NPASS Compound

Structure

NPC474444 OpenBabel07101718222D 26 28 0 0 1 0 0 0 0 0999 V2000 -3.0878 -1.7891 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 -1.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 2.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0878 1.6750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0878 1.6750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4152 3.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0878 -0.0570 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3090 2.5691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5878 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.6180 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -3.5878 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0878 -0.0570 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 -0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5878 0.8090 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 0.9511 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4152 4.3090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2872 2.7770 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.5878 0.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5878 -0.9230 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 -1.1910 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 24 1 0 0 0 0 2 25 1 0 0 0 0 3 4 2 0 0 0 0 3 7 1 0 0 0 0 4 12 1 0 0 0 0 5 6 2 0 0 0 0 5 13 1 0 0 0 0 6 16 1 0 0 0 0 7 21 2 0 0 0 0 8 12 2 0 0 0 0 8 14 1 0 0 0 0 9 12 1 0 0 0 0 9 18 2 0 0 0 0 10 13 2 0 0 0 0 10 17 1 0 0 0 0 11 15 1 0 0 0 0 11 22 1 0 0 0 0 13 19 1 0 0 0 0 14 15 1 0 0 0 0 14 20 2 0 0 0 0 15 19 1 0 0 0 0 16 17 2 0 0 0 0 16 23 1 0 0 0 0 17 24 1 0 0 0 0 18 20 1 0 0 0 0 18 25 1 0 0 0 0 19 26 1 0 0 0 0 20 26 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	356.13
Volume:	360.456
LogP:	1.836
LogD:	2.36
LogS:	-4.018
# Rotatable Bonds:	6
TPSA:	85.22
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.612
Synthetic Accessibility Score:	3.48
Fsp3:	0.25
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:	-4.761
MDCK Permeability:	7.316985374927754e-06
Pgp-inhibitor:	0.092
Pgp-substrate:	0.05
Human Intestinal Absorption (HIA):	0.027
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.003

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.177
Plasma Protein Binding (PPB):	92.15839385986328%
Volume Distribution (VD):	0.672
Pgp-substrate:	5.563852787017822%

ADMET: Metabolism

CYP1A2-inhibitor:	0.113
CYP1A2-substrate:	0.789
CYP2C19-inhibitor:	0.106
CYP2C19-substrate:	0.75
CYP2C9-inhibitor:	0.173
CYP2C9-substrate:	0.893
CYP2D6-inhibitor:	0.062
CYP2D6-substrate:	0.86
CYP3A4-inhibitor:	0.57
CYP3A4-substrate:	0.823

ADMET: Excretion

Clearance (CL):	5.199
Half-life (T1/2):	0.412

ADMET: Toxicity

hERG Blockers:	0.046
Human Hepatotoxicity (H-HT):	0.137
Drug-inuced Liver Injury (DILI):	0.13
AMES Toxicity:	0.198
Rat Oral Acute Toxicity:	0.267
Maximum Recommended Daily Dose:	0.714
Skin Sensitization:	0.66
Carcinogencity:	0.691
Eye Corrosion:	0.003
Eye Irritation:	0.035
Respiratory Toxicity:	0.59

Download Data

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

Natural Product: NPC474444

Natural Product ID:	NPC474444
*Common Name:**	(+/-)-Balanophonin
IUPAC Name:	(E)-3-[2-(4-hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-7-methoxy-2,3-dihydro-1-benzofuran-5-yl]prop-2-enal
Synonyms:	(+/-)-Balanophonin
Standard InCHIKey:	GWCSSLSMGCFIFR-ONEGZZNKSA-N
Standard InCHI:	InChI=1S/C20H20O6/c1-24-17-10-13(5-6-16(17)23)19-15(11-22)14-8-12(4-3-7-21)9-18(25-2)20(14)26-19/h3-10,15,19,22-23H,11H2,1-2H3/b4-3+
SMILES:	COC1=CC(=CC2=C1OC(C2CO)C3=CC(=C(C=C3)O)OC)C=CC=O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL468666
PubChem CID:	14274764
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0003405] 2-arylbenzofuran 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
NPO5140	Dipteryx odorata	Species	Fabaceae	Eukaryota	seeds	n.a.	n.a.	PMID[12762787]
NPO5140	Dipteryx odorata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12762809]
NPO5140	Dipteryx odorata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5140	Dipteryx odorata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5140	Dipteryx odorata	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	3
Others	2

Activity Type	# Activity
Cell Line	1
CELL-LINE	1
Individual Protein	1
NON-MOLECULAR	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT440	Individual Protein	Quinone oxidoreductase	Mus musculus	CD	=	15.1	uM	PMID[512721]
NPT65	Cell Line	HepG2	Homo sapiens	IC50	=	36500.0	nM	PMID[512722]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	48500.0	nM	PMID[512721]
NPT2	Others	Unspecified		Ratio	=	3.2	n.a.	PMID[512721]
NPT20904	CELL-LINE	Hep 3B2	Homo sapiens	IC50	=	29300.0	nM	PMID[512722]

☑ 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 NPC474444 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	358
0.1-0.2	1365
0.2-0.3	3561
0.3-0.4	9109
0.4-0.5	9654
0.5-0.6	3284
0.6-0.7	7124
0.7-0.8	6921
0.8-0.85	1041
0.85-0.9	222
0.9-0.95	41
0.95-1	17

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC93433
1.0	High Similarity	NPC264706
1.0	High Similarity	NPC284881
0.9714	High Similarity	NPC473408
0.964	High Similarity	NPC163898
0.9574	High Similarity	NPC236166
0.9485	High Similarity	NPC477939
0.9485	High Similarity	NPC209985
0.9485	High Similarity	NPC177160
0.9485	High Similarity	NPC10737
0.9485	High Similarity	NPC156502
0.9485	High Similarity	NPC54743
0.9485	High Similarity	NPC263367
0.9485	High Similarity	NPC29799
0.9379	High Similarity	NPC470769
0.9338	High Similarity	NPC249791
0.9338	High Similarity	NPC237594
0.9338	High Similarity	NPC193026
0.9338	High Similarity	NPC476387
0.9338	High Similarity	NPC187616
0.9338	High Similarity	NPC49603
0.9338	High Similarity	NPC119060
0.9286	High Similarity	NPC131971
0.9265	High Similarity	NPC26394
0.9252	High Similarity	NPC300757
0.9252	High Similarity	NPC180901
0.9214	High Similarity	NPC263261
0.9214	High Similarity	NPC87725
0.9214	High Similarity	NPC471414
0.9191	High Similarity	NPC230219
0.9149	High Similarity	NPC253878
0.913	High Similarity	NPC214729
0.9128	High Similarity	NPC470827
0.9116	High Similarity	NPC131121
0.9067	High Similarity	NPC470828
0.9051	High Similarity	NPC2190
0.9051	High Similarity	NPC18842
0.9044	High Similarity	NPC174495
0.9044	High Similarity	NPC242807
0.9044	High Similarity	NPC153739
0.9044	High Similarity	NPC42300
0.9044	High Similarity	NPC145305
0.9044	High Similarity	NPC241522
0.9044	High Similarity	NPC92164
0.9044	High Similarity	NPC257582
0.9044	High Similarity	NPC77040
0.9044	High Similarity	NPC187998
0.9044	High Similarity	NPC64201
0.9007	High Similarity	NPC267291
0.9	High Similarity	NPC477938
0.8986	High Similarity	NPC115203
0.8978	High Similarity	NPC277804
0.8971	High Similarity	NPC475875
0.8947	High Similarity	NPC478267
0.8944	High Similarity	NPC83375
0.8944	High Similarity	NPC224876
0.8921	High Similarity	NPC67247
0.8921	High Similarity	NPC16485
0.8921	High Similarity	NPC478085
0.8905	High Similarity	NPC143483
0.8897	High Similarity	NPC11258
0.8897	High Similarity	NPC21867
0.8897	High Similarity	NPC282703
0.8897	High Similarity	NPC260397
0.8897	High Similarity	NPC45774
0.8897	High Similarity	NPC128208
0.8897	High Similarity	NPC129570
0.8897	High Similarity	NPC184733
0.8897	High Similarity	NPC470084
0.8889	High Similarity	NPC45257
0.8889	High Similarity	NPC280092
0.8889	High Similarity	NPC93323
0.8889	High Similarity	NPC12641
0.8881	High Similarity	NPC67467
0.8881	High Similarity	NPC278469
0.8881	High Similarity	NPC193722
0.8873	High Similarity	NPC254759
0.8873	High Similarity	NPC309124
0.8873	High Similarity	NPC160283
0.8873	High Similarity	NPC184797
0.8865	High Similarity	NPC126206
0.8841	High Similarity	NPC228346
0.8841	High Similarity	NPC158079
0.8841	High Similarity	NPC7171
0.8841	High Similarity	NPC40432
0.8841	High Similarity	NPC161557
0.8841	High Similarity	NPC27843
0.8841	High Similarity	NPC115207
0.8836	High Similarity	NPC31325
0.8836	High Similarity	NPC114505
0.8836	High Similarity	NPC275284
0.8836	High Similarity	NPC213074
0.8836	High Similarity	NPC15956
0.8836	High Similarity	NPC193473
0.8836	High Similarity	NPC224674
0.8824	High Similarity	NPC163332
0.8824	High Similarity	NPC118787
0.8824	High Similarity	NPC98745
0.8824	High Similarity	NPC469889
0.8824	High Similarity	NPC292056
0.8824	High Similarity	NPC41706
0.8824	High Similarity	NPC111247
0.8824	High Similarity	NPC147821
0.8824	High Similarity	NPC165045
0.8824	High Similarity	NPC319625
0.8824	High Similarity	NPC183181
0.8824	High Similarity	NPC118533
0.8819	High Similarity	NPC47633
0.8819	High Similarity	NPC85264
0.8819	High Similarity	NPC477616
0.8819	High Similarity	NPC102044
0.8816	High Similarity	NPC478269
0.8811	High Similarity	NPC311530
0.8808	High Similarity	NPC228357
0.8803	High Similarity	NPC260741
0.8803	High Similarity	NPC232164
0.8803	High Similarity	NPC473739
0.8803	High Similarity	NPC236306
0.8803	High Similarity	NPC70682
0.8803	High Similarity	NPC292882
0.8794	High Similarity	NPC471664
0.8794	High Similarity	NPC471988
0.8794	High Similarity	NPC471665
0.8794	High Similarity	NPC77861
0.8786	High Similarity	NPC135127
0.8786	High Similarity	NPC287745
0.8777	High Similarity	NPC181049
0.8777	High Similarity	NPC207400
0.8759	High Similarity	NPC472968
0.8759	High Similarity	NPC63879
0.8758	High Similarity	NPC472962
0.8758	High Similarity	NPC472961
0.875	High Similarity	NPC191037
0.875	High Similarity	NPC476840
0.875	High Similarity	NPC58607
0.875	High Similarity	NPC125495
0.875	High Similarity	NPC206882
0.875	High Similarity	NPC178284
0.875	High Similarity	NPC107161
0.875	High Similarity	NPC476842
0.8732	High Similarity	NPC281780
0.8723	High Similarity	NPC256262
0.8718	High Similarity	NPC43065
0.8714	High Similarity	NPC158331
0.8714	High Similarity	NPC36490
0.8714	High Similarity	NPC475840
0.8707	High Similarity	NPC21776
0.8707	High Similarity	NPC16269
0.8707	High Similarity	NPC101376
0.8699	High Similarity	NPC476301
0.8699	High Similarity	NPC43508
0.8699	High Similarity	NPC181615
0.8696	High Similarity	NPC86030
0.8696	High Similarity	NPC5851
0.8686	High Similarity	NPC5428
0.8686	High Similarity	NPC21563
0.8681	High Similarity	NPC247291
0.8681	High Similarity	NPC471389
0.8681	High Similarity	NPC35216
0.8676	High Similarity	NPC194519
0.8676	High Similarity	NPC148627
0.8676	High Similarity	NPC81641
0.8676	High Similarity	NPC87113
0.8662	High Similarity	NPC248727
0.8662	High Similarity	NPC472334
0.8662	High Similarity	NPC16435
0.8662	High Similarity	NPC470802
0.8662	High Similarity	NPC306441
0.8662	High Similarity	NPC270456
0.8662	High Similarity	NPC472336
0.8662	High Similarity	NPC265433
0.8662	High Similarity	NPC162659
0.8658	High Similarity	NPC98624
0.8652	High Similarity	NPC326095
0.8652	High Similarity	NPC471942
0.8652	High Similarity	NPC244983
0.8643	High Similarity	NPC175067
0.8643	High Similarity	NPC204215
0.8643	High Similarity	NPC4940
0.8639	High Similarity	NPC324492
0.8639	High Similarity	NPC287495
0.8639	High Similarity	NPC317053
0.8639	High Similarity	NPC9370
0.863	High Similarity	NPC79429
0.863	High Similarity	NPC471667
0.863	High Similarity	NPC471763
0.863	High Similarity	NPC217635
0.863	High Similarity	NPC473108
0.8623	High Similarity	NPC245826
0.8623	High Similarity	NPC474178
0.8623	High Similarity	NPC252307
0.8623	High Similarity	NPC72529
0.8621	High Similarity	NPC476356
0.8621	High Similarity	NPC204347
0.8621	High Similarity	NPC41782
0.8621	High Similarity	NPC475891
0.8621	High Similarity	NPC2613
0.8621	High Similarity	NPC59841
0.8611	High Similarity	NPC55793
0.8611	High Similarity	NPC27495

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 NPC474444 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	306
0.1-0.2	851
0.2-0.3	1700
0.3-0.4	2675
0.4-0.5	1816
0.5-0.6	940
0.6-0.7	692
0.7-0.8	163
0.8-0.85	7
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8429	Intermediate Similarity	NPD3027	Phase 3
0.838	Intermediate Similarity	NPD1613	Approved
0.838	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8125	Intermediate Similarity	NPD4060	Phase 1
0.8099	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.8077	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8028	Intermediate Similarity	NPD2861	Phase 2
0.8028	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.8013	Intermediate Similarity	NPD1934	Approved
0.8	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7975	Intermediate Similarity	NPD3882	Suspended
0.7871	Intermediate Similarity	NPD1653	Approved
0.7866	Intermediate Similarity	NPD3818	Discontinued
0.7862	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7826	Intermediate Similarity	NPD5494	Approved
0.7815	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7815	Intermediate Similarity	NPD6674	Discontinued
0.78	Intermediate Similarity	NPD7266	Discontinued
0.7764	Intermediate Similarity	NPD6234	Discontinued
0.7755	Intermediate Similarity	NPD3620	Phase 2
0.7755	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.775	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7744	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7744	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7744	Intermediate Similarity	NPD6166	Phase 2
0.7736	Intermediate Similarity	NPD2801	Approved
0.7724	Intermediate Similarity	NPD4908	Phase 1
0.7721	Intermediate Similarity	NPD5283	Phase 1
0.7711	Intermediate Similarity	NPD5844	Phase 1
0.7682	Intermediate Similarity	NPD5762	Approved
0.7682	Intermediate Similarity	NPD5763	Approved
0.7679	Intermediate Similarity	NPD6559	Discontinued
0.7673	Intermediate Similarity	NPD37	Approved
0.7647	Intermediate Similarity	NPD4628	Phase 3
0.764	Intermediate Similarity	NPD4966	Approved
0.764	Intermediate Similarity	NPD4967	Phase 2
0.764	Intermediate Similarity	NPD4965	Approved
0.7632	Intermediate Similarity	NPD2424	Discontinued
0.7606	Intermediate Similarity	NPD1610	Phase 2
0.7584	Intermediate Similarity	NPD6355	Discontinued
0.7574	Intermediate Similarity	NPD228	Approved
0.7569	Intermediate Similarity	NPD8651	Approved
0.7561	Intermediate Similarity	NPD7199	Phase 2
0.7561	Intermediate Similarity	NPD8127	Discontinued
0.756	Intermediate Similarity	NPD7074	Phase 3
0.755	Intermediate Similarity	NPD5588	Approved
0.7547	Intermediate Similarity	NPD4380	Phase 2
0.7545	Intermediate Similarity	NPD7228	Approved
0.75	Intermediate Similarity	NPD7054	Approved
0.75	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD5536	Phase 2
0.75	Intermediate Similarity	NPD1511	Approved
0.75	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD4536	Approved
0.7483	Intermediate Similarity	NPD4538	Approved
0.7483	Intermediate Similarity	NPD3705	Approved
0.7467	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7467	Intermediate Similarity	NPD5124	Phase 1
0.7456	Intermediate Similarity	NPD7472	Approved
0.7451	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7451	Intermediate Similarity	NPD6005	Phase 3
0.7451	Intermediate Similarity	NPD6004	Phase 3
0.7451	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7451	Intermediate Similarity	NPD6002	Phase 3
0.7436	Intermediate Similarity	NPD5058	Phase 3
0.7432	Intermediate Similarity	NPD4625	Phase 3
0.7426	Intermediate Similarity	NPD3022	Approved
0.7426	Intermediate Similarity	NPD3021	Approved
0.7419	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD4110	Phase 3
0.7419	Intermediate Similarity	NPD6331	Phase 2
0.7415	Intermediate Similarity	NPD9494	Approved
0.7405	Intermediate Similarity	NPD1512	Approved
0.74	Intermediate Similarity	NPD1558	Phase 1
0.7386	Intermediate Similarity	NPD2935	Discontinued
0.7383	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7378	Intermediate Similarity	NPD7075	Discontinued
0.7372	Intermediate Similarity	NPD6190	Approved
0.7365	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7362	Intermediate Similarity	NPD3817	Phase 2
0.7361	Intermediate Similarity	NPD1091	Approved
0.7357	Intermediate Similarity	NPD7157	Approved
0.7355	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD2684	Approved
0.7351	Intermediate Similarity	NPD5735	Approved
0.7349	Intermediate Similarity	NPD1247	Approved
0.7343	Intermediate Similarity	NPD4626	Approved
0.7342	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD919	Approved
0.7329	Intermediate Similarity	NPD6696	Suspended
0.7324	Intermediate Similarity	NPD1548	Phase 1
0.7321	Intermediate Similarity	NPD27	Approved
0.7321	Intermediate Similarity	NPD2489	Approved
0.732	Intermediate Similarity	NPD5960	Phase 3
0.731	Intermediate Similarity	NPD6797	Phase 2
0.731	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD6232	Discontinued
0.7303	Intermediate Similarity	NPD6653	Approved
0.7301	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7301	Intermediate Similarity	NPD1465	Phase 2
0.7297	Intermediate Similarity	NPD3018	Phase 2
0.7296	Intermediate Similarity	NPD7314	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD3496	Discontinued
0.7285	Intermediate Similarity	NPD4140	Approved
0.7279	Intermediate Similarity	NPD290	Approved
0.7278	Intermediate Similarity	NPD7473	Discontinued
0.7273	Intermediate Similarity	NPD5691	Approved
0.7273	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD1357	Approved
0.7267	Intermediate Similarity	NPD7685	Pre-registration
0.7267	Intermediate Similarity	NPD6798	Discontinued
0.7267	Intermediate Similarity	NPD7251	Discontinued
0.7266	Intermediate Similarity	NPD7843	Approved
0.7262	Intermediate Similarity	NPD2970	Approved
0.7262	Intermediate Similarity	NPD2969	Approved
0.7261	Intermediate Similarity	NPD2677	Approved
0.726	Intermediate Similarity	NPD4749	Approved
0.7256	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7256	Intermediate Similarity	NPD2560	Approved
0.7256	Intermediate Similarity	NPD2563	Approved
0.7244	Intermediate Similarity	NPD4237	Approved
0.7244	Intermediate Similarity	NPD4236	Phase 3
0.7244	Intermediate Similarity	NPD1652	Phase 2
0.7241	Intermediate Similarity	NPD422	Phase 1
0.7239	Intermediate Similarity	NPD6801	Discontinued
0.7234	Intermediate Similarity	NPD6671	Approved
0.7233	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD7808	Phase 3
0.7225	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD7549	Discontinued
0.7215	Intermediate Similarity	NPD6666	Approved
0.7215	Intermediate Similarity	NPD6667	Approved
0.7208	Intermediate Similarity	NPD2799	Discontinued
0.7208	Intermediate Similarity	NPD7033	Discontinued
0.7202	Intermediate Similarity	NPD3051	Approved
0.72	Intermediate Similarity	NPD7095	Approved
0.7197	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7195	Intermediate Similarity	NPD8455	Phase 2
0.7195	Intermediate Similarity	NPD7819	Suspended
0.7188	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.7186	Intermediate Similarity	NPD4666	Phase 3
0.7184	Intermediate Similarity	NPD7313	Approved
0.7184	Intermediate Similarity	NPD7312	Approved
0.7184	Intermediate Similarity	NPD7311	Approved
0.7184	Intermediate Similarity	NPD7310	Approved
0.7179	Intermediate Similarity	NPD1549	Phase 2
0.7175	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD4357	Discontinued
0.7162	Intermediate Similarity	NPD2797	Approved
0.716	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7159	Intermediate Similarity	NPD4663	Approved
0.7159	Intermediate Similarity	NPD8434	Phase 2
0.7152	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD2983	Phase 2
0.7143	Intermediate Similarity	NPD7309	Approved
0.7143	Intermediate Similarity	NPD2982	Phase 2
0.7134	Intermediate Similarity	NPD3060	Approved
0.7134	Intermediate Similarity	NPD5177	Phase 3
0.7126	Intermediate Similarity	NPD5709	Phase 3
0.7125	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD4340	Discontinued
0.7124	Intermediate Similarity	NPD447	Suspended
0.7115	Intermediate Similarity	NPD1375	Discontinued
0.7115	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD7768	Phase 2
0.7105	Intermediate Similarity	NPD6233	Phase 2
0.7099	Intermediate Similarity	NPD3687	Approved
0.7099	Intermediate Similarity	NPD3686	Approved
0.7097	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7093	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD2977	Approved
0.7091	Intermediate Similarity	NPD2978	Approved
0.7089	Intermediate Similarity	NPD3750	Approved
0.7089	Intermediate Similarity	NPD8166	Discontinued
0.7086	Intermediate Similarity	NPD8312	Approved
0.7086	Intermediate Similarity	NPD4578	Approved
0.7086	Intermediate Similarity	NPD8313	Approved
0.7086	Intermediate Similarity	NPD4577	Approved
0.7081	Intermediate Similarity	NPD6273	Approved
0.7075	Intermediate Similarity	NPD1608	Approved
0.7075	Intermediate Similarity	NPD2981	Phase 2
0.7069	Intermediate Similarity	NPD7240	Approved
0.7063	Intermediate Similarity	NPD6799	Approved
0.7059	Intermediate Similarity	NPD3926	Phase 2
0.7059	Intermediate Similarity	NPD2238	Phase 2
0.7051	Intermediate Similarity	NPD2161	Phase 2
0.7051	Intermediate Similarity	NPD2796	Approved
0.7051	Intermediate Similarity	NPD1551	Phase 2
0.7051	Intermediate Similarity	NPD6032	Approved
0.7048	Intermediate Similarity	NPD6374	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD5402	Approved
0.7047	Intermediate Similarity	NPD3094	Phase 2
0.7041	Intermediate Similarity	NPD6959	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