NPASS Compound

Structure

CID61604 OpenBabel06191715402D 37 40 0 0 1 0 0 0 0 0999 V2000 0.6955 -4.6681 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 -2.9008 -4.9260 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 -2.1577 -5.5952 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 -3.4361 -3.2788 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7419 -3.6389 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 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6962 -4.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6929 -3.9479 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 -4.3871 -3.5878 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.1962 -3.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.2066 -5.2862 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 -0.9987 -4.3080 0.0000 C 0 0 0 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 0.8660 -0.5000 0.0000 C 0 0 2 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 -2.0000 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 -6.0052 -3.5878 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 2.5981 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.4635 -5.9553 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 -0.0000 -3.0000 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 -6.9562 -3.2788 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0477 -3.9990 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.6962 -4.5388 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 33 1 0 0 0 0 2 34 1 0 0 0 0 3 5 2 0 0 0 0 3 13 1 0 0 0 0 4 6 2 0 0 0 0 4 14 1 0 0 0 0 5 17 1 0 0 0 0 6 18 1 0 0 0 0 7 13 1 0 0 0 0 8 14 1 0 0 0 0 9 13 2 0 0 0 0 9 19 1 0 0 0 0 10 14 2 0 0 0 0 10 20 1 0 0 0 0 11 27 1 0 0 0 0 12 15 1 0 0 0 0 12 35 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 25 1 0 0 0 0 17 19 2 0 0 0 0 17 28 1 0 0 0 0 18 20 2 0 0 0 0 18 36 1 0 0 0 0 19 33 1 0 0 0 0 20 34 1 0 0 0 0 21 11 1 6 0 0 0 21 22 1 0 0 0 0 21 37 1 0 0 0 0 22 23 1 0 0 0 0 22 29 1 1 0 0 0 23 24 1 0 0 0 0 23 30 1 6 0 0 0 24 26 1 0 0 0 0 24 31 1 1 0 0 0 25 32 2 0 0 0 0 25 35 1 0 0 0 0 26 36 1 6 0 0 0 26 37 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	520.19
Volume:	502.264
LogP:	1.061
LogD:	1.226
LogS:	-3.466
# Rotatable Bonds:	9
TPSA:	164.37
# H-Bond Aceptor:	11
# H-Bond Donor:	5
# Rings:	4
# Heavy Atoms:	11

MedChem Properties

QED Drug-Likeness Score:	0.286
Synthetic Accessibility Score:	4.166
Fsp3:	0.5
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:	-6.093
MDCK Permeability:	2.32374277402414e-05
Pgp-inhibitor:	0.03
Pgp-substrate:	0.221
Human Intestinal Absorption (HIA):	0.243
20% Bioavailability (F20%):	0.006
30% Bioavailability (F30%):	0.801

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.186
Plasma Protein Binding (PPB):	80.9142837524414%
Volume Distribution (VD):	0.334
Pgp-substrate:	13.95608139038086%

ADMET: Metabolism

CYP1A2-inhibitor:	0.069
CYP1A2-substrate:	0.299
CYP2C19-inhibitor:	0.048
CYP2C19-substrate:	0.794
CYP2C9-inhibitor:	0.027
CYP2C9-substrate:	0.556
CYP2D6-inhibitor:	0.137
CYP2D6-substrate:	0.829
CYP3A4-inhibitor:	0.386
CYP3A4-substrate:	0.232

ADMET: Excretion

Clearance (CL):	11.19
Half-life (T1/2):	0.837

ADMET: Toxicity

hERG Blockers:	0.412
Human Hepatotoxicity (H-HT):	0.267
Drug-inuced Liver Injury (DILI):	0.135
AMES Toxicity:	0.119
Rat Oral Acute Toxicity:	0.009
Maximum Recommended Daily Dose:	0.063
Skin Sensitization:	0.667
Carcinogencity:	0.292
Eye Corrosion:	0.003
Eye Irritation:	0.02
Respiratory Toxicity:	0.022

Download Data

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

Natural Product: NPC61604

Natural Product ID:	NPC61604
*Common Name:**	Styraxlignolide E
IUPAC Name:	(3S,4S)-4-[(4-hydroxy-3-methoxyphenyl)methyl]-3-[[3-methoxy-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]methyl]oxolan-2-one
Synonyms:	Styraxlignolide E
Standard InCHIKey:	AAGCATAPYOEULE-ZQJJHTFWSA-N
Standard InCHI:	InChI=1S/C26H32O11/c1-33-19-9-13(3-5-17(19)28)7-15-12-35-25(32)16(15)8-14-4-6-18(20(10-14)34-2)36-26-24(31)23(30)22(29)21(11-27)37-26/h3-6,9-10,15-16,21-24,26-31H,7-8,11-12H2,1-2H3/t15-,16+,21-,22-,23+,24-,26-/m1/s1
SMILES:	COc1cc(ccc1O)C[C@@H]1COC(=O)[C@H]1Cc1ccc(c(c1)OC)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL520065
PubChem CID:	11432381
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0001392] Lignans, neolignans and related compounds [CHEMONTID:0001511] Lignan 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
NPO19805	Forsythia viridissima	Species	Oleaceae	Eukaryota	n.a.	flower	n.a.	PMID[15481244]
NPO30866	Styrax japonica	Species	Styracaceae	Eukaryota	n.a.	bark	n.a.	PMID[15577246]
NPO30866	Styrax japonica	Species	Styracaceae	Eukaryota	stem bark	n.a.	n.a.	PMID[15620237]
NPO21387	Forsythia suspensa	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17156960]
NPO21387	Forsythia suspensa	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26422318]
NPO21387	Forsythia suspensa	Species	Oleaceae	Eukaryota	Fruits	n.a.	n.a.	PMID[28218000]
NPO19805	Forsythia viridissima	Species	Oleaceae	Eukaryota	Roots	n.a.	n.a.	PMID[30676026]
NPO30866	Styrax japonica	Species	Styracaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO20535	Podocarpus spicatus	Species	Podocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19805	Forsythia viridissima	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21387	Forsythia suspensa	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO20535	Podocarpus spicatus	Species	Podocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19805	Forsythia viridissima	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17951	Styrax japonicus	Species	Styracaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21387	Forsythia suspensa	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20535	Podocarpus spicatus	Species	Podocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO19805	Forsythia viridissima	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO21387	Forsythia suspensa	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO21387	Forsythia suspensa	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17951	Styrax japonicus	Species	Styracaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20535	Podocarpus spicatus	Species	Podocarpaceae	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	1

Activity Type	# Activity
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1	Others	Radical scavenging activity		IC50	=	194000.0	nM	PMID[454390]

☑ 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 NPC61604 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	314
0.1-0.2	1221
0.2-0.3	2881
0.3-0.4	6414
0.4-0.5	10764
0.5-0.6	6377
0.6-0.7	7790
0.7-0.8	5852
0.8-0.85	811
0.85-0.9	244
0.9-0.95	16
0.95-1	13

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC245615
1.0	High Similarity	NPC299706
1.0	High Similarity	NPC115466
0.9797	High Similarity	NPC163635
0.9793	High Similarity	NPC229882
0.9793	High Similarity	NPC158635
0.9664	High Similarity	NPC478055
0.9597	High Similarity	NPC38699
0.9404	High Similarity	NPC228357
0.9338	High Similarity	NPC186316
0.931	High Similarity	NPC470950
0.931	High Similarity	NPC185307
0.9257	High Similarity	NPC116229
0.9247	High Similarity	NPC129417
0.9247	High Similarity	NPC283995
0.9247	High Similarity	NPC470235
0.9241	High Similarity	NPC476356
0.9241	High Similarity	NPC52664
0.9184	High Similarity	NPC22150
0.9184	High Similarity	NPC38041
0.9184	High Similarity	NPC279298
0.9178	High Similarity	NPC46092
0.9172	High Similarity	NPC100675
0.9172	High Similarity	NPC472711
0.9122	High Similarity	NPC112861
0.9091	High Similarity	NPC226759
0.9067	High Similarity	NPC478242
0.906	High Similarity	NPC114505
0.906	High Similarity	NPC224674
0.906	High Similarity	NPC31325
0.906	High Similarity	NPC15956
0.906	High Similarity	NPC275284
0.906	High Similarity	NPC213074
0.906	High Similarity	NPC39657
0.906	High Similarity	NPC193473
0.9054	High Similarity	NPC18979
0.9048	High Similarity	NPC477898
0.9032	High Similarity	NPC469654
0.9026	High Similarity	NPC11411
0.9026	High Similarity	NPC471405
0.902	High Similarity	NPC194095
0.902	High Similarity	NPC327032
0.902	High Similarity	NPC191046
0.902	High Similarity	NPC136757
0.9013	High Similarity	NPC478268
0.9006	High Similarity	NPC316539
0.8993	High Similarity	NPC3982
0.8986	High Similarity	NPC84181
0.898	High Similarity	NPC246947
0.8974	High Similarity	NPC44507
0.8968	High Similarity	NPC223335
0.8968	High Similarity	NPC40920
0.8966	High Similarity	NPC281780
0.8966	High Similarity	NPC138738
0.8966	High Similarity	NPC470413
0.8961	High Similarity	NPC10205
0.8954	High Similarity	NPC473236
0.8954	High Similarity	NPC44730
0.894	High Similarity	NPC474965
0.894	High Similarity	NPC216223
0.894	High Similarity	NPC51328
0.894	High Similarity	NPC174512
0.894	High Similarity	NPC111785
0.894	High Similarity	NPC55158
0.894	High Similarity	NPC477695
0.894	High Similarity	NPC293757
0.894	High Similarity	NPC145569
0.894	High Similarity	NPC286235
0.894	High Similarity	NPC668
0.8926	High Similarity	NPC223185
0.8926	High Similarity	NPC476301
0.8926	High Similarity	NPC43508
0.8924	High Similarity	NPC116759
0.8924	High Similarity	NPC14294
0.8919	High Similarity	NPC478239
0.8917	High Similarity	NPC115624
0.8912	High Similarity	NPC282291
0.8912	High Similarity	NPC166137
0.891	High Similarity	NPC173726
0.891	High Similarity	NPC179914
0.891	High Similarity	NPC241600
0.891	High Similarity	NPC478269
0.8897	High Similarity	NPC52277
0.8897	High Similarity	NPC199459
0.8897	High Similarity	NPC177035
0.8889	High Similarity	NPC36130
0.8889	High Similarity	NPC302610
0.8889	High Similarity	NPC477699
0.8889	High Similarity	NPC56184
0.8889	High Similarity	NPC134905
0.8889	High Similarity	NPC203664
0.8882	High Similarity	NPC475224
0.8882	High Similarity	NPC98624
0.8875	High Similarity	NPC185498
0.8874	High Similarity	NPC130449
0.8874	High Similarity	NPC248132
0.8868	High Similarity	NPC222531
0.8861	High Similarity	NPC22324
0.8859	High Similarity	NPC471063
0.8859	High Similarity	NPC471667
0.8859	High Similarity	NPC79429
0.8859	High Similarity	NPC472712
0.8859	High Similarity	NPC217635
0.8859	High Similarity	NPC472713
0.8859	High Similarity	NPC473046
0.8859	High Similarity	NPC118385
0.8859	High Similarity	NPC110063
0.8859	High Similarity	NPC187774
0.8854	High Similarity	NPC239966
0.8854	High Similarity	NPC203020
0.8854	High Similarity	NPC91634
0.8854	High Similarity	NPC150943
0.8854	High Similarity	NPC268718
0.8851	High Similarity	NPC31751
0.8851	High Similarity	NPC157816
0.8851	High Similarity	NPC253481
0.8851	High Similarity	NPC140502
0.8851	High Similarity	NPC253722
0.8846	High Similarity	NPC133984
0.8844	High Similarity	NPC106944
0.8839	High Similarity	NPC131532
0.8831	High Similarity	NPC157898
0.8831	High Similarity	NPC137813
0.8828	High Similarity	NPC101624
0.8828	High Similarity	NPC184938
0.8828	High Similarity	NPC113295
0.8824	High Similarity	NPC477700
0.8816	High Similarity	NPC106138
0.88	High Similarity	NPC476382
0.88	High Similarity	NPC100998
0.88	High Similarity	NPC34927
0.88	High Similarity	NPC262182
0.88	High Similarity	NPC287615
0.88	High Similarity	NPC216819
0.88	High Similarity	NPC34587
0.88	High Similarity	NPC469586
0.88	High Similarity	NPC252292
0.88	High Similarity	NPC83743
0.8797	High Similarity	NPC478267
0.8797	High Similarity	NPC149873
0.8797	High Similarity	NPC7191
0.8797	High Similarity	NPC100465
0.8797	High Similarity	NPC152424
0.8792	High Similarity	NPC470811
0.8792	High Similarity	NPC477696
0.8792	High Similarity	NPC273657
0.8792	High Similarity	NPC113680
0.8792	High Similarity	NPC106920
0.8792	High Similarity	NPC278961
0.8792	High Similarity	NPC477697
0.879	High Similarity	NPC160780
0.879	High Similarity	NPC469384
0.879	High Similarity	NPC289811
0.8784	High Similarity	NPC186406
0.8776	High Similarity	NPC156376
0.8767	High Similarity	NPC471988
0.8766	High Similarity	NPC476434
0.8765	High Similarity	NPC179240
0.8759	High Similarity	NPC476411
0.8759	High Similarity	NPC176814
0.8759	High Similarity	NPC4982
0.8759	High Similarity	NPC67247
0.8759	High Similarity	NPC300776
0.8759	High Similarity	NPC68779
0.8759	High Similarity	NPC5310
0.8759	High Similarity	NPC187194
0.8758	High Similarity	NPC470934
0.8758	High Similarity	NPC472710
0.8758	High Similarity	NPC188393
0.8758	High Similarity	NPC472709
0.875	High Similarity	NPC475738
0.8742	High Similarity	NPC276753
0.8742	High Similarity	NPC205796
0.8742	High Similarity	NPC476865
0.8742	High Similarity	NPC212890
0.8742	High Similarity	NPC199928
0.8734	High Similarity	NPC119910
0.8733	High Similarity	NPC25292
0.8733	High Similarity	NPC232228
0.8733	High Similarity	NPC473045
0.8726	High Similarity	NPC1913
0.8726	High Similarity	NPC286919
0.8726	High Similarity	NPC475663
0.8726	High Similarity	NPC472860
0.8725	High Similarity	NPC472714
0.8725	High Similarity	NPC131971
0.8725	High Similarity	NPC189115
0.8725	High Similarity	NPC302506
0.8725	High Similarity	NPC5262
0.8725	High Similarity	NPC469559
0.8725	High Similarity	NPC253878
0.8718	High Similarity	NPC238834
0.8716	High Similarity	NPC147379
0.871	High Similarity	NPC245948
0.871	High Similarity	NPC65591
0.871	High Similarity	NPC178574
0.8707	High Similarity	NPC304152
0.8704	High Similarity	NPC21956
0.8701	High Similarity	NPC32079
0.8699	High Similarity	NPC123988

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 NPC61604 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	262
0.1-0.2	736
0.2-0.3	1634
0.3-0.4	2529
0.4-0.5	2152
0.5-0.6	1136
0.6-0.7	595
0.7-0.8	95
0.8-0.85	6
0.85-0.9	5
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8875	High Similarity	NPD7228	Approved
0.879	High Similarity	NPD6234	Discontinued
0.871	High Similarity	NPD37	Approved
0.8662	High Similarity	NPD4967	Phase 2
0.8662	High Similarity	NPD4965	Approved
0.8662	High Similarity	NPD4966	Approved
0.8447	Intermediate Similarity	NPD7199	Phase 2
0.8434	Intermediate Similarity	NPD7685	Pre-registration
0.8415	Intermediate Similarity	NPD3818	Discontinued
0.84	Intermediate Similarity	NPD7266	Discontinued
0.8323	Intermediate Similarity	NPD7240	Approved
0.8313	Intermediate Similarity	NPD7074	Phase 3
0.8312	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.8253	Intermediate Similarity	NPD7054	Approved
0.8235	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.8232	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.8204	Intermediate Similarity	NPD7472	Approved
0.8187	Intermediate Similarity	NPD8455	Phase 2
0.8166	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8101	Intermediate Similarity	NPD1653	Approved
0.8086	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD7251	Discontinued
0.7953	Intermediate Similarity	NPD7808	Phase 3
0.7947	Intermediate Similarity	NPD6355	Discontinued
0.7941	Intermediate Similarity	NPD6797	Phase 2
0.7935	Intermediate Similarity	NPD6674	Discontinued
0.7933	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7919	Intermediate Similarity	NPD3027	Phase 3
0.7901	Intermediate Similarity	NPD1934	Approved
0.7895	Intermediate Similarity	NPD6559	Discontinued
0.7885	Intermediate Similarity	NPD4110	Phase 3
0.7885	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7881	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7881	Intermediate Similarity	NPD1613	Approved
0.7861	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD7680	Approved
0.7834	Intermediate Similarity	NPD6190	Approved
0.7818	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7812	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7803	Intermediate Similarity	NPD8313	Approved
0.7803	Intermediate Similarity	NPD8312	Approved
0.7784	Intermediate Similarity	NPD8127	Discontinued
0.7771	Intermediate Similarity	NPD4628	Phase 3
0.7751	Intermediate Similarity	NPD6166	Phase 2
0.7751	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7751	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7744	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7727	Intermediate Similarity	NPD7097	Phase 1
0.7697	Intermediate Similarity	NPD6233	Phase 2
0.7688	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7662	Intermediate Similarity	NPD6653	Approved
0.7651	Intermediate Similarity	NPD3882	Suspended
0.7636	Intermediate Similarity	NPD2801	Approved
0.7636	Intermediate Similarity	NPD1465	Phase 2
0.7632	Intermediate Similarity	NPD6798	Discontinued
0.763	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD3705	Approved
0.7616	Intermediate Similarity	NPD5844	Phase 1
0.7616	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7616	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.759	Intermediate Similarity	NPD3817	Phase 2
0.7584	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7568	Intermediate Similarity	NPD1608	Approved
0.7566	Intermediate Similarity	NPD7095	Approved
0.755	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.755	Intermediate Similarity	NPD2861	Phase 2
0.7532	Intermediate Similarity	NPD4060	Phase 1
0.7516	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD5494	Approved
0.75	Intermediate Similarity	NPD1091	Approved
0.75	Intermediate Similarity	NPD7075	Discontinued
0.75	Intermediate Similarity	NPD7473	Discontinued
0.7468	Intermediate Similarity	NPD6004	Phase 3
0.7468	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD6002	Phase 3
0.7468	Intermediate Similarity	NPD6005	Phase 3
0.7468	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7453	Intermediate Similarity	NPD5058	Phase 3
0.7452	Intermediate Similarity	NPD7033	Discontinued
0.7427	Intermediate Similarity	NPD3787	Discontinued
0.7427	Intermediate Similarity	NPD6232	Discontinued
0.7415	Intermediate Similarity	NPD1357	Approved
0.741	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7403	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.74	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD5647	Approved
0.7365	Intermediate Similarity	NPD17	Approved
0.7358	Intermediate Similarity	NPD5763	Approved
0.7358	Intermediate Similarity	NPD5762	Approved
0.7355	Intermediate Similarity	NPD4062	Phase 3
0.7349	Intermediate Similarity	NPD7028	Phase 2
0.7329	Intermediate Similarity	NPD8166	Discontinued
0.7329	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7326	Intermediate Similarity	NPD7229	Phase 3
0.7321	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD7819	Suspended
0.7312	Intermediate Similarity	NPD5958	Discontinued
0.7308	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD3620	Phase 2
0.7303	Intermediate Similarity	NPD2797	Approved
0.7301	Intermediate Similarity	NPD1511	Approved
0.7296	Intermediate Similarity	NPD2438	Suspended
0.7278	Intermediate Similarity	NPD5402	Approved
0.7278	Intermediate Similarity	NPD8434	Phase 2
0.7273	Intermediate Similarity	NPD4908	Phase 1
0.7261	Intermediate Similarity	NPD230	Phase 1
0.7261	Intermediate Similarity	NPD1933	Approved
0.7257	Intermediate Similarity	NPD3751	Discontinued
0.7246	Intermediate Similarity	NPD4380	Phase 2
0.7241	Intermediate Similarity	NPD5283	Phase 1
0.7219	Intermediate Similarity	NPD2978	Approved
0.7219	Intermediate Similarity	NPD2977	Approved
0.7213	Intermediate Similarity	NPD7296	Approved
0.7212	Intermediate Similarity	NPD1512	Approved
0.7212	Intermediate Similarity	NPD6273	Approved
0.7205	Intermediate Similarity	NPD4534	Discontinued
0.7197	Intermediate Similarity	NPD4140	Approved
0.7188	Intermediate Similarity	NPD6099	Approved
0.7188	Intermediate Similarity	NPD6100	Approved
0.7186	Intermediate Similarity	NPD7458	Discontinued
0.7181	Intermediate Similarity	NPD5585	Approved
0.7179	Intermediate Similarity	NPD3268	Approved
0.7179	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD3764	Approved
0.7176	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD4978	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD6801	Discontinued
0.716	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD1610	Phase 2
0.7152	Intermediate Similarity	NPD1535	Discovery
0.7152	Intermediate Similarity	NPD447	Suspended
0.7143	Intermediate Similarity	NPD7157	Approved
0.7134	Intermediate Similarity	NPD8032	Phase 2
0.7126	Intermediate Similarity	NPD3686	Approved
0.7126	Intermediate Similarity	NPD3687	Approved
0.7125	Intermediate Similarity	NPD5588	Approved
0.7124	Intermediate Similarity	NPD1283	Approved
0.7118	Intermediate Similarity	NPD5563	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD3750	Approved
0.7114	Intermediate Similarity	NPD1894	Discontinued
0.7105	Intermediate Similarity	NPD1481	Phase 2
0.7103	Intermediate Similarity	NPD228	Approved
0.7101	Intermediate Similarity	NPD6386	Approved
0.7101	Intermediate Similarity	NPD6385	Approved
0.7097	Intermediate Similarity	NPD9494	Approved
0.7095	Intermediate Similarity	NPD7039	Approved
0.7095	Intermediate Similarity	NPD7038	Approved
0.7089	Intermediate Similarity	NPD2979	Phase 3
0.7083	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD6032	Approved
0.7081	Intermediate Similarity	NPD2935	Discontinued
0.7078	Intermediate Similarity	NPD6362	Approved
0.7066	Intermediate Similarity	NPD5403	Approved
0.7063	Intermediate Similarity	NPD4536	Approved
0.7063	Intermediate Similarity	NPD4538	Approved
0.7063	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD7843	Approved
0.7044	Intermediate Similarity	NPD5735	Approved
0.7037	Intermediate Similarity	NPD1375	Discontinued
0.7037	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7035	Intermediate Similarity	NPD7768	Phase 2
0.7026	Intermediate Similarity	NPD7783	Phase 2
0.7026	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD6663	Approved
0.702	Intermediate Similarity	NPD5125	Phase 3
0.702	Intermediate Similarity	NPD5126	Approved
0.7019	Intermediate Similarity	NPD2799	Discontinued
0.7016	Intermediate Similarity	NPD7435	Discontinued
0.7	Intermediate Similarity	NPD7411	Suspended
0.6994	Remote Similarity	NPD2424	Discontinued
0.6994	Remote Similarity	NPD1549	Phase 2
0.699	Remote Similarity	NPD7827	Phase 1
0.6988	Remote Similarity	NPD6799	Approved
0.6987	Remote Similarity	NPD5736	Approved
0.6982	Remote Similarity	NPD3226	Approved
0.6981	Remote Similarity	NPD1558	Phase 1
0.6981	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD5353	Approved
0.6966	Remote Similarity	NPD3022	Approved
0.6966	Remote Similarity	NPD3021	Approved
0.6962	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6962	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD1652	Phase 2
0.6948	Remote Similarity	NPD4359	Approved
0.6946	Remote Similarity	NPD5401	Approved
0.6946	Remote Similarity	NPD3146	Approved
0.6946	Remote Similarity	NPD3688	Clinical (unspecified phase)
0.6946	Remote Similarity	NPD2532	Approved
0.6946	Remote Similarity	NPD2533	Approved
0.6946	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6946	Remote Similarity	NPD2534	Approved
0.6943	Remote Similarity	NPD7999	Approved
0.6941	Remote Similarity	NPD6599	Discontinued
0.6939	Remote Similarity	NPD5535	Approved
0.6937	Remote Similarity	NPD4622	Approved
0.6937	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD4618	Approved
0.6937	Remote Similarity	NPD4340	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