NPASS Compound

Structure

CID67346 OpenBabel06191715402D 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 1 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 1 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 1 1 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:	301.17
Volume:	306.56
LogP:	2.111
LogD:	1.51
LogS:	-2.301
# 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:	0.858
Synthetic Accessibility Score:	5.017
Fsp3:	0.667
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:	-4.923
MDCK Permeability:	1.4892167200741824e-05
Pgp-inhibitor:	0.005
Pgp-substrate:	0.998
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.996

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.98
Plasma Protein Binding (PPB):	26.980487823486328%
Volume Distribution (VD):	2.996
Pgp-substrate:	59.04198455810547%

ADMET: Metabolism

CYP1A2-inhibitor:	0.081
CYP1A2-substrate:	0.719
CYP2C19-inhibitor:	0.024
CYP2C19-substrate:	0.955
CYP2C9-inhibitor:	0.009
CYP2C9-substrate:	0.271
CYP2D6-inhibitor:	0.857
CYP2D6-substrate:	0.915
CYP3A4-inhibitor:	0.031
CYP3A4-substrate:	0.902

ADMET: Excretion

Clearance (CL):	13.823
Half-life (T1/2):	0.659

ADMET: Toxicity

hERG Blockers:	0.907
Human Hepatotoxicity (H-HT):	0.403
Drug-inuced Liver Injury (DILI):	0.283
AMES Toxicity:	0.012
Rat Oral Acute Toxicity:	0.913
Maximum Recommended Daily Dose:	0.9
Skin Sensitization:	0.676
Carcinogencity:	0.525
Eye Corrosion:	0.003
Eye Irritation:	0.01
Respiratory Toxicity:	0.974

Download Data

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

Natural Product: NPC67346

Natural Product ID:	NPC67346
*Common Name:**	Dihydrocodeine
IUPAC Name:	(4R,4aR,7S,7aR,12bS)-9-methoxy-3-methyl-2,4,4a,5,6,7,7a,13-octahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinoline-7-ol
Synonyms:	Dihydrocodeine
Standard InCHIKey:	RBOXVHNMENFORY-DNJOTXNNSA-N
Standard InCHI:	InChI=1S/C18H23NO3/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/h3,6,11-13,17,20H,4-5,7-9H2,1-2H3/t11-,12+,13-,17-,18-/m0/s1
SMILES:	COc1ccc2c3c1O[C@@H]1[C@@]43CCN([C@H](C2)[C@@H]4CC[C@@H]1O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1595
PubChem CID:	5284543
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
ED50	2
Others	9

Activity Type	# Activity
Individual Protein	6
Organism	3
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT3606	Individual Protein	Kappa-type opioid receptor	Cricetulus griseus	Inhibition	=	51.0	%	PMID[544998]
NPT3606	Individual Protein	Kappa-type opioid receptor	Cricetulus griseus	Inhibition	=	4.0	%	PMID[544998]
NPT3607	Individual Protein	Delta-type opioid receptor	Cricetulus griseus	Inhibition	=	24.0	%	PMID[544998]
NPT3607	Individual Protein	Delta-type opioid receptor	Cricetulus griseus	Inhibition	=	7.0	%	PMID[544998]
NPT145	Individual Protein	Mu opioid receptor	Homo sapiens	Inhibition	=	40.0	%	PMID[544998]
NPT145	Individual Protein	Mu opioid receptor	Homo sapiens	Inhibition	=	17.0	%	PMID[544998]
NPT32	Organism	Mus musculus	Mus musculus	ED50	=	3.8	umol.kg-1	PMID[544993]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	ED50	>	22.0	umol.kg-1	PMID[544993]
NPT605	Organism	Homo sapiens	Homo sapiens	Activity	=	0.88	%	PMID[544995]
NPT35	Others	n.a.		pKa	n.a.	8.75	n.a.	PMID[544997]
NPT2	Others	Unspecified		Inhibition	=	40.0	%	PMID[544998]

☑ 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 NPC67346 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	294
0.1-0.2	1313
0.2-0.3	3935
0.3-0.4	10305
0.4-0.5	8622
0.5-0.6	11491
0.6-0.7	5761
0.7-0.8	845
0.8-0.85	108
0.85-0.9	8
0.9-0.95	10
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.9889	High Similarity	NPC43069
0.9889	High Similarity	NPC140577
0.9779	High Similarity	NPC97086
0.967	High Similarity	NPC232533
0.9568	High Similarity	NPC157958
0.9563	High Similarity	NPC243483
0.9556	High Similarity	NPC174783
0.9305	High Similarity	NPC126211
0.9297	High Similarity	NPC311781
0.9061	High Similarity	NPC214629
0.8791	High Similarity	NPC115906
0.8587	High Similarity	NPC298339
0.8482	Intermediate Similarity	NPC66909
0.8402	Intermediate Similarity	NPC201055
0.8402	Intermediate Similarity	NPC254045
0.8402	Intermediate Similarity	NPC64576
0.8402	Intermediate Similarity	NPC151470
0.8272	Intermediate Similarity	NPC196231
0.8173	Intermediate Similarity	NPC244191
0.8115	Intermediate Similarity	NPC162694
0.8103	Intermediate Similarity	NPC279665
0.8051	Intermediate Similarity	NPC33256
0.8043	Intermediate Similarity	NPC124657
0.8	Intermediate Similarity	NPC305847
0.797	Intermediate Similarity	NPC293624
0.7958	Intermediate Similarity	NPC302449
0.7937	Intermediate Similarity	NPC35680
0.7923	Intermediate Similarity	NPC475780
0.7892	Intermediate Similarity	NPC255607
0.7892	Intermediate Similarity	NPC3375
0.7871	Intermediate Similarity	NPC476500
0.7857	Intermediate Similarity	NPC94499
0.7857	Intermediate Similarity	NPC180756
0.7857	Intermediate Similarity	NPC323443
0.7783	Intermediate Similarity	NPC80472
0.773	Intermediate Similarity	NPC226428
0.7635	Intermediate Similarity	NPC286135
0.7619	Intermediate Similarity	NPC284842
0.7614	Intermediate Similarity	NPC141440
0.7592	Intermediate Similarity	NPC227683
0.7541	Intermediate Similarity	NPC8337
0.7541	Intermediate Similarity	NPC85747
0.7536	Intermediate Similarity	NPC476495
0.7536	Intermediate Similarity	NPC94687
0.7536	Intermediate Similarity	NPC106840
0.7513	Intermediate Similarity	NPC329969
0.7488	Intermediate Similarity	NPC326895
0.7475	Intermediate Similarity	NPC230098
0.7465	Intermediate Similarity	NPC82056
0.7453	Intermediate Similarity	NPC38964
0.7451	Intermediate Similarity	NPC474427
0.7448	Intermediate Similarity	NPC263212
0.7447	Intermediate Similarity	NPC249274
0.7438	Intermediate Similarity	NPC83019
0.7421	Intermediate Similarity	NPC35345
0.7416	Intermediate Similarity	NPC46990
0.7416	Intermediate Similarity	NPC476496
0.7405	Intermediate Similarity	NPC475718
0.7398	Intermediate Similarity	NPC149285
0.7398	Intermediate Similarity	NPC32154
0.7398	Intermediate Similarity	NPC474745
0.7398	Intermediate Similarity	NPC126284
0.7398	Intermediate Similarity	NPC27887
0.7396	Intermediate Similarity	NPC470324
0.7391	Intermediate Similarity	NPC474556
0.7389	Intermediate Similarity	NPC204580
0.7389	Intermediate Similarity	NPC474432
0.7389	Intermediate Similarity	NPC475713
0.7385	Intermediate Similarity	NPC241704
0.738	Intermediate Similarity	NPC133817
0.738	Intermediate Similarity	NPC476443
0.7368	Intermediate Similarity	NPC476569
0.7363	Intermediate Similarity	NPC63152
0.7358	Intermediate Similarity	NPC191012
0.7354	Intermediate Similarity	NPC205167
0.7347	Intermediate Similarity	NPC474325
0.7344	Intermediate Similarity	NPC145832
0.7344	Intermediate Similarity	NPC158376
0.7344	Intermediate Similarity	NPC117188
0.7344	Intermediate Similarity	NPC205421
0.7344	Intermediate Similarity	NPC306555
0.7344	Intermediate Similarity	NPC12053
0.7344	Intermediate Similarity	NPC81218
0.7344	Intermediate Similarity	NPC474931
0.734	Intermediate Similarity	NPC148014
0.734	Intermediate Similarity	NPC478161
0.734	Intermediate Similarity	NPC40389
0.734	Intermediate Similarity	NPC478159
0.734	Intermediate Similarity	NPC78359
0.734	Intermediate Similarity	NPC315707
0.734	Intermediate Similarity	NPC65490
0.733	Intermediate Similarity	NPC477563
0.733	Intermediate Similarity	NPC13504
0.733	Intermediate Similarity	NPC306843
0.733	Intermediate Similarity	NPC253043
0.733	Intermediate Similarity	NPC96603
0.733	Intermediate Similarity	NPC78222
0.733	Intermediate Similarity	NPC212794
0.733	Intermediate Similarity	NPC136508
0.733	Intermediate Similarity	NPC196447
0.7323	Intermediate Similarity	NPC248642
0.7317	Intermediate Similarity	NPC267414
0.731	Intermediate Similarity	NPC99179
0.7306	Intermediate Similarity	NPC41689
0.7296	Intermediate Similarity	NPC237044
0.7287	Intermediate Similarity	NPC147091
0.7286	Intermediate Similarity	NPC474746
0.7286	Intermediate Similarity	NPC156576
0.7286	Intermediate Similarity	NPC475981
0.7286	Intermediate Similarity	NPC104682
0.7277	Intermediate Similarity	NPC324144
0.7277	Intermediate Similarity	NPC1229
0.7273	Intermediate Similarity	NPC115869
0.7268	Intermediate Similarity	NPC255787
0.7263	Intermediate Similarity	NPC18402
0.7263	Intermediate Similarity	NPC27410
0.7263	Intermediate Similarity	NPC4304
0.7263	Intermediate Similarity	NPC166014
0.7259	Intermediate Similarity	NPC320223
0.7259	Intermediate Similarity	NPC114364
0.7259	Intermediate Similarity	NPC148693
0.7259	Intermediate Similarity	NPC118633
0.7259	Intermediate Similarity	NPC294790
0.7249	Intermediate Similarity	NPC300757
0.7249	Intermediate Similarity	NPC180901
0.7245	Intermediate Similarity	NPC128560
0.7245	Intermediate Similarity	NPC304675
0.7245	Intermediate Similarity	NPC229166
0.7245	Intermediate Similarity	NPC199465
0.7243	Intermediate Similarity	NPC469539
0.7243	Intermediate Similarity	NPC469540
0.7236	Intermediate Similarity	NPC47191
0.7236	Intermediate Similarity	NPC233718
0.7234	Intermediate Similarity	NPC131121
0.7234	Intermediate Similarity	NPC60211
0.7233	Intermediate Similarity	NPC207239
0.7231	Intermediate Similarity	NPC129578
0.7231	Intermediate Similarity	NPC150131
0.7231	Intermediate Similarity	NPC186392
0.722	Intermediate Similarity	NPC24228
0.7214	Intermediate Similarity	NPC8927
0.7211	Intermediate Similarity	NPC288353
0.7211	Intermediate Similarity	NPC118804
0.72	Intermediate Similarity	NPC244903
0.7192	Intermediate Similarity	NPC226708
0.7188	Intermediate Similarity	NPC59567
0.7188	Intermediate Similarity	NPC472961
0.7188	Intermediate Similarity	NPC472962
0.7184	Intermediate Similarity	NPC73020
0.7184	Intermediate Similarity	NPC14622
0.7184	Intermediate Similarity	NPC46744
0.7184	Intermediate Similarity	NPC70290
0.7184	Intermediate Similarity	NPC124302
0.7184	Intermediate Similarity	NPC215098
0.7181	Intermediate Similarity	NPC294511
0.7181	Intermediate Similarity	NPC121615
0.7179	Intermediate Similarity	NPC118274
0.7179	Intermediate Similarity	NPC168753
0.7173	Intermediate Similarity	NPC135006
0.7166	Intermediate Similarity	NPC476579
0.7165	Intermediate Similarity	NPC298979
0.7165	Intermediate Similarity	NPC181653
0.7165	Intermediate Similarity	NPC190332
0.7165	Intermediate Similarity	NPC150879
0.7165	Intermediate Similarity	NPC475779
0.7163	Intermediate Similarity	NPC316164
0.7158	Intermediate Similarity	NPC476572
0.7158	Intermediate Similarity	NPC268008
0.7158	Intermediate Similarity	NPC129603
0.7158	Intermediate Similarity	NPC27220
0.7157	Intermediate Similarity	NPC315306
0.7157	Intermediate Similarity	NPC313717
0.715	Intermediate Similarity	NPC116284
0.715	Intermediate Similarity	NPC225774
0.715	Intermediate Similarity	NPC246877
0.7143	Intermediate Similarity	NPC239775
0.7143	Intermediate Similarity	NPC193222
0.7143	Intermediate Similarity	NPC325871
0.7143	Intermediate Similarity	NPC99659
0.7135	Intermediate Similarity	NPC228501
0.7135	Intermediate Similarity	NPC153631
0.7135	Intermediate Similarity	NPC472299
0.7129	Intermediate Similarity	NPC475747
0.7129	Intermediate Similarity	NPC214116
0.7129	Intermediate Similarity	NPC228209
0.7121	Intermediate Similarity	NPC222524
0.7121	Intermediate Similarity	NPC474470
0.712	Intermediate Similarity	NPC7059
0.7115	Intermediate Similarity	NPC226652
0.7115	Intermediate Similarity	NPC120671
0.7115	Intermediate Similarity	NPC72788
0.7115	Intermediate Similarity	NPC314100
0.7114	Intermediate Similarity	NPC475566
0.7114	Intermediate Similarity	NPC476273
0.7113	Intermediate Similarity	NPC476432
0.7113	Intermediate Similarity	NPC219341
0.7113	Intermediate Similarity	NPC24264
0.7112	Intermediate Similarity	NPC68967
0.7111	Intermediate Similarity	NPC316292
0.7108	Intermediate Similarity	NPC240808

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 NPC67346 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	201
0.1-0.2	692
0.2-0.3	1030
0.3-0.4	2412
0.4-0.5	2426
0.5-0.6	1500
0.6-0.7	689
0.7-0.8	143
0.8-0.85	28
0.85-0.9	18
0.9-0.95	8
0.95-1	3

Similarity Score	Similarity Level	Drug ID	Developmental Stage
1.0	High Similarity	NPD3057	Approved
0.9889	High Similarity	NPD2972	Approved
0.9889	High Similarity	NPD3533	Approved
0.967	High Similarity	NPD2491	Approved
0.9563	High Similarity	NPD3448	Approved
0.9468	High Similarity	NPD5676	Approved
0.9454	High Similarity	NPD4107	Approved
0.9297	High Similarity	NPD4482	Phase 3
0.9031	High Similarity	NPD4111	Phase 1
0.9031	High Similarity	NPD4665	Approved
0.8945	High Similarity	NPD5619	Clinical (unspecified phase)
0.8939	High Similarity	NPD7907	Approved
0.8913	High Similarity	NPD2490	Approved
0.8913	High Similarity	NPD2488	Approved
0.8791	High Similarity	NPD2968	Approved
0.8791	High Similarity	NPD2971	Approved
0.8737	High Similarity	NPD5980	Discovery
0.8587	High Similarity	NPD3534	Clinical (unspecified phase)
0.8497	Intermediate Similarity	NPD2494	Approved
0.8497	Intermediate Similarity	NPD2493	Approved
0.8482	Intermediate Similarity	NPD2973	Approved
0.8482	Intermediate Similarity	NPD2975	Approved
0.8482	Intermediate Similarity	NPD2974	Approved
0.8462	Intermediate Similarity	NPD4583	Approved
0.8462	Intermediate Similarity	NPD4582	Approved
0.8446	Intermediate Similarity	NPD4580	Approved
0.841	Intermediate Similarity	NPD4004	Approved
0.841	Intermediate Similarity	NPD4002	Approved
0.8402	Intermediate Similarity	NPD3452	Approved
0.8402	Intermediate Similarity	NPD3450	Approved
0.8398	Intermediate Similarity	NPD2969	Approved
0.8398	Intermediate Similarity	NPD2970	Approved
0.8389	Intermediate Similarity	NPD7048	Phase 3
0.8367	Intermediate Similarity	NPD4040	Phase 1
0.8251	Intermediate Similarity	NPD27	Approved
0.8251	Intermediate Similarity	NPD2489	Approved
0.8242	Intermediate Similarity	NPD3051	Approved
0.8	Intermediate Similarity	NPD7312	Approved
0.8	Intermediate Similarity	NPD7310	Approved
0.8	Intermediate Similarity	NPD7311	Approved
0.8	Intermediate Similarity	NPD7313	Approved
0.7958	Intermediate Similarity	NPD7309	Approved
0.7957	Intermediate Similarity	NPD4481	Phase 3
0.7874	Intermediate Similarity	NPD7047	Phase 3
0.772	Intermediate Similarity	NPD4578	Approved
0.772	Intermediate Similarity	NPD4577	Approved
0.7692	Intermediate Similarity	NPD4663	Approved
0.7653	Intermediate Similarity	NPD6997	Phase 2
0.7563	Intermediate Similarity	NPD7906	Approved
0.7527	Intermediate Similarity	NPD5616	Clinical (unspecified phase)
0.7427	Intermediate Similarity	NPD7497	Discontinued
0.7409	Intermediate Similarity	NPD2163	Approved
0.7396	Intermediate Similarity	NPD2898	Approved
0.7382	Intermediate Similarity	NPD6071	Discontinued
0.734	Intermediate Similarity	NPD2563	Approved
0.734	Intermediate Similarity	NPD2560	Approved
0.731	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7306	Intermediate Similarity	NPD4575	Clinical (unspecified phase)
0.7282	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD7667	Clinical (unspecified phase)
0.7194	Intermediate Similarity	NPD3050	Clinical (unspecified phase)
0.7184	Intermediate Similarity	NPD4420	Approved
0.7176	Intermediate Similarity	NPD8404	Phase 2
0.7158	Intermediate Similarity	NPD5977	Approved
0.7158	Intermediate Similarity	NPD5978	Approved
0.7143	Intermediate Similarity	NPD3808	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7177	Discontinued
0.709	Intermediate Similarity	NPD6386	Approved
0.709	Intermediate Similarity	NPD6385	Approved
0.7085	Intermediate Similarity	NPD7038	Approved
0.7085	Intermediate Similarity	NPD7039	Approved
0.7059	Intermediate Similarity	NPD3640	Phase 3
0.7059	Intermediate Similarity	NPD3641	Approved
0.7059	Intermediate Similarity	NPD3639	Approved
0.7059	Intermediate Similarity	NPD5525	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD5006	Approved
0.7048	Intermediate Similarity	NPD5005	Approved
0.7044	Intermediate Similarity	NPD6040	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD7291	Discontinued
0.7043	Intermediate Similarity	NPD1754	Clinical (unspecified phase)
0.7005	Intermediate Similarity	NPD3446	Phase 1
0.7	Intermediate Similarity	NPD4772	Phase 2
0.7	Intermediate Similarity	NPD4773	Phase 2
0.6973	Remote Similarity	NPD5241	Discontinued
0.6963	Remote Similarity	NPD7577	Discontinued
0.6947	Remote Similarity	NPD1337	Clinical (unspecified phase)
0.6946	Remote Similarity	NPD5036	Approved
0.6935	Remote Similarity	NPD5844	Phase 1
0.6923	Remote Similarity	NPD4361	Phase 2
0.6923	Remote Similarity	NPD4362	Clinical (unspecified phase)
0.6912	Remote Similarity	NPD5038	Approved
0.6912	Remote Similarity	NPD5037	Approved
0.6908	Remote Similarity	NPD4466	Phase 1
0.6907	Remote Similarity	NPD7833	Phase 2
0.6907	Remote Similarity	NPD7831	Phase 2
0.6907	Remote Similarity	NPD7832	Clinical (unspecified phase)
0.689	Remote Similarity	NPD5564	Approved
0.6884	Remote Similarity	NPD7701	Phase 2
0.6875	Remote Similarity	NPD4363	Phase 3
0.6875	Remote Similarity	NPD4360	Phase 2
0.6866	Remote Similarity	NPD3823	Discontinued
0.6856	Remote Similarity	NPD3882	Suspended
0.685	Remote Similarity	NPD6042	Phase 2
0.685	Remote Similarity	NPD42	Phase 2
0.6837	Remote Similarity	NPD4666	Phase 3
0.6831	Remote Similarity	NPD6029	Clinical (unspecified phase)
0.6831	Remote Similarity	NPD6028	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD8434	Phase 2
0.6829	Remote Similarity	NPD3863	Clinical (unspecified phase)
0.681	Remote Similarity	NPD7238	Clinical (unspecified phase)
0.6806	Remote Similarity	NPD2649	Approved
0.6806	Remote Similarity	NPD2651	Approved
0.6806	Remote Similarity	NPD824	Approved
0.68	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6796	Remote Similarity	NPD3142	Approved
0.6796	Remote Similarity	NPD3140	Approved
0.6788	Remote Similarity	NPD6844	Discontinued
0.6786	Remote Similarity	NPD5709	Phase 3
0.6784	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6784	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6784	Remote Similarity	NPD6166	Phase 2
0.6769	Remote Similarity	NPD5019	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD7315	Approved
0.6766	Remote Similarity	NPD5312	Approved
0.6766	Remote Similarity	NPD5313	Approved
0.6763	Remote Similarity	NPD6377	Clinical (unspecified phase)
0.6763	Remote Similarity	NPD6836	Approved
0.6755	Remote Similarity	NPD6667	Approved
0.6755	Remote Similarity	NPD6666	Approved
0.6753	Remote Similarity	NPD5773	Approved
0.6753	Remote Similarity	NPD5772	Approved
0.6751	Remote Similarity	NPD5494	Approved
0.6749	Remote Similarity	NPD5030	Phase 2
0.6749	Remote Similarity	NPD5027	Approved
0.6749	Remote Similarity	NPD5031	Approved
0.6749	Remote Similarity	NPD5029	Approved
0.674	Remote Similarity	NPD8469	Approved
0.6738	Remote Similarity	NPD4628	Phase 3
0.6736	Remote Similarity	NPD7110	Phase 1
0.6736	Remote Similarity	NPD6873	Phase 2
0.6736	Remote Similarity	NPD7109	Clinical (unspecified phase)
0.6732	Remote Similarity	NPD8053	Approved
0.6732	Remote Similarity	NPD8054	Approved
0.6732	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6728	Remote Similarity	NPD4859	Phase 1
0.6716	Remote Similarity	NPD4954	Approved
0.6716	Remote Similarity	NPD5026	Approved
0.6716	Remote Similarity	NPD36	Approved
0.6716	Remote Similarity	NPD4955	Approved
0.6716	Remote Similarity	NPD5034	Approved
0.6716	Remote Similarity	NPD5028	Approved
0.6714	Remote Similarity	NPD5457	Discontinued
0.6713	Remote Similarity	NPD7607	Clinical (unspecified phase)
0.6703	Remote Similarity	NPD3110	Approved
0.6703	Remote Similarity	NPD3109	Approved
0.6702	Remote Similarity	NPD7427	Discontinued
0.6701	Remote Similarity	NPD1934	Approved
0.6701	Remote Similarity	NPD919	Approved
0.6699	Remote Similarity	NPD7296	Approved
0.6699	Remote Similarity	NPD5968	Phase 3
0.6684	Remote Similarity	NPD4584	Approved
0.6683	Remote Similarity	NPD4078	Clinical (unspecified phase)
0.6683	Remote Similarity	NPD5035	Approved
0.6667	Remote Similarity	NPD6818	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD8319	Approved
0.6667	Remote Similarity	NPD7922	Phase 1
0.6667	Remote Similarity	NPD8320	Phase 1
0.665	Remote Similarity	NPD4956	Approved
0.665	Remote Similarity	NPD8005	Clinical (unspecified phase)
0.6649	Remote Similarity	NPD3647	Clinical (unspecified phase)
0.6636	Remote Similarity	NPD6776	Approved
0.6636	Remote Similarity	NPD6777	Approved
0.6636	Remote Similarity	NPD8161	Suspended
0.6636	Remote Similarity	NPD6778	Approved
0.6636	Remote Similarity	NPD6779	Approved
0.6636	Remote Similarity	NPD6780	Approved
0.6636	Remote Similarity	NPD6782	Approved
0.6636	Remote Similarity	NPD6781	Approved
0.6635	Remote Similarity	NPD4413	Clinical (unspecified phase)
0.6634	Remote Similarity	NPD5032	Approved
0.6634	Remote Similarity	NPD7549	Discontinued
0.6633	Remote Similarity	NPD1247	Approved
0.6633	Remote Similarity	NPD5353	Approved
0.6633	Remote Similarity	NPD8127	Discontinued
0.6632	Remote Similarity	NPD2420	Approved
0.6632	Remote Similarity	NPD2421	Approved
0.6631	Remote Similarity	NPD4664	Clinical (unspecified phase)
0.6618	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6616	Remote Similarity	NPD6862	Phase 2
0.6615	Remote Similarity	NPD7248	Discontinued
0.6608	Remote Similarity	NPD7279	Phase 2
0.6608	Remote Similarity	NPD7278	Phase 2
0.6601	Remote Similarity	NPD8156	Discontinued
0.66	Remote Similarity	NPD5710	Approved
0.66	Remote Similarity	NPD5711	Approved
0.6599	Remote Similarity	NPD4947	Clinical (unspecified phase)
0.6597	Remote Similarity	NPD3146	Approved
0.6597	Remote Similarity	NPD3688	Clinical (unspecified phase)
0.6596	Remote Similarity	NPD5177	Phase 3

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