NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	240.09
Volume:	246.15
LogP:	2.825
LogD:	2.795
LogS:	-3.461
# Rotatable Bonds:	3
TPSA:	54.98
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.701
Synthetic Accessibility Score:	2.09
Fsp3:	0.143
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.919
MDCK Permeability:	2.618635699036531e-05
Pgp-inhibitor:	0.009
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.008
30% Bioavailability (F30%):	0.013

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.856
Plasma Protein Binding (PPB):	87.61002349853516%
Volume Distribution (VD):	1.128
Pgp-substrate:	8.424802780151367%

ADMET: Metabolism

CYP1A2-inhibitor:	0.99
CYP1A2-substrate:	0.745
CYP2C19-inhibitor:	0.779
CYP2C19-substrate:	0.224
CYP2C9-inhibitor:	0.464
CYP2C9-substrate:	0.792
CYP2D6-inhibitor:	0.75
CYP2D6-substrate:	0.608
CYP3A4-inhibitor:	0.697
CYP3A4-substrate:	0.169

ADMET: Excretion

Clearance (CL):	4.612
Half-life (T1/2):	0.26

ADMET: Toxicity

hERG Blockers:	0.059
Human Hepatotoxicity (H-HT):	0.436
Drug-inuced Liver Injury (DILI):	0.952
AMES Toxicity:	0.047
Rat Oral Acute Toxicity:	0.121
Maximum Recommended Daily Dose:	0.829
Skin Sensitization:	0.584
Carcinogencity:	0.241
Eye Corrosion:	0.013
Eye Irritation:	0.969
Respiratory Toxicity:	0.968

Download Data

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

Natural Product: NPC123839

Natural Product ID:	NPC123839
*Common Name:**	Kumujian A
IUPAC Name:	ethyl 9H-pyrido[3,4-b]indole-1-carboxylate
Synonyms:
Standard InCHIKey:	CFXOOHNXLDSCHT-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C14H12N2O2/c1-2-18-14(17)13-12-10(7-8-15-13)9-5-3-4-6-11(9)16-12/h3-8,16H,2H2,1H3
SMILES:	CCOC(=O)c1nccc2c1[nH]c1c2cccc1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3401839
PubChem CID:	11701473
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
NPO25272	Celastrus angulatus	Species	Celastraceae	Eukaryota	n.a.	seed	n.a.	DOI[10.1016/S0031-9422(99)00216-2]
NPO27260	Polygala tenuifolia	Species	Polygalaceae	Eukaryota	roots	n.a.	n.a.	PMID[16989524]
NPO27260	Polygala tenuifolia	Species	Polygalaceae	Eukaryota	n.a.	rhizome	n.a.	PMID[22863942]
NPO27260	Polygala tenuifolia	Species	Polygalaceae	Eukaryota	aerial parts	n.a.	n.a.	PMID[24042007]
NPO25272	Celastrus angulatus	Species	Celastraceae	Eukaryota	seeds and root bark	Henan, China	n.a.	PMID[26295746]
NPO27260	Polygala tenuifolia	Species	Polygalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25272	Celastrus angulatus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25272	Celastrus angulatus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27260	Polygala tenuifolia	Species	Polygalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25272	Celastrus angulatus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO27260	Polygala tenuifolia	Species	Polygalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO30610	Picrasma allanthoides	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO27260	Polygala tenuifolia	Species	Polygalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO25272	Celastrus angulatus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27260	Polygala tenuifolia	Species	Polygalaceae	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
IC50	2
Others	3

Activity Type	# Activity
Individual Protein	1
NON-MOLECULAR	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT178	Individual Protein	Protein-tyrosine phosphatase 1B	Homo sapiens	Inhibition	=	26.9	%	PMID[473033]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	93.92	%	PMID[473034]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	4.87	ug.mL-1	PMID[473034]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	6.29	ug.mL-1	PMID[473034]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	70.75	%	PMID[473034]

☑ 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 NPC123839 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	430
0.1-0.2	3102
0.2-0.3	12768
0.3-0.4	16334
0.4-0.5	5632
0.5-0.6	1747
0.6-0.7	2141
0.7-0.8	494
0.8-0.85	37
0.85-0.9	8
0.9-0.95	2
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9892	High Similarity	NPC266249
0.9479	High Similarity	NPC118940
0.899	High Similarity	NPC477979
0.8932	High Similarity	NPC260434
0.8918	High Similarity	NPC132539
0.8804	High Similarity	NPC182222
0.8763	High Similarity	NPC284678
0.8684	High Similarity	NPC138370
0.8551	High Similarity	NPC122436
0.8511	High Similarity	NPC102755
0.848	Intermediate Similarity	NPC36405
0.8473	Intermediate Similarity	NPC89508
0.8462	Intermediate Similarity	NPC229893
0.8457	Intermediate Similarity	NPC191415
0.8439	Intermediate Similarity	NPC312645
0.8434	Intermediate Similarity	NPC57398
0.8392	Intermediate Similarity	NPC165599
0.8367	Intermediate Similarity	NPC141454
0.8257	Intermediate Similarity	NPC148889
0.8232	Intermediate Similarity	NPC474916
0.8229	Intermediate Similarity	NPC282103
0.8223	Intermediate Similarity	NPC102592
0.8223	Intermediate Similarity	NPC79356
0.822	Intermediate Similarity	NPC48938
0.8191	Intermediate Similarity	NPC81535
0.8177	Intermediate Similarity	NPC244741
0.8144	Intermediate Similarity	NPC278434
0.8128	Intermediate Similarity	NPC82053
0.8122	Intermediate Similarity	NPC198673
0.8119	Intermediate Similarity	NPC235685
0.8086	Intermediate Similarity	NPC27041
0.8084	Intermediate Similarity	NPC192712
0.8082	Intermediate Similarity	NPC101350
0.8019	Intermediate Similarity	NPC82370
0.7972	Intermediate Similarity	NPC315062
0.7972	Intermediate Similarity	NPC267853
0.797	Intermediate Similarity	NPC19872
0.796	Intermediate Similarity	NPC239954
0.796	Intermediate Similarity	NPC168911
0.7948	Intermediate Similarity	NPC258048
0.7943	Intermediate Similarity	NPC476287
0.794	Intermediate Similarity	NPC326422
0.7936	Intermediate Similarity	NPC244897
0.7934	Intermediate Similarity	NPC60621
0.7931	Intermediate Similarity	NPC471944
0.7908	Intermediate Similarity	NPC62749
0.7904	Intermediate Similarity	NPC53534
0.7879	Intermediate Similarity	NPC469489
0.7871	Intermediate Similarity	NPC67288
0.7864	Intermediate Similarity	NPC316411
0.7835	Intermediate Similarity	NPC469896
0.7833	Intermediate Similarity	NPC237414
0.7833	Intermediate Similarity	NPC103361
0.7824	Intermediate Similarity	NPC145885
0.7824	Intermediate Similarity	NPC14113
0.7824	Intermediate Similarity	NPC84827
0.7817	Intermediate Similarity	NPC160381
0.7811	Intermediate Similarity	NPC135950
0.7804	Intermediate Similarity	NPC323969
0.78	Intermediate Similarity	NPC55493
0.7797	Intermediate Similarity	NPC91868
0.7797	Intermediate Similarity	NPC63971
0.7793	Intermediate Similarity	NPC15801
0.7793	Intermediate Similarity	NPC104712
0.7784	Intermediate Similarity	NPC126709
0.7784	Intermediate Similarity	NPC248041
0.7778	Intermediate Similarity	NPC152620
0.7773	Intermediate Similarity	NPC234078
0.7773	Intermediate Similarity	NPC221100
0.7773	Intermediate Similarity	NPC196718
0.7773	Intermediate Similarity	NPC102593
0.7772	Intermediate Similarity	NPC151635
0.7767	Intermediate Similarity	NPC245816
0.7767	Intermediate Similarity	NPC476138
0.7767	Intermediate Similarity	NPC317701
0.7757	Intermediate Similarity	NPC74360
0.7745	Intermediate Similarity	NPC123395
0.7725	Intermediate Similarity	NPC318299
0.7716	Intermediate Similarity	NPC207851
0.7707	Intermediate Similarity	NPC214428
0.7696	Intermediate Similarity	NPC212213
0.7692	Intermediate Similarity	NPC283219
0.7692	Intermediate Similarity	NPC207686
0.7689	Intermediate Similarity	NPC317752
0.768	Intermediate Similarity	NPC267885
0.7673	Intermediate Similarity	NPC472210
0.7673	Intermediate Similarity	NPC247735
0.7673	Intermediate Similarity	NPC81802
0.7673	Intermediate Similarity	NPC269886
0.7673	Intermediate Similarity	NPC472295
0.767	Intermediate Similarity	NPC232727
0.7664	Intermediate Similarity	NPC472285
0.7644	Intermediate Similarity	NPC327592
0.7644	Intermediate Similarity	NPC41717
0.7644	Intermediate Similarity	NPC472259
0.7641	Intermediate Similarity	NPC284775
0.7633	Intermediate Similarity	NPC473761
0.7629	Intermediate Similarity	NPC110500
0.7629	Intermediate Similarity	NPC203468
0.7629	Intermediate Similarity	NPC149155
0.7624	Intermediate Similarity	NPC472292
0.7623	Intermediate Similarity	NPC97902
0.7621	Intermediate Similarity	NPC176538
0.7613	Intermediate Similarity	NPC200553
0.7613	Intermediate Similarity	NPC279189
0.7612	Intermediate Similarity	NPC324091
0.7612	Intermediate Similarity	NPC83111
0.7612	Intermediate Similarity	NPC154339
0.7609	Intermediate Similarity	NPC165964
0.7608	Intermediate Similarity	NPC317373
0.7602	Intermediate Similarity	NPC219336
0.7598	Intermediate Similarity	NPC472293
0.7592	Intermediate Similarity	NPC42372
0.7589	Intermediate Similarity	NPC57453
0.7586	Intermediate Similarity	NPC267343
0.7583	Intermediate Similarity	NPC185782
0.7573	Intermediate Similarity	NPC472296
0.7573	Intermediate Similarity	NPC472297
0.7561	Intermediate Similarity	NPC267928
0.7561	Intermediate Similarity	NPC167710
0.756	Intermediate Similarity	NPC470500
0.7559	Intermediate Similarity	NPC26679
0.7551	Intermediate Similarity	NPC217372
0.7551	Intermediate Similarity	NPC183662
0.7551	Intermediate Similarity	NPC15573
0.7549	Intermediate Similarity	NPC19692
0.7549	Intermediate Similarity	NPC202812
0.7549	Intermediate Similarity	NPC220151
0.7548	Intermediate Similarity	NPC476874
0.7545	Intermediate Similarity	NPC319232
0.7545	Intermediate Similarity	NPC24370
0.7545	Intermediate Similarity	NPC174489
0.7538	Intermediate Similarity	NPC293216
0.7536	Intermediate Similarity	NPC287208
0.7535	Intermediate Similarity	NPC322064
0.7526	Intermediate Similarity	NPC249614
0.7524	Intermediate Similarity	NPC277350
0.7513	Intermediate Similarity	NPC78020
0.7512	Intermediate Similarity	NPC245916
0.7511	Intermediate Similarity	NPC162002
0.75	Intermediate Similarity	NPC478158
0.7488	Intermediate Similarity	NPC478157
0.7488	Intermediate Similarity	NPC241024
0.7478	Intermediate Similarity	NPC26641
0.7478	Intermediate Similarity	NPC240384
0.7476	Intermediate Similarity	NPC470505
0.7475	Intermediate Similarity	NPC196251
0.7475	Intermediate Similarity	NPC102338
0.7475	Intermediate Similarity	NPC63199
0.7475	Intermediate Similarity	NPC321708
0.7475	Intermediate Similarity	NPC111602
0.7465	Intermediate Similarity	NPC281049
0.7464	Intermediate Similarity	NPC193761
0.7463	Intermediate Similarity	NPC235684
0.7462	Intermediate Similarity	NPC111275
0.7458	Intermediate Similarity	NPC74619
0.7453	Intermediate Similarity	NPC116555
0.7442	Intermediate Similarity	NPC472291
0.7441	Intermediate Similarity	NPC238457
0.7437	Intermediate Similarity	NPC314394
0.7437	Intermediate Similarity	NPC71037
0.7435	Intermediate Similarity	NPC322644
0.7427	Intermediate Similarity	NPC472116
0.7424	Intermediate Similarity	NPC213468
0.7423	Intermediate Similarity	NPC470894
0.7422	Intermediate Similarity	NPC323752
0.7419	Intermediate Similarity	NPC179787
0.7419	Intermediate Similarity	NPC201380
0.7418	Intermediate Similarity	NPC472070
0.7413	Intermediate Similarity	NPC280290
0.7413	Intermediate Similarity	NPC133003
0.7412	Intermediate Similarity	NPC37152
0.7406	Intermediate Similarity	NPC183777
0.7406	Intermediate Similarity	NPC243850
0.7404	Intermediate Similarity	NPC476167
0.7403	Intermediate Similarity	NPC178858
0.7402	Intermediate Similarity	NPC476460
0.7398	Intermediate Similarity	NPC252572
0.7395	Intermediate Similarity	NPC471194
0.7395	Intermediate Similarity	NPC471193
0.7389	Intermediate Similarity	NPC221873
0.7387	Intermediate Similarity	NPC73994
0.7383	Intermediate Similarity	NPC167860
0.7383	Intermediate Similarity	NPC123976
0.7383	Intermediate Similarity	NPC5145
0.7381	Intermediate Similarity	NPC328596
0.7381	Intermediate Similarity	NPC328318
0.738	Intermediate Similarity	NPC321911
0.7376	Intermediate Similarity	NPC315555
0.7376	Intermediate Similarity	NPC90415
0.7376	Intermediate Similarity	NPC94752
0.7373	Intermediate Similarity	NPC470799
0.7373	Intermediate Similarity	NPC471192
0.7373	Intermediate Similarity	NPC8022
0.7371	Intermediate Similarity	NPC171787
0.7368	Intermediate Similarity	NPC315491
0.7368	Intermediate Similarity	NPC45459
0.7366	Intermediate Similarity	NPC63545
0.7363	Intermediate Similarity	NPC46895
0.7363	Intermediate Similarity	NPC477003

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 NPC123839 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	242
0.1-0.2	640
0.2-0.3	812
0.3-0.4	1625
0.4-0.5	2590
0.5-0.6	2030
0.6-0.7	1105
0.7-0.8	95
0.8-0.85	9
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8964	High Similarity	NPD2121	Clinical (unspecified phase)
0.8593	High Similarity	NPD2510	Approved
0.8593	High Similarity	NPD2509	Approved
0.8551	High Similarity	NPD2921	Clinical (unspecified phase)
0.8495	Intermediate Similarity	NPD1996	Discontinued
0.848	Intermediate Similarity	NPD3394	Approved
0.848	Intermediate Similarity	NPD3393	Approved
0.848	Intermediate Similarity	NPD3389	Approved
0.8394	Intermediate Similarity	NPD5483	Clinical (unspecified phase)
0.8374	Intermediate Similarity	NPD5475	Discontinued
0.8243	Intermediate Similarity	NPD5482	Discontinued
0.8128	Intermediate Similarity	NPD4862	Clinical (unspecified phase)
0.8009	Intermediate Similarity	NPD7404	Approved
0.7871	Intermediate Similarity	NPD4987	Clinical (unspecified phase)
0.7847	Intermediate Similarity	NPD7470	Discontinued
0.7821	Intermediate Similarity	NPD5450	Discontinued
0.7773	Intermediate Similarity	NPD3794	Approved
0.7773	Intermediate Similarity	NPD3795	Approved
0.7767	Intermediate Similarity	NPD6176	Phase 1
0.7748	Intermediate Similarity	NPD3006	Discontinued
0.7729	Intermediate Similarity	NPD3947	Discontinued
0.7704	Intermediate Similarity	NPD3178	Discontinued
0.768	Intermediate Similarity	NPD749	Clinical (unspecified phase)
0.7674	Intermediate Similarity	NPD6770	Approved
0.7665	Intermediate Similarity	NPD5728	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD5003	Discontinued
0.7644	Intermediate Similarity	NPD5901	Discontinued
0.7629	Intermediate Similarity	NPD482	Approved
0.7608	Intermediate Similarity	NPD7010	Phase 3
0.7546	Intermediate Similarity	NPD4429	Discontinued
0.7545	Intermediate Similarity	NPD8289	Discontinued
0.75	Intermediate Similarity	NPD4506	Discontinued
0.7478	Intermediate Similarity	NPD4958	Clinical (unspecified phase)
0.7477	Intermediate Similarity	NPD3280	Approved
0.7438	Intermediate Similarity	NPD2564	Approved
0.7438	Intermediate Similarity	NPD2565	Phase 2
0.7434	Intermediate Similarity	NPD5891	Approved
0.7426	Intermediate Similarity	NPD4948	Discontinued
0.7419	Intermediate Similarity	NPD1591	Approved
0.7406	Intermediate Similarity	NPD6838	Clinical (unspecified phase)
0.74	Intermediate Similarity	NPD2092	Phase 2
0.74	Intermediate Similarity	NPD2094	Phase 2
0.74	Intermediate Similarity	NPD2095	Phase 2
0.7398	Intermediate Similarity	NPD750	Phase 2
0.7397	Intermediate Similarity	NPD6242	Discontinued
0.7395	Intermediate Similarity	NPD6657	Clinical (unspecified phase)
0.7385	Intermediate Similarity	NPD5632	Approved
0.7378	Intermediate Similarity	NPD6263	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD6479	Discontinued
0.7368	Intermediate Similarity	NPD484	Approved
0.7366	Intermediate Similarity	NPD4376	Phase 3
0.7366	Intermediate Similarity	NPD5022	Discontinued
0.7363	Intermediate Similarity	NPD2096	Phase 2
0.7363	Intermediate Similarity	NPD2091	Phase 2
0.7354	Intermediate Similarity	NPD7994	Phase 2
0.7353	Intermediate Similarity	NPD4499	Approved
0.7349	Intermediate Similarity	NPD5416	Discontinued
0.733	Intermediate Similarity	NPD2581	Approved
0.733	Intermediate Similarity	NPD2582	Approved
0.7327	Intermediate Similarity	NPD5293	Phase 2
0.7306	Intermediate Similarity	NPD1623	Approved
0.7302	Intermediate Similarity	NPD7998	Clinical (unspecified phase)
0.7302	Intermediate Similarity	NPD5072	Discontinued
0.7277	Intermediate Similarity	NPD1096	Discontinued
0.7273	Intermediate Similarity	NPD5065	Approved
0.7265	Intermediate Similarity	NPD4558	Phase 2
0.7252	Intermediate Similarity	NPD6160	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD8304	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD5417	Clinical (unspecified phase)
0.7232	Intermediate Similarity	NPD7603	Discontinued
0.7231	Intermediate Similarity	NPD2915	Discontinued
0.7207	Intermediate Similarity	NPD4301	Approved
0.7206	Intermediate Similarity	NPD4426	Clinical (unspecified phase)
0.7205	Intermediate Similarity	NPD7853	Phase 2
0.7204	Intermediate Similarity	NPD4501	Approved
0.7204	Intermediate Similarity	NPD4500	Approved
0.7196	Intermediate Similarity	NPD7001	Phase 3
0.7192	Intermediate Similarity	NPD6178	Phase 3
0.7182	Intermediate Similarity	NPD7823	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD7688	Phase 1
0.7178	Intermediate Similarity	NPD1783	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD2125	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD6529	Discontinued
0.717	Intermediate Similarity	NPD7903	Clinical (unspecified phase)
0.7163	Intermediate Similarity	NPD3371	Approved
0.7156	Intermediate Similarity	NPD5887	Clinical (unspecified phase)
0.7156	Intermediate Similarity	NPD7621	Clinical (unspecified phase)
0.7156	Intermediate Similarity	NPD8093	Discontinued
0.7155	Intermediate Similarity	NPD8049	Phase 2
0.715	Intermediate Similarity	NPD5912	Clinical (unspecified phase)
0.715	Intermediate Similarity	NPD5913	Phase 3
0.715	Intermediate Similarity	NPD2721	Clinical (unspecified phase)
0.715	Intermediate Similarity	NPD6288	Clinical (unspecified phase)
0.715	Intermediate Similarity	NPD5104	Approved
0.715	Intermediate Similarity	NPD820	Phase 3
0.7116	Intermediate Similarity	NPD2008	Discontinued
0.7116	Intermediate Similarity	NPD7289	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD4554	Clinical (unspecified phase)
0.7103	Intermediate Similarity	NPD2920	Discontinued
0.7103	Intermediate Similarity	NPD8072	Approved
0.7093	Intermediate Similarity	NPD1580	Clinical (unspecified phase)
0.7093	Intermediate Similarity	NPD1579	Discontinued
0.7091	Intermediate Similarity	NPD3757	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD5017	Discontinued
0.7085	Intermediate Similarity	NPD5827	Discontinued
0.7081	Intermediate Similarity	NPD1304	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD1038	Approved
0.7081	Intermediate Similarity	NPD460	Discontinued
0.7078	Intermediate Similarity	NPD3330	Phase 1
0.7073	Intermediate Similarity	NPD7424	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD1308	Approved
0.7072	Intermediate Similarity	NPD8405	Clinical (unspecified phase)
0.7072	Intermediate Similarity	NPD6578	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD6173	Approved
0.7067	Intermediate Similarity	NPD5592	Clinical (unspecified phase)
0.7064	Intermediate Similarity	NPD4051	Discontinued
0.7061	Intermediate Similarity	NPD5479	Discontinued
0.7059	Intermediate Similarity	NPD2412	Clinical (unspecified phase)
0.7053	Intermediate Similarity	NPD9271	Approved
0.7051	Intermediate Similarity	NPD2442	Approved
0.7051	Intermediate Similarity	NPD7947	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD2443	Approved
0.7048	Intermediate Similarity	NPD5975	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD7618	Phase 3
0.7048	Intermediate Similarity	NPD7268	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD7619	Phase 3
0.7045	Intermediate Similarity	NPD2823	Clinical (unspecified phase)
0.7043	Intermediate Similarity	NPD5040	Clinical (unspecified phase)
0.7042	Intermediate Similarity	NPD8248	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD706	Phase 1
0.7037	Intermediate Similarity	NPD2715	Clinical (unspecified phase)
0.7033	Intermediate Similarity	NPD4922	Phase 2
0.7032	Intermediate Similarity	NPD6567	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD4614	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD5066	Phase 2
0.7032	Intermediate Similarity	NPD5067	Phase 2
0.703	Intermediate Similarity	NPD2144	Approved
0.7027	Intermediate Similarity	NPD2787	Clinical (unspecified phase)
0.7026	Intermediate Similarity	NPD1630	Approved
0.7024	Intermediate Similarity	NPD3607	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD6281	Approved
0.7018	Intermediate Similarity	NPD5559	Phase 2
0.7014	Intermediate Similarity	NPD5512	Phase 3
0.7014	Intermediate Similarity	NPD8112	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD2951	Discontinued
0.7005	Intermediate Similarity	NPD1506	Discontinued
0.7	Intermediate Similarity	NPD4528	Approved
0.7	Intermediate Similarity	NPD7594	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD2411	Approved
0.7	Intermediate Similarity	NPD4529	Approved
0.7	Intermediate Similarity	NPD4526	Approved
0.6995	Remote Similarity	NPD3825	Phase 3
0.6995	Remote Similarity	NPD6661	Clinical (unspecified phase)
0.6991	Remote Similarity	NPD7712	Clinical (unspecified phase)
0.6991	Remote Similarity	NPD7547	Clinical (unspecified phase)
0.6991	Remote Similarity	NPD5426	Phase 3
0.6987	Remote Similarity	NPD4952	Phase 3
0.6986	Remote Similarity	NPD4900	Clinical (unspecified phase)
0.6985	Remote Similarity	NPD5069	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD8073	Approved
0.6975	Remote Similarity	NPD4896	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD3259	Approved
0.697	Remote Similarity	NPD6741	Clinical (unspecified phase)
0.6961	Remote Similarity	NPD1291	Clinical (unspecified phase)
0.6961	Remote Similarity	NPD6595	Phase 3
0.6959	Remote Similarity	NPD7958	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD7957	Phase 1
0.6955	Remote Similarity	NPD4417	Approved
0.6955	Remote Similarity	NPD8013	Clinical (unspecified phase)
0.6941	Remote Similarity	NPD1600	Suspended
0.6938	Remote Similarity	NPD3321	Discontinued
0.6936	Remote Similarity	NPD6790	Phase 1
0.6934	Remote Similarity	NPD7818	Clinical (unspecified phase)
0.6934	Remote Similarity	NPD7061	Clinical (unspecified phase)
0.693	Remote Similarity	NPD7727	Phase 2
0.6929	Remote Similarity	NPD2311	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD3038	Discontinued
0.6923	Remote Similarity	NPD3360	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD4938	Phase 2
0.6923	Remote Similarity	NPD6141	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD1631	Approved
0.6916	Remote Similarity	NPD6753	Phase 1
0.6916	Remote Similarity	NPD7000	Clinical (unspecified phase)
0.6916	Remote Similarity	NPD6999	Discontinued
0.6916	Remote Similarity	NPD6752	Phase 1
0.6912	Remote Similarity	NPD6987	Phase 1
0.6912	Remote Similarity	NPD5398	Clinical (unspecified phase)
0.6908	Remote Similarity	NPD5075	Discontinued
0.6907	Remote Similarity	NPD180	Clinical (unspecified phase)
0.6906	Remote Similarity	NPD8160	Phase 2
0.6905	Remote Similarity	NPD2336	Approved
0.6905	Remote Similarity	NPD6180	Clinical (unspecified phase)
0.69	Remote Similarity	NPD6164	Phase 2
0.69	Remote Similarity	NPD6165	Phase 2
0.6898	Remote Similarity	NPD5721	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD4373	Phase 2
0.6895	Remote Similarity	NPD7393	Clinical (unspecified phase)
0.6893	Remote Similarity	NPD5596	Phase 2
0.6892	Remote Similarity	NPD8094	Discontinued
0.6892	Remote Similarity	NPD3945	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