NPASS Compound

Structure

NPC27904 OpenBabel07101718182D 24 26 0 0 0 0 0 0 0 0999 V2000 1.7321 -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 0.0000 3.0000 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 -2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 2.0000 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 2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 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 1.7321 0.0000 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 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 0.8660 1.5000 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 -0.8660 0.5000 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 0.0000 0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 2.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 O 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 11 1 0 0 0 0 2 11 1 0 0 0 0 3 21 1 0 0 0 0 4 5 2 0 0 0 0 4 6 1 0 0 0 0 5 14 1 0 0 0 0 6 15 2 0 0 0 0 7 8 1 0 0 0 0 7 11 2 0 0 0 0 8 12 1 0 0 0 0 9 12 2 0 0 0 0 9 13 1 0 0 0 0 10 13 1 0 0 0 0 10 16 2 0 0 0 0 12 17 1 0 0 0 0 13 22 2 0 0 0 0 14 18 2 0 0 0 0 14 19 1 0 0 0 0 15 18 1 0 0 0 0 15 21 1 0 0 0 0 16 17 1 0 0 0 0 16 21 1 0 0 0 0 17 20 2 0 0 0 0 18 20 1 0 0 0 0 19 23 2 0 0 0 0 19 24 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	322.13
Volume:	336.147
LogP:	3.321
LogD:	1.645
LogS:	-3.08
# Rotatable Bonds:	3
TPSA:	72.19
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.593
Synthetic Accessibility Score:	2.916
Fsp3:	0.211
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.153
MDCK Permeability:	1.5370294931926765e-05
Pgp-inhibitor:	0.044
Pgp-substrate:	0.148
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.003

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.08
Plasma Protein Binding (PPB):	95.28618621826172%
Volume Distribution (VD):	0.556
Pgp-substrate:	1.1187031269073486%

ADMET: Metabolism

CYP1A2-inhibitor:	0.142
CYP1A2-substrate:	0.443
CYP2C19-inhibitor:	0.066
CYP2C19-substrate:	0.062
CYP2C9-inhibitor:	0.308
CYP2C9-substrate:	0.078
CYP2D6-inhibitor:	0.048
CYP2D6-substrate:	0.095
CYP3A4-inhibitor:	0.04
CYP3A4-substrate:	0.082

ADMET: Excretion

Clearance (CL):	6.251
Half-life (T1/2):	0.603

ADMET: Toxicity

hERG Blockers:	0.046
Human Hepatotoxicity (H-HT):	0.847
Drug-inuced Liver Injury (DILI):	0.974
AMES Toxicity:	0.018
Rat Oral Acute Toxicity:	0.067
Maximum Recommended Daily Dose:	0.369
Skin Sensitization:	0.038
Carcinogencity:	0.109
Eye Corrosion:	0.003
Eye Irritation:	0.034
Respiratory Toxicity:	0.954

Download Data

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

Natural Product: NPC27904

Natural Product ID:	NPC27904
*Common Name:**	Endophenazine B
IUPAC Name:	5-methyl-9-(3-methylbut-2-enyl)-7-oxophenazine-1-carboxylic acid
Synonyms:	Endophenazine B
Standard InCHIKey:	CIWWONHFDUMHHK-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C19H18N2O3/c1-11(2)7-8-12-9-13(22)10-16-17(12)20-18-14(19(23)24)5-4-6-15(18)21(16)3/h4-7,9-10H,8H2,1-3H3,(H,23,24)
SMILES:	CC(=CCc1cc(=O)cc2c1nc1c(cccc1n2C)C(=O)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1952289
PubChem CID:	9973416
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0004788] Diazanaphthalenes [CHEMONTID:0004789] Benzodiazines [CHEMONTID:0000486] Quinoxalines [CHEMONTID:0000416] Phenazines 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
NPO33382	streptomyces sp. ank 315	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[22220635]

☑ 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	3

Activity Type	# Activity
Individual Protein	1
Organism	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT204	Individual Protein	Acetylcholinesterase	Homo sapiens	IC50	>	50000.0	nM	PMID[556170]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	IC50	>	150000.0	nM	PMID[556170]
NPT27	Others	Unspecified		IC50	>	50000.0	nM	PMID[556170]

☑ 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 NPC27904 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	345
0.1-0.2	3357
0.2-0.3	12625
0.3-0.4	11749
0.4-0.5	10054
0.5-0.6	2759
0.6-0.7	1627
0.7-0.8	162
0.8-0.85	12
0.85-0.9	6
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8424	Intermediate Similarity	NPC471743
0.8235	Intermediate Similarity	NPC203635
0.8176	Intermediate Similarity	NPC243058
0.8129	Intermediate Similarity	NPC471742
0.807	Intermediate Similarity	NPC470317
0.8047	Intermediate Similarity	NPC219848
0.8035	Intermediate Similarity	NPC90415
0.8	Intermediate Similarity	NPC256268
0.7895	Intermediate Similarity	NPC253476
0.7892	Intermediate Similarity	NPC471130
0.7879	Intermediate Similarity	NPC88970
0.7844	Intermediate Similarity	NPC182131
0.7797	Intermediate Similarity	NPC313293
0.7746	Intermediate Similarity	NPC475685
0.7654	Intermediate Similarity	NPC144691
0.7619	Intermediate Similarity	NPC189116
0.7595	Intermediate Similarity	NPC43477
0.7593	Intermediate Similarity	NPC300596
0.7593	Intermediate Similarity	NPC237649
0.7572	Intermediate Similarity	NPC475607
0.7548	Intermediate Similarity	NPC184437
0.7529	Intermediate Similarity	NPC474081
0.7514	Intermediate Similarity	NPC475594
0.7468	Intermediate Similarity	NPC314098
0.7456	Intermediate Similarity	NPC476231
0.7447	Intermediate Similarity	NPC314648
0.7432	Intermediate Similarity	NPC291962
0.7432	Intermediate Similarity	NPC177684
0.7421	Intermediate Similarity	NPC472243
0.7389	Intermediate Similarity	NPC473815
0.7389	Intermediate Similarity	NPC173295
0.7386	Intermediate Similarity	NPC475761
0.7386	Intermediate Similarity	NPC474041
0.7383	Intermediate Similarity	NPC112373
0.7383	Intermediate Similarity	NPC258531
0.7383	Intermediate Similarity	NPC161956
0.7362	Intermediate Similarity	NPC478039
0.7362	Intermediate Similarity	NPC259678
0.7353	Intermediate Similarity	NPC199737
0.7333	Intermediate Similarity	NPC257490
0.7316	Intermediate Similarity	NPC313796
0.7316	Intermediate Similarity	NPC313345
0.7316	Intermediate Similarity	NPC314855
0.7316	Intermediate Similarity	NPC315638
0.7299	Intermediate Similarity	NPC318183
0.7277	Intermediate Similarity	NPC315545
0.7277	Intermediate Similarity	NPC314297
0.7268	Intermediate Similarity	NPC92803
0.7267	Intermediate Similarity	NPC130931
0.7253	Intermediate Similarity	NPC18890
0.725	Intermediate Similarity	NPC181527
0.7244	Intermediate Similarity	NPC316746
0.7226	Intermediate Similarity	NPC150863
0.7222	Intermediate Similarity	NPC472241
0.7179	Intermediate Similarity	NPC244856
0.7179	Intermediate Similarity	NPC194562
0.7171	Intermediate Similarity	NPC39818
0.7165	Intermediate Similarity	NPC314834
0.716	Intermediate Similarity	NPC471574
0.7143	Intermediate Similarity	NPC315224
0.7143	Intermediate Similarity	NPC471741
0.7143	Intermediate Similarity	NPC470343
0.7143	Intermediate Similarity	NPC205946
0.7143	Intermediate Similarity	NPC472244
0.7133	Intermediate Similarity	NPC229353
0.7128	Intermediate Similarity	NPC474916
0.712	Intermediate Similarity	NPC471196
0.712	Intermediate Similarity	NPC471195
0.7118	Intermediate Similarity	NPC84317
0.7115	Intermediate Similarity	NPC122235
0.711	Intermediate Similarity	NPC204867
0.7105	Intermediate Similarity	NPC471944
0.7102	Intermediate Similarity	NPC474814
0.7102	Intermediate Similarity	NPC112336
0.7093	Intermediate Similarity	NPC93653
0.7091	Intermediate Similarity	NPC472242
0.7089	Intermediate Similarity	NPC53044
0.7081	Intermediate Similarity	NPC159722
0.707	Intermediate Similarity	NPC472245
0.707	Intermediate Similarity	NPC314431
0.707	Intermediate Similarity	NPC280807
0.7063	Intermediate Similarity	NPC300299
0.7056	Intermediate Similarity	NPC306644
0.7056	Intermediate Similarity	NPC236424
0.7039	Intermediate Similarity	NPC179605
0.7039	Intermediate Similarity	NPC279385
0.7035	Intermediate Similarity	NPC154478
0.703	Intermediate Similarity	NPC314186
0.703	Intermediate Similarity	NPC136002
0.7021	Intermediate Similarity	NPC472540
0.7021	Intermediate Similarity	NPC472539
0.7021	Intermediate Similarity	NPC470787
0.702	Intermediate Similarity	NPC274842
0.7006	Intermediate Similarity	NPC292265
0.7	Intermediate Similarity	NPC471132
0.6993	Remote Similarity	NPC103292
0.6984	Remote Similarity	NPC472542
0.6984	Remote Similarity	NPC472541
0.6981	Remote Similarity	NPC476687
0.6981	Remote Similarity	NPC476685
0.6981	Remote Similarity	NPC476689
0.697	Remote Similarity	NPC308197
0.6968	Remote Similarity	NPC226794
0.6957	Remote Similarity	NPC150308
0.6932	Remote Similarity	NPC278887
0.6928	Remote Similarity	NPC323798
0.6927	Remote Similarity	NPC470548
0.6906	Remote Similarity	NPC474815
0.6905	Remote Similarity	NPC254798
0.6897	Remote Similarity	NPC322644
0.689	Remote Similarity	NPC315051
0.689	Remote Similarity	NPC242933
0.6889	Remote Similarity	NPC8467
0.6882	Remote Similarity	NPC183805
0.6875	Remote Similarity	NPC299582
0.6864	Remote Similarity	NPC242000
0.6856	Remote Similarity	NPC295548
0.6854	Remote Similarity	NPC472118
0.6851	Remote Similarity	NPC315631
0.6851	Remote Similarity	NPC14849
0.6848	Remote Similarity	NPC316202
0.6837	Remote Similarity	NPC471155
0.6836	Remote Similarity	NPC472114
0.6836	Remote Similarity	NPC472115
0.6828	Remote Similarity	NPC278434
0.6813	Remote Similarity	NPC231382
0.6811	Remote Similarity	NPC476341
0.6802	Remote Similarity	NPC270241
0.6796	Remote Similarity	NPC84347
0.6789	Remote Similarity	NPC202812
0.6788	Remote Similarity	NPC207554
0.6786	Remote Similarity	NPC225400
0.6772	Remote Similarity	NPC250476
0.6766	Remote Similarity	NPC314287
0.676	Remote Similarity	NPC471778
0.6751	Remote Similarity	NPC470786
0.6751	Remote Similarity	NPC472538
0.6747	Remote Similarity	NPC2823
0.6744	Remote Similarity	NPC117032
0.674	Remote Similarity	NPC328611
0.674	Remote Similarity	NPC303225
0.673	Remote Similarity	NPC58827
0.673	Remote Similarity	NPC72473
0.673	Remote Similarity	NPC307437
0.6727	Remote Similarity	NPC83214
0.6725	Remote Similarity	NPC288445
0.6721	Remote Similarity	NPC131450
0.6721	Remote Similarity	NPC182057
0.6721	Remote Similarity	NPC147298
0.672	Remote Similarity	NPC282103
0.6702	Remote Similarity	NPC198401
0.6686	Remote Similarity	NPC211525
0.6686	Remote Similarity	NPC153694
0.6685	Remote Similarity	NPC52059
0.6685	Remote Similarity	NPC298320
0.6685	Remote Similarity	NPC85613
0.6685	Remote Similarity	NPC470069
0.6667	Remote Similarity	NPC285923
0.6667	Remote Similarity	NPC478040
0.6667	Remote Similarity	NPC293458
0.6667	Remote Similarity	NPC122553
0.6667	Remote Similarity	NPC475983
0.6649	Remote Similarity	NPC317727
0.6649	Remote Similarity	NPC45850
0.6648	Remote Similarity	NPC248862
0.6648	Remote Similarity	NPC41717
0.6648	Remote Similarity	NPC36495
0.6647	Remote Similarity	NPC324445
0.6647	Remote Similarity	NPC471164
0.6647	Remote Similarity	NPC470579
0.6645	Remote Similarity	NPC226143
0.6632	Remote Similarity	NPC90229
0.6632	Remote Similarity	NPC316282
0.6629	Remote Similarity	NPC313757
0.6627	Remote Similarity	NPC130797
0.6627	Remote Similarity	NPC473804
0.6614	Remote Similarity	NPC221873
0.6603	Remote Similarity	NPC150323
0.6596	Remote Similarity	NPC194040
0.6595	Remote Similarity	NPC5167
0.6588	Remote Similarity	NPC119569
0.6579	Remote Similarity	NPC5630
0.6578	Remote Similarity	NPC97584
0.6578	Remote Similarity	NPC46895
0.6576	Remote Similarity	NPC9475
0.6573	Remote Similarity	NPC289776
0.6573	Remote Similarity	NPC133470
0.6573	Remote Similarity	NPC253667
0.6573	Remote Similarity	NPC191863
0.6573	Remote Similarity	NPC35510
0.6564	Remote Similarity	NPC81535
0.6564	Remote Similarity	NPC207428
0.6561	Remote Similarity	NPC206186
0.6559	Remote Similarity	NPC475962
0.6554	Remote Similarity	NPC263709
0.6554	Remote Similarity	NPC310403
0.6554	Remote Similarity	NPC97380
0.6554	Remote Similarity	NPC471122
0.6554	Remote Similarity	NPC243673
0.6554	Remote Similarity	NPC148468

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 NPC27904 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	221
0.1-0.2	663
0.2-0.3	877
0.3-0.4	1432
0.4-0.5	2915
0.5-0.6	2202
0.6-0.7	765
0.7-0.8	74
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
0.7816	Intermediate Similarity	NPD5923	Phase 1
0.7722	Intermediate Similarity	NPD1625	Approved
0.7658	Intermediate Similarity	NPD1189	Approved
0.7625	Intermediate Similarity	NPD6017	Discontinued
0.7593	Intermediate Similarity	NPD4888	Discontinued
0.75	Intermediate Similarity	NPD2791	Discontinued
0.7485	Intermediate Similarity	NPD212	Discontinued
0.7468	Intermediate Similarity	NPD1626	Approved
0.7439	Intermediate Similarity	NPD2737	Clinical (unspecified phase)
0.7396	Intermediate Similarity	NPD2506	Approved
0.7391	Intermediate Similarity	NPD4430	Phase 2
0.7363	Intermediate Similarity	NPD5042	Phase 1
0.7348	Intermediate Similarity	NPD7855	Clinical (unspecified phase)
0.7322	Intermediate Similarity	NPD7570	Approved
0.7322	Intermediate Similarity	NPD7569	Approved
0.7299	Intermediate Similarity	NPD3776	Discontinued
0.7278	Intermediate Similarity	NPD6163	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD7735	Clinical (unspecified phase)
0.7268	Intermediate Similarity	NPD5504	Discontinued
0.7235	Intermediate Similarity	NPD2427	Approved
0.7222	Intermediate Similarity	NPD4412	Phase 2
0.72	Intermediate Similarity	NPD1165	Clinical (unspecified phase)
0.7186	Intermediate Similarity	NPD1230	Approved
0.7184	Intermediate Similarity	NPD2037	Approved
0.716	Intermediate Similarity	NPD9477	Approved
0.7143	Intermediate Similarity	NPD13	Approved
0.7143	Intermediate Similarity	NPD700	Approved
0.7143	Intermediate Similarity	NPD699	Approved
0.7143	Intermediate Similarity	NPD12	Approved
0.7143	Intermediate Similarity	NPD697	Approved
0.7135	Intermediate Similarity	NPD3755	Clinical (unspecified phase)
0.7118	Intermediate Similarity	NPD2836	Approved
0.7117	Intermediate Similarity	NPD6414	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD9693	Approved
0.7105	Intermediate Similarity	NPD9692	Approved
0.7095	Intermediate Similarity	NPD3782	Discontinued
0.7081	Intermediate Similarity	NPD2336	Approved
0.7056	Intermediate Similarity	NPD4330	Approved
0.7056	Intermediate Similarity	NPD4329	Approved
0.7052	Intermediate Similarity	NPD1210	Approved
0.7045	Intermediate Similarity	NPD3376	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD1527	Phase 2
0.7044	Intermediate Similarity	NPD2949	Approved
0.7044	Intermediate Similarity	NPD2950	Approved
0.7043	Intermediate Similarity	NPD5937	Approved
0.7039	Intermediate Similarity	NPD3792	Approved
0.7017	Intermediate Similarity	NPD3471	Approved
0.7017	Intermediate Similarity	NPD3470	Approved
0.7011	Intermediate Similarity	NPD4948	Discontinued
0.7006	Intermediate Similarity	NPD2431	Approved
0.7006	Intermediate Similarity	NPD2432	Approved
0.7	Intermediate Similarity	NPD5086	Approved
0.6989	Remote Similarity	NPD2455	Approved
0.6989	Remote Similarity	NPD2454	Approved
0.6983	Remote Similarity	NPD2083	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD2670	Approved
0.6975	Remote Similarity	NPD4077	Clinical (unspecified phase)
0.697	Remote Similarity	NPD2820	Phase 3
0.6961	Remote Similarity	NPD5445	Approved
0.6959	Remote Similarity	NPD1514	Discontinued
0.6954	Remote Similarity	NPD4871	Phase 2
0.6949	Remote Similarity	NPD2369	Discontinued
0.6947	Remote Similarity	NPD4987	Clinical (unspecified phase)
0.6947	Remote Similarity	NPD5856	Discontinued
0.6931	Remote Similarity	NPD2307	Discontinued
0.6928	Remote Similarity	NPD6506	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD5748	Phase 2
0.6923	Remote Similarity	NPD1574	Approved
0.6919	Remote Similarity	NPD951	Approved
0.6909	Remote Similarity	NPD2365	Approved
0.6906	Remote Similarity	NPD5398	Clinical (unspecified phase)
0.6899	Remote Similarity	NPD659	Approved
0.6899	Remote Similarity	NPD656	Approved
0.6899	Remote Similarity	NPD658	Approved
0.6899	Remote Similarity	NPD662	Approved
0.6899	Remote Similarity	NPD663	Approved
0.6886	Remote Similarity	NPD5931	Phase 3
0.6886	Remote Similarity	NPD5932	Phase 3
0.6886	Remote Similarity	NPD5933	Phase 3
0.6885	Remote Similarity	NPD3253	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD3277	Phase 3
0.6879	Remote Similarity	NPD1593	Approved
0.6875	Remote Similarity	NPD1919	Approved
0.6875	Remote Similarity	NPD1920	Approved
0.6872	Remote Similarity	NPD3377	Discontinued
0.6868	Remote Similarity	NPD7014	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD6301	Phase 2
0.6864	Remote Similarity	NPD979	Approved
0.6864	Remote Similarity	NPD4942	Approved
0.6864	Remote Similarity	NPD4161	Discontinued
0.6852	Remote Similarity	NPD2470	Clinical (unspecified phase)
0.6851	Remote Similarity	NPD5498	Phase 2
0.6851	Remote Similarity	NPD4092	Approved
0.6829	Remote Similarity	NPD3170	Approved
0.6828	Remote Similarity	NPD4515	Suspended
0.6821	Remote Similarity	NPD1208	Approved
0.6821	Remote Similarity	NPD1211	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD1631	Approved
0.6813	Remote Similarity	NPD486	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD5871	Discontinued
0.68	Remote Similarity	NPD4311	Approved
0.6798	Remote Similarity	NPD2404	Discontinued
0.6798	Remote Similarity	NPD2821	Approved
0.6796	Remote Similarity	NPD4091	Approved
0.6765	Remote Similarity	NPD1664	Clinical (unspecified phase)
0.676	Remote Similarity	NPD1575	Approved
0.676	Remote Similarity	NPD1573	Approved
0.6752	Remote Similarity	NPD657	Approved
0.6752	Remote Similarity	NPD660	Approved
0.6752	Remote Similarity	NPD661	Approved
0.6752	Remote Similarity	NPD655	Approved
0.6746	Remote Similarity	NPD6416	Phase 2
0.6744	Remote Similarity	NPD3248	Phase 1
0.674	Remote Similarity	NPD3423	Phase 2
0.674	Remote Similarity	NPD3422	Phase 3
0.674	Remote Similarity	NPD7449	Clinical (unspecified phase)
0.674	Remote Similarity	NPD3522	Approved
0.673	Remote Similarity	NPD701	Approved
0.673	Remote Similarity	NPD698	Approved
0.6728	Remote Similarity	NPD1874	Clinical (unspecified phase)
0.6728	Remote Similarity	NPD1541	Approved
0.6722	Remote Similarity	NPD1913	Phase 1
0.6721	Remote Similarity	NPD3997	Approved
0.6721	Remote Similarity	NPD3999	Approved
0.6721	Remote Similarity	NPD3998	Approved
0.672	Remote Similarity	NPD5592	Clinical (unspecified phase)
0.671	Remote Similarity	NPD1362	Clinical (unspecified phase)
0.6708	Remote Similarity	NPD1619	Phase 3
0.6706	Remote Similarity	NPD1801	Approved
0.6706	Remote Similarity	NPD1802	Approved
0.6705	Remote Similarity	NPD2360	Approved
0.6704	Remote Similarity	NPD3468	Approved
0.6702	Remote Similarity	NPD5975	Clinical (unspecified phase)
0.6698	Remote Similarity	NPD6142	Phase 3
0.6684	Remote Similarity	NPD6480	Clinical (unspecified phase)
0.6684	Remote Similarity	NPD8146	Phase 2
0.6684	Remote Similarity	NPD3315	Phase 3
0.6667	Remote Similarity	NPD3992	Approved
0.6667	Remote Similarity	NPD3996	Approved
0.6667	Remote Similarity	NPD4432	Discontinued
0.6667	Remote Similarity	NPD3991	Approved
0.6667	Remote Similarity	NPD1195	Approved
0.6667	Remote Similarity	NPD1839	Phase 1
0.6667	Remote Similarity	NPD3995	Approved
0.6667	Remote Similarity	NPD721	Approved
0.6667	Remote Similarity	NPD3993	Approved
0.6667	Remote Similarity	NPD3994	Approved
0.6649	Remote Similarity	NPD3990	Phase 3
0.6649	Remote Similarity	NPD5608	Approved
0.6649	Remote Similarity	NPD5609	Approved
0.6649	Remote Similarity	NPD6483	Approved
0.6649	Remote Similarity	NPD6484	Approved
0.6648	Remote Similarity	NPD5466	Approved
0.6648	Remote Similarity	NPD3587	Clinical (unspecified phase)
0.6648	Remote Similarity	NPD1630	Approved
0.6648	Remote Similarity	NPD2359	Approved
0.6647	Remote Similarity	NPD3434	Clinical (unspecified phase)
0.6647	Remote Similarity	NPD4351	Clinical (unspecified phase)
0.6647	Remote Similarity	NPD2882	Phase 1
0.6647	Remote Similarity	NPD3278	Clinical (unspecified phase)
0.6632	Remote Similarity	NPD5195	Discontinued
0.6632	Remote Similarity	NPD5076	Approved
0.6632	Remote Similarity	NPD5077	Approved
0.6629	Remote Similarity	NPD2672	Discontinued
0.6627	Remote Similarity	NPD1196	Approved
0.6626	Remote Similarity	NPD441	Approved
0.6623	Remote Similarity	NPD181	Approved
0.6612	Remote Similarity	NPD2361	Approved
0.6612	Remote Similarity	NPD3004	Clinical (unspecified phase)
0.6611	Remote Similarity	NPD2034	Discontinued
0.6605	Remote Similarity	NPD4938	Phase 2
0.6603	Remote Similarity	NPD9272	Approved
0.6595	Remote Similarity	NPD1643	Phase 3
0.6595	Remote Similarity	NPD3989	Phase 3
0.6592	Remote Similarity	NPD7591	Clinical (unspecified phase)
0.6592	Remote Similarity	NPD3363	Clinical (unspecified phase)
0.657	Remote Similarity	NPD7528	Approved
0.657	Remote Similarity	NPD4939	Clinical (unspecified phase)
0.6569	Remote Similarity	NPD6733	Discontinued
0.6567	Remote Similarity	NPD5860	Discontinued
0.6566	Remote Similarity	NPD6987	Phase 1
0.6566	Remote Similarity	NPD5901	Discontinued
0.6566	Remote Similarity	NPD6342	Discontinued
0.6566	Remote Similarity	NPD3864	Clinical (unspecified phase)
0.6564	Remote Similarity	NPD6874	Approved
0.6562	Remote Similarity	NPD4539	Phase 1
0.6557	Remote Similarity	NPD7662	Clinical (unspecified phase)
0.6556	Remote Similarity	NPD4554	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD5663	Discontinued
0.655	Remote Similarity	NPD4082	Approved
0.655	Remote Similarity	NPD2510	Approved
0.655	Remote Similarity	NPD2509	Approved
0.6548	Remote Similarity	NPD7071	Clinical (unspecified phase)
0.6546	Remote Similarity	NPD5515	Phase 2
0.6545	Remote Similarity	NPD4370	Phase 3
0.6541	Remote Similarity	NPD5157	Phase 1
0.6541	Remote Similarity	NPD5159	Phase 2
0.6541	Remote Similarity	NPD3239	Clinical (unspecified phase)
0.6541	Remote Similarity	NPD5158	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD2210	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