NPASS Compound

Structure

NPC250753 OpenBabel07101719252D 27 30 0 0 1 0 0 0 0 0999 V2000 -1.4576 2.1380 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8709 -0.6519 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2424 1.5801 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3709 0.2141 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2472 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2472 2.1603 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6236 1.8002 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6236 -0.3600 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2650 1.0088 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9195 -0.3930 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8709 1.0801 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0646 1.2185 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3709 0.2141 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5775 0.3600 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.5630 1.1691 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.2472 0.7201 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.8709 1.8002 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.7201 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0896 0.9960 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6236 1.0801 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.8709 1.0801 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 4.8709 1.0801 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3405 2.1440 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.7369 2.3002 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6634 1.6539 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3709 0.2141 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 5 8 1 0 0 0 0 5 16 1 0 0 0 0 6 7 1 0 0 0 0 6 17 1 0 0 0 0 7 20 1 0 0 0 0 9 15 1 0 0 0 0 10 14 1 0 0 0 0 10 22 1 0 0 0 0 11 21 1 0 0 0 0 11 27 1 0 0 0 0 12 14 1 0 0 0 0 12 19 1 0 0 0 0 13 23 2 0 0 0 0 13 27 1 0 0 0 0 14 9 1 1 0 0 0 15 18 1 0 0 0 0 15 24 1 6 0 0 0 16 20 1 1 0 0 0 16 21 1 0 0 0 0 17 21 1 0 0 0 0 17 25 2 0 0 0 0 18 20 1 1 0 0 0 18 22 1 0 0 0 0 19 22 1 0 0 0 0 19 26 2 0 0 0 0 20 3 1 1 0 0 0 21 4 1 6 0 0 0 22 8 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	374.21
Volume:	388.248
LogP:	1.554
LogD:	1.635
LogS:	-3.532
# Rotatable Bonds:	3
TPSA:	80.67
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.594
Synthetic Accessibility Score:	5.909
Fsp3:	0.773
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	2
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.836
MDCK Permeability:	2.9843069569324143e-05
Pgp-inhibitor:	0.166
Pgp-substrate:	0.119
Human Intestinal Absorption (HIA):	0.011
20% Bioavailability (F20%):	0.736
30% Bioavailability (F30%):	0.918

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.88
Plasma Protein Binding (PPB):	55.72562026977539%
Volume Distribution (VD):	0.396
Pgp-substrate:	51.99600601196289%

ADMET: Metabolism

CYP1A2-inhibitor:	0.022
CYP1A2-substrate:	0.428
CYP2C19-inhibitor:	0.084
CYP2C19-substrate:	0.742
CYP2C9-inhibitor:	0.058
CYP2C9-substrate:	0.07
CYP2D6-inhibitor:	0.01
CYP2D6-substrate:	0.112
CYP3A4-inhibitor:	0.722
CYP3A4-substrate:	0.255

ADMET: Excretion

Clearance (CL):	4.327
Half-life (T1/2):	0.754

ADMET: Toxicity

hERG Blockers:	0.065
Human Hepatotoxicity (H-HT):	0.059
Drug-inuced Liver Injury (DILI):	0.078
AMES Toxicity:	0.225
Rat Oral Acute Toxicity:	0.385
Maximum Recommended Daily Dose:	0.911
Skin Sensitization:	0.754
Carcinogencity:	0.773
Eye Corrosion:	0.066
Eye Irritation:	0.148
Respiratory Toxicity:	0.967

Download Data

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

Natural Product: NPC250753

Natural Product ID:	NPC250753
*Common Name:**	Excisusin E
IUPAC Name:	n.a.
Synonyms:	Excisusin E
Standard InCHIKey:	HUQHJDCFQIVPAM-DLIGVDNUSA-N
Standard InCHI:	InChI=1S/C22H30O5/c1-12-14-9-15(24)18-20(3)7-6-17(25)21(4,11-27-13(2)23)16(20)5-8-22(18,10-14)19(12)26/h14-16,18,24H,1,5-11H2,2-4H3/t14-,15+,16+,18+,20-,21+,22-/m1/s1
SMILES:	C=C1[C@@H]2C[C@@H]([C@H]3[C@]4(C)CCC(=O)[C@@](C)(COC(=O)C)[C@H]4CC[C@]3(C2)C1=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL376605
PubChem CID:	16215672
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
NPO26913	Isodon excisus	Species	Lamiaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[10896056]
NPO26913	Isodon excisus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11374970]
NPO26913	Isodon excisus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17338565]
NPO26913	Isodon excisus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21273070]
NPO26913	Isodon excisus	Species	Lamiaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[22066578]
NPO26913	Isodon excisus	Species	Lamiaceae	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	2

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	1020.0	nM	PMID[528924]
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	1360.0	nM	PMID[528924]

☑ 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 NPC250753 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	200
0.1-0.2	1572
0.2-0.3	5996
0.3-0.4	12305
0.4-0.5	8517
0.5-0.6	6030
0.6-0.7	5205
0.7-0.8	2463
0.8-0.85	248
0.85-0.9	97
0.9-0.95	61
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9551	High Similarity	NPC13949
0.9438	High Similarity	NPC470232
0.9432	High Similarity	NPC294263
0.9341	High Similarity	NPC471038
0.9333	High Similarity	NPC329910
0.9326	High Similarity	NPC470385
0.9326	High Similarity	NPC470386
0.9326	High Similarity	NPC475118
0.9318	High Similarity	NPC211403
0.9318	High Similarity	NPC198242
0.9222	High Similarity	NPC470229
0.9222	High Similarity	NPC98639
0.9222	High Similarity	NPC210214
0.9186	High Similarity	NPC471042
0.914	High Similarity	NPC52899
0.914	High Similarity	NPC46848
0.914	High Similarity	NPC289148
0.914	High Similarity	NPC163963
0.913	High Similarity	NPC26270
0.9121	High Similarity	NPC200054
0.9121	High Similarity	NPC104568
0.9121	High Similarity	NPC470387
0.9121	High Similarity	NPC29410
0.9111	High Similarity	NPC47853
0.9059	High Similarity	NPC118800
0.9043	High Similarity	NPC246736
0.9043	High Similarity	NPC148628
0.9043	High Similarity	NPC88203
0.9043	High Similarity	NPC76866
0.9043	High Similarity	NPC214946
0.9043	High Similarity	NPC275990
0.9043	High Similarity	NPC286519
0.9043	High Similarity	NPC304832
0.9032	High Similarity	NPC287676
0.9032	High Similarity	NPC267921
0.9032	High Similarity	NPC470388
0.9022	High Similarity	NPC10864
0.8989	High Similarity	NPC180849
0.8989	High Similarity	NPC80401
0.8977	High Similarity	NPC56413
0.8953	High Similarity	NPC146683
0.8947	High Similarity	NPC277074
0.8947	High Similarity	NPC87927
0.8947	High Similarity	NPC216114
0.8947	High Similarity	NPC209298
0.8947	High Similarity	NPC470310
0.8947	High Similarity	NPC122811
0.8947	High Similarity	NPC139347
0.8936	High Similarity	NPC148279
0.8925	High Similarity	NPC38296
0.8925	High Similarity	NPC474793
0.8925	High Similarity	NPC162459
0.8925	High Similarity	NPC16911
0.8925	High Similarity	NPC38471
0.8925	High Similarity	NPC28864
0.8925	High Similarity	NPC98837
0.8925	High Similarity	NPC20479
0.8925	High Similarity	NPC89099
0.8925	High Similarity	NPC78427
0.8889	High Similarity	NPC278106
0.8889	High Similarity	NPC476168
0.8889	High Similarity	NPC470230
0.8864	High Similarity	NPC259009
0.8864	High Similarity	NPC153604
0.8864	High Similarity	NPC174619
0.8854	High Similarity	NPC84928
0.8854	High Similarity	NPC98603
0.8851	High Similarity	NPC102292
0.8837	High Similarity	NPC291320
0.8837	High Similarity	NPC471037
0.8837	High Similarity	NPC471036
0.883	High Similarity	NPC293866
0.8791	High Similarity	NPC144739
0.8791	High Similarity	NPC181594
0.8791	High Similarity	NPC82138
0.8791	High Similarity	NPC59350
0.8791	High Similarity	NPC59170
0.8763	High Similarity	NPC138908
0.8763	High Similarity	NPC200957
0.875	High Similarity	NPC96217
0.8737	High Similarity	NPC471790
0.8737	High Similarity	NPC252614
0.8737	High Similarity	NPC236585
0.8723	High Similarity	NPC109059
0.8723	High Similarity	NPC288
0.8696	High Similarity	NPC289539
0.8696	High Similarity	NPC302008
0.8696	High Similarity	NPC261333
0.8696	High Similarity	NPC191094
0.8696	High Similarity	NPC292374
0.8696	High Similarity	NPC129004
0.8696	High Similarity	NPC91772
0.8696	High Similarity	NPC104371
0.8696	High Similarity	NPC215271
0.8696	High Similarity	NPC101233
0.8696	High Similarity	NPC29247
0.8696	High Similarity	NPC153775
0.8696	High Similarity	NPC111524
0.8681	High Similarity	NPC299185
0.8673	High Similarity	NPC201908
0.8673	High Similarity	NPC176949
0.8673	High Similarity	NPC186054
0.8673	High Similarity	NPC166993
0.8667	High Similarity	NPC471043
0.866	High Similarity	NPC474558
0.866	High Similarity	NPC202793
0.8652	High Similarity	NPC165895
0.8646	High Similarity	NPC475803
0.8646	High Similarity	NPC309388
0.8636	High Similarity	NPC190704
0.8636	High Similarity	NPC471034
0.8602	High Similarity	NPC29112
0.8602	High Similarity	NPC138245
0.8602	High Similarity	NPC231060
0.8602	High Similarity	NPC84018
0.8602	High Similarity	NPC266431
0.8587	High Similarity	NPC287118
0.8587	High Similarity	NPC244356
0.8587	High Similarity	NPC471902
0.8587	High Similarity	NPC224060
0.8587	High Similarity	NPC473690
0.8586	High Similarity	NPC112895
0.8586	High Similarity	NPC211224
0.8586	High Similarity	NPC231278
0.8586	High Similarity	NPC218123
0.8586	High Similarity	NPC273155
0.8586	High Similarity	NPC63841
0.8571	High Similarity	NPC470378
0.8571	High Similarity	NPC265127
0.8571	High Similarity	NPC164600
0.8571	High Similarity	NPC149761
0.8571	High Similarity	NPC103172
0.8571	High Similarity	NPC261994
0.8557	High Similarity	NPC159442
0.8556	High Similarity	NPC474719
0.8542	High Similarity	NPC71706
0.8542	High Similarity	NPC14634
0.8542	High Similarity	NPC81530
0.8511	High Similarity	NPC264979
0.8511	High Similarity	NPC140242
0.8511	High Similarity	NPC135548
0.8506	High Similarity	NPC110780
0.8495	Intermediate Similarity	NPC272635
0.8495	Intermediate Similarity	NPC169751
0.8495	Intermediate Similarity	NPC303863
0.8485	Intermediate Similarity	NPC471474
0.8485	Intermediate Similarity	NPC96333
0.8485	Intermediate Similarity	NPC88833
0.8478	Intermediate Similarity	NPC471901
0.8478	Intermediate Similarity	NPC475416
0.8469	Intermediate Similarity	NPC13149
0.8469	Intermediate Similarity	NPC101842
0.8469	Intermediate Similarity	NPC96268
0.8469	Intermediate Similarity	NPC301787
0.8462	Intermediate Similarity	NPC213832
0.8462	Intermediate Similarity	NPC57954
0.8454	Intermediate Similarity	NPC136289
0.8444	Intermediate Similarity	NPC134197
0.8444	Intermediate Similarity	NPC57469
0.8444	Intermediate Similarity	NPC33768
0.8438	Intermediate Similarity	NPC94906
0.8438	Intermediate Similarity	NPC117685
0.8427	Intermediate Similarity	NPC201655
0.8421	Intermediate Similarity	NPC96839
0.8416	Intermediate Similarity	NPC471093
0.8404	Intermediate Similarity	NPC263135
0.8404	Intermediate Similarity	NPC288906
0.8404	Intermediate Similarity	NPC205173
0.84	Intermediate Similarity	NPC232133
0.84	Intermediate Similarity	NPC473410
0.84	Intermediate Similarity	NPC471094
0.84	Intermediate Similarity	NPC469984
0.8384	Intermediate Similarity	NPC12823
0.8384	Intermediate Similarity	NPC222833
0.8384	Intermediate Similarity	NPC295366
0.8384	Intermediate Similarity	NPC56656
0.8384	Intermediate Similarity	NPC4115
0.8384	Intermediate Similarity	NPC37600
0.8372	Intermediate Similarity	NPC471475
0.837	Intermediate Similarity	NPC169933
0.8367	Intermediate Similarity	NPC469985
0.8353	Intermediate Similarity	NPC212661
0.8353	Intermediate Similarity	NPC471035
0.8353	Intermediate Similarity	NPC106078
0.8352	Intermediate Similarity	NPC4309
0.8352	Intermediate Similarity	NPC146937
0.8352	Intermediate Similarity	NPC471900
0.8351	Intermediate Similarity	NPC121218
0.8351	Intermediate Similarity	NPC75941
0.8351	Intermediate Similarity	NPC295276
0.8351	Intermediate Similarity	NPC39683
0.8351	Intermediate Similarity	NPC253886
0.8333	Intermediate Similarity	NPC472028
0.8333	Intermediate Similarity	NPC470281
0.8333	Intermediate Similarity	NPC12774
0.8333	Intermediate Similarity	NPC2783
0.8333	Intermediate Similarity	NPC29505
0.8333	Intermediate Similarity	NPC329953
0.8333	Intermediate Similarity	NPC185638
0.8317	Intermediate Similarity	NPC469983

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 NPC250753 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	180
0.1-0.2	1960
0.2-0.3	3969
0.3-0.4	2009
0.4-0.5	545
0.5-0.6	200
0.6-0.7	157
0.7-0.8	127
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.828	Intermediate Similarity	NPD8035	Phase 2
0.828	Intermediate Similarity	NPD8034	Phase 2
0.8222	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7941	Intermediate Similarity	NPD5697	Approved
0.7895	Intermediate Similarity	NPD6079	Approved
0.7872	Intermediate Similarity	NPD5328	Approved
0.7864	Intermediate Similarity	NPD6899	Approved
0.7864	Intermediate Similarity	NPD6881	Approved
0.7864	Intermediate Similarity	NPD6011	Approved
0.7843	Intermediate Similarity	NPD5739	Approved
0.7843	Intermediate Similarity	NPD7128	Approved
0.7843	Intermediate Similarity	NPD6675	Approved
0.7843	Intermediate Similarity	NPD6402	Approved
0.7812	Intermediate Similarity	NPD6399	Phase 3
0.781	Intermediate Similarity	NPD6650	Approved
0.781	Intermediate Similarity	NPD6649	Approved
0.7802	Intermediate Similarity	NPD4788	Approved
0.7788	Intermediate Similarity	NPD6013	Approved
0.7788	Intermediate Similarity	NPD6372	Approved
0.7788	Intermediate Similarity	NPD6014	Approved
0.7788	Intermediate Similarity	NPD6373	Approved
0.7788	Intermediate Similarity	NPD6012	Approved
0.7767	Intermediate Similarity	NPD5701	Approved
0.7755	Intermediate Similarity	NPD5221	Approved
0.7755	Intermediate Similarity	NPD5222	Approved
0.7755	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7755	Intermediate Similarity	NPD4697	Phase 3
0.7742	Intermediate Similarity	NPD3618	Phase 1
0.7732	Intermediate Similarity	NPD7748	Approved
0.7714	Intermediate Similarity	NPD6883	Approved
0.7714	Intermediate Similarity	NPD7102	Approved
0.7714	Intermediate Similarity	NPD7290	Approved
0.7708	Intermediate Similarity	NPD7515	Phase 2
0.7692	Intermediate Similarity	NPD7320	Approved
0.7677	Intermediate Similarity	NPD7902	Approved
0.7677	Intermediate Similarity	NPD5173	Approved
0.7642	Intermediate Similarity	NPD8130	Phase 1
0.7642	Intermediate Similarity	NPD6617	Approved
0.7642	Intermediate Similarity	NPD6869	Approved
0.7642	Intermediate Similarity	NPD6847	Approved
0.7614	Intermediate Similarity	NPD6117	Approved
0.757	Intermediate Similarity	NPD8297	Approved
0.757	Intermediate Similarity	NPD6882	Approved
0.7553	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7528	Intermediate Similarity	NPD6116	Phase 1
0.7525	Intermediate Similarity	NPD4696	Approved
0.7525	Intermediate Similarity	NPD5286	Approved
0.7525	Intermediate Similarity	NPD5285	Approved
0.75	Intermediate Similarity	NPD6083	Phase 2
0.75	Intermediate Similarity	NPD6084	Phase 2
0.75	Intermediate Similarity	NPD4755	Approved
0.7477	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7455	Intermediate Similarity	NPD7115	Discovery
0.7451	Intermediate Similarity	NPD5223	Approved
0.7444	Intermediate Similarity	NPD6115	Approved
0.7444	Intermediate Similarity	NPD6697	Approved
0.7444	Intermediate Similarity	NPD6118	Approved
0.7444	Intermediate Similarity	NPD6114	Approved
0.7426	Intermediate Similarity	NPD7638	Approved
0.7426	Intermediate Similarity	NPD5696	Approved
0.7411	Intermediate Similarity	NPD6319	Approved
0.7396	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7396	Intermediate Similarity	NPD5737	Approved
0.7396	Intermediate Similarity	NPD6672	Approved
0.7386	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7379	Intermediate Similarity	NPD5225	Approved
0.7379	Intermediate Similarity	NPD5226	Approved
0.7379	Intermediate Similarity	NPD5224	Approved
0.7379	Intermediate Similarity	NPD4633	Approved
0.7379	Intermediate Similarity	NPD5211	Phase 2
0.7374	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7374	Intermediate Similarity	NPD7900	Approved
0.7368	Intermediate Similarity	NPD6684	Approved
0.7368	Intermediate Similarity	NPD7146	Approved
0.7368	Intermediate Similarity	NPD5330	Approved
0.7368	Intermediate Similarity	NPD7521	Approved
0.7368	Intermediate Similarity	NPD7334	Approved
0.7368	Intermediate Similarity	NPD6409	Approved
0.7364	Intermediate Similarity	NPD6274	Approved
0.7364	Intermediate Similarity	NPD6868	Approved
0.7353	Intermediate Similarity	NPD4700	Approved
0.7353	Intermediate Similarity	NPD7640	Approved
0.7353	Intermediate Similarity	NPD7639	Approved
0.7347	Intermediate Similarity	NPD6411	Approved
0.734	Intermediate Similarity	NPD3665	Phase 1
0.734	Intermediate Similarity	NPD3666	Approved
0.734	Intermediate Similarity	NPD4786	Approved
0.734	Intermediate Similarity	NPD3133	Approved
0.7339	Intermediate Similarity	NPD4632	Approved
0.7333	Intermediate Similarity	NPD6008	Approved
0.7312	Intermediate Similarity	NPD3667	Approved
0.7308	Intermediate Similarity	NPD5174	Approved
0.7308	Intermediate Similarity	NPD5175	Approved
0.7303	Intermediate Similarity	NPD3703	Phase 2
0.73	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.73	Intermediate Similarity	NPD5695	Phase 3
0.7297	Intermediate Similarity	NPD6317	Approved
0.7292	Intermediate Similarity	NPD3573	Approved
0.7273	Intermediate Similarity	NPD4202	Approved
0.7255	Intermediate Similarity	NPD4225	Approved
0.7238	Intermediate Similarity	NPD5141	Approved
0.7232	Intermediate Similarity	NPD6314	Approved
0.7232	Intermediate Similarity	NPD6335	Approved
0.7232	Intermediate Similarity	NPD6313	Approved
0.7222	Intermediate Similarity	NPD4634	Approved
0.7216	Intermediate Similarity	NPD6903	Approved
0.7196	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD6291	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD4224	Phase 2
0.7168	Intermediate Similarity	NPD7100	Approved
0.7168	Intermediate Similarity	NPD7101	Approved
0.7159	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.7159	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.7155	Intermediate Similarity	NPD7492	Approved
0.7143	Intermediate Similarity	NPD6101	Approved
0.7143	Intermediate Similarity	NPD6009	Approved
0.7143	Intermediate Similarity	NPD4753	Phase 2
0.7143	Intermediate Similarity	NPD4754	Approved
0.7143	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7129	Intermediate Similarity	NPD5210	Approved
0.7129	Intermediate Similarity	NPD4629	Approved
0.7126	Intermediate Similarity	NPD3700	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD3699	Clinical (unspecified phase)
0.7119	Intermediate Similarity	NPD7736	Approved
0.7111	Intermediate Similarity	NPD3702	Approved
0.7105	Intermediate Similarity	NPD6054	Approved
0.7094	Intermediate Similarity	NPD6616	Approved
0.7043	Intermediate Similarity	NPD5983	Phase 2
0.7043	Intermediate Similarity	NPD6015	Approved
0.7043	Intermediate Similarity	NPD6016	Approved
0.7037	Intermediate Similarity	NPD4729	Approved
0.7037	Intermediate Similarity	NPD5128	Approved
0.7037	Intermediate Similarity	NPD5168	Approved
0.7037	Intermediate Similarity	NPD4730	Approved
0.7034	Intermediate Similarity	NPD7078	Approved
0.703	Intermediate Similarity	NPD6001	Approved
0.701	Intermediate Similarity	NPD5279	Phase 3
0.7009	Intermediate Similarity	NPD4768	Approved
0.7009	Intermediate Similarity	NPD4767	Approved
0.7	Intermediate Similarity	NPD5281	Approved
0.7	Intermediate Similarity	NPD5284	Approved
0.6983	Remote Similarity	NPD5988	Approved
0.6983	Remote Similarity	NPD6370	Approved
0.697	Remote Similarity	NPD6080	Approved
0.697	Remote Similarity	NPD6904	Approved
0.697	Remote Similarity	NPD6673	Approved
0.6966	Remote Similarity	NPD6081	Approved
0.6966	Remote Similarity	NPD5777	Approved
0.6961	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD6059	Approved
0.6947	Remote Similarity	NPD4223	Phase 3
0.6947	Remote Similarity	NPD4221	Approved
0.6947	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6932	Remote Similarity	NPD3698	Phase 2
0.6923	Remote Similarity	NPD7604	Phase 2
0.6923	Remote Similarity	NPD8328	Phase 3
0.6915	Remote Similarity	NPD7525	Registered
0.6909	Remote Similarity	NPD5249	Phase 3
0.6909	Remote Similarity	NPD5250	Approved
0.6909	Remote Similarity	NPD5169	Approved
0.6909	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD5251	Approved
0.6909	Remote Similarity	NPD5248	Approved
0.6909	Remote Similarity	NPD5247	Approved
0.6909	Remote Similarity	NPD5135	Approved
0.6907	Remote Similarity	NPD1694	Approved
0.6897	Remote Similarity	NPD6908	Approved
0.6897	Remote Similarity	NPD6909	Approved
0.6891	Remote Similarity	NPD8293	Discontinued
0.6887	Remote Similarity	NPD7632	Discontinued
0.6869	Remote Similarity	NPD5208	Approved
0.686	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.6854	Remote Similarity	NPD4245	Approved
0.6854	Remote Similarity	NPD4244	Approved
0.6854	Remote Similarity	NPD4789	Approved
0.6847	Remote Similarity	NPD5127	Approved
0.6847	Remote Similarity	NPD5215	Approved
0.6847	Remote Similarity	NPD5216	Approved
0.6847	Remote Similarity	NPD5217	Approved
0.6837	Remote Similarity	NPD6098	Approved
0.6832	Remote Similarity	NPD5693	Phase 1
0.6807	Remote Similarity	NPD6336	Discontinued
0.6804	Remote Similarity	NPD3668	Phase 3
0.6804	Remote Similarity	NPD4197	Approved
0.6777	Remote Similarity	NPD7319	Approved
0.6765	Remote Similarity	NPD5779	Approved
0.6765	Remote Similarity	NPD5778	Approved
0.6737	Remote Similarity	NPD4695	Discontinued
0.6735	Remote Similarity	NPD5329	Approved
0.6733	Remote Similarity	NPD5785	Approved
0.6733	Remote Similarity	NPD5692	Phase 3
0.6733	Remote Similarity	NPD5207	Approved
0.6726	Remote Similarity	NPD8133	Approved
0.6702	Remote Similarity	NPD3617	Approved
0.6696	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4690	Approved
0.6667	Remote Similarity	NPD5690	Phase 2
0.6667	Remote Similarity	NPD5786	Approved
0.6667	Remote Similarity	NPD5205	Approved
0.6667	Remote Similarity	NPD4138	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