NPASS Compound

Structure

NPC473184 OpenBabel07101718292D 31 36 0 0 0 0 0 0 0 0999 V2000 1.5962 -2.1100 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 -5.2518 3.0648 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4344 2.5602 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8396 2.2557 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7653 3.3034 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2573 2.9602 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1254 1.6092 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4329 1.3422 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7872 3.0955 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1674 0.7377 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0335 0.2377 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 -2.0335 2.2377 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3014 2.2377 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 -1.1674 1.7377 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8506 2.0467 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1473 1.4013 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8995 1.7377 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 -4.4383 1.2377 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8995 0.7377 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4781 2.1444 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 0.3090 -0.9511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8506 0.4286 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.5646 1.7377 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.3601 -1.6942 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9781 0.2079 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 16 1 0 0 0 0 2 31 1 0 0 0 0 3 5 2 0 0 0 0 3 7 1 0 0 0 0 4 6 2 0 0 0 0 4 8 1 0 0 0 0 5 9 1 0 0 0 0 6 10 1 0 0 0 0 7 18 2 0 0 0 0 8 19 2 0 0 0 0 9 22 2 0 0 0 0 10 24 2 0 0 0 0 11 12 2 0 0 0 0 11 17 1 0 0 0 0 12 23 1 0 0 0 0 13 16 2 0 0 0 0 13 21 1 0 0 0 0 14 17 2 0 0 0 0 14 20 1 0 0 0 0 15 17 1 0 0 0 0 15 29 1 0 0 0 0 16 26 1 0 0 0 0 18 20 1 0 0 0 0 18 22 1 0 0 0 0 19 21 1 0 0 0 0 19 24 1 0 0 0 0 20 23 2 0 0 0 0 21 25 2 0 0 0 0 22 28 1 0 0 0 0 23 28 1 0 0 0 0 24 29 1 0 0 0 0 25 27 1 0 0 0 0 25 29 1 0 0 0 0 26 27 2 0 0 0 0 26 30 1 0 0 0 0 27 31 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	406.17
Volume:	432.146
LogP:	6.052
LogD:	4.46
LogS:	-6.186
# Rotatable Bonds:	3
TPSA:	50.18
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	6
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.352
Synthetic Accessibility Score:	2.431
Fsp3:	0.111
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.318
MDCK Permeability:	1.8385717339697294e-05
Pgp-inhibitor:	0.994
Pgp-substrate:	0.018
Human Intestinal Absorption (HIA):	0.01
20% Bioavailability (F20%):	0.926
30% Bioavailability (F30%):	0.979

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.047
Plasma Protein Binding (PPB):	98.7122573852539%
Volume Distribution (VD):	0.679
Pgp-substrate:	0.59816974401474%

ADMET: Metabolism

CYP1A2-inhibitor:	0.911
CYP1A2-substrate:	0.696
CYP2C19-inhibitor:	0.937
CYP2C19-substrate:	0.081
CYP2C9-inhibitor:	0.804
CYP2C9-substrate:	0.955
CYP2D6-inhibitor:	0.706
CYP2D6-substrate:	0.93
CYP3A4-inhibitor:	0.456
CYP3A4-substrate:	0.243

ADMET: Excretion

Clearance (CL):	6.406
Half-life (T1/2):	0.079

ADMET: Toxicity

hERG Blockers:	0.25
Human Hepatotoxicity (H-HT):	0.067
Drug-inuced Liver Injury (DILI):	0.631
AMES Toxicity:	0.91
Rat Oral Acute Toxicity:	0.134
Maximum Recommended Daily Dose:	0.97
Skin Sensitization:	0.881
Carcinogencity:	0.949
Eye Corrosion:	0.003
Eye Irritation:	0.879
Respiratory Toxicity:	0.721

Download Data

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

Natural Product: NPC473184

Natural Product ID:	NPC473184
*Common Name:**	XLYNVXKPNJGYBH-UHFFFAOYSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	XLYNVXKPNJGYBH-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C27H22N2O2/c1-16-13-21-19-8-4-6-10-24(19)29(25(21)27(31-2)26(16)30)15-17-11-12-23-20(14-17)18-7-3-5-9-22(18)28-23/h3-14,28,30H,15H2,1-2H3
SMILES:	COc1c(O)c(C)cc2c1n(Cc1ccc3c(c1)c1ccccc1[nH]3)c1c2cccc1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3633080
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000211] Indoles and derivatives [CHEMONTID:0000210] Carbazoles

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO33199	murraya tetramera	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26327273]

☑ 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
Others	1

Activity Type	# Activity
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT27	Others	Unspecified		Activity	<	80.0	%	PMID[545081]

☑ 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 NPC473184 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	707
0.1-0.2	4451
0.2-0.3	12901
0.3-0.4	7275
0.4-0.5	12125
0.5-0.6	3338
0.6-0.7	1488
0.7-0.8	370
0.8-0.85	32
0.85-0.9	5
0.9-0.95	3
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9904	High Similarity	NPC473183
0.9522	High Similarity	NPC473185
0.9481	High Similarity	NPC473182
0.9279	High Similarity	NPC473179
0.8962	High Similarity	NPC132642
0.894	High Similarity	NPC475253
0.89	High Similarity	NPC94157
0.8584	High Similarity	NPC202503
0.8538	High Similarity	NPC199667
0.8491	Intermediate Similarity	NPC473181
0.8458	Intermediate Similarity	NPC473180
0.8405	Intermediate Similarity	NPC473188
0.84	Intermediate Similarity	NPC277351
0.8318	Intermediate Similarity	NPC209769
0.8318	Intermediate Similarity	NPC477532
0.8317	Intermediate Similarity	NPC243834
0.8317	Intermediate Similarity	NPC70956
0.8294	Intermediate Similarity	NPC135887
0.8294	Intermediate Similarity	NPC199277
0.8273	Intermediate Similarity	NPC477533
0.8259	Intermediate Similarity	NPC252251
0.8217	Intermediate Similarity	NPC217554
0.8216	Intermediate Similarity	NPC470930
0.8186	Intermediate Similarity	NPC477531
0.8158	Intermediate Similarity	NPC39370
0.8152	Intermediate Similarity	NPC128823
0.815	Intermediate Similarity	NPC473186
0.8142	Intermediate Similarity	NPC209174
0.814	Intermediate Similarity	NPC193777
0.813	Intermediate Similarity	NPC11408
0.8122	Intermediate Similarity	NPC475085
0.8122	Intermediate Similarity	NPC291535
0.8122	Intermediate Similarity	NPC475112
0.8119	Intermediate Similarity	NPC316981
0.8112	Intermediate Similarity	NPC284141
0.8084	Intermediate Similarity	NPC475774
0.8082	Intermediate Similarity	NPC266931
0.8082	Intermediate Similarity	NPC471080
0.8082	Intermediate Similarity	NPC469592
0.8009	Intermediate Similarity	NPC476106
0.8008	Intermediate Similarity	NPC89549
0.7981	Intermediate Similarity	NPC242928
0.7962	Intermediate Similarity	NPC131017
0.7955	Intermediate Similarity	NPC48353
0.7937	Intermediate Similarity	NPC469594
0.7934	Intermediate Similarity	NPC72211
0.7928	Intermediate Similarity	NPC170114
0.7917	Intermediate Similarity	NPC162484
0.7907	Intermediate Similarity	NPC267423
0.7888	Intermediate Similarity	NPC473187
0.7883	Intermediate Similarity	NPC470549
0.7877	Intermediate Similarity	NPC43787
0.7877	Intermediate Similarity	NPC205934
0.7876	Intermediate Similarity	NPC280272
0.7874	Intermediate Similarity	NPC190007
0.7851	Intermediate Similarity	NPC227908
0.7851	Intermediate Similarity	NPC200888
0.784	Intermediate Similarity	NPC70259
0.7837	Intermediate Similarity	NPC94943
0.7818	Intermediate Similarity	NPC469589
0.7807	Intermediate Similarity	NPC179287
0.7798	Intermediate Similarity	NPC285558
0.7793	Intermediate Similarity	NPC112206
0.7793	Intermediate Similarity	NPC202605
0.7783	Intermediate Similarity	NPC11464
0.7778	Intermediate Similarity	NPC329747
0.7773	Intermediate Similarity	NPC475910
0.7773	Intermediate Similarity	NPC470931
0.7764	Intermediate Similarity	NPC132385
0.7759	Intermediate Similarity	NPC469554
0.7752	Intermediate Similarity	NPC223427
0.7743	Intermediate Similarity	NPC213530
0.7743	Intermediate Similarity	NPC193267
0.7742	Intermediate Similarity	NPC476044
0.774	Intermediate Similarity	NPC212535
0.7738	Intermediate Similarity	NPC201697
0.7735	Intermediate Similarity	NPC295228
0.7721	Intermediate Similarity	NPC153042
0.7706	Intermediate Similarity	NPC476997
0.7692	Intermediate Similarity	NPC474798
0.7686	Intermediate Similarity	NPC211416
0.7682	Intermediate Similarity	NPC101543
0.7672	Intermediate Similarity	NPC476998
0.7672	Intermediate Similarity	NPC476996
0.7665	Intermediate Similarity	NPC208084
0.765	Intermediate Similarity	NPC18487
0.7642	Intermediate Similarity	NPC118121
0.7637	Intermediate Similarity	NPC477861
0.7632	Intermediate Similarity	NPC86078
0.7629	Intermediate Similarity	NPC476994
0.7629	Intermediate Similarity	NPC314954
0.7626	Intermediate Similarity	NPC66815
0.7621	Intermediate Similarity	NPC303658
0.7621	Intermediate Similarity	NPC173080
0.7619	Intermediate Similarity	NPC84478
0.7611	Intermediate Similarity	NPC8022
0.7611	Intermediate Similarity	NPC470799
0.76	Intermediate Similarity	NPC478074
0.7556	Intermediate Similarity	NPC294620
0.7555	Intermediate Similarity	NPC150239
0.7545	Intermediate Similarity	NPC167860
0.7545	Intermediate Similarity	NPC123976
0.7544	Intermediate Similarity	NPC184408
0.7534	Intermediate Similarity	NPC11017
0.7533	Intermediate Similarity	NPC183407
0.7523	Intermediate Similarity	NPC304183
0.7511	Intermediate Similarity	NPC208284
0.7511	Intermediate Similarity	NPC46451
0.7511	Intermediate Similarity	NPC476138
0.7511	Intermediate Similarity	NPC245816
0.75	Intermediate Similarity	NPC473189
0.7479	Intermediate Similarity	NPC274640
0.7479	Intermediate Similarity	NPC184680
0.7478	Intermediate Similarity	NPC26679
0.7477	Intermediate Similarity	NPC36229
0.7477	Intermediate Similarity	NPC16452
0.7477	Intermediate Similarity	NPC476581
0.7467	Intermediate Similarity	NPC204446
0.7467	Intermediate Similarity	NPC100079
0.7467	Intermediate Similarity	NPC247803
0.7467	Intermediate Similarity	NPC23614
0.7458	Intermediate Similarity	NPC475844
0.7448	Intermediate Similarity	NPC470785
0.7445	Intermediate Similarity	NPC162530
0.7435	Intermediate Similarity	NPC148409
0.7434	Intermediate Similarity	NPC87413
0.7429	Intermediate Similarity	NPC72980
0.7422	Intermediate Similarity	NPC185782
0.7421	Intermediate Similarity	NPC232727
0.7419	Intermediate Similarity	NPC475190
0.7418	Intermediate Similarity	NPC270515
0.7417	Intermediate Similarity	NPC41501
0.7414	Intermediate Similarity	NPC162748
0.7414	Intermediate Similarity	NPC122463
0.7414	Intermediate Similarity	NPC144452
0.7407	Intermediate Similarity	NPC475666
0.7406	Intermediate Similarity	NPC476995
0.7403	Intermediate Similarity	NPC225279
0.7401	Intermediate Similarity	NPC296482
0.7401	Intermediate Similarity	NPC171409
0.7401	Intermediate Similarity	NPC202768
0.7401	Intermediate Similarity	NPC53069
0.7401	Intermediate Similarity	NPC203168
0.7401	Intermediate Similarity	NPC96405
0.7395	Intermediate Similarity	NPC246700
0.7393	Intermediate Similarity	NPC195788
0.7393	Intermediate Similarity	NPC237901
0.7389	Intermediate Similarity	NPC219664
0.7388	Intermediate Similarity	NPC472067
0.7388	Intermediate Similarity	NPC472031
0.7388	Intermediate Similarity	NPC472066
0.7385	Intermediate Similarity	NPC326634
0.7382	Intermediate Similarity	NPC51388
0.7376	Intermediate Similarity	NPC329793
0.7375	Intermediate Similarity	NPC470784
0.7373	Intermediate Similarity	NPC141915
0.7373	Intermediate Similarity	NPC280964
0.7373	Intermediate Similarity	NPC114335
0.7371	Intermediate Similarity	NPC310118
0.7368	Intermediate Similarity	NPC39500
0.7366	Intermediate Similarity	NPC208522
0.7366	Intermediate Similarity	NPC81939
0.7362	Intermediate Similarity	NPC110151
0.7357	Intermediate Similarity	NPC187501
0.7353	Intermediate Similarity	NPC180504
0.7348	Intermediate Similarity	NPC314552
0.7348	Intermediate Similarity	NPC305984
0.7346	Intermediate Similarity	NPC88363
0.7342	Intermediate Similarity	NPC31930
0.7342	Intermediate Similarity	NPC201508
0.7339	Intermediate Similarity	NPC307963
0.7336	Intermediate Similarity	NPC235076
0.7336	Intermediate Similarity	NPC118228
0.7331	Intermediate Similarity	NPC194740
0.7328	Intermediate Similarity	NPC174760
0.7325	Intermediate Similarity	NPC251160
0.7324	Intermediate Similarity	NPC176127
0.7321	Intermediate Similarity	NPC474409
0.7319	Intermediate Similarity	NPC214980
0.7317	Intermediate Similarity	NPC26543
0.7316	Intermediate Similarity	NPC473041
0.7313	Intermediate Similarity	NPC5145
0.7306	Intermediate Similarity	NPC472068
0.7302	Intermediate Similarity	NPC204385
0.7301	Intermediate Similarity	NPC39679
0.7297	Intermediate Similarity	NPC19872
0.7294	Intermediate Similarity	NPC99666
0.7293	Intermediate Similarity	NPC149471
0.7293	Intermediate Similarity	NPC271215
0.7286	Intermediate Similarity	NPC312872
0.728	Intermediate Similarity	NPC260909
0.7273	Intermediate Similarity	NPC251090
0.7273	Intermediate Similarity	NPC13880
0.7269	Intermediate Similarity	NPC46580
0.7269	Intermediate Similarity	NPC474688
0.7261	Intermediate Similarity	NPC6786
0.7257	Intermediate Similarity	NPC249583
0.7257	Intermediate Similarity	NPC253580
0.7257	Intermediate Similarity	NPC4687
0.7256	Intermediate Similarity	NPC42591

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 NPC473184 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	360
0.1-0.2	707
0.2-0.3	910
0.3-0.4	1794
0.4-0.5	2809
0.5-0.6	1924
0.6-0.7	568
0.7-0.8	76
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8295	Intermediate Similarity	NPD5902	Approved
0.8295	Intermediate Similarity	NPD5903	Approved
0.8186	Intermediate Similarity	NPD5658	Approved
0.817	Intermediate Similarity	NPD6503	Clinical (unspecified phase)
0.7926	Intermediate Similarity	NPD3003	Approved
0.789	Intermediate Similarity	NPD7222	Phase 2
0.7879	Intermediate Similarity	NPD7558	Phase 2
0.7808	Intermediate Similarity	NPD7452	Approved
0.7808	Intermediate Similarity	NPD7453	Approved
0.7778	Intermediate Similarity	NPD6985	Discontinued
0.7773	Intermediate Similarity	NPD6773	Clinical (unspecified phase)
0.7743	Intermediate Similarity	NPD7194	Discontinued
0.7725	Intermediate Similarity	NPD6494	Phase 2
0.7689	Intermediate Similarity	NPD5612	Discontinued
0.765	Intermediate Similarity	NPD1768	Approved
0.757	Intermediate Similarity	NPD8364	Approved
0.757	Intermediate Similarity	NPD8363	Approved
0.7511	Intermediate Similarity	NPD4502	Phase 2
0.7511	Intermediate Similarity	NPD3763	Approved
0.751	Intermediate Similarity	NPD8365	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6344	Clinical (unspecified phase)
0.7489	Intermediate Similarity	NPD1392	Approved
0.7489	Intermediate Similarity	NPD6160	Clinical (unspecified phase)
0.7489	Intermediate Similarity	NPD4118	Clinical (unspecified phase)
0.7403	Intermediate Similarity	NPD7678	Clinical (unspecified phase)
0.7401	Intermediate Similarity	NPD3816	Phase 1
0.7401	Intermediate Similarity	NPD3815	Phase 1
0.7393	Intermediate Similarity	NPD8429	Approved
0.7393	Intermediate Similarity	NPD8427	Approved
0.7393	Intermediate Similarity	NPD8467	Approved
0.7393	Intermediate Similarity	NPD8466	Approved
0.7393	Intermediate Similarity	NPD8465	Approved
0.7393	Intermediate Similarity	NPD8428	Approved
0.7384	Intermediate Similarity	NPD4885	Approved
0.7379	Intermediate Similarity	NPD8244	Phase 2
0.7366	Intermediate Similarity	NPD5530	Phase 1
0.7359	Intermediate Similarity	NPD3875	Discontinued
0.7357	Intermediate Similarity	NPD5067	Phase 2
0.7357	Intermediate Similarity	NPD5066	Phase 2
0.7355	Intermediate Similarity	NPD6517	Phase 3
0.7348	Intermediate Similarity	NPD5164	Discontinued
0.7339	Intermediate Similarity	NPD1038	Approved
0.7318	Intermediate Similarity	NPD7948	Phase 1
0.7317	Intermediate Similarity	NPD6243	Phase 3
0.7317	Intermediate Similarity	NPD6244	Phase 3
0.7289	Intermediate Similarity	NPD8403	Phase 1
0.728	Intermediate Similarity	NPD8425	Approved
0.728	Intermediate Similarity	NPD8459	Approved
0.728	Intermediate Similarity	NPD8460	Approved
0.728	Intermediate Similarity	NPD8426	Approved
0.7265	Intermediate Similarity	NPD4511	Phase 1
0.7253	Intermediate Similarity	NPD5930	Phase 3
0.7252	Intermediate Similarity	NPD8396	Approved
0.7252	Intermediate Similarity	NPD8395	Approved
0.7248	Intermediate Similarity	NPD5912	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD5913	Phase 3
0.7241	Intermediate Similarity	NPD5632	Approved
0.7227	Intermediate Similarity	NPD6861	Clinical (unspecified phase)
0.7211	Intermediate Similarity	NPD8091	Phase 3
0.7205	Intermediate Similarity	NPD5939	Approved
0.7205	Intermediate Similarity	NPD5936	Approved
0.7198	Intermediate Similarity	NPD7823	Clinical (unspecified phase)
0.7191	Intermediate Similarity	NPD1954	Phase 1
0.7185	Intermediate Similarity	NPD7555	Discontinued
0.7183	Intermediate Similarity	NPD3920	Phase 2
0.7182	Intermediate Similarity	NPD5575	Clinical (unspecified phase)
0.7182	Intermediate Similarity	NPD1304	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD5070	Clinical (unspecified phase)
0.7167	Intermediate Similarity	NPD8109	Clinical (unspecified phase)
0.7149	Intermediate Similarity	NPD4454	Phase 2
0.7149	Intermediate Similarity	NPD4418	Discontinued
0.7149	Intermediate Similarity	NPD3324	Clinical (unspecified phase)
0.7137	Intermediate Similarity	NPD4080	Discontinued
0.7136	Intermediate Similarity	NPD3921	Approved
0.7136	Intermediate Similarity	NPD3924	Approved
0.7136	Intermediate Similarity	NPD3923	Approved
0.7136	Intermediate Similarity	NPD3922	Approved
0.7131	Intermediate Similarity	NPD7719	Discontinued
0.7131	Intermediate Similarity	NPD6976	Clinical (unspecified phase)
0.712	Intermediate Similarity	NPD7859	Phase 2
0.7119	Intermediate Similarity	NPD7221	Approved
0.7119	Intermediate Similarity	NPD7219	Approved
0.7115	Intermediate Similarity	NPD7956	Approved
0.7115	Intermediate Similarity	NPD7955	Approved
0.7101	Intermediate Similarity	NPD7603	Discontinued
0.71	Intermediate Similarity	NPD3330	Phase 1
0.7098	Intermediate Similarity	NPD2176	Approved
0.7098	Intermediate Similarity	NPD2177	Approved
0.7098	Intermediate Similarity	NPD2175	Phase 3
0.7071	Intermediate Similarity	NPD6977	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD6978	Phase 2
0.707	Intermediate Similarity	NPD6456	Discontinued
0.7066	Intermediate Similarity	NPD6741	Clinical (unspecified phase)
0.7062	Intermediate Similarity	NPD1325	Approved
0.7062	Intermediate Similarity	NPD1326	Approved
0.7061	Intermediate Similarity	NPD8279	Clinical (unspecified phase)
0.7056	Intermediate Similarity	NPD6220	Phase 3
0.7056	Intermediate Similarity	NPD6159	Phase 2
0.7051	Intermediate Similarity	NPD5083	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD7067	Approved
0.7045	Intermediate Similarity	NPD7068	Approved
0.7042	Intermediate Similarity	NPD7710	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD5417	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD6964	Approved
0.7037	Intermediate Similarity	NPD6963	Approved
0.7031	Intermediate Similarity	NPD6290	Phase 2
0.7028	Intermediate Similarity	NPD8358	Approved
0.7023	Intermediate Similarity	NPD7479	Phase 2
0.7016	Intermediate Similarity	NPD6230	Discontinued
0.7008	Intermediate Similarity	NPD7169	Suspended
0.7	Intermediate Similarity	NPD5863	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD7671	Approved
0.7	Intermediate Similarity	NPD7672	Approved
0.7	Intermediate Similarity	NPD2916	Discontinued
0.6986	Remote Similarity	NPD5256	Discontinued
0.6985	Remote Similarity	NPD8489	Phase 1
0.6983	Remote Similarity	NPD4131	Phase 3
0.6982	Remote Similarity	NPD6569	Phase 2
0.6977	Remote Similarity	NPD8284	Discontinued
0.6977	Remote Similarity	NPD7803	Approved
0.6971	Remote Similarity	NPD5559	Phase 2
0.6964	Remote Similarity	NPD7417	Discontinued
0.6964	Remote Similarity	NPD6449	Clinical (unspecified phase)
0.6962	Remote Similarity	NPD6717	Clinical (unspecified phase)
0.6958	Remote Similarity	NPD7674	Phase 3
0.6958	Remote Similarity	NPD7676	Clinical (unspecified phase)
0.6958	Remote Similarity	NPD7675	Phase 3
0.6958	Remote Similarity	NPD7426	Phase 1
0.6957	Remote Similarity	NPD5429	Discontinued
0.6953	Remote Similarity	NPD6530	Approved
0.6953	Remote Similarity	NPD6531	Approved
0.6951	Remote Similarity	NPD802	Phase 2
0.6949	Remote Similarity	NPD8405	Clinical (unspecified phase)
0.6949	Remote Similarity	NPD7395	Discontinued
0.6948	Remote Similarity	NPD4083	Discontinued
0.6947	Remote Similarity	NPD3825	Phase 3
0.6943	Remote Similarity	NPD4795	Phase 2
0.6942	Remote Similarity	NPD5479	Discontinued
0.6942	Remote Similarity	NPD8512	Phase 3
0.6941	Remote Similarity	NPD6610	Clinical (unspecified phase)
0.6935	Remote Similarity	NPD6716	Phase 1
0.6935	Remote Similarity	NPD6473	Phase 1
0.6923	Remote Similarity	NPD2921	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD7025	Clinical (unspecified phase)
0.692	Remote Similarity	NPD6455	Phase 3
0.692	Remote Similarity	NPD3402	Phase 1
0.692	Remote Similarity	NPD6491	Clinical (unspecified phase)
0.6917	Remote Similarity	NPD6743	Phase 2
0.6917	Remote Similarity	NPD6742	Phase 2
0.6905	Remote Similarity	NPD5482	Discontinued
0.69	Remote Similarity	NPD6991	Approved
0.6894	Remote Similarity	NPD6140	Clinical (unspecified phase)
0.6891	Remote Similarity	NPD6242	Discontinued
0.6883	Remote Similarity	NPD7729	Clinical (unspecified phase)
0.6883	Remote Similarity	NPD6750	Phase 2
0.6881	Remote Similarity	NPD7414	Clinical (unspecified phase)
0.688	Remote Similarity	NPD7181	Phase 3
0.6878	Remote Similarity	NPD6141	Clinical (unspecified phase)
0.6872	Remote Similarity	NPD7567	Approved
0.6863	Remote Similarity	NPD8442	Discontinued
0.686	Remote Similarity	NPD7268	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD4373	Phase 2
0.6856	Remote Similarity	NPD6975	Discontinued
0.6855	Remote Similarity	NPD8016	Phase 3
0.6855	Remote Similarity	NPD8017	Clinical (unspecified phase)
0.6849	Remote Similarity	NPD5522	Clinical (unspecified phase)
0.6846	Remote Similarity	NPD3343	Phase 3
0.6844	Remote Similarity	NPD6590	Discontinued
0.6838	Remote Similarity	NPD6525	Clinical (unspecified phase)
0.6833	Remote Similarity	NPD6339	Approved
0.6833	Remote Similarity	NPD6340	Approved
0.6833	Remote Similarity	NPD6824	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD2951	Discontinued
0.6824	Remote Similarity	NPD2125	Clinical (unspecified phase)
0.6822	Remote Similarity	NPD7708	Approved
0.6816	Remote Similarity	NPD3746	Discontinued
0.6813	Remote Similarity	NPD5483	Clinical (unspecified phase)
0.6804	Remote Similarity	NPD4203	Approved
0.6804	Remote Similarity	NPD4204	Approved
0.6803	Remote Similarity	NPD5022	Discontinued
0.6802	Remote Similarity	NPD7853	Phase 2
0.6802	Remote Similarity	NPD3006	Discontinued
0.68	Remote Similarity	NPD4876	Phase 3
0.68	Remote Similarity	NPD4875	Phase 3
0.6797	Remote Similarity	NPD4034	Approved
0.6797	Remote Similarity	NPD4033	Approved
0.6797	Remote Similarity	NPD32	Approved
0.6797	Remote Similarity	NPD31	Approved
0.6797	Remote Similarity	NPD4037	Approved
0.6797	Remote Similarity	NPD4122	Approved
0.6797	Remote Similarity	NPD4036	Approved
0.6797	Remote Similarity	NPD4039	Approved
0.6797	Remote Similarity	NPD4035	Approved
0.6797	Remote Similarity	NPD4038	Approved
0.6793	Remote Similarity	NPD6643	Discontinued
0.6792	Remote Similarity	NPD7726	Phase 1
0.679	Remote Similarity	NPD7994	Phase 2
0.679	Remote Similarity	NPD3259	Approved
0.679	Remote Similarity	NPD6553	Clinical (unspecified phase)
0.6787	Remote Similarity	NPD7690	Clinical (unspecified phase)

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