NPASS Compound

Structure

NPC472523 OpenBabel07101718192D 25 27 0 0 0 0 0 0 0 0999 V2000 4.3301 5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 7.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 4.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 4.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 12 1 0 0 0 0 2 12 1 0 0 0 0 3 23 1 0 0 0 0 4 5 2 0 0 0 0 4 13 1 0 0 0 0 5 15 1 0 0 0 0 6 7 2 0 0 0 0 6 16 1 0 0 0 0 7 18 1 0 0 0 0 8 12 1 0 0 0 0 8 19 1 0 0 0 0 9 13 2 0 0 0 0 9 14 1 0 0 0 0 10 14 2 0 0 0 0 10 17 1 0 0 0 0 11 13 1 0 0 0 0 11 24 1 0 0 0 0 14 15 1 0 0 0 0 15 20 2 0 0 0 0 16 17 2 0 0 0 0 16 20 1 0 0 0 0 17 23 1 0 0 0 0 18 21 2 0 0 0 0 18 25 1 0 0 0 0 19 22 2 0 0 0 0 19 24 1 0 0 0 0 20 25 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	340.13
Volume:	351.666
LogP:	4.048
LogD:	3.985
LogS:	-6.577
# Rotatable Bonds:	6
TPSA:	65.74
# H-Bond Aceptor:	5
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.398
Synthetic Accessibility Score:	2.375
Fsp3:	0.3
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:	-4.709
MDCK Permeability:	2.5387402274645865e-05
Pgp-inhibitor:	0.69
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.005
30% Bioavailability (F30%):	0.994

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.135
Plasma Protein Binding (PPB):	91.40494537353516%
Volume Distribution (VD):	0.958
Pgp-substrate:	7.488180637359619%

ADMET: Metabolism

CYP1A2-inhibitor:	0.866
CYP1A2-substrate:	0.789
CYP2C19-inhibitor:	0.928
CYP2C19-substrate:	0.203
CYP2C9-inhibitor:	0.869
CYP2C9-substrate:	0.824
CYP2D6-inhibitor:	0.461
CYP2D6-substrate:	0.713
CYP3A4-inhibitor:	0.579
CYP3A4-substrate:	0.339

ADMET: Excretion

Clearance (CL):	12.478
Half-life (T1/2):	0.559

ADMET: Toxicity

hERG Blockers:	0.065
Human Hepatotoxicity (H-HT):	0.804
Drug-inuced Liver Injury (DILI):	0.956
AMES Toxicity:	0.19
Rat Oral Acute Toxicity:	0.337
Maximum Recommended Daily Dose:	0.557
Skin Sensitization:	0.36
Carcinogencity:	0.886
Eye Corrosion:	0.004
Eye Irritation:	0.079
Respiratory Toxicity:	0.134

Download Data

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

Natural Product: NPC472523

Natural Product ID:	NPC472523
*Common Name:**	JABCPDWEZKZNOT-UHFFFAOYSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	JABCPDWEZKZNOT-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C20H20O5/c1-12(2)8-19(22)24-11-13-4-5-15-14(9-13)10-17(23-3)16-6-7-18(21)25-20(15)16/h4-7,9-10,12H,8,11H2,1-3H3
SMILES:	CC(C)CC(=O)OCC1=CC2=CC(=C3C=CC(=O)OC3=C2C=C1)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3426676
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001640] Naphthopyrans

*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
NPO33003	murraya alata	Species	Rutaceae	Eukaryota	leaves	n.a.	n.a.	PMID[25621853]

☑ 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
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	9100.0	nM	PMID[564245]

☑ 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 NPC472523 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	462
0.1-0.2	1848
0.2-0.3	4115
0.3-0.4	10007
0.4-0.5	8370
0.5-0.6	4096
0.6-0.7	5722
0.7-0.8	5504
0.8-0.85	1986
0.85-0.9	523
0.9-0.95	62
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9474	High Similarity	NPC472524
0.8993	High Similarity	NPC307883
0.8971	High Similarity	NPC19157
0.8947	High Similarity	NPC101894
0.8944	High Similarity	NPC36732
0.8921	High Similarity	NPC306365
0.8881	High Similarity	NPC86069
0.8872	High Similarity	NPC471828
0.8872	High Similarity	NPC471827
0.8865	High Similarity	NPC155552
0.8849	High Similarity	NPC476455
0.8849	High Similarity	NPC128529
0.8849	High Similarity	NPC283019
0.8849	High Similarity	NPC471630
0.8849	High Similarity	NPC55615
0.8849	High Similarity	NPC160727
0.8849	High Similarity	NPC149320
0.8849	High Similarity	NPC177281
0.8828	High Similarity	NPC142863
0.8815	High Similarity	NPC472519
0.8811	High Similarity	NPC251372
0.8803	High Similarity	NPC20631
0.8803	High Similarity	NPC93640
0.8797	High Similarity	NPC201667
0.8797	High Similarity	NPC27671
0.8797	High Similarity	NPC73413
0.8786	High Similarity	NPC131198
0.8777	High Similarity	NPC471909
0.8777	High Similarity	NPC472424
0.8777	High Similarity	NPC471625
0.8777	High Similarity	NPC281241
0.8777	High Similarity	NPC86892
0.8768	High Similarity	NPC185777
0.8759	High Similarity	NPC473927
0.8732	High Similarity	NPC138149
0.8722	High Similarity	NPC472518
0.8722	High Similarity	NPC315807
0.8722	High Similarity	NPC109675
0.8722	High Similarity	NPC273772
0.8716	High Similarity	NPC189773
0.8705	High Similarity	NPC267412
0.8705	High Similarity	NPC164269
0.8705	High Similarity	NPC195343
0.8705	High Similarity	NPC287182
0.8705	High Similarity	NPC47163
0.8705	High Similarity	NPC319859
0.8705	High Similarity	NPC18804
0.8705	High Similarity	NPC198381
0.8705	High Similarity	NPC166672
0.8705	High Similarity	NPC84894
0.8705	High Similarity	NPC127888
0.8705	High Similarity	NPC260265
0.8705	High Similarity	NPC74655
0.8705	High Similarity	NPC100986
0.8667	High Similarity	NPC471826
0.8652	High Similarity	NPC14697
0.8649	High Similarity	NPC474660
0.8647	High Similarity	NPC96286
0.8647	High Similarity	NPC248429
0.8639	High Similarity	NPC146388
0.8633	High Similarity	NPC133956
0.8633	High Similarity	NPC222036
0.8633	High Similarity	NPC55147
0.8633	High Similarity	NPC296624
0.8633	High Similarity	NPC318400
0.8633	High Similarity	NPC54503
0.8633	High Similarity	NPC207002
0.8633	High Similarity	NPC469955
0.8633	High Similarity	NPC167111
0.8633	High Similarity	NPC471910
0.8633	High Similarity	NPC469952
0.8633	High Similarity	NPC7526
0.8623	High Similarity	NPC191395
0.8621	High Similarity	NPC475719
0.8621	High Similarity	NPC101255
0.8621	High Similarity	NPC189650
0.8621	High Similarity	NPC43716
0.8613	High Similarity	NPC168710
0.8582	High Similarity	NPC115861
0.8582	High Similarity	NPC283331
0.8581	High Similarity	NPC146014
0.8571	High Similarity	NPC307412
0.8571	High Similarity	NPC55149
0.8561	High Similarity	NPC14248
0.8561	High Similarity	NPC469956
0.8551	High Similarity	NPC32463
0.8551	High Similarity	NPC80170
0.854	High Similarity	NPC157212
0.854	High Similarity	NPC185066
0.854	High Similarity	NPC199204
0.8529	High Similarity	NPC234109
0.8529	High Similarity	NPC188327
0.8523	High Similarity	NPC473466
0.8519	High Similarity	NPC111347
0.8519	High Similarity	NPC291899
0.85	High Similarity	NPC31849
0.8496	Intermediate Similarity	NPC163200
0.8496	Intermediate Similarity	NPC235190
0.8496	Intermediate Similarity	NPC180006
0.8493	Intermediate Similarity	NPC71739
0.8483	Intermediate Similarity	NPC24075
0.8472	Intermediate Similarity	NPC310370
0.8472	Intermediate Similarity	NPC287286
0.8472	Intermediate Similarity	NPC183642
0.8467	Intermediate Similarity	NPC289316
0.8462	Intermediate Similarity	NPC211110
0.8456	Intermediate Similarity	NPC232387
0.8456	Intermediate Similarity	NPC233267
0.8456	Intermediate Similarity	NPC291049
0.8451	Intermediate Similarity	NPC286843
0.8444	Intermediate Similarity	NPC154176
0.8444	Intermediate Similarity	NPC50720
0.8444	Intermediate Similarity	NPC173350
0.8444	Intermediate Similarity	NPC290605
0.844	Intermediate Similarity	NPC131950
0.8433	Intermediate Similarity	NPC144418
0.8429	Intermediate Similarity	NPC175159
0.8425	Intermediate Similarity	NPC472840
0.8417	Intermediate Similarity	NPC19242
0.8411	Intermediate Similarity	NPC223720
0.8411	Intermediate Similarity	NPC273483
0.8406	Intermediate Similarity	NPC293642
0.8406	Intermediate Similarity	NPC60704
0.8406	Intermediate Similarity	NPC139595
0.8403	Intermediate Similarity	NPC312881
0.8403	Intermediate Similarity	NPC71903
0.8394	Intermediate Similarity	NPC163248
0.8392	Intermediate Similarity	NPC155963
0.8389	Intermediate Similarity	NPC105415
0.838	Intermediate Similarity	NPC229128
0.838	Intermediate Similarity	NPC234865
0.838	Intermediate Similarity	NPC469675
0.8378	Intermediate Similarity	NPC183083
0.8378	Intermediate Similarity	NPC137352
0.837	Intermediate Similarity	NPC150214
0.837	Intermediate Similarity	NPC13007
0.837	Intermediate Similarity	NPC257188
0.8367	Intermediate Similarity	NPC295696
0.8358	Intermediate Similarity	NPC322569
0.8357	Intermediate Similarity	NPC472517
0.8356	Intermediate Similarity	NPC183646
0.8356	Intermediate Similarity	NPC119640
0.8355	Intermediate Similarity	NPC477691
0.8355	Intermediate Similarity	NPC210942
0.8355	Intermediate Similarity	NPC268484
0.8355	Intermediate Similarity	NPC169990
0.8346	Intermediate Similarity	NPC298796
0.8346	Intermediate Similarity	NPC281356
0.8345	Intermediate Similarity	NPC195357
0.8345	Intermediate Similarity	NPC136095
0.8345	Intermediate Similarity	NPC473209
0.8345	Intermediate Similarity	NPC152771
0.8345	Intermediate Similarity	NPC170812
0.8344	Intermediate Similarity	NPC133856
0.8333	Intermediate Similarity	NPC158338
0.8333	Intermediate Similarity	NPC37428
0.8333	Intermediate Similarity	NPC97028
0.8333	Intermediate Similarity	NPC97029
0.8333	Intermediate Similarity	NPC270256
0.8333	Intermediate Similarity	NPC278600
0.8333	Intermediate Similarity	NPC100985
0.8333	Intermediate Similarity	NPC47040
0.8333	Intermediate Similarity	NPC144512
0.8333	Intermediate Similarity	NPC35501
0.8333	Intermediate Similarity	NPC137262
0.8333	Intermediate Similarity	NPC65589
0.8333	Intermediate Similarity	NPC151946
0.8333	Intermediate Similarity	NPC279573
0.8333	Intermediate Similarity	NPC288036
0.8333	Intermediate Similarity	NPC243688
0.8333	Intermediate Similarity	NPC477381
0.8322	Intermediate Similarity	NPC26954
0.8322	Intermediate Similarity	NPC38099
0.8311	Intermediate Similarity	NPC49282
0.8311	Intermediate Similarity	NPC471608
0.831	Intermediate Similarity	NPC62366
0.831	Intermediate Similarity	NPC213173
0.831	Intermediate Similarity	NPC224475
0.831	Intermediate Similarity	NPC473107
0.831	Intermediate Similarity	NPC180716
0.831	Intermediate Similarity	NPC50896
0.831	Intermediate Similarity	NPC204353
0.831	Intermediate Similarity	NPC326600
0.8301	Intermediate Similarity	NPC149618
0.8301	Intermediate Similarity	NPC89625
0.8299	Intermediate Similarity	NPC471824
0.8299	Intermediate Similarity	NPC476457
0.8298	Intermediate Similarity	NPC194277
0.8298	Intermediate Similarity	NPC123954
0.8289	Intermediate Similarity	NPC477690
0.8289	Intermediate Similarity	NPC87708
0.8289	Intermediate Similarity	NPC217447
0.8278	Intermediate Similarity	NPC477379
0.8278	Intermediate Similarity	NPC158866
0.8276	Intermediate Similarity	NPC36414
0.8273	Intermediate Similarity	NPC181675
0.8271	Intermediate Similarity	NPC96705
0.8271	Intermediate Similarity	NPC265547
0.8271	Intermediate Similarity	NPC152306
0.8267	Intermediate Similarity	NPC27221

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 NPC472523 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	406
0.1-0.2	1008
0.2-0.3	1595
0.3-0.4	2639
0.4-0.5	1904
0.5-0.6	1045
0.6-0.7	372
0.7-0.8	128
0.8-0.85	36
0.85-0.9	17
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8451	Intermediate Similarity	NPD3748	Approved
0.8355	Intermediate Similarity	NPD7819	Suspended
0.8346	Intermediate Similarity	NPD5691	Approved
0.8214	Intermediate Similarity	NPD4625	Phase 3
0.8187	Intermediate Similarity	NPD5844	Phase 1
0.8163	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.8163	Intermediate Similarity	NPD3750	Approved
0.8162	Intermediate Similarity	NPD1611	Approved
0.8112	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.8112	Intermediate Similarity	NPD5124	Phase 1
0.8042	Intermediate Similarity	NPD2979	Phase 3
0.8029	Intermediate Similarity	NPD1281	Approved
0.8028	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8028	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.8015	Intermediate Similarity	NPD4626	Approved
0.8014	Intermediate Similarity	NPD2796	Approved
0.7974	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7929	Intermediate Similarity	NPD3266	Approved
0.7929	Intermediate Similarity	NPD2797	Approved
0.7929	Intermediate Similarity	NPD3267	Approved
0.7917	Intermediate Similarity	NPD4060	Phase 1
0.7899	Intermediate Similarity	NPD422	Phase 1
0.7898	Intermediate Similarity	NPD7768	Phase 2
0.7891	Intermediate Similarity	NPD2438	Suspended
0.7887	Intermediate Similarity	NPD4908	Phase 1
0.7875	Intermediate Similarity	NPD7229	Phase 3
0.7857	Intermediate Similarity	NPD1283	Approved
0.7852	Intermediate Similarity	NPD1243	Approved
0.7843	Intermediate Similarity	NPD920	Approved
0.7815	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.781	Intermediate Similarity	NPD1651	Approved
0.7806	Intermediate Similarity	NPD6599	Discontinued
0.7793	Intermediate Similarity	NPD4307	Phase 2
0.7785	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD3268	Approved
0.7778	Intermediate Similarity	NPD1296	Phase 2
0.7771	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.777	Intermediate Similarity	NPD2531	Phase 2
0.777	Intermediate Similarity	NPD1610	Phase 2
0.7764	Intermediate Similarity	NPD6232	Discontinued
0.7762	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7756	Intermediate Similarity	NPD7411	Suspended
0.7742	Intermediate Similarity	NPD3226	Approved
0.7733	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.773	Intermediate Similarity	NPD7473	Discontinued
0.7724	Intermediate Similarity	NPD8032	Phase 2
0.7718	Intermediate Similarity	NPD2346	Discontinued
0.7712	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7712	Intermediate Similarity	NPD2534	Approved
0.7712	Intermediate Similarity	NPD2533	Approved
0.7712	Intermediate Similarity	NPD2532	Approved
0.7712	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7712	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7707	Intermediate Similarity	NPD6801	Discontinued
0.7702	Intermediate Similarity	NPD6959	Discontinued
0.7688	Intermediate Similarity	NPD919	Approved
0.7687	Intermediate Similarity	NPD5535	Approved
0.7682	Intermediate Similarity	NPD7003	Approved
0.7671	Intermediate Similarity	NPD4140	Approved
0.7662	Intermediate Similarity	NPD6273	Approved
0.766	Intermediate Similarity	NPD4749	Approved
0.7655	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7651	Intermediate Similarity	NPD6100	Approved
0.7651	Intermediate Similarity	NPD6099	Approved
0.7651	Intermediate Similarity	NPD1551	Phase 2
0.7647	Intermediate Similarity	NPD6799	Approved
0.7647	Intermediate Similarity	NPD7837	Clinical (unspecified phase)
0.764	Intermediate Similarity	NPD5494	Approved
0.7639	Intermediate Similarity	NPD6832	Phase 2
0.7626	Intermediate Similarity	NPD17	Approved
0.7625	Intermediate Similarity	NPD7075	Discontinued
0.7616	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.761	Intermediate Similarity	NPD3817	Phase 2
0.7609	Intermediate Similarity	NPD1548	Phase 1
0.7606	Intermediate Similarity	NPD3225	Approved
0.7595	Intermediate Similarity	NPD37	Approved
0.7593	Intermediate Similarity	NPD7199	Phase 2
0.7584	Intermediate Similarity	NPD2799	Discontinued
0.7584	Intermediate Similarity	NPD4308	Phase 3
0.7566	Intermediate Similarity	NPD4628	Phase 3
0.7562	Intermediate Similarity	NPD4966	Approved
0.7562	Intermediate Similarity	NPD4965	Approved
0.7562	Intermediate Similarity	NPD4967	Phase 2
0.7561	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7554	Intermediate Similarity	NPD5585	Approved
0.7548	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7547	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7533	Intermediate Similarity	NPD2935	Discontinued
0.7532	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD3749	Approved
0.75	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6559	Discontinued
0.75	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD4288	Approved
0.75	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1652	Phase 2
0.75	Intermediate Similarity	NPD1778	Approved
0.7484	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD5763	Approved
0.7483	Intermediate Similarity	NPD5762	Approved
0.7469	Intermediate Similarity	NPD6234	Discontinued
0.7467	Intermediate Similarity	NPD1510	Phase 2
0.7465	Intermediate Similarity	NPD1608	Approved
0.7453	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7438	Intermediate Similarity	NPD1465	Phase 2
0.7436	Intermediate Similarity	NPD7314	Clinical (unspecified phase)
0.7434	Intermediate Similarity	NPD1549	Phase 2
0.7417	Intermediate Similarity	NPD4476	Approved
0.7417	Intermediate Similarity	NPD4477	Approved
0.7415	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7413	Intermediate Similarity	NPD5327	Phase 3
0.741	Intermediate Similarity	NPD7644	Approved
0.7405	Intermediate Similarity	NPD8158	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD5402	Approved
0.7389	Intermediate Similarity	NPD5403	Approved
0.7389	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7383	Intermediate Similarity	NPD6355	Discontinued
0.7372	Intermediate Similarity	NPD5401	Approved
0.7368	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD3134	Approved
0.7365	Intermediate Similarity	NPD7177	Discontinued
0.7358	Intermediate Similarity	NPD4380	Phase 2
0.7355	Intermediate Similarity	NPD6666	Approved
0.7355	Intermediate Similarity	NPD6667	Approved
0.7351	Intermediate Similarity	NPD7033	Discontinued
0.7347	Intermediate Similarity	NPD7095	Approved
0.7342	Intermediate Similarity	NPD1653	Approved
0.7333	Intermediate Similarity	NPD1607	Approved
0.7329	Intermediate Similarity	NPD2861	Phase 2
0.7324	Intermediate Similarity	NPD3496	Discontinued
0.7315	Intermediate Similarity	NPD1613	Approved
0.7315	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD5405	Approved
0.7303	Intermediate Similarity	NPD5404	Approved
0.7303	Intermediate Similarity	NPD5406	Approved
0.7303	Intermediate Similarity	NPD5408	Approved
0.7297	Intermediate Similarity	NPD6798	Discontinued
0.7297	Intermediate Similarity	NPD2313	Discontinued
0.7297	Intermediate Similarity	NPD6812	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD7985	Registered
0.7293	Intermediate Similarity	NPD9697	Approved
0.7292	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD4359	Approved
0.7279	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD8127	Discontinued
0.7267	Intermediate Similarity	NPD1934	Approved
0.7255	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7251	Intermediate Similarity	NPD7549	Discontinued
0.7226	Intermediate Similarity	NPD3892	Phase 2
0.7222	Intermediate Similarity	NPD2801	Approved
0.7212	Intermediate Similarity	NPD6746	Phase 2
0.7211	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7211	Intermediate Similarity	NPD2237	Approved
0.72	Intermediate Similarity	NPD1240	Approved
0.7197	Intermediate Similarity	NPD1511	Approved
0.7195	Intermediate Similarity	NPD6971	Discontinued
0.7195	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD7458	Discontinued
0.7185	Intermediate Similarity	NPD1358	Approved
0.7169	Intermediate Similarity	NPD1247	Approved
0.7163	Intermediate Similarity	NPD5536	Phase 2
0.7161	Intermediate Similarity	NPD6674	Discontinued
0.716	Intermediate Similarity	NPD7228	Approved
0.7152	Intermediate Similarity	NPD4340	Discontinued
0.7152	Intermediate Similarity	NPD7446	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD2798	Approved
0.7143	Intermediate Similarity	NPD6005	Phase 3
0.7143	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6004	Phase 3
0.7143	Intermediate Similarity	NPD6002	Phase 3
0.7134	Intermediate Similarity	NPD3882	Suspended
0.7126	Intermediate Similarity	NPD5711	Approved
0.7126	Intermediate Similarity	NPD5710	Approved
0.7124	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD4108	Discontinued
0.7123	Intermediate Similarity	NPD1876	Approved
0.7123	Intermediate Similarity	NPD8651	Approved
0.7122	Intermediate Similarity	NPD1241	Discontinued
0.7122	Intermediate Similarity	NPD5283	Phase 1
0.7117	Intermediate Similarity	NPD8455	Phase 2
0.7115	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD7466	Approved
0.7114	Intermediate Similarity	NPD3027	Phase 3
0.711	Intermediate Similarity	NPD8312	Approved
0.711	Intermediate Similarity	NPD8313	Approved
0.7107	Intermediate Similarity	NPD1512	Approved
0.7105	Intermediate Similarity	NPD4579	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD4097	Suspended
0.7103	Intermediate Similarity	NPD3972	Approved
0.7097	Intermediate Similarity	NPD2897	Discontinued
0.7095	Intermediate Similarity	NPD3018	Phase 2
0.7083	Intermediate Similarity	NPD3926	Phase 2
0.7075	Intermediate Similarity	NPD1203	Approved
0.7073	Intermediate Similarity	NPD5616	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD411	Approved
0.7067	Intermediate Similarity	NPD3764	Approved
0.7063	Intermediate Similarity	NPD7427	Discontinued

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data