NPASS Compound

Structure

NPC197168 OpenBabel07101718242D 23 25 0 0 1 0 0 0 0 0999 V2000 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 3.5000 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 0.8660 1.5000 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 -4.3301 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 1 0 0 0 0 0 0 0 0 0 -4.3301 0.5000 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 -0.0000 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 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 -0.8660 1.5000 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 -1.7321 -0.0000 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 -0.0000 3.0000 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 -5.1962 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 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 2 20 1 0 0 0 0 3 21 1 0 0 0 0 4 22 1 0 0 0 0 5 8 1 0 0 0 0 5 11 1 0 0 0 0 6 9 2 0 0 0 0 6 10 1 0 0 0 0 7 9 1 0 0 0 0 7 12 2 0 0 0 0 8 1 1 6 0 0 0 8 23 1 0 0 0 0 9 20 1 0 0 0 0 10 13 2 0 0 0 0 10 16 1 0 0 0 0 11 14 1 0 0 0 0 11 18 2 0 0 0 0 12 13 1 0 0 0 0 12 21 1 0 0 0 0 13 15 1 0 0 0 0 14 15 2 0 0 0 0 14 17 1 0 0 0 0 15 19 1 0 0 0 0 16 17 2 0 0 0 0 16 22 1 0 0 0 0 17 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	318.11
Volume:	313.841
LogP:	3.679
LogD:	2.965
LogS:	-4.705
# Rotatable Bonds:	3
TPSA:	74.22
# H-Bond Aceptor:	6
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.938
Synthetic Accessibility Score:	3.099
Fsp3:	0.353
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:	-4.631
MDCK Permeability:	2.8350417778710835e-05
Pgp-inhibitor:	0.95
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.001
30% Bioavailability (F30%):	0.001

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.082
Plasma Protein Binding (PPB):	84.34207916259766%
Volume Distribution (VD):	1.024
Pgp-substrate:	14.701436042785645%

ADMET: Metabolism

CYP1A2-inhibitor:	0.776
CYP1A2-substrate:	0.938
CYP2C19-inhibitor:	0.541
CYP2C19-substrate:	0.853
CYP2C9-inhibitor:	0.453
CYP2C9-substrate:	0.885
CYP2D6-inhibitor:	0.626
CYP2D6-substrate:	0.703
CYP3A4-inhibitor:	0.491
CYP3A4-substrate:	0.275

ADMET: Excretion

Clearance (CL):	8.287
Half-life (T1/2):	0.258

ADMET: Toxicity

hERG Blockers:	0.015
Human Hepatotoxicity (H-HT):	0.281
Drug-inuced Liver Injury (DILI):	0.872
AMES Toxicity:	0.325
Rat Oral Acute Toxicity:	0.7
Maximum Recommended Daily Dose:	0.232
Skin Sensitization:	0.63
Carcinogencity:	0.506
Eye Corrosion:	0.004
Eye Irritation:	0.648
Respiratory Toxicity:	0.865

Download Data

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

Natural Product: NPC197168

Natural Product ID:	NPC197168
*Common Name:**	(2S)-5-Hydroxy-6,8,10-Trimethoxy-2-Methyl-2,3-Dihydrobenzo[G]Chromen-4-One
IUPAC Name:	(2S)-5-hydroxy-6,8,10-trimethoxy-2-methyl-2,3-dihydrobenzo[g]chromen-4-one
Synonyms:
Standard InCHIKey:	DWGSEYZQYRDTJV-QMMMGPOBSA-N
Standard InCHI:	InChI=1S/C17H18O6/c1-8-5-11(18)14-15(19)13-10(16(22-4)17(14)23-8)6-9(20-2)7-12(13)21-3/h6-8,19H,5H2,1-4H3/t8-/m0/s1
SMILES:	C[C@H]1CC(=O)c2c(c3c(cc(cc3OC)OC)c(c2O1)OC)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL497901
PubChem CID:	10710646
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001640] Naphthopyrans [CHEMONTID:0001641] Naphthopyranones

*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
NPO4343	Guanomyces polythrix	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	PMID[10869195]
NPO4343	Guanomyces polythrix	Species	n.a.	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
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT965	Organism	Amaranthus hypochondriacus	Amaranthus hypochondriacus	IC50	=	13000.0	nM	PMID[488995]
NPT117	Organism	Echinochloa crus-galli	Echinochloa crus-galli	IC50	=	40000.0	nM	PMID[488995]

☑ 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 NPC197168 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	433
0.1-0.2	1817
0.2-0.3	4216
0.3-0.4	10235
0.4-0.5	7862
0.5-0.6	3388
0.6-0.7	4939
0.7-0.8	5407
0.8-0.85	2616
0.85-0.9	1478
0.9-0.95	303
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9935	High Similarity	NPC25361
0.9742	High Similarity	NPC66288
0.9742	High Similarity	NPC474186
0.9677	High Similarity	NPC475886
0.9677	High Similarity	NPC474287
0.9675	High Similarity	NPC217677
0.9675	High Similarity	NPC165977
0.9618	High Similarity	NPC236132
0.9618	High Similarity	NPC270837
0.9615	High Similarity	NPC474351
0.9615	High Similarity	NPC474187
0.9615	High Similarity	NPC475883
0.9557	High Similarity	NPC326520
0.9554	High Similarity	NPC294965
0.9551	High Similarity	NPC228785
0.9551	High Similarity	NPC14353
0.9551	High Similarity	NPC56085
0.9497	High Similarity	NPC170245
0.9494	High Similarity	NPC7483
0.949	High Similarity	NPC278052
0.949	High Similarity	NPC40491
0.949	High Similarity	NPC61010
0.9487	High Similarity	NPC100123
0.9487	High Similarity	NPC85121
0.9437	High Similarity	NPC117854
0.9437	High Similarity	NPC6588
0.9437	High Similarity	NPC477154
0.943	High Similarity	NPC229632
0.9427	High Similarity	NPC299436
0.9427	High Similarity	NPC320359
0.9427	High Similarity	NPC36217
0.9427	High Similarity	NPC119224
0.9423	High Similarity	NPC223787
0.9423	High Similarity	NPC300727
0.9423	High Similarity	NPC241904
0.9419	High Similarity	NPC37392
0.9375	High Similarity	NPC37870
0.9375	High Similarity	NPC43319
0.9375	High Similarity	NPC272502
0.9371	High Similarity	NPC236521
0.9371	High Similarity	NPC152659
0.9371	High Similarity	NPC273959
0.9371	High Similarity	NPC248638
0.9371	High Similarity	NPC474350
0.9371	High Similarity	NPC220313
0.9371	High Similarity	NPC475985
0.9363	High Similarity	NPC95936
0.9363	High Similarity	NPC250214
0.9363	High Similarity	NPC329091
0.9363	High Similarity	NPC476242
0.9359	High Similarity	NPC274730
0.9359	High Similarity	NPC142339
0.9351	High Similarity	NPC72958
0.9351	High Similarity	NPC232645
0.9317	High Similarity	NPC474024
0.9317	High Similarity	NPC218226
0.9313	High Similarity	NPC472450
0.9313	High Similarity	NPC275780
0.9313	High Similarity	NPC239752
0.9313	High Similarity	NPC473286
0.9308	High Similarity	NPC470694
0.9308	High Similarity	NPC201800
0.9308	High Similarity	NPC52204
0.9308	High Similarity	NPC25152
0.9299	High Similarity	NPC36852
0.9299	High Similarity	NPC469584
0.9299	High Similarity	NPC475267
0.9299	High Similarity	NPC262286
0.9299	High Similarity	NPC474208
0.9299	High Similarity	NPC48208
0.9299	High Similarity	NPC474836
0.9299	High Similarity	NPC236796
0.9299	High Similarity	NPC181960
0.9299	High Similarity	NPC156057
0.9299	High Similarity	NPC78225
0.9299	High Similarity	NPC162869
0.9295	High Similarity	NPC45849
0.9295	High Similarity	NPC200761
0.9295	High Similarity	NPC226025
0.9295	High Similarity	NPC470327
0.9295	High Similarity	NPC472909
0.9295	High Similarity	NPC477503
0.929	High Similarity	NPC87708
0.9286	High Similarity	NPC338131
0.9268	High Similarity	NPC289147
0.9259	High Similarity	NPC49487
0.9259	High Similarity	NPC99613
0.9255	High Similarity	NPC120593
0.9255	High Similarity	NPC39091
0.9255	High Similarity	NPC29160
0.925	High Similarity	NPC23298
0.925	High Similarity	NPC474240
0.925	High Similarity	NPC186686
0.925	High Similarity	NPC156082
0.925	High Similarity	NPC207690
0.925	High Similarity	NPC41301
0.925	High Similarity	NPC189473
0.9245	High Similarity	NPC266314
0.9245	High Similarity	NPC32694
0.9241	High Similarity	NPC210459
0.9236	High Similarity	NPC68093
0.9236	High Similarity	NPC470328
0.9236	High Similarity	NPC235165
0.9236	High Similarity	NPC278778
0.9236	High Similarity	NPC35038
0.9236	High Similarity	NPC191146
0.9236	High Similarity	NPC255106
0.9236	High Similarity	NPC291878
0.9236	High Similarity	NPC472626
0.9236	High Similarity	NPC195796
0.9236	High Similarity	NPC138243
0.9236	High Similarity	NPC209614
0.9231	High Similarity	NPC280937
0.9231	High Similarity	NPC135522
0.9231	High Similarity	NPC472915
0.9231	High Similarity	NPC89474
0.9226	High Similarity	NPC117579
0.9202	High Similarity	NPC20543
0.9202	High Similarity	NPC239440
0.9198	High Similarity	NPC225419
0.9198	High Similarity	NPC234331
0.9193	High Similarity	NPC475888
0.9193	High Similarity	NPC293319
0.9193	High Similarity	NPC112981
0.9187	High Similarity	NPC81679
0.9187	High Similarity	NPC211107
0.9182	High Similarity	NPC45146
0.9182	High Similarity	NPC200746
0.9182	High Similarity	NPC84571
0.9182	High Similarity	NPC470810
0.9182	High Similarity	NPC321399
0.9182	High Similarity	NPC235018
0.9177	High Similarity	NPC474055
0.9177	High Similarity	NPC472914
0.9177	High Similarity	NPC476981
0.9177	High Similarity	NPC284820
0.9177	High Similarity	NPC99597
0.9177	High Similarity	NPC472911
0.9177	High Similarity	NPC27337
0.9177	High Similarity	NPC245758
0.9177	High Similarity	NPC210084
0.9177	High Similarity	NPC136674
0.9177	High Similarity	NPC222814
0.9177	High Similarity	NPC472910
0.9177	High Similarity	NPC291508
0.9177	High Similarity	NPC473272
0.9177	High Similarity	NPC96167
0.9177	High Similarity	NPC472598
0.9177	High Similarity	NPC472913
0.9172	High Similarity	NPC67396
0.9172	High Similarity	NPC31018
0.9172	High Similarity	NPC255807
0.9172	High Similarity	NPC113906
0.9167	High Similarity	NPC106976
0.9167	High Similarity	NPC474843
0.9161	High Similarity	NPC202595
0.9161	High Similarity	NPC227122
0.9161	High Similarity	NPC179183
0.9157	High Similarity	NPC246877
0.9146	High Similarity	NPC158226
0.9146	High Similarity	NPC260263
0.9146	High Similarity	NPC4200
0.9141	High Similarity	NPC165979
0.9141	High Similarity	NPC163130
0.9136	High Similarity	NPC472452
0.9136	High Similarity	NPC128293
0.9136	High Similarity	NPC472449
0.9136	High Similarity	NPC20216
0.913	High Similarity	NPC146134
0.913	High Similarity	NPC18100
0.913	High Similarity	NPC473313
0.913	High Similarity	NPC329669
0.913	High Similarity	NPC472278
0.9125	High Similarity	NPC134783
0.9125	High Similarity	NPC474239
0.9125	High Similarity	NPC311740
0.9119	High Similarity	NPC152904
0.9119	High Similarity	NPC235448
0.9119	High Similarity	NPC186113
0.9119	High Similarity	NPC473990
0.9114	High Similarity	NPC24640
0.9114	High Similarity	NPC472916
0.9114	High Similarity	NPC164427
0.9108	High Similarity	NPC213896
0.9108	High Similarity	NPC74924
0.9108	High Similarity	NPC298692
0.9108	High Similarity	NPC192083
0.9108	High Similarity	NPC18727
0.9103	High Similarity	NPC202157
0.9103	High Similarity	NPC149614
0.9103	High Similarity	NPC474417
0.9103	High Similarity	NPC208043
0.9103	High Similarity	NPC226973
0.9103	High Similarity	NPC149526
0.9102	High Similarity	NPC113446
0.9097	High Similarity	NPC100985
0.9097	High Similarity	NPC97028
0.9097	High Similarity	NPC328119
0.9097	High Similarity	NPC288036
0.9097	High Similarity	NPC97029

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 NPC197168 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	398
0.1-0.2	1003
0.2-0.3	1833
0.3-0.4	2608
0.4-0.5	1755
0.5-0.6	925
0.6-0.7	430
0.7-0.8	150
0.8-0.85	34
0.85-0.9	11
0.9-0.95	3
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9108	High Similarity	NPD2393	Clinical (unspecified phase)
0.9045	High Similarity	NPD1934	Approved
0.9024	High Similarity	NPD5844	Phase 1
0.8987	High Similarity	NPD2801	Approved
0.8951	High Similarity	NPD6232	Discontinued
0.8944	High Similarity	NPD5494	Approved
0.8902	High Similarity	NPD7473	Discontinued
0.8889	High Similarity	NPD6959	Discontinued
0.8614	High Similarity	NPD6168	Clinical (unspecified phase)
0.8614	High Similarity	NPD6167	Clinical (unspecified phase)
0.8614	High Similarity	NPD6166	Phase 2
0.8528	High Similarity	NPD3882	Suspended
0.8519	High Similarity	NPD7819	Suspended
0.8481	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8447	Intermediate Similarity	NPD4380	Phase 2
0.8418	Intermediate Similarity	NPD1511	Approved
0.8415	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8412	Intermediate Similarity	NPD7074	Phase 3
0.8402	Intermediate Similarity	NPD3818	Discontinued
0.8387	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8387	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8372	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8365	Intermediate Similarity	NPD2533	Approved
0.8365	Intermediate Similarity	NPD2532	Approved
0.8365	Intermediate Similarity	NPD2534	Approved
0.8364	Intermediate Similarity	NPD7075	Discontinued
0.8354	Intermediate Similarity	NPD3817	Phase 2
0.8354	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8353	Intermediate Similarity	NPD7054	Approved
0.8333	Intermediate Similarity	NPD1549	Phase 2
0.8313	Intermediate Similarity	NPD1512	Approved
0.8304	Intermediate Similarity	NPD7472	Approved
0.8293	Intermediate Similarity	NPD1465	Phase 2
0.8293	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8214	Intermediate Similarity	NPD1247	Approved
0.8208	Intermediate Similarity	NPD6559	Discontinued
0.8192	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.8161	Intermediate Similarity	NPD7808	Phase 3
0.815	Intermediate Similarity	NPD6797	Phase 2
0.8144	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8103	Intermediate Similarity	NPD7251	Discontinued
0.8089	Intermediate Similarity	NPD2796	Approved
0.8061	Intermediate Similarity	NPD7411	Suspended
0.8035	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8025	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.8025	Intermediate Similarity	NPD1510	Phase 2
0.8025	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8013	Intermediate Similarity	NPD1607	Approved
0.8012	Intermediate Similarity	NPD6801	Discontinued
0.8	Intermediate Similarity	NPD6599	Discontinued
0.8	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7987	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7965	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7963	Intermediate Similarity	NPD7390	Discontinued
0.7943	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7939	Intermediate Similarity	NPD3226	Approved
0.7937	Intermediate Similarity	NPD2800	Approved
0.7929	Intermediate Similarity	NPD3749	Approved
0.7925	Intermediate Similarity	NPD2346	Discontinued
0.7917	Intermediate Similarity	NPD5402	Approved
0.7907	Intermediate Similarity	NPD3926	Phase 2
0.7904	Intermediate Similarity	NPD37	Approved
0.7892	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7885	Intermediate Similarity	NPD1240	Approved
0.7882	Intermediate Similarity	NPD6234	Discontinued
0.7882	Intermediate Similarity	NPD919	Approved
0.787	Intermediate Similarity	NPD4966	Approved
0.787	Intermediate Similarity	NPD4965	Approved
0.787	Intermediate Similarity	NPD7768	Phase 2
0.787	Intermediate Similarity	NPD4967	Phase 2
0.7862	Intermediate Similarity	NPD2935	Discontinued
0.7862	Intermediate Similarity	NPD6100	Approved
0.7862	Intermediate Similarity	NPD6099	Approved
0.7853	Intermediate Similarity	NPD6799	Approved
0.7849	Intermediate Similarity	NPD5710	Approved
0.7849	Intermediate Similarity	NPD5711	Approved
0.7778	Intermediate Similarity	NPD3750	Approved
0.7771	Intermediate Similarity	NPD3751	Discontinued
0.7746	Intermediate Similarity	NPD3787	Discontinued
0.7709	Intermediate Similarity	NPD8313	Approved
0.7709	Intermediate Similarity	NPD8312	Approved
0.7701	Intermediate Similarity	NPD6782	Approved
0.7701	Intermediate Similarity	NPD6779	Approved
0.7701	Intermediate Similarity	NPD6777	Approved
0.7701	Intermediate Similarity	NPD6781	Approved
0.7701	Intermediate Similarity	NPD6776	Approved
0.7701	Intermediate Similarity	NPD6778	Approved
0.7701	Intermediate Similarity	NPD6780	Approved
0.7697	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD4625	Phase 3
0.767	Intermediate Similarity	NPD7228	Approved
0.7669	Intermediate Similarity	NPD4628	Phase 3
0.7658	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7658	Intermediate Similarity	NPD943	Approved
0.7658	Intermediate Similarity	NPD1613	Approved
0.7656	Intermediate Similarity	NPD8151	Discontinued
0.764	Intermediate Similarity	NPD1551	Phase 2
0.7624	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7607	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7605	Intermediate Similarity	NPD920	Approved
0.7586	Intermediate Similarity	NPD7199	Phase 2
0.7582	Intermediate Similarity	NPD8150	Discontinued
0.7579	Intermediate Similarity	NPD7435	Discontinued
0.7579	Intermediate Similarity	NPD7698	Approved
0.7579	Intermediate Similarity	NPD7697	Approved
0.7579	Intermediate Similarity	NPD7696	Phase 3
0.7577	Intermediate Similarity	NPD7783	Phase 2
0.7577	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7564	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7561	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7539	Intermediate Similarity	NPD7871	Phase 2
0.7539	Intermediate Similarity	NPD7870	Phase 2
0.7516	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD447	Suspended
0.75	Intermediate Similarity	NPD5403	Approved
0.75	Intermediate Similarity	NPD230	Phase 1
0.75	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1243	Approved
0.7485	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD2344	Approved
0.7469	Intermediate Similarity	NPD2799	Discontinued
0.7469	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7469	Intermediate Similarity	NPD3748	Approved
0.7468	Intermediate Similarity	NPD3027	Phase 3
0.7459	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7453	Intermediate Similarity	NPD6651	Approved
0.7444	Intermediate Similarity	NPD5953	Discontinued
0.7443	Intermediate Similarity	NPD7229	Phase 3
0.7435	Intermediate Similarity	NPD6823	Phase 2
0.7433	Intermediate Similarity	NPD6534	Approved
0.7433	Intermediate Similarity	NPD6535	Approved
0.743	Intermediate Similarity	NPD7286	Phase 2
0.7423	Intermediate Similarity	NPD7701	Phase 2
0.7421	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7421	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD8434	Phase 2
0.7381	Intermediate Similarity	NPD5401	Approved
0.7365	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD1653	Approved
0.7347	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD7874	Approved
0.734	Intermediate Similarity	NPD4363	Phase 3
0.734	Intermediate Similarity	NPD4360	Phase 2
0.7321	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD5404	Approved
0.7317	Intermediate Similarity	NPD5408	Approved
0.7317	Intermediate Similarity	NPD5406	Approved
0.7317	Intermediate Similarity	NPD5405	Approved
0.7316	Intermediate Similarity	NPD7699	Phase 2
0.7316	Intermediate Similarity	NPD7700	Phase 2
0.7312	Intermediate Similarity	NPD2313	Discontinued
0.7312	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD7801	Approved
0.7308	Intermediate Similarity	NPD7240	Approved
0.7305	Intermediate Similarity	NPD2309	Approved
0.7296	Intermediate Similarity	NPD4908	Phase 1
0.7289	Intermediate Similarity	NPD6674	Discontinued
0.7289	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7284	Intermediate Similarity	NPD1933	Approved
0.7246	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7233	Intermediate Similarity	NPD2861	Phase 2
0.7225	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD1470	Approved
0.7209	Intermediate Similarity	NPD7458	Discontinued
0.7207	Intermediate Similarity	NPD5242	Approved
0.7205	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD6190	Approved
0.72	Intermediate Similarity	NPD5353	Approved
0.7197	Intermediate Similarity	NPD4749	Approved
0.7196	Intermediate Similarity	NPD6213	Phase 3
0.7196	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7196	Intermediate Similarity	NPD6212	Phase 3
0.7184	Intermediate Similarity	NPD6844	Discontinued
0.7182	Intermediate Similarity	NPD7177	Discontinued
0.7179	Intermediate Similarity	NPD1610	Phase 2
0.7179	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD1201	Approved
0.7143	Intermediate Similarity	NPD7003	Approved
0.7125	Intermediate Similarity	NPD9494	Approved
0.712	Intermediate Similarity	NPD7685	Pre-registration
0.7117	Intermediate Similarity	NPD4060	Phase 1
0.7108	Intermediate Similarity	NPD2438	Suspended
0.7097	Intermediate Similarity	NPD1651	Approved
0.7095	Intermediate Similarity	NPD8127	Discontinued
0.7088	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD7907	Approved
0.7072	Intermediate Similarity	NPD2403	Approved
0.7066	Intermediate Similarity	NPD1471	Phase 3
0.7059	Intermediate Similarity	NPD4111	Phase 1
0.7059	Intermediate Similarity	NPD4665	Approved
0.7056	Intermediate Similarity	NPD7211	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD7033	Discontinued
0.7045	Intermediate Similarity	NPD8455	Phase 2
0.7045	Intermediate Similarity	NPD5761	Phase 2
0.7045	Intermediate Similarity	NPD5760	Phase 2
0.7044	Intermediate Similarity	NPD1283	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