NPASS Compound

Structure

CID124657 OpenBabel06191715482D 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 0.7113 -1.6187 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1529 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 2.0919 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 -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 0.4181 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 0 0 0 0 0 0 0 0 0 0 -2.8777 -0.4184 0.0000 C 0 0 2 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 -0.7034 -1.6738 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 -0.4184 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 2.1174 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0213 -2.0923 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 5 2 0 0 0 0 3 10 1 0 0 0 0 4 6 1 0 0 0 0 4 11 2 0 0 0 0 5 13 1 0 0 0 0 6 14 2 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 0 0 0 0 12 9 1 6 0 0 0 12 19 1 0 0 0 0 13 16 2 0 0 0 0 13 20 1 0 0 0 0 14 17 1 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:	2.483
LogD:	1.793
LogS:	-2.091
# Rotatable Bonds:	1
TPSA:	41.93
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.862
Synthetic Accessibility Score:	5.24
Fsp3:	0.444
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:	-4.798
MDCK Permeability:	1.9380435333005153e-05
Pgp-inhibitor:	0.007
Pgp-substrate:	0.758
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.98
30% Bioavailability (F30%):	0.974

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.997
Plasma Protein Binding (PPB):	56.145660400390625%
Volume Distribution (VD):	2.676
Pgp-substrate:	48.421607971191406%

ADMET: Metabolism

CYP1A2-inhibitor:	0.128
CYP1A2-substrate:	0.486
CYP2C19-inhibitor:	0.05
CYP2C19-substrate:	0.906
CYP2C9-inhibitor:	0.033
CYP2C9-substrate:	0.366
CYP2D6-inhibitor:	0.574
CYP2D6-substrate:	0.901
CYP3A4-inhibitor:	0.014
CYP3A4-substrate:	0.922

ADMET: Excretion

Clearance (CL):	14.613
Half-life (T1/2):	0.677

ADMET: Toxicity

hERG Blockers:	0.84
Human Hepatotoxicity (H-HT):	0.818
Drug-inuced Liver Injury (DILI):	0.121
AMES Toxicity:	0.33
Rat Oral Acute Toxicity:	0.962
Maximum Recommended Daily Dose:	0.916
Skin Sensitization:	0.718
Carcinogencity:	0.851
Eye Corrosion:	0.003
Eye Irritation:	0.013
Respiratory Toxicity:	0.962

Download Data

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

Natural Product: NPC124657

Natural Product ID:	NPC124657
*Common Name:**	Oripavine
IUPAC Name:	(4R,7aR,12bS)-7-methoxy-3-methyl-2,4,7a,13-tetrahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinoline-9-ol
Synonyms:	Oripavine
Standard InCHIKey:	ZKLXUUYLEHCAMF-UUWFMWQGSA-N
Standard InCHI:	InChI=1S/C18H19NO3/c1-19-8-7-18-11-4-6-14(21-2)17(18)22-16-13(20)5-3-10(15(16)18)9-12(11)19/h3-6,12,17,20H,7-9H2,1-2H3/t12-,17+,18+/m1/s1
SMILES:	COC1=CC=C2[C@@]34[C@H]1Oc1c4c(C[C@H]2N(CC3)C)ccc1O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL437602
PubChem CID:	5462306
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]
NPO9498	Papaver somniferum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
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]

☑ 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[570431]
NPT145	Individual Protein	Mu opioid receptor	Homo sapiens	EC50	=	277.0	nM	PMID[570431]
NPT145	Individual Protein	Mu opioid receptor	Homo sapiens	Ki	=	286.0	nM	PMID[570431]

☑ 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 NPC124657 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	295
0.1-0.2	1336
0.2-0.3	4743
0.3-0.4	12059
0.4-0.5	5924
0.5-0.6	10506
0.6-0.7	6451
0.7-0.8	1101
0.8-0.85	222
0.85-0.9	45
0.9-0.95	7
0.95-1	8

Similarity Score	Similarity Level	Natural Product ID
0.9542	High Similarity	NPC323443
0.9542	High Similarity	NPC180756
0.9152	High Similarity	NPC305847
0.9096	High Similarity	NPC302449
0.8805	High Similarity	NPC147091
0.8758	High Similarity	NPC18402
0.8758	High Similarity	NPC249274
0.872	High Similarity	NPC474931
0.872	High Similarity	NPC117188
0.872	High Similarity	NPC81218
0.872	High Similarity	NPC205421
0.872	High Similarity	NPC158376
0.872	High Similarity	NPC12053
0.872	High Similarity	NPC145832
0.872	High Similarity	NPC306555
0.8712	High Similarity	NPC78222
0.8712	High Similarity	NPC253043
0.8712	High Similarity	NPC3375
0.8712	High Similarity	NPC196447
0.8712	High Similarity	NPC306843
0.8712	High Similarity	NPC96603
0.8712	High Similarity	NPC255607
0.8712	High Similarity	NPC212794
0.8712	High Similarity	NPC477563
0.8712	High Similarity	NPC13504
0.8712	High Similarity	NPC136508
0.8683	High Similarity	NPC329969
0.865	High Similarity	NPC324144
0.865	High Similarity	NPC1229
0.8642	High Similarity	NPC27410
0.8642	High Similarity	NPC166014
0.8642	High Similarity	NPC205167
0.8639	High Similarity	NPC99179
0.8634	High Similarity	NPC148014
0.8634	High Similarity	NPC65490
0.8634	High Similarity	NPC40389
0.8634	High Similarity	NPC78359
0.8634	High Similarity	NPC315707
0.858	High Similarity	NPC320223
0.858	High Similarity	NPC114364
0.8571	High Similarity	NPC128560
0.8571	High Similarity	NPC199465
0.8571	High Similarity	NPC229166
0.8554	High Similarity	NPC83198
0.8554	High Similarity	NPC204908
0.8544	High Similarity	NPC103379
0.8544	High Similarity	NPC477565
0.8535	High Similarity	NPC191376
0.8535	High Similarity	NPC321505
0.8535	High Similarity	NPC179825
0.8528	High Similarity	NPC226428
0.8519	High Similarity	NPC129603
0.8509	High Similarity	NPC207757
0.8509	High Similarity	NPC172765
0.8509	High Similarity	NPC184026
0.8509	High Similarity	NPC189266
0.8509	High Similarity	NPC2413
0.8509	High Similarity	NPC295691
0.8509	High Similarity	NPC5238
0.8509	High Similarity	NPC193949
0.8509	High Similarity	NPC110416
0.8509	High Similarity	NPC276588
0.8509	High Similarity	NPC278799
0.8509	High Similarity	NPC127674
0.8509	High Similarity	NPC204828
0.8509	High Similarity	NPC469817
0.8509	High Similarity	NPC249797
0.8509	High Similarity	NPC39701
0.8509	High Similarity	NPC54379
0.8503	High Similarity	NPC168753
0.8503	High Similarity	NPC118274
0.85	High Similarity	NPC82285
0.85	High Similarity	NPC133011
0.8481	Intermediate Similarity	NPC24233
0.8481	Intermediate Similarity	NPC147390
0.8481	Intermediate Similarity	NPC246587
0.8481	Intermediate Similarity	NPC135538
0.8481	Intermediate Similarity	NPC476571
0.8481	Intermediate Similarity	NPC428
0.8452	Intermediate Similarity	NPC239775
0.8434	Intermediate Similarity	NPC264850
0.8434	Intermediate Similarity	NPC13916
0.8421	Intermediate Similarity	NPC126284
0.8421	Intermediate Similarity	NPC32154
0.8418	Intermediate Similarity	NPC476151
0.8408	Intermediate Similarity	NPC185838
0.8402	Intermediate Similarity	NPC66341
0.8402	Intermediate Similarity	NPC232386
0.8402	Intermediate Similarity	NPC477020
0.8402	Intermediate Similarity	NPC152680
0.8402	Intermediate Similarity	NPC192135
0.8402	Intermediate Similarity	NPC190783
0.8393	Intermediate Similarity	NPC477562
0.8393	Intermediate Similarity	NPC26240
0.8393	Intermediate Similarity	NPC69712
0.8389	Intermediate Similarity	NPC64576
0.8389	Intermediate Similarity	NPC151470
0.8389	Intermediate Similarity	NPC201055
0.8389	Intermediate Similarity	NPC254045
0.8383	Intermediate Similarity	NPC298979
0.8375	Intermediate Similarity	NPC220858
0.8375	Intermediate Similarity	NPC88249
0.8375	Intermediate Similarity	NPC192768
0.8375	Intermediate Similarity	NPC151895
0.8375	Intermediate Similarity	NPC97221
0.8373	Intermediate Similarity	NPC232514
0.8373	Intermediate Similarity	NPC24465
0.8373	Intermediate Similarity	NPC276944
0.8373	Intermediate Similarity	NPC238530
0.8372	Intermediate Similarity	NPC115906
0.8364	Intermediate Similarity	NPC60186
0.8343	Intermediate Similarity	NPC476331
0.8333	Intermediate Similarity	NPC470324
0.8333	Intermediate Similarity	NPC214629
0.8324	Intermediate Similarity	NPC248642
0.8324	Intermediate Similarity	NPC116284
0.8323	Intermediate Similarity	NPC476573
0.8323	Intermediate Similarity	NPC35627
0.8323	Intermediate Similarity	NPC81247
0.8313	Intermediate Similarity	NPC124433
0.8313	Intermediate Similarity	NPC293871
0.8304	Intermediate Similarity	NPC241704
0.8303	Intermediate Similarity	NPC4304
0.8294	Intermediate Similarity	NPC2314
0.8293	Intermediate Similarity	NPC476572
0.8282	Intermediate Similarity	NPC325871
0.8282	Intermediate Similarity	NPC99659
0.8276	Intermediate Similarity	NPC135772
0.8276	Intermediate Similarity	NPC156576
0.8274	Intermediate Similarity	NPC150879
0.8274	Intermediate Similarity	NPC210140
0.8266	Intermediate Similarity	NPC312918
0.8266	Intermediate Similarity	NPC286119
0.8266	Intermediate Similarity	NPC155442
0.8266	Intermediate Similarity	NPC476574
0.8266	Intermediate Similarity	NPC477561
0.8263	Intermediate Similarity	NPC225774
0.8261	Intermediate Similarity	NPC274026
0.8256	Intermediate Similarity	NPC294790
0.8256	Intermediate Similarity	NPC118633
0.8256	Intermediate Similarity	NPC148693
0.8242	Intermediate Similarity	NPC59028
0.8242	Intermediate Similarity	NPC92191
0.8242	Intermediate Similarity	NPC111485
0.8235	Intermediate Similarity	NPC477640
0.8235	Intermediate Similarity	NPC225597
0.8235	Intermediate Similarity	NPC470739
0.8225	Intermediate Similarity	NPC475686
0.8225	Intermediate Similarity	NPC158148
0.8225	Intermediate Similarity	NPC266176
0.8225	Intermediate Similarity	NPC58766
0.8225	Intermediate Similarity	NPC290759
0.8225	Intermediate Similarity	NPC82533
0.8221	Intermediate Similarity	NPC477564
0.8221	Intermediate Similarity	NPC2295
0.8218	Intermediate Similarity	NPC185639
0.8218	Intermediate Similarity	NPC104196
0.8218	Intermediate Similarity	NPC54654
0.8218	Intermediate Similarity	NPC290005
0.8218	Intermediate Similarity	NPC181796
0.8218	Intermediate Similarity	NPC285931
0.8218	Intermediate Similarity	NPC223690
0.8218	Intermediate Similarity	NPC311973
0.8218	Intermediate Similarity	NPC222661
0.8218	Intermediate Similarity	NPC30779
0.8218	Intermediate Similarity	NPC271013
0.8218	Intermediate Similarity	NPC258657
0.8218	Intermediate Similarity	NPC217748
0.8218	Intermediate Similarity	NPC49075
0.8218	Intermediate Similarity	NPC279228
0.8218	Intermediate Similarity	NPC8836
0.8218	Intermediate Similarity	NPC90998
0.8218	Intermediate Similarity	NPC328155
0.8218	Intermediate Similarity	NPC290582
0.8218	Intermediate Similarity	NPC182052
0.8218	Intermediate Similarity	NPC15414
0.8218	Intermediate Similarity	NPC239824
0.8218	Intermediate Similarity	NPC229373
0.8218	Intermediate Similarity	NPC7715
0.8218	Intermediate Similarity	NPC42663
0.8218	Intermediate Similarity	NPC251735
0.8214	Intermediate Similarity	NPC42549
0.8214	Intermediate Similarity	NPC250846
0.8214	Intermediate Similarity	NPC219341
0.8214	Intermediate Similarity	NPC240841
0.8214	Intermediate Similarity	NPC24264
0.8214	Intermediate Similarity	NPC268503
0.8214	Intermediate Similarity	NPC476432
0.8214	Intermediate Similarity	NPC317272
0.8214	Intermediate Similarity	NPC256012
0.821	Intermediate Similarity	NPC81733
0.821	Intermediate Similarity	NPC277669
0.821	Intermediate Similarity	NPC326316
0.821	Intermediate Similarity	NPC76213
0.8208	Intermediate Similarity	NPC474507
0.8204	Intermediate Similarity	NPC218614
0.8202	Intermediate Similarity	NPC478093
0.8198	Intermediate Similarity	NPC148709
0.8198	Intermediate Similarity	NPC476577
0.8198	Intermediate Similarity	NPC173416

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 NPC124657 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	193
0.1-0.2	702
0.2-0.3	1062
0.3-0.4	2396
0.4-0.5	2341
0.5-0.6	1516
0.6-0.7	722
0.7-0.8	168
0.8-0.85	19
0.85-0.9	23
0.9-0.95	3
0.95-1	5

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9618	High Similarity	NPD2489	Approved
0.9618	High Similarity	NPD27	Approved
0.9554	High Similarity	NPD2970	Approved
0.9554	High Similarity	NPD2969	Approved
0.9367	High Similarity	NPD3051	Approved
0.9152	High Similarity	NPD7312	Approved
0.9152	High Similarity	NPD7311	Approved
0.9152	High Similarity	NPD7310	Approved
0.9152	High Similarity	NPD7313	Approved
0.9096	High Similarity	NPD7309	Approved
0.9048	High Similarity	NPD7906	Approved
0.9036	High Similarity	NPD4578	Approved
0.9036	High Similarity	NPD4577	Approved
0.8896	High Similarity	NPD4481	Phase 3
0.8876	High Similarity	NPD4663	Approved
0.8721	High Similarity	NPD2488	Approved
0.8721	High Similarity	NPD2490	Approved
0.8659	High Similarity	NPD6071	Discontinued
0.8634	High Similarity	NPD2563	Approved
0.8634	High Similarity	NPD2560	Approved
0.8418	Intermediate Similarity	NPD1754	Clinical (unspecified phase)
0.8389	Intermediate Similarity	NPD2493	Approved
0.8389	Intermediate Similarity	NPD2494	Approved
0.8389	Intermediate Similarity	NPD3450	Approved
0.8389	Intermediate Similarity	NPD3452	Approved
0.8372	Intermediate Similarity	NPD2971	Approved
0.8372	Intermediate Similarity	NPD2968	Approved
0.8333	Intermediate Similarity	NPD2898	Approved
0.8251	Intermediate Similarity	NPD4582	Approved
0.8251	Intermediate Similarity	NPD4583	Approved
0.8228	Intermediate Similarity	NPD5241	Discontinued
0.8218	Intermediate Similarity	NPD8054	Approved
0.8218	Intermediate Similarity	NPD8053	Approved
0.8197	Intermediate Similarity	NPD4002	Approved
0.8197	Intermediate Similarity	NPD4004	Approved
0.8193	Intermediate Similarity	NPD7831	Phase 2
0.8193	Intermediate Similarity	NPD7832	Clinical (unspecified phase)
0.8193	Intermediate Similarity	NPD7833	Phase 2
0.8167	Intermediate Similarity	NPD2975	Approved
0.8167	Intermediate Similarity	NPD2974	Approved
0.8167	Intermediate Similarity	NPD2973	Approved
0.811	Intermediate Similarity	NPD4772	Phase 2
0.811	Intermediate Similarity	NPD4773	Phase 2
0.8077	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.8077	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.8075	Intermediate Similarity	NPD4584	Approved
0.8057	Intermediate Similarity	NPD3534	Clinical (unspecified phase)
0.8054	Intermediate Similarity	NPD4040	Phase 1
0.8043	Intermediate Similarity	NPD2491	Approved
0.8043	Intermediate Similarity	NPD3057	Approved
0.8043	Intermediate Similarity	NPD3448	Approved
0.8038	Intermediate Similarity	NPD4664	Clinical (unspecified phase)
0.8033	Intermediate Similarity	NPD4580	Approved
0.7946	Intermediate Similarity	NPD2972	Approved
0.7946	Intermediate Similarity	NPD3533	Approved
0.7917	Intermediate Similarity	NPD7047	Phase 3
0.7904	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.7901	Intermediate Similarity	NPD2421	Approved
0.7901	Intermediate Similarity	NPD2420	Approved
0.7874	Intermediate Similarity	NPD8156	Discontinued
0.7848	Intermediate Similarity	NPD1753	Discontinued
0.7816	Intermediate Similarity	NPD8251	Approved
0.7816	Intermediate Similarity	NPD8252	Approved
0.7816	Intermediate Similarity	NPD8099	Discontinued
0.7798	Intermediate Similarity	NPD5772	Approved
0.7798	Intermediate Similarity	NPD5773	Approved
0.7764	Intermediate Similarity	NPD4236	Phase 3
0.7764	Intermediate Similarity	NPD4237	Approved
0.7744	Intermediate Similarity	NPD4160	Clinical (unspecified phase)
0.7707	Intermediate Similarity	NPD3109	Approved
0.7707	Intermediate Similarity	NPD3110	Approved
0.7692	Intermediate Similarity	NPD2977	Approved
0.7692	Intermediate Similarity	NPD2978	Approved
0.7688	Intermediate Similarity	NPD4010	Discontinued
0.7677	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7654	Intermediate Similarity	NPD5177	Phase 3
0.7651	Intermediate Similarity	NPD6031	Approved
0.7651	Intermediate Similarity	NPD6030	Approved
0.7647	Intermediate Similarity	NPD4107	Approved
0.764	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7628	Intermediate Similarity	NPD2669	Clinical (unspecified phase)
0.7626	Intermediate Similarity	NPD7907	Approved
0.7622	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.7617	Intermediate Similarity	NPD5676	Approved
0.7588	Intermediate Similarity	NPD6997	Phase 2
0.7574	Intermediate Similarity	NPD6072	Discontinued
0.7572	Intermediate Similarity	NPD7201	Clinical (unspecified phase)
0.7571	Intermediate Similarity	NPD42	Phase 2
0.7571	Intermediate Similarity	NPD6042	Phase 2
0.7561	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.7561	Intermediate Similarity	NPD3692	Discontinued
0.756	Intermediate Similarity	NPD4017	Approved
0.7546	Intermediate Similarity	NPD3060	Approved
0.7545	Intermediate Similarity	NPD2122	Discontinued
0.7527	Intermediate Similarity	NPD7667	Clinical (unspecified phase)
0.7525	Intermediate Similarity	NPD4111	Phase 1
0.7525	Intermediate Similarity	NPD4665	Approved
0.7515	Intermediate Similarity	NPD6667	Approved
0.7515	Intermediate Similarity	NPD6666	Approved
0.7515	Intermediate Similarity	NPD2422	Clinical (unspecified phase)
0.7513	Intermediate Similarity	NPD4482	Phase 3
0.75	Intermediate Similarity	NPD6331	Phase 2
0.75	Intermediate Similarity	NPD3636	Approved
0.75	Intermediate Similarity	NPD6788	Approved
0.75	Intermediate Similarity	NPD3635	Approved
0.75	Intermediate Similarity	NPD3637	Approved
0.7485	Intermediate Similarity	NPD3647	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD7037	Approved
0.7471	Intermediate Similarity	NPD4666	Phase 3
0.7468	Intermediate Similarity	NPD5718	Phase 2
0.7455	Intermediate Similarity	NPD2677	Approved
0.7452	Intermediate Similarity	NPD3594	Approved
0.7452	Intermediate Similarity	NPD2606	Approved
0.7452	Intermediate Similarity	NPD2605	Approved
0.7452	Intermediate Similarity	NPD3595	Approved
0.744	Intermediate Similarity	NPD3641	Approved
0.744	Intermediate Similarity	NPD3639	Approved
0.744	Intermediate Similarity	NPD3640	Phase 3
0.7439	Intermediate Similarity	NPD4162	Approved
0.7427	Intermediate Similarity	NPD7298	Approved
0.7425	Intermediate Similarity	NPD7020	Approved
0.7425	Intermediate Similarity	NPD7019	Approved
0.7423	Intermediate Similarity	NPD4721	Approved
0.7423	Intermediate Similarity	NPD4726	Approved
0.7423	Intermediate Similarity	NPD4725	Approved
0.7414	Intermediate Similarity	NPD5709	Phase 3
0.741	Intermediate Similarity	NPD3845	Phase 1
0.7405	Intermediate Similarity	NPD5156	Approved
0.7405	Intermediate Similarity	NPD5155	Approved
0.7396	Intermediate Similarity	NPD4210	Discontinued
0.7376	Intermediate Similarity	NPD5619	Clinical (unspecified phase)
0.7375	Intermediate Similarity	NPD2238	Phase 2
0.7365	Intermediate Similarity	NPD7212	Phase 2
0.7365	Intermediate Similarity	NPD7213	Phase 3
0.7362	Intermediate Similarity	NPD2161	Phase 2
0.7346	Intermediate Similarity	NPD6896	Approved
0.7346	Intermediate Similarity	NPD6895	Approved
0.7337	Intermediate Similarity	NPD5976	Discontinued
0.7321	Intermediate Similarity	NPD4123	Phase 3
0.7321	Intermediate Similarity	NPD7447	Phase 1
0.7312	Intermediate Similarity	NPD2674	Phase 3
0.7305	Intermediate Similarity	NPD7124	Phase 2
0.7299	Intermediate Similarity	NPD4581	Clinical (unspecified phase)
0.7294	Intermediate Similarity	NPD3687	Approved
0.7294	Intermediate Similarity	NPD3686	Approved
0.7289	Intermediate Similarity	NPD5754	Discontinued
0.7289	Intermediate Similarity	NPD6658	Clinical (unspecified phase)
0.7284	Intermediate Similarity	NPD817	Approved
0.7284	Intermediate Similarity	NPD823	Approved
0.7278	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD3365	Discontinued
0.7267	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD3620	Phase 2
0.7263	Intermediate Similarity	NPD5602	Clinical (unspecified phase)
0.7251	Intermediate Similarity	NPD4005	Discontinued
0.7239	Intermediate Similarity	NPD2200	Suspended
0.7235	Intermediate Similarity	NPD4727	Phase 1
0.7232	Intermediate Similarity	NPD6107	Approved
0.7228	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7213	Intermediate Similarity	NPD7549	Discontinued
0.7212	Intermediate Similarity	NPD1375	Discontinued
0.7205	Intermediate Similarity	NPD4475	Approved
0.7205	Intermediate Similarity	NPD4474	Approved
0.7195	Intermediate Similarity	NPD2155	Approved
0.7195	Intermediate Similarity	NPD2156	Approved
0.7195	Intermediate Similarity	NPD2154	Approved
0.719	Intermediate Similarity	NPD2226	Clinical (unspecified phase)
0.7182	Intermediate Similarity	NPD4873	Discontinued
0.7178	Intermediate Similarity	NPD3052	Approved
0.7178	Intermediate Similarity	NPD3054	Approved
0.7176	Intermediate Similarity	NPD6090	Discontinued
0.7173	Intermediate Similarity	NPD4420	Approved
0.7169	Intermediate Similarity	NPD1372	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD1613	Approved
0.716	Intermediate Similarity	NPD1774	Approved
0.7159	Intermediate Similarity	NPD4055	Discovery
0.7156	Intermediate Similarity	NPD7048	Phase 3
0.7152	Intermediate Similarity	NPD1632	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD6523	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD5160	Discontinued
0.7143	Intermediate Similarity	NPD3145	Approved
0.7143	Intermediate Similarity	NPD6812	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD3144	Approved
0.7135	Intermediate Similarity	NPD7427	Discontinued
0.7126	Intermediate Similarity	NPD5722	Discontinued
0.7118	Intermediate Similarity	NPD1424	Approved
0.7118	Intermediate Similarity	NPD3645	Discontinued
0.711	Intermediate Similarity	NPD4678	Approved
0.711	Intermediate Similarity	NPD4675	Approved
0.7108	Intermediate Similarity	NPD7030	Discontinued
0.7107	Intermediate Similarity	NPD6584	Phase 3
0.7099	Intermediate Similarity	NPD1132	Approved
0.7099	Intermediate Similarity	NPD1136	Approved
0.7099	Intermediate Similarity	NPD1130	Approved
0.7095	Intermediate Similarity	NPD4166	Phase 2
0.7089	Intermediate Similarity	NPD7258	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD7046	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD7466	Approved

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