NPASS Compound

Structure

NPC252402 OpenBabel07101719512D 43 46 0 0 1 0 0 0 0 0999 V2000 -8.1211 -4.4890 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7350 -1.2183 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3729 -4.6634 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7796 3.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2437 0.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9406 -2.7906 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7816 -4.0778 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8916 -2.4816 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0385 -3.4087 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5759 -2.5227 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4758 -4.4379 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1582 -1.8182 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9771 -3.5408 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7796 1.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6456 -0.4067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6691 -0.7431 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5522 -2.0704 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7327 -3.7688 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5704 -2.6272 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7796 0.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1691 -1.6092 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8090 -1.4013 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.6348 -3.1507 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4269 -4.1289 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1527 -1.9228 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9716 -3.6453 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6456 1.5933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5116 0.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0874 -3.7177 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5594 -2.8363 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5116 1.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9135 -0.4067 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.5858 -2.8417 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8795 -4.6958 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.5540 -2.9408 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3776 1.5933 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.1700 -4.7980 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.7405 -1.1137 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3784 -4.5589 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6456 2.5933 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3776 -0.4067 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3443 -3.0485 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 37 1 0 0 0 0 2 38 1 0 0 0 0 3 39 1 0 0 0 0 4 40 1 0 0 0 0 5 41 1 0 0 0 0 6 8 2 0 0 0 0 6 18 1 0 0 0 0 7 9 2 0 0 0 0 7 18 1 0 0 0 0 8 23 1 0 0 0 0 9 29 1 0 0 0 0 10 19 1 0 0 0 0 11 18 2 0 0 0 0 11 24 1 0 0 0 0 12 19 2 0 0 0 0 12 25 1 0 0 0 0 13 19 1 0 0 0 0 13 26 2 0 0 0 0 14 20 2 0 0 0 0 14 27 1 0 0 0 0 15 20 1 0 0 0 0 15 28 2 0 0 0 0 16 21 1 0 0 0 0 16 43 1 0 0 0 0 17 42 1 0 0 0 0 21 10 1 6 0 0 0 21 22 1 0 0 0 0 22 17 1 6 0 0 0 22 32 1 0 0 0 0 23 24 2 0 0 0 0 23 33 1 0 0 0 0 24 37 1 0 0 0 0 25 30 2 0 0 0 0 25 38 1 0 0 0 0 26 30 1 0 0 0 0 26 39 1 0 0 0 0 27 31 2 0 0 0 0 27 40 1 0 0 0 0 28 31 1 0 0 0 0 28 41 1 0 0 0 0 29 34 2 0 0 0 0 29 42 1 0 0 0 0 30 35 1 0 0 0 0 31 36 1 0 0 0 0 32 20 1 1 0 0 0 32 43 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	596.23
Volume:	595.494
LogP:	4.03
LogD:	3.414
LogS:	-5.097
# Rotatable Bonds:	13
TPSA:	142.37
# H-Bond Aceptor:	11
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	11

MedChem Properties

QED Drug-Likeness Score:	0.199
Synthetic Accessibility Score:	3.911
Fsp3:	0.344
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.163
MDCK Permeability:	2.4680937713128515e-05
Pgp-inhibitor:	0.964
Pgp-substrate:	0.705
Human Intestinal Absorption (HIA):	0.018
20% Bioavailability (F20%):	0.046
30% Bioavailability (F30%):	0.156

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.006
Plasma Protein Binding (PPB):	90.29399871826172%
Volume Distribution (VD):	0.33
Pgp-substrate:	20.802024841308594%

ADMET: Metabolism

CYP1A2-inhibitor:	0.068
CYP1A2-substrate:	0.912
CYP2C19-inhibitor:	0.34
CYP2C19-substrate:	0.723
CYP2C9-inhibitor:	0.85
CYP2C9-substrate:	0.816
CYP2D6-inhibitor:	0.081
CYP2D6-substrate:	0.91
CYP3A4-inhibitor:	0.511
CYP3A4-substrate:	0.909

ADMET: Excretion

Clearance (CL):	10.603
Half-life (T1/2):	0.874

ADMET: Toxicity

hERG Blockers:	0.254
Human Hepatotoxicity (H-HT):	0.199
Drug-inuced Liver Injury (DILI):	0.635
AMES Toxicity:	0.041
Rat Oral Acute Toxicity:	0.092
Maximum Recommended Daily Dose:	0.894
Skin Sensitization:	0.976
Carcinogencity:	0.037
Eye Corrosion:	0.003
Eye Irritation:	0.354
Respiratory Toxicity:	0.693

Download Data

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

Natural Product: NPC252402

Natural Product ID:	NPC252402
*Common Name:**	(+)-9'-O-(E)-Feruloyl-5,5'-Dimethoxylariciresinol
IUPAC Name:	[(2S,3R,4R)-2-(4-hydroxy-3,5-dimethoxyphenyl)-4-[(4-hydroxy-3,5-dimethoxyphenyl)methyl]oxolan-3-yl]methyl (E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate
Synonyms:
Standard InCHIKey:	NTYDMYPTASSNQW-XMFFLOPHSA-N
Standard InCHI:	InChI=1S/C32H36O11/c1-37-24-11-18(6-8-23(24)33)7-9-29(34)42-17-22-21(10-19-12-25(38-2)30(35)26(13-19)39-3)16-43-32(22)20-14-27(40-4)31(36)28(15-20)41-5/h6-9,11-15,21-22,32-33,35-36H,10,16-17H2,1-5H3/b9-7+/t21-,22-,32+/m0/s1
SMILES:	COc1cc(cc(c1O)OC)[C@H]1OC[C@@H]([C@@H]1COC(=O)/C=C/c1ccc(c(c1)OC)O)Cc1cc(OC)c(c(c1)OC)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL404050
PubChem CID:	44448269
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0001392] Lignans, neolignans and related compounds [CHEMONTID:0003686] Furanoid lignans [CHEMONTID:0001604] Tetrahydrofuran lignans [CHEMONTID:0003422] 7,9'-epoxylignans

*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
NPO18723	Zanthoxylum avicennae	Species	Rutaceae	Eukaryota	stem wood	Pakuashan, Changhua County, Taiwan	2006-Jun	PMID[18211005]
NPO18723	Zanthoxylum avicennae	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18723	Zanthoxylum avicennae	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18723	Zanthoxylum avicennae	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO18723	Zanthoxylum avicennae	Species	Rutaceae	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	2

Activity Type	# Activity
NON-MOLECULAR	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	50000.0	nM	PMID[553002]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	33560.0	nM	PMID[553002]

☑ 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 NPC252402 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	315
0.1-0.2	1316
0.2-0.3	3149
0.3-0.4	7827
0.4-0.5	10912
0.5-0.6	3944
0.6-0.7	7161
0.7-0.8	6584
0.8-0.85	1190
0.85-0.9	267
0.9-0.95	28
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC102934
0.9571	High Similarity	NPC67467
0.9452	High Similarity	NPC476434
0.9396	High Similarity	NPC125495
0.9388	High Similarity	NPC475141
0.9324	High Similarity	NPC473736
0.9247	High Similarity	NPC475250
0.9205	High Similarity	NPC215400
0.9205	High Similarity	NPC230531
0.9189	High Similarity	NPC478268
0.9128	High Similarity	NPC115203
0.9128	High Similarity	NPC470769
0.9078	High Similarity	NPC120852
0.9078	High Similarity	NPC471988
0.9071	High Similarity	NPC67247
0.906	High Similarity	NPC472612
0.906	High Similarity	NPC472611
0.906	High Similarity	NPC289967
0.9041	High Similarity	NPC268515
0.9041	High Similarity	NPC40222
0.9034	High Similarity	NPC471415
0.9034	High Similarity	NPC470097
0.9034	High Similarity	NPC114119
0.9021	High Similarity	NPC106055
0.9021	High Similarity	NPC266197
0.9021	High Similarity	NPC291101
0.9021	High Similarity	NPC110699
0.9014	High Similarity	NPC281780
0.9013	High Similarity	NPC470827
0.9	High Similarity	NPC158331
0.8986	High Similarity	NPC90896
0.8986	High Similarity	NPC283839
0.8986	High Similarity	NPC474393
0.8986	High Similarity	NPC474347
0.898	High Similarity	NPC328567
0.898	High Similarity	NPC327412
0.898	High Similarity	NPC320671
0.898	High Similarity	NPC320970
0.8974	High Similarity	NPC59516
0.8973	High Similarity	NPC473909
0.8973	High Similarity	NPC477702
0.8973	High Similarity	NPC143120
0.8973	High Similarity	NPC274960
0.8954	High Similarity	NPC470828
0.8947	High Similarity	NPC11411
0.8936	High Similarity	NPC244983
0.8936	High Similarity	NPC326095
0.8936	High Similarity	NPC135127
0.8936	High Similarity	NPC287745
0.8933	High Similarity	NPC267091
0.8929	High Similarity	NPC175067
0.8929	High Similarity	NPC204215
0.8926	High Similarity	NPC470916
0.8912	High Similarity	NPC212890
0.8912	High Similarity	NPC324492
0.8912	High Similarity	NPC260397
0.8912	High Similarity	NPC317053
0.8903	High Similarity	NPC473445
0.8889	High Similarity	NPC475592
0.8882	High Similarity	NPC476065
0.8873	High Similarity	NPC99572
0.8873	High Similarity	NPC24490
0.8873	High Similarity	NPC141765
0.8873	High Similarity	NPC165155
0.8873	High Similarity	NPC34103
0.8873	High Similarity	NPC126409
0.8867	High Similarity	NPC243891
0.8859	High Similarity	NPC106138
0.8859	High Similarity	NPC470098
0.8859	High Similarity	NPC470826
0.8859	High Similarity	NPC473266
0.8846	High Similarity	NPC291977
0.8844	High Similarity	NPC181615
0.8844	High Similarity	NPC163898
0.8836	High Similarity	NPC470811
0.8836	High Similarity	NPC477697
0.8836	High Similarity	NPC106920
0.8836	High Similarity	NPC477696
0.8836	High Similarity	NPC273657
0.8831	High Similarity	NPC478269
0.8819	High Similarity	NPC22517
0.8811	High Similarity	NPC471719
0.8811	High Similarity	NPC77861
0.8808	High Similarity	NPC163598
0.8808	High Similarity	NPC120774
0.8808	High Similarity	NPC264875
0.8808	High Similarity	NPC477378
0.8808	High Similarity	NPC475229
0.8805	High Similarity	NPC180768
0.88	High Similarity	NPC24425
0.8792	High Similarity	NPC28651
0.8792	High Similarity	NPC210611
0.8792	High Similarity	NPC192763
0.8792	High Similarity	NPC80732
0.8792	High Similarity	NPC201148
0.8792	High Similarity	NPC261122
0.8792	High Similarity	NPC187398
0.8792	High Similarity	NPC215095
0.8792	High Similarity	NPC199311
0.8792	High Similarity	NPC476348
0.8792	High Similarity	NPC473408
0.8792	High Similarity	NPC3460
0.8792	High Similarity	NPC300262
0.8784	High Similarity	NPC474054
0.8782	High Similarity	NPC42797
0.8776	High Similarity	NPC472713
0.8776	High Similarity	NPC187774
0.8776	High Similarity	NPC472712
0.8776	High Similarity	NPC473046
0.8776	High Similarity	NPC297342
0.8776	High Similarity	NPC118385
0.8776	High Similarity	NPC87883
0.8767	High Similarity	NPC131971
0.8767	High Similarity	NPC278469
0.8767	High Similarity	NPC193722
0.8759	High Similarity	NPC267291
0.8759	High Similarity	NPC309124
0.8759	High Similarity	NPC184797
0.875	High Similarity	NPC126206
0.875	High Similarity	NPC477377
0.875	High Similarity	NPC65591
0.875	High Similarity	NPC149735
0.875	High Similarity	NPC178574
0.8742	High Similarity	NPC324517
0.8742	High Similarity	NPC329343
0.8742	High Similarity	NPC321972
0.8741	High Similarity	NPC93783
0.8733	High Similarity	NPC176903
0.8733	High Similarity	NPC125570
0.8733	High Similarity	NPC30688
0.8725	High Similarity	NPC295297
0.8725	High Similarity	NPC476347
0.8725	High Similarity	NPC39657
0.8723	High Similarity	NPC470095
0.8723	High Similarity	NPC470096
0.8723	High Similarity	NPC474017
0.8718	High Similarity	NPC478267
0.8718	High Similarity	NPC149873
0.8718	High Similarity	NPC7191
0.8716	High Similarity	NPC83743
0.8716	High Similarity	NPC476841
0.8716	High Similarity	NPC476843
0.8716	High Similarity	NPC287615
0.8716	High Similarity	NPC216819
0.8716	High Similarity	NPC262182
0.8714	High Similarity	NPC83062
0.8707	High Similarity	NPC469630
0.8699	High Similarity	NPC470372
0.8699	High Similarity	NPC83375
0.8699	High Similarity	NPC224876
0.8693	High Similarity	NPC268484
0.869	High Similarity	NPC473739
0.869	High Similarity	NPC236306
0.869	High Similarity	NPC232164
0.8684	High Similarity	NPC471154
0.8681	High Similarity	NPC471665
0.8681	High Similarity	NPC471664
0.8681	High Similarity	NPC143895
0.8679	High Similarity	NPC311912
0.8675	High Similarity	NPC120426
0.8675	High Similarity	NPC188393
0.8675	High Similarity	NPC205727
0.8675	High Similarity	NPC294522
0.8675	High Similarity	NPC21184
0.8675	High Similarity	NPC470934
0.8671	High Similarity	NPC111635
0.8671	High Similarity	NPC309744
0.8667	High Similarity	NPC236166
0.8662	High Similarity	NPC201587
0.8662	High Similarity	NPC253105
0.8654	High Similarity	NPC476373
0.8652	High Similarity	NPC145305
0.8652	High Similarity	NPC241522
0.8652	High Similarity	NPC42300
0.8652	High Similarity	NPC242807
0.8652	High Similarity	NPC153739
0.8652	High Similarity	NPC92164
0.8652	High Similarity	NPC187998
0.8652	High Similarity	NPC257582
0.8652	High Similarity	NPC77040
0.8652	High Similarity	NPC64201
0.8652	High Similarity	NPC174495
0.8649	High Similarity	NPC110063
0.8643	High Similarity	NPC184733
0.8643	High Similarity	NPC45774
0.8643	High Similarity	NPC282703
0.8643	High Similarity	NPC11258
0.8643	High Similarity	NPC21867
0.8643	High Similarity	NPC129570
0.8643	High Similarity	NPC109275
0.8643	High Similarity	NPC128208
0.8639	High Similarity	NPC5262
0.8639	High Similarity	NPC287124
0.8639	High Similarity	NPC472714
0.8639	High Similarity	NPC107161
0.8639	High Similarity	NPC140502
0.863	High Similarity	NPC160283
0.863	High Similarity	NPC254759
0.863	High Similarity	NPC177868
0.8627	High Similarity	NPC297271

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 NPC252402 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	257
0.1-0.2	806
0.2-0.3	1621
0.3-0.4	2643
0.4-0.5	2003
0.5-0.6	1094
0.6-0.7	596
0.7-0.8	121
0.8-0.85	9
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8582	High Similarity	NPD3027	Phase 3
0.8471	Intermediate Similarity	NPD6234	Discontinued
0.8344	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8269	Intermediate Similarity	NPD37	Approved
0.8228	Intermediate Similarity	NPD4966	Approved
0.8228	Intermediate Similarity	NPD4965	Approved
0.8228	Intermediate Similarity	NPD4967	Phase 2
0.8221	Intermediate Similarity	NPD7228	Approved
0.8188	Intermediate Similarity	NPD7266	Discontinued
0.8151	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8151	Intermediate Similarity	NPD1613	Approved
0.8129	Intermediate Similarity	NPD1653	Approved
0.8065	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.8047	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.8025	Intermediate Similarity	NPD7199	Phase 2
0.8	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7987	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7939	Intermediate Similarity	NPD7473	Discontinued
0.7931	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7927	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7925	Intermediate Similarity	NPD1934	Approved
0.7892	Intermediate Similarity	NPD3818	Discontinued
0.7879	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7879	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7879	Intermediate Similarity	NPD6166	Phase 2
0.7877	Intermediate Similarity	NPD4908	Phase 1
0.7866	Intermediate Similarity	NPD6232	Discontinued
0.7857	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD6190	Approved
0.7844	Intermediate Similarity	NPD5844	Phase 1
0.7778	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD3882	Suspended
0.777	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7764	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7716	Intermediate Similarity	NPD3817	Phase 2
0.7706	Intermediate Similarity	NPD7240	Approved
0.7706	Intermediate Similarity	NPD7685	Pre-registration
0.7697	Intermediate Similarity	NPD8127	Discontinued
0.7692	Intermediate Similarity	NPD7074	Phase 3
0.7661	Intermediate Similarity	NPD7549	Discontinued
0.7654	Intermediate Similarity	NPD2801	Approved
0.7654	Intermediate Similarity	NPD1465	Phase 2
0.7633	Intermediate Similarity	NPD7054	Approved
0.7622	Intermediate Similarity	NPD7075	Discontinued
0.7616	Intermediate Similarity	NPD230	Phase 1
0.7588	Intermediate Similarity	NPD7472	Approved
0.7572	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7564	Intermediate Similarity	NPD8166	Discontinued
0.7561	Intermediate Similarity	NPD7768	Phase 2
0.755	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.755	Intermediate Similarity	NPD4060	Phase 1
0.755	Intermediate Similarity	NPD3620	Phase 2
0.7546	Intermediate Similarity	NPD7819	Suspended
0.7534	Intermediate Similarity	NPD2982	Phase 2
0.7534	Intermediate Similarity	NPD2983	Phase 2
0.753	Intermediate Similarity	NPD5494	Approved
0.7517	Intermediate Similarity	NPD1610	Phase 2
0.75	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD5283	Phase 1
0.75	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6559	Discontinued
0.7486	Intermediate Similarity	NPD7680	Approved
0.7469	Intermediate Similarity	NPD4380	Phase 2
0.7467	Intermediate Similarity	NPD7095	Approved
0.7466	Intermediate Similarity	NPD2981	Phase 2
0.7457	Intermediate Similarity	NPD7808	Phase 3
0.7457	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7452	Intermediate Similarity	NPD4628	Phase 3
0.7452	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.745	Intermediate Similarity	NPD3018	Phase 2
0.745	Intermediate Similarity	NPD2861	Phase 2
0.7439	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7421	Intermediate Similarity	NPD4357	Discontinued
0.7421	Intermediate Similarity	NPD1511	Approved
0.7417	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7399	Intermediate Similarity	NPD7251	Discontinued
0.7397	Intermediate Similarity	NPD422	Phase 1
0.7397	Intermediate Similarity	NPD3705	Approved
0.7389	Intermediate Similarity	NPD1652	Phase 2
0.7386	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD5124	Phase 1
0.7386	Intermediate Similarity	NPD6355	Discontinued
0.7368	Intermediate Similarity	NPD6233	Phase 2
0.7363	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7357	Intermediate Similarity	NPD228	Approved
0.7342	Intermediate Similarity	NPD3750	Approved
0.7342	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7342	Intermediate Similarity	NPD4110	Phase 3
0.7341	Intermediate Similarity	NPD6797	Phase 2
0.7337	Intermediate Similarity	NPD7229	Phase 3
0.7329	Intermediate Similarity	NPD7314	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD1512	Approved
0.7317	Intermediate Similarity	NPD7411	Suspended
0.7305	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD3764	Approved
0.7303	Intermediate Similarity	NPD6798	Discontinued
0.7292	Intermediate Similarity	NPD5536	Phase 2
0.7289	Intermediate Similarity	NPD5402	Approved
0.7278	Intermediate Similarity	NPD6674	Discontinued
0.7273	Intermediate Similarity	NPD6801	Discontinued
0.7267	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7261	Intermediate Similarity	NPD5763	Approved
0.7261	Intermediate Similarity	NPD5762	Approved
0.7251	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD1548	Phase 1
0.7229	Intermediate Similarity	NPD8455	Phase 2
0.7226	Intermediate Similarity	NPD6653	Approved
0.7215	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7214	Intermediate Similarity	NPD3021	Approved
0.7214	Intermediate Similarity	NPD3022	Approved
0.7208	Intermediate Similarity	NPD4140	Approved
0.7205	Intermediate Similarity	NPD6799	Approved
0.7197	Intermediate Similarity	NPD2935	Discontinued
0.7195	Intermediate Similarity	NPD6055	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD5242	Approved
0.719	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7186	Intermediate Similarity	NPD6374	Clinical (unspecified phase)
0.7186	Intermediate Similarity	NPD5353	Approved
0.7181	Intermediate Similarity	NPD4749	Approved
0.7179	Intermediate Similarity	NPD7097	Phase 1
0.7178	Intermediate Similarity	NPD5403	Approved
0.717	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7161	Intermediate Similarity	NPD4340	Discontinued
0.716	Intermediate Similarity	NPD2533	Approved
0.716	Intermediate Similarity	NPD2532	Approved
0.716	Intermediate Similarity	NPD2534	Approved
0.7152	Intermediate Similarity	NPD6599	Discontinued
0.7134	Intermediate Similarity	NPD1510	Phase 2
0.7126	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD4625	Phase 3
0.7119	Intermediate Similarity	NPD8313	Approved
0.7119	Intermediate Similarity	NPD8312	Approved
0.7117	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD1549	Phase 2
0.7101	Intermediate Similarity	NPD6971	Discontinued
0.7101	Intermediate Similarity	NPD3749	Approved
0.7095	Intermediate Similarity	NPD8434	Phase 2
0.7093	Intermediate Similarity	NPD3926	Phase 2
0.7086	Intermediate Similarity	NPD2797	Approved
0.7076	Intermediate Similarity	NPD6959	Discontinued
0.7075	Intermediate Similarity	NPD1357	Approved
0.7071	Intermediate Similarity	NPD1358	Approved
0.7063	Intermediate Similarity	NPD7843	Approved
0.7063	Intermediate Similarity	NPD5535	Approved
0.7059	Intermediate Similarity	NPD919	Approved
0.7055	Intermediate Similarity	NPD5401	Approved
0.7055	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD5735	Approved
0.7044	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD7124	Phase 2
0.7034	Intermediate Similarity	NPD7157	Approved
0.7033	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD4626	Approved
0.7025	Intermediate Similarity	NPD3748	Approved
0.7012	Intermediate Similarity	NPD6273	Approved
0.7006	Intermediate Similarity	NPD7039	Approved
0.7006	Intermediate Similarity	NPD7038	Approved
0.7006	Intermediate Similarity	NPD6386	Approved
0.7006	Intermediate Similarity	NPD6385	Approved
0.7	Intermediate Similarity	NPD1608	Approved
0.7	Intermediate Similarity	NPD3134	Approved
0.6993	Remote Similarity	NPD5736	Approved
0.6993	Remote Similarity	NPD9494	Approved
0.6988	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6988	Remote Similarity	NPD4005	Discontinued
0.6987	Remote Similarity	NPD1558	Phase 1
0.6987	Remote Similarity	NPD1240	Approved
0.6983	Remote Similarity	NPD8053	Approved
0.6983	Remote Similarity	NPD8054	Approved
0.6981	Remote Similarity	NPD1551	Phase 2
0.6981	Remote Similarity	NPD2438	Suspended
0.6981	Remote Similarity	NPD6100	Approved
0.6981	Remote Similarity	NPD2796	Approved
0.6981	Remote Similarity	NPD6099	Approved
0.698	Remote Similarity	NPD3496	Discontinued
0.6968	Remote Similarity	NPD3268	Approved
0.6964	Remote Similarity	NPD7945	Clinical (unspecified phase)
0.6961	Remote Similarity	NPD7906	Approved
0.6959	Remote Similarity	NPD5691	Approved
0.6957	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD4236	Phase 3
0.6957	Remote Similarity	NPD4237	Approved
0.6951	Remote Similarity	NPD7447	Phase 1
0.6951	Remote Similarity	NPD7446	Clinical (unspecified phase)
0.6946	Remote Similarity	NPD4675	Approved
0.6946	Remote Similarity	NPD4678	Approved
0.6943	Remote Similarity	NPD447	Suspended
0.6937	Remote Similarity	NPD3540	Phase 1
0.6937	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD5058	Phase 3
0.6928	Remote Similarity	NPD3686	Approved
0.6928	Remote Similarity	NPD6584	Phase 3
0.6928	Remote Similarity	NPD3687	Approved
0.6923	Remote Similarity	NPD2977	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