NPASS Compound

Structure

NPC475888 OpenBabel07101718182D 39 41 0 0 1 0 0 0 0 0999 V2000 -0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -4.0000 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 -1.7321 -3.0000 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 2.5981 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 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 0.8660 -2.5000 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 -1.5000 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 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 -2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -3.0000 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 3.4641 3.0000 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 -1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 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 3.4641 -1.0000 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 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 0.0000 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 0.8660 1.5000 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 0.8660 0.5000 0.0000 C 0 0 2 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 4.3301 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 3.0000 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 -3.4641 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -1.5000 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 17 1 0 0 0 0 2 17 1 0 0 0 0 3 18 1 0 0 0 0 4 18 1 0 0 0 0 5 19 1 0 0 0 0 6 19 1 0 0 0 0 7 37 1 0 0 0 0 8 38 1 0 0 0 0 9 12 1 0 0 0 0 9 17 2 0 0 0 0 10 13 1 0 0 0 0 10 18 2 0 0 0 0 11 14 1 0 0 0 0 11 19 2 0 0 0 0 12 20 1 0 0 0 0 13 21 1 0 0 0 0 14 22 1 0 0 0 0 15 20 2 0 0 0 0 15 25 1 0 0 0 0 16 23 2 0 0 0 0 16 24 1 0 0 0 0 20 26 1 0 0 0 0 21 24 2 0 0 0 0 21 31 1 0 0 0 0 22 26 2 0 0 0 0 22 28 1 0 0 0 0 23 27 1 0 0 0 0 23 33 1 0 0 0 0 24 37 1 0 0 0 0 25 28 2 0 0 0 0 25 38 1 0 0 0 0 27 29 1 0 0 0 0 27 31 2 0 0 0 0 28 34 1 0 0 0 0 29 30 1 0 0 0 0 29 35 2 0 0 0 0 30 32 1 0 0 0 0 30 36 1 6 0 0 0 31 39 1 0 0 0 0 32 26 1 1 0 0 0 32 39 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	536.28
Volume:	571.526
LogP:	7.608
LogD:	4.328
LogS:	-2.485
# Rotatable Bonds:	9
TPSA:	105.45
# H-Bond Aceptor:	7
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.322
Synthetic Accessibility Score:	4.246
Fsp3:	0.406
Lipinski Rule-of-5:	Rejected
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:	-4.899
MDCK Permeability:	1.2399516890582163e-05
Pgp-inhibitor:	0.982
Pgp-substrate:	0.99
Human Intestinal Absorption (HIA):	0.265
20% Bioavailability (F20%):	0.972
30% Bioavailability (F30%):	0.113

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.013
Plasma Protein Binding (PPB):	75.30265045166016%
Volume Distribution (VD):	1.342
Pgp-substrate:	32.244781494140625%

ADMET: Metabolism

CYP1A2-inhibitor:	0.056
CYP1A2-substrate:	0.724
CYP2C19-inhibitor:	0.677
CYP2C19-substrate:	0.628
CYP2C9-inhibitor:	0.862
CYP2C9-substrate:	0.948
CYP2D6-inhibitor:	0.418
CYP2D6-substrate:	0.359
CYP3A4-inhibitor:	0.431
CYP3A4-substrate:	0.237

ADMET: Excretion

Clearance (CL):	9.662
Half-life (T1/2):	0.073

ADMET: Toxicity

hERG Blockers:	0.059
Human Hepatotoxicity (H-HT):	0.917
Drug-inuced Liver Injury (DILI):	0.442
AMES Toxicity:	0.017
Rat Oral Acute Toxicity:	0.311
Maximum Recommended Daily Dose:	0.077
Skin Sensitization:	0.863
Carcinogencity:	0.027
Eye Corrosion:	0.003
Eye Irritation:	0.048
Respiratory Toxicity:	0.592

Download Data

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

Natural Product: NPC475888

Natural Product ID:	NPC475888
*Common Name:**	(2R,3R)-3,5-Dihydroxy-2-(3-Hydroxy-4-Methoxy-2,6-Bis(3-Methylbut-2-Enyl)Phenyl)-7-Methoxy-8-(3-Methylbut-2-Enyl)Chroman-4-One
IUPAC Name:	(2R,3R)-3,5-dihydroxy-2-[3-hydroxy-4-methoxy-2,6-bis(3-methylbut-2-enyl)phenyl]-7-methoxy-8-(3-methylbut-2-enyl)-2,3-dihydrochromen-4-one
Synonyms:
Standard InCHIKey:	JJESTABXHZLPPK-XDFJSJKPSA-N
Standard InCHI:	InChI=1S/C32H40O7/c1-17(2)9-12-20-15-25(38-8)28(34)22(14-11-19(5)6)26(20)32-30(36)29(35)27-23(33)16-24(37-7)21(31(27)39-32)13-10-18(3)4/h9-11,15-16,30,32-34,36H,12-14H2,1-8H3/t30-,32+/m0/s1
SMILES:	CC(=CCC1=CC(=C(C(=C1C2C(C(=O)C3=C(O2)C(=C(C=C3O)OC)CC=C(C)C)O)CC=C(C)C)O)OC)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL517957
PubChem CID:	460687
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0000337] Flavans [CHEMONTID:0003645] 2'-prenylated flavans [CHEMONTID:0003588] 2'-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
NPO27127	Petalostemum purpureum	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[8289060]
NPO27127	Petalostemum purpureum	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TCMID]

☑ 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
MIC	6

Activity Type	# Activity
Organism	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT86	Organism	Mycobacterium intracellulare	Mycobacterium intracellulare	MIC	=	25.0	ug.mL-1	PMID[484773]
NPT20	Organism	Candida albicans	Candida albicans	MIC	=	5.0	ug.mL-1	PMID[484773]
NPT85	Organism	Filobasidiella neoformans	Cryptococcus neoformans	MIC	=	5.0	ug.mL-1	PMID[484773]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	=	5.0	ug.mL-1	PMID[484773]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	5.0	ug.mL-1	PMID[484773]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	=	5.0	ug.mL-1	PMID[484773]

☑ 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 NPC475888 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	419
0.1-0.2	1564
0.2-0.3	3634
0.3-0.4	9083
0.4-0.5	9380
0.5-0.6	3446
0.6-0.7	4778
0.7-0.8	5712
0.8-0.85	2874
0.85-0.9	1497
0.9-0.95	282
0.95-1	28

Similarity Score	Similarity Level	Natural Product ID
0.9935	High Similarity	NPC474240
0.9871	High Similarity	NPC211107
0.9806	High Similarity	NPC474239
0.9744	High Similarity	NPC201800
0.9615	High Similarity	NPC287328
0.9615	High Similarity	NPC470326
0.9615	High Similarity	NPC282009
0.9615	High Similarity	NPC321399
0.9615	High Similarity	NPC36217
0.9615	High Similarity	NPC299436
0.9557	High Similarity	NPC7483
0.9554	High Similarity	NPC471499
0.9551	High Similarity	NPC22192
0.9551	High Similarity	NPC210459
0.9548	High Similarity	NPC470328
0.9548	High Similarity	NPC209614
0.9548	High Similarity	NPC472626
0.9497	High Similarity	NPC293319
0.9494	High Similarity	NPC472964
0.949	High Similarity	NPC472631
0.949	High Similarity	NPC472630
0.949	High Similarity	NPC470183
0.9487	High Similarity	NPC472598
0.9487	High Similarity	NPC474055
0.9484	High Similarity	NPC477503
0.9484	High Similarity	NPC470327
0.9484	High Similarity	NPC45849
0.9484	High Similarity	NPC200761
0.9437	High Similarity	NPC471213
0.9434	High Similarity	NPC186686
0.9434	High Similarity	NPC472625
0.943	High Similarity	NPC474351
0.943	High Similarity	NPC474186
0.943	High Similarity	NPC40491
0.943	High Similarity	NPC278052
0.943	High Similarity	NPC472634
0.943	High Similarity	NPC475883
0.9427	High Similarity	NPC85121
0.9423	High Similarity	NPC13779
0.9423	High Similarity	NPC13858
0.9423	High Similarity	NPC291878
0.9423	High Similarity	NPC278778
0.9423	High Similarity	NPC250922
0.9423	High Similarity	NPC35038
0.9423	High Similarity	NPC475799
0.9423	High Similarity	NPC326037
0.9423	High Similarity	NPC320825
0.9423	High Similarity	NPC195796
0.9419	High Similarity	NPC298692
0.9379	High Similarity	NPC474024
0.9379	High Similarity	NPC477154
0.9379	High Similarity	NPC117854
0.9379	High Similarity	NPC6588
0.9379	High Similarity	NPC218226
0.9375	High Similarity	NPC62261
0.9375	High Similarity	NPC326520
0.9367	High Similarity	NPC56085
0.9367	High Similarity	NPC472902
0.9367	High Similarity	NPC174953
0.9367	High Similarity	NPC320359
0.9367	High Similarity	NPC475886
0.9367	High Similarity	NPC228785
0.9367	High Similarity	NPC474287
0.9367	High Similarity	NPC14353
0.9363	High Similarity	NPC27337
0.9363	High Similarity	NPC471479
0.9363	High Similarity	NPC273843
0.9363	High Similarity	NPC52530
0.9363	High Similarity	NPC291508
0.9363	High Similarity	NPC471515
0.9363	High Similarity	NPC223787
0.9359	High Similarity	NPC226025
0.9359	High Similarity	NPC321779
0.9359	High Similarity	NPC67396
0.9355	High Similarity	NPC106976
0.9317	High Similarity	NPC170245
0.9317	High Similarity	NPC477517
0.9317	High Similarity	NPC43319
0.9313	High Similarity	NPC236132
0.9313	High Similarity	NPC41301
0.9308	High Similarity	NPC61010
0.9308	High Similarity	NPC289771
0.9308	High Similarity	NPC471211
0.9308	High Similarity	NPC26326
0.9308	High Similarity	NPC474038
0.9308	High Similarity	NPC471212
0.9308	High Similarity	NPC474187
0.9308	High Similarity	NPC472632
0.9308	High Similarity	NPC471210
0.9304	High Similarity	NPC100123
0.9304	High Similarity	NPC473990
0.9304	High Similarity	NPC329091
0.9299	High Similarity	NPC471500
0.9299	High Similarity	NPC24640
0.9295	High Similarity	NPC18727
0.9295	High Similarity	NPC213896
0.9295	High Similarity	NPC192083
0.9295	High Similarity	NPC74924
0.9264	High Similarity	NPC102277
0.9264	High Similarity	NPC279209
0.9259	High Similarity	NPC158761
0.9259	High Similarity	NPC470456
0.9259	High Similarity	NPC150131
0.9255	High Similarity	NPC470457
0.925	High Similarity	NPC474034
0.925	High Similarity	NPC476247
0.925	High Similarity	NPC472635
0.925	High Similarity	NPC474033
0.9245	High Similarity	NPC192686
0.9245	High Similarity	NPC475784
0.9245	High Similarity	NPC118256
0.9245	High Similarity	NPC263449
0.9245	High Similarity	NPC119209
0.9245	High Similarity	NPC472624
0.9241	High Similarity	NPC236796
0.9241	High Similarity	NPC67876
0.9241	High Similarity	NPC165977
0.9241	High Similarity	NPC136674
0.9241	High Similarity	NPC217677
0.9241	High Similarity	NPC472963
0.9241	High Similarity	NPC300727
0.9241	High Similarity	NPC241904
0.9231	High Similarity	NPC9743
0.9231	High Similarity	NPC236637
0.9231	High Similarity	NPC471982
0.9231	High Similarity	NPC19721
0.9231	High Similarity	NPC240476
0.9231	High Similarity	NPC246162
0.9231	High Similarity	NPC260491
0.9231	High Similarity	NPC36835
0.9231	High Similarity	NPC302950
0.9231	High Similarity	NPC138288
0.9231	High Similarity	NPC219582
0.9231	High Similarity	NPC61506
0.9226	High Similarity	NPC338131
0.9198	High Similarity	NPC470462
0.9198	High Similarity	NPC39091
0.9193	High Similarity	NPC152659
0.9193	High Similarity	NPC475985
0.9193	High Similarity	NPC124038
0.9193	High Similarity	NPC197168
0.9193	High Similarity	NPC248638
0.9193	High Similarity	NPC18100
0.9193	High Similarity	NPC470459
0.9193	High Similarity	NPC220313
0.9193	High Similarity	NPC236521
0.9187	High Similarity	NPC187354
0.9187	High Similarity	NPC308992
0.9187	High Similarity	NPC158188
0.9187	High Similarity	NPC173137
0.9187	High Similarity	NPC134783
0.9187	High Similarity	NPC142252
0.9182	High Similarity	NPC117418
0.9182	High Similarity	NPC55738
0.9182	High Similarity	NPC250214
0.9182	High Similarity	NPC95936
0.9182	High Similarity	NPC476242
0.9182	High Similarity	NPC235448
0.9182	High Similarity	NPC53545
0.9177	High Similarity	NPC274730
0.9177	High Similarity	NPC142339
0.9177	High Similarity	NPC472907
0.9172	High Similarity	NPC325028
0.9172	High Similarity	NPC246328
0.9172	High Similarity	NPC293286
0.9172	High Similarity	NPC256346
0.9172	High Similarity	NPC27532
0.9172	High Similarity	NPC473664
0.9167	High Similarity	NPC262038
0.9167	High Similarity	NPC262039
0.9167	High Similarity	NPC319910
0.9167	High Similarity	NPC304295
0.9167	High Similarity	NPC278476
0.9167	High Similarity	NPC254412
0.9167	High Similarity	NPC205046
0.9167	High Similarity	NPC59162
0.9136	High Similarity	NPC36916
0.9136	High Similarity	NPC472450
0.9136	High Similarity	NPC58223
0.9136	High Similarity	NPC7688
0.9136	High Similarity	NPC36
0.9136	High Similarity	NPC472277
0.9136	High Similarity	NPC25361
0.9136	High Similarity	NPC7154
0.9136	High Similarity	NPC125039
0.9136	High Similarity	NPC239752
0.9136	High Similarity	NPC275780
0.9136	High Similarity	NPC473286
0.9136	High Similarity	NPC224280
0.9136	High Similarity	NPC72787
0.913	High Similarity	NPC25152
0.913	High Similarity	NPC474150
0.913	High Similarity	NPC474162
0.9125	High Similarity	NPC474960
0.9125	High Similarity	NPC119224
0.9125	High Similarity	NPC471973
0.9125	High Similarity	NPC246478
0.9119	High Similarity	NPC284820
0.9119	High Similarity	NPC471209
0.9119	High Similarity	NPC156057

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 NPC475888 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	373
0.1-0.2	937
0.2-0.3	1859
0.3-0.4	2581
0.4-0.5	1785
0.5-0.6	935
0.6-0.7	488
0.7-0.8	144
0.8-0.85	28
0.85-0.9	15
0.9-0.95	5
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9295	High Similarity	NPD2393	Clinical (unspecified phase)
0.9231	High Similarity	NPD1934	Approved
0.9136	High Similarity	NPD6167	Clinical (unspecified phase)
0.9136	High Similarity	NPD6168	Clinical (unspecified phase)
0.9136	High Similarity	NPD6166	Phase 2
0.882	High Similarity	NPD3882	Suspended
0.8812	High Similarity	NPD2801	Approved
0.8802	High Similarity	NPD7074	Phase 3
0.8765	High Similarity	NPD7075	Discontinued
0.8757	High Similarity	NPD7808	Phase 3
0.8743	High Similarity	NPD7054	Approved
0.8726	High Similarity	NPD1512	Approved
0.8698	High Similarity	NPD7251	Discontinued
0.8696	High Similarity	NPD7096	Clinical (unspecified phase)
0.8696	High Similarity	NPD7819	Suspended
0.869	High Similarity	NPD7472	Approved
0.8662	High Similarity	NPD4378	Clinical (unspecified phase)
0.8642	High Similarity	NPD3817	Phase 2
0.8639	High Similarity	NPD6797	Phase 2
0.8631	High Similarity	NPD7804	Clinical (unspecified phase)
0.8625	High Similarity	NPD4380	Phase 2
0.8599	High Similarity	NPD1511	Approved
0.8571	High Similarity	NPD3818	Discontinued
0.8545	High Similarity	NPD5494	Approved
0.8538	High Similarity	NPD4338	Clinical (unspecified phase)
0.8528	High Similarity	NPD8443	Clinical (unspecified phase)
0.8521	High Similarity	NPD5844	Phase 1
0.8512	High Similarity	NPD7473	Discontinued
0.8494	Intermediate Similarity	NPD6959	Discontinued
0.8476	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8443	Intermediate Similarity	NPD6232	Discontinued
0.8421	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8405	Intermediate Similarity	NPD6801	Discontinued
0.8333	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8313	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.828	Intermediate Similarity	NPD1549	Phase 2
0.8242	Intermediate Similarity	NPD1465	Phase 2
0.8137	Intermediate Similarity	NPD6799	Approved
0.8061	Intermediate Similarity	NPD6599	Discontinued
0.8057	Intermediate Similarity	NPD6559	Discontinued
0.8056	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.8038	Intermediate Similarity	NPD2796	Approved
0.8012	Intermediate Similarity	NPD7411	Suspended
0.7976	Intermediate Similarity	NPD5402	Approved
0.7975	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7975	Intermediate Similarity	NPD2532	Approved
0.7975	Intermediate Similarity	NPD2534	Approved
0.7975	Intermediate Similarity	NPD2533	Approved
0.7975	Intermediate Similarity	NPD1510	Phase 2
0.7953	Intermediate Similarity	NPD1247	Approved
0.7949	Intermediate Similarity	NPD1613	Approved
0.7949	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7944	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7941	Intermediate Similarity	NPD919	Approved
0.7937	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7929	Intermediate Similarity	NPD7768	Phase 2
0.7919	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7879	Intermediate Similarity	NPD5403	Approved
0.7877	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7861	Intermediate Similarity	NPD3926	Phase 2
0.7849	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7836	Intermediate Similarity	NPD6234	Discontinued
0.7834	Intermediate Similarity	NPD1240	Approved
0.7829	Intermediate Similarity	NPD7228	Approved
0.7829	Intermediate Similarity	NPD3751	Discontinued
0.7803	Intermediate Similarity	NPD3787	Discontinued
0.7778	Intermediate Similarity	NPD2800	Approved
0.7765	Intermediate Similarity	NPD8312	Approved
0.7765	Intermediate Similarity	NPD8313	Approved
0.7759	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7758	Intermediate Similarity	NPD5401	Approved
0.7756	Intermediate Similarity	NPD3027	Phase 3
0.7751	Intermediate Similarity	NPD37	Approved
0.775	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7746	Intermediate Similarity	NPD7199	Phase 2
0.7742	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7736	Intermediate Similarity	NPD1607	Approved
0.7735	Intermediate Similarity	NPD8150	Discontinued
0.773	Intermediate Similarity	NPD3750	Approved
0.7722	Intermediate Similarity	NPD943	Approved
0.7719	Intermediate Similarity	NPD4967	Phase 2
0.7719	Intermediate Similarity	NPD4966	Approved
0.7719	Intermediate Similarity	NPD4965	Approved
0.7702	Intermediate Similarity	NPD6099	Approved
0.7702	Intermediate Similarity	NPD6100	Approved
0.7692	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7674	Intermediate Similarity	NPD3749	Approved
0.764	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7637	Intermediate Similarity	NPD8434	Phase 2
0.7622	Intermediate Similarity	NPD4628	Phase 3
0.7617	Intermediate Similarity	NPD8151	Discontinued
0.7594	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7593	Intermediate Similarity	NPD2935	Discontinued
0.759	Intermediate Similarity	NPD7390	Discontinued
0.7574	Intermediate Similarity	NPD3226	Approved
0.7566	Intermediate Similarity	NPD6782	Approved
0.7566	Intermediate Similarity	NPD6776	Approved
0.7566	Intermediate Similarity	NPD6778	Approved
0.7566	Intermediate Similarity	NPD6777	Approved
0.7566	Intermediate Similarity	NPD6781	Approved
0.7566	Intermediate Similarity	NPD6780	Approved
0.7566	Intermediate Similarity	NPD6779	Approved
0.7562	Intermediate Similarity	NPD230	Phase 1
0.7561	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7546	Intermediate Similarity	NPD2346	Discontinued
0.7539	Intermediate Similarity	NPD7696	Phase 3
0.7539	Intermediate Similarity	NPD7435	Discontinued
0.7539	Intermediate Similarity	NPD7698	Approved
0.7539	Intermediate Similarity	NPD7697	Approved
0.7516	Intermediate Similarity	NPD6651	Approved
0.7514	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7870	Phase 2
0.75	Intermediate Similarity	NPD7871	Phase 2
0.75	Intermediate Similarity	NPD5710	Approved
0.75	Intermediate Similarity	NPD5711	Approved
0.7484	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7474	Intermediate Similarity	NPD7701	Phase 2
0.747	Intermediate Similarity	NPD6190	Approved
0.7459	Intermediate Similarity	NPD7685	Pre-registration
0.7456	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.744	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7423	Intermediate Similarity	NPD3748	Approved
0.7412	Intermediate Similarity	NPD1653	Approved
0.741	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7398	Intermediate Similarity	NPD7874	Approved
0.7398	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD4363	Phase 3
0.7394	Intermediate Similarity	NPD4360	Phase 2
0.7391	Intermediate Similarity	NPD4060	Phase 1
0.7389	Intermediate Similarity	NPD7286	Phase 2
0.7378	Intermediate Similarity	NPD1551	Phase 2
0.7375	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD7699	Phase 2
0.7368	Intermediate Similarity	NPD7700	Phase 2
0.7368	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7363	Intermediate Similarity	NPD7240	Approved
0.736	Intermediate Similarity	NPD7801	Approved
0.736	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.736	Intermediate Similarity	NPD7783	Phase 2
0.7353	Intermediate Similarity	NPD920	Approved
0.7349	Intermediate Similarity	NPD1243	Approved
0.7349	Intermediate Similarity	NPD6674	Discontinued
0.7346	Intermediate Similarity	NPD447	Suspended
0.7317	Intermediate Similarity	NPD2799	Discontinued
0.7312	Intermediate Similarity	NPD4625	Phase 3
0.7308	Intermediate Similarity	NPD5953	Discontinued
0.7303	Intermediate Similarity	NPD7229	Phase 3
0.7302	Intermediate Similarity	NPD6535	Approved
0.7302	Intermediate Similarity	NPD6534	Approved
0.7299	Intermediate Similarity	NPD8455	Phase 2
0.7278	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD4908	Phase 1
0.7247	Intermediate Similarity	NPD8127	Discontinued
0.7246	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7245	Intermediate Similarity	NPD7584	Approved
0.7239	Intermediate Similarity	NPD6355	Discontinued
0.7239	Intermediate Similarity	NPD1933	Approved
0.7235	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7235	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7231	Intermediate Similarity	NPD8320	Phase 1
0.7231	Intermediate Similarity	NPD8319	Approved
0.7229	Intermediate Similarity	NPD2344	Approved
0.7219	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7216	Intermediate Similarity	NPD6823	Phase 2
0.7206	Intermediate Similarity	NPD7907	Approved
0.7202	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD9494	Approved
0.7184	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7165	Intermediate Similarity	NPD2493	Approved
0.7165	Intermediate Similarity	NPD2494	Approved
0.716	Intermediate Similarity	NPD2313	Discontinued
0.716	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD6798	Discontinued
0.7159	Intermediate Similarity	NPD5353	Approved
0.7152	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD1610	Phase 2
0.7134	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7127	Intermediate Similarity	NPD2403	Approved
0.7108	Intermediate Similarity	NPD4665	Approved
0.7108	Intermediate Similarity	NPD7033	Discontinued
0.7108	Intermediate Similarity	NPD4111	Phase 1
0.7083	Intermediate Similarity	NPD4361	Phase 2
0.7083	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD2424	Discontinued
0.7077	Intermediate Similarity	NPD3452	Approved
0.7077	Intermediate Similarity	NPD3450	Approved
0.7072	Intermediate Similarity	NPD5242	Approved
0.7069	Intermediate Similarity	NPD7458	Discontinued
0.7062	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD2309	Approved
0.7059	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7056	Intermediate Similarity	NPD4582	Approved
0.7056	Intermediate Similarity	NPD4583	Approved
0.7053	Intermediate Similarity	NPD2488	Approved
0.7053	Intermediate Similarity	NPD2490	Approved
0.7045	Intermediate Similarity	NPD6844	Discontinued
0.7039	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD6832	Phase 2
0.7033	Intermediate Similarity	NPD7784	Clinical (unspecified phase)

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