NPASS Compound

Structure

NPC108706 OpenBabel07101718332D 31 33 0 0 1 0 0 0 0 0999 V2000 4.3301 -4.5000 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 3.4641 -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 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 2.5981 -4.5000 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 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 2.5981 -1.5000 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 1.7321 -1.0000 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 -0.8660 0.5000 0.0000 C 0 0 2 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 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 2 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5981 -5.5000 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 5.1962 -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 -2.5981 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -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 9 1 0 0 0 0 2 10 1 0 0 0 0 3 4 1 0 0 0 0 3 9 2 0 0 0 0 4 11 1 0 0 0 0 5 10 2 0 0 0 0 5 12 1 0 0 0 0 6 13 2 0 0 0 0 6 14 1 0 0 0 0 7 9 1 0 0 0 0 7 22 1 0 0 0 0 8 23 1 0 0 0 0 10 29 1 0 0 0 0 11 13 1 0 0 0 0 11 17 2 0 0 0 0 12 16 1 0 0 0 0 12 24 2 0 0 0 0 13 30 1 0 0 0 0 14 16 2 0 0 0 0 14 29 1 0 0 0 0 15 8 1 1 0 0 0 15 18 1 0 0 0 0 15 31 1 0 0 0 0 16 17 1 0 0 0 0 17 25 1 0 0 0 0 18 19 1 0 0 0 0 18 26 1 6 0 0 0 19 20 1 0 0 0 0 19 27 1 1 0 0 0 20 21 1 0 0 0 0 20 28 1 6 0 0 0 21 30 1 1 0 0 0 21 31 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	438.15
Volume:	418.186
LogP:	-0.262
LogD:	-0.302
LogS:	-2.304
# Rotatable Bonds:	6
TPSA:	170.05
# H-Bond Aceptor:	10
# H-Bond Donor:	6
# Rings:	3
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.322
Synthetic Accessibility Score:	4.259
Fsp3:	0.476
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.945
MDCK Permeability:	2.1981108147883788e-05
Pgp-inhibitor:	0.002
Pgp-substrate:	0.985
Human Intestinal Absorption (HIA):	0.782
20% Bioavailability (F20%):	0.054
30% Bioavailability (F30%):	0.996

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.11
Plasma Protein Binding (PPB):	87.18877410888672%
Volume Distribution (VD):	0.764
Pgp-substrate:	14.875618934631348%

ADMET: Metabolism

CYP1A2-inhibitor:	0.047
CYP1A2-substrate:	0.093
CYP2C19-inhibitor:	0.009
CYP2C19-substrate:	0.338
CYP2C9-inhibitor:	0.002
CYP2C9-substrate:	0.152
CYP2D6-inhibitor:	0.009
CYP2D6-substrate:	0.212
CYP3A4-inhibitor:	0.006
CYP3A4-substrate:	0.039

ADMET: Excretion

Clearance (CL):	1.785
Half-life (T1/2):	0.915

ADMET: Toxicity

hERG Blockers:	0.125
Human Hepatotoxicity (H-HT):	0.067
Drug-inuced Liver Injury (DILI):	0.509
AMES Toxicity:	0.401
Rat Oral Acute Toxicity:	0.024
Maximum Recommended Daily Dose:	0.01
Skin Sensitization:	0.408
Carcinogencity:	0.04
Eye Corrosion:	0.003
Eye Irritation:	0.021
Respiratory Toxicity:	0.031

Download Data

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

Natural Product: NPC108706

Natural Product ID:	NPC108706
*Common Name:**	2-Methyl-5-Hydroxy-6-(2-Butenyl-3-Hydroxymethyl)-7-(Beta-D-Glucopyranosyloxy)-4H-1-Benzopyran-4-One
IUPAC Name:	5-hydroxy-6-[(Z)-4-hydroxy-3-methylbut-2-enyl]-2-methyl-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one
Synonyms:
Standard InCHIKey:	VAWXDOOFPWDVPC-XQGMFAHKSA-N
Standard InCHI:	InChI=1S/C21H26O10/c1-9(7-22)3-4-11-13(6-14-16(17(11)25)12(24)5-10(2)29-14)30-21-20(28)19(27)18(26)15(8-23)31-21/h3,5-6,15,18-23,25-28H,4,7-8H2,1-2H3/b9-3-/t15-,18-,19+,20-,21-/m1/s1
SMILES:	OC/C(=CCc1c(O[C@@H]2O[C@H](CO)[C@H]([C@@H]([C@H]2O)O)O)cc2c(c1O)c(=O)cc(o2)C)/C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2087919
PubChem CID:	70686987
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0000011] Carbohydrates and carbohydrate conjugates [CHEMONTID:0002105] Glycosyl compounds [CHEMONTID:0004165] Phenolic glycosides

*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
NPO15544	Cnidium monnieri	Species	Apiaceae	Eukaryota	n.a.	fruit	n.a.	PMID[10785419]
NPO15544	Cnidium monnieri	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21625478]
NPO15544	Cnidium monnieri	Species	Apiaceae	Eukaryota	fruits	n.a.	n.a.	PMID[22932311]
NPO15544	Cnidium monnieri	Species	Apiaceae	Eukaryota	n.a.	fruit	n.a.	PMID[23721280]
NPO15544	Cnidium monnieri	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15544	Cnidium monnieri	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15544	Cnidium monnieri	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO15544	Cnidium monnieri	Species	Apiaceae	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
Others	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT520	Cell Line	3T3-L1	Mus musculus	Inhibition	=	87.0	%	PMID[555669]

☑ 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 NPC108706 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	382
0.1-0.2	1558
0.2-0.3	3648
0.3-0.4	9135
0.4-0.5	9666
0.5-0.6	4303
0.6-0.7	5613
0.7-0.8	4960
0.8-0.85	2388
0.85-0.9	882
0.9-0.95	150
0.95-1	12

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC211158
1.0	High Similarity	NPC87304
1.0	High Similarity	NPC268950
1.0	High Similarity	NPC78021
0.9932	High Similarity	NPC470605
0.9932	High Similarity	NPC470603
0.9932	High Similarity	NPC470604
0.9799	High Similarity	NPC470606
0.9795	High Similarity	NPC38775
0.9795	High Similarity	NPC191154
0.9733	High Similarity	NPC470607
0.9728	High Similarity	NPC134819
0.9667	High Similarity	NPC23817
0.966	High Similarity	NPC214454
0.966	High Similarity	NPC106025
0.966	High Similarity	NPC477240
0.9658	High Similarity	NPC199335
0.96	High Similarity	NPC17521
0.9597	High Similarity	NPC106625
0.9595	High Similarity	NPC190217
0.9589	High Similarity	NPC23084
0.9542	High Similarity	NPC44947
0.9542	High Similarity	NPC131745
0.9533	High Similarity	NPC95090
0.9533	High Similarity	NPC27408
0.9533	High Similarity	NPC99233
0.953	High Similarity	NPC259182
0.953	High Similarity	NPC121001
0.9524	High Similarity	NPC10097
0.9481	High Similarity	NPC124155
0.9481	High Similarity	NPC183672
0.9481	High Similarity	NPC278419
0.9481	High Similarity	NPC179198
0.9481	High Similarity	NPC257566
0.9481	High Similarity	NPC66087
0.9477	High Similarity	NPC47923
0.9474	High Similarity	NPC73511
0.947	High Similarity	NPC127406
0.947	High Similarity	NPC206378
0.9467	High Similarity	NPC210003
0.9467	High Similarity	NPC29763
0.9467	High Similarity	NPC83283
0.9467	High Similarity	NPC39360
0.9467	High Similarity	NPC143851
0.9459	High Similarity	NPC139966
0.9459	High Similarity	NPC307052
0.9416	High Similarity	NPC190450
0.9416	High Similarity	NPC259834
0.9412	High Similarity	NPC472320
0.9408	High Similarity	NPC161749
0.9408	High Similarity	NPC197896
0.9408	High Similarity	NPC44931
0.9408	High Similarity	NPC313163
0.9408	High Similarity	NPC108831
0.9408	High Similarity	NPC129827
0.9408	High Similarity	NPC258035
0.9408	High Similarity	NPC156457
0.9408	High Similarity	NPC60966
0.9408	High Similarity	NPC6985
0.9408	High Similarity	NPC43638
0.9408	High Similarity	NPC182634
0.9408	High Similarity	NPC65003
0.9408	High Similarity	NPC473512
0.9404	High Similarity	NPC26195
0.9404	High Similarity	NPC39351
0.9404	High Similarity	NPC72649
0.9404	High Similarity	NPC97052
0.9404	High Similarity	NPC169248
0.94	High Similarity	NPC259767
0.94	High Similarity	NPC88484
0.9396	High Similarity	NPC213723
0.9351	High Similarity	NPC303913
0.9346	High Similarity	NPC138811
0.9346	High Similarity	NPC41121
0.9346	High Similarity	NPC320283
0.9346	High Similarity	NPC22062
0.9346	High Similarity	NPC473634
0.9346	High Similarity	NPC111929
0.9346	High Similarity	NPC472459
0.9342	High Similarity	NPC170475
0.9342	High Similarity	NPC45165
0.9342	High Similarity	NPC203500
0.9342	High Similarity	NPC307938
0.9342	High Similarity	NPC261866
0.9342	High Similarity	NPC323593
0.9333	High Similarity	NPC250488
0.9324	High Similarity	NPC85773
0.9324	High Similarity	NPC218685
0.9286	High Similarity	NPC97285
0.9286	High Similarity	NPC271270
0.9286	High Similarity	NPC142860
0.9286	High Similarity	NPC187379
0.9286	High Similarity	NPC153342
0.9286	High Similarity	NPC246469
0.9286	High Similarity	NPC473623
0.9281	High Similarity	NPC77672
0.9281	High Similarity	NPC133671
0.9281	High Similarity	NPC54802
0.9281	High Similarity	NPC197304
0.9281	High Similarity	NPC135391
0.9281	High Similarity	NPC122809
0.9281	High Similarity	NPC78263
0.9272	High Similarity	NPC10807
0.9272	High Similarity	NPC150123
0.9272	High Similarity	NPC244583
0.9272	High Similarity	NPC256141
0.9272	High Similarity	NPC161881
0.9272	High Similarity	NPC56232
0.9257	High Similarity	NPC474302
0.9241	High Similarity	NPC259905
0.9241	High Similarity	NPC5319
0.9236	High Similarity	NPC178851
0.9226	High Similarity	NPC259957
0.9226	High Similarity	NPC476215
0.9226	High Similarity	NPC181465
0.9226	High Similarity	NPC276377
0.9226	High Similarity	NPC173582
0.9226	High Similarity	NPC253788
0.9226	High Similarity	NPC224530
0.9226	High Similarity	NPC159579
0.9226	High Similarity	NPC249281
0.9226	High Similarity	NPC48093
0.9226	High Similarity	NPC116458
0.9226	High Similarity	NPC246943
0.9226	High Similarity	NPC139320
0.9226	High Similarity	NPC163242
0.9226	High Similarity	NPC265885
0.9226	High Similarity	NPC85707
0.9226	High Similarity	NPC129217
0.9226	High Similarity	NPC215710
0.9226	High Similarity	NPC101636
0.9226	High Similarity	NPC473438
0.9226	High Similarity	NPC216496
0.9221	High Similarity	NPC308265
0.9221	High Similarity	NPC43761
0.9216	High Similarity	NPC295613
0.9216	High Similarity	NPC473657
0.9216	High Similarity	NPC149368
0.9216	High Similarity	NPC265480
0.9205	High Similarity	NPC477897
0.9205	High Similarity	NPC23253
0.9205	High Similarity	NPC328740
0.9205	High Similarity	NPC289774
0.9205	High Similarity	NPC209846
0.9195	High Similarity	NPC470670
0.9195	High Similarity	NPC91902
0.9195	High Similarity	NPC473133
0.9195	High Similarity	NPC47388
0.9182	High Similarity	NPC76047
0.9182	High Similarity	NPC150767
0.9182	High Similarity	NPC78734
0.9177	High Similarity	NPC477502
0.9172	High Similarity	NPC294722
0.9167	High Similarity	NPC298171
0.9167	High Similarity	NPC300537
0.9167	High Similarity	NPC475382
0.9167	High Similarity	NPC150164
0.9167	High Similarity	NPC473043
0.9167	High Similarity	NPC127782
0.9167	High Similarity	NPC93215
0.9167	High Similarity	NPC27942
0.9167	High Similarity	NPC240306
0.9161	High Similarity	NPC304741
0.9161	High Similarity	NPC200708
0.9161	High Similarity	NPC136761
0.9161	High Similarity	NPC470405
0.9161	High Similarity	NPC271479
0.9161	High Similarity	NPC471079
0.9156	High Similarity	NPC288084
0.915	High Similarity	NPC304745
0.915	High Similarity	NPC87404
0.915	High Similarity	NPC111341
0.915	High Similarity	NPC92395
0.9139	High Similarity	NPC180351
0.9125	High Similarity	NPC256760
0.911	High Similarity	NPC139554
0.911	High Similarity	NPC471697
0.9108	High Similarity	NPC309025
0.9108	High Similarity	NPC121703
0.9108	High Similarity	NPC222936
0.9108	High Similarity	NPC473644
0.9108	High Similarity	NPC243930
0.9108	High Similarity	NPC19709
0.9108	High Similarity	NPC94777
0.9108	High Similarity	NPC311850
0.9108	High Similarity	NPC88023
0.9108	High Similarity	NPC284960
0.9103	High Similarity	NPC195685
0.9103	High Similarity	NPC270675
0.9103	High Similarity	NPC210961
0.9103	High Similarity	NPC135846
0.9103	High Similarity	NPC64305
0.9103	High Similarity	NPC472994
0.9103	High Similarity	NPC470125
0.9103	High Similarity	NPC477628
0.9103	High Similarity	NPC477629
0.9103	High Similarity	NPC282169
0.9103	High Similarity	NPC170052
0.9103	High Similarity	NPC297987
0.9097	High Similarity	NPC104677

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 NPC108706 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	336
0.1-0.2	889
0.2-0.3	1785
0.3-0.4	2690
0.4-0.5	1956
0.5-0.6	1030
0.6-0.7	287
0.7-0.8	137
0.8-0.85	28
0.85-0.9	11
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9408	High Similarity	NPD4381	Clinical (unspecified phase)
0.9241	High Similarity	NPD7804	Clinical (unspecified phase)
0.9013	High Similarity	NPD4380	Phase 2
0.8882	High Similarity	NPD7054	Approved
0.8827	High Similarity	NPD7472	Approved
0.8827	High Similarity	NPD7074	Phase 3
0.882	High Similarity	NPD3818	Discontinued
0.879	High Similarity	NPD7075	Discontinued
0.8774	High Similarity	NPD6801	Discontinued
0.8773	High Similarity	NPD6797	Phase 2
0.872	High Similarity	NPD7251	Discontinued
0.872	High Similarity	NPD6559	Discontinued
0.8718	High Similarity	NPD2393	Clinical (unspecified phase)
0.8684	High Similarity	NPD4378	Clinical (unspecified phase)
0.8667	High Similarity	NPD7808	Phase 3
0.8599	High Similarity	NPD7096	Clinical (unspecified phase)
0.8591	High Similarity	NPD1550	Clinical (unspecified phase)
0.8591	High Similarity	NPD1552	Clinical (unspecified phase)
0.8554	High Similarity	NPD4338	Clinical (unspecified phase)
0.8535	High Similarity	NPD1934	Approved
0.8533	High Similarity	NPD1549	Phase 2
0.8471	Intermediate Similarity	NPD7411	Suspended
0.8442	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8428	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8354	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8354	Intermediate Similarity	NPD6166	Phase 2
0.8354	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8278	Intermediate Similarity	NPD2796	Approved
0.8258	Intermediate Similarity	NPD6799	Approved
0.825	Intermediate Similarity	NPD2801	Approved
0.825	Intermediate Similarity	NPD7819	Suspended
0.8217	Intermediate Similarity	NPD5403	Approved
0.8212	Intermediate Similarity	NPD1510	Phase 2
0.8199	Intermediate Similarity	NPD3817	Phase 2
0.8171	Intermediate Similarity	NPD6959	Discontinued
0.8148	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8141	Intermediate Similarity	NPD1511	Approved
0.8089	Intermediate Similarity	NPD5401	Approved
0.8067	Intermediate Similarity	NPD1240	Approved
0.8065	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.8063	Intermediate Similarity	NPD6599	Discontinued
0.8038	Intermediate Similarity	NPD1512	Approved
0.8024	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD2800	Approved
0.7978	Intermediate Similarity	NPD7584	Approved
0.7975	Intermediate Similarity	NPD5402	Approved
0.7961	Intermediate Similarity	NPD1607	Approved
0.7961	Intermediate Similarity	NPD6651	Approved
0.7955	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7935	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7927	Intermediate Similarity	NPD3882	Suspended
0.7892	Intermediate Similarity	NPD5494	Approved
0.7885	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7862	Intermediate Similarity	NPD2532	Approved
0.7862	Intermediate Similarity	NPD2534	Approved
0.7862	Intermediate Similarity	NPD2533	Approved
0.7861	Intermediate Similarity	NPD8312	Approved
0.7861	Intermediate Similarity	NPD8313	Approved
0.7826	Intermediate Similarity	NPD1653	Approved
0.7818	Intermediate Similarity	NPD7768	Phase 2
0.7805	Intermediate Similarity	NPD8455	Phase 2
0.7798	Intermediate Similarity	NPD6232	Discontinued
0.7791	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD5844	Phase 1
0.7771	Intermediate Similarity	NPD1243	Approved
0.7765	Intermediate Similarity	NPD7473	Discontinued
0.7764	Intermediate Similarity	NPD920	Approved
0.7722	Intermediate Similarity	NPD3750	Approved
0.7722	Intermediate Similarity	NPD4628	Phase 3
0.7697	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7687	Intermediate Similarity	NPD1091	Approved
0.768	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7662	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7662	Intermediate Similarity	NPD5124	Phase 1
0.765	Intermediate Similarity	NPD6776	Approved
0.765	Intermediate Similarity	NPD6782	Approved
0.765	Intermediate Similarity	NPD6781	Approved
0.765	Intermediate Similarity	NPD6778	Approved
0.765	Intermediate Similarity	NPD6779	Approved
0.765	Intermediate Similarity	NPD6780	Approved
0.765	Intermediate Similarity	NPD6777	Approved
0.764	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7625	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7606	Intermediate Similarity	NPD8151	Discontinued
0.76	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD5953	Discontinued
0.758	Intermediate Similarity	NPD2935	Discontinued
0.758	Intermediate Similarity	NPD1551	Phase 2
0.7572	Intermediate Similarity	NPD7286	Phase 2
0.756	Intermediate Similarity	NPD3749	Approved
0.7553	Intermediate Similarity	NPD7585	Approved
0.7547	Intermediate Similarity	NPD1652	Phase 2
0.7546	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.753	Intermediate Similarity	NPD37	Approved
0.7529	Intermediate Similarity	NPD7199	Phase 2
0.7527	Intermediate Similarity	NPD7435	Discontinued
0.7516	Intermediate Similarity	NPD7033	Discontinued
0.7515	Intermediate Similarity	NPD6234	Discontinued
0.7515	Intermediate Similarity	NPD919	Approved
0.7514	Intermediate Similarity	NPD7228	Approved
0.7514	Intermediate Similarity	NPD3751	Discontinued
0.75	Intermediate Similarity	NPD4966	Approved
0.75	Intermediate Similarity	NPD7583	Approved
0.75	Intermediate Similarity	NPD4967	Phase 2
0.75	Intermediate Similarity	NPD4965	Approved
0.7485	Intermediate Similarity	NPD1465	Phase 2
0.7485	Intermediate Similarity	NPD3787	Discontinued
0.7473	Intermediate Similarity	NPD4363	Phase 3
0.7473	Intermediate Similarity	NPD4360	Phase 2
0.7468	Intermediate Similarity	NPD2313	Discontinued
0.7455	Intermediate Similarity	NPD7458	Discontinued
0.7436	Intermediate Similarity	NPD1933	Approved
0.7435	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7435	Intermediate Similarity	NPD7783	Phase 2
0.7433	Intermediate Similarity	NPD7698	Approved
0.7433	Intermediate Similarity	NPD7697	Approved
0.7433	Intermediate Similarity	NPD7696	Phase 3
0.7427	Intermediate Similarity	NPD1247	Approved
0.7405	Intermediate Similarity	NPD2799	Discontinued
0.7405	Intermediate Similarity	NPD3748	Approved
0.7394	Intermediate Similarity	NPD7871	Phase 2
0.7394	Intermediate Similarity	NPD7870	Phase 2
0.7391	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7384	Intermediate Similarity	NPD5711	Approved
0.7384	Intermediate Similarity	NPD5710	Approved
0.738	Intermediate Similarity	NPD6823	Phase 2
0.7377	Intermediate Similarity	NPD6534	Approved
0.7377	Intermediate Similarity	NPD6535	Approved
0.7375	Intermediate Similarity	NPD2424	Discontinued
0.7372	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7372	Intermediate Similarity	NPD1613	Approved
0.7368	Intermediate Similarity	NPD7701	Phase 2
0.7365	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD6100	Approved
0.7358	Intermediate Similarity	NPD6099	Approved
0.7355	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7349	Intermediate Similarity	NPD3226	Approved
0.7348	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7345	Intermediate Similarity	NPD7685	Pre-registration
0.7341	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD6832	Phase 2
0.7333	Intermediate Similarity	NPD422	Phase 1
0.7333	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7325	Intermediate Similarity	NPD230	Phase 1
0.732	Intermediate Similarity	NPD2798	Approved
0.7292	Intermediate Similarity	NPD7874	Approved
0.7292	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7285	Intermediate Similarity	NPD9717	Approved
0.7258	Intermediate Similarity	NPD7699	Phase 2
0.7258	Intermediate Similarity	NPD7700	Phase 2
0.7256	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7256	Intermediate Similarity	NPD7390	Discontinued
0.7255	Intermediate Similarity	NPD1203	Approved
0.7254	Intermediate Similarity	NPD7801	Approved
0.7244	Intermediate Similarity	NPD6798	Discontinued
0.7244	Intermediate Similarity	NPD3268	Approved
0.7226	Intermediate Similarity	NPD4908	Phase 1
0.7222	Intermediate Similarity	NPD2654	Approved
0.7205	Intermediate Similarity	NPD2344	Approved
0.7205	Intermediate Similarity	NPD2346	Discontinued
0.7188	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7182	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD1548	Phase 1
0.7161	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD943	Approved
0.7151	Intermediate Similarity	NPD4361	Phase 2
0.7151	Intermediate Similarity	NPD7240	Approved
0.7151	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD8434	Phase 2
0.7143	Intermediate Similarity	NPD2797	Approved
0.7143	Intermediate Similarity	NPD3926	Phase 2
0.7135	Intermediate Similarity	NPD6213	Phase 3
0.7135	Intermediate Similarity	NPD6212	Phase 3
0.7135	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD7097	Phase 1
0.712	Intermediate Similarity	NPD8319	Approved
0.712	Intermediate Similarity	NPD8320	Phase 1
0.7117	Intermediate Similarity	NPD6674	Discontinued
0.7115	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD447	Suspended
0.7105	Intermediate Similarity	NPD1610	Phase 2
0.7102	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD7266	Discontinued
0.709	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD6233	Phase 2
0.707	Intermediate Similarity	NPD3027	Phase 3
0.7067	Intermediate Similarity	NPD9545	Approved
0.7056	Intermediate Similarity	NPD7930	Approved
0.7049	Intermediate Similarity	NPD8150	Discontinued
0.7041	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD1729	Discontinued
0.703	Intermediate Similarity	NPD2309	Approved
0.7025	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD1296	Phase 2
0.7006	Intermediate Similarity	NPD4661	Approved
0.7006	Intermediate Similarity	NPD4662	Approved
0.7006	Intermediate Similarity	NPD2403	Approved
0.7	Intermediate Similarity	NPD6355	Discontinued
0.7	Intermediate Similarity	NPD3823	Discontinued

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