NPASS Compound

Structure

NPC469935 OpenBabel07101719152D 35 37 0 0 1 0 0 0 0 0999 V2000 -3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 9.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 9.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 6.0000 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 4.3301 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 7.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 7.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 8.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 C 0 0 3 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 -0.0000 3.0000 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 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 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 0.8660 2.5000 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 -0.0000 1.0000 0.0000 C 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 -2.5981 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 3.0000 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 6 1 0 0 0 0 2 18 1 0 0 0 0 3 18 1 0 0 0 0 4 19 1 0 0 0 0 5 20 1 0 0 0 0 6 20 1 0 0 0 0 7 8 2 0 0 0 0 7 9 1 0 0 0 0 8 13 1 0 0 0 0 9 14 2 0 0 0 0 10 11 1 0 0 0 0 10 12 1 0 0 0 0 11 18 2 0 0 0 0 12 19 1 0 0 0 0 13 21 2 0 0 0 0 14 21 1 0 0 0 0 15 16 1 0 0 0 0 15 19 2 0 0 0 0 16 22 1 0 0 0 0 17 23 2 0 0 0 0 17 24 1 0 0 0 0 20 27 1 0 0 0 0 21 23 1 0 0 0 0 22 28 2 0 0 0 0 22 29 1 0 0 0 0 23 25 1 0 0 0 0 24 31 2 0 0 0 0 24 35 1 0 0 0 0 25 28 1 0 0 0 0 25 30 2 0 0 0 0 26 27 1 0 0 0 0 26 29 2 0 0 0 0 26 30 1 0 0 0 0 27 32 2 0 0 0 0 28 33 1 0 0 0 0 29 34 1 0 0 0 0 30 35 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	474.24
Volume:	516.717
LogP:	7.108
LogD:	4.451
LogS:	-4.056
# Rotatable Bonds:	9
TPSA:	87.74
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.192
Synthetic Accessibility Score:	3.463
Fsp3:	0.333
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.821
MDCK Permeability:	1.8056665794574656e-05
Pgp-inhibitor:	0.995
Pgp-substrate:	0.042
Human Intestinal Absorption (HIA):	0.013
20% Bioavailability (F20%):	0.064
30% Bioavailability (F30%):	0.053

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.003
Plasma Protein Binding (PPB):	101.83345031738281%
Volume Distribution (VD):	0.262
Pgp-substrate:	1.0882456302642822%

ADMET: Metabolism

CYP1A2-inhibitor:	0.426
CYP1A2-substrate:	0.382
CYP2C19-inhibitor:	0.891
CYP2C19-substrate:	0.068
CYP2C9-inhibitor:	0.893
CYP2C9-substrate:	0.938
CYP2D6-inhibitor:	0.092
CYP2D6-substrate:	0.298
CYP3A4-inhibitor:	0.193
CYP3A4-substrate:	0.159

ADMET: Excretion

Clearance (CL):	5.278
Half-life (T1/2):	0.062

ADMET: Toxicity

hERG Blockers:	0.02
Human Hepatotoxicity (H-HT):	0.925
Drug-inuced Liver Injury (DILI):	0.937
AMES Toxicity:	0.024
Rat Oral Acute Toxicity:	0.122
Maximum Recommended Daily Dose:	0.06
Skin Sensitization:	0.659
Carcinogencity:	0.067
Eye Corrosion:	0.003
Eye Irritation:	0.078
Respiratory Toxicity:	0.521

Download Data

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

Natural Product: NPC469935

Natural Product ID:	NPC469935
*Common Name:**	6-[(2E)-3,7-Dimethylocta-2,6-Dienyl]-5,7-Dihydroxy-8-(2-Methylbutanoyl)-4-Phenylchromen-2-One
IUPAC Name:	6-[(2E)-3,7-dimethylocta-2,6-dienyl]-5,7-dihydroxy-8-(2-methylbutanoyl)-4-phenylchromen-2-one
Synonyms:
Standard InCHIKey:	NTNREFYHTKELSQ-XDJHFCHBSA-N
Standard InCHI:	InChI=1S/C30H34O5/c1-6-20(5)27(32)26-29(34)22(16-15-19(4)12-10-11-18(2)3)28(33)25-23(17-24(31)35-30(25)26)21-13-8-7-9-14-21/h7-9,11,13-15,17,20,33-34H,6,10,12,16H2,1-5H3/b19-15+
SMILES:	CCC(C)C(=O)C1=C(C(=C(C2=C1OC(=O)C=C2C3=CC=CC=C3)O)CC=C(C)CCC=C(C)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1277774
PubChem CID:	11306030
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0001614] Neoflavonoids [CHEMONTID:0003650] Prenylated neoflavonoids

*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
NPO4756	Mesua elegans	Species	Calophyllaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20943395]
NPO4756	Mesua elegans	Species	Calophyllaceae	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	1

Activity Type	# Activity
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT66	Individual Protein	Acetylcholinesterase	Electrophorus electricus	IC50	=	3060.0	nM	PMID[490629]

☑ 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 NPC469935 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	380
0.1-0.2	1619
0.2-0.3	3863
0.3-0.4	9644
0.4-0.5	9034
0.5-0.6	3863
0.6-0.7	6000
0.7-0.8	4585
0.8-0.85	2155
0.85-0.9	1257
0.9-0.95	250
0.95-1	47

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC178627
0.9928	High Similarity	NPC196459
0.9928	High Similarity	NPC112791
0.9928	High Similarity	NPC181388
0.9928	High Similarity	NPC94794
0.9928	High Similarity	NPC188632
0.9928	High Similarity	NPC87609
0.9928	High Similarity	NPC470296
0.9856	High Similarity	NPC1886
0.9856	High Similarity	NPC196137
0.9855	High Similarity	NPC36181
0.9787	High Similarity	NPC469933
0.9786	High Similarity	NPC470322
0.9786	High Similarity	NPC154217
0.9718	High Similarity	NPC469932
0.9716	High Similarity	NPC297886
0.9716	High Similarity	NPC249942
0.9648	High Similarity	NPC208303
0.9648	High Similarity	NPC161864
0.9645	High Similarity	NPC57470
0.958	High Similarity	NPC19238
0.9577	High Similarity	NPC180477
0.9577	High Similarity	NPC140120
0.9574	High Similarity	NPC469953
0.9565	High Similarity	NPC470083
0.9565	High Similarity	NPC219584
0.9514	High Similarity	NPC474735
0.95	High Similarity	NPC282300
0.95	High Similarity	NPC470555
0.9496	High Similarity	NPC301217
0.9496	High Similarity	NPC220062
0.9496	High Similarity	NPC96565
0.9496	High Similarity	NPC216978
0.9496	High Similarity	NPC241975
0.9496	High Similarity	NPC473209
0.9496	High Similarity	NPC303633
0.9496	High Similarity	NPC217186
0.9496	High Similarity	NPC55018
0.9496	High Similarity	NPC53181
0.9496	High Similarity	NPC19476
0.9493	High Similarity	NPC138047
0.9493	High Similarity	NPC474624
0.9493	High Similarity	NPC131782
0.9448	High Similarity	NPC290671
0.9444	High Similarity	NPC104236
0.9444	High Similarity	NPC164205
0.9429	High Similarity	NPC261227
0.9429	High Similarity	NPC270883
0.9429	High Similarity	NPC241100
0.9429	High Similarity	NPC221173
0.9429	High Similarity	NPC172986
0.9429	High Similarity	NPC159275
0.9424	High Similarity	NPC199458
0.9424	High Similarity	NPC183639
0.9424	High Similarity	NPC201395
0.9388	High Similarity	NPC469934
0.9379	High Similarity	NPC151973
0.9362	High Similarity	NPC118840
0.9362	High Similarity	NPC110969
0.9362	High Similarity	NPC64908
0.9362	High Similarity	NPC147688
0.9362	High Similarity	NPC156590
0.9362	High Similarity	NPC205006
0.9357	High Similarity	NPC470986
0.9357	High Similarity	NPC472343
0.9357	High Similarity	NPC18260
0.9357	High Similarity	NPC78913
0.9315	High Similarity	NPC312549
0.9315	High Similarity	NPC209142
0.9301	High Similarity	NPC326500
0.9301	High Similarity	NPC473014
0.9301	High Similarity	NPC235217
0.9296	High Similarity	NPC266725
0.9296	High Similarity	NPC217083
0.9296	High Similarity	NPC299080
0.9296	High Similarity	NPC226636
0.9296	High Similarity	NPC214236
0.9296	High Similarity	NPC59739
0.9296	High Similarity	NPC200694
0.9296	High Similarity	NPC62840
0.9296	High Similarity	NPC78803
0.9296	High Similarity	NPC11561
0.9296	High Similarity	NPC293852
0.9291	High Similarity	NPC235239
0.9291	High Similarity	NPC69769
0.9291	High Similarity	NPC150522
0.9291	High Similarity	NPC305355
0.9291	High Similarity	NPC475680
0.9286	High Similarity	NPC470669
0.9286	High Similarity	NPC470668
0.9281	High Similarity	NPC13408
0.9236	High Similarity	NPC285630
0.9236	High Similarity	NPC153758
0.9236	High Similarity	NPC474161
0.9236	High Similarity	NPC476088
0.9236	High Similarity	NPC127059
0.9231	High Similarity	NPC9117
0.9231	High Similarity	NPC125894
0.9231	High Similarity	NPC219915
0.9231	High Similarity	NPC190637
0.9231	High Similarity	NPC212932
0.9231	High Similarity	NPC307895
0.9231	High Similarity	NPC11700
0.9231	High Similarity	NPC24821
0.9231	High Similarity	NPC107177
0.9231	High Similarity	NPC293053
0.9231	High Similarity	NPC185276
0.9231	High Similarity	NPC77794
0.9231	High Similarity	NPC85162
0.9231	High Similarity	NPC223812
0.9231	High Similarity	NPC81697
0.9231	High Similarity	NPC278249
0.9231	High Similarity	NPC470553
0.9231	High Similarity	NPC38219
0.9225	High Similarity	NPC110038
0.9225	High Similarity	NPC14871
0.9225	High Similarity	NPC248372
0.9225	High Similarity	NPC103362
0.922	High Similarity	NPC240305
0.9214	High Similarity	NPC332594
0.9195	High Similarity	NPC474609
0.9195	High Similarity	NPC78554
0.9195	High Similarity	NPC469936
0.9195	High Similarity	NPC129053
0.9195	High Similarity	NPC109967
0.9195	High Similarity	NPC321372
0.9195	High Similarity	NPC474738
0.9195	High Similarity	NPC475797
0.9172	High Similarity	NPC283234
0.9167	High Similarity	NPC236766
0.9167	High Similarity	NPC133060
0.9167	High Similarity	NPC257236
0.9167	High Similarity	NPC118059
0.9167	High Similarity	NPC473015
0.9167	High Similarity	NPC288910
0.9167	High Similarity	NPC278175
0.9167	High Similarity	NPC197252
0.9167	High Similarity	NPC470554
0.9167	High Similarity	NPC234629
0.9167	High Similarity	NPC131568
0.9167	High Similarity	NPC273538
0.9167	High Similarity	NPC473013
0.9167	High Similarity	NPC311741
0.9167	High Similarity	NPC131579
0.9167	High Similarity	NPC271288
0.9167	High Similarity	NPC216538
0.9167	High Similarity	NPC319752
0.9161	High Similarity	NPC220998
0.9161	High Similarity	NPC112829
0.9161	High Similarity	NPC32739
0.9161	High Similarity	NPC265040
0.9161	High Similarity	NPC10937
0.9161	High Similarity	NPC228504
0.9161	High Similarity	NPC227579
0.9161	High Similarity	NPC324436
0.9161	High Similarity	NPC223500
0.9161	High Similarity	NPC296917
0.9161	High Similarity	NPC64915
0.9161	High Similarity	NPC66515
0.9161	High Similarity	NPC324134
0.9161	High Similarity	NPC182852
0.9161	High Similarity	NPC161506
0.9161	High Similarity	NPC37496
0.9161	High Similarity	NPC107572
0.9161	High Similarity	NPC177354
0.9161	High Similarity	NPC78
0.9161	High Similarity	NPC166482
0.9161	High Similarity	NPC470556
0.9161	High Similarity	NPC76338
0.9161	High Similarity	NPC76372
0.9161	High Similarity	NPC40833
0.9161	High Similarity	NPC166934
0.9161	High Similarity	NPC306829
0.9161	High Similarity	NPC148757
0.9161	High Similarity	NPC125855
0.9161	High Similarity	NPC167624
0.9161	High Similarity	NPC328164
0.9161	High Similarity	NPC1089
0.9161	High Similarity	NPC194432
0.9161	High Similarity	NPC144499
0.9161	High Similarity	NPC473042
0.9155	High Similarity	NPC129853
0.9155	High Similarity	NPC471587
0.9155	High Similarity	NPC284550
0.9155	High Similarity	NPC76445
0.9149	High Similarity	NPC254168
0.9149	High Similarity	NPC272844
0.9149	High Similarity	NPC248995
0.9143	High Similarity	NPC473887
0.9143	High Similarity	NPC174999
0.9143	High Similarity	NPC194281
0.9143	High Similarity	NPC231772
0.9143	High Similarity	NPC127447
0.9143	High Similarity	NPC234133
0.9143	High Similarity	NPC47815
0.9143	High Similarity	NPC29353
0.9143	High Similarity	NPC124784
0.9137	High Similarity	NPC103842
0.9128	High Similarity	NPC108937
0.9128	High Similarity	NPC279218

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 NPC469935 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	347
0.1-0.2	964
0.2-0.3	1547
0.3-0.4	2564
0.4-0.5	2006
0.5-0.6	1169
0.6-0.7	364
0.7-0.8	122
0.8-0.85	39
0.85-0.9	19
0.9-0.95	9
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9167	High Similarity	NPD7410	Clinical (unspecified phase)
0.9167	High Similarity	NPD4378	Clinical (unspecified phase)
0.8926	High Similarity	NPD7411	Suspended
0.8882	High Similarity	NPD7075	Discontinued
0.8811	High Similarity	NPD1552	Clinical (unspecified phase)
0.8811	High Similarity	NPD1550	Clinical (unspecified phase)
0.8808	High Similarity	NPD7096	Clinical (unspecified phase)
0.8808	High Similarity	NPD7819	Suspended
0.875	High Similarity	NPD1549	Phase 2
0.875	High Similarity	NPD8443	Clinical (unspecified phase)
0.8742	High Similarity	NPD6801	Discontinued
0.8671	High Similarity	NPD1510	Phase 2
0.8652	High Similarity	NPD1240	Approved
0.863	High Similarity	NPD3750	Approved
0.8611	High Similarity	NPD2796	Approved
0.8581	High Similarity	NPD6799	Approved
0.8571	High Similarity	NPD7768	Phase 2
0.8562	High Similarity	NPD7421	Clinical (unspecified phase)
0.8562	High Similarity	NPD1243	Approved
0.8562	High Similarity	NPD2393	Clinical (unspecified phase)
0.8531	High Similarity	NPD1607	Approved
0.8511	High Similarity	NPD6859	Clinical (unspecified phase)
0.8493	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8487	Intermediate Similarity	NPD4380	Phase 2
0.8456	Intermediate Similarity	NPD1511	Approved
0.8428	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8414	Intermediate Similarity	NPD2799	Discontinued
0.8403	Intermediate Similarity	NPD6651	Approved
0.8397	Intermediate Similarity	NPD3749	Approved
0.838	Intermediate Similarity	NPD3268	Approved
0.838	Intermediate Similarity	NPD2313	Discontinued
0.8366	Intermediate Similarity	NPD6599	Discontinued
0.8344	Intermediate Similarity	NPD1512	Approved
0.8323	Intermediate Similarity	NPD2801	Approved
0.8311	Intermediate Similarity	NPD2800	Approved
0.8289	Intermediate Similarity	NPD920	Approved
0.8288	Intermediate Similarity	NPD3748	Approved
0.8286	Intermediate Similarity	NPD2797	Approved
0.8286	Intermediate Similarity	NPD1203	Approved
0.828	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8272	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8269	Intermediate Similarity	NPD3817	Phase 2
0.8267	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.8261	Intermediate Similarity	NPD7473	Discontinued
0.8258	Intermediate Similarity	NPD1934	Approved
0.8231	Intermediate Similarity	NPD1551	Phase 2
0.8231	Intermediate Similarity	NPD2935	Discontinued
0.817	Intermediate Similarity	NPD5403	Approved
0.816	Intermediate Similarity	NPD7286	Phase 2
0.8158	Intermediate Similarity	NPD2533	Approved
0.8158	Intermediate Similarity	NPD2532	Approved
0.8158	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.8158	Intermediate Similarity	NPD2534	Approved
0.8129	Intermediate Similarity	NPD422	Phase 1
0.8112	Intermediate Similarity	NPD6832	Phase 2
0.8082	Intermediate Similarity	NPD5124	Phase 1
0.8082	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.8075	Intermediate Similarity	NPD6232	Discontinued
0.8071	Intermediate Similarity	NPD9717	Approved
0.8065	Intermediate Similarity	NPD3226	Approved
0.8061	Intermediate Similarity	NPD5953	Discontinued
0.8039	Intermediate Similarity	NPD5401	Approved
0.8028	Intermediate Similarity	NPD3266	Approved
0.8028	Intermediate Similarity	NPD3267	Approved
0.8013	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.8013	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.8012	Intermediate Similarity	NPD6959	Discontinued
0.7987	Intermediate Similarity	NPD3882	Suspended
0.7964	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7958	Intermediate Similarity	NPD3225	Approved
0.7939	Intermediate Similarity	NPD7054	Approved
0.7933	Intermediate Similarity	NPD2346	Discontinued
0.7919	Intermediate Similarity	NPD7033	Discontinued
0.7919	Intermediate Similarity	NPD4308	Phase 3
0.7892	Intermediate Similarity	NPD7472	Approved
0.7892	Intermediate Similarity	NPD7074	Phase 3
0.7888	Intermediate Similarity	NPD919	Approved
0.7879	Intermediate Similarity	NPD3818	Discontinued
0.7875	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7867	Intermediate Similarity	NPD6100	Approved
0.7867	Intermediate Similarity	NPD6099	Approved
0.7866	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7866	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7866	Intermediate Similarity	NPD6166	Phase 2
0.7848	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7847	Intermediate Similarity	NPD2798	Approved
0.784	Intermediate Similarity	NPD5494	Approved
0.7831	Intermediate Similarity	NPD5844	Phase 1
0.7815	Intermediate Similarity	NPD2344	Approved
0.7812	Intermediate Similarity	NPD5402	Approved
0.7798	Intermediate Similarity	NPD7251	Discontinued
0.7798	Intermediate Similarity	NPD6559	Discontinued
0.7778	Intermediate Similarity	NPD4628	Phase 3
0.7755	Intermediate Similarity	NPD1296	Phase 2
0.7755	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7751	Intermediate Similarity	NPD7808	Phase 3
0.7751	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7738	Intermediate Similarity	NPD6797	Phase 2
0.7727	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD1608	Approved
0.7682	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7651	Intermediate Similarity	NPD4307	Phase 2
0.764	Intermediate Similarity	NPD1465	Phase 2
0.7619	Intermediate Similarity	NPD4908	Phase 1
0.7613	Intermediate Similarity	NPD2309	Approved
0.761	Intermediate Similarity	NPD7458	Discontinued
0.7593	Intermediate Similarity	NPD4288	Approved
0.7589	Intermediate Similarity	NPD1548	Phase 1
0.7562	Intermediate Similarity	NPD6585	Discontinued
0.7533	Intermediate Similarity	NPD943	Approved
0.753	Intermediate Similarity	NPD5711	Approved
0.753	Intermediate Similarity	NPD7229	Phase 3
0.753	Intermediate Similarity	NPD5710	Approved
0.7517	Intermediate Similarity	NPD411	Approved
0.7516	Intermediate Similarity	NPD5890	Approved
0.7516	Intermediate Similarity	NPD7390	Discontinued
0.7516	Intermediate Similarity	NPD5406	Approved
0.7516	Intermediate Similarity	NPD5408	Approved
0.7516	Intermediate Similarity	NPD5404	Approved
0.7516	Intermediate Similarity	NPD5889	Approved
0.7516	Intermediate Similarity	NPD5405	Approved
0.7514	Intermediate Similarity	NPD4363	Phase 3
0.7514	Intermediate Similarity	NPD4360	Phase 2
0.75	Intermediate Similarity	NPD1610	Phase 2
0.75	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7486	Intermediate Similarity	NPD4287	Approved
0.7484	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD447	Suspended
0.7483	Intermediate Similarity	NPD17	Approved
0.7483	Intermediate Similarity	NPD1933	Approved
0.7483	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7472	Intermediate Similarity	NPD4361	Phase 2
0.7472	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7465	Intermediate Similarity	NPD9545	Approved
0.7447	Intermediate Similarity	NPD9493	Approved
0.7436	Intermediate Similarity	NPD7003	Approved
0.7427	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7421	Intermediate Similarity	NPD5049	Phase 3
0.7415	Intermediate Similarity	NPD1164	Approved
0.74	Intermediate Similarity	NPD3764	Approved
0.74	Intermediate Similarity	NPD6798	Discontinued
0.7391	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7383	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7372	Intermediate Similarity	NPD2654	Approved
0.7368	Intermediate Similarity	NPD6355	Discontinued
0.7365	Intermediate Similarity	NPD1019	Discontinued
0.7365	Intermediate Similarity	NPD1247	Approved
0.7337	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD4625	Phase 3
0.7329	Intermediate Similarity	NPD1481	Phase 2
0.7303	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7299	Intermediate Similarity	NPD8312	Approved
0.7299	Intermediate Similarity	NPD8313	Approved
0.7296	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7286	Intermediate Similarity	NPD5535	Approved
0.7278	Intermediate Similarity	NPD3926	Phase 2
0.7278	Intermediate Similarity	NPD2354	Approved
0.7267	Intermediate Similarity	NPD1729	Discontinued
0.7262	Intermediate Similarity	NPD7199	Phase 2
0.7261	Intermediate Similarity	NPD1652	Phase 2
0.726	Intermediate Similarity	NPD1535	Discovery
0.7255	Intermediate Similarity	NPD230	Phase 1
0.7251	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD6005	Phase 3
0.7244	Intermediate Similarity	NPD6004	Phase 3
0.7244	Intermediate Similarity	NPD6002	Phase 3
0.7244	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD1894	Discontinued
0.7211	Intermediate Similarity	NPD3972	Approved
0.7205	Intermediate Similarity	NPD6273	Approved
0.7191	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD4060	Phase 1
0.7179	Intermediate Similarity	NPD4476	Approved
0.7179	Intermediate Similarity	NPD4477	Approved
0.7176	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7175	Intermediate Similarity	NPD8434	Phase 2
0.7166	Intermediate Similarity	NPD7584	Approved
0.7162	Intermediate Similarity	NPD4749	Approved
0.7152	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD1201	Approved
0.7134	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD2353	Approved
0.7134	Intermediate Similarity	NPD6502	Phase 2
0.7125	Intermediate Similarity	NPD7440	Discontinued
0.7125	Intermediate Similarity	NPD6667	Approved
0.7125	Intermediate Similarity	NPD6666	Approved
0.7124	Intermediate Similarity	NPD6233	Phase 2
0.7124	Intermediate Similarity	NPD8032	Phase 2
0.712	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD1283	Approved
0.7108	Intermediate Similarity	NPD8455	Phase 2
0.7086	Intermediate Similarity	NPD6104	Discontinued
0.7086	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD6971	Discontinued
0.7067	Intermediate Similarity	NPD1470	Approved
0.7066	Intermediate Similarity	NPD2296	Approved
0.7063	Intermediate Similarity	NPD3887	Approved

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