NPASS Compound

Structure

NPC474162 OpenBabel07101718322D 33 36 0 0 1 0 0 0 0 0999 V2000 3.9533 -1.3625 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1780 -0.1378 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7355 -0.4914 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.6603 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5391 0.0517 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5050 0.3105 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 2.0000 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 1.8320 0.7588 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 -4.3301 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2121 -0.3966 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 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 0 0 0 0 0 0 0 0 0 0 -4.3301 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.9282 3.0000 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 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 -1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 3 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 -3.4641 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 3.5000 0.0000 O 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 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 14 1 0 0 0 0 2 14 1 0 0 0 0 3 26 1 0 0 0 0 4 31 1 0 0 0 0 5 6 1 0 0 0 0 5 10 1 0 0 0 0 6 14 2 0 0 0 0 7 8 2 0 0 0 0 7 15 1 0 0 0 0 8 18 1 0 0 0 0 9 11 2 0 0 0 0 9 16 1 0 0 0 0 10 26 1 0 0 0 0 11 26 1 0 0 0 0 12 19 2 0 0 0 0 12 20 1 0 0 0 0 13 17 1 0 0 0 0 13 32 1 0 0 0 0 15 24 2 0 0 0 0 16 19 1 0 0 0 0 16 22 2 0 0 0 0 17 15 1 6 0 0 0 17 23 1 0 0 0 0 18 25 2 0 0 0 0 18 31 1 0 0 0 0 19 33 1 0 0 0 0 20 21 2 0 0 0 0 20 32 1 0 0 0 0 21 22 1 0 0 0 0 21 23 1 0 0 0 0 22 27 1 0 0 0 0 23 28 2 0 0 0 0 24 25 1 0 0 0 0 24 29 1 0 0 0 0 25 30 1 0 0 0 0 26 33 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	452.18
Volume:	461.83
LogP:	5.119
LogD:	3.192
LogS:	-4.133
# Rotatable Bonds:	5
TPSA:	105.45
# H-Bond Aceptor:	7
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.429
Synthetic Accessibility Score:	4.11
Fsp3:	0.346
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	2
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.855
MDCK Permeability:	1.745550434861798e-05
Pgp-inhibitor:	0.916
Pgp-substrate:	0.016
Human Intestinal Absorption (HIA):	0.049
20% Bioavailability (F20%):	0.021
30% Bioavailability (F30%):	0.01

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.001
Plasma Protein Binding (PPB):	99.96922302246094%
Volume Distribution (VD):	0.566
Pgp-substrate:	2.869880437850952%

ADMET: Metabolism

CYP1A2-inhibitor:	0.557
CYP1A2-substrate:	0.815
CYP2C19-inhibitor:	0.606
CYP2C19-substrate:	0.569
CYP2C9-inhibitor:	0.866
CYP2C9-substrate:	0.848
CYP2D6-inhibitor:	0.857
CYP2D6-substrate:	0.274
CYP3A4-inhibitor:	0.769
CYP3A4-substrate:	0.623

ADMET: Excretion

Clearance (CL):	9.421
Half-life (T1/2):	0.164

ADMET: Toxicity

hERG Blockers:	0.032
Human Hepatotoxicity (H-HT):	0.743
Drug-inuced Liver Injury (DILI):	0.649
AMES Toxicity:	0.051
Rat Oral Acute Toxicity:	0.405
Maximum Recommended Daily Dose:	0.746
Skin Sensitization:	0.934
Carcinogencity:	0.489
Eye Corrosion:	0.003
Eye Irritation:	0.356
Respiratory Toxicity:	0.375

Download Data

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

Natural Product: NPC474162

Natural Product ID:	NPC474162
*Common Name:**	(3S)-Isodiscoloranone B
IUPAC Name:	(7S)-7-(2,3-dihydroxy-4-methoxyphenyl)-5-hydroxy-2-methyl-2-(4-methylpent-3-enyl)-7,8-dihydropyrano[3,2-g]chromen-6-one
Synonyms:
Standard InCHIKey:	BFGWTNSLVFLZPM-SIHBAMTISA-N
Standard InCHI:	InChI=1S/C26H28O7/c1-14(2)6-5-10-26(3)11-9-16-19(33-26)12-20-21(22(16)27)23(28)17(13-32-20)15-7-8-18(31-4)25(30)24(15)29/h6-9,11-12,17,27,29-30H,5,10,13H2,1-4H3/t17-,26?/m1/s1
SMILES:	COc1ccc(c(c1O)O)[C@H]1COc2c(C1=O)c(O)c1c(c2)OC(C=C1)(C)CCC=C(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL463100
PubChem CID:	11995375
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002506] Isoflavonoids [CHEMONTID:0002586] O-methylated isoflavonoids [CHEMONTID:0002606] 4'-O-methylated isoflavonoids [CHEMONTID:0003651] 3'-hydroxy,4'-methoxyisoflavonoids

*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
NPO401	Berchemia discolor	Species	Rhamnaceae	Eukaryota	n.a.	Tanzanian	n.a.	PMID[17125241]
NPO401	Berchemia discolor	Species	Rhamnaceae	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
ED50	3

Activity Type	# Activity
Cell Line	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1034	Cell Line	Lu1	Homo sapiens	ED50	>	5.0	ug ml-1	PMID[475689]
NPT858	Cell Line	LNCaP	Homo sapiens	ED50	>	5.0	ug ml-1	PMID[475689]
NPT83	Cell Line	MCF7	Homo sapiens	ED50	>	5.0	ug ml-1	PMID[475689]

☑ 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 NPC474162 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	1635
0.2-0.3	3866
0.3-0.4	9650
0.4-0.5	8646
0.5-0.6	3345
0.6-0.7	4772
0.7-0.8	5553
0.8-0.85	2860
0.85-0.9	1569
0.9-0.95	355
0.95-1	33

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC474150
0.974	High Similarity	NPC118256
0.974	High Similarity	NPC119209
0.974	High Similarity	NPC192686
0.9679	High Similarity	NPC186686
0.9677	High Similarity	NPC474038
0.9675	High Similarity	NPC204879
0.9618	High Similarity	NPC239752
0.9618	High Similarity	NPC62261
0.9618	High Similarity	NPC472450
0.9618	High Similarity	NPC275780
0.9615	High Similarity	NPC472448
0.9615	High Similarity	NPC83922
0.9613	High Similarity	NPC204290
0.9613	High Similarity	NPC475784
0.9613	High Similarity	NPC471973
0.961	High Similarity	NPC129684
0.961	High Similarity	NPC27337
0.961	High Similarity	NPC52889
0.961	High Similarity	NPC218313
0.961	High Similarity	NPC299520
0.961	High Similarity	NPC284820
0.961	High Similarity	NPC473272
0.961	High Similarity	NPC474681
0.956	High Similarity	NPC288813
0.9557	High Similarity	NPC235610
0.9557	High Similarity	NPC39091
0.9557	High Similarity	NPC120593
0.9557	High Similarity	NPC43319
0.9554	High Similarity	NPC23298
0.9554	High Similarity	NPC189473
0.9554	High Similarity	NPC472625
0.9551	High Similarity	NPC234644
0.9551	High Similarity	NPC167678
0.9551	High Similarity	NPC471210
0.9551	High Similarity	NPC266314
0.9551	High Similarity	NPC57715
0.9551	High Similarity	NPC29876
0.9551	High Similarity	NPC134783
0.9551	High Similarity	NPC26326
0.9551	High Similarity	NPC472632
0.9548	High Similarity	NPC184755
0.9548	High Similarity	NPC74178
0.9545	High Similarity	NPC6633
0.9545	High Similarity	NPC291878
0.9545	High Similarity	NPC35038
0.9545	High Similarity	NPC195796
0.9545	High Similarity	NPC472455
0.9545	High Similarity	NPC5322
0.9545	High Similarity	NPC133970
0.9545	High Similarity	NPC278778
0.9545	High Similarity	NPC471985
0.9497	High Similarity	NPC218226
0.9494	High Similarity	NPC293319
0.949	High Similarity	NPC261470
0.949	High Similarity	NPC474034
0.949	High Similarity	NPC474033
0.949	High Similarity	NPC229632
0.9487	High Similarity	NPC36217
0.9487	High Similarity	NPC174953
0.9487	High Similarity	NPC474960
0.9487	High Similarity	NPC476980
0.9487	High Similarity	NPC472624
0.9487	High Similarity	NPC188433
0.9484	High Similarity	NPC472914
0.9484	High Similarity	NPC472598
0.9484	High Similarity	NPC472911
0.9484	High Similarity	NPC78225
0.9484	High Similarity	NPC245758
0.9484	High Similarity	NPC474055
0.9484	High Similarity	NPC469584
0.9484	High Similarity	NPC222814
0.9484	High Similarity	NPC472910
0.9484	High Similarity	NPC291508
0.9484	High Similarity	NPC471209
0.9484	High Similarity	NPC136674
0.9484	High Similarity	NPC96167
0.9484	High Similarity	NPC472913
0.9481	High Similarity	NPC200246
0.9481	High Similarity	NPC256925
0.9481	High Similarity	NPC470327
0.9481	High Similarity	NPC168247
0.9481	High Similarity	NPC477503
0.9481	High Similarity	NPC57674
0.9481	High Similarity	NPC152951
0.9481	High Similarity	NPC234255
0.9481	High Similarity	NPC31018
0.9481	High Similarity	NPC117992
0.9481	High Similarity	NPC230149
0.9481	High Similarity	NPC472280
0.9481	High Similarity	NPC45849
0.9481	High Similarity	NPC200761
0.9481	High Similarity	NPC255807
0.9477	High Similarity	NPC471982
0.9477	High Similarity	NPC260979
0.9477	High Similarity	NPC472912
0.9434	High Similarity	NPC472449
0.9434	High Similarity	NPC37870
0.943	High Similarity	NPC306321
0.943	High Similarity	NPC12461
0.943	High Similarity	NPC152659
0.943	High Similarity	NPC248638
0.943	High Similarity	NPC303460
0.943	High Similarity	NPC41301
0.943	High Similarity	NPC236521
0.943	High Similarity	NPC124038
0.9427	High Similarity	NPC471211
0.9427	High Similarity	NPC173137
0.9427	High Similarity	NPC259456
0.9427	High Similarity	NPC471212
0.9427	High Similarity	NPC61010
0.9427	High Similarity	NPC472634
0.9423	High Similarity	NPC250214
0.9423	High Similarity	NPC55738
0.9423	High Similarity	NPC95936
0.9423	High Similarity	NPC53545
0.9423	High Similarity	NPC473990
0.9423	High Similarity	NPC117418
0.9419	High Similarity	NPC209614
0.9419	High Similarity	NPC282307
0.9419	High Similarity	NPC470600
0.9419	High Similarity	NPC191146
0.9419	High Similarity	NPC472626
0.9419	High Similarity	NPC170026
0.9419	High Similarity	NPC470328
0.9419	High Similarity	NPC68093
0.9416	High Similarity	NPC192083
0.9416	High Similarity	NPC227337
0.9416	High Similarity	NPC74924
0.9416	High Similarity	NPC170492
0.9416	High Similarity	NPC273462
0.9416	High Similarity	NPC18727
0.9416	High Similarity	NPC49402
0.9416	High Similarity	NPC70433
0.9416	High Similarity	NPC33051
0.9416	High Similarity	NPC213896
0.9416	High Similarity	NPC469550
0.9383	High Similarity	NPC310794
0.9379	High Similarity	NPC472276
0.9375	High Similarity	NPC477154
0.9375	High Similarity	NPC117854
0.9375	High Similarity	NPC6588
0.9371	High Similarity	NPC50960
0.9371	High Similarity	NPC224280
0.9371	High Similarity	NPC303174
0.9371	High Similarity	NPC300053
0.9371	High Similarity	NPC108433
0.9371	High Similarity	NPC472277
0.9367	High Similarity	NPC329760
0.9367	High Similarity	NPC201800
0.9367	High Similarity	NPC78332
0.9367	High Similarity	NPC476247
0.9367	High Similarity	NPC25152
0.9367	High Similarity	NPC472635
0.9367	High Similarity	NPC206605
0.9363	High Similarity	NPC56085
0.9363	High Similarity	NPC287328
0.9363	High Similarity	NPC472630
0.9363	High Similarity	NPC282009
0.9363	High Similarity	NPC297212
0.9363	High Similarity	NPC228785
0.9363	High Similarity	NPC472631
0.9363	High Similarity	NPC328102
0.9363	High Similarity	NPC476280
0.9363	High Similarity	NPC139036
0.9363	High Similarity	NPC14353
0.9359	High Similarity	NPC475267
0.9359	High Similarity	NPC48208
0.9359	High Similarity	NPC474208
0.9359	High Similarity	NPC181960
0.9359	High Similarity	NPC67876
0.9359	High Similarity	NPC476981
0.9359	High Similarity	NPC223787
0.9359	High Similarity	NPC36852
0.9359	High Similarity	NPC474836
0.9359	High Similarity	NPC180011
0.9359	High Similarity	NPC262286
0.9359	High Similarity	NPC162869
0.9359	High Similarity	NPC156057
0.9359	High Similarity	NPC161960
0.9359	High Similarity	NPC304008
0.9359	High Similarity	NPC187745
0.9359	High Similarity	NPC219867
0.9355	High Similarity	NPC226025
0.9355	High Similarity	NPC472909
0.9355	High Similarity	NPC321779
0.9355	High Similarity	NPC213622
0.9355	High Similarity	NPC476169
0.9351	High Similarity	NPC39732
0.9351	High Similarity	NPC60972
0.9351	High Similarity	NPC237994
0.9351	High Similarity	NPC106976
0.9351	High Similarity	NPC477231
0.9351	High Similarity	NPC302950
0.9351	High Similarity	NPC219582
0.9351	High Similarity	NPC257648
0.9351	High Similarity	NPC236637
0.9346	High Similarity	NPC29777
0.9346	High Similarity	NPC3825
0.9346	High Similarity	NPC88804

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 NPC474162 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	367
0.1-0.2	934
0.2-0.3	1728
0.3-0.4	2648
0.4-0.5	1816
0.5-0.6	986
0.6-0.7	472
0.7-0.8	146
0.8-0.85	36
0.85-0.9	14
0.9-0.95	3
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9416	High Similarity	NPD2393	Clinical (unspecified phase)
0.9351	High Similarity	NPD1934	Approved
0.929	High Similarity	NPD2801	Approved
0.9012	High Similarity	NPD6166	Phase 2
0.9012	High Similarity	NPD6167	Clinical (unspecified phase)
0.9012	High Similarity	NPD6168	Clinical (unspecified phase)
0.9	High Similarity	NPD5494	Approved
0.8954	High Similarity	NPD1511	Approved
0.8931	High Similarity	NPD3882	Suspended
0.8854	High Similarity	NPD4380	Phase 2
0.8848	High Similarity	NPD7054	Approved
0.8839	High Similarity	NPD1512	Approved
0.8795	High Similarity	NPD7074	Phase 3
0.8795	High Similarity	NPD7472	Approved
0.8788	High Similarity	NPD3818	Discontinued
0.8774	High Similarity	NPD4378	Clinical (unspecified phase)
0.875	High Similarity	NPD3817	Phase 2
0.8696	High Similarity	NPD4868	Clinical (unspecified phase)
0.8639	High Similarity	NPD4338	Clinical (unspecified phase)
0.8634	High Similarity	NPD8443	Clinical (unspecified phase)
0.8631	High Similarity	NPD6797	Phase 2
0.8614	High Similarity	NPD7473	Discontinued
0.858	High Similarity	NPD7251	Discontinued
0.8545	High Similarity	NPD6232	Discontinued
0.8535	High Similarity	NPD7410	Clinical (unspecified phase)
0.8529	High Similarity	NPD7808	Phase 3
0.8528	High Similarity	NPD7075	Discontinued
0.8528	High Similarity	NPD4381	Clinical (unspecified phase)
0.8457	Intermediate Similarity	NPD7819	Suspended
0.8457	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8442	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8442	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8402	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8402	Intermediate Similarity	NPD5844	Phase 1
0.8387	Intermediate Similarity	NPD1549	Phase 2
0.8373	Intermediate Similarity	NPD6959	Discontinued
0.8344	Intermediate Similarity	NPD1465	Phase 2
0.8333	Intermediate Similarity	NPD7411	Suspended
0.8312	Intermediate Similarity	NPD1510	Phase 2
0.8282	Intermediate Similarity	NPD6801	Discontinued
0.8258	Intermediate Similarity	NPD2796	Approved
0.8198	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8155	Intermediate Similarity	NPD1247	Approved
0.8125	Intermediate Similarity	NPD6799	Approved
0.8118	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8072	Intermediate Similarity	NPD5402	Approved
0.8052	Intermediate Similarity	NPD1240	Approved
0.8052	Intermediate Similarity	NPD943	Approved
0.8049	Intermediate Similarity	NPD6599	Discontinued
0.8046	Intermediate Similarity	NPD6559	Discontinued
0.8038	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8036	Intermediate Similarity	NPD919	Approved
0.8024	Intermediate Similarity	NPD7768	Phase 2
0.7987	Intermediate Similarity	NPD2800	Approved
0.7976	Intermediate Similarity	NPD3749	Approved
0.7963	Intermediate Similarity	NPD2533	Approved
0.7963	Intermediate Similarity	NPD2532	Approved
0.7963	Intermediate Similarity	NPD2534	Approved
0.7953	Intermediate Similarity	NPD3926	Phase 2
0.7949	Intermediate Similarity	NPD1607	Approved
0.7937	Intermediate Similarity	NPD3750	Approved
0.7935	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7935	Intermediate Similarity	NPD1613	Approved
0.7908	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7866	Intermediate Similarity	NPD5403	Approved
0.7865	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7843	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7838	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7833	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7824	Intermediate Similarity	NPD6234	Discontinued
0.7806	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7799	Intermediate Similarity	NPD2935	Discontinued
0.7799	Intermediate Similarity	NPD6100	Approved
0.7799	Intermediate Similarity	NPD6099	Approved
0.7797	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD230	Phase 1
0.7764	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7758	Intermediate Similarity	NPD920	Approved
0.7747	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7744	Intermediate Similarity	NPD5401	Approved
0.7742	Intermediate Similarity	NPD3027	Phase 3
0.774	Intermediate Similarity	NPD7685	Pre-registration
0.7736	Intermediate Similarity	NPD2799	Discontinued
0.7733	Intermediate Similarity	NPD7199	Phase 2
0.7714	Intermediate Similarity	NPD7228	Approved
0.7714	Intermediate Similarity	NPD3751	Discontinued
0.7688	Intermediate Similarity	NPD3787	Discontinued
0.7677	Intermediate Similarity	NPD4908	Phase 1
0.7665	Intermediate Similarity	NPD3226	Approved
0.7663	Intermediate Similarity	NPD4363	Phase 3
0.7663	Intermediate Similarity	NPD4360	Phase 2
0.7658	Intermediate Similarity	NPD447	Suspended
0.7654	Intermediate Similarity	NPD8313	Approved
0.7654	Intermediate Similarity	NPD8312	Approved
0.7651	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7644	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.764	Intermediate Similarity	NPD2346	Discontinued
0.7636	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7636	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7633	Intermediate Similarity	NPD37	Approved
0.7625	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7625	Intermediate Similarity	NPD3748	Approved
0.7625	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.761	Intermediate Similarity	NPD6651	Approved
0.7607	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7607	Intermediate Similarity	NPD4628	Phase 3
0.7602	Intermediate Similarity	NPD4967	Phase 2
0.7602	Intermediate Similarity	NPD4965	Approved
0.7602	Intermediate Similarity	NPD4966	Approved
0.7584	Intermediate Similarity	NPD5953	Discontinued
0.758	Intermediate Similarity	NPD2313	Discontinued
0.758	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7578	Intermediate Similarity	NPD1551	Phase 2
0.7576	Intermediate Similarity	NPD7390	Discontinued
0.7571	Intermediate Similarity	NPD7286	Phase 2
0.7546	Intermediate Similarity	NPD1243	Approved
0.7531	Intermediate Similarity	NPD2344	Approved
0.7527	Intermediate Similarity	NPD8150	Discontinued
0.7515	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD9494	Approved
0.75	Intermediate Similarity	NPD1653	Approved
0.75	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7486	Intermediate Similarity	NPD5711	Approved
0.7486	Intermediate Similarity	NPD5710	Approved
0.747	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.746	Intermediate Similarity	NPD6780	Approved
0.746	Intermediate Similarity	NPD6779	Approved
0.746	Intermediate Similarity	NPD6782	Approved
0.746	Intermediate Similarity	NPD6777	Approved
0.746	Intermediate Similarity	NPD6776	Approved
0.746	Intermediate Similarity	NPD6781	Approved
0.746	Intermediate Similarity	NPD6778	Approved
0.7455	Intermediate Similarity	NPD6190	Approved
0.7451	Intermediate Similarity	NPD1610	Phase 2
0.7438	Intermediate Similarity	NPD5124	Phase 1
0.7438	Intermediate Similarity	NPD1933	Approved
0.7438	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7432	Intermediate Similarity	NPD8434	Phase 2
0.7425	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7409	Intermediate Similarity	NPD7584	Approved
0.7405	Intermediate Similarity	NPD4625	Phase 3
0.7394	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD7229	Phase 3
0.7368	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD3268	Approved
0.7355	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD7458	Discontinued
0.7353	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7349	Intermediate Similarity	NPD2309	Approved
0.7345	Intermediate Similarity	NPD5242	Approved
0.7344	Intermediate Similarity	NPD7435	Discontinued
0.734	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.734	Intermediate Similarity	NPD4361	Phase 2
0.7333	Intermediate Similarity	NPD8151	Discontinued
0.7325	Intermediate Similarity	NPD2798	Approved
0.7308	Intermediate Similarity	NPD7549	Discontinued
0.7303	Intermediate Similarity	NPD2403	Approved
0.7301	Intermediate Similarity	NPD7033	Discontinued
0.7273	Intermediate Similarity	NPD2424	Discontinued
0.7267	Intermediate Similarity	NPD4060	Phase 1
0.7261	Intermediate Similarity	NPD2797	Approved
0.7259	Intermediate Similarity	NPD7783	Phase 2
0.7259	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7254	Intermediate Similarity	NPD7698	Approved
0.7254	Intermediate Similarity	NPD7696	Phase 3
0.7254	Intermediate Similarity	NPD7697	Approved
0.7253	Intermediate Similarity	NPD7240	Approved
0.725	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD4749	Approved
0.7241	Intermediate Similarity	NPD5353	Approved
0.7226	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD6844	Discontinued
0.7216	Intermediate Similarity	NPD7870	Phase 2
0.7216	Intermediate Similarity	NPD7871	Phase 2
0.7202	Intermediate Similarity	NPD6823	Phase 2
0.7196	Intermediate Similarity	NPD6535	Approved
0.7196	Intermediate Similarity	NPD6534	Approved
0.7194	Intermediate Similarity	NPD7701	Phase 2
0.719	Intermediate Similarity	NPD1548	Phase 1
0.7184	Intermediate Similarity	NPD8455	Phase 2
0.7179	Intermediate Similarity	NPD1608	Approved
0.7172	Intermediate Similarity	NPD7801	Approved
0.717	Intermediate Similarity	NPD2861	Phase 2
0.7152	Intermediate Similarity	NPD1203	Approved
0.715	Intermediate Similarity	NPD2493	Approved
0.715	Intermediate Similarity	NPD2494	Approved
0.7135	Intermediate Similarity	NPD8127	Discontinued
0.7128	Intermediate Similarity	NPD4583	Approved
0.7128	Intermediate Similarity	NPD4582	Approved
0.7126	Intermediate Similarity	NPD6674	Discontinued
0.7125	Intermediate Similarity	NPD6832	Phase 2
0.7121	Intermediate Similarity	NPD7874	Approved
0.7121	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD6355	Discontinued
0.7108	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7094	Intermediate Similarity	NPD4111	Phase 1
0.7094	Intermediate Similarity	NPD4665	Approved
0.7091	Intermediate Similarity	NPD4308	Phase 3
0.7086	Intermediate Similarity	NPD5761	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