NPASS Compound

Structure

CID236756 OpenBabel06191716032D 32 35 0 0 1 0 0 0 0 0999 V2000 1.7321 -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 -1.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3660 -0.3660 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 6.9282 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 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 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 5.1962 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 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 2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 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 2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.3301 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 4.3301 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 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 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 14 1 0 0 0 0 2 14 1 0 0 0 0 3 26 1 0 0 0 0 4 26 1 0 0 0 0 5 30 1 0 0 0 0 6 7 2 0 0 0 0 6 8 1 0 0 0 0 7 9 1 0 0 0 0 8 15 2 0 0 0 0 9 18 2 0 0 0 0 10 11 1 0 0 0 0 10 14 2 0 0 0 0 11 17 1 0 0 0 0 12 13 2 0 0 0 0 12 16 1 0 0 0 0 13 26 1 0 0 0 0 15 18 1 0 0 0 0 16 20 2 0 0 0 0 16 22 1 0 0 0 0 17 22 2 0 0 0 0 17 23 1 0 0 0 0 18 27 1 0 0 0 0 19 20 1 0 0 0 0 19 21 1 0 0 0 0 19 23 2 0 0 0 0 20 28 1 0 0 0 0 21 25 1 0 0 0 0 21 29 2 0 0 0 0 22 32 1 0 0 0 0 23 31 1 0 0 0 0 24 15 1 1 0 0 0 24 25 1 0 0 0 0 24 31 1 0 0 0 0 25 30 1 6 0 0 0 26 32 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	436.19
Volume:	453.039
LogP:	6.297
LogD:	3.865
LogS:	-2.838
# Rotatable Bonds:	4
TPSA:	85.22
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.647
Synthetic Accessibility Score:	4.016
Fsp3:	0.346
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.797
MDCK Permeability:	1.5742440155008808e-05
Pgp-inhibitor:	0.99
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.053
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.004

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.026
Plasma Protein Binding (PPB):	99.73467254638672%
Volume Distribution (VD):	0.479
Pgp-substrate:	2.5737767219543457%

ADMET: Metabolism

CYP1A2-inhibitor:	0.191
CYP1A2-substrate:	0.484
CYP2C19-inhibitor:	0.602
CYP2C19-substrate:	0.411
CYP2C9-inhibitor:	0.894
CYP2C9-substrate:	0.826
CYP2D6-inhibitor:	0.866
CYP2D6-substrate:	0.184
CYP3A4-inhibitor:	0.639
CYP3A4-substrate:	0.252

ADMET: Excretion

Clearance (CL):	1.297
Half-life (T1/2):	0.048

ADMET: Toxicity

hERG Blockers:	0.039
Human Hepatotoxicity (H-HT):	0.857
Drug-inuced Liver Injury (DILI):	0.935
AMES Toxicity:	0.051
Rat Oral Acute Toxicity:	0.906
Maximum Recommended Daily Dose:	0.643
Skin Sensitization:	0.866
Carcinogencity:	0.418
Eye Corrosion:	0.003
Eye Irritation:	0.137
Respiratory Toxicity:	0.371

Download Data

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

Natural Product: NPC236756

Natural Product ID:	NPC236756
*Common Name:**	3-Methoxyminimiflorin
IUPAC Name:	(7R,8R)-5-hydroxy-8-(2-hydroxyphenyl)-7-methoxy-2,2-dimethyl-10-(3-methylbut-2-enyl)-7,8-dihydropyrano[3,2-g]chromen-6-one
Synonyms:	3-Methoxyminimiflorin
Standard InCHIKey:	ZQNJQIORXQNFHJ-RPBOFIJWSA-N
Standard InCHI:	InChI=1S/C26H28O6/c1-14(2)10-11-17-22-16(12-13-26(3,4)32-22)20(28)19-21(29)25(30-5)24(31-23(17)19)15-8-6-7-9-18(15)27/h6-10,12-13,24-25,27-28H,11H2,1-5H3/t24-,25+/m1/s1
SMILES:	CC(=CCc1c2c(C=CC(C)(C)O2)c(c2C(=O)[C@@H]([C@@H](c3ccccc3O)Oc12)OC)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL521624
PubChem CID:	10433154
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0000337] Flavans [CHEMONTID:0003642] 8-prenylated flavans [CHEMONTID:0003508] 8-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
NPO24957	Bucida buceras	Species	Combretaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12542360]
NPO28183	Cymbopogon flexuosus	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28183	Cymbopogon flexuosus	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28353	Schizanthus pinnatus	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28235	Heimia montana	Species	Lythraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11029	Bessera tenuiflora	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28564	Pterorhachis zenkeri	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28411	Hedysarum setigerum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24957	Bucida buceras	Species	Combretaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28183	Cymbopogon flexuosus	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28736	Wedelia paludosa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28113	Oria flava	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO14464	Oxalis triangularis	Species	Oxalidaceae	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	9

Activity Type	# Activity
Cell Line	7
NON-MOLECULAR	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	IC50	=	6.5	ug.mL-1	PMID[569180]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	7.6	ug.mL-1	PMID[569180]
NPT309	Cell Line	1A9	Homo sapiens	IC50	=	7.8	ug.mL-1	PMID[569180]
NPT180	Cell Line	HCT-8	Homo sapiens	IC50	=	7.2	ug.mL-1	PMID[569180]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	7.0	ug.mL-1	PMID[569180]
NPT306	Cell Line	PC-3	Homo sapiens	IC50	=	8.4	ug.mL-1	PMID[569180]
NPT147	Cell Line	SK-MEL-2	Homo sapiens	IC50	=	7.8	ug.mL-1	PMID[569180]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	7.0	ug.mL-1	PMID[569180]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	8.6	ug.mL-1	PMID[569180]

☑ 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 NPC236756 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	389
0.1-0.2	1551
0.2-0.3	3818
0.3-0.4	9600
0.4-0.5	8848
0.5-0.6	3572
0.6-0.7	5585
0.7-0.8	5133
0.8-0.85	2637
0.85-0.9	1122
0.9-0.95	386
0.95-1	56

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC311579
0.9797	High Similarity	NPC48579
0.9797	High Similarity	NPC304207
0.9797	High Similarity	NPC207809
0.9797	High Similarity	NPC217706
0.9797	High Similarity	NPC259710
0.973	High Similarity	NPC180301
0.973	High Similarity	NPC248793
0.9664	High Similarity	NPC111341
0.9664	High Similarity	NPC476169
0.9664	High Similarity	NPC304745
0.9658	High Similarity	NPC296869
0.9597	High Similarity	NPC223701
0.9597	High Similarity	NPC268193
0.9597	High Similarity	NPC472583
0.9597	High Similarity	NPC7989
0.9595	High Similarity	NPC262038
0.9595	High Similarity	NPC254412
0.9595	High Similarity	NPC319910
0.9595	High Similarity	NPC278476
0.9595	High Similarity	NPC262039
0.9589	High Similarity	NPC296998
0.9589	High Similarity	NPC473077
0.953	High Similarity	NPC216035
0.953	High Similarity	NPC35567
0.953	High Similarity	NPC56232
0.953	High Similarity	NPC150123
0.953	High Similarity	NPC475790
0.953	High Similarity	NPC138288
0.953	High Similarity	NPC244583
0.953	High Similarity	NPC210597
0.953	High Similarity	NPC171651
0.953	High Similarity	NPC243171
0.953	High Similarity	NPC217149
0.953	High Similarity	NPC161881
0.953	High Similarity	NPC10807
0.9527	High Similarity	NPC105136
0.9527	High Similarity	NPC472633
0.9527	High Similarity	NPC61258
0.9524	High Similarity	NPC244407
0.9521	High Similarity	NPC195621
0.9521	High Similarity	NPC54577
0.9521	High Similarity	NPC83357
0.9521	High Similarity	NPC5820
0.9521	High Similarity	NPC124729
0.9521	High Similarity	NPC176229
0.9521	High Similarity	NPC178343
0.9521	High Similarity	NPC301276
0.9521	High Similarity	NPC142405
0.9521	High Similarity	NPC214774
0.9521	High Similarity	NPC88964
0.9521	High Similarity	NPC267375
0.9521	High Similarity	NPC20488
0.9521	High Similarity	NPC312973
0.9521	High Similarity	NPC475052
0.9521	High Similarity	NPC306488
0.9521	High Similarity	NPC67805
0.9521	High Similarity	NPC246948
0.9521	High Similarity	NPC111786
0.9521	High Similarity	NPC470647
0.947	High Similarity	NPC215917
0.947	High Similarity	NPC20530
0.947	High Similarity	NPC10754
0.9467	High Similarity	NPC293286
0.9467	High Similarity	NPC88983
0.9467	High Similarity	NPC469405
0.9467	High Similarity	NPC20907
0.9467	High Similarity	NPC244250
0.9467	High Similarity	NPC100134
0.9467	High Similarity	NPC209760
0.9463	High Similarity	NPC471675
0.9463	High Similarity	NPC289774
0.9463	High Similarity	NPC471677
0.9463	High Similarity	NPC477897
0.9463	High Similarity	NPC474021
0.9463	High Similarity	NPC472636
0.9463	High Similarity	NPC474023
0.9463	High Similarity	NPC263384
0.9463	High Similarity	NPC471676
0.9463	High Similarity	NPC209846
0.9463	High Similarity	NPC472422
0.9463	High Similarity	NPC328740
0.9463	High Similarity	NPC244577
0.9463	High Similarity	NPC472420
0.9459	High Similarity	NPC470461
0.9459	High Similarity	NPC5173
0.9456	High Similarity	NPC166757
0.9456	High Similarity	NPC472918
0.9456	High Similarity	NPC23728
0.9456	High Similarity	NPC283234
0.9456	High Similarity	NPC14001
0.9456	High Similarity	NPC110303
0.9452	High Similarity	NPC216538
0.9452	High Similarity	NPC273538
0.9408	High Similarity	NPC284820
0.9408	High Similarity	NPC210048
0.9408	High Similarity	NPC282390
0.9408	High Similarity	NPC281137
0.9408	High Similarity	NPC473272
0.9404	High Similarity	NPC470681
0.9404	High Similarity	NPC471116
0.9404	High Similarity	NPC477958
0.94	High Similarity	NPC327269
0.94	High Similarity	NPC473996
0.94	High Similarity	NPC31627
0.94	High Similarity	NPC476238
0.9396	High Similarity	NPC471115
0.9396	High Similarity	NPC29777
0.9392	High Similarity	NPC132592
0.9392	High Similarity	NPC161191
0.9392	High Similarity	NPC160821
0.9392	High Similarity	NPC470460
0.9388	High Similarity	NPC472629
0.9388	High Similarity	NPC470458
0.9388	High Similarity	NPC220418
0.9384	High Similarity	NPC24821
0.9384	High Similarity	NPC293053
0.9384	High Similarity	NPC158874
0.9384	High Similarity	NPC316816
0.9384	High Similarity	NPC219915
0.9384	High Similarity	NPC212932
0.9384	High Similarity	NPC214166
0.9384	High Similarity	NPC478086
0.9384	High Similarity	NPC9117
0.9384	High Similarity	NPC190637
0.9355	High Similarity	NPC66087
0.9355	High Similarity	NPC472625
0.9355	High Similarity	NPC179198
0.9355	High Similarity	NPC183672
0.9355	High Similarity	NPC278419
0.9346	High Similarity	NPC264932
0.9346	High Similarity	NPC311574
0.9342	High Similarity	NPC146636
0.9338	High Similarity	NPC203080
0.9338	High Similarity	NPC326592
0.9338	High Similarity	NPC109594
0.9338	High Similarity	NPC112701
0.9333	High Similarity	NPC471229
0.9333	High Similarity	NPC472580
0.9333	High Similarity	NPC295650
0.9329	High Similarity	NPC477941
0.9329	High Similarity	NPC277032
0.9329	High Similarity	NPC473016
0.9329	High Similarity	NPC472628
0.9324	High Similarity	NPC85773
0.9324	High Similarity	NPC97716
0.9324	High Similarity	NPC44721
0.9324	High Similarity	NPC472627
0.9324	High Similarity	NPC40086
0.9324	High Similarity	NPC122828
0.9324	High Similarity	NPC201731
0.9324	High Similarity	NPC237635
0.9324	High Similarity	NPC24673
0.9324	High Similarity	NPC3779
0.9324	High Similarity	NPC476182
0.9324	High Similarity	NPC176869
0.9324	High Similarity	NPC104406
0.9324	High Similarity	NPC211466
0.9324	High Similarity	NPC79469
0.932	High Similarity	NPC326500
0.932	High Similarity	NPC131568
0.932	High Similarity	NPC209040
0.932	High Similarity	NPC224714
0.932	High Similarity	NPC470890
0.932	High Similarity	NPC87486
0.932	High Similarity	NPC131579
0.932	High Similarity	NPC319752
0.932	High Similarity	NPC124780
0.9315	High Similarity	NPC228504
0.9315	High Similarity	NPC10937
0.9315	High Similarity	NPC220998
0.9315	High Similarity	NPC182852
0.9315	High Similarity	NPC107572
0.9315	High Similarity	NPC473042
0.9315	High Similarity	NPC37496
0.9315	High Similarity	NPC78
0.9315	High Similarity	NPC64915
0.9315	High Similarity	NPC227579
0.9315	High Similarity	NPC265040
0.9315	High Similarity	NPC76338
0.9315	High Similarity	NPC166482
0.9315	High Similarity	NPC223500
0.9315	High Similarity	NPC1089
0.9315	High Similarity	NPC166934
0.9315	High Similarity	NPC161506
0.9315	High Similarity	NPC40833
0.9315	High Similarity	NPC200694
0.9315	High Similarity	NPC66515
0.9315	High Similarity	NPC32739
0.9315	High Similarity	NPC324436
0.9315	High Similarity	NPC328164
0.9315	High Similarity	NPC177354
0.9315	High Similarity	NPC306829
0.9315	High Similarity	NPC167624
0.9315	High Similarity	NPC76372
0.9315	High Similarity	NPC125855
0.9315	High Similarity	NPC194432
0.9315	High Similarity	NPC296917
0.9315	High Similarity	NPC148757
0.9315	High Similarity	NPC324134

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 NPC236756 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	337
0.1-0.2	922
0.2-0.3	1627
0.3-0.4	2632
0.4-0.5	1867
0.5-0.6	1117
0.6-0.7	448
0.7-0.8	152
0.8-0.85	30
0.85-0.9	16
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9452	High Similarity	NPD4378	Clinical (unspecified phase)
0.9281	High Similarity	NPD7075	Discontinued
0.9267	High Similarity	NPD4380	Phase 2
0.9211	High Similarity	NPD7096	Clinical (unspecified phase)
0.9119	High Similarity	NPD7804	Clinical (unspecified phase)
0.9085	High Similarity	NPD2393	Clinical (unspecified phase)
0.902	High Similarity	NPD6801	Discontinued
0.8973	High Similarity	NPD1552	Clinical (unspecified phase)
0.8973	High Similarity	NPD1550	Clinical (unspecified phase)
0.8933	High Similarity	NPD7410	Clinical (unspecified phase)
0.8912	High Similarity	NPD1549	Phase 2
0.891	High Similarity	NPD4381	Clinical (unspecified phase)
0.8903	High Similarity	NPD8443	Clinical (unspecified phase)
0.8896	High Similarity	NPD1934	Approved
0.8812	High Similarity	NPD6168	Clinical (unspecified phase)
0.8812	High Similarity	NPD6167	Clinical (unspecified phase)
0.8812	High Similarity	NPD6166	Phase 2
0.8776	High Similarity	NPD2796	Approved
0.8742	High Similarity	NPD6799	Approved
0.871	High Similarity	NPD7411	Suspended
0.8707	High Similarity	NPD1510	Phase 2
0.8662	High Similarity	NPD3817	Phase 2
0.8659	High Similarity	NPD6797	Phase 2
0.8627	High Similarity	NPD1512	Approved
0.8608	High Similarity	NPD3882	Suspended
0.8606	High Similarity	NPD7251	Discontinued
0.8599	High Similarity	NPD2801	Approved
0.8571	High Similarity	NPD5403	Approved
0.8554	High Similarity	NPD7808	Phase 3
0.8526	High Similarity	NPD6599	Discontinued
0.8509	High Similarity	NPD6959	Discontinued
0.8497	Intermediate Similarity	NPD1511	Approved
0.8481	Intermediate Similarity	NPD7819	Suspended
0.8447	Intermediate Similarity	NPD5494	Approved
0.8443	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8442	Intermediate Similarity	NPD5401	Approved
0.8435	Intermediate Similarity	NPD1240	Approved
0.8428	Intermediate Similarity	NPD5402	Approved
0.8424	Intermediate Similarity	NPD7054	Approved
0.8373	Intermediate Similarity	NPD7472	Approved
0.8373	Intermediate Similarity	NPD7074	Phase 3
0.8354	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8322	Intermediate Similarity	NPD1607	Approved
0.8261	Intermediate Similarity	NPD7768	Phase 2
0.8261	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8253	Intermediate Similarity	NPD3818	Discontinued
0.8182	Intermediate Similarity	NPD3750	Approved
0.8166	Intermediate Similarity	NPD6559	Discontinued
0.8117	Intermediate Similarity	NPD2800	Approved
0.8117	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8098	Intermediate Similarity	NPD3749	Approved
0.8095	Intermediate Similarity	NPD5844	Phase 1
0.8061	Intermediate Similarity	NPD1247	Approved
0.8049	Intermediate Similarity	NPD919	Approved
0.8012	Intermediate Similarity	NPD6232	Discontinued
0.8	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7987	Intermediate Similarity	NPD920	Approved
0.7978	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7976	Intermediate Similarity	NPD7473	Discontinued
0.7955	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7935	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7933	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7933	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7922	Intermediate Similarity	NPD1551	Phase 2
0.7922	Intermediate Similarity	NPD2935	Discontinued
0.7907	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7885	Intermediate Similarity	NPD1243	Approved
0.7865	Intermediate Similarity	NPD4360	Phase 2
0.7865	Intermediate Similarity	NPD4363	Phase 3
0.7862	Intermediate Similarity	NPD2532	Approved
0.7862	Intermediate Similarity	NPD2534	Approved
0.7862	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7862	Intermediate Similarity	NPD2533	Approved
0.7857	Intermediate Similarity	NPD3748	Approved
0.7848	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7843	Intermediate Similarity	NPD6651	Approved
0.7834	Intermediate Similarity	NPD4628	Phase 3
0.7824	Intermediate Similarity	NPD3751	Discontinued
0.7815	Intermediate Similarity	NPD2313	Discontinued
0.78	Intermediate Similarity	NPD4908	Phase 1
0.7798	Intermediate Similarity	NPD3787	Discontinued
0.7791	Intermediate Similarity	NPD5953	Discontinued
0.7778	Intermediate Similarity	NPD7286	Phase 2
0.7778	Intermediate Similarity	NPD5124	Phase 1
0.7778	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7742	Intermediate Similarity	NPD7033	Discontinued
0.7742	Intermediate Similarity	NPD2799	Discontinued
0.7722	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD6798	Discontinued
0.7692	Intermediate Similarity	NPD6099	Approved
0.7692	Intermediate Similarity	NPD6100	Approved
0.7688	Intermediate Similarity	NPD7584	Approved
0.7687	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD3926	Phase 2
0.7643	Intermediate Similarity	NPD2344	Approved
0.7602	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7597	Intermediate Similarity	NPD1613	Approved
0.7597	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.759	Intermediate Similarity	NPD1465	Phase 2
0.7578	Intermediate Similarity	NPD7390	Discontinued
0.7576	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7568	Intermediate Similarity	NPD1610	Phase 2
0.7561	Intermediate Similarity	NPD3226	Approved
0.7554	Intermediate Similarity	NPD6777	Approved
0.7554	Intermediate Similarity	NPD6780	Approved
0.7554	Intermediate Similarity	NPD6776	Approved
0.7554	Intermediate Similarity	NPD6779	Approved
0.7554	Intermediate Similarity	NPD6778	Approved
0.7554	Intermediate Similarity	NPD6781	Approved
0.7554	Intermediate Similarity	NPD6782	Approved
0.7548	Intermediate Similarity	NPD6355	Discontinued
0.7534	Intermediate Similarity	NPD1548	Phase 1
0.7532	Intermediate Similarity	NPD2346	Discontinued
0.7532	Intermediate Similarity	NPD6233	Phase 2
0.7527	Intermediate Similarity	NPD7435	Discontinued
0.7516	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD2403	Approved
0.7484	Intermediate Similarity	NPD2424	Discontinued
0.7484	Intermediate Similarity	NPD943	Approved
0.7483	Intermediate Similarity	NPD1203	Approved
0.7468	Intermediate Similarity	NPD3268	Approved
0.7458	Intermediate Similarity	NPD8312	Approved
0.7458	Intermediate Similarity	NPD8313	Approved
0.7455	Intermediate Similarity	NPD7458	Discontinued
0.7453	Intermediate Similarity	NPD3887	Approved
0.7453	Intermediate Similarity	NPD2309	Approved
0.7451	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7451	Intermediate Similarity	NPD6832	Phase 2
0.7434	Intermediate Similarity	NPD2798	Approved
0.7433	Intermediate Similarity	NPD7698	Approved
0.7433	Intermediate Similarity	NPD7697	Approved
0.7433	Intermediate Similarity	NPD7696	Phase 3
0.7432	Intermediate Similarity	NPD4361	Phase 2
0.7432	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.743	Intermediate Similarity	NPD8150	Discontinued
0.743	Intermediate Similarity	NPD8434	Phase 2
0.7423	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD4308	Phase 3
0.7403	Intermediate Similarity	NPD4625	Phase 3
0.7394	Intermediate Similarity	NPD7870	Phase 2
0.7394	Intermediate Similarity	NPD7871	Phase 2
0.7386	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7384	Intermediate Similarity	NPD5711	Approved
0.7384	Intermediate Similarity	NPD5710	Approved
0.7381	Intermediate Similarity	NPD8455	Phase 2
0.7378	Intermediate Similarity	NPD5049	Phase 3
0.7374	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7372	Intermediate Similarity	NPD4060	Phase 1
0.7368	Intermediate Similarity	NPD2797	Approved
0.7366	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7349	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7346	Intermediate Similarity	NPD2354	Approved
0.7346	Intermediate Similarity	NPD6190	Approved
0.7341	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD422	Phase 1
0.7333	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD1652	Phase 2
0.7325	Intermediate Similarity	NPD1933	Approved
0.7321	Intermediate Similarity	NPD6844	Discontinued
0.7303	Intermediate Similarity	NPD3225	Approved
0.7292	Intermediate Similarity	NPD7874	Approved
0.7292	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD3027	Phase 3
0.7288	Intermediate Similarity	NPD3823	Discontinued
0.7285	Intermediate Similarity	NPD9717	Approved
0.7283	Intermediate Similarity	NPD6534	Approved
0.7283	Intermediate Similarity	NPD6535	Approved
0.7277	Intermediate Similarity	NPD7701	Phase 2
0.7277	Intermediate Similarity	NPD7585	Approved
0.7262	Intermediate Similarity	NPD5890	Approved
0.7262	Intermediate Similarity	NPD5889	Approved
0.7253	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7235	Intermediate Similarity	NPD4288	Approved
0.7232	Intermediate Similarity	NPD1729	Discontinued
0.7225	Intermediate Similarity	NPD7583	Approved
0.7222	Intermediate Similarity	NPD2654	Approved
0.7215	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD447	Suspended
0.7215	Intermediate Similarity	NPD230	Phase 1
0.7205	Intermediate Similarity	NPD2353	Approved
0.7205	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.7205	Intermediate Similarity	NPD1471	Phase 3
0.7202	Intermediate Similarity	NPD6585	Discontinued
0.7197	Intermediate Similarity	NPD4062	Phase 3
0.7188	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7184	Intermediate Similarity	NPD7229	Phase 3
0.7166	Intermediate Similarity	NPD7699	Phase 2
0.7166	Intermediate Similarity	NPD7700	Phase 2
0.7165	Intermediate Similarity	NPD7783	Phase 2
0.7165	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7165	Intermediate Similarity	NPD7801	Approved
0.7161	Intermediate Similarity	NPD2861	Phase 2
0.7158	Intermediate Similarity	NPD4287	Approved
0.7152	Intermediate Similarity	NPD4307	Phase 2
0.7152	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD7213	Phase 3
0.7152	Intermediate Similarity	NPD7212	Phase 2
0.715	Intermediate Similarity	NPD8151	Discontinued
0.7143	Intermediate Similarity	NPD3266	Approved

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data