NPASS Compound

Structure

NPC134287 OpenBabel07101718222D 29 31 0 0 0 0 0 0 0 0999 V2000 -5.1962 1.0000 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 0.8660 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -0.0000 0.0000 C 0 0 0 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 -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 -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 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 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 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 -2.5981 -1.5000 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 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 -0.8660 -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 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 -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 4.3301 1.5000 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 1.0000 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 4.3301 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 11 1 0 0 0 0 2 11 1 0 0 0 0 3 27 1 0 0 0 0 4 28 1 0 0 0 0 5 6 1 0 0 0 0 5 11 2 0 0 0 0 6 12 1 0 0 0 0 7 13 2 0 0 0 0 7 18 1 0 0 0 0 8 15 2 0 0 0 0 8 19 1 0 0 0 0 9 16 1 0 0 0 0 9 17 2 0 0 0 0 10 14 2 0 0 0 0 10 29 1 0 0 0 0 12 15 1 0 0 0 0 12 21 2 0 0 0 0 13 14 1 0 0 0 0 13 17 1 0 0 0 0 14 22 1 0 0 0 0 15 23 1 0 0 0 0 16 18 2 0 0 0 0 16 24 1 0 0 0 0 17 27 1 0 0 0 0 18 28 1 0 0 0 0 19 20 2 0 0 0 0 19 29 1 0 0 0 0 20 21 1 0 0 0 0 20 22 1 0 0 0 0 21 25 1 0 0 0 0 22 26 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	398.14
Volume:	401.202
LogP:	4.487
LogD:	2.774
LogS:	-3.42
# Rotatable Bonds:	5
TPSA:	109.36
# H-Bond Aceptor:	7
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.555
Synthetic Accessibility Score:	2.856
Fsp3:	0.227
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.869
MDCK Permeability:	9.570552720106207e-06
Pgp-inhibitor:	0.167
Pgp-substrate:	0.854
Human Intestinal Absorption (HIA):	0.071
20% Bioavailability (F20%):	0.656
30% Bioavailability (F30%):	0.035

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.002
Plasma Protein Binding (PPB):	88.42720794677734%
Volume Distribution (VD):	0.62
Pgp-substrate:	12.65722942352295%

ADMET: Metabolism

CYP1A2-inhibitor:	0.553
CYP1A2-substrate:	0.907
CYP2C19-inhibitor:	0.757
CYP2C19-substrate:	0.063
CYP2C9-inhibitor:	0.848
CYP2C9-substrate:	0.864
CYP2D6-inhibitor:	0.735
CYP2D6-substrate:	0.602
CYP3A4-inhibitor:	0.267
CYP3A4-substrate:	0.13

ADMET: Excretion

Clearance (CL):	9.338
Half-life (T1/2):	0.714

ADMET: Toxicity

hERG Blockers:	0.013
Human Hepatotoxicity (H-HT):	0.327
Drug-inuced Liver Injury (DILI):	0.488
AMES Toxicity:	0.044
Rat Oral Acute Toxicity:	0.248
Maximum Recommended Daily Dose:	0.16
Skin Sensitization:	0.871
Carcinogencity:	0.053
Eye Corrosion:	0.003
Eye Irritation:	0.632
Respiratory Toxicity:	0.227

Download Data

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

Natural Product: NPC134287

Natural Product ID:	NPC134287
*Common Name:**	Viridiflorin
IUPAC Name:	5,7-dihydroxy-3-(4-hydroxy-2,5-dimethoxyphenyl)-6-(3-methylbut-2-enyl)chromen-4-one
Synonyms:	Viridiflorin
Standard InCHIKey:	LOFJXYSYEDFQAI-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C22H22O7/c1-11(2)5-6-12-15(23)8-19-20(21(12)25)22(26)14(10-29-19)13-7-18(28-4)16(24)9-17(13)27-3/h5,7-10,23-25H,6H2,1-4H3
SMILES:	CC(=CCc1c(cc2c(c1O)c(=O)c(co2)c1cc(c(cc1OC)O)OC)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL400361
PubChem CID:	44257314
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002506] Isoflavonoids [CHEMONTID:0001612] Isoflavans [CHEMONTID:0001827] Isoflavanones [CHEMONTID:0003526] 6-prenylated isoflavanones

*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
NPO24609	Millettia brandisiana	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18039011]
NPO24609	Millettia brandisiana	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19124248]
NPO24609	Millettia brandisiana	Species	Fabaceae	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
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT579	Cell Line	DLD-1	Homo sapiens	IC50	>	25000.0	nM	PMID[531531]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	>	25000.0	nM	PMID[531531]

☑ 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 NPC134287 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	436
0.1-0.2	1896
0.2-0.3	4655
0.3-0.4	11089
0.4-0.5	6756
0.5-0.6	3763
0.6-0.7	4954
0.7-0.8	4954
0.8-0.85	2139
0.85-0.9	1225
0.9-0.95	762
0.95-1	68

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC130589
0.9866	High Similarity	NPC78103
0.9865	High Similarity	NPC39184
0.9797	High Similarity	NPC124714
0.9797	High Similarity	NPC250557
0.9796	High Similarity	NPC45291
0.9796	High Similarity	NPC19980
0.973	High Similarity	NPC100971
0.973	High Similarity	NPC35763
0.973	High Similarity	NPC245382
0.973	High Similarity	NPC121522
0.973	High Similarity	NPC100263
0.973	High Similarity	NPC216769
0.973	High Similarity	NPC131266
0.973	High Similarity	NPC209487
0.973	High Similarity	NPC269451
0.973	High Similarity	NPC291802
0.973	High Similarity	NPC181209
0.9728	High Similarity	NPC239363
0.9662	High Similarity	NPC256406
0.9662	High Similarity	NPC262623
0.9608	High Similarity	NPC81679
0.9605	High Similarity	NPC476980
0.9603	High Similarity	NPC36852
0.9603	High Similarity	NPC262286
0.9595	High Similarity	NPC10467
0.9595	High Similarity	NPC156953
0.9592	High Similarity	NPC166036
0.9592	High Similarity	NPC203077
0.9592	High Similarity	NPC238279
0.9542	High Similarity	NPC258331
0.9536	High Similarity	NPC138243
0.9533	High Similarity	NPC280937
0.9527	High Similarity	NPC264550
0.9527	High Similarity	NPC200060
0.9527	High Similarity	NPC92722
0.9527	High Similarity	NPC195763
0.9527	High Similarity	NPC38545
0.9527	High Similarity	NPC40290
0.9527	High Similarity	NPC171916
0.9527	High Similarity	NPC102003
0.9527	High Similarity	NPC264289
0.9527	High Similarity	NPC142876
0.9527	High Similarity	NPC333691
0.9527	High Similarity	NPC69430
0.9527	High Similarity	NPC139293
0.9481	High Similarity	NPC83922
0.9481	High Similarity	NPC472448
0.9481	High Similarity	NPC261470
0.9477	High Similarity	NPC246478
0.9474	High Similarity	NPC476981
0.9474	High Similarity	NPC223787
0.9474	High Similarity	NPC78225
0.947	High Similarity	NPC113906
0.947	High Similarity	NPC20830
0.947	High Similarity	NPC208197
0.947	High Similarity	NPC256612
0.947	High Similarity	NPC213622
0.9467	High Similarity	NPC324233
0.9467	High Similarity	NPC471982
0.9467	High Similarity	NPC323626
0.9463	High Similarity	NPC472279
0.9459	High Similarity	NPC15329
0.9459	High Similarity	NPC218490
0.9459	High Similarity	NPC194653
0.9459	High Similarity	NPC203747
0.9459	High Similarity	NPC80710
0.9459	High Similarity	NPC131451
0.9459	High Similarity	NPC139364
0.9459	High Similarity	NPC287395
0.9459	High Similarity	NPC183655
0.9459	High Similarity	NPC254702
0.9419	High Similarity	NPC470459
0.9416	High Similarity	NPC259456
0.9416	High Similarity	NPC266314
0.9416	High Similarity	NPC29876
0.9416	High Similarity	NPC167678
0.9412	High Similarity	NPC95936
0.9412	High Similarity	NPC250214
0.9408	High Similarity	NPC68093
0.9408	High Similarity	NPC472455
0.9408	High Similarity	NPC191146
0.9408	High Similarity	NPC472916
0.9404	High Similarity	NPC231018
0.9404	High Similarity	NPC47781
0.9404	High Similarity	NPC22519
0.9404	High Similarity	NPC176775
0.9404	High Similarity	NPC75279
0.9404	High Similarity	NPC160951
0.9404	High Similarity	NPC274327
0.9404	High Similarity	NPC69394
0.9404	High Similarity	NPC250822
0.9404	High Similarity	NPC183878
0.9404	High Similarity	NPC145379
0.9404	High Similarity	NPC255350
0.9404	High Similarity	NPC276409
0.9392	High Similarity	NPC125449
0.9392	High Similarity	NPC119660
0.9392	High Similarity	NPC93034
0.9392	High Similarity	NPC188074
0.9359	High Similarity	NPC470457
0.9359	High Similarity	NPC50960
0.9351	High Similarity	NPC204290
0.9351	High Similarity	NPC228785
0.9351	High Similarity	NPC14353
0.9351	High Similarity	NPC84571
0.9351	High Similarity	NPC56085
0.9346	High Similarity	NPC472914
0.9346	High Similarity	NPC52889
0.9346	High Similarity	NPC245758
0.9346	High Similarity	NPC96167
0.9346	High Similarity	NPC469584
0.9346	High Similarity	NPC472911
0.9346	High Similarity	NPC162869
0.9346	High Similarity	NPC472913
0.9346	High Similarity	NPC222814
0.9346	High Similarity	NPC210084
0.9346	High Similarity	NPC475267
0.9346	High Similarity	NPC99597
0.9346	High Similarity	NPC470402
0.9346	High Similarity	NPC472910
0.9346	High Similarity	NPC156057
0.9346	High Similarity	NPC474208
0.9346	High Similarity	NPC48208
0.9346	High Similarity	NPC291508
0.9346	High Similarity	NPC474836
0.9342	High Similarity	NPC183597
0.9342	High Similarity	NPC201136
0.9342	High Similarity	NPC230149
0.9342	High Similarity	NPC472280
0.9342	High Similarity	NPC4455
0.9342	High Similarity	NPC196439
0.9342	High Similarity	NPC138360
0.9342	High Similarity	NPC280339
0.9342	High Similarity	NPC57674
0.9342	High Similarity	NPC146165
0.9342	High Similarity	NPC168247
0.9342	High Similarity	NPC2476
0.9342	High Similarity	NPC92659
0.9342	High Similarity	NPC2928
0.9342	High Similarity	NPC200761
0.9342	High Similarity	NPC167815
0.9342	High Similarity	NPC227325
0.9342	High Similarity	NPC477503
0.9342	High Similarity	NPC234255
0.9342	High Similarity	NPC117992
0.9342	High Similarity	NPC163780
0.9342	High Similarity	NPC50715
0.9342	High Similarity	NPC470327
0.9342	High Similarity	NPC45849
0.9342	High Similarity	NPC128863
0.9342	High Similarity	NPC152951
0.9338	High Similarity	NPC60972
0.9338	High Similarity	NPC71334
0.9338	High Similarity	NPC57030
0.9338	High Similarity	NPC198826
0.9338	High Similarity	NPC83508
0.9338	High Similarity	NPC100887
0.9338	High Similarity	NPC301323
0.9338	High Similarity	NPC212678
0.9338	High Similarity	NPC101996
0.9338	High Similarity	NPC131624
0.9338	High Similarity	NPC187498
0.9338	High Similarity	NPC25270
0.9338	High Similarity	NPC156222
0.9338	High Similarity	NPC256283
0.9338	High Similarity	NPC241498
0.9338	High Similarity	NPC162313
0.9338	High Similarity	NPC293183
0.9338	High Similarity	NPC120163
0.9338	High Similarity	NPC39732
0.9338	High Similarity	NPC222830
0.9338	High Similarity	NPC275722
0.9338	High Similarity	NPC188203
0.9338	High Similarity	NPC275836
0.9338	High Similarity	NPC239128
0.9338	High Similarity	NPC249570
0.9324	High Similarity	NPC216314
0.9324	High Similarity	NPC165389
0.9324	High Similarity	NPC195919
0.9324	High Similarity	NPC12377
0.9324	High Similarity	NPC226987
0.9324	High Similarity	NPC120924
0.9324	High Similarity	NPC143903
0.932	High Similarity	NPC182842
0.9299	High Similarity	NPC470462
0.9295	High Similarity	NPC41301
0.9295	High Similarity	NPC7483
0.9295	High Similarity	NPC270837
0.929	High Similarity	NPC295009
0.929	High Similarity	NPC134783
0.929	High Similarity	NPC40491
0.929	High Similarity	NPC278052
0.929	High Similarity	NPC61010
0.929	High Similarity	NPC311740
0.929	High Similarity	NPC260640
0.9286	High Similarity	NPC74178
0.9286	High Similarity	NPC204879
0.9286	High Similarity	NPC469658
0.9286	High Similarity	NPC100123

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 NPC134287 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	418
0.1-0.2	990
0.2-0.3	1901
0.3-0.4	2679
0.4-0.5	1728
0.5-0.6	933
0.6-0.7	337
0.7-0.8	112
0.8-0.85	32
0.85-0.9	15
0.9-0.95	5
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9404	High Similarity	NPD2801	Approved
0.915	High Similarity	NPD2393	Clinical (unspecified phase)
0.9085	High Similarity	NPD1934	Approved
0.891	High Similarity	NPD3882	Suspended
0.8831	High Similarity	NPD4380	Phase 2
0.8808	High Similarity	NPD1511	Approved
0.8765	High Similarity	NPD3818	Discontinued
0.8742	High Similarity	NPD5494	Approved
0.8693	High Similarity	NPD1512	Approved
0.8649	High Similarity	NPD1510	Phase 2
0.8642	High Similarity	NPD6166	Phase 2
0.8642	High Similarity	NPD6168	Clinical (unspecified phase)
0.8642	High Similarity	NPD6167	Clinical (unspecified phase)
0.8634	High Similarity	NPD6232	Discontinued
0.8627	High Similarity	NPD4378	Clinical (unspecified phase)
0.8608	High Similarity	NPD3817	Phase 2
0.8589	High Similarity	NPD7473	Discontinued
0.8553	High Similarity	NPD4868	Clinical (unspecified phase)
0.8503	High Similarity	NPD4338	Clinical (unspecified phase)
0.8485	Intermediate Similarity	NPD7054	Approved
0.8434	Intermediate Similarity	NPD7074	Phase 3
0.8434	Intermediate Similarity	NPD7472	Approved
0.8385	Intermediate Similarity	NPD7075	Discontinued
0.8378	Intermediate Similarity	NPD1240	Approved
0.8378	Intermediate Similarity	NPD943	Approved
0.8344	Intermediate Similarity	NPD1247	Approved
0.8344	Intermediate Similarity	NPD2935	Discontinued
0.8313	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8274	Intermediate Similarity	NPD6797	Phase 2
0.8272	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8269	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8267	Intermediate Similarity	NPD1607	Approved
0.8263	Intermediate Similarity	NPD5844	Phase 1
0.825	Intermediate Similarity	NPD6801	Discontinued
0.8235	Intermediate Similarity	NPD1549	Phase 2
0.8225	Intermediate Similarity	NPD7251	Discontinued
0.8224	Intermediate Similarity	NPD2796	Approved
0.8199	Intermediate Similarity	NPD7819	Suspended
0.8176	Intermediate Similarity	NPD7808	Phase 3
0.817	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.817	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8148	Intermediate Similarity	NPD5402	Approved
0.8089	Intermediate Similarity	NPD6799	Approved
0.8086	Intermediate Similarity	NPD1465	Phase 2
0.8079	Intermediate Similarity	NPD230	Phase 1
0.8075	Intermediate Similarity	NPD7411	Suspended
0.8059	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8047	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8038	Intermediate Similarity	NPD2533	Approved
0.8038	Intermediate Similarity	NPD2534	Approved
0.8038	Intermediate Similarity	NPD2532	Approved
0.8037	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8012	Intermediate Similarity	NPD6959	Discontinued
0.8	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD919	Approved
0.7937	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7933	Intermediate Similarity	NPD3027	Phase 3
0.7922	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7907	Intermediate Similarity	NPD6559	Discontinued
0.7901	Intermediate Similarity	NPD6599	Discontinued
0.7834	Intermediate Similarity	NPD2800	Approved
0.7811	Intermediate Similarity	NPD3926	Phase 2
0.7806	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.78	Intermediate Similarity	NPD9494	Approved
0.7792	Intermediate Similarity	NPD6651	Approved
0.7785	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7784	Intermediate Similarity	NPD6234	Discontinued
0.7771	Intermediate Similarity	NPD7768	Phase 2
0.7765	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7722	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7716	Intermediate Similarity	NPD5403	Approved
0.7716	Intermediate Similarity	NPD920	Approved
0.7709	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD37	Approved
0.7682	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7673	Intermediate Similarity	NPD3750	Approved
0.7662	Intermediate Similarity	NPD1613	Approved
0.7662	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7651	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.764	Intermediate Similarity	NPD7390	Discontinued
0.7632	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7627	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7625	Intermediate Similarity	NPD6190	Approved
0.7613	Intermediate Similarity	NPD447	Suspended
0.761	Intermediate Similarity	NPD1243	Approved
0.7609	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7593	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7593	Intermediate Similarity	NPD5401	Approved
0.7593	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7561	Intermediate Similarity	NPD1653	Approved
0.756	Intermediate Similarity	NPD4965	Approved
0.756	Intermediate Similarity	NPD4966	Approved
0.756	Intermediate Similarity	NPD4967	Phase 2
0.7543	Intermediate Similarity	NPD5953	Discontinued
0.7532	Intermediate Similarity	NPD1551	Phase 2
0.7532	Intermediate Similarity	NPD2313	Discontinued
0.7531	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7529	Intermediate Similarity	NPD7286	Phase 2
0.7515	Intermediate Similarity	NPD3749	Approved
0.7515	Intermediate Similarity	NPD3226	Approved
0.7471	Intermediate Similarity	NPD7228	Approved
0.7469	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD2799	Discontinued
0.7467	Intermediate Similarity	NPD9269	Phase 2
0.7458	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7453	Intermediate Similarity	NPD4628	Phase 3
0.7442	Intermediate Similarity	NPD5710	Approved
0.7442	Intermediate Similarity	NPD5711	Approved
0.7419	Intermediate Similarity	NPD6782	Approved
0.7419	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD6778	Approved
0.7419	Intermediate Similarity	NPD6776	Approved
0.7419	Intermediate Similarity	NPD6779	Approved
0.7419	Intermediate Similarity	NPD6780	Approved
0.7419	Intermediate Similarity	NPD6781	Approved
0.7419	Intermediate Similarity	NPD6777	Approved
0.7401	Intermediate Similarity	NPD7685	Pre-registration
0.7399	Intermediate Similarity	NPD5242	Approved
0.7386	Intermediate Similarity	NPD2798	Approved
0.7384	Intermediate Similarity	NPD7199	Phase 2
0.7375	Intermediate Similarity	NPD2344	Approved
0.7375	Intermediate Similarity	NPD2346	Discontinued
0.7371	Intermediate Similarity	NPD3751	Discontinued
0.7358	Intermediate Similarity	NPD3748	Approved
0.7312	Intermediate Similarity	NPD6100	Approved
0.7312	Intermediate Similarity	NPD6099	Approved
0.7305	Intermediate Similarity	NPD7458	Discontinued
0.7302	Intermediate Similarity	NPD7435	Discontinued
0.7299	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7294	Intermediate Similarity	NPD5353	Approved
0.7293	Intermediate Similarity	NPD8150	Discontinued
0.7292	Intermediate Similarity	NPD8151	Discontinued
0.7278	Intermediate Similarity	NPD1933	Approved
0.7258	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD3787	Discontinued
0.7239	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD8313	Approved
0.7222	Intermediate Similarity	NPD8312	Approved
0.7219	Intermediate Similarity	NPD6386	Approved
0.7219	Intermediate Similarity	NPD6385	Approved
0.7212	Intermediate Similarity	NPD4357	Discontinued
0.7211	Intermediate Similarity	NPD7698	Approved
0.7211	Intermediate Similarity	NPD7696	Phase 3
0.7211	Intermediate Similarity	NPD7697	Approved
0.7208	Intermediate Similarity	NPD1470	Approved
0.72	Intermediate Similarity	NPD9268	Approved
0.7198	Intermediate Similarity	NPD8434	Phase 2
0.7197	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7195	Intermediate Similarity	NPD2309	Approved
0.7181	Intermediate Similarity	NPD5536	Phase 2
0.7178	Intermediate Similarity	NPD2654	Approved
0.7176	Intermediate Similarity	NPD6844	Discontinued
0.7173	Intermediate Similarity	NPD7871	Phase 2
0.7173	Intermediate Similarity	NPD7870	Phase 2
0.7158	Intermediate Similarity	NPD6823	Phase 2
0.7151	Intermediate Similarity	NPD6534	Approved
0.7151	Intermediate Similarity	NPD4360	Phase 2
0.7151	Intermediate Similarity	NPD6535	Approved
0.7151	Intermediate Similarity	NPD4363	Phase 3
0.715	Intermediate Similarity	NPD7701	Phase 2
0.7136	Intermediate Similarity	NPD2899	Discontinued
0.7115	Intermediate Similarity	NPD3018	Phase 2
0.7099	Intermediate Similarity	NPD5405	Approved
0.7099	Intermediate Similarity	NPD5404	Approved
0.7099	Intermediate Similarity	NPD5408	Approved
0.7099	Intermediate Similarity	NPD5406	Approved
0.7098	Intermediate Similarity	NPD7584	Approved
0.7097	Intermediate Similarity	NPD1203	Approved
0.7077	Intermediate Similarity	NPD7874	Approved
0.7077	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.707	Intermediate Similarity	NPD4908	Phase 1
0.707	Intermediate Similarity	NPD6832	Phase 2
0.7063	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD1201	Approved
0.7059	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD7229	Phase 3
0.7041	Intermediate Similarity	NPD7801	Approved
0.7037	Intermediate Similarity	NPD7700	Phase 2
0.7037	Intermediate Similarity	NPD7033	Discontinued
0.7037	Intermediate Similarity	NPD7699	Phase 2
0.7021	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD4361	Phase 2
0.702	Intermediate Similarity	NPD1548	Phase 1
0.7018	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7017	Intermediate Similarity	NPD7240	Approved
0.7013	Intermediate Similarity	NPD3972	Approved
0.6995	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD3268	Approved
0.6978	Remote Similarity	NPD7549	Discontinued
0.6968	Remote Similarity	NPD2983	Phase 2
0.6968	Remote Similarity	NPD2982	Phase 2
0.6966	Remote Similarity	NPD2403	Approved
0.6954	Remote Similarity	NPD7783	Phase 2
0.6954	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD7266	Discontinued
0.6948	Remote Similarity	NPD1610	Phase 2
0.6937	Remote Similarity	NPD6233	Phase 2
0.6933	Remote Similarity	NPD4308	Phase 3
0.6928	Remote Similarity	NPD8166	Discontinued

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