NPASS Compound

Structure

NPC201837 OpenBabel07101718272D 22 24 0 0 1 0 0 0 0 0999 V2000 -2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.3301 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 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 3 1 0 0 0 0 1 6 2 0 0 0 0 2 4 2 0 0 0 0 2 6 1 0 0 0 0 3 7 2 0 0 0 0 4 7 1 0 0 0 0 5 8 2 0 0 0 0 5 9 1 0 0 0 0 7 16 1 0 0 0 0 8 11 1 0 0 0 0 8 17 1 0 0 0 0 9 10 2 0 0 0 0 9 22 1 0 0 0 0 10 12 1 0 0 0 0 10 13 1 0 0 0 0 11 12 2 0 0 0 0 11 18 1 0 0 0 0 12 19 1 0 0 0 0 13 14 1 0 0 0 0 13 20 2 0 0 0 0 14 15 1 0 0 0 0 14 21 1 6 0 0 0 15 6 1 1 0 0 0 15 22 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	304.06
Volume:	285.403
LogP:	0.362
LogD:	-0.239
LogS:	-2.451
# Rotatable Bonds:	1
TPSA:	127.45
# H-Bond Aceptor:	7
# H-Bond Donor:	5
# Rings:	3
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.501
Synthetic Accessibility Score:	3.555
Fsp3:	0.133
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.044
MDCK Permeability:	4.007436473330017e-06
Pgp-inhibitor:	0.004
Pgp-substrate:	0.009
Human Intestinal Absorption (HIA):	0.013
20% Bioavailability (F20%):	0.83
30% Bioavailability (F30%):	0.183

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.015
Plasma Protein Binding (PPB):	94.35565185546875%
Volume Distribution (VD):	0.48
Pgp-substrate:	7.97815465927124%

ADMET: Metabolism

CYP1A2-inhibitor:	0.027
CYP1A2-substrate:	0.078
CYP2C19-inhibitor:	0.025
CYP2C19-substrate:	0.065
CYP2C9-inhibitor:	0.257
CYP2C9-substrate:	0.825
CYP2D6-inhibitor:	0.035
CYP2D6-substrate:	0.223
CYP3A4-inhibitor:	0.035
CYP3A4-substrate:	0.241

ADMET: Excretion

Clearance (CL):	5.036
Half-life (T1/2):	0.825

ADMET: Toxicity

hERG Blockers:	0.061
Human Hepatotoxicity (H-HT):	0.204
Drug-inuced Liver Injury (DILI):	0.957
AMES Toxicity:	0.358
Rat Oral Acute Toxicity:	0.252
Maximum Recommended Daily Dose:	0.036
Skin Sensitization:	0.947
Carcinogencity:	0.052
Eye Corrosion:	0.003
Eye Irritation:	0.884
Respiratory Toxicity:	0.153

Download Data

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

Natural Product: NPC201837

Natural Product ID:	NPC201837
*Common Name:**	SPLXVVIJECEDFW-LSDHHAIUSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	SPLXVVIJECEDFW-LSDHHAIUSA-N
Standard InCHI:	InChI=1S/C15H12O7/c16-7-3-1-6(2-4-7)15-14(21)13(20)10-9(22-15)5-8(17)11(18)12(10)19/h1-5,14-19,21H/t14-,15+/m0/s1
SMILES:	c1cc(ccc1[C@@H]1[C@H](C(=O)c2c(cc(c(c2O)O)O)O1)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3609150
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0000337] Flavans [CHEMONTID:0001632] Flavanones [CHEMONTID:0001362] Flavanonols

*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
NPO30804	Cudrania tricuspidata	Species	Moraceae	Eukaryota	n.a.	root	n.a.	PMID[15787460]
NPO30804	Cudrania tricuspidata	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15787460]
NPO30804	Cudrania tricuspidata	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16203143]
NPO30804	Cudrania tricuspidata	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16919944]
NPO30804	Cudrania tricuspidata	Species	Moraceae	Eukaryota	root bark	n.a.	n.a.	PMID[17608532]
NPO30804	Cudrania tricuspidata	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17950599]
NPO30804	Cudrania tricuspidata	Species	Moraceae	Eukaryota	fruits	n.a.	n.a.	PMID[19113968]
NPO30804	Cudrania tricuspidata	Species	Moraceae	Eukaryota	Roots	n.a.	n.a.	PMID[19191562]
NPO30804	Cudrania tricuspidata	Species	Moraceae	Eukaryota	n.a.	root	n.a.	PMID[19280148]
NPO30804	Cudrania tricuspidata	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19285413]
NPO30804	Cudrania tricuspidata	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19660948]
NPO30804	Cudrania tricuspidata	Species	Moraceae	Eukaryota	n.a.	root	n.a.	PMID[21319773]
NPO30804	Cudrania tricuspidata	Species	Moraceae	Eukaryota	Roots	n.a.	n.a.	PMID[25322455]
NPO30804	Cudrania tricuspidata	Species	Moraceae	Eukaryota	root barks	purchased from the local herbal market, Chungbuk, Korea	2012-JUL	PMID[26227773]
NPO30804	Cudrania tricuspidata	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO30804	Cudrania tricuspidata	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]

☑ 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
Others	1

Activity Type	# Activity
Individual Protein	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1120	Individual Protein	Pancreatic triacylglycerol lipase	Sus scrofa	IC50	>	100000.0	nM	PMID[505109]
NPT1120	Individual Protein	Pancreatic triacylglycerol lipase	Sus scrofa	Inhibition	=	40.1	%	PMID[505109]

☑ 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 NPC201837 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	474
0.1-0.2	1821
0.2-0.3	4824
0.3-0.4	10800
0.4-0.5	6643
0.5-0.6	3765
0.6-0.7	4909
0.7-0.8	5351
0.8-0.85	2332
0.85-0.9	1273
0.9-0.95	463
0.95-1	42

Similarity Score	Similarity Level	Natural Product ID
0.9801	High Similarity	NPC263449
0.9797	High Similarity	NPC9743
0.9797	High Similarity	NPC61506
0.9797	High Similarity	NPC240476
0.9797	High Similarity	NPC36835
0.9797	High Similarity	NPC246162
0.9797	High Similarity	NPC260491
0.9737	High Similarity	NPC308992
0.9732	High Similarity	NPC256346
0.9732	High Similarity	NPC27532
0.9732	High Similarity	NPC246328
0.9732	High Similarity	NPC325028
0.973	High Similarity	NPC204515
0.9664	High Similarity	NPC19721
0.9603	High Similarity	NPC320825
0.9603	High Similarity	NPC13858
0.9603	High Similarity	NPC255106
0.9603	High Similarity	NPC235165
0.9603	High Similarity	NPC326037
0.9539	High Similarity	NPC474836
0.9539	High Similarity	NPC162869
0.9539	High Similarity	NPC48208
0.9539	High Similarity	NPC210084
0.9539	High Similarity	NPC475267
0.9539	High Similarity	NPC474208
0.9539	High Similarity	NPC156057
0.9539	High Similarity	NPC52530
0.9539	High Similarity	NPC99597
0.9533	High Similarity	NPC180234
0.9533	High Similarity	NPC120537
0.9533	High Similarity	NPC199100
0.953	High Similarity	NPC61620
0.953	High Similarity	NPC62042
0.9527	High Similarity	NPC294852
0.9527	High Similarity	NPC218569
0.9527	High Similarity	NPC188679
0.9527	High Similarity	NPC276930
0.9527	High Similarity	NPC321011
0.9477	High Similarity	NPC152904
0.9477	High Similarity	NPC22192
0.9474	High Similarity	NPC471500
0.9474	High Similarity	NPC474638
0.9474	High Similarity	NPC250922
0.947	High Similarity	NPC167091
0.947	High Similarity	NPC88645
0.947	High Similarity	NPC141212
0.947	High Similarity	NPC292214
0.947	High Similarity	NPC206238
0.947	High Similarity	NPC271779
0.9467	High Similarity	NPC225731
0.9467	High Similarity	NPC251110
0.9463	High Similarity	NPC183959
0.9463	High Similarity	NPC195351
0.9463	High Similarity	NPC1612
0.9459	High Similarity	NPC21835
0.9427	High Similarity	NPC42892
0.9423	High Similarity	NPC224280
0.9416	High Similarity	NPC282009
0.9416	High Similarity	NPC287328
0.9416	High Similarity	NPC470183
0.9412	High Similarity	NPC471479
0.9412	High Similarity	NPC472910
0.9412	High Similarity	NPC471515
0.9412	High Similarity	NPC472913
0.9412	High Similarity	NPC472914
0.9412	High Similarity	NPC96167
0.9412	High Similarity	NPC222814
0.9412	High Similarity	NPC472911
0.9412	High Similarity	NPC245758
0.9412	High Similarity	NPC470402
0.9408	High Similarity	NPC201451
0.9408	High Similarity	NPC37392
0.9408	High Similarity	NPC44079
0.9408	High Similarity	NPC26227
0.9408	High Similarity	NPC2928
0.9404	High Similarity	NPC219582
0.9404	High Similarity	NPC27208
0.9404	High Similarity	NPC302950
0.9404	High Similarity	NPC236637
0.9404	High Similarity	NPC101996
0.9404	High Similarity	NPC39007
0.9404	High Similarity	NPC161277
0.94	High Similarity	NPC248102
0.94	High Similarity	NPC77858
0.9396	High Similarity	NPC194856
0.9355	High Similarity	NPC471499
0.9355	High Similarity	NPC173137
0.9355	High Similarity	NPC289771
0.9351	High Similarity	NPC55738
0.9351	High Similarity	NPC250214
0.9351	High Similarity	NPC95936
0.9351	High Similarity	NPC329091
0.9346	High Similarity	NPC303255
0.9346	High Similarity	NPC43243
0.9346	High Similarity	NPC266960
0.9346	High Similarity	NPC472916
0.9346	High Similarity	NPC98661
0.9346	High Similarity	NPC245546
0.9346	High Similarity	NPC247017
0.9346	High Similarity	NPC49824
0.9342	High Similarity	NPC18727
0.9338	High Similarity	NPC171010
0.9338	High Similarity	NPC149614
0.9338	High Similarity	NPC117579
0.9333	High Similarity	NPC17286
0.9333	High Similarity	NPC259713
0.9333	High Similarity	NPC296197
0.9333	High Similarity	NPC216318
0.9329	High Similarity	NPC207729
0.9329	High Similarity	NPC130230
0.9329	High Similarity	NPC275772
0.9329	High Similarity	NPC239312
0.9324	High Similarity	NPC306607
0.9324	High Similarity	NPC4152
0.9324	High Similarity	NPC49130
0.9324	High Similarity	NPC326506
0.9324	High Similarity	NPC279417
0.9324	High Similarity	NPC208176
0.9324	High Similarity	NPC142731
0.9324	High Similarity	NPC62290
0.9304	High Similarity	NPC295082
0.9299	High Similarity	NPC470457
0.9299	High Similarity	NPC234052
0.929	High Similarity	NPC470326
0.929	High Similarity	NPC471744
0.9286	High Similarity	NPC305663
0.9286	High Similarity	NPC78225
0.9286	High Similarity	NPC101830
0.9286	High Similarity	NPC176665
0.9286	High Similarity	NPC224137
0.9286	High Similarity	NPC110070
0.9286	High Similarity	NPC203891
0.9286	High Similarity	NPC93376
0.9286	High Similarity	NPC472598
0.9286	High Similarity	NPC287979
0.9286	High Similarity	NPC75215
0.9286	High Similarity	NPC189179
0.9286	High Similarity	NPC223787
0.9286	High Similarity	NPC469584
0.9286	High Similarity	NPC67876
0.9286	High Similarity	NPC227192
0.9286	High Similarity	NPC163524
0.9286	High Similarity	NPC474055
0.9281	High Similarity	NPC214138
0.9281	High Similarity	NPC321779
0.9281	High Similarity	NPC472909
0.9281	High Similarity	NPC213622
0.9276	High Similarity	NPC71334
0.9276	High Similarity	NPC301123
0.9276	High Similarity	NPC83508
0.9276	High Similarity	NPC100887
0.9276	High Similarity	NPC275836
0.9276	High Similarity	NPC301323
0.9276	High Similarity	NPC25270
0.9276	High Similarity	NPC239128
0.9276	High Similarity	NPC156222
0.9276	High Similarity	NPC131624
0.9276	High Similarity	NPC57030
0.9276	High Similarity	NPC293183
0.9276	High Similarity	NPC256283
0.9276	High Similarity	NPC162313
0.9276	High Similarity	NPC188203
0.9276	High Similarity	NPC187498
0.9276	High Similarity	NPC275722
0.9276	High Similarity	NPC241498
0.9276	High Similarity	NPC120163
0.9276	High Similarity	NPC198826
0.9276	High Similarity	NPC222830
0.9276	High Similarity	NPC212678
0.9272	High Similarity	NPC45873
0.9272	High Similarity	NPC184136
0.9272	High Similarity	NPC29231
0.9272	High Similarity	NPC179183
0.9267	High Similarity	NPC3036
0.9267	High Similarity	NPC272721
0.9267	High Similarity	NPC12367
0.9267	High Similarity	NPC196277
0.9267	High Similarity	NPC119059
0.9267	High Similarity	NPC218490
0.9267	High Similarity	NPC118726
0.9267	High Similarity	NPC43669
0.9262	High Similarity	NPC1940
0.9262	High Similarity	NPC20791
0.9262	High Similarity	NPC148011
0.9262	High Similarity	NPC179271
0.9236	High Similarity	NPC41301
0.9236	High Similarity	NPC472625
0.9236	High Similarity	NPC470459
0.9236	High Similarity	NPC470178
0.9231	High Similarity	NPC112418
0.9231	High Similarity	NPC266314
0.9231	High Similarity	NPC228383
0.9226	High Similarity	NPC22472
0.9226	High Similarity	NPC191459
0.9226	High Similarity	NPC204854
0.9226	High Similarity	NPC130894
0.9226	High Similarity	NPC7846
0.9226	High Similarity	NPC18772
0.9226	High Similarity	NPC300943
0.9226	High Similarity	NPC288669

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 NPC201837 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	441
0.1-0.2	953
0.2-0.3	1969
0.3-0.4	2565
0.4-0.5	1695
0.5-0.6	943
0.6-0.7	404
0.7-0.8	129
0.8-0.85	30
0.85-0.9	11
0.9-0.95	10
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9404	High Similarity	NPD1934	Approved
0.9262	High Similarity	NPD1512	Approved
0.9216	High Similarity	NPD2393	Clinical (unspecified phase)
0.9216	High Similarity	NPD2801	Approved
0.9177	High Similarity	NPD6168	Clinical (unspecified phase)
0.9177	High Similarity	NPD6166	Phase 2
0.9177	High Similarity	NPD6167	Clinical (unspecified phase)
0.9128	High Similarity	NPD1511	Approved
0.9018	High Similarity	NPD4338	Clinical (unspecified phase)
0.8974	High Similarity	NPD3882	Suspended
0.8851	High Similarity	NPD1550	Clinical (unspecified phase)
0.8851	High Similarity	NPD1552	Clinical (unspecified phase)
0.8827	High Similarity	NPD3818	Discontinued
0.8792	High Similarity	NPD1549	Phase 2
0.878	High Similarity	NPD6797	Phase 2
0.8734	High Similarity	NPD4868	Clinical (unspecified phase)
0.8727	High Similarity	NPD7251	Discontinued
0.872	High Similarity	NPD7074	Phase 3
0.8671	High Similarity	NPD3817	Phase 2
0.8659	High Similarity	NPD7054	Approved
0.8654	High Similarity	NPD4380	Phase 2
0.8606	High Similarity	NPD7472	Approved
0.8571	High Similarity	NPD5494	Approved
0.8571	High Similarity	NPD4378	Clinical (unspecified phase)
0.8563	High Similarity	NPD7808	Phase 3
0.8562	High Similarity	NPD4381	Clinical (unspecified phase)
0.8562	High Similarity	NPD7075	Discontinued
0.8554	High Similarity	NPD7993	Clinical (unspecified phase)
0.8553	High Similarity	NPD5402	Approved
0.8491	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8467	Intermediate Similarity	NPD1510	Phase 2
0.8446	Intermediate Similarity	NPD1613	Approved
0.8446	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8323	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8322	Intermediate Similarity	NPD943	Approved
0.8313	Intermediate Similarity	NPD6801	Discontinued
0.8293	Intermediate Similarity	NPD1247	Approved
0.8269	Intermediate Similarity	NPD6799	Approved
0.8261	Intermediate Similarity	NPD1465	Phase 2
0.8214	Intermediate Similarity	NPD5844	Phase 1
0.82	Intermediate Similarity	NPD1240	Approved
0.8176	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.817	Intermediate Similarity	NPD2796	Approved
0.8113	Intermediate Similarity	NPD5403	Approved
0.8108	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.8101	Intermediate Similarity	NPD5401	Approved
0.8098	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8092	Intermediate Similarity	NPD1607	Approved
0.8075	Intermediate Similarity	NPD6599	Discontinued
0.8047	Intermediate Similarity	NPD3751	Discontinued
0.8037	Intermediate Similarity	NPD7819	Suspended
0.8024	Intermediate Similarity	NPD6232	Discontinued
0.7988	Intermediate Similarity	NPD7473	Discontinued
0.7987	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7965	Intermediate Similarity	NPD6559	Discontinued
0.7964	Intermediate Similarity	NPD6959	Discontinued
0.7952	Intermediate Similarity	NPD919	Approved
0.7917	Intermediate Similarity	NPD3787	Discontinued
0.7914	Intermediate Similarity	NPD7411	Suspended
0.7911	Intermediate Similarity	NPD6190	Approved
0.7908	Intermediate Similarity	NPD230	Phase 1
0.7875	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.787	Intermediate Similarity	NPD3926	Phase 2
0.784	Intermediate Similarity	NPD1653	Approved
0.7834	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7821	Intermediate Similarity	NPD1551	Phase 2
0.7784	Intermediate Similarity	NPD3749	Approved
0.7765	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7763	Intermediate Similarity	NPD3027	Phase 3
0.7736	Intermediate Similarity	NPD3750	Approved
0.7707	Intermediate Similarity	NPD2935	Discontinued
0.7677	Intermediate Similarity	NPD447	Suspended
0.7673	Intermediate Similarity	NPD2800	Approved
0.7625	Intermediate Similarity	NPD4628	Phase 3
0.7616	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7584	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7584	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7561	Intermediate Similarity	NPD920	Approved
0.7556	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7546	Intermediate Similarity	NPD2534	Approved
0.7546	Intermediate Similarity	NPD2532	Approved
0.7546	Intermediate Similarity	NPD2533	Approved
0.7546	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD9494	Approved
0.7516	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD7768	Phase 2
0.7484	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7473	Intermediate Similarity	NPD6778	Approved
0.7473	Intermediate Similarity	NPD6779	Approved
0.7473	Intermediate Similarity	NPD6781	Approved
0.7473	Intermediate Similarity	NPD6780	Approved
0.7473	Intermediate Similarity	NPD6782	Approved
0.7473	Intermediate Similarity	NPD6777	Approved
0.7473	Intermediate Similarity	NPD6776	Approved
0.7467	Intermediate Similarity	NPD1610	Phase 2
0.7457	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7455	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7453	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7444	Intermediate Similarity	NPD8434	Phase 2
0.7442	Intermediate Similarity	NPD7199	Phase 2
0.7438	Intermediate Similarity	NPD2344	Approved
0.7427	Intermediate Similarity	NPD6234	Discontinued
0.7423	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7421	Intermediate Similarity	NPD3748	Approved
0.7421	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD1203	Approved
0.738	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7375	Intermediate Similarity	NPD6100	Approved
0.7375	Intermediate Similarity	NPD6099	Approved
0.7374	Intermediate Similarity	NPD8313	Approved
0.7374	Intermediate Similarity	NPD8312	Approved
0.7372	Intermediate Similarity	NPD2313	Discontinued
0.7365	Intermediate Similarity	NPD3226	Approved
0.7354	Intermediate Similarity	NPD7435	Discontinued
0.7348	Intermediate Similarity	NPD8150	Discontinued
0.7346	Intermediate Similarity	NPD1243	Approved
0.7342	Intermediate Similarity	NPD1933	Approved
0.7337	Intermediate Similarity	NPD6844	Discontinued
0.7337	Intermediate Similarity	NPD37	Approved
0.7333	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.733	Intermediate Similarity	NPD7228	Approved
0.7329	Intermediate Similarity	NPD2346	Discontinued
0.7325	Intermediate Similarity	NPD6233	Phase 2
0.7318	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7315	Intermediate Similarity	NPD1548	Phase 1
0.7312	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD4967	Phase 2
0.731	Intermediate Similarity	NPD4966	Approved
0.731	Intermediate Similarity	NPD4965	Approved
0.7303	Intermediate Similarity	NPD5953	Discontinued
0.7303	Intermediate Similarity	NPD9269	Phase 2
0.729	Intermediate Similarity	NPD2861	Phase 2
0.7288	Intermediate Similarity	NPD7286	Phase 2
0.7273	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7263	Intermediate Similarity	NPD7685	Pre-registration
0.7263	Intermediate Similarity	NPD7697	Approved
0.7263	Intermediate Similarity	NPD7698	Approved
0.7263	Intermediate Similarity	NPD7696	Phase 3
0.7261	Intermediate Similarity	NPD6798	Discontinued
0.7256	Intermediate Similarity	NPD2309	Approved
0.7244	Intermediate Similarity	NPD4908	Phase 1
0.7225	Intermediate Similarity	NPD7871	Phase 2
0.7225	Intermediate Similarity	NPD7870	Phase 2
0.7205	Intermediate Similarity	NPD7033	Discontinued
0.7205	Intermediate Similarity	NPD2799	Discontinued
0.7204	Intermediate Similarity	NPD6534	Approved
0.7204	Intermediate Similarity	NPD4360	Phase 2
0.7204	Intermediate Similarity	NPD4363	Phase 3
0.7204	Intermediate Similarity	NPD6535	Approved
0.7202	Intermediate Similarity	NPD7701	Phase 2
0.7188	Intermediate Similarity	NPD6651	Approved
0.7152	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD1652	Phase 2
0.7128	Intermediate Similarity	NPD7874	Approved
0.7128	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD6355	Discontinued
0.7119	Intermediate Similarity	NPD2403	Approved
0.7102	Intermediate Similarity	NPD5710	Approved
0.7102	Intermediate Similarity	NPD5711	Approved
0.7092	Intermediate Similarity	NPD7801	Approved
0.7092	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7092	Intermediate Similarity	NPD7783	Phase 2
0.7091	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.709	Intermediate Similarity	NPD7700	Phase 2
0.709	Intermediate Similarity	NPD7699	Phase 2
0.7078	Intermediate Similarity	NPD9717	Approved
0.7078	Intermediate Similarity	NPD1608	Approved
0.7077	Intermediate Similarity	NPD8151	Discontinued
0.7076	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD2424	Discontinued
0.7066	Intermediate Similarity	NPD7390	Discontinued
0.7062	Intermediate Similarity	NPD5242	Approved
0.7062	Intermediate Similarity	NPD7584	Approved
0.7059	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7052	Intermediate Similarity	NPD5353	Approved
0.7051	Intermediate Similarity	NPD1470	Approved
0.7039	Intermediate Similarity	NPD9268	Approved
0.7031	Intermediate Similarity	NPD6823	Phase 2
0.7025	Intermediate Similarity	NPD6832	Phase 2
0.7024	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7015	Intermediate Similarity	NPD4665	Approved
0.7015	Intermediate Similarity	NPD4111	Phase 1
0.7013	Intermediate Similarity	NPD1201	Approved
0.7013	Intermediate Similarity	NPD422	Phase 1
0.7012	Intermediate Similarity	NPD7266	Discontinued
0.7012	Intermediate Similarity	NPD1471	Phase 3
0.6994	Remote Similarity	NPD8455	Phase 2
0.6968	Remote Similarity	NPD1481	Phase 2
0.6957	Remote Similarity	NPD4060	Phase 1
0.6946	Remote Similarity	NPD2354	Approved
0.6944	Remote Similarity	NPD2163	Approved
0.6937	Remote Similarity	NPD411	Approved
0.6937	Remote Similarity	NPD3268	Approved
0.6927	Remote Similarity	NPD7784	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD4661	Approved
0.6923	Remote Similarity	NPD4662	Approved
0.6914	Remote Similarity	NPD5124	Phase 1
0.6914	Remote Similarity	NPD5123	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