NPASS Compound

Structure

NPC147561 OpenBabel07101718192D 29 32 0 0 1 0 0 0 0 0999 V2000 -2.4616 0.0129 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0039 -2.2708 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4135 0.4593 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3090 1.4538 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9135 0.7775 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6350 -1.0987 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7690 -1.5987 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6350 -0.0987 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9030 -1.0987 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7690 0.4013 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3458 -0.9839 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6577 -1.1962 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3587 1.1194 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0827 1.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5060 -0.2819 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.0483 -1.9761 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9030 -0.0987 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1691 1.6092 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.1298 -0.7064 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.3049 0.4013 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.0370 0.4013 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2900 -0.0043 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9781 0.2079 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.3152 -2.6562 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.0370 1.4013 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8258 -1.0011 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.1709 -0.0987 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 15 1 0 0 0 0 2 16 1 0 0 0 0 3 22 1 0 0 0 0 4 22 1 0 0 0 0 5 23 1 0 0 0 0 6 7 2 0 0 0 0 6 8 1 0 0 0 0 7 9 1 0 0 0 0 8 10 2 0 0 0 0 9 17 2 0 0 0 0 10 17 1 0 0 0 0 11 12 1 0 0 0 0 11 15 1 0 0 0 0 12 19 1 0 0 0 0 13 20 1 0 0 0 0 14 18 1 0 0 0 0 15 24 1 1 0 0 0 16 25 2 0 0 0 0 16 27 1 0 0 0 0 17 21 1 0 0 0 0 18 13 1 1 0 0 0 18 22 1 0 0 0 0 19 23 1 1 0 0 0 19 27 1 0 0 0 0 20 23 1 6 0 0 0 20 28 1 0 0 0 0 21 26 2 0 0 0 0 21 28 1 0 0 0 0 22 29 1 0 0 0 0 23 24 1 6 0 0 0 24 14 1 1 0 0 0 24 29 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	400.22
Volume:	420.203
LogP:	4.781
LogD:	3.796
LogS:	-4.816
# Rotatable Bonds:	5
TPSA:	61.83
# H-Bond Aceptor:	5
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.697
Synthetic Accessibility Score:	5.326
Fsp3:	0.667
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.814
MDCK Permeability:	2.2399819499696605e-05
Pgp-inhibitor:	0.999
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.915
30% Bioavailability (F30%):	0.971

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.092
Plasma Protein Binding (PPB):	94.69339752197266%
Volume Distribution (VD):	2.018
Pgp-substrate:	8.394794464111328%

ADMET: Metabolism

CYP1A2-inhibitor:	0.118
CYP1A2-substrate:	0.084
CYP2C19-inhibitor:	0.111
CYP2C19-substrate:	0.538
CYP2C9-inhibitor:	0.417
CYP2C9-substrate:	0.125
CYP2D6-inhibitor:	0.037
CYP2D6-substrate:	0.169
CYP3A4-inhibitor:	0.632
CYP3A4-substrate:	0.394

ADMET: Excretion

Clearance (CL):	7.313
Half-life (T1/2):	0.23

ADMET: Toxicity

hERG Blockers:	0.577
Human Hepatotoxicity (H-HT):	0.567
Drug-inuced Liver Injury (DILI):	0.867
AMES Toxicity:	0.032
Rat Oral Acute Toxicity:	0.144
Maximum Recommended Daily Dose:	0.875
Skin Sensitization:	0.859
Carcinogencity:	0.427
Eye Corrosion:	0.027
Eye Irritation:	0.626
Respiratory Toxicity:	0.969

Download Data

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

Natural Product: NPC147561

Natural Product ID:	NPC147561
*Common Name:**	MDUQZKJGFROTKT-JSJPKNAYSA-N
IUPAC Name:	n.a.
Synonyms:	Triptogelin G-2
Standard InCHIKey:	MDUQZKJGFROTKT-JSJPKNAYSA-N
Standard InCHI:	InChI=1S/C24H32O5/c1-15-11-12-19(27-16(2)25)23(5)20(28-21(26)17-9-7-6-8-10-17)13-18-14-24(15,23)29-22(18,3)4/h6-10,15,18-20H,11-14H2,1-5H3/t15-,18-,19+,20+,23+,24+/m1/s1
SMILES:	C[C@@H]1CC[C@@H]([C@@]2(C)[C@H](C[C@@H]3C[C@]12OC3(C)C)OC(=O)c1ccccc1)OC(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL374470
PubChem CID:	44419629
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001550] Sesquiterpenoids [CHEMONTID:0002051] Agarofurans

*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
NPO22423	Microtropis fokienensis	Species	Celastraceae	Eukaryota	stem	n.a.	n.a.	PMID[16643054]
NPO22423	Microtropis fokienensis	Species	Celastraceae	Eukaryota	leaves	n.a.	n.a.	PMID[17125218]
NPO22423	Microtropis fokienensis	Species	Celastraceae	Eukaryota	n.a.	root	n.a.	PMID[17315960]
NPO22423	Microtropis fokienensis	Species	Celastraceae	Eukaryota	roots	n.a.	n.a.	PMID[17315960]
NPO22423	Microtropis fokienensis	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18590313]
NPO11250	Celastrus flagellaris	Species	Celastraceae	Eukaryota	seeds	Jilin, China	n.a.	PMID[26295746]
NPO11250	Celastrus flagellaris	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11250	Celastrus flagellaris	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22423	Microtropis fokienensis	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11250	Celastrus flagellaris	Species	Celastraceae	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
MIC	1
Others	6

Activity Type	# Activity
Cell Line	2
Organism	1
Others	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT519	Cell Line	SH-SY5Y	Homo sapiens	Activity	=	74.4	%	PMID[568952]
NPT80	Cell Line	Raji	Homo sapiens	Activity	=	60.0	%	PMID[568953]
NPT88	Organism	Mycobacterium tuberculosis	Mycobacterium tuberculosis	MIC	=	26000.0	nM	PMID[568951]
NPT2	Others	Unspecified		Activity	=	4.6	%	PMID[568953]
NPT2	Others	Unspecified		Activity	=	36.6	%	PMID[568953]
NPT2	Others	Unspecified		Activity	=	76.8	%	PMID[568953]
NPT2	Others	Unspecified		Activity	=	100.0	%	PMID[568953]

☑ 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 NPC147561 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	293
0.1-0.2	1194
0.2-0.3	2082
0.3-0.4	4445
0.4-0.5	9118
0.5-0.6	13313
0.6-0.7	10355
0.7-0.8	1501
0.8-0.85	189
0.85-0.9	108
0.9-0.95	85
0.95-1	14

Similarity Score	Similarity Level	Natural Product ID
0.9683	High Similarity	NPC474608
0.9606	High Similarity	NPC66761
0.9606	High Similarity	NPC17877
0.9606	High Similarity	NPC472577
0.9606	High Similarity	NPC291638
0.9606	High Similarity	NPC195647
0.9457	High Similarity	NPC283375
0.9457	High Similarity	NPC183122
0.9385	High Similarity	NPC210591
0.9385	High Similarity	NPC475652
0.9385	High Similarity	NPC214550
0.9313	High Similarity	NPC473613
0.9313	High Similarity	NPC211137
0.9313	High Similarity	NPC147880
0.9313	High Similarity	NPC43241
0.9313	High Similarity	NPC473758
0.9313	High Similarity	NPC473085
0.9313	High Similarity	NPC473109
0.9313	High Similarity	NPC171207
0.9313	High Similarity	NPC473112
0.9313	High Similarity	NPC97667
0.9313	High Similarity	NPC200592
0.9313	High Similarity	NPC48017
0.9313	High Similarity	NPC100913
0.9313	High Similarity	NPC473060
0.9313	High Similarity	NPC476094
0.9313	High Similarity	NPC275592
0.9313	High Similarity	NPC473081
0.9313	High Similarity	NPC184747
0.9313	High Similarity	NPC90614
0.9313	High Similarity	NPC4341
0.9242	High Similarity	NPC472576
0.9242	High Similarity	NPC16912
0.9242	High Similarity	NPC97947
0.9242	High Similarity	NPC27377
0.9242	High Similarity	NPC87448
0.9242	High Similarity	NPC118080
0.9242	High Similarity	NPC291599
0.9242	High Similarity	NPC41481
0.9219	High Similarity	NPC238370
0.9167	High Similarity	NPC477904
0.9167	High Similarity	NPC183270
0.916	High Similarity	NPC475373
0.9154	High Similarity	NPC473216
0.9154	High Similarity	NPC473399
0.9104	High Similarity	NPC163087
0.9104	High Similarity	NPC177340
0.9104	High Similarity	NPC139067
0.9104	High Similarity	NPC191082
0.9104	High Similarity	NPC475429
0.9104	High Similarity	NPC473673
0.9104	High Similarity	NPC246480
0.9104	High Similarity	NPC147217
0.9104	High Similarity	NPC270498
0.9084	High Similarity	NPC472551
0.9084	High Similarity	NPC472545
0.9077	High Similarity	NPC48929
0.9037	High Similarity	NPC125106
0.9037	High Similarity	NPC188865
0.9037	High Similarity	NPC95810
0.9037	High Similarity	NPC472570
0.9037	High Similarity	NPC475122
0.9037	High Similarity	NPC57628
0.9037	High Similarity	NPC241951
0.9037	High Similarity	NPC11685
0.9037	High Similarity	NPC163719
0.9037	High Similarity	NPC476974
0.9037	High Similarity	NPC25768
0.9037	High Similarity	NPC470152
0.9037	High Similarity	NPC475759
0.9037	High Similarity	NPC472569
0.9037	High Similarity	NPC95265
0.9037	High Similarity	NPC51314
0.9037	High Similarity	NPC470231
0.9037	High Similarity	NPC67777
0.9037	High Similarity	NPC70716
0.9037	High Similarity	NPC472573
0.9023	High Similarity	NPC472547
0.9015	High Similarity	NPC39549
0.8971	High Similarity	NPC171525
0.8971	High Similarity	NPC174982
0.8971	High Similarity	NPC476973
0.8971	High Similarity	NPC471107
0.8971	High Similarity	NPC472571
0.8971	High Similarity	NPC472575
0.8971	High Similarity	NPC472572
0.8971	High Similarity	NPC200471
0.8971	High Similarity	NPC472568
0.8971	High Similarity	NPC184817
0.8971	High Similarity	NPC471100
0.8971	High Similarity	NPC70403
0.8971	High Similarity	NPC470159
0.8971	High Similarity	NPC96903
0.8971	High Similarity	NPC473088
0.8971	High Similarity	NPC470157
0.8971	High Similarity	NPC158663
0.8971	High Similarity	NPC29704
0.8971	High Similarity	NPC177940
0.8971	High Similarity	NPC471104
0.8971	High Similarity	NPC469349
0.8955	High Similarity	NPC224491
0.8934	High Similarity	NPC84129
0.8905	High Similarity	NPC474935
0.8898	High Similarity	NPC473082
0.8898	High Similarity	NPC275576
0.8846	High Similarity	NPC470278
0.8841	High Similarity	NPC281717
0.8832	High Similarity	NPC472556
0.8828	High Similarity	NPC169913
0.8828	High Similarity	NPC473220
0.8828	High Similarity	NPC470753
0.8824	High Similarity	NPC477894
0.8824	High Similarity	NPC91703
0.8815	High Similarity	NPC266374
0.8779	High Similarity	NPC472394
0.8777	High Similarity	NPC266265
0.8777	High Similarity	NPC92293
0.8777	High Similarity	NPC301556
0.8777	High Similarity	NPC476975
0.8777	High Similarity	NPC270590
0.8777	High Similarity	NPC471101
0.8777	High Similarity	NPC473215
0.8768	High Similarity	NPC473602
0.875	High Similarity	NPC34012
0.875	High Similarity	NPC472546
0.875	High Similarity	NPC470765
0.8741	High Similarity	NPC475400
0.8722	High Similarity	NPC477893
0.8714	High Similarity	NPC254558
0.8714	High Similarity	NPC473214
0.8714	High Similarity	NPC470245
0.8702	High Similarity	NPC72915
0.8696	High Similarity	NPC127857
0.8689	High Similarity	NPC473869
0.8686	High Similarity	NPC131966
0.8686	High Similarity	NPC191387
0.8672	High Similarity	NPC473083
0.8667	High Similarity	NPC9905
0.8657	High Similarity	NPC472374
0.8657	High Similarity	NPC472372
0.8652	High Similarity	NPC470153
0.8652	High Similarity	NPC51602
0.8652	High Similarity	NPC471103
0.8651	High Similarity	NPC37641
0.8651	High Similarity	NPC50872
0.8651	High Similarity	NPC311175
0.8647	High Similarity	NPC329913
0.8647	High Similarity	NPC126516
0.8633	High Similarity	NPC209592
0.8633	High Similarity	NPC475552
0.8633	High Similarity	NPC48599
0.8623	High Similarity	NPC38696
0.8613	High Similarity	NPC192658
0.8603	High Similarity	NPC87934
0.8603	High Similarity	NPC162613
0.8592	High Similarity	NPC472548
0.8592	High Similarity	NPC477905
0.8583	High Similarity	NPC70973
0.8582	High Similarity	NPC477896
0.8582	High Similarity	NPC469448
0.8571	High Similarity	NPC472656
0.8571	High Similarity	NPC473760
0.8571	High Similarity	NPC473243
0.8538	High Similarity	NPC51292
0.8529	High Similarity	NPC472395
0.8529	High Similarity	NPC472371
0.8525	High Similarity	NPC128368
0.8511	High Similarity	NPC473403
0.8511	High Similarity	NPC60509
0.8511	High Similarity	NPC81698
0.8511	High Similarity	NPC250046
0.8507	High Similarity	NPC203486
0.85	High Similarity	NPC478263
0.85	High Similarity	NPC240115
0.8489	Intermediate Similarity	NPC34943
0.8478	Intermediate Similarity	NPC183540
0.8478	Intermediate Similarity	NPC182869
0.8478	Intermediate Similarity	NPC475135
0.8473	Intermediate Similarity	NPC195224
0.8472	Intermediate Similarity	NPC21410
0.8472	Intermediate Similarity	NPC473670
0.8472	Intermediate Similarity	NPC282239
0.8472	Intermediate Similarity	NPC34066
0.8472	Intermediate Similarity	NPC472549
0.8451	Intermediate Similarity	NPC31829
0.8451	Intermediate Similarity	NPC198455
0.8451	Intermediate Similarity	NPC7095
0.8451	Intermediate Similarity	NPC161239
0.8451	Intermediate Similarity	NPC165260
0.8451	Intermediate Similarity	NPC112216
0.844	Intermediate Similarity	NPC217918
0.844	Intermediate Similarity	NPC132652
0.8429	Intermediate Similarity	NPC92867
0.8429	Intermediate Similarity	NPC311825
0.8429	Intermediate Similarity	NPC125882
0.8429	Intermediate Similarity	NPC478264
0.8417	Intermediate Similarity	NPC95449
0.8414	Intermediate Similarity	NPC106895
0.8414	Intermediate Similarity	NPC217091
0.8413	Intermediate Similarity	NPC473860

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 NPC147561 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	251
0.1-0.2	768
0.2-0.3	1241
0.3-0.4	2722
0.4-0.5	2370
0.5-0.6	1336
0.6-0.7	427
0.7-0.8	33
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
0.8298	Intermediate Similarity	NPD7236	Approved
0.8074	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.8065	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.8014	Intermediate Similarity	NPD7239	Suspended
0.776	Intermediate Similarity	NPD2182	Approved
0.7727	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7721	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.7681	Intermediate Similarity	NPD7008	Discontinued
0.7669	Intermediate Similarity	NPD7457	Clinical (unspecified phase)
0.7658	Intermediate Similarity	NPD7799	Discontinued
0.7626	Intermediate Similarity	NPD3764	Approved
0.7576	Intermediate Similarity	NPD7741	Discontinued
0.7538	Intermediate Similarity	NPD5951	Approved
0.7532	Intermediate Similarity	NPD7057	Phase 3
0.7532	Intermediate Similarity	NPD7058	Phase 2
0.7519	Intermediate Similarity	NPD6858	Approved
0.7519	Intermediate Similarity	NPD7094	Approved
0.7481	Intermediate Similarity	NPD6287	Discontinued
0.7447	Intermediate Similarity	NPD7961	Discontinued
0.744	Intermediate Similarity	NPD164	Approved
0.74	Intermediate Similarity	NPD6273	Approved
0.7398	Intermediate Similarity	NPD1238	Approved
0.7391	Intermediate Similarity	NPD8470	Clinical (unspecified phase)
0.7348	Intermediate Similarity	NPD4198	Discontinued
0.7344	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD8407	Phase 2
0.7297	Intermediate Similarity	NPD4628	Phase 3
0.7297	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD2629	Approved
0.7256	Intermediate Similarity	NPD8368	Discontinued
0.7246	Intermediate Similarity	NPD8434	Phase 2
0.7211	Intermediate Similarity	NPD7702	Clinical (unspecified phase)
0.7206	Intermediate Similarity	NPD7163	Clinical (unspecified phase)
0.7203	Intermediate Similarity	NPD6663	Approved
0.7203	Intermediate Similarity	NPD8032	Phase 2
0.7192	Intermediate Similarity	NPD3748	Approved
0.7181	Intermediate Similarity	NPD8166	Discontinued
0.7181	Intermediate Similarity	NPD7003	Approved
0.7179	Intermediate Similarity	NPD5761	Phase 2
0.7179	Intermediate Similarity	NPD7819	Suspended
0.7179	Intermediate Similarity	NPD5760	Phase 2
0.7176	Intermediate Similarity	NPD1609	Clinical (unspecified phase)
0.7163	Intermediate Similarity	NPD5736	Approved
0.7143	Intermediate Similarity	NPD6591	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD8127	Discontinued
0.7114	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD7610	Discontinued
0.7105	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD2533	Approved
0.7105	Intermediate Similarity	NPD2532	Approved
0.7105	Intermediate Similarity	NPD2534	Approved
0.7083	Intermediate Similarity	NPD7713	Phase 3
0.708	Intermediate Similarity	NPD5125	Phase 3
0.708	Intermediate Similarity	NPD5126	Approved
0.7059	Intermediate Similarity	NPD8361	Approved
0.7059	Intermediate Similarity	NPD8360	Approved
0.7059	Intermediate Similarity	NPD8435	Approved
0.7041	Intermediate Similarity	NPD8424	Clinical (unspecified phase)
0.7034	Intermediate Similarity	NPD7966	Clinical (unspecified phase)
0.7034	Intermediate Similarity	NPD2979	Phase 3
0.7032	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD7458	Discontinued
0.7027	Intermediate Similarity	NPD2796	Approved
0.7023	Intermediate Similarity	NPD2067	Discontinued
0.7013	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD37	Approved
0.6993	Remote Similarity	NPD6832	Phase 2
0.6987	Remote Similarity	NPD6599	Discontinued
0.6982	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD4965	Approved
0.6981	Remote Similarity	NPD4967	Phase 2
0.6981	Remote Similarity	NPD4966	Approved
0.6981	Remote Similarity	NPD7768	Phase 2
0.698	Remote Similarity	NPD2346	Discontinued
0.698	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.697	Remote Similarity	NPD5844	Phase 1
0.6962	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD5494	Approved
0.6954	Remote Similarity	NPD3750	Approved
0.6953	Remote Similarity	NPD1930	Approved
0.6953	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.6953	Remote Similarity	NPD1929	Approved
0.6934	Remote Similarity	NPD9545	Approved
0.6929	Remote Similarity	NPD6637	Approved
0.6929	Remote Similarity	NPD3972	Approved
0.6923	Remote Similarity	NPD3226	Approved
0.6918	Remote Similarity	NPD4307	Phase 2
0.6913	Remote Similarity	NPD5406	Approved
0.6913	Remote Similarity	NPD5408	Approved
0.6913	Remote Similarity	NPD5405	Approved
0.6913	Remote Similarity	NPD2438	Suspended
0.6913	Remote Similarity	NPD2935	Discontinued
0.6913	Remote Similarity	NPD5404	Approved
0.6908	Remote Similarity	NPD7274	Clinical (unspecified phase)
0.6899	Remote Similarity	NPD5909	Discontinued
0.6894	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD6234	Discontinued
0.6892	Remote Similarity	NPD2567	Approved
0.6892	Remote Similarity	NPD2569	Approved
0.6889	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6884	Remote Similarity	NPD3024	Approved
0.6884	Remote Similarity	NPD3025	Approved
0.688	Remote Similarity	NPD1989	Approved
0.6867	Remote Similarity	NPD6005	Phase 3
0.6867	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD6004	Phase 3
0.6867	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD6002	Phase 3
0.6857	Remote Similarity	NPD1281	Approved
0.6855	Remote Similarity	NPD1202	Approved
0.685	Remote Similarity	NPD7798	Approved
0.685	Remote Similarity	NPD2066	Phase 3
0.6848	Remote Similarity	NPD7473	Discontinued
0.6846	Remote Similarity	NPD2799	Discontinued
0.6845	Remote Similarity	NPD6765	Approved
0.6845	Remote Similarity	NPD6764	Approved
0.6842	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD7411	Suspended
0.6835	Remote Similarity	NPD17	Approved
0.6832	Remote Similarity	NPD7075	Discontinued
0.6831	Remote Similarity	NPD1876	Approved
0.6822	Remote Similarity	NPD6647	Phase 2
0.6821	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD8485	Approved
0.6813	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6803	Remote Similarity	NPD4140	Approved
0.68	Remote Similarity	NPD6100	Approved
0.68	Remote Similarity	NPD6099	Approved
0.6797	Remote Similarity	NPD6190	Approved
0.6795	Remote Similarity	NPD920	Approved
0.6794	Remote Similarity	NPD6685	Approved
0.6786	Remote Similarity	NPD3023	Approved
0.6786	Remote Similarity	NPD3026	Approved
0.6781	Remote Similarity	NPD2313	Discontinued
0.6781	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.677	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD7229	Phase 3
0.6768	Remote Similarity	NPD6232	Discontinued
0.6763	Remote Similarity	NPD5585	Approved
0.6763	Remote Similarity	NPD5691	Approved
0.6761	Remote Similarity	NPD5327	Phase 3
0.6757	Remote Similarity	NPD230	Phase 1
0.6757	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD6355	Discontinued
0.6744	Remote Similarity	NPD8150	Discontinued
0.6736	Remote Similarity	NPD2798	Approved
0.6735	Remote Similarity	NPD7715	Approved
0.6735	Remote Similarity	NPD7714	Approved
0.6733	Remote Similarity	NPD7305	Phase 1
0.6733	Remote Similarity	NPD4308	Phase 3
0.6728	Remote Similarity	NPD3749	Approved
0.6714	Remote Similarity	NPD3019	Approved
0.6713	Remote Similarity	NPD2199	Approved
0.6713	Remote Similarity	NPD2198	Approved
0.6713	Remote Similarity	NPD1283	Approved
0.6713	Remote Similarity	NPD5667	Approved
0.6712	Remote Similarity	NPD6039	Approved
0.671	Remote Similarity	NPD6799	Approved
0.671	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD7228	Approved
0.6704	Remote Similarity	NPD8486	Clinical (unspecified phase)
0.6693	Remote Similarity	NPD3495	Discontinued
0.6691	Remote Similarity	NPD6010	Discontinued
0.669	Remote Similarity	NPD1608	Approved
0.6689	Remote Similarity	NPD2531	Phase 2
0.6689	Remote Similarity	NPD1551	Phase 2
0.6687	Remote Similarity	NPD6801	Discontinued
0.6686	Remote Similarity	NPD6784	Approved
0.6686	Remote Similarity	NPD6785	Approved
0.6686	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6685	Remote Similarity	NPD7497	Discontinued
0.6667	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3266	Approved
0.6667	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD8312	Approved
0.6667	Remote Similarity	NPD2797	Approved
0.6667	Remote Similarity	NPD4380	Phase 2
0.6667	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3267	Approved
0.6667	Remote Similarity	NPD8313	Approved
0.6667	Remote Similarity	NPD1243	Approved
0.6667	Remote Similarity	NPD1470	Approved
0.6647	Remote Similarity	NPD6559	Discontinued
0.6646	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6645	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6645	Remote Similarity	NPD1471	Phase 3
0.6644	Remote Similarity	NPD7055	Discontinued
0.6641	Remote Similarity	NPD1237	Approved
0.6623	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6623	Remote Similarity	NPD4110	Phase 3
0.6623	Remote Similarity	NPD7033	Discontinued
0.6623	Remote Similarity	NPD1510	Phase 2
0.6621	Remote Similarity	NPD5740	Clinical (unspecified phase)
0.6621	Remote Similarity	NPD6085	Phase 2
0.662	Remote Similarity	NPD1201	Approved
0.662	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6619	Remote Similarity	NPD6065	Approved
0.6607	Remote Similarity	NPD7893	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