NPASS Compound

Structure

CID37272 OpenBabel06191715362D 26 29 0 0 1 0 0 0 0 0999 V2000 6.0622 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.0622 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 4.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 24 1 0 0 0 0 2 25 1 0 0 0 0 3 26 1 0 0 0 0 4 5 1 0 0 0 0 4 12 1 0 0 0 0 5 21 1 0 0 0 0 6 13 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 19 1 0 0 0 0 9 14 2 0 0 0 0 9 20 1 0 0 0 0 10 15 2 0 0 0 0 10 18 1 0 0 0 0 11 14 1 0 0 0 0 11 21 1 0 0 0 0 12 15 1 0 0 0 0 13 14 1 0 0 0 0 15 16 1 0 0 0 0 16 6 1 1 0 0 0 16 21 1 0 0 0 0 17 18 2 0 0 0 0 17 22 1 0 0 0 0 18 24 1 0 0 0 0 19 20 2 0 0 0 0 19 25 1 0 0 0 0 20 26 1 0 0 0 0 21 23 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	357.16
Volume:	359.379
LogP:	1.123
LogD:	2.14
LogS:	-0.667
# Rotatable Bonds:	3
TPSA:	70.98
# H-Bond Aceptor:	6
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.675
Synthetic Accessibility Score:	3.688
Fsp3:	0.4
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:	-5.572
MDCK Permeability:	1.6639705791021697e-05
Pgp-inhibitor:	0.009
Pgp-substrate:	0.999
Human Intestinal Absorption (HIA):	0.911
20% Bioavailability (F20%):	0.993
30% Bioavailability (F30%):	0.997

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.056
Plasma Protein Binding (PPB):	46.422813415527344%
Volume Distribution (VD):	1.844
Pgp-substrate:	22.04290199279785%

ADMET: Metabolism

CYP1A2-inhibitor:	0.043
CYP1A2-substrate:	0.772
CYP2C19-inhibitor:	0.059
CYP2C19-substrate:	0.828
CYP2C9-inhibitor:	0.009
CYP2C9-substrate:	0.665
CYP2D6-inhibitor:	0.032
CYP2D6-substrate:	0.895
CYP3A4-inhibitor:	0.021
CYP3A4-substrate:	0.875

ADMET: Excretion

Clearance (CL):	13.825
Half-life (T1/2):	0.938

ADMET: Toxicity

hERG Blockers:	0.013
Human Hepatotoxicity (H-HT):	0.133
Drug-inuced Liver Injury (DILI):	0.037
AMES Toxicity:	0.055
Rat Oral Acute Toxicity:	0.177
Maximum Recommended Daily Dose:	0.995
Skin Sensitization:	0.456
Carcinogencity:	0.042
Eye Corrosion:	0.004
Eye Irritation:	0.09
Respiratory Toxicity:	0.245

Download Data

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

Natural Product: NPC37272

Natural Product ID:	NPC37272
*Common Name:**	Discretine N-Oxide
IUPAC Name:	(13aS)-2,10,11-trimethoxy-7-oxido-6,8,13,13a-tetrahydro-5H-isoquinolino[2,1-b]isoquinolin-7-ium-3-ol
Synonyms:	Discretine N-Oxide
Standard InCHIKey:	VVJSPQNTUBTZOK-BJQOMGFOSA-N
Standard InCHI:	InChI=1S/C20H23NO5/c1-24-18-10-15-12(7-17(18)22)4-5-21(23)11-14-9-20(26-3)19(25-2)8-13(14)6-16(15)21/h7-10,16,22H,4-6,11H2,1-3H3/t16-,21?/m0/s1
SMILES:	COc1cc2c(CCN3(=O)Cc4cc(c(cc4C[C@@H]23)OC)OC)cc1O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL456615
PubChem CID:	25147610
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
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	seeds	n.a.	n.a.	PMID[11141125]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12398544]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18419154]
NPO32522	desmos rostrata	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19053513]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19296389]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21910504]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	seeds	n.a.	n.a.	PMID[22011319]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	seed	n.a.	PMID[22011319]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	Barks	n.a.	n.a.	PMID[2348205]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	fruit	n.a.	PMID[8786370]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	bark	n.a.	n.a.	PMID[9214729]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO2884	Annona squamosa	Species	Annonaceae	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	2

Activity Type	# Activity
Cell Line	1
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	IC50	>	28000.0	nM	PMID[532754]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	4200.0	nM	PMID[532754]

☑ 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 NPC37272 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	275
0.1-0.2	1533
0.2-0.3	8420
0.3-0.4	9813
0.4-0.5	6378
0.5-0.6	11541
0.6-0.7	3681
0.7-0.8	688
0.8-0.85	212
0.85-0.9	108
0.9-0.95	31
0.95-1	17

Similarity Score	Similarity Level	Natural Product ID
0.932	High Similarity	NPC220858
0.932	High Similarity	NPC151895
0.932	High Similarity	NPC192768
0.932	High Similarity	NPC88249
0.932	High Similarity	NPC97221
0.9205	High Similarity	NPC475326
0.9073	High Similarity	NPC193949
0.9073	High Similarity	NPC127674
0.9073	High Similarity	NPC54379
0.9073	High Similarity	NPC276588
0.9073	High Similarity	NPC295691
0.9073	High Similarity	NPC249797
0.9073	High Similarity	NPC207757
0.9073	High Similarity	NPC278799
0.9073	High Similarity	NPC110416
0.9073	High Similarity	NPC2413
0.9073	High Similarity	NPC184026
0.9073	High Similarity	NPC469817
0.9073	High Similarity	NPC204828
0.9073	High Similarity	NPC5238
0.9073	High Similarity	NPC39701
0.9073	High Similarity	NPC189266
0.9073	High Similarity	NPC172765
0.9054	High Similarity	NPC246587
0.9054	High Similarity	NPC24233
0.9054	High Similarity	NPC428
0.9054	High Similarity	NPC135538
0.9054	High Similarity	NPC147390
0.9054	High Similarity	NPC476571
0.8986	High Similarity	NPC191376
0.8986	High Similarity	NPC321505
0.8986	High Similarity	NPC179825
0.8896	High Similarity	NPC111485
0.8851	High Similarity	NPC185838
0.8844	High Similarity	NPC476567
0.8844	High Similarity	NPC136860
0.8844	High Similarity	NPC128019
0.8742	High Similarity	NPC477565
0.8742	High Similarity	NPC103379
0.8693	High Similarity	NPC133011
0.8693	High Similarity	NPC470924
0.8693	High Similarity	NPC82285
0.869	High Similarity	NPC131204
0.869	High Similarity	NPC301050
0.8671	High Similarity	NPC238530
0.8671	High Similarity	NPC276944
0.8671	High Similarity	NPC284183
0.8671	High Similarity	NPC232514
0.8671	High Similarity	NPC4138
0.8671	High Similarity	NPC24465
0.8671	High Similarity	NPC121275
0.8645	High Similarity	NPC147091
0.8627	High Similarity	NPC76213
0.8627	High Similarity	NPC277669
0.8625	High Similarity	NPC164429
0.8616	High Similarity	NPC256012
0.8616	High Similarity	NPC317272
0.8616	High Similarity	NPC268503
0.8616	High Similarity	NPC240841
0.8616	High Similarity	NPC42549
0.8616	High Similarity	NPC13916
0.8616	High Similarity	NPC250846
0.8616	High Similarity	NPC264850
0.8609	High Similarity	NPC210437
0.8609	High Similarity	NPC106295
0.8609	High Similarity	NPC476151
0.8609	High Similarity	NPC476144
0.8609	High Similarity	NPC51957
0.8609	High Similarity	NPC16107
0.8599	High Similarity	NPC205167
0.8581	High Similarity	NPC328750
0.8581	High Similarity	NPC188163
0.8581	High Similarity	NPC213206
0.8581	High Similarity	NPC474915
0.8553	High Similarity	NPC7467
0.8533	High Similarity	NPC294249
0.8514	High Similarity	NPC314682
0.8509	High Similarity	NPC66573
0.8497	Intermediate Similarity	NPC207824
0.8497	Intermediate Similarity	NPC60538
0.8491	Intermediate Similarity	NPC324144
0.8481	Intermediate Similarity	NPC249274
0.8481	Intermediate Similarity	NPC27410
0.8481	Intermediate Similarity	NPC166014
0.8457	Intermediate Similarity	NPC109925
0.8442	Intermediate Similarity	NPC274026
0.8438	Intermediate Similarity	NPC306843
0.8438	Intermediate Similarity	NPC253043
0.8438	Intermediate Similarity	NPC13504
0.8438	Intermediate Similarity	NPC196447
0.8438	Intermediate Similarity	NPC477563
0.8438	Intermediate Similarity	NPC76116
0.8438	Intermediate Similarity	NPC78222
0.8438	Intermediate Similarity	NPC96603
0.8438	Intermediate Similarity	NPC212794
0.8438	Intermediate Similarity	NPC136508
0.8408	Intermediate Similarity	NPC186063
0.8397	Intermediate Similarity	NPC477564
0.8397	Intermediate Similarity	NPC2295
0.8387	Intermediate Similarity	NPC476579
0.8333	Intermediate Similarity	NPC306555
0.8333	Intermediate Similarity	NPC12053
0.8333	Intermediate Similarity	NPC158376
0.8333	Intermediate Similarity	NPC117188
0.8333	Intermediate Similarity	NPC205421
0.8333	Intermediate Similarity	NPC233029
0.8333	Intermediate Similarity	NPC474931
0.8333	Intermediate Similarity	NPC210148
0.8333	Intermediate Similarity	NPC145832
0.8333	Intermediate Similarity	NPC81218
0.8293	Intermediate Similarity	NPC10871
0.8293	Intermediate Similarity	NPC475215
0.8293	Intermediate Similarity	NPC108434
0.8282	Intermediate Similarity	NPC160570
0.8276	Intermediate Similarity	NPC160193
0.8258	Intermediate Similarity	NPC44869
0.825	Intermediate Similarity	NPC226428
0.8235	Intermediate Similarity	NPC130926
0.8228	Intermediate Similarity	NPC187022
0.8228	Intermediate Similarity	NPC138487
0.8228	Intermediate Similarity	NPC80129
0.8228	Intermediate Similarity	NPC216459
0.8228	Intermediate Similarity	NPC41178
0.8221	Intermediate Similarity	NPC210140
0.8199	Intermediate Similarity	NPC60186
0.8194	Intermediate Similarity	NPC475959
0.8187	Intermediate Similarity	NPC59028
0.8187	Intermediate Similarity	NPC92191
0.8182	Intermediate Similarity	NPC239775
0.8176	Intermediate Similarity	NPC247639
0.8176	Intermediate Similarity	NPC25084
0.8176	Intermediate Similarity	NPC146288
0.8171	Intermediate Similarity	NPC470324
0.8171	Intermediate Similarity	NPC83198
0.8171	Intermediate Similarity	NPC204908
0.8166	Intermediate Similarity	NPC233718
0.816	Intermediate Similarity	NPC476573
0.816	Intermediate Similarity	NPC35627
0.816	Intermediate Similarity	NPC81247
0.8155	Intermediate Similarity	NPC32154
0.8153	Intermediate Similarity	NPC476568
0.8148	Intermediate Similarity	NPC1229
0.8148	Intermediate Similarity	NPC59567
0.8141	Intermediate Similarity	NPC92541
0.8133	Intermediate Similarity	NPC253429
0.8121	Intermediate Similarity	NPC477562
0.8121	Intermediate Similarity	NPC26240
0.8121	Intermediate Similarity	NPC69712
0.8121	Intermediate Similarity	NPC329911
0.8121	Intermediate Similarity	NPC475828
0.811	Intermediate Similarity	NPC100566
0.8107	Intermediate Similarity	NPC286119
0.8101	Intermediate Similarity	NPC26601
0.8098	Intermediate Similarity	NPC134858
0.8098	Intermediate Similarity	NPC3375
0.8098	Intermediate Similarity	NPC255607
0.8095	Intermediate Similarity	NPC477560
0.8084	Intermediate Similarity	NPC199465
0.8084	Intermediate Similarity	NPC229166
0.8084	Intermediate Similarity	NPC128560
0.8075	Intermediate Similarity	NPC216816
0.8072	Intermediate Similarity	NPC476331
0.8063	Intermediate Similarity	NPC477132
0.8063	Intermediate Similarity	NPC31311
0.8063	Intermediate Similarity	NPC234392
0.8063	Intermediate Similarity	NPC477133
0.8059	Intermediate Similarity	NPC182052
0.8059	Intermediate Similarity	NPC181796
0.8059	Intermediate Similarity	NPC251735
0.8059	Intermediate Similarity	NPC311973
0.8059	Intermediate Similarity	NPC229373
0.8059	Intermediate Similarity	NPC279228
0.8059	Intermediate Similarity	NPC104196
0.8059	Intermediate Similarity	NPC49075
0.8059	Intermediate Similarity	NPC290582
0.8059	Intermediate Similarity	NPC30779
0.8059	Intermediate Similarity	NPC239824
0.8059	Intermediate Similarity	NPC285931
0.8059	Intermediate Similarity	NPC8836
0.8059	Intermediate Similarity	NPC222661
0.8059	Intermediate Similarity	NPC185639
0.8059	Intermediate Similarity	NPC54654
0.8059	Intermediate Similarity	NPC223690
0.8059	Intermediate Similarity	NPC217748
0.8059	Intermediate Similarity	NPC15414
0.8059	Intermediate Similarity	NPC7715
0.8059	Intermediate Similarity	NPC90998
0.8059	Intermediate Similarity	NPC290005
0.8059	Intermediate Similarity	NPC42663
0.8059	Intermediate Similarity	NPC258657
0.8059	Intermediate Similarity	NPC271013
0.8059	Intermediate Similarity	NPC328155
0.8049	Intermediate Similarity	NPC124657
0.8038	Intermediate Similarity	NPC81733
0.8038	Intermediate Similarity	NPC326316
0.8037	Intermediate Similarity	NPC233650
0.8036	Intermediate Similarity	NPC241704
0.8025	Intermediate Similarity	NPC215829
0.8025	Intermediate Similarity	NPC97072
0.8024	Intermediate Similarity	NPC152680

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 NPC37272 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	179
0.1-0.2	728
0.2-0.3	1130
0.3-0.4	1819
0.4-0.5	2704
0.5-0.6	1755
0.6-0.7	660
0.7-0.8	152
0.8-0.85	20
0.85-0.9	2
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8609	High Similarity	NPD4584	Approved
0.8581	High Similarity	NPD4664	Clinical (unspecified phase)
0.8397	Intermediate Similarity	NPD4772	Phase 2
0.8397	Intermediate Similarity	NPD4773	Phase 2
0.8272	Intermediate Similarity	NPD4010	Discontinued
0.8258	Intermediate Similarity	NPD3639	Approved
0.8258	Intermediate Similarity	NPD3640	Phase 3
0.8258	Intermediate Similarity	NPD3641	Approved
0.8228	Intermediate Similarity	NPD7298	Approved
0.8171	Intermediate Similarity	NPD2898	Approved
0.8059	Intermediate Similarity	NPD8053	Approved
0.8059	Intermediate Similarity	NPD8054	Approved
0.8013	Intermediate Similarity	NPD1754	Clinical (unspecified phase)
0.7927	Intermediate Similarity	NPD7201	Clinical (unspecified phase)
0.7925	Intermediate Similarity	NPD4017	Approved
0.7844	Intermediate Similarity	NPD27	Approved
0.7844	Intermediate Similarity	NPD2489	Approved
0.7821	Intermediate Similarity	NPD5241	Discontinued
0.7785	Intermediate Similarity	NPD2669	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD6107	Approved
0.773	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.7722	Intermediate Similarity	NPD3124	Discontinued
0.7722	Intermediate Similarity	NPD2420	Approved
0.7722	Intermediate Similarity	NPD2421	Approved
0.7697	Intermediate Similarity	NPD7831	Phase 2
0.7697	Intermediate Similarity	NPD7833	Phase 2
0.7697	Intermediate Similarity	NPD7832	Clinical (unspecified phase)
0.7688	Intermediate Similarity	NPD6030	Approved
0.7688	Intermediate Similarity	NPD7311	Approved
0.7688	Intermediate Similarity	NPD7312	Approved
0.7688	Intermediate Similarity	NPD7310	Approved
0.7688	Intermediate Similarity	NPD6031	Approved
0.7688	Intermediate Similarity	NPD7313	Approved
0.7682	Intermediate Similarity	NPD2674	Phase 3
0.7679	Intermediate Similarity	NPD2969	Approved
0.7679	Intermediate Similarity	NPD2970	Approved
0.7658	Intermediate Similarity	NPD3845	Phase 1
0.7647	Intermediate Similarity	NPD8251	Approved
0.7647	Intermediate Similarity	NPD8252	Approved
0.7647	Intermediate Similarity	NPD8099	Discontinued
0.7644	Intermediate Similarity	NPD7309	Approved
0.7619	Intermediate Similarity	NPD6071	Discontinued
0.7619	Intermediate Similarity	NPD4166	Phase 2
0.7602	Intermediate Similarity	NPD8156	Discontinued
0.7576	Intermediate Similarity	NPD2560	Approved
0.7576	Intermediate Similarity	NPD2563	Approved
0.7548	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7548	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7547	Intermediate Similarity	NPD2422	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD3051	Approved
0.75	Intermediate Similarity	NPD5313	Approved
0.75	Intermediate Similarity	NPD3144	Approved
0.75	Intermediate Similarity	NPD5718	Phase 2
0.75	Intermediate Similarity	NPD5312	Approved
0.75	Intermediate Similarity	NPD3145	Approved
0.7486	Intermediate Similarity	NPD3534	Clinical (unspecified phase)
0.7416	Intermediate Similarity	NPD7906	Approved
0.7414	Intermediate Similarity	NPD6297	Approved
0.7389	Intermediate Similarity	NPD1632	Clinical (unspecified phase)
0.7384	Intermediate Similarity	NPD5602	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD7802	Discontinued
0.7321	Intermediate Similarity	NPD6788	Approved
0.7288	Intermediate Similarity	NPD4577	Approved
0.7288	Intermediate Similarity	NPD4578	Approved
0.7263	Intermediate Similarity	NPD4663	Approved
0.7261	Intermediate Similarity	NPD6895	Approved
0.7261	Intermediate Similarity	NPD6896	Approved
0.7255	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD3060	Approved
0.725	Intermediate Similarity	NPD5177	Phase 3
0.7247	Intermediate Similarity	NPD6851	Approved
0.7247	Intermediate Similarity	NPD6853	Approved
0.7225	Intermediate Similarity	NPD4481	Phase 3
0.7215	Intermediate Similarity	NPD1753	Discontinued
0.7202	Intermediate Similarity	NPD2978	Approved
0.7202	Intermediate Similarity	NPD2977	Approved
0.7179	Intermediate Similarity	NPD3110	Approved
0.7179	Intermediate Similarity	NPD3109	Approved
0.7169	Intermediate Similarity	NPD824	Approved
0.7152	Intermediate Similarity	NPD2122	Discontinued
0.7143	Intermediate Similarity	NPD2488	Approved
0.7143	Intermediate Similarity	NPD2490	Approved
0.7135	Intermediate Similarity	NPD8453	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD7667	Clinical (unspecified phase)
0.7069	Intermediate Similarity	NPD6688	Approved
0.7069	Intermediate Similarity	NPD6687	Approved
0.7066	Intermediate Similarity	NPD4005	Discontinued
0.7066	Intermediate Similarity	NPD7261	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD3053	Approved
0.7059	Intermediate Similarity	NPD5977	Approved
0.7059	Intermediate Similarity	NPD3055	Approved
0.7059	Intermediate Similarity	NPD5978	Approved
0.7055	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD3692	Discontinued
0.7055	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD7132	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD4236	Phase 3
0.7037	Intermediate Similarity	NPD4162	Approved
0.7037	Intermediate Similarity	NPD4237	Approved
0.703	Intermediate Similarity	NPD1424	Approved
0.7018	Intermediate Similarity	NPD4581	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD5772	Approved
0.7	Intermediate Similarity	NPD2668	Approved
0.7	Intermediate Similarity	NPD5773	Approved
0.7	Intermediate Similarity	NPD2667	Approved
0.6988	Remote Similarity	NPD6090	Discontinued
0.6982	Remote Similarity	NPD7109	Clinical (unspecified phase)
0.6982	Remote Similarity	NPD7110	Phase 1
0.6981	Remote Similarity	NPD817	Approved
0.6981	Remote Similarity	NPD823	Approved
0.6977	Remote Similarity	NPD4055	Discovery
0.6974	Remote Similarity	NPD2233	Approved
0.6974	Remote Similarity	NPD2232	Approved
0.6974	Remote Similarity	NPD2230	Approved
0.6968	Remote Similarity	NPD3635	Approved
0.6968	Remote Similarity	NPD3636	Approved
0.6968	Remote Similarity	NPD3637	Approved
0.6961	Remote Similarity	NPD6618	Phase 2
0.6947	Remote Similarity	NPD3448	Approved
0.6947	Remote Similarity	NPD2491	Approved
0.6943	Remote Similarity	NPD2028	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD1039	Discontinued
0.6928	Remote Similarity	NPD4123	Phase 3
0.6923	Remote Similarity	NPD2606	Approved
0.6923	Remote Similarity	NPD2605	Approved
0.6923	Remote Similarity	NPD3594	Approved
0.6923	Remote Similarity	NPD3595	Approved
0.6914	Remote Similarity	NPD3656	Approved
0.6909	Remote Similarity	NPD7124	Phase 2
0.6906	Remote Similarity	NPD7280	Phase 3
0.6906	Remote Similarity	NPD7281	Phase 3
0.6906	Remote Similarity	NPD5917	Clinical (unspecified phase)
0.6899	Remote Similarity	NPD4474	Approved
0.6899	Remote Similarity	NPD554	Clinical (unspecified phase)
0.6899	Remote Similarity	NPD4475	Approved
0.6895	Remote Similarity	NPD2493	Approved
0.6895	Remote Similarity	NPD2494	Approved
0.6895	Remote Similarity	NPD3450	Approved
0.6895	Remote Similarity	NPD3452	Approved
0.689	Remote Similarity	NPD6658	Clinical (unspecified phase)
0.6886	Remote Similarity	NPD3647	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD5156	Approved
0.6879	Remote Similarity	NPD5155	Approved
0.6878	Remote Similarity	NPD8095	Phase 1
0.6871	Remote Similarity	NPD7153	Discontinued
0.6867	Remote Similarity	NPD7598	Phase 2
0.6855	Remote Similarity	NPD2238	Phase 2
0.6852	Remote Similarity	NPD2161	Phase 2
0.6849	Remote Similarity	NPD228	Approved
0.6848	Remote Similarity	NPD7291	Discontinued
0.6845	Remote Similarity	NPD6662	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD7945	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD6876	Approved
0.6824	Remote Similarity	NPD1337	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD6875	Approved
0.6821	Remote Similarity	NPD4093	Discontinued
0.681	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD1136	Approved
0.6792	Remote Similarity	NPD1132	Approved
0.6792	Remote Similarity	NPD1130	Approved
0.6788	Remote Similarity	NPD4582	Approved
0.6788	Remote Similarity	NPD4583	Approved
0.6788	Remote Similarity	NPD6748	Discontinued
0.6788	Remote Similarity	NPD6331	Phase 2
0.6782	Remote Similarity	NPD5604	Discontinued
0.678	Remote Similarity	NPD4083	Discontinued
0.6778	Remote Similarity	NPD7479	Phase 2
0.6774	Remote Similarity	NPD5525	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD7258	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD5310	Approved
0.6774	Remote Similarity	NPD5311	Approved
0.6771	Remote Similarity	NPD3057	Approved
0.6771	Remote Similarity	NPD3533	Approved
0.6771	Remote Similarity	NPD2972	Approved
0.677	Remote Similarity	NPD4579	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD7037	Approved
0.6768	Remote Similarity	NPD7045	Clinical (unspecified phase)
0.6755	Remote Similarity	NPD2226	Clinical (unspecified phase)
0.6751	Remote Similarity	NPD5676	Approved
0.675	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.675	Remote Similarity	NPD3620	Phase 2
0.6739	Remote Similarity	NPD5087	Clinical (unspecified phase)
0.6736	Remote Similarity	NPD4004	Approved
0.6736	Remote Similarity	NPD4002	Approved
0.673	Remote Similarity	NPD598	Approved
0.673	Remote Similarity	NPD601	Approved
0.673	Remote Similarity	NPD597	Approved
0.6728	Remote Similarity	NPD6111	Discontinued
0.6725	Remote Similarity	NPD4678	Approved
0.6725	Remote Similarity	NPD4675	Approved
0.6721	Remote Similarity	NPD2968	Approved
0.6721	Remote Similarity	NPD2971	Approved
0.671	Remote Similarity	NPD1669	Approved
0.671	Remote Similarity	NPD3676	Clinical (unspecified phase)
0.671	Remote Similarity	NPD1421	Approved
0.671	Remote Similarity	NPD1420	Approved
0.6705	Remote Similarity	NPD4585	Approved
0.6705	Remote Similarity	NPD5677	Discontinued
0.6705	Remote Similarity	NPD2904	Discontinued

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