NPASS Compound

Structure

NPC202613 OpenBabel07101718182D 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 2 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 2 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:	383.28
Volume:	442.522
LogP:	5.251
LogD:	4.331
LogS:	-4.263
# Rotatable Bonds:	17
TPSA:	46.17
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	1
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.269
Synthetic Accessibility Score:	2.417
Fsp3:	0.52
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:	-4.832
MDCK Permeability:	1.6436464647995308e-05
Pgp-inhibitor:	0.988
Pgp-substrate:	0.01
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.031
30% Bioavailability (F30%):	0.369

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.938
Plasma Protein Binding (PPB):	97.72745513916016%
Volume Distribution (VD):	1.119
Pgp-substrate:	0.7823852896690369%

ADMET: Metabolism

CYP1A2-inhibitor:	0.435
CYP1A2-substrate:	0.577
CYP2C19-inhibitor:	0.796
CYP2C19-substrate:	0.251
CYP2C9-inhibitor:	0.52
CYP2C9-substrate:	0.763
CYP2D6-inhibitor:	0.549
CYP2D6-substrate:	0.647
CYP3A4-inhibitor:	0.939
CYP3A4-substrate:	0.193

ADMET: Excretion

Clearance (CL):	5.135
Half-life (T1/2):	0.86

ADMET: Toxicity

hERG Blockers:	0.724
Human Hepatotoxicity (H-HT):	0.275
Drug-inuced Liver Injury (DILI):	0.024
AMES Toxicity:	0.022
Rat Oral Acute Toxicity:	0.281
Maximum Recommended Daily Dose:	0.933
Skin Sensitization:	0.963
Carcinogencity:	0.096
Eye Corrosion:	0.003
Eye Irritation:	0.029
Respiratory Toxicity:	0.86

Download Data

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

Natural Product: NPC202613

Natural Product ID:	NPC202613
*Common Name:**	(6E,8E)-N-Benzyl-5-Oxooctadeca-6,8-Dienamide
IUPAC Name:	(6E,8E)-N-benzyl-5-oxooctadeca-6,8-dienamide
Synonyms:
Standard InCHIKey:	DKMGVACNAAKVRR-MRBSYODNSA-N
Standard InCHI:	InChI=1S/C25H37NO2/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/h10-15,17-19H,2-9,16,20-22H2,1H3,(H,26,28)/b11-10+,19-15+
SMILES:	CCCCCCCCC/C=C/C=C/C(=O)CCCC(=NCc1ccccc1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2413164
PubChem CID:	71770342
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[452925]
NPT1418	Individual Protein	Anandamide amidohydrolase	Homo sapiens	Inhibition	<	10.0	%	PMID[452925]
NPT1418	Individual Protein	Anandamide amidohydrolase	Homo sapiens	Inhibition	=	26.4	%	PMID[452925]

☑ 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 NPC202613 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	883
0.2-0.3	4513
0.3-0.4	14562
0.4-0.5	17713
0.5-0.6	4119
0.6-0.7	705
0.7-0.8	90
0.8-0.85	10
0.85-0.9	7
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9388	High Similarity	NPC471317
0.8646	High Similarity	NPC74936
0.8646	High Similarity	NPC471307
0.8646	High Similarity	NPC159178
0.8646	High Similarity	NPC141139
0.8646	High Similarity	NPC209764
0.8646	High Similarity	NPC121872
0.8646	High Similarity	NPC78041
0.8542	High Similarity	NPC470877
0.844	Intermediate Similarity	NPC471318
0.8384	Intermediate Similarity	NPC471309
0.8119	Intermediate Similarity	NPC58674
0.7864	Intermediate Similarity	NPC25565
0.781	Intermediate Similarity	NPC12730
0.7788	Intermediate Similarity	NPC473501
0.7788	Intermediate Similarity	NPC475439
0.7778	Intermediate Similarity	NPC471638
0.7778	Intermediate Similarity	NPC473031
0.7757	Intermediate Similarity	NPC471310
0.7706	Intermediate Similarity	NPC327481
0.77	Intermediate Similarity	NPC12429
0.7611	Intermediate Similarity	NPC474584
0.7596	Intermediate Similarity	NPC303045
0.7596	Intermediate Similarity	NPC161972
0.7565	Intermediate Similarity	NPC188010
0.7549	Intermediate Similarity	NPC172128
0.7545	Intermediate Similarity	NPC274089
0.7545	Intermediate Similarity	NPC191215
0.7544	Intermediate Similarity	NPC35850
0.7544	Intermediate Similarity	NPC276949
0.7525	Intermediate Similarity	NPC325441
0.7523	Intermediate Similarity	NPC194390
0.7523	Intermediate Similarity	NPC113326
0.7523	Intermediate Similarity	NPC88267
0.7523	Intermediate Similarity	NPC224610
0.75	Intermediate Similarity	NPC239357
0.7478	Intermediate Similarity	NPC33742
0.7476	Intermediate Similarity	NPC226438
0.7476	Intermediate Similarity	NPC245259
0.7453	Intermediate Similarity	NPC311242
0.7436	Intermediate Similarity	NPC169328
0.7436	Intermediate Similarity	NPC254088
0.7434	Intermediate Similarity	NPC319579
0.7431	Intermediate Similarity	NPC164859
0.7414	Intermediate Similarity	NPC235421
0.7379	Intermediate Similarity	NPC258627
0.7379	Intermediate Similarity	NPC316108
0.7373	Intermediate Similarity	NPC237420
0.7373	Intermediate Similarity	NPC310467
0.7353	Intermediate Similarity	NPC477704
0.7353	Intermediate Similarity	NPC477693
0.7288	Intermediate Similarity	NPC470545
0.725	Intermediate Similarity	NPC478016
0.725	Intermediate Similarity	NPC478015
0.725	Intermediate Similarity	NPC478014
0.7232	Intermediate Similarity	NPC474804
0.7232	Intermediate Similarity	NPC231705
0.7232	Intermediate Similarity	NPC474973
0.7232	Intermediate Similarity	NPC130898
0.7228	Intermediate Similarity	NPC3210
0.7227	Intermediate Similarity	NPC470546
0.7227	Intermediate Similarity	NPC314992
0.7217	Intermediate Similarity	NPC329011
0.7203	Intermediate Similarity	NPC470544
0.72	Intermediate Similarity	NPC116057
0.7193	Intermediate Similarity	NPC258056
0.7168	Intermediate Similarity	NPC142297
0.7157	Intermediate Similarity	NPC203076
0.7154	Intermediate Similarity	NPC22746
0.7143	Intermediate Similarity	NPC314431
0.7143	Intermediate Similarity	NPC143516
0.713	Intermediate Similarity	NPC474149
0.7121	Intermediate Similarity	NPC316202
0.7119	Intermediate Similarity	NPC197470
0.7107	Intermediate Similarity	NPC190663
0.71	Intermediate Similarity	NPC14326
0.7099	Intermediate Similarity	NPC471316
0.7091	Intermediate Similarity	NPC469457
0.7087	Intermediate Similarity	NPC316746
0.7075	Intermediate Similarity	NPC323164
0.7063	Intermediate Similarity	NPC472413
0.7059	Intermediate Similarity	NPC2265
0.7049	Intermediate Similarity	NPC71684
0.7015	Intermediate Similarity	NPC314287
0.7009	Intermediate Similarity	NPC273814
0.7009	Intermediate Similarity	NPC291070
0.7009	Intermediate Similarity	NPC246757
0.6992	Remote Similarity	NPC160493
0.6972	Remote Similarity	NPC122493
0.6972	Remote Similarity	NPC10781
0.6972	Remote Similarity	NPC293628
0.6972	Remote Similarity	NPC33168
0.6972	Remote Similarity	NPC472788
0.6967	Remote Similarity	NPC80150
0.6967	Remote Similarity	NPC45777
0.6967	Remote Similarity	NPC17388
0.6967	Remote Similarity	NPC477061
0.6967	Remote Similarity	NPC471308
0.6967	Remote Similarity	NPC289330
0.6967	Remote Similarity	NPC200964
0.6967	Remote Similarity	NPC53596
0.6967	Remote Similarity	NPC160120
0.6964	Remote Similarity	NPC178902
0.696	Remote Similarity	NPC47667
0.6957	Remote Similarity	NPC473676
0.6935	Remote Similarity	NPC35996
0.6935	Remote Similarity	NPC472415
0.6935	Remote Similarity	NPC6975
0.693	Remote Similarity	NPC471447
0.693	Remote Similarity	NPC45033
0.6923	Remote Similarity	NPC275410
0.6923	Remote Similarity	NPC194326
0.6909	Remote Similarity	NPC476120
0.6909	Remote Similarity	NPC322598
0.69	Remote Similarity	NPC192623
0.6881	Remote Similarity	NPC471320
0.6881	Remote Similarity	NPC471319
0.6875	Remote Similarity	NPC478147
0.6863	Remote Similarity	NPC44830
0.6847	Remote Similarity	NPC54647
0.6842	Remote Similarity	NPC211551
0.6842	Remote Similarity	NPC476198
0.6842	Remote Similarity	NPC167336
0.6842	Remote Similarity	NPC67043
0.6833	Remote Similarity	NPC317254
0.6829	Remote Similarity	NPC27833
0.6825	Remote Similarity	NPC474926
0.6825	Remote Similarity	NPC101719
0.6825	Remote Similarity	NPC472414
0.6818	Remote Similarity	NPC240042
0.6818	Remote Similarity	NPC208725
0.6818	Remote Similarity	NPC278228
0.6818	Remote Similarity	NPC324569
0.6818	Remote Similarity	NPC289201
0.681	Remote Similarity	NPC24101
0.681	Remote Similarity	NPC96224
0.68	Remote Similarity	NPC139901
0.68	Remote Similarity	NPC151405
0.68	Remote Similarity	NPC300205
0.6797	Remote Similarity	NPC111428
0.6797	Remote Similarity	NPC150863
0.6789	Remote Similarity	NPC256452
0.6777	Remote Similarity	NPC14672
0.6777	Remote Similarity	NPC315276
0.6777	Remote Similarity	NPC285926
0.6774	Remote Similarity	NPC202521
0.6772	Remote Similarity	NPC477937
0.6768	Remote Similarity	NPC179726
0.6762	Remote Similarity	NPC198747
0.6757	Remote Similarity	NPC179411
0.6748	Remote Similarity	NPC319950
0.6746	Remote Similarity	NPC222466
0.6737	Remote Similarity	NPC98880
0.6733	Remote Similarity	NPC127343
0.6733	Remote Similarity	NPC164086
0.6731	Remote Similarity	NPC95965
0.6731	Remote Similarity	NPC123476
0.6729	Remote Similarity	NPC78154
0.6727	Remote Similarity	NPC3371
0.6726	Remote Similarity	NPC318154
0.672	Remote Similarity	NPC474862
0.672	Remote Similarity	NPC252878
0.6719	Remote Similarity	NPC319766
0.6718	Remote Similarity	NPC328070
0.6716	Remote Similarity	NPC471201
0.67	Remote Similarity	NPC285470
0.67	Remote Similarity	NPC36342
0.67	Remote Similarity	NPC2785
0.6697	Remote Similarity	NPC34243
0.6697	Remote Similarity	NPC476483
0.6696	Remote Similarity	NPC474308
0.6695	Remote Similarity	NPC323007
0.6694	Remote Similarity	NPC476990
0.6693	Remote Similarity	NPC205946
0.6693	Remote Similarity	NPC4974
0.6692	Remote Similarity	NPC183722
0.6692	Remote Similarity	NPC43755
0.6667	Remote Similarity	NPC248283
0.6667	Remote Similarity	NPC71271
0.6667	Remote Similarity	NPC187725
0.6667	Remote Similarity	NPC95289
0.6667	Remote Similarity	NPC247976
0.6667	Remote Similarity	NPC471315
0.6667	Remote Similarity	NPC182549
0.6667	Remote Similarity	NPC141607
0.6667	Remote Similarity	NPC110704
0.6667	Remote Similarity	NPC473322
0.6667	Remote Similarity	NPC472243
0.6667	Remote Similarity	NPC114741
0.6667	Remote Similarity	NPC178681
0.6667	Remote Similarity	NPC46427
0.6667	Remote Similarity	NPC471314
0.6667	Remote Similarity	NPC296712
0.6667	Remote Similarity	NPC271642
0.6641	Remote Similarity	NPC326966
0.6633	Remote Similarity	NPC299134
0.6632	Remote Similarity	NPC311343
0.6619	Remote Similarity	NPC478039
0.6615	Remote Similarity	NPC280807
0.6615	Remote Similarity	NPC472245

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 NPC202613 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	479
0.2-0.3	869
0.3-0.4	2102
0.4-0.5	3493
0.5-0.6	1750
0.6-0.7	343
0.7-0.8	24
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
0.8469	Intermediate Similarity	NPD6690	Approved
0.7589	Intermediate Similarity	NPD3642	Approved
0.7589	Intermediate Similarity	NPD3643	Approved
0.7589	Intermediate Similarity	NPD3644	Approved
0.7573	Intermediate Similarity	NPD1812	Approved
0.7573	Intermediate Similarity	NPD1814	Approved
0.75	Intermediate Similarity	NPD1080	Approved
0.7455	Intermediate Similarity	NPD999	Phase 2
0.7455	Intermediate Similarity	NPD1018	Approved
0.7429	Intermediate Similarity	NPD4814	Discontinued
0.7426	Intermediate Similarity	NPD187	Approved
0.7407	Intermediate Similarity	NPD4760	Clinical (unspecified phase)
0.7377	Intermediate Similarity	NPD6325	Discontinued
0.7297	Intermediate Similarity	NPD1040	Phase 2
0.7227	Intermediate Similarity	NPD2217	Approved
0.7227	Intermediate Similarity	NPD2218	Phase 2
0.7196	Intermediate Similarity	NPD2507	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD1066	Discontinued
0.7156	Intermediate Similarity	NPD1067	Discontinued
0.7155	Intermediate Similarity	NPD181	Approved
0.713	Intermediate Similarity	NPD1099	Approved
0.713	Intermediate Similarity	NPD2487	Clinical (unspecified phase)
0.713	Intermediate Similarity	NPD1100	Approved
0.7119	Intermediate Similarity	NPD1348	Approved
0.7103	Intermediate Similarity	NPD1081	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD5578	Approved
0.7097	Intermediate Similarity	NPD5577	Clinical (unspecified phase)
0.7094	Intermediate Similarity	NPD1680	Approved
0.7094	Intermediate Similarity	NPD1682	Approved
0.7094	Intermediate Similarity	NPD1681	Approved
0.7025	Intermediate Similarity	NPD5981	Approved
0.7009	Intermediate Similarity	NPD4165	Phase 2
0.7009	Intermediate Similarity	NPD3066	Phase 2
0.7009	Intermediate Similarity	NPD5122	Clinical (unspecified phase)
0.6972	Remote Similarity	NPD9566	Approved
0.6953	Remote Similarity	NPD6919	Clinical (unspecified phase)
0.6953	Remote Similarity	NPD4738	Phase 2
0.6923	Remote Similarity	NPD9538	Approved
0.6923	Remote Similarity	NPD9508	Approved
0.6911	Remote Similarity	NPD2956	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD253	Approved
0.6905	Remote Similarity	NPD6302	Clinical (unspecified phase)
0.69	Remote Similarity	NPD5371	Approved
0.69	Remote Similarity	NPD5372	Approved
0.6899	Remote Similarity	NPD2846	Clinical (unspecified phase)
0.6885	Remote Similarity	NPD4504	Clinical (unspecified phase)
0.688	Remote Similarity	NPD2371	Approved
0.6875	Remote Similarity	NPD813	Approved
0.6875	Remote Similarity	NPD2196	Discontinued
0.6875	Remote Similarity	NPD2171	Approved
0.6875	Remote Similarity	NPD2648	Phase 3
0.6875	Remote Similarity	NPD2193	Phase 2
0.687	Remote Similarity	NPD6406	Approved
0.687	Remote Similarity	NPD6038	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD1101	Approved
0.6847	Remote Similarity	NPD2066	Phase 3
0.6842	Remote Similarity	NPD2197	Approved
0.6842	Remote Similarity	NPD2192	Approved
0.6829	Remote Similarity	NPD4733	Approved
0.6825	Remote Similarity	NPD1036	Approved
0.6822	Remote Similarity	NPD530	Approved
0.6814	Remote Similarity	NPD1542	Approved
0.6814	Remote Similarity	NPD6647	Phase 2
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	NPD3148	Approved
0.6807	Remote Similarity	NPD2658	Approved
0.6807	Remote Similarity	NPD3147	Approved
0.6803	Remote Similarity	NPD6093	Discontinued
0.68	Remote Similarity	NPD5108	Clinical (unspecified phase)
0.6797	Remote Similarity	NPD3626	Phase 3
0.6792	Remote Similarity	NPD5346	Phase 2
0.6792	Remote Similarity	NPD5347	Phase 2
0.6789	Remote Similarity	NPD4094	Approved
0.6777	Remote Similarity	NPD3123	Discovery
0.6777	Remote Similarity	NPD5162	Approved
0.6772	Remote Similarity	NPD1593	Approved
0.6767	Remote Similarity	NPD4214	Discontinued
0.6767	Remote Similarity	NPD4077	Clinical (unspecified phase)
0.6762	Remote Similarity	NPD4793	Discontinued
0.6759	Remote Similarity	NPD752	Approved
0.6754	Remote Similarity	NPD3407	Phase 3
0.6744	Remote Similarity	NPD6359	Clinical (unspecified phase)
0.6727	Remote Similarity	NPD2895	Discontinued
0.6726	Remote Similarity	NPD4119	Approved
0.6726	Remote Similarity	NPD1540	Approved
0.6724	Remote Similarity	NPD3420	Clinical (unspecified phase)
0.6723	Remote Similarity	NPD1764	Approved
0.6723	Remote Similarity	NPD1762	Approved
0.6721	Remote Similarity	NPD1758	Phase 1
0.6718	Remote Similarity	NPD941	Approved
0.6716	Remote Similarity	NPD6864	Phase 2
0.6716	Remote Similarity	NPD6865	Phase 2
0.6697	Remote Similarity	NPD719	Approved
0.6697	Remote Similarity	NPD1394	Approved
0.6697	Remote Similarity	NPD720	Approved
0.6696	Remote Similarity	NPD5717	Approved
0.6696	Remote Similarity	NPD564	Approved
0.6696	Remote Similarity	NPD563	Approved
0.6694	Remote Similarity	NPD2622	Approved
0.6693	Remote Similarity	NPD5367	Discontinued
0.6667	Remote Similarity	NPD1759	Phase 1
0.6667	Remote Similarity	NPD4655	Approved
0.6667	Remote Similarity	NPD4657	Approved
0.6667	Remote Similarity	NPD7828	Discontinued
0.6667	Remote Similarity	NPD226	Approved
0.6667	Remote Similarity	NPD7602	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD23	Approved
0.6667	Remote Similarity	NPD3357	Discontinued
0.6667	Remote Similarity	NPD8265	Approved
0.6667	Remote Similarity	NPD2617	Discontinued
0.6667	Remote Similarity	NPD5103	Approved
0.6667	Remote Similarity	NPD2584	Suspended
0.6667	Remote Similarity	NPD2244	Clinical (unspecified phase)
0.6618	Remote Similarity	NPD7720	Phase 2
0.6617	Remote Similarity	NPD7113	Clinical (unspecified phase)
0.6617	Remote Similarity	NPD2470	Clinical (unspecified phase)
0.6615	Remote Similarity	NPD7979	Clinical (unspecified phase)
0.6614	Remote Similarity	NPD5159	Phase 2
0.6614	Remote Similarity	NPD5157	Phase 1
0.6614	Remote Similarity	NPD5158	Clinical (unspecified phase)
0.6613	Remote Similarity	NPD2210	Approved
0.6613	Remote Similarity	NPD2212	Approved
0.6609	Remote Similarity	NPD2577	Clinical (unspecified phase)
0.6609	Remote Similarity	NPD179	Clinical (unspecified phase)
0.66	Remote Similarity	NPD603	Approved
0.6593	Remote Similarity	NPD6655	Clinical (unspecified phase)
0.6589	Remote Similarity	NPD5339	Clinical (unspecified phase)
0.6589	Remote Similarity	NPD3588	Discontinued
0.6585	Remote Similarity	NPD6360	Discontinued
0.6585	Remote Similarity	NPD7522	Discontinued
0.6583	Remote Similarity	NPD480	Approved
0.6579	Remote Similarity	NPD1417	Approved
0.6579	Remote Similarity	NPD4817	Approved
0.6579	Remote Similarity	NPD4818	Approved
0.6579	Remote Similarity	NPD1419	Approved
0.6571	Remote Similarity	NPD6631	Clinical (unspecified phase)
0.6567	Remote Similarity	NPD6817	Clinical (unspecified phase)
0.6565	Remote Similarity	NPD3136	Phase 2
0.6562	Remote Similarity	NPD6330	Clinical (unspecified phase)
0.656	Remote Similarity	NPD7342	Discontinued
0.656	Remote Similarity	NPD1362	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD1677	Discontinued
0.6549	Remote Similarity	NPD9712	Approved
0.6545	Remote Similarity	NPD3719	Approved
0.6545	Remote Similarity	NPD3718	Approved
0.6545	Remote Similarity	NPD1409	Phase 3
0.6538	Remote Similarity	NPD9491	Approved
0.6532	Remote Similarity	NPD998	Approved
0.6531	Remote Similarity	NPD9728	Phase 1
0.6522	Remote Similarity	NPD1930	Approved
0.6522	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD1929	Approved
0.6518	Remote Similarity	NPD1875	Phase 1
0.6514	Remote Similarity	NPD7609	Phase 3
0.6512	Remote Similarity	NPD2585	Clinical (unspecified phase)
0.6512	Remote Similarity	NPD3606	Clinical (unspecified phase)
0.6508	Remote Similarity	NPD1079	Discontinued
0.6508	Remote Similarity	NPD5770	Phase 3
0.6504	Remote Similarity	NPD732	Approved
0.6504	Remote Similarity	NPD1344	Phase 2
0.6504	Remote Similarity	NPD733	Approved
0.65	Remote Similarity	NPD753	Approved
0.6496	Remote Similarity	NPD467	Phase 1
0.6489	Remote Similarity	NPD4125	Approved
0.6486	Remote Similarity	NPD1693	Approved
0.6484	Remote Similarity	NPD182	Clinical (unspecified phase)
0.6481	Remote Similarity	NPD800	Approved
0.648	Remote Similarity	NPD4209	Clinical (unspecified phase)
0.6476	Remote Similarity	NPD2538	Approved
0.6476	Remote Similarity	NPD2539	Approved
0.6475	Remote Similarity	NPD1711	Phase 2
0.6471	Remote Similarity	NPD1107	Approved
0.6471	Remote Similarity	NPD1108	Approved
0.6471	Remote Similarity	NPD4158	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD7728	Clinical (unspecified phase)
0.6466	Remote Similarity	NPD5729	Clinical (unspecified phase)
0.6462	Remote Similarity	NPD3608	Clinical (unspecified phase)
0.646	Remote Similarity	NPD4117	Approved
0.646	Remote Similarity	NPD9711	Approved
0.646	Remote Similarity	NPD9710	Approved
0.6457	Remote Similarity	NPD3603	Phase 3
0.6455	Remote Similarity	NPD7631	Approved
0.6452	Remote Similarity	NPD997	Clinical (unspecified phase)
0.6446	Remote Similarity	NPD2607	Approved
0.6444	Remote Similarity	NPD8172	Phase 2
0.6444	Remote Similarity	NPD8173	Phase 2
0.6441	Remote Similarity	NPD2243	Clinical (unspecified phase)
0.6435	Remote Similarity	NPD854	Approved
0.6435	Remote Similarity	NPD6027	Approved
0.6435	Remote Similarity	NPD6024	Approved
0.6435	Remote Similarity	NPD855	Approved
0.6435	Remote Similarity	NPD4803	Discontinued
0.6435	Remote Similarity	NPD4719	Phase 2
0.6435	Remote Similarity	NPD5716	Approved
0.6435	Remote Similarity	NPD1932	Approved
0.6434	Remote Similarity	NPD3125	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