NPASS Compound

Structure

CID214629 OpenBabel06191716002D 22 26 0 0 1 0 0 0 0 0999 V2000 -4.0465 -1.6059 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3617 2.8564 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1530 1.6734 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1530 -1.6738 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4282 -2.0923 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4282 2.0919 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1530 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6025 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8777 0.4180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1530 0.8365 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1530 -0.8369 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.8777 -0.4185 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.7034 -1.6738 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7034 1.6734 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4282 0.4180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7034 0.8365 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7034 -0.8369 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.4282 -0.4185 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.6025 -0.8369 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.0656 -2.1178 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0213 2.0919 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 19 1 0 0 0 0 2 21 1 0 0 0 0 3 6 2 0 0 0 0 3 10 1 0 0 0 0 4 5 2 0 0 0 0 4 11 1 0 0 0 0 5 13 1 0 0 0 0 6 14 1 0 0 0 0 7 8 1 0 0 0 0 8 19 1 0 0 0 0 9 10 1 0 0 0 0 10 15 2 0 0 0 0 11 12 1 0 0 0 0 11 18 1 1 0 0 0 12 9 1 6 0 0 0 12 19 1 0 0 0 0 13 17 1 0 0 0 0 13 20 2 0 0 0 0 14 16 2 0 0 0 0 14 21 1 0 0 0 0 15 16 1 0 0 0 0 15 18 1 0 0 0 0 16 22 1 0 0 0 0 17 18 1 1 0 0 0 17 22 1 0 0 0 0 18 7 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	297.14
Volume:	301.287
LogP:	1.533
LogD:	0.997
LogS:	-2.124
# Rotatable Bonds:	1
TPSA:	38.77
# H-Bond Aceptor:	4
# H-Bond Donor:	0
# Rings:	5
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.791
Synthetic Accessibility Score:	5.148
Fsp3:	0.5
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.737
MDCK Permeability:	2.4740382286836393e-05
Pgp-inhibitor:	0.481
Pgp-substrate:	0.044
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.471
30% Bioavailability (F30%):	0.921

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.996
Plasma Protein Binding (PPB):	44.768917083740234%
Volume Distribution (VD):	2.09
Pgp-substrate:	59.741455078125%

ADMET: Metabolism

CYP1A2-inhibitor:	0.11
CYP1A2-substrate:	0.476
CYP2C19-inhibitor:	0.063
CYP2C19-substrate:	0.947
CYP2C9-inhibitor:	0.018
CYP2C9-substrate:	0.257
CYP2D6-inhibitor:	0.662
CYP2D6-substrate:	0.901
CYP3A4-inhibitor:	0.242
CYP3A4-substrate:	0.895

ADMET: Excretion

Clearance (CL):	8.777
Half-life (T1/2):	0.368

ADMET: Toxicity

hERG Blockers:	0.43
Human Hepatotoxicity (H-HT):	0.298
Drug-inuced Liver Injury (DILI):	0.055
AMES Toxicity:	0.04
Rat Oral Acute Toxicity:	0.941
Maximum Recommended Daily Dose:	0.927
Skin Sensitization:	0.69
Carcinogencity:	0.869
Eye Corrosion:	0.003
Eye Irritation:	0.01
Respiratory Toxicity:	0.965

Download Data

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

Natural Product: NPC214629

Natural Product ID:	NPC214629
*Common Name:**	Codeinone
IUPAC Name:	(4R,4aR,7aR,12bS)-9-methoxy-3-methyl-1,2,4,4a,7a,13-hexahydro-4,12-methanobenzofuro[3,2-e]isoquinoline-7-one
Synonyms:	Codeinone
Standard InCHIKey:	XYYVYLMBEZUESM-CMKMFDCUSA-N
Standard InCHI:	InChI=1S/C18H19NO3/c1-19-8-7-18-11-4-5-13(20)17(18)22-16-14(21-2)6-3-10(15(16)18)9-12(11)19/h3-6,11-12,17H,7-9H2,1-2H3/t11-,12+,17-,18-/m0/s1
SMILES:	CN1CC[C@]23[C@H]4C=CC(=O)[C@@H]3Oc3c(ccc(C[C@@H]14)c23)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL257627
PubChem CID:	5459910
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0000058] Morphinans

*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
NPO9498	Papaver somniferum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15019787]
NPO9498	Papaver somniferum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22029392]
NPO9498	Papaver somniferum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23517479]
NPO9498	Papaver somniferum	Species	Papaveraceae	Eukaryota	Latex Exudate	n.a.	n.a.	Database[FooDB]
NPO9498	Papaver somniferum	Species	Papaveraceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO9498	Papaver somniferum	Species	Papaveraceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO9498	Papaver somniferum	Species	Papaveraceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO9498	Papaver somniferum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9498	Papaver somniferum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9498	Papaver somniferum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO9498	Papaver somniferum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO7312	Aplidium multiplicatum	Species	Polyclinidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2466	Aloe microstigma	Species	Asphodelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10176	Chrozophora prostrata	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9498	Papaver somniferum	Species	Papaveraceae	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
EC50	1
Ki	1
Others	1

Activity Type	# Activity
Individual Protein	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT145	Individual Protein	Mu opioid receptor	Homo sapiens	Emax	=	100.0	%	PMID[558821]
NPT145	Individual Protein	Mu opioid receptor	Homo sapiens	EC50	=	294.0	nM	PMID[558821]
NPT145	Individual Protein	Mu opioid receptor	Homo sapiens	Ki	=	459.0	nM	PMID[558821]

☑ 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 NPC214629 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	332
0.1-0.2	1470
0.2-0.3	3783
0.3-0.4	10627
0.4-0.5	7827
0.5-0.6	9492
0.6-0.7	8657
0.7-0.8	475
0.8-0.85	18
0.85-0.9	14
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9701	High Similarity	NPC115906
0.9261	High Similarity	NPC174783
0.9061	High Similarity	NPC67346
0.9006	High Similarity	NPC311781
0.8994	High Similarity	NPC66909
0.8956	High Similarity	NPC43069
0.8956	High Similarity	NPC140577
0.8908	High Similarity	NPC298339
0.8852	High Similarity	NPC97086
0.875	High Similarity	NPC232533
0.8696	High Similarity	NPC64576
0.8696	High Similarity	NPC254045
0.8696	High Similarity	NPC151470
0.8696	High Similarity	NPC201055
0.8683	High Similarity	NPC180756
0.8683	High Similarity	NPC323443
0.8663	High Similarity	NPC157958
0.8649	High Similarity	NPC243483
0.8639	High Similarity	NPC475780
0.8462	Intermediate Similarity	NPC196231
0.8413	Intermediate Similarity	NPC126211
0.8333	Intermediate Similarity	NPC85747
0.8333	Intermediate Similarity	NPC124657
0.8333	Intermediate Similarity	NPC8337
0.8315	Intermediate Similarity	NPC35680
0.8286	Intermediate Similarity	NPC284842
0.8254	Intermediate Similarity	NPC244191
0.8182	Intermediate Similarity	NPC279665
0.8171	Intermediate Similarity	NPC255607
0.8171	Intermediate Similarity	NPC3375
0.8138	Intermediate Similarity	NPC293624
0.8077	Intermediate Similarity	NPC305847
0.8053	Intermediate Similarity	NPC474427
0.8033	Intermediate Similarity	NPC302449
0.8022	Intermediate Similarity	NPC149285
0.8011	Intermediate Similarity	NPC476569
0.8	Intermediate Similarity	NPC162694
0.8	Intermediate Similarity	NPC226428
0.7989	Intermediate Similarity	NPC475713
0.7989	Intermediate Similarity	NPC474432
0.7957	Intermediate Similarity	NPC141440
0.7944	Intermediate Similarity	NPC227683
0.7938	Intermediate Similarity	NPC476500
0.7842	Intermediate Similarity	NPC33256
0.7841	Intermediate Similarity	NPC118804
0.7803	Intermediate Similarity	NPC476579
0.7784	Intermediate Similarity	NPC476572
0.7778	Intermediate Similarity	NPC63152
0.7771	Intermediate Similarity	NPC99659
0.7771	Intermediate Similarity	NPC325871
0.7765	Intermediate Similarity	NPC225774
0.7727	Intermediate Similarity	NPC133817
0.7727	Intermediate Similarity	NPC476443
0.7722	Intermediate Similarity	NPC219341
0.7722	Intermediate Similarity	NPC24264
0.7722	Intermediate Similarity	NPC476432
0.7701	Intermediate Similarity	NPC326316
0.7701	Intermediate Similarity	NPC81733
0.7692	Intermediate Similarity	NPC474708
0.7692	Intermediate Similarity	NPC475747
0.768	Intermediate Similarity	NPC247389
0.7667	Intermediate Similarity	NPC167546
0.7667	Intermediate Similarity	NPC16805
0.7667	Intermediate Similarity	NPC302527
0.7663	Intermediate Similarity	NPC329969
0.7644	Intermediate Similarity	NPC94499
0.764	Intermediate Similarity	NPC106786
0.7637	Intermediate Similarity	NPC475845
0.7634	Intermediate Similarity	NPC27887
0.7634	Intermediate Similarity	NPC220961
0.7622	Intermediate Similarity	NPC241704
0.7611	Intermediate Similarity	NPC59567
0.7598	Intermediate Similarity	NPC232924
0.7598	Intermediate Similarity	NPC266753
0.7598	Intermediate Similarity	NPC160298
0.7598	Intermediate Similarity	NPC306902
0.7598	Intermediate Similarity	NPC477559
0.7582	Intermediate Similarity	NPC57812
0.7582	Intermediate Similarity	NPC210918
0.7582	Intermediate Similarity	NPC474324
0.7581	Intermediate Similarity	NPC294790
0.7581	Intermediate Similarity	NPC118633
0.7581	Intermediate Similarity	NPC148693
0.7579	Intermediate Similarity	NPC237579
0.7577	Intermediate Similarity	NPC46744
0.7577	Intermediate Similarity	NPC70290
0.7577	Intermediate Similarity	NPC124302
0.7577	Intermediate Similarity	NPC73020
0.7577	Intermediate Similarity	NPC14622
0.7577	Intermediate Similarity	NPC215098
0.7576	Intermediate Similarity	NPC80472
0.7569	Intermediate Similarity	NPC2770
0.7569	Intermediate Similarity	NPC39103
0.7556	Intermediate Similarity	NPC153631
0.7541	Intermediate Similarity	NPC241055
0.7541	Intermediate Similarity	NPC470324
0.754	Intermediate Similarity	NPC99179
0.754	Intermediate Similarity	NPC32154
0.754	Intermediate Similarity	NPC126284
0.7528	Intermediate Similarity	NPC57512
0.7527	Intermediate Similarity	NPC222524
0.7526	Intermediate Similarity	NPC230098
0.75	Intermediate Similarity	NPC226652
0.75	Intermediate Similarity	NPC72788
0.75	Intermediate Similarity	NPC314100
0.75	Intermediate Similarity	NPC120671
0.75	Intermediate Similarity	NPC249274
0.7487	Intermediate Similarity	NPC83019
0.7487	Intermediate Similarity	NPC208890
0.7486	Intermediate Similarity	NPC117188
0.7486	Intermediate Similarity	NPC205421
0.7486	Intermediate Similarity	NPC12053
0.7486	Intermediate Similarity	NPC78359
0.7486	Intermediate Similarity	NPC81218
0.7486	Intermediate Similarity	NPC158376
0.7486	Intermediate Similarity	NPC65490
0.7486	Intermediate Similarity	NPC145832
0.7486	Intermediate Similarity	NPC474931
0.7486	Intermediate Similarity	NPC306555
0.7486	Intermediate Similarity	NPC148014
0.7486	Intermediate Similarity	NPC129603
0.7486	Intermediate Similarity	NPC315707
0.7486	Intermediate Similarity	NPC40389
0.7474	Intermediate Similarity	NPC477258
0.7474	Intermediate Similarity	NPC470646
0.7473	Intermediate Similarity	NPC78222
0.7473	Intermediate Similarity	NPC13504
0.7473	Intermediate Similarity	NPC96603
0.7473	Intermediate Similarity	NPC196447
0.7473	Intermediate Similarity	NPC253043
0.7473	Intermediate Similarity	NPC136508
0.7473	Intermediate Similarity	NPC212794
0.7473	Intermediate Similarity	NPC306843
0.7473	Intermediate Similarity	NPC477563
0.7473	Intermediate Similarity	NPC180306
0.7472	Intermediate Similarity	NPC244112
0.746	Intermediate Similarity	NPC248642
0.7459	Intermediate Similarity	NPC303581
0.7459	Intermediate Similarity	NPC19520
0.7459	Intermediate Similarity	NPC67978
0.7459	Intermediate Similarity	NPC149090
0.7458	Intermediate Similarity	NPC476580
0.7458	Intermediate Similarity	NPC470924
0.745	Intermediate Similarity	NPC326895
0.7447	Intermediate Similarity	NPC267408
0.7447	Intermediate Similarity	NPC474745
0.7443	Intermediate Similarity	NPC474556
0.7436	Intermediate Similarity	NPC204580
0.7435	Intermediate Similarity	NPC477259
0.7435	Intermediate Similarity	NPC169387
0.743	Intermediate Similarity	NPC203784
0.743	Intermediate Similarity	NPC170503
0.743	Intermediate Similarity	NPC126519
0.7429	Intermediate Similarity	NPC7467
0.7425	Intermediate Similarity	NPC325568
0.7424	Intermediate Similarity	NPC202771
0.7424	Intermediate Similarity	NPC286135
0.7424	Intermediate Similarity	NPC328700
0.7424	Intermediate Similarity	NPC119818
0.7424	Intermediate Similarity	NPC2173
0.7421	Intermediate Similarity	NPC156576
0.7418	Intermediate Similarity	NPC1229
0.7418	Intermediate Similarity	NPC324144
0.7413	Intermediate Similarity	NPC106840
0.7413	Intermediate Similarity	NPC476495
0.7413	Intermediate Similarity	NPC94687
0.7405	Intermediate Similarity	NPC75958
0.7405	Intermediate Similarity	NPC6152
0.7403	Intermediate Similarity	NPC27410
0.7403	Intermediate Similarity	NPC166014
0.7403	Intermediate Similarity	NPC4304
0.7403	Intermediate Similarity	NPC205167
0.7401	Intermediate Similarity	NPC218575
0.7398	Intermediate Similarity	NPC23080
0.7398	Intermediate Similarity	NPC193906
0.7394	Intermediate Similarity	NPC474325
0.7394	Intermediate Similarity	NPC114364
0.7394	Intermediate Similarity	NPC320223
0.7391	Intermediate Similarity	NPC298979
0.738	Intermediate Similarity	NPC199465
0.738	Intermediate Similarity	NPC308267
0.738	Intermediate Similarity	NPC128560
0.738	Intermediate Similarity	NPC229166
0.738	Intermediate Similarity	NPC304675
0.7377	Intermediate Similarity	NPC168409
0.7377	Intermediate Similarity	NPC306669
0.7377	Intermediate Similarity	NPC247972
0.7376	Intermediate Similarity	NPC46990
0.7376	Intermediate Similarity	NPC476496
0.7374	Intermediate Similarity	NPC78733
0.7371	Intermediate Similarity	NPC16107
0.7371	Intermediate Similarity	NPC106295
0.7371	Intermediate Similarity	NPC476144
0.7371	Intermediate Similarity	NPC210437
0.7371	Intermediate Similarity	NPC51957
0.7368	Intermediate Similarity	NPC314682
0.7366	Intermediate Similarity	NPC65403
0.736	Intermediate Similarity	NPC267414
0.736	Intermediate Similarity	NPC475718
0.7356	Intermediate Similarity	NPC130926

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 NPC214629 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	230
0.1-0.2	756
0.2-0.3	1057
0.3-0.4	2350
0.4-0.5	2489
0.5-0.6	1519
0.6-0.7	635
0.7-0.8	82
0.8-0.85	13
0.85-0.9	16
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9701	High Similarity	NPD2971	Approved
0.9701	High Similarity	NPD2968	Approved
0.9253	High Similarity	NPD2488	Approved
0.9253	High Similarity	NPD2490	Approved
0.9162	High Similarity	NPD4107	Approved
0.9061	High Similarity	NPD3057	Approved
0.9006	High Similarity	NPD4482	Phase 3
0.8994	High Similarity	NPD2974	Approved
0.8994	High Similarity	NPD2973	Approved
0.8994	High Similarity	NPD2975	Approved
0.8956	High Similarity	NPD3533	Approved
0.8956	High Similarity	NPD2972	Approved
0.895	High Similarity	NPD4580	Approved
0.8908	High Similarity	NPD3534	Clinical (unspecified phase)
0.8798	High Similarity	NPD2493	Approved
0.8798	High Similarity	NPD2494	Approved
0.8772	High Similarity	NPD4481	Phase 3
0.8757	High Similarity	NPD4582	Approved
0.8757	High Similarity	NPD4583	Approved
0.875	High Similarity	NPD2491	Approved
0.8703	High Similarity	NPD4004	Approved
0.8703	High Similarity	NPD4002	Approved
0.8696	High Similarity	NPD3452	Approved
0.8696	High Similarity	NPD3450	Approved
0.8649	High Similarity	NPD3448	Approved
0.8605	High Similarity	NPD2969	Approved
0.8605	High Similarity	NPD2970	Approved
0.8579	High Similarity	NPD5676	Approved
0.8556	High Similarity	NPD4040	Phase 1
0.8547	High Similarity	NPD3051	Approved
0.8454	Intermediate Similarity	NPD5980	Discovery
0.8448	Intermediate Similarity	NPD27	Approved
0.8448	Intermediate Similarity	NPD2489	Approved
0.8191	Intermediate Similarity	NPD7907	Approved
0.8182	Intermediate Similarity	NPD4111	Phase 1
0.8182	Intermediate Similarity	NPD4665	Approved
0.8109	Intermediate Similarity	NPD5619	Clinical (unspecified phase)
0.8077	Intermediate Similarity	NPD7313	Approved
0.8077	Intermediate Similarity	NPD7312	Approved
0.8077	Intermediate Similarity	NPD7310	Approved
0.8077	Intermediate Similarity	NPD7311	Approved
0.8033	Intermediate Similarity	NPD7309	Approved
0.7978	Intermediate Similarity	NPD4577	Approved
0.7978	Intermediate Similarity	NPD4578	Approved
0.7849	Intermediate Similarity	NPD4663	Approved
0.7807	Intermediate Similarity	NPD7906	Approved
0.7689	Intermediate Similarity	NPD7048	Phase 3
0.7688	Intermediate Similarity	NPD3641	Approved
0.7688	Intermediate Similarity	NPD3639	Approved
0.7688	Intermediate Similarity	NPD3640	Phase 3
0.7586	Intermediate Similarity	NPD7047	Phase 3
0.7584	Intermediate Similarity	NPD5978	Approved
0.7584	Intermediate Similarity	NPD5977	Approved
0.7584	Intermediate Similarity	NPD5616	Clinical (unspecified phase)
0.7577	Intermediate Similarity	NPD4420	Approved
0.7565	Intermediate Similarity	NPD7667	Clinical (unspecified phase)
0.756	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.756	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7541	Intermediate Similarity	NPD2898	Approved
0.7536	Intermediate Similarity	NPD6997	Phase 2
0.7527	Intermediate Similarity	NPD6071	Discontinued
0.7514	Intermediate Similarity	NPD6386	Approved
0.7514	Intermediate Similarity	NPD6385	Approved
0.7486	Intermediate Similarity	NPD2563	Approved
0.7486	Intermediate Similarity	NPD2560	Approved
0.7475	Intermediate Similarity	NPD7497	Discontinued
0.7435	Intermediate Similarity	NPD7291	Discontinued
0.7425	Intermediate Similarity	NPD3110	Approved
0.7425	Intermediate Similarity	NPD3109	Approved
0.7424	Intermediate Similarity	NPD5005	Approved
0.7424	Intermediate Similarity	NPD5006	Approved
0.7371	Intermediate Similarity	NPD4584	Approved
0.733	Intermediate Similarity	NPD3647	Clinical (unspecified phase)
0.7326	Intermediate Similarity	NPD5312	Approved
0.7326	Intermediate Similarity	NPD4664	Clinical (unspecified phase)
0.7326	Intermediate Similarity	NPD5313	Approved
0.7323	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7318	Intermediate Similarity	NPD7110	Phase 1
0.7318	Intermediate Similarity	NPD7109	Clinical (unspecified phase)
0.7263	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7263	Intermediate Similarity	NPD1337	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD4859	Phase 1
0.7234	Intermediate Similarity	NPD8156	Discontinued
0.7234	Intermediate Similarity	NPD3050	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD4773	Phase 2
0.7222	Intermediate Similarity	NPD4772	Phase 2
0.7213	Intermediate Similarity	NPD7832	Clinical (unspecified phase)
0.7213	Intermediate Similarity	NPD7831	Phase 2
0.7213	Intermediate Similarity	NPD7833	Phase 2
0.72	Intermediate Similarity	NPD5241	Discontinued
0.7181	Intermediate Similarity	NPD8252	Approved
0.7181	Intermediate Similarity	NPD8099	Discontinued
0.7181	Intermediate Similarity	NPD8251	Approved
0.7181	Intermediate Similarity	NPD2163	Approved
0.7175	Intermediate Similarity	NPD1754	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD5564	Approved
0.7151	Intermediate Similarity	NPD7315	Approved
0.7143	Intermediate Similarity	NPD4585	Approved
0.7135	Intermediate Similarity	NPD5494	Approved
0.7127	Intermediate Similarity	NPD6873	Phase 2
0.7118	Intermediate Similarity	NPD3140	Approved
0.7118	Intermediate Similarity	NPD3142	Approved
0.7102	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD6107	Approved
0.7095	Intermediate Similarity	NPD6662	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD4727	Phase 1
0.7092	Intermediate Similarity	NPD5525	Clinical (unspecified phase)
0.709	Intermediate Similarity	NPD7177	Discontinued
0.7088	Intermediate Similarity	NPD7248	Discontinued
0.7083	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7079	Intermediate Similarity	NPD3146	Approved
0.7079	Intermediate Similarity	NPD3688	Clinical (unspecified phase)
0.7077	Intermediate Similarity	NPD6040	Clinical (unspecified phase)
0.7072	Intermediate Similarity	NPD6876	Approved
0.7072	Intermediate Similarity	NPD6875	Approved
0.7065	Intermediate Similarity	NPD5019	Clinical (unspecified phase)
0.7065	Intermediate Similarity	NPD5457	Discontinued
0.7062	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.7056	Intermediate Similarity	NPD4210	Discontinued
0.7053	Intermediate Similarity	NPD6042	Phase 2
0.7053	Intermediate Similarity	NPD42	Phase 2
0.7045	Intermediate Similarity	NPD5754	Discontinued
0.7041	Intermediate Similarity	NPD2669	Clinical (unspecified phase)
0.7031	Intermediate Similarity	NPD7038	Approved
0.7031	Intermediate Similarity	NPD7039	Approved
0.7029	Intermediate Similarity	NPD2897	Discontinued
0.7005	Intermediate Similarity	NPD3808	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6031	Approved
0.7	Intermediate Similarity	NPD6030	Approved
0.7	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD7427	Discontinued
0.6995	Remote Similarity	NPD7577	Discontinued
0.6989	Remote Similarity	NPD5709	Phase 3
0.6984	Remote Similarity	NPD4575	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD4166	Phase 2
0.6966	Remote Similarity	NPD6667	Approved
0.6966	Remote Similarity	NPD6666	Approved
0.6954	Remote Similarity	NPD7235	Clinical (unspecified phase)
0.6952	Remote Similarity	NPD4666	Phase 3
0.694	Remote Similarity	NPD5090	Approved
0.694	Remote Similarity	NPD5089	Approved
0.6931	Remote Similarity	NPD5242	Approved
0.6923	Remote Similarity	NPD6618	Phase 2
0.6923	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD8053	Approved
0.6923	Remote Similarity	NPD8054	Approved
0.6923	Remote Similarity	NPD4017	Approved
0.6919	Remote Similarity	NPD5353	Approved
0.6915	Remote Similarity	NPD8127	Discontinued
0.6909	Remote Similarity	NPD6625	Approved
0.6907	Remote Similarity	NPD7549	Discontinued
0.6902	Remote Similarity	NPD7298	Approved
0.6901	Remote Similarity	NPD5718	Phase 2
0.6898	Remote Similarity	NPD6862	Phase 2
0.6897	Remote Similarity	NPD6895	Approved
0.6897	Remote Similarity	NPD6896	Approved
0.6893	Remote Similarity	NPD4237	Approved
0.6893	Remote Similarity	NPD4236	Phase 3
0.6893	Remote Similarity	NPD7607	Clinical (unspecified phase)
0.6884	Remote Similarity	NPD7296	Approved
0.6882	Remote Similarity	NPD6788	Approved
0.6872	Remote Similarity	NPD7124	Phase 2
0.6866	Remote Similarity	NPD4361	Phase 2
0.6866	Remote Similarity	NPD4362	Clinical (unspecified phase)
0.6865	Remote Similarity	NPD5772	Approved
0.6865	Remote Similarity	NPD6668	Clinical (unspecified phase)
0.6865	Remote Similarity	NPD5773	Approved
0.6865	Remote Similarity	NPD6818	Clinical (unspecified phase)
0.6854	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6854	Remote Similarity	NPD4110	Phase 3
0.6852	Remote Similarity	NPD7278	Phase 2
0.6852	Remote Similarity	NPD7279	Phase 2
0.6847	Remote Similarity	NPD8285	Discontinued
0.6839	Remote Similarity	NPD5190	Phase 2
0.6837	Remote Similarity	NPD6851	Approved
0.6837	Remote Similarity	NPD6853	Approved
0.6833	Remote Similarity	NPD7837	Clinical (unspecified phase)
0.6831	Remote Similarity	NPD2649	Approved
0.6831	Remote Similarity	NPD2651	Approved
0.6821	Remote Similarity	NPD7132	Clinical (unspecified phase)
0.6816	Remote Similarity	NPD4360	Phase 2
0.6816	Remote Similarity	NPD4363	Phase 3
0.6811	Remote Similarity	NPD6844	Discontinued
0.6808	Remote Similarity	NPD8404	Phase 2
0.6804	Remote Similarity	NPD6297	Approved
0.6802	Remote Similarity	NPD5087	Clinical (unspecified phase)
0.6802	Remote Similarity	NPD6812	Clinical (unspecified phase)
0.68	Remote Similarity	NPD2200	Suspended
0.6798	Remote Similarity	NPD5177	Phase 3
0.6791	Remote Similarity	NPD3882	Suspended
0.6791	Remote Similarity	NPD4947	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD4603	Phase 2
0.6788	Remote Similarity	NPD5844	Phase 1
0.6772	Remote Similarity	NPD7201	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD3863	Clinical (unspecified phase)
0.6761	Remote Similarity	NPD1753	Discontinued
0.676	Remote Similarity	NPD6331	Phase 2
0.676	Remote Similarity	NPD6658	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD4424	Discontinued
0.6755	Remote Similarity	NPD1309	Phase 2

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