NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	162.12
Volume:	178.488
LogP:	0.557
LogD:	0.931
LogS:	0.82
# Rotatable Bonds:	1
TPSA:	24.92
# H-Bond Aceptor:	2
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.682
Synthetic Accessibility Score:	2.659
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:	-4.594
MDCK Permeability:	1.5639416233170778e-05
Pgp-inhibitor:	0.002
Pgp-substrate:	0.737
Human Intestinal Absorption (HIA):	0.014
20% Bioavailability (F20%):	0.835
30% Bioavailability (F30%):	0.857

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.778
Plasma Protein Binding (PPB):	14.55611801147461%
Volume Distribution (VD):	2.355
Pgp-substrate:	81.0232925415039%

ADMET: Metabolism

CYP1A2-inhibitor:	0.118
CYP1A2-substrate:	0.817
CYP2C19-inhibitor:	0.199
CYP2C19-substrate:	0.863
CYP2C9-inhibitor:	0.018
CYP2C9-substrate:	0.516
CYP2D6-inhibitor:	0.101
CYP2D6-substrate:	0.898
CYP3A4-inhibitor:	0.315
CYP3A4-substrate:	0.462

ADMET: Excretion

Clearance (CL):	10.722
Half-life (T1/2):	0.474

ADMET: Toxicity

hERG Blockers:	0.038
Human Hepatotoxicity (H-HT):	0.784
Drug-inuced Liver Injury (DILI):	0.074
AMES Toxicity:	0.018
Rat Oral Acute Toxicity:	0.906
Maximum Recommended Daily Dose:	0.922
Skin Sensitization:	0.925
Carcinogencity:	0.09
Eye Corrosion:	0.312
Eye Irritation:	0.121
Respiratory Toxicity:	0.94

Download Data

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

Natural Product: NPC146373

Natural Product ID:	NPC146373
*Common Name:**	Anabasine
IUPAC Name:	3-[(2S)-piperidin-2-yl]pyridine
Synonyms:
Standard InCHIKey:	MTXSIJUGVMTTMU-JTQLQIEISA-N
Standard InCHI:	InChI=1S/C10H14N2/c1-2-7-12-10(5-1)9-4-3-6-11-8-9/h3-4,6,8,10,12H,1-2,5,7H2/t10-/m0/s1
SMILES:	C1CC[C@H](NC1)c1cccnc1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1526229
PubChem CID:	205586
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids 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
NPO17694	Nicotiana tabacum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11559179]
NPO17694	Nicotiana tabacum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18001808]
NPO17694	Nicotiana tabacum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20954721]
NPO17694	Nicotiana tabacum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23479199]
NPO17694	Nicotiana tabacum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17694	Nicotiana tabacum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17694	Nicotiana tabacum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO17694	Nicotiana tabacum	Species	Solanaceae	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	3
EC50	2
IC50	9
Ki	2
LD50	1
Others	5
Potency	9

Activity Type	# Activity
Individual Protein	15
ORGANISM	4
Others	8
Protein Complex	2
Protein-Protein Interaction	1
SINGLE PROTEIN	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT240	Individual Protein	Cytochrome P450 2A6	Homo sapiens	IC50	=	32400	nM	Patent: US8609708 B2
NPT213	Individual Protein	Cytochrome P450 2C19	Homo sapiens	Potency	=	1995.3	nM	PMID[524045]
NPT110	Individual Protein	Cytochrome P450 2D6	Homo sapiens	Potency	=	7943.3	nM	PMID[524045]
NPT208	Individual Protein	Cytochrome P450 1A2	Homo sapiens	AC50	=	5011.87	nM	PMID[524046]
NPT213	Individual Protein	Cytochrome P450 2C19	Homo sapiens	AC50	=	1995.26	nM	PMID[524045]
NPT110	Individual Protein	Cytochrome P450 2D6	Homo sapiens	AC50	=	7943.28	nM	PMID[524045]
NPT3925	Individual Protein	Acetylcholine receptor protein alpha chain	Torpedo californica	IC50	=	193000.0	nM	PMID[524048]
NPT3925	Individual Protein	Acetylcholine receptor protein alpha chain	Torpedo californica	IC50	=	193000.0	nM	PMID[524049]
NPT50	Individual Protein	Tyrosyl-DNA phosphodiesterase 1	Homo sapiens	Potency	n.a.	33498.3	nM	PMID[524045]
NPT50	Individual Protein	Tyrosyl-DNA phosphodiesterase 1	Homo sapiens	Potency	n.a.	3349.8	nM	PMID[524045]
NPT49	Individual Protein	DNA-(apurinic or apyrimidinic site) lyase	Homo sapiens	Potency	n.a.	44668.4	nM	PMID[524045]
NPT240	Individual Protein	Cytochrome P450 2A6	Homo sapiens	IC50	=	32400.0	nM	PMID[524050]
NPT240	Individual Protein	Cytochrome P450 2A6	Homo sapiens	IC50	=	32400.0	nM	PMID[524051]
NPT414	Individual Protein	Neuronal acetylcholine receptor protein alpha-7 subunit	Rattus norvegicus	Ki	=	390.0	nM	PMID[524055]
NPT414	Individual Protein	Neuronal acetylcholine receptor protein alpha-7 subunit	Rattus norvegicus	EC50	=	18000.0	nM	PMID[524055]
NPT2	Others	Unspecified		Potency	n.a.	2433.7	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	61130.6	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	194.9	nM	PubChem BioAssay data set
NPT197	Protein-Protein Interaction	Menin/Histone-lysine N-methyltransferase MLL	Homo sapiens	Potency	=	39810.7	nM	PMID[524045]
NPT35	Others	n.a.		pKa	=	8.48	n.a.	PMID[524047]
NPT35	Others	n.a.		pKa	=	8.7	n.a.	PMID[524047]
NPT2	Others	Unspecified		IC50	=	285.0	nM	PMID[524048]
NPT2	Others	Unspecified		IC50	=	1980.0	nM	PMID[524048]
NPT20556	SINGLE PROTEIN	Replicase polyprotein 1ab	Severe acute respiratory syndrome coronavirus 2	Inhibition	=	16.93	%	PMID[524052]
NPT20555	ORGANISM	SARS-CoV-2	Severe acute respiratory syndrome coronavirus 2	Inhibition	=	0.08	%	PMID[524053]
NPT20555	ORGANISM	SARS-CoV-2	Severe acute respiratory syndrome coronavirus 2	IC50	>	20000.0	nM	PMID[524054]
NPT20555	ORGANISM	SARS-CoV-2	Severe acute respiratory syndrome coronavirus 2	IC50	>	19952.62	nM	PMID[524054]
NPT27	Others	Unspecified		LD50	=	16.0	mg.kg-1	PMID[524055]
NPT412	Protein Complex	Neuronal acetylcholine receptor; alpha4/beta2	Rattus norvegicus	EC50	>	30000.0	nM	PMID[524055]
NPT412	Protein Complex	Neuronal acetylcholine receptor; alpha4/beta2	Rattus norvegicus	Ki	=	1100.0	nM	PMID[524055]

☑ 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 NPC146373 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	989
0.1-0.2	12705
0.2-0.3	18270
0.3-0.4	5116
0.4-0.5	2797
0.5-0.6	1787
0.6-0.7	742
0.7-0.8	238
0.8-0.85	37
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	NPC166424
1.0	High Similarity	NPC245244
0.9421	High Similarity	NPC27740
0.8862	High Similarity	NPC48564
0.8862	High Similarity	NPC265605
0.8862	High Similarity	NPC182570
0.877	High Similarity	NPC91958
0.876	High Similarity	NPC101165
0.8689	High Similarity	NPC297486
0.8689	High Similarity	NPC240136
0.8689	High Similarity	NPC471402
0.8672	High Similarity	NPC89490
0.8651	High Similarity	NPC476322
0.8605	High Similarity	NPC475105
0.8605	High Similarity	NPC329896
0.8605	High Similarity	NPC475090
0.8571	High Similarity	NPC27802
0.8538	High Similarity	NPC282398
0.8492	Intermediate Similarity	NPC329825
0.8468	Intermediate Similarity	NPC143603
0.8425	Intermediate Similarity	NPC290094
0.8397	Intermediate Similarity	NPC69914
0.8333	Intermediate Similarity	NPC471322
0.8321	Intermediate Similarity	NPC476131
0.8321	Intermediate Similarity	NPC476454
0.8319	Intermediate Similarity	NPC76540
0.8296	Intermediate Similarity	NPC105127
0.8281	Intermediate Similarity	NPC46358
0.8231	Intermediate Similarity	NPC202957
0.8231	Intermediate Similarity	NPC169625
0.8222	Intermediate Similarity	NPC96102
0.8195	Intermediate Similarity	NPC324611
0.8175	Intermediate Similarity	NPC110126
0.8162	Intermediate Similarity	NPC84911
0.813	Intermediate Similarity	NPC235843
0.8088	Intermediate Similarity	NPC261195
0.8088	Intermediate Similarity	NPC29886
0.806	Intermediate Similarity	NPC256893
0.806	Intermediate Similarity	NPC82295
0.8043	Intermediate Similarity	NPC73767
0.803	Intermediate Similarity	NPC471311
0.803	Intermediate Similarity	NPC471313
0.8028	Intermediate Similarity	NPC469811
0.7986	Intermediate Similarity	NPC469767
0.7986	Intermediate Similarity	NPC469780
0.7986	Intermediate Similarity	NPC469783
0.7986	Intermediate Similarity	NPC279081
0.7986	Intermediate Similarity	NPC469779
0.7986	Intermediate Similarity	NPC470233
0.7986	Intermediate Similarity	NPC469761
0.7986	Intermediate Similarity	NPC469768
0.7986	Intermediate Similarity	NPC469784
0.7972	Intermediate Similarity	NPC321911
0.7966	Intermediate Similarity	NPC83987
0.7958	Intermediate Similarity	NPC63545
0.7929	Intermediate Similarity	NPC469766
0.7902	Intermediate Similarity	NPC201380
0.7902	Intermediate Similarity	NPC179787
0.7899	Intermediate Similarity	NPC314102
0.7899	Intermediate Similarity	NPC251722
0.7899	Intermediate Similarity	NPC65408
0.7891	Intermediate Similarity	NPC469897
0.7887	Intermediate Similarity	NPC86288
0.7872	Intermediate Similarity	NPC190296
0.7869	Intermediate Similarity	NPC231655
0.7857	Intermediate Similarity	NPC230002
0.7832	Intermediate Similarity	NPC288838
0.7832	Intermediate Similarity	NPC143872
0.7826	Intermediate Similarity	NPC325252
0.7823	Intermediate Similarity	NPC476464
0.7808	Intermediate Similarity	NPC325903
0.7793	Intermediate Similarity	NPC40070
0.7786	Intermediate Similarity	NPC32002
0.7786	Intermediate Similarity	NPC315348
0.7786	Intermediate Similarity	NPC316811
0.7786	Intermediate Similarity	NPC88097
0.777	Intermediate Similarity	NPC167635
0.777	Intermediate Similarity	NPC193740
0.7762	Intermediate Similarity	NPC159856
0.7762	Intermediate Similarity	NPC314372
0.7718	Intermediate Similarity	NPC56765
0.7714	Intermediate Similarity	NPC169433
0.7671	Intermediate Similarity	NPC53947
0.7656	Intermediate Similarity	NPC84268
0.7655	Intermediate Similarity	NPC471957
0.7626	Intermediate Similarity	NPC198988
0.7597	Intermediate Similarity	NPC148140
0.7568	Intermediate Similarity	NPC138842
0.7566	Intermediate Similarity	NPC317105
0.7552	Intermediate Similarity	NPC473868
0.7552	Intermediate Similarity	NPC63157
0.7551	Intermediate Similarity	NPC24678
0.7551	Intermediate Similarity	NPC105818
0.755	Intermediate Similarity	NPC122141
0.755	Intermediate Similarity	NPC470204
0.7548	Intermediate Similarity	NPC201634
0.7538	Intermediate Similarity	NPC81561
0.7534	Intermediate Similarity	NPC21605
0.7533	Intermediate Similarity	NPC236711
0.7518	Intermediate Similarity	NPC471312
0.7518	Intermediate Similarity	NPC150259
0.7517	Intermediate Similarity	NPC467188
0.75	Intermediate Similarity	NPC470823
0.75	Intermediate Similarity	NPC306397
0.75	Intermediate Similarity	NPC216713
0.75	Intermediate Similarity	NPC470203
0.7483	Intermediate Similarity	NPC41257
0.7483	Intermediate Similarity	NPC115611
0.7483	Intermediate Similarity	NPC59084
0.7483	Intermediate Similarity	NPC318065
0.7483	Intermediate Similarity	NPC206819
0.7481	Intermediate Similarity	NPC162689
0.7481	Intermediate Similarity	NPC54102
0.7464	Intermediate Similarity	NPC22079
0.7451	Intermediate Similarity	NPC78375
0.7451	Intermediate Similarity	NPC90723
0.7451	Intermediate Similarity	NPC469813
0.7451	Intermediate Similarity	NPC476446
0.745	Intermediate Similarity	NPC469760
0.745	Intermediate Similarity	NPC141926
0.745	Intermediate Similarity	NPC259644
0.745	Intermediate Similarity	NPC200214
0.745	Intermediate Similarity	NPC469786
0.745	Intermediate Similarity	NPC73952
0.745	Intermediate Similarity	NPC469763
0.745	Intermediate Similarity	NPC469765
0.745	Intermediate Similarity	NPC25008
0.7447	Intermediate Similarity	NPC218268
0.7434	Intermediate Similarity	NPC44773
0.7434	Intermediate Similarity	NPC215584
0.7434	Intermediate Similarity	NPC279918
0.7417	Intermediate Similarity	NPC216643
0.7417	Intermediate Similarity	NPC286427
0.7415	Intermediate Similarity	NPC105811
0.7415	Intermediate Similarity	NPC470111
0.74	Intermediate Similarity	NPC75540
0.74	Intermediate Similarity	NPC34844
0.74	Intermediate Similarity	NPC212376
0.74	Intermediate Similarity	NPC70922
0.74	Intermediate Similarity	NPC476219
0.74	Intermediate Similarity	NPC211572
0.74	Intermediate Similarity	NPC80597
0.7397	Intermediate Similarity	NPC204141
0.7394	Intermediate Similarity	NPC125746
0.7386	Intermediate Similarity	NPC225018
0.7386	Intermediate Similarity	NPC471177
0.7386	Intermediate Similarity	NPC59779
0.7386	Intermediate Similarity	NPC282231
0.7386	Intermediate Similarity	NPC124542
0.7379	Intermediate Similarity	NPC20144
0.7372	Intermediate Similarity	NPC212125
0.7368	Intermediate Similarity	NPC135141
0.7368	Intermediate Similarity	NPC92796
0.7368	Intermediate Similarity	NPC215519
0.7361	Intermediate Similarity	NPC2949
0.7351	Intermediate Similarity	NPC469785
0.7347	Intermediate Similarity	NPC316069
0.7338	Intermediate Similarity	NPC315320
0.7328	Intermediate Similarity	NPC476566
0.7303	Intermediate Similarity	NPC469762
0.7299	Intermediate Similarity	NPC135488
0.7299	Intermediate Similarity	NPC250361
0.7296	Intermediate Similarity	NPC280852
0.7296	Intermediate Similarity	NPC474958
0.729	Intermediate Similarity	NPC274229
0.7279	Intermediate Similarity	NPC285731
0.7259	Intermediate Similarity	NPC41174
0.7244	Intermediate Similarity	NPC49954
0.7244	Intermediate Similarity	NPC474561
0.7244	Intermediate Similarity	NPC54988
0.7234	Intermediate Similarity	NPC330326
0.7233	Intermediate Similarity	NPC471579
0.7231	Intermediate Similarity	NPC473901
0.7226	Intermediate Similarity	NPC478184
0.7219	Intermediate Similarity	NPC251391
0.7215	Intermediate Similarity	NPC82331
0.7213	Intermediate Similarity	NPC213774
0.7208	Intermediate Similarity	NPC131718
0.7197	Intermediate Similarity	NPC63751
0.7194	Intermediate Similarity	NPC473762
0.719	Intermediate Similarity	NPC213914
0.7181	Intermediate Similarity	NPC477974
0.7179	Intermediate Similarity	NPC471178
0.7179	Intermediate Similarity	NPC17751
0.7179	Intermediate Similarity	NPC280864
0.7171	Intermediate Similarity	NPC476297
0.7171	Intermediate Similarity	NPC209362
0.7171	Intermediate Similarity	NPC477815
0.7165	Intermediate Similarity	NPC302790
0.7162	Intermediate Similarity	NPC470440
0.7153	Intermediate Similarity	NPC122718
0.7152	Intermediate Similarity	NPC97343
0.7152	Intermediate Similarity	NPC70406
0.7152	Intermediate Similarity	NPC194411
0.7143	Intermediate Similarity	NPC475990
0.7143	Intermediate Similarity	NPC221786
0.7143	Intermediate Similarity	NPC230869
0.7143	Intermediate Similarity	NPC473587
0.7143	Intermediate Similarity	NPC474880
0.7134	Intermediate Similarity	NPC160105

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 NPC146373 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	395
0.1-0.2	816
0.2-0.3	1088
0.3-0.4	1757
0.4-0.5	2547
0.5-0.6	1744
0.6-0.7	617
0.7-0.8	156
0.8-0.85	22
0.85-0.9	6
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.935	High Similarity	NPD991	Phase 2
0.935	High Similarity	NPD992	Clinical (unspecified phase)
0.8992	High Similarity	NPD269	Clinical (unspecified phase)
0.8864	High Similarity	NPD768	Clinical (unspecified phase)
0.8862	High Similarity	NPD270	Clinical (unspecified phase)
0.8862	High Similarity	NPD271	Approved
0.8862	High Similarity	NPD268	Approved
0.874	High Similarity	NPD1598	Discontinued
0.8689	High Similarity	NPD9392	Approved
0.8689	High Similarity	NPD9396	Approved
0.8661	High Similarity	NPD9583	Approved
0.8504	High Similarity	NPD9357	Approved
0.845	Intermediate Similarity	NPD2119	Approved
0.845	Intermediate Similarity	NPD2118	Approved
0.8397	Intermediate Similarity	NPD715	Phase 3
0.8346	Intermediate Similarity	NPD3944	Approved
0.8346	Intermediate Similarity	NPD3942	Approved
0.8346	Intermediate Similarity	NPD748	Clinical (unspecified phase)
0.8321	Intermediate Similarity	NPD1722	Approved
0.8261	Intermediate Similarity	NPD2007	Clinical (unspecified phase)
0.8258	Intermediate Similarity	NPD3476	Approved
0.8258	Intermediate Similarity	NPD3475	Approved
0.8222	Intermediate Similarity	NPD198	Clinical (unspecified phase)
0.8195	Intermediate Similarity	NPD803	Phase 1
0.8175	Intermediate Similarity	NPD786	Approved
0.8125	Intermediate Similarity	NPD9598	Discontinued
0.8074	Intermediate Similarity	NPD4029	Approved
0.8074	Intermediate Similarity	NPD4028	Approved
0.8074	Intermediate Similarity	NPD4030	Approved
0.8056	Intermediate Similarity	NPD3339	Approved
0.8056	Intermediate Similarity	NPD2837	Discontinued
0.8	Intermediate Similarity	NPD976	Approved
0.8	Intermediate Similarity	NPD975	Approved
0.8	Intermediate Similarity	NPD1995	Approved
0.8	Intermediate Similarity	NPD1993	Approved
0.8	Intermediate Similarity	NPD977	Approved
0.8	Intermediate Similarity	NPD1994	Approved
0.7984	Intermediate Similarity	NPD4823	Approved
0.7984	Intermediate Similarity	NPD4824	Approved
0.7956	Intermediate Similarity	NPD792	Discontinued
0.7899	Intermediate Similarity	NPD201	Phase 2
0.7899	Intermediate Similarity	NPD200	Phase 2
0.7869	Intermediate Similarity	NPD9098	Phase 3
0.7869	Intermediate Similarity	NPD9099	Clinical (unspecified phase)
0.7868	Intermediate Similarity	NPD1627	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD1395	Clinical (unspecified phase)
0.7852	Intermediate Similarity	NPD6771	Discontinued
0.7832	Intermediate Similarity	NPD7469	Discontinued
0.7826	Intermediate Similarity	NPD490	Clinical (unspecified phase)
0.7823	Intermediate Similarity	NPD3112	Approved
0.7823	Intermediate Similarity	NPD3115	Approved
0.7823	Intermediate Similarity	NPD3113	Approved
0.7823	Intermediate Similarity	NPD3114	Approved
0.7794	Intermediate Similarity	NPD9726	Discontinued
0.7786	Intermediate Similarity	NPD2075	Approved
0.7786	Intermediate Similarity	NPD2073	Approved
0.7786	Intermediate Similarity	NPD2070	Approved
0.7786	Intermediate Similarity	NPD2074	Approved
0.7786	Intermediate Similarity	NPD2072	Approved
0.7786	Intermediate Similarity	NPD2071	Approved
0.7786	Intermediate Similarity	NPD2068	Approved
0.7786	Intermediate Similarity	NPD2069	Approved
0.7778	Intermediate Similarity	NPD4547	Phase 3
0.7778	Intermediate Similarity	NPD4703	Approved
0.7778	Intermediate Similarity	NPD4702	Approved
0.7755	Intermediate Similarity	NPD2165	Phase 1
0.7746	Intermediate Similarity	NPD4637	Clinical (unspecified phase)
0.7733	Intermediate Similarity	NPD1853	Clinical (unspecified phase)
0.7724	Intermediate Similarity	NPD3100	Discontinued
0.7724	Intermediate Similarity	NPD4374	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD3813	Approved
0.7671	Intermediate Similarity	NPD2462	Phase 3
0.7671	Intermediate Similarity	NPD2466	Phase 3
0.7671	Intermediate Similarity	NPD2465	Approved
0.7652	Intermediate Similarity	NPD5787	Discontinued
0.7651	Intermediate Similarity	NPD2865	Clinical (unspecified phase)
0.7651	Intermediate Similarity	NPD5300	Clinical (unspecified phase)
0.7635	Intermediate Similarity	NPD1328	Approved
0.7634	Intermediate Similarity	NPD4811	Discontinued
0.7626	Intermediate Similarity	NPD2140	Approved
0.7626	Intermediate Similarity	NPD2142	Approved
0.7626	Intermediate Similarity	NPD2141	Approved
0.7622	Intermediate Similarity	NPD3717	Discontinued
0.7622	Intermediate Similarity	NPD2006	Phase 2
0.7619	Intermediate Similarity	NPD4641	Discontinued
0.7606	Intermediate Similarity	NPD9599	Approved
0.7589	Intermediate Similarity	NPD2896	Discontinued
0.7571	Intermediate Similarity	NPD1254	Approved
0.7571	Intermediate Similarity	NPD1253	Approved
0.7571	Intermediate Similarity	NPD1255	Approved
0.7571	Intermediate Similarity	NPD1256	Approved
0.7569	Intermediate Similarity	NPD1988	Phase 1
0.7568	Intermediate Similarity	NPD1917	Discontinued
0.7566	Intermediate Similarity	NPD3323	Discontinued
0.7551	Intermediate Similarity	NPD2172	Phase 1
0.7536	Intermediate Similarity	NPD809	Discontinued
0.7534	Intermediate Similarity	NPD1270	Approved
0.7533	Intermediate Similarity	NPD2145	Clinical (unspecified phase)
0.7533	Intermediate Similarity	NPD1192	Clinical (unspecified phase)
0.7518	Intermediate Similarity	NPD947	Approved
0.7516	Intermediate Similarity	NPD6044	Discontinued
0.75	Intermediate Similarity	NPD4510	Discontinued
0.75	Intermediate Similarity	NPD2385	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD9080	Approved
0.75	Intermediate Similarity	NPD1427	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD8026	Phase 1
0.7483	Intermediate Similarity	NPD1649	Discontinued
0.7483	Intermediate Similarity	NPD2430	Phase 2
0.7467	Intermediate Similarity	NPD2748	Clinical (unspecified phase)
0.7466	Intermediate Similarity	NPD1683	Approved
0.7451	Intermediate Similarity	NPD3583	Phase 2
0.7448	Intermediate Similarity	NPD1918	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD3385	Approved
0.7421	Intermediate Similarity	NPD3341	Clinical (unspecified phase)
0.7417	Intermediate Similarity	NPD6497	Approved
0.7413	Intermediate Similarity	NPD945	Clinical (unspecified phase)
0.7372	Intermediate Similarity	NPD9284	Approved
0.7372	Intermediate Similarity	NPD5436	Phase 1
0.7368	Intermediate Similarity	NPD5255	Approved
0.7368	Intermediate Similarity	NPD1679	Approved
0.7365	Intermediate Similarity	NPD1183	Approved
0.7351	Intermediate Similarity	NPD2580	Discontinued
0.7343	Intermediate Similarity	NPD1380	Discovery
0.7342	Intermediate Similarity	NPD5065	Approved
0.7342	Intermediate Similarity	NPD5322	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD9207	Approved
0.7338	Intermediate Similarity	NPD9206	Approved
0.7333	Intermediate Similarity	NPD2012	Clinical (unspecified phase)
0.7325	Intermediate Similarity	NPD3117	Approved
0.7325	Intermediate Similarity	NPD3609	Approved
0.7325	Intermediate Similarity	NPD3610	Approved
0.7325	Intermediate Similarity	NPD3116	Approved
0.7319	Intermediate Similarity	NPD1095	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD4779	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD2640	Approved
0.7308	Intermediate Similarity	NPD2641	Approved
0.7297	Intermediate Similarity	NPD1661	Suspended
0.7286	Intermediate Similarity	NPD1251	Discontinued
0.7285	Intermediate Similarity	NPD2061	Approved
0.7266	Intermediate Similarity	NPD9305	Clinical (unspecified phase)
0.7266	Intermediate Similarity	NPD3654	Approved
0.7259	Intermediate Similarity	NPD1561	Phase 2
0.7255	Intermediate Similarity	NPD5418	Discontinued
0.7254	Intermediate Similarity	NPD272	Approved
0.7244	Intermediate Similarity	NPD5611	Phase 2
0.7241	Intermediate Similarity	NPD165	Phase 2
0.7239	Intermediate Similarity	NPD7564	Discontinued
0.7237	Intermediate Similarity	NPD473	Clinical (unspecified phase)
0.7234	Intermediate Similarity	NPD9100	Approved
0.723	Intermediate Similarity	NPD6148	Clinical (unspecified phase)
0.7211	Intermediate Similarity	NPD751	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD6454	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD1404	Approved
0.7208	Intermediate Similarity	NPD1403	Approved
0.7203	Intermediate Similarity	NPD206	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD971	Clinical (unspecified phase)
0.7192	Intermediate Similarity	NPD1383	Phase 3
0.7192	Intermediate Similarity	NPD1382	Phase 2
0.7171	Intermediate Similarity	NPD2809	Approved
0.7161	Intermediate Similarity	NPD4384	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD6277	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD3262	Approved
0.7152	Intermediate Similarity	NPD5965	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD4024	Phase 3
0.7143	Intermediate Similarity	NPD4181	Approved
0.7134	Intermediate Similarity	NPD425	Approved
0.7134	Intermediate Similarity	NPD3929	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD424	Approved
0.7123	Intermediate Similarity	NPD3943	Clinical (unspecified phase)
0.7121	Intermediate Similarity	NPD60	Approved
0.7117	Intermediate Similarity	NPD5806	Clinical (unspecified phase)
0.7092	Intermediate Similarity	NPD264	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD7287	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD5069	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD2185	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD3348	Phase 2
0.7081	Intermediate Similarity	NPD4075	Phase 2
0.7078	Intermediate Similarity	NPD2581	Approved
0.7078	Intermediate Similarity	NPD2582	Approved
0.707	Intermediate Similarity	NPD2719	Clinical (unspecified phase)
0.707	Intermediate Similarity	NPD2720	Phase 1
0.7067	Intermediate Similarity	NPD2110	Approved
0.7055	Intermediate Similarity	NPD1291	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD1016	Phase 2
0.7051	Intermediate Similarity	NPD5315	Discontinued
0.7051	Intermediate Similarity	NPD1015	Phase 2
0.7048	Intermediate Similarity	NPD3378	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD175	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD2620	Phase 2
0.7044	Intermediate Similarity	NPD2619	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD4184	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD6203	Clinical (unspecified phase)
0.7034	Intermediate Similarity	NPD9506	Approved
0.7025	Intermediate Similarity	NPD2639	Approved
0.7025	Intermediate Similarity	NPD1248	Discontinued
0.7025	Intermediate Similarity	NPD2642	Approved
0.7019	Intermediate Similarity	NPD4128	Approved
0.7015	Intermediate Similarity	NPD8840	Approved
0.7013	Intermediate Similarity	NPD2150	Discontinued
0.6994	Remote Similarity	NPD2930	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