NPASS Compound

Structure

NPC471213 OpenBabel07101718292D 34 37 0 0 1 0 0 0 0 0999 V2000 2.7285 -2.5872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6945 -0.9142 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7355 -0.4914 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.6603 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5391 0.0517 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 -6.0622 -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 2.2802 -0.9142 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8320 0.7588 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 -6.0622 0.5000 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 -5.1962 0.0000 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 -6.9282 -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 -6.9282 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 -2.5981 1.5000 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 -3.4641 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.3301 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.9873 -1.6213 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -7.7942 -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 -3.4641 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.9533 -1.8801 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 0.5000 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 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 25 1 0 0 0 0 2 25 1 0 0 0 0 3 26 1 0 0 0 0 4 32 1 0 0 0 0 5 9 1 0 0 0 0 5 10 1 0 0 0 0 6 7 2 0 0 0 0 6 14 1 0 0 0 0 7 16 1 0 0 0 0 8 11 1 0 0 0 0 8 15 1 0 0 0 0 9 25 1 0 0 0 0 10 26 1 0 0 0 0 11 26 1 0 0 0 0 12 14 2 0 0 0 0 12 18 1 0 0 0 0 13 17 2 0 0 0 0 13 19 1 0 0 0 0 15 17 1 0 0 0 0 15 21 2 0 0 0 0 16 18 2 0 0 0 0 16 27 1 0 0 0 0 17 34 1 0 0 0 0 18 32 1 0 0 0 0 19 20 2 0 0 0 0 19 33 1 0 0 0 0 20 21 1 0 0 0 0 20 22 1 0 0 0 0 21 28 1 0 0 0 0 22 23 1 0 0 0 0 22 29 2 0 0 0 0 23 24 1 0 0 0 0 23 30 1 1 0 0 0 24 14 1 6 0 0 0 24 33 1 0 0 0 0 25 31 1 0 0 0 0 26 34 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	472.21
Volume:	475.893
LogP:	3.222
LogD:	2.61
LogS:	-3.981
# Rotatable Bonds:	6
TPSA:	125.68
# H-Bond Aceptor:	8
# H-Bond Donor:	4
# Rings:	4
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.5
Synthetic Accessibility Score:	4.069
Fsp3:	0.5
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.935
MDCK Permeability:	1.6413290722994134e-05
Pgp-inhibitor:	0.419
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.045
20% Bioavailability (F20%):	0.008
30% Bioavailability (F30%):	0.004

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.029
Plasma Protein Binding (PPB):	97.4073715209961%
Volume Distribution (VD):	0.695
Pgp-substrate:	3.9361298084259033%

ADMET: Metabolism

CYP1A2-inhibitor:	0.053
CYP1A2-substrate:	0.755
CYP2C19-inhibitor:	0.064
CYP2C19-substrate:	0.66
CYP2C9-inhibitor:	0.46
CYP2C9-substrate:	0.862
CYP2D6-inhibitor:	0.329
CYP2D6-substrate:	0.423
CYP3A4-inhibitor:	0.53
CYP3A4-substrate:	0.461

ADMET: Excretion

Clearance (CL):	7.44
Half-life (T1/2):	0.36

ADMET: Toxicity

hERG Blockers:	0.013
Human Hepatotoxicity (H-HT):	0.248
Drug-inuced Liver Injury (DILI):	0.429
AMES Toxicity:	0.081
Rat Oral Acute Toxicity:	0.117
Maximum Recommended Daily Dose:	0.029
Skin Sensitization:	0.218
Carcinogencity:	0.065
Eye Corrosion:	0.003
Eye Irritation:	0.011
Respiratory Toxicity:	0.027

Download Data

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

Natural Product: NPC471213

Natural Product ID:	NPC471213
*Common Name:**	(7R,8R)-5,7-Dihydroxy-8-(4-Hydroxy-3-Methoxyphenyl)-2-(4-Hydroxy-4-Methylpentyl)-2-Methyl-3,4,7,8-Tetrahydropyrano[3,2-G]Chromen-6-One
IUPAC Name:	(7R,8R)-5,7-dihydroxy-8-(4-hydroxy-3-methoxyphenyl)-2-(4-hydroxy-4-methylpentyl)-2-methyl-3,4,7,8-tetrahydropyrano[3,2-g]chromen-6-one
Synonyms:
Standard InCHIKey:	KWSGAQMDMOUWHH-GPTJOGTASA-N
Standard InCHI:	InChI=1S/C26H32O8/c1-25(2,31)9-5-10-26(3)11-8-15-17(34-26)13-19-20(21(15)28)22(29)23(30)24(33-19)14-6-7-16(27)18(12-14)32-4/h6-7,12-13,23-24,27-28,30-31H,5,8-11H2,1-4H3/t23-,24+,26?/m0/s1
SMILES:	COc1cc(ccc1O)[C@H]1Oc2cc3OC(C)(CCCC(O)(C)C)CCc3c(c2C(=O)[C@@H]1O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2387715
PubChem CID:	71659767
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0000337] Flavans [CHEMONTID:0003646] 6-prenylated flavans [CHEMONTID:0003507] 6-prenylated flavanones

*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
NPO22079	Paulownia tomentosa	Species	Paulowniaceae	Eukaryota	fruits	n.a.	n.a.	PMID[17625893]
NPO22079	Paulownia tomentosa	Species	Paulowniaceae	Eukaryota	Fruits	n.a.	n.a.	PMID[18293924]
NPO22079	Paulownia tomentosa	Species	Paulowniaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20192247]
NPO22079	Paulownia tomentosa	Species	Paulowniaceae	Eukaryota	n.a.	fruit	n.a.	PMID[21319773]
NPO22079	Paulownia tomentosa	Species	Paulowniaceae	Eukaryota	fruits	n.a.	n.a.	PMID[22445674]
NPO22079	Paulownia tomentosa	Species	Paulowniaceae	Eukaryota	fruits	n.a.	n.a.	PMID[23623680]
NPO22079	Paulownia tomentosa	Species	Paulowniaceae	Eukaryota	fruits	n.a.	n.a.	PMID[25735399]
NPO22079	Paulownia tomentosa	Species	Paulowniaceae	Eukaryota	Fruits	n.a.	n.a.	PMID[28322565]
NPO22079	Paulownia tomentosa	Species	Paulowniaceae	Eukaryota	Fruits	n.a.	n.a.	PMID[28968119]
NPO22079	Paulownia tomentosa	Species	Paulowniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22079	Paulownia tomentosa	Species	Paulowniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22079	Paulownia tomentosa	Species	Paulowniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO22079	Paulownia tomentosa	Species	Paulowniaceae	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	2
Ki	1

Activity Type	# Activity
Individual Protein	1
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT279	Individual Protein	Leukocyte elastase	Homo sapiens	IC50	=	46600.0	nM	PMID[458932]
NPT2	Others	Unspecified		Ki	=	3700.0	nM	PMID[458931]
NPT2	Others	Unspecified		IC50	=	5000.0	nM	PMID[458931]

☑ 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 NPC471213 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	418
0.1-0.2	1651
0.2-0.3	4078
0.3-0.4	9916
0.4-0.5	8169
0.5-0.6	3682
0.6-0.7	4757
0.7-0.8	5506
0.8-0.85	2714
0.85-0.9	1471
0.9-0.95	289
0.95-1	46

Similarity Score	Similarity Level	Natural Product ID
0.9745	High Similarity	NPC472625
0.9744	High Similarity	NPC472634
0.9744	High Similarity	NPC471211
0.9744	High Similarity	NPC471210
0.9744	High Similarity	NPC471212
0.9744	High Similarity	NPC472632
0.9744	High Similarity	NPC471499
0.9684	High Similarity	NPC62261
0.9682	High Similarity	NPC474034
0.9682	High Similarity	NPC474033
0.9679	High Similarity	NPC470326
0.9679	High Similarity	NPC287328
0.9679	High Similarity	NPC282009
0.9679	High Similarity	NPC472630
0.9679	High Similarity	NPC472631
0.9679	High Similarity	NPC174953
0.9618	High Similarity	NPC289771
0.9618	High Similarity	NPC474038
0.9618	High Similarity	NPC26326
0.9615	High Similarity	NPC22192
0.9615	High Similarity	NPC473990
0.956	High Similarity	NPC36
0.956	High Similarity	NPC293319
0.956	High Similarity	NPC72787
0.956	High Similarity	NPC7154
0.956	High Similarity	NPC125039
0.956	High Similarity	NPC36916
0.956	High Similarity	NPC58223
0.956	High Similarity	NPC7688
0.9557	High Similarity	NPC472635
0.9554	High Similarity	NPC192686
0.9554	High Similarity	NPC118256
0.9554	High Similarity	NPC470183
0.9554	High Similarity	NPC475784
0.9554	High Similarity	NPC119209
0.9551	High Similarity	NPC27337
0.9551	High Similarity	NPC471209
0.9551	High Similarity	NPC472598
0.9551	High Similarity	NPC474055
0.9494	High Similarity	NPC142252
0.9494	High Similarity	NPC173137
0.9494	High Similarity	NPC134783
0.9494	High Similarity	NPC158188
0.949	High Similarity	NPC117418
0.949	High Similarity	NPC53545
0.9487	High Similarity	NPC470328
0.9487	High Similarity	NPC195796
0.9487	High Similarity	NPC209614
0.9487	High Similarity	NPC250922
0.9487	High Similarity	NPC291878
0.9487	High Similarity	NPC35038
0.9487	High Similarity	NPC278778
0.9487	High Similarity	NPC320825
0.9487	High Similarity	NPC472626
0.9487	High Similarity	NPC13858
0.9487	High Similarity	NPC326037
0.9444	High Similarity	NPC102277
0.9444	High Similarity	NPC279209
0.9441	High Similarity	NPC474024
0.9441	High Similarity	NPC158761
0.9437	High Similarity	NPC224280
0.9437	High Similarity	NPC475888
0.9434	High Similarity	NPC211107
0.9434	High Similarity	NPC476247
0.943	High Similarity	NPC472624
0.9427	High Similarity	NPC291508
0.9427	High Similarity	NPC284820
0.9427	High Similarity	NPC471479
0.9427	High Similarity	NPC52530
0.9427	High Similarity	NPC67876
0.9427	High Similarity	NPC471515
0.9427	High Similarity	NPC473272
0.9423	High Similarity	NPC200761
0.9423	High Similarity	NPC470327
0.9423	High Similarity	NPC477503
0.9423	High Similarity	NPC226025
0.9423	High Similarity	NPC45849
0.9423	High Similarity	NPC321779
0.939	High Similarity	NPC108202
0.9387	High Similarity	NPC121333
0.9383	High Similarity	NPC326877
0.9383	High Similarity	NPC177480
0.9375	High Similarity	NPC186686
0.9375	High Similarity	NPC124038
0.9375	High Similarity	NPC474240
0.9375	High Similarity	NPC41301
0.9363	High Similarity	NPC20530
0.9363	High Similarity	NPC471500
0.9363	High Similarity	NPC215917
0.9363	High Similarity	NPC10754
0.9359	High Similarity	NPC192083
0.9359	High Similarity	NPC298692
0.9359	High Similarity	NPC74924
0.9359	High Similarity	NPC18727
0.9359	High Similarity	NPC213896
0.9329	High Similarity	NPC208668
0.9325	High Similarity	NPC74559
0.9321	High Similarity	NPC470456
0.9321	High Similarity	NPC477154
0.9321	High Similarity	NPC6588
0.9321	High Similarity	NPC218226
0.9321	High Similarity	NPC117854
0.9321	High Similarity	NPC260266
0.9321	High Similarity	NPC477502
0.9317	High Similarity	NPC470457
0.9317	High Similarity	NPC234052
0.9313	High Similarity	NPC474162
0.9313	High Similarity	NPC472964
0.9313	High Similarity	NPC201800
0.9313	High Similarity	NPC220912
0.9313	High Similarity	NPC474150
0.9308	High Similarity	NPC263449
0.9308	High Similarity	NPC321399
0.9308	High Similarity	NPC36217
0.9304	High Similarity	NPC237418
0.9304	High Similarity	NPC52889
0.9304	High Similarity	NPC223787
0.9299	High Similarity	NPC259710
0.9299	High Similarity	NPC304745
0.9299	High Similarity	NPC48579
0.9299	High Similarity	NPC304207
0.9299	High Similarity	NPC477958
0.9299	High Similarity	NPC217706
0.9299	High Similarity	NPC111341
0.9299	High Similarity	NPC207809
0.9295	High Similarity	NPC19721
0.9295	High Similarity	NPC9743
0.9295	High Similarity	NPC219582
0.9295	High Similarity	NPC61506
0.9295	High Similarity	NPC475790
0.9295	High Similarity	NPC246162
0.9295	High Similarity	NPC240476
0.9295	High Similarity	NPC36835
0.9295	High Similarity	NPC302950
0.9295	High Similarity	NPC106976
0.9295	High Similarity	NPC260491
0.9295	High Similarity	NPC236637
0.9295	High Similarity	NPC138288
0.9273	High Similarity	NPC294629
0.9268	High Similarity	NPC472454
0.9268	High Similarity	NPC256760
0.9268	High Similarity	NPC261254
0.9268	High Similarity	NPC257667
0.9268	High Similarity	NPC186847
0.9264	High Similarity	NPC270578
0.9264	High Similarity	NPC165456
0.9264	High Similarity	NPC475212
0.9264	High Similarity	NPC52382
0.9264	High Similarity	NPC152477
0.9264	High Similarity	NPC242395
0.9259	High Similarity	NPC43319
0.9259	High Similarity	NPC236934
0.9259	High Similarity	NPC477517
0.9259	High Similarity	NPC119589
0.9259	High Similarity	NPC470462
0.9259	High Similarity	NPC5778
0.9255	High Similarity	NPC470459
0.925	High Similarity	NPC113163
0.925	High Similarity	NPC84324
0.925	High Similarity	NPC165970
0.925	High Similarity	NPC228383
0.925	High Similarity	NPC112418
0.925	High Similarity	NPC3629
0.925	High Similarity	NPC198829
0.925	High Similarity	NPC66618
0.925	High Similarity	NPC474239
0.925	High Similarity	NPC266314
0.925	High Similarity	NPC305987
0.925	High Similarity	NPC308992
0.925	High Similarity	NPC288131
0.9245	High Similarity	NPC210459
0.9245	High Similarity	NPC74178
0.9245	High Similarity	NPC204879
0.9245	High Similarity	NPC476410
0.9245	High Similarity	NPC284127
0.9245	High Similarity	NPC172202
0.9245	High Similarity	NPC55738
0.9245	High Similarity	NPC95936
0.9245	High Similarity	NPC187792
0.9245	High Similarity	NPC152904
0.9245	High Similarity	NPC184755
0.9245	High Similarity	NPC250214
0.9241	High Similarity	NPC470600
0.9241	High Similarity	NPC474638
0.9241	High Similarity	NPC471985
0.9236	High Similarity	NPC141212
0.9236	High Similarity	NPC27532
0.9236	High Similarity	NPC268193
0.9236	High Similarity	NPC248793
0.9236	High Similarity	NPC246328
0.9236	High Similarity	NPC256346
0.9236	High Similarity	NPC325028
0.9236	High Similarity	NPC293286
0.9236	High Similarity	NPC180301
0.9231	High Similarity	NPC471677
0.9231	High Similarity	NPC278476
0.9231	High Similarity	NPC319910
0.9231	High Similarity	NPC474023
0.9231	High Similarity	NPC262038
0.9231	High Similarity	NPC262039

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 NPC471213 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	371
0.1-0.2	934
0.2-0.3	1826
0.3-0.4	2621
0.4-0.5	1801
0.5-0.6	961
0.6-0.7	456
0.7-0.8	133
0.8-0.85	29
0.85-0.9	13
0.9-0.95	5
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.956	High Similarity	NPD6168	Clinical (unspecified phase)
0.956	High Similarity	NPD6166	Phase 2
0.956	High Similarity	NPD6167	Clinical (unspecified phase)
0.9359	High Similarity	NPD2393	Clinical (unspecified phase)
0.9295	High Similarity	NPD1934	Approved
0.9207	High Similarity	NPD7074	Phase 3
0.9146	High Similarity	NPD7054	Approved
0.9096	High Similarity	NPD7251	Discontinued
0.9091	High Similarity	NPD7472	Approved
0.9042	High Similarity	NPD7808	Phase 3
0.9036	High Similarity	NPD6797	Phase 2
0.8944	High Similarity	NPD7075	Discontinued
0.8924	High Similarity	NPD4380	Phase 2
0.8916	High Similarity	NPD7804	Clinical (unspecified phase)
0.8882	High Similarity	NPD3882	Suspended
0.8875	High Similarity	NPD2801	Approved
0.882	High Similarity	NPD3817	Phase 2
0.8817	High Similarity	NPD4338	Clinical (unspecified phase)
0.879	High Similarity	NPD1512	Approved
0.8758	High Similarity	NPD7096	Clinical (unspecified phase)
0.8743	High Similarity	NPD3818	Discontinued
0.8726	High Similarity	NPD4378	Clinical (unspecified phase)
0.872	High Similarity	NPD5494	Approved
0.8662	High Similarity	NPD1511	Approved
0.865	High Similarity	NPD4868	Clinical (unspecified phase)
0.8598	High Similarity	NPD4381	Clinical (unspecified phase)
0.8589	High Similarity	NPD8443	Clinical (unspecified phase)
0.8588	High Similarity	NPD7993	Clinical (unspecified phase)
0.858	High Similarity	NPD6801	Discontinued
0.8443	Intermediate Similarity	NPD6959	Discontinued
0.8415	Intermediate Similarity	NPD7819	Suspended
0.8397	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8397	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8375	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8363	Intermediate Similarity	NPD5844	Phase 1
0.8353	Intermediate Similarity	NPD7473	Discontinued
0.8344	Intermediate Similarity	NPD1549	Phase 2
0.8293	Intermediate Similarity	NPD7411	Suspended
0.8284	Intermediate Similarity	NPD6232	Discontinued
0.8253	Intermediate Similarity	NPD5402	Approved
0.8218	Intermediate Similarity	NPD6559	Discontinued
0.8199	Intermediate Similarity	NPD6799	Approved
0.8193	Intermediate Similarity	NPD1465	Phase 2
0.816	Intermediate Similarity	NPD5403	Approved
0.8101	Intermediate Similarity	NPD2796	Approved
0.8038	Intermediate Similarity	NPD1510	Phase 2
0.8037	Intermediate Similarity	NPD5401	Approved
0.8013	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8013	Intermediate Similarity	NPD1613	Approved
0.8012	Intermediate Similarity	NPD1247	Approved
0.8012	Intermediate Similarity	NPD6599	Discontinued
0.8011	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD919	Approved
0.7977	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7933	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7919	Intermediate Similarity	NPD3926	Phase 2
0.7898	Intermediate Similarity	NPD1240	Approved
0.7882	Intermediate Similarity	NPD7768	Phase 2
0.7821	Intermediate Similarity	NPD3027	Phase 3
0.7802	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7799	Intermediate Similarity	NPD1607	Approved
0.7785	Intermediate Similarity	NPD943	Approved
0.7784	Intermediate Similarity	NPD7228	Approved
0.7784	Intermediate Similarity	NPD3751	Discontinued
0.7759	Intermediate Similarity	NPD3787	Discontinued
0.7756	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7744	Intermediate Similarity	NPD6190	Approved
0.7742	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7722	Intermediate Similarity	NPD8313	Approved
0.7722	Intermediate Similarity	NPD8312	Approved
0.7713	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD8150	Discontinued
0.7654	Intermediate Similarity	NPD2935	Discontinued
0.763	Intermediate Similarity	NPD3749	Approved
0.7622	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7622	Intermediate Similarity	NPD2800	Approved
0.7619	Intermediate Similarity	NPD6776	Approved
0.7619	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD6781	Approved
0.7619	Intermediate Similarity	NPD6780	Approved
0.7619	Intermediate Similarity	NPD6779	Approved
0.7619	Intermediate Similarity	NPD6782	Approved
0.7619	Intermediate Similarity	NPD6777	Approved
0.7619	Intermediate Similarity	NPD6778	Approved
0.7614	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7611	Intermediate Similarity	NPD7685	Pre-registration
0.7605	Intermediate Similarity	NPD2532	Approved
0.7605	Intermediate Similarity	NPD2534	Approved
0.7605	Intermediate Similarity	NPD2533	Approved
0.76	Intermediate Similarity	NPD7199	Phase 2
0.7596	Intermediate Similarity	NPD8434	Phase 2
0.7592	Intermediate Similarity	NPD7435	Discontinued
0.7592	Intermediate Similarity	NPD7698	Approved
0.7592	Intermediate Similarity	NPD7696	Phase 3
0.7592	Intermediate Similarity	NPD7697	Approved
0.7586	Intermediate Similarity	NPD6234	Discontinued
0.7578	Intermediate Similarity	NPD6651	Approved
0.7576	Intermediate Similarity	NPD3750	Approved
0.7576	Intermediate Similarity	NPD4628	Phase 3
0.7574	Intermediate Similarity	NPD1653	Approved
0.7565	Intermediate Similarity	NPD7584	Approved
0.7561	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7547	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7546	Intermediate Similarity	NPD6099	Approved
0.7546	Intermediate Similarity	NPD6100	Approved
0.7526	Intermediate Similarity	NPD7701	Phase 2
0.7516	Intermediate Similarity	NPD230	Phase 1
0.75	Intermediate Similarity	NPD37	Approved
0.7487	Intermediate Similarity	NPD8151	Discontinued
0.7485	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7473	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7471	Intermediate Similarity	NPD4965	Approved
0.7471	Intermediate Similarity	NPD4966	Approved
0.7471	Intermediate Similarity	NPD4967	Phase 2
0.7461	Intermediate Similarity	NPD7870	Phase 2
0.7461	Intermediate Similarity	NPD7871	Phase 2
0.7459	Intermediate Similarity	NPD5953	Discontinued
0.7457	Intermediate Similarity	NPD8455	Phase 2
0.7447	Intermediate Similarity	NPD4360	Phase 2
0.7447	Intermediate Similarity	NPD4363	Phase 3
0.7444	Intermediate Similarity	NPD7286	Phase 2
0.744	Intermediate Similarity	NPD7390	Discontinued
0.7439	Intermediate Similarity	NPD1551	Phase 2
0.7438	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7427	Intermediate Similarity	NPD3226	Approved
0.7421	Intermediate Similarity	NPD7699	Phase 2
0.7421	Intermediate Similarity	NPD7700	Phase 2
0.7412	Intermediate Similarity	NPD920	Approved
0.7411	Intermediate Similarity	NPD7783	Phase 2
0.7411	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD447	Suspended
0.7394	Intermediate Similarity	NPD7266	Discontinued
0.7365	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.736	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.736	Intermediate Similarity	NPD7874	Approved
0.7354	Intermediate Similarity	NPD6535	Approved
0.7354	Intermediate Similarity	NPD6534	Approved
0.7337	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7323	Intermediate Similarity	NPD7801	Approved
0.7322	Intermediate Similarity	NPD7240	Approved
0.7312	Intermediate Similarity	NPD4908	Phase 1
0.7305	Intermediate Similarity	NPD1243	Approved
0.7301	Intermediate Similarity	NPD5124	Phase 1
0.7301	Intermediate Similarity	NPD1933	Approved
0.7301	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7294	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7294	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7294	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7289	Intermediate Similarity	NPD2346	Discontinued
0.7282	Intermediate Similarity	NPD8320	Phase 1
0.7282	Intermediate Similarity	NPD8319	Approved
0.7278	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD7033	Discontinued
0.7273	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD2799	Discontinued
0.7273	Intermediate Similarity	NPD3748	Approved
0.7268	Intermediate Similarity	NPD6823	Phase 2
0.7262	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD9494	Approved
0.7246	Intermediate Similarity	NPD2424	Discontinued
0.7241	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD2313	Discontinued
0.7222	Intermediate Similarity	NPD6798	Discontinued
0.7215	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7207	Intermediate Similarity	NPD8127	Discontinued
0.7205	Intermediate Similarity	NPD6832	Phase 2
0.72	Intermediate Similarity	NPD6844	Discontinued
0.7197	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7195	Intermediate Similarity	NPD6355	Discontinued
0.7186	Intermediate Similarity	NPD2344	Approved
0.7182	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD7585	Approved
0.7171	Intermediate Similarity	NPD7907	Approved
0.7167	Intermediate Similarity	NPD5710	Approved
0.7167	Intermediate Similarity	NPD5711	Approved
0.716	Intermediate Similarity	NPD4625	Phase 3
0.7134	Intermediate Similarity	NPD4060	Phase 1
0.7128	Intermediate Similarity	NPD2493	Approved
0.7128	Intermediate Similarity	NPD2494	Approved
0.7126	Intermediate Similarity	NPD7458	Discontinued
0.7121	Intermediate Similarity	NPD7583	Approved
0.7119	Intermediate Similarity	NPD5353	Approved
0.7117	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD6674	Discontinued
0.7089	Intermediate Similarity	NPD1610	Phase 2
0.7088	Intermediate Similarity	NPD2403	Approved
0.7081	Intermediate Similarity	NPD3823	Discontinued
0.7073	Intermediate Similarity	NPD4111	Phase 1
0.7073	Intermediate Similarity	NPD6233	Phase 2
0.7073	Intermediate Similarity	NPD4665	Approved
0.7072	Intermediate Similarity	NPD7229	Phase 3
0.7047	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD4361	Phase 2
0.7041	Intermediate Similarity	NPD3452	Approved
0.7041	Intermediate Similarity	NPD3450	Approved
0.7033	Intermediate Similarity	NPD5242	Approved
0.7026	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.702	Intermediate Similarity	NPD4583	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