NPASS Compound

Structure

CID204446 OpenBabel06191715592D 24 28 0 0 0 0 0 0 0 0999 V2000 -5.1962 0.0000 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 -0.8660 -2.5000 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 -2.5981 0.5000 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 -0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1369 -2.0000 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 -1.7321 -0.0000 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 -1.7321 -1.0000 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 -3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -0.0000 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 0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 -2.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 -1.1910 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 22 1 0 0 0 0 2 3 2 0 0 0 0 2 10 1 0 0 0 0 3 12 1 0 0 0 0 4 10 2 0 0 0 0 4 17 1 0 0 0 0 5 11 2 0 0 0 0 5 16 1 0 0 0 0 6 13 2 0 0 0 0 6 15 1 0 0 0 0 7 14 2 0 0 0 0 7 18 1 0 0 0 0 8 11 1 0 0 0 0 8 20 2 0 0 0 0 9 23 1 0 0 0 0 9 24 1 0 0 0 0 10 14 1 0 0 0 0 11 13 1 0 0 0 0 12 13 1 0 0 0 0 12 19 2 0 0 0 0 14 19 1 0 0 0 0 15 16 2 0 0 0 0 15 21 1 0 0 0 0 16 22 1 0 0 0 0 17 18 2 0 0 0 0 17 23 1 0 0 0 0 18 24 1 0 0 0 0 19 20 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	319.08
Volume:	316.827
LogP:	3.941
LogD:	3.516
LogS:	-6.483
# Rotatable Bonds:	1
TPSA:	60.81
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.538
Synthetic Accessibility Score:	2.469
Fsp3:	0.105
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.998
MDCK Permeability:	3.3180476748384535e-05
Pgp-inhibitor:	0.009
Pgp-substrate:	0.025
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.474

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.027
Plasma Protein Binding (PPB):	93.3670883178711%
Volume Distribution (VD):	1.06
Pgp-substrate:	1.9947943687438965%

ADMET: Metabolism

CYP1A2-inhibitor:	0.979
CYP1A2-substrate:	0.399
CYP2C19-inhibitor:	0.934
CYP2C19-substrate:	0.12
CYP2C9-inhibitor:	0.61
CYP2C9-substrate:	0.874
CYP2D6-inhibitor:	0.873
CYP2D6-substrate:	0.93
CYP3A4-inhibitor:	0.823
CYP3A4-substrate:	0.132

ADMET: Excretion

Clearance (CL):	14.767
Half-life (T1/2):	0.266

ADMET: Toxicity

hERG Blockers:	0.195
Human Hepatotoxicity (H-HT):	0.52
Drug-inuced Liver Injury (DILI):	0.967
AMES Toxicity:	0.916
Rat Oral Acute Toxicity:	0.132
Maximum Recommended Daily Dose:	0.93
Skin Sensitization:	0.948
Carcinogencity:	0.947
Eye Corrosion:	0.004
Eye Irritation:	0.808
Respiratory Toxicity:	0.928

Download Data

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

Natural Product: NPC204446

Natural Product ID:	NPC204446
*Common Name:**	ZCMNYBNYFRAPIS-UHFFFAOYSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	ZCMNYBNYFRAPIS-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C19H13NO4/c1-22-16-5-11-8-20-19-12(13(11)6-15(16)21)3-2-10-4-17-18(7-14(10)19)24-9-23-17/h2-8,21H,9H2,1H3
SMILES:	COc1cc2cnc3c(c2cc1O)ccc1c3cc2OCOc2c1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3597757
PubChem CID:	NA
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001253] Quinolines and derivatives [CHEMONTID:0001908] Benzoquinolines [CHEMONTID:0000100] Phenanthridines and derivatives

*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
NPO15275	Briareum asbestinum	Species	Briareidae	Eukaryota	n.a.	n.a.	n.a.	PMID[12662092]
NPO8520	Mucor spinosus	Species	Mucoraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15844967]
NPO15275	Briareum asbestinum	Species	Briareidae	Eukaryota	n.a.	Caribbean	n.a.	PMID[1686898]
NPO14407	Stachyurus praecox	Species	Stachyuraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14407	Stachyurus praecox	Species	Stachyuraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14236	Physalis coztomatl	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15020	Flindersia amboinensis	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2360	Jatropha mahafalensis	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18894	Karenia mikimotoi	Species	Kareniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4424	Salvia amplexicaulis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13389	Cystoseira barbatula	Species	Sargassaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14407	Stachyurus praecox	Species	Stachyuraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13247	Stevia pilosa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10423	Sibthorpia europaea	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14567	Ursinia anethoides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8520	Mucor spinosus	Species	Mucoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15862	Eminium lehmannii	Species	Araceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15275	Briareum asbestinum	Species	Briareidae	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	2

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT393	Cell Line	HCT-116	Homo sapiens	IC50	>	10000.0	nM	PMID[497360]
NPT116	Cell Line	HL-60	Homo sapiens	IC50	>	10000.0	nM	PMID[497360]

☑ 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 NPC204446 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	631
0.1-0.2	3058
0.2-0.3	12703
0.3-0.4	5426
0.4-0.5	12978
0.5-0.6	5646
0.6-0.7	1895
0.7-0.8	304
0.8-0.85	39
0.85-0.9	7
0.9-0.95	7
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9797	High Similarity	NPC118121
0.9637	High Similarity	NPC188420
0.949	High Similarity	NPC271215
0.949	High Similarity	NPC149471
0.9442	High Similarity	NPC235076
0.93	High Similarity	NPC23614
0.93	High Similarity	NPC100079
0.9254	High Similarity	NPC46451
0.8878	High Similarity	NPC234197
0.8861	High Similarity	NPC251160
0.8706	High Similarity	NPC313189
0.8687	High Similarity	NPC477019
0.8614	High Similarity	NPC135549
0.8585	High Similarity	NPC202768
0.8585	High Similarity	NPC112206
0.8585	High Similarity	NPC202605
0.8585	High Similarity	NPC296482
0.8585	High Similarity	NPC53069
0.8571	High Similarity	NPC122463
0.8495	Intermediate Similarity	NPC171409
0.8495	Intermediate Similarity	NPC96405
0.8426	Intermediate Similarity	NPC195268
0.8426	Intermediate Similarity	NPC133140
0.8389	Intermediate Similarity	NPC174049
0.8366	Intermediate Similarity	NPC31930
0.8358	Intermediate Similarity	NPC476578
0.8358	Intermediate Similarity	NPC476582
0.8358	Intermediate Similarity	NPC4071
0.8326	Intermediate Similarity	NPC210296
0.8278	Intermediate Similarity	NPC266931
0.8244	Intermediate Similarity	NPC36229
0.8244	Intermediate Similarity	NPC16452
0.8244	Intermediate Similarity	NPC476581
0.8219	Intermediate Similarity	NPC22481
0.8194	Intermediate Similarity	NPC77878
0.8165	Intermediate Similarity	NPC278525
0.8145	Intermediate Similarity	NPC108342
0.8141	Intermediate Similarity	NPC474904
0.8122	Intermediate Similarity	NPC473822
0.8122	Intermediate Similarity	NPC173080
0.8116	Intermediate Similarity	NPC304183
0.8114	Intermediate Similarity	NPC183537
0.8108	Intermediate Similarity	NPC182907
0.8108	Intermediate Similarity	NPC189903
0.8103	Intermediate Similarity	NPC287588
0.808	Intermediate Similarity	NPC217554
0.8072	Intermediate Similarity	NPC166722
0.8061	Intermediate Similarity	NPC206201
0.8054	Intermediate Similarity	NPC96584
0.8054	Intermediate Similarity	NPC255800
0.8053	Intermediate Similarity	NPC284141
0.8048	Intermediate Similarity	NPC290689
0.8009	Intermediate Similarity	NPC208284
0.8	Intermediate Similarity	NPC148409
0.7991	Intermediate Similarity	NPC11408
0.799	Intermediate Similarity	NPC204385
0.7982	Intermediate Similarity	NPC295228
0.798	Intermediate Similarity	NPC179704
0.7964	Intermediate Similarity	NPC201508
0.7941	Intermediate Similarity	NPC162653
0.7937	Intermediate Similarity	NPC253675
0.793	Intermediate Similarity	NPC15406
0.7895	Intermediate Similarity	NPC124313
0.789	Intermediate Similarity	NPC210434
0.7887	Intermediate Similarity	NPC316981
0.7885	Intermediate Similarity	NPC207283
0.7885	Intermediate Similarity	NPC84164
0.7877	Intermediate Similarity	NPC470020
0.7873	Intermediate Similarity	NPC476997
0.785	Intermediate Similarity	NPC249405
0.7838	Intermediate Similarity	NPC476996
0.7838	Intermediate Similarity	NPC476998
0.782	Intermediate Similarity	NPC474595
0.7811	Intermediate Similarity	NPC276674
0.7811	Intermediate Similarity	NPC33902
0.7794	Intermediate Similarity	NPC141915
0.7794	Intermediate Similarity	NPC114335
0.7794	Intermediate Similarity	NPC280964
0.7793	Intermediate Similarity	NPC476994
0.7783	Intermediate Similarity	NPC214980
0.7758	Intermediate Similarity	NPC24019
0.7734	Intermediate Similarity	NPC320088
0.7727	Intermediate Similarity	NPC280272
0.7716	Intermediate Similarity	NPC312872
0.7714	Intermediate Similarity	NPC199277
0.7714	Intermediate Similarity	NPC135887
0.771	Intermediate Similarity	NPC11464
0.7696	Intermediate Similarity	NPC312531
0.7685	Intermediate Similarity	NPC236668
0.7685	Intermediate Similarity	NPC162530
0.7671	Intermediate Similarity	NPC213530
0.7671	Intermediate Similarity	NPC193267
0.767	Intermediate Similarity	NPC302001
0.7661	Intermediate Similarity	NPC473513
0.7656	Intermediate Similarity	NPC287437
0.765	Intermediate Similarity	NPC146976
0.7644	Intermediate Similarity	NPC224928
0.7632	Intermediate Similarity	NPC476995
0.7625	Intermediate Similarity	NPC132385
0.7623	Intermediate Similarity	NPC200888
0.7611	Intermediate Similarity	NPC233334
0.7604	Intermediate Similarity	NPC474594
0.7586	Intermediate Similarity	NPC208522
0.7577	Intermediate Similarity	NPC473182
0.7571	Intermediate Similarity	NPC212163
0.7564	Intermediate Similarity	NPC270515
0.7559	Intermediate Similarity	NPC285558
0.7555	Intermediate Similarity	NPC473183
0.7545	Intermediate Similarity	NPC470018
0.7544	Intermediate Similarity	NPC90875
0.7524	Intermediate Similarity	NPC296742
0.7524	Intermediate Similarity	NPC112676
0.7524	Intermediate Similarity	NPC17677
0.7524	Intermediate Similarity	NPC23080
0.7524	Intermediate Similarity	NPC193906
0.7523	Intermediate Similarity	NPC323345
0.7523	Intermediate Similarity	NPC470164
0.7512	Intermediate Similarity	NPC475774
0.7512	Intermediate Similarity	NPC251090
0.7511	Intermediate Similarity	NPC74575
0.75	Intermediate Similarity	NPC295676
0.75	Intermediate Similarity	NPC24954
0.7488	Intermediate Similarity	NPC193777
0.7477	Intermediate Similarity	NPC137929
0.7477	Intermediate Similarity	NPC164374
0.7476	Intermediate Similarity	NPC224293
0.7467	Intermediate Similarity	NPC473184
0.7463	Intermediate Similarity	NPC285941
0.7454	Intermediate Similarity	NPC470931
0.7454	Intermediate Similarity	NPC18348
0.7438	Intermediate Similarity	NPC114364
0.7438	Intermediate Similarity	NPC320223
0.7437	Intermediate Similarity	NPC298979
0.743	Intermediate Similarity	NPC223427
0.7429	Intermediate Similarity	NPC473053
0.7427	Intermediate Similarity	NPC69213
0.7426	Intermediate Similarity	NPC128560
0.7426	Intermediate Similarity	NPC199465
0.7426	Intermediate Similarity	NPC229166
0.7416	Intermediate Similarity	NPC307963
0.7416	Intermediate Similarity	NPC329541
0.7416	Intermediate Similarity	NPC78284
0.7415	Intermediate Similarity	NPC28425
0.7402	Intermediate Similarity	NPC311936
0.7401	Intermediate Similarity	NPC246381
0.7395	Intermediate Similarity	NPC329708
0.7395	Intermediate Similarity	NPC47059
0.7395	Intermediate Similarity	NPC274291
0.7395	Intermediate Similarity	NPC264166
0.7395	Intermediate Similarity	NPC244606
0.7395	Intermediate Similarity	NPC118832
0.7395	Intermediate Similarity	NPC156728
0.7395	Intermediate Similarity	NPC165349
0.7391	Intermediate Similarity	NPC277351
0.7389	Intermediate Similarity	NPC202503
0.7385	Intermediate Similarity	NPC167860
0.7385	Intermediate Similarity	NPC123976
0.7383	Intermediate Similarity	NPC66815
0.738	Intermediate Similarity	NPC49547
0.7371	Intermediate Similarity	NPC176538
0.7368	Intermediate Similarity	NPC469792
0.7368	Intermediate Similarity	NPC99666
0.7366	Intermediate Similarity	NPC119579
0.7359	Intermediate Similarity	NPC470017
0.7353	Intermediate Similarity	NPC190461
0.7339	Intermediate Similarity	NPC41501
0.7336	Intermediate Similarity	NPC471489
0.7336	Intermediate Similarity	NPC476999
0.7333	Intermediate Similarity	NPC478045
0.7328	Intermediate Similarity	NPC470022
0.7318	Intermediate Similarity	NPC48353
0.7317	Intermediate Similarity	NPC192939
0.7317	Intermediate Similarity	NPC215747
0.7308	Intermediate Similarity	NPC99891
0.7308	Intermediate Similarity	NPC296527
0.7308	Intermediate Similarity	NPC477186
0.7299	Intermediate Similarity	NPC29472
0.7299	Intermediate Similarity	NPC326634
0.7297	Intermediate Similarity	NPC8022
0.7297	Intermediate Similarity	NPC470799
0.7295	Intermediate Similarity	NPC135772
0.7294	Intermediate Similarity	NPC82548
0.7282	Intermediate Similarity	NPC155442
0.7282	Intermediate Similarity	NPC312918
0.7282	Intermediate Similarity	NPC477561
0.7282	Intermediate Similarity	NPC476574
0.7281	Intermediate Similarity	NPC474145
0.7281	Intermediate Similarity	NPC475841
0.7277	Intermediate Similarity	NPC152212
0.7273	Intermediate Similarity	NPC76748
0.7269	Intermediate Similarity	NPC159101
0.7268	Intermediate Similarity	NPC260118
0.726	Intermediate Similarity	NPC469589
0.7256	Intermediate Similarity	NPC232727
0.7249	Intermediate Similarity	NPC252251
0.7246	Intermediate Similarity	NPC116284
0.724	Intermediate Similarity	NPC203168
0.7238	Intermediate Similarity	NPC92111
0.7235	Intermediate Similarity	NPC475070
0.723	Intermediate Similarity	NPC243834

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 NPC204446 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	338
0.1-0.2	685
0.2-0.3	929
0.3-0.4	1595
0.4-0.5	2737
0.5-0.6	2100
0.6-0.7	684
0.7-0.8	76
0.8-0.85	5
0.85-0.9	0
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9254	High Similarity	NPD3763	Approved
0.8585	High Similarity	NPD3816	Phase 1
0.8585	High Similarity	NPD3815	Phase 1
0.8426	Intermediate Similarity	NPD3921	Approved
0.8426	Intermediate Similarity	NPD3922	Approved
0.8426	Intermediate Similarity	NPD3923	Approved
0.8426	Intermediate Similarity	NPD3924	Approved
0.8136	Intermediate Similarity	NPD6494	Phase 2
0.7879	Intermediate Similarity	NPD7414	Clinical (unspecified phase)
0.7868	Intermediate Similarity	NPD3920	Phase 2
0.782	Intermediate Similarity	NPD7222	Phase 2
0.7696	Intermediate Similarity	NPD5612	Discontinued
0.7606	Intermediate Similarity	NPD5530	Phase 1
0.7604	Intermediate Similarity	NPD7571	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD7567	Approved
0.7598	Intermediate Similarity	NPD6257	Clinical (unspecified phase)
0.757	Intermediate Similarity	NPD7452	Approved
0.757	Intermediate Similarity	NPD7453	Approved
0.7558	Intermediate Similarity	NPD7069	Discontinued
0.7547	Intermediate Similarity	NPD6975	Discontinued
0.7535	Intermediate Similarity	NPD5658	Approved
0.7524	Intermediate Similarity	NPD6281	Approved
0.75	Intermediate Similarity	NPD7558	Phase 2
0.749	Intermediate Similarity	NPD7169	Suspended
0.7478	Intermediate Similarity	NPD7555	Discontinued
0.7431	Intermediate Similarity	NPD4502	Phase 2
0.7416	Intermediate Similarity	NPD1038	Approved
0.7407	Intermediate Similarity	NPD5429	Discontinued
0.7395	Intermediate Similarity	NPD31	Approved
0.7395	Intermediate Similarity	NPD32	Approved
0.7395	Intermediate Similarity	NPD4037	Approved
0.7395	Intermediate Similarity	NPD4039	Approved
0.7395	Intermediate Similarity	NPD4036	Approved
0.7395	Intermediate Similarity	NPD4122	Approved
0.7395	Intermediate Similarity	NPD4035	Approved
0.7395	Intermediate Similarity	NPD4034	Approved
0.7395	Intermediate Similarity	NPD4038	Approved
0.7395	Intermediate Similarity	NPD4033	Approved
0.7383	Intermediate Similarity	NPD6477	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD4418	Discontinued
0.738	Intermediate Similarity	NPD4885	Approved
0.7368	Intermediate Similarity	NPD6569	Phase 2
0.7364	Intermediate Similarity	NPD4926	Clinical (unspecified phase)
0.7362	Intermediate Similarity	NPD6230	Discontinued
0.7353	Intermediate Similarity	NPD6503	Clinical (unspecified phase)
0.7344	Intermediate Similarity	NPD8091	Phase 3
0.733	Intermediate Similarity	NPD4889	Approved
0.7325	Intermediate Similarity	NPD7710	Clinical (unspecified phase)
0.7316	Intermediate Similarity	NPD6964	Approved
0.7316	Intermediate Similarity	NPD6963	Approved
0.7311	Intermediate Similarity	NPD7948	Phase 1
0.7309	Intermediate Similarity	NPD7395	Discontinued
0.7299	Intermediate Similarity	NPD6491	Clinical (unspecified phase)
0.7277	Intermediate Similarity	NPD1923	Clinical (unspecified phase)
0.7265	Intermediate Similarity	NPD8016	Phase 3
0.7265	Intermediate Similarity	NPD8017	Clinical (unspecified phase)
0.7257	Intermediate Similarity	NPD1856	Discontinued
0.7257	Intermediate Similarity	NPD1954	Phase 1
0.7252	Intermediate Similarity	NPD5902	Approved
0.7252	Intermediate Similarity	NPD5903	Approved
0.7251	Intermediate Similarity	NPD1304	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD6872	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD6344	Clinical (unspecified phase)
0.7235	Intermediate Similarity	NPD4795	Phase 2
0.7233	Intermediate Similarity	NPD5522	Clinical (unspecified phase)
0.7232	Intermediate Similarity	NPD3354	Phase 2
0.7217	Intermediate Similarity	NPD5801	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD7672	Approved
0.7215	Intermediate Similarity	NPD7671	Approved
0.7209	Intermediate Similarity	NPD6219	Discontinued
0.7205	Intermediate Similarity	NPD6553	Clinical (unspecified phase)
0.7195	Intermediate Similarity	NPD5939	Approved
0.7195	Intermediate Similarity	NPD5936	Approved
0.7175	Intermediate Similarity	NPD6140	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD4551	Phase 2
0.717	Intermediate Similarity	NPD5575	Clinical (unspecified phase)
0.7168	Intermediate Similarity	NPD5070	Clinical (unspecified phase)
0.7162	Intermediate Similarity	NPD7676	Clinical (unspecified phase)
0.7162	Intermediate Similarity	NPD7674	Phase 3
0.7162	Intermediate Similarity	NPD7675	Phase 3
0.7156	Intermediate Similarity	NPD8109	Clinical (unspecified phase)
0.7131	Intermediate Similarity	NPD4875	Phase 3
0.7131	Intermediate Similarity	NPD4876	Phase 3
0.7131	Intermediate Similarity	NPD6517	Phase 3
0.713	Intermediate Similarity	NPD1740	Approved
0.713	Intermediate Similarity	NPD1739	Approved
0.7124	Intermediate Similarity	NPD5040	Clinical (unspecified phase)
0.7122	Intermediate Similarity	NPD5751	Clinical (unspecified phase)
0.7116	Intermediate Similarity	NPD7889	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD5083	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD5164	Discontinued
0.7107	Intermediate Similarity	NPD7859	Phase 2
0.7101	Intermediate Similarity	NPD4204	Approved
0.7101	Intermediate Similarity	NPD4203	Approved
0.7094	Intermediate Similarity	NPD1078	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD4118	Clinical (unspecified phase)
0.7076	Intermediate Similarity	NPD7729	Clinical (unspecified phase)
0.7068	Intermediate Similarity	NPD6773	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD2739	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD4375	Approved
0.7043	Intermediate Similarity	NPD7719	Discontinued
0.7042	Intermediate Similarity	NPD5488	Discontinued
0.704	Intermediate Similarity	NPD4131	Phase 3
0.7034	Intermediate Similarity	NPD5805	Approved
0.7032	Intermediate Similarity	NPD6991	Approved
0.7025	Intermediate Similarity	NPD8101	Phase 3
0.7023	Intermediate Similarity	NPD3477	Phase 2
0.7023	Intermediate Similarity	NPD3478	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD5930	Phase 3
0.7013	Intermediate Similarity	NPD7426	Phase 1
0.7009	Intermediate Similarity	NPD6361	Phase 2
0.7005	Intermediate Similarity	NPD1620	Clinical (unspecified phase)
0.7005	Intermediate Similarity	NPD3825	Phase 3
0.6996	Remote Similarity	NPD8052	Clinical (unspecified phase)
0.6995	Remote Similarity	NPD2781	Approved
0.6991	Remote Similarity	NPD7112	Discontinued
0.699	Remote Similarity	NPD5100	Phase 3
0.699	Remote Similarity	NPD6375	Clinical (unspecified phase)
0.6987	Remote Similarity	NPD6298	Discontinued
0.6987	Remote Similarity	NPD4881	Clinical (unspecified phase)
0.6987	Remote Similarity	NPD6716	Phase 1
0.6982	Remote Similarity	NPD5863	Clinical (unspecified phase)
0.698	Remote Similarity	NPD2780	Approved
0.698	Remote Similarity	NPD2782	Approved
0.6975	Remote Similarity	NPD7025	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD5905	Phase 1
0.6974	Remote Similarity	NPD6501	Approved
0.6974	Remote Similarity	NPD6500	Approved
0.6968	Remote Similarity	NPD2060	Approved
0.6968	Remote Similarity	NPD4305	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD5067	Phase 2
0.6964	Remote Similarity	NPD5066	Phase 2
0.6957	Remote Similarity	NPD6159	Phase 2
0.6951	Remote Similarity	NPD4437	Phase 3
0.6943	Remote Similarity	NPD7678	Clinical (unspecified phase)
0.6942	Remote Similarity	NPD5602	Clinical (unspecified phase)
0.6941	Remote Similarity	NPD4511	Phase 1
0.6937	Remote Similarity	NPD6290	Phase 2
0.6937	Remote Similarity	NPD1392	Approved
0.6927	Remote Similarity	NPD4083	Discontinued
0.6927	Remote Similarity	NPD2176	Approved
0.6927	Remote Similarity	NPD2175	Phase 3
0.6927	Remote Similarity	NPD2177	Approved
0.6923	Remote Similarity	NPD3397	Phase 2
0.692	Remote Similarity	NPD6262	Clinical (unspecified phase)
0.692	Remote Similarity	NPD4454	Phase 2
0.6919	Remote Similarity	NPD7424	Clinical (unspecified phase)
0.6916	Remote Similarity	NPD2334	Discontinued
0.6916	Remote Similarity	NPD6147	Clinical (unspecified phase)
0.6913	Remote Similarity	NPD5506	Approved
0.6913	Remote Similarity	NPD5507	Approved
0.6908	Remote Similarity	NPD7862	Clinical (unspecified phase)
0.6906	Remote Similarity	NPD4859	Phase 1
0.6903	Remote Similarity	NPD5945	Phase 1
0.6903	Remote Similarity	NPD5944	Phase 1
0.6901	Remote Similarity	NPD8100	Phase 3
0.6898	Remote Similarity	NPD3396	Approved
0.6898	Remote Similarity	NPD6861	Clinical (unspecified phase)
0.6898	Remote Similarity	NPD3395	Approved
0.6898	Remote Similarity	NPD6590	Discontinued
0.6895	Remote Similarity	NPD4396	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD4996	Approved
0.6894	Remote Similarity	NPD4995	Approved
0.6893	Remote Similarity	NPD6607	Clinical (unspecified phase)
0.6892	Remote Similarity	NPD3003	Approved
0.6886	Remote Similarity	NPD7823	Clinical (unspecified phase)
0.6878	Remote Similarity	NPD2757	Phase 2
0.6875	Remote Similarity	NPD7417	Discontinued
0.687	Remote Similarity	NPD6242	Discontinued
0.6869	Remote Similarity	NPD8063	Discontinued
0.6866	Remote Similarity	NPD5512	Phase 3
0.6863	Remote Similarity	NPD7201	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD3386	Phase 2
0.6851	Remote Similarity	NPD4925	Approved
0.6849	Remote Similarity	NPD3837	Clinical (unspecified phase)
0.6845	Remote Similarity	NPD5934	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD8442	Discontinued
0.6835	Remote Similarity	NPD2952	Discontinued
0.6835	Remote Similarity	NPD6988	Phase 1
0.6835	Remote Similarity	NPD4080	Discontinued
0.6835	Remote Similarity	NPD1229	Phase 2
0.683	Remote Similarity	NPD2187	Approved
0.683	Remote Similarity	NPD2189	Approved
0.6826	Remote Similarity	NPD7194	Discontinued
0.6824	Remote Similarity	NPD3925	Approved
0.6816	Remote Similarity	NPD5601	Phase 2
0.6816	Remote Similarity	NPD6525	Clinical (unspecified phase)
0.6815	Remote Similarity	NPD8244	Phase 2
0.681	Remote Similarity	NPD6736	Discontinued
0.6802	Remote Similarity	NPD4044	Discontinued
0.6798	Remote Similarity	NPD4897	Phase 2
0.6789	Remote Similarity	NPD6550	Discontinued
0.6784	Remote Similarity	NPD6158	Phase 2
0.6784	Remote Similarity	NPD9706	Clinical (unspecified phase)
0.6784	Remote Similarity	NPD6476	Clinical (unspecified phase)
0.6783	Remote Similarity	NPD6568	Discontinued
0.6783	Remote Similarity	NPD8405	Clinical (unspecified phase)
0.678	Remote Similarity	NPD6969	Phase 2
0.678	Remote Similarity	NPD5022	Discontinued
0.678	Remote Similarity	NPD6968	Phase 2

Bioactivity similarity: Similar Natural Products in NPASS

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

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

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data