NPASS Compound

Structure

NPC475775 OpenBabel07101718272D 34 38 0 0 1 0 0 0 0 0999 V2000 -0.9525 4.9229 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5354 2.3884 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6756 3.0453 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8881 -0.4280 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9349 1.2059 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4900 4.0693 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6668 0.6512 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4815 0.9052 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3000 0.9233 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9980 3.2420 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1536 1.1752 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9648 -0.1280 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.8710 0.5648 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.4696 -0.0552 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4920 1.6042 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4432 0.9927 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.0139 1.5873 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.4817 -0.6333 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.7592 -0.2377 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.2813 1.6223 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.9684 3.2682 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5708 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.2461 0.2863 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.2708 0.9233 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.7854 -0.5706 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.1489 -0.7488 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3399 2.0770 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8228 -1.5422 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4983 -1.1728 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4310 4.1218 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2589 -1.3863 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 -1.8919 1.9628 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4764 2.4409 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 6 1 0 0 0 0 2 10 1 0 0 0 0 3 11 1 0 0 0 0 6 10 2 0 0 0 0 7 11 2 0 0 0 0 7 14 1 0 0 0 0 8 13 1 0 0 0 0 8 15 1 0 0 0 0 9 32 1 0 0 0 0 10 21 1 0 0 0 0 11 16 1 0 0 0 0 12 4 1 6 0 0 0 12 13 1 0 0 0 0 12 18 1 0 0 0 0 13 24 1 6 0 0 0 14 19 1 0 0 0 0 14 26 2 0 0 0 0 15 27 2 0 0 0 0 15 33 1 0 0 0 0 16 17 1 0 0 0 0 16 23 1 6 0 0 0 17 20 1 0 0 0 0 17 34 1 1 0 0 0 18 25 1 6 0 0 0 18 28 1 0 0 0 0 19 23 1 6 0 0 0 19 29 1 0 0 0 0 20 24 1 1 0 0 0 20 33 1 0 0 0 0 21 30 2 0 0 0 0 21 34 1 0 0 0 0 22 23 1 6 0 0 0 22 24 1 0 0 0 0 22 25 1 0 0 0 0 23 5 1 6 0 0 0 24 9 1 1 0 0 0 25 31 1 6 0 0 0 25 32 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	476.2
Volume:	464.104
LogP:	1.772
LogD:	1.27
LogS:	-4.254
# Rotatable Bonds:	3
TPSA:	136.43
# H-Bond Aceptor:	9
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.339
Synthetic Accessibility Score:	6.721
Fsp3:	0.76
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.252
MDCK Permeability:	6.127925007604063e-05
Pgp-inhibitor:	0.998
Pgp-substrate:	0.013
Human Intestinal Absorption (HIA):	0.211
20% Bioavailability (F20%):	0.007
30% Bioavailability (F30%):	0.988

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.716
Plasma Protein Binding (PPB):	50.92223358154297%
Volume Distribution (VD):	0.701
Pgp-substrate:	31.189159393310547%

ADMET: Metabolism

CYP1A2-inhibitor:	0.026
CYP1A2-substrate:	0.904
CYP2C19-inhibitor:	0.028
CYP2C19-substrate:	0.634
CYP2C9-inhibitor:	0.026
CYP2C9-substrate:	0.025
CYP2D6-inhibitor:	0.006
CYP2D6-substrate:	0.088
CYP3A4-inhibitor:	0.674
CYP3A4-substrate:	0.257

ADMET: Excretion

Clearance (CL):	4.62
Half-life (T1/2):	0.511

ADMET: Toxicity

hERG Blockers:	0.04
Human Hepatotoxicity (H-HT):	0.277
Drug-inuced Liver Injury (DILI):	0.744
AMES Toxicity:	0.061
Rat Oral Acute Toxicity:	0.831
Maximum Recommended Daily Dose:	0.283
Skin Sensitization:	0.457
Carcinogencity:	0.188
Eye Corrosion:	0.004
Eye Irritation:	0.012
Respiratory Toxicity:	0.975

Download Data

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

Natural Product: NPC475775

Natural Product ID:	NPC475775
*Common Name:**	SGZIVQRVNCEYKD-IFROXHCNSA-N
IUPAC Name:	n.a.
Synonyms:	6Alpha-Tigloyloxychaparrinone
Standard InCHIKey:	SGZIVQRVNCEYKD-IFROXHCNSA-N
Standard InCHI:	InChI=1S/C25H32O9/c1-6-10(2)21(30)34-17-16-11(3)7-14(26)19(29)23(16,5)22-24-9-32-25(22,31)18(28)12(4)13(24)8-15(27)33-20(17)24/h6-7,12-13,16-20,22,28-29,31H,8-9H2,1-5H3/b10-6-/t12-,13+,16-,17-,18-,19-,20-,22-,23-,24-,25+/m1/s1
SMILES:	CC=C(C)C(=O)OC1C2C(=CC(=O)C(C2(C3C45C1OC(=O)CC4C(C(C3(OC5)O)O)C)C)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL515198
PubChem CID:	44584046
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones [CHEMONTID:0002119] Quassinoids

*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
NPO15443	Ailanthus altissima	Species	Simaroubaceae	Eukaryota	n.a.	xylem	n.a.	DOI[10.1248/cpb.24.1532]
NPO15443	Ailanthus altissima	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19299148]
NPO15443	Ailanthus altissima	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22224661]
NPO15443	Ailanthus altissima	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22799262]
NPO15443	Ailanthus altissima	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23290052]
NPO15443	Ailanthus altissima	Species	Simaroubaceae	Eukaryota	stem barks	n.a.	n.a.	PMID[25666824]
NPO15443	Ailanthus altissima	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15443	Ailanthus altissima	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15443	Ailanthus altissima	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO15443	Ailanthus altissima	Species	Simaroubaceae	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	3
Others	2

Activity Type	# Activity
Cell Line	4
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT168	Cell Line	P388	Mus musculus	GI	<	0.01	ug ml-1	PMID[473776]
NPT168	Cell Line	P388	Mus musculus	Activity	=	34.0	%	PMID[473776]
NPT65	Cell Line	HepG2	Homo sapiens	IC50	=	16900.0	nM	PMID[473777]
NPT65	Cell Line	HepG2	Homo sapiens	IC50	=	550.0	nM	PMID[473777]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	50.0	nM	PMID[473777]

☑ 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 NPC475775 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	243
0.1-0.2	1387
0.2-0.3	3930
0.3-0.4	6724
0.4-0.5	11441
0.5-0.6	8277
0.6-0.7	5952
0.7-0.8	3957
0.8-0.85	609
0.85-0.9	122
0.9-0.95	44
0.95-1	11

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC476529
0.9909	High Similarity	NPC107338
0.9909	High Similarity	NPC109607
0.9636	High Similarity	NPC473968
0.9561	High Similarity	NPC470922
0.9455	High Similarity	NPC18547
0.9455	High Similarity	NPC474906
0.945	High Similarity	NPC11252
0.945	High Similarity	NPC289312
0.9369	High Similarity	NPC152199
0.9369	High Similarity	NPC235539
0.9369	High Similarity	NPC134869
0.9364	High Similarity	NPC51978
0.9358	High Similarity	NPC201992
0.9279	High Similarity	NPC470919
0.9279	High Similarity	NPC469877
0.9273	High Similarity	NPC302146
0.9204	High Similarity	NPC297179
0.9196	High Similarity	NPC474046
0.9196	High Similarity	NPC470628
0.9196	High Similarity	NPC259306
0.9115	High Similarity	NPC473590
0.9083	High Similarity	NPC293850
0.906	High Similarity	NPC24651
0.9043	High Similarity	NPC112038
0.9035	High Similarity	NPC188667
0.9035	High Similarity	NPC204552
0.9027	High Similarity	NPC96312
0.9027	High Similarity	NPC40632
0.9027	High Similarity	NPC328374
0.9027	High Similarity	NPC251236
0.9018	High Similarity	NPC49451
0.9	High Similarity	NPC143706
0.9	High Similarity	NPC472534
0.8974	High Similarity	NPC91693
0.8974	High Similarity	NPC265557
0.8974	High Similarity	NPC105926
0.8974	High Similarity	NPC18945
0.8974	High Similarity	NPC67251
0.8957	High Similarity	NPC122971
0.8957	High Similarity	NPC469488
0.8947	High Similarity	NPC309433
0.8938	High Similarity	NPC473798
0.8926	High Similarity	NPC471855
0.8898	High Similarity	NPC476729
0.8889	High Similarity	NPC312833
0.886	High Similarity	NPC474734
0.8818	High Similarity	NPC144854
0.8818	High Similarity	NPC3316
0.8803	High Similarity	NPC470779
0.8803	High Similarity	NPC477046
0.8803	High Similarity	NPC102822
0.8783	High Similarity	NPC470854
0.8783	High Similarity	NPC474654
0.8783	High Similarity	NPC287343
0.8783	High Similarity	NPC97908
0.8783	High Similarity	NPC122033
0.877	High Similarity	NPC478153
0.877	High Similarity	NPC478152
0.877	High Similarity	NPC478150
0.8761	High Similarity	NPC194951
0.8761	High Similarity	NPC474516
0.8761	High Similarity	NPC12046
0.876	High Similarity	NPC471407
0.875	High Similarity	NPC470780
0.8739	High Similarity	NPC189075
0.8739	High Similarity	NPC154608
0.8739	High Similarity	NPC277017
0.8739	High Similarity	NPC275539
0.8739	High Similarity	NPC192813
0.872	High Similarity	NPC596
0.8707	High Similarity	NPC251310
0.8707	High Similarity	NPC17772
0.8699	High Similarity	NPC478151
0.8689	High Similarity	NPC25998
0.8689	High Similarity	NPC172374
0.8689	High Similarity	NPC478155
0.8689	High Similarity	NPC329993
0.8689	High Similarity	NPC301639
0.8689	High Similarity	NPC475377
0.8689	High Similarity	NPC45346
0.8689	High Similarity	NPC264566
0.8689	High Similarity	NPC475167
0.8689	High Similarity	NPC478065
0.8689	High Similarity	NPC134914
0.8689	High Similarity	NPC173435
0.8689	High Similarity	NPC262796
0.8689	High Similarity	NPC477197
0.8689	High Similarity	NPC478064
0.8689	High Similarity	NPC476074
0.8684	High Similarity	NPC157441
0.8684	High Similarity	NPC208998
0.8684	High Similarity	NPC25909
0.8684	High Similarity	NPC7921
0.8661	High Similarity	NPC141350
0.8649	High Similarity	NPC110496
0.8644	High Similarity	NPC202051
0.864	High Similarity	NPC471089
0.864	High Similarity	NPC190065
0.864	High Similarity	NPC141215
0.8632	High Similarity	NPC9674
0.8632	High Similarity	NPC470777
0.8632	High Similarity	NPC77689
0.8632	High Similarity	NPC19028
0.8632	High Similarity	NPC473636
0.8621	High Similarity	NPC134430
0.8621	High Similarity	NPC474483
0.8621	High Similarity	NPC176513
0.8621	High Similarity	NPC470775
0.8618	High Similarity	NPC478154
0.8609	High Similarity	NPC243354
0.8607	High Similarity	NPC477079
0.8607	High Similarity	NPC477076
0.8607	High Similarity	NPC477196
0.8607	High Similarity	NPC477077
0.8607	High Similarity	NPC470913
0.8596	High Similarity	NPC269530
0.8584	High Similarity	NPC83005
0.8584	High Similarity	NPC5103
0.8571	High Similarity	NPC295885
0.8571	High Similarity	NPC140045
0.856	High Similarity	NPC262813
0.8559	High Similarity	NPC48692
0.8559	High Similarity	NPC102352
0.8548	High Similarity	NPC168879
0.8547	High Similarity	NPC470776
0.8534	High Similarity	NPC471816
0.8534	High Similarity	NPC44170
0.8534	High Similarity	NPC268954
0.8525	High Similarity	NPC477191
0.8525	High Similarity	NPC311534
0.8525	High Similarity	NPC473620
0.8525	High Similarity	NPC477075
0.8525	High Similarity	NPC245094
0.8525	High Similarity	NPC475281
0.8525	High Similarity	NPC477193
0.8525	High Similarity	NPC329923
0.8525	High Similarity	NPC477192
0.8525	High Similarity	NPC477078
0.8525	High Similarity	NPC477194
0.8522	High Similarity	NPC194273
0.8522	High Similarity	NPC255017
0.8522	High Similarity	NPC469496
0.8522	High Similarity	NPC311592
0.8522	High Similarity	NPC469454
0.8522	High Similarity	NPC469463
0.8522	High Similarity	NPC75167
0.8509	High Similarity	NPC146945
0.8509	High Similarity	NPC171888
0.8509	High Similarity	NPC471243
0.85	High Similarity	NPC227397
0.8496	Intermediate Similarity	NPC27814
0.8492	Intermediate Similarity	NPC251998
0.8487	Intermediate Similarity	NPC476204
0.8487	Intermediate Similarity	NPC170084
0.8482	Intermediate Similarity	NPC230541
0.8475	Intermediate Similarity	NPC211093
0.8475	Intermediate Similarity	NPC473839
0.8475	Intermediate Similarity	NPC127530
0.8475	Intermediate Similarity	NPC475041
0.8475	Intermediate Similarity	NPC473920
0.8475	Intermediate Similarity	NPC470914
0.8468	Intermediate Similarity	NPC46823
0.8468	Intermediate Similarity	NPC178264
0.8468	Intermediate Similarity	NPC102316
0.8468	Intermediate Similarity	NPC30279
0.8468	Intermediate Similarity	NPC476776
0.8468	Intermediate Similarity	NPC277212
0.8468	Intermediate Similarity	NPC477195
0.8468	Intermediate Similarity	NPC71391
0.8468	Intermediate Similarity	NPC192765
0.8468	Intermediate Similarity	NPC473918
0.8462	Intermediate Similarity	NPC470778
0.8462	Intermediate Similarity	NPC146432
0.8462	Intermediate Similarity	NPC475809
0.8462	Intermediate Similarity	NPC13713
0.8462	Intermediate Similarity	NPC284068
0.8455	Intermediate Similarity	NPC476966
0.8455	Intermediate Similarity	NPC88311
0.8455	Intermediate Similarity	NPC82380
0.8455	Intermediate Similarity	NPC97918
0.8455	Intermediate Similarity	NPC115656
0.8455	Intermediate Similarity	NPC305793
0.8455	Intermediate Similarity	NPC244296
0.8455	Intermediate Similarity	NPC141600
0.8455	Intermediate Similarity	NPC11577
0.8455	Intermediate Similarity	NPC273878
0.8455	Intermediate Similarity	NPC280029
0.8455	Intermediate Similarity	NPC470518
0.8455	Intermediate Similarity	NPC1314
0.8455	Intermediate Similarity	NPC472267
0.8455	Intermediate Similarity	NPC252657
0.8455	Intermediate Similarity	NPC9470
0.8455	Intermediate Similarity	NPC107536
0.8455	Intermediate Similarity	NPC269484
0.8455	Intermediate Similarity	NPC252289
0.8455	Intermediate Similarity	NPC470912
0.8448	Intermediate Similarity	NPC102088
0.8448	Intermediate Similarity	NPC178289
0.8448	Intermediate Similarity	NPC110861

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 NPC475775 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	216
0.1-0.2	1566
0.2-0.3	3546
0.3-0.4	2420
0.4-0.5	806
0.5-0.6	312
0.6-0.7	154
0.7-0.8	118
0.8-0.85	12
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8407	Intermediate Similarity	NPD6686	Approved
0.8211	Intermediate Similarity	NPD7507	Approved
0.8197	Intermediate Similarity	NPD8328	Phase 3
0.8016	Intermediate Similarity	NPD7319	Approved
0.7984	Intermediate Similarity	NPD7492	Approved
0.7966	Intermediate Similarity	NPD6882	Approved
0.7966	Intermediate Similarity	NPD8297	Approved
0.7951	Intermediate Similarity	NPD6054	Approved
0.7951	Intermediate Similarity	NPD6319	Approved
0.7937	Intermediate Similarity	NPD7736	Approved
0.7931	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.792	Intermediate Similarity	NPD6616	Approved
0.7899	Intermediate Similarity	NPD4632	Approved
0.7863	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7863	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD7078	Approved
0.7851	Intermediate Similarity	NPD7115	Discovery
0.7851	Intermediate Similarity	NPD6009	Approved
0.7851	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7845	Intermediate Similarity	NPD6412	Phase 2
0.7823	Intermediate Similarity	NPD6370	Approved
0.7805	Intermediate Similarity	NPD6059	Approved
0.7778	Intermediate Similarity	NPD6881	Approved
0.7778	Intermediate Similarity	NPD6899	Approved
0.7759	Intermediate Similarity	NPD5739	Approved
0.7759	Intermediate Similarity	NPD7128	Approved
0.7759	Intermediate Similarity	NPD6675	Approved
0.7759	Intermediate Similarity	NPD6402	Approved
0.7742	Intermediate Similarity	NPD6015	Approved
0.7742	Intermediate Similarity	NPD6016	Approved
0.7731	Intermediate Similarity	NPD6649	Approved
0.7731	Intermediate Similarity	NPD6650	Approved
0.7724	Intermediate Similarity	NPD7516	Approved
0.7717	Intermediate Similarity	NPD8293	Discontinued
0.7712	Intermediate Similarity	NPD6373	Approved
0.7712	Intermediate Similarity	NPD6372	Approved
0.7699	Intermediate Similarity	NPD7638	Approved
0.7699	Intermediate Similarity	NPD4225	Approved
0.7692	Intermediate Similarity	NPD5697	Approved
0.768	Intermediate Similarity	NPD5988	Approved
0.7647	Intermediate Similarity	NPD7290	Approved
0.7647	Intermediate Similarity	NPD6883	Approved
0.7647	Intermediate Similarity	NPD7102	Approved
0.7647	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7642	Intermediate Similarity	NPD7327	Approved
0.7642	Intermediate Similarity	NPD7328	Approved
0.7632	Intermediate Similarity	NPD7640	Approved
0.7632	Intermediate Similarity	NPD7639	Approved
0.7627	Intermediate Similarity	NPD7320	Approved
0.76	Intermediate Similarity	NPD8515	Approved
0.76	Intermediate Similarity	NPD7503	Approved
0.76	Intermediate Similarity	NPD8033	Approved
0.76	Intermediate Similarity	NPD8513	Phase 3
0.76	Intermediate Similarity	NPD8516	Approved
0.76	Intermediate Similarity	NPD8517	Approved
0.7583	Intermediate Similarity	NPD6617	Approved
0.7583	Intermediate Similarity	NPD6847	Approved
0.7583	Intermediate Similarity	NPD8130	Phase 1
0.7583	Intermediate Similarity	NPD6869	Approved
0.7563	Intermediate Similarity	NPD6013	Approved
0.7563	Intermediate Similarity	NPD6014	Approved
0.7563	Intermediate Similarity	NPD6012	Approved
0.7542	Intermediate Similarity	NPD5701	Approved
0.752	Intermediate Similarity	NPD8377	Approved
0.752	Intermediate Similarity	NPD8294	Approved
0.748	Intermediate Similarity	NPD7604	Phase 2
0.7479	Intermediate Similarity	NPD6011	Approved
0.746	Intermediate Similarity	NPD8380	Approved
0.746	Intermediate Similarity	NPD8378	Approved
0.746	Intermediate Similarity	NPD8379	Approved
0.746	Intermediate Similarity	NPD5983	Phase 2
0.746	Intermediate Similarity	NPD8335	Approved
0.746	Intermediate Similarity	NPD8296	Approved
0.7459	Intermediate Similarity	NPD8133	Approved
0.7438	Intermediate Similarity	NPD8413	Clinical (unspecified phase)
0.7395	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.7387	Intermediate Similarity	NPD6698	Approved
0.7387	Intermediate Similarity	NPD46	Approved
0.7364	Intermediate Similarity	NPD6336	Discontinued
0.7355	Intermediate Similarity	NPD4634	Approved
0.735	Intermediate Similarity	NPD5211	Phase 2
0.7348	Intermediate Similarity	NPD7260	Phase 2
0.7345	Intermediate Similarity	NPD7748	Approved
0.7328	Intermediate Similarity	NPD5285	Approved
0.7328	Intermediate Similarity	NPD5286	Approved
0.7328	Intermediate Similarity	NPD4696	Approved
0.7323	Intermediate Similarity	NPD6921	Approved
0.7321	Intermediate Similarity	NPD7515	Phase 2
0.7311	Intermediate Similarity	NPD6008	Approved
0.7304	Intermediate Similarity	NPD7902	Approved
0.7304	Intermediate Similarity	NPD4755	Approved
0.7295	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7252	Intermediate Similarity	NPD6033	Approved
0.7227	Intermediate Similarity	NPD5141	Approved
0.7217	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7217	Intermediate Similarity	NPD5221	Approved
0.7217	Intermediate Similarity	NPD5222	Approved
0.7203	Intermediate Similarity	NPD5224	Approved
0.7203	Intermediate Similarity	NPD4633	Approved
0.7203	Intermediate Similarity	NPD5225	Approved
0.7203	Intermediate Similarity	NPD5226	Approved
0.72	Intermediate Similarity	NPD6274	Approved
0.7179	Intermediate Similarity	NPD4700	Approved
0.7176	Intermediate Similarity	NPD8074	Phase 3
0.7168	Intermediate Similarity	NPD6079	Approved
0.7165	Intermediate Similarity	NPD7100	Approved
0.7165	Intermediate Similarity	NPD7101	Approved
0.7164	Intermediate Similarity	NPD6845	Suspended
0.7155	Intermediate Similarity	NPD5173	Approved
0.7155	Intermediate Similarity	NPD6083	Phase 2
0.7155	Intermediate Similarity	NPD6084	Phase 2
0.7143	Intermediate Similarity	NPD5175	Approved
0.7143	Intermediate Similarity	NPD5328	Approved
0.7143	Intermediate Similarity	NPD5174	Approved
0.7119	Intermediate Similarity	NPD5344	Discontinued
0.7119	Intermediate Similarity	NPD5223	Approved
0.7117	Intermediate Similarity	NPD3573	Approved
0.7107	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD6399	Phase 3
0.7097	Intermediate Similarity	NPD6053	Discontinued
0.7087	Intermediate Similarity	NPD6335	Approved
0.7069	Intermediate Similarity	NPD4697	Phase 3
0.7063	Intermediate Similarity	NPD6868	Approved
0.7059	Intermediate Similarity	NPD7632	Discontinued
0.7049	Intermediate Similarity	NPD4729	Approved
0.7049	Intermediate Similarity	NPD4730	Approved
0.7043	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7043	Intermediate Similarity	NPD7900	Approved
0.7025	Intermediate Similarity	NPD4768	Approved
0.7025	Intermediate Similarity	NPD4767	Approved
0.7008	Intermediate Similarity	NPD6317	Approved
0.6953	Remote Similarity	NPD6313	Approved
0.6953	Remote Similarity	NPD6314	Approved
0.6947	Remote Similarity	NPD6067	Discontinued
0.6937	Remote Similarity	NPD1694	Approved
0.6935	Remote Similarity	NPD5250	Approved
0.6935	Remote Similarity	NPD6371	Approved
0.6935	Remote Similarity	NPD5247	Approved
0.6935	Remote Similarity	NPD5251	Approved
0.6935	Remote Similarity	NPD5249	Phase 3
0.6935	Remote Similarity	NPD5248	Approved
0.6923	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD6908	Approved
0.6923	Remote Similarity	NPD6909	Approved
0.6911	Remote Similarity	NPD5128	Approved
0.6903	Remote Similarity	NPD5737	Approved
0.6903	Remote Similarity	NPD6672	Approved
0.6875	Remote Similarity	NPD3618	Phase 1
0.687	Remote Similarity	NPD6411	Approved
0.686	Remote Similarity	NPD4754	Approved
0.6838	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6838	Remote Similarity	NPD5695	Phase 3
0.6818	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.681	Remote Similarity	NPD5778	Approved
0.681	Remote Similarity	NPD5779	Approved
0.6807	Remote Similarity	NPD5696	Approved
0.6807	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6783	Remote Similarity	NPD7838	Discovery
0.6754	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.675	Remote Similarity	NPD6648	Approved
0.6746	Remote Similarity	NPD5216	Approved
0.6746	Remote Similarity	NPD5215	Approved
0.6746	Remote Similarity	NPD5217	Approved
0.6726	Remote Similarity	NPD6684	Approved
0.6726	Remote Similarity	NPD7334	Approved
0.6726	Remote Similarity	NPD6409	Approved
0.6726	Remote Similarity	NPD7521	Approved
0.6726	Remote Similarity	NPD5330	Approved
0.6726	Remote Similarity	NPD7146	Approved
0.6724	Remote Similarity	NPD7983	Approved
0.6724	Remote Similarity	NPD5693	Phase 1
0.6714	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6696	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6696	Remote Similarity	NPD4786	Approved
0.6696	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6696	Remote Similarity	NPD4753	Phase 2
0.6696	Remote Similarity	NPD6101	Approved
0.6667	Remote Similarity	NPD4202	Approved
0.6667	Remote Similarity	NPD5169	Approved
0.6667	Remote Similarity	NPD3667	Approved
0.6667	Remote Similarity	NPD5135	Approved
0.6667	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6643	Remote Similarity	NPD8387	Clinical (unspecified phase)
0.6642	Remote Similarity	NPD5956	Approved
0.664	Remote Similarity	NPD5168	Approved
0.6636	Remote Similarity	NPD4695	Discontinued
0.6625	Remote Similarity	NPD7799	Discontinued
0.6614	Remote Similarity	NPD5127	Approved
0.661	Remote Similarity	NPD5282	Discontinued
0.6609	Remote Similarity	NPD6903	Approved
0.6581	Remote Similarity	NPD8035	Phase 2
0.6581	Remote Similarity	NPD8034	Phase 2
0.6571	Remote Similarity	NPD8415	Approved
0.6555	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6555	Remote Similarity	NPD5210	Approved
0.6555	Remote Similarity	NPD4629	Approved
0.6554	Remote Similarity	NPD7236	Approved
0.6552	Remote Similarity	NPD6904	Approved
0.6552	Remote Similarity	NPD6673	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