NPASS Compound

Structure

NPC470229 OpenBabel07101719522D 31 34 0 0 1 0 0 0 0 0999 V2000 2.2601 1.2601 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5822 1.4138 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0407 -2.7198 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3997 -1.9105 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2321 1.0185 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2172 1.6034 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7148 1.0829 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4942 0.0373 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5050 -0.6827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6397 -1.0707 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3090 0.9511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3090 0.9511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7088 1.9008 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8327 -2.2328 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 1.5388 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.6182 0.3693 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.2579 -0.7014 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.8653 0.3880 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0108 -0.7200 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3998 -1.9254 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8868 -1.0520 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.2471 0.0187 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.6938 2.9007 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6912 -2.7457 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5878 -0.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.9127 -2.7839 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3999 -1.9404 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8503 1.3879 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8477 -1.2329 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 12 2 0 0 0 0 2 13 1 0 0 0 0 3 14 1 0 0 0 0 6 7 1 0 0 0 0 7 16 1 0 0 0 0 8 9 1 0 0 0 0 8 18 1 0 0 0 0 9 22 1 0 0 0 0 10 17 1 0 0 0 0 10 19 1 0 0 0 0 11 15 1 0 0 0 0 12 15 1 0 0 0 0 12 20 1 0 0 0 0 13 25 2 0 0 0 0 13 30 1 0 0 0 0 14 26 2 0 0 0 0 14 31 1 0 0 0 0 15 6 1 1 0 0 0 16 23 1 6 0 0 0 16 24 1 0 0 0 0 17 22 1 6 0 0 0 17 23 1 0 0 0 0 18 23 1 6 0 0 0 18 30 1 0 0 0 0 19 24 1 1 0 0 0 19 31 1 0 0 0 0 20 24 1 0 0 0 0 20 27 2 0 0 0 0 21 22 1 0 0 0 0 21 28 2 0 0 0 0 21 29 1 0 0 0 0 22 4 1 1 0 0 0 23 5 1 6 0 0 0 24 11 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	432.21
Volume:	437.784
LogP:	1.112
LogD:	1.09
LogS:	-3.65
# Rotatable Bonds:	5
TPSA:	106.97
# H-Bond Aceptor:	7
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.538
Synthetic Accessibility Score:	5.958
Fsp3:	0.75
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	2
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.162
MDCK Permeability:	7.453188300132751e-05
Pgp-inhibitor:	0.964
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.033
20% Bioavailability (F20%):	0.237
30% Bioavailability (F30%):	0.946

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.822
Plasma Protein Binding (PPB):	66.73616790771484%
Volume Distribution (VD):	0.377
Pgp-substrate:	41.87315368652344%

ADMET: Metabolism

CYP1A2-inhibitor:	0.008
CYP1A2-substrate:	0.04
CYP2C19-inhibitor:	0.009
CYP2C19-substrate:	0.075
CYP2C9-inhibitor:	0.009
CYP2C9-substrate:	0.07
CYP2D6-inhibitor:	0.029
CYP2D6-substrate:	0.102
CYP3A4-inhibitor:	0.084
CYP3A4-substrate:	0.187

ADMET: Excretion

Clearance (CL):	1.568
Half-life (T1/2):	0.429

ADMET: Toxicity

hERG Blockers:	0.079
Human Hepatotoxicity (H-HT):	0.146
Drug-inuced Liver Injury (DILI):	0.612
AMES Toxicity:	0.102
Rat Oral Acute Toxicity:	0.93
Maximum Recommended Daily Dose:	0.913
Skin Sensitization:	0.92
Carcinogencity:	0.742
Eye Corrosion:	0.25
Eye Irritation:	0.126
Respiratory Toxicity:	0.972

Download Data

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

Natural Product: NPC470229

Natural Product ID:	NPC470229
*Common Name:**	JMLPJPQQKYBNBI-WXCZESARSA-N
IUPAC Name:	n.a.
Synonyms:	1,7-O-Diacetylgeopyxin A
Standard InCHIKey:	JMLPJPQQKYBNBI-WXCZESARSA-N
Standard InCHI:	InChI=1S/C24H32O7/c1-12-15-6-7-16-23(5)17(10-19(31-14(3)26)24(16,11-15)20(12)27)22(4,21(28)29)9-8-18(23)30-13(2)25/h15-19H,1,6-11H2,2-5H3,(H,28,29)/t15-,16+,17-,18+,19+,22-,23+,24-/m1/s1
SMILES:	CC(=O)O[C@H]1CC[C@@]([C@@H]2[C@]1(C)[C@@H]1CC[C@@H]3C[C@@]1([C@H](C2)OC(=O)C)C(=O)C3=C)(C)C(=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1873045
PubChem CID:	51361445
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0003782] Kaurane diterpenoids

*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
NPO33235	geopyxis sp. az0066	Species	Pyronemataceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22264149]
NPO32738	geopyxis aff. majalis	Species	Pyronemataceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22264149]

☑ 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
Potency	11

Activity Type	# Activity
Cell Line	1
Individual Protein	8
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT65	Cell Line	HepG2	Homo sapiens	Potency	n.a.	19952.6	nM	PMID[450066]
NPT154	Individual Protein	Mothers against decapentaplegic homolog 3	Homo sapiens	Potency	n.a.	10000.0	nM	PMID[450066]
NPT477	Individual Protein	DNA dC->dU-editing enzyme APOBEC-3G	Homo sapiens	Potency	n.a.	3981.1	nM	PMID[450066]
NPT478	Individual Protein	Ataxin-2	Homo sapiens	Potency	n.a.	39810.7	nM	PMID[450066]
NPT101	Individual Protein	Glucagon-like peptide 1 receptor	Homo sapiens	Potency	n.a.	22387.2	nM	PMID[450066]
NPT50	Individual Protein	Tyrosyl-DNA phosphodiesterase 1	Homo sapiens	Potency	n.a.	4109.5	nM	PMID[450066]
NPT50	Individual Protein	Tyrosyl-DNA phosphodiesterase 1	Homo sapiens	Potency	n.a.	2059.6	nM	PMID[450066]
NPT160	Individual Protein	TAR DNA-binding protein 43	Homo sapiens	Potency	n.a.	15848.9	nM	PMID[450066]
NPT2	Others	Unspecified		Potency	n.a.	6513.1	nM	PMID[450066]
NPT861	Individual Protein	Isocitrate dehydrogenase [NADP] cytoplasmic	Homo sapiens	Potency	n.a.	6513.1	nM	PMID[450066]
NPT2	Others	Unspecified		Potency	n.a.	39810.7	nM	PMID[450066]

☑ 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 NPC470229 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	210
0.1-0.2	1632
0.2-0.3	5603
0.3-0.4	10178
0.4-0.5	10745
0.5-0.6	6013
0.6-0.7	5400
0.7-0.8	2484
0.8-0.85	255
0.85-0.9	103
0.9-0.95	61
0.95-1	13

Similarity Score	Similarity Level	Natural Product ID
0.9888	High Similarity	NPC329910
0.9886	High Similarity	NPC475118
0.9775	High Similarity	NPC470232
0.967	High Similarity	NPC471038
0.9663	High Similarity	NPC470386
0.9663	High Similarity	NPC470385
0.9663	High Similarity	NPC47853
0.9659	High Similarity	NPC470230
0.9462	High Similarity	NPC163963
0.9462	High Similarity	NPC289148
0.9462	High Similarity	NPC52899
0.9462	High Similarity	NPC46848
0.9457	High Similarity	NPC474793
0.9451	High Similarity	NPC470387
0.9451	High Similarity	NPC200054
0.9451	High Similarity	NPC29410
0.9438	High Similarity	NPC211403
0.9438	High Similarity	NPC198242
0.9432	High Similarity	NPC471043
0.9362	High Similarity	NPC275990
0.9362	High Similarity	NPC304832
0.9362	High Similarity	NPC76866
0.9362	High Similarity	NPC148628
0.9362	High Similarity	NPC286519
0.9362	High Similarity	NPC88203
0.9362	High Similarity	NPC246736
0.9362	High Similarity	NPC214946
0.9355	High Similarity	NPC287676
0.9341	High Similarity	NPC98639
0.9263	High Similarity	NPC277074
0.9263	High Similarity	NPC87927
0.9263	High Similarity	NPC122811
0.9263	High Similarity	NPC209298
0.9255	High Similarity	NPC236585
0.9247	High Similarity	NPC38296
0.9247	High Similarity	NPC28864
0.9247	High Similarity	NPC162459
0.9247	High Similarity	NPC16911
0.9247	High Similarity	NPC78427
0.9247	High Similarity	NPC20479
0.9247	High Similarity	NPC38471
0.9247	High Similarity	NPC98837
0.9222	High Similarity	NPC250753
0.9167	High Similarity	NPC98603
0.9149	High Similarity	NPC470388
0.9149	High Similarity	NPC293866
0.9121	High Similarity	NPC294263
0.9072	High Similarity	NPC138908
0.9072	High Similarity	NPC200957
0.9062	High Similarity	NPC139347
0.9062	High Similarity	NPC216114
0.9053	High Similarity	NPC252614
0.9043	High Similarity	NPC472028
0.9043	High Similarity	NPC89099
0.9032	High Similarity	NPC13949
0.8989	High Similarity	NPC259009
0.898	High Similarity	NPC201908
0.898	High Similarity	NPC176949
0.898	High Similarity	NPC166993
0.8969	High Similarity	NPC84928
0.8947	High Similarity	NPC94906
0.8947	High Similarity	NPC267921
0.8936	High Similarity	NPC10864
0.8925	High Similarity	NPC210214
0.8901	High Similarity	NPC80401
0.8889	High Similarity	NPC112895
0.8889	High Similarity	NPC273155
0.8889	High Similarity	NPC231278
0.8889	High Similarity	NPC218123
0.8876	High Similarity	NPC471042
0.8866	High Similarity	NPC469985
0.8866	High Similarity	NPC96217
0.8854	High Similarity	NPC71706
0.8854	High Similarity	NPC148279
0.8854	High Similarity	NPC75941
0.8854	High Similarity	NPC471790
0.8842	High Similarity	NPC26270
0.883	High Similarity	NPC219353
0.8804	High Similarity	NPC476168
0.8788	High Similarity	NPC186054
0.8778	High Similarity	NPC153604
0.8776	High Similarity	NPC474558
0.8776	High Similarity	NPC96268
0.8776	High Similarity	NPC202793
0.8776	High Similarity	NPC301787
0.8764	High Similarity	NPC190704
0.8764	High Similarity	NPC471034
0.8763	High Similarity	NPC309388
0.8763	High Similarity	NPC124544
0.8763	High Similarity	NPC475803
0.875	High Similarity	NPC41971
0.875	High Similarity	NPC37047
0.875	High Similarity	NPC180733
0.875	High Similarity	NPC471037
0.8737	High Similarity	NPC253586
0.8737	High Similarity	NPC96839
0.8723	High Similarity	NPC288906
0.8723	High Similarity	NPC263135
0.871	High Similarity	NPC244356
0.871	High Similarity	NPC181594
0.871	High Similarity	NPC224060
0.871	High Similarity	NPC144739
0.87	High Similarity	NPC63841
0.87	High Similarity	NPC211224
0.8687	High Similarity	NPC4115
0.8687	High Similarity	NPC295366
0.8687	High Similarity	NPC37600
0.8687	High Similarity	NPC222833
0.8673	High Similarity	NPC159442
0.8673	High Similarity	NPC470310
0.866	High Similarity	NPC121218
0.866	High Similarity	NPC253886
0.866	High Similarity	NPC14634
0.8632	High Similarity	NPC234564
0.8632	High Similarity	NPC104568
0.8627	High Similarity	NPC470281
0.8627	High Similarity	NPC329953
0.8617	High Similarity	NPC153775
0.8617	High Similarity	NPC261333
0.8617	High Similarity	NPC302008
0.8617	High Similarity	NPC215271
0.8617	High Similarity	NPC292374
0.8617	High Similarity	NPC129004
0.8617	High Similarity	NPC91772
0.8617	High Similarity	NPC29247
0.8617	High Similarity	NPC111524
0.8617	High Similarity	NPC191094
0.8617	High Similarity	NPC289539
0.8617	High Similarity	NPC104371
0.8617	High Similarity	NPC101233
0.8614	High Similarity	NPC274827
0.8602	High Similarity	NPC299185
0.8602	High Similarity	NPC471901
0.8602	High Similarity	NPC476934
0.86	High Similarity	NPC471474
0.86	High Similarity	NPC88833
0.86	High Similarity	NPC96333
0.86	High Similarity	NPC61071
0.8586	High Similarity	NPC13149
0.8586	High Similarity	NPC101842
0.8571	High Similarity	NPC170615
0.8557	High Similarity	NPC293890
0.8557	High Similarity	NPC108371
0.8542	High Similarity	NPC469810
0.8539	High Similarity	NPC471036
0.8539	High Similarity	NPC291320
0.8529	High Similarity	NPC474786
0.8529	High Similarity	NPC320383
0.8529	High Similarity	NPC471093
0.8529	High Similarity	NPC137104
0.8526	High Similarity	NPC266431
0.8526	High Similarity	NPC138245
0.8526	High Similarity	NPC84018
0.8526	High Similarity	NPC197158
0.8526	High Similarity	NPC231060
0.8526	High Similarity	NPC471624
0.8515	High Similarity	NPC232133
0.8515	High Similarity	NPC473410
0.8515	High Similarity	NPC471094
0.8515	High Similarity	NPC469984
0.8511	High Similarity	NPC471902
0.8511	High Similarity	NPC473690
0.8511	High Similarity	NPC287118
0.8511	High Similarity	NPC199543
0.85	High Similarity	NPC103172
0.85	High Similarity	NPC164600
0.85	High Similarity	NPC265127
0.85	High Similarity	NPC56656
0.85	High Similarity	NPC12823
0.8495	Intermediate Similarity	NPC180849
0.8495	Intermediate Similarity	NPC470378
0.8495	Intermediate Similarity	NPC149761
0.8495	Intermediate Similarity	NPC261994
0.8485	Intermediate Similarity	NPC312900
0.8478	Intermediate Similarity	NPC56413
0.8478	Intermediate Similarity	NPC4309
0.8469	Intermediate Similarity	NPC295276
0.8462	Intermediate Similarity	NPC471252
0.8447	Intermediate Similarity	NPC29505
0.8444	Intermediate Similarity	NPC299963
0.8444	Intermediate Similarity	NPC473336
0.8444	Intermediate Similarity	NPC146683
0.8444	Intermediate Similarity	NPC471044
0.8438	Intermediate Similarity	NPC264979
0.8438	Intermediate Similarity	NPC135548
0.8438	Intermediate Similarity	NPC140242
0.8431	Intermediate Similarity	NPC469983
0.8431	Intermediate Similarity	NPC131903
0.8427	Intermediate Similarity	NPC472504
0.8421	Intermediate Similarity	NPC169751
0.8421	Intermediate Similarity	NPC469982
0.8421	Intermediate Similarity	NPC272635
0.8404	Intermediate Similarity	NPC475416
0.8404	Intermediate Similarity	NPC198054
0.84	Intermediate Similarity	NPC47281
0.8387	Intermediate Similarity	NPC57954
0.8387	Intermediate Similarity	NPC213832
0.837	Intermediate Similarity	NPC57469
0.837	Intermediate Similarity	NPC33768
0.837	Intermediate Similarity	NPC174619

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 NPC470229 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	190
0.1-0.2	2017
0.2-0.3	3973
0.3-0.4	1921
0.4-0.5	566
0.5-0.6	211
0.6-0.7	143
0.7-0.8	127
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8211	Intermediate Similarity	NPD8034	Phase 2
0.8211	Intermediate Similarity	NPD8035	Phase 2
0.8152	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.79	Intermediate Similarity	NPD7638	Approved
0.7857	Intermediate Similarity	NPD7748	Approved
0.7835	Intermediate Similarity	NPD6079	Approved
0.7822	Intermediate Similarity	NPD7640	Approved
0.7822	Intermediate Similarity	NPD7639	Approved
0.7812	Intermediate Similarity	NPD5328	Approved
0.781	Intermediate Similarity	NPD6881	Approved
0.781	Intermediate Similarity	NPD6899	Approved
0.7788	Intermediate Similarity	NPD7128	Approved
0.7788	Intermediate Similarity	NPD5739	Approved
0.7788	Intermediate Similarity	NPD6675	Approved
0.7788	Intermediate Similarity	NPD6402	Approved
0.7778	Intermediate Similarity	NPD6115	Approved
0.7778	Intermediate Similarity	NPD6114	Approved
0.7778	Intermediate Similarity	NPD6118	Approved
0.7778	Intermediate Similarity	NPD6697	Approved
0.7755	Intermediate Similarity	NPD6399	Phase 3
0.7714	Intermediate Similarity	NPD5697	Approved
0.7679	Intermediate Similarity	NPD6319	Approved
0.7664	Intermediate Similarity	NPD7102	Approved
0.7664	Intermediate Similarity	NPD6883	Approved
0.7664	Intermediate Similarity	NPD7290	Approved
0.7653	Intermediate Similarity	NPD7515	Phase 2
0.7642	Intermediate Similarity	NPD7320	Approved
0.7642	Intermediate Similarity	NPD6011	Approved
0.7624	Intermediate Similarity	NPD7902	Approved
0.7619	Intermediate Similarity	NPD6008	Approved
0.7615	Intermediate Similarity	NPD4632	Approved
0.7593	Intermediate Similarity	NPD6649	Approved
0.7593	Intermediate Similarity	NPD8130	Phase 1
0.7593	Intermediate Similarity	NPD6847	Approved
0.7593	Intermediate Similarity	NPD6650	Approved
0.7593	Intermediate Similarity	NPD6617	Approved
0.7593	Intermediate Similarity	NPD6869	Approved
0.757	Intermediate Similarity	NPD6013	Approved
0.757	Intermediate Similarity	NPD6373	Approved
0.757	Intermediate Similarity	NPD6014	Approved
0.757	Intermediate Similarity	NPD6372	Approved
0.757	Intermediate Similarity	NPD6012	Approved
0.7565	Intermediate Similarity	NPD7492	Approved
0.7556	Intermediate Similarity	NPD6117	Approved
0.7553	Intermediate Similarity	NPD4788	Approved
0.7547	Intermediate Similarity	NPD5701	Approved
0.7525	Intermediate Similarity	NPD5221	Approved
0.7525	Intermediate Similarity	NPD5222	Approved
0.7525	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7523	Intermediate Similarity	NPD6882	Approved
0.7523	Intermediate Similarity	NPD8297	Approved
0.7522	Intermediate Similarity	NPD6054	Approved
0.7521	Intermediate Similarity	NPD7736	Approved
0.75	Intermediate Similarity	NPD6616	Approved
0.7477	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7473	Intermediate Similarity	NPD6116	Phase 1
0.7451	Intermediate Similarity	NPD5173	Approved
0.7444	Intermediate Similarity	NPD3703	Phase 2
0.7436	Intermediate Similarity	NPD7078	Approved
0.7431	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7411	Intermediate Similarity	NPD6009	Approved
0.7391	Intermediate Similarity	NPD6370	Approved
0.7368	Intermediate Similarity	NPD6059	Approved
0.7353	Intermediate Similarity	NPD4697	Phase 3
0.7347	Intermediate Similarity	NPD6672	Approved
0.7347	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD5737	Approved
0.7339	Intermediate Similarity	NPD4634	Approved
0.7333	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD7632	Discontinued
0.7328	Intermediate Similarity	NPD7604	Phase 2
0.7327	Intermediate Similarity	NPD7900	Approved
0.7327	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD6868	Approved
0.732	Intermediate Similarity	NPD6409	Approved
0.732	Intermediate Similarity	NPD3618	Phase 1
0.732	Intermediate Similarity	NPD6684	Approved
0.732	Intermediate Similarity	NPD7521	Approved
0.732	Intermediate Similarity	NPD5330	Approved
0.732	Intermediate Similarity	NPD7334	Approved
0.732	Intermediate Similarity	NPD7146	Approved
0.7308	Intermediate Similarity	NPD5286	Approved
0.7308	Intermediate Similarity	NPD4696	Approved
0.7308	Intermediate Similarity	NPD5285	Approved
0.7304	Intermediate Similarity	NPD5983	Phase 2
0.7304	Intermediate Similarity	NPD6015	Approved
0.7304	Intermediate Similarity	NPD6016	Approved
0.7292	Intermediate Similarity	NPD4786	Approved
0.7288	Intermediate Similarity	NPD8293	Discontinued
0.7282	Intermediate Similarity	NPD4755	Approved
0.7282	Intermediate Similarity	NPD6084	Phase 2
0.7282	Intermediate Similarity	NPD6083	Phase 2
0.7257	Intermediate Similarity	NPD7115	Discovery
0.7245	Intermediate Similarity	NPD3573	Approved
0.7241	Intermediate Similarity	NPD5988	Approved
0.7238	Intermediate Similarity	NPD5223	Approved
0.7203	Intermediate Similarity	NPD6336	Discontinued
0.7193	Intermediate Similarity	NPD6335	Approved
0.7179	Intermediate Similarity	NPD8328	Phase 3
0.7172	Intermediate Similarity	NPD6903	Approved
0.717	Intermediate Similarity	NPD5225	Approved
0.717	Intermediate Similarity	NPD4633	Approved
0.717	Intermediate Similarity	NPD5226	Approved
0.717	Intermediate Similarity	NPD5211	Phase 2
0.717	Intermediate Similarity	NPD5224	Approved
0.7168	Intermediate Similarity	NPD6274	Approved
0.7167	Intermediate Similarity	NPD7319	Approved
0.7143	Intermediate Similarity	NPD4700	Approved
0.7143	Intermediate Similarity	NPD8133	Approved
0.7143	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.713	Intermediate Similarity	NPD7101	Approved
0.713	Intermediate Similarity	NPD7100	Approved
0.7129	Intermediate Similarity	NPD6411	Approved
0.7111	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD6317	Approved
0.7103	Intermediate Similarity	NPD5174	Approved
0.7103	Intermediate Similarity	NPD5175	Approved
0.7087	Intermediate Similarity	NPD5695	Phase 3
0.7087	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD3667	Approved
0.7059	Intermediate Similarity	NPD4202	Approved
0.7059	Intermediate Similarity	NPD7507	Approved
0.7048	Intermediate Similarity	NPD5696	Approved
0.7043	Intermediate Similarity	NPD6313	Approved
0.7043	Intermediate Similarity	NPD6314	Approved
0.7037	Intermediate Similarity	NPD5141	Approved
0.6957	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD4754	Approved
0.6942	Remote Similarity	NPD6033	Approved
0.6939	Remote Similarity	NPD3133	Approved
0.6939	Remote Similarity	NPD3666	Approved
0.6939	Remote Similarity	NPD3665	Phase 1
0.6932	Remote Similarity	NPD4224	Phase 2
0.6931	Remote Similarity	NPD6673	Approved
0.6931	Remote Similarity	NPD6904	Approved
0.6931	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6931	Remote Similarity	NPD6080	Approved
0.6931	Remote Similarity	NPD6101	Approved
0.6923	Remote Similarity	NPD5777	Approved
0.6923	Remote Similarity	NPD6081	Approved
0.6909	Remote Similarity	NPD6412	Phase 2
0.6893	Remote Similarity	NPD5779	Approved
0.6893	Remote Similarity	NPD5778	Approved
0.6889	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD4225	Approved
0.6882	Remote Similarity	NPD3702	Approved
0.6875	Remote Similarity	NPD7525	Registered
0.6864	Remote Similarity	NPD6909	Approved
0.6864	Remote Similarity	NPD6908	Approved
0.6864	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6847	Remote Similarity	NPD4729	Approved
0.6847	Remote Similarity	NPD6686	Approved
0.6847	Remote Similarity	NPD4730	Approved
0.6847	Remote Similarity	NPD5128	Approved
0.6847	Remote Similarity	NPD5168	Approved
0.6818	Remote Similarity	NPD4767	Approved
0.6818	Remote Similarity	NPD4768	Approved
0.68	Remote Similarity	NPD6098	Approved
0.6796	Remote Similarity	NPD7637	Suspended
0.6786	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6778	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.6778	Remote Similarity	NPD5360	Phase 3
0.6768	Remote Similarity	NPD3668	Phase 3
0.6765	Remote Similarity	NPD4753	Phase 2
0.6735	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6735	Remote Similarity	NPD4221	Approved
0.6735	Remote Similarity	NPD4223	Phase 3
0.6726	Remote Similarity	NPD5249	Phase 3
0.6726	Remote Similarity	NPD5251	Approved
0.6726	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6726	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6726	Remote Similarity	NPD5247	Approved
0.6726	Remote Similarity	NPD5135	Approved
0.6726	Remote Similarity	NPD5169	Approved
0.6726	Remote Similarity	NPD5250	Approved
0.6726	Remote Similarity	NPD5248	Approved
0.6723	Remote Similarity	NPD6921	Approved
0.6719	Remote Similarity	NPD6334	Approved
0.6719	Remote Similarity	NPD6333	Approved
0.67	Remote Similarity	NPD5329	Approved
0.6667	Remote Similarity	NPD5215	Approved
0.6667	Remote Similarity	NPD5127	Approved
0.6667	Remote Similarity	NPD5208	Approved
0.6667	Remote Similarity	NPD5216	Approved
0.6667	Remote Similarity	NPD6001	Approved
0.6667	Remote Similarity	NPD5217	Approved
0.6635	Remote Similarity	NPD5693	Phase 1
0.6635	Remote Similarity	NPD5284	Approved
0.6635	Remote Similarity	NPD5281	Approved
0.6635	Remote Similarity	NPD6050	Approved
0.6634	Remote Similarity	NPD5279	Phase 3
0.663	Remote Similarity	NPD4244	Approved
0.663	Remote Similarity	NPD4789	Approved
0.663	Remote Similarity	NPD4245	Approved
0.6609	Remote Similarity	NPD6053	Discontinued
0.6604	Remote Similarity	NPD5210	Approved
0.6604	Remote Similarity	NPD4629	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