NPASS Compound

Structure

NPC101350 OpenBabel07101718242D 28 32 0 0 0 0 0 0 0 0999 V2000 -4.8253 0.2330 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5599 -0.5352 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6036 -0.9511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2272 -0.2670 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6254 -1.1590 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3612 0.2330 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2872 -1.1590 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3090 -0.9511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0932 1.2330 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2435 0.7431 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0248 2.8157 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0932 0.2330 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9126 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9563 -0.4158 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3612 1.2330 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9563 -0.4158 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6180 1.9021 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2272 1.7330 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2653 0.5352 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6473 0.5352 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6691 0.7431 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3601 1.6942 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.0193 2.7111 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.4563 1.1230 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.0292 2.4373 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.9593 -0.2670 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.8907 0.2079 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 27 1 0 0 0 0 2 28 1 0 0 0 0 3 5 2 0 0 0 0 3 13 1 0 0 0 0 4 6 2 0 0 0 0 4 12 1 0 0 0 0 5 14 1 0 0 0 0 6 15 1 0 0 0 0 7 8 1 0 0 0 0 7 16 2 0 0 0 0 8 23 2 0 0 0 0 9 12 2 0 0 0 0 9 18 1 0 0 0 0 10 13 2 0 0 0 0 10 19 1 0 0 0 0 11 17 2 0 0 0 0 11 24 1 0 0 0 0 12 27 1 0 0 0 0 13 28 1 0 0 0 0 14 16 1 0 0 0 0 14 19 2 0 0 0 0 15 17 1 0 0 0 0 15 18 2 0 0 0 0 16 20 1 0 0 0 0 17 22 1 0 0 0 0 18 24 1 0 0 0 0 19 25 1 0 0 0 0 20 21 2 0 0 0 0 20 25 1 0 0 0 0 21 22 1 0 0 0 0 21 23 1 0 0 0 0 22 26 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	371.13
Volume:	376.646
LogP:	4.323
LogD:	3.647
LogS:	-6.421
# Rotatable Bonds:	4
TPSA:	80.0
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.458
Synthetic Accessibility Score:	2.465
Fsp3:	0.091
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.319
MDCK Permeability:	6.266116997721838e-06
Pgp-inhibitor:	0.864
Pgp-substrate:	0.004
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.973

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.115
Plasma Protein Binding (PPB):	95.45970916748047%
Volume Distribution (VD):	0.714
Pgp-substrate:	4.675085544586182%

ADMET: Metabolism

CYP1A2-inhibitor:	0.972
CYP1A2-substrate:	0.915
CYP2C19-inhibitor:	0.824
CYP2C19-substrate:	0.081
CYP2C9-inhibitor:	0.862
CYP2C9-substrate:	0.949
CYP2D6-inhibitor:	0.595
CYP2D6-substrate:	0.913
CYP3A4-inhibitor:	0.929
CYP3A4-substrate:	0.194

ADMET: Excretion

Clearance (CL):	5.547
Half-life (T1/2):	0.158

ADMET: Toxicity

hERG Blockers:	0.462
Human Hepatotoxicity (H-HT):	0.934
Drug-inuced Liver Injury (DILI):	0.959
AMES Toxicity:	0.962
Rat Oral Acute Toxicity:	0.792
Maximum Recommended Daily Dose:	0.975
Skin Sensitization:	0.593
Carcinogencity:	0.561
Eye Corrosion:	0.003
Eye Irritation:	0.464
Respiratory Toxicity:	0.953

Download Data

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

Natural Product: NPC101350

Natural Product ID:	NPC101350
*Common Name:**	Trigonostemine B
IUPAC Name:	(6-methoxy-1H-indol-3-yl)-(7-methoxy-9H-pyrido[3,4-b]indol-1-yl)methanone
Synonyms:	Trigonostemine B
Standard InCHIKey:	WPMVYZFRMATFJA-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C22H17N3O3/c1-27-12-4-6-15-17(11-24-18(15)9-12)22(26)21-20-16(7-8-23-21)14-5-3-13(28-2)10-19(14)25-20/h3-11,24-25H,1-2H3
SMILES:	COc1ccc2c(c[nH]c2c1)C(=O)c1c2c(ccn1)c1ccc(cc1[nH]2)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1957109
PubChem CID:	57345602
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
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
IC50	5

Activity Type	# Activity
Cell Line	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT116	Cell Line	HL-60	Homo sapiens	IC50	>	40000.0	nM	PMID[567258]
NPT659	Cell Line	SMMC-7721	Homo sapiens	IC50	=	4780.0	nM	PMID[567258]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	8670.0	nM	PMID[567258]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	2980.0	nM	PMID[567258]
NPT660	Cell Line	SW480	Homo sapiens	IC50	=	3550.0	nM	PMID[567258]

☑ 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 NPC101350 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	683
0.1-0.2	4273
0.2-0.3	12813
0.3-0.4	7708
0.4-0.5	12526
0.5-0.6	2087
0.6-0.7	1983
0.7-0.8	557
0.8-0.85	45
0.85-0.9	14
0.9-0.95	5
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9952	High Similarity	NPC235685
0.9429	High Similarity	NPC122436
0.9367	High Similarity	NPC63971
0.9367	High Similarity	NPC91868
0.9078	High Similarity	NPC260434
0.8788	High Similarity	NPC53534
0.875	High Similarity	NPC323969
0.8694	High Similarity	NPC207686
0.8592	High Similarity	NPC167860
0.8592	High Similarity	NPC123976
0.8565	High Similarity	NPC152620
0.8539	High Similarity	NPC60621
0.8525	High Similarity	NPC27041
0.8476	Intermediate Similarity	NPC232727
0.8442	Intermediate Similarity	NPC178858
0.8432	Intermediate Similarity	NPC258048
0.8378	Intermediate Similarity	NPC229893
0.8364	Intermediate Similarity	NPC193267
0.8364	Intermediate Similarity	NPC213530
0.8357	Intermediate Similarity	NPC285558
0.8348	Intermediate Similarity	NPC148889
0.8311	Intermediate Similarity	NPC471762
0.8282	Intermediate Similarity	NPC196718
0.8273	Intermediate Similarity	NPC305984
0.823	Intermediate Similarity	NPC194740
0.8203	Intermediate Similarity	NPC174758
0.8202	Intermediate Similarity	NPC102593
0.8201	Intermediate Similarity	NPC63109
0.8157	Intermediate Similarity	NPC266249
0.815	Intermediate Similarity	NPC66777
0.8145	Intermediate Similarity	NPC322064
0.8145	Intermediate Similarity	NPC170114
0.8143	Intermediate Similarity	NPC326422
0.81	Intermediate Similarity	NPC470549
0.8082	Intermediate Similarity	NPC123839
0.8072	Intermediate Similarity	NPC264285
0.8052	Intermediate Similarity	NPC182222
0.8043	Intermediate Similarity	NPC200553
0.8043	Intermediate Similarity	NPC49547
0.8043	Intermediate Similarity	NPC279189
0.8028	Intermediate Similarity	NPC183777
0.8025	Intermediate Similarity	NPC26543
0.8009	Intermediate Similarity	NPC118940
0.8	Intermediate Similarity	NPC276657
0.8	Intermediate Similarity	NPC176538
0.7991	Intermediate Similarity	NPC314954
0.7983	Intermediate Similarity	NPC15801
0.7982	Intermediate Similarity	NPC36405
0.7982	Intermediate Similarity	NPC274982
0.7972	Intermediate Similarity	NPC317701
0.7965	Intermediate Similarity	NPC310118
0.7965	Intermediate Similarity	NPC469554
0.7955	Intermediate Similarity	NPC174672
0.7948	Intermediate Similarity	NPC74575
0.7945	Intermediate Similarity	NPC4687
0.7945	Intermediate Similarity	NPC249583
0.794	Intermediate Similarity	NPC162002
0.794	Intermediate Similarity	NPC473187
0.7932	Intermediate Similarity	NPC78609
0.793	Intermediate Similarity	NPC16352
0.7928	Intermediate Similarity	NPC110182
0.7919	Intermediate Similarity	NPC470020
0.7911	Intermediate Similarity	NPC473041
0.7911	Intermediate Similarity	NPC303658
0.7897	Intermediate Similarity	NPC174489
0.7895	Intermediate Similarity	NPC322482
0.7888	Intermediate Similarity	NPC101543
0.7875	Intermediate Similarity	NPC165964
0.787	Intermediate Similarity	NPC157931
0.787	Intermediate Similarity	NPC478078
0.7857	Intermediate Similarity	NPC208522
0.7854	Intermediate Similarity	NPC132539
0.7834	Intermediate Similarity	NPC19872
0.783	Intermediate Similarity	NPC240384
0.783	Intermediate Similarity	NPC26641
0.7822	Intermediate Similarity	NPC152768
0.7822	Intermediate Similarity	NPC148183
0.7812	Intermediate Similarity	NPC236668
0.7803	Intermediate Similarity	NPC87413
0.7792	Intermediate Similarity	NPC110151
0.7788	Intermediate Similarity	NPC74413
0.7783	Intermediate Similarity	NPC21638
0.7778	Intermediate Similarity	NPC141053
0.7778	Intermediate Similarity	NPC77101
0.7778	Intermediate Similarity	NPC146976
0.7768	Intermediate Similarity	NPC308137
0.7768	Intermediate Similarity	NPC310211
0.7764	Intermediate Similarity	NPC37152
0.7763	Intermediate Similarity	NPC260900
0.7763	Intermediate Similarity	NPC295898
0.7759	Intermediate Similarity	NPC270515
0.7749	Intermediate Similarity	NPC470018
0.7748	Intermediate Similarity	NPC82548
0.7746	Intermediate Similarity	NPC303374
0.7745	Intermediate Similarity	NPC97902
0.7729	Intermediate Similarity	NPC198503
0.7727	Intermediate Similarity	NPC476138
0.7727	Intermediate Similarity	NPC245816
0.7727	Intermediate Similarity	NPC223427
0.7724	Intermediate Similarity	NPC74619
0.7719	Intermediate Similarity	NPC269270
0.7719	Intermediate Similarity	NPC74360
0.771	Intermediate Similarity	NPC138370
0.7709	Intermediate Similarity	NPC169402
0.7706	Intermediate Similarity	NPC81535
0.7699	Intermediate Similarity	NPC477979
0.7699	Intermediate Similarity	NPC116238
0.7689	Intermediate Similarity	NPC264176
0.7689	Intermediate Similarity	NPC26679
0.7686	Intermediate Similarity	NPC150239
0.7686	Intermediate Similarity	NPC14686
0.7679	Intermediate Similarity	NPC472061
0.7679	Intermediate Similarity	NPC184680
0.7679	Intermediate Similarity	NPC471304
0.7674	Intermediate Similarity	NPC324149
0.7671	Intermediate Similarity	NPC329747
0.7671	Intermediate Similarity	NPC121772
0.7671	Intermediate Similarity	NPC132385
0.7669	Intermediate Similarity	NPC39370
0.7667	Intermediate Similarity	NPC191415
0.766	Intermediate Similarity	NPC473186
0.7658	Intermediate Similarity	NPC175602
0.7658	Intermediate Similarity	NPC472064
0.7655	Intermediate Similarity	NPC469592
0.7655	Intermediate Similarity	NPC471080
0.765	Intermediate Similarity	NPC13880
0.7647	Intermediate Similarity	NPC470784
0.7647	Intermediate Similarity	NPC470785
0.7644	Intermediate Similarity	NPC208284
0.7642	Intermediate Similarity	NPC478083
0.7637	Intermediate Similarity	NPC477549
0.7635	Intermediate Similarity	NPC81939
0.7634	Intermediate Similarity	NPC61038
0.7634	Intermediate Similarity	NPC185782
0.7615	Intermediate Similarity	NPC227582
0.7611	Intermediate Similarity	NPC219087
0.7603	Intermediate Similarity	NPC475666
0.76	Intermediate Similarity	NPC11464
0.7598	Intermediate Similarity	NPC46561
0.7598	Intermediate Similarity	NPC247803
0.7594	Intermediate Similarity	NPC84478
0.7591	Intermediate Similarity	NPC315957
0.7589	Intermediate Similarity	NPC39679
0.7589	Intermediate Similarity	NPC287208
0.7581	Intermediate Similarity	NPC76748
0.758	Intermediate Similarity	NPC67288
0.7577	Intermediate Similarity	NPC476287
0.7568	Intermediate Similarity	NPC53144
0.7566	Intermediate Similarity	NPC82370
0.7565	Intermediate Similarity	NPC208084
0.7564	Intermediate Similarity	NPC257851
0.7563	Intermediate Similarity	NPC295228
0.7561	Intermediate Similarity	NPC244543
0.7558	Intermediate Similarity	NPC307963
0.7546	Intermediate Similarity	NPC92111
0.7546	Intermediate Similarity	NPC476460
0.7544	Intermediate Similarity	NPC237740
0.7543	Intermediate Similarity	NPC216612
0.7543	Intermediate Similarity	NPC220851
0.7543	Intermediate Similarity	NPC210434
0.7542	Intermediate Similarity	NPC267853
0.7535	Intermediate Similarity	NPC296527
0.7534	Intermediate Similarity	NPC470500
0.7534	Intermediate Similarity	NPC475070
0.7532	Intermediate Similarity	NPC472099
0.7532	Intermediate Similarity	NPC174760
0.7531	Intermediate Similarity	NPC470022
0.7524	Intermediate Similarity	NPC284775
0.7523	Intermediate Similarity	NPC472069
0.7523	Intermediate Similarity	NPC472062
0.7523	Intermediate Similarity	NPC472063
0.7522	Intermediate Similarity	NPC5145
0.7522	Intermediate Similarity	NPC96321
0.7522	Intermediate Similarity	NPC469594
0.7521	Intermediate Similarity	NPC24370
0.7521	Intermediate Similarity	NPC319232
0.7511	Intermediate Similarity	NPC244897
0.7511	Intermediate Similarity	NPC252338
0.7511	Intermediate Similarity	NPC171787
0.75	Intermediate Similarity	NPC472065
0.75	Intermediate Similarity	NPC300156
0.75	Intermediate Similarity	NPC474916
0.75	Intermediate Similarity	NPC207866
0.75	Intermediate Similarity	NPC45190
0.75	Intermediate Similarity	NPC326363
0.75	Intermediate Similarity	NPC324091
0.7489	Intermediate Similarity	NPC192712
0.7489	Intermediate Similarity	NPC79356
0.7489	Intermediate Similarity	NPC168209
0.7489	Intermediate Similarity	NPC288987
0.7489	Intermediate Similarity	NPC102592
0.7489	Intermediate Similarity	NPC134848
0.7479	Intermediate Similarity	NPC329631
0.7478	Intermediate Similarity	NPC304926
0.7478	Intermediate Similarity	NPC476041
0.7477	Intermediate Similarity	NPC304203
0.7468	Intermediate Similarity	NPC315062
0.7466	Intermediate Similarity	NPC284338
0.7465	Intermediate Similarity	NPC102755
0.7456	Intermediate Similarity	NPC316981

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 NPC101350 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	379
0.1-0.2	643
0.2-0.3	857
0.3-0.4	1643
0.4-0.5	2573
0.5-0.6	1888
0.6-0.7	1052
0.7-0.8	109
0.8-0.85	6
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8546	High Similarity	NPD2921	Clinical (unspecified phase)
0.8491	Intermediate Similarity	NPD5482	Discontinued
0.8398	Intermediate Similarity	NPD5483	Clinical (unspecified phase)
0.8326	Intermediate Similarity	NPD6242	Discontinued
0.819	Intermediate Similarity	NPD6790	Phase 1
0.8074	Intermediate Similarity	NPD5450	Discontinued
0.806	Intermediate Similarity	NPD4958	Clinical (unspecified phase)
0.7991	Intermediate Similarity	NPD2509	Approved
0.7991	Intermediate Similarity	NPD2510	Approved
0.7983	Intermediate Similarity	NPD4558	Phase 2
0.7863	Intermediate Similarity	NPD3006	Discontinued
0.7832	Intermediate Similarity	NPD4429	Discontinued
0.7822	Intermediate Similarity	NPD3394	Approved
0.7822	Intermediate Similarity	NPD3393	Approved
0.7822	Intermediate Similarity	NPD3389	Approved
0.7792	Intermediate Similarity	NPD3259	Approved
0.7753	Intermediate Similarity	NPD5632	Approved
0.7748	Intermediate Similarity	NPD5658	Approved
0.7727	Intermediate Similarity	NPD2121	Clinical (unspecified phase)
0.7725	Intermediate Similarity	NPD5801	Clinical (unspecified phase)
0.7725	Intermediate Similarity	NPD5479	Discontinued
0.772	Intermediate Similarity	NPD7393	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD6531	Approved
0.7692	Intermediate Similarity	NPD6530	Approved
0.7692	Intermediate Similarity	NPD4795	Phase 2
0.7639	Intermediate Similarity	NPD7994	Phase 2
0.7633	Intermediate Similarity	NPD4926	Clinical (unspecified phase)
0.7621	Intermediate Similarity	NPD5417	Clinical (unspecified phase)
0.7611	Intermediate Similarity	NPD8091	Phase 3
0.7591	Intermediate Similarity	NPD1739	Approved
0.7591	Intermediate Similarity	NPD1740	Approved
0.7585	Intermediate Similarity	NPD4885	Approved
0.7582	Intermediate Similarity	NPD6525	Clinical (unspecified phase)
0.7574	Intermediate Similarity	NPD4952	Phase 3
0.7566	Intermediate Similarity	NPD6567	Clinical (unspecified phase)
0.7558	Intermediate Similarity	NPD1304	Clinical (unspecified phase)
0.7558	Intermediate Similarity	NPD1038	Approved
0.7555	Intermediate Similarity	NPD7823	Clinical (unspecified phase)
0.7553	Intermediate Similarity	NPD7558	Phase 2
0.7553	Intermediate Similarity	NPD5040	Clinical (unspecified phase)
0.7522	Intermediate Similarity	NPD8405	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD5022	Discontinued
0.748	Intermediate Similarity	NPD6228	Discontinued
0.7479	Intermediate Similarity	NPD4373	Phase 2
0.7479	Intermediate Similarity	NPD6741	Clinical (unspecified phase)
0.7467	Intermediate Similarity	NPD5293	Phase 2
0.7435	Intermediate Similarity	NPD2412	Clinical (unspecified phase)
0.7422	Intermediate Similarity	NPD5509	Phase 1
0.7417	Intermediate Similarity	NPD7853	Phase 2
0.7395	Intermediate Similarity	NPD6962	Phase 2
0.7393	Intermediate Similarity	NPD6824	Clinical (unspecified phase)
0.7373	Intermediate Similarity	NPD7426	Phase 1
0.7373	Intermediate Similarity	NPD7603	Discontinued
0.7355	Intermediate Similarity	NPD8279	Clinical (unspecified phase)
0.7349	Intermediate Similarity	NPD2311	Clinical (unspecified phase)
0.7342	Intermediate Similarity	NPD4987	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD4850	Phase 1
0.7319	Intermediate Similarity	NPD6160	Clinical (unspecified phase)
0.7314	Intermediate Similarity	NPD4368	Phase 2
0.7313	Intermediate Similarity	NPD1392	Approved
0.7311	Intermediate Similarity	NPD5559	Phase 2
0.7309	Intermediate Similarity	NPD3825	Phase 3
0.7308	Intermediate Similarity	NPD7198	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD7924	Phase 2
0.7305	Intermediate Similarity	NPD7925	Phase 2
0.7301	Intermediate Similarity	NPD3947	Discontinued
0.7301	Intermediate Similarity	NPD5901	Discontinued
0.7297	Intermediate Similarity	NPD7948	Phase 1
0.7294	Intermediate Similarity	NPD8284	Discontinued
0.7284	Intermediate Similarity	NPD5612	Discontinued
0.7269	Intermediate Similarity	NPD3003	Approved
0.7269	Intermediate Similarity	NPD8403	Phase 1
0.7269	Intermediate Similarity	NPD4845	Discontinued
0.7261	Intermediate Similarity	NPD5416	Discontinued
0.7261	Intermediate Similarity	NPD7470	Discontinued
0.7261	Intermediate Similarity	NPD5475	Discontinued
0.7253	Intermediate Similarity	NPD3326	Clinical (unspecified phase)
0.7234	Intermediate Similarity	NPD1996	Discontinued
0.7232	Intermediate Similarity	NPD4118	Clinical (unspecified phase)
0.7231	Intermediate Similarity	NPD6963	Approved
0.7231	Intermediate Similarity	NPD6964	Approved
0.7231	Intermediate Similarity	NPD2951	Discontinued
0.7227	Intermediate Similarity	NPD7803	Approved
0.7225	Intermediate Similarity	NPD5426	Phase 3
0.7222	Intermediate Similarity	NPD8049	Phase 2
0.722	Intermediate Similarity	NPD7689	Approved
0.7218	Intermediate Similarity	NPD8358	Approved
0.7215	Intermediate Similarity	NPD7547	Clinical (unspecified phase)
0.7207	Intermediate Similarity	NPD3324	Clinical (unspecified phase)
0.7206	Intermediate Similarity	NPD7690	Clinical (unspecified phase)
0.7205	Intermediate Similarity	NPD5867	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD4862	Clinical (unspecified phase)
0.7189	Intermediate Similarity	NPD6172	Clinical (unspecified phase)
0.7186	Intermediate Similarity	NPD5067	Phase 2
0.7186	Intermediate Similarity	NPD5066	Phase 2
0.7177	Intermediate Similarity	NPD5488	Discontinued
0.7167	Intermediate Similarity	NPD5903	Approved
0.7167	Intermediate Similarity	NPD5902	Approved
0.7167	Intermediate Similarity	NPD6140	Clinical (unspecified phase)
0.7166	Intermediate Similarity	NPD5802	Phase 2
0.7165	Intermediate Similarity	NPD7955	Approved
0.7165	Intermediate Similarity	NPD7956	Approved
0.7162	Intermediate Similarity	NPD802	Phase 2
0.7155	Intermediate Similarity	NPD7069	Discontinued
0.7143	Intermediate Similarity	NPD6306	Phase 2
0.7137	Intermediate Similarity	NPD6969	Phase 2
0.7137	Intermediate Similarity	NPD1659	Phase 1
0.7137	Intermediate Similarity	NPD5116	Phase 1
0.7137	Intermediate Similarity	NPD6968	Phase 2
0.713	Intermediate Similarity	NPD2189	Approved
0.713	Intermediate Similarity	NPD2187	Approved
0.7125	Intermediate Similarity	NPD7268	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD484	Approved
0.7124	Intermediate Similarity	NPD3945	Discontinued
0.7119	Intermediate Similarity	NPD7194	Discontinued
0.7118	Intermediate Similarity	NPD2008	Discontinued
0.7117	Intermediate Similarity	NPD3921	Approved
0.7117	Intermediate Similarity	NPD3924	Approved
0.7117	Intermediate Similarity	NPD3923	Approved
0.7117	Intermediate Similarity	NPD3922	Approved
0.7087	Intermediate Similarity	NPD6961	Discontinued
0.7085	Intermediate Similarity	NPD5575	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD8289	Discontinued
0.7082	Intermediate Similarity	NPD2411	Approved
0.708	Intermediate Similarity	NPD6999	Discontinued
0.708	Intermediate Similarity	NPD7000	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD4889	Approved
0.7074	Intermediate Similarity	NPD8349	Phase 1
0.707	Intermediate Similarity	NPD7708	Approved
0.7066	Intermediate Similarity	NPD4442	Phase 2
0.7066	Intermediate Similarity	NPD8512	Phase 3
0.7061	Intermediate Similarity	NPD5018	Phase 3
0.7056	Intermediate Similarity	NPD7666	Phase 3
0.7056	Intermediate Similarity	NPD6473	Phase 1
0.7056	Intermediate Similarity	NPD3914	Clinical (unspecified phase)
0.7056	Intermediate Similarity	NPD7665	Phase 2
0.7052	Intermediate Similarity	NPD4369	Phase 2
0.7051	Intermediate Similarity	NPD3794	Approved
0.7051	Intermediate Similarity	NPD3795	Approved
0.7046	Intermediate Similarity	NPD7404	Approved
0.7043	Intermediate Similarity	NPD5601	Phase 2
0.7031	Intermediate Similarity	NPD5513	Phase 2
0.7031	Intermediate Similarity	NPD3801	Clinical (unspecified phase)
0.7028	Intermediate Similarity	NPD7067	Approved
0.7028	Intermediate Similarity	NPD4440	Clinical (unspecified phase)
0.7028	Intermediate Similarity	NPD7068	Approved
0.7024	Intermediate Similarity	NPD6244	Phase 3
0.7024	Intermediate Similarity	NPD6243	Phase 3
0.7018	Intermediate Similarity	NPD7414	Clinical (unspecified phase)
0.7017	Intermediate Similarity	NPD5930	Phase 3
0.7013	Intermediate Similarity	NPD6838	Clinical (unspecified phase)
0.7009	Intermediate Similarity	NPD3816	Phase 1
0.7009	Intermediate Similarity	NPD3815	Phase 1
0.7008	Intermediate Similarity	NPD3960	Clinical (unspecified phase)
0.7004	Intermediate Similarity	NPD3354	Phase 2
0.7004	Intermediate Similarity	NPD4548	Discontinued
0.7004	Intermediate Similarity	NPD1768	Approved
0.7	Intermediate Similarity	NPD3962	Phase 2
0.7	Intermediate Similarity	NPD3959	Phase 2
0.6992	Remote Similarity	NPD7181	Phase 3
0.6985	Remote Similarity	NPD7408	Phase 2
0.698	Remote Similarity	NPD6494	Phase 2
0.6978	Remote Similarity	NPD4418	Discontinued
0.6978	Remote Similarity	NPD6861	Clinical (unspecified phase)
0.6976	Remote Similarity	NPD8017	Clinical (unspecified phase)
0.6976	Remote Similarity	NPD1927	Discontinued
0.6976	Remote Similarity	NPD8016	Phase 3
0.6975	Remote Similarity	NPD6770	Approved
0.6972	Remote Similarity	NPD8100	Phase 3
0.6971	Remote Similarity	NPD6247	Clinical (unspecified phase)
0.697	Remote Similarity	NPD3507	Phase 2
0.697	Remote Similarity	NPD7001	Phase 3
0.6964	Remote Similarity	NPD4372	Phase 1
0.6964	Remote Similarity	NPD6569	Phase 2
0.6964	Remote Similarity	NPD4376	Phase 3
0.6962	Remote Similarity	NPD4989	Phase 2
0.6958	Remote Similarity	NPD6995	Phase 1
0.6957	Remote Similarity	NPD6176	Phase 1
0.6948	Remote Similarity	NPD7417	Discontinued
0.6947	Remote Similarity	NPD8364	Approved
0.6947	Remote Similarity	NPD5512	Phase 3
0.6947	Remote Similarity	NPD8363	Approved
0.6945	Remote Similarity	NPD8524	Approved
0.694	Remote Similarity	NPD7222	Phase 2
0.6939	Remote Similarity	NPD6263	Clinical (unspecified phase)
0.6936	Remote Similarity	NPD5866	Approved
0.6935	Remote Similarity	NPD4314	Approved
0.6935	Remote Similarity	NPD7729	Clinical (unspecified phase)
0.6935	Remote Similarity	NPD4313	Approved
0.6933	Remote Similarity	NPD7395	Discontinued
0.6926	Remote Similarity	NPD3397	Phase 2
0.6926	Remote Similarity	NPD5924	Discontinued
0.692	Remote Similarity	NPD2433	Clinical (unspecified phase)
0.692	Remote Similarity	NPD6716	Phase 1
0.692	Remote Similarity	NPD6180	Clinical (unspecified phase)
0.6917	Remote Similarity	NPD4923	Phase 1
0.6914	Remote Similarity	NPD8246	Approved
0.6914	Remote Similarity	NPD8247	Approved
0.6914	Remote Similarity	NPD6165	Phase 2
0.6914	Remote Similarity	NPD6164	Phase 2

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