC472773
0.9226	High Similarity	NPC45101
0.9226	High Similarity	NPC472772
0.9226	High Similarity	NPC249021
0.9226	High Similarity	NPC173544
0.9221	High Similarity	NPC469336
0.9221	High Similarity	NPC469850
0.9216	High Similarity	NPC75906
0.9156	High Similarity	NPC178932
0.9114	High Similarity	NPC476197
0.9114	High Similarity	NPC469846
0.9108	High Similarity	NPC191828
0.9103	High Similarity	NPC299038
0.9103	High Similarity	NPC187149
0.9103	High Similarity	NPC167142
0.9097	High Similarity	NPC44675
0.9097	High Similarity	NPC281258
0.9097	High Similarity	NPC214541
0.9085	High Similarity	NPC469335
0.9085	High Similarity	NPC159927
0.9085	High Similarity	NPC477404
0.9085	High Similarity	NPC196864
0.9085	High Similarity	NPC46551
0.9073	High Similarity	NPC262198
0.9057	High Similarity	NPC271657
0.9051	High Similarity	NPC18347
0.9051	High Similarity	NPC149896
0.9045	High Similarity	NPC473368
0.9045	High Similarity	NPC475967
0.9032	High Similarity	NPC282445
0.9026	High Similarity	NPC18135
0.9012	High Similarity	NPC159232
0.9	High Similarity	NPC475779
0.8994	High Similarity	NPC663
0.8994	High Similarity	NPC224394
0.8981	High Similarity	NPC261597
0.8981	High Similarity	NPC36655
0.8968	High Similarity	NPC476201
0.8968	High Similarity	NPC469503
0.8951	High Similarity	NPC470995
0.894	High Similarity	NPC86935
0.8931	High Similarity	NPC207978
0.8931	High Similarity	NPC200782
0.8931	High Similarity	NPC197596
0.891	High Similarity	NPC57998
0.8909	High Similarity	NPC478177
0.8902	High Similarity	NPC471437
0.8889	High Similarity	NPC221809
0.8889	High Similarity	NPC470941
0.8882	High Similarity	NPC478178
0.8875	High Similarity	NPC419
0.8854	High Similarity	NPC476262
0.8846	High Similarity	NPC44577
0.8841	High Similarity	NPC469848
0.8839	High Similarity	NPC476122
0.8834	High Similarity	NPC82602
0.8834	High Similarity	NPC302392
0.882	High Similarity	NPC470182
0.8812	High Similarity	NPC188649
0.8805	High Similarity	NPC307383
0.879	High Similarity	NPC30222
0.8788	High Similarity	NPC236004
0.878	High Similarity	NPC160818
0.878	High Similarity	NPC169299
0.878	High Similarity	NPC285227
0.8766	High Similarity	NPC255414
0.8765	High Similarity	NPC149945
0.8765	High Similarity	NPC121995
0.8758	High Similarity	NPC288602
0.8758	High Similarity	NPC88841
0.8757	High Similarity	NPC105395
0.8757	High Similarity	NPC247563
0.8757	High Similarity	NPC242068
0.875	High Similarity	NPC287559
0.875	High Similarity	NPC470789
0.8735	High Similarity	NPC262386
0.8734	High Similarity	NPC75310
0.8734	High Similarity	NPC35000
0.8726	High Similarity	NPC268905
0.8712	High Similarity	NPC478179
0.8712	High Similarity	NPC472764
0.8712	High Similarity	NPC476224
0.8712	High Similarity	NPC270312
0.8701	High Similarity	NPC346
0.8696	High Similarity	NPC471167
0.8696	High Similarity	NPC471166
0.8696	High Similarity	NPC6326
0.8696	High Similarity	NPC68848
0.8696	High Similarity	NPC472767
0.8696	High Similarity	NPC211777
0.8696	High Similarity	NPC18986
0.8693	High Similarity	NPC476944
0.8693	High Similarity	NPC142113
0.8688	High Similarity	NPC262872
0.8684	High Similarity	NPC121158
0.8679	High Similarity	NPC41880
0.8675	High Similarity	NPC94763
0.8667	High Similarity	NPC476943
0.8662	High Similarity	NPC272590
0.8659	High Similarity	NPC472766
0.8659	High Similarity	NPC472765
0.8654	High Similarity	NPC195325
0.8654	High Similarity	NPC69647
0.8654	High Similarity	NPC472654
0.8654	High Similarity	NPC125182
0.865	High Similarity	NPC93172
0.865	High Similarity	NPC97574
0.865	High Similarity	NPC214600
0.865	High Similarity	NPC472141
0.8645	High Similarity	NPC250228
0.8642	High Similarity	NPC198047
0.8642	High Similarity	NPC165218
0.8642	High Similarity	NPC472139
0.8642	High Similarity	NPC471168
0.8627	High Similarity	NPC267632
0.8627	High Similarity	NPC243577
0.8625	High Similarity	NPC472778
0.8625	High Similarity	NPC195954
0.8625	High Similarity	NPC472777
0.8625	High Similarity	NPC88007
0.8625	High Similarity	NPC472776
0.8616	High Similarity	NPC92979
0.8608	High Similarity	NPC475777
0.8599	High Similarity	NPC156189
0.8589	High Similarity	NPC261184
0.8589	High Similarity	NPC56358
0.8589	High Similarity	NPC146991
0.858	High Similarity	NPC472668
0.8571	High Similarity	NPC474611
0.8571	High Similarity	NPC137295
0.8571	High Similarity	NPC475226
0.8571	High Similarity	NPC251865
0.8562	High Similarity	NPC204663
0.8553	High Similarity	NPC114880
0.8545	High Similarity	NPC296558
0.8545	High Similarity	NPC327922
0.8535	High Similarity	NPC211625
0.8533	High Similarity	NPC46896
0.8528	High Similarity	NPC285567

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 NPC25255 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	301
0.1-0.2	1026
0.2-0.3	2152
0.3-0.4	2645
0.4-0.5	1887
0.5-0.6	848
0.6-0.7	260
0.7-0.8	29
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
0.8385	Intermediate Similarity	NPD5761	Phase 2
0.8385	Intermediate Similarity	NPD5760	Phase 2
0.8372	Intermediate Similarity	NPD8434	Phase 2
0.8293	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7874	Intermediate Similarity	NPD6765	Approved
0.7874	Intermediate Similarity	NPD6764	Approved
0.7725	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD6785	Approved
0.7697	Intermediate Similarity	NPD6784	Approved
0.7692	Intermediate Similarity	NPD7075	Discontinued
0.7545	Intermediate Similarity	NPD6599	Discontinued
0.7515	Intermediate Similarity	NPD7819	Suspended
0.7381	Intermediate Similarity	NPD3226	Approved
0.7374	Intermediate Similarity	NPD6559	Discontinued
0.7353	Intermediate Similarity	NPD6801	Discontinued
0.7346	Intermediate Similarity	NPD1471	Phase 3
0.7317	Intermediate Similarity	NPD4628	Phase 3
0.7297	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7294	Intermediate Similarity	NPD7411	Suspended
0.7289	Intermediate Similarity	NPD6799	Approved
0.7267	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD3817	Phase 2
0.7267	Intermediate Similarity	NPD5402	Approved
0.7257	Intermediate Similarity	NPD1247	Approved
0.7241	Intermediate Similarity	NPD919	Approved
0.7239	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7213	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD5494	Approved
0.7186	Intermediate Similarity	NPD8404	Phase 2
0.7184	Intermediate Similarity	NPD3749	Approved
0.716	Intermediate Similarity	NPD920	Approved
0.716	Intermediate Similarity	NPD5403	Approved
0.7152	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD5401	Approved
0.7134	Intermediate Similarity	NPD2346	Discontinued
0.7126	Intermediate Similarity	NPD3882	Suspended
0.7111	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7104	Intermediate Similarity	NPD8313	Approved
0.7104	Intermediate Similarity	NPD8312	Approved
0.7095	Intermediate Similarity	NPD7473	Discontinued
0.7081	Intermediate Similarity	NPD8150	Discontinued
0.7056	Intermediate Similarity	NPD7799	Discontinued
0.7056	Intermediate Similarity	NPD3751	Discontinued
0.7041	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7035	Intermediate Similarity	NPD4380	Phase 2
0.7029	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD7236	Approved
0.7022	Intermediate Similarity	NPD3787	Discontinued
0.7017	Intermediate Similarity	NPD5844	Phase 1
0.7011	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6979	Remote Similarity	NPD8285	Discontinued
0.697	Remote Similarity	NPD6099	Approved
0.697	Remote Similarity	NPD6100	Approved
0.6966	Remote Similarity	NPD8127	Discontinued
0.6961	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6961	Remote Similarity	NPD3818	Discontinued
0.6957	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD1934	Approved
0.6944	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD6166	Phase 2
0.6941	Remote Similarity	NPD2532	Approved
0.6941	Remote Similarity	NPD2533	Approved
0.6941	Remote Similarity	NPD2534	Approved
0.6933	Remote Similarity	NPD6355	Discontinued
0.6927	Remote Similarity	NPD6232	Discontinued
0.6923	Remote Similarity	NPD7435	Discontinued
0.6923	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD7239	Suspended
0.6909	Remote Similarity	NPD2799	Discontinued
0.6902	Remote Similarity	NPD7251	Discontinued
0.6901	Remote Similarity	NPD6273	Approved
0.6889	Remote Similarity	NPD3926	Phase 2
0.6886	Remote Similarity	NPD1549	Phase 2
0.6882	Remote Similarity	NPD8407	Phase 2
0.6879	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD7458	Discontinued
0.6872	Remote Similarity	NPD6959	Discontinued
0.6871	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD1551	Phase 2
0.6867	Remote Similarity	NPD2796	Approved
0.6865	Remote Similarity	NPD7808	Phase 3
0.6852	Remote Similarity	NPD3268	Approved
0.6852	Remote Similarity	NPD2313	Discontinued
0.6848	Remote Similarity	NPD6797	Phase 2
0.6848	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD6832	Phase 2
0.6826	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6826	Remote Similarity	NPD5763	Approved
0.6826	Remote Similarity	NPD5762	Approved
0.6826	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6811	Remote Similarity	NPD8368	Discontinued
0.6811	Remote Similarity	NPD7685	Pre-registration
0.6807	Remote Similarity	NPD7033	Discontinued
0.6796	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6793	Remote Similarity	NPD7074	Phase 3
0.6761	Remote Similarity	NPD37	Approved
0.6746	Remote Similarity	NPD1243	Approved
0.6746	Remote Similarity	NPD2800	Approved
0.6744	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6742	Remote Similarity	NPD4967	Phase 2
0.6742	Remote Similarity	NPD4965	Approved
0.6742	Remote Similarity	NPD7768	Phase 2
0.6742	Remote Similarity	NPD4966	Approved
0.6739	Remote Similarity	NPD7054	Approved
0.6726	Remote Similarity	NPD2344	Approved
0.6723	Remote Similarity	NPD2801	Approved
0.6716	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6716	Remote Similarity	NPD7874	Approved
0.6715	Remote Similarity	NPD7907	Approved
0.6706	Remote Similarity	NPD3750	Approved
0.6703	Remote Similarity	NPD7472	Approved
0.6687	Remote Similarity	NPD7095	Approved
0.6686	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6684	Remote Similarity	NPD6781	Approved
0.6684	Remote Similarity	NPD4107	Approved
0.6684	Remote Similarity	NPD6777	Approved
0.6684	Remote Similarity	NPD6778	Approved
0.6684	Remote Similarity	NPD6780	Approved
0.6684	Remote Similarity	NPD6782	Approved
0.6684	Remote Similarity	NPD6776	Approved
0.6684	Remote Similarity	NPD6779	Approved
0.6667	Remote Similarity	NPD1608	Approved
0.6667	Remote Similarity	NPD7696	Phase 3
0.6667	Remote Similarity	NPD7697	Approved
0.6667	Remote Similarity	NPD2935	Discontinued
0.6667	Remote Similarity	NPD3887	Approved
0.6667	Remote Similarity	NPD6234	Discontinued
0.6667	Remote Similarity	NPD7698	Approved
0.6667	Remote Similarity	NPD2403	Approved
0.6667	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6651	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.6649	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6648	Remote Similarity	NPD6808	Phase 2
0.6648	Remote Similarity	NPD7229	Phase 3
0.6647	Remote Similarity	NPD7097	Phase 1
0.6646	Remote Similarity	NPD6798	Discontinued
0.6646	Remote Similarity	NPD3267	Approved
0.6646	Remote Similarity	NPD1049	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD3266	Approved
0.6633	Remote Similarity	NPD8320	Phase 1
0.6633	Remote Similarity	NPD7870	Phase 2
0.6633	Remote Similarity	NPD8319	Approved
0.6633	Remote Similarity	NPD7871	Phase 2
0.6629	Remote Similarity	NPD1465	Phase 2
0.6627	Remote Similarity	NPD447	Suspended
0.6618	Remote Similarity	NPD4111	Phase 1
0.6609	Remote Similarity	NPD1512	Approved
0.6607	Remote Similarity	NPD1510	Phase 2
0.6607	Remote Similarity	NPD3748	Approved
0.6607	Remote Similarity	NPD4308	Phase 3
0.6606	Remote Similarity	NPD6233	Phase 2
0.6595	Remote Similarity	NPD7228	Approved
0.6593	Remote Similarity	NPD7199	Phase 2
0.6576	Remote Similarity	NPD7784	Clinical (unspecified phase)
0.657	Remote Similarity	NPD2309	Approved
0.657	Remote Similarity	NPD6190	Approved
0.657	Remote Similarity	NPD2354	Approved
0.6566	Remote Similarity	NPD4482	Phase 3
0.6562	Remote Similarity	NPD8435	Approved
0.6557	Remote Similarity	NPD5710	Approved
0.6557	Remote Similarity	NPD5711	Approved
0.6556	Remote Similarity	NPD7058	Phase 2
0.6556	Remote Similarity	NPD7057	Phase 3
0.6545	Remote Similarity	NPD3764	Approved
0.6545	Remote Similarity	NPD8424	Clinical (unspecified phase)
0.6545	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6543	Remote Similarity	NPD2797	Approved
0.6538	Remote Similarity	NPD4665	Approved
0.6536	Remote Similarity	NPD8455	Phase 2
0.6535	Remote Similarity	NPD7701	Phase 2
0.6533	Remote Similarity	NPD3057	Approved
0.6531	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6529	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6529	Remote Similarity	NPD6004	Phase 3
0.6529	Remote Similarity	NPD6005	Phase 3
0.6529	Remote Similarity	NPD6002	Phase 3
0.6529	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6527	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6527	Remote Similarity	NPD1933	Approved
0.652	Remote Similarity	NPD7801	Approved
0.6517	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6515	Remote Similarity	NPD4580	Approved
0.6514	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6512	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6512	Remote Similarity	NPD4110	Phase 3
0.6512	Remote Similarity	NPD7003	Approved
0.6512	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6506	Remote Similarity	NPD8032	Phase 2
0.6505	Remote Similarity	NPD2163	Approved
0.6503	Remote Similarity	NPD2798	Approved
0.65	Remote Similarity	NPD7497	Discontinued
0.65	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6494	Remote Similarity	NPD1511	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