NPASS Compound

Structure

NPC63971 OpenBabel07101719512D 27 31 0 0 0 0 0 0 0 0999 V2000 -3.4344 1.4898 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8722 2.5761 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4655 3.4896 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2844 1.7670 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4710 3.5941 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1180 2.7681 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1399 2.5602 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5468 0.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6808 -0.2976 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4781 1.0739 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7872 2.0250 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2899 1.8716 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5468 1.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1691 1.6092 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8832 2.7851 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5000 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0827 1.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6808 1.7024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8147 1.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9487 1.7024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9781 0.2079 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8147 0.2024 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 3.8887 2.6806 0.0000 N 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 1.9487 2.7024 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7213 -0.4612 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7653 2.2329 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 27 1 0 0 0 0 2 3 2 0 0 0 0 2 4 1 0 0 0 0 3 5 1 0 0 0 0 4 12 2 0 0 0 0 5 15 2 0 0 0 0 6 7 2 0 0 0 0 6 11 1 0 0 0 0 7 14 1 0 0 0 0 8 9 2 0 0 0 0 8 13 1 0 0 0 0 9 22 1 0 0 0 0 10 11 2 0 0 0 0 10 16 1 0 0 0 0 11 27 1 0 0 0 0 12 13 1 0 0 0 0 12 15 1 0 0 0 0 13 18 2 0 0 0 0 14 16 2 0 0 0 0 14 17 1 0 0 0 0 15 23 1 0 0 0 0 16 24 1 0 0 0 0 17 20 1 0 0 0 0 17 21 2 0 0 0 0 18 19 1 0 0 0 0 18 23 1 0 0 0 0 19 20 1 0 0 0 0 19 22 2 0 0 0 0 20 25 2 0 0 0 0 21 24 1 0 0 0 0 21 26 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	357.11
Volume:	359.35
LogP:	4.297
LogD:	3.475
LogS:	-6.006
# Rotatable Bonds:	3
TPSA:	91.0
# H-Bond Aceptor:	6
# H-Bond Donor:	3
# Rings:	5
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.423
Synthetic Accessibility Score:	2.599
Fsp3:	0.048
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:	-5.53
MDCK Permeability:	6.987414053583052e-06
Pgp-inhibitor:	0.031
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.026
20% Bioavailability (F20%):	0.063
30% Bioavailability (F30%):	0.984

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.111
Plasma Protein Binding (PPB):	97.84552764892578%
Volume Distribution (VD):	0.448
Pgp-substrate:	3.5199902057647705%

ADMET: Metabolism

CYP1A2-inhibitor:	0.984
CYP1A2-substrate:	0.855
CYP2C19-inhibitor:	0.656
CYP2C19-substrate:	0.062
CYP2C9-inhibitor:	0.674
CYP2C9-substrate:	0.908
CYP2D6-inhibitor:	0.823
CYP2D6-substrate:	0.898
CYP3A4-inhibitor:	0.785
CYP3A4-substrate:	0.155

ADMET: Excretion

Clearance (CL):	3.862
Half-life (T1/2):	0.176

ADMET: Toxicity

hERG Blockers:	0.108
Human Hepatotoxicity (H-HT):	0.939
Drug-inuced Liver Injury (DILI):	0.985
AMES Toxicity:	0.944
Rat Oral Acute Toxicity:	0.863
Maximum Recommended Daily Dose:	0.944
Skin Sensitization:	0.387
Carcinogencity:	0.883
Eye Corrosion:	0.003
Eye Irritation:	0.594
Respiratory Toxicity:	0.918

Download Data

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

Natural Product: NPC63971

Natural Product ID:	NPC63971
*Common Name:**	Trigonostemine D
IUPAC Name:	n.a.
Synonyms:	Trigonostemine D
Standard InCHIKey:	KTOHBGJWOKYCIT-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C21H15N3O3/c1-27-11-6-7-14-16(10-11)24-21(26)17(14)20(25)19-18-13(8-9-22-19)12-4-2-3-5-15(12)23-18/h2-10,23-24,26H,1H3
SMILES:	COc1ccc2c(c1)[nH]c(c2C(=O)c1c2c(ccn1)c1ccccc1[nH]2)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1957111
PubChem CID:	n.a.
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[506674]
NPT659	Cell Line	SMMC-7721	Homo sapiens	IC50	>	40000.0	nM	PMID[506674]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	40000.0	nM	PMID[506674]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	13750.0	nM	PMID[506674]
NPT660	Cell Line	SW480	Homo sapiens	IC50	>	40000.0	nM	PMID[506674]

☑ 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 NPC63971 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	600
0.1-0.2	3719
0.2-0.3	13294
0.3-0.4	6375
0.4-0.5	13828
0.5-0.6	2328
0.6-0.7	1987
0.7-0.8	523
0.8-0.85	29
0.85-0.9	9
0.9-0.95	3
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC91868
0.9409	High Similarity	NPC235685
0.9367	High Similarity	NPC101350
0.9083	High Similarity	NPC122436
0.8756	High Similarity	NPC260434
0.8717	High Similarity	NPC207686
0.8643	High Similarity	NPC193267
0.8643	High Similarity	NPC213530
0.8565	High Similarity	NPC60621
0.8552	High Similarity	NPC27041
0.8547	High Similarity	NPC178858
0.8494	Intermediate Similarity	NPC53534
0.8382	Intermediate Similarity	NPC258048
0.8286	Intermediate Similarity	NPC152620
0.8283	Intermediate Similarity	NPC473187
0.8281	Intermediate Similarity	NPC167860
0.8281	Intermediate Similarity	NPC123976
0.8246	Intermediate Similarity	NPC229893
0.824	Intermediate Similarity	NPC182222
0.8194	Intermediate Similarity	NPC323969
0.8186	Intermediate Similarity	NPC264285
0.8165	Intermediate Similarity	NPC232727
0.8156	Intermediate Similarity	NPC63109
0.8117	Intermediate Similarity	NPC78609
0.8103	Intermediate Similarity	NPC194740
0.8077	Intermediate Similarity	NPC279189
0.8077	Intermediate Similarity	NPC200553
0.8035	Intermediate Similarity	NPC276657
0.8018	Intermediate Similarity	NPC322064
0.8017	Intermediate Similarity	NPC15801
0.7992	Intermediate Similarity	NPC148889
0.7982	Intermediate Similarity	NPC183777
0.7975	Intermediate Similarity	NPC162002
0.7973	Intermediate Similarity	NPC285558
0.7965	Intermediate Similarity	NPC16352
0.7949	Intermediate Similarity	NPC471762
0.7932	Intermediate Similarity	NPC174489
0.7932	Intermediate Similarity	NPC97902
0.7922	Intermediate Similarity	NPC310118
0.7904	Intermediate Similarity	NPC305984
0.7885	Intermediate Similarity	NPC110182
0.7879	Intermediate Similarity	NPC150239
0.787	Intermediate Similarity	NPC247803
0.7867	Intermediate Similarity	NPC266249
0.7866	Intermediate Similarity	NPC26641
0.7848	Intermediate Similarity	NPC196718
0.7848	Intermediate Similarity	NPC223427
0.7837	Intermediate Similarity	NPC165964
0.7833	Intermediate Similarity	NPC470784
0.7832	Intermediate Similarity	NPC174758
0.7801	Intermediate Similarity	NPC37152
0.7797	Intermediate Similarity	NPC123839
0.7797	Intermediate Similarity	NPC66777
0.7793	Intermediate Similarity	NPC176538
0.7792	Intermediate Similarity	NPC184680
0.7792	Intermediate Similarity	NPC303658
0.7783	Intermediate Similarity	NPC170114
0.7773	Intermediate Similarity	NPC102593
0.7764	Intermediate Similarity	NPC26543
0.7763	Intermediate Similarity	NPC87413
0.776	Intermediate Similarity	NPC74619
0.7759	Intermediate Similarity	NPC470785
0.7759	Intermediate Similarity	NPC74360
0.7754	Intermediate Similarity	NPC110151
0.7746	Intermediate Similarity	NPC208522
0.7743	Intermediate Similarity	NPC77101
0.7739	Intermediate Similarity	NPC470549
0.7725	Intermediate Similarity	NPC174760
0.7722	Intermediate Similarity	NPC314954
0.7717	Intermediate Similarity	NPC324149
0.7699	Intermediate Similarity	NPC175602
0.7699	Intermediate Similarity	NPC469554
0.7696	Intermediate Similarity	NPC469592
0.7696	Intermediate Similarity	NPC471080
0.7682	Intermediate Similarity	NPC269270
0.7682	Intermediate Similarity	NPC326422
0.7676	Intermediate Similarity	NPC295228
0.7676	Intermediate Similarity	NPC477549
0.7675	Intermediate Similarity	NPC61038
0.7675	Intermediate Similarity	NPC174672
0.7662	Intermediate Similarity	NPC237740
0.7655	Intermediate Similarity	NPC470500
0.7655	Intermediate Similarity	NPC475070
0.7652	Intermediate Similarity	NPC118940
0.7652	Intermediate Similarity	NPC219087
0.7652	Intermediate Similarity	NPC308137
0.7652	Intermediate Similarity	NPC310211
0.765	Intermediate Similarity	NPC14686
0.7642	Intermediate Similarity	NPC5145
0.7642	Intermediate Similarity	NPC11464
0.7638	Intermediate Similarity	NPC132385
0.7634	Intermediate Similarity	NPC19872
0.7632	Intermediate Similarity	NPC39679
0.7629	Intermediate Similarity	NPC274982
0.7629	Intermediate Similarity	NPC3207
0.7629	Intermediate Similarity	NPC470799
0.7629	Intermediate Similarity	NPC8022
0.7625	Intermediate Similarity	NPC132329
0.7625	Intermediate Similarity	NPC101543
0.7611	Intermediate Similarity	NPC134848
0.7611	Intermediate Similarity	NPC53144
0.7605	Intermediate Similarity	NPC157931
0.7605	Intermediate Similarity	NPC74575
0.7605	Intermediate Similarity	NPC478078
0.7597	Intermediate Similarity	NPC169402
0.7597	Intermediate Similarity	NPC304926
0.7597	Intermediate Similarity	NPC476041
0.759	Intermediate Similarity	NPC473188
0.7588	Intermediate Similarity	NPC4687
0.7588	Intermediate Similarity	NPC249583
0.7586	Intermediate Similarity	NPC116238
0.7585	Intermediate Similarity	NPC220851
0.7577	Intermediate Similarity	NPC472259
0.7572	Intermediate Similarity	NPC6786
0.7565	Intermediate Similarity	NPC470020
0.7564	Intermediate Similarity	NPC469594
0.7564	Intermediate Similarity	NPC46561
0.7564	Intermediate Similarity	NPC473041
0.7555	Intermediate Similarity	NPC171787
0.7554	Intermediate Similarity	NPC36405
0.7553	Intermediate Similarity	NPC322482
0.7552	Intermediate Similarity	NPC49547
0.7543	Intermediate Similarity	NPC207866
0.7542	Intermediate Similarity	NPC198503
0.7542	Intermediate Similarity	NPC326363
0.7534	Intermediate Similarity	NPC46580
0.7532	Intermediate Similarity	NPC82370
0.7532	Intermediate Similarity	NPC23294
0.7521	Intermediate Similarity	NPC141053
0.7511	Intermediate Similarity	NPC270918
0.751	Intermediate Similarity	NPC477861
0.75	Intermediate Similarity	NPC12344
0.75	Intermediate Similarity	NPC240384
0.75	Intermediate Similarity	NPC316981
0.75	Intermediate Similarity	NPC303374
0.75	Intermediate Similarity	NPC132539
0.749	Intermediate Similarity	NPC325976
0.749	Intermediate Similarity	NPC319232
0.749	Intermediate Similarity	NPC24370
0.7489	Intermediate Similarity	NPC295898
0.7489	Intermediate Similarity	NPC303951
0.748	Intermediate Similarity	NPC216369
0.7479	Intermediate Similarity	NPC148183
0.7479	Intermediate Similarity	NPC152768
0.7479	Intermediate Similarity	NPC330009
0.7478	Intermediate Similarity	NPC86834
0.7478	Intermediate Similarity	NPC82548
0.7478	Intermediate Similarity	NPC210828
0.7469	Intermediate Similarity	NPC41679
0.7468	Intermediate Similarity	NPC266931
0.7468	Intermediate Similarity	NPC236668
0.7467	Intermediate Similarity	NPC474916
0.746	Intermediate Similarity	NPC244543
0.7458	Intermediate Similarity	NPC473185
0.7456	Intermediate Similarity	NPC476138
0.7456	Intermediate Similarity	NPC245816
0.7456	Intermediate Similarity	NPC200836
0.7456	Intermediate Similarity	NPC317701
0.7451	Intermediate Similarity	NPC89549
0.7448	Intermediate Similarity	NPC179287
0.7448	Intermediate Similarity	NPC476818
0.7446	Intermediate Similarity	NPC185782
0.744	Intermediate Similarity	NPC270515
0.7439	Intermediate Similarity	NPC41501
0.7436	Intermediate Similarity	NPC146976
0.7434	Intermediate Similarity	NPC81535
0.7429	Intermediate Similarity	NPC472061
0.7425	Intermediate Similarity	NPC26679
0.7422	Intermediate Similarity	NPC70956
0.7422	Intermediate Similarity	NPC243834
0.7422	Intermediate Similarity	NPC227582
0.7417	Intermediate Similarity	NPC470018
0.7414	Intermediate Similarity	NPC471304
0.7414	Intermediate Similarity	NPC85273
0.7401	Intermediate Similarity	NPC121772
0.7398	Intermediate Similarity	NPC474183
0.7393	Intermediate Similarity	NPC89508
0.739	Intermediate Similarity	NPC81939
0.7389	Intermediate Similarity	NPC131887
0.7385	Intermediate Similarity	NPC191415
0.7382	Intermediate Similarity	NPC208284
0.7378	Intermediate Similarity	NPC13880
0.7378	Intermediate Similarity	NPC251090
0.7375	Intermediate Similarity	NPC21638
0.7373	Intermediate Similarity	NPC312645
0.7371	Intermediate Similarity	NPC469589
0.7366	Intermediate Similarity	NPC119006
0.7366	Intermediate Similarity	NPC307963
0.736	Intermediate Similarity	NPC475666
0.7359	Intermediate Similarity	NPC321428
0.7359	Intermediate Similarity	NPC193238
0.7357	Intermediate Similarity	NPC74413
0.7355	Intermediate Similarity	NPC246381
0.7354	Intermediate Similarity	NPC138370
0.735	Intermediate Similarity	NPC294620
0.735	Intermediate Similarity	NPC264176
0.7347	Intermediate Similarity	NPC39370
0.7336	Intermediate Similarity	NPC57398
0.7336	Intermediate Similarity	NPC260900
0.7336	Intermediate Similarity	NPC473186

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 NPC63971 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	320
0.1-0.2	657
0.2-0.3	941
0.3-0.4	1618
0.4-0.5	2674
0.5-0.6	1863
0.6-0.7	991
0.7-0.8	82
0.8-0.85	4
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8255	Intermediate Similarity	NPD2921	Clinical (unspecified phase)
0.8208	Intermediate Similarity	NPD5482	Discontinued
0.8117	Intermediate Similarity	NPD5483	Clinical (unspecified phase)
0.7992	Intermediate Similarity	NPD6790	Phase 1
0.7879	Intermediate Similarity	NPD6242	Discontinued
0.7817	Intermediate Similarity	NPD5450	Discontinued
0.7692	Intermediate Similarity	NPD6525	Clinical (unspecified phase)
0.7645	Intermediate Similarity	NPD4958	Clinical (unspecified phase)
0.7615	Intermediate Similarity	NPD5801	Clinical (unspecified phase)
0.7593	Intermediate Similarity	NPD5040	Clinical (unspecified phase)
0.7589	Intermediate Similarity	NPD6531	Approved
0.7589	Intermediate Similarity	NPD6530	Approved
0.7581	Intermediate Similarity	NPD4558	Phase 2
0.7579	Intermediate Similarity	NPD8091	Phase 3
0.7555	Intermediate Similarity	NPD2510	Approved
0.7555	Intermediate Similarity	NPD2509	Approved
0.7532	Intermediate Similarity	NPD6567	Clinical (unspecified phase)
0.7531	Intermediate Similarity	NPD3259	Approved
0.7521	Intermediate Similarity	NPD7558	Phase 2
0.7511	Intermediate Similarity	NPD5417	Clinical (unspecified phase)
0.7489	Intermediate Similarity	NPD4429	Discontinued
0.7489	Intermediate Similarity	NPD8405	Clinical (unspecified phase)
0.7478	Intermediate Similarity	NPD5658	Approved
0.7459	Intermediate Similarity	NPD3006	Discontinued
0.7404	Intermediate Similarity	NPD3389	Approved
0.7404	Intermediate Similarity	NPD3394	Approved
0.7404	Intermediate Similarity	NPD3393	Approved
0.7377	Intermediate Similarity	NPD4373	Phase 2
0.7366	Intermediate Similarity	NPD1038	Approved
0.7364	Intermediate Similarity	NPD6824	Clinical (unspecified phase)
0.7362	Intermediate Similarity	NPD5293	Phase 2
0.736	Intermediate Similarity	NPD5488	Discontinued
0.7348	Intermediate Similarity	NPD4795	Phase 2
0.7346	Intermediate Similarity	NPD7924	Phase 2
0.7346	Intermediate Similarity	NPD7925	Phase 2
0.7344	Intermediate Similarity	NPD7603	Discontinued
0.7342	Intermediate Similarity	NPD5632	Approved
0.7336	Intermediate Similarity	NPD4885	Approved
0.7331	Intermediate Similarity	NPD5612	Discontinued
0.7328	Intermediate Similarity	NPD5509	Phase 1
0.7325	Intermediate Similarity	NPD4952	Phase 3
0.7325	Intermediate Similarity	NPD5022	Discontinued
0.7325	Intermediate Similarity	NPD5479	Discontinued
0.7314	Intermediate Similarity	NPD4845	Discontinued
0.7304	Intermediate Similarity	NPD2121	Clinical (unspecified phase)
0.73	Intermediate Similarity	NPD7823	Clinical (unspecified phase)
0.728	Intermediate Similarity	NPD7393	Clinical (unspecified phase)
0.7269	Intermediate Similarity	NPD7948	Phase 1
0.7262	Intermediate Similarity	NPD7689	Approved
0.7255	Intermediate Similarity	NPD4926	Clinical (unspecified phase)
0.7249	Intermediate Similarity	NPD484	Approved
0.7249	Intermediate Similarity	NPD1740	Approved
0.7249	Intermediate Similarity	NPD1739	Approved
0.7248	Intermediate Similarity	NPD6228	Discontinued
0.7234	Intermediate Similarity	NPD5416	Discontinued
0.7224	Intermediate Similarity	NPD6962	Phase 2
0.7212	Intermediate Similarity	NPD1304	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD8279	Clinical (unspecified phase)
0.7206	Intermediate Similarity	NPD2951	Discontinued
0.7203	Intermediate Similarity	NPD8284	Discontinued
0.7202	Intermediate Similarity	NPD7426	Phase 1
0.7177	Intermediate Similarity	NPD7853	Phase 2
0.7172	Intermediate Similarity	NPD7994	Phase 2
0.7149	Intermediate Similarity	NPD4368	Phase 2
0.7137	Intermediate Similarity	NPD1392	Approved
0.7137	Intermediate Similarity	NPD5575	Clinical (unspecified phase)
0.7131	Intermediate Similarity	NPD3263	Phase 3
0.713	Intermediate Similarity	NPD6999	Discontinued
0.713	Intermediate Similarity	NPD7000	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD5901	Discontinued
0.7124	Intermediate Similarity	NPD5426	Phase 3
0.7121	Intermediate Similarity	NPD2311	Clinical (unspecified phase)
0.7106	Intermediate Similarity	NPD7665	Phase 2
0.7106	Intermediate Similarity	NPD7666	Phase 3
0.7102	Intermediate Similarity	NPD7268	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD6741	Clinical (unspecified phase)
0.7094	Intermediate Similarity	NPD3003	Approved
0.7089	Intermediate Similarity	NPD7470	Discontinued
0.7087	Intermediate Similarity	NPD4987	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD3326	Clinical (unspecified phase)
0.7072	Intermediate Similarity	NPD7803	Approved
0.7064	Intermediate Similarity	NPD7222	Phase 2
0.7059	Intermediate Similarity	NPD7069	Discontinued
0.705	Intermediate Similarity	NPD5867	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD8512	Phase 3
0.7042	Intermediate Similarity	NPD2412	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD7181	Phase 3
0.7028	Intermediate Similarity	NPD6494	Phase 2
0.7028	Intermediate Similarity	NPD4850	Phase 1
0.7026	Intermediate Similarity	NPD7198	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD7194	Discontinued
0.7024	Intermediate Similarity	NPD8017	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD8016	Phase 3
0.7021	Intermediate Similarity	NPD7001	Phase 3
0.7011	Intermediate Similarity	NPD7955	Approved
0.7011	Intermediate Similarity	NPD7956	Approved
0.7008	Intermediate Similarity	NPD7067	Approved
0.7008	Intermediate Similarity	NPD7068	Approved
0.7004	Intermediate Similarity	NPD5559	Phase 2
0.7	Intermediate Similarity	NPD5902	Approved
0.7	Intermediate Similarity	NPD6963	Approved
0.7	Intermediate Similarity	NPD5903	Approved
0.7	Intermediate Similarity	NPD6964	Approved
0.6996	Remote Similarity	NPD7414	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD8349	Phase 1
0.6992	Remote Similarity	NPD6838	Clinical (unspecified phase)
0.6992	Remote Similarity	NPD8358	Approved
0.6988	Remote Similarity	NPD5532	Phase 2
0.6983	Remote Similarity	NPD3354	Phase 2
0.6983	Remote Similarity	NPD3825	Phase 3
0.6983	Remote Similarity	NPD4118	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD4442	Phase 2
0.698	Remote Similarity	NPD3962	Phase 2
0.698	Remote Similarity	NPD7547	Clinical (unspecified phase)
0.698	Remote Similarity	NPD3959	Phase 2
0.6971	Remote Similarity	NPD2433	Clinical (unspecified phase)
0.697	Remote Similarity	NPD5003	Discontinued
0.6969	Remote Similarity	NPD6473	Phase 1
0.6962	Remote Similarity	NPD6376	Discontinued
0.6949	Remote Similarity	NPD4862	Clinical (unspecified phase)
0.6949	Remote Similarity	NPD6732	Clinical (unspecified phase)
0.6949	Remote Similarity	NPD8403	Phase 1
0.6949	Remote Similarity	NPD5530	Phase 1
0.6946	Remote Similarity	NPD5066	Phase 2
0.6946	Remote Similarity	NPD5067	Phase 2
0.694	Remote Similarity	NPD7690	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD6160	Clinical (unspecified phase)
0.6938	Remote Similarity	NPD3986	Discontinued
0.6929	Remote Similarity	NPD8363	Approved
0.6929	Remote Similarity	NPD7417	Discontinued
0.6929	Remote Similarity	NPD8364	Approved
0.6923	Remote Similarity	NPD8289	Discontinued
0.692	Remote Similarity	NPD3960	Clinical (unspecified phase)
0.692	Remote Similarity	NPD5151	Clinical (unspecified phase)
0.692	Remote Similarity	NPD3746	Discontinued
0.692	Remote Similarity	NPD7708	Approved
0.692	Remote Similarity	NPD7452	Approved
0.692	Remote Similarity	NPD7453	Approved
0.6917	Remote Similarity	NPD3330	Phase 1
0.6913	Remote Similarity	NPD802	Phase 2
0.6907	Remote Similarity	NPD3947	Discontinued
0.6903	Remote Similarity	NPD6344	Clinical (unspecified phase)
0.6902	Remote Similarity	NPD6716	Phase 1
0.69	Remote Similarity	NPD8467	Approved
0.69	Remote Similarity	NPD8466	Approved
0.69	Remote Similarity	NPD8465	Approved
0.6899	Remote Similarity	NPD6172	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD8247	Approved
0.6897	Remote Similarity	NPD8246	Approved
0.6895	Remote Similarity	NPD6165	Phase 2
0.6895	Remote Similarity	NPD6164	Phase 2
0.6891	Remote Similarity	NPD2916	Discontinued
0.689	Remote Similarity	NPD4561	Discontinued
0.6888	Remote Similarity	NPD3794	Approved
0.6888	Remote Similarity	NPD3795	Approved
0.6885	Remote Similarity	NPD7859	Phase 2
0.6883	Remote Similarity	NPD3324	Clinical (unspecified phase)
0.6878	Remote Similarity	NPD3507	Phase 2
0.6877	Remote Similarity	NPD8365	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD5802	Phase 2
0.6875	Remote Similarity	NPD5475	Discontinued
0.6873	Remote Similarity	NPD8101	Phase 3
0.6872	Remote Similarity	NPD4989	Phase 2
0.687	Remote Similarity	NPD7219	Approved
0.687	Remote Similarity	NPD3924	Approved
0.687	Remote Similarity	NPD8049	Phase 2
0.687	Remote Similarity	NPD3921	Approved
0.687	Remote Similarity	NPD3922	Approved
0.687	Remote Similarity	NPD6569	Phase 2
0.687	Remote Similarity	NPD3923	Approved
0.687	Remote Similarity	NPD7221	Approved
0.6868	Remote Similarity	NPD8524	Approved
0.6865	Remote Similarity	NPD2757	Phase 2
0.6864	Remote Similarity	NPD5513	Phase 2
0.686	Remote Similarity	NPD6140	Clinical (unspecified phase)
0.6858	Remote Similarity	NPD8463	Approved
0.6858	Remote Similarity	NPD6252	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD1996	Discontinued
0.6856	Remote Similarity	NPD5116	Phase 1
0.6853	Remote Similarity	NPD5512	Phase 3
0.6844	Remote Similarity	NPD7395	Discontinued
0.684	Remote Similarity	NPD7408	Phase 2
0.6838	Remote Similarity	NPD1768	Approved
0.6836	Remote Similarity	NPD1483	Discontinued
0.6834	Remote Similarity	NPD4369	Phase 2
0.6833	Remote Similarity	NPD648	Clinical (unspecified phase)
0.6823	Remote Similarity	NPD8525	Approved
0.682	Remote Similarity	NPD2187	Approved
0.682	Remote Similarity	NPD2189	Approved
0.6818	Remote Similarity	NPD3243	Approved
0.6816	Remote Similarity	NPD7203	Clinical (unspecified phase)
0.6816	Remote Similarity	NPD3343	Phase 3
0.6815	Remote Similarity	NPD3925	Approved
0.6815	Remote Similarity	NPD6247	Clinical (unspecified phase)
0.6808	Remote Similarity	NPD6244	Phase 3
0.6808	Remote Similarity	NPD6243	Phase 3
0.6807	Remote Similarity	NPD5601	Phase 2
0.6805	Remote Similarity	NPD4502	Phase 2
0.6802	Remote Similarity	NPD1954	Phase 1
0.6802	Remote Similarity	NPD6995	Phase 1

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