NPASS Compound

Structure

NPC471847 OpenBabel07101718242D 43 47 0 0 1 0 0 0 0 0999 V2000 2.5439 -1.4688 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 4.8958 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2399 0.4896 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6960 3.9167 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3919 -0.9792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 3.9167 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7839 2.9375 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9359 4.4063 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5439 0.4896 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.6318 3.4271 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7839 4.8958 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6960 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6960 1.9583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3919 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8480 3.4271 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.9359 3.4271 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5439 1.4688 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.6318 4.4063 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8480 0.4896 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8480 1.4688 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0879 2.9375 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3919 1.9583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5439 0.4896 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2399 3.4271 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0879 1.9583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3919 2.9375 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2399 1.4687 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6960 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6960 1.9583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8480 1.4688 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5439 1.4688 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.8480 0.4896 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -8.4798 4.8958 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2399 4.4063 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.9359 1.4688 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5439 3.4271 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2399 0.4896 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6960 -0.9792 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6960 2.9375 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3919 1.9583 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8480 -0.4896 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.9583 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 5 1 0 0 0 0 2 6 1 0 0 0 0 5 14 1 0 0 0 0 6 15 1 0 0 0 0 7 10 1 0 0 0 0 7 16 2 0 0 0 0 8 11 2 0 0 0 0 8 16 1 0 0 0 0 9 12 2 0 0 0 0 9 17 1 0 0 0 0 10 18 2 0 0 0 0 11 18 1 0 0 0 0 12 19 1 0 0 0 0 13 17 2 0 0 0 0 13 20 1 0 0 0 0 14 3 1 1 0 0 0 14 23 1 0 0 0 0 15 4 1 1 0 0 0 16 21 1 0 0 0 0 17 22 1 0 0 0 0 18 33 1 0 0 0 0 19 20 2 0 0 0 0 19 43 1 0 0 0 0 20 42 1 0 0 0 0 21 24 2 0 0 0 0 21 25 1 0 0 0 0 22 26 1 0 0 0 0 22 27 2 0 0 0 0 23 28 2 0 0 0 0 23 31 1 0 0 0 0 24 26 1 0 0 0 0 24 34 1 0 0 0 0 25 27 1 0 0 0 0 25 35 2 0 0 0 0 26 36 2 0 0 0 0 27 37 1 0 0 0 0 28 32 1 0 0 0 0 28 38 1 0 0 0 0 29 30 1 0 0 0 0 29 31 1 0 0 0 0 29 39 2 0 0 0 0 30 15 1 1 0 0 0 30 32 1 0 0 0 0 30 42 1 0 0 0 0 31 40 1 0 0 0 0 32 41 2 0 0 0 0 32 43 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	594.18
Volume:	571.702
LogP:	3.46
LogD:	0.866
LogS:	-0.913
# Rotatable Bonds:	6
TPSA:	193.96
# H-Bond Aceptor:	13
# H-Bond Donor:	4
# Rings:	5
# Heavy Atoms:	13

MedChem Properties

QED Drug-Likeness Score:	0.165
Synthetic Accessibility Score:	5.029
Fsp3:	0.333
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.414
MDCK Permeability:	9.407960533280857e-06
Pgp-inhibitor:	0.017
Pgp-substrate:	0.997
Human Intestinal Absorption (HIA):	0.675
20% Bioavailability (F20%):	0.404
30% Bioavailability (F30%):	0.908

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.04
Plasma Protein Binding (PPB):	99.15257263183594%
Volume Distribution (VD):	0.623
Pgp-substrate:	1.4813100099563599%

ADMET: Metabolism

CYP1A2-inhibitor:	0.138
CYP1A2-substrate:	0.097
CYP2C19-inhibitor:	0.121
CYP2C19-substrate:	0.094
CYP2C9-inhibitor:	0.856
CYP2C9-substrate:	0.969
CYP2D6-inhibitor:	0.005
CYP2D6-substrate:	0.065
CYP3A4-inhibitor:	0.258
CYP3A4-substrate:	0.92

ADMET: Excretion

Clearance (CL):	2.486
Half-life (T1/2):	0.682

ADMET: Toxicity

hERG Blockers:	0.001
Human Hepatotoxicity (H-HT):	0.835
Drug-inuced Liver Injury (DILI):	0.996
AMES Toxicity:	0.043
Rat Oral Acute Toxicity:	0.728
Maximum Recommended Daily Dose:	0.889
Skin Sensitization:	0.19
Carcinogencity:	0.588
Eye Corrosion:	0.003
Eye Irritation:	0.007
Respiratory Toxicity:	0.197

Download Data

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

Natural Product: NPC471847

Natural Product ID:	NPC471847
*Common Name:**	Episarcoviolin Beta
IUPAC Name:	2-[(5R,11aR)-3-[(2S)-butan-2-yl]-11a-[(2R)-butan-2-yl]-2,4-dihydroxy-5-oxido-1-oxopyrazino[1,2-b][1,4,2]benzodioxazin-5-ium-9-yl]-3,6-dihydroxy-5-(4-hydroxyphenyl)cyclohexa-2,5-diene-1,4-dione
Synonyms:
Standard InCHIKey:	HEXAABFDZKPMQT-DHJISALFSA-N
Standard InCHI:	InChI=1S/C30H30N2O11/c1-5-14(3)23-28(38)32(41)30(15(4)6-2,29(39)31(23)40)42-20-13-17(9-12-19(20)43-32)22-26(36)24(34)21(25(35)27(22)37)16-7-10-18(33)11-8-16/h7-15,33-34,37-38,40H,5-6H2,1-4H3/t14-,15+,30+,32+/m0/s1
SMILES:	CCC(C)C1=C([N+]2(C(C(=O)N1O)(OC3=C(O2)C=CC(=C3)C4=C(C(=O)C(=C(C4=O)O)C5=CC=C(C=C5)O)O)C(C)CC)[O-])O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3238005
PubChem CID:	90671614
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0000265] Carboxylic acids and derivatives [CHEMONTID:0000013] Amino acids, peptides, and analogues [CHEMONTID:0000347] Amino acids and derivatives [CHEMONTID:0000060] Alpha amino acids and derivatives

*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
NPO26394	Sarcodon leucopus	Species	Thelephoraceae	Eukaryota	Fruits	n.a.	n.a.	PMID[10757716]
NPO26394	Sarcodon leucopus	Species	Thelephoraceae	Eukaryota	n.a.	Tibet, China	n.a.	PMID[24645629]
NPO26394	Sarcodon leucopus	Species	Thelephoraceae	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
EC50	1
IC50	3
Others	1

Activity Type	# Activity
NON-MOLECULAR	2
Others	2
Tissue	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1	Others	Radical scavenging activity		IC50	=	12000.0	nM	PMID[547540]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	146.0	U	PMID[547540]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	EC50	=	17000.0	nM	PMID[547540]
NPT625	Tissue	Liver	Mus musculus	IC50	=	27000.0	nM	PMID[547540]
NPT2	Others	Unspecified		IC50	=	1070.0	nM	PMID[547540]

☑ 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 NPC471847 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	316
0.1-0.2	1647
0.2-0.3	6455
0.3-0.4	11878
0.4-0.5	5169
0.5-0.6	12156
0.6-0.7	5043
0.7-0.8	27
0.8-0.85	4
0.85-0.9	0
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC18633
0.8245	Intermediate Similarity	NPC119291
0.8245	Intermediate Similarity	NPC471849
0.8245	Intermediate Similarity	NPC161144
0.8245	Intermediate Similarity	NPC471848
0.7079	Intermediate Similarity	NPC474556
0.7	Intermediate Similarity	NPC32064
0.7	Intermediate Similarity	NPC475718
0.6968	Remote Similarity	NPC164608
0.6943	Remote Similarity	NPC138083
0.6908	Remote Similarity	NPC92235
0.6842	Remote Similarity	NPC239302
0.6837	Remote Similarity	NPC234069
0.6824	Remote Similarity	NPC172673
0.6821	Remote Similarity	NPC276120
0.6802	Remote Similarity	NPC64140
0.6802	Remote Similarity	NPC174122
0.68	Remote Similarity	NPC284409
0.6746	Remote Similarity	NPC471532
0.6735	Remote Similarity	NPC475566
0.6731	Remote Similarity	NPC471561
0.6723	Remote Similarity	NPC138438
0.6723	Remote Similarity	NPC908
0.6717	Remote Similarity	NPC29531
0.6698	Remote Similarity	NPC471531
0.6685	Remote Similarity	NPC236769
0.6685	Remote Similarity	NPC153644
0.6685	Remote Similarity	NPC76376
0.6684	Remote Similarity	NPC158900
0.6648	Remote Similarity	NPC469540
0.6648	Remote Similarity	NPC98009
0.6648	Remote Similarity	NPC469539
0.6647	Remote Similarity	NPC132308
0.6633	Remote Similarity	NPC298339
0.6631	Remote Similarity	NPC288353
0.6631	Remote Similarity	NPC178854
0.663	Remote Similarity	NPC50728
0.663	Remote Similarity	NPC219330
0.663	Remote Similarity	NPC166753
0.6615	Remote Similarity	NPC329816
0.6613	Remote Similarity	NPC236223
0.6613	Remote Similarity	NPC58382
0.6613	Remote Similarity	NPC179126
0.6613	Remote Similarity	NPC162351
0.6613	Remote Similarity	NPC270620
0.6613	Remote Similarity	NPC246204
0.6613	Remote Similarity	NPC78326
0.6612	Remote Similarity	NPC478189
0.6611	Remote Similarity	NPC9373
0.6608	Remote Similarity	NPC226661
0.6596	Remote Similarity	NPC183
0.6588	Remote Similarity	NPC90128
0.6588	Remote Similarity	NPC84076
0.6588	Remote Similarity	NPC303680
0.6584	Remote Similarity	NPC471563
0.6578	Remote Similarity	NPC32557
0.6578	Remote Similarity	NPC189960
0.6576	Remote Similarity	NPC159103
0.6573	Remote Similarity	NPC322021
0.6571	Remote Similarity	NPC475828
0.6569	Remote Similarity	NPC50548
0.6569	Remote Similarity	NPC293624
0.6569	Remote Similarity	NPC83019
0.6562	Remote Similarity	NPC473748
0.6561	Remote Similarity	NPC22472
0.6561	Remote Similarity	NPC25495
0.6561	Remote Similarity	NPC280680
0.6561	Remote Similarity	NPC176300
0.6561	Remote Similarity	NPC253634
0.6561	Remote Similarity	NPC300943
0.6561	Remote Similarity	NPC115798
0.6561	Remote Similarity	NPC19687
0.6561	Remote Similarity	NPC152166
0.6561	Remote Similarity	NPC7846
0.6561	Remote Similarity	NPC288669
0.6561	Remote Similarity	NPC105242
0.6561	Remote Similarity	NPC18607
0.6561	Remote Similarity	NPC4481
0.6561	Remote Similarity	NPC204854
0.6561	Remote Similarity	NPC18772
0.6561	Remote Similarity	NPC261004
0.6561	Remote Similarity	NPC191459
0.6561	Remote Similarity	NPC143828
0.6561	Remote Similarity	NPC130894
0.6561	Remote Similarity	NPC9609
0.6559	Remote Similarity	NPC123886
0.6559	Remote Similarity	NPC82325
0.6559	Remote Similarity	NPC279989
0.6557	Remote Similarity	NPC294972
0.6554	Remote Similarity	NPC231572
0.6552	Remote Similarity	NPC153453
0.655	Remote Similarity	NPC123228
0.655	Remote Similarity	NPC123722
0.655	Remote Similarity	NPC151167
0.655	Remote Similarity	NPC5018
0.655	Remote Similarity	NPC276466
0.6543	Remote Similarity	NPC55619
0.6543	Remote Similarity	NPC200388
0.6543	Remote Similarity	NPC265511
0.6543	Remote Similarity	NPC100916
0.6541	Remote Similarity	NPC295977
0.6541	Remote Similarity	NPC58310
0.6538	Remote Similarity	NPC287275
0.6534	Remote Similarity	NPC106606
0.6532	Remote Similarity	NPC66905
0.6529	Remote Similarity	NPC3221
0.6524	Remote Similarity	NPC86485
0.6524	Remote Similarity	NPC57512
0.6522	Remote Similarity	NPC195202
0.6522	Remote Similarity	NPC261548
0.652	Remote Similarity	NPC144314
0.652	Remote Similarity	NPC204580
0.6519	Remote Similarity	NPC160378
0.6514	Remote Similarity	NPC327410
0.6509	Remote Similarity	NPC242372
0.6509	Remote Similarity	NPC4181
0.6509	Remote Similarity	NPC257976
0.6509	Remote Similarity	NPC164778
0.6508	Remote Similarity	NPC287979
0.6508	Remote Similarity	NPC29841
0.6508	Remote Similarity	NPC112954
0.6508	Remote Similarity	NPC78302
0.6508	Remote Similarity	NPC227192
0.6508	Remote Similarity	NPC189179
0.6508	Remote Similarity	NPC110070
0.6508	Remote Similarity	NPC235215
0.6508	Remote Similarity	NPC75215
0.6508	Remote Similarity	NPC305663
0.6508	Remote Similarity	NPC163524
0.6508	Remote Similarity	NPC224137
0.6508	Remote Similarity	NPC472438
0.6508	Remote Similarity	NPC101830
0.6508	Remote Similarity	NPC93376
0.6508	Remote Similarity	NPC176665
0.6508	Remote Similarity	NPC7973
0.6508	Remote Similarity	NPC203891
0.6505	Remote Similarity	NPC200740
0.6505	Remote Similarity	NPC125062
0.6505	Remote Similarity	NPC306011
0.6505	Remote Similarity	NPC50403
0.6505	Remote Similarity	NPC28274
0.6505	Remote Similarity	NPC472838
0.6505	Remote Similarity	NPC252933
0.6505	Remote Similarity	NPC54394
0.6505	Remote Similarity	NPC133953
0.65	Remote Similarity	NPC472410
0.6491	Remote Similarity	NPC179777
0.6485	Remote Similarity	NPC196231
0.648	Remote Similarity	NPC288452
0.648	Remote Similarity	NPC191280
0.648	Remote Similarity	NPC289690
0.6477	Remote Similarity	NPC196708
0.6474	Remote Similarity	NPC200555
0.6474	Remote Similarity	NPC196026
0.6474	Remote Similarity	NPC193842
0.6474	Remote Similarity	NPC304622
0.6471	Remote Similarity	NPC312404
0.6471	Remote Similarity	NPC301123
0.6471	Remote Similarity	NPC273686
0.6471	Remote Similarity	NPC55205
0.6471	Remote Similarity	NPC134677
0.6471	Remote Similarity	NPC149962
0.6467	Remote Similarity	NPC33265
0.6467	Remote Similarity	NPC62536
0.6467	Remote Similarity	NPC12200
0.6467	Remote Similarity	NPC1580
0.6464	Remote Similarity	NPC169214
0.6464	Remote Similarity	NPC141817
0.6464	Remote Similarity	NPC176030
0.6464	Remote Similarity	NPC192597
0.6464	Remote Similarity	NPC229218
0.6459	Remote Similarity	NPC477666
0.6458	Remote Similarity	NPC78332
0.6458	Remote Similarity	NPC196091
0.6455	Remote Similarity	NPC98661
0.6455	Remote Similarity	NPC247017
0.6455	Remote Similarity	NPC245546
0.6455	Remote Similarity	NPC292107
0.6455	Remote Similarity	NPC474520
0.6455	Remote Similarity	NPC268161
0.6455	Remote Similarity	NPC471985
0.6455	Remote Similarity	NPC49824
0.6455	Remote Similarity	NPC266960
0.6455	Remote Similarity	NPC43243
0.6453	Remote Similarity	NPC16651
0.6453	Remote Similarity	NPC32163
0.6452	Remote Similarity	NPC58661
0.6452	Remote Similarity	NPC476580
0.6452	Remote Similarity	NPC286342
0.6452	Remote Similarity	NPC149127
0.6452	Remote Similarity	NPC300329
0.6452	Remote Similarity	NPC188871
0.645	Remote Similarity	NPC114298
0.6448	Remote Similarity	NPC324081
0.6444	Remote Similarity	NPC28398
0.6442	Remote Similarity	NPC140577
0.6442	Remote Similarity	NPC232533
0.6442	Remote Similarity	NPC43069
0.6441	Remote Similarity	NPC204592
0.6441	Remote Similarity	NPC139519

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 NPC471847 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	211
0.1-0.2	749
0.2-0.3	1267
0.3-0.4	2369
0.4-0.5	2545
0.5-0.6	1656
0.6-0.7	348
0.7-0.8	5
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
0.6927	Remote Similarity	NPD7132	Clinical (unspecified phase)
0.691	Remote Similarity	NPD3688	Clinical (unspecified phase)
0.691	Remote Similarity	NPD3146	Approved
0.6667	Remote Similarity	NPD5676	Approved
0.6633	Remote Similarity	NPD3534	Clinical (unspecified phase)
0.6585	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6584	Remote Similarity	NPD4413	Clinical (unspecified phase)
0.6576	Remote Similarity	NPD3866	Clinical (unspecified phase)
0.6557	Remote Similarity	NPD7131	Phase 3
0.6552	Remote Similarity	NPD7667	Clinical (unspecified phase)
0.6515	Remote Similarity	NPD6853	Approved
0.6515	Remote Similarity	NPD6851	Approved
0.6505	Remote Similarity	NPD7109	Clinical (unspecified phase)
0.6505	Remote Similarity	NPD7110	Phase 1
0.6486	Remote Similarity	NPD824	Approved
0.648	Remote Similarity	NPD6297	Approved
0.6467	Remote Similarity	NPD6662	Clinical (unspecified phase)
0.6459	Remote Similarity	NPD7891	Discontinued
0.645	Remote Similarity	NPD6793	Clinical (unspecified phase)
0.645	Remote Similarity	NPD4084	Clinical (unspecified phase)
0.6442	Remote Similarity	NPD3533	Approved
0.6442	Remote Similarity	NPD2972	Approved
0.6442	Remote Similarity	NPD2491	Approved
0.6402	Remote Similarity	NPD3817	Phase 2
0.6392	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6392	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6392	Remote Similarity	NPD6166	Phase 2
0.6368	Remote Similarity	NPD3882	Suspended
0.6368	Remote Similarity	NPD7585	Approved
0.6364	Remote Similarity	NPD7039	Approved
0.6364	Remote Similarity	NPD1337	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD3057	Approved
0.6364	Remote Similarity	NPD6875	Approved
0.6364	Remote Similarity	NPD7038	Approved
0.6364	Remote Similarity	NPD3448	Approved
0.6364	Remote Similarity	NPD6876	Approved
0.6355	Remote Similarity	NPD2490	Approved
0.6355	Remote Similarity	NPD2488	Approved
0.6349	Remote Similarity	NPD2801	Approved
0.6346	Remote Similarity	NPD5457	Discontinued
0.6339	Remote Similarity	NPD3281	Clinical (unspecified phase)
0.6332	Remote Similarity	NPD7808	Phase 3
0.633	Remote Similarity	NPD6385	Approved
0.633	Remote Similarity	NPD6386	Approved
0.6327	Remote Similarity	NPD2163	Approved
0.6324	Remote Similarity	NPD1512	Approved
0.6321	Remote Similarity	NPD7583	Approved
0.6319	Remote Similarity	NPD5481	Discontinued
0.6313	Remote Similarity	NPD6797	Phase 2
0.6307	Remote Similarity	NPD5745	Approved
0.6305	Remote Similarity	NPD6377	Clinical (unspecified phase)
0.6298	Remote Similarity	NPD7811	Phase 3
0.6298	Remote Similarity	NPD7810	Phase 3
0.6281	Remote Similarity	NPD7251	Discontinued
0.6271	Remote Similarity	NPD3142	Approved
0.6271	Remote Similarity	NPD3140	Approved
0.6269	Remote Similarity	NPD3251	Approved
0.6262	Remote Similarity	NPD7256	Discontinued
0.6256	Remote Similarity	NPD7291	Discontinued
0.6245	Remote Similarity	NPD7048	Phase 3
0.6244	Remote Similarity	NPD7584	Approved
0.6238	Remote Similarity	NPD4482	Phase 3
0.6238	Remote Similarity	NPD2493	Approved
0.6238	Remote Similarity	NPD2494	Approved
0.6237	Remote Similarity	NPD8127	Discontinued
0.623	Remote Similarity	NPD4110	Phase 3
0.623	Remote Similarity	NPD5977	Approved
0.623	Remote Similarity	NPD5978	Approved
0.623	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6226	Remote Similarity	NPD4582	Approved
0.6226	Remote Similarity	NPD4583	Approved
0.6224	Remote Similarity	NPD3451	Clinical (unspecified phase)
0.6223	Remote Similarity	NPD3455	Phase 2
0.6223	Remote Similarity	NPD3769	Discontinued
0.6221	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6219	Remote Similarity	NPD7281	Phase 3
0.6219	Remote Similarity	NPD7280	Phase 3
0.6218	Remote Similarity	NPD6862	Phase 2
0.6216	Remote Similarity	NPD1511	Approved
0.6216	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6212	Remote Similarity	NPD7054	Approved
0.6211	Remote Similarity	NPD1934	Approved
0.6211	Remote Similarity	NPD7577	Discontinued
0.6209	Remote Similarity	NPD3655	Clinical (unspecified phase)
0.6205	Remote Similarity	NPD7608	Discontinued
0.6203	Remote Similarity	NPD2122	Discontinued
0.6202	Remote Similarity	NPD2973	Approved
0.6202	Remote Similarity	NPD2975	Approved
0.6202	Remote Similarity	NPD2974	Approved
0.6193	Remote Similarity	NPD5746	Approved
0.619	Remote Similarity	NPD4580	Approved
0.619	Remote Similarity	NPD7255	Clinical (unspecified phase)
0.619	Remote Similarity	NPD4107	Approved
0.6188	Remote Similarity	NPD1725	Approved
0.6188	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.6183	Remote Similarity	NPD1754	Clinical (unspecified phase)
0.6181	Remote Similarity	NPD7472	Approved
0.6179	Remote Similarity	NPD4004	Approved
0.6179	Remote Similarity	NPD4002	Approved
0.6176	Remote Similarity	NPD4157	Discontinued
0.6175	Remote Similarity	NPD4236	Phase 3
0.6175	Remote Similarity	NPD4237	Approved
0.6175	Remote Similarity	NPD2976	Clinical (unspecified phase)
0.6173	Remote Similarity	NPD5242	Approved
0.6171	Remote Similarity	NPD9494	Approved
0.6171	Remote Similarity	NPD7907	Approved
0.6169	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6169	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6164	Remote Similarity	NPD8149	Discontinued
0.6162	Remote Similarity	NPD2822	Clinical (unspecified phase)
0.6161	Remote Similarity	NPD3450	Approved
0.6161	Remote Similarity	NPD7476	Discontinued
0.6161	Remote Similarity	NPD3452	Approved
0.6158	Remote Similarity	NPD6873	Phase 2
0.615	Remote Similarity	NPD4040	Phase 1
0.6146	Remote Similarity	NPD7235	Clinical (unspecified phase)
0.6146	Remote Similarity	NPD5353	Approved
0.6139	Remote Similarity	NPD2971	Approved
0.6139	Remote Similarity	NPD2968	Approved
0.6135	Remote Similarity	NPD4466	Phase 1
0.6135	Remote Similarity	NPD6181	Discontinued
0.6129	Remote Similarity	NPD5297	Approved
0.6127	Remote Similarity	NPD3863	Clinical (unspecified phase)
0.6126	Remote Similarity	NPD6844	Discontinued
0.6121	Remote Similarity	NPD7607	Clinical (unspecified phase)
0.6119	Remote Similarity	NPD5192	Clinical (unspecified phase)
0.6117	Remote Similarity	NPD5525	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD6720	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD2653	Approved
0.6108	Remote Similarity	NPD6618	Phase 2
0.6106	Remote Similarity	NPD3473	Clinical (unspecified phase)
0.61	Remote Similarity	NPD7074	Phase 3
0.6096	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6096	Remote Similarity	NPD3536	Discontinued
0.6094	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6094	Remote Similarity	NPD5773	Approved
0.6094	Remote Similarity	NPD5772	Approved
0.6093	Remote Similarity	NPD6296	Discontinued
0.6093	Remote Similarity	NPD7263	Phase 2
0.6087	Remote Similarity	NPD4162	Approved
0.6087	Remote Similarity	NPD3060	Approved
0.6085	Remote Similarity	NPD3687	Approved
0.6085	Remote Similarity	NPD4124	Clinical (unspecified phase)
0.6085	Remote Similarity	NPD3686	Approved
0.6083	Remote Similarity	NPD5914	Approved
0.6081	Remote Similarity	NPD4111	Phase 1
0.6081	Remote Similarity	NPD4665	Approved
0.608	Remote Similarity	NPD7177	Discontinued
0.6073	Remote Similarity	NPD6677	Suspended
0.6073	Remote Similarity	NPD2541	Clinical (unspecified phase)
0.6071	Remote Similarity	NPD2821	Approved
0.607	Remote Similarity	NPD6211	Clinical (unspecified phase)
0.6067	Remote Similarity	NPD5718	Phase 2
0.6061	Remote Similarity	NPD4575	Clinical (unspecified phase)
0.6061	Remote Similarity	NPD7784	Clinical (unspecified phase)
0.6054	Remote Similarity	NPD6331	Phase 2
0.6053	Remote Similarity	NPD2649	Approved
0.6053	Remote Similarity	NPD2651	Approved
0.6045	Remote Similarity	NPD2614	Approved
0.6045	Remote Similarity	NPD5752	Clinical (unspecified phase)
0.6044	Remote Similarity	NPD6028	Clinical (unspecified phase)
0.6044	Remote Similarity	NPD6029	Clinical (unspecified phase)
0.6043	Remote Similarity	NPD1774	Approved
0.6042	Remote Similarity	NPD5722	Discontinued
0.6032	Remote Similarity	NPD3639	Approved
0.6032	Remote Similarity	NPD3640	Phase 3
0.6032	Remote Similarity	NPD3641	Approved
0.6031	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6031	Remote Similarity	NPD5019	Clinical (unspecified phase)
0.6023	Remote Similarity	NPD6584	Phase 3
0.6022	Remote Similarity	NPD5241	Discontinued
0.6022	Remote Similarity	NPD2219	Phase 1
0.6021	Remote Similarity	NPD7028	Phase 2
0.602	Remote Similarity	NPD2325	Approved
0.6019	Remote Similarity	NPD5071	Phase 2
0.6011	Remote Similarity	NPD2438	Suspended
0.6011	Remote Similarity	NPD4123	Phase 3
0.6011	Remote Similarity	NPD2239	Approved
0.6011	Remote Similarity	NPD2240	Approved
0.6011	Remote Similarity	NPD7095	Approved
0.601	Remote Similarity	NPD7972	Discontinued
0.601	Remote Similarity	NPD2388	Discontinued
0.601	Remote Similarity	NPD6818	Clinical (unspecified phase)
0.601	Remote Similarity	NPD3936	Clinical (unspecified phase)
0.6	Remote Similarity	NPD1307	Phase 2
0.6	Remote Similarity	NPD1309	Phase 2
0.6	Remote Similarity	NPD8031	Discontinued
0.6	Remote Similarity	NPD826	Approved
0.6	Remote Similarity	NPD4210	Discontinued
0.6	Remote Similarity	NPD3818	Discontinued
0.6	Remote Similarity	NPD5536	Phase 2
0.6	Remote Similarity	NPD7075	Discontinued
0.6	Remote Similarity	NPD825	Approved
0.599	Remote Similarity	NPD7484	Phase 3
0.599	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.599	Remote Similarity	NPD7485	Phase 3
0.5988	Remote Similarity	NPD2423	Clinical (unspecified phase)
0.5979	Remote Similarity	NPD7318	Phase 3
0.5979	Remote Similarity	NPD5967	Approved
0.5978	Remote Similarity	NPD3268	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