NPASS Compound

Structure

CID263449 OpenBabel06191716062D 22 24 0 0 1 0 0 0 0 0999 V2000 -3.4641 3.0000 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 2.5981 -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 1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 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 -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 -0.8660 1.5000 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 -1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 2 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 -3.4641 -0.0000 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 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 0.0000 O 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 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 21 1 0 0 0 0 2 3 2 0 0 0 0 2 4 1 0 0 0 0 3 5 1 0 0 0 0 4 6 2 0 0 0 0 5 8 2 0 0 0 0 6 8 1 0 0 0 0 7 9 2 0 0 0 0 7 10 1 0 0 0 0 9 16 1 0 0 0 0 9 17 1 0 0 0 0 10 11 2 0 0 0 0 10 22 1 0 0 0 0 11 12 1 0 0 0 0 11 13 1 0 0 0 0 12 14 1 0 0 0 0 12 18 2 0 0 0 0 13 16 2 0 0 0 0 13 19 1 0 0 0 0 14 15 1 0 0 0 0 14 20 1 6 0 0 0 15 8 1 1 0 0 0 15 22 1 0 0 0 0 16 21 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	302.08
Volume:	293.909
LogP:	1.912
LogD:	1.873
LogS:	-3.312
# Rotatable Bonds:	2
TPSA:	96.22
# H-Bond Aceptor:	6
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.782
Synthetic Accessibility Score:	3.202
Fsp3:	0.188
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.398
MDCK Permeability:	9.838501682679635e-06
Pgp-inhibitor:	0.303
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.011
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.016

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.146
Plasma Protein Binding (PPB):	97.5795669555664%
Volume Distribution (VD):	0.565
Pgp-substrate:	4.011000156402588%

ADMET: Metabolism

CYP1A2-inhibitor:	0.206
CYP1A2-substrate:	0.331
CYP2C19-inhibitor:	0.127
CYP2C19-substrate:	0.377
CYP2C9-inhibitor:	0.325
CYP2C9-substrate:	0.785
CYP2D6-inhibitor:	0.524
CYP2D6-substrate:	0.289
CYP3A4-inhibitor:	0.407
CYP3A4-substrate:	0.248

ADMET: Excretion

Clearance (CL):	2.262
Half-life (T1/2):	0.404

ADMET: Toxicity

hERG Blockers:	0.066
Human Hepatotoxicity (H-HT):	0.049
Drug-inuced Liver Injury (DILI):	0.942
AMES Toxicity:	0.176
Rat Oral Acute Toxicity:	0.138
Maximum Recommended Daily Dose:	0.012
Skin Sensitization:	0.521
Carcinogencity:	0.188
Eye Corrosion:	0.003
Eye Irritation:	0.238
Respiratory Toxicity:	0.109

Download Data

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

Natural Product: NPC263449

Natural Product ID:	NPC263449
*Common Name:**	Alnustinol
IUPAC Name:	(2R,3R)-3,5,7-trihydroxy-6-methoxy-2-phenyl-2,3-dihydrochromen-4-one
Synonyms:	Alnustinol
Standard InCHIKey:	HFDPLPWGKGPTJB-LSDHHAIUSA-N
Standard InCHI:	InChI=1S/C16H14O6/c1-21-16-9(17)7-10-11(13(16)19)12(18)14(20)15(22-10)8-5-3-2-4-6-8/h2-7,14-15,17,19-20H,1H3/t14-,15+/m0/s1
SMILES:	COc1c(O)cc2c(c1O)C(=O)[C@@H]([C@H](O2)c1ccccc1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL252704
PubChem CID:	44446838
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0002585] O-methylated flavonoids [CHEMONTID:0002591] 6-O-methylated flavonoids

*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
NPO33288	Brazilian Red Propolis	Strain	n.a.	n.a.	n.a.	Brazilian	n.a.	PMID[17950610]
NPO33288	Brazilian Red Propolis	Strain	n.a.	n.a.	n.a.	Brazilian	n.a.	PMID[18440233]
NPO33288	Brazilian Red Propolis	Strain	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[26938776]
NPO33288	Brazilian Red Propolis	Strain	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[32525315]
NPO8300	Apis mellifera ligustica	Species	Apidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]

☑ 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	6
Others	1

Activity Type	# Activity
Cell Line	4
NON-MOLECULAR	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT461	Cell Line	PANC-1	Homo sapiens	CD100	>	100.0	uM	PMID[545621]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	100000.0	nM	PMID[545622]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	>	100000.0	nM	PMID[545622]
NPT453	Cell Line	HT-1080	Homo sapiens	IC50	>	100000.0	nM	PMID[545622]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	100000.0	nM	PMID[545622]

☑ 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 NPC263449 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	1700
0.2-0.3	4448
0.3-0.4	10314
0.4-0.5	7453
0.5-0.6	3619
0.6-0.7	4811
0.7-0.8	5336
0.8-0.85	2478
0.85-0.9	1454
0.9-0.95	592
0.95-1	80

Similarity Score	Similarity Level	Natural Product ID
0.9934	High Similarity	NPC308992
0.9801	High Similarity	NPC320825
0.9801	High Similarity	NPC326037
0.9801	High Similarity	NPC255106
0.9801	High Similarity	NPC201837
0.9801	High Similarity	NPC235165
0.9801	High Similarity	NPC13858
0.9737	High Similarity	NPC210084
0.9737	High Similarity	NPC48208
0.9737	High Similarity	NPC99597
0.9737	High Similarity	NPC474836
0.9737	High Similarity	NPC162869
0.9737	High Similarity	NPC52530
0.9737	High Similarity	NPC156057
0.9737	High Similarity	NPC474208
0.9737	High Similarity	NPC475267
0.9673	High Similarity	NPC152904
0.9671	High Similarity	NPC250922
0.9615	High Similarity	NPC224280
0.961	High Similarity	NPC282009
0.961	High Similarity	NPC287328
0.9608	High Similarity	NPC471479
0.9608	High Similarity	NPC471515
0.9608	High Similarity	NPC470402
0.9608	High Similarity	NPC245758
0.9608	High Similarity	NPC472913
0.9608	High Similarity	NPC96167
0.9608	High Similarity	NPC472911
0.9608	High Similarity	NPC472910
0.9608	High Similarity	NPC222814
0.9608	High Similarity	NPC472914
0.9605	High Similarity	NPC201451
0.9605	High Similarity	NPC26227
0.9605	High Similarity	NPC37392
0.9605	High Similarity	NPC44079
0.9605	High Similarity	NPC2928
0.9603	High Similarity	NPC61506
0.9603	High Similarity	NPC120537
0.9603	High Similarity	NPC36835
0.9603	High Similarity	NPC240476
0.9603	High Similarity	NPC199100
0.9603	High Similarity	NPC219582
0.9603	High Similarity	NPC180234
0.9603	High Similarity	NPC260491
0.9603	High Similarity	NPC302950
0.9603	High Similarity	NPC246162
0.9603	High Similarity	NPC236637
0.9603	High Similarity	NPC9743
0.9548	High Similarity	NPC471499
0.9548	High Similarity	NPC173137
0.9545	High Similarity	NPC250214
0.9545	High Similarity	NPC55738
0.9545	High Similarity	NPC95936
0.9545	High Similarity	NPC22192
0.9542	High Similarity	NPC303255
0.9542	High Similarity	NPC266960
0.9542	High Similarity	NPC49824
0.9542	High Similarity	NPC247017
0.9542	High Similarity	NPC98661
0.9542	High Similarity	NPC43243
0.9542	High Similarity	NPC471500
0.9542	High Similarity	NPC474638
0.9542	High Similarity	NPC472916
0.9542	High Similarity	NPC245546
0.9539	High Similarity	NPC325028
0.9539	High Similarity	NPC246328
0.9539	High Similarity	NPC206238
0.9539	High Similarity	NPC292214
0.9539	High Similarity	NPC88645
0.9539	High Similarity	NPC271779
0.9539	High Similarity	NPC256346
0.9539	High Similarity	NPC167091
0.9539	High Similarity	NPC18727
0.9539	High Similarity	NPC27532
0.9536	High Similarity	NPC204515
0.9536	High Similarity	NPC117579
0.9494	High Similarity	NPC42892
0.9494	High Similarity	NPC295082
0.949	High Similarity	NPC234052
0.949	High Similarity	NPC470457
0.9484	High Similarity	NPC470326
0.9484	High Similarity	NPC470183
0.9481	High Similarity	NPC472598
0.9481	High Similarity	NPC227192
0.9481	High Similarity	NPC203891
0.9481	High Similarity	NPC189179
0.9481	High Similarity	NPC101830
0.9481	High Similarity	NPC93376
0.9481	High Similarity	NPC223787
0.9481	High Similarity	NPC78225
0.9481	High Similarity	NPC75215
0.9481	High Similarity	NPC474055
0.9481	High Similarity	NPC469584
0.9481	High Similarity	NPC305663
0.9481	High Similarity	NPC287979
0.9481	High Similarity	NPC110070
0.9481	High Similarity	NPC176665
0.9481	High Similarity	NPC224137
0.9481	High Similarity	NPC67876
0.9481	High Similarity	NPC163524
0.9477	High Similarity	NPC472909
0.9477	High Similarity	NPC213622
0.9474	High Similarity	NPC120163
0.9474	High Similarity	NPC101996
0.9474	High Similarity	NPC275836
0.9474	High Similarity	NPC301323
0.9474	High Similarity	NPC198826
0.9474	High Similarity	NPC293183
0.9474	High Similarity	NPC25270
0.9474	High Similarity	NPC162313
0.9474	High Similarity	NPC212678
0.9474	High Similarity	NPC39007
0.9474	High Similarity	NPC131624
0.9474	High Similarity	NPC83508
0.9474	High Similarity	NPC239128
0.9474	High Similarity	NPC222830
0.9474	High Similarity	NPC156222
0.9474	High Similarity	NPC256283
0.9474	High Similarity	NPC187498
0.9474	High Similarity	NPC57030
0.9474	High Similarity	NPC71334
0.9474	High Similarity	NPC301123
0.9474	High Similarity	NPC161277
0.9474	High Similarity	NPC241498
0.9474	High Similarity	NPC188203
0.9474	High Similarity	NPC100887
0.9474	High Similarity	NPC275722
0.9474	High Similarity	NPC19721
0.947	High Similarity	NPC62042
0.947	High Similarity	NPC61620
0.9427	High Similarity	NPC41301
0.9427	High Similarity	NPC470459
0.9427	High Similarity	NPC472625
0.9423	High Similarity	NPC266314
0.9419	High Similarity	NPC143828
0.9419	High Similarity	NPC288669
0.9419	High Similarity	NPC25495
0.9419	High Similarity	NPC22472
0.9419	High Similarity	NPC204854
0.9419	High Similarity	NPC115798
0.9419	High Similarity	NPC253634
0.9419	High Similarity	NPC18772
0.9419	High Similarity	NPC130894
0.9419	High Similarity	NPC4481
0.9419	High Similarity	NPC191459
0.9419	High Similarity	NPC18607
0.9419	High Similarity	NPC7846
0.9419	High Similarity	NPC300943
0.9419	High Similarity	NPC105242
0.9419	High Similarity	NPC19687
0.9419	High Similarity	NPC176300
0.9419	High Similarity	NPC261004
0.9419	High Similarity	NPC329091
0.9419	High Similarity	NPC9609
0.9419	High Similarity	NPC152166
0.9416	High Similarity	NPC474520
0.9416	High Similarity	NPC191146
0.9416	High Similarity	NPC195796
0.9416	High Similarity	NPC291878
0.9416	High Similarity	NPC68093
0.9416	High Similarity	NPC35038
0.9416	High Similarity	NPC292107
0.9416	High Similarity	NPC278778
0.9412	High Similarity	NPC69394
0.9412	High Similarity	NPC183878
0.9412	High Similarity	NPC145379
0.9412	High Similarity	NPC472915
0.9412	High Similarity	NPC255350
0.9412	High Similarity	NPC86485
0.9412	High Similarity	NPC274327
0.9412	High Similarity	NPC47781
0.9412	High Similarity	NPC22519
0.9412	High Similarity	NPC176775
0.9412	High Similarity	NPC160951
0.9412	High Similarity	NPC231018
0.9412	High Similarity	NPC141212
0.9408	High Similarity	NPC252933
0.9408	High Similarity	NPC171010
0.9408	High Similarity	NPC54394
0.9408	High Similarity	NPC225731
0.9408	High Similarity	NPC149614
0.9408	High Similarity	NPC251110
0.9408	High Similarity	NPC200740
0.9408	High Similarity	NPC125062
0.9408	High Similarity	NPC31363
0.9371	High Similarity	NPC243877
0.9371	High Similarity	NPC470456
0.9371	High Similarity	NPC158761
0.9371	High Similarity	NPC14662
0.9367	High Similarity	NPC36
0.9367	High Similarity	NPC7688
0.9367	High Similarity	NPC125039
0.9367	High Similarity	NPC58223
0.9367	High Similarity	NPC7154
0.9367	High Similarity	NPC72787
0.9367	High Similarity	NPC62261
0.9367	High Similarity	NPC36916
0.9359	High Similarity	NPC471744
0.9359	High Similarity	NPC246478
0.9355	High Similarity	NPC181960

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 NPC263449 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	378
0.1-0.2	944
0.2-0.3	1860
0.3-0.4	2620
0.4-0.5	1750
0.5-0.6	957
0.6-0.7	449
0.7-0.8	138
0.8-0.85	30
0.85-0.9	14
0.9-0.95	9
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9603	High Similarity	NPD1934	Approved
0.9412	High Similarity	NPD2801	Approved
0.9367	High Similarity	NPD6166	Phase 2
0.9367	High Similarity	NPD6168	Clinical (unspecified phase)
0.9367	High Similarity	NPD6167	Clinical (unspecified phase)
0.9286	High Similarity	NPD2393	Clinical (unspecified phase)
0.9167	High Similarity	NPD3882	Suspended
0.9085	High Similarity	NPD4338	Clinical (unspecified phase)
0.9079	High Similarity	NPD1512	Approved
0.8947	High Similarity	NPD1511	Approved
0.8902	High Similarity	NPD7074	Phase 3
0.8896	High Similarity	NPD3818	Discontinued
0.8861	High Similarity	NPD3817	Phase 2
0.8848	High Similarity	NPD6797	Phase 2
0.8841	High Similarity	NPD7054	Approved
0.8795	High Similarity	NPD7251	Discontinued
0.8788	High Similarity	NPD7472	Approved
0.8758	High Similarity	NPD5494	Approved
0.8743	High Similarity	NPD7808	Phase 3
0.8688	High Similarity	NPD4868	Clinical (unspecified phase)
0.8675	High Similarity	NPD1552	Clinical (unspecified phase)
0.8675	High Similarity	NPD1550	Clinical (unspecified phase)
0.8645	High Similarity	NPD4378	Clinical (unspecified phase)
0.8634	High Similarity	NPD7075	Discontinued
0.8618	High Similarity	NPD1549	Phase 2
0.8608	High Similarity	NPD4380	Phase 2
0.8562	High Similarity	NPD7096	Clinical (unspecified phase)
0.8519	High Similarity	NPD4381	Clinical (unspecified phase)
0.8512	High Similarity	NPD7993	Clinical (unspecified phase)
0.8509	High Similarity	NPD5402	Approved
0.8393	Intermediate Similarity	NPD5844	Phase 1
0.8393	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8385	Intermediate Similarity	NPD6801	Discontinued
0.8364	Intermediate Similarity	NPD1247	Approved
0.8344	Intermediate Similarity	NPD6799	Approved
0.8301	Intermediate Similarity	NPD1510	Phase 2
0.8278	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8278	Intermediate Similarity	NPD1613	Approved
0.8247	Intermediate Similarity	NPD2796	Approved
0.8221	Intermediate Similarity	NPD1465	Phase 2
0.8204	Intermediate Similarity	NPD6232	Discontinued
0.8171	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8166	Intermediate Similarity	NPD7473	Discontinued
0.8158	Intermediate Similarity	NPD1240	Approved
0.8158	Intermediate Similarity	NPD943	Approved
0.8148	Intermediate Similarity	NPD6599	Discontinued
0.811	Intermediate Similarity	NPD7819	Suspended
0.8075	Intermediate Similarity	NPD5403	Approved
0.8063	Intermediate Similarity	NPD5401	Approved
0.8052	Intermediate Similarity	NPD1607	Approved
0.8047	Intermediate Similarity	NPD3926	Phase 2
0.8036	Intermediate Similarity	NPD6959	Discontinued
0.8035	Intermediate Similarity	NPD6559	Discontinued
0.8024	Intermediate Similarity	NPD919	Approved
0.8013	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.8012	Intermediate Similarity	NPD3751	Discontinued
0.7988	Intermediate Similarity	NPD7411	Suspended
0.7961	Intermediate Similarity	NPD3027	Phase 3
0.795	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7947	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7882	Intermediate Similarity	NPD3787	Discontinued
0.7875	Intermediate Similarity	NPD6190	Approved
0.7871	Intermediate Similarity	NPD230	Phase 1
0.7834	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7833	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7805	Intermediate Similarity	NPD1653	Approved
0.7799	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7785	Intermediate Similarity	NPD2935	Discontinued
0.7756	Intermediate Similarity	NPD447	Suspended
0.7753	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7751	Intermediate Similarity	NPD3749	Approved
0.775	Intermediate Similarity	NPD2800	Approved
0.7722	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7702	Intermediate Similarity	NPD3750	Approved
0.7702	Intermediate Similarity	NPD4628	Phase 3
0.7688	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7673	Intermediate Similarity	NPD1551	Phase 2
0.7636	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.763	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7622	Intermediate Similarity	NPD2533	Approved
0.7622	Intermediate Similarity	NPD2534	Approved
0.7622	Intermediate Similarity	NPD2532	Approved
0.7616	Intermediate Similarity	NPD7199	Phase 2
0.7602	Intermediate Similarity	NPD6234	Discontinued
0.7597	Intermediate Similarity	NPD9494	Approved
0.7593	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7588	Intermediate Similarity	NPD7768	Phase 2
0.7564	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.754	Intermediate Similarity	NPD6777	Approved
0.754	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.754	Intermediate Similarity	NPD6780	Approved
0.754	Intermediate Similarity	NPD6782	Approved
0.754	Intermediate Similarity	NPD6776	Approved
0.754	Intermediate Similarity	NPD6779	Approved
0.754	Intermediate Similarity	NPD6781	Approved
0.754	Intermediate Similarity	NPD6778	Approved
0.7532	Intermediate Similarity	NPD1933	Approved
0.7531	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.753	Intermediate Similarity	NPD920	Approved
0.7516	Intermediate Similarity	NPD2344	Approved
0.7515	Intermediate Similarity	NPD37	Approved
0.7514	Intermediate Similarity	NPD8434	Phase 2
0.75	Intermediate Similarity	NPD7228	Approved
0.7485	Intermediate Similarity	NPD4965	Approved
0.7485	Intermediate Similarity	NPD4966	Approved
0.7485	Intermediate Similarity	NPD4967	Phase 2
0.7455	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7453	Intermediate Similarity	NPD6100	Approved
0.7453	Intermediate Similarity	NPD6099	Approved
0.744	Intermediate Similarity	NPD3226	Approved
0.7434	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.743	Intermediate Similarity	NPD7685	Pre-registration
0.7421	Intermediate Similarity	NPD7435	Discontinued
0.7418	Intermediate Similarity	NPD8150	Discontinued
0.7412	Intermediate Similarity	NPD6844	Discontinued
0.741	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD2346	Discontinued
0.7405	Intermediate Similarity	NPD6233	Phase 2
0.7391	Intermediate Similarity	NPD3748	Approved
0.7391	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.738	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7374	Intermediate Similarity	NPD5953	Discontinued
0.736	Intermediate Similarity	NPD7286	Phase 2
0.7348	Intermediate Similarity	NPD8312	Approved
0.7348	Intermediate Similarity	NPD8313	Approved
0.7342	Intermediate Similarity	NPD2313	Discontinued
0.7342	Intermediate Similarity	NPD6798	Discontinued
0.7338	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD2309	Approved
0.733	Intermediate Similarity	NPD7697	Approved
0.733	Intermediate Similarity	NPD7696	Phase 3
0.733	Intermediate Similarity	NPD7698	Approved
0.7325	Intermediate Similarity	NPD4908	Phase 1
0.732	Intermediate Similarity	NPD1610	Phase 2
0.7317	Intermediate Similarity	NPD1243	Approved
0.7305	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD7871	Phase 2
0.7292	Intermediate Similarity	NPD7870	Phase 2
0.7289	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7284	Intermediate Similarity	NPD2799	Discontinued
0.7284	Intermediate Similarity	NPD7033	Discontinued
0.7273	Intermediate Similarity	NPD6535	Approved
0.7273	Intermediate Similarity	NPD6534	Approved
0.7273	Intermediate Similarity	NPD4360	Phase 2
0.7273	Intermediate Similarity	NPD4363	Phase 3
0.7268	Intermediate Similarity	NPD7701	Phase 2
0.7267	Intermediate Similarity	NPD6651	Approved
0.7261	Intermediate Similarity	NPD2861	Phase 2
0.7244	Intermediate Similarity	NPD1203	Approved
0.7233	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7232	Intermediate Similarity	NPD5242	Approved
0.7225	Intermediate Similarity	NPD5353	Approved
0.7205	Intermediate Similarity	NPD6355	Discontinued
0.7205	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7194	Intermediate Similarity	NPD7874	Approved
0.7194	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7191	Intermediate Similarity	NPD2403	Approved
0.7175	Intermediate Similarity	NPD5711	Approved
0.7175	Intermediate Similarity	NPD5710	Approved
0.7171	Intermediate Similarity	NPD1548	Phase 1
0.7169	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7161	Intermediate Similarity	NPD9269	Phase 2
0.7158	Intermediate Similarity	NPD7699	Phase 2
0.7158	Intermediate Similarity	NPD7700	Phase 2
0.7157	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7157	Intermediate Similarity	NPD7783	Phase 2
0.7157	Intermediate Similarity	NPD7801	Approved
0.7152	Intermediate Similarity	NPD2424	Discontinued
0.7151	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7390	Discontinued
0.7143	Intermediate Similarity	NPD8151	Discontinued
0.7128	Intermediate Similarity	NPD7584	Approved
0.7111	Intermediate Similarity	NPD2163	Approved
0.7108	Intermediate Similarity	NPD1652	Phase 2
0.7107	Intermediate Similarity	NPD6832	Phase 2
0.7101	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7098	Intermediate Similarity	NPD6823	Phase 2
0.7091	Intermediate Similarity	NPD7266	Discontinued
0.7079	Intermediate Similarity	NPD4111	Phase 1
0.7079	Intermediate Similarity	NPD4665	Approved
0.7052	Intermediate Similarity	NPD6385	Approved
0.7052	Intermediate Similarity	NPD6386	Approved
0.7051	Intermediate Similarity	NPD9717	Approved
0.7051	Intermediate Similarity	NPD1608	Approved
0.7049	Intermediate Similarity	NPD7240	Approved
0.7047	Intermediate Similarity	NPD2494	Approved
0.7047	Intermediate Similarity	NPD2493	Approved
0.7037	Intermediate Similarity	NPD4060	Phase 1
0.7035	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD2354	Approved
0.7019	Intermediate Similarity	NPD3268	Approved
0.7011	Intermediate Similarity	NPD7549	Discontinued
0.701	Intermediate Similarity	NPD7907	Approved
0.7	Intermediate Similarity	NPD4661	Approved
0.7	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD4662	Approved
0.6995	Remote Similarity	NPD2899	Discontinued
0.6994	Remote Similarity	NPD5124	Phase 1
0.6994	Remote Similarity	NPD5123	Clinical (unspecified phase)

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