NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	167.07
Volume:	185.617
LogP:	3.628
LogD:	3.522
LogS:	-4.265
# Rotatable Bonds:	0
TPSA:	15.79
# H-Bond Aceptor:	1
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	1

MedChem Properties

QED Drug-Likeness Score:	0.528
Synthetic Accessibility Score:	1.469
Fsp3:	0.0
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.635
MDCK Permeability:	1.662615431996528e-05
Pgp-inhibitor:	0.011
Pgp-substrate:	0.024
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.986
30% Bioavailability (F30%):	0.844

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.742
Plasma Protein Binding (PPB):	95.04378509521484%
Volume Distribution (VD):	1.316
Pgp-substrate:	3.3132150173187256%

ADMET: Metabolism

CYP1A2-inhibitor:	0.994
CYP1A2-substrate:	0.651
CYP2C19-inhibitor:	0.712
CYP2C19-substrate:	0.256
CYP2C9-inhibitor:	0.278
CYP2C9-substrate:	0.899
CYP2D6-inhibitor:	0.686
CYP2D6-substrate:	0.913
CYP3A4-inhibitor:	0.283
CYP3A4-substrate:	0.201

ADMET: Excretion

Clearance (CL):	5.367
Half-life (T1/2):	0.437

ADMET: Toxicity

hERG Blockers:	0.024
Human Hepatotoxicity (H-HT):	0.147
Drug-inuced Liver Injury (DILI):	0.589
AMES Toxicity:	0.759
Rat Oral Acute Toxicity:	0.134
Maximum Recommended Daily Dose:	0.623
Skin Sensitization:	0.924
Carcinogencity:	0.81
Eye Corrosion:	0.54
Eye Irritation:	0.996
Respiratory Toxicity:	0.987

Download Data

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

Natural Product: NPC250361

Natural Product ID:	NPC250361
*Common Name:**	Carbazole
IUPAC Name:	9H-carbazole
Synonyms:	9H-Carbazole; Carbazole
Standard InCHIKey:	UJOBWOGCFQCDNV-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C12H9N/c1-3-7-11-9(5-1)10-6-2-4-8-12(10)13-11/h1-8,13H
SMILES:	c1ccc2c(c1)[nH]c1c2cccc1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL243580
PubChem CID:	6854
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000211] Indoles and derivatives [CHEMONTID:0000210] Carbazoles

*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
NPO3364	Murraya koenigii	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12662104]
NPO3364	Murraya koenigii	Species	Rutaceae	Eukaryota	n.a.	Sri Lankan	n.a.	PMID[23376010]
NPO3364	Murraya koenigii	Species	Rutaceae	Eukaryota	fruits	Coimbatore, India	2010-JUN	PMID[23691929]
NPO3364	Murraya koenigii	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27136692]
NPO3364	Murraya koenigii	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3364	Murraya koenigii	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3364	Murraya koenigii	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO3364	Murraya koenigii	Species	Rutaceae	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	1
IC50	2
Others	26
Potency	25

Activity Type	# Activity
Cell Line	1
CELL-LINE	10
Individual Protein	16
Organism	1
Others	26

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT149	Individual Protein	Endoplasmic reticulum-associated amyloid beta-peptide-binding protein	Homo sapiens	Potency	=	39810.7	nM	PMID[561931]
NPT149	Individual Protein	Endoplasmic reticulum-associated amyloid beta-peptide-binding protein	Homo sapiens	Potency	=	25118.9	nM	PMID[561931]
NPT153	Individual Protein	Androgen Receptor	Homo sapiens	Potency	n.a.	50118.7	nM	PMID[561932]
NPT466	Cell Line	U-937	Homo sapiens	IC50	=	5560.0	nM	PMID[561933]
NPT1474	Individual Protein	ATP-dependent Clp protease proteolytic subunit	Bacillus subtilis (strain 168)	Potency	n.a.	35481.3	nM	PMID[561934]
NPT103	Individual Protein	Nuclear receptor ROR-gamma	Homo sapiens	Potency	n.a.	26603.2	nM	PMID[561931]
NPT43	Individual Protein	Tyrosinase	Agaricus bisporus	Inhibition	=	0.1	%	PMID[561935]
NPT43	Individual Protein	Tyrosinase	Agaricus bisporus	Inhibition	=	1.7	%	PMID[561935]
NPT43	Individual Protein	Tyrosinase	Agaricus bisporus	Inhibition	=	-2.2	%	PMID[561935]
NPT43	Individual Protein	Tyrosinase	Agaricus bisporus	Inhibition	=	-1.8	%	PMID[561935]
NPT43	Individual Protein	Tyrosinase	Agaricus bisporus	Inhibition	=	1.0	%	PMID[561935]
NPT535	Individual Protein	Parathyroid hormone receptor	Homo sapiens	Potency	n.a.	7079.5	nM	PMID[561934]
NPT152	Individual Protein	Nuclear factor erythroid 2-related factor 2	Homo sapiens	Potency	n.a.	68589.6	nM	PMID[561932]
NPT153	Individual Protein	Androgen Receptor	Homo sapiens	Potency	n.a.	60605.5	nM	PMID[25437304]
NPT162	Individual Protein	Heat shock protein beta-1	Homo sapiens	Potency	n.a.	61644.8	nM	PMID[11754614]
NPT20950	CELL-LINE	Erythrocyte	n.a.	Activity	=	265.0	min	PMID[561927]
NPT20950	CELL-LINE	Erythrocyte	n.a.	Activity	=	298.0	min	PMID[561927]
NPT20950	CELL-LINE	Erythrocyte	n.a.	Activity	=	327.0	min	PMID[561927]
NPT20950	CELL-LINE	Erythrocyte	n.a.	Activity	=	364.0	min	PMID[561927]
NPT20950	CELL-LINE	Erythrocyte	n.a.	Activity	=	406.0	min	PMID[561927]
NPT20950	CELL-LINE	Erythrocyte	n.a.	Activity	=	68.0	min	PMID[561927]
NPT20950	CELL-LINE	Erythrocyte	n.a.	Activity	=	101.0	min	PMID[561927]
NPT20950	CELL-LINE	Erythrocyte	n.a.	Activity	=	130.0	min	PMID[561927]
NPT20950	CELL-LINE	Erythrocyte	n.a.	Activity	=	167.0	min	PMID[561927]
NPT20950	CELL-LINE	Erythrocyte	n.a.	Activity	=	209.0	min	PMID[561927]
NPT3573	Organism	Bovine viral diarrhea virus	Bovine viral diarrhea virus 1	EC50	=	64000.0	nM	PMID[561928]
NPT27	Others	Unspecified		CC50	>	100000.0	nM	PMID[561928]
NPT27	Others	Unspecified		log Ks	=	2.44	n.a.	PMID[561929]
NPT832	Individual Protein	Kinesin-like protein 1	Homo sapiens	Inhibition	=	10.0	%	PMID[561930]
NPT94	Individual Protein	Aldehyde dehydrogenase 1A1	Homo sapiens	Potency	=	39810.7	nM	PMID[561931]
NPT2	Others	Unspecified		Potency	n.a.	59557.2	nM	PMID[561931]
NPT27	Others	Unspecified		Activity	=	94.2	%	PMID[561935]
NPT27	Others	Unspecified		Activity	=	105.0	%	PMID[561935]
NPT27	Others	Unspecified		Activity	=	107.5	%	PMID[561935]
NPT27	Others	Unspecified		Activity	=	107.8	%	PMID[561935]
NPT2	Others	Unspecified		IC50	>	100000.0	nM	PMID[561935]
NPT2	Others	Unspecified		Inhibition	=	33.8	%	PMID[561935]
NPT2	Others	Unspecified		Inhibition	=	36.8	%	PMID[561935]
NPT2	Others	Unspecified		Inhibition	=	33.5	%	PMID[561935]
NPT2	Others	Unspecified		Inhibition	=	31.3	%	PMID[561935]
NPT2	Others	Unspecified		Potency	n.a.	27306	nM	PMID[23819871]
NPT2	Others	Unspecified		Potency	n.a.	54482.7	nM	PMID[10579868]
NPT2	Others	Unspecified		Potency	n.a.	21689.9	nM	PMID[24766560]
NPT2	Others	Unspecified		Potency	n.a.	611.3	nM	PMID[23122818]
NPT2	Others	Unspecified		Potency	n.a.	54014.7	nM	PMID[12773056]
NPT2	Others	Unspecified		Potency	n.a.	6859	nM	PMID[14640526]
NPT2	Others	Unspecified		Potency	n.a.	18997.5	nM	PMID[12608857]
NPT2	Others	Unspecified		Potency	n.a.	21315.5	nM	PMID[1602301]
NPT2	Others	Unspecified		Potency	n.a.	47719.5	nM	PMID[19128055]
NPT2	Others	Unspecified		Potency	n.a.	26834.6	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	30109	nM	PMID[26860736]
NPT2	Others	Unspecified		Potency	n.a.	21689.9	nM	PMID[19113968]
NPT2	Others	Unspecified		Potency	n.a.	60605.5	nM	PMID[21543140]
NPT2	Others	Unspecified		Potency	n.a.	10962.2	nM	DOI[10.1007/s00044-012-0205-9]

☑ 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 NPC250361 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	1383
0.1-0.2	14159
0.2-0.3	16502
0.3-0.4	5577
0.4-0.5	2195
0.5-0.6	1511
0.6-0.7	937
0.7-0.8	335
0.8-0.85	54
0.85-0.9	32
0.9-0.95	5
0.95-1	7

Similarity Score	Similarity Level	Natural Product ID
0.9835	High Similarity	NPC473762
0.9754	High Similarity	NPC473587
0.9675	High Similarity	NPC475428
0.9597	High Similarity	NPC475450
0.9597	High Similarity	NPC179365
0.952	High Similarity	NPC473930
0.95	High Similarity	NPC41174
0.936	High Similarity	NPC22079
0.9084	High Similarity	NPC312092
0.907	High Similarity	NPC198988
0.9	High Similarity	NPC325252
0.8872	High Similarity	NPC115611
0.8872	High Similarity	NPC284635
0.8855	High Similarity	NPC29886
0.8855	High Similarity	NPC218268
0.8855	High Similarity	NPC96102
0.8855	High Similarity	NPC261195
0.8852	High Similarity	NPC162689
0.8852	High Similarity	NPC54102
0.8797	High Similarity	NPC88097
0.8788	High Similarity	NPC84911
0.8788	High Similarity	NPC105127
0.8731	High Similarity	NPC59084
0.8731	High Similarity	NPC2949
0.8692	High Similarity	NPC82295
0.8689	High Similarity	NPC148140
0.8686	High Similarity	NPC288838
0.8667	High Similarity	NPC63157
0.8667	High Similarity	NPC473868
0.8657	High Similarity	NPC73767
0.8657	High Similarity	NPC110126
0.8647	High Similarity	NPC125746
0.8618	High Similarity	NPC81561
0.8593	High Similarity	NPC469783
0.8593	High Similarity	NPC279081
0.8593	High Similarity	NPC469767
0.8593	High Similarity	NPC469768
0.8593	High Similarity	NPC469779
0.8593	High Similarity	NPC469784
0.8593	High Similarity	NPC469761
0.8593	High Similarity	NPC469780
0.8551	High Similarity	NPC63545
0.854	High Similarity	NPC242556
0.8529	High Similarity	NPC469766
0.85	High Similarity	NPC53947
0.8489	Intermediate Similarity	NPC179787
0.8489	Intermediate Similarity	NPC469811
0.8489	Intermediate Similarity	NPC201380
0.8489	Intermediate Similarity	NPC477134
0.8478	Intermediate Similarity	NPC470440
0.8478	Intermediate Similarity	NPC204141
0.8467	Intermediate Similarity	NPC190296
0.8456	Intermediate Similarity	NPC230002
0.8438	Intermediate Similarity	NPC122718
0.8429	Intermediate Similarity	NPC321911
0.8417	Intermediate Similarity	NPC143872
0.8413	Intermediate Similarity	NPC215519
0.838	Intermediate Similarity	NPC325903
0.8369	Intermediate Similarity	NPC33421
0.8357	Intermediate Similarity	NPC21605
0.8345	Intermediate Similarity	NPC314372
0.8345	Intermediate Similarity	NPC159856
0.8298	Intermediate Similarity	NPC37548
0.8298	Intermediate Similarity	NPC124005
0.8239	Intermediate Similarity	NPC148592
0.8227	Intermediate Similarity	NPC471957
0.8207	Intermediate Similarity	NPC216643
0.8207	Intermediate Similarity	NPC76982
0.8169	Intermediate Similarity	NPC2272
0.8151	Intermediate Similarity	NPC221786
0.8151	Intermediate Similarity	NPC92796
0.8151	Intermediate Similarity	NPC475990
0.8151	Intermediate Similarity	NPC474791
0.8151	Intermediate Similarity	NPC135141
0.8151	Intermediate Similarity	NPC474880
0.8112	Intermediate Similarity	NPC105818
0.8112	Intermediate Similarity	NPC24678
0.8095	Intermediate Similarity	NPC215584
0.8095	Intermediate Similarity	NPC229173
0.8095	Intermediate Similarity	NPC44773
0.8082	Intermediate Similarity	NPC286427
0.8082	Intermediate Similarity	NPC236711
0.8069	Intermediate Similarity	NPC470507
0.8069	Intermediate Similarity	NPC471458
0.8069	Intermediate Similarity	NPC38736
0.8056	Intermediate Similarity	NPC470233
0.8056	Intermediate Similarity	NPC216713
0.8056	Intermediate Similarity	NPC470823
0.8042	Intermediate Similarity	NPC187951
0.8028	Intermediate Similarity	NPC129042
0.8027	Intermediate Similarity	NPC56765
0.8027	Intermediate Similarity	NPC41257
0.8027	Intermediate Similarity	NPC318065
0.8027	Intermediate Similarity	NPC206819
0.8014	Intermediate Similarity	NPC285469
0.8014	Intermediate Similarity	NPC184476
0.8014	Intermediate Similarity	NPC141353
0.8	Intermediate Similarity	NPC141926
0.8	Intermediate Similarity	NPC259644
0.8	Intermediate Similarity	NPC469763
0.8	Intermediate Similarity	NPC25008
0.8	Intermediate Similarity	NPC469760
0.8	Intermediate Similarity	NPC73952
0.8	Intermediate Similarity	NPC469765
0.8	Intermediate Similarity	NPC469786
0.8	Intermediate Similarity	NPC200214
0.7987	Intermediate Similarity	NPC317105
0.7973	Intermediate Similarity	NPC470204
0.7973	Intermediate Similarity	NPC122141
0.7959	Intermediate Similarity	NPC299594
0.7945	Intermediate Similarity	NPC75540
0.7945	Intermediate Similarity	NPC70922
0.7945	Intermediate Similarity	NPC80597
0.7945	Intermediate Similarity	NPC34844
0.7945	Intermediate Similarity	NPC212376
0.7945	Intermediate Similarity	NPC211572
0.7939	Intermediate Similarity	NPC46358
0.7919	Intermediate Similarity	NPC470203
0.7902	Intermediate Similarity	NPC316069
0.7895	Intermediate Similarity	NPC476140
0.7891	Intermediate Similarity	NPC469785
0.7877	Intermediate Similarity	NPC232798
0.7867	Intermediate Similarity	NPC162799
0.7857	Intermediate Similarity	NPC104483
0.7852	Intermediate Similarity	NPC279918
0.7852	Intermediate Similarity	NPC473320
0.7847	Intermediate Similarity	NPC114209
0.7842	Intermediate Similarity	NPC314102
0.7842	Intermediate Similarity	NPC150259
0.7842	Intermediate Similarity	NPC251722
0.7838	Intermediate Similarity	NPC469762
0.7829	Intermediate Similarity	NPC63751
0.7823	Intermediate Similarity	NPC476219
0.7823	Intermediate Similarity	NPC476297
0.7815	Intermediate Similarity	NPC274229
0.7805	Intermediate Similarity	NPC302790
0.78	Intermediate Similarity	NPC282231
0.78	Intermediate Similarity	NPC16667
0.7786	Intermediate Similarity	NPC169433
0.7785	Intermediate Similarity	NPC230869
0.7778	Intermediate Similarity	NPC474897
0.7748	Intermediate Similarity	NPC247987
0.7748	Intermediate Similarity	NPC8104
0.7748	Intermediate Similarity	NPC21174
0.7748	Intermediate Similarity	NPC271797
0.7748	Intermediate Similarity	NPC90723
0.7748	Intermediate Similarity	NPC271734
0.7733	Intermediate Similarity	NPC131718
0.7712	Intermediate Similarity	NPC154293
0.7712	Intermediate Similarity	NPC201700
0.7703	Intermediate Similarity	NPC207726
0.7697	Intermediate Similarity	NPC17751
0.7697	Intermediate Similarity	NPC280864
0.7697	Intermediate Similarity	NPC115232
0.7692	Intermediate Similarity	NPC20144
0.7682	Intermediate Similarity	NPC214106
0.7677	Intermediate Similarity	NPC474409
0.7677	Intermediate Similarity	NPC477611
0.7662	Intermediate Similarity	NPC97343
0.7662	Intermediate Similarity	NPC194411
0.7655	Intermediate Similarity	NPC478186
0.7647	Intermediate Similarity	NPC474561
0.7647	Intermediate Similarity	NPC49954
0.7647	Intermediate Similarity	NPC54988
0.7635	Intermediate Similarity	NPC161108
0.7632	Intermediate Similarity	NPC102423
0.7632	Intermediate Similarity	NPC40779
0.7632	Intermediate Similarity	NPC311276
0.7613	Intermediate Similarity	NPC82331
0.7603	Intermediate Similarity	NPC470111
0.7597	Intermediate Similarity	NPC317430
0.758	Intermediate Similarity	NPC280852
0.7564	Intermediate Similarity	NPC252572
0.7564	Intermediate Similarity	NPC97525
0.7557	Intermediate Similarity	NPC91958
0.7552	Intermediate Similarity	NPC238499
0.755	Intermediate Similarity	NPC67056
0.7548	Intermediate Similarity	NPC280548
0.7548	Intermediate Similarity	NPC471943
0.7536	Intermediate Similarity	NPC282398
0.7532	Intermediate Similarity	NPC109447
0.7532	Intermediate Similarity	NPC284775
0.7532	Intermediate Similarity	NPC49217
0.7532	Intermediate Similarity	NPC160105
0.7532	Intermediate Similarity	NPC59269
0.7532	Intermediate Similarity	NPC470509
0.7516	Intermediate Similarity	NPC329688
0.7516	Intermediate Similarity	NPC37423
0.7516	Intermediate Similarity	NPC189812
0.7516	Intermediate Similarity	NPC472587
0.7516	Intermediate Similarity	NPC275305
0.7516	Intermediate Similarity	NPC149265
0.75	Intermediate Similarity	NPC470498
0.75	Intermediate Similarity	NPC40070
0.75	Intermediate Similarity	NPC277157
0.75	Intermediate Similarity	NPC6982
0.7484	Intermediate Similarity	NPC78020
0.7484	Intermediate Similarity	NPC88363
0.7481	Intermediate Similarity	NPC27740
0.7468	Intermediate Similarity	NPC151635

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 NPC250361 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	582
0.1-0.2	925
0.2-0.3	1008
0.3-0.4	2177
0.4-0.5	2370
0.5-0.6	1460
0.6-0.7	519
0.7-0.8	89
0.8-0.85	12
0.85-0.9	6
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9225	High Similarity	NPD1262	Discovery
0.9015	High Similarity	NPD3943	Clinical (unspecified phase)
0.8855	High Similarity	NPD198	Clinical (unspecified phase)
0.8815	High Similarity	NPD5254	Discontinued
0.8686	High Similarity	NPD1528	Clinical (unspecified phase)
0.8667	High Similarity	NPD1722	Approved
0.8657	High Similarity	NPD786	Approved
0.8561	High Similarity	NPD4374	Clinical (unspecified phase)
0.8538	High Similarity	NPD947	Approved
0.85	High Similarity	NPD4463	Approved
0.85	High Similarity	NPD4462	Approved
0.8496	Intermediate Similarity	NPD4880	Discontinued
0.8467	Intermediate Similarity	NPD4637	Clinical (unspecified phase)
0.8421	Intermediate Similarity	NPD3385	Approved
0.8298	Intermediate Similarity	NPD3100	Discontinued
0.8258	Intermediate Similarity	NPD3654	Approved
0.8252	Intermediate Similarity	NPD2837	Discontinued
0.8162	Intermediate Similarity	NPD1255	Approved
0.8162	Intermediate Similarity	NPD1256	Approved
0.8162	Intermediate Similarity	NPD1254	Approved
0.8162	Intermediate Similarity	NPD1253	Approved
0.8156	Intermediate Similarity	NPD1683	Approved
0.8134	Intermediate Similarity	NPD1251	Discontinued
0.8112	Intermediate Similarity	NPD2172	Phase 1
0.8	Intermediate Similarity	NPD1592	Phase 3
0.7987	Intermediate Similarity	NPD3323	Discontinued
0.7986	Intermediate Similarity	NPD3833	Phase 3
0.7986	Intermediate Similarity	NPD3835	Phase 3
0.7971	Intermediate Similarity	NPD6554	Approved
0.7971	Intermediate Similarity	NPD45	Approved
0.7919	Intermediate Similarity	NPD972	Clinical (unspecified phase)
0.7919	Intermediate Similarity	NPD1853	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD680	Discontinued
0.7829	Intermediate Similarity	NPD5069	Clinical (unspecified phase)
0.7815	Intermediate Similarity	NPD5744	Clinical (unspecified phase)
0.7733	Intermediate Similarity	NPD1404	Approved
0.7733	Intermediate Similarity	NPD1403	Approved
0.7704	Intermediate Similarity	NPD992	Clinical (unspecified phase)
0.7704	Intermediate Similarity	NPD991	Phase 2
0.7662	Intermediate Similarity	NPD1325	Approved
0.7662	Intermediate Similarity	NPD1326	Approved
0.7628	Intermediate Similarity	NPD5065	Approved
0.7613	Intermediate Similarity	NPD3610	Approved
0.7613	Intermediate Similarity	NPD3609	Approved
0.7603	Intermediate Similarity	NPD4547	Phase 3
0.7597	Intermediate Similarity	NPD2641	Approved
0.7597	Intermediate Similarity	NPD2640	Approved
0.7594	Intermediate Similarity	NPD1561	Phase 2
0.7569	Intermediate Similarity	NPD2006	Phase 2
0.7564	Intermediate Similarity	NPD4112	Clinical (unspecified phase)
0.7551	Intermediate Similarity	NPD2430	Phase 2
0.7536	Intermediate Similarity	NPD3476	Approved
0.7536	Intermediate Similarity	NPD3475	Approved
0.7533	Intermediate Similarity	NPD2150	Discontinued
0.7532	Intermediate Similarity	NPD2642	Approved
0.7532	Intermediate Similarity	NPD2639	Approved
0.7532	Intermediate Similarity	NPD6203	Clinical (unspecified phase)
0.7517	Intermediate Similarity	NPD3401	Clinical (unspecified phase)
0.7517	Intermediate Similarity	NPD4509	Discontinued
0.7516	Intermediate Similarity	NPD4128	Approved
0.75	Intermediate Similarity	NPD3834	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD993	Approved
0.75	Intermediate Similarity	NPD990	Approved
0.7484	Intermediate Similarity	NPD5021	Discontinued
0.7484	Intermediate Similarity	NPD2185	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD1192	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD4075	Phase 2
0.7448	Intermediate Similarity	NPD4047	Discontinued
0.7445	Intermediate Similarity	NPD2119	Approved
0.7445	Intermediate Similarity	NPD2118	Approved
0.7438	Intermediate Similarity	NPD6595	Phase 3
0.7438	Intermediate Similarity	NPD8464	Clinical (unspecified phase)
0.7438	Intermediate Similarity	NPD6277	Clinical (unspecified phase)
0.7438	Intermediate Similarity	NPD5473	Discontinued
0.7436	Intermediate Similarity	NPD4184	Clinical (unspecified phase)
0.7421	Intermediate Similarity	NPD3505	Approved
0.7421	Intermediate Similarity	NPD4181	Approved
0.7421	Intermediate Similarity	NPD3506	Approved
0.7391	Intermediate Similarity	NPD1895	Discontinued
0.7389	Intermediate Similarity	NPD6827	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD6828	Phase 2
0.7375	Intermediate Similarity	NPD4076	Approved
0.7375	Intermediate Similarity	NPD4079	Approved
0.7368	Intermediate Similarity	NPD4326	Phase 2
0.7351	Intermediate Similarity	NPD1597	Phase 1
0.7346	Intermediate Similarity	NPD3318	Approved
0.7346	Intermediate Similarity	NPD5105	Approved
0.7346	Intermediate Similarity	NPD3320	Approved
0.7346	Intermediate Similarity	NPD5106	Approved
0.7346	Intermediate Similarity	NPD3319	Phase 1
0.7329	Intermediate Similarity	NPD2007	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD1554	Clinical (unspecified phase)
0.7315	Intermediate Similarity	NPD5538	Clinical (unspecified phase)
0.7296	Intermediate Similarity	NPD482	Approved
0.7267	Intermediate Similarity	NPD8386	Phase 2
0.7261	Intermediate Similarity	NPD4779	Clinical (unspecified phase)
0.7256	Intermediate Similarity	NPD6610	Clinical (unspecified phase)
0.7254	Intermediate Similarity	NPD4029	Approved
0.7254	Intermediate Similarity	NPD4030	Approved
0.7254	Intermediate Similarity	NPD4028	Approved
0.725	Intermediate Similarity	NPD749	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD9583	Approved
0.7222	Intermediate Similarity	NPD702	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD6158	Phase 2
0.7219	Intermediate Similarity	NPD6476	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD5436	Phase 1
0.7212	Intermediate Similarity	NPD6217	Discontinued
0.7212	Intermediate Similarity	NPD4426	Clinical (unspecified phase)
0.7206	Intermediate Similarity	NPD5787	Discontinued
0.7205	Intermediate Similarity	NPD2144	Approved
0.7197	Intermediate Similarity	NPD1248	Discontinued
0.7195	Intermediate Similarity	NPD3607	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD2580	Discontinued
0.719	Intermediate Similarity	NPD473	Clinical (unspecified phase)
0.7185	Intermediate Similarity	NPD4811	Discontinued
0.7179	Intermediate Similarity	NPD5140	Approved
0.7179	Intermediate Similarity	NPD5138	Approved
0.7178	Intermediate Similarity	NPD1707	Approved
0.7178	Intermediate Similarity	NPD1708	Approved
0.7169	Intermediate Similarity	NPD5590	Clinical (unspecified phase)
0.7169	Intermediate Similarity	NPD8431	Approved
0.7163	Intermediate Similarity	NPD715	Phase 3
0.7162	Intermediate Similarity	NPD1918	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD2330	Approved
0.7143	Intermediate Similarity	NPD2865	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD5728	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD4550	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD1332	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD3942	Approved
0.7133	Intermediate Similarity	NPD3944	Approved
0.7132	Intermediate Similarity	NPD270	Clinical (unspecified phase)
0.7132	Intermediate Similarity	NPD271	Approved
0.7132	Intermediate Similarity	NPD268	Approved
0.7126	Intermediate Similarity	NPD8110	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD1534	Approved
0.7124	Intermediate Similarity	NPD2165	Phase 1
0.7124	Intermediate Similarity	NPD977	Approved
0.7124	Intermediate Similarity	NPD976	Approved
0.7124	Intermediate Similarity	NPD975	Approved
0.7123	Intermediate Similarity	NPD768	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD2385	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD5315	Discontinued
0.7105	Intermediate Similarity	NPD2882	Phase 1
0.7101	Intermediate Similarity	NPD9357	Approved
0.7099	Intermediate Similarity	NPD4398	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD2392	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD3114	Approved
0.7078	Intermediate Similarity	NPD2927	Phase 3
0.7078	Intermediate Similarity	NPD3112	Approved
0.7078	Intermediate Similarity	NPD2748	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD3115	Approved
0.7078	Intermediate Similarity	NPD3113	Approved
0.7073	Intermediate Similarity	NPD3038	Discontinued
0.7071	Intermediate Similarity	NPD1598	Discontinued
0.7066	Intermediate Similarity	NPD3961	Discontinued
0.7066	Intermediate Similarity	NPD3486	Clinical (unspecified phase)
0.7066	Intermediate Similarity	NPD6141	Clinical (unspecified phase)
0.7066	Intermediate Similarity	NPD2310	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD2844	Phase 3
0.7041	Intermediate Similarity	NPD5912	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD5913	Phase 3
0.7041	Intermediate Similarity	NPD6180	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD2092	Phase 2
0.703	Intermediate Similarity	NPD2094	Phase 2
0.703	Intermediate Similarity	NPD2095	Phase 2
0.7027	Intermediate Similarity	NPD5020	Approved
0.7013	Intermediate Similarity	NPD6285	Phase 2
0.7012	Intermediate Similarity	NPD5962	Phase 2
0.6988	Remote Similarity	NPD2091	Phase 2
0.6988	Remote Similarity	NPD2096	Phase 2
0.6974	Remote Similarity	NPD3852	Clinical (unspecified phase)
0.6972	Remote Similarity	NPD6451	Discontinued
0.697	Remote Similarity	NPD4399	Phase 2
0.697	Remote Similarity	NPD4649	Clinical (unspecified phase)
0.6963	Remote Similarity	NPD9392	Approved
0.6963	Remote Similarity	NPD9396	Approved
0.6962	Remote Similarity	NPD404	Discontinued
0.6959	Remote Similarity	NPD5575	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD1567	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD6448	Phase 1
0.6946	Remote Similarity	NPD1227	Phase 2
0.6941	Remote Similarity	NPD6630	Clinical (unspecified phase)
0.694	Remote Similarity	NPD269	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD4638	Approved
0.6937	Remote Similarity	NPD4639	Approved
0.6937	Remote Similarity	NPD4640	Approved
0.6923	Remote Similarity	NPD1648	Phase 1
0.6923	Remote Similarity	NPD1647	Phase 1
0.6919	Remote Similarity	NPD7619	Phase 3
0.6919	Remote Similarity	NPD7618	Phase 3
0.6918	Remote Similarity	NPD1313	Approved
0.6918	Remote Similarity	NPD509	Phase 3
0.6918	Remote Similarity	NPD2915	Discontinued
0.6914	Remote Similarity	NPD750	Phase 2
0.6908	Remote Similarity	NPD1661	Suspended
0.6892	Remote Similarity	NPD2070	Approved
0.6892	Remote Similarity	NPD2073	Approved
0.6892	Remote Similarity	NPD2075	Approved
0.6892	Remote Similarity	NPD2071	Approved
0.6892	Remote Similarity	NPD2068	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