NPASS Compound

Structure

CID26679 OpenBabel06191715352D 21 23 0 0 0 0 0 0 0 0999 V2000 -0.8915 -2.7391 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6264 -1.1708 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4626 3.4774 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5181 1.4536 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6791 1.9383 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5179 0.4840 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6794 -0.9686 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7158 -1.0701 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5180 1.4546 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8394 1.4539 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6792 0.0003 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6787 -0.0003 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6788 1.9389 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8393 1.4542 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8392 0.4844 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8395 0.4847 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5182 0.4850 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.3219 -1.9553 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6786 -0.9693 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6787 2.9079 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 19 1 0 0 0 0 2 20 1 0 0 0 0 3 21 1 0 0 0 0 4 5 2 0 0 0 0 4 6 1 0 0 0 0 5 10 1 0 0 0 0 6 12 2 0 0 0 0 7 8 1 0 0 0 0 7 11 1 0 0 0 0 8 19 1 0 0 0 0 9 13 1 0 0 0 0 9 17 2 0 0 0 0 10 14 1 0 0 0 0 10 15 2 0 0 0 0 11 16 2 0 0 0 0 11 17 1 0 0 0 0 12 15 1 0 0 0 0 12 20 1 0 0 0 0 13 14 2 0 0 0 0 13 21 1 0 0 0 0 14 16 1 0 0 0 0 15 18 1 0 0 0 0 16 18 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	286.13
Volume:	292.168
LogP:	2.169
LogD:	2.697
LogS:	-2.309
# Rotatable Bonds:	5
TPSA:	56.37
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.783
Synthetic Accessibility Score:	2.512
Fsp3:	0.312
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.839
MDCK Permeability:	1.566027640365064e-05
Pgp-inhibitor:	0.036
Pgp-substrate:	0.946
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.009
30% Bioavailability (F30%):	0.041

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.712
Plasma Protein Binding (PPB):	83.04280853271484%
Volume Distribution (VD):	1.029
Pgp-substrate:	14.025461196899414%

ADMET: Metabolism

CYP1A2-inhibitor:	0.986
CYP1A2-substrate:	0.982
CYP2C19-inhibitor:	0.815
CYP2C19-substrate:	0.808
CYP2C9-inhibitor:	0.553
CYP2C9-substrate:	0.818
CYP2D6-inhibitor:	0.695
CYP2D6-substrate:	0.879
CYP3A4-inhibitor:	0.739
CYP3A4-substrate:	0.883

ADMET: Excretion

Clearance (CL):	6.47
Half-life (T1/2):	0.644

ADMET: Toxicity

hERG Blockers:	0.025
Human Hepatotoxicity (H-HT):	0.549
Drug-inuced Liver Injury (DILI):	0.95
AMES Toxicity:	0.558
Rat Oral Acute Toxicity:	0.963
Maximum Recommended Daily Dose:	0.195
Skin Sensitization:	0.407
Carcinogencity:	0.728
Eye Corrosion:	0.017
Eye Irritation:	0.382
Respiratory Toxicity:	0.977

Download Data

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

Natural Product: NPC26679

Natural Product ID:	NPC26679
*Common Name:**	Picrasidine B
IUPAC Name:	4,8-dimethoxy-1-(2-methoxyethyl)-9H-pyrido[3,4-b]indole
Synonyms:
Standard InCHIKey:	VXIBHGSYBDCYKB-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C16H18N2O3/c1-19-8-7-11-16-14(13(21-3)9-17-11)10-5-4-6-12(20-2)15(10)18-16/h4-6,9,18H,7-8H2,1-3H3
SMILES:	COCCc1ncc(c2c1[nH]c1c2cccc1OC)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3400672
PubChem CID:	5316865
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0001140] Harmala alkaloids

*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
NPO25272	Celastrus angulatus	Species	Celastraceae	Eukaryota	n.a.	seed	n.a.	DOI[10.1016/S0031-9422(99)00216-2]
NPO8372	Picrasma quassioides	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19586051]
NPO8372	Picrasma quassioides	Species	Simaroubaceae	Eukaryota	stems	n.a.	n.a.	PMID[20095629]
NPO8372	Picrasma quassioides	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25506718]
NPO25272	Celastrus angulatus	Species	Celastraceae	Eukaryota	seeds and root bark	Henan, China	n.a.	PMID[26295746]
NPO8372	Picrasma quassioides	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27494664]
NPO8372	Picrasma quassioides	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[30917277]
NPO15413	Glycyrrhiza pallidiflora	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25272	Celastrus angulatus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8372	Picrasma quassioides	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8372	Picrasma quassioides	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25272	Celastrus angulatus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15413	Glycyrrhiza pallidiflora	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8372	Picrasma quassioides	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO25272	Celastrus angulatus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO15413	Glycyrrhiza pallidiflora	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO8372	Picrasma quassioides	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO25272	Celastrus angulatus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8372	Picrasma quassioides	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15413	Glycyrrhiza pallidiflora	Species	Fabaceae	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
Others	1

Activity Type	# Activity
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT178	Individual Protein	Protein-tyrosine phosphatase 1B	Homo sapiens	Inhibition	=	28.6	%	PMID[543852]

☑ 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 NPC26679 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	615
0.1-0.2	4210
0.2-0.3	13034
0.3-0.4	10598
0.4-0.5	9321
0.5-0.6	2773
0.6-0.7	1725
0.7-0.8	367
0.8-0.85	29
0.85-0.9	14
0.9-0.95	7
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.984	High Similarity	NPC185782
0.9536	High Similarity	NPC8022
0.9536	High Similarity	NPC470799
0.9368	High Similarity	NPC476138
0.9368	High Similarity	NPC245816
0.9171	High Similarity	NPC469554
0.911	High Similarity	NPC19872
0.9078	High Similarity	NPC101543
0.8945	High Similarity	NPC476287
0.8814	High Similarity	NPC176538
0.8756	High Similarity	NPC267928
0.8692	High Similarity	NPC148889
0.8673	High Similarity	NPC232727
0.8634	High Similarity	NPC292958
0.8571	High Similarity	NPC476167
0.852	High Similarity	NPC192315
0.85	High Similarity	NPC26543
0.8483	Intermediate Similarity	NPC314954
0.8462	Intermediate Similarity	NPC310118
0.8424	Intermediate Similarity	NPC123976
0.8424	Intermediate Similarity	NPC167860
0.8377	Intermediate Similarity	NPC284678
0.8349	Intermediate Similarity	NPC110151
0.8333	Intermediate Similarity	NPC5145
0.8325	Intermediate Similarity	NPC287208
0.8311	Intermediate Similarity	NPC53534
0.8308	Intermediate Similarity	NPC475774
0.8278	Intermediate Similarity	NPC213530
0.8278	Intermediate Similarity	NPC193267
0.8272	Intermediate Similarity	NPC474798
0.8267	Intermediate Similarity	NPC285558
0.8256	Intermediate Similarity	NPC76748
0.8223	Intermediate Similarity	NPC307963
0.8214	Intermediate Similarity	NPC92111
0.8205	Intermediate Similarity	NPC296527
0.8177	Intermediate Similarity	NPC470500
0.8174	Intermediate Similarity	NPC152620
0.8164	Intermediate Similarity	NPC94157
0.8141	Intermediate Similarity	NPC251090
0.8131	Intermediate Similarity	NPC84853
0.8116	Intermediate Similarity	NPC208284
0.8113	Intermediate Similarity	NPC60621
0.8112	Intermediate Similarity	NPC242928
0.8069	Intermediate Similarity	NPC315957
0.8065	Intermediate Similarity	NPC260434
0.8058	Intermediate Similarity	NPC82548
0.8039	Intermediate Similarity	NPC223427
0.8	Intermediate Similarity	NPC475070
0.7981	Intermediate Similarity	NPC132642
0.798	Intermediate Similarity	NPC121772
0.796	Intermediate Similarity	NPC13880
0.7955	Intermediate Similarity	NPC182222
0.7953	Intermediate Similarity	NPC122436
0.795	Intermediate Similarity	NPC475190
0.7933	Intermediate Similarity	NPC174672
0.7933	Intermediate Similarity	NPC174758
0.7931	Intermediate Similarity	NPC187558
0.7931	Intermediate Similarity	NPC128823
0.7913	Intermediate Similarity	NPC470930
0.7895	Intermediate Similarity	NPC11464
0.7877	Intermediate Similarity	NPC170114
0.7877	Intermediate Similarity	NPC288349
0.7857	Intermediate Similarity	NPC48938
0.7857	Intermediate Similarity	NPC176127
0.7844	Intermediate Similarity	NPC473185
0.7843	Intermediate Similarity	NPC18487
0.7838	Intermediate Similarity	NPC295228
0.783	Intermediate Similarity	NPC470549
0.7826	Intermediate Similarity	NPC329708
0.7826	Intermediate Similarity	NPC274291
0.7826	Intermediate Similarity	NPC47059
0.7826	Intermediate Similarity	NPC264166
0.7826	Intermediate Similarity	NPC118832
0.7826	Intermediate Similarity	NPC165349
0.781	Intermediate Similarity	NPC199667
0.7804	Intermediate Similarity	NPC469594
0.7783	Intermediate Similarity	NPC162530
0.7783	Intermediate Similarity	NPC266931
0.7783	Intermediate Similarity	NPC469592
0.7783	Intermediate Similarity	NPC471080
0.7772	Intermediate Similarity	NPC226202
0.7772	Intermediate Similarity	NPC198673
0.7763	Intermediate Similarity	NPC471891
0.7762	Intermediate Similarity	NPC473181
0.7748	Intermediate Similarity	NPC180504
0.7738	Intermediate Similarity	NPC476451
0.7738	Intermediate Similarity	NPC475253
0.7737	Intermediate Similarity	NPC118511
0.7736	Intermediate Similarity	NPC473180
0.7736	Intermediate Similarity	NPC316981
0.7727	Intermediate Similarity	NPC84478
0.7725	Intermediate Similarity	NPC258048
0.7723	Intermediate Similarity	NPC324149
0.7718	Intermediate Similarity	NPC329793
0.7716	Intermediate Similarity	NPC161887
0.7714	Intermediate Similarity	NPC476465
0.771	Intermediate Similarity	NPC274982
0.7707	Intermediate Similarity	NPC168911
0.7703	Intermediate Similarity	NPC472111
0.7689	Intermediate Similarity	NPC101350
0.7689	Intermediate Similarity	NPC30540
0.7688	Intermediate Similarity	NPC20249
0.7685	Intermediate Similarity	NPC473179
0.7668	Intermediate Similarity	NPC141053
0.7644	Intermediate Similarity	NPC235685
0.7635	Intermediate Similarity	NPC99666
0.7633	Intermediate Similarity	NPC329747
0.7629	Intermediate Similarity	NPC252590
0.7626	Intermediate Similarity	NPC219963
0.7623	Intermediate Similarity	NPC473186
0.7621	Intermediate Similarity	NPC239954
0.7602	Intermediate Similarity	NPC224764
0.76	Intermediate Similarity	NPC42591
0.76	Intermediate Similarity	NPC314002
0.7598	Intermediate Similarity	NPC472434
0.7594	Intermediate Similarity	NPC209769
0.7593	Intermediate Similarity	NPC304926
0.7593	Intermediate Similarity	NPC476041
0.758	Intermediate Similarity	NPC470501
0.7577	Intermediate Similarity	NPC476518
0.757	Intermediate Similarity	NPC118940
0.7566	Intermediate Similarity	NPC473183
0.7562	Intermediate Similarity	NPC171171
0.7561	Intermediate Similarity	NPC131017
0.7559	Intermediate Similarity	NPC123839
0.7556	Intermediate Similarity	NPC39370
0.755	Intermediate Similarity	NPC204717
0.7549	Intermediate Similarity	NPC195268
0.7549	Intermediate Similarity	NPC133140
0.7548	Intermediate Similarity	NPC234197
0.7547	Intermediate Similarity	NPC266249
0.7547	Intermediate Similarity	NPC475910
0.7544	Intermediate Similarity	NPC81175
0.7538	Intermediate Similarity	NPC266551
0.7538	Intermediate Similarity	NPC121658
0.7538	Intermediate Similarity	NPC14651
0.7534	Intermediate Similarity	NPC470502
0.7525	Intermediate Similarity	NPC46580
0.7525	Intermediate Similarity	NPC42979
0.7523	Intermediate Similarity	NPC187501
0.7512	Intermediate Similarity	NPC469589
0.7512	Intermediate Similarity	NPC31930
0.75	Intermediate Similarity	NPC287437
0.75	Intermediate Similarity	NPC220765
0.7488	Intermediate Similarity	NPC476581
0.7488	Intermediate Similarity	NPC16452
0.7488	Intermediate Similarity	NPC36229
0.7478	Intermediate Similarity	NPC473184
0.7477	Intermediate Similarity	NPC471304
0.7477	Intermediate Similarity	NPC219664
0.7476	Intermediate Similarity	NPC66815
0.7466	Intermediate Similarity	NPC470503
0.7465	Intermediate Similarity	NPC148183
0.7465	Intermediate Similarity	NPC152768
0.7465	Intermediate Similarity	NPC477111
0.7464	Intermediate Similarity	NPC249040
0.745	Intermediate Similarity	NPC118776
0.745	Intermediate Similarity	NPC314394
0.7444	Intermediate Similarity	NPC6215
0.7443	Intermediate Similarity	NPC17565
0.7443	Intermediate Similarity	NPC208084
0.7443	Intermediate Similarity	NPC288987
0.7441	Intermediate Similarity	NPC162484
0.7435	Intermediate Similarity	NPC473312
0.7432	Intermediate Similarity	NPC21638
0.7427	Intermediate Similarity	NPC106937
0.7425	Intermediate Similarity	NPC91868
0.7425	Intermediate Similarity	NPC63971
0.7424	Intermediate Similarity	NPC477861
0.7416	Intermediate Similarity	NPC476582
0.7416	Intermediate Similarity	NPC4071
0.7416	Intermediate Similarity	NPC476578
0.7415	Intermediate Similarity	NPC472435
0.7411	Intermediate Similarity	NPC111624
0.7409	Intermediate Similarity	NPC225279
0.7409	Intermediate Similarity	NPC177404
0.7407	Intermediate Similarity	NPC296482
0.7407	Intermediate Similarity	NPC203168
0.7407	Intermediate Similarity	NPC202768
0.7407	Intermediate Similarity	NPC53069
0.7404	Intermediate Similarity	NPC70956
0.7404	Intermediate Similarity	NPC243834
0.7404	Intermediate Similarity	NPC77555
0.7398	Intermediate Similarity	NPC314940
0.7398	Intermediate Similarity	NPC473764
0.7393	Intermediate Similarity	NPC211813
0.7393	Intermediate Similarity	NPC473761
0.7391	Intermediate Similarity	NPC99891
0.7389	Intermediate Similarity	NPC49547
0.7389	Intermediate Similarity	NPC196718
0.7387	Intermediate Similarity	NPC65277
0.7385	Intermediate Similarity	NPC477110
0.7381	Intermediate Similarity	NPC477019
0.738	Intermediate Similarity	NPC11408
0.7373	Intermediate Similarity	NPC221100
0.7373	Intermediate Similarity	NPC39500
0.7373	Intermediate Similarity	NPC234078
0.7373	Intermediate Similarity	NPC478074
0.7371	Intermediate Similarity	NPC323345
0.7371	Intermediate Similarity	NPC470164

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 NPC26679 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	314
0.1-0.2	675
0.2-0.3	829
0.3-0.4	1607
0.4-0.5	2585
0.5-0.6	2127
0.6-0.7	860
0.7-0.8	147
0.8-0.85	6
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8223	Intermediate Similarity	NPD1304	Clinical (unspecified phase)
0.8223	Intermediate Similarity	NPD1038	Approved
0.8177	Intermediate Similarity	NPD4795	Phase 2
0.8165	Intermediate Similarity	NPD3006	Discontinued
0.8136	Intermediate Similarity	NPD2921	Clinical (unspecified phase)
0.8089	Intermediate Similarity	NPD5482	Discontinued
0.8072	Intermediate Similarity	NPD5483	Clinical (unspecified phase)
0.8069	Intermediate Similarity	NPD1740	Approved
0.8069	Intermediate Similarity	NPD1739	Approved
0.802	Intermediate Similarity	NPD3825	Phase 3
0.7991	Intermediate Similarity	NPD1856	Discontinued
0.7971	Intermediate Similarity	NPD5658	Approved
0.789	Intermediate Similarity	NPD5559	Phase 2
0.7877	Intermediate Similarity	NPD5612	Discontinued
0.784	Intermediate Similarity	NPD7823	Clinical (unspecified phase)
0.7837	Intermediate Similarity	NPD1392	Approved
0.7828	Intermediate Similarity	NPD7558	Phase 2
0.7828	Intermediate Similarity	NPD5256	Discontinued
0.7826	Intermediate Similarity	NPD31	Approved
0.7826	Intermediate Similarity	NPD4033	Approved
0.7826	Intermediate Similarity	NPD4037	Approved
0.7826	Intermediate Similarity	NPD4039	Approved
0.7826	Intermediate Similarity	NPD32	Approved
0.7826	Intermediate Similarity	NPD4035	Approved
0.7826	Intermediate Similarity	NPD4122	Approved
0.7826	Intermediate Similarity	NPD4038	Approved
0.7826	Intermediate Similarity	NPD4034	Approved
0.7826	Intermediate Similarity	NPD4036	Approved
0.7822	Intermediate Similarity	NPD3324	Clinical (unspecified phase)
0.7793	Intermediate Similarity	NPD6643	Discontinued
0.7773	Intermediate Similarity	NPD5066	Phase 2
0.7773	Intermediate Similarity	NPD4502	Phase 2
0.7773	Intermediate Similarity	NPD5067	Phase 2
0.7756	Intermediate Similarity	NPD4118	Clinical (unspecified phase)
0.7721	Intermediate Similarity	NPD4429	Discontinued
0.7714	Intermediate Similarity	NPD2187	Approved
0.7714	Intermediate Similarity	NPD2189	Approved
0.7709	Intermediate Similarity	NPD4440	Clinical (unspecified phase)
0.7703	Intermediate Similarity	NPD3003	Approved
0.7696	Intermediate Similarity	NPD3477	Phase 2
0.7696	Intermediate Similarity	NPD3478	Clinical (unspecified phase)
0.7689	Intermediate Similarity	NPD3939	Suspended
0.7685	Intermediate Similarity	NPD3514	Clinical (unspecified phase)
0.7682	Intermediate Similarity	NPD6961	Discontinued
0.7679	Intermediate Similarity	NPD4454	Phase 2
0.7679	Intermediate Similarity	NPD5450	Discontinued
0.767	Intermediate Similarity	NPD4548	Discontinued
0.7664	Intermediate Similarity	NPD6140	Clinical (unspecified phase)
0.7636	Intermediate Similarity	NPD7603	Discontinued
0.7632	Intermediate Similarity	NPD9705	Discontinued
0.7632	Intermediate Similarity	NPD112	Approved
0.7605	Intermediate Similarity	NPD3343	Phase 3
0.7604	Intermediate Similarity	NPD3402	Phase 1
0.7583	Intermediate Similarity	NPD7222	Phase 2
0.7569	Intermediate Similarity	NPD6242	Discontinued
0.7566	Intermediate Similarity	NPD4958	Clinical (unspecified phase)
0.7555	Intermediate Similarity	NPD7067	Approved
0.7555	Intermediate Similarity	NPD7068	Approved
0.7549	Intermediate Similarity	NPD3924	Approved
0.7549	Intermediate Similarity	NPD3922	Approved
0.7549	Intermediate Similarity	NPD4372	Phase 1
0.7549	Intermediate Similarity	NPD3921	Approved
0.7549	Intermediate Similarity	NPD6569	Phase 2
0.7549	Intermediate Similarity	NPD3923	Approved
0.7525	Intermediate Similarity	NPD1034	Phase 3
0.7525	Intermediate Similarity	NPD1033	Clinical (unspecified phase)
0.7523	Intermediate Similarity	NPD4131	Phase 3
0.7512	Intermediate Similarity	NPD5575	Clinical (unspecified phase)
0.7511	Intermediate Similarity	NPD6494	Phase 2
0.75	Intermediate Similarity	NPD2177	Approved
0.75	Intermediate Similarity	NPD2175	Phase 3
0.75	Intermediate Similarity	NPD5902	Approved
0.75	Intermediate Similarity	NPD2176	Approved
0.75	Intermediate Similarity	NPD5903	Approved
0.75	Intermediate Similarity	NPD5999	Phase 2
0.75	Intermediate Similarity	NPD1768	Approved
0.7489	Intermediate Similarity	NPD5930	Phase 3
0.7455	Intermediate Similarity	NPD5022	Discontinued
0.7455	Intermediate Similarity	NPD4881	Clinical (unspecified phase)
0.7454	Intermediate Similarity	NPD1322	Clinical (unspecified phase)
0.745	Intermediate Similarity	NPD4204	Approved
0.745	Intermediate Similarity	NPD4203	Approved
0.7444	Intermediate Similarity	NPD6553	Clinical (unspecified phase)
0.7443	Intermediate Similarity	NPD7194	Discontinued
0.7427	Intermediate Similarity	NPD802	Phase 2
0.7418	Intermediate Similarity	NPD7452	Approved
0.7418	Intermediate Similarity	NPD7453	Approved
0.7418	Intermediate Similarity	NPD5018	Phase 3
0.7407	Intermediate Similarity	NPD3330	Phase 1
0.7407	Intermediate Similarity	NPD3815	Phase 1
0.7407	Intermediate Similarity	NPD3816	Phase 1
0.7398	Intermediate Similarity	NPD565	Phase 2
0.7383	Intermediate Similarity	NPD5863	Clinical (unspecified phase)
0.7378	Intermediate Similarity	NPD8512	Phase 3
0.7376	Intermediate Similarity	NPD5083	Clinical (unspecified phase)
0.7371	Intermediate Similarity	NPD5530	Phase 1
0.7361	Intermediate Similarity	NPD949	Phase 1
0.7357	Intermediate Similarity	NPD6741	Clinical (unspecified phase)
0.7352	Intermediate Similarity	NPD5164	Discontinued
0.7349	Intermediate Similarity	NPD4437	Phase 3
0.7349	Intermediate Similarity	NPD2125	Clinical (unspecified phase)
0.7342	Intermediate Similarity	NPD8442	Discontinued
0.7342	Intermediate Similarity	NPD6160	Clinical (unspecified phase)
0.7327	Intermediate Similarity	NPD6202	Discontinued
0.7321	Intermediate Similarity	NPD7948	Phase 1
0.7321	Intermediate Similarity	NPD1273	Discontinued
0.7309	Intermediate Similarity	NPD6306	Phase 2
0.7308	Intermediate Similarity	NPD6861	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD4418	Discontinued
0.7304	Intermediate Similarity	NPD4920	Clinical (unspecified phase)
0.7304	Intermediate Similarity	NPD4921	Phase 3
0.7304	Intermediate Similarity	NPD4919	Phase 3
0.7281	Intermediate Similarity	NPD5936	Approved
0.7281	Intermediate Similarity	NPD5939	Approved
0.7281	Intermediate Similarity	NPD6223	Clinical (unspecified phase)
0.7277	Intermediate Similarity	NPD4558	Phase 2
0.7277	Intermediate Similarity	NPD3386	Phase 2
0.7259	Intermediate Similarity	NPD6872	Clinical (unspecified phase)
0.7256	Intermediate Similarity	NPD6290	Phase 2
0.7254	Intermediate Similarity	NPD2581	Approved
0.7254	Intermediate Similarity	NPD2582	Approved
0.7252	Intermediate Similarity	NPD6856	Discontinued
0.7246	Intermediate Similarity	NPD5912	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD5913	Phase 3
0.7243	Intermediate Similarity	NPD3397	Phase 2
0.724	Intermediate Similarity	NPD6985	Discontinued
0.724	Intermediate Similarity	NPD5632	Approved
0.7225	Intermediate Similarity	NPD6969	Phase 2
0.7225	Intermediate Similarity	NPD6968	Phase 2
0.7213	Intermediate Similarity	NPD4442	Phase 2
0.721	Intermediate Similarity	NPD6473	Phase 1
0.7209	Intermediate Similarity	NPD3842	Clinical (unspecified phase)
0.7209	Intermediate Similarity	NPD5601	Phase 2
0.7209	Intermediate Similarity	NPD8403	Phase 1
0.7207	Intermediate Similarity	NPD3763	Approved
0.7205	Intermediate Similarity	NPD2471	Approved
0.7205	Intermediate Similarity	NPD2472	Approved
0.7203	Intermediate Similarity	NPD5644	Phase 1
0.7202	Intermediate Similarity	NPD3570	Phase 2
0.7202	Intermediate Similarity	NPD6220	Phase 3
0.72	Intermediate Similarity	NPD9690	Approved
0.72	Intermediate Similarity	NPD1258	Discontinued
0.7198	Intermediate Similarity	NPD4858	Phase 2
0.7196	Intermediate Similarity	NPD2121	Clinical (unspecified phase)
0.7192	Intermediate Similarity	NPD7414	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD6550	Discontinued
0.7186	Intermediate Similarity	NPD4343	Phase 1
0.7186	Intermediate Similarity	NPD4344	Clinical (unspecified phase)
0.7186	Intermediate Similarity	NPD1078	Clinical (unspecified phase)
0.7184	Intermediate Similarity	NPD6257	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD1418	Phase 2
0.7174	Intermediate Similarity	NPD6963	Approved
0.7174	Intermediate Similarity	NPD6964	Approved
0.7173	Intermediate Similarity	NPD6243	Phase 3
0.7173	Intermediate Similarity	NPD6244	Phase 3
0.7171	Intermediate Similarity	NPD4889	Approved
0.7156	Intermediate Similarity	NPD1229	Phase 2
0.7149	Intermediate Similarity	NPD6147	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD5528	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD5529	Phase 1
0.7136	Intermediate Similarity	NPD5944	Phase 1
0.7136	Intermediate Similarity	NPD5945	Phase 1
0.7136	Intermediate Similarity	NPD484	Approved
0.713	Intermediate Similarity	NPD3875	Discontinued
0.7129	Intermediate Similarity	NPD4072	Approved
0.7129	Intermediate Similarity	NPD4071	Approved
0.7119	Intermediate Similarity	NPD8100	Phase 3
0.7117	Intermediate Similarity	NPD3440	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD5065	Approved
0.7111	Intermediate Similarity	NPD6824	Clinical (unspecified phase)
0.71	Intermediate Similarity	NPD2951	Discontinued
0.7095	Intermediate Similarity	NPD4551	Phase 2
0.7095	Intermediate Similarity	NPD5911	Clinical (unspecified phase)
0.7094	Intermediate Similarity	NPD1620	Clinical (unspecified phase)
0.7094	Intermediate Similarity	NPD3920	Phase 2
0.7093	Intermediate Similarity	NPD7426	Phase 1
0.7093	Intermediate Similarity	NPD7050	Clinical (unspecified phase)
0.7093	Intermediate Similarity	NPD7675	Phase 3
0.7093	Intermediate Similarity	NPD7676	Clinical (unspecified phase)
0.7093	Intermediate Similarity	NPD7051	Phase 3
0.7093	Intermediate Similarity	NPD7674	Phase 3
0.7091	Intermediate Similarity	NPD7069	Discontinued
0.7087	Intermediate Similarity	NPD4885	Approved
0.7085	Intermediate Similarity	NPD8109	Clinical (unspecified phase)
0.7085	Intermediate Similarity	NPD3354	Phase 2
0.7085	Intermediate Similarity	NPD6568	Discontinued
0.7082	Intermediate Similarity	NPD7729	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD2952	Discontinued
0.7075	Intermediate Similarity	NPD6769	Clinical (unspecified phase)
0.7074	Intermediate Similarity	NPD5479	Discontinued
0.7072	Intermediate Similarity	NPD6803	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD6503	Clinical (unspecified phase)
0.7062	Intermediate Similarity	NPD3396	Approved
0.7062	Intermediate Similarity	NPD6590	Discontinued
0.7062	Intermediate Similarity	NPD3395	Approved
0.7053	Intermediate Similarity	NPD4375	Approved
0.7051	Intermediate Similarity	NPD4862	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD4890	Phase 2
0.7048	Intermediate Similarity	NPD3938	Phase 1
0.7044	Intermediate Similarity	NPD1032	Phase 2

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