NPASS Compound

Structure

NPC472534 OpenBabel07101718312D 27 31 0 0 1 0 0 0 0 0999 V2000 4.6679 0.4665 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2675 1.7974 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4358 1.3995 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8599 1.8661 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0518 -0.4665 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4921 -0.2156 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5484 -0.7548 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8599 0.9330 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7579 0.7005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0518 0.4665 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.8778 0.0394 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.0518 2.3326 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.2438 -0.9330 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.4511 -0.6762 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1662 1.0189 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.2438 1.8661 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.4358 0.4665 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.2438 0.9330 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.4358 -0.4665 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.5484 0.7548 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.0518 3.2656 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2954 -1.3335 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2081 1.9510 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4358 2.3326 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1751 1.3440 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 1.7856 -0.9955 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 8 1 0 0 0 0 2 9 2 0 0 0 0 4 8 2 0 0 0 0 4 12 1 0 0 0 0 5 10 1 0 0 0 0 5 13 1 0 0 0 0 6 11 1 0 0 0 0 6 14 1 0 0 0 0 7 26 1 0 0 0 0 8 10 1 0 0 0 0 9 11 1 0 0 0 0 9 15 1 0 0 0 0 10 18 1 6 0 0 0 11 19 1 1 0 0 0 12 16 1 0 0 0 0 12 21 1 1 0 0 0 13 19 1 6 0 0 0 13 27 1 0 0 0 0 14 22 2 0 0 0 0 14 27 1 0 0 0 0 15 20 1 1 0 0 0 15 23 1 0 0 0 0 16 18 1 6 0 0 0 16 24 1 0 0 0 0 17 18 1 6 0 0 0 17 19 1 0 0 0 0 17 20 1 0 0 0 0 18 3 1 6 0 0 0 19 7 1 1 0 0 0 20 25 1 6 0 0 0 20 26 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	378.17
Volume:	365.316
LogP:	1.257
LogD:	0.681
LogS:	-3.272
# Rotatable Bonds:	0
TPSA:	116.45
# H-Bond Aceptor:	7
# H-Bond Donor:	4
# Rings:	5
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.343
Synthetic Accessibility Score:	6.667
Fsp3:	0.75
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.877
MDCK Permeability:	6.0147849580971524e-05
Pgp-inhibitor:	0.002
Pgp-substrate:	0.999
Human Intestinal Absorption (HIA):	0.024
20% Bioavailability (F20%):	0.15
30% Bioavailability (F30%):	0.686

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.262
Plasma Protein Binding (PPB):	41.968624114990234%
Volume Distribution (VD):	0.741
Pgp-substrate:	67.1353530883789%

ADMET: Metabolism

CYP1A2-inhibitor:	0.014
CYP1A2-substrate:	0.515
CYP2C19-inhibitor:	0.014
CYP2C19-substrate:	0.108
CYP2C9-inhibitor:	0.002
CYP2C9-substrate:	0.022
CYP2D6-inhibitor:	0.008
CYP2D6-substrate:	0.126
CYP3A4-inhibitor:	0.044
CYP3A4-substrate:	0.103

ADMET: Excretion

Clearance (CL):	2.36
Half-life (T1/2):	0.666

ADMET: Toxicity

hERG Blockers:	0.047
Human Hepatotoxicity (H-HT):	0.735
Drug-inuced Liver Injury (DILI):	0.185
AMES Toxicity:	0.044
Rat Oral Acute Toxicity:	0.867
Maximum Recommended Daily Dose:	0.97
Skin Sensitization:	0.232
Carcinogencity:	0.323
Eye Corrosion:	0.01
Eye Irritation:	0.017
Respiratory Toxicity:	0.983

Download Data

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

Natural Product: NPC472534

Natural Product ID:	NPC472534
*Common Name:**	Shinjulactone A
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	RSGAOKBKALIZEE-RSIVDQDWSA-N
Standard InCHI:	InChI=1S/C20H26O7/c1-8-4-12(21)16(24)18(3)10(8)5-13-19-7-26-20(25,17(18)19)15(23)9(2)11(19)6-14(22)27-13/h4,10-13,15-17,21,23-25H,2,5-7H2,1,3H3/t10-,11-,12-,13+,15-,16+,17+,18+,19+,20-/m0/s1
SMILES:	O=C1O[C@@H]2C[C@H]3C(=C[C@@H]([C@H]([C@@]3([C@@H]3[C@@]42[C@@H](C1)C(=C)[C@@H]([C@@]3(OC4)O)O)C)O)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL349383
PubChem CID:	44375396
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
EC50	1
IC50	5
Others	1

Activity Type	# Activity
Cell Line	4
NON-MOLECULAR	1
Organism	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT759	Cell Line	H9	Homo sapiens	IC50	=	5000.0	nM	PMID[456329]
NPT65	Cell Line	HepG2	Homo sapiens	IC50	>	50000.0	nM	PMID[456330]
NPT65	Cell Line	HepG2	Homo sapiens	IC50	=	4670.0	nM	PMID[456330]
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	56400.0	nM	PMID[456331]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	EC50	=	5000.0	nM	PMID[456329]
NPT27	Others	Unspecified		Therapeutic index	=	1.0	n.a.	PMID[456329]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	8010.0	nM	PMID[456330]

☑ 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 NPC472534 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	218
0.1-0.2	1287
0.2-0.3	3828
0.3-0.4	7101
0.4-0.5	13125
0.5-0.6	6798
0.6-0.7	5417
0.7-0.8	4182
0.8-0.85	628
0.85-0.9	82
0.9-0.95	21
0.95-1	10

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC143706
0.9709	High Similarity	NPC302146
0.9524	High Similarity	NPC470919
0.9524	High Similarity	NPC469877
0.9434	High Similarity	NPC474046
0.9434	High Similarity	NPC259306
0.9434	High Similarity	NPC470628
0.9429	High Similarity	NPC51978
0.9346	High Similarity	NPC473968
0.9238	High Similarity	NPC201992
0.9223	High Similarity	NPC230541
0.9174	High Similarity	NPC122971
0.9151	High Similarity	NPC289312
0.9151	High Similarity	NPC11252
0.9074	High Similarity	NPC474734
0.9048	High Similarity	NPC141350
0.9	High Similarity	NPC476529
0.9	High Similarity	NPC475775
0.8991	High Similarity	NPC470775
0.8991	High Similarity	NPC176513
0.8981	High Similarity	NPC474906
0.8981	High Similarity	NPC18547
0.8981	High Similarity	NPC472274
0.8919	High Similarity	NPC112038
0.8919	High Similarity	NPC107338
0.8919	High Similarity	NPC109607
0.8909	High Similarity	NPC470776
0.8899	High Similarity	NPC235539
0.8899	High Similarity	NPC134869
0.8899	High Similarity	NPC152199
0.8818	High Similarity	NPC473590
0.8818	High Similarity	NPC470171
0.8807	High Similarity	NPC117712
0.8807	High Similarity	NPC243354
0.8796	High Similarity	NPC472002
0.8774	High Similarity	NPC293850
0.8772	High Similarity	NPC470922
0.8762	High Similarity	NPC102352
0.8762	High Similarity	NPC127609
0.8739	High Similarity	NPC297179
0.8739	High Similarity	NPC188667
0.8739	High Similarity	NPC204552
0.8727	High Similarity	NPC179626
0.8716	High Similarity	NPC49451
0.8716	High Similarity	NPC194273
0.8704	High Similarity	NPC188738
0.8704	High Similarity	NPC471243
0.8679	High Similarity	NPC293512
0.8679	High Similarity	NPC144854
0.8679	High Similarity	NPC3316
0.8667	High Similarity	NPC152966
0.8636	High Similarity	NPC475633
0.8624	High Similarity	NPC174836
0.8598	High Similarity	NPC192813
0.8598	High Similarity	NPC277017
0.8598	High Similarity	NPC154608
0.8571	High Similarity	NPC251310
0.8559	High Similarity	NPC40632
0.8559	High Similarity	NPC251236
0.8559	High Similarity	NPC96312
0.8559	High Similarity	NPC328374
0.8532	High Similarity	NPC285410
0.8532	High Similarity	NPC263827
0.8532	High Similarity	NPC250481
0.8532	High Similarity	NPC56025
0.8529	High Similarity	NPC256227
0.8522	High Similarity	NPC67251
0.8509	High Similarity	NPC202051
0.8509	High Similarity	NPC477046
0.8509	High Similarity	NPC102822
0.8496	Intermediate Similarity	NPC469488
0.8491	Intermediate Similarity	NPC475036
0.8491	Intermediate Similarity	NPC258532
0.8482	Intermediate Similarity	NPC287343
0.8482	Intermediate Similarity	NPC97908
0.8482	Intermediate Similarity	NPC470854
0.8482	Intermediate Similarity	NPC122033
0.8482	Intermediate Similarity	NPC309433
0.8482	Intermediate Similarity	NPC471547
0.8482	Intermediate Similarity	NPC13713
0.8482	Intermediate Similarity	NPC474654
0.8476	Intermediate Similarity	NPC295791
0.8468	Intermediate Similarity	NPC473798
0.8468	Intermediate Similarity	NPC181145
0.8462	Intermediate Similarity	NPC470780
0.8455	Intermediate Similarity	NPC269530
0.8455	Intermediate Similarity	NPC12046
0.8455	Intermediate Similarity	NPC116794
0.8455	Intermediate Similarity	NPC474516
0.8455	Intermediate Similarity	NPC194951
0.844	Intermediate Similarity	NPC75747
0.844	Intermediate Similarity	NPC108709
0.844	Intermediate Similarity	NPC274507
0.844	Intermediate Similarity	NPC110139
0.844	Intermediate Similarity	NPC199457
0.844	Intermediate Similarity	NPC83005
0.844	Intermediate Similarity	NPC102914
0.844	Intermediate Similarity	NPC7870
0.844	Intermediate Similarity	NPC220984
0.844	Intermediate Similarity	NPC68419
0.8426	Intermediate Similarity	NPC472218
0.8426	Intermediate Similarity	NPC275539
0.8426	Intermediate Similarity	NPC295389
0.8426	Intermediate Similarity	NPC189075
0.8426	Intermediate Similarity	NPC472219
0.8426	Intermediate Similarity	NPC472217
0.8407	Intermediate Similarity	NPC17772
0.8407	Intermediate Similarity	NPC18233
0.8407	Intermediate Similarity	NPC276758
0.8393	Intermediate Similarity	NPC138372
0.8393	Intermediate Similarity	NPC106228
0.8378	Intermediate Similarity	NPC255017
0.8378	Intermediate Similarity	NPC269315
0.8378	Intermediate Similarity	NPC7921
0.8378	Intermediate Similarity	NPC474410
0.8378	Intermediate Similarity	NPC208998
0.8378	Intermediate Similarity	NPC311592
0.8378	Intermediate Similarity	NPC293658
0.8378	Intermediate Similarity	NPC271138
0.8378	Intermediate Similarity	NPC75167
0.8378	Intermediate Similarity	NPC320118
0.8378	Intermediate Similarity	NPC157441
0.8364	Intermediate Similarity	NPC247031
0.8364	Intermediate Similarity	NPC211798
0.8364	Intermediate Similarity	NPC474846
0.8364	Intermediate Similarity	NPC473481
0.8364	Intermediate Similarity	NPC469655
0.8364	Intermediate Similarity	NPC235841
0.8364	Intermediate Similarity	NPC297208
0.8364	Intermediate Similarity	NPC469656
0.8364	Intermediate Similarity	NPC100329
0.8364	Intermediate Similarity	NPC97939
0.8364	Intermediate Similarity	NPC132790
0.8364	Intermediate Similarity	NPC171888
0.8364	Intermediate Similarity	NPC146945
0.8364	Intermediate Similarity	NPC30397
0.8364	Intermediate Similarity	NPC108748
0.8364	Intermediate Similarity	NPC179434
0.8364	Intermediate Similarity	NPC191763
0.8349	Intermediate Similarity	NPC137917
0.8349	Intermediate Similarity	NPC204407
0.8349	Intermediate Similarity	NPC127853
0.8349	Intermediate Similarity	NPC237503
0.8349	Intermediate Similarity	NPC218853
0.8349	Intermediate Similarity	NPC57362
0.8349	Intermediate Similarity	NPC306746
0.8349	Intermediate Similarity	NPC167383
0.8333	Intermediate Similarity	NPC110496
0.8333	Intermediate Similarity	NPC470957
0.8333	Intermediate Similarity	NPC477071
0.8333	Intermediate Similarity	NPC475041
0.8333	Intermediate Similarity	NPC470958
0.8333	Intermediate Similarity	NPC59530
0.8333	Intermediate Similarity	NPC283849
0.8319	Intermediate Similarity	NPC53396
0.8319	Intermediate Similarity	NPC469684
0.8319	Intermediate Similarity	NPC473405
0.8319	Intermediate Similarity	NPC218970
0.8319	Intermediate Similarity	NPC98249
0.8318	Intermediate Similarity	NPC470768
0.8318	Intermediate Similarity	NPC471293
0.8318	Intermediate Similarity	NPC222161
0.8304	Intermediate Similarity	NPC220293
0.8304	Intermediate Similarity	NPC110861
0.8304	Intermediate Similarity	NPC102088
0.8291	Intermediate Similarity	NPC24651
0.8291	Intermediate Similarity	NPC476729
0.8288	Intermediate Similarity	NPC125923
0.8288	Intermediate Similarity	NPC37739
0.8288	Intermediate Similarity	NPC256798
0.8288	Intermediate Similarity	NPC64106
0.8288	Intermediate Similarity	NPC212968
0.8288	Intermediate Similarity	NPC65590
0.8288	Intermediate Similarity	NPC139894
0.8288	Intermediate Similarity	NPC128925
0.8288	Intermediate Similarity	NPC473383
0.8288	Intermediate Similarity	NPC46388
0.8288	Intermediate Similarity	NPC126691
0.8288	Intermediate Similarity	NPC48249
0.8276	Intermediate Similarity	NPC312833
0.8276	Intermediate Similarity	NPC28532
0.8273	Intermediate Similarity	NPC90856
0.8273	Intermediate Similarity	NPC59804
0.8273	Intermediate Similarity	NPC476884
0.8273	Intermediate Similarity	NPC42776
0.8273	Intermediate Similarity	NPC476886
0.8273	Intermediate Similarity	NPC174679
0.8273	Intermediate Similarity	NPC476880
0.8273	Intermediate Similarity	NPC475296
0.8273	Intermediate Similarity	NPC127056
0.8273	Intermediate Similarity	NPC474589
0.8273	Intermediate Similarity	NPC478211
0.8273	Intermediate Similarity	NPC476882
0.8273	Intermediate Similarity	NPC129340
0.8273	Intermediate Similarity	NPC476885
0.8273	Intermediate Similarity	NPC210005
0.8273	Intermediate Similarity	NPC476883
0.8273	Intermediate Similarity	NPC476887
0.8273	Intermediate Similarity	NPC474567
0.8273	Intermediate Similarity	NPC136877

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 NPC472534 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	183
0.1-0.2	1475
0.2-0.3	3649
0.3-0.4	2464
0.4-0.5	802
0.5-0.6	279
0.6-0.7	197
0.7-0.8	96
0.8-0.85	5
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8018	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7928	Intermediate Similarity	NPD6686	Approved
0.7917	Intermediate Similarity	NPD7507	Approved
0.7857	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7845	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7838	Intermediate Similarity	NPD6412	Phase 2
0.775	Intermediate Similarity	NPD8328	Phase 3
0.7731	Intermediate Similarity	NPD8513	Phase 3
0.7731	Intermediate Similarity	NPD8516	Approved
0.7731	Intermediate Similarity	NPD8515	Approved
0.7731	Intermediate Similarity	NPD8517	Approved
0.7724	Intermediate Similarity	NPD7319	Approved
0.7685	Intermediate Similarity	NPD4225	Approved
0.7615	Intermediate Similarity	NPD7640	Approved
0.7615	Intermediate Similarity	NPD7639	Approved
0.7611	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD4632	Approved
0.7542	Intermediate Similarity	NPD7115	Discovery
0.7542	Intermediate Similarity	NPD6009	Approved
0.7541	Intermediate Similarity	NPD7492	Approved
0.7523	Intermediate Similarity	NPD7638	Approved
0.75	Intermediate Similarity	NPD7736	Approved
0.75	Intermediate Similarity	NPD6054	Approved
0.75	Intermediate Similarity	NPD6319	Approved
0.75	Intermediate Similarity	NPD6059	Approved
0.748	Intermediate Similarity	NPD6616	Approved
0.7478	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7438	Intermediate Similarity	NPD6015	Approved
0.7438	Intermediate Similarity	NPD6016	Approved
0.7436	Intermediate Similarity	NPD8133	Approved
0.7434	Intermediate Similarity	NPD6402	Approved
0.7434	Intermediate Similarity	NPD5739	Approved
0.7434	Intermediate Similarity	NPD6675	Approved
0.7434	Intermediate Similarity	NPD7128	Approved
0.7434	Intermediate Similarity	NPD6008	Approved
0.7419	Intermediate Similarity	NPD8293	Discontinued
0.7419	Intermediate Similarity	NPD7078	Approved
0.7417	Intermediate Similarity	NPD7516	Approved
0.7383	Intermediate Similarity	NPD6399	Phase 3
0.7383	Intermediate Similarity	NPD5778	Approved
0.7383	Intermediate Similarity	NPD5779	Approved
0.7377	Intermediate Similarity	NPD5988	Approved
0.7377	Intermediate Similarity	NPD6370	Approved
0.7368	Intermediate Similarity	NPD5701	Approved
0.7368	Intermediate Similarity	NPD5697	Approved
0.735	Intermediate Similarity	NPD8297	Approved
0.735	Intermediate Similarity	NPD6882	Approved
0.7333	Intermediate Similarity	NPD7328	Approved
0.7333	Intermediate Similarity	NPD7327	Approved
0.7315	Intermediate Similarity	NPD7748	Approved
0.7304	Intermediate Similarity	NPD6881	Approved
0.7304	Intermediate Similarity	NPD7320	Approved
0.7304	Intermediate Similarity	NPD6899	Approved
0.7295	Intermediate Similarity	NPD8033	Approved
0.729	Intermediate Similarity	NPD7515	Phase 2
0.729	Intermediate Similarity	NPD6411	Approved
0.728	Intermediate Similarity	NPD8074	Phase 3
0.7273	Intermediate Similarity	NPD7902	Approved
0.7265	Intermediate Similarity	NPD8413	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD6014	Approved
0.7241	Intermediate Similarity	NPD6372	Approved
0.7241	Intermediate Similarity	NPD6373	Approved
0.7241	Intermediate Similarity	NPD6013	Approved
0.7241	Intermediate Similarity	NPD6012	Approved
0.7217	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.7213	Intermediate Similarity	NPD8377	Approved
0.7213	Intermediate Similarity	NPD8294	Approved
0.7179	Intermediate Similarity	NPD7102	Approved
0.7179	Intermediate Similarity	NPD7290	Approved
0.7179	Intermediate Similarity	NPD6883	Approved
0.7168	Intermediate Similarity	NPD5211	Phase 2
0.7155	Intermediate Similarity	NPD6011	Approved
0.7154	Intermediate Similarity	NPD5983	Phase 2
0.7154	Intermediate Similarity	NPD8378	Approved
0.7154	Intermediate Similarity	NPD8380	Approved
0.7154	Intermediate Similarity	NPD8335	Approved
0.7154	Intermediate Similarity	NPD7503	Approved
0.7154	Intermediate Similarity	NPD8379	Approved
0.7154	Intermediate Similarity	NPD8296	Approved
0.713	Intermediate Similarity	NPD7983	Approved
0.7119	Intermediate Similarity	NPD6649	Approved
0.7119	Intermediate Similarity	NPD6617	Approved
0.7119	Intermediate Similarity	NPD8130	Phase 1
0.7119	Intermediate Similarity	NPD6650	Approved
0.7119	Intermediate Similarity	NPD6847	Approved
0.7119	Intermediate Similarity	NPD6869	Approved
0.7117	Intermediate Similarity	NPD4755	Approved
0.7103	Intermediate Similarity	NPD6101	Approved
0.7103	Intermediate Similarity	NPD5328	Approved
0.7103	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7087	Intermediate Similarity	NPD3667	Approved
0.7075	Intermediate Similarity	NPD3573	Approved
0.7043	Intermediate Similarity	NPD5141	Approved
0.704	Intermediate Similarity	NPD7604	Phase 2
0.7037	Intermediate Similarity	NPD46	Approved
0.7037	Intermediate Similarity	NPD6698	Approved
0.7034	Intermediate Similarity	NPD4634	Approved
0.7018	Intermediate Similarity	NPD7632	Discontinued
0.7	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD7900	Approved
0.6991	Remote Similarity	NPD4700	Approved
0.6991	Remote Similarity	NPD4696	Approved
0.6991	Remote Similarity	NPD5285	Approved
0.6991	Remote Similarity	NPD5286	Approved
0.6981	Remote Similarity	NPD3618	Phase 1
0.6975	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6972	Remote Similarity	NPD6079	Approved
0.6972	Remote Similarity	NPD8035	Phase 2
0.6972	Remote Similarity	NPD8034	Phase 2
0.6953	Remote Similarity	NPD6033	Approved
0.6952	Remote Similarity	NPD4786	Approved
0.693	Remote Similarity	NPD5344	Discontinued
0.6929	Remote Similarity	NPD6336	Discontinued
0.6917	Remote Similarity	NPD6053	Discontinued
0.6905	Remote Similarity	NPD6067	Discontinued
0.6887	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6885	Remote Similarity	NPD6274	Approved
0.688	Remote Similarity	NPD6921	Approved
0.6875	Remote Similarity	NPD5222	Approved
0.6875	Remote Similarity	NPD5221	Approved
0.6875	Remote Similarity	NPD4697	Phase 3
0.6875	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.687	Remote Similarity	NPD5225	Approved
0.687	Remote Similarity	NPD4633	Approved
0.687	Remote Similarity	NPD5226	Approved
0.687	Remote Similarity	NPD5224	Approved
0.6818	Remote Similarity	NPD7637	Suspended
0.6814	Remote Similarity	NPD6084	Phase 2
0.6814	Remote Similarity	NPD6083	Phase 2
0.6814	Remote Similarity	NPD5173	Approved
0.681	Remote Similarity	NPD5174	Approved
0.681	Remote Similarity	NPD5175	Approved
0.6783	Remote Similarity	NPD5223	Approved
0.6759	Remote Similarity	NPD7524	Approved
0.6757	Remote Similarity	NPD4202	Approved
0.6752	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6726	Remote Similarity	NPD7839	Suspended
0.672	Remote Similarity	NPD7101	Approved
0.672	Remote Similarity	NPD7100	Approved
0.6697	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6695	Remote Similarity	NPD4767	Approved
0.6695	Remote Similarity	NPD4768	Approved
0.6694	Remote Similarity	NPD6317	Approved
0.6667	Remote Similarity	NPD7521	Approved
0.6667	Remote Similarity	NPD4754	Approved
0.6667	Remote Similarity	NPD7146	Approved
0.6667	Remote Similarity	NPD5330	Approved
0.6667	Remote Similarity	NPD7334	Approved
0.6667	Remote Similarity	NPD6684	Approved
0.6667	Remote Similarity	NPD6409	Approved
0.664	Remote Similarity	NPD6335	Approved
0.664	Remote Similarity	NPD6313	Approved
0.664	Remote Similarity	NPD6314	Approved
0.6637	Remote Similarity	NPD5695	Phase 3
0.6636	Remote Similarity	NPD3665	Phase 1
0.6636	Remote Similarity	NPD3666	Approved
0.6636	Remote Similarity	NPD3668	Phase 3
0.6636	Remote Similarity	NPD3133	Approved
0.6635	Remote Similarity	NPD7645	Phase 2
0.6614	Remote Similarity	NPD6909	Approved
0.6614	Remote Similarity	NPD6908	Approved
0.6614	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6613	Remote Similarity	NPD6868	Approved
0.6612	Remote Similarity	NPD6371	Approved
0.6609	Remote Similarity	NPD5696	Approved
0.6604	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6583	Remote Similarity	NPD4729	Approved
0.6583	Remote Similarity	NPD4730	Approved
0.6583	Remote Similarity	NPD5128	Approved
0.6574	Remote Similarity	NPD1694	Approved
0.6552	Remote Similarity	NPD6648	Approved
0.6545	Remote Similarity	NPD5737	Approved
0.6545	Remote Similarity	NPD6903	Approved
0.6545	Remote Similarity	NPD6672	Approved
0.6541	Remote Similarity	NPD7260	Phase 2
0.6514	Remote Similarity	NPD4249	Approved
0.6491	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6491	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6486	Remote Similarity	NPD4753	Phase 2
0.6481	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6475	Remote Similarity	NPD5250	Approved
0.6475	Remote Similarity	NPD5248	Approved
0.6475	Remote Similarity	NPD5251	Approved
0.6475	Remote Similarity	NPD5249	Phase 3
0.6475	Remote Similarity	NPD5247	Approved
0.6466	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6455	Remote Similarity	NPD4251	Approved
0.6455	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6455	Remote Similarity	NPD4250	Approved
0.6423	Remote Similarity	NPD5215	Approved
0.6423	Remote Similarity	NPD5217	Approved
0.6423	Remote Similarity	NPD5216	Approved
0.6415	Remote Similarity	NPD7525	Registered
0.6404	Remote Similarity	NPD5282	Discontinued
0.6389	Remote Similarity	NPD7154	Phase 3
0.6389	Remote Similarity	NPD6695	Phase 3
0.6381	Remote Similarity	NPD6115	Approved
0.6381	Remote Similarity	NPD6118	Approved
0.6381	Remote Similarity	NPD6114	Approved
0.6381	Remote Similarity	NPD6697	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