NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	186.08
Volume:	190.744
LogP:	2.181
LogD:	2.168
LogS:	-2.773
# Rotatable Bonds:	0
TPSA:	44.89
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.642
Synthetic Accessibility Score:	2.275
Fsp3:	0.182
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:	-4.903
MDCK Permeability:	1.211540075019002e-05
Pgp-inhibitor:	0.003
Pgp-substrate:	0.775
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.034
30% Bioavailability (F30%):	0.945

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.844
Plasma Protein Binding (PPB):	60.43206787109375%
Volume Distribution (VD):	1.289
Pgp-substrate:	23.544748306274414%

ADMET: Metabolism

CYP1A2-inhibitor:	0.983
CYP1A2-substrate:	0.447
CYP2C19-inhibitor:	0.355
CYP2C19-substrate:	0.225
CYP2C9-inhibitor:	0.114
CYP2C9-substrate:	0.916
CYP2D6-inhibitor:	0.253
CYP2D6-substrate:	0.795
CYP3A4-inhibitor:	0.171
CYP3A4-substrate:	0.214

ADMET: Excretion

Clearance (CL):	7.349
Half-life (T1/2):	0.692

ADMET: Toxicity

hERG Blockers:	0.039
Human Hepatotoxicity (H-HT):	0.661
Drug-inuced Liver Injury (DILI):	0.12
AMES Toxicity:	0.34
Rat Oral Acute Toxicity:	0.475
Maximum Recommended Daily Dose:	0.838
Skin Sensitization:	0.584
Carcinogencity:	0.099
Eye Corrosion:	0.005
Eye Irritation:	0.411
Respiratory Toxicity:	0.967

Download Data

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

Natural Product: NPC141353

Natural Product ID:	NPC141353
*Common Name:**
IUPAC Name:	2,3,4,9-tetrahydropyrido[3,4-b]indol-1-one
Synonyms:
Standard InCHIKey:	FZHZQHNKCPJTNQ-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C11H10N2O/c14-11-10-8(5-6-12-11)7-3-1-2-4-9(7)13-10/h1-4,13H,5-6H2,(H,12,14)
SMILES:	c1ccc2c(c1)c1CCN=C(c1[nH]2)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL444810
PubChem CID:	87371
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000211] Indoles and derivatives [CHEMONTID:0001213] Pyridoindoles [CHEMONTID:0001914] Beta carbolines

*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
NPO32531	sponge sp.	Species	n.a.	n.a.	n.a.	collected from vertical slopes between 33 and 40 m from Knife Cape, Manado Bay, Indonesia	2011-MAR	PMID[12828469]
NPO503	Trigonostemon lii	Species	Euphorbiaceae	Eukaryota	leaves	n.a.	n.a.	PMID[22342628]
NPO503	Trigonostemon lii	Species	Euphorbiaceae	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
IC50	5
Others	8
Potency	14

Activity Type	# Activity
Cell Line	5
Individual Protein	13
Organism	9
Others	1
Protein-Protein Interaction	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT48	Individual Protein	Lysine-specific demethylase 4D-like	Homo sapiens	Potency	=	28183.8	nM	PMID[470716]
NPT48	Individual Protein	Lysine-specific demethylase 4D-like	Homo sapiens	Potency	=	31622.8	nM	PMID[470717]
NPT1197	Individual Protein	Huntingtin	Homo sapiens	Potency	=	5011.9	nM	PMID[470717]
NPT56	Individual Protein	Beta-lactamase AmpC	Escherichia coli K-12	Potency	=	7079.5	nM	PMID[470716]
NPT151	Individual Protein	15-hydroxyprostaglandin dehydrogenase [NAD+]	Homo sapiens	Potency	=	28183.8	nM	PMID[470716]
NPT208	Individual Protein	Cytochrome P450 1A2	Homo sapiens	AC50	=	2818.38	nM	PMID[470716]
NPT213	Individual Protein	Cytochrome P450 2C19	Homo sapiens	AC50	=	15848.93	nM	PMID[470716]
NPT116	Cell Line	HL-60	Homo sapiens	IC50	>	40000.0	nM	PMID[470719]
NPT659	Cell Line	SMMC-7721	Homo sapiens	IC50	>	40000.0	nM	PMID[470719]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	40000.0	nM	PMID[470719]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	40000.0	nM	PMID[470719]
NPT660	Cell Line	SW480	Homo sapiens	IC50	>	40000.0	nM	PMID[470719]
NPT1474	Individual Protein	ATP-dependent Clp protease proteolytic subunit	Bacillus subtilis (strain 168)	Potency	n.a.	25118.9	nM	PMID[470718]
NPT11	Individual Protein	Guanine nucleotide-binding protein G(s), subunit alpha	Homo sapiens	Potency	n.a.	25118.9	nM	PMID[470718]
NPT105	Individual Protein	Muscleblind-like protein 1	Homo sapiens	Potency	n.a.	7079.5	nM	PMID[470717]
NPT197	Protein-Protein Interaction	Menin/Histone-lysine N-methyltransferase MLL	Homo sapiens	Potency	=	3548.1	nM	PMID[470716]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Potency	n.a.	14715.7	nM	PMID[470717]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Potency	n.a.	16511.3	nM	PMID[470716]
NPT9	Individual Protein	DNA polymerase eta	Homo sapiens	Potency	n.a.	39810.7	nM	PMID[470718]
NPT7	Individual Protein	Thioredoxin reductase 1, cytoplasmic	Rattus norvegicus	Potency	n.a.	14125.4	nM	PMID[470718]
NPT755	Individual Protein	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	Homo sapiens	Potency	n.a.	95283.4	nM	PMID[470718]
NPT35	Others	n.a.		Solubility	n.a.	1258900.0	nM	PMID[470720]
NPT19	Organism	Escherichia coli	Escherichia coli	Inhibition	=	-11.15	%	PMID[470721]
NPT20	Organism	Candida albicans	Candida albicans	Inhibition	=	2.99	%	PMID[470721]
NPT85	Organism	Filobasidiella neoformans	Cryptococcus neoformans	Inhibition	=	-7.2	%	PMID[470721]
NPT2922	Organism	Staphylococcus aureus subsp. aureus	Staphylococcus aureus subsp. aureus	Inhibition	=	-13.58	%	PMID[470721]
NPT747	Organism	Acinetobacter baumannii	Acinetobacter baumannii	Inhibition	=	-2.97	%	PMID[470721]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	Inhibition	=	-19.46	%	PMID[470721]
NPT173	Organism	Klebsiella pneumoniae	Klebsiella pneumoniae	Inhibition	=	6.5	%	PMID[470721]

☑ 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 NPC141353 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	514
0.1-0.2	4948
0.2-0.3	13150
0.3-0.4	15720
0.4-0.5	3885
0.5-0.6	2340
0.6-0.7	1514
0.7-0.8	557
0.8-0.85	60
0.85-0.9	8
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8824	High Similarity	NPC285469
0.8774	High Similarity	NPC131718
0.8742	High Similarity	NPC37548
0.8704	High Similarity	NPC72980
0.86	High Similarity	NPC242556
0.8599	High Similarity	NPC16667
0.8571	High Similarity	NPC34508
0.8544	High Similarity	NPC102423
0.8535	High Similarity	NPC279918
0.8516	High Similarity	NPC207726
0.8516	High Similarity	NPC470507
0.8516	High Similarity	NPC38736
0.8497	Intermediate Similarity	NPC187951
0.8485	Intermediate Similarity	NPC314394
0.8481	Intermediate Similarity	NPC282231
0.8434	Intermediate Similarity	NPC48938
0.8414	Intermediate Similarity	NPC22079
0.8397	Intermediate Similarity	NPC471458
0.8377	Intermediate Similarity	NPC124005
0.8364	Intermediate Similarity	NPC472443
0.8364	Intermediate Similarity	NPC270009
0.8354	Intermediate Similarity	NPC230869
0.8354	Intermediate Similarity	NPC67056
0.8344	Intermediate Similarity	NPC474409
0.8333	Intermediate Similarity	NPC280548
0.8323	Intermediate Similarity	NPC54988
0.8323	Intermediate Similarity	NPC474561
0.8323	Intermediate Similarity	NPC49954
0.8301	Intermediate Similarity	NPC159856
0.8294	Intermediate Similarity	NPC221873
0.8272	Intermediate Similarity	NPC317430
0.8272	Intermediate Similarity	NPC63751
0.8263	Intermediate Similarity	NPC192270
0.8242	Intermediate Similarity	NPC288785
0.8232	Intermediate Similarity	NPC313791
0.8217	Intermediate Similarity	NPC73952
0.8217	Intermediate Similarity	NPC469763
0.8217	Intermediate Similarity	NPC25008
0.8217	Intermediate Similarity	NPC469765
0.8217	Intermediate Similarity	NPC469786
0.8217	Intermediate Similarity	NPC469760
0.8217	Intermediate Similarity	NPC259644
0.8214	Intermediate Similarity	NPC472444
0.8199	Intermediate Similarity	NPC476118
0.8193	Intermediate Similarity	NPC293472
0.8187	Intermediate Similarity	NPC473320
0.8176	Intermediate Similarity	NPC299594
0.8171	Intermediate Similarity	NPC158129
0.8165	Intermediate Similarity	NPC75540
0.8165	Intermediate Similarity	NPC80597
0.8165	Intermediate Similarity	NPC70922
0.8165	Intermediate Similarity	NPC211572
0.8165	Intermediate Similarity	NPC212376
0.8161	Intermediate Similarity	NPC276517
0.8148	Intermediate Similarity	NPC470508
0.8144	Intermediate Similarity	NPC88363
0.8129	Intermediate Similarity	NPC129042
0.8118	Intermediate Similarity	NPC15102
0.8113	Intermediate Similarity	NPC469785
0.8113	Intermediate Similarity	NPC184476
0.8107	Intermediate Similarity	NPC176127
0.8107	Intermediate Similarity	NPC220765
0.8089	Intermediate Similarity	NPC24678
0.8089	Intermediate Similarity	NPC105818
0.8086	Intermediate Similarity	NPC194640
0.8072	Intermediate Similarity	NPC472586
0.8065	Intermediate Similarity	NPC314372
0.8063	Intermediate Similarity	NPC469762
0.8061	Intermediate Similarity	NPC470498
0.8059	Intermediate Similarity	NPC204717
0.8059	Intermediate Similarity	NPC84478
0.8052	Intermediate Similarity	NPC190296
0.8023	Intermediate Similarity	NPC306376
0.8023	Intermediate Similarity	NPC46580
0.8014	Intermediate Similarity	NPC250361
0.8012	Intermediate Similarity	NPC314002
0.8011	Intermediate Similarity	NPC242209
0.8	Intermediate Similarity	NPC212535
0.7988	Intermediate Similarity	NPC160105
0.7987	Intermediate Similarity	NPC60553
0.7977	Intermediate Similarity	NPC46413
0.7976	Intermediate Similarity	NPC59269
0.7976	Intermediate Similarity	NPC183662
0.7976	Intermediate Similarity	NPC15573
0.7976	Intermediate Similarity	NPC217372
0.7976	Intermediate Similarity	NPC248454
0.7975	Intermediate Similarity	NPC311276
0.7975	Intermediate Similarity	NPC472587
0.7975	Intermediate Similarity	NPC271734
0.7965	Intermediate Similarity	NPC171171
0.7953	Intermediate Similarity	NPC190007
0.7953	Intermediate Similarity	NPC284678
0.7952	Intermediate Similarity	NPC6982
0.7947	Intermediate Similarity	NPC198988
0.7929	Intermediate Similarity	NPC219336
0.7921	Intermediate Similarity	NPC192315
0.7917	Intermediate Similarity	NPC134586
0.7907	Intermediate Similarity	NPC476319
0.7907	Intermediate Similarity	NPC94943
0.7905	Intermediate Similarity	NPC473762
0.7904	Intermediate Similarity	NPC472123
0.7901	Intermediate Similarity	NPC92796
0.7901	Intermediate Similarity	NPC135141
0.7895	Intermediate Similarity	NPC325252
0.7877	Intermediate Similarity	NPC476167
0.787	Intermediate Similarity	NPC211997
0.787	Intermediate Similarity	NPC96890
0.787	Intermediate Similarity	NPC184964
0.7865	Intermediate Similarity	NPC141454
0.7862	Intermediate Similarity	NPC41174
0.7857	Intermediate Similarity	NPC329688
0.7857	Intermediate Similarity	NPC189812
0.7853	Intermediate Similarity	NPC195314
0.7852	Intermediate Similarity	NPC473587
0.7843	Intermediate Similarity	NPC125746
0.7841	Intermediate Similarity	NPC99666
0.7834	Intermediate Similarity	NPC470440
0.78	Intermediate Similarity	NPC475428
0.7798	Intermediate Similarity	NPC314603
0.7791	Intermediate Similarity	NPC19679
0.7791	Intermediate Similarity	NPC163055
0.7778	Intermediate Similarity	NPC91179
0.7778	Intermediate Similarity	NPC218268
0.7778	Intermediate Similarity	NPC96102
0.7778	Intermediate Similarity	NPC32200
0.7771	Intermediate Similarity	NPC246700
0.7771	Intermediate Similarity	NPC128751
0.7771	Intermediate Similarity	NPC49217
0.7771	Intermediate Similarity	NPC109447
0.7765	Intermediate Similarity	NPC111275
0.7765	Intermediate Similarity	NPC232130
0.7751	Intermediate Similarity	NPC110500
0.7751	Intermediate Similarity	NPC203468
0.7751	Intermediate Similarity	NPC149155
0.7748	Intermediate Similarity	NPC179365
0.7748	Intermediate Similarity	NPC475450
0.7742	Intermediate Similarity	NPC88097
0.774	Intermediate Similarity	NPC324149
0.7736	Intermediate Similarity	NPC471957
0.7727	Intermediate Similarity	NPC469497
0.7727	Intermediate Similarity	NPC84911
0.7727	Intermediate Similarity	NPC106833
0.7727	Intermediate Similarity	NPC105127
0.7725	Intermediate Similarity	NPC201700
0.7725	Intermediate Similarity	NPC78020
0.7722	Intermediate Similarity	NPC470499
0.7719	Intermediate Similarity	NPC248041
0.7719	Intermediate Similarity	NPC42979
0.7719	Intermediate Similarity	NPC126709
0.7719	Intermediate Similarity	NPC283219
0.7706	Intermediate Similarity	NPC224764
0.7706	Intermediate Similarity	NPC267885
0.7705	Intermediate Similarity	NPC476098
0.7701	Intermediate Similarity	NPC188387
0.7701	Intermediate Similarity	NPC163421
0.7697	Intermediate Similarity	NPC473930
0.7692	Intermediate Similarity	NPC59084
0.7692	Intermediate Similarity	NPC115611
0.7692	Intermediate Similarity	NPC2949
0.7688	Intermediate Similarity	NPC288445
0.768	Intermediate Similarity	NPC128823
0.7679	Intermediate Similarity	NPC194411
0.7673	Intermediate Similarity	NPC143872
0.767	Intermediate Similarity	NPC242928
0.7667	Intermediate Similarity	NPC77555
0.7662	Intermediate Similarity	NPC29886
0.7662	Intermediate Similarity	NPC261195
0.7651	Intermediate Similarity	NPC40779
0.7643	Intermediate Similarity	NPC63157
0.7643	Intermediate Similarity	NPC473868
0.7637	Intermediate Similarity	NPC470497
0.7637	Intermediate Similarity	NPC249040
0.763	Intermediate Similarity	NPC233936
0.763	Intermediate Similarity	NPC71037
0.7628	Intermediate Similarity	NPC110126
0.7628	Intermediate Similarity	NPC73767
0.7627	Intermediate Similarity	NPC83111
0.7622	Intermediate Similarity	NPC212742
0.7619	Intermediate Similarity	NPC154293
0.7616	Intermediate Similarity	NPC176199
0.7616	Intermediate Similarity	NPC215795
0.7614	Intermediate Similarity	NPC278434
0.7609	Intermediate Similarity	NPC165599
0.76	Intermediate Similarity	NPC473189
0.7596	Intermediate Similarity	NPC471944
0.7593	Intermediate Similarity	NPC216713
0.7586	Intermediate Similarity	NPC472108
0.7586	Intermediate Similarity	NPC139291
0.758	Intermediate Similarity	NPC469761
0.758	Intermediate Similarity	NPC469768
0.758	Intermediate Similarity	NPC469784
0.758	Intermediate Similarity	NPC469783
0.758	Intermediate Similarity	NPC469767
0.758	Intermediate Similarity	NPC279081
0.758	Intermediate Similarity	NPC469779
0.758	Intermediate Similarity	NPC469780
0.7572	Intermediate Similarity	NPC469896
0.7569	Intermediate Similarity	NPC156704
0.7568	Intermediate Similarity	NPC470500
0.7568	Intermediate Similarity	NPC470505

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 NPC141353 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	265
0.1-0.2	670
0.2-0.3	824
0.3-0.4	1328
0.4-0.5	2717
0.5-0.6	2418
0.6-0.7	775
0.7-0.8	140
0.8-0.85	11
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8797	High Similarity	NPD1325	Approved
0.8797	High Similarity	NPD1326	Approved
0.8591	High Similarity	NPD1592	Phase 3
0.8405	Intermediate Similarity	NPD5065	Approved
0.8343	Intermediate Similarity	NPD6141	Clinical (unspecified phase)
0.8205	Intermediate Similarity	NPD4463	Approved
0.8205	Intermediate Similarity	NPD4462	Approved
0.8199	Intermediate Similarity	NPD5140	Approved
0.8199	Intermediate Similarity	NPD5138	Approved
0.8038	Intermediate Similarity	NPD6158	Phase 2
0.8038	Intermediate Similarity	NPD6476	Clinical (unspecified phase)
0.8025	Intermediate Similarity	NPD972	Clinical (unspecified phase)
0.8011	Intermediate Similarity	NPD6449	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD5575	Clinical (unspecified phase)
0.7925	Intermediate Similarity	NPD2882	Phase 1
0.7917	Intermediate Similarity	NPD2381	Approved
0.7917	Intermediate Similarity	NPD2380	Approved
0.7917	Intermediate Similarity	NPD2382	Approved
0.7901	Intermediate Similarity	NPD1554	Clinical (unspecified phase)
0.7895	Intermediate Similarity	NPD5596	Phase 2
0.7892	Intermediate Similarity	NPD4184	Clinical (unspecified phase)
0.7882	Intermediate Similarity	NPD6452	Discontinued
0.7861	Intermediate Similarity	NPD706	Phase 1
0.7853	Intermediate Similarity	NPD3791	Clinical (unspecified phase)
0.784	Intermediate Similarity	NPD4671	Clinical (unspecified phase)
0.784	Intermediate Similarity	NPD4670	Clinical (unspecified phase)
0.784	Intermediate Similarity	NPD4669	Clinical (unspecified phase)
0.7831	Intermediate Similarity	NPD2844	Phase 3
0.7831	Intermediate Similarity	NPD5069	Clinical (unspecified phase)
0.7784	Intermediate Similarity	NPD5913	Phase 3
0.7784	Intermediate Similarity	NPD5912	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD198	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD8464	Clinical (unspecified phase)
0.7765	Intermediate Similarity	NPD7948	Phase 1
0.7751	Intermediate Similarity	NPD482	Approved
0.7706	Intermediate Similarity	NPD749	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD3943	Clinical (unspecified phase)
0.7674	Intermediate Similarity	NPD6595	Phase 3
0.7667	Intermediate Similarity	NPD5003	Discontinued
0.7663	Intermediate Similarity	NPD5901	Discontinued
0.7661	Intermediate Similarity	NPD6203	Clinical (unspecified phase)
0.7643	Intermediate Similarity	NPD1722	Approved
0.7628	Intermediate Similarity	NPD786	Approved
0.7616	Intermediate Similarity	NPD4076	Approved
0.7616	Intermediate Similarity	NPD4079	Approved
0.7616	Intermediate Similarity	NPD8386	Phase 2
0.7614	Intermediate Similarity	NPD2383	Phase 1
0.7613	Intermediate Similarity	NPD1262	Discovery
0.7605	Intermediate Similarity	NPD5744	Clinical (unspecified phase)
0.7598	Intermediate Similarity	NPD1304	Clinical (unspecified phase)
0.7596	Intermediate Similarity	NPD4511	Phase 1
0.7582	Intermediate Similarity	NPD3814	Phase 1
0.7578	Intermediate Similarity	NPD4374	Clinical (unspecified phase)
0.7578	Intermediate Similarity	NPD3100	Discontinued
0.7576	Intermediate Similarity	NPD5255	Approved
0.7571	Intermediate Similarity	NPD6965	Clinical (unspecified phase)
0.7558	Intermediate Similarity	NPD3505	Approved
0.7558	Intermediate Similarity	NPD3506	Approved
0.7558	Intermediate Similarity	NPD6159	Phase 2
0.7547	Intermediate Similarity	NPD5254	Discontinued
0.7544	Intermediate Similarity	NPD6492	Phase 2
0.7542	Intermediate Similarity	NPD3404	Approved
0.7541	Intermediate Similarity	NPD484	Approved
0.7528	Intermediate Similarity	NPD2565	Phase 2
0.7528	Intermediate Similarity	NPD2564	Approved
0.75	Intermediate Similarity	NPD802	Phase 2
0.75	Intermediate Similarity	NPD6344	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6610	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1038	Approved
0.7486	Intermediate Similarity	NPD2094	Phase 2
0.7486	Intermediate Similarity	NPD2095	Phase 2
0.7486	Intermediate Similarity	NPD2092	Phase 2
0.7486	Intermediate Similarity	NPD5728	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD1685	Approved
0.7485	Intermediate Similarity	NPD1684	Approved
0.7484	Intermediate Similarity	NPD3525	Discontinued
0.7473	Intermediate Similarity	NPD2721	Clinical (unspecified phase)
0.7457	Intermediate Similarity	NPD2144	Approved
0.7443	Intermediate Similarity	NPD2091	Phase 2
0.7443	Intermediate Similarity	NPD2096	Phase 2
0.7433	Intermediate Similarity	NPD3003	Approved
0.7423	Intermediate Similarity	NPD3835	Phase 3
0.7423	Intermediate Similarity	NPD3833	Phase 3
0.7416	Intermediate Similarity	NPD8431	Approved
0.7391	Intermediate Similarity	NPD2175	Phase 3
0.7391	Intermediate Similarity	NPD2176	Approved
0.7391	Intermediate Similarity	NPD2177	Approved
0.7391	Intermediate Similarity	NPD1768	Approved
0.7384	Intermediate Similarity	NPD750	Phase 2
0.7374	Intermediate Similarity	NPD8110	Clinical (unspecified phase)
0.734	Intermediate Similarity	NPD2715	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD4499	Approved
0.733	Intermediate Similarity	NPD4203	Approved
0.733	Intermediate Similarity	NPD4204	Approved
0.733	Intermediate Similarity	NPD3038	Discontinued
0.7326	Intermediate Similarity	NPD5934	Clinical (unspecified phase)
0.7325	Intermediate Similarity	NPD3864	Clinical (unspecified phase)
0.7318	Intermediate Similarity	NPD4948	Discontinued
0.731	Intermediate Similarity	NPD5021	Discontinued
0.7301	Intermediate Similarity	NPD4702	Approved
0.7301	Intermediate Similarity	NPD4703	Approved
0.7299	Intermediate Similarity	NPD5100	Phase 3
0.7297	Intermediate Similarity	NPD4118	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD8395	Approved
0.7297	Intermediate Similarity	NPD8396	Approved
0.7283	Intermediate Similarity	NPD4112	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD1534	Approved
0.7273	Intermediate Similarity	NPD3654	Approved
0.7268	Intermediate Similarity	NPD3810	Clinical (unspecified phase)
0.7268	Intermediate Similarity	NPD3324	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD4637	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD995	Clinical (unspecified phase)
0.7251	Intermediate Similarity	NPD425	Approved
0.7251	Intermediate Similarity	NPD424	Approved
0.7251	Intermediate Similarity	NPD4554	Clinical (unspecified phase)
0.7249	Intermediate Similarity	NPD4862	Clinical (unspecified phase)
0.7243	Intermediate Similarity	NPD3230	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD4128	Approved
0.7241	Intermediate Similarity	NPD9690	Approved
0.724	Intermediate Similarity	NPD7470	Discontinued
0.7238	Intermediate Similarity	NPD1043	Phase 3
0.7232	Intermediate Similarity	NPD3178	Discontinued
0.7229	Intermediate Similarity	NPD2837	Discontinued
0.7222	Intermediate Similarity	NPD3813	Approved
0.7219	Intermediate Similarity	NPD112	Approved
0.7219	Intermediate Similarity	NPD9705	Discontinued
0.7216	Intermediate Similarity	NPD3417	Phase 1
0.7212	Intermediate Similarity	NPD2172	Phase 1
0.7209	Intermediate Similarity	NPD4640	Approved
0.7209	Intermediate Similarity	NPD4639	Approved
0.7209	Intermediate Similarity	NPD4638	Approved
0.7207	Intermediate Similarity	NPD6227	Discontinued
0.7205	Intermediate Similarity	NPD3834	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD3330	Phase 1
0.7202	Intermediate Similarity	NPD2581	Approved
0.7202	Intermediate Similarity	NPD8093	Discontinued
0.7202	Intermediate Similarity	NPD2582	Approved
0.7198	Intermediate Similarity	NPD5592	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD3385	Approved
0.7193	Intermediate Similarity	NPD925	Approved
0.7193	Intermediate Similarity	NPD926	Approved
0.7184	Intermediate Similarity	NPD3224	Phase 2
0.7179	Intermediate Similarity	NPD5612	Discontinued
0.7143	Intermediate Similarity	NPD2121	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD5117	Phase 2
0.7143	Intermediate Similarity	NPD2920	Discontinued
0.7135	Intermediate Similarity	NPD7867	Phase 1
0.7134	Intermediate Similarity	NPD1683	Approved
0.7134	Intermediate Similarity	NPD1528	Clinical (unspecified phase)
0.7128	Intermediate Similarity	NPD5903	Approved
0.7128	Intermediate Similarity	NPD5902	Approved
0.7127	Intermediate Similarity	NPD3961	Discontinued
0.712	Intermediate Similarity	NPD1392	Approved
0.712	Intermediate Similarity	NPD6838	Clinical (unspecified phase)
0.7119	Intermediate Similarity	NPD1503	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD8405	Clinical (unspecified phase)
0.7104	Intermediate Similarity	NPD6630	Clinical (unspecified phase)
0.7102	Intermediate Similarity	NPD6375	Clinical (unspecified phase)
0.7102	Intermediate Similarity	NPD4075	Phase 2
0.7101	Intermediate Similarity	NPD4326	Phase 2
0.7099	Intermediate Similarity	NPD5020	Approved
0.7095	Intermediate Similarity	NPD5522	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD2391	Clinical (unspecified phase)
0.7093	Intermediate Similarity	NPD2915	Discontinued
0.7062	Intermediate Similarity	NPD5067	Phase 2
0.7062	Intermediate Similarity	NPD5936	Approved
0.7062	Intermediate Similarity	NPD5939	Approved
0.7062	Intermediate Similarity	NPD5066	Phase 2
0.7055	Intermediate Similarity	NPD6506	Clinical (unspecified phase)
0.7053	Intermediate Similarity	NPD4886	Phase 2
0.7051	Intermediate Similarity	NPD947	Approved
0.7047	Intermediate Similarity	NPD2125	Clinical (unspecified phase)
0.7031	Intermediate Similarity	NPD6290	Phase 2
0.7021	Intermediate Similarity	NPD7621	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD3825	Phase 3
0.7018	Intermediate Similarity	NPD1403	Approved
0.7018	Intermediate Similarity	NPD1404	Approved
0.7016	Intermediate Similarity	NPD5426	Phase 3
0.7011	Intermediate Similarity	NPD4699	Discontinued
0.7005	Intermediate Similarity	NPD6803	Clinical (unspecified phase)
0.6995	Remote Similarity	NPD5658	Approved
0.6995	Remote Similarity	NPD2916	Discontinued
0.6995	Remote Similarity	NPD7947	Clinical (unspecified phase)
0.699	Remote Similarity	NPD8094	Discontinued
0.6984	Remote Similarity	NPD4600	Approved
0.6984	Remote Similarity	NPD4601	Approved
0.6977	Remote Similarity	NPD1853	Clinical (unspecified phase)
0.6973	Remote Similarity	NPD4909	Approved
0.6966	Remote Similarity	NPD4181	Approved
0.6961	Remote Similarity	NPD5083	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD6281	Approved
0.6954	Remote Similarity	NPD3757	Clinical (unspecified phase)
0.6947	Remote Similarity	NPD6145	Phase 1
0.6943	Remote Similarity	NPD7452	Approved
0.6943	Remote Similarity	NPD7222	Phase 2
0.6943	Remote Similarity	NPD7453	Approved
0.694	Remote Similarity	NPD3486	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD4880	Discontinued
0.6936	Remote Similarity	NPD3323	Discontinued
0.6935	Remote Similarity	NPD6985	Discontinued

Bioactivity similarity: Similar Natural Products in NPASS

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

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

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data