NPASS Compound

Structure

NPC471322 OpenBabel07101718312D 28 28 0 0 0 0 0 0 0 0999 V2000 -12.9904 6.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -13.8564 6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -13.8564 5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.9904 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.9904 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.1244 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.1244 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.2583 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.2583 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.3923 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.5263 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.6603 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -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 0.0000 2.0000 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 -4.3301 0.5000 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 -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 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 C 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 -3.4641 -0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 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 20 1 0 0 0 0 17 18 2 0 0 0 0 17 19 1 0 0 0 0 18 23 1 0 0 0 0 19 25 2 0 0 0 0 20 26 1 0 0 0 0 21 23 2 0 0 0 0 21 25 1 0 0 0 0 22 23 1 0 0 0 0 22 27 1 0 0 0 0 24 26 2 3 0 0 0 24 27 1 0 0 0 0 24 28 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	387.32
Volume:	443.702
LogP:	5.643
LogD:	4.199
LogS:	-2.477
# Rotatable Bonds:	19
TPSA:	54.02
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	1
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.236
Synthetic Accessibility Score:	2.248
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:	-5.064
MDCK Permeability:	3.0271956347860396e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.022
20% Bioavailability (F20%):	0.911
30% Bioavailability (F30%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.642
Plasma Protein Binding (PPB):	97.32280731201172%
Volume Distribution (VD):	1.123
Pgp-substrate:	1.016237497329712%

ADMET: Metabolism

CYP1A2-inhibitor:	0.345
CYP1A2-substrate:	0.471
CYP2C19-inhibitor:	0.77
CYP2C19-substrate:	0.603
CYP2C9-inhibitor:	0.509
CYP2C9-substrate:	0.979
CYP2D6-inhibitor:	0.858
CYP2D6-substrate:	0.883
CYP3A4-inhibitor:	0.954
CYP3A4-substrate:	0.123

ADMET: Excretion

Clearance (CL):	5.464
Half-life (T1/2):	0.768

ADMET: Toxicity

hERG Blockers:	0.639
Human Hepatotoxicity (H-HT):	0.064
Drug-inuced Liver Injury (DILI):	0.024
AMES Toxicity:	0.008
Rat Oral Acute Toxicity:	0.031
Maximum Recommended Daily Dose:	0.067
Skin Sensitization:	0.945
Carcinogencity:	0.041
Eye Corrosion:	0.003
Eye Irritation:	0.018
Respiratory Toxicity:	0.722

Download Data

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

Natural Product: NPC471322

Natural Product ID:	NPC471322
*Common Name:**	1-[(Z)-Heptadec-8-Enyl]-3-(Pyridin-3-Ylmethyl)Urea
IUPAC Name:	1-[(Z)-heptadec-8-enyl]-3-(pyridin-3-ylmethyl)urea
Synonyms:
Standard InCHIKey:	QPVHCPOCTLFHEW-KTKRTIGZSA-N
Standard InCHI:	InChI=1S/C24H41N3O/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-20-26-24(28)27-22-23-18-17-19-25-21-23/h9-10,17-19,21H,2-8,11-16,20,22H2,1H3,(H2,26,27,28)/b10-9-
SMILES:	CCCCCCCCC=CCCCCCCCNC(=O)NCC1=CN=CC=C1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2413180
PubChem CID:	71770552
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000089] Pyridines and derivatives

*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[473861]
NPT1418	Individual Protein	Anandamide amidohydrolase	Homo sapiens	Inhibition	=	22.0	%	PMID[473861]
NPT1418	Individual Protein	Anandamide amidohydrolase	Homo sapiens	Inhibition	=	42.6	%	PMID[473861]

☑ 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 NPC471322 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	506
0.1-0.2	11430
0.2-0.3	19515
0.3-0.4	5642
0.4-0.5	2958
0.5-0.6	1854
0.6-0.7	657
0.7-0.8	114
0.8-0.85	17
0.85-0.9	3
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8769	High Similarity	NPC471311
0.8769	High Similarity	NPC471313
0.8702	High Similarity	NPC89490
0.8636	High Similarity	NPC475090
0.8636	High Similarity	NPC329896
0.8636	High Similarity	NPC475105
0.8605	High Similarity	NPC290094
0.8409	Intermediate Similarity	NPC202957
0.8409	Intermediate Similarity	NPC169625
0.8397	Intermediate Similarity	NPC27740
0.837	Intermediate Similarity	NPC101165
0.8333	Intermediate Similarity	NPC166424
0.8333	Intermediate Similarity	NPC146373
0.8333	Intermediate Similarity	NPC245244
0.8281	Intermediate Similarity	NPC240136
0.8281	Intermediate Similarity	NPC297486
0.8281	Intermediate Similarity	NPC471402
0.8201	Intermediate Similarity	NPC471312
0.8168	Intermediate Similarity	NPC265605
0.8168	Intermediate Similarity	NPC48564
0.8168	Intermediate Similarity	NPC182570
0.816	Intermediate Similarity	NPC27802
0.812	Intermediate Similarity	NPC476322
0.8065	Intermediate Similarity	NPC76540
0.7971	Intermediate Similarity	NPC324611
0.7939	Intermediate Similarity	NPC91958
0.7836	Intermediate Similarity	NPC329825
0.7826	Intermediate Similarity	NPC476131
0.7803	Intermediate Similarity	NPC143603
0.777	Intermediate Similarity	NPC69914
0.774	Intermediate Similarity	NPC471323
0.7718	Intermediate Similarity	NPC105818
0.7718	Intermediate Similarity	NPC24678
0.7714	Intermediate Similarity	NPC256893
0.7687	Intermediate Similarity	NPC314372
0.7681	Intermediate Similarity	NPC212125
0.7681	Intermediate Similarity	NPC306397
0.7671	Intermediate Similarity	NPC190296
0.7655	Intermediate Similarity	NPC469761
0.7655	Intermediate Similarity	NPC469767
0.7655	Intermediate Similarity	NPC469780
0.7655	Intermediate Similarity	NPC469783
0.7655	Intermediate Similarity	NPC469779
0.7655	Intermediate Similarity	NPC469784
0.7655	Intermediate Similarity	NPC469768
0.7643	Intermediate Similarity	NPC282398
0.7616	Intermediate Similarity	NPC259644
0.7616	Intermediate Similarity	NPC469765
0.7616	Intermediate Similarity	NPC469760
0.7616	Intermediate Similarity	NPC469786
0.7616	Intermediate Similarity	NPC469763
0.7616	Intermediate Similarity	NPC73952
0.7616	Intermediate Similarity	NPC25008
0.7615	Intermediate Similarity	NPC235843
0.7603	Intermediate Similarity	NPC469766
0.7581	Intermediate Similarity	NPC83987
0.7576	Intermediate Similarity	NPC84268
0.7569	Intermediate Similarity	NPC65408
0.7566	Intermediate Similarity	NPC80597
0.7566	Intermediate Similarity	NPC75540
0.7566	Intermediate Similarity	NPC211572
0.7566	Intermediate Similarity	NPC212376
0.7566	Intermediate Similarity	NPC70922
0.7518	Intermediate Similarity	NPC46358
0.75	Intermediate Similarity	NPC231655
0.7467	Intermediate Similarity	NPC471957
0.7466	Intermediate Similarity	NPC73767
0.7466	Intermediate Similarity	NPC110126
0.745	Intermediate Similarity	NPC159856
0.7448	Intermediate Similarity	NPC105127
0.7448	Intermediate Similarity	NPC314102
0.7448	Intermediate Similarity	NPC84911
0.7448	Intermediate Similarity	NPC251722
0.7405	Intermediate Similarity	NPC49217
0.7403	Intermediate Similarity	NPC469785
0.7394	Intermediate Similarity	NPC315320
0.7379	Intermediate Similarity	NPC96102
0.7379	Intermediate Similarity	NPC29886
0.7379	Intermediate Similarity	NPC261195
0.7365	Intermediate Similarity	NPC476454
0.7355	Intermediate Similarity	NPC469762
0.7347	Intermediate Similarity	NPC32002
0.7347	Intermediate Similarity	NPC316811
0.7347	Intermediate Similarity	NPC315348
0.7343	Intermediate Similarity	NPC82295
0.7325	Intermediate Similarity	NPC470203
0.7305	Intermediate Similarity	NPC165370
0.729	Intermediate Similarity	NPC476464
0.7285	Intermediate Similarity	NPC143872
0.7278	Intermediate Similarity	NPC311276
0.7261	Intermediate Similarity	NPC470204
0.726	Intermediate Similarity	NPC29702
0.7237	Intermediate Similarity	NPC477974
0.7219	Intermediate Similarity	NPC467188
0.7215	Intermediate Similarity	NPC225018
0.7211	Intermediate Similarity	NPC150259
0.7208	Intermediate Similarity	NPC216713
0.7208	Intermediate Similarity	NPC470233
0.7197	Intermediate Similarity	NPC135141
0.7197	Intermediate Similarity	NPC92796
0.719	Intermediate Similarity	NPC321911
0.7188	Intermediate Similarity	NPC160105
0.7181	Intermediate Similarity	NPC279081
0.7172	Intermediate Similarity	NPC322488
0.717	Intermediate Similarity	NPC476446
0.717	Intermediate Similarity	NPC469813
0.717	Intermediate Similarity	NPC40779
0.717	Intermediate Similarity	NPC78375
0.7161	Intermediate Similarity	NPC200214
0.7143	Intermediate Similarity	NPC53947
0.7134	Intermediate Similarity	NPC469897
0.7134	Intermediate Similarity	NPC129721
0.7132	Intermediate Similarity	NPC476566
0.7124	Intermediate Similarity	NPC105811
0.7124	Intermediate Similarity	NPC179787
0.7124	Intermediate Similarity	NPC469811
0.7124	Intermediate Similarity	NPC201380
0.7124	Intermediate Similarity	NPC470111
0.7115	Intermediate Similarity	NPC209362
0.7107	Intermediate Similarity	NPC71079
0.7089	Intermediate Similarity	NPC56765
0.7081	Intermediate Similarity	NPC474561
0.7081	Intermediate Similarity	NPC49954
0.7067	Intermediate Similarity	NPC230002
0.7063	Intermediate Similarity	NPC474217
0.7059	Intermediate Similarity	NPC63545
0.7059	Intermediate Similarity	NPC288838
0.7055	Intermediate Similarity	NPC330326
0.7051	Intermediate Similarity	NPC325903
0.7044	Intermediate Similarity	NPC122141
0.7037	Intermediate Similarity	NPC473901
0.7037	Intermediate Similarity	NPC201700
0.7032	Intermediate Similarity	NPC40070
0.7025	Intermediate Similarity	NPC193740
0.7025	Intermediate Similarity	NPC167635
0.7019	Intermediate Similarity	NPC85918
0.7014	Intermediate Similarity	NPC471589
0.7012	Intermediate Similarity	NPC314603
0.7006	Intermediate Similarity	NPC16659
0.7006	Intermediate Similarity	NPC477815
0.7	Intermediate Similarity	NPC471177
0.7	Intermediate Similarity	NPC282231
0.7	Intermediate Similarity	NPC124542
0.7	Intermediate Similarity	NPC59779
0.6994	Remote Similarity	NPC194411
0.6993	Remote Similarity	NPC204141
0.6993	Remote Similarity	NPC285731
0.698	Remote Similarity	NPC125746
0.6977	Remote Similarity	NPC474430
0.6975	Remote Similarity	NPC278366
0.6975	Remote Similarity	NPC98187
0.6975	Remote Similarity	NPC127730
0.697	Remote Similarity	NPC317054
0.6957	Remote Similarity	NPC81561
0.6957	Remote Similarity	NPC194640
0.6957	Remote Similarity	NPC90723
0.6954	Remote Similarity	NPC59084
0.6951	Remote Similarity	NPC201634
0.6946	Remote Similarity	NPC265710
0.6944	Remote Similarity	NPC278451
0.6943	Remote Similarity	NPC251391
0.6937	Remote Similarity	NPC279918
0.6937	Remote Similarity	NPC131718
0.6933	Remote Similarity	NPC169433
0.6933	Remote Similarity	NPC63751
0.6933	Remote Similarity	NPC104049
0.6918	Remote Similarity	NPC213914
0.6918	Remote Similarity	NPC236711
0.6918	Remote Similarity	NPC286427
0.6914	Remote Similarity	NPC477975
0.6914	Remote Similarity	NPC471178
0.6913	Remote Similarity	NPC325252
0.6908	Remote Similarity	NPC63157
0.6908	Remote Similarity	NPC473868
0.6905	Remote Similarity	NPC471319
0.6905	Remote Similarity	NPC471320
0.6887	Remote Similarity	NPC104483
0.6884	Remote Similarity	NPC148140
0.6883	Remote Similarity	NPC86288
0.6882	Remote Similarity	NPC108011
0.6879	Remote Similarity	NPC470823
0.6879	Remote Similarity	NPC70406
0.6875	Remote Similarity	NPC206819
0.6875	Remote Similarity	NPC41257
0.6875	Remote Similarity	NPC230869
0.6875	Remote Similarity	NPC213774
0.6875	Remote Similarity	NPC318065
0.6867	Remote Similarity	NPC275305
0.6867	Remote Similarity	NPC37423
0.6863	Remote Similarity	NPC477977
0.6857	Remote Similarity	NPC11863
0.6852	Remote Similarity	NPC317105
0.6846	Remote Similarity	NPC198988
0.6842	Remote Similarity	NPC2949
0.6835	Remote Similarity	NPC141926
0.6832	Remote Similarity	NPC44773
0.6832	Remote Similarity	NPC215584
0.6831	Remote Similarity	NPC56856
0.6813	Remote Similarity	NPC216643
0.6813	Remote Similarity	NPC212742

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 NPC471322 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	247
0.1-0.2	847
0.2-0.3	1059
0.3-0.4	1821
0.4-0.5	2635
0.5-0.6	1786
0.6-0.7	628
0.7-0.8	120
0.8-0.85	5
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8626	High Similarity	NPD1598	Discontinued
0.856	High Similarity	NPD269	Clinical (unspecified phase)
0.8235	Intermediate Similarity	NPD9726	Discontinued
0.8175	Intermediate Similarity	NPD4823	Approved
0.8175	Intermediate Similarity	NPD4824	Approved
0.8169	Intermediate Similarity	NPD2007	Clinical (unspecified phase)
0.8168	Intermediate Similarity	NPD270	Clinical (unspecified phase)
0.8168	Intermediate Similarity	NPD268	Approved
0.8168	Intermediate Similarity	NPD271	Approved
0.814	Intermediate Similarity	NPD9396	Approved
0.814	Intermediate Similarity	NPD9392	Approved
0.8074	Intermediate Similarity	NPD991	Phase 2
0.8074	Intermediate Similarity	NPD992	Clinical (unspecified phase)
0.8058	Intermediate Similarity	NPD2142	Approved
0.8058	Intermediate Similarity	NPD2140	Approved
0.8058	Intermediate Similarity	NPD2141	Approved
0.8013	Intermediate Similarity	NPD8026	Phase 1
0.8	Intermediate Similarity	NPD9583	Approved
0.7987	Intermediate Similarity	NPD2748	Clinical (unspecified phase)
0.7985	Intermediate Similarity	NPD9357	Approved
0.7941	Intermediate Similarity	NPD2118	Approved
0.7941	Intermediate Similarity	NPD2119	Approved
0.7842	Intermediate Similarity	NPD809	Discontinued
0.7793	Intermediate Similarity	NPD3717	Discontinued
0.777	Intermediate Similarity	NPD3475	Approved
0.777	Intermediate Similarity	NPD3476	Approved
0.7742	Intermediate Similarity	NPD5611	Phase 2
0.7703	Intermediate Similarity	NPD4702	Approved
0.7703	Intermediate Similarity	NPD4703	Approved
0.7681	Intermediate Similarity	NPD9284	Approved
0.7681	Intermediate Similarity	NPD9080	Approved
0.7671	Intermediate Similarity	NPD1427	Clinical (unspecified phase)
0.766	Intermediate Similarity	NPD1993	Approved
0.766	Intermediate Similarity	NPD1994	Approved
0.766	Intermediate Similarity	NPD1995	Approved
0.7655	Intermediate Similarity	NPD1395	Clinical (unspecified phase)
0.7643	Intermediate Similarity	NPD4024	Phase 3
0.7639	Intermediate Similarity	NPD2896	Discontinued
0.7635	Intermediate Similarity	NPD7469	Discontinued
0.7619	Intermediate Similarity	NPD1988	Phase 1
0.7606	Intermediate Similarity	NPD3944	Approved
0.7606	Intermediate Similarity	NPD4030	Approved
0.7606	Intermediate Similarity	NPD4029	Approved
0.7606	Intermediate Similarity	NPD4028	Approved
0.7606	Intermediate Similarity	NPD3942	Approved
0.7589	Intermediate Similarity	NPD803	Phase 1
0.7574	Intermediate Similarity	NPD748	Clinical (unspecified phase)
0.7569	Intermediate Similarity	NPD201	Phase 2
0.7569	Intermediate Similarity	NPD200	Phase 2
0.755	Intermediate Similarity	NPD3262	Approved
0.7535	Intermediate Similarity	NPD1627	Clinical (unspecified phase)
0.7518	Intermediate Similarity	NPD715	Phase 3
0.7517	Intermediate Similarity	NPD6148	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD4181	Approved
0.75	Intermediate Similarity	NPD1095	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD9099	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1917	Discontinued
0.75	Intermediate Similarity	NPD9098	Phase 3
0.75	Intermediate Similarity	NPD3813	Approved
0.75	Intermediate Similarity	NPD792	Discontinued
0.7485	Intermediate Similarity	NPD4891	Phase 2
0.7483	Intermediate Similarity	NPD2466	Phase 3
0.7483	Intermediate Similarity	NPD2465	Approved
0.7483	Intermediate Similarity	NPD1722	Approved
0.7483	Intermediate Similarity	NPD2462	Phase 3
0.7467	Intermediate Similarity	NPD2110	Approved
0.7466	Intermediate Similarity	NPD768	Clinical (unspecified phase)
0.7466	Intermediate Similarity	NPD786	Approved
0.741	Intermediate Similarity	NPD7026	Phase 2
0.7394	Intermediate Similarity	NPD9207	Approved
0.7394	Intermediate Similarity	NPD9206	Approved
0.7391	Intermediate Similarity	NPD4128	Approved
0.7386	Intermediate Similarity	NPD2012	Clinical (unspecified phase)
0.7379	Intermediate Similarity	NPD198	Clinical (unspecified phase)
0.7372	Intermediate Similarity	NPD9598	Discontinued
0.7358	Intermediate Similarity	NPD2390	Clinical (unspecified phase)
0.7355	Intermediate Similarity	NPD5300	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD2075	Approved
0.7347	Intermediate Similarity	NPD2070	Approved
0.7347	Intermediate Similarity	NPD2072	Approved
0.7347	Intermediate Similarity	NPD2071	Approved
0.7347	Intermediate Similarity	NPD2073	Approved
0.7347	Intermediate Similarity	NPD2074	Approved
0.7347	Intermediate Similarity	NPD2069	Approved
0.7347	Intermediate Similarity	NPD2068	Approved
0.7346	Intermediate Similarity	NPD2367	Phase 2
0.7338	Intermediate Similarity	NPD5358	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD2165	Phase 1
0.7338	Intermediate Similarity	NPD2061	Approved
0.7325	Intermediate Similarity	NPD6771	Discontinued
0.732	Intermediate Similarity	NPD4641	Discontinued
0.7319	Intermediate Similarity	NPD5787	Discontinued
0.7315	Intermediate Similarity	NPD2006	Phase 2
0.7312	Intermediate Similarity	NPD2619	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD2620	Phase 2
0.731	Intermediate Similarity	NPD272	Approved
0.7297	Intermediate Similarity	NPD1649	Discontinued
0.729	Intermediate Similarity	NPD3112	Approved
0.729	Intermediate Similarity	NPD3114	Approved
0.729	Intermediate Similarity	NPD3113	Approved
0.729	Intermediate Similarity	NPD3115	Approved
0.7284	Intermediate Similarity	NPD2928	Phase 2
0.7279	Intermediate Similarity	NPD1380	Discovery
0.7267	Intermediate Similarity	NPD3116	Approved
0.7267	Intermediate Similarity	NPD3117	Approved
0.7267	Intermediate Similarity	NPD751	Clinical (unspecified phase)
0.726	Intermediate Similarity	NPD206	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD4805	Approved
0.7244	Intermediate Similarity	NPD2865	Clinical (unspecified phase)
0.7237	Intermediate Similarity	NPD1661	Suspended
0.7226	Intermediate Similarity	NPD1328	Approved
0.7215	Intermediate Similarity	NPD2385	Clinical (unspecified phase)
0.7211	Intermediate Similarity	NPD9506	Approved
0.72	Intermediate Similarity	NPD4510	Discontinued
0.719	Intermediate Similarity	NPD3100	Discontinued
0.7181	Intermediate Similarity	NPD2222	Discontinued
0.7181	Intermediate Similarity	NPD9599	Approved
0.7174	Intermediate Similarity	NPD4811	Discontinued
0.717	Intermediate Similarity	NPD5925	Phase 1
0.717	Intermediate Similarity	NPD3583	Phase 2
0.7162	Intermediate Similarity	NPD203	Clinical (unspecified phase)
0.7161	Intermediate Similarity	NPD2837	Discontinued
0.7161	Intermediate Similarity	NPD3339	Approved
0.7152	Intermediate Similarity	NPD1352	Discontinued
0.7143	Intermediate Similarity	NPD490	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD2172	Phase 1
0.7133	Intermediate Similarity	NPD1382	Phase 2
0.7133	Intermediate Similarity	NPD1383	Phase 3
0.7124	Intermediate Similarity	NPD2089	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD4547	Phase 3
0.7115	Intermediate Similarity	NPD6285	Phase 2
0.7115	Intermediate Similarity	NPD2809	Approved
0.7114	Intermediate Similarity	NPD4804	Approved
0.7107	Intermediate Similarity	NPD2480	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD2872	Phase 2
0.7097	Intermediate Similarity	NPD5965	Clinical (unspecified phase)
0.7093	Intermediate Similarity	NPD4615	Phase 2
0.7089	Intermediate Similarity	NPD5255	Approved
0.7086	Intermediate Similarity	NPD4637	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD1183	Approved
0.7078	Intermediate Similarity	NPD2430	Phase 2
0.7078	Intermediate Similarity	NPD4374	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD5065	Approved
0.7073	Intermediate Similarity	NPD5322	Clinical (unspecified phase)
0.707	Intermediate Similarity	NPD6026	Approved
0.7066	Intermediate Similarity	NPD8408	Discontinued
0.7055	Intermediate Similarity	NPD9100	Approved
0.7052	Intermediate Similarity	NPD3485	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD3341	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD2511	Approved
0.7039	Intermediate Similarity	NPD1918	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD6044	Discontinued
0.7029	Intermediate Similarity	NPD6664	Approved
0.7025	Intermediate Similarity	NPD5541	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD2145	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD6363	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD1270	Approved
0.7011	Intermediate Similarity	NPD4998	Phase 3
0.7011	Intermediate Similarity	NPD4999	Phase 3
0.7007	Intermediate Similarity	NPD3385	Approved
0.7	Intermediate Similarity	NPD4239	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD3378	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD4184	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD5436	Phase 1
0.6994	Remote Similarity	NPD2127	Suspended
0.6981	Remote Similarity	NPD604	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD1248	Discontinued
0.6966	Remote Similarity	NPD3654	Approved
0.6966	Remote Similarity	NPD9305	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD5806	Clinical (unspecified phase)
0.6962	Remote Similarity	NPD2150	Discontinued
0.6957	Remote Similarity	NPD3323	Discontinued
0.6951	Remote Similarity	NPD1567	Clinical (unspecified phase)
0.6934	Remote Similarity	NPD60	Approved
0.6933	Remote Similarity	NPD4779	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD5069	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD2641	Approved
0.6933	Remote Similarity	NPD2640	Approved
0.6933	Remote Similarity	NPD6872	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD971	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD7913	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD7175	Phase 1
0.6918	Remote Similarity	NPD2581	Approved
0.6918	Remote Similarity	NPD2582	Approved
0.6914	Remote Similarity	NPD1333	Phase 3
0.6914	Remote Similarity	NPD509	Phase 3
0.6912	Remote Similarity	NPD1813	Discontinued
0.6908	Remote Similarity	NPD5020	Approved
0.6901	Remote Similarity	NPD706	Phase 1
0.6899	Remote Similarity	NPD976	Approved
0.6899	Remote Similarity	NPD977	Approved
0.6899	Remote Similarity	NPD975	Approved
0.6894	Remote Similarity	NPD1016	Phase 2
0.6894	Remote Similarity	NPD1015	Phase 2
0.689	Remote Similarity	NPD2875	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD174	Discontinued
0.6883	Remote Similarity	NPD175	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD1679	Approved
0.6867	Remote Similarity	NPD3799	Suspended
0.6867	Remote Similarity	NPD2829	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