NPASS Compound

Structure

CID236668 OpenBabel06191716032D 24 26 0 0 0 0 0 0 0 0999 V2000 5.1962 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -4.5000 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 2.5981 0.5000 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 -1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -2.5000 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 -1.0000 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 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -4.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 22 1 0 0 0 0 2 23 1 0 0 0 0 3 24 1 0 0 0 0 4 6 1 0 0 0 0 4 12 2 0 0 0 0 5 7 2 0 0 0 0 5 12 1 0 0 0 0 6 14 2 0 0 0 0 7 14 1 0 0 0 0 8 9 2 0 0 0 0 8 13 1 0 0 0 0 9 20 1 0 0 0 0 10 13 2 0 0 0 0 10 16 1 0 0 0 0 11 15 2 0 0 0 0 11 17 1 0 0 0 0 12 19 1 0 0 0 0 13 15 1 0 0 0 0 14 22 1 0 0 0 0 15 18 1 0 0 0 0 16 17 2 0 0 0 0 16 23 1 0 0 0 0 17 24 1 0 0 0 0 18 19 1 0 0 0 0 18 20 2 0 0 0 0 19 21 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	323.12
Volume:	333.94
LogP:	3.082
LogD:	3.011
LogS:	-4.672
# Rotatable Bonds:	5
TPSA:	57.65
# H-Bond Aceptor:	5
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.673
Synthetic Accessibility Score:	1.981
Fsp3:	0.158
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.756
MDCK Permeability:	3.627142359619029e-05
Pgp-inhibitor:	0.436
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.314

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.376
Plasma Protein Binding (PPB):	90.47038269042969%
Volume Distribution (VD):	0.801
Pgp-substrate:	3.3238396644592285%

ADMET: Metabolism

CYP1A2-inhibitor:	0.759
CYP1A2-substrate:	0.954
CYP2C19-inhibitor:	0.804
CYP2C19-substrate:	0.662
CYP2C9-inhibitor:	0.668
CYP2C9-substrate:	0.894
CYP2D6-inhibitor:	0.046
CYP2D6-substrate:	0.912
CYP3A4-inhibitor:	0.821
CYP3A4-substrate:	0.655

ADMET: Excretion

Clearance (CL):	9.928
Half-life (T1/2):	0.445

ADMET: Toxicity

hERG Blockers:	0.561
Human Hepatotoxicity (H-HT):	0.313
Drug-inuced Liver Injury (DILI):	0.944
AMES Toxicity:	0.872
Rat Oral Acute Toxicity:	0.153
Maximum Recommended Daily Dose:	0.432
Skin Sensitization:	0.138
Carcinogencity:	0.761
Eye Corrosion:	0.003
Eye Irritation:	0.234
Respiratory Toxicity:	0.902

Download Data

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

Natural Product: NPC236668

Natural Product ID:	NPC236668
*Common Name:**	(6,7-Dimethoxyisoquinolin-1-Yl)-(4-Methoxyphenyl)Methanone
IUPAC Name:	(6,7-dimethoxyisoquinolin-1-yl)-(4-methoxyphenyl)methanone
Synonyms:
Standard InCHIKey:	UZNKGMPIZWBDHA-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C19H17NO4/c1-22-14-6-4-12(5-7-14)19(21)18-15-11-17(24-3)16(23-2)10-13(15)8-9-20-18/h4-11H,1-3H3
SMILES:	COc1ccc(cc1)C(=O)c1nccc2c1cc(OC)c(c2)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL94263
PubChem CID:	44326993
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0002566] Isoquinolines and derivatives [CHEMONTID:0000054] Benzylisoquinolines

*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
NPO8327	Cyclopia subternata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15315375]
NPO8327	Cyclopia subternata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19272608]
NPO5218	Seriphidium finitum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5218	Seriphidium finitum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO8327	Cyclopia subternata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO818	Erysimum cuspidatum	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24782	Aquilegia hybrid	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5218	Seriphidium finitum	Species	Asteraceae	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	2
Others	2

Activity Type	# Activity
Others	4

Target ID	Target Type	Target Name	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified	Inhibition	=	20.0	%	PMID[538858]
NPT2	Others	Unspecified	IC50	=	97000.0	nM	PMID[538858]
NPT2	Others	Unspecified	Inhibition	=	4.0	%	PMID[538858]
NPT2	Others	Unspecified	IC50	=	64700.0	nM	PMID[538858]

☑ 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 NPC236668 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	480
0.1-0.2	3006
0.2-0.3	11921
0.3-0.4	4525
0.4-0.5	10737
0.5-0.6	9493
0.6-0.7	2056
0.7-0.8	392
0.8-0.85	57
0.85-0.9	19
0.9-0.95	9
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9947	High Similarity	NPC146976
0.9397	High Similarity	NPC210434
0.931	High Similarity	NPC24019
0.9082	High Similarity	NPC22481
0.9038	High Similarity	NPC90875
0.9034	High Similarity	NPC233334
0.9029	High Similarity	NPC278525
0.8995	High Similarity	NPC108342
0.8995	High Similarity	NPC195268
0.8995	High Similarity	NPC133140
0.8952	High Similarity	NPC182907
0.8952	High Similarity	NPC189903
0.8826	High Similarity	NPC119134
0.8821	High Similarity	NPC166722
0.875	High Similarity	NPC470020
0.8744	High Similarity	NPC15406
0.8738	High Similarity	NPC210296
0.8704	High Similarity	NPC124313
0.8698	High Similarity	NPC84164
0.8698	High Similarity	NPC207283
0.8622	High Similarity	NPC4071
0.8622	High Similarity	NPC476582
0.8622	High Similarity	NPC476578
0.8507	High Similarity	NPC183537
0.8505	High Similarity	NPC253675
0.85	High Similarity	NPC476581
0.85	High Similarity	NPC16452
0.85	High Similarity	NPC36229
0.8485	Intermediate Similarity	NPC477019
0.8423	Intermediate Similarity	NPC77878
0.8416	Intermediate Similarity	NPC270515
0.835	Intermediate Similarity	NPC31930
0.8341	Intermediate Similarity	NPC322482
0.8325	Intermediate Similarity	NPC313189
0.83	Intermediate Similarity	NPC234197
0.8293	Intermediate Similarity	NPC290689
0.8271	Intermediate Similarity	NPC246381
0.8213	Intermediate Similarity	NPC296482
0.8213	Intermediate Similarity	NPC112206
0.8213	Intermediate Similarity	NPC202768
0.8213	Intermediate Similarity	NPC202605
0.8213	Intermediate Similarity	NPC53069
0.8208	Intermediate Similarity	NPC216612
0.8178	Intermediate Similarity	NPC470018
0.8146	Intermediate Similarity	NPC135549
0.814	Intermediate Similarity	NPC74575
0.8125	Intermediate Similarity	NPC251160
0.8073	Intermediate Similarity	NPC49547
0.8058	Intermediate Similarity	NPC193238
0.8038	Intermediate Similarity	NPC171409
0.8038	Intermediate Similarity	NPC96405
0.8028	Intermediate Similarity	NPC54066
0.8018	Intermediate Similarity	NPC41501
0.7983	Intermediate Similarity	NPC132385
0.7964	Intermediate Similarity	NPC470017
0.7943	Intermediate Similarity	NPC188420
0.7934	Intermediate Similarity	NPC473822
0.7928	Intermediate Similarity	NPC470022
0.7915	Intermediate Similarity	NPC271215
0.7915	Intermediate Similarity	NPC149471
0.7895	Intermediate Similarity	NPC134637
0.7876	Intermediate Similarity	NPC312872
0.787	Intermediate Similarity	NPC122463
0.786	Intermediate Similarity	NPC174049
0.7834	Intermediate Similarity	NPC122436
0.7812	Intermediate Similarity	NPC101350
0.7797	Intermediate Similarity	NPC208522
0.7793	Intermediate Similarity	NPC235076
0.7768	Intermediate Similarity	NPC235685
0.7767	Intermediate Similarity	NPC100079
0.7767	Intermediate Similarity	NPC23614
0.7763	Intermediate Similarity	NPC107123
0.7736	Intermediate Similarity	NPC220337
0.7718	Intermediate Similarity	NPC287437
0.7706	Intermediate Similarity	NPC137353
0.7696	Intermediate Similarity	NPC146724
0.7689	Intermediate Similarity	NPC472061
0.7685	Intermediate Similarity	NPC204446
0.767	Intermediate Similarity	NPC127085
0.7664	Intermediate Similarity	NPC266931
0.7664	Intermediate Similarity	NPC162530
0.765	Intermediate Similarity	NPC46451
0.765	Intermediate Similarity	NPC318068
0.7639	Intermediate Similarity	NPC473513
0.7632	Intermediate Similarity	NPC72905
0.7623	Intermediate Similarity	NPC201508
0.7598	Intermediate Similarity	NPC142385
0.7594	Intermediate Similarity	NPC82548
0.7591	Intermediate Similarity	NPC94842
0.7589	Intermediate Similarity	NPC471004
0.7588	Intermediate Similarity	NPC148889
0.7585	Intermediate Similarity	NPC129897
0.7583	Intermediate Similarity	NPC470164
0.7583	Intermediate Similarity	NPC323345
0.7581	Intermediate Similarity	NPC232225
0.7556	Intermediate Similarity	NPC255800
0.7556	Intermediate Similarity	NPC96584
0.7545	Intermediate Similarity	NPC260434
0.7545	Intermediate Similarity	NPC118121
0.7534	Intermediate Similarity	NPC469439
0.7532	Intermediate Similarity	NPC478045
0.7525	Intermediate Similarity	NPC204385
0.7523	Intermediate Similarity	NPC173080
0.7522	Intermediate Similarity	NPC208898
0.75	Intermediate Similarity	NPC71124
0.75	Intermediate Similarity	NPC206201
0.7489	Intermediate Similarity	NPC478078
0.7478	Intermediate Similarity	NPC172222
0.7477	Intermediate Similarity	NPC174758
0.7468	Intermediate Similarity	NPC63971
0.7468	Intermediate Similarity	NPC91868
0.7465	Intermediate Similarity	NPC308943
0.7464	Intermediate Similarity	NPC5374
0.7452	Intermediate Similarity	NPC224928
0.7426	Intermediate Similarity	NPC13603
0.7418	Intermediate Similarity	NPC472286
0.7418	Intermediate Similarity	NPC472287
0.7412	Intermediate Similarity	NPC295228
0.7407	Intermediate Similarity	NPC208284
0.7406	Intermediate Similarity	NPC207971
0.7406	Intermediate Similarity	NPC191489
0.7401	Intermediate Similarity	NPC329631
0.7397	Intermediate Similarity	NPC27041
0.7391	Intermediate Similarity	NPC254957
0.7385	Intermediate Similarity	NPC237740
0.7384	Intermediate Similarity	NPC53255
0.7384	Intermediate Similarity	NPC303374
0.7384	Intermediate Similarity	NPC475301
0.7384	Intermediate Similarity	NPC326930
0.7384	Intermediate Similarity	NPC85879
0.7382	Intermediate Similarity	NPC58661
0.7381	Intermediate Similarity	NPC123395
0.7381	Intermediate Similarity	NPC280714
0.7376	Intermediate Similarity	NPC323969
0.7373	Intermediate Similarity	NPC264176
0.7371	Intermediate Similarity	NPC210256
0.7371	Intermediate Similarity	NPC268077
0.7371	Intermediate Similarity	NPC327592
0.7371	Intermediate Similarity	NPC285558
0.7366	Intermediate Similarity	NPC44354
0.7362	Intermediate Similarity	NPC51854
0.7361	Intermediate Similarity	NPC471304
0.7361	Intermediate Similarity	NPC124086
0.7357	Intermediate Similarity	NPC207686
0.734	Intermediate Similarity	NPC207851
0.7336	Intermediate Similarity	NPC300156
0.7336	Intermediate Similarity	NPC45190
0.7336	Intermediate Similarity	NPC317373
0.7333	Intermediate Similarity	NPC473833
0.7331	Intermediate Similarity	NPC302807
0.7319	Intermediate Similarity	NPC9729
0.7318	Intermediate Similarity	NPC246658
0.7315	Intermediate Similarity	NPC174672
0.7313	Intermediate Similarity	NPC474688
0.7309	Intermediate Similarity	NPC477788
0.7304	Intermediate Similarity	NPC15801
0.7302	Intermediate Similarity	NPC222561
0.73	Intermediate Similarity	NPC84347
0.7297	Intermediate Similarity	NPC472099
0.7294	Intermediate Similarity	NPC316981
0.7284	Intermediate Similarity	NPC475844
0.7284	Intermediate Similarity	NPC315634
0.7284	Intermediate Similarity	NPC88923
0.7284	Intermediate Similarity	NPC100734
0.728	Intermediate Similarity	NPC53534
0.7277	Intermediate Similarity	NPC295898
0.7273	Intermediate Similarity	NPC328928
0.7273	Intermediate Similarity	NPC274982
0.7268	Intermediate Similarity	NPC118084
0.7265	Intermediate Similarity	NPC280799
0.7265	Intermediate Similarity	NPC60621
0.7264	Intermediate Similarity	NPC176538
0.726	Intermediate Similarity	NPC141915
0.726	Intermediate Similarity	NPC280964
0.726	Intermediate Similarity	NPC56170
0.726	Intermediate Similarity	NPC114335
0.7257	Intermediate Similarity	NPC157931
0.7252	Intermediate Similarity	NPC74360
0.7248	Intermediate Similarity	NPC146418
0.7246	Intermediate Similarity	NPC76748
0.7243	Intermediate Similarity	NPC152620
0.7237	Intermediate Similarity	NPC217176
0.7233	Intermediate Similarity	NPC206186
0.7232	Intermediate Similarity	NPC144452
0.7232	Intermediate Similarity	NPC280272
0.7227	Intermediate Similarity	NPC190401
0.7227	Intermediate Similarity	NPC239763
0.7227	Intermediate Similarity	NPC55470
0.7225	Intermediate Similarity	NPC307963
0.7222	Intermediate Similarity	NPC4687
0.7222	Intermediate Similarity	NPC316224
0.7222	Intermediate Similarity	NPC249583
0.722	Intermediate Similarity	NPC295158
0.722	Intermediate Similarity	NPC225279
0.722	Intermediate Similarity	NPC276657
0.7215	Intermediate Similarity	NPC219087
0.7215	Intermediate Similarity	NPC318299
0.7215	Intermediate Similarity	NPC472098
0.7212	Intermediate Similarity	NPC92111
0.7212	Intermediate Similarity	NPC473506

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 NPC236668 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	301
0.1-0.2	689
0.2-0.3	878
0.3-0.4	1277
0.4-0.5	2529
0.5-0.6	2379
0.6-0.7	968
0.7-0.8	123
0.8-0.85	4
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8995	High Similarity	NPD3923	Approved
0.8995	High Similarity	NPD3922	Approved
0.8995	High Similarity	NPD3921	Approved
0.8995	High Similarity	NPD3924	Approved
0.8413	Intermediate Similarity	NPD3920	Phase 2
0.8213	Intermediate Similarity	NPD3816	Phase 1
0.8213	Intermediate Similarity	NPD3815	Phase 1
0.8079	Intermediate Similarity	NPD8091	Phase 3
0.8026	Intermediate Similarity	NPD4926	Clinical (unspecified phase)
0.802	Intermediate Similarity	NPD6257	Clinical (unspecified phase)
0.8018	Intermediate Similarity	NPD7885	Phase 2
0.8018	Intermediate Similarity	NPD7886	Phase 2
0.7952	Intermediate Similarity	NPD7069	Discontinued
0.7944	Intermediate Similarity	NPD6242	Discontinued
0.7919	Intermediate Similarity	NPD4889	Approved
0.7851	Intermediate Similarity	NPD8350	Clinical (unspecified phase)
0.785	Intermediate Similarity	NPD4429	Discontinued
0.783	Intermediate Similarity	NPD7571	Clinical (unspecified phase)
0.7804	Intermediate Similarity	NPD3326	Clinical (unspecified phase)
0.7783	Intermediate Similarity	NPD5866	Approved
0.7766	Intermediate Similarity	NPD7414	Clinical (unspecified phase)
0.7743	Intermediate Similarity	NPD6790	Phase 1
0.7692	Intermediate Similarity	NPD1923	Clinical (unspecified phase)
0.7658	Intermediate Similarity	NPD5801	Clinical (unspecified phase)
0.7658	Intermediate Similarity	NPD5022	Discontinued
0.765	Intermediate Similarity	NPD3763	Approved
0.7642	Intermediate Similarity	NPD5483	Clinical (unspecified phase)
0.7632	Intermediate Similarity	NPD1483	Discontinued
0.7604	Intermediate Similarity	NPD6568	Discontinued
0.7596	Intermediate Similarity	NPD6219	Discontinued
0.7589	Intermediate Similarity	NPD4885	Approved
0.7571	Intermediate Similarity	NPD5513	Phase 2
0.7556	Intermediate Similarity	NPD6494	Phase 2
0.7524	Intermediate Similarity	NPD6477	Clinical (unspecified phase)
0.7523	Intermediate Similarity	NPD7395	Discontinued
0.7522	Intermediate Similarity	NPD6963	Approved
0.7522	Intermediate Similarity	NPD6964	Approved
0.7512	Intermediate Similarity	NPD6569	Phase 2
0.7512	Intermediate Similarity	NPD5658	Approved
0.7511	Intermediate Similarity	NPD6525	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD8052	Clinical (unspecified phase)
0.7487	Intermediate Similarity	NPD6872	Clinical (unspecified phase)
0.7466	Intermediate Similarity	NPD2285	Clinical (unspecified phase)
0.7443	Intermediate Similarity	NPD3354	Phase 2
0.744	Intermediate Similarity	NPD4418	Discontinued
0.7436	Intermediate Similarity	NPD7588	Discontinued
0.743	Intermediate Similarity	NPD7467	Discontinued
0.7411	Intermediate Similarity	NPD3259	Approved
0.7406	Intermediate Similarity	NPD6228	Discontinued
0.7406	Intermediate Similarity	NPD7708	Approved
0.7401	Intermediate Similarity	NPD6741	Clinical (unspecified phase)
0.7397	Intermediate Similarity	NPD4989	Phase 2
0.7391	Intermediate Similarity	NPD2921	Clinical (unspecified phase)
0.7385	Intermediate Similarity	NPD2780	Approved
0.7385	Intermediate Similarity	NPD2782	Approved
0.738	Intermediate Similarity	NPD5805	Approved
0.7376	Intermediate Similarity	NPD8479	Phase 2
0.7366	Intermediate Similarity	NPD3263	Phase 3
0.7362	Intermediate Similarity	NPD5482	Discontinued
0.7361	Intermediate Similarity	NPD5914	Approved
0.7348	Intermediate Similarity	NPD6727	Phase 2
0.7345	Intermediate Similarity	NPD4952	Phase 3
0.7336	Intermediate Similarity	NPD5601	Phase 2
0.7328	Intermediate Similarity	NPD6716	Phase 1
0.7327	Intermediate Similarity	NPD3386	Phase 2
0.7327	Intermediate Similarity	NPD7927	Clinical (unspecified phase)
0.7325	Intermediate Similarity	NPD5040	Clinical (unspecified phase)
0.7319	Intermediate Similarity	NPD4558	Phase 2
0.731	Intermediate Similarity	NPD2781	Approved
0.7308	Intermediate Similarity	NPD4551	Phase 2
0.7302	Intermediate Similarity	NPD5429	Discontinued
0.729	Intermediate Similarity	NPD3946	Clinical (unspecified phase)
0.7289	Intermediate Similarity	NPD7426	Phase 1
0.7289	Intermediate Similarity	NPD5640	Discontinued
0.7284	Intermediate Similarity	NPD7803	Approved
0.7281	Intermediate Similarity	NPD4997	Clinical (unspecified phase)
0.7265	Intermediate Similarity	NPD4923	Phase 1
0.7265	Intermediate Similarity	NPD6230	Discontinued
0.7264	Intermediate Similarity	NPD4396	Clinical (unspecified phase)
0.7249	Intermediate Similarity	NPD4373	Phase 2
0.7238	Intermediate Similarity	NPD5512	Phase 3
0.7237	Intermediate Similarity	NPD6962	Phase 2
0.7227	Intermediate Similarity	NPD3257	Approved
0.7225	Intermediate Similarity	NPD1038	Approved
0.7225	Intermediate Similarity	NPD1304	Clinical (unspecified phase)
0.722	Intermediate Similarity	NPD5070	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD7225	Discontinued
0.7209	Intermediate Similarity	NPD4795	Phase 2
0.7198	Intermediate Similarity	NPD7729	Clinical (unspecified phase)
0.7195	Intermediate Similarity	NPD8149	Discontinued
0.7195	Intermediate Similarity	NPD5612	Discontinued
0.719	Intermediate Similarity	NPD5975	Clinical (unspecified phase)
0.7189	Intermediate Similarity	NPD5863	Clinical (unspecified phase)
0.7186	Intermediate Similarity	NPD3006	Discontinued
0.7175	Intermediate Similarity	NPD3258	Approved
0.7169	Intermediate Similarity	NPD7703	Clinical (unspecified phase)
0.7169	Intermediate Similarity	NPD4131	Phase 3
0.716	Intermediate Similarity	NPD3217	Phase 2
0.7156	Intermediate Similarity	NPD6824	Clinical (unspecified phase)
0.7155	Intermediate Similarity	NPD4958	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD5977	Approved
0.7143	Intermediate Similarity	NPD7222	Phase 2
0.7143	Intermediate Similarity	NPD5978	Approved
0.7143	Intermediate Similarity	NPD8304	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7180	Phase 3
0.7131	Intermediate Similarity	NPD3328	Phase 2
0.713	Intermediate Similarity	NPD4038	Approved
0.713	Intermediate Similarity	NPD2831	Approved
0.713	Intermediate Similarity	NPD4122	Approved
0.713	Intermediate Similarity	NPD4034	Approved
0.713	Intermediate Similarity	NPD4037	Approved
0.713	Intermediate Similarity	NPD4036	Approved
0.713	Intermediate Similarity	NPD4039	Approved
0.713	Intermediate Similarity	NPD32	Approved
0.713	Intermediate Similarity	NPD5632	Approved
0.713	Intermediate Similarity	NPD4035	Approved
0.713	Intermediate Similarity	NPD31	Approved
0.713	Intermediate Similarity	NPD4033	Approved
0.7129	Intermediate Similarity	NPD2334	Discontinued
0.7124	Intermediate Similarity	NPD7278	Phase 2
0.7124	Intermediate Similarity	NPD7279	Phase 2
0.7118	Intermediate Similarity	NPD1659	Phase 1
0.7117	Intermediate Similarity	NPD2433	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD7291	Discontinued
0.7109	Intermediate Similarity	NPD3395	Approved
0.7109	Intermediate Similarity	NPD3396	Approved
0.7106	Intermediate Similarity	NPD6517	Phase 3
0.7105	Intermediate Similarity	NPD4845	Discontinued
0.7105	Intermediate Similarity	NPD7994	Phase 2
0.7105	Intermediate Similarity	NPD4328	Approved
0.7103	Intermediate Similarity	NPD1739	Approved
0.7103	Intermediate Similarity	NPD1740	Approved
0.7097	Intermediate Similarity	NPD7010	Phase 3
0.7091	Intermediate Similarity	NPD6567	Clinical (unspecified phase)
0.709	Intermediate Similarity	NPD7862	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD5488	Discontinued
0.7083	Intermediate Similarity	NPD7859	Phase 2
0.7079	Intermediate Similarity	NPD5602	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD7956	Approved
0.7078	Intermediate Similarity	NPD7955	Approved
0.7075	Intermediate Similarity	NPD3478	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD3477	Phase 2
0.7074	Intermediate Similarity	NPD7710	Clinical (unspecified phase)
0.7072	Intermediate Similarity	NPD7538	Clinical (unspecified phase)
0.7069	Intermediate Similarity	NPD7807	Clinical (unspecified phase)
0.7065	Intermediate Similarity	NPD1078	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD3397	Phase 2
0.7048	Intermediate Similarity	NPD7547	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD6262	Clinical (unspecified phase)
0.7035	Intermediate Similarity	NPD5147	Discontinued
0.7034	Intermediate Similarity	NPD4876	Phase 3
0.7034	Intermediate Similarity	NPD4875	Phase 3
0.7032	Intermediate Similarity	NPD2739	Clinical (unspecified phase)
0.7031	Intermediate Similarity	NPD6553	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD3945	Discontinued
0.7023	Intermediate Similarity	NPD4491	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD8017	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD8016	Phase 3
0.7019	Intermediate Similarity	NPD2917	Approved
0.7019	Intermediate Similarity	NPD4375	Approved
0.7018	Intermediate Similarity	NPD5530	Phase 1
0.7018	Intermediate Similarity	NPD6247	Clinical (unspecified phase)
0.7017	Intermediate Similarity	NPD8100	Phase 3
0.7014	Intermediate Similarity	NPD4502	Phase 2
0.7014	Intermediate Similarity	NPD4372	Phase 1
0.701	Intermediate Similarity	NPD5751	Clinical (unspecified phase)
0.7009	Intermediate Similarity	NPD5071	Phase 2
0.7004	Intermediate Similarity	NPD6160	Clinical (unspecified phase)
0.7004	Intermediate Similarity	NPD5450	Discontinued
0.6996	Remote Similarity	NPD5417	Clinical (unspecified phase)
0.6996	Remote Similarity	NPD6140	Clinical (unspecified phase)
0.6991	Remote Similarity	NPD5930	Phase 3
0.6986	Remote Similarity	NPD7452	Approved
0.6986	Remote Similarity	NPD7453	Approved
0.698	Remote Similarity	NPD6530	Approved
0.698	Remote Similarity	NPD6531	Approved
0.6979	Remote Similarity	NPD6825	Phase 1
0.6977	Remote Similarity	NPD3825	Phase 3
0.6977	Remote Similarity	NPD4118	Clinical (unspecified phase)
0.6972	Remote Similarity	NPD3947	Discontinued
0.697	Remote Similarity	NPD5479	Discontinued
0.6966	Remote Similarity	NPD5469	Phase 3
0.6964	Remote Similarity	NPD3394	Approved
0.6964	Remote Similarity	NPD3393	Approved
0.6964	Remote Similarity	NPD2412	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD3389	Approved
0.6958	Remote Similarity	NPD7403	Phase 1
0.6958	Remote Similarity	NPD7012	Phase 3
0.6958	Remote Similarity	NPD7013	Phase 3
0.6958	Remote Similarity	NPD4369	Phase 2
0.6951	Remote Similarity	NPD3794	Approved
0.6951	Remote Similarity	NPD3795	Approved
0.6948	Remote Similarity	NPD6861	Clinical (unspecified phase)
0.6947	Remote Similarity	NPD5519	Discontinued
0.6947	Remote Similarity	NPD6974	Phase 3
0.6943	Remote Similarity	NPD4132	Clinical (unspecified phase)
0.6942	Remote Similarity	NPD2601	Approved
0.6942	Remote Similarity	NPD2600	Approved
0.6942	Remote Similarity	NPD2599	Approved
0.6937	Remote Similarity	NPD5416	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