NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	184.1
Volume:	199.25
LogP:	2.904
LogD:	2.327
LogS:	-2.798
# Rotatable Bonds:	0
TPSA:	28.15
# H-Bond Aceptor:	2
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.651
Synthetic Accessibility Score:	2.557
Fsp3:	0.25
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:	-4.966
MDCK Permeability:	2.6719797460827976e-05
Pgp-inhibitor:	0.161
Pgp-substrate:	0.985
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.043
30% Bioavailability (F30%):	0.003

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.944
Plasma Protein Binding (PPB):	78.1200942993164%
Volume Distribution (VD):	1.538
Pgp-substrate:	16.7565860748291%

ADMET: Metabolism

CYP1A2-inhibitor:	0.899
CYP1A2-substrate:	0.95
CYP2C19-inhibitor:	0.061
CYP2C19-substrate:	0.321
CYP2C9-inhibitor:	0.028
CYP2C9-substrate:	0.841
CYP2D6-inhibitor:	0.797
CYP2D6-substrate:	0.908
CYP3A4-inhibitor:	0.025
CYP3A4-substrate:	0.415

ADMET: Excretion

Clearance (CL):	8.294
Half-life (T1/2):	0.3

ADMET: Toxicity

hERG Blockers:	0.076
Human Hepatotoxicity (H-HT):	0.436
Drug-inuced Liver Injury (DILI):	0.049
AMES Toxicity:	0.03
Rat Oral Acute Toxicity:	0.879
Maximum Recommended Daily Dose:	0.878
Skin Sensitization:	0.696
Carcinogencity:	0.09
Eye Corrosion:	0.169
Eye Irritation:	0.94
Respiratory Toxicity:	0.984

Download Data

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

Natural Product: NPC22079

Natural Product ID:	NPC22079
*Common Name:**	CWOYLIJQLSNRRN-UHFFFAOYSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	CWOYLIJQLSNRRN-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C12H12N2/c1-8-12-10(6-7-13-8)9-4-2-3-5-11(9)14-12/h2-5,14H,6-7H2,1H3
SMILES:	CC1=NCCc2c3ccccc3[nH]c12
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL295234
PubChem CID:	NA
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0001140] Harmala alkaloids

*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
NPO3808	Elaeagnus angustifolia	Species	Elaeagnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3808	Elaeagnus angustifolia	Species	Elaeagnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3808	Elaeagnus angustifolia	Species	Elaeagnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO3808	Elaeagnus angustifolia	Species	Elaeagnaceae	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
EC50	4
IC50	1
Ki	18
Others	2
Potency	18

Activity Type	# Activity
Cell Line	3
Individual Protein	26
Organism	3
Others	3
Protein Complex	5
Protein Family	3
Protein-Protein Interaction	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1759	Cell Line	FM3A	Mus musculus	EC50	=	45000.0	nM	PMID[573396]
NPT1759	Cell Line	FM3A	Mus musculus	Selective toxicity	=	2.1	n.a.	PMID[573396]
NPT1778	Individual Protein	Serotonin 2a (5-HT2a) receptor	Rattus norvegicus	Ki	=	1150.0	nM	PMID[573397]
NPT292	Individual Protein	Serotonin 2c (5-HT2c) receptor	Homo sapiens	Ki	=	1860.0	nM	PMID[573397]
NPT1784	Individual Protein	Serotonin 5a (5-HT5a) receptor	Homo sapiens	Ki	=	845.0	nM	PMID[573397]
NPT294	Individual Protein	Serotonin 6 (5-HT6) receptor	Homo sapiens	Ki	=	1450.0	nM	PMID[573397]
NPT1785	Individual Protein	Serotonin 7 (5-HT7) receptor	Homo sapiens	Ki	=	280.0	nM	PMID[573397]
NPT295	Individual Protein	Serotonin transporter	Homo sapiens	Ki	>	10000.0	nM	PMID[573397]
NPT228	Individual Protein	Norepinephrine transporter	Homo sapiens	Ki	>	10000.0	nM	PMID[573397]
NPT1790	Individual Protein	Dopamine transporter	Bos taurus	Ki	>	10000.0	nM	PMID[573397]
NPT1791	Individual Protein	Nischarin	Homo sapiens	Ki	=	46.0	nM	PMID[573397]
NPT1791	Individual Protein	Nischarin	Homo sapiens	Ki	=	148.0	nM	PMID[573397]
NPT759	Cell Line	H9	Homo sapiens	IC50	=	110300.0	nM	PMID[573398]
NPT48	Individual Protein	Lysine-specific demethylase 4D-like	Homo sapiens	Potency	=	28183.8	nM	PMID[573399]
NPT51	Individual Protein	Microtubule-associated protein tau	Homo sapiens	Potency	=	14125.4	nM	PMID[573399]
NPT51	Individual Protein	Microtubule-associated protein tau	Homo sapiens	Potency	=	12589.3	nM	PMID[573399]
NPT56	Individual Protein	Beta-lactamase AmpC	Escherichia coli K-12	Potency	=	6309.6	nM	PMID[573399]
NPT59	Individual Protein	DNA polymerase beta	Homo sapiens	Potency	=	79432.8	nM	PMID[573399]
NPT532	Individual Protein	Lysine-specific demethylase 4A	Homo sapiens	Potency	n.a.	50118.7	nM	PMID[573399]
NPT5	Individual Protein	Histone-lysine N-methyltransferase, H3 lysine-9 specific 3	Homo sapiens	Potency	n.a.	44668.4	nM	PMID[573399]
NPT63	Individual Protein	Bromodomain adjacent to zinc finger domain protein 2B	Homo sapiens	Potency	n.a.	35481.3	nM	PMID[573399]
NPT226	Individual Protein	Beta-2 adrenergic receptor	Homo sapiens	EC50	=	2770.0	nM	PMID[573399]
NPT1474	Individual Protein	ATP-dependent Clp protease proteolytic subunit	Bacillus subtilis (strain 168)	Potency	n.a.	15848.9	nM	PMID[573399]
NPT160	Individual Protein	TAR DNA-binding protein 43	Homo sapiens	Potency	n.a.	501.2	nM	PMID[573399]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	EC50	=	18000.0	nM	PMID[573396]
NPT92	Individual Protein	Serotonin 1a (5-HT1a) receptor	Homo sapiens	Ki	>	1670.0	nM	PMID[573397]
NPT973	Individual Protein	Serotonin 1b (5-HT1b) receptor	Homo sapiens	Ki	>	10000.0	nM	PMID[573397]
NPT974	Individual Protein	Serotonin 1d (5-HT1d) receptor	Homo sapiens	Ki	>	10000.0	nM	PMID[573397]
NPT1783	Protein Complex	Serotonin 3 (5-HT3) receptor	Homo sapiens	Ki	>	10000.0	nM	PMID[573397]
NPT1786	Protein Family	Dopamine receptor	Homo sapiens	Ki	>	10000.0	nM	PMID[573397]
NPT805	Protein Complex	GABA-A receptor; anion channel	Rattus norvegicus	Ki	>	10000.0	nM	PMID[573397]
NPT1787	Protein Family	Metabotropic glutamate receptor	Rattus norvegicus	Ki	>	10000.0	nM	PMID[573397]
NPT1302	Protein Family	Muscarinic acetylcholine receptor	Homo sapiens	Ki	>	10000.0	nM	PMID[573397]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	EC50	=	32000.0	nM	PMID[573398]
NPT27	Others	Unspecified		Ratio IC50/EC50	=	3.4	uM	PMID[573398]
NPT197	Protein-Protein Interaction	Menin/Histone-lysine N-methyltransferase MLL	Homo sapiens	Potency	=	25118.9	nM	PMID[573399]
NPT2	Others	Unspecified		Potency	=	25929.0	nM	PMID[573399]
NPT21702	PROTEIN-PROTEIN INTERACTION	Importin subunit beta-1/Snurportin-1	Homo sapiens	Potency	n.a.	63095.7	nM	PMID[573399]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Potency	n.a.	2078.7	nM	PMID[573399]
NPT20798	PROTEIN COMPLEX	GTP-binding nuclear protein Ran/Importin subunit beta-1/Snurportin-1	Homo sapiens	Potency	n.a.	11582.1	nM	PMID[573399]
NPT803	Individual Protein	Flap endonuclease 1	Homo sapiens	Potency	n.a.	28183.8	nM	PMID[573399]
NPT755	Individual Protein	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	Homo sapiens	Potency	n.a.	19952.6	nM	PMID[573399]
NPT2	Others	Unspecified		Potency	n.a.	8912.5	nM	PMID[573399]

☑ 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 NPC22079 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	972
0.1-0.2	12672
0.2-0.3	17280
0.3-0.4	5961
0.4-0.5	2586
0.5-0.6	1686
0.6-0.7	979
0.7-0.8	404
0.8-0.85	103
0.85-0.9	37
0.9-0.95	14
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.938	High Similarity	NPC198988
0.936	High Similarity	NPC250361
0.935	High Similarity	NPC41174
0.9308	High Similarity	NPC325252
0.9291	High Similarity	NPC473587
0.9219	High Similarity	NPC475428
0.9213	High Similarity	NPC473762
0.9147	High Similarity	NPC475450
0.9147	High Similarity	NPC179365
0.9091	High Similarity	NPC84911
0.9091	High Similarity	NPC125746
0.903	High Similarity	NPC115611
0.903	High Similarity	NPC59084
0.903	High Similarity	NPC2949
0.9015	High Similarity	NPC261195
0.9015	High Similarity	NPC218268
0.9015	High Similarity	NPC96102
0.9015	High Similarity	NPC29886
0.8963	High Similarity	NPC63157
0.8963	High Similarity	NPC473868
0.8955	High Similarity	NPC88097
0.8955	High Similarity	NPC110126
0.8955	High Similarity	NPC73767
0.8947	High Similarity	NPC105127
0.8931	High Similarity	NPC473930
0.8889	High Similarity	NPC469779
0.8889	High Similarity	NPC469767
0.8889	High Similarity	NPC469780
0.8889	High Similarity	NPC469784
0.8889	High Similarity	NPC469783
0.8889	High Similarity	NPC469761
0.8889	High Similarity	NPC469768
0.8849	High Similarity	NPC37548
0.8841	High Similarity	NPC143872
0.8832	High Similarity	NPC242556
0.8824	High Similarity	NPC469766
0.8786	High Similarity	NPC148592
0.8768	High Similarity	NPC470440
0.8759	High Similarity	NPC190296
0.875	High Similarity	NPC279081
0.8712	High Similarity	NPC82295
0.8643	High Similarity	NPC179787
0.8643	High Similarity	NPC21605
0.8643	High Similarity	NPC201380
0.8633	High Similarity	NPC314372
0.8633	High Similarity	NPC204141
0.8613	High Similarity	NPC230002
0.8601	High Similarity	NPC470507
0.8601	High Similarity	NPC38736
0.8582	High Similarity	NPC321911
0.8582	High Similarity	NPC124005
0.8582	High Similarity	NPC187951
0.8571	High Similarity	NPC63545
0.8571	High Similarity	NPC288838
0.856	High Similarity	NPC148140
0.8542	High Similarity	NPC285469
0.854	High Similarity	NPC312092
0.8521	High Similarity	NPC33421
0.8521	High Similarity	NPC53947
0.8511	High Similarity	NPC469811
0.8511	High Similarity	NPC471957
0.85	High Similarity	NPC159856
0.8492	Intermediate Similarity	NPC81561
0.8478	Intermediate Similarity	NPC284635
0.8451	Intermediate Similarity	NPC2272
0.8425	Intermediate Similarity	NPC318065
0.8425	Intermediate Similarity	NPC206819
0.8425	Intermediate Similarity	NPC475990
0.8414	Intermediate Similarity	NPC141353
0.8392	Intermediate Similarity	NPC24678
0.8392	Intermediate Similarity	NPC105818
0.838	Intermediate Similarity	NPC477134
0.8345	Intermediate Similarity	NPC471458
0.8333	Intermediate Similarity	NPC470823
0.8311	Intermediate Similarity	NPC16667
0.8311	Intermediate Similarity	NPC282231
0.831	Intermediate Similarity	NPC129042
0.8295	Intermediate Similarity	NPC215519
0.8288	Intermediate Similarity	NPC184476
0.8281	Intermediate Similarity	NPC162689
0.8281	Intermediate Similarity	NPC54102
0.8276	Intermediate Similarity	NPC469760
0.8276	Intermediate Similarity	NPC141926
0.8276	Intermediate Similarity	NPC259644
0.8276	Intermediate Similarity	NPC469765
0.8276	Intermediate Similarity	NPC232798
0.8276	Intermediate Similarity	NPC73952
0.8276	Intermediate Similarity	NPC469786
0.8276	Intermediate Similarity	NPC325903
0.8276	Intermediate Similarity	NPC25008
0.8276	Intermediate Similarity	NPC200214
0.8276	Intermediate Similarity	NPC469763
0.8243	Intermediate Similarity	NPC279918
0.8243	Intermediate Similarity	NPC122141
0.8231	Intermediate Similarity	NPC286427
0.8231	Intermediate Similarity	NPC299594
0.8231	Intermediate Similarity	NPC236711
0.8227	Intermediate Similarity	NPC20144
0.8219	Intermediate Similarity	NPC207726
0.8219	Intermediate Similarity	NPC70922
0.8219	Intermediate Similarity	NPC34844
0.8219	Intermediate Similarity	NPC80597
0.8219	Intermediate Similarity	NPC212376
0.8219	Intermediate Similarity	NPC75540
0.8219	Intermediate Similarity	NPC211572
0.8207	Intermediate Similarity	NPC470233
0.8207	Intermediate Similarity	NPC216713
0.8176	Intermediate Similarity	NPC221786
0.8176	Intermediate Similarity	NPC41257
0.8176	Intermediate Similarity	NPC474880
0.8176	Intermediate Similarity	NPC56765
0.8146	Intermediate Similarity	NPC474561
0.8146	Intermediate Similarity	NPC49954
0.8143	Intermediate Similarity	NPC104483
0.8129	Intermediate Similarity	NPC150259
0.8121	Intermediate Similarity	NPC229173
0.8121	Intermediate Similarity	NPC473320
0.8121	Intermediate Similarity	NPC44773
0.8121	Intermediate Similarity	NPC215584
0.8108	Intermediate Similarity	NPC216643
0.8079	Intermediate Similarity	NPC280864
0.8079	Intermediate Similarity	NPC17751
0.8054	Intermediate Similarity	NPC92796
0.8054	Intermediate Similarity	NPC135141
0.8054	Intermediate Similarity	NPC67056
0.8045	Intermediate Similarity	NPC122718
0.8041	Intermediate Similarity	NPC469785
0.8039	Intermediate Similarity	NPC280548
0.8039	Intermediate Similarity	NPC194411
0.8026	Intermediate Similarity	NPC54988
0.8013	Intermediate Similarity	NPC271797
0.8013	Intermediate Similarity	NPC90723
0.8013	Intermediate Similarity	NPC21174
0.8013	Intermediate Similarity	NPC472587
0.8013	Intermediate Similarity	NPC271734
0.8	Intermediate Similarity	NPC470204
0.7987	Intermediate Similarity	NPC469762
0.7987	Intermediate Similarity	NPC470498
0.7987	Intermediate Similarity	NPC6982
0.7974	Intermediate Similarity	NPC63751
0.7973	Intermediate Similarity	NPC476219
0.7973	Intermediate Similarity	NPC476297
0.797	Intermediate Similarity	NPC46358
0.7958	Intermediate Similarity	NPC238499
0.7947	Intermediate Similarity	NPC470203
0.7935	Intermediate Similarity	NPC34508
0.7931	Intermediate Similarity	NPC316069
0.7895	Intermediate Similarity	NPC194640
0.7895	Intermediate Similarity	NPC247987
0.7895	Intermediate Similarity	NPC317105
0.7895	Intermediate Similarity	NPC311276
0.7885	Intermediate Similarity	NPC37423
0.7885	Intermediate Similarity	NPC275305
0.7881	Intermediate Similarity	NPC131718
0.7872	Intermediate Similarity	NPC314102
0.7872	Intermediate Similarity	NPC251722
0.7843	Intermediate Similarity	NPC274229
0.7843	Intermediate Similarity	NPC470508
0.7834	Intermediate Similarity	NPC288785
0.7815	Intermediate Similarity	NPC474791
0.7815	Intermediate Similarity	NPC230869
0.7808	Intermediate Similarity	NPC478186
0.7806	Intermediate Similarity	NPC474897
0.7794	Intermediate Similarity	NPC476140
0.7792	Intermediate Similarity	NPC49217
0.7792	Intermediate Similarity	NPC109447
0.7792	Intermediate Similarity	NPC160105
0.7785	Intermediate Similarity	NPC248454
0.7785	Intermediate Similarity	NPC281094
0.7785	Intermediate Similarity	NPC68354
0.7778	Intermediate Similarity	NPC162799
0.7778	Intermediate Similarity	NPC277157
0.7778	Intermediate Similarity	NPC149265
0.7778	Intermediate Similarity	NPC40779
0.7756	Intermediate Similarity	NPC82331
0.7755	Intermediate Similarity	NPC470111
0.7748	Intermediate Similarity	NPC76982
0.7742	Intermediate Similarity	NPC201700
0.7742	Intermediate Similarity	NPC317430
0.774	Intermediate Similarity	NPC285731
0.7736	Intermediate Similarity	NPC72980
0.7736	Intermediate Similarity	NPC215795
0.7736	Intermediate Similarity	NPC11126
0.7736	Intermediate Similarity	NPC270009
0.7736	Intermediate Similarity	NPC176199
0.7712	Intermediate Similarity	NPC225018
0.7707	Intermediate Similarity	NPC472123
0.7707	Intermediate Similarity	NPC161861
0.7698	Intermediate Similarity	NPC282398
0.7692	Intermediate Similarity	NPC97343
0.7688	Intermediate Similarity	NPC91179
0.7682	Intermediate Similarity	NPC51054
0.7673	Intermediate Similarity	NPC59269
0.7662	Intermediate Similarity	NPC102423
0.7658	Intermediate Similarity	NPC189812
0.7658	Intermediate Similarity	NPC329688
0.7658	Intermediate Similarity	NPC280297
0.7651	Intermediate Similarity	NPC40070
0.7647	Intermediate Similarity	NPC27740
0.764	Intermediate Similarity	NPC192270

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 NPC22079 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	402
0.1-0.2	882
0.2-0.3	953
0.3-0.4	1854
0.4-0.5	2444
0.5-0.6	1812
0.6-0.7	628
0.7-0.8	152
0.8-0.85	9
0.85-0.9	12
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.903	High Similarity	NPD3943	Clinical (unspecified phase)
0.9015	High Similarity	NPD198	Clinical (unspecified phase)
0.8955	High Similarity	NPD786	Approved
0.8849	High Similarity	NPD3100	Discontinued
0.8832	High Similarity	NPD5254	Discontinued
0.8824	High Similarity	NPD1722	Approved
0.8806	High Similarity	NPD1262	Discovery
0.8714	High Similarity	NPD4374	Clinical (unspecified phase)
0.8561	High Similarity	NPD3654	Approved
0.8521	High Similarity	NPD4462	Approved
0.8521	High Similarity	NPD4463	Approved
0.8489	Intermediate Similarity	NPD4637	Clinical (unspecified phase)
0.8444	Intermediate Similarity	NPD3385	Approved
0.8392	Intermediate Similarity	NPD2172	Phase 1
0.831	Intermediate Similarity	NPD1683	Approved
0.8276	Intermediate Similarity	NPD2837	Discontinued
0.8182	Intermediate Similarity	NPD1528	Clinical (unspecified phase)
0.8148	Intermediate Similarity	NPD947	Approved
0.8058	Intermediate Similarity	NPD1254	Approved
0.8058	Intermediate Similarity	NPD1253	Approved
0.8058	Intermediate Similarity	NPD1255	Approved
0.8058	Intermediate Similarity	NPD1256	Approved
0.8028	Intermediate Similarity	NPD1592	Phase 3
0.8013	Intermediate Similarity	NPD3323	Discontinued
0.8	Intermediate Similarity	NPD1403	Approved
0.8	Intermediate Similarity	NPD1404	Approved
0.7986	Intermediate Similarity	NPD4880	Discontinued
0.7972	Intermediate Similarity	NPD4047	Discontinued
0.7961	Intermediate Similarity	NPD5744	Clinical (unspecified phase)
0.7947	Intermediate Similarity	NPD1853	Clinical (unspecified phase)
0.7899	Intermediate Similarity	NPD1251	Discontinued
0.7891	Intermediate Similarity	NPD3835	Phase 3
0.7891	Intermediate Similarity	NPD3833	Phase 3
0.7887	Intermediate Similarity	NPD680	Discontinued
0.7885	Intermediate Similarity	NPD4128	Approved
0.7872	Intermediate Similarity	NPD45	Approved
0.7872	Intermediate Similarity	NPD6554	Approved
0.7868	Intermediate Similarity	NPD992	Clinical (unspecified phase)
0.7868	Intermediate Similarity	NPD991	Phase 2
0.7857	Intermediate Similarity	NPD2640	Approved
0.7857	Intermediate Similarity	NPD2641	Approved
0.7834	Intermediate Similarity	NPD4075	Phase 2
0.7826	Intermediate Similarity	NPD3476	Approved
0.7826	Intermediate Similarity	NPD3475	Approved
0.7806	Intermediate Similarity	NPD1326	Approved
0.7806	Intermediate Similarity	NPD1325	Approved
0.78	Intermediate Similarity	NPD2150	Discontinued
0.7792	Intermediate Similarity	NPD2639	Approved
0.7792	Intermediate Similarity	NPD2642	Approved
0.7785	Intermediate Similarity	NPD3505	Approved
0.7785	Intermediate Similarity	NPD3506	Approved
0.7756	Intermediate Similarity	NPD3609	Approved
0.7756	Intermediate Similarity	NPD3610	Approved
0.7755	Intermediate Similarity	NPD4547	Phase 3
0.7742	Intermediate Similarity	NPD2185	Clinical (unspecified phase)
0.7742	Intermediate Similarity	NPD5069	Clinical (unspecified phase)
0.7737	Intermediate Similarity	NPD2118	Approved
0.7737	Intermediate Similarity	NPD2119	Approved
0.7736	Intermediate Similarity	NPD4076	Approved
0.7736	Intermediate Similarity	NPD4079	Approved
0.7724	Intermediate Similarity	NPD2006	Phase 2
0.7712	Intermediate Similarity	NPD972	Clinical (unspecified phase)
0.7707	Intermediate Similarity	NPD4112	Clinical (unspecified phase)
0.7703	Intermediate Similarity	NPD2430	Phase 2
0.7692	Intermediate Similarity	NPD4184	Clinical (unspecified phase)
0.768	Intermediate Similarity	NPD993	Approved
0.768	Intermediate Similarity	NPD990	Approved
0.7643	Intermediate Similarity	NPD6828	Phase 2
0.7643	Intermediate Similarity	NPD6827	Clinical (unspecified phase)
0.763	Intermediate Similarity	NPD1561	Phase 2
0.7562	Intermediate Similarity	NPD4181	Approved
0.7551	Intermediate Similarity	NPD3401	Clinical (unspecified phase)
0.7547	Intermediate Similarity	NPD5065	Approved
0.7536	Intermediate Similarity	NPD9583	Approved
0.7535	Intermediate Similarity	NPD4030	Approved
0.7535	Intermediate Similarity	NPD4028	Approved
0.7535	Intermediate Similarity	NPD4029	Approved
0.7534	Intermediate Similarity	NPD3834	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD5021	Discontinued
0.7516	Intermediate Similarity	NPD1192	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD749	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD2007	Clinical (unspecified phase)
0.7469	Intermediate Similarity	NPD6595	Phase 3
0.7469	Intermediate Similarity	NPD8464	Clinical (unspecified phase)
0.7455	Intermediate Similarity	NPD6217	Discontinued
0.7453	Intermediate Similarity	NPD2144	Approved
0.7453	Intermediate Similarity	NPD6203	Clinical (unspecified phase)
0.7452	Intermediate Similarity	NPD1248	Discontinued
0.7451	Intermediate Similarity	NPD473	Clinical (unspecified phase)
0.7451	Intermediate Similarity	NPD2580	Discontinued
0.7447	Intermediate Similarity	NPD715	Phase 3
0.7438	Intermediate Similarity	NPD482	Approved
0.7436	Intermediate Similarity	NPD5140	Approved
0.7436	Intermediate Similarity	NPD5138	Approved
0.7432	Intermediate Similarity	NPD4509	Discontinued
0.7426	Intermediate Similarity	NPD271	Approved
0.7426	Intermediate Similarity	NPD270	Clinical (unspecified phase)
0.7426	Intermediate Similarity	NPD268	Approved
0.7413	Intermediate Similarity	NPD3942	Approved
0.7413	Intermediate Similarity	NPD3944	Approved
0.741	Intermediate Similarity	NPD3961	Discontinued
0.7405	Intermediate Similarity	NPD4779	Clinical (unspecified phase)
0.7403	Intermediate Similarity	NPD2865	Clinical (unspecified phase)
0.7403	Intermediate Similarity	NPD4326	Phase 2
0.7391	Intermediate Similarity	NPD9357	Approved
0.7389	Intermediate Similarity	NPD2915	Discontinued
0.7386	Intermediate Similarity	NPD2165	Phase 1
0.7378	Intermediate Similarity	NPD5106	Approved
0.7378	Intermediate Similarity	NPD3319	Phase 1
0.7378	Intermediate Similarity	NPD3318	Approved
0.7378	Intermediate Similarity	NPD3320	Approved
0.7378	Intermediate Similarity	NPD5105	Approved
0.7372	Intermediate Similarity	NPD5787	Discontinued
0.7362	Intermediate Similarity	NPD6277	Clinical (unspecified phase)
0.7362	Intermediate Similarity	NPD5473	Discontinued
0.7355	Intermediate Similarity	NPD1554	Clinical (unspecified phase)
0.7351	Intermediate Similarity	NPD5538	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD3114	Approved
0.7338	Intermediate Similarity	NPD3115	Approved
0.7338	Intermediate Similarity	NPD3113	Approved
0.7338	Intermediate Similarity	NPD3112	Approved
0.7333	Intermediate Similarity	NPD3607	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD4499	Approved
0.7317	Intermediate Similarity	NPD3038	Discontinued
0.7317	Intermediate Similarity	NPD1895	Discontinued
0.7317	Intermediate Similarity	NPD1707	Approved
0.7317	Intermediate Similarity	NPD1708	Approved
0.7313	Intermediate Similarity	NPD7481	Approved
0.7313	Intermediate Similarity	NPD7480	Approved
0.7301	Intermediate Similarity	NPD8386	Phase 2
0.7297	Intermediate Similarity	NPD5020	Approved
0.7296	Intermediate Similarity	NPD4638	Approved
0.7296	Intermediate Similarity	NPD4640	Approved
0.7296	Intermediate Similarity	NPD4639	Approved
0.7289	Intermediate Similarity	NPD6610	Clinical (unspecified phase)
0.7279	Intermediate Similarity	NPD768	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD1332	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD5728	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD1597	Phase 1
0.7273	Intermediate Similarity	NPD975	Approved
0.7273	Intermediate Similarity	NPD976	Approved
0.7273	Intermediate Similarity	NPD977	Approved
0.7261	Intermediate Similarity	NPD2385	Clinical (unspecified phase)
0.7261	Intermediate Similarity	NPD5315	Discontinued
0.7259	Intermediate Similarity	NPD9392	Approved
0.7259	Intermediate Similarity	NPD9396	Approved
0.7255	Intermediate Similarity	NPD6158	Phase 2
0.7255	Intermediate Similarity	NPD6476	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD5436	Phase 1
0.7246	Intermediate Similarity	NPD4426	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD269	Clinical (unspecified phase)
0.7234	Intermediate Similarity	NPD1598	Discontinued
0.7226	Intermediate Similarity	NPD4811	Discontinued
0.7202	Intermediate Similarity	NPD5590	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD8431	Approved
0.7202	Intermediate Similarity	NPD3486	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD1918	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD1304	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD6180	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD4550	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD1313	Approved
0.717	Intermediate Similarity	NPD509	Phase 3
0.7169	Intermediate Similarity	NPD2095	Phase 2
0.7169	Intermediate Similarity	NPD2094	Phase 2
0.7169	Intermediate Similarity	NPD2092	Phase 2
0.7162	Intermediate Similarity	NPD2068	Approved
0.7162	Intermediate Similarity	NPD2071	Approved
0.7162	Intermediate Similarity	NPD2072	Approved
0.7162	Intermediate Similarity	NPD2073	Approved
0.7162	Intermediate Similarity	NPD2074	Approved
0.7162	Intermediate Similarity	NPD2069	Approved
0.7162	Intermediate Similarity	NPD2075	Approved
0.7162	Intermediate Similarity	NPD2070	Approved
0.716	Intermediate Similarity	NPD8110	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD750	Phase 2
0.7152	Intermediate Similarity	NPD702	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD5962	Phase 2
0.7143	Intermediate Similarity	NPD2882	Phase 1
0.7126	Intermediate Similarity	NPD2091	Phase 2
0.7126	Intermediate Similarity	NPD2096	Phase 2
0.7101	Intermediate Similarity	NPD2310	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD6141	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD1567	Clinical (unspecified phase)
0.7093	Intermediate Similarity	NPD5575	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD40	Phase 2
0.7091	Intermediate Similarity	NPD5730	Phase 2
0.7081	Intermediate Similarity	NPD2844	Phase 3
0.7076	Intermediate Similarity	NPD6630	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD5104	Approved
0.7059	Intermediate Similarity	NPD1661	Suspended
0.7059	Intermediate Similarity	NPD4702	Approved
0.7059	Intermediate Similarity	NPD4703	Approved
0.7051	Intermediate Similarity	NPD6285	Phase 2
0.7034	Intermediate Similarity	NPD803	Phase 1
0.703	Intermediate Similarity	NPD4398	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD5145	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD2748	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD2927	Phase 3
0.7	Intermediate Similarity	NPD748	Clinical (unspecified phase)
0.6992	Remote Similarity	NPD3001	Approved

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data