NPASS Compound

Structure

NPC472452 OpenBabel07101718202D 30 33 0 0 1 0 0 0 0 0999 V2000 -1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7913 -5.2213 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6277 -5.4487 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 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.1222 -4.4781 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1277 -4.5827 0.0000 C 0 0 2 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 0.8660 -3.5000 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 4.3301 -3.5000 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 5.1962 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -2.0000 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 -4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.7210 -3.6691 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 2.5981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3 10 1 0 0 0 0 4 11 1 0 0 0 0 7 14 2 0 0 0 0 7 15 1 0 0 0 0 8 1 1 6 0 0 0 8 13 1 0 0 0 0 8 16 1 0 0 0 0 9 2 1 6 0 0 0 9 12 1 0 0 0 0 9 17 1 0 0 0 0 10 14 1 0 0 0 0 10 16 2 0 0 0 0 11 17 2 0 0 0 0 11 19 1 0 0 0 0 12 5 1 1 0 0 0 12 28 1 0 0 0 0 13 6 1 1 0 0 0 13 29 1 0 0 0 0 14 24 1 0 0 0 0 15 18 2 0 0 0 0 15 30 1 0 0 0 0 16 18 1 0 0 0 0 17 21 1 0 0 0 0 18 23 1 0 0 0 0 19 20 2 0 0 0 0 19 25 1 0 0 0 0 20 22 1 0 0 0 0 20 26 1 0 0 0 0 21 22 2 0 0 0 0 21 28 1 0 0 0 0 22 30 1 0 0 0 0 23 27 2 0 0 0 0 23 29 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	414.17
Volume:	415.215
LogP:	5.287
LogD:	3.058
LogS:	-4.268
# Rotatable Bonds:	2
TPSA:	105.45
# H-Bond Aceptor:	7
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.481
Synthetic Accessibility Score:	4.559
Fsp3:	0.435
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.163
MDCK Permeability:	2.9759796234429814e-05
Pgp-inhibitor:	0.085
Pgp-substrate:	0.008
Human Intestinal Absorption (HIA):	0.123
20% Bioavailability (F20%):	0.006
30% Bioavailability (F30%):	0.002

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.013
Plasma Protein Binding (PPB):	98.76538848876953%
Volume Distribution (VD):	0.484
Pgp-substrate:	3.7029166221618652%

ADMET: Metabolism

CYP1A2-inhibitor:	0.73
CYP1A2-substrate:	0.913
CYP2C19-inhibitor:	0.491
CYP2C19-substrate:	0.236
CYP2C9-inhibitor:	0.723
CYP2C9-substrate:	0.823
CYP2D6-inhibitor:	0.476
CYP2D6-substrate:	0.184
CYP3A4-inhibitor:	0.177
CYP3A4-substrate:	0.235

ADMET: Excretion

Clearance (CL):	7.7
Half-life (T1/2):	0.377

ADMET: Toxicity

hERG Blockers:	0.004
Human Hepatotoxicity (H-HT):	0.062
Drug-inuced Liver Injury (DILI):	0.854
AMES Toxicity:	0.023
Rat Oral Acute Toxicity:	0.983
Maximum Recommended Daily Dose:	0.913
Skin Sensitization:	0.79
Carcinogencity:	0.403
Eye Corrosion:	0.003
Eye Irritation:	0.915
Respiratory Toxicity:	0.315

Download Data

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

Natural Product: NPC472452

Natural Product ID:	NPC472452
*Common Name:**	AYBJCDJOJFEQJW-NRMKKVEVSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	AYBJCDJOJFEQJW-NRMKKVEVSA-N
Standard InCHI:	InChI=1S/C23H26O7/c1-8-13(6)29-23(27)18-15(7-14(24)10(3)16(8)18)30-22-20(26)19(25)11(4)17-9(2)12(5)28-21(17)22/h7-9,12-13,24-26H,1-6H3/t8-,9-,12-,13-/m1/s1
SMILES:	CC1C(OC2=C(C(=C(C(=C12)C)O)O)OC3=C4C(=C(C(=C3)O)C)C(C(OC4=O)C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3422273
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0000254] Ethers [CHEMONTID:0002463] Diarylethers

*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
NPO32511	Penicillium chrysogenum	Under-species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[25611519]

☑ 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	5

Activity Type	# Activity
Cell Line	3
NON-MOLECULAR	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	IC50	=	9600.0	nM	PMID[506253]
NPT71	Cell Line	HEK293	Homo sapiens	IC50	=	6400.0	nM	PMID[506253]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	3400.0	nM	PMID[506253]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	3500.0	nM	PMID[506253]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	7000.0	nM	PMID[506253]

☑ 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 NPC472452 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	378
0.1-0.2	1644
0.2-0.3	3730
0.3-0.4	9062
0.4-0.5	9444
0.5-0.6	3501
0.6-0.7	5020
0.7-0.8	6261
0.8-0.85	2838
0.85-0.9	720
0.9-0.95	98
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.956	High Similarity	NPC326520
0.95	High Similarity	NPC170245
0.9375	High Similarity	NPC475985
0.9317	High Similarity	NPC473286
0.9308	High Similarity	NPC228785
0.9308	High Similarity	NPC14353
0.9308	High Similarity	NPC36217
0.9308	High Similarity	NPC56085
0.9304	High Similarity	NPC223787
0.9255	High Similarity	NPC273959
0.9255	High Similarity	NPC474350
0.9255	High Similarity	NPC7483
0.925	High Similarity	NPC40491
0.925	High Similarity	NPC278052
0.925	High Similarity	NPC474186
0.925	High Similarity	NPC61010
0.9245	High Similarity	NPC100123
0.9241	High Similarity	NPC227062
0.9241	High Similarity	NPC150227
0.9202	High Similarity	NPC6588
0.9202	High Similarity	NPC117854
0.9202	High Similarity	NPC477154
0.9198	High Similarity	NPC25361
0.9193	High Similarity	NPC201800
0.9193	High Similarity	NPC81679
0.9187	High Similarity	NPC472624
0.9187	High Similarity	NPC320359
0.9187	High Similarity	NPC292415
0.9187	High Similarity	NPC475886
0.9187	High Similarity	NPC474287
0.9182	High Similarity	NPC469584
0.9182	High Similarity	NPC190020
0.9182	High Similarity	NPC217677
0.9182	High Similarity	NPC241904
0.9182	High Similarity	NPC77679
0.9182	High Similarity	NPC84935
0.9182	High Similarity	NPC165977
0.9182	High Similarity	NPC300727
0.9177	High Similarity	NPC477503
0.9177	High Similarity	NPC199926
0.9177	High Similarity	NPC470327
0.9177	High Similarity	NPC45849
0.9177	High Similarity	NPC200761
0.9136	High Similarity	NPC205265
0.9136	High Similarity	NPC329669
0.9136	High Similarity	NPC472281
0.9136	High Similarity	NPC156082
0.9136	High Similarity	NPC236521
0.9136	High Similarity	NPC248638
0.9136	High Similarity	NPC197168
0.9136	High Similarity	NPC18100
0.9136	High Similarity	NPC236132
0.9136	High Similarity	NPC186686
0.9136	High Similarity	NPC220313
0.9136	High Similarity	NPC473313
0.9136	High Similarity	NPC472278
0.9136	High Similarity	NPC152659
0.913	High Similarity	NPC475883
0.913	High Similarity	NPC474187
0.913	High Similarity	NPC266314
0.913	High Similarity	NPC103201
0.913	High Similarity	NPC474351
0.913	High Similarity	NPC473106
0.9125	High Similarity	NPC210459
0.9125	High Similarity	NPC250214
0.9125	High Similarity	NPC83763
0.9125	High Similarity	NPC476242
0.9125	High Similarity	NPC95936
0.9125	High Similarity	NPC168616
0.9125	High Similarity	NPC238381
0.9125	High Similarity	NPC329091
0.9125	High Similarity	NPC85121
0.9119	High Similarity	NPC35038
0.9119	High Similarity	NPC274730
0.9119	High Similarity	NPC209614
0.9119	High Similarity	NPC278778
0.9119	High Similarity	NPC291878
0.9119	High Similarity	NPC142339
0.9119	High Similarity	NPC195796
0.9119	High Similarity	NPC470328
0.9119	High Similarity	NPC472626
0.9091	High Similarity	NPC124470
0.9091	High Similarity	NPC109827
0.9091	High Similarity	NPC17219
0.9091	High Similarity	NPC472276
0.9085	High Similarity	NPC126204
0.908	High Similarity	NPC112981
0.908	High Similarity	NPC239752
0.908	High Similarity	NPC472450
0.908	High Similarity	NPC472277
0.908	High Similarity	NPC275780
0.908	High Similarity	NPC293319
0.908	High Similarity	NPC475888
0.9074	High Similarity	NPC211107
0.9074	High Similarity	NPC25152
0.9074	High Similarity	NPC472635
0.9074	High Similarity	NPC144843
0.9074	High Similarity	NPC215612
0.9074	High Similarity	NPC472402
0.9068	High Similarity	NPC321399
0.9068	High Similarity	NPC299436
0.9068	High Similarity	NPC200594
0.9062	High Similarity	NPC474836
0.9062	High Similarity	NPC472910
0.9062	High Similarity	NPC236796
0.9062	High Similarity	NPC222814
0.9062	High Similarity	NPC96167
0.9062	High Similarity	NPC472913
0.9062	High Similarity	NPC475267
0.9062	High Similarity	NPC474208
0.9062	High Similarity	NPC472598
0.9062	High Similarity	NPC291508
0.9062	High Similarity	NPC472911
0.9062	High Similarity	NPC162869
0.9062	High Similarity	NPC27337
0.9062	High Similarity	NPC48208
0.9062	High Similarity	NPC474055
0.9062	High Similarity	NPC156057
0.9062	High Similarity	NPC262286
0.9062	High Similarity	NPC108456
0.9062	High Similarity	NPC472914
0.9062	High Similarity	NPC78225
0.9062	High Similarity	NPC245758
0.9062	High Similarity	NPC36852
0.9057	High Similarity	NPC20541
0.9057	High Similarity	NPC67396
0.9057	High Similarity	NPC16082
0.9057	High Similarity	NPC79998
0.9057	High Similarity	NPC82592
0.9051	High Similarity	NPC106976
0.9051	High Similarity	NPC289968
0.9051	High Similarity	NPC295646
0.9051	High Similarity	NPC199773
0.9036	High Similarity	NPC158226
0.903	High Similarity	NPC475805
0.903	High Similarity	NPC163130
0.903	High Similarity	NPC165979
0.9024	High Similarity	NPC13481
0.9024	High Similarity	NPC128293
0.9024	High Similarity	NPC207575
0.9024	High Similarity	NPC20216
0.9024	High Similarity	NPC235610
0.9024	High Similarity	NPC173292
0.9024	High Similarity	NPC43319
0.9024	High Similarity	NPC39091
0.9018	High Similarity	NPC124038
0.9018	High Similarity	NPC270837
0.9018	High Similarity	NPC41301
0.9018	High Similarity	NPC189473
0.9018	High Similarity	NPC234004
0.9018	High Similarity	NPC23298
0.9018	High Similarity	NPC474240
0.9018	High Similarity	NPC146134
0.9012	High Similarity	NPC32694
0.9012	High Similarity	NPC349525
0.9006	High Similarity	NPC45846
0.9	High Similarity	NPC255106
0.9	High Similarity	NPC54928
0.9	High Similarity	NPC150977
0.9	High Similarity	NPC24640
0.9	High Similarity	NPC191146
0.9	High Similarity	NPC235165
0.9	High Similarity	NPC138243
0.9	High Similarity	NPC68093
0.8994	High Similarity	NPC113446
0.8994	High Similarity	NPC74924
0.8994	High Similarity	NPC213896
0.8994	High Similarity	NPC298692
0.8994	High Similarity	NPC89474
0.8994	High Similarity	NPC18727
0.8994	High Similarity	NPC281477
0.8994	High Similarity	NPC192083
0.8976	High Similarity	NPC279209
0.8976	High Similarity	NPC102277
0.8976	High Similarity	NPC101107
0.897	High Similarity	NPC292788
0.897	High Similarity	NPC150131
0.897	High Similarity	NPC272485
0.897	High Similarity	NPC474024
0.897	High Similarity	NPC218226
0.8963	High Similarity	NPC300053
0.8963	High Similarity	NPC37183
0.8963	High Similarity	NPC108433
0.8957	High Similarity	NPC469575
0.8957	High Similarity	NPC294965
0.8957	High Similarity	NPC474150
0.8957	High Similarity	NPC474162
0.8957	High Similarity	NPC472964
0.8957	High Similarity	NPC52204
0.8957	High Similarity	NPC229632
0.8957	High Similarity	NPC8300
0.8957	High Similarity	NPC220912
0.8951	High Similarity	NPC282009
0.8951	High Similarity	NPC200746
0.8951	High Similarity	NPC476283
0.8951	High Similarity	NPC161947
0.8951	High Similarity	NPC472630
0.8951	High Similarity	NPC47623
0.8951	High Similarity	NPC192686
0.8951	High Similarity	NPC472631

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 NPC472452 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	326
0.1-0.2	955
0.2-0.3	1916
0.3-0.4	2580
0.4-0.5	1787
0.5-0.6	952
0.6-0.7	458
0.7-0.8	137
0.8-0.85	34
0.85-0.9	5
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8994	High Similarity	NPD2393	Clinical (unspecified phase)
0.8931	High Similarity	NPD1934	Approved
0.8834	High Similarity	NPD5494	Approved
0.8802	High Similarity	NPD5844	Phase 1
0.8758	High Similarity	NPD2801	Approved
0.865	High Similarity	NPD4868	Clinical (unspecified phase)
0.8614	High Similarity	NPD6232	Discontinued
0.8571	High Similarity	NPD7473	Discontinued
0.8537	High Similarity	NPD3882	Suspended
0.8528	High Similarity	NPD1465	Phase 2
0.8528	High Similarity	NPD7819	Suspended
0.8521	High Similarity	NPD3818	Discontinued
0.8512	High Similarity	NPD6166	Phase 2
0.8512	High Similarity	NPD6167	Clinical (unspecified phase)
0.8512	High Similarity	NPD6168	Clinical (unspecified phase)
0.8488	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8485	Intermediate Similarity	NPD7075	Discontinued
0.8476	Intermediate Similarity	NPD3817	Phase 2
0.8421	Intermediate Similarity	NPD7074	Phase 3
0.8415	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8375	Intermediate Similarity	NPD2532	Approved
0.8375	Intermediate Similarity	NPD2533	Approved
0.8375	Intermediate Similarity	NPD2534	Approved
0.8363	Intermediate Similarity	NPD7054	Approved
0.8333	Intermediate Similarity	NPD6959	Discontinued
0.8323	Intermediate Similarity	NPD6234	Discontinued
0.8314	Intermediate Similarity	NPD7472	Approved
0.8313	Intermediate Similarity	NPD1511	Approved
0.8242	Intermediate Similarity	NPD6801	Discontinued
0.8232	Intermediate Similarity	NPD4380	Phase 2
0.8228	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.821	Intermediate Similarity	NPD1512	Approved
0.8161	Intermediate Similarity	NPD6797	Phase 2
0.8148	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8144	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8133	Intermediate Similarity	NPD37	Approved
0.8118	Intermediate Similarity	NPD7199	Phase 2
0.8114	Intermediate Similarity	NPD7251	Discontinued
0.8114	Intermediate Similarity	NPD6559	Discontinued
0.8095	Intermediate Similarity	NPD4965	Approved
0.8095	Intermediate Similarity	NPD4966	Approved
0.8095	Intermediate Similarity	NPD4967	Phase 2
0.8092	Intermediate Similarity	NPD7228	Approved
0.8072	Intermediate Similarity	NPD7411	Suspended
0.8068	Intermediate Similarity	NPD7808	Phase 3
0.8057	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.805	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.805	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8047	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8023	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD1549	Phase 2
0.8	Intermediate Similarity	NPD919	Approved
0.8	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7987	Intermediate Similarity	NPD2935	Discontinued
0.7975	Intermediate Similarity	NPD6799	Approved
0.7943	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7941	Intermediate Similarity	NPD3749	Approved
0.7933	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7929	Intermediate Similarity	NPD5402	Approved
0.7907	Intermediate Similarity	NPD1247	Approved
0.7904	Intermediate Similarity	NPD6599	Discontinued
0.7882	Intermediate Similarity	NPD7768	Phase 2
0.7874	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7861	Intermediate Similarity	NPD5710	Approved
0.7861	Intermediate Similarity	NPD5711	Approved
0.784	Intermediate Similarity	NPD2800	Approved
0.7814	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7791	Intermediate Similarity	NPD3750	Approved
0.7764	Intermediate Similarity	NPD2796	Approved
0.7736	Intermediate Similarity	NPD230	Phase 1
0.7725	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7725	Intermediate Similarity	NPD920	Approved
0.7711	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7702	Intermediate Similarity	NPD1510	Phase 2
0.7683	Intermediate Similarity	NPD4628	Phase 3
0.7679	Intermediate Similarity	NPD1653	Approved
0.7673	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7673	Intermediate Similarity	NPD1613	Approved
0.7657	Intermediate Similarity	NPD7229	Phase 3
0.7651	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7633	Intermediate Similarity	NPD3226	Approved
0.7624	Intermediate Similarity	NPD8312	Approved
0.7624	Intermediate Similarity	NPD8313	Approved
0.7622	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7622	Intermediate Similarity	NPD1243	Approved
0.7619	Intermediate Similarity	NPD5403	Approved
0.7614	Intermediate Similarity	NPD3926	Phase 2
0.7611	Intermediate Similarity	NPD7240	Approved
0.7607	Intermediate Similarity	NPD2346	Discontinued
0.7596	Intermediate Similarity	NPD8434	Phase 2
0.758	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7576	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7562	Intermediate Similarity	NPD1240	Approved
0.7547	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7547	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7546	Intermediate Similarity	NPD1551	Phase 2
0.7532	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7529	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7526	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD447	Suspended
0.7514	Intermediate Similarity	NPD7685	Pre-registration
0.75	Intermediate Similarity	NPD8150	Discontinued
0.75	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD5401	Approved
0.7486	Intermediate Similarity	NPD3751	Discontinued
0.7485	Intermediate Similarity	NPD3748	Approved
0.7485	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD2799	Discontinued
0.7484	Intermediate Similarity	NPD3027	Phase 3
0.7473	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7469	Intermediate Similarity	NPD1607	Approved
0.7458	Intermediate Similarity	NPD3787	Discontinued
0.7453	Intermediate Similarity	NPD4060	Phase 1
0.7453	Intermediate Similarity	NPD943	Approved
0.7444	Intermediate Similarity	NPD7286	Phase 2
0.7439	Intermediate Similarity	NPD6100	Approved
0.7439	Intermediate Similarity	NPD6099	Approved
0.7425	Intermediate Similarity	NPD6190	Approved
0.7411	Intermediate Similarity	NPD7783	Phase 2
0.7411	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7409	Intermediate Similarity	NPD7435	Discontinued
0.7407	Intermediate Similarity	NPD1933	Approved
0.7398	Intermediate Similarity	NPD8151	Discontinued
0.7396	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7378	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7363	Intermediate Similarity	NPD5953	Discontinued
0.7362	Intermediate Similarity	NPD6651	Approved
0.7344	Intermediate Similarity	NPD6781	Approved
0.7344	Intermediate Similarity	NPD6779	Approved
0.7344	Intermediate Similarity	NPD6782	Approved
0.7344	Intermediate Similarity	NPD6778	Approved
0.7344	Intermediate Similarity	NPD6780	Approved
0.7344	Intermediate Similarity	NPD6777	Approved
0.7344	Intermediate Similarity	NPD6776	Approved
0.7341	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7337	Intermediate Similarity	NPD7390	Discontinued
0.7329	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7314	Intermediate Similarity	NPD5353	Approved
0.7303	Intermediate Similarity	NPD8127	Discontinued
0.7301	Intermediate Similarity	NPD6355	Discontinued
0.7292	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD7033	Discontinued
0.7251	Intermediate Similarity	NPD6273	Approved
0.725	Intermediate Similarity	NPD2861	Phase 2
0.7222	Intermediate Similarity	NPD2313	Discontinued
0.7222	Intermediate Similarity	NPD5242	Approved
0.7205	Intermediate Similarity	NPD4908	Phase 1
0.7202	Intermediate Similarity	NPD6674	Discontinued
0.7195	Intermediate Similarity	NPD5124	Phase 1
0.7195	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7189	Intermediate Similarity	NPD7549	Discontinued
0.7188	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7186	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7186	Intermediate Similarity	NPD7874	Approved
0.7186	Intermediate Similarity	NPD2344	Approved
0.7179	Intermediate Similarity	NPD5006	Approved
0.7179	Intermediate Similarity	NPD5005	Approved
0.7178	Intermediate Similarity	NPD6233	Phase 2
0.7173	Intermediate Similarity	NPD4363	Phase 3
0.7173	Intermediate Similarity	NPD4360	Phase 2
0.716	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD4625	Phase 3
0.716	Intermediate Similarity	NPD4110	Phase 3
0.716	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7159	Intermediate Similarity	NPD8455	Phase 2
0.7152	Intermediate Similarity	NPD1608	Approved
0.7143	Intermediate Similarity	NPD7680	Approved
0.7143	Intermediate Similarity	NPD7697	Approved
0.7143	Intermediate Similarity	NPD7698	Approved
0.7143	Intermediate Similarity	NPD7696	Phase 3
0.7129	Intermediate Similarity	NPD7930	Approved
0.7126	Intermediate Similarity	NPD5405	Approved
0.7126	Intermediate Similarity	NPD5406	Approved
0.7126	Intermediate Similarity	NPD5404	Approved
0.7126	Intermediate Similarity	NPD7458	Discontinued
0.7126	Intermediate Similarity	NPD5408	Approved
0.7125	Intermediate Similarity	NPD1203	Approved
0.7125	Intermediate Similarity	NPD2797	Approved
0.7117	Intermediate Similarity	NPD3764	Approved
0.7117	Intermediate Similarity	NPD3268	Approved
0.7117	Intermediate Similarity	NPD6798	Discontinued
0.7107	Intermediate Similarity	NPD7870	Phase 2
0.7107	Intermediate Similarity	NPD7871	Phase 2
0.7099	Intermediate Similarity	NPD6832	Phase 2
0.7095	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7092	Intermediate Similarity	NPD6823	Phase 2
0.7091	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD1610	Phase 2
0.7088	Intermediate Similarity	NPD2403	Approved
0.7085	Intermediate Similarity	NPD7701	Phase 2
0.7083	Intermediate Similarity	NPD6002	Phase 3
0.7083	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD6005	Phase 3
0.7083	Intermediate Similarity	NPD6004	Phase 3
0.7083	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD6535	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