NPASS Compound

Structure

CID19158 OpenBabel06191715342D 26 28 0 0 0 0 0 0 0 0999 V2000 -0.0233 -2.0126 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8330 1.5874 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1711 1.2411 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7376 1.2411 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3394 0.9953 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2480 0.9953 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6012 -0.5523 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2480 -0.0788 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7273 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4543 0.3795 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4543 -1.4535 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8187 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2480 -0.9953 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6926 0.5523 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6012 0.5523 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3394 -0.9953 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6926 -0.5523 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3394 -0.0788 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2133 0.4429 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2133 -0.4429 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 -2.4270 0.9500 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.1331 0.3795 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9295 1.8760 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3581 -1.1595 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9165 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 25 1 0 0 0 0 2 26 1 0 0 0 0 3 4 1 0 0 0 0 3 5 1 0 0 0 0 4 6 1 0 0 0 0 5 14 1 0 0 0 0 6 15 1 0 0 0 0 7 9 1 0 0 0 0 7 13 1 0 0 0 0 8 10 2 0 0 0 0 8 13 1 0 0 0 0 9 15 1 0 0 0 0 10 18 1 0 0 0 0 11 13 2 0 0 0 0 11 16 1 0 0 0 0 12 14 2 0 0 0 0 12 17 1 0 0 0 0 14 19 1 0 0 0 0 15 22 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 23 1 0 0 0 0 19 21 2 0 0 0 0 19 24 1 0 0 0 0 20 21 1 0 0 0 0 20 25 1 0 0 0 0 21 26 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	356.16
Volume:	371.599
LogP:	3.359
LogD:	2.912
LogS:	-4.283
# Rotatable Bonds:	2
TPSA:	75.99
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.85
Synthetic Accessibility Score:	4.234
Fsp3:	0.381
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-4.86
MDCK Permeability:	1.7488806406618096e-05
Pgp-inhibitor:	0.113
Pgp-substrate:	0.127
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.271
30% Bioavailability (F30%):	0.035

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.024
Plasma Protein Binding (PPB):	97.4575424194336%
Volume Distribution (VD):	0.472
Pgp-substrate:	1.2512234449386597%

ADMET: Metabolism

CYP1A2-inhibitor:	0.898
CYP1A2-substrate:	0.947
CYP2C19-inhibitor:	0.806
CYP2C19-substrate:	0.176
CYP2C9-inhibitor:	0.685
CYP2C9-substrate:	0.898
CYP2D6-inhibitor:	0.669
CYP2D6-substrate:	0.918
CYP3A4-inhibitor:	0.489
CYP3A4-substrate:	0.234

ADMET: Excretion

Clearance (CL):	9.182
Half-life (T1/2):	0.782

ADMET: Toxicity

hERG Blockers:	0.149
Human Hepatotoxicity (H-HT):	0.282
Drug-inuced Liver Injury (DILI):	0.076
AMES Toxicity:	0.27
Rat Oral Acute Toxicity:	0.126
Maximum Recommended Daily Dose:	0.792
Skin Sensitization:	0.783
Carcinogencity:	0.034
Eye Corrosion:	0.003
Eye Irritation:	0.212
Respiratory Toxicity:	0.131

Download Data

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

Natural Product: NPC19158

Natural Product ID:	NPC19158
*Common Name:**	Myricanone
IUPAC Name:	n.a.
Synonyms:	Myricanone
Standard InCHIKey:	ZTSNTUQTNQSIDC-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C21H24O5/c1-25-20-17-12-14(19(24)21(20)26-2)5-3-4-6-15(22)9-7-13-8-10-18(23)16(17)11-13/h8,10-12,23-24H,3-7,9H2,1-2H3
SMILES:	COc1c2cc(c(c1OC)O)CCCCC(=O)CCc1cc2c(O)cc1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2152655
PubChem CID:	161748
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
NPO3152	Morella rubra	Species	Myricaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19407970]
NPO3152	Morella rubra	Species	Myricaceae	Eukaryota	n.a.	bark	n.a.	PMID[21553897]
NPO31026	Myrica rubra	Species	Myricaceae	Eukaryota	barks	n.a.	n.a.	PMID[23066712]
NPO31026	Myrica rubra	Species	Myricaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3152	Morella rubra	Species	Myricaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO31026	Myrica rubra	Species	Myricaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO3152	Morella rubra	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

Activity Type	# Activity
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	1000.0	ug.mL-1	PMID[511500]

☑ 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 NPC19158 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	360
0.1-0.2	1416
0.2-0.3	3694
0.3-0.4	10503
0.4-0.5	8073
0.5-0.6	3607
0.6-0.7	5282
0.7-0.8	7278
0.8-0.85	1967
0.85-0.9	502
0.9-0.95	10
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.9779	High Similarity	NPC16353
0.9638	High Similarity	NPC474799
0.9624	High Similarity	NPC152209
0.9565	High Similarity	NPC474982
0.9348	High Similarity	NPC472335
0.9348	High Similarity	NPC472332
0.922	High Similarity	NPC157133
0.9191	High Similarity	NPC256262
0.9098	High Similarity	NPC28765
0.9098	High Similarity	NPC154866
0.9023	High Similarity	NPC266555
0.9023	High Similarity	NPC293054
0.9023	High Similarity	NPC246620
0.9023	High Similarity	NPC169474
0.9023	High Similarity	NPC282000
0.9023	High Similarity	NPC124452
0.9023	High Similarity	NPC324112
0.9023	High Similarity	NPC21563
0.9023	High Similarity	NPC159968
0.9023	High Similarity	NPC236791
0.9023	High Similarity	NPC252131
0.9023	High Similarity	NPC82679
0.9023	High Similarity	NPC74817
0.9021	High Similarity	NPC472333
0.9021	High Similarity	NPC208507
0.9014	High Similarity	NPC207732
0.9014	High Similarity	NPC105213
0.8986	High Similarity	NPC143139
0.8986	High Similarity	NPC202846
0.8971	High Similarity	NPC6451
0.8963	High Similarity	NPC126836
0.8963	High Similarity	NPC311680
0.8963	High Similarity	NPC299221
0.8963	High Similarity	NPC234488
0.8963	High Similarity	NPC51840
0.8947	High Similarity	NPC44748
0.8947	High Similarity	NPC223953
0.8947	High Similarity	NPC78974
0.8947	High Similarity	NPC214406
0.8947	High Similarity	NPC223136
0.8947	High Similarity	NPC103823
0.8947	High Similarity	NPC18924
0.8947	High Similarity	NPC28730
0.8944	High Similarity	NPC50954
0.8936	High Similarity	NPC110419
0.8929	High Similarity	NPC295719
0.8929	High Similarity	NPC34431
0.8929	High Similarity	NPC12668
0.8929	High Similarity	NPC165026
0.8929	High Similarity	NPC73505
0.8929	High Similarity	NPC308768
0.8929	High Similarity	NPC266650
0.8921	High Similarity	NPC242715
0.8921	High Similarity	NPC56329
0.8913	High Similarity	NPC158142
0.8913	High Similarity	NPC69029
0.8913	High Similarity	NPC294884
0.8913	High Similarity	NPC200557
0.8913	High Similarity	NPC108198
0.8913	High Similarity	NPC10314
0.8913	High Similarity	NPC241241
0.8905	High Similarity	NPC32778
0.8904	High Similarity	NPC472279
0.8897	High Similarity	NPC474356
0.8897	High Similarity	NPC232275
0.8897	High Similarity	NPC45715
0.8897	High Similarity	NPC12275
0.8897	High Similarity	NPC15543
0.8889	High Similarity	NPC58164
0.8889	High Similarity	NPC165389
0.8889	High Similarity	NPC30720
0.8889	High Similarity	NPC10225
0.8881	High Similarity	NPC127587
0.8873	High Similarity	NPC273657
0.8873	High Similarity	NPC312256
0.8873	High Similarity	NPC106920
0.8872	High Similarity	NPC82483
0.8872	High Similarity	NPC299584
0.8872	High Similarity	NPC251855
0.8872	High Similarity	NPC234400
0.8872	High Similarity	NPC17943
0.8872	High Similarity	NPC265483
0.8872	High Similarity	NPC208950
0.8872	High Similarity	NPC60885
0.8872	High Similarity	NPC57490
0.8872	High Similarity	NPC475169
0.8872	High Similarity	NPC233410
0.8872	High Similarity	NPC53305
0.8872	High Similarity	NPC105925
0.8872	High Similarity	NPC221077
0.8872	High Similarity	NPC116907
0.8872	High Similarity	NPC298757
0.8872	High Similarity	NPC257589
0.8872	High Similarity	NPC117214
0.8872	High Similarity	NPC472093
0.8872	High Similarity	NPC193544
0.8872	High Similarity	NPC203133
0.8857	High Similarity	NPC243996
0.8857	High Similarity	NPC218131
0.8857	High Similarity	NPC132804
0.8857	High Similarity	NPC243759
0.8857	High Similarity	NPC79622
0.8857	High Similarity	NPC275061
0.8857	High Similarity	NPC29868
0.8857	High Similarity	NPC212942
0.8857	High Similarity	NPC260741
0.8857	High Similarity	NPC220344
0.8857	High Similarity	NPC70682
0.8857	High Similarity	NPC105847
0.8849	High Similarity	NPC30632
0.8849	High Similarity	NPC471182
0.8844	High Similarity	NPC256406
0.8844	High Similarity	NPC78505
0.8844	High Similarity	NPC272566
0.8841	High Similarity	NPC7515
0.8841	High Similarity	NPC125649
0.8841	High Similarity	NPC56764
0.8841	High Similarity	NPC160697
0.8841	High Similarity	NPC276026
0.8841	High Similarity	NPC555
0.8841	High Similarity	NPC188378
0.8841	High Similarity	NPC206737
0.8841	High Similarity	NPC289258
0.8841	High Similarity	NPC469659
0.8824	High Similarity	NPC224157
0.8824	High Similarity	NPC143483
0.8824	High Similarity	NPC192687
0.8815	High Similarity	NPC266691
0.8815	High Similarity	NPC472968
0.8806	High Similarity	NPC92207
0.8806	High Similarity	NPC127937
0.8806	High Similarity	NPC76451
0.8803	High Similarity	NPC175838
0.8803	High Similarity	NPC41782
0.8797	High Similarity	NPC206487
0.8797	High Similarity	NPC5796
0.8786	High Similarity	NPC6262
0.8786	High Similarity	NPC230919
0.8786	High Similarity	NPC73535
0.8786	High Similarity	NPC25111
0.8786	High Similarity	NPC272157
0.8786	High Similarity	NPC22902
0.8786	High Similarity	NPC201145
0.8786	High Similarity	NPC266453
0.8786	High Similarity	NPC90615
0.8786	High Similarity	NPC200935
0.8786	High Similarity	NPC151656
0.8786	High Similarity	NPC266006
0.8784	High Similarity	NPC471982
0.8784	High Similarity	NPC199773
0.8777	High Similarity	NPC214853
0.8777	High Similarity	NPC240279
0.8777	High Similarity	NPC313081
0.8777	High Similarity	NPC55239
0.8777	High Similarity	NPC180602
0.8759	High Similarity	NPC474017
0.875	High Similarity	NPC212015
0.875	High Similarity	NPC190144
0.875	High Similarity	NPC476968
0.875	High Similarity	NPC170844
0.8741	High Similarity	NPC236760
0.8741	High Similarity	NPC470811
0.8741	High Similarity	NPC477697
0.8741	High Similarity	NPC477696
0.8733	High Similarity	NPC195796
0.8733	High Similarity	NPC291878
0.8733	High Similarity	NPC278778
0.8733	High Similarity	NPC35038
0.8732	High Similarity	NPC35216
0.8732	High Similarity	NPC263261
0.8732	High Similarity	NPC87725
0.8723	High Similarity	NPC184613
0.8722	High Similarity	NPC136319
0.8722	High Similarity	NPC282496
0.8722	High Similarity	NPC95168
0.8722	High Similarity	NPC228922
0.8722	High Similarity	NPC84086
0.8722	High Similarity	NPC233526
0.8722	High Similarity	NPC121115
0.8722	High Similarity	NPC197757
0.8714	High Similarity	NPC476639
0.8714	High Similarity	NPC300846
0.8714	High Similarity	NPC248727
0.8714	High Similarity	NPC205442
0.8714	High Similarity	NPC162659
0.8714	High Similarity	NPC265433
0.8714	High Similarity	NPC114155
0.8714	High Similarity	NPC270456
0.8714	High Similarity	NPC133025
0.8707	High Similarity	NPC102003
0.8707	High Similarity	NPC92722
0.8707	High Similarity	NPC38545
0.8707	High Similarity	NPC171916
0.8705	High Similarity	NPC209199
0.8699	High Similarity	NPC304821
0.8699	High Similarity	NPC77598
0.8696	High Similarity	NPC202762
0.8696	High Similarity	NPC86655
0.8696	High Similarity	NPC127624
0.8684	High Similarity	NPC36217

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 NPC19158 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	327
0.1-0.2	874
0.2-0.3	1637
0.3-0.4	2726
0.4-0.5	1787
0.5-0.6	982
0.6-0.7	647
0.7-0.8	152
0.8-0.85	15
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.875	High Similarity	NPD3027	Phase 3
0.86	High Similarity	NPD2393	Clinical (unspecified phase)
0.8533	High Similarity	NPD1934	Approved
0.8477	Intermediate Similarity	NPD2801	Approved
0.8406	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD6232	Discontinued
0.8333	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.8298	Intermediate Similarity	NPD1613	Approved
0.8298	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8291	Intermediate Similarity	NPD7473	Discontinued
0.8258	Intermediate Similarity	NPD6234	Discontinued
0.8247	Intermediate Similarity	NPD3882	Suspended
0.8243	Intermediate Similarity	NPD1511	Approved
0.8175	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.817	Intermediate Similarity	NPD37	Approved
0.8133	Intermediate Similarity	NPD1512	Approved
0.8113	Intermediate Similarity	NPD6166	Phase 2
0.8113	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8113	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8067	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8039	Intermediate Similarity	NPD4380	Phase 2
0.8013	Intermediate Similarity	NPD4966	Approved
0.8013	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8013	Intermediate Similarity	NPD4965	Approved
0.8013	Intermediate Similarity	NPD4967	Phase 2
0.7963	Intermediate Similarity	NPD5844	Phase 1
0.7949	Intermediate Similarity	NPD3817	Phase 2
0.7943	Intermediate Similarity	NPD3018	Phase 2
0.7917	Intermediate Similarity	NPD1240	Approved
0.7914	Intermediate Similarity	NPD7074	Phase 3
0.7902	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7902	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7901	Intermediate Similarity	NPD7228	Approved
0.7901	Intermediate Similarity	NPD3818	Discontinued
0.7891	Intermediate Similarity	NPD2935	Discontinued
0.7885	Intermediate Similarity	NPD1465	Phase 2
0.7862	Intermediate Similarity	NPD5494	Approved
0.7853	Intermediate Similarity	NPD7054	Approved
0.7832	Intermediate Similarity	NPD4625	Phase 3
0.7823	Intermediate Similarity	NPD1510	Phase 2
0.7812	Intermediate Similarity	NPD7199	Phase 2
0.781	Intermediate Similarity	NPD1651	Approved
0.7808	Intermediate Similarity	NPD1607	Approved
0.7805	Intermediate Similarity	NPD7472	Approved
0.7793	Intermediate Similarity	NPD943	Approved
0.7786	Intermediate Similarity	NPD2983	Phase 2
0.7786	Intermediate Similarity	NPD2982	Phase 2
0.777	Intermediate Similarity	NPD6100	Approved
0.777	Intermediate Similarity	NPD6099	Approved
0.7762	Intermediate Similarity	NPD4908	Phase 1
0.7761	Intermediate Similarity	NPD5283	Phase 1
0.7744	Intermediate Similarity	NPD228	Approved
0.7736	Intermediate Similarity	NPD7075	Discontinued
0.7727	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7716	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7714	Intermediate Similarity	NPD2981	Phase 2
0.7682	Intermediate Similarity	NPD3750	Approved
0.7671	Intermediate Similarity	NPD4060	Phase 1
0.7664	Intermediate Similarity	NPD5536	Phase 2
0.7658	Intermediate Similarity	NPD7819	Suspended
0.7658	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7651	Intermediate Similarity	NPD6797	Phase 2
0.7647	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7643	Intermediate Similarity	NPD1610	Phase 2
0.7619	Intermediate Similarity	NPD230	Phase 1
0.761	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7606	Intermediate Similarity	NPD1283	Approved
0.7605	Intermediate Similarity	NPD7251	Discontinued
0.7605	Intermediate Similarity	NPD6559	Discontinued
0.76	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7597	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7593	Intermediate Similarity	NPD6959	Discontinued
0.7566	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7562	Intermediate Similarity	NPD7768	Phase 2
0.756	Intermediate Similarity	NPD7808	Phase 3
0.756	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.755	Intermediate Similarity	NPD1549	Phase 2
0.755	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7545	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7535	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD4357	Discontinued
0.7532	Intermediate Similarity	NPD6799	Approved
0.7516	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6355	Discontinued
0.75	Intermediate Similarity	NPD3926	Phase 2
0.7485	Intermediate Similarity	NPD1247	Approved
0.7484	Intermediate Similarity	NPD2532	Approved
0.7484	Intermediate Similarity	NPD2534	Approved
0.7484	Intermediate Similarity	NPD2533	Approved
0.7484	Intermediate Similarity	NPD6801	Discontinued
0.7482	Intermediate Similarity	NPD1548	Phase 1
0.7469	Intermediate Similarity	NPD919	Approved
0.7468	Intermediate Similarity	NPD6599	Discontinued
0.7463	Intermediate Similarity	NPD3022	Approved
0.7463	Intermediate Similarity	NPD3021	Approved
0.7452	Intermediate Similarity	NPD1653	Approved
0.7448	Intermediate Similarity	NPD9494	Approved
0.7439	Intermediate Similarity	NPD7229	Phase 3
0.7427	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7425	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7421	Intermediate Similarity	NPD7411	Suspended
0.7421	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7417	Intermediate Similarity	NPD2796	Approved
0.7415	Intermediate Similarity	NPD6798	Discontinued
0.7413	Intermediate Similarity	NPD4749	Approved
0.7403	Intermediate Similarity	NPD6190	Approved
0.7399	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7396	Intermediate Similarity	NPD7240	Approved
0.7394	Intermediate Similarity	NPD1281	Approved
0.7386	Intermediate Similarity	NPD2800	Approved
0.7386	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7379	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD3540	Phase 1
0.7368	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7351	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7351	Intermediate Similarity	NPD3748	Approved
0.7349	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7343	Intermediate Similarity	NPD1608	Approved
0.7338	Intermediate Similarity	NPD4110	Phase 3
0.7338	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD4628	Phase 3
0.7333	Intermediate Similarity	NPD3787	Discontinued
0.7333	Intermediate Similarity	NPD6651	Approved
0.7329	Intermediate Similarity	NPD8455	Phase 2
0.7329	Intermediate Similarity	NPD2861	Phase 2
0.7325	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7315	Intermediate Similarity	NPD2979	Phase 3
0.7315	Intermediate Similarity	NPD3620	Phase 2
0.7315	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD2797	Approved
0.7308	Intermediate Similarity	NPD7390	Discontinued
0.7303	Intermediate Similarity	NPD2438	Suspended
0.7303	Intermediate Similarity	NPD3539	Phase 1
0.7297	Intermediate Similarity	NPD3268	Approved
0.7297	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7284	Intermediate Similarity	NPD5402	Approved
0.7273	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD422	Phase 1
0.7267	Intermediate Similarity	NPD447	Suspended
0.7261	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7261	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7254	Intermediate Similarity	NPD4626	Approved
0.7248	Intermediate Similarity	NPD6233	Phase 2
0.7237	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7237	Intermediate Similarity	NPD2799	Discontinued
0.723	Intermediate Similarity	NPD7095	Approved
0.7226	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD8166	Discontinued
0.7212	Intermediate Similarity	NPD6746	Phase 2
0.7208	Intermediate Similarity	NPD2424	Discontinued
0.72	Intermediate Similarity	NPD1558	Phase 1
0.719	Intermediate Similarity	NPD1551	Phase 2
0.7186	Intermediate Similarity	NPD5242	Approved
0.7179	Intermediate Similarity	NPD2219	Phase 1
0.717	Intermediate Similarity	NPD5403	Approved
0.7161	Intermediate Similarity	NPD6674	Discontinued
0.716	Intermediate Similarity	NPD3751	Discontinued
0.7153	Intermediate Similarity	NPD3705	Approved
0.7143	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6005	Phase 3
0.7143	Intermediate Similarity	NPD7028	Phase 2
0.7143	Intermediate Similarity	NPD7266	Discontinued
0.7143	Intermediate Similarity	NPD6004	Phase 3
0.7143	Intermediate Similarity	NPD6002	Phase 3
0.7143	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD7124	Phase 2
0.7133	Intermediate Similarity	NPD17	Approved
0.7123	Intermediate Similarity	NPD8651	Approved
0.7115	Intermediate Similarity	NPD7003	Approved
0.7103	Intermediate Similarity	NPD9269	Phase 2
0.7099	Intermediate Similarity	NPD5090	Approved
0.7099	Intermediate Similarity	NPD5089	Approved
0.7091	Intermediate Similarity	NPD4055	Discovery
0.7091	Intermediate Similarity	NPD3749	Approved
0.7091	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD3847	Discontinued
0.7081	Intermediate Similarity	NPD4005	Discontinued
0.7081	Intermediate Similarity	NPD7458	Discontinued
0.7081	Intermediate Similarity	NPD3226	Approved
0.708	Intermediate Similarity	NPD4750	Phase 3
0.7078	Intermediate Similarity	NPD4477	Approved
0.7078	Intermediate Similarity	NPD4476	Approved
0.7072	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7068	Intermediate Similarity	NPD846	Approved
0.7068	Intermediate Similarity	NPD940	Approved
0.7066	Intermediate Similarity	NPD8127	Discontinued
0.7063	Intermediate Similarity	NPD920	Approved
0.7051	Intermediate Similarity	NPD1243	Approved
0.7044	Intermediate Similarity	NPD5401	Approved
0.7039	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD5124	Phase 1
0.7037	Intermediate Similarity	NPD4675	Approved
0.7037	Intermediate Similarity	NPD4678	Approved
0.7034	Intermediate Similarity	NPD1535	Discovery
0.7033	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD2344	Approved
0.7032	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD2346	Discontinued

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