NPASS Compound

Structure

CID326500 OpenBabel06191716192D 31 33 0 0 1 0 0 0 0 0999 V2000 5.1962 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -3.0000 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 4.3301 -1.5000 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 -1.7321 -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 -2.5981 -1.5000 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 1.7321 -1.0000 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 5.1962 -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 2.5981 -1.5000 0.0000 C 0 0 3 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 1.7321 -0.0000 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 1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 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 -4.3301 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 2.0000 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 13 1 0 0 0 0 2 13 1 0 0 0 0 3 14 2 0 0 0 0 4 14 1 0 0 0 0 5 6 1 0 0 0 0 5 13 2 0 0 0 0 6 16 1 0 0 0 0 7 9 1 0 0 0 0 7 15 2 0 0 0 0 8 10 2 0 0 0 0 8 15 1 0 0 0 0 9 17 2 0 0 0 0 10 17 1 0 0 0 0 11 16 1 0 0 0 0 11 18 1 0 0 0 0 12 19 2 0 0 0 0 12 20 1 0 0 0 0 14 16 1 0 0 0 0 15 24 1 0 0 0 0 17 26 1 0 0 0 0 18 19 1 0 0 0 0 18 25 2 0 0 0 0 19 27 1 0 0 0 0 20 21 2 0 0 0 0 20 28 1 0 0 0 0 21 22 1 0 0 0 0 21 25 1 0 0 0 0 22 23 1 0 0 0 0 22 29 2 0 0 0 0 23 24 2 0 0 0 0 23 30 1 0 0 0 0 24 31 1 0 0 0 0 25 31 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	422.17
Volume:	441.663
LogP:	5.833
LogD:	3.353
LogS:	-3.156
# Rotatable Bonds:	5
TPSA:	111.13
# H-Bond Aceptor:	6
# H-Bond Donor:	4
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.403
Synthetic Accessibility Score:	3.212
Fsp3:	0.24
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.871
MDCK Permeability:	1.3353880603972357e-05
Pgp-inhibitor:	0.158
Pgp-substrate:	0.635
Human Intestinal Absorption (HIA):	0.02
20% Bioavailability (F20%):	0.94
30% Bioavailability (F30%):	0.53

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.007
Plasma Protein Binding (PPB):	94.72270965576172%
Volume Distribution (VD):	0.719
Pgp-substrate:	3.440211057662964%

ADMET: Metabolism

CYP1A2-inhibitor:	0.701
CYP1A2-substrate:	0.141
CYP2C19-inhibitor:	0.906
CYP2C19-substrate:	0.052
CYP2C9-inhibitor:	0.862
CYP2C9-substrate:	0.89
CYP2D6-inhibitor:	0.742
CYP2D6-substrate:	0.176
CYP3A4-inhibitor:	0.224
CYP3A4-substrate:	0.097

ADMET: Excretion

Clearance (CL):	8.407
Half-life (T1/2):	0.72

ADMET: Toxicity

hERG Blockers:	0.009
Human Hepatotoxicity (H-HT):	0.652
Drug-inuced Liver Injury (DILI):	0.985
AMES Toxicity:	0.662
Rat Oral Acute Toxicity:	0.376
Maximum Recommended Daily Dose:	0.023
Skin Sensitization:	0.529
Carcinogencity:	0.112
Eye Corrosion:	0.003
Eye Irritation:	0.758
Respiratory Toxicity:	0.23

Download Data

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

Natural Product: NPC326500

Natural Product ID:	NPC326500
*Common Name:**	8-Lavandulylkaempferol
IUPAC Name:	3,5,7-trihydroxy-2-(4-hydroxyphenyl)-8-(5-methyl-2-prop-1-en-2-ylhex-4-enyl)chromen-4-one
Synonyms:	8-Lavandulylkaempferol
Standard InCHIKey:	RLJJIYPLHFCLRD-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C25H26O6/c1-13(2)5-6-16(14(3)4)11-18-19(27)12-20(28)21-22(29)23(30)24(31-25(18)21)15-7-9-17(26)10-8-15/h5,7-10,12,16,26-28,30H,3,6,11H2,1-2,4H3
SMILES:	CC(=CCC(CC1=C2C(=C(C=C1O)O)C(=O)C(=C(O2)C3=CC=C(C=C3)O)O)C(=C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL463941
PubChem CID:	16083184
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001615] Flavones [CHEMONTID:0003504] 8-prenylated flavones

*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
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10654410]
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	n.a.	root	n.a.	PMID[10843587]
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	Roots	n.a.	n.a.	PMID[15568770]
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	n.a.	root	n.a.	PMID[16392664]
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	roots	Hualien Hsien, Taiwan	2003-JUL	PMID[16933887]
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	n.a.	root	n.a.	PMID[16933887]
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	n.a.	root	n.a.	PMID[17951038]
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18175961]
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24295087]
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27575476]
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	Roots	n.a.	n.a.	PMID[30298740]
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	Roots	n.a.	n.a.	PMID[9868163]
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	n.a.	root	n.a.	Database[Article]
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO19231	Sophora flavescens	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	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	IC50	=	24.3	ug.mL-1	PMID[497172]

☑ 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 NPC326500 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	430
0.1-0.2	1704
0.2-0.3	4357
0.3-0.4	10613
0.4-0.5	7468
0.5-0.6	3832
0.6-0.7	5384
0.7-0.8	4439
0.8-0.85	2334
0.85-0.9	1609
0.9-0.95	473
0.95-1	54

Similarity Score	Similarity Level	Natural Product ID
0.9928	High Similarity	NPC293053
0.9928	High Similarity	NPC190637
0.9928	High Similarity	NPC9117
0.9928	High Similarity	NPC24821
0.9928	High Similarity	NPC212932
0.9856	High Similarity	NPC216538
0.9856	High Similarity	NPC273538
0.9855	High Similarity	NPC473042
0.9855	High Similarity	NPC200694
0.9786	High Similarity	NPC178343
0.9786	High Similarity	NPC124729
0.9786	High Similarity	NPC306488
0.9786	High Similarity	NPC5820
0.9718	High Similarity	NPC470461
0.9716	High Similarity	NPC166757
0.9716	High Similarity	NPC14001
0.9648	High Similarity	NPC244407
0.9648	High Similarity	NPC296869
0.9648	High Similarity	NPC470460
0.9645	High Similarity	NPC220418
0.9643	High Similarity	NPC158874
0.964	High Similarity	NPC282300
0.9638	High Similarity	NPC55018
0.9638	High Similarity	NPC301217
0.9638	High Similarity	NPC303633
0.9638	High Similarity	NPC220062
0.9638	High Similarity	NPC96565
0.9638	High Similarity	NPC216978
0.958	High Similarity	NPC269420
0.9568	High Similarity	NPC172986
0.9568	High Similarity	NPC261227
0.9568	High Similarity	NPC241100
0.9568	High Similarity	NPC270883
0.9568	High Similarity	NPC159275
0.9565	High Similarity	NPC201395
0.9514	High Similarity	NPC61258
0.9507	High Similarity	NPC154217
0.9507	High Similarity	NPC470458
0.9504	High Similarity	NPC11700
0.9504	High Similarity	NPC219915
0.95	High Similarity	NPC90582
0.95	High Similarity	NPC147688
0.95	High Similarity	NPC118840
0.95	High Similarity	NPC156590
0.95	High Similarity	NPC110969
0.95	High Similarity	NPC262094
0.95	High Similarity	NPC205006
0.95	High Similarity	NPC64908
0.9496	High Similarity	NPC78913
0.9496	High Similarity	NPC152042
0.9496	High Similarity	NPC241838
0.9496	High Similarity	NPC217186
0.9496	High Similarity	NPC143799
0.9496	High Similarity	NPC53181
0.9496	High Similarity	NPC18260
0.9441	High Similarity	NPC308200
0.9437	High Similarity	NPC271288
0.9437	High Similarity	NPC224714
0.9437	High Similarity	NPC234629
0.9437	High Similarity	NPC1886
0.9437	High Similarity	NPC196137
0.9437	High Similarity	NPC311741
0.9433	High Similarity	NPC59739
0.9433	High Similarity	NPC293852
0.9433	High Similarity	NPC204469
0.9433	High Similarity	NPC214236
0.9433	High Similarity	NPC144499
0.9433	High Similarity	NPC62840
0.9433	High Similarity	NPC78803
0.9433	High Similarity	NPC226636
0.9433	High Similarity	NPC217083
0.9433	High Similarity	NPC299080
0.9433	High Similarity	NPC11561
0.9429	High Similarity	NPC269652
0.9429	High Similarity	NPC305355
0.9429	High Similarity	NPC475680
0.9429	High Similarity	NPC150522
0.9429	High Similarity	NPC69769
0.9429	High Similarity	NPC230285
0.9429	High Similarity	NPC235239
0.9429	High Similarity	NPC103342
0.9429	High Similarity	NPC59951
0.9429	High Similarity	NPC146679
0.9429	High Similarity	NPC103904
0.9429	High Similarity	NPC184536
0.9429	High Similarity	NPC281207
0.9424	High Similarity	NPC276905
0.9424	High Similarity	NPC470669
0.9424	High Similarity	NPC470668
0.942	High Similarity	NPC216361
0.942	High Similarity	NPC13408
0.942	High Similarity	NPC281917
0.942	High Similarity	NPC116775
0.942	High Similarity	NPC187432
0.942	High Similarity	NPC256042
0.9384	High Similarity	NPC216035
0.9384	High Similarity	NPC217149
0.9384	High Similarity	NPC142527
0.9384	High Similarity	NPC157784
0.9384	High Similarity	NPC37684
0.9384	High Similarity	NPC63187
0.9384	High Similarity	NPC45934
0.9379	High Similarity	NPC471115
0.9379	High Similarity	NPC29777
0.9375	High Similarity	NPC168085
0.9375	High Similarity	NPC145467
0.9375	High Similarity	NPC39195
0.9371	High Similarity	NPC474161
0.9371	High Similarity	NPC477955
0.9371	High Similarity	NPC329678
0.9371	High Similarity	NPC476088
0.9371	High Similarity	NPC472629
0.9371	High Similarity	NPC470322
0.9371	High Similarity	NPC181388
0.9366	High Similarity	NPC81697
0.9366	High Similarity	NPC188632
0.9366	High Similarity	NPC18585
0.9366	High Similarity	NPC38219
0.9366	High Similarity	NPC112791
0.9366	High Similarity	NPC166138
0.9366	High Similarity	NPC125894
0.9366	High Similarity	NPC107177
0.9366	High Similarity	NPC196459
0.9366	High Similarity	NPC470296
0.9366	High Similarity	NPC223812
0.9366	High Similarity	NPC77794
0.9366	High Similarity	NPC85162
0.9366	High Similarity	NPC278249
0.9366	High Similarity	NPC106985
0.9366	High Similarity	NPC87609
0.9366	High Similarity	NPC94794
0.9362	High Similarity	NPC136840
0.9362	High Similarity	NPC469404
0.9362	High Similarity	NPC14871
0.9362	High Similarity	NPC103362
0.9353	High Similarity	NPC228661
0.9353	High Similarity	NPC299379
0.9324	High Similarity	NPC192587
0.932	High Similarity	NPC193200
0.932	High Similarity	NPC311579
0.932	High Similarity	NPC236756
0.9315	High Similarity	NPC254412
0.9315	High Similarity	NPC319910
0.9315	High Similarity	NPC262038
0.9315	High Similarity	NPC278476
0.9315	High Similarity	NPC205046
0.9315	High Similarity	NPC59162
0.9315	High Similarity	NPC304295
0.9315	High Similarity	NPC262039
0.931	High Similarity	NPC317492
0.931	High Similarity	NPC5173
0.931	High Similarity	NPC471114
0.9306	High Similarity	NPC24673
0.9306	High Similarity	NPC97716
0.9306	High Similarity	NPC237635
0.9306	High Similarity	NPC104406
0.9306	High Similarity	NPC201731
0.9306	High Similarity	NPC296998
0.9306	High Similarity	NPC79469
0.9306	High Similarity	NPC473077
0.9301	High Similarity	NPC131568
0.9301	High Similarity	NPC319752
0.9301	High Similarity	NPC473015
0.9301	High Similarity	NPC328623
0.9301	High Similarity	NPC311144
0.9301	High Similarity	NPC469935
0.9301	High Similarity	NPC470890
0.9301	High Similarity	NPC178627
0.9301	High Similarity	NPC131579
0.9301	High Similarity	NPC473013
0.9301	High Similarity	NPC87486
0.9301	High Similarity	NPC473014
0.9301	High Similarity	NPC235217
0.9301	High Similarity	NPC124780
0.9296	High Similarity	NPC10937
0.9296	High Similarity	NPC296917
0.9296	High Similarity	NPC324134
0.9296	High Similarity	NPC64915
0.9296	High Similarity	NPC227579
0.9296	High Similarity	NPC37496
0.9296	High Similarity	NPC324436
0.9296	High Similarity	NPC223500
0.9296	High Similarity	NPC328164
0.9296	High Similarity	NPC40833
0.9296	High Similarity	NPC265040
0.9296	High Similarity	NPC76338
0.9296	High Similarity	NPC1089
0.9296	High Similarity	NPC182852
0.9296	High Similarity	NPC161506
0.9296	High Similarity	NPC32739
0.9296	High Similarity	NPC36181
0.9296	High Similarity	NPC78
0.9296	High Similarity	NPC66515
0.9296	High Similarity	NPC166482
0.9296	High Similarity	NPC306829
0.9296	High Similarity	NPC194432
0.9296	High Similarity	NPC228504
0.9296	High Similarity	NPC177354
0.9296	High Similarity	NPC220998
0.9296	High Similarity	NPC125855

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 NPC326500 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	386
0.1-0.2	943
0.2-0.3	1673
0.3-0.4	2712
0.4-0.5	1876
0.5-0.6	1022
0.6-0.7	364
0.7-0.8	109
0.8-0.85	45
0.85-0.9	14
0.9-0.95	5
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9856	High Similarity	NPD4378	Clinical (unspecified phase)
0.9167	High Similarity	NPD7410	Clinical (unspecified phase)
0.8973	High Similarity	NPD1512	Approved
0.8944	High Similarity	NPD1552	Clinical (unspecified phase)
0.8944	High Similarity	NPD1550	Clinical (unspecified phase)
0.8936	High Similarity	NPD1510	Phase 2
0.8933	High Similarity	NPD2393	Clinical (unspecified phase)
0.8882	High Similarity	NPD7075	Discontinued
0.8881	High Similarity	NPD1549	Phase 2
0.8874	High Similarity	NPD8443	Clinical (unspecified phase)
0.8873	High Similarity	NPD2796	Approved
0.8859	High Similarity	NPD4380	Phase 2
0.8836	High Similarity	NPD1511	Approved
0.8808	High Similarity	NPD7096	Clinical (unspecified phase)
0.8786	High Similarity	NPD1240	Approved
0.8742	High Similarity	NPD6801	Discontinued
0.8684	High Similarity	NPD2801	Approved
0.8675	High Similarity	NPD7411	Suspended
0.8662	High Similarity	NPD1607	Approved
0.8618	High Similarity	NPD1934	Approved
0.8616	High Similarity	NPD7804	Clinical (unspecified phase)
0.8581	High Similarity	NPD6799	Approved
0.8562	High Similarity	NPD2800	Approved
0.8562	High Similarity	NPD7819	Suspended
0.8516	High Similarity	NPD4381	Clinical (unspecified phase)
0.8506	High Similarity	NPD3817	Phase 2
0.8503	High Similarity	NPD3750	Approved
0.8452	Intermediate Similarity	NPD3882	Suspended
0.8428	Intermediate Similarity	NPD6166	Phase 2
0.8428	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8428	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8367	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8366	Intermediate Similarity	NPD6599	Discontinued
0.8354	Intermediate Similarity	NPD6959	Discontinued
0.8333	Intermediate Similarity	NPD7768	Phase 2
0.8313	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8311	Intermediate Similarity	NPD1243	Approved
0.8311	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8288	Intermediate Similarity	NPD2799	Discontinued
0.8276	Intermediate Similarity	NPD6651	Approved
0.8252	Intermediate Similarity	NPD2313	Discontinued
0.8231	Intermediate Similarity	NPD2935	Discontinued
0.8182	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.8176	Intermediate Similarity	NPD5494	Approved
0.8171	Intermediate Similarity	NPD6797	Phase 2
0.817	Intermediate Similarity	NPD920	Approved
0.817	Intermediate Similarity	NPD5403	Approved
0.8165	Intermediate Similarity	NPD3749	Approved
0.8163	Intermediate Similarity	NPD3748	Approved
0.8148	Intermediate Similarity	NPD7473	Discontinued
0.8125	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8121	Intermediate Similarity	NPD7251	Discontinued
0.8108	Intermediate Similarity	NPD1551	Phase 2
0.8098	Intermediate Similarity	NPD3818	Discontinued
0.8075	Intermediate Similarity	NPD6232	Discontinued
0.8072	Intermediate Similarity	NPD7808	Phase 3
0.8054	Intermediate Similarity	NPD2344	Approved
0.8049	Intermediate Similarity	NPD7054	Approved
0.8039	Intermediate Similarity	NPD2533	Approved
0.8039	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.8039	Intermediate Similarity	NPD2534	Approved
0.8039	Intermediate Similarity	NPD5401	Approved
0.8039	Intermediate Similarity	NPD2532	Approved
0.8038	Intermediate Similarity	NPD5402	Approved
0.8026	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD7074	Phase 3
0.8	Intermediate Similarity	NPD7472	Approved
0.8	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD3268	Approved
0.7987	Intermediate Similarity	NPD6099	Approved
0.7987	Intermediate Similarity	NPD6100	Approved
0.7972	Intermediate Similarity	NPD2798	Approved
0.7964	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7952	Intermediate Similarity	NPD5953	Discontinued
0.7949	Intermediate Similarity	NPD3226	Approved
0.7939	Intermediate Similarity	NPD7286	Phase 2
0.7919	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7904	Intermediate Similarity	NPD6559	Discontinued
0.7902	Intermediate Similarity	NPD2797	Approved
0.7902	Intermediate Similarity	NPD1203	Approved
0.7901	Intermediate Similarity	NPD1247	Approved
0.7895	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7888	Intermediate Similarity	NPD919	Approved
0.7875	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7862	Intermediate Similarity	NPD4908	Phase 1
0.7857	Intermediate Similarity	NPD7390	Discontinued
0.7843	Intermediate Similarity	NPD2309	Approved
0.7816	Intermediate Similarity	NPD4363	Phase 3
0.7816	Intermediate Similarity	NPD4360	Phase 2
0.7815	Intermediate Similarity	NPD2346	Discontinued
0.7778	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.777	Intermediate Similarity	NPD943	Approved
0.7746	Intermediate Similarity	NPD422	Phase 1
0.7746	Intermediate Similarity	NPD1610	Phase 2
0.7725	Intermediate Similarity	NPD5844	Phase 1
0.7714	Intermediate Similarity	NPD1548	Phase 1
0.7697	Intermediate Similarity	NPD3926	Phase 2
0.7692	Intermediate Similarity	NPD9717	Approved
0.7682	Intermediate Similarity	NPD7033	Discontinued
0.7682	Intermediate Similarity	NPD4308	Phase 3
0.767	Intermediate Similarity	NPD4361	Phase 2
0.767	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7662	Intermediate Similarity	NPD4628	Phase 3
0.7655	Intermediate Similarity	NPD3266	Approved
0.7655	Intermediate Similarity	NPD3267	Approved
0.7633	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7627	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7625	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7622	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD6832	Phase 2
0.76	Intermediate Similarity	NPD5124	Phase 1
0.76	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD3225	Approved
0.7569	Intermediate Similarity	NPD1608	Approved
0.7568	Intermediate Similarity	NPD4625	Phase 3
0.7531	Intermediate Similarity	NPD1465	Phase 2
0.75	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD4288	Approved
0.7484	Intermediate Similarity	NPD2654	Approved
0.7468	Intermediate Similarity	NPD1471	Phase 3
0.7451	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.744	Intermediate Similarity	NPD2403	Approved
0.7432	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7425	Intermediate Similarity	NPD5711	Approved
0.7425	Intermediate Similarity	NPD5710	Approved
0.7425	Intermediate Similarity	NPD7229	Phase 3
0.7417	Intermediate Similarity	NPD4307	Phase 2
0.7401	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.74	Intermediate Similarity	NPD1296	Phase 2
0.74	Intermediate Similarity	NPD6798	Discontinued
0.7397	Intermediate Similarity	NPD4749	Approved
0.7391	Intermediate Similarity	NPD7458	Discontinued
0.7379	Intermediate Similarity	NPD1201	Approved
0.7375	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD1729	Discontinued
0.7368	Intermediate Similarity	NPD447	Suspended
0.7368	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD6355	Discontinued
0.7361	Intermediate Similarity	NPD17	Approved
0.7358	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7355	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD3972	Approved
0.7325	Intermediate Similarity	NPD7003	Approved
0.7312	Intermediate Similarity	NPD5049	Phase 3
0.7303	Intermediate Similarity	NPD4060	Phase 1
0.7303	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD1613	Approved
0.7297	Intermediate Similarity	NPD1470	Approved
0.7297	Intermediate Similarity	NPD1164	Approved
0.729	Intermediate Similarity	NPD5406	Approved
0.729	Intermediate Similarity	NPD5408	Approved
0.729	Intermediate Similarity	NPD5405	Approved
0.729	Intermediate Similarity	NPD5404	Approved
0.7285	Intermediate Similarity	NPD411	Approved
0.7285	Intermediate Similarity	NPD3764	Approved
0.7284	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD2354	Approved
0.7273	Intermediate Similarity	NPD8434	Phase 2
0.7273	Intermediate Similarity	NPD2296	Approved
0.7258	Intermediate Similarity	NPD7584	Approved
0.7255	Intermediate Similarity	NPD1933	Approved
0.7255	Intermediate Similarity	NPD230	Phase 1
0.7251	Intermediate Similarity	NPD3751	Discontinued
0.7239	Intermediate Similarity	NPD6585	Discontinued
0.7237	Intermediate Similarity	NPD6233	Phase 2
0.7235	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD9545	Approved
0.7219	Intermediate Similarity	NPD3787	Discontinued
0.7213	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7211	Intermediate Similarity	NPD1481	Phase 2
0.7203	Intermediate Similarity	NPD9493	Approved
0.72	Intermediate Similarity	NPD8312	Approved
0.72	Intermediate Similarity	NPD8313	Approved
0.72	Intermediate Similarity	NPD2861	Phase 2
0.7195	Intermediate Similarity	NPD5890	Approved
0.7195	Intermediate Similarity	NPD5889	Approved
0.7191	Intermediate Similarity	NPD4287	Approved
0.7188	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7171	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD7199	Phase 2
0.7152	Intermediate Similarity	NPD6844	Discontinued
0.7143	Intermediate Similarity	NPD1535	Discovery
0.7134	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD2353	Approved
0.7134	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD6002	Phase 3
0.7134	Intermediate Similarity	NPD6004	Phase 3
0.7134	Intermediate Similarity	NPD6005	Phase 3
0.7133	Intermediate Similarity	NPD1019	Discontinued
0.712	Intermediate Similarity	NPD6780	Approved
0.712	Intermediate Similarity	NPD6782	Approved
0.712	Intermediate Similarity	NPD6778	Approved
0.712	Intermediate Similarity	NPD6777	Approved
0.712	Intermediate Similarity	NPD6776	Approved
0.712	Intermediate Similarity	NPD6781	Approved
0.712	Intermediate Similarity	NPD6779	Approved
0.7114	Intermediate Similarity	NPD1876	Approved
0.7113	Intermediate Similarity	NPD1241	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