NPASS Compound

Structure

NPC473834 OpenBabel07101718312D 39 43 0 0 1 0 0 0 0 0999 V2000 2.3005 5.1808 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0000 -1.7321 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 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8412 4.1354 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 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1720 4.8785 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5322 3.1843 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 3.4641 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 -3.1939 4.6706 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5540 2.9764 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 -2.0000 1.7321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1636 5.1808 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 0.5685 4.1808 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 3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8849 3.7195 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 -1.1636 4.1808 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 -0.2976 5.6808 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2976 3.6808 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5685 5.1808 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5000 2.5981 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 -1.9067 3.5116 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -3.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2976 6.6808 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4345 5.6808 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.7321 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5055 2.7026 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 36 1 0 0 0 0 2 37 1 0 0 0 0 3 38 1 0 0 0 0 4 6 2 0 0 0 0 4 7 1 0 0 0 0 5 8 2 0 0 0 0 5 9 1 0 0 0 0 6 11 1 0 0 0 0 7 12 2 0 0 0 0 8 14 1 0 0 0 0 9 15 2 0 0 0 0 10 13 2 0 0 0 0 10 16 1 0 0 0 0 11 22 2 0 0 0 0 12 22 1 0 0 0 0 13 22 1 0 0 0 0 14 23 2 0 0 0 0 15 23 1 0 0 0 0 16 33 1 0 0 0 0 17 24 1 0 0 0 0 17 30 1 0 0 0 0 18 25 2 0 0 0 0 18 27 1 0 0 0 0 19 26 1 0 0 0 0 19 31 2 0 0 0 0 20 28 2 0 0 0 0 20 29 1 0 0 0 0 21 24 2 0 0 0 0 21 33 1 0 0 0 0 23 32 1 0 0 0 0 24 26 1 0 0 0 0 25 28 1 0 0 0 0 25 32 1 0 0 0 0 26 34 2 0 0 0 0 27 29 2 0 0 0 0 27 35 1 0 0 0 0 28 39 1 0 0 0 0 29 36 1 0 0 0 0 30 32 2 0 0 0 0 30 39 1 0 0 0 0 31 33 1 0 0 0 0 31 37 1 0 0 0 0 33 38 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	522.2
Volume:	552.373
LogP:	4.83
LogD:	4.257
LogS:	-5.636
# Rotatable Bonds:	9
TPSA:	78.13
# H-Bond Aceptor:	6
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.258
Synthetic Accessibility Score:	3.729
Fsp3:	0.182
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.04
MDCK Permeability:	9.943287295754999e-06
Pgp-inhibitor:	0.999
Pgp-substrate:	0.006
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.354

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.026
Plasma Protein Binding (PPB):	101.691162109375%
Volume Distribution (VD):	0.378
Pgp-substrate:	0.8613515496253967%

ADMET: Metabolism

CYP1A2-inhibitor:	0.884
CYP1A2-substrate:	0.934
CYP2C19-inhibitor:	0.97
CYP2C19-substrate:	0.206
CYP2C9-inhibitor:	0.95
CYP2C9-substrate:	0.882
CYP2D6-inhibitor:	0.933
CYP2D6-substrate:	0.802
CYP3A4-inhibitor:	0.958
CYP3A4-substrate:	0.91

ADMET: Excretion

Clearance (CL):	5.849
Half-life (T1/2):	0.134

ADMET: Toxicity

hERG Blockers:	0.236
Human Hepatotoxicity (H-HT):	0.91
Drug-inuced Liver Injury (DILI):	0.945
AMES Toxicity:	0.625
Rat Oral Acute Toxicity:	0.688
Maximum Recommended Daily Dose:	0.909
Skin Sensitization:	0.477
Carcinogencity:	0.797
Eye Corrosion:	0.003
Eye Irritation:	0.009
Respiratory Toxicity:	0.952

Download Data

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

Natural Product: NPC473834

Natural Product ID:	NPC473834
*Common Name:**	2-[4,5-Dimethoxy-5-(3-Phenyl-Trans-Allyl)Cyclohexa-3,6-Dien-2-On-1-Ylmethyl]-5-Hydroxy-6-Methoxy-3-Phenylbenzofuran
IUPAC Name:	2-[(5-hydroxy-6-methoxy-3-phenyl-1-benzofuran-2-yl)methyl]-4,5-dimethoxy-4-[(E)-3-phenylprop-2-enyl]cyclohexa-2,5-dien-1-one
Synonyms:
Standard InCHIKey:	TZBPQIOKLWLNNI-JLHYYAGUSA-N
Standard InCHI:	InChI=1S/C33H30O6/c1-36-29-20-28-25(18-27(29)35)32(23-14-8-5-9-15-23)30(39-28)17-24-21-33(38-3,31(37-2)19-26(24)34)16-10-13-22-11-6-4-7-12-22/h4-15,18-21,35H,16-17H2,1-3H3/b13-10+
SMILES:	COC1=CC(=O)C(=CC1(OC)C/C=C/c1ccccc1)Cc1oc2c(c1c1ccccc1)cc(c(c2)OC)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL453028
PubChem CID:	10052458
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000301] Benzofurans [CHEMONTID:0002584] Phenylbenzofurans

*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
NPO29428	Dalbergia cochinchinensis	Species	Fabaceae	Eukaryota	n.a.	seed	n.a.	DOI[10.1016/S0031-9422(98)00552-4]
NPO29428	Dalbergia cochinchinensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12932142]
NPO29428	Dalbergia cochinchinensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29428	Dalbergia cochinchinensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29428	Dalbergia cochinchinensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO29428	Dalbergia cochinchinensis	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
Others	3

Activity Type	# Activity
Others	3

Target ID	Target Type	Target Name	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified	Inhibition	=	0.6	%	PMID[473757]
NPT2	Others	Unspecified	Inhibition	=	3.8	%	PMID[473757]
NPT2	Others	Unspecified	Inhibition	=	17.0	%	PMID[473757]

☑ 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 NPC473834 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	453
0.1-0.2	1815
0.2-0.3	4225
0.3-0.4	10736
0.4-0.5	7440
0.5-0.6	3682
0.6-0.7	5253
0.7-0.8	5418
0.8-0.85	2182
0.85-0.9	1197
0.9-0.95	294
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9693	High Similarity	NPC174700
0.9503	High Similarity	NPC312056
0.9503	High Similarity	NPC84515
0.9441	High Similarity	NPC188486
0.9398	High Similarity	NPC216842
0.9398	High Similarity	NPC476640
0.9398	High Similarity	NPC82217
0.9398	High Similarity	NPC310794
0.939	High Similarity	NPC50394
0.9341	High Similarity	NPC287243
0.9337	High Similarity	NPC54098
0.9337	High Similarity	NPC230619
0.9325	High Similarity	NPC133065
0.9317	High Similarity	NPC16935
0.9317	High Similarity	NPC196879
0.9286	High Similarity	NPC8127
0.9286	High Similarity	NPC49667
0.9277	High Similarity	NPC476641
0.9273	High Similarity	NPC470704
0.9273	High Similarity	NPC247973
0.9268	High Similarity	NPC36320
0.9268	High Similarity	NPC39306
0.9268	High Similarity	NPC45449
0.9212	High Similarity	NPC277480
0.9207	High Similarity	NPC1706
0.9207	High Similarity	NPC59295
0.9207	High Similarity	NPC39305
0.9207	High Similarity	NPC263092
0.9207	High Similarity	NPC1755
0.9193	High Similarity	NPC45131
0.9167	High Similarity	NPC65885
0.9152	High Similarity	NPC291110
0.9152	High Similarity	NPC37183
0.9146	High Similarity	NPC238995
0.9146	High Similarity	NPC272722
0.9141	High Similarity	NPC188967
0.9123	High Similarity	NPC47883
0.9118	High Similarity	NPC297807
0.9112	High Similarity	NPC227906
0.9107	High Similarity	NPC248593
0.9107	High Similarity	NPC28589
0.908	High Similarity	NPC154304
0.908	High Similarity	NPC190487
0.9059	High Similarity	NPC164384
0.9053	High Similarity	NPC149846
0.9053	High Similarity	NPC261471
0.9048	High Similarity	NPC131866
0.9042	High Similarity	NPC86477
0.9036	High Similarity	NPC29411
0.903	High Similarity	NPC83922
0.903	High Similarity	NPC472448
0.9024	High Similarity	NPC476980
0.9023	High Similarity	NPC73929
0.9023	High Similarity	NPC47905
0.9023	High Similarity	NPC139683
0.9018	High Similarity	NPC185526
0.9017	High Similarity	NPC154527
0.9012	High Similarity	NPC256612
0.9012	High Similarity	NPC20830
0.9006	High Similarity	NPC475783
0.9006	High Similarity	NPC98546
0.9006	High Similarity	NPC125300
0.8988	High Similarity	NPC202470
0.8988	High Similarity	NPC247136
0.8976	High Similarity	NPC272064
0.8976	High Similarity	NPC475985
0.897	High Similarity	NPC29876
0.897	High Similarity	NPC167678
0.897	High Similarity	NPC259456
0.8966	High Similarity	NPC304322
0.8966	High Similarity	NPC226725
0.8963	High Similarity	NPC195832
0.8963	High Similarity	NPC476242
0.8957	High Similarity	NPC472916
0.8957	High Similarity	NPC472461
0.8951	High Similarity	NPC274327
0.8951	High Similarity	NPC292214
0.8951	High Similarity	NPC145379
0.8951	High Similarity	NPC88645
0.8951	High Similarity	NPC255350
0.8951	High Similarity	NPC22519
0.8951	High Similarity	NPC160951
0.8951	High Similarity	NPC271779
0.8951	High Similarity	NPC47781
0.8951	High Similarity	NPC176775
0.8951	High Similarity	NPC231018
0.8951	High Similarity	NPC206238
0.8951	High Similarity	NPC183878
0.8951	High Similarity	NPC69394
0.8951	High Similarity	NPC167091
0.8941	High Similarity	NPC37606
0.8935	High Similarity	NPC218533
0.8935	High Similarity	NPC472276
0.8935	High Similarity	NPC78830
0.8929	High Similarity	NPC243877
0.8929	High Similarity	NPC14662
0.8922	High Similarity	NPC275780
0.8922	High Similarity	NPC239752
0.8922	High Similarity	NPC224280
0.8922	High Similarity	NPC472450
0.8922	High Similarity	NPC234052
0.8922	High Similarity	NPC26386
0.8916	High Similarity	NPC81679
0.8916	High Similarity	NPC261470
0.8914	High Similarity	NPC248315
0.8909	High Similarity	NPC200746
0.8909	High Similarity	NPC204290
0.8909	High Similarity	NPC139036
0.8908	High Similarity	NPC476170
0.8902	High Similarity	NPC99597
0.8902	High Similarity	NPC210084
0.8902	High Similarity	NPC472911
0.8902	High Similarity	NPC475267
0.8902	High Similarity	NPC474208
0.8902	High Similarity	NPC472914
0.8902	High Similarity	NPC96167
0.8902	High Similarity	NPC299520
0.8902	High Similarity	NPC245758
0.8902	High Similarity	NPC300727
0.8902	High Similarity	NPC262286
0.8902	High Similarity	NPC78225
0.8902	High Similarity	NPC469584
0.8902	High Similarity	NPC472910
0.8902	High Similarity	NPC156057
0.8902	High Similarity	NPC36852
0.8902	High Similarity	NPC97523
0.8902	High Similarity	NPC472913
0.8902	High Similarity	NPC48208
0.8902	High Similarity	NPC476981
0.8902	High Similarity	NPC181960
0.8902	High Similarity	NPC162869
0.8902	High Similarity	NPC222814
0.8902	High Similarity	NPC241904
0.8902	High Similarity	NPC129684
0.8902	High Similarity	NPC474836
0.8896	High Similarity	NPC50715
0.8896	High Similarity	NPC201136
0.8896	High Similarity	NPC2928
0.8896	High Similarity	NPC92659
0.8896	High Similarity	NPC196439
0.8896	High Similarity	NPC227325
0.8896	High Similarity	NPC2476
0.8896	High Similarity	NPC128863
0.8896	High Similarity	NPC213622
0.8896	High Similarity	NPC167815
0.8896	High Similarity	NPC146165
0.8896	High Similarity	NPC138360
0.8896	High Similarity	NPC280339
0.8896	High Similarity	NPC183597
0.8896	High Similarity	NPC163780
0.8896	High Similarity	NPC208197
0.8896	High Similarity	NPC4455
0.8889	High Similarity	NPC222830
0.8889	High Similarity	NPC198826
0.8889	High Similarity	NPC120537
0.8889	High Similarity	NPC180234
0.8889	High Similarity	NPC199100
0.8889	High Similarity	NPC25270
0.8889	High Similarity	NPC162313
0.8889	High Similarity	NPC187498
0.8889	High Similarity	NPC275836
0.8889	High Similarity	NPC39007
0.8889	High Similarity	NPC275722
0.8889	High Similarity	NPC241498
0.8889	High Similarity	NPC71334
0.8889	High Similarity	NPC101996
0.8889	High Similarity	NPC156222
0.8889	High Similarity	NPC120163
0.8889	High Similarity	NPC289244
0.8889	High Similarity	NPC60972
0.8889	High Similarity	NPC188203
0.8889	High Similarity	NPC57030
0.8889	High Similarity	NPC131624
0.8889	High Similarity	NPC83508
0.8889	High Similarity	NPC301323
0.8889	High Similarity	NPC39732
0.8889	High Similarity	NPC293183
0.8889	High Similarity	NPC239128
0.8889	High Similarity	NPC161277
0.8889	High Similarity	NPC100887
0.8889	High Similarity	NPC212678
0.8889	High Similarity	NPC256283
0.8876	High Similarity	NPC152477
0.8876	High Similarity	NPC288813
0.8869	High Similarity	NPC39091
0.8869	High Similarity	NPC173292
0.8869	High Similarity	NPC170245
0.8869	High Similarity	NPC235610
0.8869	High Similarity	NPC272560
0.8862	High Similarity	NPC159508
0.8862	High Similarity	NPC152659
0.8862	High Similarity	NPC306321
0.8862	High Similarity	NPC248638
0.8862	High Similarity	NPC124038
0.8862	High Similarity	NPC23298
0.8862	High Similarity	NPC303460
0.8862	High Similarity	NPC189473
0.8862	High Similarity	NPC236521
0.8862	High Similarity	NPC89131
0.8855	High Similarity	NPC196179

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 NPC473834 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	390
0.1-0.2	970
0.2-0.3	1779
0.3-0.4	2690
0.4-0.5	1831
0.5-0.6	959
0.6-0.7	363
0.7-0.8	128
0.8-0.85	26
0.85-0.9	13
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8951	High Similarity	NPD2801	Approved
0.8727	High Similarity	NPD3882	Suspended
0.8659	High Similarity	NPD1934	Approved
0.8588	High Similarity	NPD6166	Phase 2
0.8588	High Similarity	NPD6167	Clinical (unspecified phase)
0.8588	High Similarity	NPD6168	Clinical (unspecified phase)
0.8571	High Similarity	NPD5494	Approved
0.8494	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8488	Intermediate Similarity	NPD3818	Discontinued
0.8452	Intermediate Similarity	NPD3749	Approved
0.8421	Intermediate Similarity	NPD3926	Phase 2
0.8395	Intermediate Similarity	NPD1511	Approved
0.8393	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8363	Intermediate Similarity	NPD6232	Discontinued
0.8324	Intermediate Similarity	NPD7473	Discontinued
0.8293	Intermediate Similarity	NPD1512	Approved
0.8229	Intermediate Similarity	NPD5844	Phase 1
0.8198	Intermediate Similarity	NPD1247	Approved
0.8182	Intermediate Similarity	NPD7074	Phase 3
0.8146	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8136	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8125	Intermediate Similarity	NPD7054	Approved
0.8121	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8118	Intermediate Similarity	NPD3817	Phase 2
0.8079	Intermediate Similarity	NPD7472	Approved
0.8077	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.8059	Intermediate Similarity	NPD1465	Phase 2
0.8025	Intermediate Similarity	NPD2344	Approved
0.8012	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8012	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7989	Intermediate Similarity	NPD6559	Discontinued
0.7989	Intermediate Similarity	NPD6959	Discontinued
0.7988	Intermediate Similarity	NPD4380	Phase 2
0.7965	Intermediate Similarity	NPD7768	Phase 2
0.7955	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7944	Intermediate Similarity	NPD7808	Phase 3
0.7933	Intermediate Similarity	NPD6797	Phase 2
0.7919	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7889	Intermediate Similarity	NPD7251	Discontinued
0.7874	Intermediate Similarity	NPD919	Approved
0.7866	Intermediate Similarity	NPD1549	Phase 2
0.7849	Intermediate Similarity	NPD7819	Suspended
0.7836	Intermediate Similarity	NPD7411	Suspended
0.7831	Intermediate Similarity	NPD2309	Approved
0.7816	Intermediate Similarity	NPD7075	Discontinued
0.7811	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7805	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7805	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7803	Intermediate Similarity	NPD5402	Approved
0.7791	Intermediate Similarity	NPD1510	Phase 2
0.7765	Intermediate Similarity	NPD3751	Discontinued
0.7764	Intermediate Similarity	NPD1240	Approved
0.7764	Intermediate Similarity	NPD943	Approved
0.7746	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7744	Intermediate Similarity	NPD2796	Approved
0.7738	Intermediate Similarity	NPD6799	Approved
0.7717	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7711	Intermediate Similarity	NPD2800	Approved
0.7676	Intermediate Similarity	NPD8434	Phase 2
0.7674	Intermediate Similarity	NPD6599	Discontinued
0.7669	Intermediate Similarity	NPD1607	Approved
0.7665	Intermediate Similarity	NPD3750	Approved
0.7624	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7606	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7602	Intermediate Similarity	NPD920	Approved
0.7586	Intermediate Similarity	NPD6801	Discontinued
0.7584	Intermediate Similarity	NPD7199	Phase 2
0.753	Intermediate Similarity	NPD2935	Discontinued
0.7529	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD4287	Approved
0.75	Intermediate Similarity	NPD1243	Approved
0.75	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD2532	Approved
0.7485	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD2533	Approved
0.7485	Intermediate Similarity	NPD2534	Approved
0.7472	Intermediate Similarity	NPD6234	Discontinued
0.7444	Intermediate Similarity	NPD3787	Discontinued
0.744	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7427	Intermediate Similarity	NPD7390	Discontinued
0.7414	Intermediate Similarity	NPD3226	Approved
0.7407	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7399	Intermediate Similarity	NPD5403	Approved
0.7396	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD230	Phase 1
0.7394	Intermediate Similarity	NPD447	Suspended
0.7368	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD3748	Approved
0.7365	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7346	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD1613	Approved
0.7326	Intermediate Similarity	NPD8312	Approved
0.7326	Intermediate Similarity	NPD8313	Approved
0.7312	Intermediate Similarity	NPD7685	Pre-registration
0.731	Intermediate Similarity	NPD6190	Approved
0.7303	Intermediate Similarity	NPD2296	Approved
0.7288	Intermediate Similarity	NPD37	Approved
0.7283	Intermediate Similarity	NPD7228	Approved
0.7283	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD5401	Approved
0.7263	Intermediate Similarity	NPD4965	Approved
0.7263	Intermediate Similarity	NPD4966	Approved
0.7263	Intermediate Similarity	NPD4967	Phase 2
0.7256	Intermediate Similarity	NPD3027	Phase 3
0.7251	Intermediate Similarity	NPD4628	Phase 3
0.7245	Intermediate Similarity	NPD6779	Approved
0.7245	Intermediate Similarity	NPD6776	Approved
0.7245	Intermediate Similarity	NPD6782	Approved
0.7245	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7245	Intermediate Similarity	NPD6780	Approved
0.7245	Intermediate Similarity	NPD6778	Approved
0.7245	Intermediate Similarity	NPD6777	Approved
0.7245	Intermediate Similarity	NPD6781	Approved
0.7219	Intermediate Similarity	NPD1551	Phase 2
0.7219	Intermediate Similarity	NPD6100	Approved
0.7219	Intermediate Similarity	NPD6099	Approved
0.7214	Intermediate Similarity	NPD8151	Discontinued
0.7211	Intermediate Similarity	NPD8150	Discontinued
0.7195	Intermediate Similarity	NPD4908	Phase 1
0.7186	Intermediate Similarity	NPD7871	Phase 2
0.7186	Intermediate Similarity	NPD7870	Phase 2
0.7184	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7174	Intermediate Similarity	NPD2403	Approved
0.7166	Intermediate Similarity	NPD5953	Discontinued
0.7163	Intermediate Similarity	NPD7907	Approved
0.716	Intermediate Similarity	NPD2799	Discontinued
0.7159	Intermediate Similarity	NPD1653	Approved
0.7158	Intermediate Similarity	NPD7229	Phase 3
0.7151	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7783	Phase 2
0.7143	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7136	Intermediate Similarity	NPD7435	Discontinued
0.7136	Intermediate Similarity	NPD7696	Phase 3
0.7136	Intermediate Similarity	NPD7698	Approved
0.7136	Intermediate Similarity	NPD7697	Approved
0.7134	Intermediate Similarity	NPD9494	Approved
0.7108	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD3764	Approved
0.7099	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD6280	Approved
0.7095	Intermediate Similarity	NPD6279	Approved
0.7092	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.709	Intermediate Similarity	NPD7549	Discontinued
0.7083	Intermediate Similarity	NPD1933	Approved
0.7079	Intermediate Similarity	NPD7701	Phase 2
0.7076	Intermediate Similarity	NPD1471	Phase 3
0.7076	Intermediate Similarity	NPD2346	Discontinued
0.7067	Intermediate Similarity	NPD4111	Phase 1
0.7067	Intermediate Similarity	NPD4665	Approved
0.7059	Intermediate Similarity	NPD7286	Phase 2
0.7056	Intermediate Similarity	NPD5761	Phase 2
0.7056	Intermediate Similarity	NPD5760	Phase 2
0.7041	Intermediate Similarity	NPD6651	Approved
0.7027	Intermediate Similarity	NPD5242	Approved
0.7018	Intermediate Similarity	NPD5404	Approved
0.7018	Intermediate Similarity	NPD5406	Approved
0.7018	Intermediate Similarity	NPD5405	Approved
0.7018	Intermediate Similarity	NPD5408	Approved
0.701	Intermediate Similarity	NPD7874	Approved
0.701	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD2313	Discontinued
0.699	Remote Similarity	NPD6534	Approved
0.699	Remote Similarity	NPD6535	Approved
0.6976	Remote Similarity	NPD7801	Approved
0.6973	Remote Similarity	NPD6808	Phase 2
0.6973	Remote Similarity	NPD5710	Approved
0.6973	Remote Similarity	NPD5711	Approved
0.697	Remote Similarity	NPD7699	Phase 2
0.697	Remote Similarity	NPD7700	Phase 2
0.6961	Remote Similarity	NPD8455	Phase 2
0.6927	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD8127	Discontinued
0.6915	Remote Similarity	NPD2163	Approved
0.6915	Remote Similarity	NPD6823	Phase 2
0.6909	Remote Similarity	NPD1203	Approved
0.6909	Remote Similarity	NPD1470	Approved
0.6906	Remote Similarity	NPD6844	Discontinued
0.6898	Remote Similarity	NPD4575	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD2798	Approved
0.6866	Remote Similarity	NPD2493	Approved
0.6866	Remote Similarity	NPD2494	Approved
0.6864	Remote Similarity	NPD6233	Phase 2
0.686	Remote Similarity	NPD7033	Discontinued
0.6859	Remote Similarity	NPD7240	Approved
0.6857	Remote Similarity	NPD8166	Discontinued
0.6845	Remote Similarity	NPD4625	Phase 3
0.6836	Remote Similarity	NPD4357	Discontinued
0.6833	Remote Similarity	NPD7458	Discontinued
0.6831	Remote Similarity	NPD4288	Approved
0.6829	Remote Similarity	NPD9269	Phase 2
0.6826	Remote Similarity	NPD2861	Phase 2
0.6825	Remote Similarity	NPD7177	Discontinued
0.6818	Remote Similarity	NPD4360	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