NPASS Compound

Structure

NPC83763 OpenBabel07101718242D 31 33 0 0 0 0 0 0 0 0999 V2000 5.1120 -0.8765 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2459 -2.3765 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0904 3.3780 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9609 1.6508 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7818 3.6235 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3799 -0.8765 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5299 2.6265 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3799 0.1235 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9665 1.8003 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6479 0.1235 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5382 2.8507 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2459 -1.3765 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5271 2.5518 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5139 0.6235 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9693 1.8750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5355 2.7760 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9749 2.0245 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7818 0.6235 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4088 1.1235 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5139 1.6235 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4060 1.0488 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7818 1.6235 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6479 2.1235 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9749 0.2225 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0988 3.6022 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 -2.8399 0.1478 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5984 -0.5593 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6479 3.1235 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 2.2470 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 12 1 0 0 0 0 2 12 1 0 0 0 0 3 13 1 0 0 0 0 4 13 1 0 0 0 0 5 29 1 0 0 0 0 6 8 1 0 0 0 0 6 12 2 0 0 0 0 7 9 1 0 0 0 0 7 13 2 0 0 0 0 8 14 1 0 0 0 0 9 15 1 0 0 0 0 10 14 2 0 0 0 0 10 18 1 0 0 0 0 11 16 2 0 0 0 0 11 17 1 0 0 0 0 14 20 1 0 0 0 0 15 16 1 0 0 0 0 15 21 2 0 0 0 0 16 25 1 0 0 0 0 17 19 2 0 0 0 0 17 30 1 0 0 0 0 18 22 2 0 0 0 0 18 31 1 0 0 0 0 19 21 1 0 0 0 0 19 24 1 0 0 0 0 20 23 2 0 0 0 0 20 26 1 0 0 0 0 21 27 1 0 0 0 0 22 23 1 0 0 0 0 22 30 1 0 0 0 0 23 29 1 0 0 0 0 24 28 2 0 0 0 0 24 31 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	426.17
Volume:	435.794
LogP:	6.415
LogD:	3.67
LogS:	-3.681
# Rotatable Bonds:	5
TPSA:	105.45
# H-Bond Aceptor:	7
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.345
Synthetic Accessibility Score:	3.372
Fsp3:	0.292
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:	-4.99
MDCK Permeability:	1.781190985639114e-05
Pgp-inhibitor:	0.843
Pgp-substrate:	0.294
Human Intestinal Absorption (HIA):	0.163
20% Bioavailability (F20%):	0.939
30% Bioavailability (F30%):	0.004

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.004
Plasma Protein Binding (PPB):	90.29573822021484%
Volume Distribution (VD):	0.815
Pgp-substrate:	16.334768295288086%

ADMET: Metabolism

CYP1A2-inhibitor:	0.385
CYP1A2-substrate:	0.174
CYP2C19-inhibitor:	0.831
CYP2C19-substrate:	0.084
CYP2C9-inhibitor:	0.73
CYP2C9-substrate:	0.822
CYP2D6-inhibitor:	0.032
CYP2D6-substrate:	0.236
CYP3A4-inhibitor:	0.17
CYP3A4-substrate:	0.114

ADMET: Excretion

Clearance (CL):	12.764
Half-life (T1/2):	0.241

ADMET: Toxicity

hERG Blockers:	0.009
Human Hepatotoxicity (H-HT):	0.193
Drug-inuced Liver Injury (DILI):	0.341
AMES Toxicity:	0.019
Rat Oral Acute Toxicity:	0.951
Maximum Recommended Daily Dose:	0.656
Skin Sensitization:	0.926
Carcinogencity:	0.119
Eye Corrosion:	0.003
Eye Irritation:	0.895
Respiratory Toxicity:	0.653

Download Data

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

Natural Product: NPC83763

Natural Product ID:	NPC83763
*Common Name:**	Paucinervin A
IUPAC Name:	2,7,9-trihydroxy-1-methoxy-3,8-bis(3-methylbut-2-enyl)benzo[b][1,4]benzodioxepin-6-one
Synonyms:
Standard InCHIKey:	CZKGIKZOHGKQSQ-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C24H26O7/c1-12(2)6-8-14-10-18-22(23(29-5)20(14)26)30-17-11-16(25)15(9-7-13(3)4)21(27)19(17)24(28)31-18/h6-7,10-11,25-27H,8-9H2,1-5H3
SMILES:	COc1c2Oc3cc(O)c(c(c3C(=O)Oc2cc(c1O)CC=C(C)C)O)CC=C(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1253932
PubChem CID:	52949770
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0001645] Depsides and depsidones

*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
NPO15264	Garcinia paucinervis	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20594858]
NPO15264	Garcinia paucinervis	Species	Clusiaceae	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
IC50	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	95600.0	nM	PMID[519175]

☑ 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 NPC83763 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	1730
0.2-0.3	4560
0.3-0.4	10143
0.4-0.5	7742
0.5-0.6	3517
0.6-0.7	4973
0.7-0.8	5835
0.8-0.85	2681
0.85-0.9	954
0.9-0.95	175
0.95-1	9

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC168616
0.974	High Similarity	NPC234004
0.9735	High Similarity	NPC472456
0.9675	High Similarity	NPC8300
0.9608	High Similarity	NPC238381
0.9551	High Similarity	NPC85057
0.9551	High Similarity	NPC130920
0.9536	High Similarity	NPC289968
0.9487	High Similarity	NPC156082
0.9427	High Similarity	NPC112981
0.9412	High Similarity	NPC471800
0.9408	High Similarity	NPC199773
0.9367	High Similarity	NPC20216
0.9308	High Similarity	NPC272485
0.9308	High Similarity	NPC292788
0.9304	High Similarity	NPC8070
0.9295	High Similarity	NPC292415
0.929	High Similarity	NPC36852
0.929	High Similarity	NPC78225
0.929	High Similarity	NPC262286
0.929	High Similarity	NPC223787
0.9281	High Similarity	NPC471982
0.9259	High Similarity	NPC139350
0.9241	High Similarity	NPC474350
0.9241	High Similarity	NPC300984
0.9236	High Similarity	NPC103201
0.9236	High Similarity	NPC349525
0.9236	High Similarity	NPC303565
0.9236	High Similarity	NPC473106
0.9226	High Similarity	NPC138243
0.9226	High Similarity	NPC54928
0.9226	High Similarity	NPC191146
0.9226	High Similarity	NPC68093
0.9221	High Similarity	NPC298802
0.9221	High Similarity	NPC475895
0.9193	High Similarity	NPC239440
0.9193	High Similarity	NPC17219
0.9193	High Similarity	NPC109827
0.9193	High Similarity	NPC20543
0.9193	High Similarity	NPC124470
0.9193	High Similarity	NPC246716
0.9182	High Similarity	NPC267153
0.9177	High Similarity	NPC93739
0.9172	High Similarity	NPC200594
0.9172	High Similarity	NPC14353
0.9172	High Similarity	NPC228785
0.9172	High Similarity	NPC246478
0.9172	High Similarity	NPC476980
0.9172	High Similarity	NPC56085
0.9161	High Similarity	NPC470327
0.9161	High Similarity	NPC113906
0.9161	High Similarity	NPC45849
0.9161	High Similarity	NPC200761
0.9161	High Similarity	NPC286052
0.9161	High Similarity	NPC477503
0.9156	High Similarity	NPC249570
0.9136	High Similarity	NPC158226
0.913	High Similarity	NPC26568
0.913	High Similarity	NPC163130
0.913	High Similarity	NPC165979
0.9125	High Similarity	NPC472452
0.9119	High Similarity	NPC284007
0.9114	High Similarity	NPC61010
0.9114	High Similarity	NPC278052
0.9114	High Similarity	NPC40491
0.9114	High Similarity	NPC266314
0.9114	High Similarity	NPC258331
0.9108	High Similarity	NPC250214
0.9108	High Similarity	NPC100123
0.9108	High Similarity	NPC95936
0.9103	High Similarity	NPC209614
0.9103	High Similarity	NPC278778
0.9103	High Similarity	NPC291878
0.9103	High Similarity	NPC472626
0.9103	High Similarity	NPC470328
0.9103	High Similarity	NPC195796
0.9103	High Similarity	NPC35038
0.9097	High Similarity	NPC231018
0.9097	High Similarity	NPC47781
0.9097	High Similarity	NPC145379
0.9097	High Similarity	NPC276409
0.9097	High Similarity	NPC22519
0.9097	High Similarity	NPC476631
0.9097	High Similarity	NPC176775
0.9097	High Similarity	NPC274327
0.9097	High Similarity	NPC75279
0.9097	High Similarity	NPC183878
0.9097	High Similarity	NPC160951
0.9097	High Similarity	NPC255350
0.9097	High Similarity	NPC250822
0.9097	High Similarity	NPC69394
0.9091	High Similarity	NPC113446
0.9085	High Similarity	NPC177298
0.9085	High Similarity	NPC328119
0.9085	High Similarity	NPC48479
0.908	High Similarity	NPC181523
0.9074	High Similarity	NPC10576
0.9074	High Similarity	NPC1827
0.9057	High Similarity	NPC83922
0.9057	High Similarity	NPC81679
0.9057	High Similarity	NPC472448
0.9051	High Similarity	NPC204290
0.9051	High Similarity	NPC320359
0.9045	High Similarity	NPC474836
0.9045	High Similarity	NPC222814
0.9045	High Similarity	NPC300727
0.9045	High Similarity	NPC96167
0.9045	High Similarity	NPC475267
0.9045	High Similarity	NPC469584
0.9045	High Similarity	NPC472913
0.9045	High Similarity	NPC472910
0.9045	High Similarity	NPC156057
0.9045	High Similarity	NPC472598
0.9045	High Similarity	NPC291508
0.9045	High Similarity	NPC472911
0.9045	High Similarity	NPC27337
0.9045	High Similarity	NPC241904
0.9045	High Similarity	NPC48208
0.9045	High Similarity	NPC474208
0.9045	High Similarity	NPC162869
0.9045	High Similarity	NPC108456
0.9045	High Similarity	NPC165977
0.9045	High Similarity	NPC474055
0.9045	High Similarity	NPC472914
0.9045	High Similarity	NPC217677
0.9045	High Similarity	NPC476981
0.9045	High Similarity	NPC245758
0.9038	High Similarity	NPC117992
0.9038	High Similarity	NPC230149
0.9038	High Similarity	NPC196439
0.9038	High Similarity	NPC4455
0.9038	High Similarity	NPC227325
0.9038	High Similarity	NPC213622
0.9038	High Similarity	NPC130589
0.9038	High Similarity	NPC2476
0.9038	High Similarity	NPC201136
0.9038	High Similarity	NPC128863
0.9038	High Similarity	NPC57674
0.9038	High Similarity	NPC20541
0.9038	High Similarity	NPC168247
0.9038	High Similarity	NPC138360
0.9038	High Similarity	NPC280339
0.9038	High Similarity	NPC50715
0.9038	High Similarity	NPC256612
0.9038	High Similarity	NPC146165
0.9038	High Similarity	NPC20830
0.9038	High Similarity	NPC183597
0.9038	High Similarity	NPC92659
0.9038	High Similarity	NPC134287
0.9038	High Similarity	NPC208197
0.9038	High Similarity	NPC234255
0.9038	High Similarity	NPC163780
0.9038	High Similarity	NPC152951
0.9038	High Similarity	NPC167815
0.9032	High Similarity	NPC131624
0.9032	High Similarity	NPC188203
0.9032	High Similarity	NPC106976
0.9032	High Similarity	NPC239128
0.9032	High Similarity	NPC156222
0.9032	High Similarity	NPC275722
0.9032	High Similarity	NPC199100
0.9032	High Similarity	NPC83508
0.9032	High Similarity	NPC100887
0.9032	High Similarity	NPC241498
0.9032	High Similarity	NPC198826
0.9032	High Similarity	NPC301323
0.9032	High Similarity	NPC101996
0.9032	High Similarity	NPC212678
0.9032	High Similarity	NPC180234
0.9032	High Similarity	NPC275836
0.9032	High Similarity	NPC25270
0.9032	High Similarity	NPC71334
0.9032	High Similarity	NPC222830
0.9032	High Similarity	NPC187498
0.9032	High Similarity	NPC256283
0.9032	High Similarity	NPC162313
0.9032	High Similarity	NPC57030
0.9032	High Similarity	NPC293183
0.9032	High Similarity	NPC120163
0.9032	High Similarity	NPC120537
0.9026	High Similarity	NPC225129
0.9026	High Similarity	NPC3825
0.9026	High Similarity	NPC88804
0.9024	High Similarity	NPC289147
0.902	High Similarity	NPC120464
0.9012	High Similarity	NPC49487
0.9012	High Similarity	NPC99613
0.9006	High Similarity	NPC29160
0.9	High Similarity	NPC248638
0.9	High Similarity	NPC470459
0.9	High Similarity	NPC41301
0.9	High Similarity	NPC270837
0.9	High Similarity	NPC236521
0.9	High Similarity	NPC220313
0.9	High Similarity	NPC236132
0.9	High Similarity	NPC152659
0.9	High Similarity	NPC7483
0.8994	High Similarity	NPC29876
0.8994	High Similarity	NPC167678
0.8994	High Similarity	NPC259456

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 NPC83763 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	345
0.1-0.2	983
0.2-0.3	1951
0.3-0.4	2605
0.4-0.5	1676
0.5-0.6	973
0.6-0.7	445
0.7-0.8	127
0.8-0.85	33
0.85-0.9	10
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9097	High Similarity	NPD2801	Approved
0.8974	High Similarity	NPD2393	Clinical (unspecified phase)
0.891	High Similarity	NPD1934	Approved
0.8679	High Similarity	NPD3817	Phase 2
0.8636	High Similarity	NPD1511	Approved
0.8625	High Similarity	NPD4868	Clinical (unspecified phase)
0.8625	High Similarity	NPD3882	Suspended
0.8589	High Similarity	NPD6232	Discontinued
0.8554	High Similarity	NPD5844	Phase 1
0.8526	High Similarity	NPD1512	Approved
0.8485	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8485	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8485	Intermediate Similarity	NPD6166	Phase 2
0.8462	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8462	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8457	Intermediate Similarity	NPD7075	Discontinued
0.8434	Intermediate Similarity	NPD7473	Discontinued
0.8421	Intermediate Similarity	NPD2935	Discontinued
0.8393	Intermediate Similarity	NPD7074	Phase 3
0.8385	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8385	Intermediate Similarity	NPD1465	Phase 2
0.8383	Intermediate Similarity	NPD3818	Discontinued
0.8354	Intermediate Similarity	NPD5494	Approved
0.8333	Intermediate Similarity	NPD7054	Approved
0.8284	Intermediate Similarity	NPD7472	Approved
0.828	Intermediate Similarity	NPD6799	Approved
0.8272	Intermediate Similarity	NPD7819	Suspended
0.821	Intermediate Similarity	NPD6801	Discontinued
0.8199	Intermediate Similarity	NPD4380	Phase 2
0.8194	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8182	Intermediate Similarity	NPD919	Approved
0.8148	Intermediate Similarity	NPD7411	Suspended
0.8129	Intermediate Similarity	NPD6797	Phase 2
0.8129	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8113	Intermediate Similarity	NPD2532	Approved
0.8113	Intermediate Similarity	NPD2534	Approved
0.8113	Intermediate Similarity	NPD2533	Approved
0.8086	Intermediate Similarity	NPD6599	Discontinued
0.8081	Intermediate Similarity	NPD7251	Discontinued
0.8039	Intermediate Similarity	NPD230	Phase 1
0.8039	Intermediate Similarity	NPD447	Suspended
0.8035	Intermediate Similarity	NPD7808	Phase 3
0.8013	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8013	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8012	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD5402	Approved
0.7976	Intermediate Similarity	NPD1247	Approved
0.7974	Intermediate Similarity	NPD1240	Approved
0.7962	Intermediate Similarity	NPD1549	Phase 2
0.7952	Intermediate Similarity	NPD7768	Phase 2
0.7911	Intermediate Similarity	NPD1243	Approved
0.7907	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7892	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7885	Intermediate Similarity	NPD1510	Phase 2
0.7885	Intermediate Similarity	NPD2799	Discontinued
0.7874	Intermediate Similarity	NPD6559	Discontinued
0.7871	Intermediate Similarity	NPD1607	Approved
0.787	Intermediate Similarity	NPD6959	Discontinued
0.7865	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD943	Approved
0.7843	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7836	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7834	Intermediate Similarity	NPD1551	Phase 2
0.7834	Intermediate Similarity	NPD2796	Approved
0.7799	Intermediate Similarity	NPD2800	Approved
0.7799	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7791	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7791	Intermediate Similarity	NPD920	Approved
0.7763	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7751	Intermediate Similarity	NPD6234	Discontinued
0.775	Intermediate Similarity	NPD4628	Phase 3
0.775	Intermediate Similarity	NPD3750	Approved
0.7744	Intermediate Similarity	NPD1653	Approved
0.7716	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7712	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD3226	Approved
0.7692	Intermediate Similarity	NPD3749	Approved
0.7683	Intermediate Similarity	NPD5403	Approved
0.7674	Intermediate Similarity	NPD3926	Phase 2
0.7669	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7662	Intermediate Similarity	NPD3027	Phase 3
0.7661	Intermediate Similarity	NPD7199	Phase 2
0.7654	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7632	Intermediate Similarity	NPD1203	Approved
0.7628	Intermediate Similarity	NPD1613	Approved
0.7628	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7614	Intermediate Similarity	NPD5953	Discontinued
0.76	Intermediate Similarity	NPD7286	Phase 2
0.758	Intermediate Similarity	NPD1933	Approved
0.7572	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7561	Intermediate Similarity	NPD5401	Approved
0.756	Intermediate Similarity	NPD37	Approved
0.7532	Intermediate Similarity	NPD6651	Approved
0.7531	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7531	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7529	Intermediate Similarity	NPD4967	Phase 2
0.7529	Intermediate Similarity	NPD4966	Approved
0.7529	Intermediate Similarity	NPD4965	Approved
0.7514	Intermediate Similarity	NPD5711	Approved
0.7514	Intermediate Similarity	NPD5710	Approved
0.75	Intermediate Similarity	NPD2313	Discontinued
0.75	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7486	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD6190	Approved
0.7484	Intermediate Similarity	NPD6832	Phase 2
0.7468	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7453	Intermediate Similarity	NPD2346	Discontinued
0.7443	Intermediate Similarity	NPD7228	Approved
0.7438	Intermediate Similarity	NPD3748	Approved
0.7438	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7434	Intermediate Similarity	NPD9717	Approved
0.7434	Intermediate Similarity	NPD9269	Phase 2
0.7371	Intermediate Similarity	NPD5242	Approved
0.7368	Intermediate Similarity	NPD422	Phase 1
0.7329	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD1608	Approved
0.7308	Intermediate Similarity	NPD9494	Approved
0.7302	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7296	Intermediate Similarity	NPD4060	Phase 1
0.729	Intermediate Similarity	NPD2797	Approved
0.7289	Intermediate Similarity	NPD7390	Discontinued
0.7284	Intermediate Similarity	NPD6099	Approved
0.7284	Intermediate Similarity	NPD6100	Approved
0.7278	Intermediate Similarity	NPD3268	Approved
0.7278	Intermediate Similarity	NPD411	Approved
0.7273	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD5353	Approved
0.7239	Intermediate Similarity	NPD2344	Approved
0.7238	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7234	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7233	Intermediate Similarity	NPD6233	Phase 2
0.7222	Intermediate Similarity	NPD7033	Discontinued
0.7222	Intermediate Similarity	NPD4308	Phase 3
0.7216	Intermediate Similarity	NPD7229	Phase 3
0.7202	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7198	Intermediate Similarity	NPD8312	Approved
0.7198	Intermediate Similarity	NPD8313	Approved
0.7194	Intermediate Similarity	NPD7783	Phase 2
0.7194	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD6386	Approved
0.7193	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD6385	Approved
0.7182	Intermediate Similarity	NPD7685	Pre-registration
0.7174	Intermediate Similarity	NPD8434	Phase 2
0.7171	Intermediate Similarity	NPD9268	Approved
0.717	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD1296	Phase 2
0.717	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD6798	Discontinued
0.7151	Intermediate Similarity	NPD3751	Discontinued
0.7143	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7549	Discontinued
0.7143	Intermediate Similarity	NPD6355	Discontinued
0.7143	Intermediate Similarity	NPD5124	Phase 1
0.7143	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD17	Approved
0.7119	Intermediate Similarity	NPD3787	Discontinued
0.7115	Intermediate Similarity	NPD3225	Approved
0.7098	Intermediate Similarity	NPD7435	Discontinued
0.7097	Intermediate Similarity	NPD1481	Phase 2
0.7092	Intermediate Similarity	NPD8151	Discontinued
0.7081	Intermediate Similarity	NPD8150	Discontinued
0.7078	Intermediate Similarity	NPD3496	Discontinued
0.7076	Intermediate Similarity	NPD7458	Discontinued
0.7076	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD5408	Approved
0.7073	Intermediate Similarity	NPD4476	Approved
0.7073	Intermediate Similarity	NPD4477	Approved
0.7073	Intermediate Similarity	NPD5405	Approved
0.7073	Intermediate Similarity	NPD5406	Approved
0.7073	Intermediate Similarity	NPD5404	Approved
0.7066	Intermediate Similarity	NPD2309	Approved
0.7062	Intermediate Similarity	NPD8127	Discontinued
0.7048	Intermediate Similarity	NPD1652	Phase 2
0.7044	Intermediate Similarity	NPD4908	Phase 1
0.7032	Intermediate Similarity	NPD1535	Discovery
0.7031	Intermediate Similarity	NPD6781	Approved
0.7031	Intermediate Similarity	NPD6780	Approved
0.7031	Intermediate Similarity	NPD6776	Approved
0.7031	Intermediate Similarity	NPD6777	Approved
0.7031	Intermediate Similarity	NPD6778	Approved
0.7031	Intermediate Similarity	NPD6779	Approved
0.7031	Intermediate Similarity	NPD6782	Approved
0.7025	Intermediate Similarity	NPD1019	Discontinued
0.7011	Intermediate Similarity	NPD8455	Phase 2
0.7006	Intermediate Similarity	NPD4110	Phase 3
0.7006	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD5049	Phase 3
0.7	Intermediate Similarity	NPD4625	Phase 3
0.6995	Remote Similarity	NPD7039	Approved
0.6995	Remote Similarity	NPD7240	Approved
0.6995	Remote Similarity	NPD7038	Approved
0.6993	Remote Similarity	NPD9545	Approved
0.6981	Remote Similarity	NPD3018	Phase 2
0.6975	Remote Similarity	NPD4307	Phase 2
0.6974	Remote Similarity	NPD9493	Approved
0.6973	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6971	Remote Similarity	NPD4288	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