NPASS Compound

Structure

NPC471162 OpenBabel07101719512D 41 45 0 0 1 0 0 0 0 0999 V2000 -2.2479 1.9838 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0698 3.2535 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5064 2.6361 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9076 1.6180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2709 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7512 0.2515 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3173 1.1525 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5633 -0.1738 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5633 -0.8262 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6249 0.2967 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.9340 -0.6544 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6468 0.5046 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2648 -1.3975 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9777 -0.2386 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6176 -1.9328 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6394 -1.7248 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7568 -1.4010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7818 -1.6235 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2924 2.2786 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9131 1.7226 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2709 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.2867 -1.1896 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1906 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.9703 -2.4680 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7568 0.4010 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.6831 -1.3090 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 -0.7818 0.6235 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7540 0.3262 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.2793 -3.4190 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5593 1.5984 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.9921 -2.2601 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3253 0.9135 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 20 2 0 0 0 0 2 20 1 0 0 0 0 3 21 2 0 0 0 0 4 21 1 0 0 0 0 6 32 1 0 0 0 0 7 32 1 0 0 0 0 8 33 1 0 0 0 0 10 11 2 0 0 0 0 10 12 1 0 0 0 0 11 13 1 0 0 0 0 12 14 2 0 0 0 0 13 23 2 0 0 0 0 14 23 1 0 0 0 0 15 16 2 0 0 0 0 15 23 1 0 0 0 0 16 25 1 0 0 0 0 17 18 1 0 0 0 0 18 33 1 0 0 0 0 19 22 1 0 0 0 0 19 35 1 0 0 0 0 20 39 1 0 0 0 0 21 41 1 0 0 0 0 22 5 1 6 0 0 0 22 28 1 0 0 0 0 24 17 1 6 0 0 0 24 26 1 0 0 0 0 24 32 1 0 0 0 0 25 36 2 0 0 0 0 25 40 1 0 0 0 0 26 30 1 0 0 0 0 26 32 1 6 0 0 0 27 28 1 0 0 0 0 27 29 1 0 0 0 0 27 35 1 6 0 0 0 28 40 1 6 0 0 0 29 33 1 1 0 0 0 29 37 1 0 0 0 0 30 34 1 1 0 0 0 30 39 1 0 0 0 0 31 34 1 0 0 0 0 31 35 1 0 0 0 0 31 38 2 0 0 0 0 33 34 1 6 0 0 0 34 9 1 1 0 0 0 35 41 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	562.33
Volume:	602.783
LogP:	5.817
LogD:	5.067
LogS:	-5.296
# Rotatable Bonds:	8
TPSA:	82.06
# H-Bond Aceptor:	6
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.232
Synthetic Accessibility Score:	5.365
Fsp3:	0.6
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.051
MDCK Permeability:	2.5541259674355388e-05
Pgp-inhibitor:	0.859
Pgp-substrate:	0.147
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.038
30% Bioavailability (F30%):	0.937

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.956
Plasma Protein Binding (PPB):	80.50728607177734%
Volume Distribution (VD):	2.819
Pgp-substrate:	12.18072509765625%

ADMET: Metabolism

CYP1A2-inhibitor:	0.052
CYP1A2-substrate:	0.15
CYP2C19-inhibitor:	0.51
CYP2C19-substrate:	0.533
CYP2C9-inhibitor:	0.936
CYP2C9-substrate:	0.325
CYP2D6-inhibitor:	0.686
CYP2D6-substrate:	0.209
CYP3A4-inhibitor:	0.955
CYP3A4-substrate:	0.758

ADMET: Excretion

Clearance (CL):	9.984
Half-life (T1/2):	0.484

ADMET: Toxicity

hERG Blockers:	0.724
Human Hepatotoxicity (H-HT):	0.725
Drug-inuced Liver Injury (DILI):	0.812
AMES Toxicity:	0.011
Rat Oral Acute Toxicity:	0.402
Maximum Recommended Daily Dose:	0.028
Skin Sensitization:	0.842
Carcinogencity:	0.113
Eye Corrosion:	0.032
Eye Irritation:	0.059
Respiratory Toxicity:	0.936

Download Data

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

Natural Product: NPC471162

Natural Product ID:	NPC471162
*Common Name:**	ZGWIUHSCLOOVHO-HLIATGGQSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	ZGWIUHSCLOOVHO-HLIATGGQSA-N
Standard InCHI:	InChI=1S/C35H46O6/c1-20(2)39-30-26-24(32(26,6)7)17-18-33(8)29(37)27-28(40-25(36)16-15-23-13-11-10-12-14-23)22(5)19-35(27,41-21(3)4)31(38)34(30,33)9/h10-16,22,24,26-30,37H,1,3,17-19H2,2,4-9H3/b16-15+/t22-,24-,26-,27+,28-,29+,30+,33-,34+,35+/m0/s1
SMILES:	CC(=C)O[C@]12C[C@@H]([C@@H]([C@@H]1[C@@H](O)[C@]1([C@](C2=O)(C)[C@H](OC(=C)C)[C@@H]2[C@H](CC1)C2(C)C)C)OC(=O)/C=C/c1ccccc1)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2385646
PubChem CID:	73348882
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000476] Cinnamic acids and derivatives [CHEMONTID:0003480] Cinnamic acid esters

*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
NPO25837	Euphorbia micractina	Species	Euphorbiaceae	Eukaryota	Roots	Zhang County, Gansu Province, China	2002-Sep	PMID[19702283]
NPO25837	Euphorbia micractina	Species	Euphorbiaceae	Eukaryota	n.a.	root	n.a.	PMID[21534583]
NPO25837	Euphorbia micractina	Species	Euphorbiaceae	Eukaryota	Roots	n.a.	n.a.	PMID[23691978]
NPO25837	Euphorbia micractina	Species	Euphorbiaceae	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
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	IC50	=	8800.0	nM	PMID[512232]

☑ 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 NPC471162 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	313
0.1-0.2	1118
0.2-0.3	2470
0.3-0.4	5369
0.4-0.5	10292
0.5-0.6	16427
0.6-0.7	5765
0.7-0.8	863
0.8-0.85	70
0.85-0.9	3
0.9-0.95	6
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9034	High Similarity	NPC125033
0.8551	High Similarity	NPC477370
0.854	High Similarity	NPC477366
0.854	High Similarity	NPC477363
0.8503	High Similarity	NPC277053
0.8503	High Similarity	NPC301946
0.8489	Intermediate Similarity	NPC37968
0.8478	Intermediate Similarity	NPC477365
0.8467	Intermediate Similarity	NPC477369
0.8452	Intermediate Similarity	NPC55744
0.8435	Intermediate Similarity	NPC80895
0.8435	Intermediate Similarity	NPC471912
0.8429	Intermediate Similarity	NPC475671
0.8429	Intermediate Similarity	NPC475452
0.8425	Intermediate Similarity	NPC140021
0.8425	Intermediate Similarity	NPC63737
0.8394	Intermediate Similarity	NPC477362
0.8394	Intermediate Similarity	NPC8990
0.838	Intermediate Similarity	NPC15850
0.8366	Intermediate Similarity	NPC11410
0.8345	Intermediate Similarity	NPC477357
0.8301	Intermediate Similarity	NPC251139
0.8299	Intermediate Similarity	NPC183540
0.8289	Intermediate Similarity	NPC469647
0.8289	Intermediate Similarity	NPC138641
0.8289	Intermediate Similarity	NPC22571
0.8289	Intermediate Similarity	NPC469648
0.8289	Intermediate Similarity	NPC283875
0.8288	Intermediate Similarity	NPC473440
0.8278	Intermediate Similarity	NPC25484
0.8278	Intermediate Similarity	NPC232583
0.8276	Intermediate Similarity	NPC184109
0.8267	Intermediate Similarity	NPC205389
0.8247	Intermediate Similarity	NPC70344
0.8243	Intermediate Similarity	NPC153214
0.8235	Intermediate Similarity	NPC477098
0.8235	Intermediate Similarity	NPC477100
0.8231	Intermediate Similarity	NPC473497
0.8219	Intermediate Similarity	NPC276652
0.8194	Intermediate Similarity	NPC477368
0.817	Intermediate Similarity	NPC233581
0.817	Intermediate Similarity	NPC145649
0.8158	Intermediate Similarity	NPC477101
0.8158	Intermediate Similarity	NPC477099
0.8158	Intermediate Similarity	NPC477097
0.8146	Intermediate Similarity	NPC132652
0.8141	Intermediate Similarity	NPC49297
0.8138	Intermediate Similarity	NPC477367
0.8138	Intermediate Similarity	NPC270364
0.8138	Intermediate Similarity	NPC232888
0.8129	Intermediate Similarity	NPC154675
0.8125	Intermediate Similarity	NPC477364
0.8121	Intermediate Similarity	NPC45307
0.8121	Intermediate Similarity	NPC82467
0.8121	Intermediate Similarity	NPC131966
0.8121	Intermediate Similarity	NPC95449
0.8121	Intermediate Similarity	NPC191387
0.8108	Intermediate Similarity	NPC475413
0.8108	Intermediate Similarity	NPC474303
0.8108	Intermediate Similarity	NPC473654
0.8105	Intermediate Similarity	NPC472398
0.8105	Intermediate Similarity	NPC51602
0.8105	Intermediate Similarity	NPC471103
0.8101	Intermediate Similarity	NPC475536
0.8101	Intermediate Similarity	NPC165234
0.8079	Intermediate Similarity	NPC475552
0.8079	Intermediate Similarity	NPC477095
0.8077	Intermediate Similarity	NPC181924
0.8075	Intermediate Similarity	NPC40138
0.8069	Intermediate Similarity	NPC4242
0.8069	Intermediate Similarity	NPC471911
0.8065	Intermediate Similarity	NPC21410
0.8065	Intermediate Similarity	NPC473670
0.805	Intermediate Similarity	NPC475437
0.805	Intermediate Similarity	NPC475464
0.805	Intermediate Similarity	NPC475505
0.805	Intermediate Similarity	NPC473797
0.805	Intermediate Similarity	NPC473641
0.805	Intermediate Similarity	NPC475300
0.8042	Intermediate Similarity	NPC49272
0.8041	Intermediate Similarity	NPC251294
0.8039	Intermediate Similarity	NPC7095
0.8027	Intermediate Similarity	NPC86772
0.8013	Intermediate Similarity	NPC106895
0.8013	Intermediate Similarity	NPC127857
0.8	Intermediate Similarity	NPC477096
0.8	Intermediate Similarity	NPC477094
0.7987	Intermediate Similarity	NPC306799
0.7987	Intermediate Similarity	NPC43304
0.7987	Intermediate Similarity	NPC275477
0.7987	Intermediate Similarity	NPC477188
0.7987	Intermediate Similarity	NPC477190
0.7987	Intermediate Similarity	NPC242355
0.7987	Intermediate Similarity	NPC101043
0.7974	Intermediate Similarity	NPC473403
0.7974	Intermediate Similarity	NPC250046
0.7974	Intermediate Similarity	NPC60509
0.7974	Intermediate Similarity	NPC81698
0.7973	Intermediate Similarity	NPC325805
0.7973	Intermediate Similarity	NPC272523
0.7961	Intermediate Similarity	NPC312393
0.7961	Intermediate Similarity	NPC170668
0.7959	Intermediate Similarity	NPC477358
0.795	Intermediate Similarity	NPC325732
0.795	Intermediate Similarity	NPC324769
0.7949	Intermediate Similarity	NPC471176
0.7949	Intermediate Similarity	NPC282239
0.7945	Intermediate Similarity	NPC477359
0.7943	Intermediate Similarity	NPC284022
0.7933	Intermediate Similarity	NPC192658
0.7931	Intermediate Similarity	NPC476976
0.7931	Intermediate Similarity	NPC80599
0.7931	Intermediate Similarity	NPC209851
0.7922	Intermediate Similarity	NPC161239
0.7922	Intermediate Similarity	NPC165260
0.7922	Intermediate Similarity	NPC198455
0.7922	Intermediate Similarity	NPC112216
0.7919	Intermediate Similarity	NPC162613
0.7919	Intermediate Similarity	NPC475660
0.7919	Intermediate Similarity	NPC87934
0.7917	Intermediate Similarity	NPC3450
0.7917	Intermediate Similarity	NPC42234
0.7917	Intermediate Similarity	NPC122504
0.7902	Intermediate Similarity	NPC58061
0.7898	Intermediate Similarity	NPC217091
0.7895	Intermediate Similarity	NPC471107
0.7895	Intermediate Similarity	NPC25043
0.7895	Intermediate Similarity	NPC471100
0.7895	Intermediate Similarity	NPC134131
0.7891	Intermediate Similarity	NPC265459
0.7891	Intermediate Similarity	NPC290833
0.7891	Intermediate Similarity	NPC475262
0.7885	Intermediate Similarity	NPC472030
0.7885	Intermediate Similarity	NPC473414
0.7885	Intermediate Similarity	NPC257213
0.7885	Intermediate Similarity	NPC158333
0.7885	Intermediate Similarity	NPC256142
0.7885	Intermediate Similarity	NPC219419
0.7885	Intermediate Similarity	NPC304876
0.7885	Intermediate Similarity	NPC1173
0.7885	Intermediate Similarity	NPC242262
0.7885	Intermediate Similarity	NPC237549
0.7885	Intermediate Similarity	NPC146310
0.7885	Intermediate Similarity	NPC472005
0.7885	Intermediate Similarity	NPC265395
0.7885	Intermediate Similarity	NPC249471
0.7885	Intermediate Similarity	NPC472022
0.7867	Intermediate Similarity	NPC187566
0.7862	Intermediate Similarity	NPC476977
0.7852	Intermediate Similarity	NPC9905
0.7848	Intermediate Similarity	NPC472393
0.7847	Intermediate Similarity	NPC225103
0.7843	Intermediate Similarity	NPC478263
0.784	Intermediate Similarity	NPC61891
0.7838	Intermediate Similarity	NPC285221
0.7838	Intermediate Similarity	NPC194769
0.7834	Intermediate Similarity	NPC259144
0.7834	Intermediate Similarity	NPC114357
0.7834	Intermediate Similarity	NPC472549
0.7834	Intermediate Similarity	NPC112523
0.7834	Intermediate Similarity	NPC114410
0.7834	Intermediate Similarity	NPC469456
0.7834	Intermediate Similarity	NPC155329
0.7834	Intermediate Similarity	NPC228204
0.7834	Intermediate Similarity	NPC26033
0.7829	Intermediate Similarity	NPC34943
0.7826	Intermediate Similarity	NPC66193
0.7823	Intermediate Similarity	NPC472250
0.7815	Intermediate Similarity	NPC182869
0.7808	Intermediate Similarity	NPC477360
0.7806	Intermediate Similarity	NPC254558
0.78	Intermediate Similarity	NPC79921
0.7799	Intermediate Similarity	NPC471102
0.7799	Intermediate Similarity	NPC159692
0.7793	Intermediate Similarity	NPC473443
0.7793	Intermediate Similarity	NPC272946
0.7793	Intermediate Similarity	NPC472388
0.7792	Intermediate Similarity	NPC327031
0.7791	Intermediate Similarity	NPC161151
0.7778	Intermediate Similarity	NPC471134
0.7778	Intermediate Similarity	NPC125882
0.7778	Intermediate Similarity	NPC195224
0.7778	Intermediate Similarity	NPC478264
0.7771	Intermediate Similarity	NPC77719
0.7771	Intermediate Similarity	NPC11588
0.7771	Intermediate Similarity	NPC229545
0.7771	Intermediate Similarity	NPC134685
0.7771	Intermediate Similarity	NPC248265
0.777	Intermediate Similarity	NPC79699
0.7763	Intermediate Similarity	NPC477894
0.7762	Intermediate Similarity	NPC473082
0.7748	Intermediate Similarity	NPC266374
0.7748	Intermediate Similarity	NPC325078
0.7742	Intermediate Similarity	NPC473215
0.774	Intermediate Similarity	NPC72915
0.774	Intermediate Similarity	NPC472418
0.7736	Intermediate Similarity	NPC469771
0.773	Intermediate Similarity	NPC477491
0.7727	Intermediate Similarity	NPC473602
0.7727	Intermediate Similarity	NPC20255

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 NPC471162 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	1802
0.3-0.4	3236
0.4-0.5	2011
0.5-0.6	863
0.6-0.7	205
0.7-0.8	8
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
0.8133	Intermediate Similarity	NPD7236	Approved
0.7871	Intermediate Similarity	NPD7239	Suspended
0.7758	Intermediate Similarity	NPD7799	Discontinued
0.7755	Intermediate Similarity	NPD7966	Clinical (unspecified phase)
0.7568	Intermediate Similarity	NPD7961	Discontinued
0.7423	Intermediate Similarity	NPD7057	Phase 3
0.7423	Intermediate Similarity	NPD7058	Phase 2
0.723	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.7206	Intermediate Similarity	NPD6685	Approved
0.7168	Intermediate Similarity	NPD8368	Discontinued
0.7143	Intermediate Similarity	NPD7094	Approved
0.7143	Intermediate Similarity	NPD8407	Phase 2
0.7143	Intermediate Similarity	NPD6858	Approved
0.7091	Intermediate Similarity	NPD5760	Phase 2
0.7091	Intermediate Similarity	NPD5761	Phase 2
0.7062	Intermediate Similarity	NPD8434	Phase 2
0.7029	Intermediate Similarity	NPD6881	Approved
0.7029	Intermediate Similarity	NPD6899	Approved
0.7	Intermediate Similarity	NPD8130	Phase 1
0.7	Intermediate Similarity	NPD6649	Approved
0.7	Intermediate Similarity	NPD6650	Approved
0.6985	Remote Similarity	NPD5765	Approved
0.6966	Remote Similarity	NPD6319	Approved
0.6966	Remote Similarity	NPD7741	Discontinued
0.6957	Remote Similarity	NPD5697	Approved
0.695	Remote Similarity	NPD8297	Approved
0.6939	Remote Similarity	NPD7457	Clinical (unspecified phase)
0.6929	Remote Similarity	NPD7102	Approved
0.6929	Remote Similarity	NPD6883	Approved
0.6929	Remote Similarity	NPD7290	Approved
0.691	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6892	Remote Similarity	NPD7492	Approved
0.6889	Remote Similarity	NPD8435	Approved
0.6884	Remote Similarity	NPD6402	Approved
0.6884	Remote Similarity	NPD5739	Approved
0.6884	Remote Similarity	NPD5048	Discontinued
0.6884	Remote Similarity	NPD7128	Approved
0.6884	Remote Similarity	NPD6675	Approved
0.6879	Remote Similarity	NPD6617	Approved
0.6879	Remote Similarity	NPD6869	Approved
0.6879	Remote Similarity	NPD6847	Approved
0.6875	Remote Similarity	NPD6765	Approved
0.6875	Remote Similarity	NPD6764	Approved
0.6872	Remote Similarity	NPD8424	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD7736	Approved
0.6857	Remote Similarity	NPD6373	Approved
0.6857	Remote Similarity	NPD6372	Approved
0.6857	Remote Similarity	NPD6013	Approved
0.6857	Remote Similarity	NPD6012	Approved
0.6857	Remote Similarity	NPD6014	Approved
0.6853	Remote Similarity	NPD6010	Discontinued
0.6849	Remote Similarity	NPD6054	Approved
0.6846	Remote Similarity	NPD6616	Approved
0.6831	Remote Similarity	NPD6912	Phase 3
0.6831	Remote Similarity	NPD6882	Approved
0.6824	Remote Similarity	NPD7604	Phase 2
0.68	Remote Similarity	NPD7078	Approved
0.6796	Remote Similarity	NPD8361	Approved
0.6796	Remote Similarity	NPD8360	Approved
0.6792	Remote Similarity	NPD5763	Approved
0.6792	Remote Similarity	NPD5762	Approved
0.6786	Remote Similarity	NPD6011	Approved
0.6786	Remote Similarity	NPD7320	Approved
0.6776	Remote Similarity	NPD5740	Clinical (unspecified phase)
0.6776	Remote Similarity	NPD6085	Phase 2
0.6772	Remote Similarity	NPD7305	Phase 1
0.6757	Remote Similarity	NPD6370	Approved
0.6744	Remote Similarity	NPD8127	Discontinued
0.6739	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD6647	Phase 2
0.6722	Remote Similarity	NPD6784	Approved
0.6722	Remote Similarity	NPD6785	Approved
0.6714	Remote Similarity	NPD5701	Approved
0.6707	Remote Similarity	NPD6599	Discontinued
0.669	Remote Similarity	NPD2067	Discontinued
0.669	Remote Similarity	NPD2629	Approved
0.6689	Remote Similarity	NPD6015	Approved
0.6689	Remote Similarity	NPD6016	Approved
0.6689	Remote Similarity	NPD8293	Discontinued
0.6687	Remote Similarity	NPD6002	Phase 3
0.6687	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD6004	Phase 3
0.6687	Remote Similarity	NPD6005	Phase 3
0.6686	Remote Similarity	NPD7819	Suspended
0.6686	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6273	Approved
0.6667	Remote Similarity	NPD6663	Approved
0.6667	Remote Similarity	NPD8485	Approved
0.6667	Remote Similarity	NPD7610	Discontinued
0.6667	Remote Similarity	NPD4632	Approved
0.6648	Remote Similarity	NPD7962	Phase 2
0.6644	Remote Similarity	NPD7115	Discovery
0.6644	Remote Similarity	NPD6009	Approved
0.6644	Remote Similarity	NPD5988	Approved
0.663	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6626	Remote Similarity	NPD7274	Clinical (unspecified phase)
0.6626	Remote Similarity	NPD6190	Approved
0.6623	Remote Similarity	NPD5736	Approved
0.6622	Remote Similarity	NPD6059	Approved
0.661	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.6601	Remote Similarity	NPD7319	Approved
0.6592	Remote Similarity	NPD7685	Pre-registration
0.6581	Remote Similarity	NPD7055	Discontinued
0.6577	Remote Similarity	NPD5983	Phase 2
0.6573	Remote Similarity	NPD4634	Approved
0.657	Remote Similarity	NPD7075	Discontinued
0.6564	Remote Similarity	NPD4628	Phase 3
0.6561	Remote Similarity	NPD8486	Clinical (unspecified phase)
0.6554	Remote Similarity	NPD7101	Approved
0.6554	Remote Similarity	NPD7100	Approved
0.6547	Remote Similarity	NPD5211	Phase 2
0.6532	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6531	Remote Similarity	NPD3317	Approved
0.6531	Remote Similarity	NPD4198	Discontinued
0.6528	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD5285	Approved
0.6522	Remote Similarity	NPD5286	Approved
0.6522	Remote Similarity	NPD4696	Approved
0.6513	Remote Similarity	NPD6336	Discontinued
0.651	Remote Similarity	NPD7009	Phase 2
0.6506	Remote Similarity	NPD2533	Approved
0.6506	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6506	Remote Similarity	NPD2532	Approved
0.6506	Remote Similarity	NPD2534	Approved
0.6503	Remote Similarity	NPD8150	Discontinued
0.6486	Remote Similarity	NPD6335	Approved
0.6483	Remote Similarity	NPD6053	Discontinued
0.6478	Remote Similarity	NPD6355	Discontinued
0.6463	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6463	Remote Similarity	NPD8166	Discontinued
0.6463	Remote Similarity	NPD6274	Approved
0.646	Remote Similarity	NPD7033	Discontinued
0.6458	Remote Similarity	NPD6371	Approved
0.6454	Remote Similarity	NPD5141	Approved
0.6454	Remote Similarity	NPD5909	Discontinued
0.6449	Remote Similarity	NPD7638	Approved
0.6446	Remote Similarity	NPD6799	Approved
0.6434	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6433	Remote Similarity	NPD6801	Discontinued
0.6433	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD5226	Approved
0.6429	Remote Similarity	NPD4633	Approved
0.6429	Remote Similarity	NPD5224	Approved
0.6429	Remote Similarity	NPD5225	Approved
0.6424	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6419	Remote Similarity	NPD6317	Approved
0.6415	Remote Similarity	NPD4140	Approved
0.6414	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6408	Remote Similarity	NPD6008	Approved
0.6405	Remote Similarity	NPD7507	Approved
0.6405	Remote Similarity	NPD6637	Approved
0.6403	Remote Similarity	NPD7640	Approved
0.6403	Remote Similarity	NPD7639	Approved
0.6383	Remote Similarity	NPD5174	Approved
0.6383	Remote Similarity	NPD5175	Approved
0.6377	Remote Similarity	NPD4755	Approved
0.6377	Remote Similarity	NPD6084	Phase 2
0.6377	Remote Similarity	NPD6083	Phase 2
0.6376	Remote Similarity	NPD6313	Approved
0.6376	Remote Similarity	NPD6314	Approved
0.6369	Remote Similarity	NPD3751	Discontinued
0.6364	Remote Similarity	NPD8462	Phase 1
0.6358	Remote Similarity	NPD2799	Discontinued
0.6357	Remote Similarity	NPD5223	Approved
0.6352	Remote Similarity	NPD8032	Phase 2
0.6351	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6328	Remote Similarity	NPD3787	Discontinued
0.6319	Remote Similarity	NPD6100	Approved
0.6319	Remote Similarity	NPD6099	Approved
0.6313	Remote Similarity	NPD7473	Discontinued
0.631	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6306	Remote Similarity	NPD7084	Phase 3
0.6301	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6292	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6289	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6289	Remote Similarity	NPD7497	Discontinued
0.6286	Remote Similarity	NPD4700	Approved
0.6286	Remote Similarity	NPD2066	Phase 3
0.628	Remote Similarity	NPD2346	Discontinued
0.6277	Remote Similarity	NPD5122	Clinical (unspecified phase)
0.6264	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6264	Remote Similarity	NPD3817	Phase 2
0.6264	Remote Similarity	NPD5402	Approved
0.6257	Remote Similarity	NPD3226	Approved
0.6256	Remote Similarity	NPD8319	Approved
0.6256	Remote Similarity	NPD8320	Phase 1
0.625	Remote Similarity	NPD6909	Approved
0.625	Remote Similarity	NPD7503	Approved
0.625	Remote Similarity	NPD6908	Approved
0.625	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.625	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6243	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6243	Remote Similarity	NPD37	Approved
0.6242	Remote Similarity	NPD5647	Approved
0.6242	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6235	Remote Similarity	NPD6653	Approved
0.6235	Remote Similarity	NPD7606	Phase 3
0.6229	Remote Similarity	NPD4965	Approved
0.6229	Remote Similarity	NPD4966	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