NPASS Compound

Structure

NPC152904 OpenBabel07101719242D 26 28 0 0 1 0 0 0 0 0999 V2000 4.3301 -2.5000 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 1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0000 1.7321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0000 1.7321 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 -0.5000 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5000 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5000 0.8660 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 -1.0000 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 3.4641 0.0000 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 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.5000 0.8660 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 -1.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 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 23 1 0 0 0 0 2 24 1 0 0 0 0 3 25 1 0 0 0 0 4 6 1 0 0 0 0 4 11 2 0 0 0 0 5 7 2 0 0 0 0 5 11 1 0 0 0 0 6 12 2 0 0 0 0 7 12 1 0 0 0 0 8 13 2 0 0 0 0 8 14 1 0 0 0 0 9 11 1 0 0 0 0 9 19 1 0 0 0 0 10 19 1 0 0 0 0 10 26 1 0 0 0 0 12 20 1 0 0 0 0 13 15 1 0 0 0 0 13 26 1 0 0 0 0 14 16 2 0 0 0 0 14 23 1 0 0 0 0 15 17 2 0 0 0 0 15 18 1 0 0 0 0 16 17 1 0 0 0 0 16 24 1 0 0 0 0 17 25 1 0 0 0 0 18 19 1 0 0 0 0 18 21 2 0 0 0 0 19 22 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	360.12
Volume:	354.587
LogP:	1.855
LogD:	2.266
LogS:	-3.702
# Rotatable Bonds:	5
TPSA:	94.45
# H-Bond Aceptor:	7
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.842
Synthetic Accessibility Score:	3.168
Fsp3:	0.316
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:	-4.722
MDCK Permeability:	1.740587867971044e-05
Pgp-inhibitor:	0.006
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.017
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.003

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.094
Plasma Protein Binding (PPB):	94.0892105102539%
Volume Distribution (VD):	0.538
Pgp-substrate:	8.19880485534668%

ADMET: Metabolism

CYP1A2-inhibitor:	0.496
CYP1A2-substrate:	0.88
CYP2C19-inhibitor:	0.708
CYP2C19-substrate:	0.839
CYP2C9-inhibitor:	0.585
CYP2C9-substrate:	0.858
CYP2D6-inhibitor:	0.287
CYP2D6-substrate:	0.816
CYP3A4-inhibitor:	0.664
CYP3A4-substrate:	0.826

ADMET: Excretion

Clearance (CL):	5.703
Half-life (T1/2):	0.559

ADMET: Toxicity

hERG Blockers:	0.233
Human Hepatotoxicity (H-HT):	0.166
Drug-inuced Liver Injury (DILI):	0.299
AMES Toxicity:	0.145
Rat Oral Acute Toxicity:	0.082
Maximum Recommended Daily Dose:	0.071
Skin Sensitization:	0.168
Carcinogencity:	0.081
Eye Corrosion:	0.003
Eye Irritation:	0.058
Respiratory Toxicity:	0.018

Download Data

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

Natural Product: NPC152904

Natural Product ID:	NPC152904
*Common Name:**	(3R)-3-Hydroxy-3-(4'-Hydroxybenzyl)-5,6,7-Trimethoxychroman-4-One
IUPAC Name:	(3R)-3-hydroxy-3-[(4-hydroxyphenyl)methyl]-5,6,7-trimethoxy-2H-chromen-4-one
Synonyms:
Standard InCHIKey:	TUFKNPQRBPYABA-LJQANCHMSA-N
Standard InCHI:	InChI=1S/C19H20O7/c1-23-14-8-13-15(17(25-3)16(14)24-2)18(21)19(22,10-26-13)9-11-4-6-12(20)7-5-11/h4-8,20,22H,9-10H2,1-3H3/t19-/m1/s1
SMILES:	COc1cc2c(c(c1OC)OC)C(=O)[C@@](Cc1ccc(cc1)O)(CO2)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2375665
PubChem CID:	71713106
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002507] Homoisoflavonoids [CHEMONTID:0002508] Homoisoflavans

*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
NPO27354	Urginea depressa	Species	Hyacinthaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23659371]
NPO27354	Urginea depressa	Species	Hyacinthaceae	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	3

Activity Type	# Activity
Cell Line	2
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT179	Cell Line	A2780	Homo sapiens	IC50	=	3400.0	nM	PMID[501745]
NPT1383	Cell Line	A2058	Homo sapiens	IC50	>	10000.0	nM	PMID[501745]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	6780.0	nM	PMID[501745]

☑ 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 NPC152904 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	413
0.1-0.2	1737
0.2-0.3	4595
0.3-0.4	10668
0.4-0.5	6932
0.5-0.6	3588
0.6-0.7	4865
0.7-0.8	5417
0.8-0.85	2427
0.85-0.9	1409
0.9-0.95	588
0.95-1	58

Similarity Score	Similarity Level	Natural Product ID
0.9867	High Similarity	NPC303255
0.9677	High Similarity	NPC224280
0.9677	High Similarity	NPC234052
0.9673	High Similarity	NPC263449
0.9671	High Similarity	NPC472910
0.9671	High Similarity	NPC474836
0.9671	High Similarity	NPC472911
0.9671	High Similarity	NPC245758
0.9671	High Similarity	NPC222814
0.9671	High Similarity	NPC162869
0.9671	High Similarity	NPC156057
0.9671	High Similarity	NPC472914
0.9671	High Similarity	NPC475267
0.9671	High Similarity	NPC474208
0.9671	High Similarity	NPC48208
0.9671	High Similarity	NPC67876
0.9671	High Similarity	NPC96167
0.9671	High Similarity	NPC472913
0.9669	High Similarity	NPC37392
0.9669	High Similarity	NPC472909
0.9613	High Similarity	NPC41301
0.961	High Similarity	NPC308992
0.9608	High Similarity	NPC55738
0.9605	High Similarity	NPC49824
0.9605	High Similarity	NPC472916
0.9605	High Similarity	NPC255106
0.9605	High Similarity	NPC474638
0.9605	High Similarity	NPC235165
0.9603	High Similarity	NPC472915
0.9603	High Similarity	NPC86485
0.96	High Similarity	NPC117579
0.9542	High Similarity	NPC471479
0.9542	High Similarity	NPC93376
0.9542	High Similarity	NPC210084
0.9542	High Similarity	NPC471515
0.9542	High Similarity	NPC110070
0.9542	High Similarity	NPC99597
0.9542	High Similarity	NPC75215
0.9542	High Similarity	NPC224137
0.9542	High Similarity	NPC78225
0.9542	High Similarity	NPC227192
0.9542	High Similarity	NPC203891
0.9542	High Similarity	NPC181960
0.9542	High Similarity	NPC469584
0.9542	High Similarity	NPC101830
0.9542	High Similarity	NPC189179
0.9539	High Similarity	NPC32557
0.9539	High Similarity	NPC44079
0.9539	High Similarity	NPC2928
0.9539	High Similarity	NPC213622
0.9539	High Similarity	NPC189960
0.9539	High Similarity	NPC201451
0.9539	High Similarity	NPC26227
0.9536	High Similarity	NPC180234
0.9536	High Similarity	NPC301123
0.9536	High Similarity	NPC120537
0.9536	High Similarity	NPC199100
0.9484	High Similarity	NPC266314
0.9484	High Similarity	NPC173137
0.9481	High Similarity	NPC25495
0.9481	High Similarity	NPC300943
0.9481	High Similarity	NPC261004
0.9481	High Similarity	NPC105242
0.9481	High Similarity	NPC253634
0.9481	High Similarity	NPC191459
0.9481	High Similarity	NPC250214
0.9481	High Similarity	NPC176300
0.9481	High Similarity	NPC143828
0.9481	High Similarity	NPC18607
0.9481	High Similarity	NPC19687
0.9481	High Similarity	NPC22472
0.9481	High Similarity	NPC4481
0.9481	High Similarity	NPC115798
0.9481	High Similarity	NPC95936
0.9481	High Similarity	NPC18772
0.9481	High Similarity	NPC152166
0.9481	High Similarity	NPC7846
0.9481	High Similarity	NPC204854
0.9481	High Similarity	NPC9609
0.9481	High Similarity	NPC288669
0.9481	High Similarity	NPC476242
0.9481	High Similarity	NPC130894
0.9477	High Similarity	NPC471500
0.9477	High Similarity	NPC474520
0.9477	High Similarity	NPC247017
0.9477	High Similarity	NPC178854
0.9477	High Similarity	NPC245546
0.9477	High Similarity	NPC326037
0.9477	High Similarity	NPC191146
0.9477	High Similarity	NPC98661
0.9477	High Similarity	NPC43243
0.9477	High Similarity	NPC201837
0.9477	High Similarity	NPC320825
0.9477	High Similarity	NPC13858
0.9477	High Similarity	NPC266960
0.9477	High Similarity	NPC68093
0.9477	High Similarity	NPC292107
0.9474	High Similarity	NPC145379
0.9474	High Similarity	NPC22519
0.9474	High Similarity	NPC69394
0.9474	High Similarity	NPC183878
0.9474	High Similarity	NPC280937
0.9474	High Similarity	NPC167091
0.9474	High Similarity	NPC231018
0.9474	High Similarity	NPC206238
0.9474	High Similarity	NPC88645
0.9474	High Similarity	NPC255350
0.9474	High Similarity	NPC47781
0.9474	High Similarity	NPC160951
0.9474	High Similarity	NPC176775
0.9474	High Similarity	NPC18727
0.9474	High Similarity	NPC274327
0.9474	High Similarity	NPC141212
0.9474	High Similarity	NPC271779
0.9474	High Similarity	NPC292214
0.947	High Similarity	NPC208043
0.947	High Similarity	NPC149614
0.947	High Similarity	NPC226973
0.9427	High Similarity	NPC62261
0.9423	High Similarity	NPC83922
0.9423	High Similarity	NPC472448
0.9419	High Similarity	NPC282009
0.9419	High Similarity	NPC287328
0.9419	High Similarity	NPC470183
0.9419	High Similarity	NPC246478
0.9419	High Similarity	NPC476980
0.9419	High Similarity	NPC204290
0.9416	High Similarity	NPC7973
0.9416	High Similarity	NPC262286
0.9416	High Similarity	NPC29841
0.9416	High Similarity	NPC129684
0.9416	High Similarity	NPC176665
0.9416	High Similarity	NPC52530
0.9416	High Similarity	NPC287979
0.9416	High Similarity	NPC241904
0.9416	High Similarity	NPC235215
0.9416	High Similarity	NPC27337
0.9416	High Similarity	NPC299520
0.9416	High Similarity	NPC476981
0.9416	High Similarity	NPC223787
0.9416	High Similarity	NPC78302
0.9416	High Similarity	NPC300727
0.9416	High Similarity	NPC470402
0.9416	High Similarity	NPC163524
0.9416	High Similarity	NPC472438
0.9416	High Similarity	NPC36852
0.9416	High Similarity	NPC305663
0.9412	High Similarity	NPC128863
0.9412	High Similarity	NPC163780
0.9412	High Similarity	NPC227325
0.9412	High Similarity	NPC31018
0.9412	High Similarity	NPC167815
0.9412	High Similarity	NPC50715
0.9412	High Similarity	NPC201136
0.9412	High Similarity	NPC196439
0.9412	High Similarity	NPC256612
0.9412	High Similarity	NPC255807
0.9412	High Similarity	NPC146165
0.9412	High Similarity	NPC4455
0.9412	High Similarity	NPC92659
0.9412	High Similarity	NPC20830
0.9412	High Similarity	NPC183597
0.9412	High Similarity	NPC2476
0.9412	High Similarity	NPC138360
0.9412	High Similarity	NPC280339
0.9408	High Similarity	NPC39007
0.9408	High Similarity	NPC71334
0.9408	High Similarity	NPC188203
0.9408	High Similarity	NPC131624
0.9408	High Similarity	NPC302950
0.9408	High Similarity	NPC256283
0.9408	High Similarity	NPC219582
0.9408	High Similarity	NPC100887
0.9408	High Similarity	NPC241498
0.9408	High Similarity	NPC83508
0.9408	High Similarity	NPC134677
0.9408	High Similarity	NPC257648
0.9408	High Similarity	NPC236637
0.9408	High Similarity	NPC120163
0.9408	High Similarity	NPC187498
0.9408	High Similarity	NPC198826
0.9408	High Similarity	NPC275722
0.9408	High Similarity	NPC301323
0.9408	High Similarity	NPC275836
0.9408	High Similarity	NPC212678
0.9408	High Similarity	NPC101996
0.9408	High Similarity	NPC162313
0.9408	High Similarity	NPC477231
0.9408	High Similarity	NPC25270
0.9408	High Similarity	NPC293183
0.9408	High Similarity	NPC472912
0.9408	High Similarity	NPC156222
0.9408	High Similarity	NPC239128
0.9408	High Similarity	NPC222830
0.9408	High Similarity	NPC57030
0.9408	High Similarity	NPC161277
0.9404	High Similarity	NPC61620
0.9404	High Similarity	NPC306821
0.9404	High Similarity	NPC338131
0.9404	High Similarity	NPC62042

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 NPC152904 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	376
0.1-0.2	978
0.2-0.3	1818
0.3-0.4	2641
0.4-0.5	1713
0.5-0.6	984
0.6-0.7	440
0.7-0.8	151
0.8-0.85	28
0.85-0.9	11
0.9-0.95	10
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9474	High Similarity	NPD2801	Approved
0.9408	High Similarity	NPD1934	Approved
0.9226	High Similarity	NPD3882	Suspended
0.9221	High Similarity	NPD2393	Clinical (unspecified phase)
0.9182	High Similarity	NPD6168	Clinical (unspecified phase)
0.9182	High Similarity	NPD6166	Phase 2
0.9182	High Similarity	NPD6167	Clinical (unspecified phase)
0.9038	High Similarity	NPD3817	Phase 2
0.9013	High Similarity	NPD1512	Approved
0.8909	High Similarity	NPD4338	Clinical (unspecified phase)
0.8882	High Similarity	NPD1511	Approved
0.8824	High Similarity	NPD4378	Clinical (unspecified phase)
0.8812	High Similarity	NPD5494	Approved
0.8727	High Similarity	NPD7074	Phase 3
0.872	High Similarity	NPD3818	Discontinued
0.8688	High Similarity	NPD7075	Discontinued
0.8683	High Similarity	NPD7808	Phase 3
0.8675	High Similarity	NPD6797	Phase 2
0.8667	High Similarity	NPD7054	Approved
0.8625	High Similarity	NPD4868	Clinical (unspecified phase)
0.8623	High Similarity	NPD7251	Discontinued
0.8616	High Similarity	NPD7096	Clinical (unspecified phase)
0.8614	High Similarity	NPD7472	Approved
0.8609	High Similarity	NPD1550	Clinical (unspecified phase)
0.8609	High Similarity	NPD1552	Clinical (unspecified phase)
0.8553	High Similarity	NPD1549	Phase 2
0.8544	High Similarity	NPD4380	Phase 2
0.8516	High Similarity	NPD6799	Approved
0.8457	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8447	Intermediate Similarity	NPD5402	Approved
0.8415	Intermediate Similarity	NPD1247	Approved
0.8364	Intermediate Similarity	NPD6232	Discontinued
0.8355	Intermediate Similarity	NPD1510	Phase 2
0.8343	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD5844	Phase 1
0.8333	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8323	Intermediate Similarity	NPD6801	Discontinued
0.8323	Intermediate Similarity	NPD7473	Discontinued
0.8313	Intermediate Similarity	NPD6599	Discontinued
0.8301	Intermediate Similarity	NPD2796	Approved
0.8272	Intermediate Similarity	NPD7819	Suspended
0.8228	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8221	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8212	Intermediate Similarity	NPD1240	Approved
0.8204	Intermediate Similarity	NPD3926	Phase 2
0.816	Intermediate Similarity	NPD1465	Phase 2
0.8148	Intermediate Similarity	NPD7411	Suspended
0.8105	Intermediate Similarity	NPD1607	Approved
0.8092	Intermediate Similarity	NPD943	Approved
0.8084	Intermediate Similarity	NPD6959	Discontinued
0.8072	Intermediate Similarity	NPD919	Approved
0.8012	Intermediate Similarity	NPD5403	Approved
0.7977	Intermediate Similarity	NPD6559	Discontinued
0.7974	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7974	Intermediate Similarity	NPD1613	Approved
0.7953	Intermediate Similarity	NPD3751	Discontinued
0.7949	Intermediate Similarity	NPD2935	Discontinued
0.7947	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7929	Intermediate Similarity	NPD3787	Discontinued
0.7904	Intermediate Similarity	NPD3749	Approved
0.7888	Intermediate Similarity	NPD5401	Approved
0.7881	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7877	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7848	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7836	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7812	Intermediate Similarity	NPD6190	Approved
0.7806	Intermediate Similarity	NPD230	Phase 1
0.7806	Intermediate Similarity	NPD447	Suspended
0.7799	Intermediate Similarity	NPD2800	Approved
0.7797	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7791	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD2533	Approved
0.7778	Intermediate Similarity	NPD3027	Phase 3
0.7778	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD2534	Approved
0.7778	Intermediate Similarity	NPD2532	Approved
0.7771	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.775	Intermediate Similarity	NPD3750	Approved
0.7738	Intermediate Similarity	NPD7768	Phase 2
0.7727	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7722	Intermediate Similarity	NPD6100	Approved
0.7722	Intermediate Similarity	NPD6099	Approved
0.7722	Intermediate Similarity	NPD1551	Phase 2
0.7688	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7676	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7667	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7661	Intermediate Similarity	NPD7199	Phase 2
0.764	Intermediate Similarity	NPD4628	Phase 3
0.7636	Intermediate Similarity	NPD1653	Approved
0.7607	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7581	Intermediate Similarity	NPD6779	Approved
0.7581	Intermediate Similarity	NPD6778	Approved
0.7581	Intermediate Similarity	NPD6781	Approved
0.7581	Intermediate Similarity	NPD6776	Approved
0.7581	Intermediate Similarity	NPD6782	Approved
0.7581	Intermediate Similarity	NPD6780	Approved
0.7581	Intermediate Similarity	NPD6777	Approved
0.758	Intermediate Similarity	NPD1933	Approved
0.7576	Intermediate Similarity	NPD920	Approved
0.7562	Intermediate Similarity	NPD2344	Approved
0.7556	Intermediate Similarity	NPD8434	Phase 2
0.7544	Intermediate Similarity	NPD6234	Discontinued
0.7532	Intermediate Similarity	NPD9494	Approved
0.7531	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD5953	Discontinued
0.75	Intermediate Similarity	NPD7286	Phase 2
0.7485	Intermediate Similarity	NPD3226	Approved
0.7484	Intermediate Similarity	NPD4908	Phase 1
0.746	Intermediate Similarity	NPD7435	Discontinued
0.7459	Intermediate Similarity	NPD8150	Discontinued
0.7456	Intermediate Similarity	NPD37	Approved
0.7455	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7453	Intermediate Similarity	NPD2346	Discontinued
0.7452	Intermediate Similarity	NPD6233	Phase 2
0.7438	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7438	Intermediate Similarity	NPD2799	Discontinued
0.7438	Intermediate Similarity	NPD3748	Approved
0.743	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD2403	Approved
0.7427	Intermediate Similarity	NPD4965	Approved
0.7427	Intermediate Similarity	NPD4967	Phase 2
0.7427	Intermediate Similarity	NPD4966	Approved
0.7423	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7421	Intermediate Similarity	NPD6651	Approved
0.7389	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD6798	Discontinued
0.7389	Intermediate Similarity	NPD2313	Discontinued
0.7386	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7378	Intermediate Similarity	NPD2309	Approved
0.7374	Intermediate Similarity	NPD7685	Pre-registration
0.7371	Intermediate Similarity	NPD5242	Approved
0.7368	Intermediate Similarity	NPD7698	Approved
0.7368	Intermediate Similarity	NPD7696	Phase 3
0.7368	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD7697	Approved
0.7368	Intermediate Similarity	NPD1610	Phase 2
0.7362	Intermediate Similarity	NPD1243	Approved
0.7353	Intermediate Similarity	NPD6844	Discontinued
0.7345	Intermediate Similarity	NPD7228	Approved
0.7333	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.733	Intermediate Similarity	NPD7871	Phase 2
0.733	Intermediate Similarity	NPD7870	Phase 2
0.7329	Intermediate Similarity	NPD7033	Discontinued
0.7326	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7314	Intermediate Similarity	NPD5711	Approved
0.7314	Intermediate Similarity	NPD5710	Approved
0.7312	Intermediate Similarity	NPD6535	Approved
0.7312	Intermediate Similarity	NPD6534	Approved
0.7308	Intermediate Similarity	NPD2861	Phase 2
0.7306	Intermediate Similarity	NPD7701	Phase 2
0.7293	Intermediate Similarity	NPD8312	Approved
0.7293	Intermediate Similarity	NPD8313	Approved
0.729	Intermediate Similarity	NPD1203	Approved
0.7289	Intermediate Similarity	NPD7390	Discontinued
0.7267	Intermediate Similarity	NPD5353	Approved
0.7261	Intermediate Similarity	NPD6832	Phase 2
0.725	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD6355	Discontinued
0.7246	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7238	Intermediate Similarity	NPD7549	Discontinued
0.7231	Intermediate Similarity	NPD7874	Approved
0.7231	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD4363	Phase 3
0.7219	Intermediate Similarity	NPD4360	Phase 2
0.7219	Intermediate Similarity	NPD1548	Phase 1
0.7215	Intermediate Similarity	NPD4625	Phase 3
0.7196	Intermediate Similarity	NPD7700	Phase 2
0.7196	Intermediate Similarity	NPD7699	Phase 2
0.7195	Intermediate Similarity	NPD2424	Discontinued
0.7194	Intermediate Similarity	NPD7783	Phase 2
0.7194	Intermediate Similarity	NPD7801	Approved
0.7194	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD6386	Approved
0.7193	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD6385	Approved
0.7188	Intermediate Similarity	NPD4060	Phase 1
0.717	Intermediate Similarity	NPD3268	Approved
0.7169	Intermediate Similarity	NPD2354	Approved
0.7165	Intermediate Similarity	NPD7584	Approved
0.7161	Intermediate Similarity	NPD4749	Approved
0.7143	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD6823	Phase 2
0.7134	Intermediate Similarity	NPD2798	Approved
0.7119	Intermediate Similarity	NPD7229	Phase 3
0.7117	Intermediate Similarity	NPD4308	Phase 3
0.7107	Intermediate Similarity	NPD7095	Approved
0.7097	Intermediate Similarity	NPD1608	Approved
0.7097	Intermediate Similarity	NPD9717	Approved
0.7097	Intermediate Similarity	NPD9269	Phase 2
0.7092	Intermediate Similarity	NPD8151	Discontinued
0.7089	Intermediate Similarity	NPD3018	Phase 2
0.7083	Intermediate Similarity	NPD2493	Approved
0.7083	Intermediate Similarity	NPD2494	Approved
0.7083	Intermediate Similarity	NPD4357	Discontinued
0.707	Intermediate Similarity	NPD2797	Approved
0.7066	Intermediate Similarity	NPD3887	Approved
0.7063	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7056	Intermediate Similarity	NPD2163	Approved
0.7048	Intermediate Similarity	NPD2654	Approved
0.7048	Intermediate Similarity	NPD1652	Phase 2

Bioactivity similarity: Similar Natural Products in NPASS

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

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

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data