NPASS Compound

Structure

NPC471311 OpenBabel07101718282D 27 27 0 0 0 0 0 0 0 0999 V2000 -13.8564 6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -14.7224 5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -14.7224 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -13.8564 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -13.8564 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.9904 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.9904 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.1244 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.1244 0.0000 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 -0.8660 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 -5.1962 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 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 -1.7321 0.0000 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 0.0000 -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 -4.3301 -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 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 19 1 0 0 0 0 17 18 2 0 0 0 0 17 20 1 0 0 0 0 18 23 1 0 0 0 0 19 24 1 0 0 0 0 20 25 2 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 26 1 0 0 0 0 24 26 2 3 0 0 0 24 27 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	372.31
Volume:	432.705
LogP:	5.999
LogD:	4.263
LogS:	-2.756
# Rotatable Bonds:	18
TPSA:	41.99
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	1
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.243
Synthetic Accessibility Score:	2.176
Fsp3:	0.667
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.91
MDCK Permeability:	2.1147996449144557e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.016
20% Bioavailability (F20%):	0.986
30% Bioavailability (F30%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.473
Plasma Protein Binding (PPB):	97.88236236572266%
Volume Distribution (VD):	1.741
Pgp-substrate:	0.891804575920105%

ADMET: Metabolism

CYP1A2-inhibitor:	0.271
CYP1A2-substrate:	0.446
CYP2C19-inhibitor:	0.721
CYP2C19-substrate:	0.172
CYP2C9-inhibitor:	0.525
CYP2C9-substrate:	0.916
CYP2D6-inhibitor:	0.878
CYP2D6-substrate:	0.502
CYP3A4-inhibitor:	0.96
CYP3A4-substrate:	0.145

ADMET: Excretion

Clearance (CL):	5.56
Half-life (T1/2):	0.825

ADMET: Toxicity

hERG Blockers:	0.811
Human Hepatotoxicity (H-HT):	0.091
Drug-inuced Liver Injury (DILI):	0.026
AMES Toxicity:	0.008
Rat Oral Acute Toxicity:	0.061
Maximum Recommended Daily Dose:	0.051
Skin Sensitization:	0.963
Carcinogencity:	0.047
Eye Corrosion:	0.004
Eye Irritation:	0.043
Respiratory Toxicity:	0.733

Download Data

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

Natural Product: NPC471311

Natural Product ID:	NPC471311
*Common Name:**	N-(Pyridin-3-Ylmethyl)Oleamide
IUPAC Name:	(Z)-N-(pyridin-3-ylmethyl)octadec-9-enamide
Synonyms:
Standard InCHIKey:	ZAHBDLONEIBKSF-KTKRTIGZSA-N
Standard InCHI:	InChI=1S/C24H40N2O/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-19-24(27)26-22-23-18-17-20-25-21-23/h9-10,17-18,20-21H,2-8,11-16,19,22H2,1H3,(H,26,27)/b10-9-
SMILES:	CCCCCCCC/C=CCCCCCCCC(=NCc1cccnc1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2413169
PubChem CID:	71770311
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	3

Activity Type	# Activity
Individual Protein	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1418	Individual Protein	Anandamide amidohydrolase	Homo sapiens	IC50	=	7570.0	nM	PMID[529983]
NPT1418	Individual Protein	Anandamide amidohydrolase	Homo sapiens	Imax	=	90.0	%	PMID[529983]
NPT1418	Individual Protein	Anandamide amidohydrolase	Homo sapiens	Inhibition	=	56.8	%	PMID[529983]
NPT1418	Individual Protein	Anandamide amidohydrolase	Homo sapiens	Inhibition	=	81.2	%	PMID[529983]

☑ 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 NPC471311 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	261
0.1-0.2	3495
0.2-0.3	18670
0.3-0.4	13076
0.4-0.5	3769
0.5-0.6	2303
0.6-0.7	912
0.7-0.8	181
0.8-0.85	22
0.85-0.9	4
0.9-0.95	2
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC471313
0.9302	High Similarity	NPC471312
0.9062	High Similarity	NPC324611
0.888	High Similarity	NPC290094
0.8769	High Similarity	NPC471322
0.8672	High Similarity	NPC202957
0.8672	High Similarity	NPC169625
0.8548	High Similarity	NPC471402
0.8548	High Similarity	NPC297486
0.8548	High Similarity	NPC240136
0.8538	High Similarity	NPC89490
0.8473	Intermediate Similarity	NPC475105
0.8473	Intermediate Similarity	NPC329896
0.8473	Intermediate Similarity	NPC475090
0.8462	Intermediate Similarity	NPC212125
0.843	Intermediate Similarity	NPC27802
0.8425	Intermediate Similarity	NPC265605
0.8425	Intermediate Similarity	NPC182570
0.8425	Intermediate Similarity	NPC48564
0.8372	Intermediate Similarity	NPC476322
0.8345	Intermediate Similarity	NPC471323
0.8333	Intermediate Similarity	NPC76540
0.8271	Intermediate Similarity	NPC315320
0.8189	Intermediate Similarity	NPC91958
0.8182	Intermediate Similarity	NPC306397
0.8092	Intermediate Similarity	NPC27740
0.8077	Intermediate Similarity	NPC329825
0.8074	Intermediate Similarity	NPC256893
0.8069	Intermediate Similarity	NPC259644
0.8069	Intermediate Similarity	NPC469760
0.8069	Intermediate Similarity	NPC469786
0.8069	Intermediate Similarity	NPC25008
0.8069	Intermediate Similarity	NPC73952
0.8069	Intermediate Similarity	NPC469763
0.8069	Intermediate Similarity	NPC469765
0.806	Intermediate Similarity	NPC476131
0.8047	Intermediate Similarity	NPC143603
0.8045	Intermediate Similarity	NPC165370
0.803	Intermediate Similarity	NPC146373
0.803	Intermediate Similarity	NPC166424
0.803	Intermediate Similarity	NPC245244
0.8027	Intermediate Similarity	NPC129721
0.8015	Intermediate Similarity	NPC322488
0.8014	Intermediate Similarity	NPC70922
0.8014	Intermediate Similarity	NPC211572
0.8014	Intermediate Similarity	NPC80597
0.8014	Intermediate Similarity	NPC212376
0.8014	Intermediate Similarity	NPC75540
0.8	Intermediate Similarity	NPC69914
0.7971	Intermediate Similarity	NPC29702
0.7914	Intermediate Similarity	NPC65408
0.791	Intermediate Similarity	NPC278451
0.7867	Intermediate Similarity	NPC124542
0.7867	Intermediate Similarity	NPC59779
0.7867	Intermediate Similarity	NPC71079
0.7867	Intermediate Similarity	NPC471177
0.7857	Intermediate Similarity	NPC235843
0.7838	Intermediate Similarity	NPC469785
0.7833	Intermediate Similarity	NPC83987
0.7815	Intermediate Similarity	NPC474217
0.7785	Intermediate Similarity	NPC469762
0.7763	Intermediate Similarity	NPC85918
0.7763	Intermediate Similarity	NPC471178
0.7744	Intermediate Similarity	NPC46358
0.7742	Intermediate Similarity	NPC231655
0.7712	Intermediate Similarity	NPC127730
0.7712	Intermediate Similarity	NPC278366
0.7697	Intermediate Similarity	NPC311276
0.7681	Intermediate Similarity	NPC101165
0.766	Intermediate Similarity	NPC314102
0.766	Intermediate Similarity	NPC251722
0.7655	Intermediate Similarity	NPC314372
0.7647	Intermediate Similarity	NPC477975
0.7609	Intermediate Similarity	NPC282398
0.7597	Intermediate Similarity	NPC160105
0.7597	Intermediate Similarity	NPC98187
0.7589	Intermediate Similarity	NPC328029
0.7582	Intermediate Similarity	NPC469813
0.7582	Intermediate Similarity	NPC97367
0.7582	Intermediate Similarity	NPC476446
0.7582	Intermediate Similarity	NPC473057
0.7582	Intermediate Similarity	NPC78375
0.7568	Intermediate Similarity	NPC105818
0.7568	Intermediate Similarity	NPC24678
0.7552	Intermediate Similarity	NPC32002
0.7552	Intermediate Similarity	NPC315348
0.7552	Intermediate Similarity	NPC316811
0.7551	Intermediate Similarity	NPC477974
0.7517	Intermediate Similarity	NPC190296
0.75	Intermediate Similarity	NPC151489
0.7484	Intermediate Similarity	NPC474561
0.7484	Intermediate Similarity	NPC49954
0.7484	Intermediate Similarity	NPC108469
0.7468	Intermediate Similarity	NPC40779
0.7436	Intermediate Similarity	NPC201700
0.7413	Intermediate Similarity	NPC150259
0.7405	Intermediate Similarity	NPC314603
0.7403	Intermediate Similarity	NPC282231
0.7379	Intermediate Similarity	NPC469768
0.7379	Intermediate Similarity	NPC469779
0.7379	Intermediate Similarity	NPC469784
0.7379	Intermediate Similarity	NPC469761
0.7379	Intermediate Similarity	NPC469780
0.7379	Intermediate Similarity	NPC469783
0.7379	Intermediate Similarity	NPC469767
0.7372	Intermediate Similarity	NPC41717
0.7358	Intermediate Similarity	NPC469938
0.7355	Intermediate Similarity	NPC194640
0.7348	Intermediate Similarity	NPC476566
0.7338	Intermediate Similarity	NPC131718
0.7338	Intermediate Similarity	NPC279918
0.7338	Intermediate Similarity	NPC471589
0.7329	Intermediate Similarity	NPC469766
0.7329	Intermediate Similarity	NPC248462
0.7325	Intermediate Similarity	NPC63751
0.7315	Intermediate Similarity	NPC470111
0.7312	Intermediate Similarity	NPC203754
0.7312	Intermediate Similarity	NPC150048
0.7297	Intermediate Similarity	NPC159856
0.7296	Intermediate Similarity	NPC477976
0.7292	Intermediate Similarity	NPC114310
0.7273	Intermediate Similarity	NPC230869
0.7252	Intermediate Similarity	NPC473901
0.7219	Intermediate Similarity	NPC40070
0.72	Intermediate Similarity	NPC471957
0.7192	Intermediate Similarity	NPC73767
0.7192	Intermediate Similarity	NPC110126
0.7181	Intermediate Similarity	NPC285731
0.7181	Intermediate Similarity	NPC167400
0.7172	Intermediate Similarity	NPC84911
0.7172	Intermediate Similarity	NPC105127
0.7164	Intermediate Similarity	NPC81561
0.716	Intermediate Similarity	NPC64436
0.716	Intermediate Similarity	NPC248454
0.7152	Intermediate Similarity	NPC54988
0.7143	Intermediate Similarity	NPC84268
0.7134	Intermediate Similarity	NPC102423
0.7134	Intermediate Similarity	NPC233936
0.7133	Intermediate Similarity	NPC330326
0.7123	Intermediate Similarity	NPC169433
0.7115	Intermediate Similarity	NPC25899
0.7103	Intermediate Similarity	NPC96102
0.7103	Intermediate Similarity	NPC29886
0.7103	Intermediate Similarity	NPC261195
0.7097	Intermediate Similarity	NPC138018
0.7097	Intermediate Similarity	NPC213774
0.7095	Intermediate Similarity	NPC476454
0.709	Intermediate Similarity	NPC148140
0.7081	Intermediate Similarity	NPC313791
0.7075	Intermediate Similarity	NPC104483
0.7073	Intermediate Similarity	NPC300688
0.7073	Intermediate Similarity	NPC471997
0.7067	Intermediate Similarity	NPC86288
0.7067	Intermediate Similarity	NPC467188
0.7066	Intermediate Similarity	NPC474707
0.7063	Intermediate Similarity	NPC174421
0.7063	Intermediate Similarity	NPC82295
0.7063	Intermediate Similarity	NPC314940
0.7063	Intermediate Similarity	NPC473764
0.7059	Intermediate Similarity	NPC11863
0.7059	Intermediate Similarity	NPC470233
0.7055	Intermediate Similarity	NPC151939
0.7055	Intermediate Similarity	NPC59269
0.7051	Intermediate Similarity	NPC92796
0.7051	Intermediate Similarity	NPC135141
0.7047	Intermediate Similarity	NPC477977
0.7032	Intermediate Similarity	NPC476464
0.7029	Intermediate Similarity	NPC56856
0.7025	Intermediate Similarity	NPC478182
0.7012	Intermediate Similarity	NPC213468
0.7	Intermediate Similarity	NPC230085
0.7	Intermediate Similarity	NPC159630
0.7	Intermediate Similarity	NPC78020
0.7	Intermediate Similarity	NPC473763
0.7	Intermediate Similarity	NPC117244
0.6994	Remote Similarity	NPC267885
0.6988	Remote Similarity	NPC163055
0.6982	Remote Similarity	NPC173028
0.6982	Remote Similarity	NPC65215
0.6974	Remote Similarity	NPC179787
0.6974	Remote Similarity	NPC201380
0.6974	Remote Similarity	NPC105811
0.6968	Remote Similarity	NPC209362
0.6968	Remote Similarity	NPC263455
0.6964	Remote Similarity	NPC94752
0.6962	Remote Similarity	NPC48192
0.6957	Remote Similarity	NPC194411
0.695	Remote Similarity	NPC135488
0.6948	Remote Similarity	NPC216713
0.6948	Remote Similarity	NPC70406
0.6941	Remote Similarity	NPC95783
0.6933	Remote Similarity	NPC110500
0.6933	Remote Similarity	NPC149155
0.6933	Remote Similarity	NPC203468
0.6928	Remote Similarity	NPC321911
0.6923	Remote Similarity	NPC317030
0.6923	Remote Similarity	NPC285469
0.6923	Remote Similarity	NPC51054
0.6923	Remote Similarity	NPC204565
0.6914	Remote Similarity	NPC158129

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 NPC471311 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	183
0.1-0.2	620
0.2-0.3	1056
0.3-0.4	1487
0.4-0.5	3092
0.5-0.6	1962
0.6-0.7	599
0.7-0.8	135
0.8-0.85	16
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.854	High Similarity	NPD3717	Discontinued
0.8538	High Similarity	NPD1095	Clinical (unspecified phase)
0.8519	High Similarity	NPD2896	Discontinued
0.8489	Intermediate Similarity	NPD6148	Clinical (unspecified phase)
0.8462	Intermediate Similarity	NPD9284	Approved
0.8443	Intermediate Similarity	NPD4823	Approved
0.8443	Intermediate Similarity	NPD4824	Approved
0.8429	Intermediate Similarity	NPD4703	Approved
0.8429	Intermediate Similarity	NPD4702	Approved
0.8425	Intermediate Similarity	NPD271	Approved
0.8425	Intermediate Similarity	NPD270	Clinical (unspecified phase)
0.8425	Intermediate Similarity	NPD268	Approved
0.8271	Intermediate Similarity	NPD9207	Approved
0.8271	Intermediate Similarity	NPD9206	Approved
0.824	Intermediate Similarity	NPD269	Clinical (unspecified phase)
0.8214	Intermediate Similarity	NPD3813	Approved
0.8214	Intermediate Similarity	NPD751	Clinical (unspecified phase)
0.8182	Intermediate Similarity	NPD2118	Approved
0.8182	Intermediate Similarity	NPD9080	Approved
0.8182	Intermediate Similarity	NPD2119	Approved
0.8125	Intermediate Similarity	NPD3262	Approved
0.8071	Intermediate Similarity	NPD4805	Approved
0.8	Intermediate Similarity	NPD3476	Approved
0.8	Intermediate Similarity	NPD3475	Approved
0.8	Intermediate Similarity	NPD1649	Discontinued
0.7987	Intermediate Similarity	NPD8026	Phase 1
0.7973	Intermediate Similarity	NPD5255	Approved
0.7972	Intermediate Similarity	NPD7469	Discontinued
0.797	Intermediate Similarity	NPD9583	Approved
0.7959	Intermediate Similarity	NPD6026	Approved
0.7955	Intermediate Similarity	NPD9357	Approved
0.7945	Intermediate Similarity	NPD2012	Clinical (unspecified phase)
0.7929	Intermediate Similarity	NPD4804	Approved
0.7919	Intermediate Similarity	NPD2511	Approved
0.7914	Intermediate Similarity	NPD9506	Approved
0.7914	Intermediate Similarity	NPD201	Phase 2
0.7914	Intermediate Similarity	NPD200	Phase 2
0.791	Intermediate Similarity	NPD992	Clinical (unspecified phase)
0.791	Intermediate Similarity	NPD991	Phase 2
0.791	Intermediate Similarity	NPD1598	Discontinued
0.7905	Intermediate Similarity	NPD5541	Clinical (unspecified phase)
0.7883	Intermediate Similarity	NPD1993	Approved
0.7883	Intermediate Similarity	NPD1627	Clinical (unspecified phase)
0.7883	Intermediate Similarity	NPD1995	Approved
0.7883	Intermediate Similarity	NPD1994	Approved
0.7857	Intermediate Similarity	NPD203	Clinical (unspecified phase)
0.7832	Intermediate Similarity	NPD1352	Discontinued
0.7829	Intermediate Similarity	NPD9396	Approved
0.7829	Intermediate Similarity	NPD9392	Approved
0.7826	Intermediate Similarity	NPD4029	Approved
0.7826	Intermediate Similarity	NPD3944	Approved
0.7826	Intermediate Similarity	NPD4030	Approved
0.7826	Intermediate Similarity	NPD4028	Approved
0.7826	Intermediate Similarity	NPD3942	Approved
0.7803	Intermediate Similarity	NPD748	Clinical (unspecified phase)
0.7793	Intermediate Similarity	NPD1661	Suspended
0.777	Intermediate Similarity	NPD2809	Approved
0.7742	Intermediate Similarity	NPD9099	Clinical (unspecified phase)
0.7742	Intermediate Similarity	NPD9098	Phase 3
0.7737	Intermediate Similarity	NPD715	Phase 3
0.7714	Intermediate Similarity	NPD792	Discontinued
0.7697	Intermediate Similarity	NPD5088	Discontinued
0.7681	Intermediate Similarity	NPD9726	Discontinued
0.7677	Intermediate Similarity	NPD5934	Clinical (unspecified phase)
0.7667	Intermediate Similarity	NPD2581	Approved
0.7667	Intermediate Similarity	NPD2582	Approved
0.7662	Intermediate Similarity	NPD6872	Clinical (unspecified phase)
0.7651	Intermediate Similarity	NPD5358	Clinical (unspecified phase)
0.7643	Intermediate Similarity	NPD272	Approved
0.7643	Intermediate Similarity	NPD2141	Approved
0.7643	Intermediate Similarity	NPD2140	Approved
0.7643	Intermediate Similarity	NPD2142	Approved
0.7606	Intermediate Similarity	NPD1380	Discovery
0.7595	Intermediate Similarity	NPD8123	Approved
0.7595	Intermediate Similarity	NPD8122	Approved
0.7589	Intermediate Similarity	NPD206	Clinical (unspecified phase)
0.7552	Intermediate Similarity	NPD2068	Approved
0.7552	Intermediate Similarity	NPD2071	Approved
0.7552	Intermediate Similarity	NPD2074	Approved
0.7552	Intermediate Similarity	NPD2072	Approved
0.7552	Intermediate Similarity	NPD2075	Approved
0.7552	Intermediate Similarity	NPD2073	Approved
0.7552	Intermediate Similarity	NPD2070	Approved
0.7552	Intermediate Similarity	NPD2069	Approved
0.7548	Intermediate Similarity	NPD5862	Discovery
0.7532	Intermediate Similarity	NPD6375	Clinical (unspecified phase)
0.7517	Intermediate Similarity	NPD1427	Clinical (unspecified phase)
0.7517	Intermediate Similarity	NPD2006	Phase 2
0.75	Intermediate Similarity	NPD2620	Phase 2
0.75	Intermediate Similarity	NPD3576	Approved
0.75	Intermediate Similarity	NPD3575	Approved
0.75	Intermediate Similarity	NPD2619	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD5611	Phase 2
0.7468	Intermediate Similarity	NPD6635	Approved
0.7468	Intermediate Similarity	NPD5925	Phase 1
0.7468	Intermediate Similarity	NPD5322	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD5065	Approved
0.7464	Intermediate Similarity	NPD5352	Clinical (unspecified phase)
0.7448	Intermediate Similarity	NPD1382	Phase 2
0.7448	Intermediate Similarity	NPD1383	Phase 3
0.7432	Intermediate Similarity	NPD2089	Clinical (unspecified phase)
0.7421	Intermediate Similarity	NPD5100	Phase 3
0.7419	Intermediate Similarity	NPD925	Approved
0.7419	Intermediate Similarity	NPD926	Approved
0.7417	Intermediate Similarity	NPD2061	Approved
0.7403	Intermediate Similarity	NPD4239	Clinical (unspecified phase)
0.74	Intermediate Similarity	NPD2882	Phase 1
0.74	Intermediate Similarity	NPD5965	Clinical (unspecified phase)
0.7397	Intermediate Similarity	NPD4510	Discontinued
0.7389	Intermediate Similarity	NPD4184	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD604	Clinical (unspecified phase)
0.7383	Intermediate Similarity	NPD1183	Approved
0.7379	Intermediate Similarity	NPD1395	Clinical (unspecified phase)
0.7375	Intermediate Similarity	NPD5751	Clinical (unspecified phase)
0.7355	Intermediate Similarity	NPD8129	Discovery
0.7346	Intermediate Similarity	NPD8408	Discontinued
0.7315	Intermediate Similarity	NPD1270	Approved
0.7315	Intermediate Similarity	NPD4547	Phase 3
0.7305	Intermediate Similarity	NPD803	Phase 1
0.7285	Intermediate Similarity	NPD6476	Clinical (unspecified phase)
0.7285	Intermediate Similarity	NPD9706	Clinical (unspecified phase)
0.7285	Intermediate Similarity	NPD6158	Phase 2
0.7279	Intermediate Similarity	NPD2007	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD2430	Phase 2
0.7261	Intermediate Similarity	NPD425	Approved
0.7261	Intermediate Similarity	NPD424	Approved
0.7261	Intermediate Similarity	NPD4174	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD2323	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD7414	Clinical (unspecified phase)
0.723	Intermediate Similarity	NPD1918	Clinical (unspecified phase)
0.7229	Intermediate Similarity	NPD8020	Approved
0.7229	Intermediate Similarity	NPD8021	Approved
0.7222	Intermediate Similarity	NPD8037	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD8036	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD7913	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD3082	Discontinued
0.7212	Intermediate Similarity	NPD6610	Clinical (unspecified phase)
0.7211	Intermediate Similarity	NPD5020	Approved
0.7211	Intermediate Similarity	NPD1722	Approved
0.7206	Intermediate Similarity	NPD9598	Discontinued
0.7203	Intermediate Similarity	NPD3385	Approved
0.7195	Intermediate Similarity	NPD5728	Clinical (unspecified phase)
0.7192	Intermediate Similarity	NPD786	Approved
0.7192	Intermediate Similarity	NPD768	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD2077	Approved
0.7188	Intermediate Similarity	NPD2076	Approved
0.7181	Intermediate Similarity	NPD9074	Approved
0.7181	Intermediate Similarity	NPD9075	Approved
0.7181	Intermediate Similarity	NPD175	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD6771	Discontinued
0.7171	Intermediate Similarity	NPD4641	Discontinued
0.7171	Intermediate Similarity	NPD510	Phase 1
0.7163	Intermediate Similarity	NPD3654	Approved
0.7161	Intermediate Similarity	NPD3433	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD2748	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD9599	Approved
0.7143	Intermediate Similarity	NPD60	Approved
0.7133	Intermediate Similarity	NPD9100	Approved
0.7125	Intermediate Similarity	NPD3116	Approved
0.7125	Intermediate Similarity	NPD3117	Approved
0.7123	Intermediate Similarity	NPD9076	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD1620	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD5555	Phase 1
0.7108	Intermediate Similarity	NPD6241	Phase 1
0.7107	Intermediate Similarity	NPD2781	Approved
0.7107	Intermediate Similarity	NPD4638	Approved
0.7107	Intermediate Similarity	NPD7287	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD4640	Approved
0.7107	Intermediate Similarity	NPD4639	Approved
0.7105	Intermediate Similarity	NPD2465	Approved
0.7105	Intermediate Similarity	NPD2462	Phase 3
0.7105	Intermediate Similarity	NPD2466	Phase 3
0.7103	Intermediate Similarity	NPD198	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD4669	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD4671	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD4670	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD5213	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD2391	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD2782	Approved
0.7089	Intermediate Similarity	NPD2780	Approved
0.7086	Intermediate Similarity	NPD2110	Approved
0.7083	Intermediate Similarity	NPD6363	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD750	Phase 2
0.7078	Intermediate Similarity	NPD2165	Phase 1
0.7073	Intermediate Similarity	NPD6595	Phase 3
0.707	Intermediate Similarity	NPD4384	Clinical (unspecified phase)
0.7066	Intermediate Similarity	NPD4375	Approved
0.7063	Intermediate Similarity	NPD809	Discontinued
0.7055	Intermediate Similarity	NPD2144	Approved
0.7051	Intermediate Similarity	NPD704	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD6178	Phase 3
0.7047	Intermediate Similarity	NPD3525	Discontinued
0.7041	Intermediate Similarity	NPD8063	Discontinued
0.7037	Intermediate Similarity	NPD8840	Approved
0.7037	Intermediate Similarity	NPD2928	Phase 2
0.7032	Intermediate Similarity	NPD3114	Approved
0.7032	Intermediate Similarity	NPD3112	Approved
0.7032	Intermediate Similarity	NPD3113	Approved
0.7032	Intermediate Similarity	NPD3115	Approved
0.7029	Intermediate Similarity	NPD5787	Discontinued

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