NPASS Compound

Structure

CID118633 OpenBabel06191715472D 26 31 0 0 1 0 0 0 0 0999 V2000 -4.2459 -1.4493 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8460 -3.4135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0008 -2.9259 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3803 -4.8758 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0697 -4.8753 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0697 -2.9248 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5349 -1.4619 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.4150 -3.9000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8443 -0.4878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2251 -4.3877 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6903 -2.9257 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2251 -3.4124 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6900 -1.9500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5354 -4.3886 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -0.0005 -1.9502 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9143 -4.3877 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9143 -3.4124 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5354 -3.4134 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -3.3803 -2.9253 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -0.8449 -1.4624 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3800 -1.9496 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.6696 -4.8889 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8446 -1.4625 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.8418 -4.6890 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.8418 -3.1111 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 21 1 0 0 0 0 2 3 2 0 0 0 0 2 11 1 0 0 0 0 3 15 1 0 0 0 0 4 10 1 0 0 0 0 4 14 1 0 0 0 0 5 10 2 0 0 0 0 5 16 1 0 0 0 0 6 12 2 0 0 0 0 6 17 1 0 0 0 0 7 13 1 0 0 0 0 7 21 1 0 0 0 0 8 24 1 0 0 0 0 8 25 1 0 0 0 0 9 23 1 0 0 0 0 9 26 1 0 0 0 0 10 12 1 0 0 0 0 11 13 2 0 0 0 0 11 18 1 0 0 0 0 12 19 1 0 0 0 0 13 20 1 0 0 0 0 14 18 1 0 0 0 0 14 22 1 0 0 0 0 15 20 2 0 0 0 0 15 23 1 0 0 0 0 16 17 2 0 0 0 0 16 24 1 0 0 0 0 17 25 1 0 0 0 0 18 19 1 0 0 0 0 19 21 1 0 0 0 0 20 26 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	353.13
Volume:	342.267
LogP:	2.395
LogD:	2.583
LogS:	-3.606
# Rotatable Bonds:	0
TPSA:	60.39
# H-Bond Aceptor:	6
# H-Bond Donor:	1
# Rings:	6
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.784
Synthetic Accessibility Score:	3.87
Fsp3:	0.4
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:	-4.829
MDCK Permeability:	3.0054734452278353e-05
Pgp-inhibitor:	0.011
Pgp-substrate:	0.089
Human Intestinal Absorption (HIA):	0.002
20% Bioavailability (F20%):	0.02
30% Bioavailability (F30%):	0.02

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.959
Plasma Protein Binding (PPB):	94.7863998413086%
Volume Distribution (VD):	1.734
Pgp-substrate:	6.346943378448486%

ADMET: Metabolism

CYP1A2-inhibitor:	0.841
CYP1A2-substrate:	0.611
CYP2C19-inhibitor:	0.909
CYP2C19-substrate:	0.906
CYP2C9-inhibitor:	0.054
CYP2C9-substrate:	0.832
CYP2D6-inhibitor:	0.965
CYP2D6-substrate:	0.905
CYP3A4-inhibitor:	0.955
CYP3A4-substrate:	0.918

ADMET: Excretion

Clearance (CL):	16.682
Half-life (T1/2):	0.135

ADMET: Toxicity

hERG Blockers:	0.027
Human Hepatotoxicity (H-HT):	0.105
Drug-inuced Liver Injury (DILI):	0.176
AMES Toxicity:	0.543
Rat Oral Acute Toxicity:	0.46
Maximum Recommended Daily Dose:	0.911
Skin Sensitization:	0.22
Carcinogencity:	0.929
Eye Corrosion:	0.003
Eye Irritation:	0.012
Respiratory Toxicity:	0.826

Download Data

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

Natural Product: NPC118633

Natural Product ID:	NPC118633
*Common Name:**	Chelidonine (+)
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	GHKISGDRQRSCII-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C20H19NO5/c1-21-7-13-11(2-3-15-20(13)26-9-23-15)18-14(22)4-10-5-16-17(25-8-24-16)6-12(10)19(18)21/h2-3,5-6,14,18-19,22H,4,7-9H2,1H3
SMILES:	CN1Cc2c(ccc3c2OCO3)C2C(Cc3cc4c(cc3C12)OCO4)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL436279
PubChem CID:	10147
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0002665] Benzophenanthridine alkaloids [CHEMONTID:0002666] Hexahydrobenzophenanthridine alkaloids

*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
NPO11457	Chelidonium majus	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11457	Chelidonium majus	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11457	Chelidonium majus	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO11457	Chelidonium majus	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]

☑ 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
GI50	1
IC50	4
Others	4
Potency	17

Activity Type	# Activity
Cell Line	1
Individual Protein	13
ORGANISM	2
Others	9
Protein-Protein Interaction	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT517	Cell Line	Panel NCI-60 (60 carcinoma cell lines)	Homo sapiens	GI50	=	433.0	nM	PMID[451126]
NPT483	Individual Protein	Prelamin-A/C	Homo sapiens	Potency	=	15848.9	nM	PMID[451128]
NPT53	Individual Protein	4'-phosphopantetheinyl transferase ffp	Bacillus subtilis	Potency	=	89125.1	nM	PMID[451127]
NPT109	Individual Protein	Cytochrome P450 3A4	Homo sapiens	Potency	=	5011.9	nM	PMID[451127]
NPT109	Individual Protein	Cytochrome P450 3A4	Homo sapiens	Potency	=	12589.3	nM	PMID[451128]
NPT50	Individual Protein	Tyrosyl-DNA phosphodiesterase 1	Homo sapiens	Potency	n.a.	1883.7	nM	PMID[451129]
NPT50	Individual Protein	Tyrosyl-DNA phosphodiesterase 1	Homo sapiens	Potency	n.a.	4109.5	nM	PMID[451130]
NPT50	Individual Protein	Tyrosyl-DNA phosphodiesterase 1	Homo sapiens	Potency	n.a.	2660.9	nM	PMID[451129]
NPT197	Protein-Protein Interaction	Menin/Histone-lysine N-methyltransferase MLL	Homo sapiens	Potency	=	39810.7	nM	PMID[451127]
NPT94	Individual Protein	Aldehyde dehydrogenase 1A1	Homo sapiens	Potency	=	39810.7	nM	PMID[451127]
NPT2	Others	Unspecified		Potency	=	1995.3	nM	PMID[451127]
NPT2	Others	Unspecified		Potency	=	7079.5	nM	PMID[451128]
NPT73	Individual Protein	Solute carrier organic anion transporter family member 1B1	Homo sapiens	Inhibition	=	59.5	%	PMID[451131]
NPT72	Individual Protein	Solute carrier organic anion transporter family member 1B3	Homo sapiens	Inhibition	=	82.29	%	PMID[451131]
NPT2	Others	Unspecified		Potency	n.a.	4466.8	nM	PMID[451130]
NPT2	Others	Unspecified		Potency	n.a.	5623.4	nM	PMID[451130]
NPT2	Others	Unspecified		Potency	n.a.	3548.1	nM	PMID[451129]
NPT2	Others	Unspecified		IC50	=	11000.0	nM	PMID[451132]
NPT2	Others	Unspecified		IC50	=	9000.0	nM	PMID[451132]
NPT2	Others	Unspecified		FC	=	3.0	n.a.	PMID[451132]
NPT2	Others	Unspecified		FC	=	6.0	n.a.	PMID[451132]
NPT20555	ORGANISM	SARS-CoV-2	Severe acute respiratory syndrome coronavirus 2	IC50	>	20000.0	nM	PMID[451133]
NPT20555	ORGANISM	SARS-CoV-2	Severe acute respiratory syndrome coronavirus 2	IC50	>	19952.62	nM	PMID[451133]

☑ 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 NPC118633 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	291
0.1-0.2	1357
0.2-0.3	4809
0.3-0.4	12208
0.4-0.5	6154
0.5-0.6	12578
0.6-0.7	4215
0.7-0.8	713
0.8-0.85	228
0.85-0.9	122
0.9-0.95	18
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC294790
1.0	High Similarity	NPC148693
0.9578	High Similarity	NPC275132
0.9231	High Similarity	NPC248642
0.9226	High Similarity	NPC126284
0.9207	High Similarity	NPC210918
0.9176	High Similarity	NPC156576
0.9146	High Similarity	NPC24264
0.9146	High Similarity	NPC476432
0.9141	High Similarity	NPC320104
0.9102	High Similarity	NPC2314
0.9096	High Similarity	NPC311991
0.9091	High Similarity	NPC190332
0.9091	High Similarity	NPC247389
0.9091	High Similarity	NPC181653
0.9085	High Similarity	NPC225774
0.9085	High Similarity	NPC16805
0.9085	High Similarity	NPC302527
0.9085	High Similarity	NPC167546
0.9053	High Similarity	NPC320223
0.9053	High Similarity	NPC114364
0.9048	High Similarity	NPC229166
0.9048	High Similarity	NPC199465
0.9048	High Similarity	NPC128560
0.9048	High Similarity	NPC187678
0.903	High Similarity	NPC219341
0.8976	High Similarity	NPC298979
0.8976	High Similarity	NPC100566
0.896	High Similarity	NPC214116
0.8935	High Similarity	NPC304675
0.8922	High Similarity	NPC82533
0.8922	High Similarity	NPC158148
0.8922	High Similarity	NPC266176
0.8922	High Similarity	NPC290759
0.8902	High Similarity	NPC266753
0.8902	High Similarity	NPC306902
0.8902	High Similarity	NPC160298
0.8902	High Similarity	NPC232924
0.8902	High Similarity	NPC477559
0.8882	High Similarity	NPC237044
0.8834	High Similarity	NPC234392
0.8834	High Similarity	NPC31311
0.8834	High Similarity	NPC146288
0.883	High Similarity	NPC474325
0.883	High Similarity	NPC15919
0.8817	High Similarity	NPC19520
0.8817	High Similarity	NPC470739
0.8817	High Similarity	NPC149090
0.8817	High Similarity	NPC477640
0.8817	High Similarity	NPC225597
0.881	High Similarity	NPC58766
0.881	High Similarity	NPC475686
0.8786	High Similarity	NPC476575
0.8786	High Similarity	NPC116284
0.8779	High Similarity	NPC474745
0.8779	High Similarity	NPC244554
0.8773	High Similarity	NPC41178
0.8773	High Similarity	NPC138487
0.8773	High Similarity	NPC216459
0.8757	High Similarity	NPC474475
0.8757	High Similarity	NPC6152
0.875	High Similarity	NPC57812
0.875	High Similarity	NPC474324
0.8743	High Similarity	NPC238530
0.8743	High Similarity	NPC232514
0.8743	High Similarity	NPC276944
0.8736	High Similarity	NPC135772
0.8728	High Similarity	NPC312918
0.8728	High Similarity	NPC477561
0.8728	High Similarity	NPC155442
0.8728	High Similarity	NPC476574
0.8713	High Similarity	NPC477558
0.8706	High Similarity	NPC65403
0.8698	High Similarity	NPC475845
0.8686	High Similarity	NPC9867
0.8675	High Similarity	NPC215829
0.8675	High Similarity	NPC97072
0.8671	High Similarity	NPC267408
0.8667	High Similarity	NPC476572
0.8663	High Similarity	NPC474470
0.8659	High Similarity	NPC325871
0.8659	High Similarity	NPC99659
0.8652	High Similarity	NPC117717
0.865	High Similarity	NPC233029
0.865	High Similarity	NPC210148
0.8647	High Similarity	NPC474708
0.8647	High Similarity	NPC75958
0.8639	High Similarity	NPC158376
0.8639	High Similarity	NPC12053
0.8639	High Similarity	NPC81218
0.8639	High Similarity	NPC145832
0.8639	High Similarity	NPC306555
0.8639	High Similarity	NPC150879
0.8639	High Similarity	NPC205421
0.8639	High Similarity	NPC117188
0.8639	High Similarity	NPC474931
0.8634	High Similarity	NPC475959
0.8631	High Similarity	NPC78222
0.8631	High Similarity	NPC136508
0.8631	High Similarity	NPC212794
0.8631	High Similarity	NPC196447
0.8631	High Similarity	NPC13504
0.8631	High Similarity	NPC96603
0.8631	High Similarity	NPC306843
0.8631	High Similarity	NPC477563
0.8631	High Similarity	NPC253043
0.8629	High Similarity	NPC474746
0.8629	High Similarity	NPC475981
0.8614	High Similarity	NPC477080
0.8596	High Similarity	NPC475754
0.8588	High Similarity	NPC237579
0.8588	High Similarity	NPC241055
0.858	High Similarity	NPC304659
0.858	High Similarity	NPC86144
0.858	High Similarity	NPC476002
0.8571	High Similarity	NPC233718
0.8571	High Similarity	NPC324144
0.8563	High Similarity	NPC4304
0.8563	High Similarity	NPC249274
0.8563	High Similarity	NPC205167
0.8545	High Similarity	NPC78733
0.8539	High Similarity	NPC82763
0.8538	High Similarity	NPC152212
0.8531	High Similarity	NPC57036
0.8531	High Similarity	NPC230098
0.8521	High Similarity	NPC168409
0.8514	High Similarity	NPC474506
0.8514	High Similarity	NPC32413
0.8506	High Similarity	NPC23219
0.8503	High Similarity	NPC111485
0.8483	Intermediate Similarity	NPC186546
0.8483	Intermediate Similarity	NPC476576
0.8476	Intermediate Similarity	NPC81733
0.8476	Intermediate Similarity	NPC326316
0.8462	Intermediate Similarity	NPC233650
0.8462	Intermediate Similarity	NPC1229
0.8462	Intermediate Similarity	NPC189470
0.8457	Intermediate Similarity	NPC470879
0.8457	Intermediate Similarity	NPC258695
0.8453	Intermediate Similarity	NPC162653
0.8452	Intermediate Similarity	NPC166014
0.8452	Intermediate Similarity	NPC27410
0.8448	Intermediate Similarity	NPC112575
0.8434	Intermediate Similarity	NPC76079
0.8434	Intermediate Similarity	NPC244112
0.8434	Intermediate Similarity	NPC93593
0.8424	Intermediate Similarity	NPC148898
0.8412	Intermediate Similarity	NPC247972
0.8412	Intermediate Similarity	NPC134858
0.8405	Intermediate Similarity	NPC7467
0.8402	Intermediate Similarity	NPC60186
0.8391	Intermediate Similarity	NPC49353
0.8382	Intermediate Similarity	NPC239775
0.8353	Intermediate Similarity	NPC218614
0.8352	Intermediate Similarity	NPC99179
0.8344	Intermediate Similarity	NPC476151
0.8344	Intermediate Similarity	NPC210437
0.8344	Intermediate Similarity	NPC476144
0.8344	Intermediate Similarity	NPC51957
0.8344	Intermediate Similarity	NPC106295
0.8344	Intermediate Similarity	NPC16107
0.8343	Intermediate Similarity	NPC241704
0.8333	Intermediate Similarity	NPC192135
0.8333	Intermediate Similarity	NPC477020
0.8333	Intermediate Similarity	NPC66341
0.8324	Intermediate Similarity	NPC168753
0.8324	Intermediate Similarity	NPC26240
0.8324	Intermediate Similarity	NPC477562
0.8324	Intermediate Similarity	NPC118274
0.8324	Intermediate Similarity	NPC69712
0.8323	Intermediate Similarity	NPC193949
0.8323	Intermediate Similarity	NPC207757
0.8323	Intermediate Similarity	NPC278799
0.8323	Intermediate Similarity	NPC5238
0.8323	Intermediate Similarity	NPC204828
0.8323	Intermediate Similarity	NPC469817
0.8323	Intermediate Similarity	NPC39701
0.8323	Intermediate Similarity	NPC172765
0.8323	Intermediate Similarity	NPC110416
0.8323	Intermediate Similarity	NPC189266
0.8323	Intermediate Similarity	NPC54379
0.8323	Intermediate Similarity	NPC2413
0.8323	Intermediate Similarity	NPC127674
0.8323	Intermediate Similarity	NPC276588
0.8323	Intermediate Similarity	NPC184026
0.8323	Intermediate Similarity	NPC249797
0.8323	Intermediate Similarity	NPC295691
0.8314	Intermediate Similarity	NPC210140
0.8314	Intermediate Similarity	NPC252960
0.8305	Intermediate Similarity	NPC179704
0.8304	Intermediate Similarity	NPC180306
0.8304	Intermediate Similarity	NPC169743
0.8286	Intermediate Similarity	NPC329969
0.8284	Intermediate Similarity	NPC59028
0.8284	Intermediate Similarity	NPC92191
0.8274	Intermediate Similarity	NPC323443
0.8274	Intermediate Similarity	NPC180756
0.8258	Intermediate Similarity	NPC73492
0.8258	Intermediate Similarity	NPC299990
0.8256	Intermediate Similarity	NPC264850

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 NPC118633 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	193
0.1-0.2	679
0.2-0.3	950
0.3-0.4	2172
0.4-0.5	2648
0.5-0.6	1676
0.6-0.7	664
0.7-0.8	147
0.8-0.85	21
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.869	High Similarity	NPD3051	Approved
0.8529	High Similarity	NPD2970	Approved
0.8529	High Similarity	NPD2969	Approved
0.8372	Intermediate Similarity	NPD2489	Approved
0.8372	Intermediate Similarity	NPD27	Approved
0.8344	Intermediate Similarity	NPD4584	Approved
0.8272	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.8266	Intermediate Similarity	NPD4481	Phase 3
0.8199	Intermediate Similarity	NPD4664	Clinical (unspecified phase)
0.8066	Intermediate Similarity	NPD4663	Approved
0.8059	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.8047	Intermediate Similarity	NPD4773	Phase 2
0.8047	Intermediate Similarity	NPD4772	Phase 2
0.8022	Intermediate Similarity	NPD7906	Approved
0.8	Intermediate Similarity	NPD7313	Approved
0.8	Intermediate Similarity	NPD4577	Approved
0.8	Intermediate Similarity	NPD4578	Approved
0.8	Intermediate Similarity	NPD7312	Approved
0.8	Intermediate Similarity	NPD7310	Approved
0.8	Intermediate Similarity	NPD7311	Approved
0.7956	Intermediate Similarity	NPD7309	Approved
0.7943	Intermediate Similarity	NPD6071	Discontinued
0.7939	Intermediate Similarity	NPD5241	Discontinued
0.7921	Intermediate Similarity	NPD8156	Discontinued
0.7907	Intermediate Similarity	NPD2563	Approved
0.7907	Intermediate Similarity	NPD2560	Approved
0.7892	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.7872	Intermediate Similarity	NPD4420	Approved
0.7865	Intermediate Similarity	NPD8251	Approved
0.7865	Intermediate Similarity	NPD8252	Approved
0.7865	Intermediate Similarity	NPD8099	Discontinued
0.7857	Intermediate Similarity	NPD8053	Approved
0.7857	Intermediate Similarity	NPD8054	Approved
0.7829	Intermediate Similarity	NPD7201	Clinical (unspecified phase)
0.7816	Intermediate Similarity	NPD7832	Clinical (unspecified phase)
0.7816	Intermediate Similarity	NPD7831	Phase 2
0.7816	Intermediate Similarity	NPD7833	Phase 2
0.7802	Intermediate Similarity	NPD2971	Approved
0.7802	Intermediate Similarity	NPD2968	Approved
0.7801	Intermediate Similarity	NPD5006	Approved
0.7801	Intermediate Similarity	NPD5005	Approved
0.7759	Intermediate Similarity	NPD6788	Approved
0.7746	Intermediate Similarity	NPD2977	Approved
0.7746	Intermediate Similarity	NPD2978	Approved
0.7742	Intermediate Similarity	NPD2488	Approved
0.7742	Intermediate Similarity	NPD2490	Approved
0.7738	Intermediate Similarity	NPD2421	Approved
0.7738	Intermediate Similarity	NPD2420	Approved
0.7705	Intermediate Similarity	NPD7280	Phase 3
0.7705	Intermediate Similarity	NPD7281	Phase 3
0.7688	Intermediate Similarity	NPD7298	Approved
0.7672	Intermediate Similarity	NPD7667	Clinical (unspecified phase)
0.7632	Intermediate Similarity	NPD2973	Approved
0.7632	Intermediate Similarity	NPD2975	Approved
0.7632	Intermediate Similarity	NPD2974	Approved
0.7616	Intermediate Similarity	NPD4017	Approved
0.7605	Intermediate Similarity	NPD4237	Approved
0.7605	Intermediate Similarity	NPD4236	Phase 3
0.7604	Intermediate Similarity	NPD4580	Approved
0.7602	Intermediate Similarity	NPD4727	Phase 1
0.7579	Intermediate Similarity	NPD5582	Discontinued
0.7576	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7576	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7568	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7556	Intermediate Similarity	NPD2898	Approved
0.7514	Intermediate Similarity	NPD5604	Discontinued
0.75	Intermediate Similarity	NPD3641	Approved
0.75	Intermediate Similarity	NPD5177	Phase 3
0.75	Intermediate Similarity	NPD3639	Approved
0.75	Intermediate Similarity	NPD6031	Approved
0.75	Intermediate Similarity	NPD3640	Phase 3
0.75	Intermediate Similarity	NPD6030	Approved
0.7486	Intermediate Similarity	NPD6107	Approved
0.7474	Intermediate Similarity	NPD2494	Approved
0.7474	Intermediate Similarity	NPD3452	Approved
0.7474	Intermediate Similarity	NPD3450	Approved
0.7474	Intermediate Similarity	NPD2493	Approved
0.7461	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.745	Intermediate Similarity	NPD7827	Phase 1
0.7449	Intermediate Similarity	NPD4583	Approved
0.7449	Intermediate Similarity	NPD4582	Approved
0.7447	Intermediate Similarity	NPD7243	Clinical (unspecified phase)
0.7444	Intermediate Similarity	NPD4010	Discontinued
0.7439	Intermediate Similarity	NPD3110	Approved
0.7439	Intermediate Similarity	NPD3109	Approved
0.7426	Intermediate Similarity	NPD7047	Phase 3
0.7398	Intermediate Similarity	NPD4004	Approved
0.7398	Intermediate Similarity	NPD4002	Approved
0.7384	Intermediate Similarity	NPD1754	Clinical (unspecified phase)
0.7379	Intermediate Similarity	NPD6997	Phase 2
0.7368	Intermediate Similarity	NPD2422	Clinical (unspecified phase)
0.736	Intermediate Similarity	NPD4581	Clinical (unspecified phase)
0.736	Intermediate Similarity	NPD4040	Phase 1
0.7345	Intermediate Similarity	NPD5773	Approved
0.7345	Intermediate Similarity	NPD5772	Approved
0.733	Intermediate Similarity	NPD7296	Approved
0.7326	Intermediate Similarity	NPD3534	Clinical (unspecified phase)
0.7318	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7314	Intermediate Similarity	NPD7261	Clinical (unspecified phase)
0.7294	Intermediate Similarity	NPD3060	Approved
0.7288	Intermediate Similarity	NPD7945	Clinical (unspecified phase)
0.7259	Intermediate Similarity	NPD3057	Approved
0.7258	Intermediate Similarity	NPD6297	Approved
0.7257	Intermediate Similarity	NPD4210	Discontinued
0.7256	Intermediate Similarity	NPD2669	Clinical (unspecified phase)
0.7251	Intermediate Similarity	NPD5754	Discontinued
0.7243	Intermediate Similarity	NPD5312	Approved
0.7243	Intermediate Similarity	NPD5313	Approved
0.7229	Intermediate Similarity	NPD2238	Phase 2
0.7228	Intermediate Similarity	NPD5602	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD4055	Discovery
0.7216	Intermediate Similarity	NPD4005	Discontinued
0.7212	Intermediate Similarity	NPD5718	Phase 2
0.7209	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7209	Intermediate Similarity	NPD5160	Discontinued
0.72	Intermediate Similarity	NPD5976	Discontinued
0.7198	Intermediate Similarity	NPD7802	Discontinued
0.7196	Intermediate Similarity	NPD6853	Approved
0.7196	Intermediate Similarity	NPD6851	Approved
0.7193	Intermediate Similarity	NPD6674	Discontinued
0.7184	Intermediate Similarity	NPD1424	Approved
0.7182	Intermediate Similarity	NPD7400	Phase 3
0.7181	Intermediate Similarity	NPD8453	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD2972	Approved
0.7172	Intermediate Similarity	NPD3533	Approved
0.7169	Intermediate Similarity	NPD554	Clinical (unspecified phase)
0.7169	Intermediate Similarity	NPD4475	Approved
0.7169	Intermediate Similarity	NPD4474	Approved
0.7168	Intermediate Similarity	NPD6667	Approved
0.7168	Intermediate Similarity	NPD6666	Approved
0.7168	Intermediate Similarity	NPD3845	Phase 1
0.7167	Intermediate Similarity	NPD4967	Phase 2
0.7167	Intermediate Similarity	NPD4965	Approved
0.7167	Intermediate Similarity	NPD4966	Approved
0.7158	Intermediate Similarity	NPD4166	Phase 2
0.7157	Intermediate Similarity	NPD4107	Approved
0.715	Intermediate Similarity	NPD3763	Approved
0.715	Intermediate Similarity	NPD6723	Discontinued
0.7143	Intermediate Similarity	NPD6090	Discontinued
0.7126	Intermediate Similarity	NPD3124	Discontinued
0.7118	Intermediate Similarity	NPD1632	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD8095	Phase 1
0.7101	Intermediate Similarity	NPD6896	Approved
0.7101	Intermediate Similarity	NPD6895	Approved
0.7098	Intermediate Similarity	NPD5525	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD37	Approved
0.7093	Intermediate Similarity	NPD4162	Approved
0.7091	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.709	Intermediate Similarity	NPD7549	Discontinued
0.7088	Intermediate Similarity	NPD5709	Phase 3
0.7086	Intermediate Similarity	NPD7019	Approved
0.7086	Intermediate Similarity	NPD7020	Approved
0.7085	Intermediate Similarity	NPD3448	Approved
0.7085	Intermediate Similarity	NPD2491	Approved
0.7079	Intermediate Similarity	NPD4859	Phase 1
0.7069	Intermediate Similarity	NPD7124	Phase 2
0.7068	Intermediate Similarity	NPD5087	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD6042	Phase 2
0.7059	Intermediate Similarity	NPD4108	Discontinued
0.7059	Intermediate Similarity	NPD42	Phase 2
0.7059	Intermediate Similarity	NPD1753	Discontinued
0.7052	Intermediate Similarity	NPD6748	Discontinued
0.7052	Intermediate Similarity	NPD6331	Phase 2
0.705	Intermediate Similarity	NPD7497	Discontinued
0.7049	Intermediate Similarity	NPD4666	Phase 3
0.7048	Intermediate Similarity	NPD5156	Approved
0.7048	Intermediate Similarity	NPD5155	Approved
0.7047	Intermediate Similarity	NPD7235	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD3647	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD4579	Clinical (unspecified phase)
0.7035	Intermediate Similarity	NPD4482	Phase 3
0.7035	Intermediate Similarity	NPD7037	Approved
0.7029	Intermediate Similarity	NPD7598	Phase 2
0.7027	Intermediate Similarity	NPD6688	Approved
0.7027	Intermediate Similarity	NPD6687	Approved
0.7021	Intermediate Similarity	NPD7479	Phase 2
0.7017	Intermediate Similarity	NPD5977	Approved
0.7017	Intermediate Similarity	NPD5978	Approved
0.7014	Intermediate Similarity	NPD5619	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD2677	Approved
0.701	Intermediate Similarity	NPD3808	Clinical (unspecified phase)
0.7005	Intermediate Similarity	NPD7228	Approved
0.7	Intermediate Similarity	NPD3382	Approved
0.7	Intermediate Similarity	NPD3384	Approved
0.7	Intermediate Similarity	NPD3383	Approved
0.6995	Remote Similarity	NPD6234	Discontinued
0.6991	Remote Similarity	NPD6625	Approved
0.6989	Remote Similarity	NPD4123	Phase 3
0.6989	Remote Similarity	NPD6365	Clinical (unspecified phase)
0.6988	Remote Similarity	NPD2605	Approved
0.6988	Remote Similarity	NPD3594	Approved
0.6988	Remote Similarity	NPD3595	Approved
0.6988	Remote Similarity	NPD2606	Approved
0.6984	Remote Similarity	NPD7007	Discovery
0.6977	Remote Similarity	NPD4725	Approved
0.6977	Remote Similarity	NPD1375	Discontinued
0.6977	Remote Similarity	NPD4726	Approved
0.6977	Remote Similarity	NPD4721	Approved
0.6976	Remote Similarity	NPD5676	Approved
0.6951	Remote Similarity	NPD7258	Clinical (unspecified phase)

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