NPASS Compound

Structure

NPC471312 OpenBabel07101718282D 28 28 0 0 0 0 0 0 0 0999 V2000 10.3923 9.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.3923 10.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.5263 10.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6603 10.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 10.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 10.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 10.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 10.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 10.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 10.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 9.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 8.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 7.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 7.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 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 -0.8660 2.5000 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 -0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 Cl 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 -0.0000 3.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 0 0 0 2 3 1 0 0 0 0 3 4 1 0 0 0 0 4 5 1 0 0 0 0 5 6 1 0 0 0 0 6 7 1 0 0 0 0 7 8 1 0 0 0 0 8 9 1 0 0 0 0 9 10 2 0 0 0 0 10 11 1 0 0 0 0 11 12 1 0 0 0 0 12 13 1 0 0 0 0 13 14 1 0 0 0 0 14 15 1 0 0 0 0 15 16 1 0 0 0 0 16 17 1 0 0 0 0 17 24 1 0 0 0 0 18 19 2 0 0 0 0 18 22 1 0 0 0 0 19 23 1 0 0 0 0 20 22 2 0 0 0 0 20 26 1 0 0 0 0 21 22 1 0 0 0 0 21 27 1 0 0 0 0 23 25 1 0 0 0 0 23 26 2 0 0 0 0 24 27 2 3 0 0 0 24 28 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	406.28
Volume:	447.916
LogP:	6.647
LogD:	4.263
LogS:	-2.728
# Rotatable Bonds:	18
TPSA:	41.99
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	1
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.166
Synthetic Accessibility Score:	2.284
Fsp3:	0.667
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.884
MDCK Permeability:	1.535472802061122e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.868
30% Bioavailability (F30%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.273
Plasma Protein Binding (PPB):	99.31742095947266%
Volume Distribution (VD):	2.32
Pgp-substrate:	0.7097181677818298%

ADMET: Metabolism

CYP1A2-inhibitor:	0.133
CYP1A2-substrate:	0.542
CYP2C19-inhibitor:	0.499
CYP2C19-substrate:	0.073
CYP2C9-inhibitor:	0.293
CYP2C9-substrate:	0.921
CYP2D6-inhibitor:	0.679
CYP2D6-substrate:	0.775
CYP3A4-inhibitor:	0.613
CYP3A4-substrate:	0.093

ADMET: Excretion

Clearance (CL):	4.59
Half-life (T1/2):	0.684

ADMET: Toxicity

hERG Blockers:	0.874
Human Hepatotoxicity (H-HT):	0.23
Drug-inuced Liver Injury (DILI):	0.051
AMES Toxicity:	0.008
Rat Oral Acute Toxicity:	0.097
Maximum Recommended Daily Dose:	0.099
Skin Sensitization:	0.951
Carcinogencity:	0.063
Eye Corrosion:	0.004
Eye Irritation:	0.03
Respiratory Toxicity:	0.903

Download Data

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

Natural Product: NPC471312

Natural Product ID:	NPC471312
*Common Name:**	N-[(2-Chloropyridin-5-Yl)Methyl]Oleamide
IUPAC Name:	(Z)-N-[(6-chloropyridin-3-yl)methyl]octadec-9-enamide
Synonyms:
Standard InCHIKey:	JIAIJNCBLCMFJI-KTKRTIGZSA-N
Standard InCHI:	InChI=1S/C24H39ClN2O/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-24(28)27-21-22-18-19-23(25)26-20-22/h9-10,18-20H,2-8,11-17,21H2,1H3,(H,27,28)/b10-9-
SMILES:	CCCCCCCCC=CCCCCCCCC(=O)NCC1=CN=C(C=C1)Cl
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2413170
PubChem CID:	71770312
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000089] Pyridines and derivatives [CHEMONTID:0003970] Halopyridines [CHEMONTID:0004532] 2-halopyridines

*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
NPO18988	Lepidium meyenii	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12932133]
NPO18988	Lepidium meyenii	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23891163]
NPO18988	Lepidium meyenii	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24972328]
NPO18988	Lepidium meyenii	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[33320645]
NPO18988	Lepidium meyenii	Species	Brassicaceae	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	3

Activity Type	# Activity
Individual Protein	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1418	Individual Protein	Anandamide amidohydrolase	Homo sapiens	IC50	=	15300.0	nM	PMID[537759]
NPT1418	Individual Protein	Anandamide amidohydrolase	Homo sapiens	Imax	=	79.0	%	PMID[537759]
NPT1418	Individual Protein	Anandamide amidohydrolase	Homo sapiens	Inhibition	=	43.5	%	PMID[537759]
NPT1418	Individual Protein	Anandamide amidohydrolase	Homo sapiens	Inhibition	=	76.1	%	PMID[537759]

☑ 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 NPC471312 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	301
0.1-0.2	4630
0.2-0.3	20464
0.3-0.4	11011
0.4-0.5	3489
0.5-0.6	2054
0.6-0.7	629
0.7-0.8	112
0.8-0.85	4
0.85-0.9	0
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9302	High Similarity	NPC471311
0.9302	High Similarity	NPC471313
0.8467	Intermediate Similarity	NPC324611
0.8284	Intermediate Similarity	NPC290094
0.8201	Intermediate Similarity	NPC471322
0.8182	Intermediate Similarity	NPC315348
0.8182	Intermediate Similarity	NPC32002
0.8102	Intermediate Similarity	NPC169625
0.8102	Intermediate Similarity	NPC202957
0.7986	Intermediate Similarity	NPC89490
0.797	Intermediate Similarity	NPC240136
0.797	Intermediate Similarity	NPC297486
0.797	Intermediate Similarity	NPC471402
0.7929	Intermediate Similarity	NPC475090
0.7929	Intermediate Similarity	NPC475105
0.7929	Intermediate Similarity	NPC329896
0.7914	Intermediate Similarity	NPC212125
0.7868	Intermediate Similarity	NPC265605
0.7868	Intermediate Similarity	NPC48564
0.7868	Intermediate Similarity	NPC182570
0.7846	Intermediate Similarity	NPC27802
0.7838	Intermediate Similarity	NPC471323
0.7826	Intermediate Similarity	NPC476322
0.7752	Intermediate Similarity	NPC76540
0.7746	Intermediate Similarity	NPC315320
0.7703	Intermediate Similarity	NPC476454
0.766	Intermediate Similarity	NPC306397
0.7647	Intermediate Similarity	NPC91958
0.7613	Intermediate Similarity	NPC476464
0.7597	Intermediate Similarity	NPC259644
0.7597	Intermediate Similarity	NPC73952
0.7597	Intermediate Similarity	NPC469786
0.7597	Intermediate Similarity	NPC469760
0.7597	Intermediate Similarity	NPC469765
0.7597	Intermediate Similarity	NPC469763
0.7597	Intermediate Similarity	NPC25008
0.7571	Intermediate Similarity	NPC27740
0.7569	Intermediate Similarity	NPC256893
0.7564	Intermediate Similarity	NPC129721
0.7554	Intermediate Similarity	NPC329825
0.7552	Intermediate Similarity	NPC476131
0.7548	Intermediate Similarity	NPC80597
0.7548	Intermediate Similarity	NPC70922
0.7548	Intermediate Similarity	NPC212376
0.7548	Intermediate Similarity	NPC211572
0.7548	Intermediate Similarity	NPC75540
0.7535	Intermediate Similarity	NPC165370
0.7518	Intermediate Similarity	NPC146373
0.7518	Intermediate Similarity	NPC143603
0.7518	Intermediate Similarity	NPC245244
0.7518	Intermediate Similarity	NPC166424
0.7517	Intermediate Similarity	NPC322488
0.75	Intermediate Similarity	NPC69914
0.7483	Intermediate Similarity	NPC29702
0.7432	Intermediate Similarity	NPC65408
0.7421	Intermediate Similarity	NPC59779
0.7421	Intermediate Similarity	NPC71079
0.7421	Intermediate Similarity	NPC124542
0.7421	Intermediate Similarity	NPC471177
0.7413	Intermediate Similarity	NPC278451
0.7407	Intermediate Similarity	NPC116961
0.7389	Intermediate Similarity	NPC469785
0.7375	Intermediate Similarity	NPC474217
0.7342	Intermediate Similarity	NPC469762
0.7333	Intermediate Similarity	NPC235843
0.7329	Intermediate Similarity	NPC471178
0.7329	Intermediate Similarity	NPC85918
0.7287	Intermediate Similarity	NPC83987
0.7284	Intermediate Similarity	NPC278366
0.7284	Intermediate Similarity	NPC127730
0.7267	Intermediate Similarity	NPC311276
0.7254	Intermediate Similarity	NPC46358
0.7222	Intermediate Similarity	NPC477975
0.7218	Intermediate Similarity	NPC231655
0.7211	Intermediate Similarity	NPC101165
0.7208	Intermediate Similarity	NPC314372
0.72	Intermediate Similarity	NPC251722
0.72	Intermediate Similarity	NPC314102
0.7188	Intermediate Similarity	NPC477591
0.7178	Intermediate Similarity	NPC160105
0.7178	Intermediate Similarity	NPC98187
0.716	Intermediate Similarity	NPC476446
0.716	Intermediate Similarity	NPC473057
0.716	Intermediate Similarity	NPC97367
0.716	Intermediate Similarity	NPC469813
0.716	Intermediate Similarity	NPC78375
0.7143	Intermediate Similarity	NPC282398
0.7134	Intermediate Similarity	NPC24678
0.7134	Intermediate Similarity	NPC105818
0.7133	Intermediate Similarity	NPC328029
0.7115	Intermediate Similarity	NPC477974
0.7105	Intermediate Similarity	NPC316811
0.7078	Intermediate Similarity	NPC190296
0.7073	Intermediate Similarity	NPC474561
0.7073	Intermediate Similarity	NPC108469
0.7073	Intermediate Similarity	NPC49954
0.7055	Intermediate Similarity	NPC40779
0.7034	Intermediate Similarity	NPC151489
0.703	Intermediate Similarity	NPC201700
0.7006	Intermediate Similarity	NPC314603
0.6994	Remote Similarity	NPC282231
0.6974	Remote Similarity	NPC150259
0.697	Remote Similarity	NPC41717
0.6964	Remote Similarity	NPC469938
0.6951	Remote Similarity	NPC194640
0.6948	Remote Similarity	NPC469767
0.6948	Remote Similarity	NPC469768
0.6948	Remote Similarity	NPC469779
0.6948	Remote Similarity	NPC469780
0.6948	Remote Similarity	NPC469761
0.6948	Remote Similarity	NPC469784
0.6948	Remote Similarity	NPC469783
0.6941	Remote Similarity	NPC248462
0.6933	Remote Similarity	NPC279918
0.6933	Remote Similarity	NPC131718
0.6928	Remote Similarity	NPC63751
0.6923	Remote Similarity	NPC150048
0.6923	Remote Similarity	NPC203754
0.6905	Remote Similarity	NPC477976
0.6903	Remote Similarity	NPC469766
0.6899	Remote Similarity	NPC470111
0.6892	Remote Similarity	NPC471589
0.6879	Remote Similarity	NPC476566
0.6879	Remote Similarity	NPC159856
0.6871	Remote Similarity	NPC230869
0.6863	Remote Similarity	NPC114310
0.6842	Remote Similarity	NPC471310
0.6813	Remote Similarity	NPC40070
0.6792	Remote Similarity	NPC471957
0.679	Remote Similarity	NPC229055
0.6786	Remote Similarity	NPC473901
0.6784	Remote Similarity	NPC248454
0.6784	Remote Similarity	NPC64436
0.6774	Remote Similarity	NPC110126
0.6774	Remote Similarity	NPC73767
0.6772	Remote Similarity	NPC285731
0.6772	Remote Similarity	NPC167400
0.6766	Remote Similarity	NPC54988
0.6763	Remote Similarity	NPC233936
0.6753	Remote Similarity	NPC105127
0.6753	Remote Similarity	NPC84911
0.6747	Remote Similarity	NPC102423
0.6727	Remote Similarity	NPC25899
0.6724	Remote Similarity	NPC133306
0.6713	Remote Similarity	NPC81561
0.6711	Remote Similarity	NPC330326
0.671	Remote Similarity	NPC169433
0.6707	Remote Similarity	NPC138018
0.6706	Remote Similarity	NPC313791
0.6705	Remote Similarity	NPC474707
0.6705	Remote Similarity	NPC300688
0.6705	Remote Similarity	NPC471997
0.669	Remote Similarity	NPC84268
0.6688	Remote Similarity	NPC29886
0.6688	Remote Similarity	NPC96102
0.6688	Remote Similarity	NPC261195
0.6686	Remote Similarity	NPC59269
0.6686	Remote Similarity	NPC151939
0.6686	Remote Similarity	NPC314940
0.6686	Remote Similarity	NPC473764
0.6667	Remote Similarity	NPC467188
0.6667	Remote Similarity	NPC470233
0.6667	Remote Similarity	NPC86288
0.6667	Remote Similarity	NPC92796
0.6667	Remote Similarity	NPC135141
0.6667	Remote Similarity	NPC104483
0.6648	Remote Similarity	NPC117244
0.6648	Remote Similarity	NPC473763
0.6647	Remote Similarity	NPC213468
0.6647	Remote Similarity	NPC478182
0.6646	Remote Similarity	NPC477977
0.6645	Remote Similarity	NPC174421
0.6645	Remote Similarity	NPC82295
0.6643	Remote Similarity	NPC148140
0.6629	Remote Similarity	NPC65215
0.6629	Remote Similarity	NPC173028
0.6629	Remote Similarity	NPC163055
0.6628	Remote Similarity	NPC267885
0.6627	Remote Similarity	NPC78020
0.6621	Remote Similarity	NPC11863
0.6617	Remote Similarity	NPC213774
0.661	Remote Similarity	NPC94752
0.6609	Remote Similarity	NPC314919
0.6604	Remote Similarity	NPC230085
0.6604	Remote Similarity	NPC159630
0.6599	Remote Similarity	NPC56856
0.6592	Remote Similarity	NPC95783
0.6588	Remote Similarity	NPC194411
0.6587	Remote Similarity	NPC48192
0.6585	Remote Similarity	NPC263455
0.6585	Remote Similarity	NPC209362
0.6584	Remote Similarity	NPC201380
0.6584	Remote Similarity	NPC105811
0.6584	Remote Similarity	NPC179787
0.6573	Remote Similarity	NPC204565
0.6573	Remote Similarity	NPC317030
0.657	Remote Similarity	NPC149155
0.657	Remote Similarity	NPC203468
0.657	Remote Similarity	NPC110500
0.6564	Remote Similarity	NPC70406

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 NPC471312 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	196
0.1-0.2	696
0.2-0.3	1090
0.3-0.4	1664
0.4-0.5	3013
0.5-0.6	1909
0.6-0.7	481
0.7-0.8	100
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
0.8514	High Similarity	NPD5541	Clinical (unspecified phase)
0.8182	Intermediate Similarity	NPD2073	Approved
0.8182	Intermediate Similarity	NPD2075	Approved
0.8182	Intermediate Similarity	NPD2072	Approved
0.8182	Intermediate Similarity	NPD2074	Approved
0.8014	Intermediate Similarity	NPD3717	Discontinued
0.7986	Intermediate Similarity	NPD2896	Discontinued
0.7986	Intermediate Similarity	NPD1095	Clinical (unspecified phase)
0.7973	Intermediate Similarity	NPD6148	Clinical (unspecified phase)
0.7919	Intermediate Similarity	NPD4702	Approved
0.7919	Intermediate Similarity	NPD4703	Approved
0.7914	Intermediate Similarity	NPD9284	Approved
0.7868	Intermediate Similarity	NPD271	Approved
0.7868	Intermediate Similarity	NPD270	Clinical (unspecified phase)
0.7868	Intermediate Similarity	NPD268	Approved
0.7863	Intermediate Similarity	NPD4823	Approved
0.7863	Intermediate Similarity	NPD4824	Approved
0.7808	Intermediate Similarity	NPD768	Clinical (unspecified phase)
0.775	Intermediate Similarity	NPD2076	Approved
0.775	Intermediate Similarity	NPD2077	Approved
0.7746	Intermediate Similarity	NPD9206	Approved
0.7746	Intermediate Similarity	NPD9207	Approved
0.774	Intermediate Similarity	NPD1380	Discovery
0.7718	Intermediate Similarity	NPD3813	Approved
0.7718	Intermediate Similarity	NPD751	Clinical (unspecified phase)
0.7688	Intermediate Similarity	NPD3117	Approved
0.7688	Intermediate Similarity	NPD3116	Approved
0.7687	Intermediate Similarity	NPD269	Clinical (unspecified phase)
0.7682	Intermediate Similarity	NPD2110	Approved
0.7662	Intermediate Similarity	NPD2165	Phase 1
0.766	Intermediate Similarity	NPD2118	Approved
0.766	Intermediate Similarity	NPD2119	Approved
0.766	Intermediate Similarity	NPD9080	Approved
0.7647	Intermediate Similarity	NPD3262	Approved
0.7643	Intermediate Similarity	NPD4384	Clinical (unspecified phase)
0.7636	Intermediate Similarity	NPD5213	Clinical (unspecified phase)
0.7613	Intermediate Similarity	NPD3112	Approved
0.7613	Intermediate Similarity	NPD3113	Approved
0.7613	Intermediate Similarity	NPD3114	Approved
0.7613	Intermediate Similarity	NPD3115	Approved
0.7584	Intermediate Similarity	NPD1382	Phase 2
0.7584	Intermediate Similarity	NPD4805	Approved
0.7584	Intermediate Similarity	NPD1383	Phase 3
0.7564	Intermediate Similarity	NPD6497	Approved
0.7564	Intermediate Similarity	NPD2865	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD8026	Phase 1
0.7517	Intermediate Similarity	NPD1649	Discontinued
0.7516	Intermediate Similarity	NPD5255	Approved
0.75	Intermediate Similarity	NPD3476	Approved
0.75	Intermediate Similarity	NPD3475	Approved
0.75	Intermediate Similarity	NPD7469	Discontinued
0.75	Intermediate Similarity	NPD3929	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6026	Approved
0.7484	Intermediate Similarity	NPD3339	Approved
0.7484	Intermediate Similarity	NPD2012	Clinical (unspecified phase)
0.747	Intermediate Similarity	NPD4891	Phase 2
0.7468	Intermediate Similarity	NPD2511	Approved
0.7465	Intermediate Similarity	NPD9583	Approved
0.745	Intermediate Similarity	NPD4804	Approved
0.745	Intermediate Similarity	NPD945	Clinical (unspecified phase)
0.7447	Intermediate Similarity	NPD9357	Approved
0.7432	Intermediate Similarity	NPD9506	Approved
0.7432	Intermediate Similarity	NPD200	Phase 2
0.7432	Intermediate Similarity	NPD201	Phase 2
0.7425	Intermediate Similarity	NPD6194	Discontinued
0.7413	Intermediate Similarity	NPD992	Clinical (unspecified phase)
0.7413	Intermediate Similarity	NPD1598	Discontinued
0.7413	Intermediate Similarity	NPD991	Phase 2
0.7407	Intermediate Similarity	NPD4973	Approved
0.7397	Intermediate Similarity	NPD1993	Approved
0.7397	Intermediate Similarity	NPD1627	Clinical (unspecified phase)
0.7397	Intermediate Similarity	NPD1995	Approved
0.7397	Intermediate Similarity	NPD1994	Approved
0.7383	Intermediate Similarity	NPD203	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD1352	Discontinued
0.7347	Intermediate Similarity	NPD4030	Approved
0.7347	Intermediate Similarity	NPD4028	Approved
0.7347	Intermediate Similarity	NPD4029	Approved
0.7347	Intermediate Similarity	NPD3942	Approved
0.7347	Intermediate Similarity	NPD3944	Approved
0.7338	Intermediate Similarity	NPD1661	Suspended
0.7326	Intermediate Similarity	NPD4699	Discontinued
0.7325	Intermediate Similarity	NPD2809	Approved
0.7321	Intermediate Similarity	NPD5092	Clinical (unspecified phase)
0.7319	Intermediate Similarity	NPD9392	Approved
0.7319	Intermediate Similarity	NPD9396	Approved
0.7305	Intermediate Similarity	NPD748	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD5088	Discontinued
0.726	Intermediate Similarity	NPD715	Phase 3
0.7256	Intermediate Similarity	NPD5934	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD792	Discontinued
0.7241	Intermediate Similarity	NPD4529	Approved
0.7241	Intermediate Similarity	NPD4526	Approved
0.7241	Intermediate Similarity	NPD4528	Approved
0.7239	Intermediate Similarity	NPD6872	Clinical (unspecified phase)
0.7233	Intermediate Similarity	NPD2582	Approved
0.7233	Intermediate Similarity	NPD2581	Approved
0.7218	Intermediate Similarity	NPD9099	Clinical (unspecified phase)
0.7218	Intermediate Similarity	NPD9098	Phase 3
0.7215	Intermediate Similarity	NPD5358	Clinical (unspecified phase)
0.7211	Intermediate Similarity	NPD9726	Discontinued
0.7186	Intermediate Similarity	NPD8123	Approved
0.7186	Intermediate Similarity	NPD8122	Approved
0.7181	Intermediate Similarity	NPD272	Approved
0.7181	Intermediate Similarity	NPD2142	Approved
0.7181	Intermediate Similarity	NPD2140	Approved
0.7181	Intermediate Similarity	NPD2141	Approved
0.7134	Intermediate Similarity	NPD5862	Discovery
0.7133	Intermediate Similarity	NPD206	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD6375	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD6471	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD3928	Approved
0.7111	Intermediate Similarity	NPD3931	Approved
0.7108	Intermediate Similarity	NPD7217	Approved
0.7108	Intermediate Similarity	NPD7216	Approved
0.7105	Intermediate Similarity	NPD2068	Approved
0.7105	Intermediate Similarity	NPD2070	Approved
0.7105	Intermediate Similarity	NPD2071	Approved
0.7105	Intermediate Similarity	NPD2069	Approved
0.7091	Intermediate Similarity	NPD2619	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD2620	Phase 2
0.7079	Intermediate Similarity	NPD3231	Approved
0.7078	Intermediate Similarity	NPD2006	Phase 2
0.7078	Intermediate Similarity	NPD1427	Clinical (unspecified phase)
0.7076	Intermediate Similarity	NPD4484	Phase 1
0.7073	Intermediate Similarity	NPD5611	Phase 2
0.707	Intermediate Similarity	NPD3576	Approved
0.707	Intermediate Similarity	NPD3575	Approved
0.707	Intermediate Similarity	NPD5538	Clinical (unspecified phase)
0.7066	Intermediate Similarity	NPD5322	Clinical (unspecified phase)
0.7066	Intermediate Similarity	NPD5065	Approved
0.7063	Intermediate Similarity	NPD473	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD6635	Approved
0.7055	Intermediate Similarity	NPD5925	Phase 1
0.7024	Intermediate Similarity	NPD5100	Phase 3
0.7024	Intermediate Similarity	NPD2771	Approved
0.7012	Intermediate Similarity	NPD926	Approved
0.7012	Intermediate Similarity	NPD925	Approved
0.7007	Intermediate Similarity	NPD5352	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD2089	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD2536	Discontinued
0.7	Intermediate Similarity	NPD2061	Approved
0.7	Intermediate Similarity	NPD3927	Phase 2
0.6995	Remote Similarity	NPD3932	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD4239	Clinical (unspecified phase)
0.6988	Remote Similarity	NPD4184	Clinical (unspecified phase)
0.6982	Remote Similarity	NPD5751	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD2882	Phase 1
0.6981	Remote Similarity	NPD5965	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD5892	Approved
0.6975	Remote Similarity	NPD1554	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD604	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD4510	Discontinued
0.6962	Remote Similarity	NPD1183	Approved
0.6959	Remote Similarity	NPD8408	Discontinued
0.6959	Remote Similarity	NPD4011	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD3930	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD8129	Discovery
0.6948	Remote Similarity	NPD1395	Clinical (unspecified phase)
0.6948	Remote Similarity	NPD165	Phase 2
0.6923	Remote Similarity	NPD8823	Approved
0.6914	Remote Similarity	NPD2373	Clinical (unspecified phase)
0.6899	Remote Similarity	NPD1270	Approved
0.6899	Remote Similarity	NPD4547	Phase 3
0.6893	Remote Similarity	NPD9689	Approved
0.6875	Remote Similarity	NPD9343	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD1213	Phase 3
0.6875	Remote Similarity	NPD6476	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD6158	Phase 2
0.6875	Remote Similarity	NPD9706	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD424	Approved
0.6867	Remote Similarity	NPD803	Phase 1
0.6867	Remote Similarity	NPD4174	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD425	Approved
0.6865	Remote Similarity	NPD4533	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD2829	Clinical (unspecified phase)
0.686	Remote Similarity	NPD7414	Clinical (unspecified phase)
0.686	Remote Similarity	NPD4383	Clinical (unspecified phase)
0.6859	Remote Similarity	NPD2007	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD8021	Approved
0.6857	Remote Similarity	NPD8020	Approved
0.6855	Remote Similarity	NPD2430	Phase 2
0.6842	Remote Similarity	NPD8036	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD8037	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD6610	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD3082	Discontinued
0.6821	Remote Similarity	NPD5728	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD2323	Clinical (unspecified phase)
0.6815	Remote Similarity	NPD1918	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD2305	Discontinued
0.6813	Remote Similarity	NPD7913	Clinical (unspecified phase)
0.6805	Remote Similarity	NPD4112	Clinical (unspecified phase)
0.6798	Remote Similarity	NPD4909	Approved
0.6795	Remote Similarity	NPD5020	Approved
0.6795	Remote Similarity	NPD1722	Approved
0.6788	Remote Similarity	NPD6771	Discontinued
0.6788	Remote Similarity	NPD972	Clinical (unspecified phase)
0.6776	Remote Similarity	NPD3385	Approved
0.6774	Remote Similarity	NPD786	Approved
0.6772	Remote Similarity	NPD175	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