NPASS Compound

Structure

NPC471310 OpenBabel07101718282D 26 26 0 0 0 0 0 0 0 0999 V2000 -10.3923 -13.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.5263 -13.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.6603 -13.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.6603 -12.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 -11.5000 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 -6.9282 -9.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -8.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -7.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -7.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -4.0000 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 -0.8660 -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 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -2.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -2.5000 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 1 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 23 1 0 0 0 0 16 18 1 0 0 0 0 16 21 2 0 0 0 0 17 19 2 0 0 0 0 17 21 1 0 0 0 0 18 22 2 0 0 0 0 19 22 1 0 0 0 0 20 21 1 0 0 0 0 20 25 1 0 0 0 0 22 24 1 0 0 0 0 23 25 2 3 0 0 0 23 26 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	379.26
Volume:	422.26
LogP:	8.218
LogD:	4.51
LogS:	-5.766
# Rotatable Bonds:	17
TPSA:	29.1
# H-Bond Aceptor:	2
# H-Bond Donor:	1
# Rings:	1
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.297
Synthetic Accessibility Score:	1.814
Fsp3:	0.696
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.826
MDCK Permeability:	8.094460099528078e-06
Pgp-inhibitor:	0.041
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.002
20% Bioavailability (F20%):	0.066
30% Bioavailability (F30%):	0.965

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.136
Plasma Protein Binding (PPB):	98.9068374633789%
Volume Distribution (VD):	2.077
Pgp-substrate:	0.826765775680542%

ADMET: Metabolism

CYP1A2-inhibitor:	0.163
CYP1A2-substrate:	0.217
CYP2C19-inhibitor:	0.541
CYP2C19-substrate:	0.062
CYP2C9-inhibitor:	0.188
CYP2C9-substrate:	0.873
CYP2D6-inhibitor:	0.883
CYP2D6-substrate:	0.254
CYP3A4-inhibitor:	0.48
CYP3A4-substrate:	0.139

ADMET: Excretion

Clearance (CL):	4.781
Half-life (T1/2):	0.121

ADMET: Toxicity

hERG Blockers:	0.98
Human Hepatotoxicity (H-HT):	0.068
Drug-inuced Liver Injury (DILI):	0.247
AMES Toxicity:	0.01
Rat Oral Acute Toxicity:	0.047
Maximum Recommended Daily Dose:	0.023
Skin Sensitization:	0.936
Carcinogencity:	0.026
Eye Corrosion:	0.005
Eye Irritation:	0.081
Respiratory Toxicity:	0.502

Download Data

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

Natural Product: NPC471310

Natural Product ID:	NPC471310
*Common Name:**	N-(4-Chlorobenzyl)Palmitamide
IUPAC Name:	N-[(4-chlorophenyl)methyl]hexadecanamide
Synonyms:
Standard InCHIKey:	MJCZNJOEMYOWQI-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C23H38ClNO/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-23(26)25-20-21-16-18-22(24)19-17-21/h16-19H,2-15,20H2,1H3,(H,25,26)
SMILES:	CCCCCCCCCCCCCCCC(=O)NCC1=CC=C(C=C1)Cl
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2413168
PubChem CID:	71770310
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0000035] Halobenzenes [CHEMONTID:0001099] Chlorobenzenes

*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
Others	2

Activity Type	# Activity
Individual Protein	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1418	Individual Protein	Anandamide amidohydrolase	Homo sapiens	Inhibition	=	16.0	%	PMID[488985]
NPT1418	Individual Protein	Anandamide amidohydrolase	Homo sapiens	Inhibition	=	65.0	%	PMID[488985]

☑ 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 NPC471310 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	149
0.1-0.2	2072
0.2-0.3	11743
0.3-0.4	19268
0.4-0.5	7598
0.5-0.6	1583
0.6-0.7	237
0.7-0.8	30
0.8-0.85	6
0.85-0.9	10
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8962	High Similarity	NPC471318
0.8842	High Similarity	NPC78041
0.8842	High Similarity	NPC121872
0.8842	High Similarity	NPC471307
0.8842	High Similarity	NPC159178
0.8842	High Similarity	NPC74936
0.8842	High Similarity	NPC141139
0.8842	High Similarity	NPC209764
0.8737	High Similarity	NPC470877
0.8571	High Similarity	NPC471309
0.8247	Intermediate Similarity	NPC12429
0.7941	Intermediate Similarity	NPC58674
0.7925	Intermediate Similarity	NPC471317
0.7864	Intermediate Similarity	NPC25565
0.7788	Intermediate Similarity	NPC475439
0.7788	Intermediate Similarity	NPC473501
0.7778	Intermediate Similarity	NPC473031
0.7757	Intermediate Similarity	NPC202613
0.76	Intermediate Similarity	NPC471638
0.7596	Intermediate Similarity	NPC303045
0.7596	Intermediate Similarity	NPC161972
0.7549	Intermediate Similarity	NPC316108
0.7549	Intermediate Similarity	NPC172128
0.7476	Intermediate Similarity	NPC226438
0.7455	Intermediate Similarity	NPC474559
0.7453	Intermediate Similarity	NPC311242
0.7364	Intermediate Similarity	NPC88267
0.7364	Intermediate Similarity	NPC113326
0.7364	Intermediate Similarity	NPC194390
0.7364	Intermediate Similarity	NPC224610
0.7308	Intermediate Similarity	NPC245259
0.7184	Intermediate Similarity	NPC325441
0.7157	Intermediate Similarity	NPC203076
0.713	Intermediate Similarity	NPC313981
0.71	Intermediate Similarity	NPC14326
0.7071	Intermediate Similarity	NPC192623
0.7048	Intermediate Similarity	NPC258627
0.7043	Intermediate Similarity	NPC258056
0.7	Intermediate Similarity	NPC12730
0.6983	Remote Similarity	NPC474149
0.6972	Remote Similarity	NPC33168
0.6937	Remote Similarity	NPC469457
0.693	Remote Similarity	NPC327481
0.693	Remote Similarity	NPC231705
0.6923	Remote Similarity	NPC198747
0.6893	Remote Similarity	NPC3210
0.6881	Remote Similarity	NPC471320
0.6881	Remote Similarity	NPC471319
0.687	Remote Similarity	NPC142297
0.6864	Remote Similarity	NPC474584
0.6842	Remote Similarity	NPC471312
0.6842	Remote Similarity	NPC211551
0.6829	Remote Similarity	NPC53596
0.6829	Remote Similarity	NPC289330
0.6829	Remote Similarity	NPC160120
0.6829	Remote Similarity	NPC317564
0.6829	Remote Similarity	NPC471308
0.6829	Remote Similarity	NPC17388
0.6814	Remote Similarity	NPC178681
0.681	Remote Similarity	NPC77294
0.6807	Remote Similarity	NPC276949
0.6807	Remote Similarity	NPC35850
0.675	Remote Similarity	NPC33742
0.6729	Remote Similarity	NPC78154
0.6697	Remote Similarity	NPC476483
0.6695	Remote Similarity	NPC319579
0.6694	Remote Similarity	NPC317254
0.6667	Remote Similarity	NPC178902
0.6667	Remote Similarity	NPC164859
0.6667	Remote Similarity	NPC271642
0.6639	Remote Similarity	NPC470544
0.6638	Remote Similarity	NPC274089
0.6638	Remote Similarity	NPC191215
0.6633	Remote Similarity	NPC299134
0.6606	Remote Similarity	NPC265521
0.6585	Remote Similarity	NPC254088
0.6585	Remote Similarity	NPC470545
0.6585	Remote Similarity	NPC169328
0.6566	Remote Similarity	NPC98976
0.6535	Remote Similarity	NPC471314
0.6535	Remote Similarity	NPC471315
0.6532	Remote Similarity	NPC470546
0.6532	Remote Similarity	NPC237420
0.6532	Remote Similarity	NPC310467
0.6531	Remote Similarity	NPC244738
0.6525	Remote Similarity	NPC24101
0.6525	Remote Similarity	NPC96224
0.65	Remote Similarity	NPC329011
0.6491	Remote Similarity	NPC214200
0.6491	Remote Similarity	NPC228400
0.648	Remote Similarity	NPC283760
0.6475	Remote Similarity	NPC118202
0.6436	Remote Similarity	NPC325662
0.6436	Remote Similarity	NPC98269
0.6435	Remote Similarity	NPC318154
0.6429	Remote Similarity	NPC208302
0.6429	Remote Similarity	NPC478016
0.6429	Remote Similarity	NPC478015
0.6429	Remote Similarity	NPC478014
0.6429	Remote Similarity	NPC45777
0.6429	Remote Similarity	NPC476990
0.6429	Remote Similarity	NPC3371
0.6429	Remote Similarity	NPC477061
0.6423	Remote Similarity	NPC197470
0.6423	Remote Similarity	NPC188010
0.6418	Remote Similarity	NPC313352
0.64	Remote Similarity	NPC189371
0.64	Remote Similarity	NPC314992
0.6397	Remote Similarity	NPC316906
0.6387	Remote Similarity	NPC153690
0.6381	Remote Similarity	NPC15839
0.6381	Remote Similarity	NPC477770
0.6378	Remote Similarity	NPC202521
0.6378	Remote Similarity	NPC71684
0.6373	Remote Similarity	NPC12857
0.6371	Remote Similarity	NPC82963
0.6371	Remote Similarity	NPC2265
0.6356	Remote Similarity	NPC130898
0.6356	Remote Similarity	NPC474973
0.6356	Remote Similarity	NPC474804
0.6341	Remote Similarity	NPC470550
0.6341	Remote Similarity	NPC205652
0.6339	Remote Similarity	NPC20142
0.6339	Remote Similarity	NPC215351
0.6339	Remote Similarity	NPC108339
0.6328	Remote Similarity	NPC252878
0.6327	Remote Similarity	NPC219246
0.632	Remote Similarity	NPC311737
0.632	Remote Similarity	NPC38458
0.6316	Remote Similarity	NPC226096
0.6316	Remote Similarity	NPC290515
0.6316	Remote Similarity	NPC303611
0.6316	Remote Similarity	NPC164514
0.6316	Remote Similarity	NPC108606
0.6306	Remote Similarity	NPC323164
0.63	Remote Similarity	NPC108218
0.6299	Remote Similarity	NPC190663
0.6293	Remote Similarity	NPC327226
0.6279	Remote Similarity	NPC6975
0.6279	Remote Similarity	NPC46427
0.6271	Remote Similarity	NPC143516
0.627	Remote Similarity	NPC320656
0.626	Remote Similarity	NPC474544
0.626	Remote Similarity	NPC1986
0.625	Remote Similarity	NPC164449
0.625	Remote Similarity	NPC184030
0.625	Remote Similarity	NPC309279
0.624	Remote Similarity	NPC147957
0.624	Remote Similarity	NPC239357
0.6231	Remote Similarity	NPC22746
0.6228	Remote Similarity	NPC293628
0.6228	Remote Similarity	NPC122493
0.6228	Remote Similarity	NPC10781
0.6226	Remote Similarity	NPC104070
0.6226	Remote Similarity	NPC146703
0.622	Remote Similarity	NPC43275
0.622	Remote Similarity	NPC268572
0.6214	Remote Similarity	NPC224544
0.621	Remote Similarity	NPC142599
0.6207	Remote Similarity	NPC155847
0.6207	Remote Similarity	NPC289381
0.6202	Remote Similarity	NPC160493
0.619	Remote Similarity	NPC307456
0.619	Remote Similarity	NPC231986
0.6187	Remote Similarity	NPC469427
0.6187	Remote Similarity	NPC469426
0.6186	Remote Similarity	NPC304761
0.6186	Remote Similarity	NPC226778
0.6186	Remote Similarity	NPC150254
0.6186	Remote Similarity	NPC147000
0.6183	Remote Similarity	NPC101719
0.6183	Remote Similarity	NPC47667
0.6179	Remote Similarity	NPC273814
0.6176	Remote Similarity	NPC313737
0.6176	Remote Similarity	NPC6854
0.6176	Remote Similarity	NPC139658
0.6176	Remote Similarity	NPC285078
0.6174	Remote Similarity	NPC322598
0.6172	Remote Similarity	NPC200964
0.6172	Remote Similarity	NPC80150
0.6168	Remote Similarity	NPC169016
0.6165	Remote Similarity	NPC471311
0.6165	Remote Similarity	NPC471313
0.6162	Remote Similarity	NPC229235
0.616	Remote Similarity	NPC235421
0.6154	Remote Similarity	NPC472415
0.6154	Remote Similarity	NPC35996
0.6139	Remote Similarity	NPC113000
0.6139	Remote Similarity	NPC112609
0.6139	Remote Similarity	NPC122327
0.6136	Remote Similarity	NPC477937
0.6134	Remote Similarity	NPC476198
0.6134	Remote Similarity	NPC67043
0.6132	Remote Similarity	NPC475199
0.6132	Remote Similarity	NPC73637
0.6132	Remote Similarity	NPC283012
0.6132	Remote Similarity	NPC121478
0.6127	Remote Similarity	NPC477890
0.6107	Remote Similarity	NPC222466
0.6103	Remote Similarity	NPC130595

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 NPC471310 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	116
0.1-0.2	732
0.2-0.3	1053
0.3-0.4	2736
0.4-0.5	3000
0.5-0.6	1250
0.6-0.7	238
0.7-0.8	23
0.8-0.85	1
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.866	High Similarity	NPD6690	Approved
0.8144	Intermediate Similarity	NPD187	Approved
0.8	Intermediate Similarity	NPD3651	Discontinued
0.7925	Intermediate Similarity	NPD1415	Approved
0.7619	Intermediate Similarity	NPD1076	Approved
0.7573	Intermediate Similarity	NPD1812	Approved
0.7573	Intermediate Similarity	NPD1814	Approved
0.757	Intermediate Similarity	NPD2657	Approved
0.7521	Intermediate Similarity	NPD2617	Discontinued
0.75	Intermediate Similarity	NPD9721	Approved
0.75	Intermediate Similarity	NPD9722	Approved
0.7456	Intermediate Similarity	NPD7121	Approved
0.7434	Intermediate Similarity	NPD801	Discontinued
0.7429	Intermediate Similarity	NPD4814	Discontinued
0.7407	Intermediate Similarity	NPD4760	Clinical (unspecified phase)
0.7345	Intermediate Similarity	NPD7120	Approved
0.7333	Intermediate Similarity	NPD1080	Approved
0.7321	Intermediate Similarity	NPD1401	Approved
0.7273	Intermediate Similarity	NPD3603	Phase 3
0.7217	Intermediate Similarity	NPD2499	Approved
0.7217	Intermediate Similarity	NPD2500	Approved
0.72	Intermediate Similarity	NPD9701	Discontinued
0.7196	Intermediate Similarity	NPD2507	Clinical (unspecified phase)
0.7155	Intermediate Similarity	NPD3066	Phase 2
0.7155	Intermediate Similarity	NPD4165	Phase 2
0.7154	Intermediate Similarity	NPD2371	Approved
0.7143	Intermediate Similarity	NPD1359	Approved
0.713	Intermediate Similarity	NPD188	Approved
0.713	Intermediate Similarity	NPD189	Phase 3
0.713	Intermediate Similarity	NPD2487	Clinical (unspecified phase)
0.7103	Intermediate Similarity	NPD2655	Approved
0.7103	Intermediate Similarity	NPD2656	Approved
0.7073	Intermediate Similarity	NPD5335	Discontinued
0.7054	Intermediate Similarity	NPD2937	Phase 1
0.7054	Intermediate Similarity	NPD2939	Approved
0.7031	Intermediate Similarity	NPD2078	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD263	Approved
0.703	Intermediate Similarity	NPD262	Approved
0.7018	Intermediate Similarity	NPD6038	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD9538	Approved
0.69	Remote Similarity	NPD5371	Approved
0.69	Remote Similarity	NPD5372	Approved
0.6875	Remote Similarity	NPD4119	Approved
0.686	Remote Similarity	NPD828	Approved
0.6857	Remote Similarity	NPD1101	Approved
0.6855	Remote Similarity	NPD3974	Phase 2
0.6847	Remote Similarity	NPD3097	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD5717	Approved
0.6838	Remote Similarity	NPD3643	Approved
0.6838	Remote Similarity	NPD3642	Approved
0.6838	Remote Similarity	NPD3644	Approved
0.6832	Remote Similarity	NPD472	Approved
0.6825	Remote Similarity	NPD3098	Discontinued
0.6822	Remote Similarity	NPD530	Approved
0.6822	Remote Similarity	NPD2372	Approved
0.6814	Remote Similarity	NPD1542	Approved
0.681	Remote Similarity	NPD2679	Approved
0.681	Remote Similarity	NPD2678	Approved
0.6807	Remote Similarity	NPD3149	Approved
0.6807	Remote Similarity	NPD2659	Approved
0.6807	Remote Similarity	NPD3150	Approved
0.6807	Remote Similarity	NPD3147	Approved
0.6807	Remote Similarity	NPD3148	Approved
0.6807	Remote Similarity	NPD2658	Approved
0.6794	Remote Similarity	NPD1106	Discontinued
0.6791	Remote Similarity	NPD1884	Approved
0.6789	Remote Similarity	NPD1081	Clinical (unspecified phase)
0.6759	Remote Similarity	NPD752	Approved
0.6754	Remote Similarity	NPD179	Clinical (unspecified phase)
0.6752	Remote Similarity	NPD6236	Approved
0.6752	Remote Similarity	NPD6235	Approved
0.6748	Remote Similarity	NPD2212	Approved
0.6748	Remote Similarity	NPD2210	Approved
0.6742	Remote Similarity	NPD6086	Phase 2
0.6742	Remote Similarity	NPD3851	Clinical (unspecified phase)
0.6727	Remote Similarity	NPD2895	Discontinued
0.6726	Remote Similarity	NPD1540	Approved
0.6724	Remote Similarity	NPD6406	Approved
0.6723	Remote Similarity	NPD1764	Approved
0.6723	Remote Similarity	NPD1762	Approved
0.6697	Remote Similarity	NPD1394	Approved
0.6696	Remote Similarity	NPD564	Approved
0.6696	Remote Similarity	NPD1067	Discontinued
0.6696	Remote Similarity	NPD563	Approved
0.6694	Remote Similarity	NPD2622	Approved
0.6694	Remote Similarity	NPD4631	Approved
0.6694	Remote Similarity	NPD4630	Approved
0.6694	Remote Similarity	NPD5407	Approved
0.6667	Remote Similarity	NPD2988	Approved
0.6667	Remote Similarity	NPD1903	Approved
0.6667	Remote Similarity	NPD2035	Discontinued
0.6667	Remote Similarity	NPD7059	Approved
0.6667	Remote Similarity	NPD7060	Approved
0.6667	Remote Similarity	NPD2665	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5103	Approved
0.6667	Remote Similarity	NPD2991	Approved
0.6667	Remote Similarity	NPD1498	Approved
0.6667	Remote Similarity	NPD2244	Clinical (unspecified phase)
0.6609	Remote Similarity	NPD3407	Phase 3
0.6607	Remote Similarity	NPD4117	Approved
0.6607	Remote Similarity	NPD728	Approved
0.66	Remote Similarity	NPD603	Approved
0.6585	Remote Similarity	NPD6360	Discontinued
0.6585	Remote Similarity	NPD2108	Phase 2
0.6585	Remote Similarity	NPD2109	Clinical (unspecified phase)
0.6579	Remote Similarity	NPD1417	Approved
0.6579	Remote Similarity	NPD4817	Approved
0.6579	Remote Similarity	NPD1419	Approved
0.6579	Remote Similarity	NPD4818	Approved
0.6579	Remote Similarity	NPD5753	Discontinued
0.6579	Remote Similarity	NPD5716	Approved
0.6567	Remote Similarity	NPD5212	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD2031	Discontinued
0.656	Remote Similarity	NPD4594	Approved
0.656	Remote Similarity	NPD2597	Suspended
0.656	Remote Similarity	NPD2596	Phase 2
0.656	Remote Similarity	NPD4593	Approved
0.6552	Remote Similarity	NPD1018	Approved
0.6552	Remote Similarity	NPD999	Phase 2
0.6549	Remote Similarity	NPD523	Approved
0.6549	Remote Similarity	NPD524	Approved
0.6545	Remote Similarity	NPD3719	Approved
0.6545	Remote Similarity	NPD1066	Discontinued
0.6545	Remote Similarity	NPD3718	Approved
0.6545	Remote Similarity	NPD1409	Phase 3
0.6545	Remote Similarity	NPD719	Approved
0.6545	Remote Similarity	NPD720	Approved
0.6532	Remote Similarity	NPD4016	Approved
0.6531	Remote Similarity	NPD9728	Phase 1
0.6493	Remote Similarity	NPD7431	Approved
0.6493	Remote Similarity	NPD7430	Approved
0.6489	Remote Similarity	NPD4698	Clinical (unspecified phase)
0.6476	Remote Similarity	NPD2538	Approved
0.6476	Remote Similarity	NPD2539	Approved
0.6471	Remote Similarity	NPD1107	Approved
0.6471	Remote Similarity	NPD1108	Approved
0.6462	Remote Similarity	NPD1516	Approved
0.6457	Remote Similarity	NPD4323	Clinical (unspecified phase)
0.6455	Remote Similarity	NPD9251	Approved
0.6452	Remote Similarity	NPD7522	Discontinued
0.6446	Remote Similarity	NPD181	Approved
0.6441	Remote Similarity	NPD2243	Clinical (unspecified phase)
0.6435	Remote Similarity	NPD4719	Phase 2
0.6435	Remote Similarity	NPD855	Approved
0.6435	Remote Similarity	NPD854	Approved
0.6434	Remote Similarity	NPD6325	Discontinued
0.6429	Remote Similarity	NPD1320	Phase 1
0.6429	Remote Similarity	NPD7342	Discontinued
0.6423	Remote Similarity	NPD1348	Approved
0.6412	Remote Similarity	NPD6984	Approved
0.641	Remote Similarity	NPD1040	Phase 2
0.64	Remote Similarity	NPD2217	Approved
0.64	Remote Similarity	NPD2218	Phase 2
0.6397	Remote Similarity	NPD7231	Approved
0.6397	Remote Similarity	NPD7230	Approved
0.6393	Remote Similarity	NPD1680	Approved
0.6393	Remote Similarity	NPD1681	Approved
0.6393	Remote Similarity	NPD1682	Approved
0.6387	Remote Similarity	NPD7156	Discontinued
0.6372	Remote Similarity	NPD1875	Phase 1
0.637	Remote Similarity	NPD1384	Approved
0.637	Remote Similarity	NPD1859	Approved
0.6364	Remote Similarity	NPD6359	Clinical (unspecified phase)
0.6357	Remote Similarity	NPD7099	Approved
0.6349	Remote Similarity	NPD5981	Approved
0.6348	Remote Similarity	NPD1616	Discontinued
0.6341	Remote Similarity	NPD1020	Approved
0.6341	Remote Similarity	NPD1022	Approved
0.6341	Remote Similarity	NPD1021	Approved
0.6341	Remote Similarity	NPD1023	Approved
0.6336	Remote Similarity	NPD4531	Approved
0.6336	Remote Similarity	NPD4530	Approved
0.6336	Remote Similarity	NPD4525	Approved
0.6336	Remote Similarity	NPD4527	Approved
0.6331	Remote Similarity	NPD1214	Approved
0.6328	Remote Similarity	NPD1703	Clinical (unspecified phase)
0.6327	Remote Similarity	NPD5541	Clinical (unspecified phase)
0.6327	Remote Similarity	NPD6726	Phase 2
0.6327	Remote Similarity	NPD6725	Clinical (unspecified phase)
0.632	Remote Similarity	NPD5130	Phase 3
0.6316	Remote Similarity	NPD1500	Approved
0.6316	Remote Similarity	NPD9609	Approved
0.6316	Remote Similarity	NPD9612	Approved
0.6316	Remote Similarity	NPD9611	Approved
0.6312	Remote Similarity	NPD7575	Phase 3
0.6311	Remote Similarity	NPD507	Approved
0.6311	Remote Similarity	NPD508	Approved
0.6308	Remote Similarity	NPD5578	Approved
0.6308	Remote Similarity	NPD5577	Clinical (unspecified phase)
0.6303	Remote Similarity	NPD9532	Phase 3
0.629	Remote Similarity	NPD7508	Discontinued
0.6288	Remote Similarity	NPD4895	Clinical (unspecified phase)
0.6281	Remote Similarity	NPD4253	Approved
0.6281	Remote Similarity	NPD4254	Approved
0.6275	Remote Similarity	NPD4147	Approved
0.6275	Remote Similarity	NPD4144	Approved
0.627	Remote Similarity	NPD474	Approved
0.627	Remote Similarity	NPD2395	Approved
0.627	Remote Similarity	NPD2396	Approved
0.627	Remote Similarity	NPD152	Suspended

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