NPASS Compound

Structure

NPC63628 OpenBabel07101718192D 33 35 0 0 1 0 0 0 0 0999 V2000 -6.0622 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 3.0000 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 -3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -0.0000 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 -4.3301 3.5000 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 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 3.5000 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 -5.1962 -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 2 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 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 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 -0.8660 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.4641 2.0000 0.0000 N 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 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 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 -6.0622 -1.5000 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 31 1 0 0 0 0 2 3 2 0 0 0 0 2 4 1 0 0 0 0 3 5 1 0 0 0 0 4 6 2 0 0 0 0 5 15 2 0 0 0 0 6 15 1 0 0 0 0 7 12 2 0 0 0 0 7 15 1 0 0 0 0 8 10 1 0 0 0 0 8 16 2 0 0 0 0 9 11 2 0 0 0 0 9 16 1 0 0 0 0 10 17 2 0 0 0 0 11 17 1 0 0 0 0 12 20 1 0 0 0 0 13 25 1 0 0 0 0 14 26 1 0 0 0 0 16 18 1 0 0 0 0 17 31 1 0 0 0 0 18 13 1 1 0 0 0 18 32 1 0 0 0 0 19 14 1 1 0 0 0 19 21 1 0 0 0 0 19 33 1 0 0 0 0 20 25 2 3 0 0 0 20 27 1 0 0 0 0 21 22 1 0 0 0 0 21 28 1 6 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 32 1 1 0 0 0 24 33 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	459.19
Volume:	458.218
LogP:	1.487
LogD:	1.784
LogS:	-3.721
# Rotatable Bonds:	10
TPSA:	137.71
# H-Bond Aceptor:	9
# H-Bond Donor:	5
# Rings:	3
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.34
Synthetic Accessibility Score:	3.767
Fsp3:	0.375
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.28
MDCK Permeability:	5.46259616385214e-06
Pgp-inhibitor:	0.016
Pgp-substrate:	0.218
Human Intestinal Absorption (HIA):	0.833
20% Bioavailability (F20%):	0.904
30% Bioavailability (F30%):	0.997

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.269
Plasma Protein Binding (PPB):	87.98169708251953%
Volume Distribution (VD):	0.54
Pgp-substrate:	5.38299560546875%

ADMET: Metabolism

CYP1A2-inhibitor:	0.098
CYP1A2-substrate:	0.03
CYP2C19-inhibitor:	0.212
CYP2C19-substrate:	0.452
CYP2C9-inhibitor:	0.063
CYP2C9-substrate:	0.706
CYP2D6-inhibitor:	0.035
CYP2D6-substrate:	0.73
CYP3A4-inhibitor:	0.056
CYP3A4-substrate:	0.148

ADMET: Excretion

Clearance (CL):	5.181
Half-life (T1/2):	0.623

ADMET: Toxicity

hERG Blockers:	0.379
Human Hepatotoxicity (H-HT):	0.22
Drug-inuced Liver Injury (DILI):	0.46
AMES Toxicity:	0.577
Rat Oral Acute Toxicity:	0.022
Maximum Recommended Daily Dose:	0.008
Skin Sensitization:	0.674
Carcinogencity:	0.148
Eye Corrosion:	0.003
Eye Irritation:	0.045
Respiratory Toxicity:	0.042

Download Data

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

Natural Product: NPC63628

Natural Product ID:	NPC63628
*Common Name:**	Aegelinoside A
IUPAC Name:	(E)-N-[(2S)-2-(4-methoxyphenyl)-2-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyethyl]-3-phenylprop-2-enamide
Synonyms:
Standard InCHIKey:	ZWNXGPYGBYQKIY-ODZYCVCSSA-N
Standard InCHI:	InChI=1S/C24H29NO8/c1-31-17-10-8-16(9-11-17)18(13-25-20(27)12-7-15-5-3-2-4-6-15)32-24-23(30)22(29)21(28)19(14-26)33-24/h2-12,18-19,21-24,26,28-30H,13-14H2,1H3,(H,25,27)/b12-7+/t18-,19-,21-,22+,23-,24-/m1/s1
SMILES:	OC[C@H]1O[C@@H](O[C@@H](c2ccc(cc2)OC)CN=C(/C=C/c2ccccc2)O)[C@@H]([C@H]([C@@H]1O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL491204
PubChem CID:	44579743
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0003909] Fatty Acyls [CHEMONTID:0001766] Fatty acyl glycosides [CHEMONTID:0003861] Fatty acyl glycosides of mono- and disaccharides

*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
NPO5045	Aegle marmelos	Species	Rutaceae	Eukaryota	leaves	n.a.	n.a.	PMID[18760601]
NPO5045	Aegle marmelos	Species	Rutaceae	Eukaryota	n.a.	bark	n.a.	PMID[21875114]
NPO5045	Aegle marmelos	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23434131]
NPO5045	Aegle marmelos	Species	Rutaceae	Eukaryota	n.a.	fruit	n.a.	PMID[26247834]
NPO5045	Aegle marmelos	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[30579794]
NPO5045	Aegle marmelos	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5045	Aegle marmelos	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5045	Aegle marmelos	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]

☑ 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	4

Activity Type	# Activity
Others	4

Target ID	Target Type	Target Name	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified	Inhibition	=	6.1	%	PMID[533991]
NPT2	Others	Unspecified	Inhibition	=	11.6	%	PMID[533991]
NPT2	Others	Unspecified	Inhibition	=	17.6	%	PMID[533991]
NPT2	Others	Unspecified	Inhibition	=	4.6	%	PMID[533991]

☑ 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 NPC63628 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	199
0.1-0.2	1103
0.2-0.3	3923
0.3-0.4	11267
0.4-0.5	7482
0.5-0.6	10703
0.6-0.7	6817
0.7-0.8	1134
0.8-0.85	58
0.85-0.9	9
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC178466
0.9161	High Similarity	NPC114659
0.9161	High Similarity	NPC139699
0.8912	High Similarity	NPC187028
0.8912	High Similarity	NPC305700
0.8912	High Similarity	NPC10221
0.8912	High Similarity	NPC197741
0.8912	High Similarity	NPC18249
0.8912	High Similarity	NPC140915
0.8732	High Similarity	NPC195814
0.8731	High Similarity	NPC62101
0.8731	High Similarity	NPC95733
0.8657	High Similarity	NPC211218
0.8529	High Similarity	NPC29477
0.8462	Intermediate Similarity	NPC36434
0.8462	Intermediate Similarity	NPC299583
0.8446	Intermediate Similarity	NPC470935
0.8446	Intermediate Similarity	NPC471032
0.8444	Intermediate Similarity	NPC476142
0.8403	Intermediate Similarity	NPC298821
0.8392	Intermediate Similarity	NPC160607
0.8392	Intermediate Similarity	NPC41473
0.8392	Intermediate Similarity	NPC204848
0.8392	Intermediate Similarity	NPC14600
0.8392	Intermediate Similarity	NPC312770
0.8378	Intermediate Similarity	NPC115144
0.8378	Intermediate Similarity	NPC277857
0.8345	Intermediate Similarity	NPC123761
0.8299	Intermediate Similarity	NPC97004
0.8299	Intermediate Similarity	NPC136951
0.8299	Intermediate Similarity	NPC161155
0.8243	Intermediate Similarity	NPC97282
0.8243	Intermediate Similarity	NPC313414
0.8169	Intermediate Similarity	NPC475067
0.8162	Intermediate Similarity	NPC469412
0.8162	Intermediate Similarity	NPC198734
0.8162	Intermediate Similarity	NPC269242
0.8146	Intermediate Similarity	NPC182119
0.8143	Intermediate Similarity	NPC198798
0.8138	Intermediate Similarity	NPC52277
0.8138	Intermediate Similarity	NPC254610
0.8138	Intermediate Similarity	NPC199459
0.8138	Intermediate Similarity	NPC177035
0.8133	Intermediate Similarity	NPC476743
0.8125	Intermediate Similarity	NPC187194
0.8088	Intermediate Similarity	NPC263835
0.8088	Intermediate Similarity	NPC60589
0.8088	Intermediate Similarity	NPC469708
0.8082	Intermediate Similarity	NPC262328
0.8082	Intermediate Similarity	NPC138738
0.8082	Intermediate Similarity	NPC87777
0.8082	Intermediate Similarity	NPC470413
0.8079	Intermediate Similarity	NPC476744
0.8069	Intermediate Similarity	NPC79957
0.8058	Intermediate Similarity	NPC287429
0.8056	Intermediate Similarity	NPC115022
0.8056	Intermediate Similarity	NPC294166
0.8042	Intermediate Similarity	NPC65942
0.8042	Intermediate Similarity	NPC248307
0.8029	Intermediate Similarity	NPC469704
0.8029	Intermediate Similarity	NPC201402
0.8029	Intermediate Similarity	NPC160854
0.8029	Intermediate Similarity	NPC469703
0.8015	Intermediate Similarity	NPC43275
0.8	Intermediate Similarity	NPC35731
0.8	Intermediate Similarity	NPC476411
0.7986	Intermediate Similarity	NPC85799
0.7986	Intermediate Similarity	NPC165686
0.7986	Intermediate Similarity	NPC303422
0.7986	Intermediate Similarity	NPC212176
0.7986	Intermediate Similarity	NPC26080
0.7974	Intermediate Similarity	NPC476742
0.7972	Intermediate Similarity	NPC472024
0.7972	Intermediate Similarity	NPC80600
0.7971	Intermediate Similarity	NPC469686
0.7959	Intermediate Similarity	NPC296898
0.7945	Intermediate Similarity	NPC238243
0.7926	Intermediate Similarity	NPC175771
0.7926	Intermediate Similarity	NPC148055
0.7922	Intermediate Similarity	NPC476741
0.7919	Intermediate Similarity	NPC472711
0.7919	Intermediate Similarity	NPC210192
0.7917	Intermediate Similarity	NPC9912
0.7917	Intermediate Similarity	NPC214869
0.7917	Intermediate Similarity	NPC121376
0.7914	Intermediate Similarity	NPC471067
0.7902	Intermediate Similarity	NPC195749
0.7902	Intermediate Similarity	NPC307110
0.7902	Intermediate Similarity	NPC248355
0.7902	Intermediate Similarity	NPC35961
0.7902	Intermediate Similarity	NPC295970
0.7902	Intermediate Similarity	NPC166040
0.7902	Intermediate Similarity	NPC270849
0.7902	Intermediate Similarity	NPC52029
0.7902	Intermediate Similarity	NPC26653
0.7891	Intermediate Similarity	NPC40664
0.7891	Intermediate Similarity	NPC197723
0.7891	Intermediate Similarity	NPC166180
0.7891	Intermediate Similarity	NPC3293
0.7891	Intermediate Similarity	NPC138350
0.7891	Intermediate Similarity	NPC165482
0.7887	Intermediate Similarity	NPC288416
0.7887	Intermediate Similarity	NPC251571
0.7877	Intermediate Similarity	NPC130496
0.7877	Intermediate Similarity	NPC470881
0.7877	Intermediate Similarity	NPC188555
0.7872	Intermediate Similarity	NPC470510
0.7867	Intermediate Similarity	NPC230718
0.7867	Intermediate Similarity	NPC84207
0.7867	Intermediate Similarity	NPC189115
0.7867	Intermediate Similarity	NPC60249
0.7867	Intermediate Similarity	NPC5253
0.7867	Intermediate Similarity	NPC139976
0.7867	Intermediate Similarity	NPC128337
0.7867	Intermediate Similarity	NPC469559
0.7867	Intermediate Similarity	NPC49542
0.7867	Intermediate Similarity	NPC140502
0.7867	Intermediate Similarity	NPC48309
0.7862	Intermediate Similarity	NPC50380
0.7862	Intermediate Similarity	NPC179250
0.7857	Intermediate Similarity	NPC178449
0.7857	Intermediate Similarity	NPC232454
0.7857	Intermediate Similarity	NPC470907
0.7852	Intermediate Similarity	NPC106944
0.7847	Intermediate Similarity	NPC114102
0.7842	Intermediate Similarity	NPC55608
0.7842	Intermediate Similarity	NPC226712
0.7838	Intermediate Similarity	NPC304152
0.7838	Intermediate Similarity	NPC124149
0.7832	Intermediate Similarity	NPC302378
0.7832	Intermediate Similarity	NPC155838
0.7826	Intermediate Similarity	NPC198741
0.7826	Intermediate Similarity	NPC469702
0.7826	Intermediate Similarity	NPC282409
0.7817	Intermediate Similarity	NPC301713
0.7815	Intermediate Similarity	NPC113680
0.7815	Intermediate Similarity	NPC46092
0.7815	Intermediate Similarity	NPC477898
0.7815	Intermediate Similarity	NPC470950
0.7815	Intermediate Similarity	NPC473044
0.7815	Intermediate Similarity	NPC278961
0.7815	Intermediate Similarity	NPC185307
0.7815	Intermediate Similarity	NPC116922
0.7808	Intermediate Similarity	NPC25821
0.7808	Intermediate Similarity	NPC6836
0.7806	Intermediate Similarity	NPC474560
0.78	Intermediate Similarity	NPC469661
0.78	Intermediate Similarity	NPC108674
0.78	Intermediate Similarity	NPC76871
0.7794	Intermediate Similarity	NPC473556
0.7794	Intermediate Similarity	NPC301651
0.7793	Intermediate Similarity	NPC138777
0.7793	Intermediate Similarity	NPC246869
0.7793	Intermediate Similarity	NPC471953
0.7793	Intermediate Similarity	NPC235294
0.7793	Intermediate Similarity	NPC225384
0.7793	Intermediate Similarity	NPC46137
0.7785	Intermediate Similarity	NPC156376
0.7785	Intermediate Similarity	NPC98777
0.7785	Intermediate Similarity	NPC212770
0.7778	Intermediate Similarity	NPC97326
0.7778	Intermediate Similarity	NPC218003
0.7778	Intermediate Similarity	NPC157338
0.7778	Intermediate Similarity	NPC313193
0.777	Intermediate Similarity	NPC242028
0.777	Intermediate Similarity	NPC83279
0.777	Intermediate Similarity	NPC469548
0.777	Intermediate Similarity	NPC469383
0.777	Intermediate Similarity	NPC203230
0.777	Intermediate Similarity	NPC476448
0.777	Intermediate Similarity	NPC476445
0.7763	Intermediate Similarity	NPC473045
0.7763	Intermediate Similarity	NPC177597
0.7763	Intermediate Similarity	NPC25292
0.7763	Intermediate Similarity	NPC5462
0.7763	Intermediate Similarity	NPC470235
0.7763	Intermediate Similarity	NPC84181
0.7763	Intermediate Similarity	NPC283995
0.7763	Intermediate Similarity	NPC129417
0.7763	Intermediate Similarity	NPC225445
0.7755	Intermediate Similarity	NPC48863
0.7755	Intermediate Similarity	NPC13745
0.7755	Intermediate Similarity	NPC251981
0.7755	Intermediate Similarity	NPC107478
0.7748	Intermediate Similarity	NPC5262
0.7748	Intermediate Similarity	NPC472714
0.7748	Intermediate Similarity	NPC475084
0.7748	Intermediate Similarity	NPC246947
0.7748	Intermediate Similarity	NPC472353
0.7748	Intermediate Similarity	NPC476356
0.774	Intermediate Similarity	NPC252833
0.774	Intermediate Similarity	NPC254275
0.7722	Intermediate Similarity	NPC476194
0.7718	Intermediate Similarity	NPC59324
0.7718	Intermediate Similarity	NPC65530
0.7718	Intermediate Similarity	NPC134260
0.7712	Intermediate Similarity	NPC286245
0.7712	Intermediate Similarity	NPC100998
0.7712	Intermediate Similarity	NPC279298
0.7712	Intermediate Similarity	NPC226722

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 NPC63628 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	146
0.1-0.2	584
0.2-0.3	973
0.3-0.4	2356
0.4-0.5	2550
0.5-0.6	1632
0.6-0.7	820
0.7-0.8	89
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8014	Intermediate Similarity	NPD4108	Discontinued
0.7911	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD3685	Discontinued
0.7842	Intermediate Similarity	NPD1091	Approved
0.7818	Intermediate Similarity	NPD7007	Discovery
0.7778	Intermediate Similarity	NPD4123	Phase 3
0.7667	Intermediate Similarity	NPD1375	Discontinued
0.7643	Intermediate Similarity	NPD4675	Approved
0.7643	Intermediate Similarity	NPD4678	Approved
0.7635	Intermediate Similarity	NPD3054	Approved
0.7635	Intermediate Similarity	NPD3052	Approved
0.761	Intermediate Similarity	NPD2977	Approved
0.761	Intermediate Similarity	NPD2978	Approved
0.7606	Intermediate Similarity	NPD3676	Clinical (unspecified phase)
0.7548	Intermediate Similarity	NPD3536	Discontinued
0.7547	Intermediate Similarity	NPD7945	Clinical (unspecified phase)
0.7517	Intermediate Similarity	NPD1772	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD5773	Approved
0.75	Intermediate Similarity	NPD5837	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7089	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD5772	Approved
0.7484	Intermediate Similarity	NPD7213	Phase 3
0.7484	Intermediate Similarity	NPD7212	Phase 2
0.7484	Intermediate Similarity	NPD6072	Discontinued
0.7483	Intermediate Similarity	NPD6582	Phase 2
0.7483	Intermediate Similarity	NPD3056	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD6583	Phase 3
0.7468	Intermediate Similarity	NPD4005	Discontinued
0.7451	Intermediate Similarity	NPD4236	Phase 3
0.7451	Intermediate Similarity	NPD4237	Approved
0.7451	Intermediate Similarity	NPD3060	Approved
0.7434	Intermediate Similarity	NPD7266	Discontinued
0.7432	Intermediate Similarity	NPD840	Approved
0.7432	Intermediate Similarity	NPD7477	Discontinued
0.7432	Intermediate Similarity	NPD839	Approved
0.7403	Intermediate Similarity	NPD6331	Phase 2
0.7397	Intermediate Similarity	NPD4993	Discontinued
0.7389	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD1048	Approved
0.7362	Intermediate Similarity	NPD5604	Discontinued
0.7361	Intermediate Similarity	NPD1669	Approved
0.7329	Intermediate Similarity	NPD6584	Phase 3
0.7325	Intermediate Similarity	NPD7447	Phase 1
0.7325	Intermediate Similarity	NPD4739	Approved
0.732	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7315	Intermediate Similarity	NPD2674	Phase 3
0.7308	Intermediate Similarity	NPD5058	Phase 3
0.7308	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD3122	Phase 3
0.7299	Intermediate Similarity	NPD7243	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD3179	Approved
0.7297	Intermediate Similarity	NPD3180	Approved
0.7297	Intermediate Similarity	NPD3027	Phase 3
0.729	Intermediate Similarity	NPD6658	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD7596	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD2238	Phase 2
0.7256	Intermediate Similarity	NPD8031	Discontinued
0.7241	Intermediate Similarity	NPD4659	Approved
0.7226	Intermediate Similarity	NPD2976	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD4162	Approved
0.7226	Intermediate Similarity	NPD5177	Phase 3
0.7215	Intermediate Similarity	NPD3985	Discontinued
0.7203	Intermediate Similarity	NPD2667	Approved
0.7203	Intermediate Similarity	NPD5238	Clinical (unspecified phase)
0.7203	Intermediate Similarity	NPD2668	Approved
0.72	Intermediate Similarity	NPD1423	Approved
0.7197	Intermediate Similarity	NPD5756	Phase 2
0.7192	Intermediate Similarity	NPD7258	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD3687	Approved
0.7188	Intermediate Similarity	NPD3686	Approved
0.7183	Intermediate Similarity	NPD6581	Approved
0.7183	Intermediate Similarity	NPD6580	Approved
0.7178	Intermediate Similarity	NPD5563	Clinical (unspecified phase)
0.7178	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD2231	Phase 2
0.7172	Intermediate Similarity	NPD2235	Phase 2
0.717	Intermediate Similarity	NPD7527	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD7526	Approved
0.717	Intermediate Similarity	NPD52	Approved
0.7163	Intermediate Similarity	NPD3596	Phase 2
0.7161	Intermediate Similarity	NPD7153	Discontinued
0.7152	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD1613	Approved
0.7143	Intermediate Similarity	NPD4103	Phase 2
0.7143	Intermediate Similarity	NPD4104	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD2161	Phase 2
0.7134	Intermediate Similarity	NPD5241	Discontinued
0.7134	Intermediate Similarity	NPD2677	Approved
0.7134	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD3145	Approved
0.7133	Intermediate Similarity	NPD6830	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD3144	Approved
0.7125	Intermediate Similarity	NPD2122	Discontinued
0.7124	Intermediate Similarity	NPD4536	Approved
0.7124	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD4538	Approved
0.7122	Intermediate Similarity	NPD7843	Approved
0.7122	Intermediate Similarity	NPD821	Approved
0.7117	Intermediate Similarity	NPD4433	Discontinued
0.7115	Intermediate Similarity	NPD5061	Approved
0.7115	Intermediate Similarity	NPD5062	Approved
0.7102	Intermediate Similarity	NPD6841	Approved
0.7102	Intermediate Similarity	NPD6843	Phase 3
0.7102	Intermediate Similarity	NPD6842	Approved
0.7086	Intermediate Similarity	NPD3532	Approved
0.7086	Intermediate Similarity	NPD3531	Approved
0.7086	Intermediate Similarity	NPD3530	Approved
0.708	Intermediate Similarity	NPD2684	Approved
0.7073	Intermediate Similarity	NPD8455	Phase 2
0.7073	Intermediate Similarity	NPD7972	Discontinued
0.7066	Intermediate Similarity	NPD6746	Phase 2
0.7055	Intermediate Similarity	NPD2562	Approved
0.7055	Intermediate Similarity	NPD2561	Approved
0.7048	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD6032	Approved
0.7032	Intermediate Similarity	NPD3175	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD1819	Approved
0.7027	Intermediate Similarity	NPD1818	Approved
0.7027	Intermediate Similarity	NPD1820	Approved
0.7027	Intermediate Similarity	NPD1817	Approved
0.7025	Intermediate Similarity	NPD3692	Discontinued
0.7019	Intermediate Similarity	NPD7131	Phase 3
0.7014	Intermediate Similarity	NPD6382	Discontinued
0.7006	Intermediate Similarity	NPD6674	Discontinued
0.7	Intermediate Similarity	NPD6419	Discontinued
0.7	Intermediate Similarity	NPD4908	Phase 1
0.7	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD7959	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD6502	Phase 2
0.6994	Remote Similarity	NPD3823	Discontinued
0.6987	Remote Similarity	NPD3656	Approved
0.6986	Remote Similarity	NPD776	Approved
0.6986	Remote Similarity	NPD3705	Approved
0.6982	Remote Similarity	NPD7608	Discontinued
0.6981	Remote Similarity	NPD6667	Approved
0.6981	Remote Similarity	NPD6666	Approved
0.698	Remote Similarity	NPD558	Phase 2
0.6975	Remote Similarity	NPD1653	Approved
0.6974	Remote Similarity	NPD6233	Phase 2
0.6974	Remote Similarity	NPD5745	Approved
0.6974	Remote Similarity	NPD6405	Approved
0.6974	Remote Similarity	NPD6407	Approved
0.6972	Remote Similarity	NPD2557	Approved
0.6972	Remote Similarity	NPD7157	Approved
0.697	Remote Similarity	NPD3465	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD5588	Approved
0.6968	Remote Similarity	NPD5960	Phase 3
0.6966	Remote Similarity	NPD5125	Phase 3
0.6966	Remote Similarity	NPD5723	Approved
0.6966	Remote Similarity	NPD5126	Approved
0.6964	Remote Similarity	NPD4666	Phase 3
0.6954	Remote Similarity	NPD3167	Approved
0.6954	Remote Similarity	NPD8014	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD3164	Approved
0.6954	Remote Similarity	NPD6179	Discontinued
0.6954	Remote Similarity	NPD3166	Approved
0.6954	Remote Similarity	NPD3165	Approved
0.6951	Remote Similarity	NPD3778	Approved
0.6944	Remote Similarity	NPD1548	Phase 1
0.6939	Remote Similarity	NPD2233	Approved
0.6939	Remote Similarity	NPD2232	Approved
0.6939	Remote Similarity	NPD2230	Approved
0.6933	Remote Similarity	NPD8158	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD5266	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD2861	Phase 2
0.6928	Remote Similarity	NPD1558	Phase 1
0.6928	Remote Similarity	NPD3061	Approved
0.6928	Remote Similarity	NPD3597	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD3062	Approved
0.6928	Remote Similarity	NPD3059	Approved
0.6913	Remote Similarity	NPD4098	Discontinued
0.6909	Remote Similarity	NPD4018	Clinical (unspecified phase)
0.6908	Remote Similarity	NPD5718	Phase 2
0.6908	Remote Similarity	NPD3374	Clinical (unspecified phase)
0.6908	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6906	Remote Similarity	NPD9380	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD5709	Phase 3
0.6903	Remote Similarity	NPD2200	Suspended
0.6903	Remote Similarity	NPD3553	Approved
0.6903	Remote Similarity	NPD3554	Approved
0.6903	Remote Similarity	NPD3552	Approved
0.6903	Remote Similarity	NPD3555	Approved
0.6903	Remote Similarity	NPD7097	Phase 1
0.6899	Remote Similarity	NPD2460	Phase 3
0.6899	Remote Similarity	NPD2459	Approved
0.6899	Remote Similarity	NPD2458	Approved
0.6899	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6899	Remote Similarity	NPD5289	Phase 2
0.6897	Remote Similarity	NPD2594	Approved
0.6897	Remote Similarity	NPD1357	Approved
0.6897	Remote Similarity	NPD2595	Approved
0.6894	Remote Similarity	NPD4160	Clinical (unspecified phase)
0.6892	Remote Similarity	NPD6542	Approved
0.6892	Remote Similarity	NPD2429	Approved
0.6892	Remote Similarity	NPD2428	Approved
0.6892	Remote Similarity	NPD6543	Approved
0.6892	Remote Similarity	NPD6539	Approved
0.6892	Remote Similarity	NPD6540	Phase 3
0.6887	Remote Similarity	NPD596	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