NPASS Compound

Structure

CID154217 OpenBabel06191715522D 25 27 0 0 0 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 -2.5981 -1.5000 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 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 -1.7321 0.0000 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 0.0000 3.0000 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 2.5981 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 -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 0.8660 -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 0.0000 1.0000 0.0000 C 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 0.8660 -1.5000 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 11 1 0 0 0 0 2 11 1 0 0 0 0 3 4 2 0 0 0 0 3 5 1 0 0 0 0 4 6 1 0 0 0 0 5 7 2 0 0 0 0 6 12 2 0 0 0 0 7 12 1 0 0 0 0 8 11 1 0 0 0 0 8 14 1 0 0 0 0 9 13 2 0 0 0 0 9 17 1 0 0 0 0 10 15 2 0 0 0 0 10 16 1 0 0 0 0 12 13 1 0 0 0 0 13 18 1 0 0 0 0 14 19 1 0 0 0 0 14 21 2 0 0 0 0 15 18 1 0 0 0 0 15 22 1 0 0 0 0 16 19 2 0 0 0 0 16 23 1 0 0 0 0 17 24 2 0 0 0 0 17 25 1 0 0 0 0 18 20 2 0 0 0 0 19 20 1 0 0 0 0 20 25 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	338.12
Volume:	349.03
LogP:	4.584
LogD:	3.549
LogS:	-4.857
# Rotatable Bonds:	4
TPSA:	87.74
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.552
Synthetic Accessibility Score:	2.519
Fsp3:	0.2
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:	-4.814
MDCK Permeability:	1.5469457139261067e-05
Pgp-inhibitor:	0.007
Pgp-substrate:	0.014
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.456
30% Bioavailability (F30%):	0.994

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.03
Plasma Protein Binding (PPB):	98.79009246826172%
Volume Distribution (VD):	0.502
Pgp-substrate:	0.9153263568878174%

ADMET: Metabolism

CYP1A2-inhibitor:	0.898
CYP1A2-substrate:	0.37
CYP2C19-inhibitor:	0.854
CYP2C19-substrate:	0.061
CYP2C9-inhibitor:	0.849
CYP2C9-substrate:	0.9
CYP2D6-inhibitor:	0.622
CYP2D6-substrate:	0.23
CYP3A4-inhibitor:	0.266
CYP3A4-substrate:	0.113

ADMET: Excretion

Clearance (CL):	8.929
Half-life (T1/2):	0.437

ADMET: Toxicity

hERG Blockers:	0.015
Human Hepatotoxicity (H-HT):	0.263
Drug-inuced Liver Injury (DILI):	0.977
AMES Toxicity:	0.476
Rat Oral Acute Toxicity:	0.129
Maximum Recommended Daily Dose:	0.165
Skin Sensitization:	0.588
Carcinogencity:	0.661
Eye Corrosion:	0.005
Eye Irritation:	0.809
Respiratory Toxicity:	0.359

Download Data

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

Natural Product: NPC154217

Natural Product ID:	NPC154217
*Common Name:**	Isodispar B
IUPAC Name:	5,7-dihydroxy-8-(3-methylbutanoyl)-4-phenylchromen-2-one
Synonyms:
Standard InCHIKey:	GKEWZBRIASMMCY-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C20H18O5/c1-11(2)8-14(21)19-16(23)10-15(22)18-13(9-17(24)25-20(18)19)12-6-4-3-5-7-12/h3-7,9-11,22-23H,8H2,1-2H3
SMILES:	CC(CC(=O)c1c(O)cc(c2c1oc(=O)cc2c1ccccc1)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL198873
PubChem CID:	6483316
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
NPO27228	Calophyllum dispar	Species	Calophyllaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11374944]
NPO33501	marila pluricostata	Species	Calophyllaceae	Eukaryota	leaves	n.a.	n.a.	PMID[15787438]
NPO27228	Calophyllum dispar	Species	Calophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]

☑ 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
GI50	3
IC50	1
Others	5

Activity Type	# Activity
Cell Line	6
Individual Protein	1
NON-MOLECULAR	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT459	Individual Protein	Human immunodeficiency virus type 1 reverse transcriptase	Human immunodeficiency virus 1	IC50	=	6900.0	nM	PMID[560360]
NPT165	Cell Line	HeLa	Homo sapiens	Inhibition	=	42.0	%	PMID[560360]
NPT165	Cell Line	HeLa	Homo sapiens	Inhibition	=	69.4	%	PMID[560360]
NPT460	Cell Line	MT2	Homo sapiens	Cell death	=	17.2	%	PMID[560360]
NPT83	Cell Line	MCF7	Homo sapiens	GI50	=	1.5	ug.mL-1	PMID[560361]
NPT397	Cell Line	NCI-H460	Homo sapiens	GI50	=	1.9	ug.mL-1	PMID[560361]
NPT395	Cell Line	SF-268	Homo sapiens	GI50	=	1.8	ug.mL-1	PMID[560361]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	81.0	%	PMID[560360]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	85.6	%	PMID[560360]

☑ 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 NPC154217 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	382
0.1-0.2	1712
0.2-0.3	4063
0.3-0.4	10111
0.4-0.5	8382
0.5-0.6	3990
0.6-0.7	5944
0.7-0.8	4500
0.8-0.85	2093
0.85-0.9	1210
0.9-0.95	264
0.95-1	46

Similarity Score	Similarity Level	Natural Product ID
0.9928	High Similarity	NPC1886
0.9928	High Similarity	NPC196137
0.9857	High Similarity	NPC181388
0.9857	High Similarity	NPC470322
0.9856	High Similarity	NPC188632
0.9856	High Similarity	NPC94794
0.9856	High Similarity	NPC196459
0.9856	High Similarity	NPC87609
0.9856	High Similarity	NPC470296
0.9856	High Similarity	NPC112791
0.9786	High Similarity	NPC178627
0.9786	High Similarity	NPC469935
0.9784	High Similarity	NPC36181
0.9718	High Similarity	NPC161864
0.9718	High Similarity	NPC208303
0.965	High Similarity	NPC469932
0.9648	High Similarity	NPC297886
0.9648	High Similarity	NPC140120
0.9648	High Similarity	NPC249942
0.9583	High Similarity	NPC474735
0.958	High Similarity	NPC469933
0.9577	High Similarity	NPC57470
0.9571	High Similarity	NPC282300
0.9568	High Similarity	NPC216978
0.9568	High Similarity	NPC55018
0.9568	High Similarity	NPC301217
0.9568	High Similarity	NPC303633
0.9568	High Similarity	NPC473209
0.9568	High Similarity	NPC220062
0.9568	High Similarity	NPC96565
0.9517	High Similarity	NPC290671
0.9514	High Similarity	NPC19238
0.951	High Similarity	NPC180477
0.9507	High Similarity	NPC469953
0.9507	High Similarity	NPC326500
0.95	High Similarity	NPC270883
0.95	High Similarity	NPC172986
0.95	High Similarity	NPC159275
0.95	High Similarity	NPC241100
0.95	High Similarity	NPC261227
0.9496	High Similarity	NPC199458
0.9496	High Similarity	NPC183639
0.9496	High Similarity	NPC201395
0.9437	High Similarity	NPC9117
0.9437	High Similarity	NPC24821
0.9437	High Similarity	NPC190637
0.9437	High Similarity	NPC11700
0.9437	High Similarity	NPC293053
0.9437	High Similarity	NPC219915
0.9437	High Similarity	NPC212932
0.9433	High Similarity	NPC147688
0.9433	High Similarity	NPC156590
0.9433	High Similarity	NPC110969
0.9433	High Similarity	NPC205006
0.9433	High Similarity	NPC118840
0.9433	High Similarity	NPC64908
0.9433	High Similarity	NPC470555
0.9429	High Similarity	NPC78913
0.9429	High Similarity	NPC53181
0.9429	High Similarity	NPC241975
0.9429	High Similarity	NPC217186
0.9429	High Similarity	NPC19476
0.9429	High Similarity	NPC18260
0.9424	High Similarity	NPC474624
0.9424	High Similarity	NPC131782
0.9424	High Similarity	NPC138047
0.9384	High Similarity	NPC209142
0.9384	High Similarity	NPC312549
0.9379	High Similarity	NPC104236
0.9379	High Similarity	NPC164205
0.9371	High Similarity	NPC216538
0.9371	High Similarity	NPC234629
0.9371	High Similarity	NPC271288
0.9371	High Similarity	NPC311741
0.9371	High Similarity	NPC273538
0.9366	High Similarity	NPC78803
0.9366	High Similarity	NPC144499
0.9366	High Similarity	NPC226636
0.9366	High Similarity	NPC59739
0.9366	High Similarity	NPC217083
0.9366	High Similarity	NPC293852
0.9366	High Similarity	NPC214236
0.9366	High Similarity	NPC62840
0.9366	High Similarity	NPC473042
0.9366	High Similarity	NPC299080
0.9366	High Similarity	NPC11561
0.9366	High Similarity	NPC200694
0.9362	High Similarity	NPC69769
0.9362	High Similarity	NPC475680
0.9362	High Similarity	NPC305355
0.9362	High Similarity	NPC221173
0.9362	High Similarity	NPC235239
0.9362	High Similarity	NPC150522
0.9357	High Similarity	NPC470669
0.9357	High Similarity	NPC470083
0.9357	High Similarity	NPC470668
0.9357	High Similarity	NPC219584
0.9353	High Similarity	NPC13408
0.9324	High Similarity	NPC469934
0.9315	High Similarity	NPC151973
0.9306	High Similarity	NPC476088
0.9306	High Similarity	NPC25844
0.9306	High Similarity	NPC5820
0.9306	High Similarity	NPC124729
0.9306	High Similarity	NPC153758
0.9306	High Similarity	NPC474161
0.9306	High Similarity	NPC178343
0.9306	High Similarity	NPC477955
0.9306	High Similarity	NPC306488
0.9301	High Similarity	NPC81697
0.9301	High Similarity	NPC38219
0.9301	High Similarity	NPC125894
0.9301	High Similarity	NPC107177
0.9301	High Similarity	NPC223812
0.9301	High Similarity	NPC77794
0.9301	High Similarity	NPC85162
0.9301	High Similarity	NPC106985
0.9301	High Similarity	NPC18585
0.9301	High Similarity	NPC278249
0.9301	High Similarity	NPC166138
0.9296	High Similarity	NPC14871
0.9296	High Similarity	NPC103362
0.9291	High Similarity	NPC472343
0.9291	High Similarity	NPC470986
0.9286	High Similarity	NPC332594
0.9286	High Similarity	NPC103001
0.9286	High Similarity	NPC228661
0.9262	High Similarity	NPC474609
0.9262	High Similarity	NPC475797
0.9262	High Similarity	NPC109967
0.9262	High Similarity	NPC474738
0.9262	High Similarity	NPC321372
0.9262	High Similarity	NPC469936
0.9262	High Similarity	NPC78554
0.9262	High Similarity	NPC129053
0.9252	High Similarity	NPC148945
0.9252	High Similarity	NPC316960
0.9252	High Similarity	NPC204561
0.9252	High Similarity	NPC309512
0.9252	High Similarity	NPC317715
0.9252	High Similarity	NPC78835
0.9247	High Similarity	NPC470461
0.9241	High Similarity	NPC308200
0.9241	High Similarity	NPC237635
0.9241	High Similarity	NPC79469
0.9241	High Similarity	NPC24673
0.9241	High Similarity	NPC201731
0.9241	High Similarity	NPC14001
0.9241	High Similarity	NPC166757
0.9241	High Similarity	NPC473077
0.9241	High Similarity	NPC104406
0.9241	High Similarity	NPC97716
0.9241	High Similarity	NPC296998
0.9236	High Similarity	NPC473013
0.9236	High Similarity	NPC131568
0.9236	High Similarity	NPC235217
0.9236	High Similarity	NPC473014
0.9236	High Similarity	NPC131579
0.9236	High Similarity	NPC473015
0.9236	High Similarity	NPC319752
0.9236	High Similarity	NPC224714
0.9231	High Similarity	NPC306829
0.9231	High Similarity	NPC470556
0.9231	High Similarity	NPC166934
0.9231	High Similarity	NPC227579
0.9231	High Similarity	NPC296917
0.9231	High Similarity	NPC266725
0.9231	High Similarity	NPC324134
0.9231	High Similarity	NPC223500
0.9231	High Similarity	NPC1089
0.9231	High Similarity	NPC32739
0.9231	High Similarity	NPC177354
0.9231	High Similarity	NPC37496
0.9231	High Similarity	NPC40833
0.9231	High Similarity	NPC324436
0.9231	High Similarity	NPC328164
0.9231	High Similarity	NPC194432
0.9231	High Similarity	NPC78
0.9231	High Similarity	NPC125855
0.9231	High Similarity	NPC265040
0.9231	High Similarity	NPC76372
0.9231	High Similarity	NPC66515
0.9231	High Similarity	NPC76338
0.9231	High Similarity	NPC161506
0.9231	High Similarity	NPC228504
0.9231	High Similarity	NPC148757
0.9231	High Similarity	NPC166482
0.9231	High Similarity	NPC10937
0.9231	High Similarity	NPC220998
0.9231	High Similarity	NPC64915
0.9231	High Similarity	NPC182852
0.9231	High Similarity	NPC167624
0.9231	High Similarity	NPC107572
0.9225	High Similarity	NPC259166
0.9225	High Similarity	NPC144118
0.9225	High Similarity	NPC204985
0.9225	High Similarity	NPC80962
0.9225	High Similarity	NPC76445
0.9225	High Similarity	NPC326109
0.9225	High Similarity	NPC48624

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 NPC154217 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	359
0.1-0.2	971
0.2-0.3	1551
0.3-0.4	2619
0.4-0.5	1961
0.5-0.6	1147
0.6-0.7	354
0.7-0.8	119
0.8-0.85	38
0.85-0.9	21
0.9-0.95	10
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9371	High Similarity	NPD4378	Clinical (unspecified phase)
0.9103	High Similarity	NPD7410	Clinical (unspecified phase)
0.8993	High Similarity	NPD7411	Suspended
0.8947	High Similarity	NPD7075	Discontinued
0.8881	High Similarity	NPD1552	Clinical (unspecified phase)
0.8881	High Similarity	NPD1550	Clinical (unspecified phase)
0.8874	High Similarity	NPD7096	Clinical (unspecified phase)
0.8874	High Similarity	NPD7819	Suspended
0.8873	High Similarity	NPD1510	Phase 2
0.8828	High Similarity	NPD3750	Approved
0.8819	High Similarity	NPD1549	Phase 2
0.8816	High Similarity	NPD8443	Clinical (unspecified phase)
0.8811	High Similarity	NPD2796	Approved
0.8808	High Similarity	NPD6801	Discontinued
0.8759	High Similarity	NPD1243	Approved
0.875	High Similarity	NPD2393	Clinical (unspecified phase)
0.8723	High Similarity	NPD1240	Approved
0.869	High Similarity	NPD970	Clinical (unspecified phase)
0.8675	High Similarity	NPD4380	Phase 2
0.8649	High Similarity	NPD6799	Approved
0.8649	High Similarity	NPD1511	Approved
0.8636	High Similarity	NPD7768	Phase 2
0.863	High Similarity	NPD7421	Clinical (unspecified phase)
0.8611	High Similarity	NPD2799	Discontinued
0.8608	High Similarity	NPD7852	Clinical (unspecified phase)
0.8601	High Similarity	NPD1607	Approved
0.8581	High Similarity	NPD3749	Approved
0.8533	High Similarity	NPD1512	Approved
0.8506	High Similarity	NPD2801	Approved
0.8483	Intermediate Similarity	NPD3748	Approved
0.8477	Intermediate Similarity	NPD920	Approved
0.8462	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8456	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.8452	Intermediate Similarity	NPD3817	Phase 2
0.8451	Intermediate Similarity	NPD2313	Discontinued
0.8451	Intermediate Similarity	NPD3268	Approved
0.8451	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8442	Intermediate Similarity	NPD1934	Approved
0.8431	Intermediate Similarity	NPD6599	Discontinued
0.8425	Intermediate Similarity	NPD2935	Discontinued
0.8425	Intermediate Similarity	NPD1551	Phase 2
0.8378	Intermediate Similarity	NPD2800	Approved
0.8357	Intermediate Similarity	NPD1203	Approved
0.8357	Intermediate Similarity	NPD2797	Approved
0.8344	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8323	Intermediate Similarity	NPD7473	Discontinued
0.825	Intermediate Similarity	NPD6232	Discontinued
0.8247	Intermediate Similarity	NPD3226	Approved
0.8235	Intermediate Similarity	NPD5403	Approved
0.8232	Intermediate Similarity	NPD5953	Discontinued
0.8224	Intermediate Similarity	NPD2534	Approved
0.8224	Intermediate Similarity	NPD2533	Approved
0.8224	Intermediate Similarity	NPD2532	Approved
0.8219	Intermediate Similarity	NPD6651	Approved
0.8201	Intermediate Similarity	NPD422	Phase 1
0.82	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.8187	Intermediate Similarity	NPD6959	Discontinued
0.8165	Intermediate Similarity	NPD3882	Suspended
0.8143	Intermediate Similarity	NPD9717	Approved
0.8133	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.811	Intermediate Similarity	NPD7286	Phase 2
0.8108	Intermediate Similarity	NPD4308	Phase 3
0.8105	Intermediate Similarity	NPD5401	Approved
0.8099	Intermediate Similarity	NPD3266	Approved
0.8099	Intermediate Similarity	NPD3267	Approved
0.8079	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.8063	Intermediate Similarity	NPD919	Approved
0.8056	Intermediate Similarity	NPD6832	Phase 2
0.805	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8049	Intermediate Similarity	NPD3818	Discontinued
0.8042	Intermediate Similarity	NPD2798	Approved
0.8037	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8037	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8037	Intermediate Similarity	NPD6166	Phase 2
0.8028	Intermediate Similarity	NPD3225	Approved
0.8027	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.8027	Intermediate Similarity	NPD5124	Phase 1
0.8012	Intermediate Similarity	NPD5494	Approved
0.8	Intermediate Similarity	NPD5844	Phase 1
0.8	Intermediate Similarity	NPD7054	Approved
0.8	Intermediate Similarity	NPD2346	Discontinued
0.8	Intermediate Similarity	NPD2344	Approved
0.7987	Intermediate Similarity	NPD7033	Discontinued
0.7987	Intermediate Similarity	NPD5402	Approved
0.7964	Intermediate Similarity	NPD6559	Discontinued
0.7961	Intermediate Similarity	NPD4628	Phase 3
0.7952	Intermediate Similarity	NPD7074	Phase 3
0.7952	Intermediate Similarity	NPD7472	Approved
0.7945	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7933	Intermediate Similarity	NPD6100	Approved
0.7933	Intermediate Similarity	NPD6099	Approved
0.7917	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7904	Intermediate Similarity	NPD6797	Phase 2
0.7887	Intermediate Similarity	NPD1608	Approved
0.7867	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD7251	Discontinued
0.7838	Intermediate Similarity	NPD4307	Phase 2
0.7823	Intermediate Similarity	NPD1296	Phase 2
0.7812	Intermediate Similarity	NPD1465	Phase 2
0.7811	Intermediate Similarity	NPD7808	Phase 3
0.7808	Intermediate Similarity	NPD4908	Phase 1
0.7799	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7792	Intermediate Similarity	NPD2309	Approved
0.7764	Intermediate Similarity	NPD4288	Approved
0.7718	Intermediate Similarity	NPD943	Approved
0.7703	Intermediate Similarity	NPD411	Approved
0.7692	Intermediate Similarity	NPD1610	Phase 2
0.7692	Intermediate Similarity	NPD7390	Discontinued
0.7684	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7676	Intermediate Similarity	NPD17	Approved
0.7673	Intermediate Similarity	NPD7458	Discontinued
0.767	Intermediate Similarity	NPD4363	Phase 3
0.767	Intermediate Similarity	NPD4360	Phase 2
0.7667	Intermediate Similarity	NPD447	Suspended
0.7667	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.766	Intermediate Similarity	NPD1548	Phase 1
0.7658	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7643	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7627	Intermediate Similarity	NPD4361	Phase 2
0.7627	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7613	Intermediate Similarity	NPD7003	Approved
0.7603	Intermediate Similarity	NPD1164	Approved
0.759	Intermediate Similarity	NPD5711	Approved
0.759	Intermediate Similarity	NPD7229	Phase 3
0.759	Intermediate Similarity	NPD5710	Approved
0.7588	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7584	Intermediate Similarity	NPD3764	Approved
0.7582	Intermediate Similarity	NPD5404	Approved
0.7582	Intermediate Similarity	NPD5406	Approved
0.7582	Intermediate Similarity	NPD5405	Approved
0.7582	Intermediate Similarity	NPD5408	Approved
0.7569	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7562	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.755	Intermediate Similarity	NPD1933	Approved
0.7543	Intermediate Similarity	NPD4287	Approved
0.7535	Intermediate Similarity	NPD9545	Approved
0.7532	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.753	Intermediate Similarity	NPD1247	Approved
0.7518	Intermediate Similarity	NPD9493	Approved
0.7517	Intermediate Similarity	NPD4625	Phase 3
0.7516	Intermediate Similarity	NPD6585	Discontinued
0.7469	Intermediate Similarity	NPD5889	Approved
0.7469	Intermediate Similarity	NPD5890	Approved
0.7468	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7467	Intermediate Similarity	NPD6798	Discontinued
0.745	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.744	Intermediate Similarity	NPD3926	Phase 2
0.7436	Intermediate Similarity	NPD2654	Approved
0.7434	Intermediate Similarity	NPD230	Phase 1
0.7434	Intermediate Similarity	NPD6355	Discontinued
0.7432	Intermediate Similarity	NPD1019	Discontinued
0.7425	Intermediate Similarity	NPD7199	Phase 2
0.7397	Intermediate Similarity	NPD1481	Phase 2
0.7375	Intermediate Similarity	NPD5049	Phase 3
0.7375	Intermediate Similarity	NPD6273	Approved
0.7368	Intermediate Similarity	NPD4060	Phase 1
0.736	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7357	Intermediate Similarity	NPD5535	Approved
0.7356	Intermediate Similarity	NPD8312	Approved
0.7356	Intermediate Similarity	NPD8313	Approved
0.7355	Intermediate Similarity	NPD4476	Approved
0.7355	Intermediate Similarity	NPD4477	Approved
0.7347	Intermediate Similarity	NPD4749	Approved
0.7342	Intermediate Similarity	NPD2354	Approved
0.7337	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD1201	Approved
0.7329	Intermediate Similarity	NPD1535	Discovery
0.7326	Intermediate Similarity	NPD1729	Discontinued
0.7325	Intermediate Similarity	NPD1652	Phase 2
0.731	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD6002	Phase 3
0.7308	Intermediate Similarity	NPD6004	Phase 3
0.7308	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD6005	Phase 3
0.7297	Intermediate Similarity	NPD1283	Approved
0.7294	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7279	Intermediate Similarity	NPD3972	Approved
0.7267	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD1470	Approved
0.7247	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD6971	Discontinued
0.7232	Intermediate Similarity	NPD8434	Phase 2
0.7229	Intermediate Similarity	NPD2296	Approved
0.7219	Intermediate Similarity	NPD2614	Approved
0.7219	Intermediate Similarity	NPD7584	Approved
0.7212	Intermediate Similarity	NPD37	Approved
0.7209	Intermediate Similarity	NPD7177	Discontinued
0.7202	Intermediate Similarity	NPD6234	Discontinued
0.7197	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD1471	Phase 3
0.7197	Intermediate Similarity	NPD2353	Approved
0.7195	Intermediate Similarity	NPD6502	Phase 2
0.719	Intermediate Similarity	NPD6233	Phase 2
0.719	Intermediate Similarity	NPD8032	Phase 2
0.7188	Intermediate Similarity	NPD6667	Approved
0.7188	Intermediate Similarity	NPD6666	Approved
0.7186	Intermediate Similarity	NPD4966	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