NPASS Compound

Structure

NPC22192 OpenBabel07101719152D 32 34 0 0 1 0 0 0 0 0999 V2000 -6.0622 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 1.5000 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 -6.0622 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -1.5000 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 2.5981 -0.5000 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 3.4641 -0.0000 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 -1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 1.0000 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 1.7321 -0.0000 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 3.4641 1.0000 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 2.5981 1.5000 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 -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 -0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 1 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 4.3301 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 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 13 1 0 0 0 0 2 13 1 0 0 0 0 3 14 1 0 0 0 0 4 5 1 0 0 0 0 4 6 1 0 0 0 0 5 13 2 0 0 0 0 6 14 1 0 0 0 0 7 9 1 0 0 0 0 7 14 2 0 0 0 0 8 10 2 0 0 0 0 8 15 1 0 0 0 0 9 16 1 0 0 0 0 10 17 1 0 0 0 0 11 15 2 0 0 0 0 11 19 1 0 0 0 0 12 18 2 0 0 0 0 12 20 1 0 0 0 0 16 18 1 0 0 0 0 16 22 2 0 0 0 0 17 19 2 0 0 0 0 17 26 1 0 0 0 0 18 27 1 0 0 0 0 19 28 1 0 0 0 0 20 21 2 0 0 0 0 20 32 1 0 0 0 0 21 22 1 0 0 0 0 21 23 1 0 0 0 0 22 29 1 0 0 0 0 23 24 1 0 0 0 0 23 30 2 0 0 0 0 24 25 1 0 0 0 0 24 31 1 1 0 0 0 25 15 1 6 0 0 0 25 32 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	440.18
Volume:	453.09
LogP:	5.028
LogD:	3.15
LogS:	-2.974
# Rotatable Bonds:	6
TPSA:	127.45
# H-Bond Aceptor:	7
# H-Bond Donor:	5
# Rings:	3
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.332
Synthetic Accessibility Score:	3.833
Fsp3:	0.32
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.167
MDCK Permeability:	8.251601684605703e-06
Pgp-inhibitor:	0.148
Pgp-substrate:	0.006
Human Intestinal Absorption (HIA):	0.03
20% Bioavailability (F20%):	0.964
30% Bioavailability (F30%):	0.995

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.005
Plasma Protein Binding (PPB):	96.70258331298828%
Volume Distribution (VD):	0.618
Pgp-substrate:	3.0938382148742676%

ADMET: Metabolism

CYP1A2-inhibitor:	0.196
CYP1A2-substrate:	0.163
CYP2C19-inhibitor:	0.469
CYP2C19-substrate:	0.058
CYP2C9-inhibitor:	0.866
CYP2C9-substrate:	0.807
CYP2D6-inhibitor:	0.905
CYP2D6-substrate:	0.253
CYP3A4-inhibitor:	0.254
CYP3A4-substrate:	0.155

ADMET: Excretion

Clearance (CL):	8.837
Half-life (T1/2):	0.53

ADMET: Toxicity

hERG Blockers:	0.011
Human Hepatotoxicity (H-HT):	0.244
Drug-inuced Liver Injury (DILI):	0.747
AMES Toxicity:	0.19
Rat Oral Acute Toxicity:	0.209
Maximum Recommended Daily Dose:	0.026
Skin Sensitization:	0.917
Carcinogencity:	0.17
Eye Corrosion:	0.003
Eye Irritation:	0.56
Respiratory Toxicity:	0.085

Download Data

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

Natural Product: NPC22192

Natural Product ID:	NPC22192
*Common Name:**	Diplacol
IUPAC Name:	(2R,3R)-2-(3,4-dihydroxyphenyl)-6-[(2E)-3,7-dimethylocta-2,6-dienyl]-3,5,7-trihydroxy-2,3-dihydrochromen-4-one
Synonyms:	Diplacol
Standard InCHIKey:	UESFDRVOHWXYIQ-PRANAVDNSA-N
Standard InCHI:	InChI=1S/C25H28O7/c1-13(2)5-4-6-14(3)7-9-16-18(27)12-20-21(22(16)29)23(30)24(31)25(32-20)15-8-10-17(26)19(28)11-15/h5,7-8,10-12,24-29,31H,4,6,9H2,1-3H3/b14-7+/t24-,25+/m0/s1
SMILES:	CC(=CCC/C(=C/Cc1c(cc2c(c1O)C(=O)[C@@H]([C@@H](c1ccc(c(c1)O)O)O2)O)O)/C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL411385
PubChem CID:	639466
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0000337] Flavans [CHEMONTID:0003646] 6-prenylated flavans [CHEMONTID:0003507] 6-prenylated flavanones

*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
NPO27255	Macaranga alnifolia	Species	Euphorbiaceae	Eukaryota	n.a.	leaf	n.a.	DOI[10.1016/0031-9422(92)80315-6]
NPO27255	Macaranga alnifolia	Species	Euphorbiaceae	Eukaryota	n.a.	Madagascar rainforest	n.a.	PMID[17326683]
NPO27255	Macaranga alnifolia	Species	Euphorbiaceae	Eukaryota	n.a.	fruit	n.a.	PMID[17326683]
NPO27255	Macaranga alnifolia	Species	Euphorbiaceae	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
NPT571	Cell Line	A2780cisR	Homo sapiens	IC50	=	11500.0	nM	PMID[468385]

☑ 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 NPC22192 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	403
0.1-0.2	1526
0.2-0.3	3925
0.3-0.4	9468
0.4-0.5	8737
0.5-0.6	3400
0.6-0.7	4738
0.7-0.8	5331
0.8-0.85	2887
0.85-0.9	1756
0.9-0.95	424
0.95-1	102

Similarity Score	Similarity Level	Natural Product ID
0.9934	High Similarity	NPC287328
0.9934	High Similarity	NPC282009
0.9868	High Similarity	NPC471499
0.9803	High Similarity	NPC470326
0.9801	High Similarity	NPC472598
0.9801	High Similarity	NPC474055
0.98	High Similarity	NPC321779
0.974	High Similarity	NPC472625
0.9739	High Similarity	NPC289771
0.9735	High Similarity	NPC471500
0.9735	High Similarity	NPC35038
0.9735	High Similarity	NPC320825
0.9735	High Similarity	NPC326037
0.9735	High Similarity	NPC195796
0.9735	High Similarity	NPC278778
0.9735	High Similarity	NPC13858
0.9735	High Similarity	NPC291878
0.9733	High Similarity	NPC192083
0.9733	High Similarity	NPC213896
0.9675	High Similarity	NPC211107
0.9673	High Similarity	NPC470183
0.9671	High Similarity	NPC27337
0.9671	High Similarity	NPC52530
0.9671	High Similarity	NPC291508
0.9671	High Similarity	NPC471515
0.9671	High Similarity	NPC471479
0.9669	High Similarity	NPC200761
0.9669	High Similarity	NPC45849
0.9669	High Similarity	NPC470327
0.9669	High Similarity	NPC477503
0.9667	High Similarity	NPC246162
0.9667	High Similarity	NPC36835
0.9667	High Similarity	NPC240476
0.9667	High Similarity	NPC260491
0.9667	High Similarity	NPC106976
0.9667	High Similarity	NPC9743
0.9667	High Similarity	NPC61506
0.9615	High Similarity	NPC471213
0.961	High Similarity	NPC472632
0.961	High Similarity	NPC142252
0.961	High Similarity	NPC474038
0.961	High Similarity	NPC472634
0.961	High Similarity	NPC26326
0.9608	High Similarity	NPC117418
0.9608	High Similarity	NPC53545
0.9605	High Similarity	NPC209614
0.9605	High Similarity	NPC470328
0.9605	High Similarity	NPC250922
0.9605	High Similarity	NPC472626
0.9603	High Similarity	NPC74924
0.9603	High Similarity	NPC325028
0.9603	High Similarity	NPC18727
0.9603	High Similarity	NPC298692
0.9603	High Similarity	NPC246328
0.9603	High Similarity	NPC256346
0.9603	High Similarity	NPC27532
0.96	High Similarity	NPC254412
0.96	High Similarity	NPC278476
0.96	High Similarity	NPC262039
0.96	High Similarity	NPC262038
0.96	High Similarity	NPC319910
0.9551	High Similarity	NPC62261
0.9551	High Similarity	NPC475888
0.9548	High Similarity	NPC474033
0.9548	High Similarity	NPC472635
0.9548	High Similarity	NPC474034
0.9548	High Similarity	NPC476247
0.9545	High Similarity	NPC321399
0.9545	High Similarity	NPC263449
0.9545	High Similarity	NPC119209
0.9545	High Similarity	NPC118256
0.9545	High Similarity	NPC472624
0.9545	High Similarity	NPC472630
0.9545	High Similarity	NPC475784
0.9545	High Similarity	NPC174953
0.9545	High Similarity	NPC36217
0.9545	High Similarity	NPC472631
0.9545	High Similarity	NPC192686
0.9542	High Similarity	NPC471209
0.9542	High Similarity	NPC223787
0.9542	High Similarity	NPC67876
0.9539	High Similarity	NPC133392
0.9539	High Similarity	NPC226025
0.9536	High Similarity	NPC243171
0.9536	High Similarity	NPC19721
0.9536	High Similarity	NPC171651
0.9536	High Similarity	NPC35567
0.9536	High Similarity	NPC219582
0.9536	High Similarity	NPC302950
0.9536	High Similarity	NPC236637
0.9536	High Similarity	NPC217149
0.9536	High Similarity	NPC157784
0.9536	High Similarity	NPC138288
0.9536	High Similarity	NPC63187
0.9536	High Similarity	NPC37684
0.9536	High Similarity	NPC216035
0.9533	High Similarity	NPC105136
0.9487	High Similarity	NPC124038
0.9487	High Similarity	NPC474240
0.9484	High Similarity	NPC471210
0.9484	High Similarity	NPC308992
0.9484	High Similarity	NPC112418
0.9481	High Similarity	NPC250214
0.9481	High Similarity	NPC95936
0.9481	High Similarity	NPC473990
0.9481	High Similarity	NPC210459
0.9477	High Similarity	NPC201837
0.9474	High Similarity	NPC293286
0.9474	High Similarity	NPC141212
0.947	High Similarity	NPC205046
0.947	High Similarity	NPC59162
0.947	High Similarity	NPC304295
0.9434	High Similarity	NPC102277
0.9434	High Similarity	NPC279209
0.943	High Similarity	NPC260266
0.9427	High Similarity	NPC125039
0.9427	High Similarity	NPC470457
0.9427	High Similarity	NPC36916
0.9427	High Similarity	NPC7688
0.9427	High Similarity	NPC7154
0.9427	High Similarity	NPC72787
0.9427	High Similarity	NPC58223
0.9427	High Similarity	NPC36
0.9423	High Similarity	NPC471745
0.9423	High Similarity	NPC201800
0.9419	High Similarity	NPC328102
0.9419	High Similarity	NPC471744
0.9416	High Similarity	NPC78225
0.9416	High Similarity	NPC474836
0.9416	High Similarity	NPC473272
0.9416	High Similarity	NPC48208
0.9416	High Similarity	NPC156057
0.9416	High Similarity	NPC162869
0.9416	High Similarity	NPC475267
0.9416	High Similarity	NPC284820
0.9416	High Similarity	NPC474208
0.9412	High Similarity	NPC117992
0.9412	High Similarity	NPC259710
0.9412	High Similarity	NPC230149
0.9412	High Similarity	NPC48579
0.9412	High Similarity	NPC168247
0.9412	High Similarity	NPC304207
0.9412	High Similarity	NPC217706
0.9412	High Similarity	NPC304745
0.9412	High Similarity	NPC57674
0.9412	High Similarity	NPC111341
0.9412	High Similarity	NPC67396
0.9412	High Similarity	NPC152951
0.9412	High Similarity	NPC207809
0.9408	High Similarity	NPC472912
0.9408	High Similarity	NPC324233
0.9408	High Similarity	NPC471982
0.9408	High Similarity	NPC323626
0.9404	High Similarity	NPC338131
0.9404	High Similarity	NPC88804
0.9404	High Similarity	NPC3825
0.94	High Similarity	NPC294852
0.94	High Similarity	NPC321011
0.94	High Similarity	NPC218569
0.94	High Similarity	NPC188679
0.9363	High Similarity	NPC470459
0.9363	High Similarity	NPC472582
0.9363	High Similarity	NPC186686
0.9363	High Similarity	NPC41301
0.9359	High Similarity	NPC187354
0.9359	High Similarity	NPC266314
0.9359	High Similarity	NPC471212
0.9359	High Similarity	NPC474239
0.9359	High Similarity	NPC173137
0.9359	High Similarity	NPC471211
0.9359	High Similarity	NPC158188
0.9359	High Similarity	NPC134783
0.9355	High Similarity	NPC85121
0.9355	High Similarity	NPC55738
0.9355	High Similarity	NPC152904
0.9351	High Similarity	NPC10754
0.9351	High Similarity	NPC191146
0.9351	High Similarity	NPC474638
0.9351	High Similarity	NPC208152
0.9351	High Similarity	NPC235165
0.9351	High Similarity	NPC255106
0.9351	High Similarity	NPC24640
0.9351	High Similarity	NPC3980
0.9351	High Similarity	NPC20530
0.9351	High Similarity	NPC68093
0.9351	High Similarity	NPC78492
0.9351	High Similarity	NPC215917
0.9346	High Similarity	NPC20907
0.9346	High Similarity	NPC248793
0.9346	High Similarity	NPC273462
0.9346	High Similarity	NPC78326
0.9346	High Similarity	NPC270620
0.9346	High Similarity	NPC33051
0.9346	High Similarity	NPC227337
0.9346	High Similarity	NPC70433
0.9346	High Similarity	NPC49402
0.9346	High Similarity	NPC244250
0.9346	High Similarity	NPC268193
0.9346	High Similarity	NPC180301
0.9346	High Similarity	NPC236223

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 NPC22192 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	352
0.1-0.2	910
0.2-0.3	1768
0.3-0.4	2588
0.4-0.5	1811
0.5-0.6	1002
0.6-0.7	512
0.7-0.8	149
0.8-0.85	33
0.85-0.9	18
0.9-0.95	5
0.95-1	2

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9733	High Similarity	NPD2393	Clinical (unspecified phase)
0.9536	High Similarity	NPD1934	Approved
0.9427	High Similarity	NPD6168	Clinical (unspecified phase)
0.9427	High Similarity	NPD6167	Clinical (unspecified phase)
0.9427	High Similarity	NPD6166	Phase 2
0.9139	High Similarity	NPD1512	Approved
0.9103	High Similarity	NPD3882	Suspended
0.9097	High Similarity	NPD2801	Approved
0.9073	High Similarity	NPD4378	Clinical (unspecified phase)
0.9045	High Similarity	NPD7075	Discontinued
0.9026	High Similarity	NPD4380	Phase 2
0.9018	High Similarity	NPD6797	Phase 2
0.9007	High Similarity	NPD1511	Approved
0.8974	High Similarity	NPD7096	Clinical (unspecified phase)
0.8963	High Similarity	NPD7251	Discontinued
0.8957	High Similarity	NPD7074	Phase 3
0.8917	High Similarity	NPD3817	Phase 2
0.8896	High Similarity	NPD7054	Approved
0.8841	High Similarity	NPD7472	Approved
0.8834	High Similarity	NPD3818	Discontinued
0.8795	High Similarity	NPD4338	Clinical (unspecified phase)
0.8795	High Similarity	NPD7808	Phase 3
0.879	High Similarity	NPD6801	Discontinued
0.878	High Similarity	NPD7804	Clinical (unspecified phase)
0.8742	High Similarity	NPD4868	Clinical (unspecified phase)
0.8733	High Similarity	NPD1550	Clinical (unspecified phase)
0.8733	High Similarity	NPD1552	Clinical (unspecified phase)
0.8696	High Similarity	NPD5494	Approved
0.8688	High Similarity	NPD4381	Clinical (unspecified phase)
0.8675	High Similarity	NPD1549	Phase 2
0.8563	High Similarity	NPD7993	Clinical (unspecified phase)
0.8562	High Similarity	NPD8443	Clinical (unspecified phase)
0.8516	High Similarity	NPD6799	Approved
0.85	High Similarity	NPD7819	Suspended
0.8443	Intermediate Similarity	NPD5844	Phase 1
0.8421	Intermediate Similarity	NPD2796	Approved
0.8415	Intermediate Similarity	NPD6959	Discontinued
0.8402	Intermediate Similarity	NPD6559	Discontinued
0.8375	Intermediate Similarity	NPD7411	Suspended
0.8364	Intermediate Similarity	NPD6232	Discontinued
0.8355	Intermediate Similarity	NPD1510	Phase 2
0.8344	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD1613	Approved
0.8333	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD5402	Approved
0.8323	Intermediate Similarity	NPD7473	Discontinued
0.8313	Intermediate Similarity	NPD6599	Discontinued
0.8239	Intermediate Similarity	NPD5403	Approved
0.8212	Intermediate Similarity	NPD1240	Approved
0.8193	Intermediate Similarity	NPD1247	Approved
0.8182	Intermediate Similarity	NPD919	Approved
0.8113	Intermediate Similarity	NPD5401	Approved
0.8105	Intermediate Similarity	NPD1607	Approved
0.8092	Intermediate Similarity	NPD943	Approved
0.8067	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.8049	Intermediate Similarity	NPD1465	Phase 2
0.8047	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8013	Intermediate Similarity	NPD3027	Phase 3
0.8	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7988	Intermediate Similarity	NPD3926	Phase 2
0.7952	Intermediate Similarity	NPD7768	Phase 2
0.7949	Intermediate Similarity	NPD2935	Discontinued
0.7911	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7911	Intermediate Similarity	NPD2800	Approved
0.7888	Intermediate Similarity	NPD2532	Approved
0.7888	Intermediate Similarity	NPD2534	Approved
0.7888	Intermediate Similarity	NPD2533	Approved
0.7877	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7862	Intermediate Similarity	NPD4628	Phase 3
0.7849	Intermediate Similarity	NPD3751	Discontinued
0.7848	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7824	Intermediate Similarity	NPD3787	Discontinued
0.7812	Intermediate Similarity	NPD6190	Approved
0.7806	Intermediate Similarity	NPD230	Phase 1
0.7771	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.775	Intermediate Similarity	NPD3750	Approved
0.7727	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7727	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7722	Intermediate Similarity	NPD1551	Phase 2
0.7705	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD3749	Approved
0.7683	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7683	Intermediate Similarity	NPD920	Approved
0.7676	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7674	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7667	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7661	Intermediate Similarity	NPD7199	Phase 2
0.7647	Intermediate Similarity	NPD6234	Discontinued
0.7643	Intermediate Similarity	NPD6651	Approved
0.7636	Intermediate Similarity	NPD1653	Approved
0.7614	Intermediate Similarity	NPD5953	Discontinued
0.7613	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.761	Intermediate Similarity	NPD6100	Approved
0.761	Intermediate Similarity	NPD6099	Approved
0.76	Intermediate Similarity	NPD7286	Phase 2
0.7596	Intermediate Similarity	NPD4360	Phase 2
0.7596	Intermediate Similarity	NPD4363	Phase 3
0.759	Intermediate Similarity	NPD3226	Approved
0.7584	Intermediate Similarity	NPD8312	Approved
0.7584	Intermediate Similarity	NPD8313	Approved
0.7581	Intermediate Similarity	NPD6778	Approved
0.7581	Intermediate Similarity	NPD6777	Approved
0.7581	Intermediate Similarity	NPD6779	Approved
0.7581	Intermediate Similarity	NPD6781	Approved
0.7581	Intermediate Similarity	NPD6776	Approved
0.7581	Intermediate Similarity	NPD6780	Approved
0.7581	Intermediate Similarity	NPD6782	Approved
0.758	Intermediate Similarity	NPD447	Suspended
0.7578	Intermediate Similarity	NPD1243	Approved
0.7562	Intermediate Similarity	NPD2346	Discontinued
0.7561	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.756	Intermediate Similarity	NPD37	Approved
0.7556	Intermediate Similarity	NPD8150	Discontinued
0.7556	Intermediate Similarity	NPD8434	Phase 2
0.7547	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7547	Intermediate Similarity	NPD2799	Discontinued
0.7546	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7543	Intermediate Similarity	NPD7228	Approved
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
0.75	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6798	Discontinued
0.75	Intermediate Similarity	NPD2313	Discontinued
0.75	Intermediate Similarity	NPD7390	Discontinued
0.7484	Intermediate Similarity	NPD4908	Phase 1
0.7483	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD1933	Approved
0.746	Intermediate Similarity	NPD7435	Discontinued
0.7455	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7453	Intermediate Similarity	NPD2344	Approved
0.7438	Intermediate Similarity	NPD3748	Approved
0.7438	Intermediate Similarity	NPD7033	Discontinued
0.7435	Intermediate Similarity	NPD7584	Approved
0.7423	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD9494	Approved
0.7414	Intermediate Similarity	NPD5711	Approved
0.7414	Intermediate Similarity	NPD5710	Approved
0.7407	Intermediate Similarity	NPD2424	Discontinued
0.7405	Intermediate Similarity	NPD4060	Phase 1
0.7396	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7374	Intermediate Similarity	NPD7685	Pre-registration
0.7368	Intermediate Similarity	NPD7698	Approved
0.7368	Intermediate Similarity	NPD7696	Phase 3
0.7368	Intermediate Similarity	NPD7697	Approved
0.7368	Intermediate Similarity	NPD1610	Phase 2
0.7358	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD5124	Phase 1
0.7358	Intermediate Similarity	NPD8151	Discontinued
0.7358	Intermediate Similarity	NPD6355	Discontinued
0.7349	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7342	Intermediate Similarity	NPD6233	Phase 2
0.733	Intermediate Similarity	NPD7871	Phase 2
0.733	Intermediate Similarity	NPD7870	Phase 2
0.7325	Intermediate Similarity	NPD4625	Phase 3
0.7312	Intermediate Similarity	NPD6535	Approved
0.7312	Intermediate Similarity	NPD6534	Approved
0.731	Intermediate Similarity	NPD8455	Phase 2
0.7306	Intermediate Similarity	NPD7701	Phase 2
0.729	Intermediate Similarity	NPD1203	Approved
0.7273	Intermediate Similarity	NPD2309	Approved
0.7273	Intermediate Similarity	NPD4361	Phase 2
0.7273	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7261	Intermediate Similarity	NPD6832	Phase 2
0.7256	Intermediate Similarity	NPD1652	Phase 2
0.7256	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7251	Intermediate Similarity	NPD6844	Discontinued
0.725	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD7266	Discontinued
0.7232	Intermediate Similarity	NPD2403	Approved
0.7231	Intermediate Similarity	NPD7874	Approved
0.7231	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD3823	Discontinued
0.7219	Intermediate Similarity	NPD1548	Phase 1
0.7216	Intermediate Similarity	NPD7229	Phase 3
0.7197	Intermediate Similarity	NPD2861	Phase 2
0.7196	Intermediate Similarity	NPD7700	Phase 2
0.7196	Intermediate Similarity	NPD7699	Phase 2
0.7194	Intermediate Similarity	NPD7783	Phase 2
0.7194	Intermediate Similarity	NPD7801	Approved
0.7194	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD7458	Discontinued
0.7175	Intermediate Similarity	NPD5242	Approved
0.717	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD3268	Approved
0.7168	Intermediate Similarity	NPD5353	Approved
0.7151	Intermediate Similarity	NPD2163	Approved
0.7143	Intermediate Similarity	NPD4661	Approved
0.7143	Intermediate Similarity	NPD4662	Approved
0.7135	Intermediate Similarity	NPD6823	Phase 2
0.7135	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD2798	Approved
0.7101	Intermediate Similarity	NPD5049	Phase 3
0.7097	Intermediate Similarity	NPD9717	Approved
0.7097	Intermediate Similarity	NPD9269	Phase 2
0.7097	Intermediate Similarity	NPD1608	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