NPASS Compound

Structure

NPC472631 OpenBabel07101718182D 37 39 0 0 1 0 0 0 0 0999 V2000 3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0981 5.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0981 5.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 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 3.4641 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 -0.0000 -2.0000 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 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -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 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 4.0000 0.0000 C 0 0 3 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 0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 4.5000 0.0000 C 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 -1.7321 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 4.0000 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 1 15 1 0 0 0 0 2 28 1 0 0 0 0 3 28 1 0 0 0 0 4 34 1 0 0 0 0 5 35 1 0 0 0 0 6 36 1 0 0 0 0 7 9 1 0 0 0 0 7 15 2 0 0 0 0 8 10 1 0 0 0 0 8 15 1 0 0 0 0 9 17 1 0 0 0 0 10 24 1 0 0 0 0 11 16 2 0 0 0 0 11 22 1 0 0 0 0 12 16 1 0 0 0 0 12 23 2 0 0 0 0 13 18 2 0 0 0 0 13 21 1 0 0 0 0 14 19 1 0 0 0 0 14 20 1 0 0 0 0 16 20 1 0 0 0 0 17 18 1 0 0 0 0 17 26 2 0 0 0 0 18 29 1 0 0 0 0 19 25 1 0 0 0 0 19 30 2 0 0 0 0 20 37 1 0 0 0 0 21 25 2 0 0 0 0 21 37 1 0 0 0 0 22 27 2 0 0 0 0 22 34 1 0 0 0 0 23 27 1 0 0 0 0 23 35 1 0 0 0 0 24 28 1 0 0 0 0 24 31 1 0 0 0 0 25 26 1 0 0 0 0 26 32 1 0 0 0 0 27 33 1 0 0 0 0 28 36 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	516.24
Volume:	525.195
LogP:	3.561
LogD:	2.876
LogS:	-4.417
# Rotatable Bonds:	10
TPSA:	134.91
# H-Bond Aceptor:	9
# H-Bond Donor:	4
# Rings:	3
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.335
Synthetic Accessibility Score:	4.002
Fsp3:	0.464
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.088
MDCK Permeability:	8.940281077229884e-06
Pgp-inhibitor:	0.319
Pgp-substrate:	0.972
Human Intestinal Absorption (HIA):	0.393
20% Bioavailability (F20%):	0.007
30% Bioavailability (F30%):	0.012

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.004
Plasma Protein Binding (PPB):	95.5887680053711%
Volume Distribution (VD):	0.425
Pgp-substrate:	4.359498023986816%

ADMET: Metabolism

CYP1A2-inhibitor:	0.05
CYP1A2-substrate:	0.807
CYP2C19-inhibitor:	0.235
CYP2C19-substrate:	0.562
CYP2C9-inhibitor:	0.733
CYP2C9-substrate:	0.801
CYP2D6-inhibitor:	0.404
CYP2D6-substrate:	0.532
CYP3A4-inhibitor:	0.399
CYP3A4-substrate:	0.489

ADMET: Excretion

Clearance (CL):	8.551
Half-life (T1/2):	0.665

ADMET: Toxicity

hERG Blockers:	0.013
Human Hepatotoxicity (H-HT):	0.124
Drug-inuced Liver Injury (DILI):	0.254
AMES Toxicity:	0.026
Rat Oral Acute Toxicity:	0.353
Maximum Recommended Daily Dose:	0.603
Skin Sensitization:	0.934
Carcinogencity:	0.035
Eye Corrosion:	0.003
Eye Irritation:	0.024
Respiratory Toxicity:	0.705

Download Data

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

Natural Product: NPC472631

Natural Product ID:	NPC472631
*Common Name:**	UTJACGGIQKDKBW-VIZOYTHASA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	UTJACGGIQKDKBW-VIZOYTHASA-N
Standard InCHI:	InChI=1S/C28H36O9/c1-15(8-10-24(31)28(2,3)36-6)7-9-17-18(29)13-21-25(26(17)32)19(30)14-20(37-21)16-11-22(34-4)27(33)23(12-16)35-5/h7,11-13,20,24,29,31-33H,8-10,14H2,1-6H3/b15-7+
SMILES:	COc1cc(cc(c1O)OC)C1CC(=O)c2c(O1)cc(c(c2O)C/C=C(/CCC(C(OC)(C)C)O)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3581351
PubChem CID:	n.a.
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	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1970	Cell Line	THP-1	Homo sapiens	IC50	>	10000.0	nM	PMID[490503]

☑ 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 NPC472631 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	409
0.1-0.2	1541
0.2-0.3	3682
0.3-0.4	9120
0.4-0.5	9343
0.5-0.6	3537
0.6-0.7	4676
0.7-0.8	5530
0.8-0.85	2935
0.85-0.9	1544
0.9-0.95	311
0.95-1	69

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC472630
0.9934	High Similarity	NPC472634
0.9804	High Similarity	NPC471211
0.9804	High Similarity	NPC471212
0.9801	High Similarity	NPC472626
0.9801	High Similarity	NPC470328
0.9801	High Similarity	NPC209614
0.974	High Similarity	NPC472635
0.9739	High Similarity	NPC174953
0.9739	High Similarity	NPC470326
0.9737	High Similarity	NPC472598
0.9737	High Similarity	NPC27337
0.9737	High Similarity	NPC474055
0.9735	High Similarity	NPC200761
0.9735	High Similarity	NPC477503
0.9735	High Similarity	NPC45849
0.9735	High Similarity	NPC470327
0.9679	High Similarity	NPC471213
0.9675	High Similarity	NPC471499
0.9675	High Similarity	NPC474038
0.9675	High Similarity	NPC26326
0.9675	High Similarity	NPC472632
0.9675	High Similarity	NPC471210
0.9673	High Similarity	NPC473990
0.9671	High Similarity	NPC35038
0.9671	High Similarity	NPC195796
0.9671	High Similarity	NPC291878
0.9671	High Similarity	NPC278778
0.9669	High Similarity	NPC74924
0.9669	High Similarity	NPC298692
0.9613	High Similarity	NPC474033
0.9613	High Similarity	NPC474034
0.961	High Similarity	NPC282009
0.961	High Similarity	NPC119209
0.961	High Similarity	NPC287328
0.961	High Similarity	NPC472624
0.961	High Similarity	NPC475784
0.961	High Similarity	NPC192686
0.961	High Similarity	NPC118256
0.9608	High Similarity	NPC291508
0.9608	High Similarity	NPC223787
0.9605	High Similarity	NPC321779
0.9605	High Similarity	NPC226025
0.9603	High Similarity	NPC106976
0.9551	High Similarity	NPC472625
0.9551	High Similarity	NPC124038
0.9548	High Similarity	NPC134783
0.9548	High Similarity	NPC142252
0.9548	High Similarity	NPC158188
0.9545	High Similarity	NPC117418
0.9545	High Similarity	NPC53545
0.9545	High Similarity	NPC22192
0.9542	High Similarity	NPC250922
0.9539	High Similarity	NPC213896
0.9539	High Similarity	NPC192083
0.9539	High Similarity	NPC18727
0.9494	High Similarity	NPC474024
0.9494	High Similarity	NPC158761
0.949	High Similarity	NPC293319
0.949	High Similarity	NPC475888
0.9487	High Similarity	NPC476247
0.9487	High Similarity	NPC211107
0.9487	High Similarity	NPC201800
0.9487	High Similarity	NPC472964
0.9484	High Similarity	NPC36217
0.9484	High Similarity	NPC321399
0.9484	High Similarity	NPC470183
0.9481	High Similarity	NPC52889
0.9481	High Similarity	NPC284820
0.9481	High Similarity	NPC471209
0.9481	High Similarity	NPC473272
0.9474	High Similarity	NPC471982
0.9474	High Similarity	NPC219582
0.9474	High Similarity	NPC302950
0.9474	High Similarity	NPC236637
0.947	High Similarity	NPC338131
0.943	High Similarity	NPC119589
0.9427	High Similarity	NPC41301
0.9427	High Similarity	NPC474240
0.9427	High Similarity	NPC186686
0.9427	High Similarity	NPC7483
0.9423	High Similarity	NPC289771
0.9423	High Similarity	NPC266314
0.9419	High Similarity	NPC210459
0.9419	High Similarity	NPC250214
0.9419	High Similarity	NPC95936
0.9416	High Similarity	NPC326037
0.9416	High Similarity	NPC320825
0.9416	High Similarity	NPC13858
0.9408	High Similarity	NPC471677
0.9371	High Similarity	NPC117854
0.9371	High Similarity	NPC470456
0.9371	High Similarity	NPC477502
0.9371	High Similarity	NPC477154
0.9371	High Similarity	NPC6588
0.9371	High Similarity	NPC218226
0.9367	High Similarity	NPC300053
0.9367	High Similarity	NPC108433
0.9367	High Similarity	NPC470457
0.9367	High Similarity	NPC62261
0.9363	High Similarity	NPC474150
0.9363	High Similarity	NPC474162
0.9363	High Similarity	NPC220912
0.9359	High Similarity	NPC328102
0.9359	High Similarity	NPC299436
0.9359	High Similarity	NPC101731
0.9359	High Similarity	NPC472902
0.9355	High Similarity	NPC475267
0.9355	High Similarity	NPC471479
0.9355	High Similarity	NPC474208
0.9355	High Similarity	NPC52530
0.9355	High Similarity	NPC471515
0.9355	High Similarity	NPC474836
0.9355	High Similarity	NPC156057
0.9355	High Similarity	NPC36852
0.9355	High Similarity	NPC262286
0.9355	High Similarity	NPC162869
0.9355	High Similarity	NPC67876
0.9355	High Similarity	NPC78225
0.9355	High Similarity	NPC48208
0.9351	High Similarity	NPC234255
0.9351	High Similarity	NPC117992
0.9351	High Similarity	NPC152951
0.9351	High Similarity	NPC57674
0.9351	High Similarity	NPC230149
0.9351	High Similarity	NPC256925
0.9351	High Similarity	NPC168247
0.9346	High Similarity	NPC19721
0.9346	High Similarity	NPC472912
0.9313	High Similarity	NPC475212
0.9308	High Similarity	NPC170245
0.9308	High Similarity	NPC13481
0.9308	High Similarity	NPC207575
0.9308	High Similarity	NPC43319
0.9308	High Similarity	NPC470462
0.9304	High Similarity	NPC470459
0.9304	High Similarity	NPC18100
0.9299	High Similarity	NPC66618
0.9299	High Similarity	NPC198829
0.9299	High Similarity	NPC84324
0.9299	High Similarity	NPC61010
0.9299	High Similarity	NPC40491
0.9299	High Similarity	NPC305987
0.9299	High Similarity	NPC165970
0.9299	High Similarity	NPC113163
0.9299	High Similarity	NPC349525
0.9299	High Similarity	NPC474239
0.9299	High Similarity	NPC474186
0.9299	High Similarity	NPC278052
0.9299	High Similarity	NPC288131
0.9299	High Similarity	NPC228383
0.9295	High Similarity	NPC476410
0.9295	High Similarity	NPC184755
0.9295	High Similarity	NPC172202
0.9295	High Similarity	NPC187792
0.9295	High Similarity	NPC74178
0.9295	High Similarity	NPC469658
0.9295	High Similarity	NPC204879
0.9295	High Similarity	NPC284127
0.9295	High Similarity	NPC85121
0.929	High Similarity	NPC471985
0.929	High Similarity	NPC138243
0.929	High Similarity	NPC255106
0.929	High Similarity	NPC20530
0.929	High Similarity	NPC215917
0.929	High Similarity	NPC235165
0.929	High Similarity	NPC472455
0.929	High Similarity	NPC471500
0.929	High Similarity	NPC24640
0.929	High Similarity	NPC10754
0.929	High Similarity	NPC68093
0.929	High Similarity	NPC191146
0.9286	High Similarity	NPC33051
0.9286	High Similarity	NPC227337
0.9286	High Similarity	NPC273462
0.9286	High Similarity	NPC70433
0.9286	High Similarity	NPC49402
0.9281	High Similarity	NPC474023
0.9281	High Similarity	NPC472422
0.9281	High Similarity	NPC472420
0.9281	High Similarity	NPC474021
0.9281	High Similarity	NPC263384
0.9281	High Similarity	NPC244577
0.9281	High Similarity	NPC471676
0.9276	High Similarity	NPC177298
0.9276	High Similarity	NPC472628
0.9276	High Similarity	NPC48479
0.9272	High Similarity	NPC91902
0.9259	High Similarity	NPC208668
0.9255	High Similarity	NPC102277
0.9255	High Similarity	NPC279209
0.9245	High Similarity	NPC72787
0.9245	High Similarity	NPC7154
0.9245	High Similarity	NPC36916
0.9245	High Similarity	NPC472277
0.9245	High Similarity	NPC326520
0.9245	High Similarity	NPC50960
0.9245	High Similarity	NPC36
0.9245	High Similarity	NPC58223
0.9245	High Similarity	NPC125039

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 NPC472631 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	360
0.1-0.2	921
0.2-0.3	1882
0.3-0.4	2581
0.4-0.5	1789
0.5-0.6	966
0.6-0.7	463
0.7-0.8	140
0.8-0.85	27
0.85-0.9	16
0.9-0.95	5
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9539	High Similarity	NPD2393	Clinical (unspecified phase)
0.9474	High Similarity	NPD1934	Approved
0.9245	High Similarity	NPD6166	Phase 2
0.9245	High Similarity	NPD6168	Clinical (unspecified phase)
0.9245	High Similarity	NPD6167	Clinical (unspecified phase)
0.9136	High Similarity	NPD7074	Phase 3
0.9074	High Similarity	NPD7054	Approved
0.9038	High Similarity	NPD2801	Approved
0.9018	High Similarity	NPD7472	Approved
0.8968	High Similarity	NPD4380	Phase 2
0.8896	High Similarity	NPD3818	Discontinued
0.8868	High Similarity	NPD7075	Discontinued
0.8824	High Similarity	NPD1511	Approved
0.8805	High Similarity	NPD4868	Clinical (unspecified phase)
0.8805	High Similarity	NPD3882	Suspended
0.8795	High Similarity	NPD7251	Discontinued
0.8743	High Similarity	NPD7808	Phase 3
0.8742	High Similarity	NPD3817	Phase 2
0.8735	High Similarity	NPD6797	Phase 2
0.871	High Similarity	NPD1512	Approved
0.8679	High Similarity	NPD7096	Clinical (unspecified phase)
0.8645	High Similarity	NPD4378	Clinical (unspecified phase)
0.8642	High Similarity	NPD5494	Approved
0.8634	High Similarity	NPD4381	Clinical (unspecified phase)
0.8631	High Similarity	NPD4338	Clinical (unspecified phase)
0.8625	High Similarity	NPD8443	Clinical (unspecified phase)
0.8614	High Similarity	NPD7804	Clinical (unspecified phase)
0.8562	High Similarity	NPD7819	Suspended
0.8553	High Similarity	NPD1550	Clinical (unspecified phase)
0.8553	High Similarity	NPD1552	Clinical (unspecified phase)
0.85	High Similarity	NPD6801	Discontinued
0.8497	Intermediate Similarity	NPD1549	Phase 2
0.8494	Intermediate Similarity	NPD7473	Discontinued
0.8476	Intermediate Similarity	NPD6959	Discontinued
0.8424	Intermediate Similarity	NPD6232	Discontinued
0.8408	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8402	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8393	Intermediate Similarity	NPD5844	Phase 1
0.8353	Intermediate Similarity	NPD6559	Discontinued
0.8323	Intermediate Similarity	NPD7411	Suspended
0.8247	Intermediate Similarity	NPD2796	Approved
0.8221	Intermediate Similarity	NPD1465	Phase 2
0.8182	Intermediate Similarity	NPD1510	Phase 2
0.8158	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8158	Intermediate Similarity	NPD1613	Approved
0.8113	Intermediate Similarity	NPD6799	Approved
0.8061	Intermediate Similarity	NPD5402	Approved
0.8039	Intermediate Similarity	NPD1240	Approved
0.8	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7963	Intermediate Similarity	NPD5403	Approved
0.7961	Intermediate Similarity	NPD3027	Phase 3
0.7947	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7935	Intermediate Similarity	NPD1607	Approved
0.7929	Intermediate Similarity	NPD1247	Approved
0.7927	Intermediate Similarity	NPD6599	Discontinued
0.7922	Intermediate Similarity	NPD943	Approved
0.7917	Intermediate Similarity	NPD919	Approved
0.7904	Intermediate Similarity	NPD7768	Phase 2
0.7895	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7862	Intermediate Similarity	NPD2800	Approved
0.784	Intermediate Similarity	NPD5401	Approved
0.784	Intermediate Similarity	NPD2532	Approved
0.784	Intermediate Similarity	NPD2533	Approved
0.784	Intermediate Similarity	NPD2534	Approved
0.7836	Intermediate Similarity	NPD3926	Phase 2
0.7833	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7826	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7821	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7821	Intermediate Similarity	NPD6651	Approved
0.7811	Intermediate Similarity	NPD6234	Discontinued
0.7803	Intermediate Similarity	NPD7228	Approved
0.7799	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7785	Intermediate Similarity	NPD2935	Discontinued
0.7785	Intermediate Similarity	NPD6100	Approved
0.7785	Intermediate Similarity	NPD6099	Approved
0.7756	Intermediate Similarity	NPD230	Phase 1
0.7753	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.775	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7744	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7725	Intermediate Similarity	NPD37	Approved
0.7719	Intermediate Similarity	NPD7199	Phase 2
0.7702	Intermediate Similarity	NPD4628	Phase 3
0.7697	Intermediate Similarity	NPD1653	Approved
0.7692	Intermediate Similarity	NPD4966	Approved
0.7692	Intermediate Similarity	NPD4965	Approved
0.7692	Intermediate Similarity	NPD4967	Phase 2
0.7677	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7654	Intermediate Similarity	NPD6190	Approved
0.7647	Intermediate Similarity	NPD3749	Approved
0.764	Intermediate Similarity	NPD8313	Approved
0.764	Intermediate Similarity	NPD8312	Approved
0.7627	Intermediate Similarity	NPD7685	Pre-registration
0.76	Intermediate Similarity	NPD3751	Discontinued
0.7593	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7593	Intermediate Similarity	NPD3750	Approved
0.7584	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7579	Intermediate Similarity	NPD7584	Approved
0.7572	Intermediate Similarity	NPD3787	Discontinued
0.7571	Intermediate Similarity	NPD5953	Discontinued
0.7568	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7562	Intermediate Similarity	NPD1551	Phase 2
0.7561	Intermediate Similarity	NPD7390	Discontinued
0.7557	Intermediate Similarity	NPD7286	Phase 2
0.7545	Intermediate Similarity	NPD3226	Approved
0.7532	Intermediate Similarity	NPD447	Suspended
0.7531	Intermediate Similarity	NPD1243	Approved
0.753	Intermediate Similarity	NPD920	Approved
0.7529	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD8150	Discontinued
0.7514	Intermediate Similarity	NPD8434	Phase 2
0.75	Intermediate Similarity	NPD8151	Discontinued
0.75	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7459	Intermediate Similarity	NPD4360	Phase 2
0.7459	Intermediate Similarity	NPD4363	Phase 3
0.7455	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7452	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7447	Intermediate Similarity	NPD6780	Approved
0.7447	Intermediate Similarity	NPD6778	Approved
0.7447	Intermediate Similarity	NPD6776	Approved
0.7447	Intermediate Similarity	NPD6782	Approved
0.7447	Intermediate Similarity	NPD6781	Approved
0.7447	Intermediate Similarity	NPD6777	Approved
0.7447	Intermediate Similarity	NPD6779	Approved
0.7421	Intermediate Similarity	NPD1933	Approved
0.7421	Intermediate Similarity	NPD7435	Discontinued
0.741	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD2346	Discontinued
0.7394	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD2799	Discontinued
0.7391	Intermediate Similarity	NPD7033	Discontinued
0.7391	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7378	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7372	Intermediate Similarity	NPD9494	Approved
0.7371	Intermediate Similarity	NPD5710	Approved
0.7371	Intermediate Similarity	NPD5711	Approved
0.7368	Intermediate Similarity	NPD8455	Phase 2
0.7362	Intermediate Similarity	NPD2424	Discontinued
0.7353	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7342	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7342	Intermediate Similarity	NPD2313	Discontinued
0.7338	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD7240	Approved
0.7333	Intermediate Similarity	NPD7783	Phase 2
0.733	Intermediate Similarity	NPD7697	Approved
0.733	Intermediate Similarity	NPD7696	Phase 3
0.733	Intermediate Similarity	NPD7698	Approved
0.7326	Intermediate Similarity	NPD5353	Approved
0.7325	Intermediate Similarity	NPD6832	Phase 2
0.7325	Intermediate Similarity	NPD4908	Phase 1
0.732	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD5124	Phase 1
0.7305	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7301	Intermediate Similarity	NPD7266	Discontinued
0.7301	Intermediate Similarity	NPD2344	Approved
0.7292	Intermediate Similarity	NPD7871	Phase 2
0.7292	Intermediate Similarity	NPD7870	Phase 2
0.7284	Intermediate Similarity	NPD3748	Approved
0.7278	Intermediate Similarity	NPD4625	Phase 3
0.7277	Intermediate Similarity	NPD6823	Phase 2
0.7268	Intermediate Similarity	NPD7701	Phase 2
0.7235	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7216	Intermediate Similarity	NPD8127	Discontinued
0.7212	Intermediate Similarity	NPD6674	Discontinued
0.7209	Intermediate Similarity	NPD6844	Discontinued
0.7208	Intermediate Similarity	NPD1610	Phase 2
0.7194	Intermediate Similarity	NPD7874	Approved
0.7194	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7182	Intermediate Similarity	NPD3823	Discontinued
0.7181	Intermediate Similarity	NPD6534	Approved
0.7181	Intermediate Similarity	NPD6535	Approved
0.7179	Intermediate Similarity	NPD7585	Approved
0.7175	Intermediate Similarity	NPD7229	Phase 3
0.7158	Intermediate Similarity	NPD7699	Phase 2
0.7158	Intermediate Similarity	NPD7700	Phase 2
0.7157	Intermediate Similarity	NPD7801	Approved
0.7143	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD4361	Phase 2
0.7135	Intermediate Similarity	NPD7458	Discontinued
0.7135	Intermediate Similarity	NPD5242	Approved
0.7134	Intermediate Similarity	NPD1203	Approved
0.7128	Intermediate Similarity	NPD7583	Approved
0.7126	Intermediate Similarity	NPD2309	Approved
0.7125	Intermediate Similarity	NPD6798	Discontinued
0.7115	Intermediate Similarity	NPD4749	Approved
0.7108	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD1652	Phase 2
0.7099	Intermediate Similarity	NPD6355	Discontinued
0.7099	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD2403	Approved
0.7069	Intermediate Similarity	NPD5760	Phase 2
0.7069	Intermediate Similarity	NPD5761	Phase 2
0.7059	Intermediate Similarity	NPD1548	Phase 1
0.7052	Intermediate Similarity	NPD6385	Approved
0.7052	Intermediate Similarity	NPD6386	Approved
0.7051	Intermediate Similarity	NPD9269	Phase 2
0.7044	Intermediate Similarity	NPD2861	Phase 2
0.7044	Intermediate Similarity	NPD3018	Phase 2

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