NPASS Compound

Structure

NPC471317 OpenBabel07101718282D 28 28 0 0 0 0 0 0 0 0999 V2000 -9.5263 -13.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.6603 -14.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 -13.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 -12.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 -12.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 -11.0000 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 -6.0622 -9.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -9.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -8.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -7.5000 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 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -6.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -3.5000 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 -3.4641 -6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -3.0000 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 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 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 15 1 0 0 0 0 12 13 2 0 0 0 0 12 14 1 0 0 0 0 13 17 1 0 0 0 0 14 18 2 0 0 0 0 15 19 1 0 0 0 0 16 20 1 0 0 0 0 16 21 1 0 0 0 0 17 23 2 0 0 0 0 18 23 1 0 0 0 0 19 24 1 0 0 0 0 20 24 1 0 0 0 0 21 25 1 0 0 0 0 22 23 1 0 0 0 0 22 26 1 0 0 0 0 24 27 2 0 0 0 0 25 26 2 3 0 0 0 25 28 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	387.31
Volume:	447.795
LogP:	6.238
LogD:	4.514
LogS:	-4.412
# Rotatable Bonds:	19
TPSA:	46.17
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	1
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.283
Synthetic Accessibility Score:	1.973
Fsp3:	0.68
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:	-4.856
MDCK Permeability:	1.2282244824746158e-05
Pgp-inhibitor:	0.119
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.942
30% Bioavailability (F30%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.68
Plasma Protein Binding (PPB):	98.01551818847656%
Volume Distribution (VD):	1.138
Pgp-substrate:	0.5334007740020752%

ADMET: Metabolism

CYP1A2-inhibitor:	0.168
CYP1A2-substrate:	0.408
CYP2C19-inhibitor:	0.581
CYP2C19-substrate:	0.059
CYP2C9-inhibitor:	0.307
CYP2C9-substrate:	0.834
CYP2D6-inhibitor:	0.502
CYP2D6-substrate:	0.262
CYP3A4-inhibitor:	0.805
CYP3A4-substrate:	0.133

ADMET: Excretion

Clearance (CL):	5.879
Half-life (T1/2):	0.746

ADMET: Toxicity

hERG Blockers:	0.715
Human Hepatotoxicity (H-HT):	0.108
Drug-inuced Liver Injury (DILI):	0.037
AMES Toxicity:	0.006
Rat Oral Acute Toxicity:	0.044
Maximum Recommended Daily Dose:	0.025
Skin Sensitization:	0.876
Carcinogencity:	0.023
Eye Corrosion:	0.004
Eye Irritation:	0.072
Respiratory Toxicity:	0.115

Download Data

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

Natural Product: NPC471317

Natural Product ID:	NPC471317
*Common Name:**	N-Benzyl-5-Oxooctadecanamide
IUPAC Name:	N-benzyl-5-oxooctadecanamide
Synonyms:
Standard InCHIKey:	MNAGXGIWSMFPEB-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C25H41NO2/c1-2-3-4-5-6-7-8-9-10-11-15-19-24(27)20-16-21-25(28)26-22-23-17-13-12-14-18-23/h12-14,17-18H,2-11,15-16,19-22H2,1H3,(H,26,28)
SMILES:	CCCCCCCCCCCCCC(=O)CCCC(=O)NCC1=CC=CC=C1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2413175
PubChem CID:	71770428
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0003909] Fatty Acyls [CHEMONTID:0000331] Fatty amides [CHEMONTID:0001096] N-acyl amines

*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	2

Activity Type	# Activity
Individual Protein	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1418	Individual Protein	Anandamide amidohydrolase	Homo sapiens	IC50	>	500000.0	nM	PMID[497627]
NPT1418	Individual Protein	Anandamide amidohydrolase	Homo sapiens	Inhibition	=	11.0	%	PMID[497627]

☑ 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 NPC471317 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	93
0.1-0.2	814
0.2-0.3	3841
0.3-0.4	14252
0.4-0.5	18429
0.5-0.6	4290
0.6-0.7	828
0.7-0.8	127
0.8-0.85	10
0.85-0.9	10
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9388	High Similarity	NPC202613
0.8962	High Similarity	NPC471318
0.8842	High Similarity	NPC74936
0.8842	High Similarity	NPC78041
0.8842	High Similarity	NPC471307
0.8842	High Similarity	NPC159178
0.8842	High Similarity	NPC121872
0.8842	High Similarity	NPC141139
0.8842	High Similarity	NPC209764
0.8737	High Similarity	NPC470877
0.8571	High Similarity	NPC471309
0.8333	Intermediate Similarity	NPC12730
0.83	Intermediate Similarity	NPC58674
0.8091	Intermediate Similarity	NPC474584
0.8039	Intermediate Similarity	NPC25565
0.8036	Intermediate Similarity	NPC188010
0.8018	Intermediate Similarity	NPC35850
0.8018	Intermediate Similarity	NPC276949
0.7961	Intermediate Similarity	NPC475439
0.7961	Intermediate Similarity	NPC473501
0.7946	Intermediate Similarity	NPC33742
0.7925	Intermediate Similarity	NPC471310
0.7925	Intermediate Similarity	NPC164859
0.7909	Intermediate Similarity	NPC319579
0.7895	Intermediate Similarity	NPC169328
0.787	Intermediate Similarity	NPC327481
0.7826	Intermediate Similarity	NPC310467
0.7778	Intermediate Similarity	NPC471638
0.7778	Intermediate Similarity	NPC473031
0.7767	Intermediate Similarity	NPC303045
0.7767	Intermediate Similarity	NPC161972
0.7723	Intermediate Similarity	NPC172128
0.77	Intermediate Similarity	NPC325441
0.77	Intermediate Similarity	NPC12429
0.7692	Intermediate Similarity	NPC478014
0.7692	Intermediate Similarity	NPC478015
0.7692	Intermediate Similarity	NPC478016
0.7685	Intermediate Similarity	NPC113326
0.7685	Intermediate Similarity	NPC194390
0.7685	Intermediate Similarity	NPC88267
0.7685	Intermediate Similarity	NPC224610
0.7679	Intermediate Similarity	NPC329011
0.7647	Intermediate Similarity	NPC226438
0.7619	Intermediate Similarity	NPC311242
0.7586	Intermediate Similarity	NPC254088
0.7573	Intermediate Similarity	NPC323164
0.7565	Intermediate Similarity	NPC197470
0.7549	Intermediate Similarity	NPC258627
0.7549	Intermediate Similarity	NPC316108
0.7545	Intermediate Similarity	NPC274089
0.7545	Intermediate Similarity	NPC191215
0.7542	Intermediate Similarity	NPC190663
0.7525	Intermediate Similarity	NPC477704
0.7525	Intermediate Similarity	NPC477693
0.7521	Intermediate Similarity	NPC237420
0.7476	Intermediate Similarity	NPC245259
0.7453	Intermediate Similarity	NPC10781
0.7453	Intermediate Similarity	NPC122493
0.7453	Intermediate Similarity	NPC293628
0.7436	Intermediate Similarity	NPC470545
0.7417	Intermediate Similarity	NPC160493
0.7395	Intermediate Similarity	NPC80150
0.7383	Intermediate Similarity	NPC322598
0.7377	Intermediate Similarity	NPC47667
0.7374	Intermediate Similarity	NPC44830
0.7373	Intermediate Similarity	NPC314992
0.7373	Intermediate Similarity	NPC470546
0.7355	Intermediate Similarity	NPC35996
0.735	Intermediate Similarity	NPC470544
0.7345	Intermediate Similarity	NPC258056
0.7297	Intermediate Similarity	NPC67043
0.7297	Intermediate Similarity	NPC476198
0.729	Intermediate Similarity	NPC324569
0.7281	Intermediate Similarity	NPC474149
0.728	Intermediate Similarity	NPC478147
0.725	Intermediate Similarity	NPC200964
0.7245	Intermediate Similarity	NPC127343
0.7236	Intermediate Similarity	NPC474926
0.7236	Intermediate Similarity	NPC101719
0.7232	Intermediate Similarity	NPC231705
0.7232	Intermediate Similarity	NPC45033
0.7228	Intermediate Similarity	NPC95965
0.7228	Intermediate Similarity	NPC3210
0.7203	Intermediate Similarity	NPC2265
0.72	Intermediate Similarity	NPC116057
0.72	Intermediate Similarity	NPC472413
0.72	Intermediate Similarity	NPC111428
0.719	Intermediate Similarity	NPC71684
0.7177	Intermediate Similarity	NPC477937
0.7168	Intermediate Similarity	NPC142297
0.7167	Intermediate Similarity	NPC319950
0.7157	Intermediate Similarity	NPC203076
0.7154	Intermediate Similarity	NPC222466
0.7143	Intermediate Similarity	NPC141607
0.7143	Intermediate Similarity	NPC187725
0.713	Intermediate Similarity	NPC33168
0.7121	Intermediate Similarity	NPC316202
0.7119	Intermediate Similarity	NPC235421
0.7107	Intermediate Similarity	NPC289330
0.7107	Intermediate Similarity	NPC45777
0.7107	Intermediate Similarity	NPC160120
0.7107	Intermediate Similarity	NPC53596
0.7107	Intermediate Similarity	NPC471308
0.7107	Intermediate Similarity	NPC477061
0.7107	Intermediate Similarity	NPC17388
0.71	Intermediate Similarity	NPC14326
0.7099	Intermediate Similarity	NPC471316
0.7097	Intermediate Similarity	NPC4974
0.7091	Intermediate Similarity	NPC469457
0.7087	Intermediate Similarity	NPC183722
0.7087	Intermediate Similarity	NPC316746
0.7073	Intermediate Similarity	NPC6975
0.7073	Intermediate Similarity	NPC472415
0.7071	Intermediate Similarity	NPC192623
0.7064	Intermediate Similarity	NPC271475
0.7063	Intermediate Similarity	NPC296712
0.7063	Intermediate Similarity	NPC473322
0.7059	Intermediate Similarity	NPC14672
0.7059	Intermediate Similarity	NPC285926
0.7059	Intermediate Similarity	NPC315276
0.7059	Intermediate Similarity	NPC239357
0.7054	Intermediate Similarity	NPC248283
0.703	Intermediate Similarity	NPC285773
0.7015	Intermediate Similarity	NPC314287
0.7009	Intermediate Similarity	NPC273814
0.7008	Intermediate Similarity	NPC314431
0.7	Intermediate Similarity	NPC54647
0.6991	Remote Similarity	NPC211551
0.6977	Remote Similarity	NPC244866
0.6975	Remote Similarity	NPC317254
0.6972	Remote Similarity	NPC477767
0.6964	Remote Similarity	NPC178902
0.696	Remote Similarity	NPC472414
0.6953	Remote Similarity	NPC255447
0.6952	Remote Similarity	NPC231591
0.6947	Remote Similarity	NPC74458
0.6944	Remote Similarity	NPC206764
0.6937	Remote Similarity	NPC94487
0.6923	Remote Similarity	NPC322387
0.6923	Remote Similarity	NPC198747
0.6911	Remote Similarity	NPC202521
0.6899	Remote Similarity	NPC246913
0.6887	Remote Similarity	NPC86670
0.6887	Remote Similarity	NPC84288
0.6887	Remote Similarity	NPC70940
0.6887	Remote Similarity	NPC274455
0.6881	Remote Similarity	NPC471320
0.6881	Remote Similarity	NPC471319
0.6881	Remote Similarity	NPC3371
0.688	Remote Similarity	NPC22746
0.688	Remote Similarity	NPC317758
0.6875	Remote Similarity	NPC285679
0.6875	Remote Similarity	NPC325651
0.6875	Remote Similarity	NPC475978
0.6875	Remote Similarity	NPC318154
0.6875	Remote Similarity	NPC474820
0.6857	Remote Similarity	NPC329064
0.6855	Remote Similarity	NPC27581
0.6855	Remote Similarity	NPC474862
0.6855	Remote Similarity	NPC142577
0.6855	Remote Similarity	NPC252878
0.6852	Remote Similarity	NPC34243
0.6852	Remote Similarity	NPC476483
0.6852	Remote Similarity	NPC291070
0.6852	Remote Similarity	NPC246757
0.685	Remote Similarity	NPC319766
0.6846	Remote Similarity	NPC328070
0.6842	Remote Similarity	NPC471201
0.6829	Remote Similarity	NPC476990
0.6822	Remote Similarity	NPC86987
0.6818	Remote Similarity	NPC208725
0.6818	Remote Similarity	NPC289201
0.6814	Remote Similarity	NPC178681
0.681	Remote Similarity	NPC24101
0.681	Remote Similarity	NPC96224
0.68	Remote Similarity	NPC471314
0.68	Remote Similarity	NPC175726
0.68	Remote Similarity	NPC474082
0.68	Remote Similarity	NPC272260
0.68	Remote Similarity	NPC471315
0.68	Remote Similarity	NPC46427
0.6797	Remote Similarity	NPC71271
0.6786	Remote Similarity	NPC158623
0.6783	Remote Similarity	NPC130898
0.6783	Remote Similarity	NPC474804
0.6783	Remote Similarity	NPC473498
0.6783	Remote Similarity	NPC474973
0.6783	Remote Similarity	NPC244933
0.6783	Remote Similarity	NPC85560
0.6769	Remote Similarity	NPC326966
0.6768	Remote Similarity	NPC9796
0.6759	Remote Similarity	NPC265521
0.675	Remote Similarity	NPC118202
0.6748	Remote Similarity	NPC283760
0.6744	Remote Similarity	NPC200589
0.6742	Remote Similarity	NPC314835
0.6731	Remote Similarity	NPC123476
0.6729	Remote Similarity	NPC78154
0.6719	Remote Similarity	NPC210950
0.6719	Remote Similarity	NPC476353

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 NPC471317 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	89
0.1-0.2	489
0.2-0.3	799
0.3-0.4	2078
0.4-0.5	3417
0.5-0.6	1771
0.6-0.7	463
0.7-0.8	43
0.8-0.85	0
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
0.8073	Intermediate Similarity	NPD3642	Approved
0.8073	Intermediate Similarity	NPD3643	Approved
0.8073	Intermediate Similarity	NPD3644	Approved
0.7944	Intermediate Similarity	NPD1018	Approved
0.7667	Intermediate Similarity	NPD6325	Discontinued
0.7615	Intermediate Similarity	NPD999	Phase 2
0.7611	Intermediate Similarity	NPD181	Approved
0.7596	Intermediate Similarity	NPD4814	Discontinued
0.7573	Intermediate Similarity	NPD1812	Approved
0.7573	Intermediate Similarity	NPD1814	Approved
0.757	Intermediate Similarity	NPD4760	Clinical (unspecified phase)
0.7565	Intermediate Similarity	NPD1348	Approved
0.7544	Intermediate Similarity	NPD1682	Approved
0.7544	Intermediate Similarity	NPD1680	Approved
0.7544	Intermediate Similarity	NPD1681	Approved
0.7521	Intermediate Similarity	NPD5577	Clinical (unspecified phase)
0.7521	Intermediate Similarity	NPD5578	Approved
0.75	Intermediate Similarity	NPD1080	Approved
0.7458	Intermediate Similarity	NPD5981	Approved
0.7455	Intermediate Similarity	NPD1040	Phase 2
0.7453	Intermediate Similarity	NPD9566	Approved
0.7426	Intermediate Similarity	NPD187	Approved
0.7383	Intermediate Similarity	NPD253	Approved
0.7373	Intermediate Similarity	NPD2218	Phase 2
0.7373	Intermediate Similarity	NPD2217	Approved
0.736	Intermediate Similarity	NPD4738	Phase 2
0.7333	Intermediate Similarity	NPD1066	Discontinued
0.7317	Intermediate Similarity	NPD6302	Clinical (unspecified phase)
0.7315	Intermediate Similarity	NPD1067	Discontinued
0.7311	Intermediate Similarity	NPD4504	Clinical (unspecified phase)
0.7282	Intermediate Similarity	NPD5346	Phase 2
0.7282	Intermediate Similarity	NPD5347	Phase 2
0.7255	Intermediate Similarity	NPD4793	Discontinued
0.7236	Intermediate Similarity	NPD1036	Approved
0.7213	Intermediate Similarity	NPD5108	Clinical (unspecified phase)
0.7203	Intermediate Similarity	NPD5162	Approved
0.7196	Intermediate Similarity	NPD2507	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD226	Approved
0.717	Intermediate Similarity	NPD5122	Clinical (unspecified phase)
0.7155	Intermediate Similarity	NPD3066	Phase 2
0.7155	Intermediate Similarity	NPD4165	Phase 2
0.7143	Intermediate Similarity	NPD1758	Phase 1
0.713	Intermediate Similarity	NPD2487	Clinical (unspecified phase)
0.7103	Intermediate Similarity	NPD4094	Approved
0.7103	Intermediate Similarity	NPD1081	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD6864	Phase 2
0.7099	Intermediate Similarity	NPD6865	Phase 2
0.7087	Intermediate Similarity	NPD9538	Approved
0.7083	Intermediate Similarity	NPD2617	Discontinued
0.7083	Intermediate Similarity	NPD1759	Phase 1
0.7063	Intermediate Similarity	NPD7828	Discontinued
0.7063	Intermediate Similarity	NPD3626	Phase 3
0.7049	Intermediate Similarity	NPD2956	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD9491	Approved
0.7019	Intermediate Similarity	NPD1101	Approved
0.7018	Intermediate Similarity	NPD6406	Approved
0.7018	Intermediate Similarity	NPD6038	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD7113	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD530	Approved
0.6972	Remote Similarity	NPD4657	Approved
0.6972	Remote Similarity	NPD1099	Approved
0.6972	Remote Similarity	NPD4655	Approved
0.6972	Remote Similarity	NPD1100	Approved
0.6964	Remote Similarity	NPD1542	Approved
0.6952	Remote Similarity	NPD800	Approved
0.6944	Remote Similarity	NPD1693	Approved
0.6942	Remote Similarity	NPD998	Approved
0.6942	Remote Similarity	NPD6093	Discontinued
0.6935	Remote Similarity	NPD2584	Suspended
0.693	Remote Similarity	NPD467	Phase 1
0.6923	Remote Similarity	NPD9508	Approved
0.6917	Remote Similarity	NPD733	Approved
0.6917	Remote Similarity	NPD732	Approved
0.6917	Remote Similarity	NPD3123	Discovery
0.6916	Remote Similarity	NPD752	Approved
0.69	Remote Similarity	NPD5371	Approved
0.69	Remote Similarity	NPD5372	Approved
0.6891	Remote Similarity	NPD1711	Phase 2
0.6887	Remote Similarity	NPD1086	Approved
0.6887	Remote Similarity	NPD1090	Approved
0.6887	Remote Similarity	NPD1089	Approved
0.6875	Remote Similarity	NPD4125	Approved
0.6875	Remote Similarity	NPD6359	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD1540	Approved
0.6875	Remote Similarity	NPD4119	Approved
0.6869	Remote Similarity	NPD227	Approved
0.6869	Remote Similarity	NPD225	Approved
0.6864	Remote Similarity	NPD2607	Approved
0.6864	Remote Similarity	NPD480	Approved
0.6855	Remote Similarity	NPD3603	Phase 3
0.6852	Remote Similarity	NPD1394	Approved
0.6852	Remote Similarity	NPD720	Approved
0.6852	Remote Similarity	NPD719	Approved
0.685	Remote Similarity	NPD3608	Clinical (unspecified phase)
0.685	Remote Similarity	NPD5339	Clinical (unspecified phase)
0.6847	Remote Similarity	NPD2066	Phase 3
0.6842	Remote Similarity	NPD5717	Approved
0.6825	Remote Similarity	NPD5367	Discontinued
0.6818	Remote Similarity	NPD8172	Phase 2
0.6818	Remote Similarity	NPD8173	Phase 2
0.681	Remote Similarity	NPD2679	Approved
0.681	Remote Similarity	NPD476	Approved
0.681	Remote Similarity	NPD2678	Approved
0.6807	Remote Similarity	NPD2650	Approved
0.6807	Remote Similarity	NPD3149	Approved
0.6807	Remote Similarity	NPD2652	Approved
0.6807	Remote Similarity	NPD2659	Approved
0.6807	Remote Similarity	NPD3150	Approved
0.6807	Remote Similarity	NPD3147	Approved
0.6807	Remote Similarity	NPD3598	Phase 3
0.6807	Remote Similarity	NPD3148	Approved
0.6807	Remote Similarity	NPD2658	Approved
0.6794	Remote Similarity	NPD8265	Approved
0.678	Remote Similarity	NPD753	Approved
0.6772	Remote Similarity	NPD1593	Approved
0.6769	Remote Similarity	NPD2846	Clinical (unspecified phase)
0.6767	Remote Similarity	NPD4214	Discontinued
0.6767	Remote Similarity	NPD6852	Discontinued
0.6759	Remote Similarity	NPD1088	Approved
0.6754	Remote Similarity	NPD179	Clinical (unspecified phase)
0.6754	Remote Similarity	NPD3407	Phase 3
0.6748	Remote Similarity	NPD2212	Approved
0.6748	Remote Similarity	NPD2210	Approved
0.6727	Remote Similarity	NPD2895	Discontinued
0.6726	Remote Similarity	NPD2196	Discontinued
0.6726	Remote Similarity	NPD2171	Approved
0.6726	Remote Similarity	NPD6024	Approved
0.6726	Remote Similarity	NPD4817	Approved
0.6726	Remote Similarity	NPD2193	Phase 2
0.6726	Remote Similarity	NPD4803	Discontinued
0.6726	Remote Similarity	NPD2648	Phase 3
0.6726	Remote Similarity	NPD813	Approved
0.6726	Remote Similarity	NPD6027	Approved
0.6726	Remote Similarity	NPD4818	Approved
0.6723	Remote Similarity	NPD1764	Approved
0.6723	Remote Similarity	NPD1762	Approved
0.6721	Remote Similarity	NPD7522	Discontinued
0.6721	Remote Similarity	NPD6360	Discontinued
0.6697	Remote Similarity	NPD3718	Approved
0.6697	Remote Similarity	NPD3719	Approved
0.6697	Remote Similarity	NPD1409	Phase 3
0.6696	Remote Similarity	NPD2192	Approved
0.6696	Remote Similarity	NPD563	Approved
0.6696	Remote Similarity	NPD2197	Approved
0.6696	Remote Similarity	NPD564	Approved
0.6696	Remote Similarity	NPD9712	Approved
0.6695	Remote Similarity	NPD188	Approved
0.6695	Remote Similarity	NPD189	Phase 3
0.6694	Remote Similarity	NPD2622	Approved
0.6694	Remote Similarity	NPD4733	Approved
0.6694	Remote Similarity	NPD7342	Discontinued
0.6692	Remote Similarity	NPD3136	Phase 2
0.6692	Remote Similarity	NPD6919	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1360	Approved
0.6667	Remote Similarity	NPD7450	Phase 2
0.6667	Remote Similarity	NPD14	Approved
0.6667	Remote Similarity	NPD7602	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1875	Phase 1
0.6667	Remote Similarity	NPD23	Approved
0.6667	Remote Similarity	NPD3357	Discontinued
0.6667	Remote Similarity	NPD2244	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5103	Approved
0.6667	Remote Similarity	NPD8416	Discontinued
0.6667	Remote Similarity	NPD731	Approved
0.6642	Remote Similarity	NPD4077	Clinical (unspecified phase)
0.6641	Remote Similarity	NPD2585	Clinical (unspecified phase)
0.6641	Remote Similarity	NPD3606	Clinical (unspecified phase)
0.664	Remote Similarity	NPD5770	Phase 3
0.6634	Remote Similarity	NPD9490	Approved
0.6618	Remote Similarity	NPD7720	Phase 2
0.6617	Remote Similarity	NPD8643	Discontinued
0.6615	Remote Similarity	NPD7979	Clinical (unspecified phase)
0.6614	Remote Similarity	NPD5157	Phase 1
0.6614	Remote Similarity	NPD1755	Approved
0.6614	Remote Similarity	NPD5159	Phase 2
0.6614	Remote Similarity	NPD5158	Clinical (unspecified phase)
0.6613	Remote Similarity	NPD4209	Clinical (unspecified phase)
0.661	Remote Similarity	NPD1756	Approved
0.661	Remote Similarity	NPD1752	Approved
0.6607	Remote Similarity	NPD9710	Approved
0.6607	Remote Similarity	NPD9711	Approved
0.6607	Remote Similarity	NPD4117	Approved
0.6604	Remote Similarity	NPD1087	Approved
0.66	Remote Similarity	NPD603	Approved
0.6593	Remote Similarity	NPD7728	Clinical (unspecified phase)
0.6591	Remote Similarity	NPD941	Approved
0.6591	Remote Similarity	NPD5729	Clinical (unspecified phase)
0.6589	Remote Similarity	NPD3588	Discontinued
0.6587	Remote Similarity	NPD2609	Approved
0.6587	Remote Similarity	NPD2608	Approved
0.6587	Remote Similarity	NPD4217	Approved
0.6587	Remote Similarity	NPD4218	Approved
0.6587	Remote Similarity	NPD3131	Approved
0.6587	Remote Similarity	NPD4216	Approved
0.6587	Remote Similarity	NPD2611	Approved
0.6587	Remote Similarity	NPD3132	Approved
0.6587	Remote Similarity	NPD2612	Approved
0.6587	Remote Similarity	NPD4215	Approved
0.6587	Remote Similarity	NPD2610	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