NPASS Compound

Structure

CID106920 OpenBabel06191715452D 29 31 0 0 1 0 0 0 0 0999 V2000 2.9641 1.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3975 5.5328 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7859 4.8126 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0428 5.4817 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3660 4.0388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2321 4.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2601 1.2601 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5000 2.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2321 2.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7248 2.9074 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4190 2.5472 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3660 3.0388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4680 2.2382 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3090 0.9511 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.5000 1.5388 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.0981 4.0388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0981 3.0388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9328 3.8855 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6270 3.5254 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8838 4.1945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3090 0.9511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9641 4.5388 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2601 1.2601 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.9641 2.5388 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1896 4.5546 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.5780 3.8344 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0917 5.1727 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 25 1 0 0 0 0 2 26 1 0 0 0 0 3 27 1 0 0 0 0 4 28 1 0 0 0 0 5 6 2 0 0 0 0 5 13 1 0 0 0 0 6 17 1 0 0 0 0 7 14 1 0 0 0 0 8 13 1 0 0 0 0 9 13 2 0 0 0 0 9 18 1 0 0 0 0 10 14 2 0 0 0 0 10 19 1 0 0 0 0 11 14 1 0 0 0 0 11 20 2 0 0 0 0 12 15 1 0 0 0 0 12 29 1 0 0 0 0 15 7 1 6 0 0 0 15 16 1 0 0 0 0 16 8 1 1 0 0 0 16 22 1 0 0 0 0 17 18 2 0 0 0 0 17 23 1 0 0 0 0 18 25 1 0 0 0 0 19 21 2 0 0 0 0 19 26 1 0 0 0 0 20 21 1 0 0 0 0 20 27 1 0 0 0 0 21 28 1 0 0 0 0 22 24 2 0 0 0 0 22 29 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	284.09
Volume:	265.431
LogP:	-0.701
LogD:	-0.207
LogS:	-1.357
# Rotatable Bonds:	5
TPSA:	82.63
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.82
Synthetic Accessibility Score:	3.471
Fsp3:	0.333
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.064
MDCK Permeability:	6.908353498147335e-06
Pgp-inhibitor:	0.002
Pgp-substrate:	0.007
Human Intestinal Absorption (HIA):	0.307
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.026

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.963
Plasma Protein Binding (PPB):	48.0715217590332%
Volume Distribution (VD):	2.084
Pgp-substrate:	59.50144958496094%

ADMET: Metabolism

CYP1A2-inhibitor:	0.025
CYP1A2-substrate:	0.836
CYP2C19-inhibitor:	0.041
CYP2C19-substrate:	0.067
CYP2C9-inhibitor:	0.015
CYP2C9-substrate:	0.859
CYP2D6-inhibitor:	0.181
CYP2D6-substrate:	0.852
CYP3A4-inhibitor:	0.007
CYP3A4-substrate:	0.095

ADMET: Excretion

Clearance (CL):	3.65
Half-life (T1/2):	0.894

ADMET: Toxicity

hERG Blockers:	0.072
Human Hepatotoxicity (H-HT):	0.652
Drug-inuced Liver Injury (DILI):	0.035
AMES Toxicity:	0.114
Rat Oral Acute Toxicity:	0.237
Maximum Recommended Daily Dose:	0.931
Skin Sensitization:	0.922
Carcinogencity:	0.191
Eye Corrosion:	0.1
Eye Irritation:	0.08
Respiratory Toxicity:	0.732

Download Data

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

Natural Product: NPC106920

Natural Product ID:	NPC106920
*Common Name:**	(3R,4R)-3-(4-Hydroxy-3-Methoxybenzyl)-4-(3,4,5-Trimethoxybenzyl)Dihydrofuran-2(3H)-One
IUPAC Name:	(3R,4R)-3-[(4-hydroxy-3-methoxyphenyl)methyl]-4-[(3,4,5-trimethoxyphenyl)methyl]oxolan-2-one
Synonyms:
Standard InCHIKey:	DRHBSAJKORZXET-JKSUJKDBSA-N
Standard InCHI:	InChI=1S/C22H26O7/c1-25-18-9-13(5-6-17(18)23)8-16-15(12-29-22(16)24)7-14-10-19(26-2)21(28-4)20(11-14)27-3/h5-6,9-11,15-16,23H,7-8,12H2,1-4H3/t15-,16+/m0/s1
SMILES:	COc1cc(ccc1O)C[C@@H]1[C@@H](Cc2cc(c(c(c2)OC)OC)OC)COC1=O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3578258
PubChem CID:	10069677
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0001392] Lignans, neolignans and related compounds [CHEMONTID:0003686] Furanoid lignans [CHEMONTID:0001604] Tetrahydrofuran lignans [CHEMONTID:0003424] 9,9'-epoxylignans [CHEMONTID:0001613] Dibenzylbutyrolactone lignans

*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
NPO683	Rosa canina	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12880322]
NPO7267	Glycosmis chlorosperma	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24798019]
NPO12235	Trachelospermum jasminoides	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO683	Rosa canina	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14834	Trachelospermum asiaticum	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14834	Trachelospermum asiaticum	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12235	Trachelospermum jasminoides	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10398	Myrica gale	Species	Myricaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8340	Stachys sylvatica	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO683	Rosa canina	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7267	Glycosmis chlorosperma	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12235	Trachelospermum jasminoides	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO683	Rosa canina	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO10398	Myrica gale	Species	Myricaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO14834	Trachelospermum asiaticum	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO12235	Trachelospermum jasminoides	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO6760	Saussurea conica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO683	Rosa canina	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8340	Stachys sylvatica	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28466	Torreya nucifera	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7267	Glycosmis chlorosperma	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12235	Trachelospermum jasminoides	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10398	Myrica gale	Species	Myricaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19459	Dictyota kunthii	Species	Dictyotaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14834	Trachelospermum asiaticum	Species	Apocynaceae	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	3

Activity Type	# Activity
Cell Line	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT839	Cell Line	L6	Rattus norvegicus	Activity	=	128.8	%	PMID[449791]
NPT839	Cell Line	L6	Rattus norvegicus	Activity	=	233.9	%	PMID[449791]
NPT839	Cell Line	L6	Rattus norvegicus	Ratio	=	0.551	n.a.	PMID[449791]

☑ 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 NPC106920 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	303
0.1-0.2	1208
0.2-0.3	2925
0.3-0.4	7217
0.4-0.5	11459
0.5-0.6	3811
0.6-0.7	7075
0.7-0.8	7341
0.8-0.85	1109
0.85-0.9	190
0.9-0.95	51
0.95-1	8

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC273657
0.9853	High Similarity	NPC477697
0.9853	High Similarity	NPC470811
0.9853	High Similarity	NPC477696
0.9574	High Similarity	NPC145569
0.9574	High Similarity	NPC216223
0.9493	High Similarity	NPC253722
0.9493	High Similarity	NPC31751
0.9493	High Similarity	NPC253481
0.9481	High Similarity	NPC211386
0.9437	High Similarity	NPC474965
0.9437	High Similarity	NPC125570
0.9437	High Similarity	NPC668
0.9437	High Similarity	NPC174512
0.9437	High Similarity	NPC293757
0.9437	High Similarity	NPC477695
0.942	High Similarity	NPC100675
0.9407	High Similarity	NPC68779
0.9407	High Similarity	NPC300776
0.9407	High Similarity	NPC176814
0.9407	High Similarity	NPC5310
0.9407	High Similarity	NPC4982
0.9375	High Similarity	NPC476434
0.9338	High Similarity	NPC72796
0.9338	High Similarity	NPC44245
0.931	High Similarity	NPC473236
0.9306	High Similarity	NPC477700
0.9291	High Similarity	NPC223185
0.9241	High Similarity	NPC477699
0.922	High Similarity	NPC27159
0.9203	High Similarity	NPC281780
0.9178	High Similarity	NPC178574
0.9178	High Similarity	NPC65591
0.9172	High Similarity	NPC32079
0.913	High Similarity	NPC90431
0.9124	High Similarity	NPC67247
0.9116	High Similarity	NPC136757
0.9116	High Similarity	NPC30009
0.9116	High Similarity	NPC103197
0.9078	High Similarity	NPC210354
0.9078	High Similarity	NPC176586
0.9071	High Similarity	NPC147379
0.9058	High Similarity	NPC113295
0.9051	High Similarity	NPC158331
0.9007	High Similarity	NPC282291
0.9007	High Similarity	NPC166137
0.9007	High Similarity	NPC29599
0.9007	High Similarity	NPC470991
0.8993	High Similarity	NPC471988
0.8986	High Similarity	NPC287745
0.898	High Similarity	NPC56184
0.8978	High Similarity	NPC175067
0.8978	High Similarity	NPC204215
0.8951	High Similarity	NPC191158
0.8951	High Similarity	NPC177644
0.8944	High Similarity	NPC40237
0.8944	High Similarity	NPC52664
0.8944	High Similarity	NPC151423
0.8936	High Similarity	NPC203351
0.8933	High Similarity	NPC181168
0.8933	High Similarity	NPC115281
0.8933	High Similarity	NPC163527
0.8921	High Similarity	NPC126409
0.8921	High Similarity	NPC99572
0.8904	High Similarity	NPC477698
0.8889	High Similarity	NPC477702
0.8889	High Similarity	NPC223807
0.8889	High Similarity	NPC127587
0.8873	High Similarity	NPC19158
0.8859	High Similarity	NPC25127
0.8851	High Similarity	NPC246566
0.8851	High Similarity	NPC95498
0.8849	High Similarity	NPC326095
0.8849	High Similarity	NPC244983
0.8836	High Similarity	NPC102934
0.8836	High Similarity	NPC252402
0.8828	High Similarity	NPC472560
0.8828	High Similarity	NPC212890
0.8819	High Similarity	NPC92693
0.8819	High Similarity	NPC18211
0.8819	High Similarity	NPC218841
0.8819	High Similarity	NPC475000
0.8816	High Similarity	NPC268718
0.8816	High Similarity	NPC150943
0.8816	High Similarity	NPC91634
0.8815	High Similarity	NPC76451
0.8811	High Similarity	NPC472335
0.8811	High Similarity	NPC472332
0.88	High Similarity	NPC238834
0.88	High Similarity	NPC476642
0.8794	High Similarity	NPC308976
0.8792	High Similarity	NPC245615
0.8792	High Similarity	NPC299706
0.8792	High Similarity	NPC115466
0.8792	High Similarity	NPC61604
0.8786	High Similarity	NPC165155
0.8786	High Similarity	NPC470990
0.8786	High Similarity	NPC24490
0.8786	High Similarity	NPC34103
0.8786	High Similarity	NPC141765
0.8784	High Similarity	NPC164082
0.8776	High Similarity	NPC474903
0.8768	High Similarity	NPC474017
0.8767	High Similarity	NPC30720
0.8759	High Similarity	NPC241354
0.875	High Similarity	NPC474288
0.8741	High Similarity	NPC17943
0.8741	High Similarity	NPC173608
0.8741	High Similarity	NPC116907
0.8741	High Similarity	NPC221077
0.8741	High Similarity	NPC280767
0.8741	High Similarity	NPC472093
0.8741	High Similarity	NPC117214
0.8741	High Similarity	NPC298757
0.8741	High Similarity	NPC193544
0.8741	High Similarity	NPC203133
0.8741	High Similarity	NPC233410
0.8741	High Similarity	NPC475169
0.8741	High Similarity	NPC57490
0.8741	High Similarity	NPC208950
0.8741	High Similarity	NPC251855
0.8733	High Similarity	NPC287504
0.8725	High Similarity	NPC267091
0.8725	High Similarity	NPC75695
0.8725	High Similarity	NPC151425
0.8723	High Similarity	NPC209229
0.8701	High Similarity	NPC76687
0.8699	High Similarity	NPC474799
0.8699	High Similarity	NPC3982
0.8699	High Similarity	NPC193779
0.8696	High Similarity	NPC64201
0.8696	High Similarity	NPC187998
0.8696	High Similarity	NPC153739
0.8696	High Similarity	NPC242807
0.8696	High Similarity	NPC145305
0.8696	High Similarity	NPC42300
0.8696	High Similarity	NPC257582
0.8696	High Similarity	NPC92164
0.8696	High Similarity	NPC77040
0.8696	High Similarity	NPC241522
0.8696	High Similarity	NPC174495
0.869	High Similarity	NPC143092
0.869	High Similarity	NPC87883
0.869	High Similarity	NPC16353
0.8686	High Similarity	NPC470213
0.8686	High Similarity	NPC45774
0.8686	High Similarity	NPC282703
0.8686	High Similarity	NPC21867
0.8686	High Similarity	NPC128208
0.8686	High Similarity	NPC184733
0.8686	High Similarity	NPC129570
0.8686	High Similarity	NPC11258
0.8686	High Similarity	NPC98631
0.8686	High Similarity	NPC186843
0.8686	High Similarity	NPC206615
0.8681	High Similarity	NPC67467
0.8681	High Similarity	NPC131971
0.8675	High Similarity	NPC38699
0.8671	High Similarity	NPC309124
0.8671	High Similarity	NPC254759
0.8671	High Similarity	NPC160283
0.8671	High Similarity	NPC184797
0.8671	High Similarity	NPC289690
0.8671	High Similarity	NPC177868
0.8671	High Similarity	NPC288452
0.8667	High Similarity	NPC199773
0.8667	High Similarity	NPC474606
0.8667	High Similarity	NPC245948
0.8662	High Similarity	NPC474039
0.8658	High Similarity	NPC243891
0.8658	High Similarity	NPC475756
0.8645	High Similarity	NPC14294
0.8645	High Similarity	NPC116759
0.8639	High Similarity	NPC304687
0.8639	High Similarity	NPC472333
0.8639	High Similarity	NPC101755
0.8639	High Similarity	NPC80230
0.8639	High Similarity	NPC104024
0.8639	High Similarity	NPC65574
0.8639	High Similarity	NPC208507
0.8633	High Similarity	NPC40432
0.8633	High Similarity	NPC7171
0.8633	High Similarity	NPC158079
0.8633	High Similarity	NPC27843
0.8633	High Similarity	NPC277804
0.8633	High Similarity	NPC115207
0.8633	High Similarity	NPC161557
0.8633	High Similarity	NPC228346
0.863	High Similarity	NPC474982
0.863	High Similarity	NPC207732
0.8623	High Similarity	NPC475875
0.8623	High Similarity	NPC170844
0.8623	High Similarity	NPC476968
0.8621	High Similarity	NPC255566
0.8621	High Similarity	NPC298317
0.8618	High Similarity	NPC163635
0.8618	High Similarity	NPC150227
0.8618	High Similarity	NPC237946
0.8618	High Similarity	NPC478055
0.8618	High Similarity	NPC32373

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 NPC106920 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	252
0.1-0.2	773
0.2-0.3	1590
0.3-0.4	2516
0.4-0.5	2095
0.5-0.6	1107
0.6-0.7	643
0.7-0.8	157
0.8-0.85	13
0.85-0.9	4
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8874	High Similarity	NPD6234	Discontinued
0.8667	High Similarity	NPD37	Approved
0.8623	High Similarity	NPD3027	Phase 3
0.8618	High Similarity	NPD4967	Phase 2
0.8618	High Similarity	NPD4966	Approved
0.8618	High Similarity	NPD4965	Approved
0.8481	Intermediate Similarity	NPD7228	Approved
0.8397	Intermediate Similarity	NPD7199	Phase 2
0.8377	Intermediate Similarity	NPD3882	Suspended
0.8291	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.8258	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8255	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.8182	Intermediate Similarity	NPD1934	Approved
0.8169	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8129	Intermediate Similarity	NPD2801	Approved
0.8125	Intermediate Similarity	NPD230	Phase 1
0.8121	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.8092	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.8056	Intermediate Similarity	NPD1613	Approved
0.8056	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8054	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.8054	Intermediate Similarity	NPD4110	Phase 3
0.8028	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.8025	Intermediate Similarity	NPD3818	Discontinued
0.8013	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD6355	Discontinued
0.8	Intermediate Similarity	NPD6232	Discontinued
0.7963	Intermediate Similarity	NPD7473	Discontinued
0.7962	Intermediate Similarity	NPD3817	Phase 2
0.7958	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7939	Intermediate Similarity	NPD7240	Approved
0.7929	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7898	Intermediate Similarity	NPD1465	Phase 2
0.7881	Intermediate Similarity	NPD6190	Approved
0.7857	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD1608	Approved
0.7815	Intermediate Similarity	NPD4628	Phase 3
0.7808	Intermediate Similarity	NPD4060	Phase 1
0.78	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7791	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7791	Intermediate Similarity	NPD6166	Phase 2
0.7791	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD5283	Phase 1
0.7778	Intermediate Similarity	NPD1511	Approved
0.7778	Intermediate Similarity	NPD4908	Phase 1
0.7764	Intermediate Similarity	NPD5494	Approved
0.7758	Intermediate Similarity	NPD5844	Phase 1
0.7727	Intermediate Similarity	NPD2534	Approved
0.7727	Intermediate Similarity	NPD2532	Approved
0.7727	Intermediate Similarity	NPD2533	Approved
0.7711	Intermediate Similarity	NPD7074	Phase 3
0.7697	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD3750	Approved
0.7679	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7677	Intermediate Similarity	NPD1512	Approved
0.7676	Intermediate Similarity	NPD2982	Phase 2
0.7676	Intermediate Similarity	NPD2983	Phase 2
0.7671	Intermediate Similarity	NPD6798	Discontinued
0.7671	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7669	Intermediate Similarity	NPD7229	Phase 3
0.7665	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7662	Intermediate Similarity	NPD4357	Discontinued
0.7662	Intermediate Similarity	NPD6799	Approved
0.766	Intermediate Similarity	NPD1610	Phase 2
0.7651	Intermediate Similarity	NPD7054	Approved
0.7643	Intermediate Similarity	NPD17	Approved
0.764	Intermediate Similarity	NPD7075	Discontinued
0.763	Intermediate Similarity	NPD228	Approved
0.7622	Intermediate Similarity	NPD1283	Approved
0.7622	Intermediate Similarity	NPD5242	Approved
0.7619	Intermediate Similarity	NPD6233	Phase 2
0.7619	Intermediate Similarity	NPD7685	Pre-registration
0.7613	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7606	Intermediate Similarity	NPD2981	Phase 2
0.7605	Intermediate Similarity	NPD7472	Approved
0.7603	Intermediate Similarity	NPD7095	Approved
0.7595	Intermediate Similarity	NPD6599	Discontinued
0.7586	Intermediate Similarity	NPD9494	Approved
0.7586	Intermediate Similarity	NPD3018	Phase 2
0.7582	Intermediate Similarity	NPD8166	Discontinued
0.758	Intermediate Similarity	NPD1653	Approved
0.7571	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7569	Intermediate Similarity	NPD2797	Approved
0.7562	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7562	Intermediate Similarity	NPD7819	Suspended
0.7551	Intermediate Similarity	NPD3764	Approved
0.755	Intermediate Similarity	NPD2935	Discontinued
0.755	Intermediate Similarity	NPD2438	Suspended
0.755	Intermediate Similarity	NPD6099	Approved
0.755	Intermediate Similarity	NPD6100	Approved
0.7547	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7535	Intermediate Similarity	NPD3705	Approved
0.75	Intermediate Similarity	NPD7680	Approved
0.75	Intermediate Similarity	NPD7266	Discontinued
0.75	Intermediate Similarity	NPD4062	Phase 3
0.7485	Intermediate Similarity	NPD919	Approved
0.7484	Intermediate Similarity	NPD4380	Phase 2
0.7483	Intermediate Similarity	NPD1510	Phase 2
0.7481	Intermediate Similarity	NPD3022	Approved
0.7481	Intermediate Similarity	NPD3021	Approved
0.7469	Intermediate Similarity	NPD7768	Phase 2
0.7467	Intermediate Similarity	NPD6653	Approved
0.7456	Intermediate Similarity	NPD6797	Phase 2
0.7451	Intermediate Similarity	NPD5958	Discontinued
0.745	Intermediate Similarity	NPD2979	Phase 3
0.745	Intermediate Similarity	NPD3620	Phase 2
0.745	Intermediate Similarity	NPD943	Approved
0.745	Intermediate Similarity	NPD1240	Approved
0.745	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7434	Intermediate Similarity	NPD1551	Phase 2
0.7432	Intermediate Similarity	NPD3268	Approved
0.7429	Intermediate Similarity	NPD5536	Phase 2
0.7413	Intermediate Similarity	NPD422	Phase 1
0.7413	Intermediate Similarity	NPD1281	Approved
0.7412	Intermediate Similarity	NPD7251	Discontinued
0.7412	Intermediate Similarity	NPD6559	Discontinued
0.741	Intermediate Similarity	NPD3926	Phase 2
0.7407	Intermediate Similarity	NPD5353	Approved
0.7407	Intermediate Similarity	NPD5402	Approved
0.74	Intermediate Similarity	NPD447	Suspended
0.7397	Intermediate Similarity	NPD5647	Approved
0.7394	Intermediate Similarity	NPD8127	Discontinued
0.7391	Intermediate Similarity	NPD6801	Discontinued
0.7389	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD6002	Phase 3
0.7386	Intermediate Similarity	NPD6004	Phase 3
0.7386	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD6005	Phase 3
0.7386	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7376	Intermediate Similarity	NPD1548	Phase 1
0.7376	Intermediate Similarity	NPD1894	Discontinued
0.7368	Intermediate Similarity	NPD7808	Phase 3
0.7368	Intermediate Similarity	NPD7033	Discontinued
0.7368	Intermediate Similarity	NPD3748	Approved
0.7361	Intermediate Similarity	NPD9269	Phase 2
0.7355	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7351	Intermediate Similarity	NPD1607	Approved
0.7347	Intermediate Similarity	NPD2861	Phase 2
0.7343	Intermediate Similarity	NPD3847	Discontinued
0.7338	Intermediate Similarity	NPD1549	Phase 2
0.7338	Intermediate Similarity	NPD4534	Discontinued
0.7329	Intermediate Similarity	NPD6386	Approved
0.7329	Intermediate Similarity	NPD6385	Approved
0.7329	Intermediate Similarity	NPD7411	Suspended
0.7324	Intermediate Similarity	NPD5585	Approved
0.7317	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD3749	Approved
0.731	Intermediate Similarity	NPD4749	Approved
0.7308	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7301	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7296	Intermediate Similarity	NPD5403	Approved
0.7292	Intermediate Similarity	NPD1535	Discovery
0.729	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD5763	Approved
0.7273	Intermediate Similarity	NPD5762	Approved
0.7267	Intermediate Similarity	NPD7028	Phase 2
0.7255	Intermediate Similarity	NPD2799	Discontinued
0.7248	Intermediate Similarity	NPD4625	Phase 3
0.7241	Intermediate Similarity	NPD1481	Phase 2
0.7233	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7229	Intermediate Similarity	NPD6746	Phase 2
0.7219	Intermediate Similarity	NPD825	Approved
0.7219	Intermediate Similarity	NPD1558	Phase 1
0.7219	Intermediate Similarity	NPD826	Approved
0.7216	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD6971	Discontinued
0.7208	Intermediate Similarity	NPD2796	Approved
0.7208	Intermediate Similarity	NPD2531	Phase 2
0.7205	Intermediate Similarity	NPD3455	Phase 2
0.7203	Intermediate Similarity	NPD1357	Approved
0.7203	Intermediate Similarity	NPD1651	Approved
0.72	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7186	Intermediate Similarity	NPD1247	Approved
0.7171	Intermediate Similarity	NPD5124	Phase 1
0.7171	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD3688	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD3146	Approved
0.717	Intermediate Similarity	NPD5401	Approved
0.7168	Intermediate Similarity	NPD7549	Discontinued
0.7162	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD1778	Approved
0.7152	Intermediate Similarity	NPD6663	Approved
0.7152	Intermediate Similarity	NPD7124	Phase 2
0.7152	Intermediate Similarity	NPD8032	Phase 2
0.7143	Intermediate Similarity	NPD3787	Discontinued
0.7143	Intermediate Similarity	NPD5711	Approved
0.7143	Intermediate Similarity	NPD5710	Approved
0.7134	Intermediate Similarity	NPD5563	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD8455	Phase 2
0.7133	Intermediate Similarity	NPD9545	Approved
0.7125	Intermediate Similarity	NPD6273	Approved
0.7114	Intermediate Similarity	NPD5736	Approved
0.7105	Intermediate Similarity	NPD4140	Approved
0.7099	Intermediate Similarity	NPD4005	Discontinued
0.7097	Intermediate Similarity	NPD4477	Approved
0.7097	Intermediate Similarity	NPD4476	Approved
0.7097	Intermediate Similarity	NPD6032	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