NPASS Compound

Structure

NPC471212 OpenBabel07101718292D 35 38 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 -6.9282 -3.0000 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 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 -5.1962 -1.0000 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 -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 -3.4641 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 0.5000 0.0000 C 0 0 1 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 -6.9282 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 -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 -6.9282 -1.0000 0.0000 C 0 0 0 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 -3.4641 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 -7.7942 -1.5000 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 -6.0622 -2.5000 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 26 1 0 0 0 0 2 26 1 0 0 0 0 3 27 1 0 0 0 0 4 32 1 0 0 0 0 5 33 1 0 0 0 0 6 8 1 0 0 0 0 6 9 1 0 0 0 0 7 10 1 0 0 0 0 7 16 1 0 0 0 0 8 26 1 0 0 0 0 9 27 1 0 0 0 0 10 27 1 0 0 0 0 11 15 2 0 0 0 0 11 21 1 0 0 0 0 12 15 1 0 0 0 0 12 22 2 0 0 0 0 13 17 1 0 0 0 0 13 18 1 0 0 0 0 14 19 2 0 0 0 0 14 20 1 0 0 0 0 16 19 1 0 0 0 0 16 24 2 0 0 0 0 17 23 1 0 0 0 0 17 28 2 0 0 0 0 18 15 1 6 0 0 0 18 34 1 0 0 0 0 19 35 1 0 0 0 0 20 23 2 0 0 0 0 20 34 1 0 0 0 0 21 25 2 0 0 0 0 21 32 1 0 0 0 0 22 25 1 0 0 0 0 22 33 1 0 0 0 0 23 24 1 0 0 0 0 24 29 1 0 0 0 0 25 30 1 0 0 0 0 26 31 1 0 0 0 0 27 35 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	486.23
Volume:	493.189
LogP:	4.095
LogD:	2.959
LogS:	-4.726
# Rotatable Bonds:	7
TPSA:	114.68
# H-Bond Aceptor:	8
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.509
Synthetic Accessibility Score:	3.867
Fsp3:	0.519
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:	-4.739
MDCK Permeability:	2.0002533346996643e-05
Pgp-inhibitor:	0.957
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.01
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.003

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.026
Plasma Protein Binding (PPB):	88.9338607788086%
Volume Distribution (VD):	0.812
Pgp-substrate:	13.016722679138184%

ADMET: Metabolism

CYP1A2-inhibitor:	0.066
CYP1A2-substrate:	0.955
CYP2C19-inhibitor:	0.189
CYP2C19-substrate:	0.773
CYP2C9-inhibitor:	0.507
CYP2C9-substrate:	0.871
CYP2D6-inhibitor:	0.213
CYP2D6-substrate:	0.566
CYP3A4-inhibitor:	0.529
CYP3A4-substrate:	0.565

ADMET: Excretion

Clearance (CL):	13.176
Half-life (T1/2):	0.481

ADMET: Toxicity

hERG Blockers:	0.012
Human Hepatotoxicity (H-HT):	0.627
Drug-inuced Liver Injury (DILI):	0.487
AMES Toxicity:	0.045
Rat Oral Acute Toxicity:	0.697
Maximum Recommended Daily Dose:	0.399
Skin Sensitization:	0.674
Carcinogencity:	0.209
Eye Corrosion:	0.003
Eye Irritation:	0.027
Respiratory Toxicity:	0.863

Download Data

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

Natural Product: NPC471212

Natural Product ID:	NPC471212
*Common Name:**	(8S)-5-Hydroxy-8-(4-Hydroxy-3,5-Dimethoxyphenyl)-2-(4-Hydroxy-4-Methylpentyl)-2-Methyl-3,4,7,8-Tetrahydropyrano[3,2-G]Chromen-6-One
IUPAC Name:	(8S)-5-hydroxy-8-(4-hydroxy-3,5-dimethoxyphenyl)-2-(4-hydroxy-4-methylpentyl)-2-methyl-3,4,7,8-tetrahydropyrano[3,2-g]chromen-6-one
Synonyms:
Standard InCHIKey:	DHYMKZKAVOUQFT-HSYKDVHTSA-N
Standard InCHI:	InChI=1S/C27H34O8/c1-26(2,31)8-6-9-27(3)10-7-16-19(35-27)14-20-23(24(16)29)17(28)13-18(34-20)15-11-21(32-4)25(30)22(12-15)33-5/h11-12,14,18,29-31H,6-10,13H2,1-5H3/t18-,27?/m0/s1
SMILES:	COc1cc(cc(c1O)OC)[C@@H]1CC(=O)c2c(O1)cc1c(c2O)CCC(O1)(C)CCCC(O)(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2387714
PubChem CID:	71659766
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	>	100000.0	nM	PMID[486140]
NPT2	Others	Unspecified		Ki	=	13000.0	nM	PMID[486139]
NPT2	Others	Unspecified		IC50	=	12500.0	nM	PMID[486139]

☑ 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 NPC471212 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	412
0.1-0.2	1665
0.2-0.3	4113
0.3-0.4	10001
0.4-0.5	8202
0.5-0.6	3489
0.6-0.7	4697
0.7-0.8	5472
0.8-0.85	2837
0.85-0.9	1454
0.9-0.95	288
0.95-1	67

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC471211
0.9869	High Similarity	NPC471210
0.9804	High Similarity	NPC174953
0.9804	High Similarity	NPC472630
0.9804	High Similarity	NPC472631
0.9744	High Similarity	NPC471213
0.974	High Similarity	NPC472634
0.974	High Similarity	NPC472632
0.974	High Similarity	NPC134783
0.9739	High Similarity	NPC473990
0.9737	High Similarity	NPC472626
0.9737	High Similarity	NPC470328
0.9737	High Similarity	NPC209614
0.9679	High Similarity	NPC293319
0.9677	High Similarity	NPC474033
0.9677	High Similarity	NPC474034
0.9675	High Similarity	NPC119209
0.9675	High Similarity	NPC192686
0.9675	High Similarity	NPC118256
0.9673	High Similarity	NPC27337
0.9673	High Similarity	NPC471209
0.9671	High Similarity	NPC477503
0.9671	High Similarity	NPC45849
0.9671	High Similarity	NPC200761
0.9671	High Similarity	NPC470327
0.9613	High Similarity	NPC26326
0.9613	High Similarity	NPC474038
0.9608	High Similarity	NPC195796
0.9608	High Similarity	NPC291878
0.9608	High Similarity	NPC278778
0.9608	High Similarity	NPC35038
0.9605	High Similarity	NPC298692
0.9605	High Similarity	NPC74924
0.9557	High Similarity	NPC474024
0.9554	High Similarity	NPC62261
0.9551	High Similarity	NPC472635
0.9548	High Similarity	NPC472624
0.9548	High Similarity	NPC475784
0.9548	High Similarity	NPC470326
0.9545	High Similarity	NPC474055
0.9545	High Similarity	NPC52889
0.9545	High Similarity	NPC284820
0.9545	High Similarity	NPC291508
0.9545	High Similarity	NPC473272
0.9545	High Similarity	NPC223787
0.9545	High Similarity	NPC472598
0.9542	High Similarity	NPC226025
0.9539	High Similarity	NPC106976
0.949	High Similarity	NPC186686
0.949	High Similarity	NPC472625
0.9487	High Similarity	NPC471499
0.9487	High Similarity	NPC158188
0.9487	High Similarity	NPC142252
0.9484	High Similarity	NPC53545
0.9484	High Similarity	NPC117418
0.9477	High Similarity	NPC192083
0.9477	High Similarity	NPC18727
0.9477	High Similarity	NPC213896
0.9434	High Similarity	NPC218226
0.9434	High Similarity	NPC6588
0.9434	High Similarity	NPC117854
0.9434	High Similarity	NPC477154
0.9434	High Similarity	NPC477502
0.9427	High Similarity	NPC220912
0.9427	High Similarity	NPC476247
0.9427	High Similarity	NPC201800
0.9427	High Similarity	NPC474162
0.9427	High Similarity	NPC474150
0.9423	High Similarity	NPC287328
0.9423	High Similarity	NPC282009
0.9423	High Similarity	NPC36217
0.9416	High Similarity	NPC321779
0.9412	High Similarity	NPC471982
0.9412	High Similarity	NPC219582
0.9412	High Similarity	NPC302950
0.9412	High Similarity	NPC236637
0.9408	High Similarity	NPC338131
0.9371	High Similarity	NPC43319
0.9367	High Similarity	NPC236521
0.9367	High Similarity	NPC152659
0.9367	High Similarity	NPC124038
0.9367	High Similarity	NPC41301
0.9367	High Similarity	NPC248638
0.9363	High Similarity	NPC173137
0.9363	High Similarity	NPC289771
0.9363	High Similarity	NPC228383
0.9363	High Similarity	NPC266314
0.9359	High Similarity	NPC204879
0.9359	High Similarity	NPC184755
0.9359	High Similarity	NPC250214
0.9359	High Similarity	NPC74178
0.9359	High Similarity	NPC95936
0.9359	High Similarity	NPC22192
0.9359	High Similarity	NPC469658
0.9359	High Similarity	NPC210459
0.9355	High Similarity	NPC471985
0.9355	High Similarity	NPC470600
0.9355	High Similarity	NPC250922
0.9346	High Similarity	NPC474021
0.9346	High Similarity	NPC474023
0.9321	High Similarity	NPC208668
0.9313	High Similarity	NPC158761
0.9308	High Similarity	NPC224280
0.9308	High Similarity	NPC300053
0.9308	High Similarity	NPC36
0.9308	High Similarity	NPC108433
0.9308	High Similarity	NPC477840
0.9308	High Similarity	NPC125039
0.9308	High Similarity	NPC475888
0.9308	High Similarity	NPC7688
0.9308	High Similarity	NPC58223
0.9308	High Similarity	NPC72787
0.9308	High Similarity	NPC7154
0.9308	High Similarity	NPC36916
0.9304	High Similarity	NPC211107
0.9304	High Similarity	NPC477841
0.9304	High Similarity	NPC472448
0.9304	High Similarity	NPC472964
0.9304	High Similarity	NPC83922
0.9304	High Similarity	NPC25152
0.9299	High Similarity	NPC204290
0.9299	High Similarity	NPC328102
0.9299	High Similarity	NPC299436
0.9299	High Similarity	NPC101731
0.9299	High Similarity	NPC470183
0.9299	High Similarity	NPC321399
0.9295	High Similarity	NPC36852
0.9295	High Similarity	NPC218313
0.9295	High Similarity	NPC474681
0.9295	High Similarity	NPC471479
0.9295	High Similarity	NPC262286
0.9295	High Similarity	NPC474208
0.9295	High Similarity	NPC48208
0.9295	High Similarity	NPC474836
0.9295	High Similarity	NPC471515
0.9295	High Similarity	NPC67876
0.9295	High Similarity	NPC156057
0.9295	High Similarity	NPC475267
0.9295	High Similarity	NPC78225
0.9295	High Similarity	NPC162869
0.929	High Similarity	NPC117992
0.929	High Similarity	NPC256925
0.929	High Similarity	NPC477958
0.929	High Similarity	NPC234255
0.929	High Similarity	NPC152951
0.929	High Similarity	NPC57674
0.929	High Similarity	NPC230149
0.929	High Similarity	NPC168247
0.9286	High Similarity	NPC475790
0.9286	High Similarity	NPC472912
0.9264	High Similarity	NPC108202
0.9259	High Similarity	NPC261254
0.9259	High Similarity	NPC256760
0.9255	High Similarity	NPC475212
0.9255	High Similarity	NPC326877
0.9255	High Similarity	NPC288813
0.9255	High Similarity	NPC177480
0.925	High Similarity	NPC119589
0.925	High Similarity	NPC5778
0.925	High Similarity	NPC170245
0.925	High Similarity	NPC236934
0.925	High Similarity	NPC120593
0.925	High Similarity	NPC13481
0.925	High Similarity	NPC39091
0.925	High Similarity	NPC207575
0.9245	High Similarity	NPC7483
0.9245	High Similarity	NPC273959
0.9245	High Similarity	NPC18100
0.9245	High Similarity	NPC474240
0.9241	High Similarity	NPC165970
0.9241	High Similarity	NPC474186
0.9241	High Similarity	NPC278052
0.9241	High Similarity	NPC288131
0.9241	High Similarity	NPC66618
0.9241	High Similarity	NPC3629
0.9241	High Similarity	NPC61010
0.9241	High Similarity	NPC167678
0.9241	High Similarity	NPC40491
0.9241	High Similarity	NPC113163
0.9241	High Similarity	NPC305987
0.9241	High Similarity	NPC29876
0.9241	High Similarity	NPC84324
0.9241	High Similarity	NPC198829
0.9236	High Similarity	NPC172202
0.9236	High Similarity	NPC476410
0.9236	High Similarity	NPC284127
0.9236	High Similarity	NPC85121
0.9236	High Similarity	NPC187792
0.9231	High Similarity	NPC472455
0.9231	High Similarity	NPC24640
0.9231	High Similarity	NPC5322
0.9231	High Similarity	NPC320825
0.9231	High Similarity	NPC235165
0.9231	High Similarity	NPC6633
0.9231	High Similarity	NPC326037
0.9231	High Similarity	NPC191146
0.9231	High Similarity	NPC68093
0.9231	High Similarity	NPC255106
0.9231	High Similarity	NPC170026
0.9231	High Similarity	NPC471500

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 NPC471212 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	367
0.1-0.2	949
0.2-0.3	1862
0.3-0.4	2612
0.4-0.5	1767
0.5-0.6	972
0.6-0.7	444
0.7-0.8	130
0.8-0.85	30
0.85-0.9	12
0.9-0.95	5
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9477	High Similarity	NPD2393	Clinical (unspecified phase)
0.9412	High Similarity	NPD1934	Approved
0.9308	High Similarity	NPD6167	Clinical (unspecified phase)
0.9308	High Similarity	NPD6168	Clinical (unspecified phase)
0.9308	High Similarity	NPD6166	Phase 2
0.9198	High Similarity	NPD7074	Phase 3
0.9136	High Similarity	NPD7054	Approved
0.908	High Similarity	NPD7472	Approved
0.8981	High Similarity	NPD2801	Approved
0.891	High Similarity	NPD4380	Phase 2
0.8868	High Similarity	NPD4868	Clinical (unspecified phase)
0.8855	High Similarity	NPD7251	Discontinued
0.882	High Similarity	NPD5494	Approved
0.8812	High Similarity	NPD7075	Discontinued
0.8802	High Similarity	NPD7808	Phase 3
0.8795	High Similarity	NPD6797	Phase 2
0.8766	High Similarity	NPD1511	Approved
0.875	High Similarity	NPD3882	Suspended
0.8727	High Similarity	NPD3818	Discontinued
0.8688	High Similarity	NPD3817	Phase 2
0.8688	High Similarity	NPD8443	Clinical (unspecified phase)
0.8675	High Similarity	NPD7804	Clinical (unspecified phase)
0.8654	High Similarity	NPD1512	Approved
0.865	High Similarity	NPD6959	Discontinued
0.8625	High Similarity	NPD7096	Clinical (unspecified phase)
0.859	High Similarity	NPD4378	Clinical (unspecified phase)
0.858	High Similarity	NPD4381	Clinical (unspecified phase)
0.858	High Similarity	NPD4338	Clinical (unspecified phase)
0.8509	High Similarity	NPD7819	Suspended
0.8497	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8497	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8471	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8462	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8443	Intermediate Similarity	NPD7473	Discontinued
0.8442	Intermediate Similarity	NPD1549	Phase 2
0.8395	Intermediate Similarity	NPD1465	Phase 2
0.8385	Intermediate Similarity	NPD7411	Suspended
0.8373	Intermediate Similarity	NPD6232	Discontinued
0.8343	Intermediate Similarity	NPD5844	Phase 1
0.8333	Intermediate Similarity	NPD6801	Discontinued
0.8198	Intermediate Similarity	NPD6559	Discontinued
0.8194	Intermediate Similarity	NPD2796	Approved
0.8129	Intermediate Similarity	NPD1510	Phase 2
0.8063	Intermediate Similarity	NPD6799	Approved
0.8059	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8012	Intermediate Similarity	NPD5402	Approved
0.7987	Intermediate Similarity	NPD1240	Approved
0.7987	Intermediate Similarity	NPD1613	Approved
0.7987	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7964	Intermediate Similarity	NPD7768	Phase 2
0.7914	Intermediate Similarity	NPD5403	Approved
0.7895	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7885	Intermediate Similarity	NPD1607	Approved
0.7882	Intermediate Similarity	NPD1247	Approved
0.7879	Intermediate Similarity	NPD6599	Discontinued
0.7877	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7871	Intermediate Similarity	NPD943	Approved
0.787	Intermediate Similarity	NPD919	Approved
0.7861	Intermediate Similarity	NPD7228	Approved
0.7843	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7812	Intermediate Similarity	NPD2800	Approved
0.7809	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7792	Intermediate Similarity	NPD3027	Phase 3
0.7791	Intermediate Similarity	NPD2533	Approved
0.7791	Intermediate Similarity	NPD2534	Approved
0.7791	Intermediate Similarity	NPD2532	Approved
0.7791	Intermediate Similarity	NPD3926	Phase 2
0.7791	Intermediate Similarity	NPD5401	Approved
0.779	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7784	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD6651	Approved
0.7765	Intermediate Similarity	NPD6234	Discontinued
0.775	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7736	Intermediate Similarity	NPD6099	Approved
0.7736	Intermediate Similarity	NPD6100	Approved
0.7736	Intermediate Similarity	NPD2935	Discontinued
0.7707	Intermediate Similarity	NPD230	Phase 1
0.7706	Intermediate Similarity	NPD3749	Approved
0.7702	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD8312	Approved
0.7697	Intermediate Similarity	NPD8313	Approved
0.7697	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7654	Intermediate Similarity	NPD3750	Approved
0.7628	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7622	Intermediate Similarity	NPD7390	Discontinued
0.7584	Intermediate Similarity	NPD7685	Pre-registration
0.7574	Intermediate Similarity	NPD37	Approved
0.7572	Intermediate Similarity	NPD7199	Phase 2
0.7557	Intermediate Similarity	NPD3751	Discontinued
0.7552	Intermediate Similarity	NPD8151	Discontinued
0.7546	Intermediate Similarity	NPD4628	Phase 3
0.7546	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7545	Intermediate Similarity	NPD1653	Approved
0.7544	Intermediate Similarity	NPD4967	Phase 2
0.7544	Intermediate Similarity	NPD4966	Approved
0.7544	Intermediate Similarity	NPD4965	Approved
0.7539	Intermediate Similarity	NPD7584	Approved
0.7529	Intermediate Similarity	NPD3787	Discontinued
0.7528	Intermediate Similarity	NPD5953	Discontinued
0.7527	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD1551	Phase 2
0.7514	Intermediate Similarity	NPD7286	Phase 2
0.75	Intermediate Similarity	NPD6190	Approved
0.75	Intermediate Similarity	NPD3226	Approved
0.7486	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD1243	Approved
0.7485	Intermediate Similarity	NPD920	Approved
0.7484	Intermediate Similarity	NPD447	Suspended
0.7473	Intermediate Similarity	NPD8150	Discontinued
0.747	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7453	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7444	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7427	Intermediate Similarity	NPD8455	Phase 2
0.7419	Intermediate Similarity	NPD4360	Phase 2
0.7419	Intermediate Similarity	NPD4363	Phase 3
0.741	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD6778	Approved
0.7407	Intermediate Similarity	NPD6776	Approved
0.7407	Intermediate Similarity	NPD6780	Approved
0.7407	Intermediate Similarity	NPD6782	Approved
0.7407	Intermediate Similarity	NPD6781	Approved
0.7407	Intermediate Similarity	NPD6777	Approved
0.7407	Intermediate Similarity	NPD6779	Approved
0.7389	Intermediate Similarity	NPD4908	Phase 1
0.7389	Intermediate Similarity	NPD7240	Approved
0.7385	Intermediate Similarity	NPD7783	Phase 2
0.7385	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7382	Intermediate Similarity	NPD7697	Approved
0.7382	Intermediate Similarity	NPD7698	Approved
0.7382	Intermediate Similarity	NPD7435	Discontinued
0.7382	Intermediate Similarity	NPD7696	Phase 3
0.7377	Intermediate Similarity	NPD8434	Phase 2
0.7375	Intermediate Similarity	NPD1933	Approved
0.7365	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7362	Intermediate Similarity	NPD7266	Discontinued
0.7362	Intermediate Similarity	NPD2346	Discontinued
0.7349	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7346	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7346	Intermediate Similarity	NPD3748	Approved
0.7346	Intermediate Similarity	NPD2799	Discontinued
0.733	Intermediate Similarity	NPD5710	Approved
0.733	Intermediate Similarity	NPD5711	Approved
0.7325	Intermediate Similarity	NPD9494	Approved
0.732	Intermediate Similarity	NPD7701	Phase 2
0.731	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7296	Intermediate Similarity	NPD2313	Discontinued
0.729	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD5353	Approved
0.7278	Intermediate Similarity	NPD6832	Phase 2
0.7273	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD5124	Phase 1
0.7262	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7256	Intermediate Similarity	NPD2344	Approved
0.7254	Intermediate Similarity	NPD7870	Phase 2
0.7254	Intermediate Similarity	NPD7871	Phase 2
0.724	Intermediate Similarity	NPD6823	Phase 2
0.7239	Intermediate Similarity	NPD7033	Discontinued
0.7233	Intermediate Similarity	NPD4625	Phase 3
0.7229	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD2424	Discontinued
0.7211	Intermediate Similarity	NPD7700	Phase 2
0.7211	Intermediate Similarity	NPD7699	Phase 2
0.7193	Intermediate Similarity	NPD7458	Discontinued
0.7193	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7175	Intermediate Similarity	NPD8127	Discontinued
0.7169	Intermediate Similarity	NPD6674	Discontinued
0.7168	Intermediate Similarity	NPD6844	Discontinued
0.7161	Intermediate Similarity	NPD1610	Phase 2
0.7157	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7157	Intermediate Similarity	NPD7874	Approved
0.7143	Intermediate Similarity	NPD6534	Approved
0.7143	Intermediate Similarity	NPD6535	Approved
0.7143	Intermediate Similarity	NPD7585	Approved
0.7135	Intermediate Similarity	NPD7229	Phase 3
0.7121	Intermediate Similarity	NPD7801	Approved
0.7095	Intermediate Similarity	NPD5242	Approved
0.7092	Intermediate Similarity	NPD7583	Approved
0.7089	Intermediate Similarity	NPD1203	Approved
0.7083	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD2309	Approved
0.7081	Intermediate Similarity	NPD6798	Discontinued
0.7077	Intermediate Similarity	NPD8320	Phase 1
0.7077	Intermediate Similarity	NPD8319	Approved
0.707	Intermediate Similarity	NPD4749	Approved
0.7059	Intermediate Similarity	NPD7907	Approved
0.7056	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7056	Intermediate Similarity	NPD2403	Approved
0.7055	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD6355	Discontinued
0.7049	Intermediate Similarity	NPD3823	Discontinued
0.7016	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7016	Intermediate Similarity	NPD4361	Phase 2
0.7013	Intermediate Similarity	NPD1548	Phase 1
0.7011	Intermediate Similarity	NPD6385	Approved
0.7011	Intermediate Similarity	NPD6386	Approved
0.701	Intermediate Similarity	NPD2493	Approved
0.701	Intermediate Similarity	NPD2494	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