NPASS Compound

Structure

NPC470350 OpenBabel07101719522D 27 30 0 0 1 0 0 0 0 0999 V2000 4.7261 -0.9523 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9345 -1.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7861 -1.9305 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8601 -0.4523 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0685 -1.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9941 -0.9523 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2024 -1.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1280 -0.4523 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3364 -1.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8601 0.5477 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0685 -2.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1280 0.5477 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3364 -2.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9941 1.0477 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2024 -3.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3849 -1.1215 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.4067 -0.9135 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9945 -0.1045 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 4.7261 1.0477 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.9345 -3.0827 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2620 1.0477 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5296 -3.0827 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.9941 2.0477 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2024 -4.0827 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6637 0.6386 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7916 -2.0350 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 4 1 0 0 0 0 2 5 1 0 0 0 0 3 6 1 0 0 0 0 3 26 1 0 0 0 0 4 6 2 0 0 0 0 4 10 1 0 0 0 0 5 7 2 0 0 0 0 5 11 1 0 0 0 0 6 8 1 0 0 0 0 7 9 1 0 0 0 0 7 18 1 0 0 0 0 8 12 2 0 0 0 0 9 13 2 0 0 0 0 10 14 2 0 0 0 0 10 19 1 0 0 0 0 11 15 2 0 0 0 0 11 20 1 0 0 0 0 12 14 1 0 0 0 0 12 21 1 0 0 0 0 13 15 1 0 0 0 0 13 22 1 0 0 0 0 14 23 1 0 0 0 0 15 24 1 0 0 0 0 16 8 1 1 0 0 0 16 17 1 0 0 0 0 16 26 1 0 0 0 0 17 9 1 6 0 0 0 17 27 1 0 0 0 0 18 25 1 0 0 0 0 18 27 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	378.1
Volume:	348.952
LogP:	0.552
LogD:	0.07
LogS:	-3.051
# Rotatable Bonds:	1
TPSA:	160.07
# H-Bond Aceptor:	9
# H-Bond Donor:	7
# Rings:	4
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.367
Synthetic Accessibility Score:	4.545
Fsp3:	0.333
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.308
MDCK Permeability:	3.660974698505015e-06
Pgp-inhibitor:	0.014
Pgp-substrate:	0.85
Human Intestinal Absorption (HIA):	0.936
20% Bioavailability (F20%):	0.654
30% Bioavailability (F30%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.013
Plasma Protein Binding (PPB):	97.1202621459961%
Volume Distribution (VD):	0.546
Pgp-substrate:	10.963117599487305%

ADMET: Metabolism

CYP1A2-inhibitor:	0.026
CYP1A2-substrate:	0.321
CYP2C19-inhibitor:	0.01
CYP2C19-substrate:	0.077
CYP2C9-inhibitor:	0.051
CYP2C9-substrate:	0.162
CYP2D6-inhibitor:	0.013
CYP2D6-substrate:	0.138
CYP3A4-inhibitor:	0.008
CYP3A4-substrate:	0.035

ADMET: Excretion

Clearance (CL):	1.813
Half-life (T1/2):	0.92

ADMET: Toxicity

hERG Blockers:	0.167
Human Hepatotoxicity (H-HT):	0.244
Drug-inuced Liver Injury (DILI):	0.66
AMES Toxicity:	0.355
Rat Oral Acute Toxicity:	0.034
Maximum Recommended Daily Dose:	0.576
Skin Sensitization:	0.967
Carcinogencity:	0.073
Eye Corrosion:	0.003
Eye Irritation:	0.907
Respiratory Toxicity:	0.027

Download Data

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

Natural Product: NPC470350

Natural Product ID:	NPC470350
*Common Name:**	Flavimycin A
IUPAC Name:	(3S)-7-methyl-3-[(1R)-5,6,7-trihydroxy-4-methyl-1,3-dihydro-2-benzofuran-1-yl]-1,3-dihydro-2-benzofuran-1,4,5,6-tetrol
Synonyms:	Flavimycin A
Standard InCHIKey:	VJXHTAZAWHMKML-DVKDBIPTSA-N
Standard InCHI:	InChI=1S/C18H18O9/c1-4-6-3-26-16(8(6)12(21)14(23)10(4)19)17-9-7(18(25)27-17)5(2)11(20)15(24)13(9)22/h16-25H,3H2,1-2H3/t16-,17+,18?/m1/s1
SMILES:	Oc1c(O)c(O)c(c2c1[C@@H](OC2)[C@H]1OC(c2c1c(O)c(c(c2C)O)O)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2012550
PubChem CID:	57345646
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0004191] Isocoumarans

*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
NPO18099	Aspergillus flavipes	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22329646]
NPO18099	Aspergillus flavipes	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31674782]
NPO18099	Aspergillus flavipes	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32568536]
NPO18099	Aspergillus flavipes	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7517439]
NPO18099	Aspergillus flavipes	Species	Aspergillaceae	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	1
MIC	3

Activity Type	# Activity
Individual Protein	1
Organism	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT6558	Individual Protein	Peptide deformylase	Staphylococcus aureus	IC50	=	35800.0	nM	PMID[450892]
NPT1101	Organism	Staphylococcus aureus subsp. aureus RN4220	Staphylococcus aureus subsp. aureus RN4220	MIC	=	32.0	ug.mL-1	PMID[450892]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	32.0	ug.mL-1	PMID[450892]

☑ 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 NPC470350 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	381
0.1-0.2	1801
0.2-0.3	4591
0.3-0.4	11308
0.4-0.5	8107
0.5-0.6	6074
0.6-0.7	8076
0.7-0.8	2230
0.8-0.85	126
0.85-0.9	1
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC470351
0.8493	Intermediate Similarity	NPC472709
0.8493	Intermediate Similarity	NPC472710
0.8472	Intermediate Similarity	NPC154971
0.8472	Intermediate Similarity	NPC252286
0.8451	Intermediate Similarity	NPC41782
0.844	Intermediate Similarity	NPC177868
0.8414	Intermediate Similarity	NPC116019
0.8403	Intermediate Similarity	NPC166506
0.8403	Intermediate Similarity	NPC180953
0.8403	Intermediate Similarity	NPC110763
0.8403	Intermediate Similarity	NPC197352
0.8403	Intermediate Similarity	NPC189239
0.8403	Intermediate Similarity	NPC475868
0.8392	Intermediate Similarity	NPC185071
0.8392	Intermediate Similarity	NPC12728
0.8367	Intermediate Similarity	NPC182368
0.8367	Intermediate Similarity	NPC469706
0.8367	Intermediate Similarity	NPC145979
0.8367	Intermediate Similarity	NPC185955
0.8367	Intermediate Similarity	NPC469707
0.8367	Intermediate Similarity	NPC214326
0.8367	Intermediate Similarity	NPC9933
0.8367	Intermediate Similarity	NPC218041
0.8367	Intermediate Similarity	NPC225815
0.8367	Intermediate Similarity	NPC260781
0.8356	Intermediate Similarity	NPC130449
0.8356	Intermediate Similarity	NPC248132
0.8345	Intermediate Similarity	NPC212890
0.8333	Intermediate Similarity	NPC118385
0.8333	Intermediate Similarity	NPC121661
0.8333	Intermediate Similarity	NPC473046
0.8333	Intermediate Similarity	NPC472713
0.8333	Intermediate Similarity	NPC73467
0.8333	Intermediate Similarity	NPC472712
0.8333	Intermediate Similarity	NPC187774
0.8333	Intermediate Similarity	NPC172171
0.8333	Intermediate Similarity	NPC239254
0.8321	Intermediate Similarity	NPC258483
0.8299	Intermediate Similarity	NPC51328
0.8299	Intermediate Similarity	NPC286235
0.8299	Intermediate Similarity	NPC55158
0.8298	Intermediate Similarity	NPC474039
0.8298	Intermediate Similarity	NPC283949
0.8286	Intermediate Similarity	NPC141765
0.8286	Intermediate Similarity	NPC24490
0.8286	Intermediate Similarity	NPC34103
0.8286	Intermediate Similarity	NPC165155
0.8276	Intermediate Similarity	NPC477702
0.8264	Intermediate Similarity	NPC298317
0.8264	Intermediate Similarity	NPC324962
0.8264	Intermediate Similarity	NPC265154
0.8264	Intermediate Similarity	NPC255566
0.8264	Intermediate Similarity	NPC474808
0.8255	Intermediate Similarity	NPC21902
0.8252	Intermediate Similarity	NPC87725
0.8252	Intermediate Similarity	NPC471414
0.8252	Intermediate Similarity	NPC263261
0.8243	Intermediate Similarity	NPC98624
0.8243	Intermediate Similarity	NPC473989
0.8243	Intermediate Similarity	NPC24425
0.8231	Intermediate Similarity	NPC270751
0.8231	Intermediate Similarity	NPC71726
0.8219	Intermediate Similarity	NPC190714
0.8219	Intermediate Similarity	NPC99515
0.8214	Intermediate Similarity	NPC244983
0.8214	Intermediate Similarity	NPC326095
0.8194	Intermediate Similarity	NPC191231
0.8194	Intermediate Similarity	NPC133934
0.8194	Intermediate Similarity	NPC103637
0.8194	Intermediate Similarity	NPC184684
0.8194	Intermediate Similarity	NPC253878
0.8194	Intermediate Similarity	NPC36531
0.8194	Intermediate Similarity	NPC229172
0.8194	Intermediate Similarity	NPC184641
0.8194	Intermediate Similarity	NPC230538
0.8194	Intermediate Similarity	NPC5262
0.8194	Intermediate Similarity	NPC472714
0.8188	Intermediate Similarity	NPC475756
0.8182	Intermediate Similarity	NPC226547
0.8182	Intermediate Similarity	NPC46591
0.8182	Intermediate Similarity	NPC56091
0.8175	Intermediate Similarity	NPC311293
0.8175	Intermediate Similarity	NPC148366
0.8169	Intermediate Similarity	NPC185908
0.8163	Intermediate Similarity	NPC31325
0.8163	Intermediate Similarity	NPC224674
0.8163	Intermediate Similarity	NPC275284
0.8163	Intermediate Similarity	NPC193473
0.8163	Intermediate Similarity	NPC15956
0.8163	Intermediate Similarity	NPC39657
0.8163	Intermediate Similarity	NPC114505
0.8163	Intermediate Similarity	NPC213074
0.8156	Intermediate Similarity	NPC126409
0.8156	Intermediate Similarity	NPC256262
0.8156	Intermediate Similarity	NPC99572
0.8156	Intermediate Similarity	NPC236522
0.8156	Intermediate Similarity	NPC150534
0.8151	Intermediate Similarity	NPC475096
0.8151	Intermediate Similarity	NPC161700
0.8151	Intermediate Similarity	NPC277867
0.8146	Intermediate Similarity	NPC159922
0.8138	Intermediate Similarity	NPC477898
0.8138	Intermediate Similarity	NPC473044
0.8138	Intermediate Similarity	NPC37793
0.8133	Intermediate Similarity	NPC471154
0.8125	Intermediate Similarity	NPC311530
0.8117	Intermediate Similarity	NPC268718
0.8117	Intermediate Similarity	NPC150943
0.8117	Intermediate Similarity	NPC91634
0.8112	Intermediate Similarity	NPC230124
0.8112	Intermediate Similarity	NPC114171
0.8112	Intermediate Similarity	NPC32630
0.8112	Intermediate Similarity	NPC9068
0.8112	Intermediate Similarity	NPC6369
0.8112	Intermediate Similarity	NPC30951
0.8112	Intermediate Similarity	NPC6300
0.8108	Intermediate Similarity	NPC325720
0.8108	Intermediate Similarity	NPC316676
0.8108	Intermediate Similarity	NPC301961
0.8108	Intermediate Similarity	NPC179809
0.8108	Intermediate Similarity	NPC166584
0.8108	Intermediate Similarity	NPC175976
0.8099	Intermediate Similarity	NPC470802
0.8095	Intermediate Similarity	NPC260397
0.8095	Intermediate Similarity	NPC226540
0.8095	Intermediate Similarity	NPC324492
0.8095	Intermediate Similarity	NPC125755
0.8095	Intermediate Similarity	NPC317053
0.8095	Intermediate Similarity	NPC33832
0.8088	Intermediate Similarity	NPC476653
0.8085	Intermediate Similarity	NPC287745
0.8085	Intermediate Similarity	NPC107478
0.8082	Intermediate Similarity	NPC138227
0.8082	Intermediate Similarity	NPC76176
0.8082	Intermediate Similarity	NPC168579
0.8082	Intermediate Similarity	NPC473045
0.8082	Intermediate Similarity	NPC25292
0.8082	Intermediate Similarity	NPC469313
0.8082	Intermediate Similarity	NPC84181
0.8079	Intermediate Similarity	NPC474606
0.8077	Intermediate Similarity	NPC14294
0.8077	Intermediate Similarity	NPC116759
0.8071	Intermediate Similarity	NPC175067
0.8071	Intermediate Similarity	NPC204215
0.8069	Intermediate Similarity	NPC287124
0.8069	Intermediate Similarity	NPC189115
0.8069	Intermediate Similarity	NPC475084
0.8056	Intermediate Similarity	NPC103448
0.8056	Intermediate Similarity	NPC284464
0.8056	Intermediate Similarity	NPC216434
0.8054	Intermediate Similarity	NPC240521
0.8042	Intermediate Similarity	NPC301765
0.8042	Intermediate Similarity	NPC156948
0.8042	Intermediate Similarity	NPC3072
0.8042	Intermediate Similarity	NPC46277
0.8042	Intermediate Similarity	NPC477938
0.8042	Intermediate Similarity	NPC86605
0.8041	Intermediate Similarity	NPC227902
0.8041	Intermediate Similarity	NPC327412
0.8041	Intermediate Similarity	NPC15538
0.8041	Intermediate Similarity	NPC320671
0.8041	Intermediate Similarity	NPC320970
0.8041	Intermediate Similarity	NPC473480
0.8041	Intermediate Similarity	NPC328567
0.8028	Intermediate Similarity	NPC135777
0.8028	Intermediate Similarity	NPC101624
0.8028	Intermediate Similarity	NPC142547
0.8028	Intermediate Similarity	NPC184938
0.8027	Intermediate Similarity	NPC279298
0.8027	Intermediate Similarity	NPC476301
0.8027	Intermediate Similarity	NPC43508
0.8027	Intermediate Similarity	NPC221318
0.8027	Intermediate Similarity	NPC18979
0.8027	Intermediate Similarity	NPC22150
0.8027	Intermediate Similarity	NPC307466
0.8027	Intermediate Similarity	NPC38041
0.8026	Intermediate Similarity	NPC312763
0.8015	Intermediate Similarity	NPC257682
0.8015	Intermediate Similarity	NPC146355
0.8015	Intermediate Similarity	NPC131747
0.8014	Intermediate Similarity	NPC112237
0.8014	Intermediate Similarity	NPC474104
0.8014	Intermediate Similarity	NPC471390
0.8014	Intermediate Similarity	NPC474453
0.8014	Intermediate Similarity	NPC102044
0.8014	Intermediate Similarity	NPC47633
0.8014	Intermediate Similarity	NPC81638
0.8014	Intermediate Similarity	NPC58585
0.8014	Intermediate Similarity	NPC471391
0.8014	Intermediate Similarity	NPC85264
0.8014	Intermediate Similarity	NPC158331
0.8013	Intermediate Similarity	NPC474442
0.8013	Intermediate Similarity	NPC302610
0.8	Intermediate Similarity	NPC469661
0.8	Intermediate Similarity	NPC15543
0.8	Intermediate Similarity	NPC472711
0.8	Intermediate Similarity	NPC238140
0.8	Intermediate Similarity	NPC265075
0.7987	Intermediate Similarity	NPC181168

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 NPC470350 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	325
0.1-0.2	1027
0.2-0.3	2436
0.3-0.4	2931
0.4-0.5	1366
0.5-0.6	820
0.6-0.7	229
0.7-0.8	16
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8052	Intermediate Similarity	NPD6234	Discontinued
0.7925	Intermediate Similarity	NPD7228	Approved
0.7922	Intermediate Similarity	NPD4966	Approved
0.7922	Intermediate Similarity	NPD4965	Approved
0.7922	Intermediate Similarity	NPD4967	Phase 2
0.7857	Intermediate Similarity	NPD3027	Phase 3
0.7755	Intermediate Similarity	NPD6674	Discontinued
0.7727	Intermediate Similarity	NPD37	Approved
0.7692	Intermediate Similarity	NPD1613	Approved
0.7692	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7266	Discontinued
0.7465	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7413	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD7240	Approved
0.7391	Intermediate Similarity	NPD7199	Phase 2
0.7286	Intermediate Similarity	NPD3705	Approved
0.7273	Intermediate Similarity	NPD3818	Discontinued
0.7266	Intermediate Similarity	NPD5125	Phase 3
0.7266	Intermediate Similarity	NPD5126	Approved
0.7244	Intermediate Similarity	NPD1653	Approved
0.7195	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD7074	Phase 3
0.7079	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD7054	Approved
0.7019	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD4625	Phase 3
0.7	Intermediate Similarity	NPD6559	Discontinued
0.6982	Remote Similarity	NPD7472	Approved
0.698	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.698	Remote Similarity	NPD3620	Phase 2
0.698	Remote Similarity	NPD4060	Phase 1
0.6977	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6948	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD2532	Approved
0.6943	Remote Similarity	NPD2533	Approved
0.6943	Remote Similarity	NPD2534	Approved
0.6941	Remote Similarity	NPD6797	Phase 2
0.6939	Remote Similarity	NPD4908	Phase 1
0.6933	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD7680	Approved
0.6923	Remote Similarity	NPD1091	Approved
0.6901	Remote Similarity	NPD7251	Discontinued
0.6871	Remote Similarity	NPD3018	Phase 2
0.6852	Remote Similarity	NPD1934	Approved
0.6838	Remote Similarity	NPD3021	Approved
0.6838	Remote Similarity	NPD3022	Approved
0.6826	Remote Similarity	NPD6232	Discontinued
0.6824	Remote Similarity	NPD5844	Phase 1
0.6806	Remote Similarity	NPD1610	Phase 2
0.6803	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD7975	Clinical (unspecified phase)
0.6763	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6763	Remote Similarity	NPD7808	Phase 3
0.6757	Remote Similarity	NPD2861	Phase 2
0.6752	Remote Similarity	NPD6190	Approved
0.6746	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6746	Remote Similarity	NPD6166	Phase 2
0.6746	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6743	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6735	Remote Similarity	NPD3094	Phase 2
0.6733	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6733	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.673	Remote Similarity	NPD4160	Clinical (unspecified phase)
0.6728	Remote Similarity	NPD4380	Phase 2
0.6727	Remote Similarity	NPD3882	Suspended
0.6725	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6713	Remote Similarity	NPD1357	Approved
0.6712	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6712	Remote Similarity	NPD2982	Phase 2
0.6712	Remote Similarity	NPD2983	Phase 2
0.6711	Remote Similarity	NPD5124	Phase 1
0.6711	Remote Similarity	NPD230	Phase 1
0.6711	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6709	Remote Similarity	NPD5058	Phase 3
0.6707	Remote Similarity	NPD1465	Phase 2
0.6706	Remote Similarity	NPD7473	Discontinued
0.6667	Remote Similarity	NPD6696	Suspended
0.6667	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6644	Remote Similarity	NPD2981	Phase 2
0.6643	Remote Similarity	NPD1398	Phase 1
0.6643	Remote Similarity	NPD1548	Phase 1
0.662	Remote Similarity	NPD7340	Approved
0.6606	Remote Similarity	NPD2978	Approved
0.6606	Remote Similarity	NPD8455	Phase 2
0.6606	Remote Similarity	NPD2801	Approved
0.6606	Remote Similarity	NPD2977	Approved
0.6603	Remote Similarity	NPD5763	Approved
0.6603	Remote Similarity	NPD5762	Approved
0.6599	Remote Similarity	NPD4749	Approved
0.6594	Remote Similarity	NPD4750	Phase 3
0.6582	Remote Similarity	NPD7982	Clinical (unspecified phase)
0.6575	Remote Similarity	NPD3092	Approved
0.6573	Remote Similarity	NPD6842	Approved
0.6573	Remote Similarity	NPD6843	Phase 3
0.6573	Remote Similarity	NPD6841	Approved
0.6568	Remote Similarity	NPD6959	Discontinued
0.6566	Remote Similarity	NPD6374	Clinical (unspecified phase)
0.6564	Remote Similarity	NPD4005	Discontinued
0.6552	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6543	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6525	Remote Similarity	NPD5283	Phase 1
0.6522	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6513	Remote Similarity	NPD7985	Registered
0.6509	Remote Similarity	NPD5494	Approved
0.6506	Remote Similarity	NPD7819	Suspended
0.65	Remote Similarity	NPD228	Approved
0.6494	Remote Similarity	NPD5735	Approved
0.6488	Remote Similarity	NPD7075	Discontinued
0.6481	Remote Similarity	NPD1940	Clinical (unspecified phase)
0.6478	Remote Similarity	NPD3892	Phase 2
0.6474	Remote Similarity	NPD4108	Discontinued
0.6474	Remote Similarity	NPD5588	Approved
0.6467	Remote Similarity	NPD3817	Phase 2
0.6464	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6463	Remote Similarity	NPD6055	Clinical (unspecified phase)
0.646	Remote Similarity	NPD1511	Approved
0.6454	Remote Similarity	NPD7635	Approved
0.6446	Remote Similarity	NPD6801	Discontinued
0.6444	Remote Similarity	NPD940	Approved
0.6444	Remote Similarity	NPD846	Approved
0.6444	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6443	Remote Similarity	NPD8651	Approved
0.6438	Remote Similarity	NPD2677	Approved
0.6438	Remote Similarity	NPD5084	Clinical (unspecified phase)
0.6438	Remote Similarity	NPD5307	Clinical (unspecified phase)
0.6433	Remote Similarity	NPD5711	Approved
0.6433	Remote Similarity	NPD7229	Phase 3
0.6433	Remote Similarity	NPD5710	Approved
0.6433	Remote Similarity	NPD3787	Discontinued
0.642	Remote Similarity	NPD7685	Pre-registration
0.6415	Remote Similarity	NPD2800	Approved
0.6414	Remote Similarity	NPD3091	Approved
0.6414	Remote Similarity	NPD7741	Discontinued
0.641	Remote Similarity	NPD4537	Clinical (unspecified phase)
0.641	Remote Similarity	NPD4978	Clinical (unspecified phase)
0.641	Remote Similarity	NPD4538	Approved
0.641	Remote Similarity	NPD4536	Approved
0.6405	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6393	Remote Similarity	NPD6535	Approved
0.6393	Remote Similarity	NPD6534	Approved
0.6392	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6392	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6392	Remote Similarity	NPD6005	Phase 3
0.6392	Remote Similarity	NPD3540	Phase 1
0.6392	Remote Similarity	NPD6004	Phase 3
0.6392	Remote Similarity	NPD6002	Phase 3
0.6389	Remote Similarity	NPD7906	Approved
0.638	Remote Similarity	NPD1512	Approved
0.6376	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.637	Remote Similarity	NPD1242	Phase 1
0.6369	Remote Similarity	NPD2560	Approved
0.6369	Remote Similarity	NPD2563	Approved
0.6358	Remote Similarity	NPD2489	Approved
0.6358	Remote Similarity	NPD27	Approved
0.6352	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6348	Remote Similarity	NPD8312	Approved
0.6348	Remote Similarity	NPD8313	Approved
0.6346	Remote Similarity	NPD6651	Approved
0.6333	Remote Similarity	NPD4663	Approved
0.6329	Remote Similarity	NPD3539	Phase 1
0.6327	Remote Similarity	NPD4626	Approved
0.6323	Remote Similarity	NPD2238	Phase 2
0.6323	Remote Similarity	NPD943	Approved
0.6319	Remote Similarity	NPD7157	Approved
0.6319	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD4666	Phase 3
0.6312	Remote Similarity	NPD4237	Approved
0.6312	Remote Similarity	NPD4236	Phase 3
0.6312	Remote Similarity	NPD1652	Phase 2
0.631	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6302	Remote Similarity	NPD8151	Discontinued
0.6301	Remote Similarity	NPD2970	Approved
0.6301	Remote Similarity	NPD2969	Approved
0.6294	Remote Similarity	NPD4055	Discovery
0.629	Remote Similarity	NPD7699	Phase 2
0.629	Remote Similarity	NPD7700	Phase 2
0.6289	Remote Similarity	NPD1375	Discontinued
0.6286	Remote Similarity	NPD3751	Discontinued
0.6282	Remote Similarity	NPD6355	Discontinued
0.628	Remote Similarity	NPD5261	Clinical (unspecified phase)
0.6273	Remote Similarity	NPD3750	Approved
0.6273	Remote Similarity	NPD8166	Discontinued
0.6272	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6266	Remote Similarity	NPD5960	Phase 3
0.6259	Remote Similarity	NPD5691	Approved
0.6258	Remote Similarity	NPD6407	Approved
0.6258	Remote Similarity	NPD6405	Approved
0.6258	Remote Similarity	NPD7390	Discontinued
0.6257	Remote Similarity	NPD7313	Approved
0.6257	Remote Similarity	NPD4577	Approved
0.6257	Remote Similarity	NPD4578	Approved
0.6257	Remote Similarity	NPD7311	Approved
0.6257	Remote Similarity	NPD7312	Approved
0.6257	Remote Similarity	NPD5709	Phase 3
0.6257	Remote Similarity	NPD7310	Approved
0.625	Remote Similarity	NPD2424	Discontinued
0.6243	Remote Similarity	NPD3051	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