NPASS Compound

Structure

NPC472453 OpenBabel07101718202D 24 26 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 -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 -2.0000 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 -0.8660 -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 0.8660 -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 -0.0000 -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 -0.8660 -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 -3.4641 -0.0000 0.0000 C 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 -0.0000 -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 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 -3.4641 1.0000 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 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 23 1 0 0 0 0 2 3 2 0 0 0 0 2 7 1 0 0 0 0 3 8 1 0 0 0 0 4 6 2 0 0 0 0 4 9 1 0 0 0 0 5 6 1 0 0 0 0 5 10 2 0 0 0 0 6 17 1 0 0 0 0 7 11 1 0 0 0 0 7 14 2 0 0 0 0 8 12 2 0 0 0 0 8 16 1 0 0 0 0 9 11 1 0 0 0 0 9 13 2 0 0 0 0 10 13 1 0 0 0 0 10 15 1 0 0 0 0 11 18 2 0 0 0 0 12 14 1 0 0 0 0 12 19 1 0 0 0 0 13 24 1 0 0 0 0 14 24 1 0 0 0 0 15 20 2 0 0 0 0 15 21 1 0 0 0 0 16 22 2 0 0 0 0 16 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	330.04
Volume:	306.217
LogP:	2.982
LogD:	1.868
LogS:	-3.805
# Rotatable Bonds:	3
TPSA:	134.27
# H-Bond Aceptor:	8
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.478
Synthetic Accessibility Score:	2.579
Fsp3:	0.062
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-5.475
MDCK Permeability:	1.4099331565375905e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.343
20% Bioavailability (F20%):	0.145
30% Bioavailability (F30%):	0.977

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.1
Plasma Protein Binding (PPB):	82.55461883544922%
Volume Distribution (VD):	0.838
Pgp-substrate:	14.6060791015625%

ADMET: Metabolism

CYP1A2-inhibitor:	0.163
CYP1A2-substrate:	0.148
CYP2C19-inhibitor:	0.032
CYP2C19-substrate:	0.046
CYP2C9-inhibitor:	0.319
CYP2C9-substrate:	0.098
CYP2D6-inhibitor:	0.184
CYP2D6-substrate:	0.11
CYP3A4-inhibitor:	0.092
CYP3A4-substrate:	0.017

ADMET: Excretion

Clearance (CL):	1.855
Half-life (T1/2):	0.921

ADMET: Toxicity

hERG Blockers:	0.002
Human Hepatotoxicity (H-HT):	0.805
Drug-inuced Liver Injury (DILI):	0.993
AMES Toxicity:	0.032
Rat Oral Acute Toxicity:	0.034
Maximum Recommended Daily Dose:	0.055
Skin Sensitization:	0.431
Carcinogencity:	0.036
Eye Corrosion:	0.003
Eye Irritation:	0.068
Respiratory Toxicity:	0.344

Download Data

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

Natural Product: NPC472453

Natural Product ID:	NPC472453
*Common Name:**	PTYYVBPXCVLOAP-UHFFFAOYSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	PTYYVBPXCVLOAP-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C16H10O8/c1-23-16(22)8-3-2-7-11(18)9-4-6(17)5-10(15(20)21)13(9)24-14(7)12(8)19/h2-5,17,19H,1H3,(H,20,21)
SMILES:	COC(=O)c1ccc2c(c1O)oc1c(c2=O)cc(cc1C(=O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3422275
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000123] Benzopyrans [CHEMONTID:0003410] 1-benzopyrans [CHEMONTID:0002817] Dibenzopyrans [CHEMONTID:0000200] Xanthenes [CHEMONTID:0000204] Xanthones

*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
NPO32511	Penicillium chrysogenum	Under-species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[25611519]

☑ 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	5

Activity Type	# Activity
Cell Line	3
NON-MOLECULAR	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	IC50	=	16900.0	nM	PMID[466428]
NPT71	Cell Line	HEK293	Homo sapiens	IC50	=	28500.0	nM	PMID[466428]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	10000.0	nM	PMID[466428]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	19000.0	nM	PMID[466428]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	30600.0	nM	PMID[466428]

☑ 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 NPC472453 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	412
0.1-0.2	1954
0.2-0.3	5052
0.3-0.4	11229
0.4-0.5	6350
0.5-0.6	4473
0.6-0.7	6277
0.7-0.8	5471
0.8-0.85	1139
0.85-0.9	337
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8903	High Similarity	NPC75069
0.8889	High Similarity	NPC55327
0.8875	High Similarity	NPC477689
0.8868	High Similarity	NPC258331
0.8834	High Similarity	NPC124470
0.8834	High Similarity	NPC109827
0.8831	High Similarity	NPC294502
0.8831	High Similarity	NPC200221
0.8805	High Similarity	NPC130955
0.8797	High Similarity	NPC78225
0.8797	High Similarity	NPC262286
0.8797	High Similarity	NPC36852
0.878	High Similarity	NPC158226
0.8773	High Similarity	NPC165979
0.8773	High Similarity	NPC163130
0.875	High Similarity	NPC266314
0.8734	High Similarity	NPC68093
0.8734	High Similarity	NPC191146
0.8734	High Similarity	NPC138243
0.8726	High Similarity	NPC88645
0.8726	High Similarity	NPC271779
0.8726	High Similarity	NPC206238
0.8726	High Similarity	NPC292214
0.8726	High Similarity	NPC167091
0.8712	High Similarity	NPC234331
0.871	High Similarity	NPC106334
0.871	High Similarity	NPC285527
0.8701	High Similarity	NPC46941
0.8696	High Similarity	NPC472448
0.8696	High Similarity	NPC83922
0.8688	High Similarity	NPC476980
0.8679	High Similarity	NPC99597
0.8679	High Similarity	NPC210084
0.8675	High Similarity	NPC245975
0.8671	High Similarity	NPC2928
0.8671	High Similarity	NPC57674
0.8671	High Similarity	NPC168247
0.8671	High Similarity	NPC152951
0.8671	High Similarity	NPC230149
0.8671	High Similarity	NPC113906
0.8671	High Similarity	NPC117992
0.8662	High Similarity	NPC101996
0.8662	High Similarity	NPC120537
0.8662	High Similarity	NPC39007
0.8662	High Similarity	NPC199100
0.8662	High Similarity	NPC161277
0.8662	High Similarity	NPC180234
0.8659	High Similarity	NPC99613
0.8659	High Similarity	NPC49487
0.8654	High Similarity	NPC213382
0.8654	High Similarity	NPC164527
0.865	High Similarity	NPC29160
0.8642	High Similarity	NPC474350
0.8642	High Similarity	NPC236132
0.8636	High Similarity	NPC209278
0.8636	High Similarity	NPC211565
0.8634	High Similarity	NPC167678
0.8634	High Similarity	NPC29876
0.8631	High Similarity	NPC113446
0.8625	High Similarity	NPC95936
0.8625	High Similarity	NPC250214
0.8616	High Similarity	NPC255106
0.8616	High Similarity	NPC235165
0.8616	High Similarity	NPC472916
0.8608	High Similarity	NPC227337
0.8608	High Similarity	NPC33051
0.8608	High Similarity	NPC471981
0.8608	High Similarity	NPC273462
0.8608	High Similarity	NPC70433
0.8608	High Similarity	NPC49402
0.8599	High Similarity	NPC251110
0.8599	High Similarity	NPC171010
0.8599	High Similarity	NPC118427
0.8599	High Similarity	NPC117579
0.8599	High Similarity	NPC149614
0.858	High Similarity	NPC294965
0.8571	High Similarity	NPC228785
0.8571	High Similarity	NPC207467
0.8571	High Similarity	NPC56085
0.8571	High Similarity	NPC14353
0.8571	High Similarity	NPC204290
0.8563	High Similarity	NPC139350
0.8562	High Similarity	NPC475267
0.8562	High Similarity	NPC222814
0.8562	High Similarity	NPC96167
0.8562	High Similarity	NPC472910
0.8562	High Similarity	NPC474836
0.8562	High Similarity	NPC472913
0.8562	High Similarity	NPC162869
0.8562	High Similarity	NPC156057
0.8562	High Similarity	NPC291508
0.8562	High Similarity	NPC472914
0.8562	High Similarity	NPC476981
0.8562	High Similarity	NPC223787
0.8562	High Similarity	NPC474208
0.8562	High Similarity	NPC48208
0.8562	High Similarity	NPC245758
0.8562	High Similarity	NPC222689
0.8562	High Similarity	NPC35598
0.8562	High Similarity	NPC472911
0.8554	High Similarity	NPC247964
0.8554	High Similarity	NPC271848
0.8554	High Similarity	NPC81332
0.8554	High Similarity	NPC262580
0.8554	High Similarity	NPC212038
0.8554	High Similarity	NPC289396
0.8553	High Similarity	NPC256612
0.8553	High Similarity	NPC2476
0.8553	High Similarity	NPC280339
0.8553	High Similarity	NPC39184
0.8553	High Similarity	NPC227325
0.8553	High Similarity	NPC167815
0.8553	High Similarity	NPC138360
0.8553	High Similarity	NPC4455
0.8553	High Similarity	NPC146165
0.8553	High Similarity	NPC50715
0.8553	High Similarity	NPC20830
0.8553	High Similarity	NPC183597
0.8553	High Similarity	NPC128863
0.8553	High Similarity	NPC208197
0.8553	High Similarity	NPC201136
0.8553	High Similarity	NPC256925
0.8553	High Similarity	NPC196439
0.8553	High Similarity	NPC92659
0.8553	High Similarity	NPC163780
0.8544	High Similarity	NPC164912
0.8544	High Similarity	NPC293183
0.8544	High Similarity	NPC222830
0.8544	High Similarity	NPC275722
0.8544	High Similarity	NPC57030
0.8544	High Similarity	NPC241498
0.8544	High Similarity	NPC275836
0.8544	High Similarity	NPC239128
0.8544	High Similarity	NPC256283
0.8544	High Similarity	NPC162313
0.8544	High Similarity	NPC198826
0.8544	High Similarity	NPC212678
0.8544	High Similarity	NPC83508
0.8544	High Similarity	NPC71334
0.8544	High Similarity	NPC131624
0.8544	High Similarity	NPC187498
0.8544	High Similarity	NPC25270
0.8544	High Similarity	NPC199773
0.8544	High Similarity	NPC156222
0.8544	High Similarity	NPC289968
0.8544	High Similarity	NPC142540
0.8544	High Similarity	NPC120163
0.8544	High Similarity	NPC100887
0.8544	High Similarity	NPC301323
0.8544	High Similarity	NPC188203
0.8537	High Similarity	NPC13481
0.8537	High Similarity	NPC37870
0.8537	High Similarity	NPC207575
0.8535	High Similarity	NPC61620
0.8535	High Similarity	NPC225129
0.8535	High Similarity	NPC62042
0.8535	High Similarity	NPC179183
0.8535	High Similarity	NPC248102
0.8535	High Similarity	NPC29231
0.8528	High Similarity	NPC270837
0.8528	High Similarity	NPC220313
0.8528	High Similarity	NPC41301
0.8528	High Similarity	NPC234004
0.8521	High Similarity	NPC473785
0.8519	High Similarity	NPC61010
0.8519	High Similarity	NPC259456
0.8519	High Similarity	NPC40491
0.8519	High Similarity	NPC311740
0.8519	High Similarity	NPC472275
0.8519	High Similarity	NPC308992
0.8519	High Similarity	NPC278052
0.8516	High Similarity	NPC60389
0.8514	High Similarity	NPC287533
0.8509	High Similarity	NPC172770
0.8509	High Similarity	NPC204879
0.8509	High Similarity	NPC100123
0.8509	High Similarity	NPC83763
0.8509	High Similarity	NPC168616
0.8509	High Similarity	NPC185258
0.8506	High Similarity	NPC59551
0.8503	High Similarity	NPC181523
0.85	High Similarity	NPC5322
0.85	High Similarity	NPC98661
0.85	High Similarity	NPC278778
0.85	High Similarity	NPC472455
0.85	High Similarity	NPC133970
0.85	High Similarity	NPC247017
0.85	High Similarity	NPC6633
0.85	High Similarity	NPC35038
0.85	High Similarity	NPC291878
0.85	High Similarity	NPC195796
0.8494	Intermediate Similarity	NPC10576
0.8491	Intermediate Similarity	NPC176775
0.8491	Intermediate Similarity	NPC472915
0.8491	Intermediate Similarity	NPC255350
0.8491	Intermediate Similarity	NPC274327
0.8491	Intermediate Similarity	NPC183878
0.8491	Intermediate Similarity	NPC145379
0.8491	Intermediate Similarity	NPC276409
0.8491	Intermediate Similarity	NPC475895

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 NPC472453 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	397
0.1-0.2	1012
0.2-0.3	1804
0.3-0.4	2650
0.4-0.5	1813
0.5-0.6	1004
0.6-0.7	326
0.7-0.8	121
0.8-0.85	22
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8491	Intermediate Similarity	NPD2801	Approved
0.8477	Intermediate Similarity	NPD2346	Discontinued
0.8471	Intermediate Similarity	NPD3226	Approved
0.8428	Intermediate Similarity	NPD1934	Approved
0.8411	Intermediate Similarity	NPD2935	Discontinued
0.8389	Intermediate Similarity	NPD447	Suspended
0.8375	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8242	Intermediate Similarity	NPD6232	Discontinued
0.8204	Intermediate Similarity	NPD7473	Discontinued
0.8188	Intermediate Similarity	NPD2313	Discontinued
0.816	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8146	Intermediate Similarity	NPD1933	Approved
0.8129	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.811	Intermediate Similarity	NPD7075	Discontinued
0.8107	Intermediate Similarity	NPD5844	Phase 1
0.8098	Intermediate Similarity	NPD3817	Phase 2
0.8057	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.8049	Intermediate Similarity	NPD3882	Suspended
0.8047	Intermediate Similarity	NPD3818	Discontinued
0.8038	Intermediate Similarity	NPD1511	Approved
0.8036	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8036	Intermediate Similarity	NPD6166	Phase 2
0.8036	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8025	Intermediate Similarity	NPD7411	Suspended
0.8012	Intermediate Similarity	NPD5494	Approved
0.7988	Intermediate Similarity	NPD5402	Approved
0.7953	Intermediate Similarity	NPD7074	Phase 3
0.7937	Intermediate Similarity	NPD1512	Approved
0.7927	Intermediate Similarity	NPD1465	Phase 2
0.7927	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7927	Intermediate Similarity	NPD7819	Suspended
0.7895	Intermediate Similarity	NPD7054	Approved
0.7871	Intermediate Similarity	NPD2799	Discontinued
0.7861	Intermediate Similarity	NPD6559	Discontinued
0.7853	Intermediate Similarity	NPD4380	Phase 2
0.7852	Intermediate Similarity	NPD1203	Approved
0.7849	Intermediate Similarity	NPD7472	Approved
0.7785	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD8312	Approved
0.7771	Intermediate Similarity	NPD8313	Approved
0.7765	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7764	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7758	Intermediate Similarity	NPD6801	Discontinued
0.7756	Intermediate Similarity	NPD4308	Phase 3
0.7751	Intermediate Similarity	NPD1247	Approved
0.7719	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7712	Intermediate Similarity	NPD411	Approved
0.7712	Intermediate Similarity	NPD3268	Approved
0.7707	Intermediate Similarity	NPD1551	Phase 2
0.7701	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7701	Intermediate Similarity	NPD6797	Phase 2
0.7697	Intermediate Similarity	NPD6832	Phase 2
0.7683	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7679	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7677	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7665	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7657	Intermediate Similarity	NPD7251	Discontinued
0.7651	Intermediate Similarity	NPD9717	Approved
0.7636	Intermediate Similarity	NPD6599	Discontinued
0.7614	Intermediate Similarity	NPD7808	Phase 3
0.761	Intermediate Similarity	NPD1549	Phase 2
0.7593	Intermediate Similarity	NPD6799	Approved
0.7561	Intermediate Similarity	NPD5403	Approved
0.7547	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7547	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7546	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7546	Intermediate Similarity	NPD5401	Approved
0.7544	Intermediate Similarity	NPD6959	Discontinued
0.7542	Intermediate Similarity	NPD8150	Discontinued
0.7529	Intermediate Similarity	NPD919	Approved
0.7516	Intermediate Similarity	NPD1607	Approved
0.7516	Intermediate Similarity	NPD4628	Phase 3
0.75	Intermediate Similarity	NPD3267	Approved
0.75	Intermediate Similarity	NPD943	Approved
0.75	Intermediate Similarity	NPD4307	Phase 2
0.75	Intermediate Similarity	NPD3266	Approved
0.7486	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7486	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7467	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7439	Intermediate Similarity	NPD2534	Approved
0.7439	Intermediate Similarity	NPD2533	Approved
0.7439	Intermediate Similarity	NPD2532	Approved
0.7438	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7438	Intermediate Similarity	NPD2344	Approved
0.7421	Intermediate Similarity	NPD1510	Phase 2
0.7412	Intermediate Similarity	NPD7768	Phase 2
0.7407	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD3750	Approved
0.7403	Intermediate Similarity	NPD9494	Approved
0.7389	Intermediate Similarity	NPD1240	Approved
0.7386	Intermediate Similarity	NPD2797	Approved
0.7381	Intermediate Similarity	NPD5890	Approved
0.7381	Intermediate Similarity	NPD5889	Approved
0.738	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD3749	Approved
0.7368	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD7458	Discontinued
0.7354	Intermediate Similarity	NPD7435	Discontinued
0.7349	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7348	Intermediate Similarity	NPD8434	Phase 2
0.7342	Intermediate Similarity	NPD230	Phase 1
0.7338	Intermediate Similarity	NPD2798	Approved
0.7337	Intermediate Similarity	NPD6844	Discontinued
0.7326	Intermediate Similarity	NPD6234	Discontinued
0.7321	Intermediate Similarity	NPD6585	Discontinued
0.7305	Intermediate Similarity	NPD1653	Approved
0.7301	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD9493	Approved
0.7287	Intermediate Similarity	NPD6779	Approved
0.7287	Intermediate Similarity	NPD6780	Approved
0.7287	Intermediate Similarity	NPD6778	Approved
0.7287	Intermediate Similarity	NPD6781	Approved
0.7287	Intermediate Similarity	NPD6777	Approved
0.7287	Intermediate Similarity	NPD6782	Approved
0.7287	Intermediate Similarity	NPD6776	Approved
0.7284	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD2796	Approved
0.7257	Intermediate Similarity	NPD3926	Phase 2
0.7256	Intermediate Similarity	NPD2309	Approved
0.7256	Intermediate Similarity	NPD6190	Approved
0.7246	Intermediate Similarity	NPD920	Approved
0.7244	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7229	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7229	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD1019	Discontinued
0.7222	Intermediate Similarity	NPD1471	Phase 3
0.7215	Intermediate Similarity	NPD6233	Phase 2
0.7208	Intermediate Similarity	NPD3225	Approved
0.7207	Intermediate Similarity	NPD5953	Discontinued
0.7205	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7195	Intermediate Similarity	NPD7003	Approved
0.7179	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD1613	Approved
0.717	Intermediate Similarity	NPD4060	Phase 1
0.7167	Intermediate Similarity	NPD7685	Pre-registration
0.7161	Intermediate Similarity	NPD1470	Approved
0.716	Intermediate Similarity	NPD5405	Approved
0.716	Intermediate Similarity	NPD5406	Approved
0.716	Intermediate Similarity	NPD5408	Approved
0.716	Intermediate Similarity	NPD5404	Approved
0.7152	Intermediate Similarity	NPD6798	Discontinued
0.7135	Intermediate Similarity	NPD3751	Discontinued
0.7135	Intermediate Similarity	NPD7228	Approved
0.7135	Intermediate Similarity	NPD37	Approved
0.7134	Intermediate Similarity	NPD1243	Approved
0.7134	Intermediate Similarity	NPD2800	Approved
0.7128	Intermediate Similarity	NPD7874	Approved
0.7128	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD1611	Approved
0.712	Intermediate Similarity	NPD6823	Phase 2
0.711	Intermediate Similarity	NPD4966	Approved
0.711	Intermediate Similarity	NPD4965	Approved
0.711	Intermediate Similarity	NPD4967	Phase 2
0.7099	Intermediate Similarity	NPD3748	Approved
0.7097	Intermediate Similarity	NPD1283	Approved
0.7095	Intermediate Similarity	NPD7286	Phase 2
0.7092	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7092	Intermediate Similarity	NPD7783	Phase 2
0.7091	Intermediate Similarity	NPD8166	Discontinued
0.7083	Intermediate Similarity	NPD7697	Approved
0.7083	Intermediate Similarity	NPD7698	Approved
0.7083	Intermediate Similarity	NPD7696	Phase 3
0.7083	Intermediate Similarity	NPD5049	Phase 3
0.7078	Intermediate Similarity	NPD1481	Phase 2
0.7078	Intermediate Similarity	NPD1608	Approved
0.7059	Intermediate Similarity	NPD6213	Phase 3
0.7059	Intermediate Similarity	NPD3496	Discontinued
0.7059	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD6212	Phase 3
0.7055	Intermediate Similarity	NPD6100	Approved
0.7055	Intermediate Similarity	NPD6099	Approved
0.7053	Intermediate Similarity	NPD8285	Discontinued
0.7051	Intermediate Similarity	NPD1164	Approved
0.7048	Intermediate Similarity	NPD2354	Approved
0.7047	Intermediate Similarity	NPD7871	Phase 2
0.7047	Intermediate Similarity	NPD7870	Phase 2
0.7045	Intermediate Similarity	NPD8127	Discontinued
0.7045	Intermediate Similarity	NPD7199	Phase 2
0.7026	Intermediate Similarity	NPD7701	Phase 2
0.7021	Intermediate Similarity	NPD6534	Approved
0.7021	Intermediate Similarity	NPD6535	Approved
0.7019	Intermediate Similarity	NPD6355	Discontinued
0.7013	Intermediate Similarity	NPD1201	Approved
0.7013	Intermediate Similarity	NPD1535	Discovery
0.7006	Intermediate Similarity	NPD5711	Approved
0.7006	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD5710	Approved
0.6994	Remote Similarity	NPD7033	Discontinued
0.6994	Remote Similarity	NPD651	Clinical (unspecified phase)
0.699	Remote Similarity	NPD8151	Discontinued
0.6988	Remote Similarity	NPD4110	Phase 3
0.6988	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6982	Remote Similarity	NPD6273	Approved
0.697	Remote Similarity	NPD2424	Discontinued
0.6966	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD7390	Discontinued
0.6951	Remote Similarity	NPD2438	Suspended

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