NPASS Compound

Structure

NPC473181 OpenBabel07101718292D 30 35 0 0 0 0 0 0 0 0999 V2000 -0.2079 -3.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8060 -1.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4745 -3.8052 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9836 -0.1045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0623 -2.9962 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5768 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4800 -3.7007 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3958 -0.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6556 -2.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5823 0.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3902 -1.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2562 -0.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0739 -2.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5241 -2.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2562 -2.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2079 -2.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3902 -2.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0733 -2.7872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4013 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6581 -2.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1222 -2.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6611 -1.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9945 0.1045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1222 -1.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0739 -1.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6581 -1.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2079 -0.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0733 -1.1691 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 -1.9400 -0.9781 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 16 1 0 0 0 0 2 30 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 23 2 0 0 0 0 11 12 2 0 0 0 0 11 17 1 0 0 0 0 12 24 1 0 0 0 0 13 16 2 0 0 0 0 13 25 1 0 0 0 0 14 17 1 0 0 0 0 14 20 1 0 0 0 0 15 17 2 0 0 0 0 15 21 1 0 0 0 0 16 20 1 0 0 0 0 18 21 1 0 0 0 0 18 22 1 0 0 0 0 19 23 1 0 0 0 0 19 26 1 0 0 0 0 20 26 2 0 0 0 0 21 24 2 0 0 0 0 22 28 1 0 0 0 0 23 29 1 0 0 0 0 24 28 1 0 0 0 0 25 27 2 0 0 0 0 25 30 1 0 0 0 0 26 27 1 0 0 0 0 27 29 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	390.17
Volume:	423.356
LogP:	6.603
LogD:	4.759
LogS:	-6.989
# Rotatable Bonds:	3
TPSA:	40.81
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	6
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.34
Synthetic Accessibility Score:	2.412
Fsp3:	0.111
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.623
MDCK Permeability:	8.125125532387756e-06
Pgp-inhibitor:	0.988
Pgp-substrate:	0.068
Human Intestinal Absorption (HIA):	0.011
20% Bioavailability (F20%):	0.817
30% Bioavailability (F30%):	0.985

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.115
Plasma Protein Binding (PPB):	99.05905151367188%
Volume Distribution (VD):	1.241
Pgp-substrate:	0.7945874929428101%

ADMET: Metabolism

CYP1A2-inhibitor:	0.937
CYP1A2-substrate:	0.93
CYP2C19-inhibitor:	0.758
CYP2C19-substrate:	0.081
CYP2C9-inhibitor:	0.733
CYP2C9-substrate:	0.958
CYP2D6-inhibitor:	0.623
CYP2D6-substrate:	0.948
CYP3A4-inhibitor:	0.462
CYP3A4-substrate:	0.72

ADMET: Excretion

Clearance (CL):	4.913
Half-life (T1/2):	0.14

ADMET: Toxicity

hERG Blockers:	0.096
Human Hepatotoxicity (H-HT):	0.173
Drug-inuced Liver Injury (DILI):	0.932
AMES Toxicity:	0.884
Rat Oral Acute Toxicity:	0.169
Maximum Recommended Daily Dose:	0.954
Skin Sensitization:	0.911
Carcinogencity:	0.911
Eye Corrosion:	0.003
Eye Irritation:	0.932
Respiratory Toxicity:	0.985

Download Data

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

Natural Product: NPC473181

Natural Product ID:	NPC473181
*Common Name:**	VPSSOBMDZQKCLI-UHFFFAOYSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	VPSSOBMDZQKCLI-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C27H22N2O/c1-16-13-25(30-2)27-26(19-8-4-6-10-23(19)29-27)20(16)14-17-11-12-24-21(15-17)18-7-3-5-9-22(18)28-24/h3-13,15,28-29H,14H2,1-2H3
SMILES:	COc1cc(C)c(c2c1[nH]c1c2cccc1)Cc1ccc2c(c1)c1ccccc1[nH]2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3633077
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
IC50	1

Activity Type	# Activity
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	26700.0	nM	PMID[495111]

☑ 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 NPC473181 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	936
0.1-0.2	5221
0.2-0.3	12186
0.3-0.4	9386
0.4-0.5	10456
0.5-0.6	2918
0.6-0.7	1267
0.7-0.8	271
0.8-0.85	41
0.85-0.9	9
0.9-0.95	3
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9946	High Similarity	NPC199667
0.9632	High Similarity	NPC473180
0.9227	High Similarity	NPC94157
0.9141	High Similarity	NPC473179
0.9027	High Similarity	NPC242928
0.8981	High Similarity	NPC473182
0.8905	High Similarity	NPC132642
0.8829	High Similarity	NPC473185
0.878	High Similarity	NPC202503
0.8703	High Similarity	NPC474798
0.8702	High Similarity	NPC475253
0.8608	High Similarity	NPC128823
0.8537	High Similarity	NPC225279
0.8498	Intermediate Similarity	NPC473183
0.8491	Intermediate Similarity	NPC473184
0.8485	Intermediate Similarity	NPC470930
0.8483	Intermediate Similarity	NPC473186
0.8454	Intermediate Similarity	NPC144452
0.8429	Intermediate Similarity	NPC252251
0.8404	Intermediate Similarity	NPC39370
0.8349	Intermediate Similarity	NPC477531
0.8325	Intermediate Similarity	NPC208284
0.8317	Intermediate Similarity	NPC201697
0.8308	Intermediate Similarity	NPC193777
0.8302	Intermediate Similarity	NPC209174
0.8263	Intermediate Similarity	NPC474688
0.8256	Intermediate Similarity	NPC475190
0.8255	Intermediate Similarity	NPC274640
0.8241	Intermediate Similarity	NPC267423
0.8214	Intermediate Similarity	NPC131017
0.8182	Intermediate Similarity	NPC72211
0.8182	Intermediate Similarity	NPC86078
0.8177	Intermediate Similarity	NPC473189
0.8173	Intermediate Similarity	NPC70259
0.8159	Intermediate Similarity	NPC162484
0.8146	Intermediate Similarity	NPC187501
0.8143	Intermediate Similarity	NPC477532
0.8137	Intermediate Similarity	NPC209769
0.8131	Intermediate Similarity	NPC70956
0.8131	Intermediate Similarity	NPC243834
0.8122	Intermediate Similarity	NPC43787
0.8122	Intermediate Similarity	NPC205934
0.8107	Intermediate Similarity	NPC48353
0.8095	Intermediate Similarity	NPC477533
0.8069	Intermediate Similarity	NPC475774
0.8069	Intermediate Similarity	NPC245816
0.8069	Intermediate Similarity	NPC223427
0.8069	Intermediate Similarity	NPC476138
0.8068	Intermediate Similarity	NPC39500
0.8048	Intermediate Similarity	NPC208084
0.7991	Intermediate Similarity	NPC227908
0.7981	Intermediate Similarity	NPC51388
0.7979	Intermediate Similarity	NPC176127
0.7972	Intermediate Similarity	NPC469554
0.7972	Intermediate Similarity	NPC101543
0.797	Intermediate Similarity	NPC476044
0.7964	Intermediate Similarity	NPC475844
0.7959	Intermediate Similarity	NPC246700
0.7941	Intermediate Similarity	NPC285558
0.7938	Intermediate Similarity	NPC84478
0.7931	Intermediate Similarity	NPC475085
0.7931	Intermediate Similarity	NPC475112
0.7931	Intermediate Similarity	NPC291535
0.7921	Intermediate Similarity	NPC329747
0.7915	Intermediate Similarity	NPC184408
0.7871	Intermediate Similarity	NPC18487
0.7867	Intermediate Similarity	NPC293151
0.7861	Intermediate Similarity	NPC118511
0.7861	Intermediate Similarity	NPC153042
0.7857	Intermediate Similarity	NPC470549
0.7833	Intermediate Similarity	NPC329793
0.782	Intermediate Similarity	NPC170114
0.7816	Intermediate Similarity	NPC476106
0.7812	Intermediate Similarity	NPC56618
0.7778	Intermediate Similarity	NPC179287
0.7778	Intermediate Similarity	NPC128751
0.7773	Intermediate Similarity	NPC180504
0.7763	Intermediate Similarity	NPC474701
0.7763	Intermediate Similarity	NPC473188
0.7762	Intermediate Similarity	NPC26679
0.7739	Intermediate Similarity	NPC106833
0.7739	Intermediate Similarity	NPC469497
0.7732	Intermediate Similarity	NPC88363
0.7727	Intermediate Similarity	NPC49547
0.7721	Intermediate Similarity	NPC280799
0.7716	Intermediate Similarity	NPC94943
0.7703	Intermediate Similarity	NPC473187
0.7703	Intermediate Similarity	NPC185782
0.77	Intermediate Similarity	NPC314552
0.7678	Intermediate Similarity	NPC294620
0.7671	Intermediate Similarity	NPC314954
0.7667	Intermediate Similarity	NPC123976
0.7667	Intermediate Similarity	NPC167860
0.7665	Intermediate Similarity	NPC190007
0.7661	Intermediate Similarity	NPC470018
0.7659	Intermediate Similarity	NPC19872
0.7659	Intermediate Similarity	NPC11017
0.765	Intermediate Similarity	NPC76748
0.7644	Intermediate Similarity	NPC45190
0.7644	Intermediate Similarity	NPC300156
0.7642	Intermediate Similarity	NPC476287
0.7642	Intermediate Similarity	NPC478074
0.7642	Intermediate Similarity	NPC471080
0.7642	Intermediate Similarity	NPC469592
0.7626	Intermediate Similarity	NPC74575
0.7621	Intermediate Similarity	NPC208522
0.7614	Intermediate Similarity	NPC212535
0.7612	Intermediate Similarity	NPC92111
0.7608	Intermediate Similarity	NPC4687
0.7608	Intermediate Similarity	NPC249583
0.7606	Intermediate Similarity	NPC118228
0.76	Intermediate Similarity	NPC296527
0.7585	Intermediate Similarity	NPC135887
0.7585	Intermediate Similarity	NPC199277
0.7583	Intermediate Similarity	NPC471304
0.7578	Intermediate Similarity	NPC277351
0.7577	Intermediate Similarity	NPC312872
0.7573	Intermediate Similarity	NPC176538
0.7571	Intermediate Similarity	NPC475910
0.7556	Intermediate Similarity	NPC11408
0.7537	Intermediate Similarity	NPC307963
0.7536	Intermediate Similarity	NPC232727
0.7532	Intermediate Similarity	NPC89549
0.7523	Intermediate Similarity	NPC280272
0.75	Intermediate Similarity	NPC200888
0.75	Intermediate Similarity	NPC469594
0.7489	Intermediate Similarity	NPC217554
0.7489	Intermediate Similarity	NPC477066
0.7488	Intermediate Similarity	NPC280964
0.7488	Intermediate Similarity	NPC114335
0.7488	Intermediate Similarity	NPC141915
0.7488	Intermediate Similarity	NPC470931
0.7488	Intermediate Similarity	NPC8022
0.7488	Intermediate Similarity	NPC470799
0.7465	Intermediate Similarity	NPC292958
0.7465	Intermediate Similarity	NPC87413
0.7463	Intermediate Similarity	NPC473177
0.746	Intermediate Similarity	NPC26850
0.7456	Intermediate Similarity	NPC478081
0.745	Intermediate Similarity	NPC42591
0.7441	Intermediate Similarity	NPC283117
0.743	Intermediate Similarity	NPC308137
0.743	Intermediate Similarity	NPC310211
0.7424	Intermediate Similarity	NPC478032
0.7419	Intermediate Similarity	NPC303658
0.7419	Intermediate Similarity	NPC46561
0.7415	Intermediate Similarity	NPC195314
0.7414	Intermediate Similarity	NPC26543
0.7413	Intermediate Similarity	NPC204385
0.7397	Intermediate Similarity	NPC198503
0.7395	Intermediate Similarity	NPC266931
0.7393	Intermediate Similarity	NPC304183
0.7391	Intermediate Similarity	NPC284141
0.7387	Intermediate Similarity	NPC206201
0.7385	Intermediate Similarity	NPC193267
0.7385	Intermediate Similarity	NPC213530
0.738	Intermediate Similarity	NPC477067
0.738	Intermediate Similarity	NPC478082
0.7379	Intermediate Similarity	NPC251090
0.7373	Intermediate Similarity	NPC169402
0.7373	Intermediate Similarity	NPC305984
0.7363	Intermediate Similarity	NPC476319
0.7361	Intermediate Similarity	NPC116238
0.7357	Intermediate Similarity	NPC6786
0.7356	Intermediate Similarity	NPC476167
0.7352	Intermediate Similarity	NPC150239
0.7346	Intermediate Similarity	NPC164374
0.7346	Intermediate Similarity	NPC137929
0.7339	Intermediate Similarity	NPC96321
0.7339	Intermediate Similarity	NPC473041
0.7336	Intermediate Similarity	NPC188420
0.7331	Intermediate Similarity	NPC53534
0.7315	Intermediate Similarity	NPC149471
0.7315	Intermediate Similarity	NPC271215
0.7315	Intermediate Similarity	NPC162530
0.7313	Intermediate Similarity	NPC295228
0.7308	Intermediate Similarity	NPC192315
0.7304	Intermediate Similarity	NPC473540
0.7302	Intermediate Similarity	NPC9894
0.7302	Intermediate Similarity	NPC294375
0.7302	Intermediate Similarity	NPC26872
0.7301	Intermediate Similarity	NPC329631
0.7286	Intermediate Similarity	NPC72980
0.7286	Intermediate Similarity	NPC470586
0.7284	Intermediate Similarity	NPC475666
0.7282	Intermediate Similarity	NPC473178
0.7269	Intermediate Similarity	NPC251160
0.7269	Intermediate Similarity	NPC38237
0.726	Intermediate Similarity	NPC247803
0.7256	Intermediate Similarity	NPC11464
0.7253	Intermediate Similarity	NPC17437
0.7252	Intermediate Similarity	NPC167908
0.7243	Intermediate Similarity	NPC477111
0.7243	Intermediate Similarity	NPC39679
0.7241	Intermediate Similarity	NPC81939
0.7237	Intermediate Similarity	NPC470017
0.7233	Intermediate Similarity	NPC99666
0.7227	Intermediate Similarity	NPC46451
0.7212	Intermediate Similarity	NPC13880
0.7209	Intermediate Similarity	NPC469589

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 NPC473181 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	498
0.1-0.2	695
0.2-0.3	890
0.3-0.4	1651
0.4-0.5	2959
0.5-0.6	1841
0.6-0.7	535
0.7-0.8	80
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8104	Intermediate Similarity	NPD6160	Clinical (unspecified phase)
0.7971	Intermediate Similarity	NPD4502	Phase 2
0.796	Intermediate Similarity	NPD4118	Clinical (unspecified phase)
0.7925	Intermediate Similarity	NPD7678	Clinical (unspecified phase)
0.774	Intermediate Similarity	NPD5658	Approved
0.7707	Intermediate Similarity	NPD4511	Phase 1
0.77	Intermediate Similarity	NPD5912	Clinical (unspecified phase)
0.77	Intermediate Similarity	NPD5913	Phase 3
0.77	Intermediate Similarity	NPD5164	Discontinued
0.7692	Intermediate Similarity	NPD7222	Phase 2
0.7673	Intermediate Similarity	NPD6491	Clinical (unspecified phase)
0.7673	Intermediate Similarity	NPD3324	Clinical (unspecified phase)
0.7644	Intermediate Similarity	NPD8403	Phase 1
0.763	Intermediate Similarity	NPD5939	Approved
0.763	Intermediate Similarity	NPD5936	Approved
0.7624	Intermediate Similarity	NPD1304	Clinical (unspecified phase)
0.7609	Intermediate Similarity	NPD6503	Clinical (unspecified phase)
0.7608	Intermediate Similarity	NPD7453	Approved
0.7608	Intermediate Similarity	NPD5429	Discontinued
0.7608	Intermediate Similarity	NPD7452	Approved
0.7551	Intermediate Similarity	NPD3920	Phase 2
0.7537	Intermediate Similarity	NPD1038	Approved
0.7524	Intermediate Similarity	NPD2176	Approved
0.7524	Intermediate Similarity	NPD2175	Phase 3
0.7524	Intermediate Similarity	NPD8395	Approved
0.7524	Intermediate Similarity	NPD2177	Approved
0.7524	Intermediate Similarity	NPD8396	Approved
0.7523	Intermediate Similarity	NPD5902	Approved
0.7523	Intermediate Similarity	NPD5903	Approved
0.7487	Intermediate Similarity	NPD5083	Clinical (unspecified phase)
0.7476	Intermediate Similarity	NPD3003	Approved
0.7476	Intermediate Similarity	NPD5530	Phase 1
0.7441	Intermediate Similarity	NPD6290	Phase 2
0.744	Intermediate Similarity	NPD3825	Phase 3
0.7419	Intermediate Similarity	NPD8109	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD5612	Discontinued
0.7385	Intermediate Similarity	NPD3875	Discontinued
0.7379	Intermediate Similarity	NPD6550	Discontinued
0.7361	Intermediate Similarity	NPD6140	Clinical (unspecified phase)
0.7356	Intermediate Similarity	NPD4548	Discontinued
0.7339	Intermediate Similarity	NPD7395	Discontinued
0.7333	Intermediate Similarity	NPD3746	Discontinued
0.733	Intermediate Similarity	NPD6590	Discontinued
0.733	Intermediate Similarity	NPD4418	Discontinued
0.7321	Intermediate Similarity	NPD5479	Discontinued
0.7311	Intermediate Similarity	NPD6150	Discontinued
0.7306	Intermediate Similarity	NPD3402	Phase 1
0.7303	Intermediate Similarity	NPD6773	Clinical (unspecified phase)
0.7301	Intermediate Similarity	NPD6741	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD2125	Clinical (unspecified phase)
0.7287	Intermediate Similarity	NPD3835	Phase 3
0.7287	Intermediate Similarity	NPD3833	Phase 3
0.7277	Intermediate Similarity	NPD6344	Clinical (unspecified phase)
0.726	Intermediate Similarity	NPD6985	Discontinued
0.726	Intermediate Similarity	NPD6988	Phase 1
0.726	Intermediate Similarity	NPD7948	Phase 1
0.7257	Intermediate Similarity	NPD4885	Approved
0.7257	Intermediate Similarity	NPD8244	Phase 2
0.7253	Intermediate Similarity	NPD8358	Approved
0.7246	Intermediate Similarity	NPD6861	Clinical (unspecified phase)
0.7245	Intermediate Similarity	NPD1325	Approved
0.7245	Intermediate Similarity	NPD1326	Approved
0.7241	Intermediate Similarity	NPD5256	Discontinued
0.7227	Intermediate Similarity	NPD3763	Approved
0.7227	Intermediate Similarity	NPD7194	Discontinued
0.7225	Intermediate Similarity	NPD7558	Phase 2
0.7212	Intermediate Similarity	NPD5512	Phase 3
0.72	Intermediate Similarity	NPD5559	Phase 2
0.72	Intermediate Similarity	NPD7710	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD1768	Approved
0.717	Intermediate Similarity	NPD6208	Discontinued
0.7163	Intermediate Similarity	NPD2189	Approved
0.7163	Intermediate Similarity	NPD6251	Discontinued
0.7163	Intermediate Similarity	NPD2187	Approved
0.715	Intermediate Similarity	NPD3924	Approved
0.715	Intermediate Similarity	NPD3923	Approved
0.715	Intermediate Similarity	NPD3922	Approved
0.715	Intermediate Similarity	NPD5810	Discontinued
0.715	Intermediate Similarity	NPD3921	Approved
0.715	Intermediate Similarity	NPD6159	Phase 2
0.7149	Intermediate Similarity	NPD6494	Phase 2
0.7143	Intermediate Similarity	NPD5067	Phase 2
0.7143	Intermediate Similarity	NPD5066	Phase 2
0.7136	Intermediate Similarity	NPD7823	Clinical (unspecified phase)
0.713	Intermediate Similarity	NPD1856	Discontinued
0.7129	Intermediate Similarity	NPD7414	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD6242	Discontinued
0.7115	Intermediate Similarity	NPD5575	Clinical (unspecified phase)
0.711	Intermediate Similarity	NPD4927	Discontinued
0.7104	Intermediate Similarity	NPD4429	Discontinued
0.7103	Intermediate Similarity	NPD4795	Phase 2
0.7095	Intermediate Similarity	NPD5003	Discontinued
0.7094	Intermediate Similarity	NPD5522	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD7672	Approved
0.7083	Intermediate Similarity	NPD7671	Approved
0.707	Intermediate Similarity	NPD3842	Clinical (unspecified phase)
0.7064	Intermediate Similarity	NPD6220	Phase 3
0.7054	Intermediate Similarity	NPD7219	Approved
0.7054	Intermediate Similarity	NPD2285	Clinical (unspecified phase)
0.7054	Intermediate Similarity	NPD7221	Approved
0.7054	Intermediate Similarity	NPD6736	Discontinued
0.7051	Intermediate Similarity	NPD7592	Phase 2
0.7045	Intermediate Similarity	NPD5417	Clinical (unspecified phase)
0.7043	Intermediate Similarity	NPD6760	Discontinued
0.7033	Intermediate Similarity	NPD8364	Approved
0.7033	Intermediate Similarity	NPD8363	Approved
0.7027	Intermediate Similarity	NPD5632	Approved
0.7021	Intermediate Similarity	NPD5483	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD6969	Phase 2
0.7018	Intermediate Similarity	NPD6968	Phase 2
0.7015	Intermediate Similarity	NPD4354	Approved
0.7013	Intermediate Similarity	NPD4454	Phase 2
0.7013	Intermediate Similarity	NPD3006	Discontinued
0.7009	Intermediate Similarity	NPD5669	Clinical (unspecified phase)
0.7009	Intermediate Similarity	NPD4881	Clinical (unspecified phase)
0.7004	Intermediate Similarity	NPD7994	Phase 2
0.7	Intermediate Similarity	NPD6607	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD3945	Discontinued
0.7	Intermediate Similarity	NPD3810	Clinical (unspecified phase)
0.6996	Remote Similarity	NPD8017	Clinical (unspecified phase)
0.6996	Remote Similarity	NPD8016	Phase 3
0.6995	Remote Similarity	NPD1739	Approved
0.6995	Remote Similarity	NPD1740	Approved
0.6991	Remote Similarity	NPD6976	Clinical (unspecified phase)
0.6987	Remote Similarity	NPD7659	Discontinued
0.6986	Remote Similarity	NPD5416	Discontinued
0.6986	Remote Similarity	NPD6569	Phase 2
0.6978	Remote Similarity	NPD6824	Clinical (unspecified phase)
0.6976	Remote Similarity	NPD8365	Clinical (unspecified phase)
0.6967	Remote Similarity	NPD6449	Clinical (unspecified phase)
0.6967	Remote Similarity	NPD3478	Clinical (unspecified phase)
0.6967	Remote Similarity	NPD3477	Phase 2
0.6959	Remote Similarity	NPD1392	Approved
0.6955	Remote Similarity	NPD3816	Phase 1
0.6955	Remote Similarity	NPD3815	Phase 1
0.6951	Remote Similarity	NPD4442	Phase 2
0.6949	Remote Similarity	NPD5044	Phase 2
0.6948	Remote Similarity	NPD5999	Phase 2
0.6942	Remote Similarity	NPD6610	Clinical (unspecified phase)
0.694	Remote Similarity	NPD7853	Phase 2
0.6937	Remote Similarity	NPD6147	Clinical (unspecified phase)
0.6936	Remote Similarity	NPD6716	Phase 1
0.6934	Remote Similarity	NPD6769	Clinical (unspecified phase)
0.693	Remote Similarity	NPD6977	Clinical (unspecified phase)
0.693	Remote Similarity	NPD6978	Phase 2
0.692	Remote Similarity	NPD3514	Clinical (unspecified phase)
0.6912	Remote Similarity	NPD8464	Clinical (unspecified phase)
0.6907	Remote Similarity	NPD4440	Clinical (unspecified phase)
0.69	Remote Similarity	NPD7555	Discontinued
0.6898	Remote Similarity	NPD2920	Discontinued
0.6897	Remote Similarity	NPD6203	Clinical (unspecified phase)
0.689	Remote Similarity	NPD2564	Approved
0.689	Remote Similarity	NPD2565	Phase 2
0.6889	Remote Similarity	NPD5070	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD5930	Phase 3
0.6886	Remote Similarity	NPD7603	Discontinued
0.688	Remote Similarity	NPD6750	Phase 2
0.6878	Remote Similarity	NPD4204	Approved
0.6878	Remote Similarity	NPD4203	Approved
0.6878	Remote Similarity	NPD6202	Discontinued
0.6875	Remote Similarity	NPD6141	Clinical (unspecified phase)
0.687	Remote Similarity	NPD6456	Discontinued
0.6864	Remote Similarity	NPD6517	Phase 3
0.686	Remote Similarity	NPD7424	Clinical (unspecified phase)
0.6853	Remote Similarity	NPD112	Approved
0.6853	Remote Similarity	NPD9705	Discontinued
0.6852	Remote Similarity	NPD6975	Discontinued
0.685	Remote Similarity	NPD5021	Discontinued
0.6847	Remote Similarity	NPD1322	Clinical (unspecified phase)
0.684	Remote Similarity	NPD7688	Phase 1
0.6835	Remote Similarity	NPD6245	Phase 2
0.6833	Remote Similarity	NPD6243	Phase 3
0.6833	Remote Similarity	NPD6244	Phase 3
0.6831	Remote Similarity	NPD6961	Discontinued
0.683	Remote Similarity	NPD3440	Clinical (unspecified phase)
0.6828	Remote Similarity	NPD6995	Phase 1
0.6826	Remote Similarity	NPD1624	Phase 2
0.6824	Remote Similarity	NPD2951	Discontinued
0.6822	Remote Similarity	NPD7889	Clinical (unspecified phase)
0.682	Remote Similarity	NPD6991	Approved
0.6816	Remote Similarity	NPD4724	Clinical (unspecified phase)
0.681	Remote Similarity	NPD6281	Approved
0.6806	Remote Similarity	NPD1305	Clinical (unspecified phase)
0.6802	Remote Similarity	NPD3330	Phase 1
0.68	Remote Similarity	NPD8405	Clinical (unspecified phase)
0.6798	Remote Similarity	NPD8465	Approved
0.6798	Remote Similarity	NPD8466	Approved
0.6798	Remote Similarity	NPD8428	Approved
0.6798	Remote Similarity	NPD8429	Approved
0.6798	Remote Similarity	NPD8427	Approved
0.6798	Remote Similarity	NPD8467	Approved
0.6797	Remote Similarity	NPD5022	Discontinued
0.6794	Remote Similarity	NPD8431	Approved
0.6793	Remote Similarity	NPD6473	Phase 1
0.6791	Remote Similarity	NPD3814	Phase 1
0.6789	Remote Similarity	NPD4038	Approved
0.6789	Remote Similarity	NPD4035	Approved
0.6789	Remote Similarity	NPD4034	Approved
0.6789	Remote Similarity	NPD3397	Phase 2
0.6789	Remote Similarity	NPD4033	Approved

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