NPASS Compound

Structure

NPC473968 OpenBabel07101719252D 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 1 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 1 1 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:	478.22
Volume:	466.74
LogP:	2.052
LogD:	1.556
LogS:	-3.594
# Rotatable Bonds:	3
TPSA:	142.75
# H-Bond Aceptor:	9
# H-Bond Donor:	4
# Rings:	5
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.253
Synthetic Accessibility Score:	6.754
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:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.587
MDCK Permeability:	8.366807014681399e-05
Pgp-inhibitor:	0.764
Pgp-substrate:	0.996
Human Intestinal Absorption (HIA):	0.909
20% Bioavailability (F20%):	0.016
30% Bioavailability (F30%):	0.991

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.132
Plasma Protein Binding (PPB):	49.095767974853516%
Volume Distribution (VD):	0.939
Pgp-substrate:	22.65493392944336%

ADMET: Metabolism

CYP1A2-inhibitor:	0.02
CYP1A2-substrate:	0.821
CYP2C19-inhibitor:	0.017
CYP2C19-substrate:	0.54
CYP2C9-inhibitor:	0.006
CYP2C9-substrate:	0.016
CYP2D6-inhibitor:	0.006
CYP2D6-substrate:	0.085
CYP3A4-inhibitor:	0.262
CYP3A4-substrate:	0.189

ADMET: Excretion

Clearance (CL):	3.247
Half-life (T1/2):	0.83

ADMET: Toxicity

hERG Blockers:	0.068
Human Hepatotoxicity (H-HT):	0.818
Drug-inuced Liver Injury (DILI):	0.575
AMES Toxicity:	0.028
Rat Oral Acute Toxicity:	0.715
Maximum Recommended Daily Dose:	0.057
Skin Sensitization:	0.218
Carcinogencity:	0.022
Eye Corrosion:	0.003
Eye Irritation:	0.013
Respiratory Toxicity:	0.969

Download Data

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

Natural Product: NPC473968

Natural Product ID:	NPC473968
*Common Name:**	NMMILYGYICKSOQ-HHLMMFKLSA-N
IUPAC Name:	n.a.
Synonyms:	6Alpha-Tigloyloxychaparrin
Standard InCHIKey:	NMMILYGYICKSOQ-HHLMMFKLSA-N
Standard InCHI:	InChI=1S/C25H34O9/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/h6-7,12-14,16-20,22,26,28-29,31H,8-9H2,1-5H3/b10-6-/t12-,13+,14+,16-,17-,18-,19-,20-,22-,23-,24-,25+/m1/s1
SMILES:	CC=C(C)C(=O)OC1C2C(=CC(C(C2(C3C45C1OC(=O)CC4C(C(C3(OC5)O)O)C)C)O)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL456736
PubChem CID:	44584045
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	1

Activity Type	# Activity
Cell Line	3
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	=	0.24	ug ml-1	PMID[533010]
NPT65	Cell Line	HepG2	Homo sapiens	IC50	>	50000.0	nM	PMID[533011]
NPT65	Cell Line	HepG2	Homo sapiens	IC50	=	10540.0	nM	PMID[533011]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	2430.0	nM	PMID[533011]

☑ 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 NPC473968 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	236
0.1-0.2	1333
0.2-0.3	3731
0.3-0.4	6516
0.4-0.5	11644
0.5-0.6	8249
0.6-0.7	6039
0.7-0.8	4092
0.8-0.85	701
0.85-0.9	121
0.9-0.95	27
0.95-1	8

Similarity Score	Similarity Level	Natural Product ID
0.9636	High Similarity	NPC476529
0.9636	High Similarity	NPC475775
0.955	High Similarity	NPC107338
0.955	High Similarity	NPC109607
0.9386	High Similarity	NPC470922
0.9346	High Similarity	NPC143706
0.9346	High Similarity	NPC472534
0.9286	High Similarity	NPC122971
0.9273	High Similarity	NPC469877
0.9273	High Similarity	NPC470919
0.9266	High Similarity	NPC302146
0.9189	High Similarity	NPC259306
0.9189	High Similarity	NPC474046
0.9189	High Similarity	NPC470628
0.9182	High Similarity	NPC51978
0.9099	High Similarity	NPC474906
0.9099	High Similarity	NPC18547
0.9091	High Similarity	NPC289312
0.9091	High Similarity	NPC11252
0.9018	High Similarity	NPC152199
0.9018	High Similarity	NPC235539
0.9018	High Similarity	NPC134869
0.9	High Similarity	NPC201992
0.8966	High Similarity	NPC67251
0.8938	High Similarity	NPC473590
0.8919	High Similarity	NPC194951
0.8919	High Similarity	NPC269530
0.8919	High Similarity	NPC12046
0.8899	High Similarity	NPC275539
0.8899	High Similarity	NPC189075
0.887	High Similarity	NPC112038
0.886	High Similarity	NPC297179
0.885	High Similarity	NPC474734
0.8839	High Similarity	NPC25909
0.8839	High Similarity	NPC157441
0.8807	High Similarity	NPC110496
0.8793	High Similarity	NPC202051
0.8783	High Similarity	NPC473636
0.8783	High Similarity	NPC77689
0.8772	High Similarity	NPC474483
0.8772	High Similarity	NPC134430
0.8761	High Similarity	NPC472274
0.8729	High Similarity	NPC24651
0.8729	High Similarity	NPC476729
0.8727	High Similarity	NPC293850
0.8716	High Similarity	NPC127609
0.8707	High Similarity	NPC48692
0.8696	High Similarity	NPC204552
0.8696	High Similarity	NPC188667
0.8684	High Similarity	NPC251236
0.8684	High Similarity	NPC268954
0.8684	High Similarity	NPC96312
0.8684	High Similarity	NPC471816
0.8684	High Similarity	NPC40632
0.8684	High Similarity	NPC44170
0.8684	High Similarity	NPC328374
0.8673	High Similarity	NPC264153
0.8673	High Similarity	NPC49451
0.8644	High Similarity	NPC18945
0.8644	High Similarity	NPC265557
0.8644	High Similarity	NPC105926
0.8644	High Similarity	NPC91693
0.8636	High Similarity	NPC230541
0.8632	High Similarity	NPC476204
0.8632	High Similarity	NPC170084
0.8621	High Similarity	NPC469488
0.8621	High Similarity	NPC470914
0.8621	High Similarity	NPC211093
0.8621	High Similarity	NPC475041
0.8621	High Similarity	NPC473839
0.8611	High Similarity	NPC295791
0.8609	High Similarity	NPC13713
0.8609	High Similarity	NPC309433
0.8609	High Similarity	NPC470775
0.8609	High Similarity	NPC176513
0.8609	High Similarity	NPC475809
0.8607	High Similarity	NPC471855
0.8607	High Similarity	NPC478153
0.8607	High Similarity	NPC478150
0.8607	High Similarity	NPC478152
0.8596	High Similarity	NPC181145
0.8596	High Similarity	NPC110861
0.8596	High Similarity	NPC473798
0.8596	High Similarity	NPC243354
0.8584	High Similarity	NPC472002
0.8583	High Similarity	NPC470780
0.8571	High Similarity	NPC5103
0.8571	High Similarity	NPC318135
0.8571	High Similarity	NPC83005
0.8559	High Similarity	NPC269642
0.8559	High Similarity	NPC392
0.8559	High Similarity	NPC177524
0.8559	High Similarity	NPC312833
0.8559	High Similarity	NPC219900
0.8559	High Similarity	NPC475263
0.8547	High Similarity	NPC476150
0.8547	High Similarity	NPC470312
0.8547	High Similarity	NPC476127
0.8545	High Similarity	NPC102352
0.8537	High Similarity	NPC478151
0.8534	High Similarity	NPC251310
0.8534	High Similarity	NPC470776
0.8532	High Similarity	NPC254202
0.8525	High Similarity	NPC173435
0.8525	High Similarity	NPC478065
0.8525	High Similarity	NPC25998
0.8525	High Similarity	NPC264566
0.8525	High Similarity	NPC301639
0.8525	High Similarity	NPC478064
0.8525	High Similarity	NPC476074
0.8525	High Similarity	NPC134914
0.8525	High Similarity	NPC329993
0.8525	High Similarity	NPC262796
0.8525	High Similarity	NPC172374
0.8525	High Similarity	NPC478155
0.8525	High Similarity	NPC477197
0.8525	High Similarity	NPC475167
0.8525	High Similarity	NPC475377
0.8525	High Similarity	NPC45346
0.8522	High Similarity	NPC106228
0.8522	High Similarity	NPC138372
0.8512	High Similarity	NPC473620
0.8512	High Similarity	NPC245094
0.8512	High Similarity	NPC311534
0.8509	High Similarity	NPC469496
0.8509	High Similarity	NPC311592
0.8509	High Similarity	NPC75167
0.8509	High Similarity	NPC293658
0.8509	High Similarity	NPC194273
0.8509	High Similarity	NPC469463
0.8509	High Similarity	NPC469454
0.8509	High Similarity	NPC255017
0.8509	High Similarity	NPC474410
0.85	High Similarity	NPC293112
0.8496	Intermediate Similarity	NPC132790
0.8496	Intermediate Similarity	NPC471243
0.8496	Intermediate Similarity	NPC474846
0.8496	Intermediate Similarity	NPC469655
0.8496	Intermediate Similarity	NPC97939
0.8496	Intermediate Similarity	NPC247031
0.8496	Intermediate Similarity	NPC100329
0.8496	Intermediate Similarity	NPC188738
0.8496	Intermediate Similarity	NPC469656
0.8487	Intermediate Similarity	NPC469789
0.8487	Intermediate Similarity	NPC469382
0.8487	Intermediate Similarity	NPC27363
0.8482	Intermediate Similarity	NPC112457
0.8482	Intermediate Similarity	NPC141350
0.8475	Intermediate Similarity	NPC102822
0.8475	Intermediate Similarity	NPC470779
0.8475	Intermediate Similarity	NPC477046
0.8468	Intermediate Similarity	NPC187435
0.8468	Intermediate Similarity	NPC293512
0.8468	Intermediate Similarity	NPC67321
0.8468	Intermediate Similarity	NPC3316
0.8468	Intermediate Similarity	NPC144854
0.8468	Intermediate Similarity	NPC473586
0.8462	Intermediate Similarity	NPC9674
0.8462	Intermediate Similarity	NPC19028
0.8462	Intermediate Similarity	NPC469380
0.8462	Intermediate Similarity	NPC477071
0.8455	Intermediate Similarity	NPC478154
0.8448	Intermediate Similarity	NPC98249
0.8448	Intermediate Similarity	NPC470854
0.8448	Intermediate Similarity	NPC470171
0.8448	Intermediate Similarity	NPC122033
0.8448	Intermediate Similarity	NPC53396
0.8448	Intermediate Similarity	NPC97908
0.8448	Intermediate Similarity	NPC474654
0.8448	Intermediate Similarity	NPC469684
0.8448	Intermediate Similarity	NPC287343
0.8448	Intermediate Similarity	NPC473405
0.8448	Intermediate Similarity	NPC284068
0.8443	Intermediate Similarity	NPC477077
0.8443	Intermediate Similarity	NPC476966
0.8443	Intermediate Similarity	NPC477076
0.8443	Intermediate Similarity	NPC477079
0.8443	Intermediate Similarity	NPC470913
0.8443	Intermediate Similarity	NPC477196
0.8443	Intermediate Similarity	NPC471407
0.8435	Intermediate Similarity	NPC475633
0.8435	Intermediate Similarity	NPC102088
0.843	Intermediate Similarity	NPC42399
0.8421	Intermediate Similarity	NPC90952
0.8421	Intermediate Similarity	NPC277769
0.8421	Intermediate Similarity	NPC321272
0.8421	Intermediate Similarity	NPC174836
0.8421	Intermediate Similarity	NPC328074
0.8421	Intermediate Similarity	NPC470025
0.8421	Intermediate Similarity	NPC474516
0.8421	Intermediate Similarity	NPC317460
0.8417	Intermediate Similarity	NPC172154
0.8417	Intermediate Similarity	NPC469379
0.8417	Intermediate Similarity	NPC81736
0.8417	Intermediate Similarity	NPC86346
0.8417	Intermediate Similarity	NPC8369
0.8417	Intermediate Similarity	NPC75856
0.8413	Intermediate Similarity	NPC596
0.8413	Intermediate Similarity	NPC140045
0.8413	Intermediate Similarity	NPC295885

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 NPC473968 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	202
0.1-0.2	1507
0.2-0.3	3505
0.3-0.4	2449
0.4-0.5	878
0.5-0.6	327
0.6-0.7	176
0.7-0.8	99
0.8-0.85	7
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8559	High Similarity	NPD6686	Approved
0.8347	Intermediate Similarity	NPD7507	Approved
0.8145	Intermediate Similarity	NPD7319	Approved
0.8	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD4225	Approved
0.7983	Intermediate Similarity	NPD7115	Discovery
0.7928	Intermediate Similarity	NPD7640	Approved
0.7928	Intermediate Similarity	NPD7639	Approved
0.7886	Intermediate Similarity	NPD8328	Phase 3
0.7869	Intermediate Similarity	NPD8517	Approved
0.7869	Intermediate Similarity	NPD8513	Phase 3
0.7869	Intermediate Similarity	NPD8515	Approved
0.7869	Intermediate Similarity	NPD8516	Approved
0.7851	Intermediate Similarity	NPD7516	Approved
0.7845	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7838	Intermediate Similarity	NPD7638	Approved
0.7826	Intermediate Similarity	NPD6412	Phase 2
0.7778	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7769	Intermediate Similarity	NPD7327	Approved
0.7769	Intermediate Similarity	NPD7328	Approved
0.7724	Intermediate Similarity	NPD8033	Approved
0.7724	Intermediate Similarity	NPD7503	Approved
0.7686	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.768	Intermediate Similarity	NPD7492	Approved
0.7647	Intermediate Similarity	NPD8297	Approved
0.7647	Intermediate Similarity	NPD6882	Approved
0.7642	Intermediate Similarity	NPD8377	Approved
0.7642	Intermediate Similarity	NPD6319	Approved
0.7642	Intermediate Similarity	NPD6054	Approved
0.7642	Intermediate Similarity	NPD8294	Approved
0.7638	Intermediate Similarity	NPD7736	Approved
0.7619	Intermediate Similarity	NPD6616	Approved
0.7607	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7583	Intermediate Similarity	NPD8133	Approved
0.7583	Intermediate Similarity	NPD4632	Approved
0.7581	Intermediate Similarity	NPD8378	Approved
0.7581	Intermediate Similarity	NPD8380	Approved
0.7581	Intermediate Similarity	NPD8296	Approved
0.7581	Intermediate Similarity	NPD8335	Approved
0.7581	Intermediate Similarity	NPD8379	Approved
0.7559	Intermediate Similarity	NPD7078	Approved
0.7541	Intermediate Similarity	NPD6009	Approved
0.7523	Intermediate Similarity	NPD6698	Approved
0.7523	Intermediate Similarity	NPD46	Approved
0.7521	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.752	Intermediate Similarity	NPD6370	Approved
0.75	Intermediate Similarity	NPD6059	Approved
0.7458	Intermediate Similarity	NPD6899	Approved
0.7458	Intermediate Similarity	NPD6881	Approved
0.744	Intermediate Similarity	NPD6015	Approved
0.744	Intermediate Similarity	NPD6016	Approved
0.7436	Intermediate Similarity	NPD6402	Approved
0.7436	Intermediate Similarity	NPD5739	Approved
0.7436	Intermediate Similarity	NPD7128	Approved
0.7436	Intermediate Similarity	NPD6675	Approved
0.7422	Intermediate Similarity	NPD8074	Phase 3
0.7422	Intermediate Similarity	NPD8293	Discontinued
0.7417	Intermediate Similarity	NPD8413	Clinical (unspecified phase)
0.7417	Intermediate Similarity	NPD6650	Approved
0.7417	Intermediate Similarity	NPD6649	Approved
0.7395	Intermediate Similarity	NPD6373	Approved
0.7395	Intermediate Similarity	NPD6372	Approved
0.7391	Intermediate Similarity	NPD5344	Discontinued
0.7381	Intermediate Similarity	NPD5988	Approved
0.7373	Intermediate Similarity	NPD5697	Approved
0.7333	Intermediate Similarity	NPD7102	Approved
0.7333	Intermediate Similarity	NPD6883	Approved
0.7333	Intermediate Similarity	NPD7290	Approved
0.7328	Intermediate Similarity	NPD7632	Discontinued
0.7321	Intermediate Similarity	NPD7748	Approved
0.7311	Intermediate Similarity	NPD7320	Approved
0.7297	Intermediate Similarity	NPD7515	Phase 2
0.7288	Intermediate Similarity	NPD6008	Approved
0.7281	Intermediate Similarity	NPD7902	Approved
0.7273	Intermediate Similarity	NPD6617	Approved
0.7273	Intermediate Similarity	NPD6869	Approved
0.7273	Intermediate Similarity	NPD6847	Approved
0.7273	Intermediate Similarity	NPD8130	Phase 1
0.725	Intermediate Similarity	NPD6014	Approved
0.725	Intermediate Similarity	NPD6013	Approved
0.725	Intermediate Similarity	NPD6012	Approved
0.7227	Intermediate Similarity	NPD5701	Approved
0.7213	Intermediate Similarity	NPD6053	Discontinued
0.7188	Intermediate Similarity	NPD7604	Phase 2
0.7179	Intermediate Similarity	NPD5211	Phase 2
0.7167	Intermediate Similarity	NPD6011	Approved
0.7165	Intermediate Similarity	NPD5983	Phase 2
0.7143	Intermediate Similarity	NPD6079	Approved
0.7117	Intermediate Similarity	NPD5328	Approved
0.7091	Intermediate Similarity	NPD3573	Approved
0.708	Intermediate Similarity	NPD5778	Approved
0.708	Intermediate Similarity	NPD5779	Approved
0.708	Intermediate Similarity	NPD6399	Phase 3
0.7077	Intermediate Similarity	NPD6336	Discontinued
0.7069	Intermediate Similarity	NPD8029	Clinical (unspecified phase)
0.7068	Intermediate Similarity	NPD7260	Phase 2
0.7059	Intermediate Similarity	NPD5141	Approved
0.7049	Intermediate Similarity	NPD6371	Approved
0.7049	Intermediate Similarity	NPD4634	Approved
0.7031	Intermediate Similarity	NPD6921	Approved
0.7018	Intermediate Similarity	NPD7900	Approved
0.7018	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7009	Intermediate Similarity	NPD6648	Approved
0.7009	Intermediate Similarity	NPD5286	Approved
0.7009	Intermediate Similarity	NPD4696	Approved
0.7009	Intermediate Similarity	NPD5285	Approved
0.6992	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6991	Remote Similarity	NPD7983	Approved
0.6991	Remote Similarity	NPD6411	Approved
0.6983	Remote Similarity	NPD4755	Approved
0.697	Remote Similarity	NPD6033	Approved
0.6944	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6942	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD6067	Discontinued
0.6909	Remote Similarity	NPD1694	Approved
0.6905	Remote Similarity	NPD6274	Approved
0.6903	Remote Similarity	NPD7838	Discovery
0.6897	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD5221	Approved
0.6897	Remote Similarity	NPD5222	Approved
0.6891	Remote Similarity	NPD4633	Approved
0.6891	Remote Similarity	NPD5226	Approved
0.6891	Remote Similarity	NPD5225	Approved
0.6891	Remote Similarity	NPD5224	Approved
0.6889	Remote Similarity	NPD6845	Suspended
0.6875	Remote Similarity	NPD7100	Approved
0.6875	Remote Similarity	NPD7101	Approved
0.6864	Remote Similarity	NPD4700	Approved
0.6847	Remote Similarity	NPD3618	Phase 1
0.6838	Remote Similarity	NPD5173	Approved
0.6838	Remote Similarity	NPD6084	Phase 2
0.6838	Remote Similarity	NPD6083	Phase 2
0.6833	Remote Similarity	NPD5174	Approved
0.6833	Remote Similarity	NPD5175	Approved
0.6814	Remote Similarity	NPD6101	Approved
0.6814	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.681	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6807	Remote Similarity	NPD5223	Approved
0.6797	Remote Similarity	NPD6335	Approved
0.6772	Remote Similarity	NPD6868	Approved
0.6752	Remote Similarity	NPD4697	Phase 3
0.6748	Remote Similarity	NPD4729	Approved
0.6748	Remote Similarity	NPD4730	Approved
0.6726	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6721	Remote Similarity	NPD4767	Approved
0.6721	Remote Similarity	NPD4768	Approved
0.6719	Remote Similarity	NPD6317	Approved
0.6696	Remote Similarity	NPD7334	Approved
0.6696	Remote Similarity	NPD8035	Phase 2
0.6696	Remote Similarity	NPD6684	Approved
0.6696	Remote Similarity	NPD7521	Approved
0.6696	Remote Similarity	NPD8034	Phase 2
0.6696	Remote Similarity	NPD6409	Approved
0.6696	Remote Similarity	NPD7146	Approved
0.6696	Remote Similarity	NPD5330	Approved
0.6667	Remote Similarity	NPD6314	Approved
0.6667	Remote Similarity	NPD4786	Approved
0.6667	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6313	Approved
0.6641	Remote Similarity	NPD6908	Approved
0.6641	Remote Similarity	NPD6909	Approved
0.6641	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.664	Remote Similarity	NPD5248	Approved
0.664	Remote Similarity	NPD5251	Approved
0.664	Remote Similarity	NPD5250	Approved
0.664	Remote Similarity	NPD5247	Approved
0.664	Remote Similarity	NPD5249	Phase 3
0.6639	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6638	Remote Similarity	NPD4202	Approved
0.6636	Remote Similarity	NPD3667	Approved
0.6613	Remote Similarity	NPD5128	Approved
0.661	Remote Similarity	NPD7839	Suspended
0.6607	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6579	Remote Similarity	NPD6672	Approved
0.6579	Remote Similarity	NPD6903	Approved
0.6579	Remote Similarity	NPD5737	Approved
0.6571	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6557	Remote Similarity	NPD4754	Approved
0.6552	Remote Similarity	NPD7637	Suspended
0.6541	Remote Similarity	NPD7830	Approved
0.6541	Remote Similarity	NPD7829	Approved
0.6525	Remote Similarity	NPD5695	Phase 3
0.6525	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6518	Remote Similarity	NPD3665	Phase 1
0.6518	Remote Similarity	NPD3666	Approved
0.6518	Remote Similarity	NPD3133	Approved
0.65	Remote Similarity	NPD5696	Approved
0.65	Remote Similarity	NPD8387	Clinical (unspecified phase)
0.6491	Remote Similarity	NPD7524	Approved
0.6466	Remote Similarity	NPD5785	Approved
0.646	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6457	Remote Similarity	NPD5217	Approved
0.6457	Remote Similarity	NPD5216	Approved
0.6457	Remote Similarity	NPD5215	Approved
0.641	Remote Similarity	NPD5693	Phase 1
0.6398	Remote Similarity	NPD7799	Discontinued
0.6395	Remote Similarity	NPD7625	Phase 1
0.6379	Remote Similarity	NPD4753	Phase 2
0.6379	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6378	Remote Similarity	NPD5134	Clinical (unspecified phase)

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