NPASS Compound

Structure

NPC472634 OpenBabel07101718182D 35 37 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 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 -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 -2.0000 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 -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 -5.1962 -3.0000 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 -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 1 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 -0.8660 -1.5000 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 2.5981 4.5000 0.0000 C 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 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 -4.3301 -4.5000 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 27 1 0 0 0 0 3 27 1 0 0 0 0 4 33 1 0 0 0 0 5 34 1 0 0 0 0 6 9 1 0 0 0 0 6 15 2 0 0 0 0 7 11 1 0 0 0 0 7 15 1 0 0 0 0 8 10 2 0 0 0 0 8 16 1 0 0 0 0 9 17 1 0 0 0 0 10 18 1 0 0 0 0 11 24 1 0 0 0 0 12 16 2 0 0 0 0 12 22 1 0 0 0 0 13 19 2 0 0 0 0 13 23 1 0 0 0 0 14 20 1 0 0 0 0 14 21 1 0 0 0 0 17 19 1 0 0 0 0 17 26 2 0 0 0 0 18 22 2 0 0 0 0 18 28 1 0 0 0 0 19 29 1 0 0 0 0 20 25 1 0 0 0 0 20 30 2 0 0 0 0 21 16 1 6 0 0 0 21 35 1 0 0 0 0 22 33 1 0 0 0 0 23 25 2 0 0 0 0 23 35 1 0 0 0 0 24 27 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 34 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	486.23
Volume:	499.109
LogP:	3.774
LogD:	3.004
LogS:	-3.822
# Rotatable Bonds:	9
TPSA:	125.68
# H-Bond Aceptor:	8
# H-Bond Donor:	4
# Rings:	3
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.38
Synthetic Accessibility Score:	3.95
Fsp3:	0.444
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:	-4.917
MDCK Permeability:	1.3233348909125198e-05
Pgp-inhibitor:	0.421
Pgp-substrate:	0.982
Human Intestinal Absorption (HIA):	0.092
20% Bioavailability (F20%):	0.006
30% Bioavailability (F30%):	0.029

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.011
Plasma Protein Binding (PPB):	97.13355255126953%
Volume Distribution (VD):	0.441
Pgp-substrate:	2.5394468307495117%

ADMET: Metabolism

CYP1A2-inhibitor:	0.087
CYP1A2-substrate:	0.848
CYP2C19-inhibitor:	0.465
CYP2C19-substrate:	0.301
CYP2C9-inhibitor:	0.844
CYP2C9-substrate:	0.883
CYP2D6-inhibitor:	0.8
CYP2D6-substrate:	0.726
CYP3A4-inhibitor:	0.385
CYP3A4-substrate:	0.359

ADMET: Excretion

Clearance (CL):	9.804
Half-life (T1/2):	0.639

ADMET: Toxicity

hERG Blockers:	0.011
Human Hepatotoxicity (H-HT):	0.227
Drug-inuced Liver Injury (DILI):	0.484
AMES Toxicity:	0.046
Rat Oral Acute Toxicity:	0.612
Maximum Recommended Daily Dose:	0.632
Skin Sensitization:	0.908
Carcinogencity:	0.112
Eye Corrosion:	0.003
Eye Irritation:	0.08
Respiratory Toxicity:	0.931

Download Data

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

Natural Product: NPC472634

Natural Product ID:	NPC472634
*Common Name:**	Tomentodiplacone G
IUPAC Name:	(2S)-5,7-dihydroxy-6-[(E)-6-hydroxy-7-methoxy-3,7-dimethyloct-2-enyl]-2-(4-hydroxy-3-methoxyphenyl)-2,3-dihydrochromen-4-one
Synonyms:
Standard InCHIKey:	IPSAJBVTBHIOPK-QFKXSIOCSA-N
Standard InCHI:	InChI=1S/C27H34O8/c1-15(7-11-24(31)27(2,3)34-5)6-9-17-19(29)13-23-25(26(17)32)20(30)14-21(35-23)16-8-10-18(28)22(12-16)33-4/h6,8,10,12-13,21,24,28-29,31-32H,7,9,11,14H2,1-5H3/b15-6+/t21-,24?/m0/s1
SMILES:	CC(=CCC1=C(C2=C(C=C1O)OC(CC2=O)C3=CC(=C(C=C3)O)OC)O)CCC(C(C)(C)OC)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3581356
PubChem CID:	71682406
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[512728]

☑ 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 NPC472634 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	408
0.1-0.2	1555
0.2-0.3	3800
0.3-0.4	9415
0.4-0.5	8878
0.5-0.6	3390
0.6-0.7	4697
0.7-0.8	5365
0.8-0.85	2861
0.85-0.9	1843
0.9-0.95	390
0.95-1	95

Similarity Score	Similarity Level	Natural Product ID
0.9934	High Similarity	NPC472631
0.9934	High Similarity	NPC472630
0.9805	High Similarity	NPC472635
0.9803	High Similarity	NPC27337
0.9803	High Similarity	NPC472598
0.9803	High Similarity	NPC474055
0.9744	High Similarity	NPC471213
0.974	High Similarity	NPC471210
0.974	High Similarity	NPC471211
0.974	High Similarity	NPC474038
0.974	High Similarity	NPC471212
0.974	High Similarity	NPC26326
0.974	High Similarity	NPC472632
0.974	High Similarity	NPC471499
0.9737	High Similarity	NPC35038
0.9737	High Similarity	NPC195796
0.9737	High Similarity	NPC472626
0.9737	High Similarity	NPC470328
0.9737	High Similarity	NPC278778
0.9737	High Similarity	NPC291878
0.9737	High Similarity	NPC209614
0.9677	High Similarity	NPC474033
0.9677	High Similarity	NPC474034
0.9675	High Similarity	NPC470326
0.9675	High Similarity	NPC282009
0.9675	High Similarity	NPC287328
0.9675	High Similarity	NPC119209
0.9675	High Similarity	NPC472624
0.9675	High Similarity	NPC475784
0.9675	High Similarity	NPC192686
0.9675	High Similarity	NPC118256
0.9675	High Similarity	NPC174953
0.9673	High Similarity	NPC291508
0.9671	High Similarity	NPC477503
0.9671	High Similarity	NPC45849
0.9671	High Similarity	NPC200761
0.9671	High Similarity	NPC470327
0.9671	High Similarity	NPC226025
0.9671	High Similarity	NPC321779
0.9615	High Similarity	NPC124038
0.9615	High Similarity	NPC472625
0.9613	High Similarity	NPC142252
0.9613	High Similarity	NPC158188
0.961	High Similarity	NPC22192
0.961	High Similarity	NPC473990
0.961	High Similarity	NPC117418
0.961	High Similarity	NPC53545
0.9605	High Similarity	NPC192083
0.9605	High Similarity	NPC74924
0.9605	High Similarity	NPC18727
0.9605	High Similarity	NPC213896
0.9605	High Similarity	NPC298692
0.9554	High Similarity	NPC293319
0.9551	High Similarity	NPC472964
0.9551	High Similarity	NPC476247
0.9551	High Similarity	NPC201800
0.9548	High Similarity	NPC470183
0.9548	High Similarity	NPC321399
0.9548	High Similarity	NPC36217
0.9545	High Similarity	NPC284820
0.9545	High Similarity	NPC471209
0.9545	High Similarity	NPC473272
0.9545	High Similarity	NPC223787
0.9539	High Similarity	NPC106976
0.9539	High Similarity	NPC302950
0.9539	High Similarity	NPC219582
0.9539	High Similarity	NPC236637
0.9494	High Similarity	NPC119589
0.949	High Similarity	NPC186686
0.9487	High Similarity	NPC134783
0.9487	High Similarity	NPC289771
0.9487	High Similarity	NPC266314
0.9484	High Similarity	NPC250214
0.9484	High Similarity	NPC95936
0.9484	High Similarity	NPC210459
0.9481	High Similarity	NPC250922
0.9481	High Similarity	NPC320825
0.9481	High Similarity	NPC13858
0.9481	High Similarity	NPC326037
0.9474	High Similarity	NPC471677
0.9434	High Similarity	NPC474024
0.9434	High Similarity	NPC218226
0.9434	High Similarity	NPC158761
0.943	High Similarity	NPC108433
0.943	High Similarity	NPC62261
0.943	High Similarity	NPC300053
0.943	High Similarity	NPC475888
0.9427	High Similarity	NPC211107
0.9427	High Similarity	NPC474162
0.9427	High Similarity	NPC474150
0.9423	High Similarity	NPC472902
0.9423	High Similarity	NPC328102
0.9423	High Similarity	NPC299436
0.9419	High Similarity	NPC471479
0.9419	High Similarity	NPC78225
0.9419	High Similarity	NPC474836
0.9419	High Similarity	NPC52530
0.9419	High Similarity	NPC471515
0.9419	High Similarity	NPC67876
0.9419	High Similarity	NPC48208
0.9419	High Similarity	NPC156057
0.9419	High Similarity	NPC162869
0.9419	High Similarity	NPC52889
0.9419	High Similarity	NPC474208
0.9419	High Similarity	NPC475267
0.9416	High Similarity	NPC117992
0.9416	High Similarity	NPC230149
0.9416	High Similarity	NPC234255
0.9416	High Similarity	NPC152951
0.9416	High Similarity	NPC256925
0.9416	High Similarity	NPC57674
0.9416	High Similarity	NPC168247
0.9412	High Similarity	NPC471982
0.9412	High Similarity	NPC472912
0.9408	High Similarity	NPC338131
0.9375	High Similarity	NPC475212
0.9371	High Similarity	NPC43319
0.9367	High Similarity	NPC7483
0.9367	High Similarity	NPC474240
0.9367	High Similarity	NPC41301
0.9363	High Similarity	NPC288131
0.9363	High Similarity	NPC349525
0.9363	High Similarity	NPC305987
0.9363	High Similarity	NPC198829
0.9363	High Similarity	NPC66618
0.9363	High Similarity	NPC113163
0.9363	High Similarity	NPC84324
0.9363	High Similarity	NPC165970
0.9359	High Similarity	NPC204879
0.9359	High Similarity	NPC172202
0.9359	High Similarity	NPC284127
0.9359	High Similarity	NPC476410
0.9359	High Similarity	NPC74178
0.9359	High Similarity	NPC187792
0.9359	High Similarity	NPC184755
0.9355	High Similarity	NPC10754
0.9355	High Similarity	NPC191146
0.9355	High Similarity	NPC24640
0.9355	High Similarity	NPC471500
0.9355	High Similarity	NPC255106
0.9355	High Similarity	NPC471985
0.9355	High Similarity	NPC20530
0.9355	High Similarity	NPC235165
0.9355	High Similarity	NPC68093
0.9355	High Similarity	NPC472455
0.9355	High Similarity	NPC215917
0.9351	High Similarity	NPC33051
0.9351	High Similarity	NPC227337
0.9351	High Similarity	NPC70433
0.9351	High Similarity	NPC49402
0.9351	High Similarity	NPC273462
0.9346	High Similarity	NPC472422
0.9346	High Similarity	NPC472420
0.9346	High Similarity	NPC471676
0.9346	High Similarity	NPC244577
0.9346	High Similarity	NPC263384
0.9342	High Similarity	NPC472628
0.9321	High Similarity	NPC208668
0.9317	High Similarity	NPC279209
0.9317	High Similarity	NPC102277
0.9313	High Similarity	NPC470456
0.9313	High Similarity	NPC477502
0.9313	High Similarity	NPC477154
0.9313	High Similarity	NPC6588
0.9313	High Similarity	NPC117854
0.9308	High Similarity	NPC36
0.9308	High Similarity	NPC125039
0.9308	High Similarity	NPC472277
0.9308	High Similarity	NPC470457
0.9308	High Similarity	NPC50960
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	NPC127782
0.9304	High Similarity	NPC472448
0.9304	High Similarity	NPC300537
0.9304	High Similarity	NPC83922
0.9304	High Similarity	NPC220912
0.9299	High Similarity	NPC204290
0.9299	High Similarity	NPC476980
0.9299	High Similarity	NPC101731
0.9299	High Similarity	NPC263449
0.9295	High Similarity	NPC36852
0.9295	High Similarity	NPC474681
0.9295	High Similarity	NPC470402
0.9295	High Similarity	NPC183851
0.9295	High Similarity	NPC218313
0.9295	High Similarity	NPC299520
0.9295	High Similarity	NPC262286
0.9295	High Similarity	NPC472910
0.9295	High Similarity	NPC472911
0.9295	High Similarity	NPC245758
0.9295	High Similarity	NPC78071
0.9295	High Similarity	NPC63454
0.9295	High Similarity	NPC96167
0.9295	High Similarity	NPC129684
0.9295	High Similarity	NPC472913
0.9295	High Similarity	NPC472963

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 NPC472634 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	362
0.1-0.2	910
0.2-0.3	1787
0.3-0.4	2598
0.4-0.5	1799
0.5-0.6	996
0.6-0.7	496
0.7-0.8	146
0.8-0.85	30
0.85-0.9	20
0.9-0.95	4
0.95-1	2

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9605	High Similarity	NPD2393	Clinical (unspecified phase)
0.9539	High Similarity	NPD1934	Approved
0.9308	High Similarity	NPD6166	Phase 2
0.9308	High Similarity	NPD6167	Clinical (unspecified phase)
0.9308	High Similarity	NPD6168	Clinical (unspecified phase)
0.9198	High Similarity	NPD7074	Phase 3
0.9136	High Similarity	NPD7054	Approved
0.9103	High Similarity	NPD2801	Approved
0.908	High Similarity	NPD7472	Approved
0.9032	High Similarity	NPD4380	Phase 2
0.8957	High Similarity	NPD3818	Discontinued
0.8931	High Similarity	NPD7075	Discontinued
0.8889	High Similarity	NPD1511	Approved
0.8868	High Similarity	NPD3882	Suspended
0.8855	High Similarity	NPD7251	Discontinued
0.8805	High Similarity	NPD3817	Phase 2
0.8802	High Similarity	NPD7808	Phase 3
0.8795	High Similarity	NPD6797	Phase 2
0.8774	High Similarity	NPD1512	Approved
0.875	High Similarity	NPD4868	Clinical (unspecified phase)
0.8742	High Similarity	NPD7096	Clinical (unspecified phase)
0.871	High Similarity	NPD4378	Clinical (unspecified phase)
0.8704	High Similarity	NPD5494	Approved
0.8696	High Similarity	NPD4381	Clinical (unspecified phase)
0.869	High Similarity	NPD4338	Clinical (unspecified phase)
0.8688	High Similarity	NPD8443	Clinical (unspecified phase)
0.8675	High Similarity	NPD7804	Clinical (unspecified phase)
0.8625	High Similarity	NPD7819	Suspended
0.8618	High Similarity	NPD1552	Clinical (unspecified phase)
0.8618	High Similarity	NPD1550	Clinical (unspecified phase)
0.8562	High Similarity	NPD6801	Discontinued
0.8562	High Similarity	NPD1549	Phase 2
0.8554	High Similarity	NPD7473	Discontinued
0.8485	Intermediate Similarity	NPD6232	Discontinued
0.8471	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8452	Intermediate Similarity	NPD5844	Phase 1
0.8424	Intermediate Similarity	NPD6959	Discontinued
0.8412	Intermediate Similarity	NPD6559	Discontinued
0.8385	Intermediate Similarity	NPD7411	Suspended
0.8353	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8312	Intermediate Similarity	NPD2796	Approved
0.8247	Intermediate Similarity	NPD1510	Phase 2
0.8224	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8224	Intermediate Similarity	NPD1613	Approved
0.8176	Intermediate Similarity	NPD6799	Approved
0.8171	Intermediate Similarity	NPD1465	Phase 2
0.8121	Intermediate Similarity	NPD5402	Approved
0.8105	Intermediate Similarity	NPD1240	Approved
0.8059	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8026	Intermediate Similarity	NPD3027	Phase 3
0.8025	Intermediate Similarity	NPD5403	Approved
0.8	Intermediate Similarity	NPD1607	Approved
0.7988	Intermediate Similarity	NPD6599	Discontinued
0.7988	Intermediate Similarity	NPD1247	Approved
0.7987	Intermediate Similarity	NPD943	Approved
0.7976	Intermediate Similarity	NPD919	Approved
0.7964	Intermediate Similarity	NPD7768	Phase 2
0.7961	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7901	Intermediate Similarity	NPD5401	Approved
0.7895	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7895	Intermediate Similarity	NPD3926	Phase 2
0.7889	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.788	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7877	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7848	Intermediate Similarity	NPD2935	Discontinued
0.7812	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7812	Intermediate Similarity	NPD2800	Approved
0.7809	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7805	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7791	Intermediate Similarity	NPD2533	Approved
0.7791	Intermediate Similarity	NPD2534	Approved
0.7791	Intermediate Similarity	NPD2532	Approved
0.7778	Intermediate Similarity	NPD7199	Phase 2
0.7771	Intermediate Similarity	NPD6651	Approved
0.7765	Intermediate Similarity	NPD6234	Discontinued
0.7764	Intermediate Similarity	NPD4628	Phase 3
0.7759	Intermediate Similarity	NPD7228	Approved
0.7758	Intermediate Similarity	NPD1653	Approved
0.775	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7742	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7736	Intermediate Similarity	NPD6099	Approved
0.7736	Intermediate Similarity	NPD6100	Approved
0.7716	Intermediate Similarity	NPD6190	Approved
0.7707	Intermediate Similarity	NPD230	Phase 1
0.7706	Intermediate Similarity	NPD3749	Approved
0.7697	Intermediate Similarity	NPD8312	Approved
0.7697	Intermediate Similarity	NPD8313	Approved
0.7684	Intermediate Similarity	NPD7685	Pre-registration
0.7679	Intermediate Similarity	NPD37	Approved
0.7657	Intermediate Similarity	NPD3751	Discontinued
0.7654	Intermediate Similarity	NPD3750	Approved
0.7647	Intermediate Similarity	NPD4966	Approved
0.7647	Intermediate Similarity	NPD4965	Approved
0.7647	Intermediate Similarity	NPD4967	Phase 2
0.764	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7632	Intermediate Similarity	NPD7584	Approved
0.763	Intermediate Similarity	NPD3787	Discontinued
0.7627	Intermediate Similarity	NPD5953	Discontinued
0.7625	Intermediate Similarity	NPD1551	Phase 2
0.7622	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7614	Intermediate Similarity	NPD7286	Phase 2
0.7605	Intermediate Similarity	NPD3226	Approved
0.7595	Intermediate Similarity	NPD447	Suspended
0.759	Intermediate Similarity	NPD920	Approved
0.7586	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7569	Intermediate Similarity	NPD8150	Discontinued
0.7569	Intermediate Similarity	NPD8434	Phase 2
0.7546	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD7390	Discontinued
0.7514	Intermediate Similarity	NPD4363	Phase 3
0.7514	Intermediate Similarity	NPD4360	Phase 2
0.75	Intermediate Similarity	NPD6781	Approved
0.75	Intermediate Similarity	NPD6777	Approved
0.75	Intermediate Similarity	NPD6780	Approved
0.75	Intermediate Similarity	NPD6778	Approved
0.75	Intermediate Similarity	NPD6776	Approved
0.75	Intermediate Similarity	NPD6779	Approved
0.75	Intermediate Similarity	NPD6782	Approved
0.7485	Intermediate Similarity	NPD1243	Approved
0.7484	Intermediate Similarity	NPD1933	Approved
0.7474	Intermediate Similarity	NPD7435	Discontinued
0.747	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7469	Intermediate Similarity	NPD2346	Discontinued
0.7461	Intermediate Similarity	NPD8151	Discontinued
0.7455	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7453	Intermediate Similarity	NPD7033	Discontinued
0.7453	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7453	Intermediate Similarity	NPD2799	Discontinued
0.7453	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7439	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD9494	Approved
0.7427	Intermediate Similarity	NPD8455	Phase 2
0.7423	Intermediate Similarity	NPD2424	Discontinued
0.7412	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD2313	Discontinued
0.7403	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD6832	Phase 2
0.7389	Intermediate Similarity	NPD4908	Phase 1
0.7386	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7385	Intermediate Similarity	NPD7783	Phase 2
0.7385	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7382	Intermediate Similarity	NPD7698	Approved
0.7382	Intermediate Similarity	NPD7697	Approved
0.7382	Intermediate Similarity	NPD7696	Phase 3
0.7375	Intermediate Similarity	NPD5124	Phase 1
0.7375	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7362	Intermediate Similarity	NPD7266	Discontinued
0.7362	Intermediate Similarity	NPD2344	Approved
0.7346	Intermediate Similarity	NPD3748	Approved
0.7344	Intermediate Similarity	NPD7871	Phase 2
0.7344	Intermediate Similarity	NPD7870	Phase 2
0.7342	Intermediate Similarity	NPD4625	Phase 3
0.733	Intermediate Similarity	NPD6823	Phase 2
0.733	Intermediate Similarity	NPD5710	Approved
0.733	Intermediate Similarity	NPD5711	Approved
0.732	Intermediate Similarity	NPD7701	Phase 2
0.7296	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7294	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7293	Intermediate Similarity	NPD7240	Approved
0.7283	Intermediate Similarity	NPD5353	Approved
0.7273	Intermediate Similarity	NPD8127	Discontinued
0.7273	Intermediate Similarity	NPD1610	Phase 2
0.7267	Intermediate Similarity	NPD6844	Discontinued
0.7245	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7245	Intermediate Similarity	NPD7874	Approved
0.7238	Intermediate Similarity	NPD3823	Discontinued
0.7234	Intermediate Similarity	NPD6535	Approved
0.7234	Intermediate Similarity	NPD6534	Approved
0.7232	Intermediate Similarity	NPD7229	Phase 3
0.7231	Intermediate Similarity	NPD7585	Approved
0.7211	Intermediate Similarity	NPD7700	Phase 2
0.7211	Intermediate Similarity	NPD7699	Phase 2
0.7208	Intermediate Similarity	NPD7801	Approved
0.7197	Intermediate Similarity	NPD1203	Approved
0.7196	Intermediate Similarity	NPD4361	Phase 2
0.7196	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD7458	Discontinued
0.7191	Intermediate Similarity	NPD5242	Approved
0.7188	Intermediate Similarity	NPD6798	Discontinued
0.7186	Intermediate Similarity	NPD2309	Approved
0.7179	Intermediate Similarity	NPD7583	Approved
0.7169	Intermediate Similarity	NPD6674	Discontinued
0.7169	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7169	Intermediate Similarity	NPD1652	Phase 2
0.716	Intermediate Similarity	NPD6355	Discontinued
0.716	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD5761	Phase 2
0.7126	Intermediate Similarity	NPD5760	Phase 2
0.7124	Intermediate Similarity	NPD1548	Phase 1
0.711	Intermediate Similarity	NPD6386	Approved
0.711	Intermediate Similarity	NPD6385	Approved
0.7107	Intermediate Similarity	NPD3018	Phase 2
0.7107	Intermediate Similarity	NPD2861	Phase 2
0.7099	Intermediate Similarity	NPD4060	Phase 1
0.7081	Intermediate Similarity	NPD3268	Approved
0.7077	Intermediate Similarity	NPD8320	Phase 1

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