NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	162.12
Volume:	178.488
LogP:	0.672
LogD:	0.844
LogS:	0.613
# Rotatable Bonds:	1
TPSA:	16.13
# H-Bond Aceptor:	2
# H-Bond Donor:	0
# Rings:	2
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.626
Synthetic Accessibility Score:	2.5
Fsp3:	0.5
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.231
MDCK Permeability:	1.890912426461e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.007
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.02
30% Bioavailability (F30%):	0.424

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.974
Plasma Protein Binding (PPB):	22.25753402709961%
Volume Distribution (VD):	2.609
Pgp-substrate:	77.29618835449219%

ADMET: Metabolism

CYP1A2-inhibitor:	0.143
CYP1A2-substrate:	0.861
CYP2C19-inhibitor:	0.129
CYP2C19-substrate:	0.943
CYP2C9-inhibitor:	0.018
CYP2C9-substrate:	0.5
CYP2D6-inhibitor:	0.173
CYP2D6-substrate:	0.894
CYP3A4-inhibitor:	0.199
CYP3A4-substrate:	0.684

ADMET: Excretion

Clearance (CL):	14.816
Half-life (T1/2):	0.727

ADMET: Toxicity

hERG Blockers:	0.052
Human Hepatotoxicity (H-HT):	0.191
Drug-inuced Liver Injury (DILI):	0.061
AMES Toxicity:	0.01
Rat Oral Acute Toxicity:	0.829
Maximum Recommended Daily Dose:	0.915
Skin Sensitization:	0.915
Carcinogencity:	0.143
Eye Corrosion:	0.01
Eye Irritation:	0.063
Respiratory Toxicity:	0.946

Download Data

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

Natural Product: NPC265605

Natural Product ID:	NPC265605
*Common Name:**	R-Nicotine
IUPAC Name:	3-[(2R)-1-methylpyrrolidin-2-yl]pyridine
Synonyms:	(R)-(+)-Nicotine
Standard InCHIKey:	SNICXCGAKADSCV-SNVBAGLBSA-N
Standard InCHI:	InChI=1S/C10H14N2/c1-12-7-3-5-10(12)9-4-2-6-11-8-9/h2,4,6,8,10H,3,5,7H2,1H3/p+1/t10-/m1/s1
SMILES:	CN1CCC[C@@H]1c1ccc[nH+]c1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL9732
PubChem CID:	157672
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000089] Pyridines and derivatives [CHEMONTID:0001975] Pyrrolidinylpyridines

*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
NPO28928	Piper nigrum	Species	Piperaceae	Eukaryota	n.a.	fruit	n.a.	DOI[10.1016/S0040-4039(01)00209-X]
NPO28928	Piper nigrum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10575373]
NPO28928	Piper nigrum	Species	Piperaceae	Eukaryota	n.a.	leaf	n.a.	PMID[15467205]
NPO28928	Piper nigrum	Species	Piperaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[16808005]
NPO28928	Piper nigrum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23102654]
NPO28928	Piper nigrum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31103896]
NPO28928	Piper nigrum	Species	Piperaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO28928	Piper nigrum	Species	Piperaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO28928	Piper nigrum	Species	Piperaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO28928	Piper nigrum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28928	Piper nigrum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28928	Piper nigrum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO28928	Piper nigrum	Species	Piperaceae	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
AC50	2
ED50	4
IC50	4
Ki	9
Others	18
Potency	10

Activity Type	# Activity
Individual Protein	10
NON-MOLECULAR	10
Organism	8
Others	14
Protein Complex	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT240	Individual Protein	Cytochrome P450 2A6	Homo sapiens	IC50	=	580000.0	nM	PMID[550658]
NPT1420	Individual Protein	Cytochrome P450 2A5	Mus musculus	IC50	=	160000.0	nM	PMID[550658]
NPT483	Individual Protein	Prelamin-A/C	Homo sapiens	Potency	=	4.5	nM	PMID[550660]
NPT50	Individual Protein	Tyrosyl-DNA phosphodiesterase 1	Homo sapiens	Potency	=	141.3	nM	PMID[550660]
NPT443	Individual Protein	Histone acetyltransferase GCN5	Homo sapiens	Potency	n.a.	35481.3	nM	PMID[550660]
NPT1304	Individual Protein	Nicotinic acetylcholine receptor alpha 5 subunit	Musca domestica	IC50	=	422000.0	nM	PMID[550661]
NPT1304	Individual Protein	Nicotinic acetylcholine receptor alpha 5 subunit	Musca domestica	Activity	=	422.0	uM	PMID[550662]
NPT3925	Individual Protein	Acetylcholine receptor protein alpha chain	Torpedo californica	IC50	=	54400.0	nM	PMID[550663]
NPT413	Protein Complex	Neuronal acetylcholine receptor	Rattus norvegicus	Ki	=	16.0	nM	PMID[550654]
NPT413	Protein Complex	Neuronal acetylcholine receptor	Rattus norvegicus	Dopamine release	=	114.0	%	PMID[550654]
NPT412	Protein Complex	Neuronal acetylcholine receptor; alpha4/beta2	Rattus norvegicus	Ki	=	38.0	nM	PMID[550655]
NPT412	Protein Complex	Neuronal acetylcholine receptor; alpha4/beta2	Rattus norvegicus	Ki	=	87.0	nM	PMID[550656]
NPT2	Others	Unspecified		Ki	=	16.0	nM	PMID[550657]
NPT2	Others	Unspecified		Ki	=	32.0	nM	PMID[550657]
NPT2	Others	Unspecified		Ki	>	20000.0	nM	PMID[550657]
NPT2	Others	Unspecified		Ki	=	1500.0	nM	PMID[550657]
NPT27	Others	Unspecified		Ratio	=	3.8	n.a.	PMID[550658]
NPT412	Protein Complex	Neuronal acetylcholine receptor; alpha4/beta2	Rattus norvegicus	Ki	=	35.0	nM	PMID[550659]
NPT32	Organism	Mus musculus	Mus musculus	ED50	=	8.0	mg.kg-1	PMID[550659]
NPT32	Organism	Mus musculus	Mus musculus	ED50	=	3.9	mg.kg-1	PMID[550659]
NPT32	Organism	Mus musculus	Mus musculus	ED50	=	7.6	mg.kg-1	PMID[550659]
NPT32	Organism	Mus musculus	Mus musculus	ED50	=	2.9	mg.kg-1	PMID[550659]
NPT94	Individual Protein	Aldehyde dehydrogenase 1A1	Homo sapiens	Potency	=	4466.8	nM	PMID[550660]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Potency	n.a.	15101.4	nM	PMID[550660]
NPT2	Others	Unspecified		Potency	n.a.	20587.8	nM	PMID[550660]
NPT734	Organism	Musca domestica	Musca domestica	Activity	=	40.0	%	PMID[550662]
NPT26271	ORGANISM	Periplaneta americana	Periplaneta americana	MLD	=	160.0	nmol	PMID[550662]
NPT26271	ORGANISM	Periplaneta americana	Periplaneta americana	MLD	=	320.0	nmol	PMID[550662]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	66.4	%	PMID[550664]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	57.3	%	PMID[550664]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	61.5	%	PMID[550664]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	66.5	%	PMID[550664]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	68.1	%	PMID[550664]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	65.4	%	PMID[550664]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	65.8	%	PMID[550664]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	67.1	%	PMID[550664]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	63.8	%	PMID[550664]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	64.6	%	PMID[550664]
NPT2	Others	Unspecified		Potency	n.a.	14125.4	nM	PMID[550665]
NPT2	Others	Unspecified		Ac50	n.a.	0.631	uM	PMID[550666]
NPT2	Others	Unspecified		AC50	n.a.	631.0	nM	PMID[550666]
NPT2	Others	Unspecified		Potency	n.a.	26832.5	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	23710.1	nM	PubChem BioAssay data set
NPT74	Individual Protein	Proto-oncogene c-JUN	Homo sapiens	Potency	n.a.	190	nM	PubChem BioAssay data set

☑ 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 NPC265605 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	978
0.1-0.2	12252
0.2-0.3	18663
0.3-0.4	5188
0.4-0.5	2808
0.5-0.6	1890
0.6-0.7	670
0.7-0.8	200
0.8-0.85	32
0.85-0.9	12
0.9-0.95	1
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC182570
1.0	High Similarity	NPC48564
0.9412	High Similarity	NPC27740
0.9035	High Similarity	NPC27802
0.8983	High Similarity	NPC297486
0.8983	High Similarity	NPC471402
0.8983	High Similarity	NPC240136
0.8862	High Similarity	NPC166424
0.8862	High Similarity	NPC146373
0.8862	High Similarity	NPC245244
0.8837	High Similarity	NPC65408
0.8772	High Similarity	NPC76540
0.875	High Similarity	NPC91958
0.8699	High Similarity	NPC290094
0.8629	High Similarity	NPC476322
0.8595	High Similarity	NPC143603
0.8594	High Similarity	NPC324611
0.8492	Intermediate Similarity	NPC169625
0.8492	Intermediate Similarity	NPC202957
0.8425	Intermediate Similarity	NPC471311
0.8425	Intermediate Similarity	NPC471313
0.8403	Intermediate Similarity	NPC235843
0.84	Intermediate Similarity	NPC46358
0.8359	Intermediate Similarity	NPC89490
0.832	Intermediate Similarity	NPC329825
0.8295	Intermediate Similarity	NPC475090
0.8295	Intermediate Similarity	NPC475105
0.8295	Intermediate Similarity	NPC329896
0.8295	Intermediate Similarity	NPC476131
0.8291	Intermediate Similarity	NPC231655
0.8284	Intermediate Similarity	NPC110126
0.8271	Intermediate Similarity	NPC150259
0.8246	Intermediate Similarity	NPC83987
0.8231	Intermediate Similarity	NPC282398
0.8231	Intermediate Similarity	NPC69914
0.8168	Intermediate Similarity	NPC101165
0.8168	Intermediate Similarity	NPC471322
0.8162	Intermediate Similarity	NPC476454
0.8148	Intermediate Similarity	NPC73767
0.8143	Intermediate Similarity	NPC40070
0.8134	Intermediate Similarity	NPC84911
0.8134	Intermediate Similarity	NPC105127
0.8134	Intermediate Similarity	NPC251722
0.8134	Intermediate Similarity	NPC314102
0.813	Intermediate Similarity	NPC476566
0.806	Intermediate Similarity	NPC29886
0.806	Intermediate Similarity	NPC261195
0.806	Intermediate Similarity	NPC96102
0.803	Intermediate Similarity	NPC256893
0.803	Intermediate Similarity	NPC82295
0.8015	Intermediate Similarity	NPC316811
0.8015	Intermediate Similarity	NPC32002
0.8015	Intermediate Similarity	NPC315348
0.7956	Intermediate Similarity	NPC469784
0.7956	Intermediate Similarity	NPC469761
0.7956	Intermediate Similarity	NPC469768
0.7956	Intermediate Similarity	NPC469767
0.7956	Intermediate Similarity	NPC469783
0.7956	Intermediate Similarity	NPC469779
0.7956	Intermediate Similarity	NPC469780
0.7899	Intermediate Similarity	NPC469766
0.7872	Intermediate Similarity	NPC470111
0.7872	Intermediate Similarity	NPC201380
0.7872	Intermediate Similarity	NPC179787
0.7868	Intermediate Similarity	NPC471312
0.7857	Intermediate Similarity	NPC285731
0.7842	Intermediate Similarity	NPC190296
0.7832	Intermediate Similarity	NPC470233
0.7826	Intermediate Similarity	NPC279081
0.7817	Intermediate Similarity	NPC321911
0.7801	Intermediate Similarity	NPC63545
0.7746	Intermediate Similarity	NPC469811
0.773	Intermediate Similarity	NPC314372
0.773	Intermediate Similarity	NPC86288
0.7727	Intermediate Similarity	NPC212125
0.7721	Intermediate Similarity	NPC198988
0.7714	Intermediate Similarity	NPC20144
0.7698	Intermediate Similarity	NPC148140
0.7698	Intermediate Similarity	NPC230002
0.7687	Intermediate Similarity	NPC56765
0.7681	Intermediate Similarity	NPC169433
0.7664	Intermediate Similarity	NPC325252
0.7643	Intermediate Similarity	NPC473868
0.7643	Intermediate Similarity	NPC63157
0.7638	Intermediate Similarity	NPC81561
0.7626	Intermediate Similarity	NPC104483
0.7622	Intermediate Similarity	NPC471957
0.7619	Intermediate Similarity	NPC129721
0.7607	Intermediate Similarity	NPC213774
0.7606	Intermediate Similarity	NPC159856
0.76	Intermediate Similarity	NPC473901
0.7571	Intermediate Similarity	NPC59084
0.7568	Intermediate Similarity	NPC477591
0.7556	Intermediate Similarity	NPC315320
0.7552	Intermediate Similarity	NPC288838
0.7552	Intermediate Similarity	NPC143872
0.7551	Intermediate Similarity	NPC51054
0.7551	Intermediate Similarity	NPC476464
0.7534	Intermediate Similarity	NPC200214
0.7534	Intermediate Similarity	NPC325903
0.7517	Intermediate Similarity	NPC53947
0.7517	Intermediate Similarity	NPC24678
0.7517	Intermediate Similarity	NPC105818
0.75	Intermediate Similarity	NPC88097
0.75	Intermediate Similarity	NPC236711
0.7483	Intermediate Similarity	NPC34844
0.7481	Intermediate Similarity	NPC41174
0.748	Intermediate Similarity	NPC84268
0.7466	Intermediate Similarity	NPC470823
0.7463	Intermediate Similarity	NPC306397
0.7462	Intermediate Similarity	NPC215519
0.745	Intermediate Similarity	NPC206819
0.745	Intermediate Similarity	NPC293487
0.745	Intermediate Similarity	NPC318065
0.7447	Intermediate Similarity	NPC2949
0.7442	Intermediate Similarity	NPC162689
0.7442	Intermediate Similarity	NPC54102
0.7426	Intermediate Similarity	NPC22079
0.7417	Intermediate Similarity	NPC478184
0.7417	Intermediate Similarity	NPC90723
0.7417	Intermediate Similarity	NPC478182
0.7415	Intermediate Similarity	NPC138842
0.7415	Intermediate Similarity	NPC469763
0.7415	Intermediate Similarity	NPC141926
0.7415	Intermediate Similarity	NPC25008
0.7415	Intermediate Similarity	NPC73952
0.7415	Intermediate Similarity	NPC259644
0.7415	Intermediate Similarity	NPC469765
0.7415	Intermediate Similarity	NPC469786
0.7415	Intermediate Similarity	NPC469760
0.7413	Intermediate Similarity	NPC471323
0.74	Intermediate Similarity	NPC215584
0.74	Intermediate Similarity	NPC44773
0.7397	Intermediate Similarity	NPC473878
0.7379	Intermediate Similarity	NPC477974
0.7379	Intermediate Similarity	NPC21605
0.7365	Intermediate Similarity	NPC75540
0.7365	Intermediate Similarity	NPC211572
0.7365	Intermediate Similarity	NPC80597
0.7365	Intermediate Similarity	NPC212376
0.7365	Intermediate Similarity	NPC70922
0.7347	Intermediate Similarity	NPC216713
0.7333	Intermediate Similarity	NPC41257
0.7333	Intermediate Similarity	NPC165370
0.7324	Intermediate Similarity	NPC115611
0.7319	Intermediate Similarity	NPC322488
0.731	Intermediate Similarity	NPC316069
0.7303	Intermediate Similarity	NPC317105
0.729	Intermediate Similarity	NPC82331
0.7286	Intermediate Similarity	NPC29702
0.7286	Intermediate Similarity	NPC218268
0.7285	Intermediate Similarity	NPC470204
0.7285	Intermediate Similarity	NPC122141
0.7279	Intermediate Similarity	NPC471589
0.7267	Intermediate Similarity	NPC286427
0.7267	Intermediate Similarity	NPC469897
0.7252	Intermediate Similarity	NPC11863
0.7241	Intermediate Similarity	NPC467188
0.7241	Intermediate Similarity	NPC470440
0.7239	Intermediate Similarity	NPC122718
0.7237	Intermediate Similarity	NPC470203
0.7237	Intermediate Similarity	NPC124542
0.7237	Intermediate Similarity	NPC282231
0.7237	Intermediate Similarity	NPC59779
0.7237	Intermediate Similarity	NPC478185
0.7237	Intermediate Similarity	NPC471177
0.7237	Intermediate Similarity	NPC225018
0.7234	Intermediate Similarity	NPC125746
0.723	Intermediate Similarity	NPC470679
0.723	Intermediate Similarity	NPC472260
0.723	Intermediate Similarity	NPC217021
0.7226	Intermediate Similarity	NPC91895
0.7218	Intermediate Similarity	NPC56856
0.7208	Intermediate Similarity	NPC98187
0.7208	Intermediate Similarity	NPC478183
0.7208	Intermediate Similarity	NPC56233
0.72	Intermediate Similarity	NPC469785
0.7194	Intermediate Similarity	NPC330326
0.719	Intermediate Similarity	NPC78375
0.719	Intermediate Similarity	NPC469813
0.719	Intermediate Similarity	NPC476446
0.7171	Intermediate Similarity	NPC279918
0.7162	Intermediate Similarity	NPC33421
0.7152	Intermediate Similarity	NPC474958
0.7152	Intermediate Similarity	NPC216643
0.7152	Intermediate Similarity	NPC469762
0.7152	Intermediate Similarity	NPC280852
0.7143	Intermediate Similarity	NPC105811
0.7143	Intermediate Similarity	NPC274229
0.7143	Intermediate Similarity	NPC100726
0.7133	Intermediate Similarity	NPC476219
0.7133	Intermediate Similarity	NPC476297
0.7133	Intermediate Similarity	NPC477815
0.7132	Intermediate Similarity	NPC250361
0.7132	Intermediate Similarity	NPC135488
0.7132	Intermediate Similarity	NPC476140
0.7123	Intermediate Similarity	NPC204141
0.7123	Intermediate Similarity	NPC469525
0.7115	Intermediate Similarity	NPC32534
0.7115	Intermediate Similarity	NPC194411

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 NPC265605 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	354
0.1-0.2	838
0.2-0.3	1047
0.3-0.4	1852
0.4-0.5	2671
0.5-0.6	1667
0.6-0.7	559
0.7-0.8	125
0.8-0.85	26
0.85-0.9	8
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Drug ID	Developmental Stage
1.0	High Similarity	NPD270	Clinical (unspecified phase)
1.0	High Similarity	NPD271	Approved
1.0	High Similarity	NPD268	Approved
0.9244	High Similarity	NPD748	Clinical (unspecified phase)
0.896	High Similarity	NPD3475	Approved
0.896	High Similarity	NPD3476	Approved
0.8837	High Similarity	NPD201	Phase 2
0.8837	High Similarity	NPD200	Phase 2
0.872	High Similarity	NPD2119	Approved
0.872	High Similarity	NPD2118	Approved
0.872	High Similarity	NPD992	Clinical (unspecified phase)
0.872	High Similarity	NPD991	Phase 2
0.8655	High Similarity	NPD269	Clinical (unspecified phase)
0.864	High Similarity	NPD9583	Approved
0.8629	High Similarity	NPD9357	Approved
0.8559	High Similarity	NPD4824	Approved
0.8559	High Similarity	NPD4823	Approved
0.8462	Intermediate Similarity	NPD4030	Approved
0.8462	Intermediate Similarity	NPD4028	Approved
0.8462	Intermediate Similarity	NPD4029	Approved
0.8425	Intermediate Similarity	NPD1598	Discontinued
0.8387	Intermediate Similarity	NPD9598	Discontinued
0.8361	Intermediate Similarity	NPD9392	Approved
0.8361	Intermediate Similarity	NPD9396	Approved
0.8321	Intermediate Similarity	NPD3942	Approved
0.8321	Intermediate Similarity	NPD3944	Approved
0.8308	Intermediate Similarity	NPD803	Phase 1
0.8291	Intermediate Similarity	NPD9099	Clinical (unspecified phase)
0.8291	Intermediate Similarity	NPD9098	Phase 3
0.8284	Intermediate Similarity	NPD768	Clinical (unspecified phase)
0.8244	Intermediate Similarity	NPD1995	Approved
0.8244	Intermediate Similarity	NPD1994	Approved
0.8244	Intermediate Similarity	NPD1993	Approved
0.8235	Intermediate Similarity	NPD2006	Phase 2
0.8231	Intermediate Similarity	NPD715	Phase 3
0.8148	Intermediate Similarity	NPD786	Approved
0.8129	Intermediate Similarity	NPD4547	Phase 3
0.806	Intermediate Similarity	NPD198	Clinical (unspecified phase)
0.806	Intermediate Similarity	NPD206	Clinical (unspecified phase)
0.8045	Intermediate Similarity	NPD3385	Approved
0.8029	Intermediate Similarity	NPD1722	Approved
0.8015	Intermediate Similarity	NPD2070	Approved
0.8015	Intermediate Similarity	NPD2073	Approved
0.8015	Intermediate Similarity	NPD2068	Approved
0.8015	Intermediate Similarity	NPD2072	Approved
0.8015	Intermediate Similarity	NPD2071	Approved
0.8015	Intermediate Similarity	NPD3654	Approved
0.8015	Intermediate Similarity	NPD2069	Approved
0.8015	Intermediate Similarity	NPD2074	Approved
0.8015	Intermediate Similarity	NPD2075	Approved
0.7985	Intermediate Similarity	NPD2142	Approved
0.7985	Intermediate Similarity	NPD2140	Approved
0.7985	Intermediate Similarity	NPD2141	Approved
0.797	Intermediate Similarity	NPD1627	Clinical (unspecified phase)
0.7943	Intermediate Similarity	NPD2430	Phase 2
0.7926	Intermediate Similarity	NPD792	Discontinued
0.7926	Intermediate Similarity	NPD490	Clinical (unspecified phase)
0.7801	Intermediate Similarity	NPD7469	Discontinued
0.7778	Intermediate Similarity	NPD2837	Discontinued
0.7746	Intermediate Similarity	NPD4703	Approved
0.7746	Intermediate Similarity	NPD4702	Approved
0.7727	Intermediate Similarity	NPD9284	Approved
0.7721	Intermediate Similarity	NPD272	Approved
0.7714	Intermediate Similarity	NPD2007	Clinical (unspecified phase)
0.7714	Intermediate Similarity	NPD4637	Clinical (unspecified phase)
0.7714	Intermediate Similarity	NPD3717	Discontinued
0.7692	Intermediate Similarity	NPD3100	Discontinued
0.766	Intermediate Similarity	NPD1918	Clinical (unspecified phase)
0.766	Intermediate Similarity	NPD3813	Approved
0.7639	Intermediate Similarity	NPD2465	Approved
0.7639	Intermediate Similarity	NPD2466	Phase 3
0.7639	Intermediate Similarity	NPD2462	Phase 3
0.763	Intermediate Similarity	NPD9726	Discontinued
0.7626	Intermediate Similarity	NPD945	Clinical (unspecified phase)
0.7609	Intermediate Similarity	NPD6554	Approved
0.7609	Intermediate Similarity	NPD45	Approved
0.7589	Intermediate Similarity	NPD4510	Discontinued
0.7584	Intermediate Similarity	NPD5315	Discontinued
0.7571	Intermediate Similarity	NPD1395	Clinical (unspecified phase)
0.7556	Intermediate Similarity	NPD9206	Approved
0.7556	Intermediate Similarity	NPD9207	Approved
0.7554	Intermediate Similarity	NPD2896	Discontinued
0.7552	Intermediate Similarity	NPD6148	Clinical (unspecified phase)
0.7551	Intermediate Similarity	NPD3113	Approved
0.7551	Intermediate Similarity	NPD473	Clinical (unspecified phase)
0.7551	Intermediate Similarity	NPD3112	Approved
0.7551	Intermediate Similarity	NPD3114	Approved
0.7551	Intermediate Similarity	NPD3115	Approved
0.7551	Intermediate Similarity	NPD2580	Discontinued
0.7537	Intermediate Similarity	NPD1095	Clinical (unspecified phase)
0.7535	Intermediate Similarity	NPD649	Clinical (unspecified phase)
0.7533	Intermediate Similarity	NPD3323	Discontinued
0.7517	Intermediate Similarity	NPD2172	Phase 1
0.75	Intermediate Similarity	NPD2865	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1192	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD2089	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD2165	Phase 1
0.7483	Intermediate Similarity	NPD175	Clinical (unspecified phase)
0.7467	Intermediate Similarity	NPD2385	Clinical (unspecified phase)
0.7463	Intermediate Similarity	NPD9080	Approved
0.7448	Intermediate Similarity	NPD4374	Clinical (unspecified phase)
0.7447	Intermediate Similarity	NPD1649	Discontinued
0.7447	Intermediate Similarity	NPD9599	Approved
0.7431	Intermediate Similarity	NPD1683	Approved
0.7415	Intermediate Similarity	NPD2012	Clinical (unspecified phase)
0.7413	Intermediate Similarity	NPD751	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD1254	Approved
0.741	Intermediate Similarity	NPD1256	Approved
0.741	Intermediate Similarity	NPD1255	Approved
0.741	Intermediate Similarity	NPD1253	Approved
0.7403	Intermediate Similarity	NPD5934	Clinical (unspecified phase)
0.74	Intermediate Similarity	NPD6454	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD5020	Approved
0.7386	Intermediate Similarity	NPD4779	Clinical (unspecified phase)
0.7383	Intermediate Similarity	NPD6497	Approved
0.7379	Intermediate Similarity	NPD1270	Approved
0.7379	Intermediate Similarity	NPD2110	Approved
0.7379	Intermediate Similarity	NPD1661	Suspended
0.7376	Intermediate Similarity	NPD174	Discontinued
0.7372	Intermediate Similarity	NPD809	Discontinued
0.7351	Intermediate Similarity	NPD6771	Discontinued
0.7351	Intermediate Similarity	NPD1853	Clinical (unspecified phase)
0.7344	Intermediate Similarity	NPD60	Approved
0.7343	Intermediate Similarity	NPD4047	Discontinued
0.7333	Intermediate Similarity	NPD5255	Approved
0.7329	Intermediate Similarity	NPD1183	Approved
0.7324	Intermediate Similarity	NPD165	Phase 2
0.732	Intermediate Similarity	NPD4174	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD1380	Discovery
0.7292	Intermediate Similarity	NPD1352	Discontinued
0.729	Intermediate Similarity	NPD3610	Approved
0.729	Intermediate Similarity	NPD3609	Approved
0.7285	Intermediate Similarity	NPD1404	Approved
0.7285	Intermediate Similarity	NPD1403	Approved
0.7279	Intermediate Similarity	NPD1031	Discontinued
0.7273	Intermediate Similarity	NPD2641	Approved
0.7273	Intermediate Similarity	NPD1343	Approved
0.7273	Intermediate Similarity	NPD2390	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD2640	Approved
0.7267	Intermediate Similarity	NPD2581	Approved
0.7267	Intermediate Similarity	NPD2582	Approved
0.7261	Intermediate Similarity	NPD6044	Discontinued
0.7248	Intermediate Similarity	NPD977	Approved
0.7248	Intermediate Similarity	NPD975	Approved
0.7248	Intermediate Similarity	NPD976	Approved
0.7234	Intermediate Similarity	NPD9506	Approved
0.7231	Intermediate Similarity	NPD8840	Approved
0.723	Intermediate Similarity	NPD4641	Discontinued
0.723	Intermediate Similarity	NPD1257	Approved
0.7226	Intermediate Similarity	NPD5436	Phase 1
0.7222	Intermediate Similarity	NPD1427	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD704	Clinical (unspecified phase)
0.7218	Intermediate Similarity	NPD5787	Discontinued
0.7218	Intermediate Similarity	NPD1561	Phase 2
0.7211	Intermediate Similarity	NPD5538	Clinical (unspecified phase)
0.7203	Intermediate Similarity	NPD3943	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD2150	Discontinued
0.7197	Intermediate Similarity	NPD5065	Approved
0.7194	Intermediate Similarity	NPD9100	Approved
0.719	Intermediate Similarity	NPD8129	Discovery
0.7183	Intermediate Similarity	NPD203	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD3339	Approved
0.7181	Intermediate Similarity	NPD1917	Discontinued
0.7179	Intermediate Similarity	NPD1078	Clinical (unspecified phase)
0.7161	Intermediate Similarity	NPD2185	Clinical (unspecified phase)
0.7161	Intermediate Similarity	NPD4640	Approved
0.7161	Intermediate Similarity	NPD2333	Discontinued
0.7161	Intermediate Similarity	NPD4639	Approved
0.7161	Intermediate Similarity	NPD4638	Approved
0.7153	Intermediate Similarity	NPD1383	Phase 3
0.7153	Intermediate Similarity	NPD1382	Phase 2
0.7152	Intermediate Similarity	NPD6375	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD1328	Approved
0.7133	Intermediate Similarity	NPD2809	Approved
0.7133	Intermediate Similarity	NPD4804	Approved
0.7124	Intermediate Similarity	NPD8026	Phase 1
0.7124	Intermediate Similarity	NPD4384	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD3262	Approved
0.7114	Intermediate Similarity	NPD5965	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD4181	Approved
0.7105	Intermediate Similarity	NPD5418	Discontinued
0.7101	Intermediate Similarity	NPD9305	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD947	Approved
0.7097	Intermediate Similarity	NPD2639	Approved
0.7097	Intermediate Similarity	NPD3929	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD2642	Approved
0.7086	Intermediate Similarity	NPD6026	Approved
0.7086	Intermediate Similarity	NPD2748	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD3583	Phase 2
0.707	Intermediate Similarity	NPD3117	Approved
0.707	Intermediate Similarity	NPD3116	Approved
0.707	Intermediate Similarity	NPD1567	Clinical (unspecified phase)
0.7068	Intermediate Similarity	NPD4811	Discontinued
0.7063	Intermediate Similarity	NPD2323	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD3341	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD2511	Approved
0.7055	Intermediate Similarity	NPD5254	Discontinued
0.7051	Intermediate Similarity	NPD7287	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD4075	Phase 2
0.7039	Intermediate Similarity	NPD5300	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