NPASS Compound

Structure

CID238530 OpenBabel06191716042D 24 28 0 0 1 0 0 0 0 0999 V2000 7.0132 -4.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4152 -2.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2812 -3.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4152 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 -1.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 -0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2812 -0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5878 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4152 -1.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2812 -1.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 -0.1910 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.1472 -2.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1472 -1.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4152 0.3090 0.0000 N 0 0 3 0 0 0 0 0 0 0 0 0 7.0132 -1.1910 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.0132 -3.1910 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.6180 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 22 1 0 0 0 0 2 3 2 0 0 0 0 2 11 1 0 0 0 0 3 16 1 0 0 0 0 4 5 1 0 0 0 0 4 12 1 0 0 0 0 5 20 1 0 0 0 0 6 11 1 0 0 0 0 6 15 1 0 0 0 0 7 12 2 0 0 0 0 7 17 1 0 0 0 0 8 13 2 0 0 0 0 8 18 1 0 0 0 0 9 14 1 0 0 0 0 9 20 1 0 0 0 0 10 23 1 0 0 0 0 10 24 1 0 0 0 0 11 14 2 0 0 0 0 12 13 1 0 0 0 0 13 15 1 0 0 0 0 14 19 1 0 0 0 0 15 20 1 1 0 0 0 16 19 2 0 0 0 0 16 22 1 0 0 0 0 17 18 2 0 0 0 0 17 23 1 0 0 0 0 18 24 1 0 0 0 0 19 21 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	325.13
Volume:	324.737
LogP:	2.59
LogD:	2.706
LogS:	-2.482
# Rotatable Bonds:	1
TPSA:	51.16
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.874
Synthetic Accessibility Score:	3.045
Fsp3:	0.368
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.109
MDCK Permeability:	2.7408470486989245e-05
Pgp-inhibitor:	0.165
Pgp-substrate:	0.438
Human Intestinal Absorption (HIA):	0.002
20% Bioavailability (F20%):	0.006
30% Bioavailability (F30%):	0.007

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.987
Plasma Protein Binding (PPB):	94.74393463134766%
Volume Distribution (VD):	1.347
Pgp-substrate:	5.496337890625%

ADMET: Metabolism

CYP1A2-inhibitor:	0.886
CYP1A2-substrate:	0.898
CYP2C19-inhibitor:	0.761
CYP2C19-substrate:	0.826
CYP2C9-inhibitor:	0.046
CYP2C9-substrate:	0.474
CYP2D6-inhibitor:	0.969
CYP2D6-substrate:	0.92
CYP3A4-inhibitor:	0.878
CYP3A4-substrate:	0.88

ADMET: Excretion

Clearance (CL):	20.375
Half-life (T1/2):	0.596

ADMET: Toxicity

hERG Blockers:	0.041
Human Hepatotoxicity (H-HT):	0.168
Drug-inuced Liver Injury (DILI):	0.464
AMES Toxicity:	0.153
Rat Oral Acute Toxicity:	0.671
Maximum Recommended Daily Dose:	0.966
Skin Sensitization:	0.667
Carcinogencity:	0.91
Eye Corrosion:	0.003
Eye Irritation:	0.024
Respiratory Toxicity:	0.943

Download Data

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

Natural Product: NPC238530

Natural Product ID:	NPC238530
*Common Name:**	PQECCKIOFCWGRJ-HNNXBMFYSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	PQECCKIOFCWGRJ-HNNXBMFYSA-N
Standard InCHI:	InChI=1S/C19H19NO4/c1-22-16-3-2-11-6-15-13-8-18-17(23-10-24-18)7-12(13)4-5-20(15)9-14(11)19(16)21/h2-3,7-8,15,21H,4-6,9-10H2,1H3/t15-/m0/s1
SMILES:	COc1ccc2c(c1O)CN1[C@@H](C2)c2cc3OCOc3cc2CC1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2314732
PubChem CID:	12313091
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0001909] Protoberberine alkaloids and derivatives

*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
NPO4986	Eschscholzia californica	Species	Papaveraceae	Eukaryota	n.a.	Oakham, MA, US	n.a.	PMID[16562853]
NPO4986	Eschscholzia californica	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17250743]
NPO3504	Argemone mexicana	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21094631]
NPO4986	Eschscholzia californica	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3504	Argemone mexicana	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO4986	Eschscholzia californica	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3504	Argemone mexicana	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4986	Eschscholzia californica	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO3504	Argemone mexicana	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO4986	Eschscholzia californica	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3504	Argemone mexicana	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
IC50	1
Ki	3
Others	4

Activity Type	# Activity
Individual Protein	8

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT243	Individual Protein	Dopamine D2 receptor	Homo sapiens	Ki	>	5000.0	nM	PMID[507001]
NPT242	Individual Protein	Dopamine D1 receptor	Homo sapiens	Ki	=	60.0	nM	PMID[507001]
NPT242	Individual Protein	Dopamine D1 receptor	Homo sapiens	Inhibition	=	98.7	%	PMID[507001]
NPT243	Individual Protein	Dopamine D2 receptor	Homo sapiens	Inhibition	=	78.0	%	PMID[507001]
NPT290	Individual Protein	Serotonin 2a (5-HT2a) receptor	Homo sapiens	Inhibition	=	49.1	%	PMID[507001]
NPT677	Individual Protein	Coagulation factor III	Homo sapiens	IC50	=	36.41	nM	PMID[507000]
NPT92	Individual Protein	Serotonin 1a (5-HT1a) receptor	Homo sapiens	Ki	>	5000.0	nM	PMID[507001]
NPT92	Individual Protein	Serotonin 1a (5-HT1a) receptor	Homo sapiens	Inhibition	=	82.8	%	PMID[507001]

☑ 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 NPC238530 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	1486
0.2-0.3	7538
0.3-0.4	10532
0.4-0.5	5873
0.5-0.6	11230
0.6-0.7	4464
0.7-0.8	827
0.8-0.85	252
0.85-0.9	139
0.9-0.95	55
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC276944
1.0	High Similarity	NPC232514
0.9737	High Similarity	NPC111485
0.9539	High Similarity	NPC469817
0.9539	High Similarity	NPC193949
0.9539	High Similarity	NPC276588
0.9539	High Similarity	NPC2413
0.9539	High Similarity	NPC39701
0.9539	High Similarity	NPC216459
0.9539	High Similarity	NPC5238
0.9539	High Similarity	NPC138487
0.9539	High Similarity	NPC189266
0.9539	High Similarity	NPC110416
0.9539	High Similarity	NPC295691
0.9539	High Similarity	NPC249797
0.9539	High Similarity	NPC41178
0.9539	High Similarity	NPC184026
0.9539	High Similarity	NPC54379
0.9539	High Similarity	NPC204828
0.9539	High Similarity	NPC172765
0.9539	High Similarity	NPC278799
0.9539	High Similarity	NPC207757
0.9539	High Similarity	NPC127674
0.9477	High Similarity	NPC146288
0.9351	High Similarity	NPC234392
0.9351	High Similarity	NPC31311
0.9276	High Similarity	NPC97221
0.9276	High Similarity	NPC220858
0.9276	High Similarity	NPC88249
0.9276	High Similarity	NPC192768
0.9276	High Similarity	NPC151895
0.9255	High Similarity	NPC2314
0.9211	High Similarity	NPC103379
0.9211	High Similarity	NPC477565
0.9156	High Similarity	NPC210148
0.9156	High Similarity	NPC233029
0.9145	High Similarity	NPC147390
0.9145	High Similarity	NPC246587
0.9145	High Similarity	NPC428
0.9145	High Similarity	NPC475959
0.9145	High Similarity	NPC135538
0.9145	High Similarity	NPC24233
0.9145	High Similarity	NPC476571
0.9125	High Similarity	NPC298979
0.9085	High Similarity	NPC320223
0.9085	High Similarity	NPC114364
0.908	High Similarity	NPC199465
0.908	High Similarity	NPC128560
0.908	High Similarity	NPC229166
0.9079	High Similarity	NPC210437
0.9079	High Similarity	NPC476151
0.9079	High Similarity	NPC191376
0.9079	High Similarity	NPC476144
0.9079	High Similarity	NPC106295
0.9079	High Similarity	NPC179825
0.9079	High Similarity	NPC51957
0.9079	High Similarity	NPC321505
0.9079	High Similarity	NPC16107
0.9062	High Similarity	NPC13916
0.9062	High Similarity	NPC264850
0.902	High Similarity	NPC7467
0.9	High Similarity	NPC24465
0.8947	High Similarity	NPC185838
0.8917	High Similarity	NPC93593
0.8889	High Similarity	NPC24260
0.8854	High Similarity	NPC477564
0.8854	High Similarity	NPC2295
0.8816	High Similarity	NPC128019
0.8816	High Similarity	NPC476567
0.8816	High Similarity	NPC136860
0.8812	High Similarity	NPC160298
0.8812	High Similarity	NPC232924
0.8812	High Similarity	NPC266753
0.8812	High Similarity	NPC477559
0.8812	High Similarity	NPC166014
0.8812	High Similarity	NPC306902
0.8812	High Similarity	NPC27410
0.881	High Similarity	NPC116284
0.8757	High Similarity	NPC135772
0.875	High Similarity	NPC476574
0.875	High Similarity	NPC155442
0.875	High Similarity	NPC312918
0.875	High Similarity	NPC477080
0.875	High Similarity	NPC477561
0.8743	High Similarity	NPC294790
0.8743	High Similarity	NPC148693
0.8743	High Similarity	NPC118633
0.8742	High Similarity	NPC147091
0.8736	High Similarity	NPC24228
0.8726	High Similarity	NPC277669
0.8726	High Similarity	NPC76213
0.8712	High Similarity	NPC24264
0.8712	High Similarity	NPC250846
0.8712	High Similarity	NPC317272
0.8712	High Similarity	NPC42549
0.8712	High Similarity	NPC256012
0.8712	High Similarity	NPC476432
0.8712	High Similarity	NPC240841
0.8712	High Similarity	NPC268503
0.8704	High Similarity	NPC59567
0.8704	High Similarity	NPC324144
0.8696	High Similarity	NPC215829
0.8696	High Similarity	NPC97072
0.869	High Similarity	NPC32154
0.8684	High Similarity	NPC328750
0.8684	High Similarity	NPC188163
0.8684	High Similarity	NPC213206
0.8684	High Similarity	NPC474915
0.8671	High Similarity	NPC37272
0.8671	High Similarity	NPC82285
0.8671	High Similarity	NPC133011
0.8667	High Similarity	NPC152212
0.8659	High Similarity	NPC474931
0.8659	High Similarity	NPC12053
0.8659	High Similarity	NPC81218
0.8659	High Similarity	NPC158376
0.8659	High Similarity	NPC306555
0.8659	High Similarity	NPC145832
0.8659	High Similarity	NPC117188
0.8659	High Similarity	NPC205421
0.8659	High Similarity	NPC100566
0.8659	High Similarity	NPC247389
0.865	High Similarity	NPC16805
0.865	High Similarity	NPC121275
0.865	High Similarity	NPC284183
0.865	High Similarity	NPC306843
0.865	High Similarity	NPC302527
0.865	High Similarity	NPC78222
0.865	High Similarity	NPC4138
0.865	High Similarity	NPC212794
0.865	High Similarity	NPC96603
0.865	High Similarity	NPC225774
0.865	High Similarity	NPC196447
0.865	High Similarity	NPC167546
0.865	High Similarity	NPC136508
0.865	High Similarity	NPC253043
0.865	High Similarity	NPC13504
0.865	High Similarity	NPC477563
0.8642	High Similarity	NPC60186
0.8625	High Similarity	NPC186063
0.8623	High Similarity	NPC187678
0.8618	High Similarity	NPC314682
0.8606	High Similarity	NPC83198
0.8606	High Similarity	NPC204908
0.8599	High Similarity	NPC207824
0.8599	High Similarity	NPC60538
0.8598	High Similarity	NPC219341
0.8588	High Similarity	NPC475654
0.8588	High Similarity	NPC248642
0.858	High Similarity	NPC126284
0.858	High Similarity	NPC205167
0.8571	High Similarity	NPC241704
0.8562	High Similarity	NPC78733
0.8555	High Similarity	NPC82763
0.8554	High Similarity	NPC311991
0.8553	High Similarity	NPC148898
0.8545	High Similarity	NPC210918
0.8545	High Similarity	NPC210140
0.8545	High Similarity	NPC181653
0.8545	High Similarity	NPC190332
0.8538	High Similarity	NPC156576
0.8519	High Similarity	NPC106786
0.8512	High Similarity	NPC477558
0.8503	High Similarity	NPC477640
0.8503	High Similarity	NPC470739
0.8503	High Similarity	NPC225597
0.8497	Intermediate Similarity	NPC186546
0.8497	Intermediate Similarity	NPC476576
0.8494	Intermediate Similarity	NPC241055
0.8494	Intermediate Similarity	NPC266176
0.8494	Intermediate Similarity	NPC82533
0.8494	Intermediate Similarity	NPC158148
0.8494	Intermediate Similarity	NPC475686
0.8494	Intermediate Similarity	NPC58766
0.8494	Intermediate Similarity	NPC66573
0.8494	Intermediate Similarity	NPC290759
0.8485	Intermediate Similarity	NPC81247
0.8485	Intermediate Similarity	NPC35627
0.8485	Intermediate Similarity	NPC304659
0.8485	Intermediate Similarity	NPC476573
0.8485	Intermediate Similarity	NPC86144
0.848	Intermediate Similarity	NPC49075
0.848	Intermediate Similarity	NPC311973
0.848	Intermediate Similarity	NPC54654
0.848	Intermediate Similarity	NPC15414
0.848	Intermediate Similarity	NPC185639
0.848	Intermediate Similarity	NPC182052
0.848	Intermediate Similarity	NPC285931
0.848	Intermediate Similarity	NPC181796
0.848	Intermediate Similarity	NPC73492
0.848	Intermediate Similarity	NPC42663
0.848	Intermediate Similarity	NPC290582
0.848	Intermediate Similarity	NPC222661
0.848	Intermediate Similarity	NPC217748
0.848	Intermediate Similarity	NPC251735
0.848	Intermediate Similarity	NPC258657
0.848	Intermediate Similarity	NPC7715
0.848	Intermediate Similarity	NPC299990
0.848	Intermediate Similarity	NPC223690
0.848	Intermediate Similarity	NPC239824

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 NPC238530 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	183
0.1-0.2	726
0.2-0.3	1047
0.3-0.4	1930
0.4-0.5	2604
0.5-0.6	1788
0.6-0.7	695
0.7-0.8	157
0.8-0.85	18
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9079	High Similarity	NPD4584	Approved
0.8684	High Similarity	NPD4664	Clinical (unspecified phase)
0.848	Intermediate Similarity	NPD8053	Approved
0.848	Intermediate Similarity	NPD8054	Approved
0.8274	Intermediate Similarity	NPD2898	Approved
0.8272	Intermediate Similarity	NPD4773	Phase 2
0.8272	Intermediate Similarity	NPD4772	Phase 2
0.8263	Intermediate Similarity	NPD4010	Discontinued
0.8221	Intermediate Similarity	NPD7298	Approved
0.8166	Intermediate Similarity	NPD2489	Approved
0.8166	Intermediate Similarity	NPD27	Approved
0.8165	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.8125	Intermediate Similarity	NPD1754	Clinical (unspecified phase)
0.807	Intermediate Similarity	NPD8252	Approved
0.807	Intermediate Similarity	NPD8251	Approved
0.807	Intermediate Similarity	NPD8099	Discontinued
0.8063	Intermediate Similarity	NPD2421	Approved
0.8063	Intermediate Similarity	NPD2420	Approved
0.8061	Intermediate Similarity	NPD2978	Approved
0.8061	Intermediate Similarity	NPD2977	Approved
0.8037	Intermediate Similarity	NPD4017	Approved
0.8036	Intermediate Similarity	NPD7201	Clinical (unspecified phase)
0.8025	Intermediate Similarity	NPD3639	Approved
0.8025	Intermediate Similarity	NPD3640	Phase 3
0.8025	Intermediate Similarity	NPD3641	Approved
0.8023	Intermediate Similarity	NPD8156	Discontinued
0.8	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD2970	Approved
0.8	Intermediate Similarity	NPD2969	Approved
0.7941	Intermediate Similarity	NPD3051	Approved
0.7937	Intermediate Similarity	NPD5241	Discontinued
0.7917	Intermediate Similarity	NPD7833	Phase 2
0.7917	Intermediate Similarity	NPD7831	Phase 2
0.7917	Intermediate Similarity	NPD7832	Clinical (unspecified phase)
0.7898	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7898	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7848	Intermediate Similarity	NPD1632	Clinical (unspecified phase)
0.7844	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.7836	Intermediate Similarity	NPD6071	Discontinued
0.7821	Intermediate Similarity	NPD7906	Approved
0.7805	Intermediate Similarity	NPD6031	Approved
0.7805	Intermediate Similarity	NPD6030	Approved
0.7798	Intermediate Similarity	NPD2560	Approved
0.7798	Intermediate Similarity	NPD2563	Approved
0.7797	Intermediate Similarity	NPD7310	Approved
0.7797	Intermediate Similarity	NPD7313	Approved
0.7797	Intermediate Similarity	NPD7312	Approved
0.7797	Intermediate Similarity	NPD7281	Phase 3
0.7797	Intermediate Similarity	NPD7280	Phase 3
0.7797	Intermediate Similarity	NPD7311	Approved
0.7778	Intermediate Similarity	NPD6107	Approved
0.7778	Intermediate Similarity	NPD3845	Phase 1
0.7753	Intermediate Similarity	NPD7309	Approved
0.7751	Intermediate Similarity	NPD6788	Approved
0.7697	Intermediate Similarity	NPD4577	Approved
0.7697	Intermediate Similarity	NPD4578	Approved
0.7677	Intermediate Similarity	NPD2669	Clinical (unspecified phase)
0.7669	Intermediate Similarity	NPD2422	Clinical (unspecified phase)
0.7667	Intermediate Similarity	NPD4663	Approved
0.7644	Intermediate Similarity	NPD4481	Phase 3
0.763	Intermediate Similarity	NPD4166	Phase 2
0.7628	Intermediate Similarity	NPD5718	Phase 2
0.7627	Intermediate Similarity	NPD6297	Approved
0.7622	Intermediate Similarity	NPD3124	Discontinued
0.7602	Intermediate Similarity	NPD5604	Discontinued
0.7598	Intermediate Similarity	NPD3534	Clinical (unspecified phase)
0.7593	Intermediate Similarity	NPD5177	Phase 3
0.7581	Intermediate Similarity	NPD4420	Approved
0.758	Intermediate Similarity	NPD2674	Phase 3
0.758	Intermediate Similarity	NPD554	Clinical (unspecified phase)
0.7541	Intermediate Similarity	NPD2488	Approved
0.7541	Intermediate Similarity	NPD2490	Approved
0.7514	Intermediate Similarity	NPD5312	Approved
0.7514	Intermediate Similarity	NPD5313	Approved
0.7513	Intermediate Similarity	NPD5005	Approved
0.7513	Intermediate Similarity	NPD5006	Approved
0.75	Intermediate Similarity	NPD5602	Clinical (unspecified phase)
0.7473	Intermediate Similarity	NPD7667	Clinical (unspecified phase)
0.7471	Intermediate Similarity	NPD7945	Clinical (unspecified phase)
0.7471	Intermediate Similarity	NPD7802	Discontinued
0.7459	Intermediate Similarity	NPD6851	Approved
0.7459	Intermediate Similarity	NPD6853	Approved
0.7444	Intermediate Similarity	NPD8453	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD3145	Approved
0.7405	Intermediate Similarity	NPD3144	Approved
0.7391	Intermediate Similarity	NPD6895	Approved
0.7391	Intermediate Similarity	NPD6896	Approved
0.7389	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.738	Intermediate Similarity	NPD5582	Discontinued
0.7378	Intermediate Similarity	NPD3060	Approved
0.7378	Intermediate Similarity	NPD4236	Phase 3
0.7378	Intermediate Similarity	NPD4237	Approved
0.7363	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD4474	Approved
0.7358	Intermediate Similarity	NPD4475	Approved
0.7347	Intermediate Similarity	NPD3815	Phase 1
0.7347	Intermediate Similarity	NPD3816	Phase 1
0.7346	Intermediate Similarity	NPD1753	Discontinued
0.7341	Intermediate Similarity	NPD4581	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD2492	Phase 1
0.7321	Intermediate Similarity	NPD6090	Discontinued
0.7305	Intermediate Similarity	NPD7598	Phase 2
0.7299	Intermediate Similarity	NPD4055	Discovery
0.7283	Intermediate Similarity	NPD5978	Approved
0.7283	Intermediate Similarity	NPD5977	Approved
0.7277	Intermediate Similarity	NPD2494	Approved
0.7277	Intermediate Similarity	NPD3452	Approved
0.7277	Intermediate Similarity	NPD3450	Approved
0.7277	Intermediate Similarity	NPD2493	Approved
0.7273	Intermediate Similarity	NPD4162	Approved
0.7263	Intermediate Similarity	NPD8095	Phase 1
0.7262	Intermediate Similarity	NPD1424	Approved
0.7229	Intermediate Similarity	NPD6748	Discontinued
0.7226	Intermediate Similarity	NPD2233	Approved
0.7226	Intermediate Similarity	NPD2230	Approved
0.7226	Intermediate Similarity	NPD2232	Approved
0.7225	Intermediate Similarity	NPD5773	Approved
0.7225	Intermediate Similarity	NPD5772	Approved
0.7222	Intermediate Similarity	NPD4873	Discontinued
0.7219	Intermediate Similarity	NPD3647	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD7045	Clinical (unspecified phase)
0.7205	Intermediate Similarity	NPD3109	Approved
0.7205	Intermediate Similarity	NPD3110	Approved
0.7197	Intermediate Similarity	NPD3055	Approved
0.7197	Intermediate Similarity	NPD3053	Approved
0.7193	Intermediate Similarity	NPD7261	Clinical (unspecified phase)
0.7186	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7186	Intermediate Similarity	NPD3692	Discontinued
0.7176	Intermediate Similarity	NPD4727	Phase 1
0.7173	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7166	Intermediate Similarity	NPD5525	Clinical (unspecified phase)
0.7165	Intermediate Similarity	NPD4582	Approved
0.7165	Intermediate Similarity	NPD4583	Approved
0.7152	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD2668	Approved
0.7143	Intermediate Similarity	NPD2667	Approved
0.7134	Intermediate Similarity	NPD4108	Discontinued
0.7126	Intermediate Similarity	NPD5754	Discontinued
0.7126	Intermediate Similarity	NPD3977	Clinical (unspecified phase)
0.712	Intermediate Similarity	NPD2971	Approved
0.712	Intermediate Similarity	NPD2968	Approved
0.7113	Intermediate Similarity	NPD4002	Approved
0.7113	Intermediate Similarity	NPD4004	Approved
0.7112	Intermediate Similarity	NPD3408	Clinical (unspecified phase)
0.711	Intermediate Similarity	NPD7109	Clinical (unspecified phase)
0.711	Intermediate Similarity	NPD7110	Phase 1
0.7108	Intermediate Similarity	NPD7037	Approved
0.7099	Intermediate Similarity	NPD2238	Phase 2
0.7093	Intermediate Similarity	NPD824	Approved
0.7093	Intermediate Similarity	NPD4005	Discontinued
0.7088	Intermediate Similarity	NPD3885	Approved
0.7085	Intermediate Similarity	NPD7827	Phase 1
0.7083	Intermediate Similarity	NPD5160	Discontinued
0.7081	Intermediate Similarity	NPD2028	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD6618	Phase 2
0.7077	Intermediate Similarity	NPD4040	Phase 1
0.7076	Intermediate Similarity	NPD2122	Discontinued
0.7074	Intermediate Similarity	NPD6656	Clinical (unspecified phase)
0.7068	Intermediate Similarity	NPD2973	Approved
0.7068	Intermediate Similarity	NPD2974	Approved
0.7068	Intermediate Similarity	NPD2975	Approved
0.7065	Intermediate Similarity	NPD7132	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD7243	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD3349	Phase 2
0.7059	Intermediate Similarity	NPD4123	Phase 3
0.7048	Intermediate Similarity	NPD3656	Approved
0.7047	Intermediate Similarity	NPD5457	Discontinued
0.7044	Intermediate Similarity	NPD8318	Clinical (unspecified phase)
0.7043	Intermediate Similarity	NPD5087	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD7124	Phase 2
0.7041	Intermediate Similarity	NPD7607	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD7296	Approved
0.7024	Intermediate Similarity	NPD6658	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD6331	Phase 2
0.7022	Intermediate Similarity	NPD4666	Phase 3
0.7019	Intermediate Similarity	NPD5155	Approved
0.7019	Intermediate Similarity	NPD5156	Approved
0.7013	Intermediate Similarity	NPD2226	Clinical (unspecified phase)
0.7012	Intermediate Similarity	NPD4579	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD3635	Approved
0.7	Intermediate Similarity	NPD3637	Approved
0.7	Intermediate Similarity	NPD6688	Approved
0.7	Intermediate Similarity	NPD3636	Approved
0.7	Intermediate Similarity	NPD6687	Approved
0.6995	Remote Similarity	NPD7479	Phase 2
0.698	Remote Similarity	NPD7047	Phase 3
0.6977	Remote Similarity	NPD1914	Approved
0.6977	Remote Similarity	NPD6662	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD5976	Discontinued
0.6973	Remote Similarity	NPD7549	Discontinued
0.697	Remote Similarity	NPD7718	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD4093	Discontinued
0.6968	Remote Similarity	NPD7291	Discontinued
0.6966	Remote Similarity	NPD5709	Phase 3
0.6966	Remote Similarity	NPD7400	Phase 3
0.6959	Remote Similarity	NPD4580	Approved
0.6957	Remote Similarity	NPD3594	Approved
0.6957	Remote Similarity	NPD2605	Approved
0.6957	Remote Similarity	NPD3595	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