NPASS Compound

Structure

CID219170 OpenBabel06191716012D 24 27 0 0 0 0 0 0 0 0999 V2000 -3.0408 2.5654 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1618 4.1821 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2894 5.0645 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0871 1.4159 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2696 1.8878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0872 0.4720 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6350 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4522 1.4158 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4523 0.4718 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8173 0.4719 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2698 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6349 1.8875 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8176 1.4157 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.8875 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6348 2.8314 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0001 2.8316 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8174 3.3035 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8173 1.4157 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -3.2699 -0.9932 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7565 1.6673 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4523 3.3034 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8171 3.3036 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8175 4.2472 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 22 1 0 0 0 0 2 23 1 0 0 0 0 3 24 1 0 0 0 0 4 5 2 0 0 0 0 4 6 1 0 0 0 0 5 8 1 0 0 0 0 6 11 2 0 0 0 0 7 9 2 0 0 0 0 7 10 1 0 0 0 0 8 9 1 0 0 0 0 8 12 2 0 0 0 0 9 11 1 0 0 0 0 10 13 2 0 0 0 0 10 19 1 0 0 0 0 11 20 1 0 0 0 0 12 13 1 0 0 0 0 12 15 1 0 0 0 0 13 14 1 0 0 0 0 14 16 2 0 0 0 0 14 18 1 0 0 0 0 15 17 2 0 0 0 0 15 22 1 0 0 0 0 16 17 1 0 0 0 0 16 23 1 0 0 0 0 17 24 1 0 0 0 0 18 19 2 0 0 0 0 18 21 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	325.1
Volume:	319.515
LogP:	3.406
LogD:	2.748
LogS:	-5.867
# Rotatable Bonds:	3
TPSA:	77.02
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.723
Synthetic Accessibility Score:	2.781
Fsp3:	0.167
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.906
MDCK Permeability:	1.983555375772994e-05
Pgp-inhibitor:	0.028
Pgp-substrate:	0.01
Human Intestinal Absorption (HIA):	0.022
20% Bioavailability (F20%):	0.001
30% Bioavailability (F30%):	0.001

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.027
Plasma Protein Binding (PPB):	90.52139282226562%
Volume Distribution (VD):	0.698
Pgp-substrate:	10.614951133728027%

ADMET: Metabolism

CYP1A2-inhibitor:	0.85
CYP1A2-substrate:	0.968
CYP2C19-inhibitor:	0.233
CYP2C19-substrate:	0.768
CYP2C9-inhibitor:	0.575
CYP2C9-substrate:	0.848
CYP2D6-inhibitor:	0.491
CYP2D6-substrate:	0.403
CYP3A4-inhibitor:	0.292
CYP3A4-substrate:	0.185

ADMET: Excretion

Clearance (CL):	2.274
Half-life (T1/2):	0.331

ADMET: Toxicity

hERG Blockers:	0.057
Human Hepatotoxicity (H-HT):	0.118
Drug-inuced Liver Injury (DILI):	0.94
AMES Toxicity:	0.754
Rat Oral Acute Toxicity:	0.319
Maximum Recommended Daily Dose:	0.216
Skin Sensitization:	0.606
Carcinogencity:	0.083
Eye Corrosion:	0.005
Eye Irritation:	0.897
Respiratory Toxicity:	0.402

Download Data

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

Natural Product: NPC219170

Natural Product ID:	NPC219170
*Common Name:**	Oldhamactam
IUPAC Name:	n.a.
Synonyms:	Oldhamactam
Standard InCHIKey:	XPAJKJNXGTXSLZ-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C18H15NO5/c1-22-15-12-8-5-4-6-11(20)9(8)7-10-13(12)14(18(21)19-10)16(23-2)17(15)24-3/h4-7,20H,1-3H3,(H,19,21)
SMILES:	COc1c(OC)c(OC)c2c3c1c1cccc(c1cc3N=C2O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL412823
PubChem CID:	44422603
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0002663] Aristolactams

*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
NPO18509	Fissistigma oldhamii	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10978218]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	seeds	n.a.	n.a.	PMID[11141125]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12398544]
NPO18509	Fissistigma oldhamii	Species	Annonaceae	Eukaryota	stem	n.a.	n.a.	PMID[17081761]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18419154]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19296389]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21910504]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	seeds	n.a.	n.a.	PMID[22011319]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	seed	n.a.	PMID[22011319]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	Barks	n.a.	n.a.	PMID[2348205]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	fruit	n.a.	PMID[8786370]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	bark	n.a.	n.a.	PMID[9214729]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO18509	Fissistigma oldhamii	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2884	Annona squamosa	Species	Annonaceae	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
Others	3

Activity Type	# Activity
Cell Line	1
Others	4

Target ID	Target Type	Target Name	Activity Type	Activity Relation	Value	Unit	Reference
NPT1076	Cell Line	B-cells	IC50	=	41700.0	nM	PMID[524536]
NPT27	Others	Unspecified	CC50	=	201000.0	nM	PMID[524536]
NPT2	Others	Unspecified	IC50	=	22800.0	nM	PMID[524536]
NPT2	Others	Unspecified	Ratio CC50/IC50	=	9.0	n.a.	PMID[524536]
NPT2	Others	Unspecified	Ratio CC50/IC50	=	5.0	n.a.	PMID[524536]

☑ 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 NPC219170 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	468
0.1-0.2	2115
0.2-0.3	9301
0.3-0.4	8390
0.4-0.5	5873
0.5-0.6	11145
0.6-0.7	4737
0.7-0.8	631
0.8-0.85	17
0.85-0.9	1
0.9-0.95	12
0.95-1	7

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC180253
0.988	High Similarity	NPC276060
0.9821	High Similarity	NPC22928
0.9641	High Similarity	NPC215747
0.9641	High Similarity	NPC192939
0.9581	High Similarity	NPC260118
0.9527	High Similarity	NPC28425
0.9521	High Similarity	NPC265383
0.9467	High Similarity	NPC119579
0.9425	High Similarity	NPC29472
0.9408	High Similarity	NPC311936
0.931	High Similarity	NPC294244
0.9195	High Similarity	NPC296742
0.9195	High Similarity	NPC112676
0.9138	High Similarity	NPC224293
0.908	High Similarity	NPC69213
0.8631	High Similarity	NPC235628
0.8602	High Similarity	NPC159101
0.8352	Intermediate Similarity	NPC231371
0.8333	Intermediate Similarity	NPC68328
0.8197	Intermediate Similarity	NPC320088
0.8087	Intermediate Similarity	NPC33902
0.8087	Intermediate Similarity	NPC276674
0.8066	Intermediate Similarity	NPC190461
0.8045	Intermediate Similarity	NPC168153
0.8021	Intermediate Similarity	NPC78284
0.8012	Intermediate Similarity	NPC52475
0.7965	Intermediate Similarity	NPC18614
0.7901	Intermediate Similarity	NPC474051
0.7901	Intermediate Similarity	NPC285941
0.7901	Intermediate Similarity	NPC228040
0.7886	Intermediate Similarity	NPC206736
0.7886	Intermediate Similarity	NPC195766
0.7861	Intermediate Similarity	NPC474904
0.7861	Intermediate Similarity	NPC312531
0.785	Intermediate Similarity	NPC240684
0.7845	Intermediate Similarity	NPC239775
0.7841	Intermediate Similarity	NPC329837
0.78	Intermediate Similarity	NPC290227
0.779	Intermediate Similarity	NPC168753
0.779	Intermediate Similarity	NPC118274
0.7767	Intermediate Similarity	NPC200888
0.7755	Intermediate Similarity	NPC261388
0.7749	Intermediate Similarity	NPC162653
0.7742	Intermediate Similarity	NPC249405
0.773	Intermediate Similarity	NPC474507
0.7725	Intermediate Similarity	NPC266006
0.768	Intermediate Similarity	NPC158376
0.768	Intermediate Similarity	NPC306555
0.768	Intermediate Similarity	NPC117188
0.768	Intermediate Similarity	NPC145832
0.768	Intermediate Similarity	NPC205421
0.768	Intermediate Similarity	NPC12053
0.768	Intermediate Similarity	NPC81218
0.768	Intermediate Similarity	NPC474931
0.7679	Intermediate Similarity	NPC218131
0.7679	Intermediate Similarity	NPC105847
0.7679	Intermediate Similarity	NPC243759
0.7638	Intermediate Similarity	NPC121510
0.7638	Intermediate Similarity	NPC171882
0.7638	Intermediate Similarity	NPC85661
0.7633	Intermediate Similarity	NPC12668
0.7633	Intermediate Similarity	NPC308768
0.7622	Intermediate Similarity	NPC148709
0.7622	Intermediate Similarity	NPC173416
0.7622	Intermediate Similarity	NPC476577
0.7621	Intermediate Similarity	NPC122463
0.7619	Intermediate Similarity	NPC151656
0.7619	Intermediate Similarity	NPC200935
0.7619	Intermediate Similarity	NPC230919
0.7619	Intermediate Similarity	NPC57036
0.7619	Intermediate Similarity	NPC266453
0.7614	Intermediate Similarity	NPC10730
0.7614	Intermediate Similarity	NPC10875
0.7588	Intermediate Similarity	NPC46679
0.7574	Intermediate Similarity	NPC220344
0.7574	Intermediate Similarity	NPC243996
0.7574	Intermediate Similarity	NPC275061
0.7574	Intermediate Similarity	NPC132804
0.7569	Intermediate Similarity	NPC78222
0.7569	Intermediate Similarity	NPC96603
0.7569	Intermediate Similarity	NPC212794
0.7569	Intermediate Similarity	NPC13504
0.7569	Intermediate Similarity	NPC306843
0.7569	Intermediate Similarity	NPC477563
0.7569	Intermediate Similarity	NPC196447
0.7569	Intermediate Similarity	NPC253043
0.7569	Intermediate Similarity	NPC136508
0.7557	Intermediate Similarity	NPC275027
0.7556	Intermediate Similarity	NPC79402
0.7556	Intermediate Similarity	NPC80759
0.7556	Intermediate Similarity	NPC204179
0.7544	Intermediate Similarity	NPC175838
0.7543	Intermediate Similarity	NPC265473
0.7543	Intermediate Similarity	NPC276665
0.7525	Intermediate Similarity	NPC91234
0.7515	Intermediate Similarity	NPC56329
0.7515	Intermediate Similarity	NPC242715
0.7515	Intermediate Similarity	NPC22902
0.7514	Intermediate Similarity	NPC19555
0.7514	Intermediate Similarity	NPC192135
0.7514	Intermediate Similarity	NPC1229
0.7514	Intermediate Similarity	NPC324144
0.7514	Intermediate Similarity	NPC477020
0.7514	Intermediate Similarity	NPC66341
0.75	Intermediate Similarity	NPC235143
0.75	Intermediate Similarity	NPC271388
0.75	Intermediate Similarity	NPC205255
0.75	Intermediate Similarity	NPC127402
0.75	Intermediate Similarity	NPC179704
0.75	Intermediate Similarity	NPC230956
0.75	Intermediate Similarity	NPC90185
0.75	Intermediate Similarity	NPC119649
0.7487	Intermediate Similarity	NPC186546
0.7487	Intermediate Similarity	NPC114364
0.7487	Intermediate Similarity	NPC476576
0.7487	Intermediate Similarity	NPC320223
0.7486	Intermediate Similarity	NPC204947
0.7486	Intermediate Similarity	NPC77359
0.7486	Intermediate Similarity	NPC476572
0.7486	Intermediate Similarity	NPC306366
0.7461	Intermediate Similarity	NPC478093
0.7461	Intermediate Similarity	NPC302001
0.7459	Intermediate Similarity	NPC60186
0.7459	Intermediate Similarity	NPC19520
0.7459	Intermediate Similarity	NPC149090
0.7458	Intermediate Similarity	NPC114124
0.7456	Intermediate Similarity	NPC205442
0.7456	Intermediate Similarity	NPC30632
0.7456	Intermediate Similarity	NPC202846
0.7456	Intermediate Similarity	NPC143139
0.7448	Intermediate Similarity	NPC82763
0.7444	Intermediate Similarity	NPC221864
0.7442	Intermediate Similarity	NPC183709
0.744	Intermediate Similarity	NPC174049
0.744	Intermediate Similarity	NPC160697
0.7437	Intermediate Similarity	NPC164374
0.7437	Intermediate Similarity	NPC137929
0.7437	Intermediate Similarity	NPC38961
0.7435	Intermediate Similarity	NPC214116
0.7433	Intermediate Similarity	NPC287588
0.743	Intermediate Similarity	NPC291359
0.7427	Intermediate Similarity	NPC73505
0.7427	Intermediate Similarity	NPC295719
0.7427	Intermediate Similarity	NPC34431
0.7427	Intermediate Similarity	NPC165026
0.7423	Intermediate Similarity	NPC473589
0.7423	Intermediate Similarity	NPC478091
0.7423	Intermediate Similarity	NPC478092
0.7423	Intermediate Similarity	NPC30182
0.7413	Intermediate Similarity	NPC100573
0.7413	Intermediate Similarity	NPC207873
0.7407	Intermediate Similarity	NPC32413
0.7407	Intermediate Similarity	NPC474506
0.7405	Intermediate Similarity	NPC26240
0.7405	Intermediate Similarity	NPC477562
0.7405	Intermediate Similarity	NPC69712
0.7403	Intermediate Similarity	NPC27410
0.7403	Intermediate Similarity	NPC166014
0.74	Intermediate Similarity	NPC304183
0.7398	Intermediate Similarity	NPC17677
0.7396	Intermediate Similarity	NPC200557
0.7396	Intermediate Similarity	NPC108198
0.7396	Intermediate Similarity	NPC294884
0.7396	Intermediate Similarity	NPC158142
0.7396	Intermediate Similarity	NPC111655
0.7396	Intermediate Similarity	NPC69029
0.7396	Intermediate Similarity	NPC241241
0.7396	Intermediate Similarity	NPC10314
0.7396	Intermediate Similarity	NPC126637
0.7382	Intermediate Similarity	NPC302245
0.7382	Intermediate Similarity	NPC95426
0.7382	Intermediate Similarity	NPC16357
0.738	Intermediate Similarity	NPC199465
0.738	Intermediate Similarity	NPC229166
0.738	Intermediate Similarity	NPC128560
0.7374	Intermediate Similarity	NPC107602
0.7374	Intermediate Similarity	NPC99659
0.7374	Intermediate Similarity	NPC325871
0.7371	Intermediate Similarity	NPC16436
0.7368	Intermediate Similarity	NPC212942
0.7368	Intermediate Similarity	NPC79622
0.7368	Intermediate Similarity	NPC29868
0.7365	Intermediate Similarity	NPC471983
0.7365	Intermediate Similarity	NPC149337
0.7354	Intermediate Similarity	NPC258695
0.7354	Intermediate Similarity	NPC470879
0.7351	Intermediate Similarity	NPC182257
0.7347	Intermediate Similarity	NPC234318
0.7344	Intermediate Similarity	NPC139783
0.7344	Intermediate Similarity	NPC65312
0.7337	Intermediate Similarity	NPC125649
0.7337	Intermediate Similarity	NPC56887
0.7337	Intermediate Similarity	NPC264850
0.7337	Intermediate Similarity	NPC13916
0.7337	Intermediate Similarity	NPC257354
0.7337	Intermediate Similarity	NPC193853
0.7337	Intermediate Similarity	NPC223077
0.733	Intermediate Similarity	NPC135772
0.7323	Intermediate Similarity	NPC25897

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 NPC219170 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	306
0.1-0.2	791
0.2-0.3	975
0.3-0.4	2100
0.4-0.5	2550
0.5-0.6	1900
0.6-0.7	500
0.7-0.8	28
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7557	Intermediate Similarity	NPD5617	Suspended
0.75	Intermediate Similarity	NPD4055	Discovery
0.7433	Intermediate Similarity	NPD6996	Clinical (unspecified phase)
0.7432	Intermediate Similarity	NPD4606	Clinical (unspecified phase)
0.7401	Intermediate Similarity	NPD4005	Discontinued
0.7312	Intermediate Similarity	NPD5602	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD5811	Approved
0.7249	Intermediate Similarity	NPD6184	Discontinued
0.7247	Intermediate Similarity	NPD2883	Discontinued
0.7228	Intermediate Similarity	NPD1850	Phase 3
0.7222	Intermediate Similarity	NPD3778	Approved
0.7204	Intermediate Similarity	NPD4083	Discontinued
0.7167	Intermediate Similarity	NPD4678	Approved
0.7167	Intermediate Similarity	NPD4675	Approved
0.7128	Intermediate Similarity	NPD2843	Phase 2
0.7128	Intermediate Similarity	NPD2845	Phase 2
0.712	Intermediate Similarity	NPD3453	Discontinued
0.7119	Intermediate Similarity	NPD4357	Discontinued
0.7108	Intermediate Similarity	NPD7263	Phase 2
0.7107	Intermediate Similarity	NPD7125	Discontinued
0.7104	Intermediate Similarity	NPD2358	Clinical (unspecified phase)
0.7098	Intermediate Similarity	NPD8054	Approved
0.7098	Intermediate Similarity	NPD8053	Approved
0.7072	Intermediate Similarity	NPD3296	Phase 1
0.7051	Intermediate Similarity	NPD8067	Phase 3
0.7033	Intermediate Similarity	NPD2789	Approved
0.7027	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7026	Intermediate Similarity	NPD4951	Discontinued
0.7016	Intermediate Similarity	NPD3920	Phase 2
0.6995	Remote Similarity	NPD3516	Approved
0.6995	Remote Similarity	NPD3812	Clinical (unspecified phase)
0.6995	Remote Similarity	NPD3515	Approved
0.699	Remote Similarity	NPD7906	Approved
0.6961	Remote Similarity	NPD950	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD5917	Clinical (unspecified phase)
0.6952	Remote Similarity	NPD7201	Clinical (unspecified phase)
0.694	Remote Similarity	NPD3237	Clinical (unspecified phase)
0.694	Remote Similarity	NPD3236	Phase 3
0.6927	Remote Similarity	NPD7479	Phase 2
0.6919	Remote Similarity	NPD5641	Discontinued
0.6919	Remote Similarity	NPD5599	Discontinued
0.6915	Remote Similarity	NPD2821	Approved
0.6911	Remote Similarity	NPD8099	Discontinued
0.6911	Remote Similarity	NPD8251	Approved
0.6911	Remote Similarity	NPD8252	Approved
0.691	Remote Similarity	NPD5307	Clinical (unspecified phase)
0.6907	Remote Similarity	NPD8453	Clinical (unspecified phase)
0.6895	Remote Similarity	NPD6607	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD4123	Phase 3
0.6878	Remote Similarity	NPD3051	Approved
0.6875	Remote Similarity	NPD8156	Discontinued
0.6875	Remote Similarity	NPD5810	Discontinued
0.6872	Remote Similarity	NPD4577	Approved
0.6872	Remote Similarity	NPD4578	Approved
0.6869	Remote Similarity	NPD3408	Clinical (unspecified phase)
0.6868	Remote Similarity	NPD4003	Phase 3
0.6862	Remote Similarity	NPD6746	Phase 2
0.686	Remote Similarity	NPD2674	Phase 3
0.6859	Remote Similarity	NPD5966	Clinical (unspecified phase)
0.6853	Remote Similarity	NPD4663	Approved
0.6851	Remote Similarity	NPD5261	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD5090	Approved
0.6848	Remote Similarity	NPD5089	Approved
0.6842	Remote Similarity	NPD2970	Approved
0.6842	Remote Similarity	NPD2969	Approved
0.6839	Remote Similarity	NPD4097	Suspended
0.6834	Remote Similarity	NPD6656	Clinical (unspecified phase)
0.6823	Remote Similarity	NPD7493	Clinical (unspecified phase)
0.6822	Remote Similarity	NPD3763	Approved
0.6818	Remote Similarity	NPD5800	Discontinued
0.6818	Remote Similarity	NPD3398	Discontinued
0.6806	Remote Similarity	NPD2489	Approved
0.6806	Remote Similarity	NPD677	Clinical (unspecified phase)
0.6806	Remote Similarity	NPD27	Approved
0.6804	Remote Similarity	NPD6496	Clinical (unspecified phase)
0.6791	Remote Similarity	NPD6788	Approved
0.6789	Remote Similarity	NPD6232	Discontinued
0.6786	Remote Similarity	NPD7313	Approved
0.6786	Remote Similarity	NPD7310	Approved
0.6786	Remote Similarity	NPD7311	Approved
0.6786	Remote Similarity	NPD7312	Approved
0.6766	Remote Similarity	NPD7262	Phase 1
0.676	Remote Similarity	NPD6331	Phase 2
0.6757	Remote Similarity	NPD6723	Discontinued
0.6751	Remote Similarity	NPD7309	Approved
0.6749	Remote Similarity	NPD4604	Approved
0.6749	Remote Similarity	NPD7034	Discontinued
0.6749	Remote Similarity	NPD4605	Approved
0.6744	Remote Similarity	NPD4625	Phase 3
0.6744	Remote Similarity	NPD3027	Phase 3
0.6742	Remote Similarity	NPD4664	Clinical (unspecified phase)
0.674	Remote Similarity	NPD2420	Approved
0.674	Remote Similarity	NPD2421	Approved
0.6739	Remote Similarity	NPD7261	Clinical (unspecified phase)
0.6737	Remote Similarity	NPD4986	Clinical (unspecified phase)
0.6734	Remote Similarity	NPD1898	Discontinued
0.6732	Remote Similarity	NPD6612	Phase 2
0.6722	Remote Similarity	NPD5241	Discontinued
0.6722	Remote Similarity	NPD3301	Approved
0.6716	Remote Similarity	NPD3921	Approved
0.6716	Remote Similarity	NPD3924	Approved
0.6716	Remote Similarity	NPD3923	Approved
0.6716	Remote Similarity	NPD3922	Approved
0.671	Remote Similarity	NPD6503	Clinical (unspecified phase)
0.6705	Remote Similarity	NPD3144	Approved
0.6705	Remote Similarity	NPD3145	Approved
0.6703	Remote Similarity	NPD4584	Approved
0.6702	Remote Similarity	NPD4581	Clinical (unspecified phase)
0.6698	Remote Similarity	NPD7827	Phase 1
0.6686	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6684	Remote Similarity	NPD7473	Discontinued
0.6684	Remote Similarity	NPD5929	Approved
0.6682	Remote Similarity	NPD6494	Phase 2
0.6667	Remote Similarity	NPD6658	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7831	Phase 2
0.6667	Remote Similarity	NPD7238	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7832	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5848	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5788	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6527	Approved
0.6667	Remote Similarity	NPD7833	Phase 2
0.6652	Remote Similarity	NPD7654	Discontinued
0.6651	Remote Similarity	NPD5530	Phase 1
0.665	Remote Similarity	NPD3349	Phase 2
0.6649	Remote Similarity	NPD2560	Approved
0.6649	Remote Similarity	NPD2563	Approved
0.6648	Remote Similarity	NPD2752	Clinical (unspecified phase)
0.6634	Remote Similarity	NPD3963	Phase 1
0.6629	Remote Similarity	NPD2161	Phase 2
0.6629	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6629	Remote Similarity	NPD1613	Approved
0.6628	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6616	Remote Similarity	NPD7546	Discontinued
0.6609	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6597	Remote Similarity	NPD6037	Discontinued
0.6596	Remote Similarity	NPD6818	Clinical (unspecified phase)
0.6592	Remote Similarity	NPD1375	Discontinued
0.6588	Remote Similarity	NPD1669	Approved
0.6578	Remote Similarity	NPD980	Clinical (unspecified phase)
0.6578	Remote Similarity	NPD3796	Clinical (unspecified phase)
0.6575	Remote Similarity	NPD5819	Phase 2
0.6574	Remote Similarity	NPD5164	Discontinued
0.6573	Remote Similarity	NPD4502	Phase 2
0.6569	Remote Similarity	NPD7686	Clinical (unspecified phase)
0.6561	Remote Similarity	NPD3556	Approved
0.6561	Remote Similarity	NPD3557	Approved
0.6561	Remote Similarity	NPD3559	Clinical (unspecified phase)
0.6561	Remote Similarity	NPD3558	Approved
0.6561	Remote Similarity	NPD3560	Approved
0.6546	Remote Similarity	NPD4481	Phase 3
0.6546	Remote Similarity	NPD2898	Approved
0.6543	Remote Similarity	NPD37	Approved
0.6541	Remote Similarity	NPD6031	Approved
0.6541	Remote Similarity	NPD6030	Approved
0.6538	Remote Similarity	NPD2494	Approved
0.6538	Remote Similarity	NPD3452	Approved
0.6538	Remote Similarity	NPD2493	Approved
0.6538	Remote Similarity	NPD3450	Approved
0.6537	Remote Similarity	NPD5582	Discontinued
0.6531	Remote Similarity	NPD5844	Phase 1
0.6528	Remote Similarity	NPD8149	Discontinued
0.6528	Remote Similarity	NPD6071	Discontinued
0.6524	Remote Similarity	NPD3538	Suspended
0.6524	Remote Similarity	NPD6502	Phase 2
0.652	Remote Similarity	NPD6526	Approved
0.6505	Remote Similarity	NPD2974	Approved
0.6505	Remote Similarity	NPD6284	Clinical (unspecified phase)
0.6505	Remote Similarity	NPD2973	Approved
0.6505	Remote Similarity	NPD2975	Approved
0.6503	Remote Similarity	NPD7124	Phase 2
0.6494	Remote Similarity	NPD4908	Phase 1
0.6477	Remote Similarity	NPD7477	Discontinued
0.6474	Remote Similarity	NPD6063	Approved
0.6468	Remote Similarity	NPD6340	Approved
0.6468	Remote Similarity	NPD6339	Approved
0.6465	Remote Similarity	NPD3815	Phase 1
0.6465	Remote Similarity	NPD3816	Phase 1
0.646	Remote Similarity	NPD7922	Phase 1
0.6458	Remote Similarity	NPD6234	Discontinued
0.6456	Remote Similarity	NPD8249	Clinical (unspecified phase)
0.6453	Remote Similarity	NPD8367	Approved
0.6453	Remote Similarity	NPD3342	Phase 2
0.6448	Remote Similarity	NPD2219	Phase 1
0.6446	Remote Similarity	NPD6773	Clinical (unspecified phase)
0.6445	Remote Similarity	NPD4582	Approved
0.6445	Remote Similarity	NPD4583	Approved
0.6444	Remote Similarity	NPD6522	Clinical (unspecified phase)
0.6442	Remote Similarity	NPD3837	Clinical (unspecified phase)
0.6442	Remote Similarity	NPD6874	Approved
0.644	Remote Similarity	NPD4965	Approved
0.644	Remote Similarity	NPD7773	Phase 2
0.644	Remote Similarity	NPD4967	Phase 2
0.644	Remote Similarity	NPD4966	Approved
0.6439	Remote Similarity	NPD6361	Phase 2
0.6438	Remote Similarity	NPD2899	Discontinued
0.6432	Remote Similarity	NPD4859	Phase 1
0.6429	Remote Similarity	NPD5177	Phase 3
0.6429	Remote Similarity	NPD7590	Clinical (unspecified phase)
0.6425	Remote Similarity	NPD6621	Clinical (unspecified phase)
0.6422	Remote Similarity	NPD2490	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