NPASS Compound

Structure

NPC122971 OpenBabel07101719522D 38 43 0 0 1 0 0 0 0 0999 V2000 2.7943 -3.8876 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2560 -1.9708 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9696 -0.5548 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6189 -2.4593 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1450 -2.9354 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5708 -1.4289 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0929 -3.8876 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3873 -0.8699 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7943 -2.9354 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5162 -1.1962 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9696 -2.4593 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9931 -1.6396 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.6189 -1.5071 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.0929 -2.9354 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.3203 -2.4593 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.1428 -1.6276 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9175 -2.4593 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 6.9175 -1.5071 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.0929 -1.0310 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.4957 -0.5108 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.7943 -1.0310 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.2682 -1.5071 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.1450 -1.0310 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.9696 -1.5071 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.3203 -1.5071 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9470 -0.0995 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 6.9175 -4.3637 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3293 -0.4194 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.7422 -2.9354 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.7422 -1.0310 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0929 -0.0787 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3408 -0.0722 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.7943 -0.0787 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0985 0.8406 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 4.4436 -1.0310 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.2682 -2.4593 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0313 -2.0862 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 9 1 0 0 0 0 2 10 2 0 0 0 0 4 9 2 0 0 0 0 4 13 1 0 0 0 0 5 11 1 0 0 0 0 5 15 1 0 0 0 0 6 12 1 0 0 0 0 6 16 1 0 0 0 0 7 27 1 0 0 0 0 8 35 1 0 0 0 0 9 11 1 0 0 0 0 10 12 1 0 0 0 0 10 20 1 0 0 0 0 11 24 1 6 0 0 0 12 25 1 1 0 0 0 13 21 1 0 0 0 0 13 36 1 1 0 0 0 14 7 1 1 0 0 0 14 17 1 0 0 0 0 14 37 1 0 0 0 0 15 25 1 6 0 0 0 15 38 1 0 0 0 0 16 28 2 0 0 0 0 16 38 1 0 0 0 0 17 18 1 0 0 0 0 17 29 1 6 0 0 0 18 19 1 0 0 0 0 18 30 1 1 0 0 0 19 22 1 0 0 0 0 19 31 1 6 0 0 0 20 26 1 6 0 0 0 20 32 1 0 0 0 0 21 24 1 6 0 0 0 21 33 1 0 0 0 0 22 36 1 1 0 0 0 22 37 1 0 0 0 0 23 24 1 6 0 0 0 23 25 1 0 0 0 0 23 26 1 0 0 0 0 24 3 1 6 0 0 0 25 8 1 1 0 0 0 26 34 1 6 0 0 0 26 35 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	540.22
Volume:	504.487
LogP:	0.009
LogD:	-0.132
LogS:	-3.159
# Rotatable Bonds:	3
TPSA:	195.6
# H-Bond Aceptor:	12
# H-Bond Donor:	7
# Rings:	6
# Heavy Atoms:	12

MedChem Properties

QED Drug-Likeness Score:	0.15
Synthetic Accessibility Score:	6.904
Fsp3:	0.808
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.647
MDCK Permeability:	0.00012909132055938244
Pgp-inhibitor:	0.005
Pgp-substrate:	1.0
Human Intestinal Absorption (HIA):	0.967
20% Bioavailability (F20%):	0.543
30% Bioavailability (F30%):	0.997

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.14
Plasma Protein Binding (PPB):	45.07682800292969%
Volume Distribution (VD):	0.475
Pgp-substrate:	51.5665283203125%

ADMET: Metabolism

CYP1A2-inhibitor:	0.005
CYP1A2-substrate:	0.131
CYP2C19-inhibitor:	0.01
CYP2C19-substrate:	0.067
CYP2C9-inhibitor:	0.001
CYP2C9-substrate:	0.007
CYP2D6-inhibitor:	0.007
CYP2D6-substrate:	0.084
CYP3A4-inhibitor:	0.024
CYP3A4-substrate:	0.037

ADMET: Excretion

Clearance (CL):	1.202
Half-life (T1/2):	0.677

ADMET: Toxicity

hERG Blockers:	0.084
Human Hepatotoxicity (H-HT):	0.684
Drug-inuced Liver Injury (DILI):	0.642
AMES Toxicity:	0.51
Rat Oral Acute Toxicity:	0.703
Maximum Recommended Daily Dose:	0.959
Skin Sensitization:	0.158
Carcinogencity:	0.047
Eye Corrosion:	0.003
Eye Irritation:	0.012
Respiratory Toxicity:	0.974

Download Data

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

Natural Product: NPC122971

Natural Product ID:	NPC122971
*Common Name:**	NNJOUYDCJDTDEP-VBEDBJTFSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	NNJOUYDCJDTDEP-VBEDBJTFSA-N
Standard InCHI:	InChI=1S/C26H36O12/c1-9-4-13(36-22-19(31)18(30)17(29)14(7-27)37-22)21(33)24(3)11(9)5-15-25-8-35-26(34,23(24)25)20(32)10(2)12(25)6-16(28)38-15/h4,11-15,17-23,27,29-34H,2,5-8H2,1,3H3/t11-,12-,13-,14+,15+,17+,18-,19+,20+,21+,22+,23+,24+,25+,26-/m0/s1
SMILES:	OC[C@H]1O[C@@H](O[C@H]2C=C(C)[C@H]3[C@@]([C@@H]2O)(C)[C@H]2[C@@]4(O)OC[C@]52[C@@H](C3)OC(=O)C[C@H]5C(=C)[C@H]4O)[C@@H]([C@H]([C@@H]1O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3403683
PubChem CID:	n.a.
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	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	100000.0	nM	PMID[449647]

☑ 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 NPC122971 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	252
0.1-0.2	1527
0.2-0.3	4129
0.3-0.4	7605
0.4-0.5	11984
0.5-0.6	7878
0.6-0.7	5196
0.7-0.8	2692
0.8-0.85	976
0.85-0.9	449
0.9-0.95	8
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9286	High Similarity	NPC473968
0.9231	High Similarity	NPC470780
0.9174	High Similarity	NPC143706
0.9174	High Similarity	NPC472534
0.9115	High Similarity	NPC473405
0.9107	High Similarity	NPC472274
0.9107	High Similarity	NPC469877
0.9107	High Similarity	NPC470919
0.9099	High Similarity	NPC302146
0.9035	High Similarity	NPC471548
0.9027	High Similarity	NPC470628
0.9027	High Similarity	NPC259306
0.9027	High Similarity	NPC474046
0.8957	High Similarity	NPC476529
0.8957	High Similarity	NPC475775
0.8947	High Similarity	NPC471547
0.8947	High Similarity	NPC309433
0.8938	High Similarity	NPC181145
0.8938	High Similarity	NPC475633
0.8919	High Similarity	NPC83005
0.8879	High Similarity	NPC109607
0.8879	High Similarity	NPC107338
0.887	High Similarity	NPC276758
0.887	High Similarity	NPC18233
0.885	High Similarity	NPC311592
0.885	High Similarity	NPC75167
0.885	High Similarity	NPC474410
0.885	High Similarity	NPC293658
0.8843	High Similarity	NPC329993
0.8843	High Similarity	NPC475167
0.8843	High Similarity	NPC262796
0.8843	High Similarity	NPC134914
0.8843	High Similarity	NPC45346
0.8843	High Similarity	NPC476074
0.8843	High Similarity	NPC478064
0.8843	High Similarity	NPC475377
0.8843	High Similarity	NPC173435
0.8843	High Similarity	NPC478065
0.8843	High Similarity	NPC301639
0.8843	High Similarity	NPC172374
0.8843	High Similarity	NPC264566
0.8839	High Similarity	NPC30397
0.8839	High Similarity	NPC473481
0.8839	High Similarity	NPC108748
0.8839	High Similarity	NPC235841
0.8839	High Similarity	NPC179434
0.8839	High Similarity	NPC297208
0.8839	High Similarity	NPC211798
0.8818	High Similarity	NPC293512
0.8803	High Similarity	NPC476204
0.8803	High Similarity	NPC170084
0.8793	High Similarity	NPC477071
0.8793	High Similarity	NPC470914
0.8783	High Similarity	NPC474483
0.8783	High Similarity	NPC473590
0.877	High Similarity	NPC478153
0.877	High Similarity	NPC478150
0.877	High Similarity	NPC478152
0.8761	High Similarity	NPC473383
0.8761	High Similarity	NPC174836
0.8761	High Similarity	NPC128925
0.8761	High Similarity	NPC116794
0.8761	High Similarity	NPC139894
0.8761	High Similarity	NPC256798
0.875	High Similarity	NPC59804
0.875	High Similarity	NPC108709
0.875	High Similarity	NPC164194
0.875	High Similarity	NPC269095
0.875	High Similarity	NPC274507
0.875	High Similarity	NPC29069
0.875	High Similarity	NPC220984
0.875	High Similarity	NPC174679
0.875	High Similarity	NPC7870
0.875	High Similarity	NPC127056
0.875	High Similarity	NPC68419
0.875	High Similarity	NPC270667
0.875	High Similarity	NPC102914
0.875	High Similarity	NPC119550
0.875	High Similarity	NPC279554
0.875	High Similarity	NPC136877
0.875	High Similarity	NPC475296
0.875	High Similarity	NPC56713
0.875	High Similarity	NPC75747
0.875	High Similarity	NPC474589
0.875	High Similarity	NPC110139
0.875	High Similarity	NPC199457
0.875	High Similarity	NPC90856
0.875	High Similarity	NPC78046
0.8739	High Similarity	NPC318135
0.8739	High Similarity	NPC217921
0.8739	High Similarity	NPC128795
0.8739	High Similarity	NPC135015
0.8739	High Similarity	NPC48548
0.8739	High Similarity	NPC470922
0.8727	High Similarity	NPC127609
0.8718	High Similarity	NPC476127
0.8718	High Similarity	NPC476150
0.8718	High Similarity	NPC129393
0.8707	High Similarity	NPC475899
0.8699	High Similarity	NPC478151
0.8696	High Similarity	NPC474734
0.8689	High Similarity	NPC25998
0.8689	High Similarity	NPC478155
0.8689	High Similarity	NPC477197
0.8684	High Similarity	NPC271138
0.8684	High Similarity	NPC258885
0.8684	High Similarity	NPC189884
0.8684	High Similarity	NPC157441
0.8684	High Similarity	NPC51978
0.8684	High Similarity	NPC150400
0.8684	High Similarity	NPC124296
0.8684	High Similarity	NPC47063
0.8684	High Similarity	NPC238935
0.8684	High Similarity	NPC134835
0.8684	High Similarity	NPC475208
0.8684	High Similarity	NPC269315
0.8684	High Similarity	NPC96641
0.8684	High Similarity	NPC73318
0.8684	High Similarity	NPC204458
0.8684	High Similarity	NPC163183
0.8684	High Similarity	NPC473343
0.8684	High Similarity	NPC138334
0.8684	High Similarity	NPC251309
0.8678	High Similarity	NPC329923
0.8678	High Similarity	NPC475281
0.8678	High Similarity	NPC477078
0.8678	High Similarity	NPC477075
0.8673	High Similarity	NPC191763
0.8673	High Similarity	NPC164419
0.8673	High Similarity	NPC263827
0.8673	High Similarity	NPC250481
0.8673	High Similarity	NPC285410
0.8661	High Similarity	NPC137917
0.8661	High Similarity	NPC316974
0.8661	High Similarity	NPC306746
0.8661	High Similarity	NPC204407
0.8661	High Similarity	NPC40728
0.8661	High Similarity	NPC167383
0.8661	High Similarity	NPC237503
0.8661	High Similarity	NPC127853
0.8661	High Similarity	NPC57362
0.8655	High Similarity	NPC478066
0.8649	High Similarity	NPC125423
0.8649	High Similarity	NPC88013
0.8644	High Similarity	NPC202051
0.864	High Similarity	NPC251998
0.8636	High Similarity	NPC470768
0.8632	High Similarity	NPC477464
0.8632	High Similarity	NPC473401
0.8618	High Similarity	NPC478154
0.8609	High Similarity	NPC473882
0.8609	High Similarity	NPC474906
0.8609	High Similarity	NPC102088
0.8609	High Similarity	NPC18547
0.8607	High Similarity	NPC477079
0.8607	High Similarity	NPC470912
0.8607	High Similarity	NPC477076
0.8607	High Similarity	NPC477196
0.8607	High Similarity	NPC477077
0.8607	High Similarity	NPC470913
0.8596	High Similarity	NPC139044
0.8596	High Similarity	NPC475516
0.8596	High Similarity	NPC324875
0.8596	High Similarity	NPC46388
0.8596	High Similarity	NPC10320
0.8596	High Similarity	NPC473373
0.8596	High Similarity	NPC102439
0.8596	High Similarity	NPC125923
0.8596	High Similarity	NPC104400
0.8596	High Similarity	NPC257468
0.8596	High Similarity	NPC12046
0.8596	High Similarity	NPC475504
0.8596	High Similarity	NPC37739
0.8596	High Similarity	NPC104071
0.8596	High Similarity	NPC276093
0.8596	High Similarity	NPC233003
0.8596	High Similarity	NPC289312
0.8596	High Similarity	NPC65590
0.8596	High Similarity	NPC1046
0.8596	High Similarity	NPC292677
0.8596	High Similarity	NPC11252
0.8596	High Similarity	NPC109079
0.8596	High Similarity	NPC195132
0.8596	High Similarity	NPC212968
0.8596	High Similarity	NPC469946
0.8596	High Similarity	NPC101744
0.8596	High Similarity	NPC471383
0.8596	High Similarity	NPC64106
0.8596	High Similarity	NPC161434
0.8596	High Similarity	NPC48249
0.8596	High Similarity	NPC80843
0.8596	High Similarity	NPC79718
0.8596	High Similarity	NPC194951
0.8595	High Similarity	NPC240070
0.8595	High Similarity	NPC329784
0.8584	High Similarity	NPC476883
0.8584	High Similarity	NPC476885
0.8584	High Similarity	NPC476881
0.8584	High Similarity	NPC476882
0.8584	High Similarity	NPC476880

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 NPC122971 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	1681
0.2-0.3	3687
0.3-0.4	2296
0.4-0.5	704
0.5-0.6	340
0.6-0.7	177
0.7-0.8	29
0.8-0.85	17
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8487	Intermediate Similarity	NPD8515	Approved
0.8487	Intermediate Similarity	NPD8513	Phase 3
0.8487	Intermediate Similarity	NPD8516	Approved
0.8487	Intermediate Similarity	NPD8517	Approved
0.8407	Intermediate Similarity	NPD6686	Approved
0.8361	Intermediate Similarity	NPD7507	Approved
0.8333	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.8305	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.8205	Intermediate Similarity	NPD8133	Approved
0.8197	Intermediate Similarity	NPD8328	Phase 3
0.816	Intermediate Similarity	NPD7319	Approved
0.8033	Intermediate Similarity	NPD8033	Approved
0.7951	Intermediate Similarity	NPD8377	Approved
0.7951	Intermediate Similarity	NPD8294	Approved
0.7886	Intermediate Similarity	NPD8378	Approved
0.7886	Intermediate Similarity	NPD8380	Approved
0.7886	Intermediate Similarity	NPD8296	Approved
0.7886	Intermediate Similarity	NPD8379	Approved
0.7886	Intermediate Similarity	NPD8335	Approved
0.7869	Intermediate Similarity	NPD7516	Approved
0.7845	Intermediate Similarity	NPD6412	Phase 2
0.7787	Intermediate Similarity	NPD7328	Approved
0.7787	Intermediate Similarity	NPD7327	Approved
0.7742	Intermediate Similarity	NPD7503	Approved
0.7731	Intermediate Similarity	NPD8413	Clinical (unspecified phase)
0.7578	Intermediate Similarity	NPD8074	Phase 3
0.7563	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7519	Intermediate Similarity	NPD7736	Approved
0.7479	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7478	Intermediate Similarity	NPD7640	Approved
0.7478	Intermediate Similarity	NPD7639	Approved
0.7442	Intermediate Similarity	NPD8293	Discontinued
0.7419	Intermediate Similarity	NPD7115	Discovery
0.7402	Intermediate Similarity	NPD6370	Approved
0.7391	Intermediate Similarity	NPD7638	Approved
0.7391	Intermediate Similarity	NPD4225	Approved
0.7355	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7287	Intermediate Similarity	NPD7492	Approved
0.7244	Intermediate Similarity	NPD6054	Approved
0.7244	Intermediate Similarity	NPD6059	Approved
0.7236	Intermediate Similarity	NPD6882	Approved
0.7231	Intermediate Similarity	NPD6616	Approved
0.7227	Intermediate Similarity	NPD8170	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD7078	Approved
0.7143	Intermediate Similarity	NPD6009	Approved
0.7109	Intermediate Similarity	NPD6319	Approved
0.7107	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD8297	Approved
0.708	Intermediate Similarity	NPD46	Approved
0.708	Intermediate Similarity	NPD6698	Approved
0.7054	Intermediate Similarity	NPD6015	Approved
0.7054	Intermediate Similarity	NPD6016	Approved
0.7043	Intermediate Similarity	NPD7748	Approved
0.704	Intermediate Similarity	NPD4632	Approved
0.7025	Intermediate Similarity	NPD7128	Approved
0.7025	Intermediate Similarity	NPD5739	Approved
0.7025	Intermediate Similarity	NPD6675	Approved
0.7025	Intermediate Similarity	NPD6402	Approved
0.7018	Intermediate Similarity	NPD7515	Phase 2
0.7009	Intermediate Similarity	NPD7902	Approved
0.7	Intermediate Similarity	NPD5988	Approved
0.6992	Remote Similarity	NPD6372	Approved
0.6992	Remote Similarity	NPD6373	Approved
0.6957	Remote Similarity	NPD5779	Approved
0.6957	Remote Similarity	NPD5778	Approved
0.6957	Remote Similarity	NPD6399	Phase 3
0.6947	Remote Similarity	NPD6067	Discontinued
0.6923	Remote Similarity	NPD6921	Approved
0.6917	Remote Similarity	NPD7632	Discontinued
0.6911	Remote Similarity	NPD7320	Approved
0.6911	Remote Similarity	NPD6899	Approved
0.6911	Remote Similarity	NPD6881	Approved
0.6885	Remote Similarity	NPD6008	Approved
0.688	Remote Similarity	NPD6650	Approved
0.688	Remote Similarity	NPD6649	Approved
0.687	Remote Similarity	NPD7983	Approved
0.687	Remote Similarity	NPD6411	Approved
0.6833	Remote Similarity	NPD5344	Discontinued
0.6829	Remote Similarity	NPD5701	Approved
0.6829	Remote Similarity	NPD5697	Approved
0.6825	Remote Similarity	NPD6053	Discontinued
0.6807	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.68	Remote Similarity	NPD7102	Approved
0.68	Remote Similarity	NPD6883	Approved
0.68	Remote Similarity	NPD7290	Approved
0.6752	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6752	Remote Similarity	NPD7900	Approved
0.6746	Remote Similarity	NPD6869	Approved
0.6746	Remote Similarity	NPD6847	Approved
0.6746	Remote Similarity	NPD8130	Phase 1
0.6746	Remote Similarity	NPD6617	Approved
0.6741	Remote Similarity	NPD6033	Approved
0.672	Remote Similarity	NPD6014	Approved
0.672	Remote Similarity	NPD6013	Approved
0.672	Remote Similarity	NPD6012	Approved
0.6696	Remote Similarity	NPD6101	Approved
0.6696	Remote Similarity	NPD5328	Approved
0.6696	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6692	Remote Similarity	NPD7604	Phase 2
0.6667	Remote Similarity	NPD5983	Phase 2
0.6644	Remote Similarity	NPD7625	Phase 1
0.664	Remote Similarity	NPD6011	Approved
0.6639	Remote Similarity	NPD5211	Phase 2
0.6614	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6594	Remote Similarity	NPD7260	Phase 2
0.6593	Remote Similarity	NPD8451	Approved
0.6593	Remote Similarity	NPD6336	Discontinued
0.6583	Remote Similarity	NPD4755	Approved
0.6581	Remote Similarity	NPD8035	Phase 2
0.6581	Remote Similarity	NPD6079	Approved
0.6581	Remote Similarity	NPD8034	Phase 2
0.6567	Remote Similarity	NPD7829	Approved
0.6567	Remote Similarity	NPD7830	Approved
0.6549	Remote Similarity	NPD4786	Approved
0.6549	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6544	Remote Similarity	NPD8448	Approved
0.6535	Remote Similarity	NPD6371	Approved
0.6535	Remote Similarity	NPD4634	Approved
0.6532	Remote Similarity	NPD5141	Approved
0.6525	Remote Similarity	NPD8171	Discontinued
0.6525	Remote Similarity	NPD8387	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD3573	Approved
0.6522	Remote Similarity	NPD8390	Approved
0.6522	Remote Similarity	NPD8392	Approved
0.6522	Remote Similarity	NPD8391	Approved
0.6519	Remote Similarity	NPD8341	Approved
0.6519	Remote Similarity	NPD8299	Approved
0.6519	Remote Similarity	NPD8340	Approved
0.6519	Remote Similarity	NPD8342	Approved
0.6518	Remote Similarity	NPD3667	Approved
0.65	Remote Similarity	NPD7839	Suspended
0.6491	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6475	Remote Similarity	NPD5285	Approved
0.6475	Remote Similarity	NPD5286	Approved
0.6475	Remote Similarity	NPD6648	Approved
0.6475	Remote Similarity	NPD4700	Approved
0.6475	Remote Similarity	NPD4696	Approved
0.6446	Remote Similarity	NPD6084	Phase 2
0.6446	Remote Similarity	NPD6083	Phase 2
0.6441	Remote Similarity	NPD7637	Suspended
0.6435	Remote Similarity	NPD3618	Phase 1
0.6429	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD6845	Suspended
0.6429	Remote Similarity	NPD8449	Approved
0.642	Remote Similarity	NPD7228	Approved
0.6418	Remote Similarity	NPD8444	Approved
0.6412	Remote Similarity	NPD6274	Approved
0.6396	Remote Similarity	NPD7645	Phase 2
0.6391	Remote Similarity	NPD7100	Approved
0.6391	Remote Similarity	NPD7101	Approved
0.6383	Remote Similarity	NPD8450	Suspended
0.6379	Remote Similarity	NPD7524	Approved
0.6372	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6371	Remote Similarity	NPD5226	Approved
0.6371	Remote Similarity	NPD4633	Approved
0.6371	Remote Similarity	NPD5225	Approved
0.6371	Remote Similarity	NPD5224	Approved
0.6364	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD5221	Approved
0.6364	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD5222	Approved
0.6364	Remote Similarity	NPD4697	Phase 3
0.6356	Remote Similarity	NPD7838	Discovery
0.6349	Remote Similarity	NPD4767	Approved
0.6349	Remote Similarity	NPD4768	Approved
0.6348	Remote Similarity	NPD1694	Approved
0.6338	Remote Similarity	NPD8415	Approved
0.6325	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.632	Remote Similarity	NPD5174	Approved
0.632	Remote Similarity	NPD5175	Approved
0.6319	Remote Similarity	NPD7799	Discontinued
0.6316	Remote Similarity	NPD6335	Approved
0.6311	Remote Similarity	NPD5173	Approved
0.6296	Remote Similarity	NPD6908	Approved
0.6296	Remote Similarity	NPD6909	Approved
0.6293	Remote Similarity	NPD7146	Approved
0.6293	Remote Similarity	NPD6409	Approved
0.6293	Remote Similarity	NPD7334	Approved
0.6293	Remote Similarity	NPD5330	Approved
0.6293	Remote Similarity	NPD7521	Approved
0.6293	Remote Similarity	NPD6684	Approved
0.629	Remote Similarity	NPD5223	Approved
0.6288	Remote Similarity	NPD6868	Approved
0.6286	Remote Similarity	NPD6914	Discontinued
0.6281	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.625	Remote Similarity	NPD4202	Approved
0.625	Remote Similarity	NPD4730	Approved
0.625	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.625	Remote Similarity	NPD4729	Approved
0.6241	Remote Similarity	NPD6317	Approved
0.6204	Remote Similarity	NPD7642	Approved
0.6194	Remote Similarity	NPD7641	Discontinued
0.6194	Remote Similarity	NPD6314	Approved
0.6194	Remote Similarity	NPD6313	Approved
0.619	Remote Similarity	NPD4754	Approved
0.6186	Remote Similarity	NPD5737	Approved
0.6186	Remote Similarity	NPD6672	Approved
0.6186	Remote Similarity	NPD6903	Approved
0.6182	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.6176	Remote Similarity	NPD6291	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