NPASS Compound

Structure

CID174783 OpenBabel06191715552D 23 27 0 0 1 0 0 0 0 0999 V2000 -4.0830 -1.6204 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3650 2.8821 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7177 -1.6333 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1723 1.6885 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1724 -1.6889 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4410 2.1107 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4411 -2.1111 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1724 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6350 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9037 0.4218 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1724 0.8440 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1724 -0.8444 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.9037 -0.4222 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.7098 1.6885 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7098 -1.6889 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.4411 0.4218 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7098 0.8440 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7098 -0.8445 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.4411 -0.4222 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.6350 -0.8444 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.0216 2.1107 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0215 -2.1111 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 20 1 0 0 0 0 2 21 1 0 0 0 0 3 22 1 0 0 0 0 4 6 2 0 0 0 0 4 11 1 0 0 0 0 5 7 2 0 0 0 0 5 12 1 0 0 0 0 6 14 1 0 0 0 0 7 15 1 0 0 0 0 8 9 1 0 0 0 0 9 20 1 0 0 0 0 10 11 1 0 0 0 0 11 16 2 0 0 0 0 12 13 1 0 0 0 0 12 19 1 1 0 0 0 13 10 1 6 0 0 0 13 20 1 0 0 0 0 14 17 2 0 0 0 0 14 21 1 0 0 0 0 15 18 1 0 0 0 0 15 22 1 1 0 0 0 16 17 1 0 0 0 0 16 19 1 0 0 0 0 17 23 1 0 0 0 0 18 19 1 1 0 0 0 18 23 1 0 0 0 0 19 8 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	313.17
Volume:	321.219
LogP:	2.489
LogD:	1.586
LogS:	-2.608
# Rotatable Bonds:	2
TPSA:	30.93
# H-Bond Aceptor:	4
# H-Bond Donor:	0
# Rings:	5
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.783
Synthetic Accessibility Score:	5.214
Fsp3:	0.579
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:	-4.773
MDCK Permeability:	2.098181903420482e-05
Pgp-inhibitor:	0.107
Pgp-substrate:	0.988
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.094
30% Bioavailability (F30%):	0.99

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.996
Plasma Protein Binding (PPB):	23.343507766723633%
Volume Distribution (VD):	3.215
Pgp-substrate:	53.728248596191406%

ADMET: Metabolism

CYP1A2-inhibitor:	0.052
CYP1A2-substrate:	0.871
CYP2C19-inhibitor:	0.027
CYP2C19-substrate:	0.951
CYP2C9-inhibitor:	0.027
CYP2C9-substrate:	0.214
CYP2D6-inhibitor:	0.746
CYP2D6-substrate:	0.919
CYP3A4-inhibitor:	0.2
CYP3A4-substrate:	0.906

ADMET: Excretion

Clearance (CL):	14.73
Half-life (T1/2):	0.673

ADMET: Toxicity

hERG Blockers:	0.6
Human Hepatotoxicity (H-HT):	0.152
Drug-inuced Liver Injury (DILI):	0.518
AMES Toxicity:	0.024
Rat Oral Acute Toxicity:	0.835
Maximum Recommended Daily Dose:	0.861
Skin Sensitization:	0.385
Carcinogencity:	0.074
Eye Corrosion:	0.003
Eye Irritation:	0.009
Respiratory Toxicity:	0.97

Download Data

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

Natural Product: NPC174783

Natural Product ID:	NPC174783
*Common Name:**	Codeine-6-Methyl Ether
IUPAC Name:	(4R,4aR,7S,7aR,12bS)-7,9-dimethoxy-3-methyl-2,4,4a,7,7a,13-hexahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinoline
Synonyms:	Codeine-6-Methyl Ether
Standard InCHIKey:	HGPQAWTZLJXCTC-SSTWWWIQSA-N
Standard InCHI:	InChI=1S/C19H23NO3/c1-20-9-8-19-12-5-7-15(22-3)18(19)23-17-14(21-2)6-4-11(16(17)19)10-13(12)20/h4-7,12-13,15,18H,8-10H2,1-3H3/t12-,13+,15-,18-,19-/m0/s1
SMILES:	CO[C@H]1C=C[C@@H]2[C@@]34[C@H]1Oc1c4c(C[C@H]2N(CC3)C)ccc1OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL412301
PubChem CID:	5492619
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	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	Latex Exudate	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
Ki	3
Others	2

Activity Type	# Activity
Individual Protein	3
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT272	Individual Protein	Kappa opioid receptor	Homo sapiens	Ki	=	5430.0	nM	PMID[533360]
NPT271	Individual Protein	Delta opioid receptor	Homo sapiens	Ki	=	4410.0	nM	PMID[533360]
NPT145	Individual Protein	Mu opioid receptor	Homo sapiens	Ki	=	1910.0	nM	PMID[533360]
NPT2	Others	Unspecified		Ratio Ki	=	2.0	n.a.	PMID[533360]
NPT2	Others	Unspecified		Ratio Ki	=	3.0	n.a.	PMID[533360]

☑ 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 NPC174783 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	350
0.1-0.2	1448
0.2-0.3	5106
0.3-0.4	12073
0.4-0.5	6060
0.5-0.6	12387
0.6-0.7	4454
0.7-0.8	671
0.8-0.85	121
0.85-0.9	12
0.9-0.95	8
0.95-1	7

Similarity Score	Similarity Level	Natural Product ID
0.9719	High Similarity	NPC311781
0.9665	High Similarity	NPC140577
0.9665	High Similarity	NPC43069
0.9556	High Similarity	NPC67346
0.9448	High Similarity	NPC232533
0.9348	High Similarity	NPC157958
0.9341	High Similarity	NPC243483
0.9341	High Similarity	NPC97086
0.9261	High Similarity	NPC214629
0.9086	High Similarity	NPC126211
0.8983	High Similarity	NPC115906
0.836	Intermediate Similarity	NPC66909
0.8261	Intermediate Similarity	NPC298339
0.8098	Intermediate Similarity	NPC35680
0.8093	Intermediate Similarity	NPC254045
0.8093	Intermediate Similarity	NPC201055
0.8093	Intermediate Similarity	NPC64576
0.8093	Intermediate Similarity	NPC151470
0.809	Intermediate Similarity	NPC475780
0.8023	Intermediate Similarity	NPC180756
0.8023	Intermediate Similarity	NPC323443
0.7958	Intermediate Similarity	NPC196231
0.7868	Intermediate Similarity	NPC244191
0.7801	Intermediate Similarity	NPC162694
0.7795	Intermediate Similarity	NPC279665
0.7772	Intermediate Similarity	NPC284842
0.776	Intermediate Similarity	NPC141440
0.7742	Intermediate Similarity	NPC227683
0.7717	Intermediate Similarity	NPC124657
0.7697	Intermediate Similarity	NPC85747
0.7697	Intermediate Similarity	NPC8337
0.7684	Intermediate Similarity	NPC305847
0.7665	Intermediate Similarity	NPC293624
0.7662	Intermediate Similarity	NPC476500
0.7653	Intermediate Similarity	NPC33256
0.7644	Intermediate Similarity	NPC302449
0.7588	Intermediate Similarity	NPC474427
0.7568	Intermediate Similarity	NPC3375
0.7568	Intermediate Similarity	NPC255607
0.7539	Intermediate Similarity	NPC149285
0.7539	Intermediate Similarity	NPC27887
0.7527	Intermediate Similarity	NPC476443
0.7527	Intermediate Similarity	NPC133817
0.7525	Intermediate Similarity	NPC474432
0.7525	Intermediate Similarity	NPC475713
0.7514	Intermediate Similarity	NPC476569
0.75	Intermediate Similarity	NPC63152
0.7462	Intermediate Similarity	NPC94499
0.7405	Intermediate Similarity	NPC226428
0.7402	Intermediate Similarity	NPC80472
0.7363	Intermediate Similarity	NPC470924
0.7351	Intermediate Similarity	NPC118804
0.7313	Intermediate Similarity	NPC73020
0.7313	Intermediate Similarity	NPC124302
0.7313	Intermediate Similarity	NPC70290
0.7313	Intermediate Similarity	NPC14622
0.7313	Intermediate Similarity	NPC215098
0.7313	Intermediate Similarity	NPC46744
0.7308	Intermediate Similarity	NPC476579
0.7303	Intermediate Similarity	NPC27220
0.7297	Intermediate Similarity	NPC476572
0.7287	Intermediate Similarity	NPC225774
0.7283	Intermediate Similarity	NPC99659
0.7283	Intermediate Similarity	NPC325871
0.7282	Intermediate Similarity	NPC326895
0.7273	Intermediate Similarity	NPC153631
0.7255	Intermediate Similarity	NPC286135
0.7255	Intermediate Similarity	NPC475747
0.7254	Intermediate Similarity	NPC222524
0.7251	Intermediate Similarity	NPC38964
0.7249	Intermediate Similarity	NPC24264
0.7249	Intermediate Similarity	NPC476432
0.7249	Intermediate Similarity	NPC219341
0.7246	Intermediate Similarity	NPC94687
0.7246	Intermediate Similarity	NPC476495
0.7246	Intermediate Similarity	NPC106840
0.7241	Intermediate Similarity	NPC120671
0.7241	Intermediate Similarity	NPC72788
0.7241	Intermediate Similarity	NPC314100
0.7241	Intermediate Similarity	NPC226652
0.7228	Intermediate Similarity	NPC83019
0.7225	Intermediate Similarity	NPC298071
0.7225	Intermediate Similarity	NPC474708
0.7222	Intermediate Similarity	NPC208890
0.7214	Intermediate Similarity	NPC477258
0.7213	Intermediate Similarity	NPC81733
0.7213	Intermediate Similarity	NPC326316
0.7212	Intermediate Similarity	NPC46990
0.7211	Intermediate Similarity	NPC247389
0.7196	Intermediate Similarity	NPC16805
0.7196	Intermediate Similarity	NPC302527
0.7196	Intermediate Similarity	NPC167546
0.7188	Intermediate Similarity	NPC67978
0.7188	Intermediate Similarity	NPC303581
0.7183	Intermediate Similarity	NPC82056
0.7179	Intermediate Similarity	NPC220961
0.7178	Intermediate Similarity	NPC204580
0.7173	Intermediate Similarity	NPC475845
0.7172	Intermediate Similarity	NPC477259
0.7172	Intermediate Similarity	NPC169387
0.7171	Intermediate Similarity	NPC202771
0.7171	Intermediate Similarity	NPC2173
0.7171	Intermediate Similarity	NPC328700
0.7171	Intermediate Similarity	NPC119818
0.7166	Intermediate Similarity	NPC106786
0.7165	Intermediate Similarity	NPC241704
0.7158	Intermediate Similarity	NPC472839
0.7143	Intermediate Similarity	NPC59567
0.7136	Intermediate Similarity	NPC166979
0.7136	Intermediate Similarity	NPC237579
0.7129	Intermediate Similarity	NPC476496
0.7128	Intermediate Similarity	NPC306902
0.7128	Intermediate Similarity	NPC232924
0.7128	Intermediate Similarity	NPC477559
0.7128	Intermediate Similarity	NPC266753
0.7128	Intermediate Similarity	NPC160298
0.7128	Intermediate Similarity	NPC26353
0.712	Intermediate Similarity	NPC132054
0.712	Intermediate Similarity	NPC119669
0.712	Intermediate Similarity	NPC474324
0.712	Intermediate Similarity	NPC210918
0.712	Intermediate Similarity	NPC57812
0.7115	Intermediate Similarity	NPC308943
0.7113	Intermediate Similarity	NPC329969
0.7113	Intermediate Similarity	NPC308267
0.7107	Intermediate Similarity	NPC233718
0.7105	Intermediate Similarity	NPC35345
0.7105	Intermediate Similarity	NPC39103
0.7105	Intermediate Similarity	NPC2770
0.7104	Intermediate Similarity	NPC470088
0.7097	Intermediate Similarity	NPC10429
0.7092	Intermediate Similarity	NPC126284
0.7092	Intermediate Similarity	NPC32154
0.7085	Intermediate Similarity	NPC230098
0.7083	Intermediate Similarity	NPC41689
0.7083	Intermediate Similarity	NPC279768
0.7083	Intermediate Similarity	NPC241055
0.7083	Intermediate Similarity	NPC470324
0.7065	Intermediate Similarity	NPC474556
0.7059	Intermediate Similarity	NPC477133
0.7059	Intermediate Similarity	NPC477132
0.7059	Intermediate Similarity	NPC57512
0.7059	Intermediate Similarity	NPC71124
0.7053	Intermediate Similarity	NPC207971
0.7049	Intermediate Similarity	NPC71821
0.7047	Intermediate Similarity	NPC191012
0.7047	Intermediate Similarity	NPC475109
0.7047	Intermediate Similarity	NPC263212
0.7044	Intermediate Similarity	NPC470646
0.7042	Intermediate Similarity	NPC55470
0.7041	Intermediate Similarity	NPC148693
0.7041	Intermediate Similarity	NPC294790
0.7041	Intermediate Similarity	NPC118633
0.7037	Intermediate Similarity	NPC249274
0.7033	Intermediate Similarity	NPC308006
0.7033	Intermediate Similarity	NPC472836
0.7031	Intermediate Similarity	NPC117188
0.7031	Intermediate Similarity	NPC205421
0.7031	Intermediate Similarity	NPC145832
0.7031	Intermediate Similarity	NPC81218
0.7031	Intermediate Similarity	NPC12053
0.7031	Intermediate Similarity	NPC158376
0.7031	Intermediate Similarity	NPC474931
0.7031	Intermediate Similarity	NPC306555
0.7021	Intermediate Similarity	NPC315707
0.7021	Intermediate Similarity	NPC148014
0.7021	Intermediate Similarity	NPC478161
0.7021	Intermediate Similarity	NPC40389
0.7021	Intermediate Similarity	NPC478159
0.7021	Intermediate Similarity	NPC78359
0.7021	Intermediate Similarity	NPC65490
0.702	Intermediate Similarity	NPC248642
0.7016	Intermediate Similarity	NPC212794
0.7016	Intermediate Similarity	NPC78222
0.7016	Intermediate Similarity	NPC168409
0.7016	Intermediate Similarity	NPC180306
0.7016	Intermediate Similarity	NPC477563
0.7016	Intermediate Similarity	NPC196447
0.7016	Intermediate Similarity	NPC253043
0.7016	Intermediate Similarity	NPC13504
0.7016	Intermediate Similarity	NPC136508
0.7016	Intermediate Similarity	NPC96603
0.7016	Intermediate Similarity	NPC306843
0.701	Intermediate Similarity	NPC149090
0.701	Intermediate Similarity	NPC19520
0.7005	Intermediate Similarity	NPC99179
0.7005	Intermediate Similarity	NPC474745
0.7005	Intermediate Similarity	NPC244112
0.7005	Intermediate Similarity	NPC60211
0.7005	Intermediate Similarity	NPC267408
0.7005	Intermediate Similarity	NPC27615
0.7	Intermediate Similarity	NPC250076
0.7	Intermediate Similarity	NPC474009
0.6995	Remote Similarity	NPC86469
0.6991	Remote Similarity	NPC256422
0.6989	Remote Similarity	NPC476580
0.6989	Remote Similarity	NPC475718
0.6985	Remote Similarity	NPC156576
0.6985	Remote Similarity	NPC104682
0.698	Remote Similarity	NPC226708

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 NPC174783 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	226
0.1-0.2	768
0.2-0.3	990
0.3-0.4	2538
0.4-0.5	2280
0.5-0.6	1533
0.6-0.7	603
0.7-0.8	165
0.8-0.85	30
0.85-0.9	6
0.9-0.95	8
0.95-1	3

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9719	High Similarity	NPD4482	Phase 3
0.9665	High Similarity	NPD2972	Approved
0.9665	High Similarity	NPD3533	Approved
0.9663	High Similarity	NPD4107	Approved
0.9556	High Similarity	NPD3057	Approved
0.9448	High Similarity	NPD2491	Approved
0.9341	High Similarity	NPD3448	Approved
0.9251	High Similarity	NPD5676	Approved
0.8983	High Similarity	NPD2968	Approved
0.8983	High Similarity	NPD2971	Approved
0.8912	High Similarity	NPD5980	Discovery
0.8737	High Similarity	NPD5619	Clinical (unspecified phase)
0.8636	High Similarity	NPD7907	Approved
0.8629	High Similarity	NPD4665	Approved
0.8629	High Similarity	NPD4111	Phase 1
0.8587	High Similarity	NPD2490	Approved
0.8587	High Similarity	NPD2488	Approved
0.836	Intermediate Similarity	NPD2974	Approved
0.836	Intermediate Similarity	NPD2975	Approved
0.836	Intermediate Similarity	NPD2973	Approved
0.8325	Intermediate Similarity	NPD4580	Approved
0.8261	Intermediate Similarity	NPD3534	Clinical (unspecified phase)
0.8187	Intermediate Similarity	NPD2493	Approved
0.8187	Intermediate Similarity	NPD2494	Approved
0.8154	Intermediate Similarity	NPD4583	Approved
0.8154	Intermediate Similarity	NPD4582	Approved
0.8122	Intermediate Similarity	NPD4481	Phase 3
0.8104	Intermediate Similarity	NPD7048	Phase 3
0.8103	Intermediate Similarity	NPD4004	Approved
0.8103	Intermediate Similarity	NPD4002	Approved
0.8093	Intermediate Similarity	NPD3452	Approved
0.8093	Intermediate Similarity	NPD3450	Approved
0.8061	Intermediate Similarity	NPD4040	Phase 1
0.7967	Intermediate Similarity	NPD2969	Approved
0.7967	Intermediate Similarity	NPD2970	Approved
0.7912	Intermediate Similarity	NPD3051	Approved
0.7826	Intermediate Similarity	NPD2489	Approved
0.7826	Intermediate Similarity	NPD27	Approved
0.7684	Intermediate Similarity	NPD7311	Approved
0.7684	Intermediate Similarity	NPD7313	Approved
0.7684	Intermediate Similarity	NPD7310	Approved
0.7684	Intermediate Similarity	NPD7312	Approved
0.768	Intermediate Similarity	NPD5616	Clinical (unspecified phase)
0.7644	Intermediate Similarity	NPD7309	Approved
0.7585	Intermediate Similarity	NPD7047	Phase 3
0.7409	Intermediate Similarity	NPD4578	Approved
0.7409	Intermediate Similarity	NPD4577	Approved
0.7371	Intermediate Similarity	NPD6997	Phase 2
0.733	Intermediate Similarity	NPD3050	Clinical (unspecified phase)
0.7313	Intermediate Similarity	NPD4420	Approved
0.7297	Intermediate Similarity	NPD5977	Approved
0.7297	Intermediate Similarity	NPD5978	Approved
0.7296	Intermediate Similarity	NPD4663	Approved
0.7259	Intermediate Similarity	NPD7906	Approved
0.7228	Intermediate Similarity	NPD6385	Approved
0.7228	Intermediate Similarity	NPD6386	Approved
0.722	Intermediate Similarity	NPD7497	Discontinued
0.7198	Intermediate Similarity	NPD3641	Approved
0.7198	Intermediate Similarity	NPD3639	Approved
0.7198	Intermediate Similarity	NPD3640	Phase 3
0.7188	Intermediate Similarity	NPD2163	Approved
0.7172	Intermediate Similarity	NPD7291	Discontinued
0.7172	Intermediate Similarity	NPD6040	Clinical (unspecified phase)
0.7171	Intermediate Similarity	NPD5006	Approved
0.7171	Intermediate Similarity	NPD5005	Approved
0.7129	Intermediate Similarity	NPD7667	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD2898	Approved
0.7081	Intermediate Similarity	NPD1337	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7068	Intermediate Similarity	NPD6071	Discontinued
0.7021	Intermediate Similarity	NPD2560	Approved
0.7021	Intermediate Similarity	NPD2563	Approved
0.701	Intermediate Similarity	NPD5564	Approved
0.7005	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD6029	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD6028	Clinical (unspecified phase)
0.6932	Remote Similarity	NPD3142	Approved
0.6932	Remote Similarity	NPD3140	Approved
0.6931	Remote Similarity	NPD5525	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD7177	Discontinued
0.6923	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6907	Remote Similarity	NPD4575	Clinical (unspecified phase)
0.6895	Remote Similarity	NPD5019	Clinical (unspecified phase)
0.6888	Remote Similarity	NPD5312	Approved
0.6888	Remote Similarity	NPD5313	Approved
0.6875	Remote Similarity	NPD5494	Approved
0.6872	Remote Similarity	NPD3446	Phase 1
0.6862	Remote Similarity	NPD7110	Phase 1
0.6862	Remote Similarity	NPD7109	Clinical (unspecified phase)
0.6862	Remote Similarity	NPD6873	Phase 2
0.6847	Remote Similarity	NPD3808	Clinical (unspecified phase)
0.684	Remote Similarity	NPD4859	Phase 1
0.6836	Remote Similarity	NPD3110	Approved
0.6836	Remote Similarity	NPD3109	Approved
0.6827	Remote Similarity	NPD5457	Discontinued
0.6823	Remote Similarity	NPD919	Approved
0.682	Remote Similarity	NPD8404	Phase 2
0.6811	Remote Similarity	NPD4584	Approved
0.68	Remote Similarity	NPD4078	Clinical (unspecified phase)
0.6784	Remote Similarity	NPD7039	Approved
0.6784	Remote Similarity	NPD7038	Approved
0.6774	Remote Similarity	NPD3647	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD4773	Phase 2
0.6772	Remote Similarity	NPD4772	Phase 2
0.6758	Remote Similarity	NPD4664	Clinical (unspecified phase)
0.6754	Remote Similarity	NPD5353	Approved
0.6753	Remote Similarity	NPD1247	Approved
0.6737	Remote Similarity	NPD7248	Discontinued
0.6737	Remote Similarity	NPD7577	Discontinued
0.672	Remote Similarity	NPD3146	Approved
0.672	Remote Similarity	NPD1754	Clinical (unspecified phase)
0.672	Remote Similarity	NPD3688	Clinical (unspecified phase)
0.6719	Remote Similarity	NPD4947	Clinical (unspecified phase)
0.6717	Remote Similarity	NPD8156	Discontinued
0.6712	Remote Similarity	NPD7279	Phase 2
0.6712	Remote Similarity	NPD7278	Phase 2
0.6702	Remote Similarity	NPD4585	Approved
0.6696	Remote Similarity	NPD6625	Approved
0.6684	Remote Similarity	NPD7832	Clinical (unspecified phase)
0.6684	Remote Similarity	NPD7833	Phase 2
0.6684	Remote Similarity	NPD5242	Approved
0.6684	Remote Similarity	NPD7831	Phase 2
0.6683	Remote Similarity	NPD6618	Phase 2
0.6682	Remote Similarity	NPD4505	Phase 1
0.6667	Remote Similarity	NPD7607	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6107	Approved
0.6667	Remote Similarity	NPD8251	Approved
0.6667	Remote Similarity	NPD8252	Approved
0.6667	Remote Similarity	NPD8099	Discontinued
0.6667	Remote Similarity	NPD2897	Discontinued
0.6649	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6649	Remote Similarity	NPD6862	Phase 2
0.6649	Remote Similarity	NPD5241	Discontinued
0.6649	Remote Similarity	NPD6662	Clinical (unspecified phase)
0.6635	Remote Similarity	NPD4361	Phase 2
0.6635	Remote Similarity	NPD4362	Clinical (unspecified phase)
0.6633	Remote Similarity	NPD7315	Approved
0.6633	Remote Similarity	NPD5844	Phase 1
0.6633	Remote Similarity	NPD4166	Phase 2
0.6632	Remote Similarity	NPD6875	Approved
0.6632	Remote Similarity	NPD6876	Approved
0.6619	Remote Similarity	NPD8285	Discontinued
0.6618	Remote Similarity	NPD4466	Phase 1
0.6614	Remote Similarity	NPD4210	Discontinued
0.6598	Remote Similarity	NPD1307	Phase 2
0.6598	Remote Similarity	NPD1309	Phase 2
0.6587	Remote Similarity	NPD4363	Phase 3
0.6587	Remote Similarity	NPD4360	Phase 2
0.6584	Remote Similarity	NPD7190	Clinical (unspecified phase)
0.6579	Remote Similarity	NPD2651	Approved
0.6579	Remote Similarity	NPD2649	Approved
0.6573	Remote Similarity	NPD2669	Clinical (unspecified phase)
0.6569	Remote Similarity	NPD5036	Approved
0.6562	Remote Similarity	NPD6279	Approved
0.6562	Remote Similarity	NPD6280	Approved
0.6562	Remote Similarity	NPD6844	Discontinued
0.6561	Remote Similarity	NPD4727	Phase 1
0.6561	Remote Similarity	NPD7427	Discontinued
0.6559	Remote Similarity	NPD5084	Clinical (unspecified phase)
0.6557	Remote Similarity	NPD6321	Discontinued
0.655	Remote Similarity	NPD42	Phase 2
0.655	Remote Similarity	NPD6042	Phase 2
0.6546	Remote Similarity	NPD3882	Suspended
0.6541	Remote Similarity	NPD2654	Approved
0.6537	Remote Similarity	NPD5037	Approved
0.6537	Remote Similarity	NPD5038	Approved
0.6537	Remote Similarity	NPD3863	Clinical (unspecified phase)
0.6535	Remote Similarity	NPD1298	Discontinued
0.6528	Remote Similarity	NPD7701	Phase 2
0.6524	Remote Similarity	NPD6783	Clinical (unspecified phase)
0.6517	Remote Similarity	NPD5752	Clinical (unspecified phase)
0.6515	Remote Similarity	NPD3926	Phase 2
0.651	Remote Similarity	NPD5090	Approved
0.651	Remote Similarity	NPD5089	Approved
0.6507	Remote Similarity	NPD4413	Clinical (unspecified phase)
0.6505	Remote Similarity	NPD5754	Discontinued
0.6494	Remote Similarity	NPD3752	Phase 2
0.6492	Remote Similarity	NPD824	Approved
0.649	Remote Similarity	NPD7296	Approved
0.6485	Remote Similarity	NPD3823	Discontinued
0.648	Remote Similarity	NPD5709	Phase 3
0.6476	Remote Similarity	NPD8469	Approved
0.6474	Remote Similarity	NPD6030	Approved
0.6474	Remote Similarity	NPD6031	Approved
0.6473	Remote Similarity	NPD6836	Approved
0.6473	Remote Similarity	NPD6377	Clinical (unspecified phase)
0.6473	Remote Similarity	NPD7235	Clinical (unspecified phase)
0.6468	Remote Similarity	NPD5914	Approved
0.6459	Remote Similarity	NPD6181	Discontinued
0.6456	Remote Similarity	NPD8434	Phase 2
0.6453	Remote Similarity	NPD5027	Approved
0.6453	Remote Similarity	NPD5031	Approved
0.6453	Remote Similarity	NPD5029	Approved
0.6449	Remote Similarity	NPD7626	Approved
0.6449	Remote Similarity	NPD7627	Approved
0.6447	Remote Similarity	NPD4666	Phase 3
0.6445	Remote Similarity	NPD7238	Clinical (unspecified phase)
0.6443	Remote Similarity	NPD5772	Approved
0.6443	Remote Similarity	NPD5773	Approved
0.6443	Remote Similarity	NPD6668	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