NPASS Compound

Structure

CID314795 OpenBabel06191716132D 33 37 0 0 1 0 0 0 0 0999 V2000 -0.0000 -2.9211 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5297 2.4342 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0594 -0.9737 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2162 -1.4605 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0594 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8432 2.4342 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7236 -1.6252 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6865 -2.9211 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8432 -3.4079 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6865 1.9474 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.3729 -0.9737 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2162 0.4868 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.9474 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 -0.9737 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.3276 -2.5147 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3729 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5297 0.4868 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6865 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5297 -1.4605 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.9737 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8432 -1.4605 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6865 -0.9737 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8432 0.4868 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8432 -4.3816 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2162 1.4605 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8432 2.4342 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8144 -3.3579 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5297 1.4605 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5297 -2.4342 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8432 0.4868 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6408 -2.4129 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6865 0.9737 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 9 1 0 0 0 0 3 4 2 0 0 0 0 3 5 1 0 0 0 0 4 11 1 0 0 0 0 5 12 2 0 0 0 0 6 10 1 0 0 0 0 6 13 1 0 0 0 0 7 15 1 0 0 0 0 8 9 1 0 0 0 0 9 24 2 0 0 0 0 10 2 1 1 0 0 0 10 32 1 0 0 0 0 11 16 2 0 0 0 0 11 19 1 0 0 0 0 12 16 1 0 0 0 0 12 25 1 0 0 0 0 13 20 1 0 0 0 0 13 26 1 1 0 0 0 14 7 1 1 0 0 0 14 21 1 0 0 0 0 14 33 1 0 0 0 0 15 27 2 0 0 0 0 15 31 1 0 0 0 0 16 17 1 0 0 0 0 17 18 1 0 0 0 0 17 28 2 0 0 0 0 18 22 1 6 0 0 0 18 23 1 0 0 0 0 19 22 1 0 0 0 0 19 29 2 0 0 0 0 20 23 1 6 0 0 0 20 30 1 0 0 0 0 21 22 1 1 0 0 0 21 31 1 0 0 0 0 22 8 1 1 0 0 0 23 32 1 6 0 0 0 23 33 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	460.14
Volume:	433.029
LogP:	0.923
LogD:	0.146
LogS:	-3.354
# Rotatable Bonds:	2
TPSA:	156.66
# H-Bond Aceptor:	10
# H-Bond Donor:	3
# Rings:	5
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.524
Synthetic Accessibility Score:	5.629
Fsp3:	0.565
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.128
MDCK Permeability:	1.1956729395024013e-05
Pgp-inhibitor:	0.035
Pgp-substrate:	0.998
Human Intestinal Absorption (HIA):	0.129
20% Bioavailability (F20%):	0.342
30% Bioavailability (F30%):	0.993

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.163
Plasma Protein Binding (PPB):	54.464054107666016%
Volume Distribution (VD):	0.785
Pgp-substrate:	36.07350158691406%

ADMET: Metabolism

CYP1A2-inhibitor:	0.017
CYP1A2-substrate:	0.811
CYP2C19-inhibitor:	0.022
CYP2C19-substrate:	0.152
CYP2C9-inhibitor:	0.018
CYP2C9-substrate:	0.138
CYP2D6-inhibitor:	0.007
CYP2D6-substrate:	0.129
CYP3A4-inhibitor:	0.593
CYP3A4-substrate:	0.259

ADMET: Excretion

Clearance (CL):	7.142
Half-life (T1/2):	0.292

ADMET: Toxicity

hERG Blockers:	0.086
Human Hepatotoxicity (H-HT):	0.937
Drug-inuced Liver Injury (DILI):	0.867
AMES Toxicity:	0.259
Rat Oral Acute Toxicity:	0.647
Maximum Recommended Daily Dose:	0.354
Skin Sensitization:	0.759
Carcinogencity:	0.482
Eye Corrosion:	0.003
Eye Irritation:	0.012
Respiratory Toxicity:	0.952

Download Data

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

Natural Product: NPC314795

Natural Product ID:	NPC314795
*Common Name:**	Griseusin F
IUPAC Name:	n.a.
Synonyms:	Griseusin F
Standard InCHIKey:	YETMEGFEJOTNIJ-ZYVHMCLZSA-N
Standard InCHI:	InChI=1S/C23H24O10/c1-9(24)8-22-18(17(28)16-11(19(22)29)4-3-5-12(16)25)23(20(30)13(26)6-10(2)32-23)33-14-7-15(27)31-21(14)22/h3-5,10,13-14,18,20-21,25-26,30H,6-8H2,1-2H3/t10-,13+,14-,18-,20-,21+,22-,23-/m1/s1
SMILES:	CC(=O)C[C@@]12[C@@H](C(=O)c3c(cccc3O)C1=O)[C@]1([C@@H]([C@H](C[C@@H](C)O1)O)O)O[C@@H]1CC(=O)O[C@H]21
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2164968
PubChem CID:	71460593
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001640] Naphthopyrans [CHEMONTID:0001641] Naphthopyranones

*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
NPO40248	0cardiopsis sp. YIM DT266	Strain	0cardiopsaceae	Bacteria	n.a.	n.a.	n.a.	PMID[23095059]

☑ 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
MIC	3

Activity Type	# Activity
Cell Line	4
NON-MOLECULAR	1
Organism	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT393	Cell Line	HCT-116	Homo sapiens	IC50	=	700.0	nM	PMID[558779]
NPT369	Cell Line	ACHN	Homo sapiens	IC50	=	550.0	nM	PMID[558779]
NPT2316	Cell Line	CFPAC-1	Homo sapiens	IC50	=	640.0	nM	PMID[558779]
NPT319	Cell Line	B16	Mus musculus	IC50	=	430.0	nM	PMID[558779]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	=	1.65	ug.mL-1	PMID[558779]
NPT729	Organism	Micrococcus luteus	Micrococcus luteus	MIC	=	1.27	ug.mL-1	PMID[558779]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	0.91	ug.mL-1	PMID[558779]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	820.0	nM	PMID[558779]

☑ 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 NPC314795 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	341
0.1-0.2	1184
0.2-0.3	2620
0.3-0.4	4700
0.4-0.5	9659
0.5-0.6	10273
0.6-0.7	8264
0.7-0.8	5436
0.8-0.85	195
0.85-0.9	23
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9167	High Similarity	NPC29552
0.8974	High Similarity	NPC209393
0.8974	High Similarity	NPC205172
0.8917	High Similarity	NPC3449
0.8896	High Similarity	NPC94781
0.8861	High Similarity	NPC283480
0.8861	High Similarity	NPC148323
0.8839	High Similarity	NPC44378
0.8839	High Similarity	NPC280753
0.8805	High Similarity	NPC208651
0.8805	High Similarity	NPC206641
0.8797	High Similarity	NPC174599
0.8797	High Similarity	NPC192219
0.8797	High Similarity	NPC82190
0.8758	High Similarity	NPC477627
0.8704	High Similarity	NPC97637
0.8704	High Similarity	NPC187934
0.8701	High Similarity	NPC170055
0.8659	High Similarity	NPC469419
0.8645	High Similarity	NPC285122
0.8636	High Similarity	NPC103910
0.8636	High Similarity	NPC300684
0.8636	High Similarity	NPC218866
0.8636	High Similarity	NPC84568
0.8636	High Similarity	NPC48130
0.8634	High Similarity	NPC53139
0.8599	High Similarity	NPC120171
0.8571	High Similarity	NPC21873
0.8562	High Similarity	NPC266469
0.8526	High Similarity	NPC120536
0.8509	High Similarity	NPC474861
0.8503	High Similarity	NPC478021
0.8491	Intermediate Similarity	NPC205918
0.8485	Intermediate Similarity	NPC470735
0.8485	Intermediate Similarity	NPC478022
0.8485	Intermediate Similarity	NPC478020
0.8485	Intermediate Similarity	NPC329647
0.8485	Intermediate Similarity	NPC178281
0.8485	Intermediate Similarity	NPC478026
0.8481	Intermediate Similarity	NPC474310
0.8452	Intermediate Similarity	NPC294501
0.8452	Intermediate Similarity	NPC183441
0.8452	Intermediate Similarity	NPC13989
0.8438	Intermediate Similarity	NPC474534
0.8438	Intermediate Similarity	NPC474533
0.8428	Intermediate Similarity	NPC475407
0.8428	Intermediate Similarity	NPC315520
0.8408	Intermediate Similarity	NPC470330
0.8402	Intermediate Similarity	NPC472054
0.8395	Intermediate Similarity	NPC478027
0.8385	Intermediate Similarity	NPC470408
0.8385	Intermediate Similarity	NPC218870
0.8385	Intermediate Similarity	NPC182921
0.8385	Intermediate Similarity	NPC474622
0.8385	Intermediate Similarity	NPC474824
0.8385	Intermediate Similarity	NPC474621
0.8377	Intermediate Similarity	NPC315578
0.8365	Intermediate Similarity	NPC267469
0.8365	Intermediate Similarity	NPC116292
0.8365	Intermediate Similarity	NPC179128
0.8365	Intermediate Similarity	NPC87630
0.8364	Intermediate Similarity	NPC278329
0.8364	Intermediate Similarity	NPC101116
0.8364	Intermediate Similarity	NPC146837
0.8364	Intermediate Similarity	NPC212099
0.8363	Intermediate Similarity	NPC469418
0.8354	Intermediate Similarity	NPC5568
0.8333	Intermediate Similarity	NPC191653
0.8333	Intermediate Similarity	NPC175477
0.8323	Intermediate Similarity	NPC469459
0.8312	Intermediate Similarity	NPC26924
0.8312	Intermediate Similarity	NPC295339
0.8304	Intermediate Similarity	NPC176246
0.8303	Intermediate Similarity	NPC293568
0.8303	Intermediate Similarity	NPC117943
0.8294	Intermediate Similarity	NPC203751
0.8274	Intermediate Similarity	NPC471295
0.8274	Intermediate Similarity	NPC63470
0.8272	Intermediate Similarity	NPC472128
0.8272	Intermediate Similarity	NPC472127
0.8269	Intermediate Similarity	NPC474300
0.8266	Intermediate Similarity	NPC475161
0.8266	Intermediate Similarity	NPC477860
0.8258	Intermediate Similarity	NPC327916
0.8258	Intermediate Similarity	NPC42262
0.8258	Intermediate Similarity	NPC147542
0.8258	Intermediate Similarity	NPC37992
0.8258	Intermediate Similarity	NPC241349
0.8258	Intermediate Similarity	NPC220496
0.8258	Intermediate Similarity	NPC32749
0.825	Intermediate Similarity	NPC35160
0.825	Intermediate Similarity	NPC247219
0.825	Intermediate Similarity	NPC162569
0.8247	Intermediate Similarity	NPC197666
0.8247	Intermediate Similarity	NPC126739
0.8247	Intermediate Similarity	NPC61590
0.8246	Intermediate Similarity	NPC474345
0.8246	Intermediate Similarity	NPC68381
0.8246	Intermediate Similarity	NPC294149
0.8242	Intermediate Similarity	NPC328093
0.8235	Intermediate Similarity	NPC472620
0.8232	Intermediate Similarity	NPC257309
0.8225	Intermediate Similarity	NPC222455
0.8221	Intermediate Similarity	NPC474501
0.8217	Intermediate Similarity	NPC476473
0.8217	Intermediate Similarity	NPC100242
0.8214	Intermediate Similarity	NPC149002
0.8214	Intermediate Similarity	NPC469396
0.8214	Intermediate Similarity	NPC469458
0.8214	Intermediate Similarity	NPC88176
0.8208	Intermediate Similarity	NPC72783
0.8205	Intermediate Similarity	NPC2681
0.8205	Intermediate Similarity	NPC272907
0.8205	Intermediate Similarity	NPC257003
0.8198	Intermediate Similarity	NPC324220
0.8198	Intermediate Similarity	NPC312630
0.8198	Intermediate Similarity	NPC475246
0.8198	Intermediate Similarity	NPC475233
0.8198	Intermediate Similarity	NPC289876
0.8198	Intermediate Similarity	NPC475054
0.8198	Intermediate Similarity	NPC102053
0.8194	Intermediate Similarity	NPC111422
0.8194	Intermediate Similarity	NPC29771
0.8194	Intermediate Similarity	NPC256463
0.8194	Intermediate Similarity	NPC216312
0.8194	Intermediate Similarity	NPC476477
0.8194	Intermediate Similarity	NPC306835
0.8194	Intermediate Similarity	NPC471602
0.8194	Intermediate Similarity	NPC299405
0.8193	Intermediate Similarity	NPC69868
0.8187	Intermediate Similarity	NPC471871
0.8187	Intermediate Similarity	NPC199357
0.8187	Intermediate Similarity	NPC85368
0.8187	Intermediate Similarity	NPC65118
0.8176	Intermediate Similarity	NPC314437
0.8171	Intermediate Similarity	NPC10945
0.8166	Intermediate Similarity	NPC107009
0.816	Intermediate Similarity	NPC469417
0.8155	Intermediate Similarity	NPC99216
0.8155	Intermediate Similarity	NPC265600
0.8155	Intermediate Similarity	NPC474301
0.815	Intermediate Similarity	NPC80360
0.8144	Intermediate Similarity	NPC472664
0.8144	Intermediate Similarity	NPC216752
0.8144	Intermediate Similarity	NPC315772
0.8141	Intermediate Similarity	NPC3218
0.814	Intermediate Similarity	NPC186800
0.814	Intermediate Similarity	NPC19056
0.814	Intermediate Similarity	NPC470667
0.814	Intermediate Similarity	NPC472665
0.814	Intermediate Similarity	NPC470583
0.814	Intermediate Similarity	NPC70862
0.814	Intermediate Similarity	NPC3718
0.8137	Intermediate Similarity	NPC478219
0.8133	Intermediate Similarity	NPC208676
0.8133	Intermediate Similarity	NPC130489
0.8133	Intermediate Similarity	NPC472055
0.8129	Intermediate Similarity	NPC478002
0.8129	Intermediate Similarity	NPC76128
0.8129	Intermediate Similarity	NPC324262
0.8129	Intermediate Similarity	NPC271385
0.8129	Intermediate Similarity	NPC477617
0.8129	Intermediate Similarity	NPC62800
0.8129	Intermediate Similarity	NPC5029
0.8129	Intermediate Similarity	NPC270027
0.8129	Intermediate Similarity	NPC30432
0.8129	Intermediate Similarity	NPC111536
0.8125	Intermediate Similarity	NPC81835
0.8118	Intermediate Similarity	NPC246274
0.8118	Intermediate Similarity	NPC476017
0.8118	Intermediate Similarity	NPC472619
0.8114	Intermediate Similarity	NPC478001
0.8113	Intermediate Similarity	NPC208293
0.8113	Intermediate Similarity	NPC212808
0.811	Intermediate Similarity	NPC471456
0.811	Intermediate Similarity	NPC314257
0.8103	Intermediate Similarity	NPC58538
0.8103	Intermediate Similarity	NPC195114
0.8098	Intermediate Similarity	NPC257847
0.8095	Intermediate Similarity	NPC121995
0.8092	Intermediate Similarity	NPC170018
0.8092	Intermediate Similarity	NPC92403
0.8092	Intermediate Similarity	NPC46958
0.8092	Intermediate Similarity	NPC66820
0.8092	Intermediate Similarity	NPC76112
0.8089	Intermediate Similarity	NPC471444
0.8086	Intermediate Similarity	NPC133430
0.8086	Intermediate Similarity	NPC469477
0.8086	Intermediate Similarity	NPC473966
0.8081	Intermediate Similarity	NPC98776
0.8075	Intermediate Similarity	NPC473719
0.8072	Intermediate Similarity	NPC470339
0.807	Intermediate Similarity	NPC477573
0.807	Intermediate Similarity	NPC298778
0.807	Intermediate Similarity	NPC475058
0.807	Intermediate Similarity	NPC470580
0.807	Intermediate Similarity	NPC477572
0.807	Intermediate Similarity	NPC477571
0.8061	Intermediate Similarity	NPC478223
0.8059	Intermediate Similarity	NPC472660

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 NPC314795 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	287
0.1-0.2	763
0.2-0.3	1579
0.3-0.4	2696
0.4-0.5	2289
0.5-0.6	1094
0.6-0.7	344
0.7-0.8	95
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
0.8092	Intermediate Similarity	NPD8312	Approved
0.8092	Intermediate Similarity	NPD8313	Approved
0.7978	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7853	Intermediate Similarity	NPD8150	Discontinued
0.7805	Intermediate Similarity	NPD3226	Approved
0.7701	Intermediate Similarity	NPD8319	Approved
0.7701	Intermediate Similarity	NPD8320	Phase 1
0.7692	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.767	Intermediate Similarity	NPD6559	Discontinued
0.7654	Intermediate Similarity	NPD8434	Phase 2
0.7651	Intermediate Similarity	NPD4380	Phase 2
0.7644	Intermediate Similarity	NPD3818	Discontinued
0.7632	Intermediate Similarity	NPD1470	Approved
0.7598	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7596	Intermediate Similarity	NPD6534	Approved
0.7596	Intermediate Similarity	NPD6535	Approved
0.7586	Intermediate Similarity	NPD7473	Discontinued
0.7569	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7568	Intermediate Similarity	NPD7699	Phase 2
0.7568	Intermediate Similarity	NPD7700	Phase 2
0.7557	Intermediate Similarity	NPD7074	Phase 3
0.7553	Intermediate Similarity	NPD7435	Discontinued
0.7541	Intermediate Similarity	NPD6213	Phase 3
0.7541	Intermediate Similarity	NPD6212	Phase 3
0.7541	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD7819	Suspended
0.7514	Intermediate Similarity	NPD6232	Discontinued
0.75	Intermediate Similarity	NPD7054	Approved
0.75	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7487	Intermediate Similarity	NPD6777	Approved
0.7487	Intermediate Similarity	NPD6779	Approved
0.7487	Intermediate Similarity	NPD6782	Approved
0.7487	Intermediate Similarity	NPD6778	Approved
0.7487	Intermediate Similarity	NPD6780	Approved
0.7487	Intermediate Similarity	NPD6781	Approved
0.7487	Intermediate Similarity	NPD6776	Approved
0.7485	Intermediate Similarity	NPD7075	Discontinued
0.7458	Intermediate Similarity	NPD7472	Approved
0.7455	Intermediate Similarity	NPD2533	Approved
0.7455	Intermediate Similarity	NPD2534	Approved
0.7455	Intermediate Similarity	NPD2532	Approved
0.7443	Intermediate Similarity	NPD7228	Approved
0.7438	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.743	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7423	Intermediate Similarity	NPD4628	Phase 3
0.7416	Intermediate Similarity	NPD6797	Phase 2
0.7405	Intermediate Similarity	NPD7966	Clinical (unspecified phase)
0.7399	Intermediate Similarity	NPD5494	Approved
0.7396	Intermediate Similarity	NPD7411	Suspended
0.7391	Intermediate Similarity	NPD5405	Approved
0.7391	Intermediate Similarity	NPD5408	Approved
0.7391	Intermediate Similarity	NPD5406	Approved
0.7391	Intermediate Similarity	NPD5404	Approved
0.7381	Intermediate Similarity	NPD7458	Discontinued
0.7374	Intermediate Similarity	NPD7251	Discontinued
0.7368	Intermediate Similarity	NPD7698	Approved
0.7368	Intermediate Similarity	NPD5402	Approved
0.7368	Intermediate Similarity	NPD7696	Phase 3
0.7368	Intermediate Similarity	NPD7697	Approved
0.7368	Intermediate Similarity	NPD1201	Approved
0.7368	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD8151	Discontinued
0.7356	Intermediate Similarity	NPD6959	Discontinued
0.7353	Intermediate Similarity	NPD37	Approved
0.7349	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7349	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7346	Intermediate Similarity	NPD7266	Discontinued
0.7346	Intermediate Similarity	NPD2346	Discontinued
0.7345	Intermediate Similarity	NPD7799	Discontinued
0.7341	Intermediate Similarity	NPD6234	Discontinued
0.7333	Intermediate Similarity	NPD7808	Phase 3
0.733	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.733	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.733	Intermediate Similarity	NPD6166	Phase 2
0.7326	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7326	Intermediate Similarity	NPD4965	Approved
0.7326	Intermediate Similarity	NPD4967	Phase 2
0.7326	Intermediate Similarity	NPD4966	Approved
0.7325	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD7874	Approved
0.7317	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7306	Intermediate Similarity	NPD7701	Phase 2
0.7303	Intermediate Similarity	NPD5844	Phase 1
0.7289	Intermediate Similarity	NPD7390	Discontinued
0.7278	Intermediate Similarity	NPD7685	Pre-registration
0.7251	Intermediate Similarity	NPD6801	Discontinued
0.7251	Intermediate Similarity	NPD1934	Approved
0.7247	Intermediate Similarity	NPD3751	Discontinued
0.7241	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.724	Intermediate Similarity	NPD7870	Phase 2
0.724	Intermediate Similarity	NPD7871	Phase 2
0.7235	Intermediate Similarity	NPD6599	Discontinued
0.7232	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7229	Intermediate Similarity	NPD3300	Phase 2
0.7212	Intermediate Similarity	NPD8166	Discontinued
0.7195	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7194	Intermediate Similarity	NPD7801	Approved
0.7184	Intermediate Similarity	NPD3749	Approved
0.7176	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD3764	Approved
0.7169	Intermediate Similarity	NPD6190	Approved
0.716	Intermediate Similarity	NPD5403	Approved
0.7158	Intermediate Similarity	NPD8407	Phase 2
0.7152	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD6823	Phase 2
0.7127	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD3882	Suspended
0.7125	Intermediate Similarity	NPD6663	Approved
0.711	Intermediate Similarity	NPD1465	Phase 2
0.7107	Intermediate Similarity	NPD7783	Phase 2
0.7107	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD6273	Approved
0.7089	Intermediate Similarity	NPD5736	Approved
0.7088	Intermediate Similarity	NPD7240	Approved
0.7088	Intermediate Similarity	NPD8368	Discontinued
0.7086	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD943	Approved
0.7073	Intermediate Similarity	NPD2935	Discontinued
0.7069	Intermediate Similarity	NPD3817	Phase 2
0.7062	Intermediate Similarity	NPD7199	Phase 2
0.7041	Intermediate Similarity	NPD5401	Approved
0.7026	Intermediate Similarity	NPD7211	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD7236	Approved
0.7022	Intermediate Similarity	NPD5710	Approved
0.7022	Intermediate Similarity	NPD3787	Discontinued
0.7022	Intermediate Similarity	NPD5711	Approved
0.7012	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD2801	Approved
0.7011	Intermediate Similarity	NPD8455	Phase 2
0.7006	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.6988	Remote Similarity	NPD1549	Phase 2
0.6982	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6982	Remote Similarity	NPD6799	Approved
0.6976	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD8127	Discontinued
0.6961	Remote Similarity	NPD8155	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD5026	Approved
0.6957	Remote Similarity	NPD4954	Approved
0.6957	Remote Similarity	NPD36	Approved
0.6957	Remote Similarity	NPD5028	Approved
0.6957	Remote Similarity	NPD5034	Approved
0.6957	Remote Similarity	NPD4955	Approved
0.6941	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD230	Phase 1
0.6928	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD7239	Suspended
0.6918	Remote Similarity	NPD2798	Approved
0.6915	Remote Similarity	NPD8360	Approved
0.6915	Remote Similarity	NPD8361	Approved
0.6915	Remote Similarity	NPD7930	Approved
0.6914	Remote Similarity	NPD5760	Phase 2
0.6914	Remote Similarity	NPD5761	Phase 2
0.6909	Remote Similarity	NPD2799	Discontinued
0.6909	Remote Similarity	NPD1510	Phase 2
0.6905	Remote Similarity	NPD7003	Approved
0.6905	Remote Similarity	NPD3750	Approved
0.6903	Remote Similarity	NPD3019	Approved
0.6903	Remote Similarity	NPD2932	Approved
0.6902	Remote Similarity	NPD5030	Phase 2
0.6898	Remote Similarity	NPD5037	Approved
0.6898	Remote Similarity	NPD5038	Approved
0.6891	Remote Similarity	NPD8285	Discontinued
0.6889	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD6099	Approved
0.6867	Remote Similarity	NPD6100	Approved
0.6855	Remote Similarity	NPD3094	Phase 2
0.6852	Remote Similarity	NPD2313	Discontinued
0.6845	Remote Similarity	NPD2800	Approved
0.6845	Remote Similarity	NPD5036	Approved
0.6842	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD2629	Approved
0.6836	Remote Similarity	NPD7768	Phase 2
0.6831	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.6828	Remote Similarity	NPD5035	Approved
0.6826	Remote Similarity	NPD2344	Approved
0.6826	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6826	Remote Similarity	NPD1471	Phase 3
0.6825	Remote Similarity	NPD8435	Approved
0.6811	Remote Similarity	NPD6764	Approved
0.6811	Remote Similarity	NPD6765	Approved
0.6807	Remote Similarity	NPD3299	Clinical (unspecified phase)
0.6807	Remote Similarity	NPD7033	Discontinued
0.6795	Remote Similarity	NPD5125	Phase 3
0.6795	Remote Similarity	NPD5126	Approved
0.6788	Remote Similarity	NPD1607	Approved
0.6784	Remote Similarity	NPD1511	Approved
0.6776	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD9545	Approved
0.6768	Remote Similarity	NPD1240	Approved
0.6766	Remote Similarity	NPD1551	Phase 2
0.6766	Remote Similarity	NPD2796	Approved
0.6765	Remote Similarity	NPD8404	Phase 2
0.6753	Remote Similarity	NPD9493	Approved
0.675	Remote Similarity	NPD1164	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