NPASS Compound

Structure

NPC152209 OpenBabel07101718312D 24 26 0 0 0 0 0 0 0 0999 V2000 1.7327 0.3827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4194 -1.8375 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0376 -1.8375 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1376 -1.5693 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5945 -1.5693 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9799 0.1194 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5945 -0.3973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1175 -0.4833 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7285 -0.8973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7285 1.1027 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6605 -0.4833 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.9666 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5945 0.6027 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5230 -1.0860 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9799 -1.0860 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1376 0.6027 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5230 0.1194 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1376 -0.3973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2327 -0.4833 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8809 -1.5198 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0036 -0.8973 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6235 0.7818 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2327 -0.4833 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 24 1 0 0 0 0 2 3 1 0 0 0 0 2 4 1 0 0 0 0 3 5 1 0 0 0 0 4 14 1 0 0 0 0 5 15 1 0 0 0 0 6 8 1 0 0 0 0 6 13 1 0 0 0 0 7 9 2 0 0 0 0 7 13 1 0 0 0 0 8 15 1 0 0 0 0 9 18 1 0 0 0 0 10 13 2 0 0 0 0 10 16 1 0 0 0 0 11 14 2 0 0 0 0 11 17 1 0 0 0 0 12 14 1 0 0 0 0 12 19 2 0 0 0 0 15 21 2 0 0 0 0 16 17 1 0 0 0 0 16 18 2 0 0 0 0 17 20 2 0 0 0 0 18 22 1 0 0 0 0 19 20 1 0 0 0 0 19 24 1 0 0 0 0 20 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	326.15
Volume:	345.512
LogP:	3.661
LogD:	3.077
LogS:	-4.44
# Rotatable Bonds:	1
TPSA:	66.76
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.831
Synthetic Accessibility Score:	4.196
Fsp3:	0.35
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.873
MDCK Permeability:	1.8190006812801585e-05
Pgp-inhibitor:	0.981
Pgp-substrate:	0.078
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.991
30% Bioavailability (F30%):	0.204

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.041
Plasma Protein Binding (PPB):	98.69274139404297%
Volume Distribution (VD):	0.574
Pgp-substrate:	1.013036847114563%

ADMET: Metabolism

CYP1A2-inhibitor:	0.948
CYP1A2-substrate:	0.933
CYP2C19-inhibitor:	0.867
CYP2C19-substrate:	0.089
CYP2C9-inhibitor:	0.721
CYP2C9-substrate:	0.898
CYP2D6-inhibitor:	0.856
CYP2D6-substrate:	0.925
CYP3A4-inhibitor:	0.503
CYP3A4-substrate:	0.227

ADMET: Excretion

Clearance (CL):	10.654
Half-life (T1/2):	0.873

ADMET: Toxicity

hERG Blockers:	0.069
Human Hepatotoxicity (H-HT):	0.255
Drug-inuced Liver Injury (DILI):	0.111
AMES Toxicity:	0.384
Rat Oral Acute Toxicity:	0.205
Maximum Recommended Daily Dose:	0.896
Skin Sensitization:	0.767
Carcinogencity:	0.052
Eye Corrosion:	0.004
Eye Irritation:	0.188
Respiratory Toxicity:	0.289

Download Data

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

Natural Product: NPC152209

Natural Product ID:	NPC152209
*Common Name:**	Myricananin C
IUPAC Name:	n.a.
Synonyms:	Myricananin C
Standard InCHIKey:	KNELQMDBXBOTFN-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C20H22O4/c1-24-19-12-14-4-2-3-5-15(21)8-6-13-7-9-18(22)16(10-13)17(11-14)20(19)23/h7,9-12,22-23H,2-6,8H2,1H3
SMILES:	COc1cc2CCCCC(=O)CCc3ccc(c(-c(c2)c1O)c3)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL522962
PubChem CID:	44579884
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002650] Diarylheptanoids [CHEMONTID:0002652] Cyclic diarylheptanoids [CHEMONTID:0003524] Meta,meta-bridged biphenyls

*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
NPO15146	Myrica nana	Species	Myricaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18723353]
NPO15146	Myrica nana	Species	Myricaceae	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
Others	5

Activity Type	# Activity
Others	6

Target ID	Target Type	Target Name	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified	Inhibition	=	17.31	%	PMID[503996]
NPT2	Others	Unspecified	Inhibition	=	32.82	%	PMID[503996]
NPT2	Others	Unspecified	Inhibition	=	39.12	%	PMID[503996]
NPT2	Others	Unspecified	Inhibition	=	42.57	%	PMID[503996]
NPT2	Others	Unspecified	Inhibition	=	50.07	%	PMID[503996]
NPT2	Others	Unspecified	IC50	=	63510.0	nM	PMID[503996]

☑ 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 NPC152209 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	331
0.1-0.2	1406
0.2-0.3	3393
0.3-0.4	9654
0.4-0.5	9094
0.5-0.6	3515
0.6-0.7	6511
0.7-0.8	7522
0.8-0.85	1073
0.85-0.9	180
0.9-0.95	16
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9624	High Similarity	NPC19158
0.9412	High Similarity	NPC16353
0.9375	High Similarity	NPC21563
0.9275	High Similarity	NPC474799
0.927	High Similarity	NPC50954
0.9219	High Similarity	NPC257589
0.9219	High Similarity	NPC53305
0.9203	High Similarity	NPC474982
0.916	High Similarity	NPC143483
0.9154	High Similarity	NPC472968
0.9147	High Similarity	NPC92207
0.9147	High Similarity	NPC127937
0.9008	High Similarity	NPC226661
0.9	High Similarity	NPC303680
0.9	High Similarity	NPC84076
0.9	High Similarity	NPC90128
0.8986	High Similarity	NPC472335
0.8986	High Similarity	NPC472332
0.8955	High Similarity	NPC170185
0.8939	High Similarity	NPC304622
0.8931	High Similarity	NPC5018
0.8931	High Similarity	NPC151167
0.8931	High Similarity	NPC123228
0.8931	High Similarity	NPC123722
0.8931	High Similarity	NPC276466
0.8929	High Similarity	NPC275278
0.8915	High Similarity	NPC163083
0.8906	High Similarity	NPC201777
0.8872	High Similarity	NPC137427
0.8872	High Similarity	NPC311419
0.8872	High Similarity	NPC215941
0.8872	High Similarity	NPC244246
0.8872	High Similarity	NPC65935
0.8872	High Similarity	NPC123196
0.8872	High Similarity	NPC142985
0.8872	High Similarity	NPC319282
0.8872	High Similarity	NPC275724
0.8865	High Similarity	NPC157133
0.8855	High Similarity	NPC179777
0.8824	High Similarity	NPC256262
0.8806	High Similarity	NPC469480
0.8779	High Similarity	NPC3221
0.875	High Similarity	NPC193026
0.875	High Similarity	NPC49603
0.875	High Similarity	NPC187616
0.8741	High Similarity	NPC228843
0.8731	High Similarity	NPC195292
0.8722	High Similarity	NPC154866
0.8722	High Similarity	NPC28765
0.8705	High Similarity	NPC474784
0.8686	High Similarity	NPC113295
0.8672	High Similarity	NPC299406
0.8671	High Similarity	NPC472333
0.8671	High Similarity	NPC208507
0.8662	High Similarity	NPC105213
0.8662	High Similarity	NPC207732
0.8647	High Similarity	NPC165045
0.8647	High Similarity	NPC106511
0.8647	High Similarity	NPC20404
0.8647	High Similarity	NPC124452
0.8647	High Similarity	NPC74817
0.8647	High Similarity	NPC266555
0.8647	High Similarity	NPC5428
0.8647	High Similarity	NPC246620
0.8647	High Similarity	NPC324112
0.8647	High Similarity	NPC293054
0.8647	High Similarity	NPC169474
0.8647	High Similarity	NPC82679
0.8647	High Similarity	NPC236791
0.8647	High Similarity	NPC20287
0.8647	High Similarity	NPC118533
0.8647	High Similarity	NPC252131
0.8647	High Similarity	NPC282000
0.8647	High Similarity	NPC293641
0.8647	High Similarity	NPC159968
0.8647	High Similarity	NPC12022
0.8643	High Similarity	NPC100675
0.8636	High Similarity	NPC148627
0.863	High Similarity	NPC70320
0.8626	High Similarity	NPC257976
0.8626	High Similarity	NPC242372
0.8626	High Similarity	NPC4181
0.8626	High Similarity	NPC164778
0.8626	High Similarity	NPC471693
0.8623	High Similarity	NPC177160
0.8623	High Similarity	NPC143139
0.8623	High Similarity	NPC10737
0.8623	High Similarity	NPC263367
0.8623	High Similarity	NPC202846
0.8623	High Similarity	NPC54743
0.8623	High Similarity	NPC29799
0.8623	High Similarity	NPC209985
0.8623	High Similarity	NPC156502
0.8623	High Similarity	NPC477939
0.8613	High Similarity	NPC176814
0.8613	High Similarity	NPC68779
0.8613	High Similarity	NPC300776
0.8613	High Similarity	NPC4982
0.8613	High Similarity	NPC5310
0.8605	High Similarity	NPC227217
0.8605	High Similarity	NPC242885
0.8605	High Similarity	NPC95614
0.8605	High Similarity	NPC232316
0.8605	High Similarity	NPC165133
0.8605	High Similarity	NPC56214
0.8605	High Similarity	NPC117780
0.8603	High Similarity	NPC239302
0.8603	High Similarity	NPC303144
0.8603	High Similarity	NPC6451
0.8594	High Similarity	NPC470626
0.8593	High Similarity	NPC126836
0.8593	High Similarity	NPC51840
0.8593	High Similarity	NPC311680
0.8593	High Similarity	NPC234488
0.8593	High Similarity	NPC299221
0.8593	High Similarity	NPC172673
0.8592	High Similarity	NPC46161
0.8592	High Similarity	NPC239608
0.8582	High Similarity	NPC478215
0.8582	High Similarity	NPC184733
0.8582	High Similarity	NPC128208
0.8582	High Similarity	NPC253722
0.8582	High Similarity	NPC110419
0.8582	High Similarity	NPC131971
0.8582	High Similarity	NPC31751
0.8582	High Similarity	NPC253481
0.8582	High Similarity	NPC278308
0.8582	High Similarity	NPC11258
0.8582	High Similarity	NPC129570
0.8582	High Similarity	NPC282703
0.8582	High Similarity	NPC45774
0.8582	High Similarity	NPC21867
0.8581	High Similarity	NPC268008
0.8571	High Similarity	NPC295719
0.8571	High Similarity	NPC276014
0.8571	High Similarity	NPC165026
0.8571	High Similarity	NPC34431
0.8571	High Similarity	NPC137125
0.8571	High Similarity	NPC78974
0.8571	High Similarity	NPC223136
0.8571	High Similarity	NPC12668
0.8571	High Similarity	NPC214406
0.8571	High Similarity	NPC308768
0.8571	High Similarity	NPC103823
0.8571	High Similarity	NPC28730
0.8571	High Similarity	NPC322021
0.8571	High Similarity	NPC3744
0.8571	High Similarity	NPC18924
0.8571	High Similarity	NPC44748
0.8571	High Similarity	NPC266650
0.8571	High Similarity	NPC73505
0.8571	High Similarity	NPC223953
0.8571	High Similarity	NPC131121
0.8562	High Similarity	NPC472279
0.8561	High Similarity	NPC56329
0.8561	High Similarity	NPC242715
0.8561	High Similarity	NPC281780
0.8561	High Similarity	NPC312404
0.8561	High Similarity	NPC273686
0.8551	High Similarity	NPC294884
0.8551	High Similarity	NPC10314
0.8551	High Similarity	NPC69029
0.8551	High Similarity	NPC241241
0.8551	High Similarity	NPC158142
0.8551	High Similarity	NPC200557
0.8551	High Similarity	NPC108198
0.855	High Similarity	NPC114298
0.855	High Similarity	NPC85488
0.8542	High Similarity	NPC58752
0.8542	High Similarity	NPC165389
0.8542	High Similarity	NPC39361
0.8542	High Similarity	NPC30720
0.854	High Similarity	NPC327410
0.854	High Similarity	NPC32778
0.8538	High Similarity	NPC158949
0.8531	High Similarity	NPC223185
0.8529	High Similarity	NPC45715
0.8529	High Similarity	NPC15543
0.8529	High Similarity	NPC474356
0.8529	High Similarity	NPC12275
0.8529	High Similarity	NPC232275
0.8527	High Similarity	NPC281298
0.8527	High Similarity	NPC310338
0.8521	High Similarity	NPC106920
0.8521	High Similarity	NPC312256
0.8521	High Similarity	NPC273657
0.8519	High Similarity	NPC241354
0.8519	High Similarity	NPC10225
0.8519	High Similarity	NPC58164
0.8516	High Similarity	NPC293619
0.8507	High Similarity	NPC127587
0.8507	High Similarity	NPC281020
0.8503	High Similarity	NPC75377
0.8503	High Similarity	NPC78505
0.8503	High Similarity	NPC272566
0.8503	High Similarity	NPC256406
0.8503	High Similarity	NPC473201
0.8503	High Similarity	NPC302783
0.85	High Similarity	NPC212942
0.85	High Similarity	NPC260741

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 NPC152209 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	299
0.1-0.2	893
0.2-0.3	1494
0.3-0.4	2638
0.4-0.5	1877
0.5-0.6	1045
0.6-0.7	729
0.7-0.8	167
0.8-0.85	7
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8485	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.8382	Intermediate Similarity	NPD3027	Phase 3
0.8267	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.82	Intermediate Similarity	NPD1934	Approved
0.8146	Intermediate Similarity	NPD2801	Approved
0.8106	Intermediate Similarity	NPD1651	Approved
0.8062	Intermediate Similarity	NPD5283	Phase 1
0.8047	Intermediate Similarity	NPD228	Approved
0.8043	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.8013	Intermediate Similarity	NPD6232	Discontinued
0.7975	Intermediate Similarity	NPD7473	Discontinued
0.7971	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7955	Intermediate Similarity	NPD5536	Phase 2
0.7943	Intermediate Similarity	NPD1613	Approved
0.7943	Intermediate Similarity	NPD4060	Phase 1
0.7943	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7935	Intermediate Similarity	NPD6234	Discontinued
0.7922	Intermediate Similarity	NPD3882	Suspended
0.7917	Intermediate Similarity	NPD2935	Discontinued
0.7905	Intermediate Similarity	NPD1511	Approved
0.7905	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7883	Intermediate Similarity	NPD1283	Approved
0.7843	Intermediate Similarity	NPD37	Approved
0.781	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.78	Intermediate Similarity	NPD1512	Approved
0.7799	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7799	Intermediate Similarity	NPD6166	Phase 2
0.7799	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7762	Intermediate Similarity	NPD6355	Discontinued
0.7752	Intermediate Similarity	NPD3022	Approved
0.7752	Intermediate Similarity	NPD3021	Approved
0.7733	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7714	Intermediate Similarity	NPD9494	Approved
0.7712	Intermediate Similarity	NPD4380	Phase 2
0.7692	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD4966	Approved
0.7692	Intermediate Similarity	NPD4965	Approved
0.7692	Intermediate Similarity	NPD4967	Phase 2
0.7676	Intermediate Similarity	NPD6798	Discontinued
0.7664	Intermediate Similarity	NPD1281	Approved
0.7654	Intermediate Similarity	NPD5844	Phase 1
0.7635	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7628	Intermediate Similarity	NPD3817	Phase 2
0.7619	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7609	Intermediate Similarity	NPD1608	Approved
0.7607	Intermediate Similarity	NPD7074	Phase 3
0.7593	Intermediate Similarity	NPD3818	Discontinued
0.7593	Intermediate Similarity	NPD7228	Approved
0.7589	Intermediate Similarity	NPD3018	Phase 2
0.7589	Intermediate Similarity	NPD2861	Phase 2
0.7584	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7584	Intermediate Similarity	NPD4628	Phase 3
0.7584	Intermediate Similarity	NPD4110	Phase 3
0.7569	Intermediate Similarity	NPD3620	Phase 2
0.7569	Intermediate Similarity	NPD2979	Phase 3
0.7569	Intermediate Similarity	NPD1240	Approved
0.7569	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7564	Intermediate Similarity	NPD1465	Phase 2
0.7552	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7552	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7547	Intermediate Similarity	NPD5494	Approved
0.7546	Intermediate Similarity	NPD7054	Approved
0.7518	Intermediate Similarity	NPD4626	Approved
0.75	Intermediate Similarity	NPD7199	Phase 2
0.75	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7472	Approved
0.7483	Intermediate Similarity	NPD4625	Phase 3
0.7483	Intermediate Similarity	NPD7095	Approved
0.7483	Intermediate Similarity	NPD2799	Discontinued
0.7483	Intermediate Similarity	NPD1510	Phase 2
0.7467	Intermediate Similarity	NPD8166	Discontinued
0.7466	Intermediate Similarity	NPD1607	Approved
0.7452	Intermediate Similarity	NPD8455	Phase 2
0.7448	Intermediate Similarity	NPD1558	Phase 1
0.7448	Intermediate Similarity	NPD943	Approved
0.744	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7432	Intermediate Similarity	NPD6100	Approved
0.7432	Intermediate Similarity	NPD6099	Approved
0.7432	Intermediate Similarity	NPD2438	Suspended
0.7429	Intermediate Similarity	NPD2983	Phase 2
0.7429	Intermediate Similarity	NPD2982	Phase 2
0.7421	Intermediate Similarity	NPD7075	Discontinued
0.7417	Intermediate Similarity	NPD6190	Approved
0.7413	Intermediate Similarity	NPD4908	Phase 1
0.741	Intermediate Similarity	NPD3705	Approved
0.7407	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7403	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.74	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD17	Approved
0.7379	Intermediate Similarity	NPD6233	Phase 2
0.7376	Intermediate Similarity	NPD8651	Approved
0.7372	Intermediate Similarity	NPD7028	Phase 2
0.7357	Intermediate Similarity	NPD2981	Phase 2
0.7351	Intermediate Similarity	NPD3750	Approved
0.7351	Intermediate Similarity	NPD7003	Approved
0.7349	Intermediate Similarity	NPD6797	Phase 2
0.7342	Intermediate Similarity	NPD7819	Suspended
0.7342	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD3847	Discontinued
0.7324	Intermediate Similarity	NPD2797	Approved
0.7315	Intermediate Similarity	NPD4476	Approved
0.7315	Intermediate Similarity	NPD4477	Approved
0.731	Intermediate Similarity	NPD3268	Approved
0.7308	Intermediate Similarity	NPD3226	Approved
0.7308	Intermediate Similarity	NPD7458	Discontinued
0.7305	Intermediate Similarity	NPD7251	Discontinued
0.7305	Intermediate Similarity	NPD6559	Discontinued
0.7296	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7286	Intermediate Similarity	NPD1610	Phase 2
0.7286	Intermediate Similarity	NPD1535	Discovery
0.7285	Intermediate Similarity	NPD6674	Discontinued
0.7284	Intermediate Similarity	NPD6959	Discontinued
0.7284	Intermediate Similarity	NPD8127	Discontinued
0.7279	Intermediate Similarity	NPD447	Suspended
0.7279	Intermediate Similarity	NPD6671	Approved
0.7279	Intermediate Similarity	NPD230	Phase 1
0.7273	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD2798	Approved
0.7267	Intermediate Similarity	NPD6002	Phase 3
0.7267	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD6004	Phase 3
0.7267	Intermediate Similarity	NPD6005	Phase 3
0.7267	Intermediate Similarity	NPD7266	Discontinued
0.7267	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD2346	Discontinued
0.7267	Intermediate Similarity	NPD2344	Approved
0.7267	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7266	Intermediate Similarity	NPD3019	Approved
0.7266	Intermediate Similarity	NPD2932	Approved
0.7262	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7262	Intermediate Similarity	NPD7808	Phase 3
0.726	Intermediate Similarity	NPD4062	Phase 3
0.725	Intermediate Similarity	NPD7768	Phase 2
0.7246	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7237	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7234	Intermediate Similarity	NPD3972	Approved
0.7234	Intermediate Similarity	NPD1481	Phase 2
0.7219	Intermediate Similarity	NPD1549	Phase 2
0.7219	Intermediate Similarity	NPD2424	Discontinued
0.7219	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD4357	Discontinued
0.7208	Intermediate Similarity	NPD6799	Approved
0.7205	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD2531	Phase 2
0.7195	Intermediate Similarity	NPD3926	Phase 2
0.7194	Intermediate Similarity	NPD5691	Approved
0.7192	Intermediate Similarity	NPD2313	Discontinued
0.7178	Intermediate Similarity	NPD1247	Approved
0.7171	Intermediate Similarity	NPD3060	Approved
0.717	Intermediate Similarity	NPD6801	Discontinued
0.7163	Intermediate Similarity	NPD1201	Approved
0.7163	Intermediate Similarity	NPD1611	Approved
0.7161	Intermediate Similarity	NPD2533	Approved
0.7161	Intermediate Similarity	NPD2532	Approved
0.7161	Intermediate Similarity	NPD2534	Approved
0.716	Intermediate Similarity	NPD919	Approved
0.7153	Intermediate Similarity	NPD7157	Approved
0.7152	Intermediate Similarity	NPD6599	Discontinued
0.7152	Intermediate Similarity	NPD5762	Approved
0.7152	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD5763	Approved
0.7143	Intermediate Similarity	NPD1778	Approved
0.7143	Intermediate Similarity	NPD2674	Phase 3
0.7143	Intermediate Similarity	NPD2684	Approved
0.7134	Intermediate Similarity	NPD3787	Discontinued
0.7134	Intermediate Similarity	NPD7229	Phase 3
0.7134	Intermediate Similarity	NPD2370	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD1653	Approved
0.7133	Intermediate Similarity	NPD1876	Approved
0.7133	Intermediate Similarity	NPD6696	Suspended
0.7133	Intermediate Similarity	NPD7033	Discontinued
0.7126	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7122	Intermediate Similarity	NPD1894	Discontinued
0.7122	Intermediate Similarity	NPD1548	Phase 1
0.7118	Intermediate Similarity	NPD3534	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD7411	Suspended
0.7107	Intermediate Similarity	NPD6386	Approved
0.7107	Intermediate Similarity	NPD6873	Phase 2
0.7107	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD6385	Approved
0.7105	Intermediate Similarity	NPD4534	Discontinued
0.7101	Intermediate Similarity	NPD7240	Approved
0.7101	Intermediate Similarity	NPD7685	Pre-registration
0.7086	Intermediate Similarity	NPD2796	Approved
0.7086	Intermediate Similarity	NPD6032	Approved
0.7083	Intermediate Similarity	NPD1470	Approved
0.7078	Intermediate Similarity	NPD2309	Approved
0.7076	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD5109	Approved
0.7075	Intermediate Similarity	NPD5111	Phase 2
0.7075	Intermediate Similarity	NPD5110	Phase 2
0.7075	Intermediate Similarity	NPD3764	Approved
0.7071	Intermediate Similarity	NPD1357	Approved
0.7071	Intermediate Similarity	NPD5585	Approved
0.7067	Intermediate Similarity	NPD4536	Approved
0.7067	Intermediate Similarity	NPD4537	Clinical (unspecified phase)

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