NPASS Compound

Structure

NPC470605 OpenBabel07101719142D 32 34 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 -2.5981 -4.5000 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 -2.5981 -2.5000 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 -3.4641 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -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 -3.4641 -3.0000 0.0000 C 0 0 3 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 -4.3301 3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -2.5000 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 8 2 0 0 0 0 2 8 1 0 0 0 0 3 9 2 0 0 0 0 3 12 1 0 0 0 0 4 10 1 0 0 0 0 4 11 1 0 0 0 0 5 13 2 0 0 0 0 5 14 1 0 0 0 0 6 9 1 0 0 0 0 6 22 1 0 0 0 0 7 23 1 0 0 0 0 8 11 1 0 0 0 0 9 30 1 0 0 0 0 10 13 1 0 0 0 0 10 17 2 0 0 0 0 11 24 1 0 0 0 0 12 16 1 0 0 0 0 12 25 2 0 0 0 0 13 31 1 0 0 0 0 14 16 2 0 0 0 0 14 30 1 0 0 0 0 15 7 1 6 0 0 0 15 18 1 0 0 0 0 15 32 1 0 0 0 0 16 17 1 0 0 0 0 17 26 1 0 0 0 0 18 19 1 0 0 0 0 18 27 1 1 0 0 0 19 20 1 0 0 0 0 19 28 1 6 0 0 0 20 21 1 0 0 0 0 20 29 1 1 0 0 0 21 31 1 6 0 0 0 21 32 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	454.15
Volume:	426.977
LogP:	-0.407
LogD:	-0.427
LogS:	-1.832
# Rotatable Bonds:	7
TPSA:	190.28
# H-Bond Aceptor:	11
# H-Bond Donor:	7
# Rings:	3
# Heavy Atoms:	11

MedChem Properties

QED Drug-Likeness Score:	0.245
Synthetic Accessibility Score:	4.467
Fsp3:	0.476
Lipinski Rule-of-5:	Rejected
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:	-6.199
MDCK Permeability:	2.2414827981265262e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.979
Human Intestinal Absorption (HIA):	0.85
20% Bioavailability (F20%):	0.084
30% Bioavailability (F30%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.144
Plasma Protein Binding (PPB):	59.3356819152832%
Volume Distribution (VD):	0.869
Pgp-substrate:	31.11029815673828%

ADMET: Metabolism

CYP1A2-inhibitor:	0.031
CYP1A2-substrate:	0.048
CYP2C19-inhibitor:	0.006
CYP2C19-substrate:	0.172
CYP2C9-inhibitor:	0.001
CYP2C9-substrate:	0.135
CYP2D6-inhibitor:	0.003
CYP2D6-substrate:	0.16
CYP3A4-inhibitor:	0.003
CYP3A4-substrate:	0.019

ADMET: Excretion

Clearance (CL):	1.614
Half-life (T1/2):	0.815

ADMET: Toxicity

hERG Blockers:	0.064
Human Hepatotoxicity (H-HT):	0.329
Drug-inuced Liver Injury (DILI):	0.459
AMES Toxicity:	0.332
Rat Oral Acute Toxicity:	0.02
Maximum Recommended Daily Dose:	0.012
Skin Sensitization:	0.392
Carcinogencity:	0.023
Eye Corrosion:	0.003
Eye Irritation:	0.01
Respiratory Toxicity:	0.03

Download Data

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

Natural Product: NPC470605

Natural Product ID:	NPC470605
*Common Name:**	Monnieriside E
IUPAC Name:	5-hydroxy-2-(hydroxymethyl)-6-(2-hydroxy-3-methylbut-3-enyl)-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one
Synonyms:	Monnieriside E
Standard InCHIKey:	XSPWOFSAKVZGQN-KAICPEJPSA-N
Standard InCHI:	InChI=1S/C21H26O11/c1-8(2)11(24)4-10-13(31-21-20(29)19(28)18(27)15(7-23)32-21)5-14-16(17(10)26)12(25)3-9(6-22)30-14/h3,5,11,15,18-24,26-29H,1,4,6-7H2,2H3/t11?,15-,18-,19+,20-,21-/m1/s1
SMILES:	OC[C@H]1O[C@@H](Oc2cc3oc(CO)cc(=O)c3c(c2CC(C(=C)C)O)O)[C@@H]([C@H]([C@@H]1O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2087925
PubChem CID:	70689052
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	=	82.2	%	PMID[529948]

☑ 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 NPC470605 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	1637
0.2-0.3	3677
0.3-0.4	8883
0.4-0.5	9617
0.5-0.6	4524
0.6-0.7	5538
0.7-0.8	4832
0.8-0.85	2515
0.85-0.9	913
0.9-0.95	147
0.95-1	15

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC470603
1.0	High Similarity	NPC470604
0.9932	High Similarity	NPC268950
0.9932	High Similarity	NPC78021
0.9932	High Similarity	NPC108706
0.9932	High Similarity	NPC87304
0.9932	High Similarity	NPC211158
0.9866	High Similarity	NPC470606
0.98	High Similarity	NPC470607
0.9728	High Similarity	NPC38775
0.9728	High Similarity	NPC191154
0.9667	High Similarity	NPC17521
0.9662	High Similarity	NPC134819
0.9662	High Similarity	NPC190217
0.9608	High Similarity	NPC44947
0.9608	High Similarity	NPC131745
0.9603	High Similarity	NPC23817
0.9595	High Similarity	NPC106025
0.9595	High Similarity	NPC477240
0.9595	High Similarity	NPC214454
0.9592	High Similarity	NPC10097
0.9592	High Similarity	NPC199335
0.9545	High Similarity	NPC183672
0.9545	High Similarity	NPC179198
0.9545	High Similarity	NPC124155
0.9545	High Similarity	NPC257566
0.9545	High Similarity	NPC66087
0.9545	High Similarity	NPC278419
0.9542	High Similarity	NPC47923
0.9539	High Similarity	NPC73511
0.9533	High Similarity	NPC106625
0.9527	High Similarity	NPC307052
0.9527	High Similarity	NPC139966
0.9524	High Similarity	NPC23084
0.9481	High Similarity	NPC259834
0.9477	High Similarity	NPC472320
0.9474	High Similarity	NPC156457
0.9474	High Similarity	NPC197896
0.9474	High Similarity	NPC313163
0.9474	High Similarity	NPC258035
0.9474	High Similarity	NPC161749
0.947	High Similarity	NPC95090
0.947	High Similarity	NPC99233
0.947	High Similarity	NPC27408
0.9467	High Similarity	NPC121001
0.9467	High Similarity	NPC259182
0.9416	High Similarity	NPC303913
0.9408	High Similarity	NPC45165
0.9408	High Similarity	NPC127406
0.9408	High Similarity	NPC206378
0.9408	High Similarity	NPC261866
0.9404	High Similarity	NPC143851
0.9404	High Similarity	NPC29763
0.9404	High Similarity	NPC210003
0.9404	High Similarity	NPC83283
0.9404	High Similarity	NPC39360
0.9392	High Similarity	NPC85773
0.9355	High Similarity	NPC190450
0.9346	High Similarity	NPC473512
0.9346	High Similarity	NPC108831
0.9346	High Similarity	NPC129827
0.9346	High Similarity	NPC6985
0.9346	High Similarity	NPC44931
0.9346	High Similarity	NPC43638
0.9346	High Similarity	NPC182634
0.9346	High Similarity	NPC65003
0.9346	High Similarity	NPC60966
0.9342	High Similarity	NPC39351
0.9342	High Similarity	NPC72649
0.9342	High Similarity	NPC97052
0.9342	High Similarity	NPC169248
0.9342	High Similarity	NPC26195
0.9338	High Similarity	NPC56232
0.9338	High Similarity	NPC150123
0.9338	High Similarity	NPC10807
0.9338	High Similarity	NPC88484
0.9338	High Similarity	NPC259767
0.9338	High Similarity	NPC161881
0.9338	High Similarity	NPC244583
0.9338	High Similarity	NPC256141
0.9333	High Similarity	NPC213723
0.9324	High Similarity	NPC474302
0.9304	High Similarity	NPC5319
0.9304	High Similarity	NPC259905
0.9299	High Similarity	NPC178851
0.9286	High Similarity	NPC43761
0.9286	High Similarity	NPC472459
0.9286	High Similarity	NPC308265
0.9286	High Similarity	NPC41121
0.9286	High Similarity	NPC320283
0.9286	High Similarity	NPC22062
0.9286	High Similarity	NPC111929
0.9286	High Similarity	NPC138811
0.9286	High Similarity	NPC473634
0.9281	High Similarity	NPC323593
0.9281	High Similarity	NPC307938
0.9281	High Similarity	NPC203500
0.9281	High Similarity	NPC170475
0.9272	High Similarity	NPC250488
0.9272	High Similarity	NPC209846
0.9272	High Similarity	NPC477897
0.9272	High Similarity	NPC328740
0.9272	High Similarity	NPC289774
0.9262	High Similarity	NPC218685
0.9262	High Similarity	NPC91902
0.9262	High Similarity	NPC47388
0.9262	High Similarity	NPC473133
0.9262	High Similarity	NPC470670
0.9245	High Similarity	NPC76047
0.9245	High Similarity	NPC78734
0.9245	High Similarity	NPC150767
0.9241	High Similarity	NPC477502
0.9236	High Similarity	NPC294722
0.9231	High Similarity	NPC93215
0.9231	High Similarity	NPC127782
0.9231	High Similarity	NPC300537
0.9231	High Similarity	NPC473043
0.9226	High Similarity	NPC142860
0.9226	High Similarity	NPC97285
0.9226	High Similarity	NPC187379
0.9226	High Similarity	NPC246469
0.9226	High Similarity	NPC271270
0.9226	High Similarity	NPC271479
0.9226	High Similarity	NPC153342
0.9226	High Similarity	NPC473623
0.9221	High Similarity	NPC77672
0.9221	High Similarity	NPC54802
0.9221	High Similarity	NPC78263
0.9221	High Similarity	NPC133671
0.9221	High Similarity	NPC122809
0.9221	High Similarity	NPC197304
0.9221	High Similarity	NPC135391
0.9216	High Similarity	NPC304745
0.9216	High Similarity	NPC92395
0.9216	High Similarity	NPC111341
0.9216	High Similarity	NPC87404
0.9205	High Similarity	NPC180351
0.9187	High Similarity	NPC256760
0.9172	High Similarity	NPC19709
0.9172	High Similarity	NPC284960
0.9172	High Similarity	NPC88023
0.9172	High Similarity	NPC243930
0.9172	High Similarity	NPC309025
0.9172	High Similarity	NPC222936
0.9172	High Similarity	NPC94777
0.9167	High Similarity	NPC215710
0.9167	High Similarity	NPC224530
0.9167	High Similarity	NPC85707
0.9167	High Similarity	NPC48093
0.9167	High Similarity	NPC249281
0.9167	High Similarity	NPC181465
0.9167	High Similarity	NPC163242
0.9167	High Similarity	NPC129217
0.9167	High Similarity	NPC473438
0.9167	High Similarity	NPC101636
0.9167	High Similarity	NPC246943
0.9167	High Similarity	NPC265885
0.9167	High Similarity	NPC276377
0.9167	High Similarity	NPC159579
0.9167	High Similarity	NPC259957
0.9167	High Similarity	NPC253788
0.9167	High Similarity	NPC139320
0.9167	High Similarity	NPC116458
0.9167	High Similarity	NPC216496
0.9167	High Similarity	NPC173582
0.9167	High Similarity	NPC476215
0.9156	High Similarity	NPC265480
0.9156	High Similarity	NPC149368
0.9156	High Similarity	NPC295613
0.9156	High Similarity	NPC473657
0.915	High Similarity	NPC268193
0.915	High Similarity	NPC223701
0.915	High Similarity	NPC112701
0.915	High Similarity	NPC472583
0.915	High Similarity	NPC121910
0.915	High Similarity	NPC7989
0.915	High Similarity	NPC168805
0.915	High Similarity	NPC109594
0.915	High Similarity	NPC469405
0.915	High Similarity	NPC326592
0.9145	High Similarity	NPC262039
0.9145	High Similarity	NPC471677
0.9145	High Similarity	NPC319910
0.9145	High Similarity	NPC471676
0.9145	High Similarity	NPC262038
0.9145	High Similarity	NPC472420
0.9145	High Similarity	NPC263384
0.9145	High Similarity	NPC278476
0.9145	High Similarity	NPC254412
0.9145	High Similarity	NPC474021
0.9145	High Similarity	NPC472422
0.9145	High Similarity	NPC474023
0.9145	High Similarity	NPC23253
0.9145	High Similarity	NPC244577
0.9139	High Similarity	NPC89442
0.9139	High Similarity	NPC88886
0.9139	High Similarity	NPC104172
0.9133	High Similarity	NPC202494
0.913	High Similarity	NPC213052
0.913	High Similarity	NPC25724

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 NPC470605 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	345
0.1-0.2	910
0.2-0.3	1832
0.3-0.4	2669
0.4-0.5	1949
0.5-0.6	978
0.6-0.7	298
0.7-0.8	125
0.8-0.85	27
0.85-0.9	16
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9474	High Similarity	NPD4381	Clinical (unspecified phase)
0.9304	High Similarity	NPD7804	Clinical (unspecified phase)
0.9079	High Similarity	NPD4380	Phase 2
0.8944	High Similarity	NPD7054	Approved
0.8889	High Similarity	NPD7472	Approved
0.8889	High Similarity	NPD7074	Phase 3
0.8882	High Similarity	NPD3818	Discontinued
0.8854	High Similarity	NPD7075	Discontinued
0.8834	High Similarity	NPD6797	Phase 2
0.8782	High Similarity	NPD2393	Clinical (unspecified phase)
0.878	High Similarity	NPD7251	Discontinued
0.878	High Similarity	NPD6559	Discontinued
0.875	High Similarity	NPD4378	Clinical (unspecified phase)
0.8727	High Similarity	NPD7808	Phase 3
0.8718	High Similarity	NPD6801	Discontinued
0.8662	High Similarity	NPD7096	Clinical (unspecified phase)
0.8614	High Similarity	NPD4338	Clinical (unspecified phase)
0.8599	High Similarity	NPD1934	Approved
0.8533	High Similarity	NPD1550	Clinical (unspecified phase)
0.8533	High Similarity	NPD1552	Clinical (unspecified phase)
0.8491	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8477	Intermediate Similarity	NPD1549	Phase 2
0.8418	Intermediate Similarity	NPD7411	Suspended
0.8415	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8415	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8415	Intermediate Similarity	NPD6166	Phase 2
0.8387	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8344	Intermediate Similarity	NPD2796	Approved
0.8313	Intermediate Similarity	NPD2801	Approved
0.8313	Intermediate Similarity	NPD7819	Suspended
0.8278	Intermediate Similarity	NPD1510	Phase 2
0.8261	Intermediate Similarity	NPD3817	Phase 2
0.8232	Intermediate Similarity	NPD6959	Discontinued
0.821	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8205	Intermediate Similarity	NPD1511	Approved
0.8205	Intermediate Similarity	NPD6799	Approved
0.8165	Intermediate Similarity	NPD5403	Approved
0.8129	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.8101	Intermediate Similarity	NPD1512	Approved
0.8084	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8065	Intermediate Similarity	NPD2800	Approved
0.8038	Intermediate Similarity	NPD5401	Approved
0.8037	Intermediate Similarity	NPD5402	Approved
0.8033	Intermediate Similarity	NPD7584	Approved
0.8013	Intermediate Similarity	NPD1240	Approved
0.8012	Intermediate Similarity	NPD6599	Discontinued
0.8011	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7988	Intermediate Similarity	NPD3882	Suspended
0.7952	Intermediate Similarity	NPD5494	Approved
0.7925	Intermediate Similarity	NPD2533	Approved
0.7925	Intermediate Similarity	NPD2532	Approved
0.7925	Intermediate Similarity	NPD2534	Approved
0.7919	Intermediate Similarity	NPD8312	Approved
0.7919	Intermediate Similarity	NPD8313	Approved
0.7908	Intermediate Similarity	NPD1607	Approved
0.7908	Intermediate Similarity	NPD6651	Approved
0.7888	Intermediate Similarity	NPD1653	Approved
0.7879	Intermediate Similarity	NPD7768	Phase 2
0.7866	Intermediate Similarity	NPD8455	Phase 2
0.7857	Intermediate Similarity	NPD6232	Discontinued
0.7849	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7836	Intermediate Similarity	NPD5844	Phase 1
0.7834	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7834	Intermediate Similarity	NPD1243	Approved
0.7826	Intermediate Similarity	NPD920	Approved
0.7824	Intermediate Similarity	NPD7473	Discontinued
0.7785	Intermediate Similarity	NPD4628	Phase 3
0.7785	Intermediate Similarity	NPD3750	Approved
0.7705	Intermediate Similarity	NPD6778	Approved
0.7705	Intermediate Similarity	NPD6782	Approved
0.7705	Intermediate Similarity	NPD6776	Approved
0.7705	Intermediate Similarity	NPD6781	Approved
0.7705	Intermediate Similarity	NPD6777	Approved
0.7705	Intermediate Similarity	NPD6779	Approved
0.7705	Intermediate Similarity	NPD6780	Approved
0.7702	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7688	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.766	Intermediate Similarity	NPD8151	Discontinued
0.7657	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7644	Intermediate Similarity	NPD5953	Discontinued
0.7643	Intermediate Similarity	NPD2935	Discontinued
0.7643	Intermediate Similarity	NPD1551	Phase 2
0.7637	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7635	Intermediate Similarity	NPD1091	Approved
0.7619	Intermediate Similarity	NPD3749	Approved
0.7613	Intermediate Similarity	NPD5124	Phase 1
0.7613	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7607	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7606	Intermediate Similarity	NPD7585	Approved
0.759	Intermediate Similarity	NPD37	Approved
0.7588	Intermediate Similarity	NPD7199	Phase 2
0.7581	Intermediate Similarity	NPD7435	Discontinued
0.7574	Intermediate Similarity	NPD6234	Discontinued
0.7574	Intermediate Similarity	NPD919	Approved
0.7572	Intermediate Similarity	NPD7228	Approved
0.7572	Intermediate Similarity	NPD3751	Discontinued
0.756	Intermediate Similarity	NPD4967	Phase 2
0.756	Intermediate Similarity	NPD4966	Approved
0.756	Intermediate Similarity	NPD4965	Approved
0.7553	Intermediate Similarity	NPD7583	Approved
0.7545	Intermediate Similarity	NPD1465	Phase 2
0.7544	Intermediate Similarity	NPD3787	Discontinued
0.7532	Intermediate Similarity	NPD2313	Discontinued
0.7529	Intermediate Similarity	NPD7286	Phase 2
0.7527	Intermediate Similarity	NPD4360	Phase 2
0.7527	Intermediate Similarity	NPD4363	Phase 3
0.7515	Intermediate Similarity	NPD7458	Discontinued
0.75	Intermediate Similarity	NPD1652	Phase 2
0.7487	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7487	Intermediate Similarity	NPD7697	Approved
0.7487	Intermediate Similarity	NPD7783	Phase 2
0.7487	Intermediate Similarity	NPD7698	Approved
0.7487	Intermediate Similarity	NPD7696	Phase 3
0.7485	Intermediate Similarity	NPD1247	Approved
0.7468	Intermediate Similarity	NPD7033	Discontinued
0.7468	Intermediate Similarity	NPD2799	Discontinued
0.7468	Intermediate Similarity	NPD3748	Approved
0.7453	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7447	Intermediate Similarity	NPD7871	Phase 2
0.7447	Intermediate Similarity	NPD7870	Phase 2
0.7442	Intermediate Similarity	NPD5710	Approved
0.7442	Intermediate Similarity	NPD5711	Approved
0.7438	Intermediate Similarity	NPD2424	Discontinued
0.7436	Intermediate Similarity	NPD1613	Approved
0.7436	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7433	Intermediate Similarity	NPD6823	Phase 2
0.7432	Intermediate Similarity	NPD6535	Approved
0.7432	Intermediate Similarity	NPD6534	Approved
0.7421	Intermediate Similarity	NPD7701	Phase 2
0.7421	Intermediate Similarity	NPD6099	Approved
0.7421	Intermediate Similarity	NPD6100	Approved
0.7419	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD3226	Approved
0.7403	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7401	Intermediate Similarity	NPD7685	Pre-registration
0.7399	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD1933	Approved
0.7389	Intermediate Similarity	NPD230	Phase 1
0.7386	Intermediate Similarity	NPD2798	Approved
0.7344	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7344	Intermediate Similarity	NPD7874	Approved
0.7321	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD7390	Discontinued
0.7317	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD7699	Phase 2
0.7312	Intermediate Similarity	NPD7700	Phase 2
0.7306	Intermediate Similarity	NPD7801	Approved
0.729	Intermediate Similarity	NPD4908	Phase 1
0.729	Intermediate Similarity	NPD6832	Phase 2
0.7285	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7285	Intermediate Similarity	NPD422	Phase 1
0.7267	Intermediate Similarity	NPD2344	Approved
0.7267	Intermediate Similarity	NPD2346	Discontinued
0.725	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7238	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7237	Intermediate Similarity	NPD9717	Approved
0.7226	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD943	Approved
0.7208	Intermediate Similarity	NPD1203	Approved
0.7207	Intermediate Similarity	NPD7240	Approved
0.7204	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7204	Intermediate Similarity	NPD4361	Phase 2
0.72	Intermediate Similarity	NPD3926	Phase 2
0.7198	Intermediate Similarity	NPD8434	Phase 2
0.7197	Intermediate Similarity	NPD6798	Discontinued
0.7197	Intermediate Similarity	NPD3268	Approved
0.7189	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7189	Intermediate Similarity	NPD6213	Phase 3
0.7189	Intermediate Similarity	NPD6212	Phase 3
0.7179	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7178	Intermediate Similarity	NPD2654	Approved
0.7178	Intermediate Similarity	NPD6674	Discontinued
0.7173	Intermediate Similarity	NPD8319	Approved
0.7173	Intermediate Similarity	NPD8320	Phase 1
0.7171	Intermediate Similarity	NPD1610	Phase 2
0.717	Intermediate Similarity	NPD447	Suspended
0.7169	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD7266	Discontinued
0.7143	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD3027	Phase 3
0.7133	Intermediate Similarity	NPD1548	Phase 1
0.7107	Intermediate Similarity	NPD7930	Approved
0.7104	Intermediate Similarity	NPD8150	Discontinued
0.7101	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD2797	Approved
0.7091	Intermediate Similarity	NPD2309	Approved
0.7089	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD7097	Phase 1
0.7063	Intermediate Similarity	NPD6355	Discontinued
0.7062	Intermediate Similarity	NPD2403	Approved
0.7062	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7056	Intermediate Similarity	NPD3823	Discontinued
0.7055	Intermediate Similarity	NPD6004	Phase 3
0.7055	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD6002	Phase 3
0.7055	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD6005	Phase 3
0.7048	Intermediate Similarity	NPD5058	Phase 3

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