NPASS Compound

Structure

NPC472635 OpenBabel07101718182D 34 37 0 0 1 0 0 0 0 0999 V2000 1.4476 2.2514 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2749 2.0704 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4593 -1.4135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6554 2.5865 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5215 -0.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.3875 -0.4135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6092 0.1691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4013 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6554 0.5865 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4593 -2.4135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1913 -0.4135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7894 -1.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6386 1.6637 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6554 -0.4135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3253 -1.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.3875 0.5865 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3253 -0.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9234 -2.4135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7431 0.6691 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -4.7894 -0.9135 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.5215 1.0865 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0574 -0.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4067 -1.9135 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -3.0574 -1.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1913 -2.4135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4067 -0.9135 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -8.2535 1.0865 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.4593 -0.4135 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.9234 -3.4135 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2728 -2.4135 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1913 -3.4135 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.5215 2.0865 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.9234 -0.4135 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 13 2 0 0 0 0 2 13 1 0 0 0 0 3 26 1 0 0 0 0 4 32 1 0 0 0 0 5 6 2 0 0 0 0 5 14 1 0 0 0 0 6 16 1 0 0 0 0 7 8 1 0 0 0 0 7 19 1 0 0 0 0 8 26 1 0 0 0 0 9 14 2 0 0 0 0 9 21 1 0 0 0 0 10 15 1 0 0 0 0 10 23 1 0 0 0 0 11 17 2 0 0 0 0 11 22 1 0 0 0 0 12 18 1 0 0 0 0 12 20 1 0 0 0 0 13 19 1 0 0 0 0 15 17 1 0 0 0 0 15 25 2 0 0 0 0 16 21 2 0 0 0 0 16 27 1 0 0 0 0 17 28 1 0 0 0 0 18 24 1 0 0 0 0 18 29 2 0 0 0 0 19 34 1 0 0 0 0 20 14 1 1 0 0 0 20 33 1 0 0 0 0 21 32 1 0 0 0 0 22 24 2 0 0 0 0 22 33 1 0 0 0 0 23 26 1 0 0 0 0 23 30 1 0 0 0 0 24 25 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:	470.19
Volume:	473.256
LogP:	3.537
LogD:	2.859
LogS:	-4.077
# 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:	0.468
Synthetic Accessibility Score:	4.413
Fsp3:	0.423
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:	-5.076
MDCK Permeability:	8.343597073690034e-06
Pgp-inhibitor:	0.163
Pgp-substrate:	0.491
Human Intestinal Absorption (HIA):	0.076
20% Bioavailability (F20%):	0.007
30% Bioavailability (F30%):	0.484

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.016
Plasma Protein Binding (PPB):	96.14569091796875%
Volume Distribution (VD):	0.799
Pgp-substrate:	3.963775157928467%

ADMET: Metabolism

CYP1A2-inhibitor:	0.05
CYP1A2-substrate:	0.874
CYP2C19-inhibitor:	0.125
CYP2C19-substrate:	0.434
CYP2C9-inhibitor:	0.499
CYP2C9-substrate:	0.8
CYP2D6-inhibitor:	0.31
CYP2D6-substrate:	0.557
CYP3A4-inhibitor:	0.356
CYP3A4-substrate:	0.448

ADMET: Excretion

Clearance (CL):	16.903
Half-life (T1/2):	0.442

ADMET: Toxicity

hERG Blockers:	0.023
Human Hepatotoxicity (H-HT):	0.567
Drug-inuced Liver Injury (DILI):	0.578
AMES Toxicity:	0.057
Rat Oral Acute Toxicity:	0.691
Maximum Recommended Daily Dose:	0.886
Skin Sensitization:	0.898
Carcinogencity:	0.463
Eye Corrosion:	0.003
Eye Irritation:	0.365
Respiratory Toxicity:	0.932

Download Data

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

Natural Product: NPC472635

Natural Product ID:	NPC472635
*Common Name:**	RCMQOODWNSIEOO-XWJACEEYSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	RCMQOODWNSIEOO-XWJACEEYSA-N
Standard InCHI:	InChI=1S/C26H30O8/c1-13(2)19-7-8-26(3,34-19)23(30)10-15-17(28)11-22-24(25(15)31)18(29)12-20(33-22)14-5-6-16(27)21(9-14)32-4/h5-6,9,11,19-20,23,27-28,30-31H,1,7-8,10,12H2,2-4H3/t19?,20-,23?,26?/m0/s1
SMILES:	COc1cc(ccc1O)[C@@H]1CC(=O)c2c(O1)cc(c(c2O)CC(C1(C)CCC(O1)C(=C)C)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3581357
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[492403]

☑ 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 NPC472635 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	399
0.1-0.2	1544
0.2-0.3	3414
0.3-0.4	9004
0.4-0.5	9621
0.5-0.6	3818
0.6-0.7	4904
0.7-0.8	6012
0.8-0.85	2805
0.85-0.9	990
0.9-0.95	166
0.95-1	20

Similarity Score	Similarity Level	Natural Product ID
0.9869	High Similarity	NPC472624
0.9806	High Similarity	NPC124038
0.9805	High Similarity	NPC472634
0.974	High Similarity	NPC472630
0.974	High Similarity	NPC472631
0.9739	High Similarity	NPC472598
0.9739	High Similarity	NPC27337
0.9739	High Similarity	NPC474055
0.9682	High Similarity	NPC119589
0.9677	High Similarity	NPC471499
0.9677	High Similarity	NPC472632
0.9677	High Similarity	NPC474038
0.9677	High Similarity	NPC26326
0.9673	High Similarity	NPC278778
0.9673	High Similarity	NPC35038
0.9673	High Similarity	NPC195796
0.9673	High Similarity	NPC291878
0.9618	High Similarity	NPC300053
0.9618	High Similarity	NPC108433
0.9615	High Similarity	NPC474033
0.9615	High Similarity	NPC474034
0.9613	High Similarity	NPC287328
0.9613	High Similarity	NPC470326
0.9613	High Similarity	NPC282009
0.9613	High Similarity	NPC328102
0.9613	High Similarity	NPC119209
0.9613	High Similarity	NPC475784
0.9613	High Similarity	NPC118256
0.9613	High Similarity	NPC192686
0.9613	High Similarity	NPC174953
0.961	High Similarity	NPC291508
0.9608	High Similarity	NPC321779
0.9608	High Similarity	NPC470327
0.9608	High Similarity	NPC477503
0.9608	High Similarity	NPC45849
0.9608	High Similarity	NPC200761
0.9557	High Similarity	NPC471213
0.9554	High Similarity	NPC472625
0.9551	High Similarity	NPC471210
0.9551	High Similarity	NPC471212
0.9551	High Similarity	NPC142252
0.9551	High Similarity	NPC471211
0.9548	High Similarity	NPC473990
0.9548	High Similarity	NPC117418
0.9548	High Similarity	NPC22192
0.9548	High Similarity	NPC53545
0.9545	High Similarity	NPC209614
0.9545	High Similarity	NPC470328
0.9545	High Similarity	NPC472626
0.9542	High Similarity	NPC192083
0.9542	High Similarity	NPC213896
0.9542	High Similarity	NPC18727
0.9542	High Similarity	NPC74924
0.95	High Similarity	NPC279209
0.95	High Similarity	NPC102277
0.9494	High Similarity	NPC472277
0.949	High Similarity	NPC476247
0.9487	High Similarity	NPC36217
0.9484	High Similarity	NPC284820
0.9484	High Similarity	NPC471209
0.9484	High Similarity	NPC223787
0.9484	High Similarity	NPC473272
0.9481	High Similarity	NPC226025
0.9477	High Similarity	NPC236637
0.9477	High Similarity	NPC106976
0.9477	High Similarity	NPC219582
0.9477	High Similarity	NPC302950
0.9437	High Similarity	NPC288813
0.9434	High Similarity	NPC235610
0.9434	High Similarity	NPC170245
0.943	High Similarity	NPC18100
0.943	High Similarity	NPC186686
0.943	High Similarity	NPC472281
0.943	High Similarity	NPC205265
0.9427	High Similarity	NPC134783
0.9427	High Similarity	NPC158188
0.9427	High Similarity	NPC289771
0.9427	High Similarity	NPC266314
0.9423	High Similarity	NPC250214
0.9423	High Similarity	NPC95936
0.9419	High Similarity	NPC250922
0.9419	High Similarity	NPC326037
0.9419	High Similarity	NPC320825
0.9419	High Similarity	NPC13858
0.9416	High Similarity	NPC298692
0.9412	High Similarity	NPC472636
0.9379	High Similarity	NPC212748
0.9375	High Similarity	NPC474024
0.9371	High Similarity	NPC62261
0.9371	High Similarity	NPC293319
0.9371	High Similarity	NPC326520
0.9367	High Similarity	NPC201800
0.9367	High Similarity	NPC474150
0.9367	High Similarity	NPC81679
0.9367	High Similarity	NPC125991
0.9367	High Similarity	NPC474162
0.9367	High Similarity	NPC472964
0.9363	High Similarity	NPC472902
0.9363	High Similarity	NPC470183
0.9363	High Similarity	NPC321399
0.9363	High Similarity	NPC476283
0.9359	High Similarity	NPC471479
0.9359	High Similarity	NPC48208
0.9359	High Similarity	NPC474208
0.9359	High Similarity	NPC52530
0.9359	High Similarity	NPC471515
0.9359	High Similarity	NPC475267
0.9359	High Similarity	NPC52889
0.9359	High Similarity	NPC162869
0.9359	High Similarity	NPC67876
0.9359	High Similarity	NPC156057
0.9359	High Similarity	NPC474836
0.9359	High Similarity	NPC78225
0.9355	High Similarity	NPC234255
0.9355	High Similarity	NPC117992
0.9355	High Similarity	NPC168247
0.9355	High Similarity	NPC152951
0.9355	High Similarity	NPC57674
0.9355	High Similarity	NPC230149
0.9355	High Similarity	NPC256925
0.9351	High Similarity	NPC473996
0.9351	High Similarity	NPC471982
0.9351	High Similarity	NPC472912
0.9346	High Similarity	NPC338131
0.9321	High Similarity	NPC121333
0.9321	High Similarity	NPC261254
0.9321	High Similarity	NPC235575
0.9317	High Similarity	NPC475212
0.9317	High Similarity	NPC165456
0.9313	High Similarity	NPC43319
0.9308	High Similarity	NPC475985
0.9308	High Similarity	NPC472582
0.9308	High Similarity	NPC41301
0.9304	High Similarity	NPC305987
0.9304	High Similarity	NPC349525
0.9304	High Similarity	NPC198829
0.9304	High Similarity	NPC66618
0.9304	High Similarity	NPC113163
0.9304	High Similarity	NPC165970
0.9304	High Similarity	NPC84324
0.9304	High Similarity	NPC288131
0.9299	High Similarity	NPC184755
0.9299	High Similarity	NPC284127
0.9299	High Similarity	NPC172202
0.9299	High Similarity	NPC187792
0.9299	High Similarity	NPC476410
0.9299	High Similarity	NPC74178
0.9299	High Similarity	NPC204879
0.9299	High Similarity	NPC210459
0.9295	High Similarity	NPC471985
0.9295	High Similarity	NPC472455
0.9295	High Similarity	NPC471500
0.9295	High Similarity	NPC191146
0.9295	High Similarity	NPC255106
0.9295	High Similarity	NPC235165
0.9295	High Similarity	NPC68093
0.9295	High Similarity	NPC24640
0.929	High Similarity	NPC70433
0.929	High Similarity	NPC33051
0.929	High Similarity	NPC49402
0.929	High Similarity	NPC273462
0.929	High Similarity	NPC227337
0.9286	High Similarity	NPC471675
0.9286	High Similarity	NPC474744
0.9286	High Similarity	NPC472422
0.9286	High Similarity	NPC472420
0.9286	High Similarity	NPC263384
0.9286	High Similarity	NPC472423
0.9286	High Similarity	NPC471676
0.9286	High Similarity	NPC471677
0.9286	High Similarity	NPC472580
0.9286	High Similarity	NPC474772
0.9286	High Similarity	NPC244577
0.9259	High Similarity	NPC472276
0.9255	High Similarity	NPC117854
0.9255	High Similarity	NPC477154
0.9255	High Similarity	NPC158761
0.9255	High Similarity	NPC477502
0.9255	High Similarity	NPC150131
0.9255	High Similarity	NPC6588
0.9255	High Similarity	NPC218226
0.925	High Similarity	NPC470457
0.925	High Similarity	NPC58223
0.925	High Similarity	NPC36916
0.925	High Similarity	NPC36
0.925	High Similarity	NPC72787
0.925	High Similarity	NPC7688
0.925	High Similarity	NPC7154
0.925	High Similarity	NPC125039
0.925	High Similarity	NPC50960
0.925	High Similarity	NPC475888
0.9245	High Similarity	NPC211107
0.9245	High Similarity	NPC300537
0.9245	High Similarity	NPC220912
0.9245	High Similarity	NPC83922
0.9245	High Similarity	NPC472448
0.9245	High Similarity	NPC127782
0.9241	High Similarity	NPC263449
0.9241	High Similarity	NPC476980
0.9241	High Similarity	NPC299436

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 NPC472635 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	343
0.1-0.2	861
0.2-0.3	1770
0.3-0.4	2606
0.4-0.5	1933
0.5-0.6	1004
0.6-0.7	467
0.7-0.8	124
0.8-0.85	31
0.85-0.9	9
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9542	High Similarity	NPD2393	Clinical (unspecified phase)
0.9477	High Similarity	NPD1934	Approved
0.925	High Similarity	NPD6166	Phase 2
0.925	High Similarity	NPD6168	Clinical (unspecified phase)
0.925	High Similarity	NPD6167	Clinical (unspecified phase)
0.9136	High Similarity	NPD3818	Discontinued
0.9051	High Similarity	NPD3882	Suspended
0.9045	High Similarity	NPD2801	Approved
0.9024	High Similarity	NPD7074	Phase 3
0.8974	High Similarity	NPD4380	Phase 2
0.8963	High Similarity	NPD7054	Approved
0.8909	High Similarity	NPD7472	Approved
0.8882	High Similarity	NPD5494	Approved
0.8831	High Similarity	NPD1511	Approved
0.8758	High Similarity	NPD7075	Discontinued
0.875	High Similarity	NPD3817	Phase 2
0.8743	High Similarity	NPD6797	Phase 2
0.8718	High Similarity	NPD1512	Approved
0.8696	High Similarity	NPD4868	Clinical (unspecified phase)
0.869	High Similarity	NPD7251	Discontinued
0.8654	High Similarity	NPD4378	Clinical (unspecified phase)
0.8642	High Similarity	NPD4381	Clinical (unspecified phase)
0.8639	High Similarity	NPD7808	Phase 3
0.8639	High Similarity	NPD4338	Clinical (unspecified phase)
0.858	High Similarity	NPD6559	Discontinued
0.8571	High Similarity	NPD7096	Clinical (unspecified phase)
0.8562	High Similarity	NPD1550	Clinical (unspecified phase)
0.8562	High Similarity	NPD1552	Clinical (unspecified phase)
0.8519	High Similarity	NPD8443	Clinical (unspecified phase)
0.8512	High Similarity	NPD7804	Clinical (unspecified phase)
0.8509	High Similarity	NPD6801	Discontinued
0.8506	High Similarity	NPD1549	Phase 2
0.8457	Intermediate Similarity	NPD7819	Suspended
0.8434	Intermediate Similarity	NPD6232	Discontinued
0.8418	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8402	Intermediate Similarity	NPD5844	Phase 1
0.8393	Intermediate Similarity	NPD7473	Discontinued
0.8373	Intermediate Similarity	NPD6959	Discontinued
0.8333	Intermediate Similarity	NPD7411	Suspended
0.8304	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8258	Intermediate Similarity	NPD2796	Approved
0.8194	Intermediate Similarity	NPD1510	Phase 2
0.817	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.817	Intermediate Similarity	NPD1613	Approved
0.8155	Intermediate Similarity	NPD1247	Approved
0.8144	Intermediate Similarity	NPD919	Approved
0.8125	Intermediate Similarity	NPD6799	Approved
0.8121	Intermediate Similarity	NPD1465	Phase 2
0.8072	Intermediate Similarity	NPD5402	Approved
0.8059	Intermediate Similarity	NPD3926	Phase 2
0.8052	Intermediate Similarity	NPD1240	Approved
0.8012	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7987	Intermediate Similarity	NPD2800	Approved
0.7975	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7975	Intermediate Similarity	NPD5403	Approved
0.7974	Intermediate Similarity	NPD3027	Phase 3
0.7963	Intermediate Similarity	NPD2533	Approved
0.7963	Intermediate Similarity	NPD2532	Approved
0.7963	Intermediate Similarity	NPD2534	Approved
0.7949	Intermediate Similarity	NPD1607	Approved
0.7941	Intermediate Similarity	NPD7199	Phase 2
0.7939	Intermediate Similarity	NPD6599	Discontinued
0.7935	Intermediate Similarity	NPD943	Approved
0.7929	Intermediate Similarity	NPD6234	Discontinued
0.7908	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.787	Intermediate Similarity	NPD3749	Approved
0.7865	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7853	Intermediate Similarity	NPD5401	Approved
0.7844	Intermediate Similarity	NPD37	Approved
0.7843	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7816	Intermediate Similarity	NPD7228	Approved
0.7811	Intermediate Similarity	NPD7768	Phase 2
0.7811	Intermediate Similarity	NPD4966	Approved
0.7811	Intermediate Similarity	NPD4965	Approved
0.7811	Intermediate Similarity	NPD4967	Phase 2
0.7799	Intermediate Similarity	NPD2935	Discontinued
0.7797	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7764	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7758	Intermediate Similarity	NPD920	Approved
0.7747	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7746	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7742	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7735	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7716	Intermediate Similarity	NPD4628	Phase 3
0.7711	Intermediate Similarity	NPD1653	Approved
0.7702	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7683	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7669	Intermediate Similarity	NPD6190	Approved
0.7658	Intermediate Similarity	NPD230	Phase 1
0.7654	Intermediate Similarity	NPD1243	Approved
0.764	Intermediate Similarity	NPD7685	Pre-registration
0.7636	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7624	Intermediate Similarity	NPD8434	Phase 2
0.7622	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7614	Intermediate Similarity	NPD3751	Discontinued
0.761	Intermediate Similarity	NPD6651	Approved
0.7607	Intermediate Similarity	NPD3750	Approved
0.7586	Intermediate Similarity	NPD3787	Discontinued
0.7584	Intermediate Similarity	NPD5953	Discontinued
0.758	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7578	Intermediate Similarity	NPD6100	Approved
0.7578	Intermediate Similarity	NPD1551	Phase 2
0.7578	Intermediate Similarity	NPD6099	Approved
0.756	Intermediate Similarity	NPD3226	Approved
0.7556	Intermediate Similarity	NPD8312	Approved
0.7556	Intermediate Similarity	NPD8313	Approved
0.7547	Intermediate Similarity	NPD447	Suspended
0.7531	Intermediate Similarity	NPD2344	Approved
0.7516	Intermediate Similarity	NPD7033	Discontinued
0.75	Intermediate Similarity	NPD7584	Approved
0.7487	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7486	Intermediate Similarity	NPD5711	Approved
0.7486	Intermediate Similarity	NPD5710	Approved
0.7485	Intermediate Similarity	NPD2424	Discontinued
0.7473	Intermediate Similarity	NPD4363	Phase 3
0.7473	Intermediate Similarity	NPD4360	Phase 2
0.7472	Intermediate Similarity	NPD7286	Phase 2
0.747	Intermediate Similarity	NPD7390	Discontinued
0.7468	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.746	Intermediate Similarity	NPD6780	Approved
0.746	Intermediate Similarity	NPD6779	Approved
0.746	Intermediate Similarity	NPD6782	Approved
0.746	Intermediate Similarity	NPD6777	Approved
0.746	Intermediate Similarity	NPD6776	Approved
0.746	Intermediate Similarity	NPD6781	Approved
0.746	Intermediate Similarity	NPD6778	Approved
0.7438	Intermediate Similarity	NPD1933	Approved
0.7432	Intermediate Similarity	NPD8150	Discontinued
0.7425	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7423	Intermediate Similarity	NPD2346	Discontinued
0.7407	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD2799	Discontinued
0.7407	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD9494	Approved
0.7358	Intermediate Similarity	NPD2313	Discontinued
0.7355	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7349	Intermediate Similarity	NPD2309	Approved
0.7348	Intermediate Similarity	NPD7240	Approved
0.7344	Intermediate Similarity	NPD7435	Discontinued
0.7342	Intermediate Similarity	NPD4908	Phase 1
0.734	Intermediate Similarity	NPD4361	Phase 2
0.734	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD8151	Discontinued
0.7329	Intermediate Similarity	NPD5124	Phase 1
0.7329	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7301	Intermediate Similarity	NPD3748	Approved
0.7296	Intermediate Similarity	NPD4625	Phase 3
0.7288	Intermediate Similarity	NPD7229	Phase 3
0.7283	Intermediate Similarity	NPD8455	Phase 2
0.7267	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7259	Intermediate Similarity	NPD7783	Phase 2
0.7259	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7254	Intermediate Similarity	NPD7698	Approved
0.7254	Intermediate Similarity	NPD7696	Phase 3
0.7254	Intermediate Similarity	NPD7697	Approved
0.7251	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7233	Intermediate Similarity	NPD6832	Phase 2
0.7232	Intermediate Similarity	NPD8127	Discontinued
0.7226	Intermediate Similarity	NPD1610	Phase 2
0.7216	Intermediate Similarity	NPD7870	Phase 2
0.7216	Intermediate Similarity	NPD7871	Phase 2
0.7212	Intermediate Similarity	NPD7266	Discontinued
0.7207	Intermediate Similarity	NPD2403	Approved
0.7202	Intermediate Similarity	NPD6823	Phase 2
0.7198	Intermediate Similarity	NPD3823	Discontinued
0.7196	Intermediate Similarity	NPD6535	Approved
0.7196	Intermediate Similarity	NPD6534	Approved
0.7194	Intermediate Similarity	NPD7701	Phase 2
0.7184	Intermediate Similarity	NPD5760	Phase 2
0.7184	Intermediate Similarity	NPD5761	Phase 2
0.717	Intermediate Similarity	NPD2861	Phase 2
0.7152	Intermediate Similarity	NPD1203	Approved
0.7151	Intermediate Similarity	NPD5242	Approved
0.715	Intermediate Similarity	NPD2494	Approved
0.715	Intermediate Similarity	NPD2493	Approved
0.7143	Intermediate Similarity	NPD1729	Discontinued
0.7143	Intermediate Similarity	NPD5353	Approved
0.7143	Intermediate Similarity	NPD6798	Discontinued
0.7143	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7127	Intermediate Similarity	NPD2163	Approved
0.7126	Intermediate Similarity	NPD6844	Discontinued
0.7126	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD2654	Approved
0.7126	Intermediate Similarity	NPD1652	Phase 2
0.7121	Intermediate Similarity	NPD7874	Approved
0.7121	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD6355	Discontinued
0.7108	Intermediate Similarity	NPD7907	Approved
0.7107	Intermediate Similarity	NPD7585	Approved
0.7102	Intermediate Similarity	NPD5019	Clinical (unspecified phase)
0.7094	Intermediate Similarity	NPD4111	Phase 1
0.7094	Intermediate Similarity	NPD4665	Approved
0.7085	Intermediate Similarity	NPD7801	Approved
0.7083	Intermediate Similarity	NPD7700	Phase 2
0.7083	Intermediate Similarity	NPD7699	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