NPASS Compound

Structure

NPC8300 OpenBabel07101719522D 35 38 0 0 0 0 0 0 0 0999 V2000 9.3409 -1.5273 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.2114 0.1999 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0560 -4.6786 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6165 -5.4301 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5000 1.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7803 -0.7758 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4871 -3.7029 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3464 -1.6768 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4843 -3.6282 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 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 8.7775 -0.7011 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0532 -4.6039 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3492 -1.7515 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9182 -2.7272 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 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7887 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9154 -2.6525 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7859 -0.9253 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 2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3548 -1.9010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3548 -0.0990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.4787 -3.4787 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.2198 -0.0243 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.9783 0.6828 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3799 -2.1235 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3799 0.1235 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 14 1 0 0 0 0 2 14 1 0 0 0 0 3 15 1 0 0 0 0 4 15 1 0 0 0 0 5 28 1 0 0 0 0 6 28 1 0 0 0 0 7 9 1 0 0 0 0 7 14 2 0 0 0 0 8 10 1 0 0 0 0 8 15 2 0 0 0 0 9 16 1 0 0 0 0 10 17 1 0 0 0 0 11 12 2 0 0 0 0 11 18 1 0 0 0 0 12 28 1 0 0 0 0 13 19 2 0 0 0 0 13 20 1 0 0 0 0 16 22 2 0 0 0 0 16 23 1 0 0 0 0 17 22 1 0 0 0 0 17 26 2 0 0 0 0 18 24 2 0 0 0 0 18 25 1 0 0 0 0 19 24 1 0 0 0 0 19 29 1 0 0 0 0 20 25 2 0 0 0 0 20 33 1 0 0 0 0 21 23 2 0 0 0 0 21 26 1 0 0 0 0 21 27 1 0 0 0 0 22 30 1 0 0 0 0 23 31 1 0 0 0 0 24 35 1 0 0 0 0 25 34 1 0 0 0 0 26 33 1 0 0 0 0 27 32 2 0 0 0 0 27 34 1 0 0 0 0 28 35 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	478.2
Volume:	493.785
LogP:	7.937
LogD:	4.74
LogS:	-2.249
# Rotatable Bonds:	4
TPSA:	105.45
# H-Bond Aceptor:	7
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.268
Synthetic Accessibility Score:	3.689
Fsp3:	0.321
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.111
MDCK Permeability:	2.0235889678588137e-05
Pgp-inhibitor:	0.985
Pgp-substrate:	0.01
Human Intestinal Absorption (HIA):	0.818
20% Bioavailability (F20%):	0.968
30% Bioavailability (F30%):	0.005

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.003
Plasma Protein Binding (PPB):	94.57576751708984%
Volume Distribution (VD):	1.722
Pgp-substrate:	11.165120124816895%

ADMET: Metabolism

CYP1A2-inhibitor:	0.255
CYP1A2-substrate:	0.145
CYP2C19-inhibitor:	0.683
CYP2C19-substrate:	0.073
CYP2C9-inhibitor:	0.678
CYP2C9-substrate:	0.898
CYP2D6-inhibitor:	0.034
CYP2D6-substrate:	0.169
CYP3A4-inhibitor:	0.205
CYP3A4-substrate:	0.127

ADMET: Excretion

Clearance (CL):	7.328
Half-life (T1/2):	0.115

ADMET: Toxicity

hERG Blockers:	0.013
Human Hepatotoxicity (H-HT):	0.762
Drug-inuced Liver Injury (DILI):	0.102
AMES Toxicity:	0.011
Rat Oral Acute Toxicity:	0.999
Maximum Recommended Daily Dose:	0.792
Skin Sensitization:	0.899
Carcinogencity:	0.467
Eye Corrosion:	0.003
Eye Irritation:	0.608
Respiratory Toxicity:	0.776

Download Data

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

Natural Product: NPC8300

Natural Product ID:	NPC8300
*Common Name:**	Garcinisidone E
IUPAC Name:	n.a.
Synonyms:	Garcinisidone E
Standard InCHIKey:	OJUCEDRVOIIDBB-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C28H30O7/c1-14(2)7-9-16-22(30)17(10-8-15(3)4)26-21(23(16)31)27(32)34-25-18-11-12-28(5,6)35-24(18)19(29)13-20(25)33-26/h7-8,11-13,29-31H,9-10H2,1-6H3
SMILES:	CC(=CCc1c2Oc3cc(O)c4c(c3OC(=O)c2c(c(c1O)CC=C(C)C)O)C=CC(O4)(C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL518632
PubChem CID:	10838374
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000123] Benzopyrans [CHEMONTID:0003410] 1-benzopyrans [CHEMONTID:0003522] 2,2-dimethyl-1-benzopyrans

*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
NPO32536	Garcinia	Genus	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11429990]

☑ 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	1
Others	8

Activity Type	# Activity
Cell Line	4
Others	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT80	Cell Line	Raji	Homo sapiens	Activity	>	80.0	%	PMID[494790]
NPT80	Cell Line	Raji	Homo sapiens	Activity	=	70.0	%	PMID[494790]
NPT2	Others	Unspecified		Activity	=	0.0	%	PMID[494790]
NPT2	Others	Unspecified		Activity	=	40.0	%	PMID[494790]
NPT2	Others	Unspecified		Activity	=	71.1	%	PMID[494790]
NPT2	Others	Unspecified		Activity	=	90.2	%	PMID[494790]
NPT2	Others	Unspecified		IC50	=	350.0	molar ratio	PMID[494790]

☑ 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 NPC8300 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	396
0.1-0.2	1781
0.2-0.3	4537
0.3-0.4	10452
0.4-0.5	7389
0.5-0.6	3682
0.6-0.7	5220
0.7-0.8	6107
0.8-0.85	2389
0.85-0.9	667
0.9-0.95	71
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
0.9935	High Similarity	NPC234004
0.9871	High Similarity	NPC130920
0.9871	High Similarity	NPC85057
0.9675	High Similarity	NPC83763
0.9675	High Similarity	NPC168616
0.9545	High Similarity	NPC472456
0.9363	High Similarity	NPC204290
0.9363	High Similarity	NPC476980
0.9304	High Similarity	NPC29876
0.9304	High Similarity	NPC167678
0.9304	High Similarity	NPC259456
0.9299	High Similarity	NPC238381
0.9295	High Similarity	NPC471985
0.9295	High Similarity	NPC276444
0.9295	High Similarity	NPC191146
0.9295	High Similarity	NPC68093
0.9245	High Similarity	NPC472448
0.9245	High Similarity	NPC83922
0.9236	High Similarity	NPC476981
0.9236	High Similarity	NPC218871
0.9236	High Similarity	NPC476630
0.9236	High Similarity	NPC78225
0.9231	High Similarity	NPC472280
0.9231	High Similarity	NPC234255
0.9231	High Similarity	NPC471800
0.9226	High Similarity	NPC199773
0.9226	High Similarity	NPC289968
0.9226	High Similarity	NPC249570
0.9226	High Similarity	NPC471982
0.9226	High Similarity	NPC237994
0.9221	High Similarity	NPC88804
0.9221	High Similarity	NPC3825
0.9187	High Similarity	NPC23298
0.9187	High Similarity	NPC156082
0.9187	High Similarity	NPC189473
0.9182	High Similarity	NPC258331
0.9182	High Similarity	NPC349525
0.9172	High Similarity	NPC472455
0.9172	High Similarity	NPC138243
0.9167	High Similarity	NPC274327
0.9167	High Similarity	NPC69394
0.9167	High Similarity	NPC47781
0.9167	High Similarity	NPC255350
0.9167	High Similarity	NPC170492
0.9167	High Similarity	NPC160951
0.9167	High Similarity	NPC476631
0.9167	High Similarity	NPC231018
0.9167	High Similarity	NPC176775
0.9167	High Similarity	NPC145379
0.9167	High Similarity	NPC183878
0.9167	High Similarity	NPC22519
0.9167	High Similarity	NPC475895
0.9161	High Similarity	NPC154345
0.9141	High Similarity	NPC124470
0.9141	High Similarity	NPC109827
0.913	High Similarity	NPC275780
0.913	High Similarity	NPC112981
0.913	High Similarity	NPC8070
0.913	High Similarity	NPC472450
0.913	High Similarity	NPC239752
0.9125	High Similarity	NPC261470
0.9119	High Similarity	NPC292415
0.9119	High Similarity	NPC118256
0.9119	High Similarity	NPC192686
0.9119	High Similarity	NPC246478
0.9119	High Similarity	NPC119209
0.9114	High Similarity	NPC223787
0.9114	High Similarity	NPC27337
0.9114	High Similarity	NPC218313
0.9114	High Similarity	NPC36852
0.9114	High Similarity	NPC262286
0.9114	High Similarity	NPC474681
0.9108	High Similarity	NPC20830
0.9108	High Similarity	NPC183597
0.9108	High Similarity	NPC163780
0.9108	High Similarity	NPC128863
0.9108	High Similarity	NPC92659
0.9108	High Similarity	NPC50715
0.9108	High Similarity	NPC146165
0.9108	High Similarity	NPC227325
0.9108	High Similarity	NPC286052
0.9108	High Similarity	NPC2476
0.9108	High Similarity	NPC201136
0.9108	High Similarity	NPC256612
0.9108	High Similarity	NPC196439
0.9108	High Similarity	NPC167815
0.9108	High Similarity	NPC4455
0.9108	High Similarity	NPC138360
0.9108	High Similarity	NPC213622
0.9108	High Similarity	NPC280339
0.9103	High Similarity	NPC198826
0.9103	High Similarity	NPC256283
0.9103	High Similarity	NPC57030
0.9103	High Similarity	NPC100887
0.9103	High Similarity	NPC120163
0.9103	High Similarity	NPC212678
0.9103	High Similarity	NPC131624
0.9103	High Similarity	NPC25270
0.9103	High Similarity	NPC71334
0.9103	High Similarity	NPC162313
0.9103	High Similarity	NPC241498
0.9103	High Similarity	NPC239128
0.9103	High Similarity	NPC301323
0.9103	High Similarity	NPC293183
0.9103	High Similarity	NPC187498
0.9103	High Similarity	NPC188203
0.9103	High Similarity	NPC37684
0.9103	High Similarity	NPC63187
0.9103	High Similarity	NPC83508
0.9103	High Similarity	NPC157784
0.9103	High Similarity	NPC156222
0.9103	High Similarity	NPC222830
0.9103	High Similarity	NPC275836
0.9103	High Similarity	NPC275722
0.9085	High Similarity	NPC475669
0.9074	High Similarity	NPC37870
0.9074	High Similarity	NPC39091
0.9074	High Similarity	NPC472449
0.9074	High Similarity	NPC20216
0.9068	High Similarity	NPC306321
0.9068	High Similarity	NPC303460
0.9068	High Similarity	NPC474350
0.9062	High Similarity	NPC266314
0.9062	High Similarity	NPC473106
0.9062	High Similarity	NPC103201
0.9062	High Similarity	NPC61010
0.9062	High Similarity	NPC198829
0.9062	High Similarity	NPC303565
0.9062	High Similarity	NPC474038
0.9057	High Similarity	NPC100123
0.9057	High Similarity	NPC204879
0.9057	High Similarity	NPC184755
0.9057	High Similarity	NPC250214
0.9057	High Similarity	NPC74178
0.9057	High Similarity	NPC95936
0.9051	High Similarity	NPC5322
0.9051	High Similarity	NPC49824
0.9051	High Similarity	NPC195796
0.9051	High Similarity	NPC6633
0.9051	High Similarity	NPC35038
0.9051	High Similarity	NPC278778
0.9051	High Similarity	NPC133970
0.9051	High Similarity	NPC291878
0.9045	High Similarity	NPC227337
0.9045	High Similarity	NPC298802
0.9045	High Similarity	NPC273462
0.9045	High Similarity	NPC49402
0.9045	High Similarity	NPC250822
0.9045	High Similarity	NPC33051
0.9045	High Similarity	NPC276409
0.9045	High Similarity	NPC70433
0.9045	High Similarity	NPC75279
0.9042	High Similarity	NPC113446
0.9038	High Similarity	NPC308451
0.9038	High Similarity	NPC205046
0.9038	High Similarity	NPC208043
0.9038	High Similarity	NPC226973
0.9038	High Similarity	NPC59162
0.9038	High Similarity	NPC304295
0.9032	High Similarity	NPC223579
0.9032	High Similarity	NPC328119
0.9032	High Similarity	NPC137062
0.9032	High Similarity	NPC259713
0.9032	High Similarity	NPC48479
0.9032	High Similarity	NPC216318
0.9032	High Similarity	NPC52005
0.9032	High Similarity	NPC183950
0.9032	High Similarity	NPC17286
0.9032	High Similarity	NPC287101
0.9032	High Similarity	NPC296197
0.9032	High Similarity	NPC177298
0.9018	High Similarity	NPC272485
0.9018	High Similarity	NPC292788
0.9012	High Similarity	NPC50960
0.9006	High Similarity	NPC229632
0.9006	High Similarity	NPC474150
0.9006	High Similarity	NPC329760
0.9006	High Similarity	NPC93739
0.9006	High Similarity	NPC474162
0.9006	High Similarity	NPC81679
0.9006	High Similarity	NPC25152
0.9006	High Similarity	NPC194427
0.9006	High Similarity	NPC78332
0.9	High Similarity	NPC228785
0.9	High Similarity	NPC320359
0.9	High Similarity	NPC14353
0.9	High Similarity	NPC472624
0.9	High Similarity	NPC139036
0.9	High Similarity	NPC471973
0.9	High Similarity	NPC56085
0.9	High Similarity	NPC475784
0.9	High Similarity	NPC328102
0.8994	High Similarity	NPC291508
0.8994	High Similarity	NPC237418
0.8994	High Similarity	NPC136674
0.8994	High Similarity	NPC93376
0.8994	High Similarity	NPC162869
0.8994	High Similarity	NPC224137
0.8994	High Similarity	NPC203891
0.8994	High Similarity	NPC472913

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 NPC8300 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	361
0.1-0.2	981
0.2-0.3	1852
0.3-0.4	2672
0.4-0.5	1739
0.5-0.6	970
0.6-0.7	413
0.7-0.8	132
0.8-0.85	27
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9167	High Similarity	NPD2801	Approved
0.8924	High Similarity	NPD2393	Clinical (unspecified phase)
0.8861	High Similarity	NPD1934	Approved
0.8831	High Similarity	NPD1511	Approved
0.875	High Similarity	NPD3817	Phase 2
0.8718	High Similarity	NPD1512	Approved
0.8545	High Similarity	NPD6232	Discontinued
0.8535	High Similarity	NPD4378	Clinical (unspecified phase)
0.8529	High Similarity	NPD4338	Clinical (unspecified phase)
0.8512	High Similarity	NPD5844	Phase 1
0.8466	Intermediate Similarity	NPD3882	Suspended
0.8466	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8452	Intermediate Similarity	NPD3818	Discontinued
0.8443	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8443	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8443	Intermediate Similarity	NPD6166	Phase 2
0.8415	Intermediate Similarity	NPD7075	Discontinued
0.8402	Intermediate Similarity	NPD7054	Approved
0.8393	Intermediate Similarity	NPD7473	Discontinued
0.8353	Intermediate Similarity	NPD7074	Phase 3
0.8353	Intermediate Similarity	NPD7472	Approved
0.8344	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8344	Intermediate Similarity	NPD1465	Phase 2
0.8313	Intermediate Similarity	NPD5494	Approved
0.8302	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8282	Intermediate Similarity	NPD6801	Discontinued
0.8272	Intermediate Similarity	NPD4380	Phase 2
0.8258	Intermediate Similarity	NPD2935	Discontinued
0.8232	Intermediate Similarity	NPD7819	Suspended
0.8198	Intermediate Similarity	NPD6797	Phase 2
0.815	Intermediate Similarity	NPD7251	Discontinued
0.8144	Intermediate Similarity	NPD919	Approved
0.8125	Intermediate Similarity	NPD6799	Approved
0.811	Intermediate Similarity	NPD7411	Suspended
0.8103	Intermediate Similarity	NPD7808	Phase 3
0.8084	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8072	Intermediate Similarity	NPD5402	Approved
0.8038	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD447	Suspended
0.7989	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7977	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7975	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7975	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7962	Intermediate Similarity	NPD1510	Phase 2
0.7941	Intermediate Similarity	NPD1247	Approved
0.7939	Intermediate Similarity	NPD6599	Discontinued
0.7937	Intermediate Similarity	NPD3750	Approved
0.7925	Intermediate Similarity	NPD1549	Phase 2
0.7917	Intermediate Similarity	NPD7768	Phase 2
0.7911	Intermediate Similarity	NPD2796	Approved
0.7875	Intermediate Similarity	NPD1243	Approved
0.787	Intermediate Similarity	NPD3749	Approved
0.7857	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7853	Intermediate Similarity	NPD2533	Approved
0.7853	Intermediate Similarity	NPD2534	Approved
0.7853	Intermediate Similarity	NPD2532	Approved
0.7848	Intermediate Similarity	NPD2799	Discontinued
0.7841	Intermediate Similarity	NPD6559	Discontinued
0.7833	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7821	Intermediate Similarity	NPD943	Approved
0.7821	Intermediate Similarity	NPD1240	Approved
0.7818	Intermediate Similarity	NPD1653	Approved
0.7803	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7792	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD230	Phase 1
0.7771	Intermediate Similarity	NPD3226	Approved
0.7764	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7758	Intermediate Similarity	NPD920	Approved
0.7758	Intermediate Similarity	NPD5403	Approved
0.7758	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7733	Intermediate Similarity	NPD6959	Discontinued
0.7727	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7722	Intermediate Similarity	NPD1607	Approved
0.7692	Intermediate Similarity	NPD2313	Discontinued
0.7692	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7688	Intermediate Similarity	NPD1551	Phase 2
0.7683	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7654	Intermediate Similarity	NPD2800	Approved
0.7636	Intermediate Similarity	NPD5401	Approved
0.7636	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.763	Intermediate Similarity	NPD7199	Phase 2
0.7625	Intermediate Similarity	NPD3748	Approved
0.7622	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7616	Intermediate Similarity	NPD6234	Discontinued
0.7607	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7607	Intermediate Similarity	NPD4628	Phase 3
0.7597	Intermediate Similarity	NPD1203	Approved
0.7595	Intermediate Similarity	NPD1613	Approved
0.7595	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7569	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7561	Intermediate Similarity	NPD6190	Approved
0.7554	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7547	Intermediate Similarity	NPD1933	Approved
0.7543	Intermediate Similarity	NPD3926	Phase 2
0.7543	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7531	Intermediate Similarity	NPD2346	Discontinued
0.7516	Intermediate Similarity	NPD4308	Phase 3
0.7516	Intermediate Similarity	NPD3027	Phase 3
0.75	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7486	Intermediate Similarity	NPD5953	Discontinued
0.7484	Intermediate Similarity	NPD2797	Approved
0.7472	Intermediate Similarity	NPD7286	Phase 2
0.7468	Intermediate Similarity	NPD3268	Approved
0.7451	Intermediate Similarity	NPD422	Phase 1
0.7427	Intermediate Similarity	NPD37	Approved
0.7407	Intermediate Similarity	NPD7033	Discontinued
0.7407	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7403	Intermediate Similarity	NPD9717	Approved
0.7399	Intermediate Similarity	NPD4966	Approved
0.7399	Intermediate Similarity	NPD4967	Phase 2
0.7399	Intermediate Similarity	NPD4965	Approved
0.7362	Intermediate Similarity	NPD6099	Approved
0.7362	Intermediate Similarity	NPD6100	Approved
0.7348	Intermediate Similarity	NPD7685	Pre-registration
0.7342	Intermediate Similarity	NPD6832	Phase 2
0.7329	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD5124	Phase 1
0.7329	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7318	Intermediate Similarity	NPD7228	Approved
0.7308	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD7549	Discontinued
0.7308	Intermediate Similarity	NPD3225	Approved
0.7302	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7301	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD9269	Phase 2
0.729	Intermediate Similarity	NPD1608	Approved
0.7288	Intermediate Similarity	NPD5710	Approved
0.7288	Intermediate Similarity	NPD5711	Approved
0.7284	Intermediate Similarity	NPD6651	Approved
0.7277	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD4307	Phase 2
0.7262	Intermediate Similarity	NPD7390	Discontinued
0.7259	Intermediate Similarity	NPD7783	Phase 2
0.7259	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD411	Approved
0.725	Intermediate Similarity	NPD1296	Phase 2
0.7247	Intermediate Similarity	NPD5242	Approved
0.7243	Intermediate Similarity	NPD8434	Phase 2
0.7222	Intermediate Similarity	NPD3751	Discontinued
0.7212	Intermediate Similarity	NPD2344	Approved
0.7205	Intermediate Similarity	NPD6233	Phase 2
0.7191	Intermediate Similarity	NPD3787	Discontinued
0.7191	Intermediate Similarity	NPD7229	Phase 3
0.7188	Intermediate Similarity	NPD4625	Phase 3
0.7174	Intermediate Similarity	NPD8312	Approved
0.7174	Intermediate Similarity	NPD8313	Approved
0.717	Intermediate Similarity	NPD9494	Approved
0.7168	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7165	Intermediate Similarity	NPD7435	Discontinued
0.716	Intermediate Similarity	NPD4060	Phase 1
0.7152	Intermediate Similarity	NPD5404	Approved
0.7152	Intermediate Similarity	NPD5406	Approved
0.7152	Intermediate Similarity	NPD5405	Approved
0.7152	Intermediate Similarity	NPD5408	Approved
0.7152	Intermediate Similarity	NPD3266	Approved
0.7152	Intermediate Similarity	NPD3267	Approved
0.7151	Intermediate Similarity	NPD8150	Discontinued
0.7143	Intermediate Similarity	NPD4288	Approved
0.7143	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6798	Discontinued
0.7134	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD1652	Phase 2
0.7118	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD2798	Approved
0.7098	Intermediate Similarity	NPD6779	Approved
0.7098	Intermediate Similarity	NPD6776	Approved
0.7098	Intermediate Similarity	NPD6777	Approved
0.7098	Intermediate Similarity	NPD6782	Approved
0.7098	Intermediate Similarity	NPD6780	Approved
0.7098	Intermediate Similarity	NPD6781	Approved
0.7098	Intermediate Similarity	NPD6778	Approved
0.7097	Intermediate Similarity	NPD17	Approved
0.7081	Intermediate Similarity	NPD7095	Approved
0.7076	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7076	Intermediate Similarity	NPD5049	Phase 3
0.707	Intermediate Similarity	NPD1481	Phase 2
0.7069	Intermediate Similarity	NPD6386	Approved
0.7069	Intermediate Similarity	NPD6385	Approved
0.7056	Intermediate Similarity	NPD7584	Approved
0.7052	Intermediate Similarity	NPD7458	Discontinued
0.7052	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD5353	Approved
0.7041	Intermediate Similarity	NPD2354	Approved
0.7041	Intermediate Similarity	NPD2309	Approved
0.7039	Intermediate Similarity	NPD8127	Discontinued
0.7037	Intermediate Similarity	NPD3764	Approved
0.7032	Intermediate Similarity	NPD9268	Approved
0.702	Intermediate Similarity	NPD7585	Approved
0.7019	Intermediate Similarity	NPD4908	Phase 1
0.7018	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7016	Intermediate Similarity	NPD4363	Phase 3
0.7016	Intermediate Similarity	NPD4360	Phase 2
0.7012	Intermediate Similarity	NPD6355	Discontinued
0.7006	Intermediate Similarity	NPD1535	Discovery
0.6989	Remote Similarity	NPD8455	Phase 2
0.6985	Remote Similarity	NPD8151	Discontinued
0.6984	Remote Similarity	NPD4287	Approved
0.6973	Remote Similarity	NPD7038	Approved
0.6973	Remote Similarity	NPD7039	Approved
0.697	Remote Similarity	NPD7583	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