NPASS Compound

Structure

NPC232386 OpenBabel07101719242D 23 26 0 0 1 0 0 0 0 0999 V2000 2.3534 -2.6413 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7618 -2.1803 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3534 1.3587 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4873 1.8587 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2194 -0.1413 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2194 -1.1413 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 -0.1857 -1.9356 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9031 -0.6930 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3534 0.3587 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1730 -1.3143 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4873 -1.1413 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.6213 1.3587 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9031 -1.9356 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1857 -0.6930 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2618 -1.3143 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4873 -0.1413 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6213 0.3587 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3534 -1.6413 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.2447 1.8587 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4031 -2.8017 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2618 -1.3143 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 22 1 0 0 0 0 3 4 2 0 0 0 0 3 10 1 0 0 0 0 4 13 1 0 0 0 0 5 6 1 0 0 0 0 5 10 1 0 0 0 0 6 19 1 0 0 0 0 7 11 1 0 0 0 0 8 11 2 0 0 0 0 8 14 1 0 0 0 0 9 15 2 0 0 0 0 9 16 1 0 0 0 0 10 17 2 0 0 0 0 11 15 1 0 0 0 0 12 7 1 1 0 0 0 12 17 1 0 0 0 0 12 19 1 0 0 0 0 13 18 2 0 0 0 0 13 20 1 0 0 0 0 14 16 2 0 0 0 0 14 21 1 0 0 0 0 15 23 1 0 0 0 0 16 22 1 0 0 0 0 17 18 1 0 0 0 0 18 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	313.13
Volume:	315.997
LogP:	2.24
LogD:	2.551
LogS:	-2.354
# Rotatable Bonds:	1
TPSA:	62.16
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.847
Synthetic Accessibility Score:	3.165
Fsp3:	0.333
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:	-4.926
MDCK Permeability:	2.0811829017475247e-05
Pgp-inhibitor:	0.028
Pgp-substrate:	0.886
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.577
30% Bioavailability (F30%):	0.361

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.86
Plasma Protein Binding (PPB):	58.490882873535156%
Volume Distribution (VD):	1.772
Pgp-substrate:	23.97601318359375%

ADMET: Metabolism

CYP1A2-inhibitor:	0.845
CYP1A2-substrate:	0.952
CYP2C19-inhibitor:	0.11
CYP2C19-substrate:	0.731
CYP2C9-inhibitor:	0.057
CYP2C9-substrate:	0.69
CYP2D6-inhibitor:	0.282
CYP2D6-substrate:	0.92
CYP3A4-inhibitor:	0.039
CYP3A4-substrate:	0.885

ADMET: Excretion

Clearance (CL):	15.917
Half-life (T1/2):	0.824

ADMET: Toxicity

hERG Blockers:	0.309
Human Hepatotoxicity (H-HT):	0.023
Drug-inuced Liver Injury (DILI):	0.412
AMES Toxicity:	0.225
Rat Oral Acute Toxicity:	0.947
Maximum Recommended Daily Dose:	0.967
Skin Sensitization:	0.932
Carcinogencity:	0.381
Eye Corrosion:	0.003
Eye Irritation:	0.035
Respiratory Toxicity:	0.93

Download Data

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

Natural Product: NPC232386

Natural Product ID:	NPC232386
*Common Name:**	Breoganine
IUPAC Name:	n.a.
Synonyms:	Breoganine
Standard InCHIKey:	NEQWPVBUZDJIHK-LBPRGKRZSA-N
Standard InCHI:	InChI=1S/C18H19NO4/c1-19-6-5-10-3-4-13(20)18-17(10)12(19)7-11-8-14(21)16(22-2)9-15(11)23-18/h3-4,8-9,12,20-21H,5-7H2,1-2H3/t12-/m0/s1
SMILES:	CN1CCc2ccc(c3c2[C@@H]1Cc1cc(c(cc1O3)OC)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL452510
PubChem CID:	177725
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0002657] Cularin 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
NPO33048	sarcuapnos crassfolia	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[8676127]

☑ 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	4
Others	2

Activity Type	# Activity
Individual Protein	4
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1857	Individual Protein	Dopamine D1 receptor	Rattus norvegicus	IC50	=	100.0	nM	PMID[497103]
NPT1858	Individual Protein	Dopamine D2 receptor	Rattus norvegicus	IC50	=	200.0	nM	PMID[497103]
NPT1073	Individual Protein	Dopamine transporter	Rattus norvegicus	IC50	=	57000.0	nM	PMID[497103]
NPT1073	Individual Protein	Dopamine transporter	Rattus norvegicus	IC50	=	56500.0	nM	PMID[497104]
NPT2	Others	Unspecified		Ratio IC50	=	0.002	n.a.	PMID[497104]
NPT2	Others	Unspecified		Ratio IC50	=	0.004	n.a.	PMID[497104]

☑ 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 NPC232386 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	364
0.1-0.2	1774
0.2-0.3	8807
0.3-0.4	9533
0.4-0.5	5154
0.5-0.6	8231
0.6-0.7	6943
0.7-0.8	1550
0.8-0.85	189
0.85-0.9	106
0.9-0.95	41
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC152680
1.0	High Similarity	NPC190783
0.981	High Similarity	NPC204908
0.981	High Similarity	NPC83198
0.9317	High Similarity	NPC264850
0.9317	High Similarity	NPC13916
0.9255	High Similarity	NPC24465
0.9231	High Similarity	NPC116465
0.9231	High Similarity	NPC212237
0.9053	High Similarity	NPC239824
0.9053	High Similarity	NPC258657
0.9053	High Similarity	NPC54654
0.9053	High Similarity	NPC285931
0.9053	High Similarity	NPC217748
0.9053	High Similarity	NPC251735
0.9053	High Similarity	NPC229373
0.9053	High Similarity	NPC290582
0.9053	High Similarity	NPC8836
0.9053	High Similarity	NPC290005
0.9053	High Similarity	NPC181796
0.9053	High Similarity	NPC279228
0.9053	High Similarity	NPC311973
0.9053	High Similarity	NPC42663
0.9053	High Similarity	NPC185639
0.9053	High Similarity	NPC104196
0.9053	High Similarity	NPC15414
0.9053	High Similarity	NPC182052
0.9053	High Similarity	NPC49075
0.9053	High Similarity	NPC328155
0.9053	High Similarity	NPC271013
0.9053	High Similarity	NPC7715
0.9053	High Similarity	NPC223690
0.9053	High Similarity	NPC222661
0.9053	High Similarity	NPC90998
0.9012	High Similarity	NPC206900
0.9	High Similarity	NPC254441
0.9	High Similarity	NPC274716
0.9	High Similarity	NPC167116
0.8994	High Similarity	NPC475557
0.8994	High Similarity	NPC286119
0.8953	High Similarity	NPC275680
0.8953	High Similarity	NPC22115
0.8941	High Similarity	NPC30779
0.8862	High Similarity	NPC239775
0.8861	High Similarity	NPC103379
0.8861	High Similarity	NPC477565
0.8837	High Similarity	NPC16357
0.8837	High Similarity	NPC95426
0.8837	High Similarity	NPC302245
0.882	High Similarity	NPC204828
0.882	High Similarity	NPC207757
0.882	High Similarity	NPC276588
0.882	High Similarity	NPC127674
0.882	High Similarity	NPC189266
0.882	High Similarity	NPC110416
0.882	High Similarity	NPC295691
0.882	High Similarity	NPC172765
0.882	High Similarity	NPC54379
0.882	High Similarity	NPC5238
0.882	High Similarity	NPC278799
0.882	High Similarity	NPC469817
0.882	High Similarity	NPC2413
0.882	High Similarity	NPC39701
0.882	High Similarity	NPC249797
0.882	High Similarity	NPC184026
0.882	High Similarity	NPC193949
0.8817	High Similarity	NPC293093
0.8802	High Similarity	NPC118274
0.8802	High Similarity	NPC168753
0.8797	High Similarity	NPC24233
0.8797	High Similarity	NPC135538
0.8797	High Similarity	NPC147390
0.8797	High Similarity	NPC246587
0.8797	High Similarity	NPC428
0.8797	High Similarity	NPC476571
0.8793	High Similarity	NPC48490
0.8793	High Similarity	NPC175890
0.8793	High Similarity	NPC274661
0.8793	High Similarity	NPC11296
0.8793	High Similarity	NPC82457
0.8786	High Similarity	NPC139783
0.8786	High Similarity	NPC65312
0.8743	High Similarity	NPC191132
0.8743	High Similarity	NPC60295
0.8734	High Similarity	NPC179825
0.8734	High Similarity	NPC321505
0.8734	High Similarity	NPC191376
0.8734	High Similarity	NPC476151
0.8693	High Similarity	NPC24260
0.8683	High Similarity	NPC306555
0.8683	High Similarity	NPC205421
0.8683	High Similarity	NPC474931
0.8683	High Similarity	NPC117188
0.8683	High Similarity	NPC12053
0.8683	High Similarity	NPC158376
0.8683	High Similarity	NPC81218
0.8683	High Similarity	NPC145832
0.8659	High Similarity	NPC329837
0.8644	High Similarity	NPC85381
0.8639	High Similarity	NPC276890
0.8639	High Similarity	NPC76682
0.8639	High Similarity	NPC317145
0.8639	High Similarity	NPC63646
0.8639	High Similarity	NPC10908
0.8639	High Similarity	NPC115284
0.8639	High Similarity	NPC198498
0.8639	High Similarity	NPC317439
0.8639	High Similarity	NPC227060
0.8636	High Similarity	NPC318805
0.8636	High Similarity	NPC41122
0.8608	High Similarity	NPC185838
0.8605	High Similarity	NPC474507
0.8588	High Similarity	NPC12424
0.8588	High Similarity	NPC41376
0.8588	High Similarity	NPC129518
0.8588	High Similarity	NPC251580
0.8588	High Similarity	NPC478093
0.8571	High Similarity	NPC97221
0.8571	High Similarity	NPC192768
0.8571	High Similarity	NPC88249
0.8571	High Similarity	NPC220858
0.8571	High Similarity	NPC151895
0.8563	High Similarity	NPC477563
0.8563	High Similarity	NPC78222
0.8563	High Similarity	NPC13504
0.8563	High Similarity	NPC306843
0.8563	High Similarity	NPC253043
0.8563	High Similarity	NPC96603
0.8563	High Similarity	NPC136508
0.8563	High Similarity	NPC196447
0.8563	High Similarity	NPC212794
0.8554	High Similarity	NPC80759
0.8554	High Similarity	NPC60186
0.8554	High Similarity	NPC79402
0.8553	High Similarity	NPC473934
0.8547	High Similarity	NPC234318
0.8539	High Similarity	NPC478091
0.8539	High Similarity	NPC473589
0.8539	High Similarity	NPC478092
0.8539	High Similarity	NPC30182
0.8539	High Similarity	NPC256124
0.8528	High Similarity	NPC2295
0.8528	High Similarity	NPC477564
0.8503	High Similarity	NPC1229
0.8503	High Similarity	NPC324144
0.8494	Intermediate Similarity	NPC119649
0.8494	Intermediate Similarity	NPC230956
0.8494	Intermediate Similarity	NPC271388
0.8494	Intermediate Similarity	NPC205255
0.8494	Intermediate Similarity	NPC235143
0.8488	Intermediate Similarity	NPC148709
0.8488	Intermediate Similarity	NPC476577
0.8488	Intermediate Similarity	NPC173416
0.8452	Intermediate Similarity	NPC232514
0.8452	Intermediate Similarity	NPC276944
0.8452	Intermediate Similarity	NPC238530
0.8434	Intermediate Similarity	NPC221864
0.8407	Intermediate Similarity	NPC475654
0.8405	Intermediate Similarity	NPC76213
0.8405	Intermediate Similarity	NPC277669
0.8402	Intermediate Similarity	NPC42549
0.8402	Intermediate Similarity	NPC250846
0.8402	Intermediate Similarity	NPC317272
0.8402	Intermediate Similarity	NPC124657
0.8402	Intermediate Similarity	NPC256012
0.8402	Intermediate Similarity	NPC268503
0.8402	Intermediate Similarity	NPC240841
0.8391	Intermediate Similarity	NPC32154
0.8391	Intermediate Similarity	NPC243454
0.8391	Intermediate Similarity	NPC475479
0.8385	Intermediate Similarity	NPC16107
0.8385	Intermediate Similarity	NPC51957
0.8385	Intermediate Similarity	NPC210437
0.8385	Intermediate Similarity	NPC106295
0.8385	Intermediate Similarity	NPC476144
0.8383	Intermediate Similarity	NPC18402
0.8383	Intermediate Similarity	NPC166014
0.8383	Intermediate Similarity	NPC27410
0.8373	Intermediate Similarity	NPC129603
0.8372	Intermediate Similarity	NPC192135
0.8372	Intermediate Similarity	NPC477020
0.8372	Intermediate Similarity	NPC66341
0.8354	Intermediate Similarity	NPC474915
0.8354	Intermediate Similarity	NPC213206
0.8354	Intermediate Similarity	NPC188163
0.8354	Intermediate Similarity	NPC328750
0.8343	Intermediate Similarity	NPC239584
0.8333	Intermediate Similarity	NPC114364
0.8333	Intermediate Similarity	NPC320223
0.8333	Intermediate Similarity	NPC7467
0.8295	Intermediate Similarity	NPC73492
0.8295	Intermediate Similarity	NPC299990
0.8291	Intermediate Similarity	NPC314682
0.8282	Intermediate Similarity	NPC60538
0.8282	Intermediate Similarity	NPC207824
0.8276	Intermediate Similarity	NPC241704
0.8274	Intermediate Similarity	NPC205167
0.8274	Intermediate Similarity	NPC249274
0.8268	Intermediate Similarity	NPC82763
0.8266	Intermediate Similarity	NPC2314

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 NPC232386 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	218
0.1-0.2	795
0.2-0.3	1176
0.3-0.4	2245
0.4-0.5	2392
0.5-0.6	1478
0.6-0.7	685
0.7-0.8	147
0.8-0.85	8
0.85-0.9	4
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9053	High Similarity	NPD8054	Approved
0.9053	High Similarity	NPD8053	Approved
0.8639	High Similarity	NPD8251	Approved
0.8639	High Similarity	NPD8252	Approved
0.8639	High Similarity	NPD8099	Discontinued
0.8588	High Similarity	NPD8156	Discontinued
0.8385	Intermediate Similarity	NPD4584	Approved
0.8354	Intermediate Similarity	NPD4664	Clinical (unspecified phase)
0.8294	Intermediate Similarity	NPD6071	Discontinued
0.8263	Intermediate Similarity	NPD2560	Approved
0.8263	Intermediate Similarity	NPD2563	Approved
0.8258	Intermediate Similarity	NPD7906	Approved
0.8214	Intermediate Similarity	NPD6788	Approved
0.8101	Intermediate Similarity	NPD4663	Approved
0.8092	Intermediate Similarity	NPD27	Approved
0.8092	Intermediate Similarity	NPD2489	Approved
0.8084	Intermediate Similarity	NPD4772	Phase 2
0.8084	Intermediate Similarity	NPD4773	Phase 2
0.8049	Intermediate Similarity	NPD1754	Clinical (unspecified phase)
0.8035	Intermediate Similarity	NPD2969	Approved
0.8035	Intermediate Similarity	NPD2970	Approved
0.8034	Intermediate Similarity	NPD7312	Approved
0.8034	Intermediate Similarity	NPD4578	Approved
0.8034	Intermediate Similarity	NPD7311	Approved
0.8034	Intermediate Similarity	NPD4577	Approved
0.8034	Intermediate Similarity	NPD7313	Approved
0.8034	Intermediate Similarity	NPD7310	Approved
0.7989	Intermediate Similarity	NPD7309	Approved
0.7977	Intermediate Similarity	NPD3051	Approved
0.7977	Intermediate Similarity	NPD4010	Discontinued
0.7975	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7965	Intermediate Similarity	NPD5677	Discontinued
0.7953	Intermediate Similarity	NPD4055	Discovery
0.7886	Intermediate Similarity	NPD2898	Approved
0.7882	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.7877	Intermediate Similarity	NPD7549	Discontinued
0.7844	Intermediate Similarity	NPD6031	Approved
0.7844	Intermediate Similarity	NPD6030	Approved
0.7831	Intermediate Similarity	NPD1424	Approved
0.7811	Intermediate Similarity	NPD4675	Approved
0.7811	Intermediate Similarity	NPD4678	Approved
0.7766	Intermediate Similarity	NPD8095	Phase 1
0.7751	Intermediate Similarity	NPD7261	Clinical (unspecified phase)
0.7751	Intermediate Similarity	NPD4017	Approved
0.7746	Intermediate Similarity	NPD7832	Clinical (unspecified phase)
0.7746	Intermediate Similarity	NPD7831	Phase 2
0.7746	Intermediate Similarity	NPD7833	Phase 2
0.7716	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7716	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.768	Intermediate Similarity	NPD8453	Clinical (unspecified phase)
0.7679	Intermediate Similarity	NPD6090	Discontinued
0.7665	Intermediate Similarity	NPD2420	Approved
0.7665	Intermediate Similarity	NPD2421	Approved
0.7658	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7657	Intermediate Similarity	NPD7201	Clinical (unspecified phase)
0.7651	Intermediate Similarity	NPD5241	Discontinued
0.7647	Intermediate Similarity	NPD4005	Discontinued
0.7636	Intermediate Similarity	NPD5177	Phase 3
0.7619	Intermediate Similarity	NPD7447	Phase 1
0.7616	Intermediate Similarity	NPD7298	Approved
0.7606	Intermediate Similarity	NPD7667	Clinical (unspecified phase)
0.7605	Intermediate Similarity	NPD7124	Phase 2
0.7595	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7592	Intermediate Similarity	NPD3452	Approved
0.7592	Intermediate Similarity	NPD3450	Approved
0.7592	Intermediate Similarity	NPD2494	Approved
0.7592	Intermediate Similarity	NPD2493	Approved
0.7584	Intermediate Similarity	NPD4481	Phase 3
0.7578	Intermediate Similarity	NPD1613	Approved
0.7578	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7561	Intermediate Similarity	NPD1632	Clinical (unspecified phase)
0.756	Intermediate Similarity	NPD7212	Phase 2
0.756	Intermediate Similarity	NPD7213	Phase 3
0.7552	Intermediate Similarity	NPD5005	Approved
0.7552	Intermediate Similarity	NPD5006	Approved
0.7529	Intermediate Similarity	NPD3639	Approved
0.7529	Intermediate Similarity	NPD3641	Approved
0.7529	Intermediate Similarity	NPD3640	Phase 3
0.7515	Intermediate Similarity	NPD4123	Phase 3
0.7487	Intermediate Similarity	NPD2488	Approved
0.7487	Intermediate Similarity	NPD2490	Approved
0.7486	Intermediate Similarity	NPD4581	Clinical (unspecified phase)
0.7474	Intermediate Similarity	NPD4583	Approved
0.7474	Intermediate Similarity	NPD4582	Approved
0.7471	Intermediate Similarity	NPD5772	Approved
0.7471	Intermediate Similarity	NPD5773	Approved
0.7439	Intermediate Similarity	NPD2200	Suspended
0.7438	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7423	Intermediate Similarity	NPD4002	Approved
0.7423	Intermediate Similarity	NPD4004	Approved
0.741	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD4474	Approved
0.7407	Intermediate Similarity	NPD4475	Approved
0.7396	Intermediate Similarity	NPD3845	Phase 1
0.7391	Intermediate Similarity	NPD3027	Phase 3
0.7382	Intermediate Similarity	NPD2974	Approved
0.7382	Intermediate Similarity	NPD2975	Approved
0.7382	Intermediate Similarity	NPD2973	Approved
0.7381	Intermediate Similarity	NPD6748	Discontinued
0.7371	Intermediate Similarity	NPD4585	Approved
0.7371	Intermediate Similarity	NPD2978	Approved
0.7371	Intermediate Similarity	NPD2977	Approved
0.7362	Intermediate Similarity	NPD2238	Phase 2
0.7356	Intermediate Similarity	NPD6072	Discontinued
0.7356	Intermediate Similarity	NPD5090	Approved
0.7356	Intermediate Similarity	NPD5089	Approved
0.7346	Intermediate Similarity	NPD5718	Phase 2
0.7345	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7344	Intermediate Similarity	NPD4420	Approved
0.7337	Intermediate Similarity	NPD3692	Discontinued
0.7337	Intermediate Similarity	NPD2677	Approved
0.7321	Intermediate Similarity	NPD4162	Approved
0.7321	Intermediate Similarity	NPD4237	Approved
0.7321	Intermediate Similarity	NPD3060	Approved
0.7321	Intermediate Similarity	NPD4236	Phase 3
0.7318	Intermediate Similarity	NPD6107	Approved
0.7314	Intermediate Similarity	NPD3383	Approved
0.7314	Intermediate Similarity	NPD3382	Approved
0.7314	Intermediate Similarity	NPD3384	Approved
0.7312	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7302	Intermediate Similarity	NPD3808	Clinical (unspecified phase)
0.7301	Intermediate Similarity	NPD2674	Phase 3
0.7294	Intermediate Similarity	NPD2422	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD6621	Clinical (unspecified phase)
0.7289	Intermediate Similarity	NPD1753	Discontinued
0.7284	Intermediate Similarity	NPD2669	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD6297	Approved
0.7277	Intermediate Similarity	NPD7047	Phase 3
0.7268	Intermediate Similarity	NPD4580	Approved
0.7268	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7258	Intermediate Similarity	NPD3534	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD4098	Discontinued
0.7233	Intermediate Similarity	NPD6997	Phase 2
0.7225	Intermediate Similarity	NPD2122	Discontinued
0.7219	Intermediate Similarity	NPD6853	Approved
0.7219	Intermediate Similarity	NPD6851	Approved
0.7196	Intermediate Similarity	NPD6842	Approved
0.7196	Intermediate Similarity	NPD6841	Approved
0.7196	Intermediate Similarity	NPD6843	Phase 3
0.7193	Intermediate Similarity	NPD6667	Approved
0.7193	Intermediate Similarity	NPD6666	Approved
0.7176	Intermediate Similarity	NPD3977	Clinical (unspecified phase)
0.7174	Intermediate Similarity	NPD6042	Phase 2
0.7174	Intermediate Similarity	NPD42	Phase 2
0.7171	Intermediate Similarity	NPD2899	Discontinued
0.7168	Intermediate Similarity	NPD3647	Clinical (unspecified phase)
0.7167	Intermediate Similarity	NPD4666	Phase 3
0.7166	Intermediate Similarity	NPD2971	Approved
0.7166	Intermediate Similarity	NPD2968	Approved
0.7158	Intermediate Similarity	NPD5602	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD5242	Approved
0.7135	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD5160	Discontinued
0.7134	Intermediate Similarity	NPD3145	Approved
0.7134	Intermediate Similarity	NPD3144	Approved
0.7127	Intermediate Similarity	NPD7802	Discontinued
0.7126	Intermediate Similarity	NPD6111	Discontinued
0.7126	Intermediate Similarity	NPD6895	Approved
0.7126	Intermediate Similarity	NPD6896	Approved
0.7126	Intermediate Similarity	NPD5976	Discontinued
0.7117	Intermediate Similarity	NPD4908	Phase 1
0.7112	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD5709	Phase 3
0.7097	Intermediate Similarity	NPD6996	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD4873	Discontinued
0.7081	Intermediate Similarity	NPD5312	Approved
0.7081	Intermediate Similarity	NPD5313	Approved
0.7079	Intermediate Similarity	NPD7046	Clinical (unspecified phase)
0.7079	Intermediate Similarity	NPD2801	Approved
0.7076	Intermediate Similarity	NPD6658	Clinical (unspecified phase)
0.7076	Intermediate Similarity	NPD7466	Approved
0.7073	Intermediate Similarity	NPD4625	Phase 3
0.7063	Intermediate Similarity	NPD2232	Approved
0.7063	Intermediate Similarity	NPD2233	Approved
0.7063	Intermediate Similarity	NPD2230	Approved
0.7062	Intermediate Similarity	NPD7110	Phase 1
0.7062	Intermediate Similarity	NPD7109	Clinical (unspecified phase)
0.7056	Intermediate Similarity	NPD5604	Discontinued
0.7052	Intermediate Similarity	NPD1774	Approved
0.7052	Intermediate Similarity	NPD3124	Discontinued
0.7045	Intermediate Similarity	NPD6523	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD7827	Phase 1
0.7041	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7035	Intermediate Similarity	NPD4040	Phase 1
0.7031	Intermediate Similarity	NPD5525	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD2028	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7026	Intermediate Similarity	NPD4605	Approved
0.7026	Intermediate Similarity	NPD4604	Approved
0.7022	Intermediate Similarity	NPD1934	Approved
0.7019	Intermediate Similarity	NPD7907	Approved
0.7011	Intermediate Similarity	NPD4160	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD3656	Approved
0.7	Intermediate Similarity	NPD1610	Phase 2
0.7	Intermediate Similarity	NPD1375	Discontinued
0.6995	Remote Similarity	NPD4166	Phase 2
0.6994	Remote Similarity	NPD6783	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD3687	Approved
0.6989	Remote Similarity	NPD3686	Approved
0.6989	Remote Similarity	NPD4210	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