NPASS Compound

Structure

NPC168753 OpenBabel07101718332D 23 26 0 0 1 0 0 0 0 0999 V2000 -0.8660 4.0860 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4072 0.0763 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 3.4641 2.5860 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 1.5860 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 3.0860 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.0860 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.5860 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 2.5860 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 3.0860 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.5860 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.5860 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.0860 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 2.5860 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 1.5860 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.0860 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6945 0.3345 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6945 0.3345 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 -0.8660 3.0860 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.4763 -0.2890 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4763 -0.2890 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 20 1 0 0 0 0 2 22 1 0 0 0 0 3 23 1 0 0 0 0 4 5 2 0 0 0 0 4 6 1 0 0 0 0 5 7 1 0 0 0 0 6 11 2 0 0 0 0 7 12 2 0 0 0 0 8 9 1 0 0 0 0 8 13 1 0 0 0 0 9 20 1 0 0 0 0 10 11 1 0 0 0 0 11 12 1 0 0 0 0 12 16 1 0 0 0 0 13 15 2 0 0 0 0 13 18 1 0 0 0 0 14 10 1 6 0 0 0 14 15 1 0 0 0 0 14 20 1 0 0 0 0 15 16 1 0 0 0 0 16 17 2 0 0 0 0 17 19 1 0 0 0 0 17 21 1 0 0 0 0 18 19 2 0 0 0 0 18 22 1 0 0 0 0 19 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	311.15
Volume:	324.503
LogP:	3.223
LogD:	2.696
LogS:	-1.946
# Rotatable Bonds:	2
TPSA:	41.93
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.925
Synthetic Accessibility Score:	3.039
Fsp3:	0.368
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.823
MDCK Permeability:	2.7202208002563566e-05
Pgp-inhibitor:	0.053
Pgp-substrate:	0.922
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.012

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.994
Plasma Protein Binding (PPB):	94.73834991455078%
Volume Distribution (VD):	1.475
Pgp-substrate:	4.569814205169678%

ADMET: Metabolism

CYP1A2-inhibitor:	0.584
CYP1A2-substrate:	0.963
CYP2C19-inhibitor:	0.057
CYP2C19-substrate:	0.932
CYP2C9-inhibitor:	0.02
CYP2C9-substrate:	0.811
CYP2D6-inhibitor:	0.284
CYP2D6-substrate:	0.9
CYP3A4-inhibitor:	0.119
CYP3A4-substrate:	0.913

ADMET: Excretion

Clearance (CL):	5.914
Half-life (T1/2):	0.32

ADMET: Toxicity

hERG Blockers:	0.279
Human Hepatotoxicity (H-HT):	0.149
Drug-inuced Liver Injury (DILI):	0.184
AMES Toxicity:	0.444
Rat Oral Acute Toxicity:	0.843
Maximum Recommended Daily Dose:	0.943
Skin Sensitization:	0.326
Carcinogencity:	0.059
Eye Corrosion:	0.003
Eye Irritation:	0.011
Respiratory Toxicity:	0.896

Download Data

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

Natural Product: NPC168753

Natural Product ID:	NPC168753
*Common Name:**	N-Methyisopiline
IUPAC Name:	(6aR)-2,3-dimethoxy-6-methyl-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinoline-1-ol
Synonyms:	N-Methyisopiline
Standard InCHIKey:	BIIHCZLUQVXIQY-CQSZACIVSA-N
Standard InCHI:	InChI=1S/C19H21NO3/c1-20-9-8-13-15-14(20)10-11-6-4-5-7-12(11)16(15)17(21)19(23-3)18(13)22-2/h4-7,14,21H,8-10H2,1-3H3/t14-/m1/s1
SMILES:	CN1CCc2c3[C@H]1Cc1ccccc1-c3c(c(c2OC)OC)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL519236
PubChem CID:	14140119
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0000381] Aporphines

*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
NPO10649	Guatteria ouregou	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8676127]
NPO10649	Guatteria ouregou	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	1
Others	2

Activity Type	# Activity
Individual Protein	1
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1073	Individual Protein	Dopamine transporter	Rattus norvegicus	IC50	=	46400.0	nM	PMID[530773]
NPT2	Others	Unspecified		Ratio IC50	=	0.37	n.a.	PMID[530773]
NPT2	Others	Unspecified		Ratio IC50	=	0.06	n.a.	PMID[530773]

☑ 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 NPC168753 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	353
0.1-0.2	1776
0.2-0.3	8334
0.3-0.4	9871
0.4-0.5	5446
0.5-0.6	9819
0.6-0.7	5572
0.7-0.8	1118
0.8-0.85	211
0.85-0.9	150
0.9-0.95	42
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC118274
0.981	High Similarity	NPC239775
0.9627	High Similarity	NPC476577
0.9627	High Similarity	NPC148709
0.9627	High Similarity	NPC173416
0.9509	High Similarity	NPC474507
0.9497	High Similarity	NPC145832
0.9497	High Similarity	NPC474931
0.9497	High Similarity	NPC306555
0.9497	High Similarity	NPC158376
0.9497	High Similarity	NPC12053
0.9497	High Similarity	NPC81218
0.9497	High Similarity	NPC117188
0.9497	High Similarity	NPC205421
0.9494	High Similarity	NPC136508
0.9494	High Similarity	NPC306843
0.9494	High Similarity	NPC78222
0.9494	High Similarity	NPC212794
0.9494	High Similarity	NPC96603
0.9494	High Similarity	NPC477563
0.9494	High Similarity	NPC13504
0.9494	High Similarity	NPC253043
0.9494	High Similarity	NPC196447
0.943	High Similarity	NPC324144
0.943	High Similarity	NPC1229
0.9427	High Similarity	NPC27410
0.9427	High Similarity	NPC166014
0.9193	High Similarity	NPC264850
0.9193	High Similarity	NPC13916
0.9146	High Similarity	NPC477020
0.9146	High Similarity	NPC192135
0.9146	High Similarity	NPC66341
0.9141	High Similarity	NPC26240
0.9141	High Similarity	NPC477562
0.9141	High Similarity	NPC69712
0.913	High Similarity	NPC24465
0.9123	High Similarity	NPC478093
0.9118	High Similarity	NPC82763
0.9096	High Similarity	NPC114364
0.9096	High Similarity	NPC320223
0.9091	High Similarity	NPC229166
0.9091	High Similarity	NPC128560
0.9091	High Similarity	NPC199465
0.9074	High Similarity	NPC476573
0.9074	High Similarity	NPC81247
0.9074	High Similarity	NPC35627
0.907	High Similarity	NPC30182
0.907	High Similarity	NPC473589
0.907	High Similarity	NPC478092
0.907	High Similarity	NPC478091
0.9059	High Similarity	NPC186546
0.9059	High Similarity	NPC476576
0.9057	High Similarity	NPC476572
0.9051	High Similarity	NPC99659
0.9051	High Similarity	NPC325871
0.9018	High Similarity	NPC204947
0.9006	High Similarity	NPC60186
0.9	High Similarity	NPC214116
0.8981	High Similarity	NPC326316
0.8981	High Similarity	NPC81733
0.897	High Similarity	NPC231371
0.897	High Similarity	NPC149090
0.897	High Similarity	NPC19520
0.8963	High Similarity	NPC83198
0.8963	High Similarity	NPC204908
0.8944	High Similarity	NPC230956
0.8944	High Similarity	NPC235143
0.8944	High Similarity	NPC205255
0.8944	High Similarity	NPC271388
0.8944	High Similarity	NPC119649
0.8902	High Similarity	NPC298979
0.8889	High Similarity	NPC80759
0.8889	High Similarity	NPC79402
0.8889	High Similarity	NPC57036
0.8882	High Similarity	NPC221864
0.8837	High Similarity	NPC275680
0.8837	High Similarity	NPC22115
0.8824	High Similarity	NPC116284
0.881	High Similarity	NPC112575
0.8802	High Similarity	NPC232386
0.8802	High Similarity	NPC190783
0.8802	High Similarity	NPC152680
0.878	High Similarity	NPC225774
0.8772	High Similarity	NPC135772
0.8765	High Similarity	NPC312918
0.8765	High Similarity	NPC477561
0.8765	High Similarity	NPC155442
0.8765	High Similarity	NPC286119
0.8765	High Similarity	NPC476574
0.8734	High Similarity	NPC477565
0.8734	High Similarity	NPC103379
0.8727	High Similarity	NPC476432
0.8727	High Similarity	NPC219341
0.8727	High Similarity	NPC68328
0.8727	High Similarity	NPC24264
0.8726	High Similarity	NPC191376
0.8726	High Similarity	NPC179825
0.8726	High Similarity	NPC321505
0.8721	High Similarity	NPC16357
0.8721	High Similarity	NPC302245
0.8721	High Similarity	NPC95426
0.8713	High Similarity	NPC54654
0.8713	High Similarity	NPC182052
0.8713	High Similarity	NPC311973
0.8713	High Similarity	NPC290582
0.8713	High Similarity	NPC30779
0.8713	High Similarity	NPC229373
0.8713	High Similarity	NPC217748
0.8713	High Similarity	NPC104196
0.8713	High Similarity	NPC223690
0.8713	High Similarity	NPC49075
0.8713	High Similarity	NPC328155
0.8713	High Similarity	NPC90998
0.8713	High Similarity	NPC271013
0.8713	High Similarity	NPC7715
0.8713	High Similarity	NPC181796
0.8713	High Similarity	NPC285931
0.8713	High Similarity	NPC279228
0.8713	High Similarity	NPC239824
0.8713	High Similarity	NPC8836
0.8713	High Similarity	NPC222661
0.8713	High Similarity	NPC258657
0.8713	High Similarity	NPC15414
0.8713	High Similarity	NPC42663
0.8713	High Similarity	NPC185639
0.8713	High Similarity	NPC251735
0.8713	High Similarity	NPC290005
0.8706	High Similarity	NPC126284
0.8696	High Similarity	NPC207757
0.8696	High Similarity	NPC295691
0.8696	High Similarity	NPC193949
0.8696	High Similarity	NPC278799
0.8696	High Similarity	NPC54379
0.8696	High Similarity	NPC5238
0.8696	High Similarity	NPC110416
0.8696	High Similarity	NPC172765
0.8696	High Similarity	NPC204828
0.8696	High Similarity	NPC2413
0.8696	High Similarity	NPC127674
0.8696	High Similarity	NPC39701
0.8696	High Similarity	NPC184026
0.8696	High Similarity	NPC469817
0.8696	High Similarity	NPC276588
0.8696	High Similarity	NPC189266
0.8696	High Similarity	NPC249797
0.8686	High Similarity	NPC117717
0.8678	High Similarity	NPC206900
0.8675	High Similarity	NPC247389
0.8671	High Similarity	NPC65312
0.8671	High Similarity	NPC135538
0.8671	High Similarity	NPC24233
0.8671	High Similarity	NPC147390
0.8671	High Similarity	NPC139783
0.8671	High Similarity	NPC476571
0.8671	High Similarity	NPC246587
0.8671	High Similarity	NPC428
0.8667	High Similarity	NPC167546
0.8667	High Similarity	NPC16805
0.8667	High Similarity	NPC302527
0.8663	High Similarity	NPC302275
0.8663	High Similarity	NPC274716
0.8663	High Similarity	NPC254441
0.8663	High Similarity	NPC167116
0.8655	High Similarity	NPC474506
0.8655	High Similarity	NPC32413
0.8647	High Similarity	NPC23219
0.8642	High Similarity	NPC170503
0.8642	High Similarity	NPC126519
0.8642	High Similarity	NPC203784
0.8639	High Similarity	NPC477558
0.8614	High Similarity	NPC56887
0.8614	High Similarity	NPC193853
0.8614	High Similarity	NPC223077
0.8608	High Similarity	NPC476151
0.8605	High Similarity	NPC248642
0.8599	High Similarity	NPC185838
0.8598	High Similarity	NPC160298
0.8598	High Similarity	NPC232924
0.8598	High Similarity	NPC266753
0.8598	High Similarity	NPC306902
0.8598	High Similarity	NPC477559
0.8596	High Similarity	NPC470879
0.8596	High Similarity	NPC258695
0.858	High Similarity	NPC123323
0.8563	High Similarity	NPC210918
0.8563	High Similarity	NPC116465
0.8563	High Similarity	NPC212237
0.8562	High Similarity	NPC88249
0.8562	High Similarity	NPC151895
0.8562	High Similarity	NPC192768
0.8562	High Similarity	NPC97221
0.8562	High Similarity	NPC220858
0.8555	High Similarity	NPC156576
0.8554	High Similarity	NPC209377
0.8529	High Similarity	NPC329969
0.8528	High Similarity	NPC186063
0.8503	High Similarity	NPC124657
0.8488	Intermediate Similarity	NPC32154
0.8466	Intermediate Similarity	NPC48490
0.8466	Intermediate Similarity	NPC11296

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 NPC168753 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	215
0.1-0.2	833
0.2-0.3	1090
0.3-0.4	2146
0.4-0.5	2570
0.5-0.6	1587
0.6-0.7	557
0.7-0.8	132
0.8-0.85	16
0.85-0.9	4
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8713	High Similarity	NPD8053	Approved
0.8713	High Similarity	NPD8054	Approved
0.8662	High Similarity	NPD2421	Approved
0.8662	High Similarity	NPD2420	Approved
0.8402	Intermediate Similarity	NPD2489	Approved
0.8402	Intermediate Similarity	NPD27	Approved
0.8393	Intermediate Similarity	NPD3051	Approved
0.8352	Intermediate Similarity	NPD7906	Approved
0.8343	Intermediate Similarity	NPD2970	Approved
0.8343	Intermediate Similarity	NPD2969	Approved
0.8333	Intermediate Similarity	NPD4577	Approved
0.8333	Intermediate Similarity	NPD4578	Approved
0.8313	Intermediate Similarity	NPD6788	Approved
0.8304	Intermediate Similarity	NPD8251	Approved
0.8304	Intermediate Similarity	NPD8252	Approved
0.8304	Intermediate Similarity	NPD8099	Discontinued
0.8261	Intermediate Similarity	NPD4584	Approved
0.8256	Intermediate Similarity	NPD8156	Discontinued
0.8228	Intermediate Similarity	NPD4664	Clinical (unspecified phase)
0.8192	Intermediate Similarity	NPD4663	Approved
0.8125	Intermediate Similarity	NPD7311	Approved
0.8125	Intermediate Similarity	NPD7310	Approved
0.8125	Intermediate Similarity	NPD7313	Approved
0.8125	Intermediate Similarity	NPD7312	Approved
0.8081	Intermediate Similarity	NPD2898	Approved
0.8079	Intermediate Similarity	NPD7309	Approved
0.7976	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.7966	Intermediate Similarity	NPD8453	Clinical (unspecified phase)
0.7963	Intermediate Similarity	NPD5241	Discontinued
0.7953	Intermediate Similarity	NPD7201	Clinical (unspecified phase)
0.7914	Intermediate Similarity	NPD3845	Phase 1
0.7914	Intermediate Similarity	NPD2422	Clinical (unspecified phase)
0.7861	Intermediate Similarity	NPD4010	Discontinued
0.7857	Intermediate Similarity	NPD2490	Approved
0.7857	Intermediate Similarity	NPD2488	Approved
0.7844	Intermediate Similarity	NPD7261	Clinical (unspecified phase)
0.7836	Intermediate Similarity	NPD4055	Discovery
0.7836	Intermediate Similarity	NPD7831	Phase 2
0.7836	Intermediate Similarity	NPD7833	Phase 2
0.7836	Intermediate Similarity	NPD7832	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD4481	Phase 3
0.7766	Intermediate Similarity	NPD3452	Approved
0.7766	Intermediate Similarity	NPD2493	Approved
0.7766	Intermediate Similarity	NPD3450	Approved
0.7766	Intermediate Similarity	NPD2494	Approved
0.7759	Intermediate Similarity	NPD6071	Discontinued
0.7738	Intermediate Similarity	NPD4017	Approved
0.7722	Intermediate Similarity	NPD3534	Clinical (unspecified phase)
0.7719	Intermediate Similarity	NPD2563	Approved
0.7719	Intermediate Similarity	NPD2560	Approved
0.7711	Intermediate Similarity	NPD1424	Approved
0.7711	Intermediate Similarity	NPD1754	Clinical (unspecified phase)
0.7674	Intermediate Similarity	NPD4581	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD4773	Phase 2
0.7647	Intermediate Similarity	NPD4772	Phase 2
0.7644	Intermediate Similarity	NPD4582	Approved
0.7644	Intermediate Similarity	NPD4583	Approved
0.7636	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7602	Intermediate Similarity	NPD7298	Approved
0.7592	Intermediate Similarity	NPD4002	Approved
0.7592	Intermediate Similarity	NPD4004	Approved
0.7562	Intermediate Similarity	NPD3110	Approved
0.7562	Intermediate Similarity	NPD3109	Approved
0.7553	Intermediate Similarity	NPD2975	Approved
0.7553	Intermediate Similarity	NPD2973	Approved
0.7553	Intermediate Similarity	NPD2974	Approved
0.7529	Intermediate Similarity	NPD4005	Discontinued
0.7527	Intermediate Similarity	NPD2971	Approved
0.7527	Intermediate Similarity	NPD2968	Approved
0.7515	Intermediate Similarity	NPD3641	Approved
0.7515	Intermediate Similarity	NPD3639	Approved
0.7515	Intermediate Similarity	NPD5177	Phase 3
0.7515	Intermediate Similarity	NPD3640	Phase 3
0.7485	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD7124	Phase 2
0.7474	Intermediate Similarity	NPD8095	Phase 1
0.7437	Intermediate Similarity	NPD7047	Phase 3
0.7435	Intermediate Similarity	NPD4580	Approved
0.7412	Intermediate Similarity	NPD6030	Approved
0.7412	Intermediate Similarity	NPD6031	Approved
0.7407	Intermediate Similarity	NPD7667	Clinical (unspecified phase)
0.7396	Intermediate Similarity	NPD7447	Phase 1
0.7391	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD6997	Phase 2
0.7375	Intermediate Similarity	NPD5155	Approved
0.7375	Intermediate Similarity	NPD5156	Approved
0.7363	Intermediate Similarity	NPD6996	Clinical (unspecified phase)
0.7337	Intermediate Similarity	NPD7213	Phase 3
0.7337	Intermediate Similarity	NPD7212	Phase 2
0.7333	Intermediate Similarity	NPD5602	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD1632	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD5718	Phase 2
0.7321	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD3594	Approved
0.7312	Intermediate Similarity	NPD2605	Approved
0.7312	Intermediate Similarity	NPD3595	Approved
0.7312	Intermediate Similarity	NPD2606	Approved
0.7289	Intermediate Similarity	NPD4725	Approved
0.7289	Intermediate Similarity	NPD4726	Approved
0.7289	Intermediate Similarity	NPD4721	Approved
0.7286	Intermediate Similarity	NPD7827	Phase 1
0.7284	Intermediate Similarity	NPD2674	Phase 3
0.7283	Intermediate Similarity	NPD4678	Approved
0.7283	Intermediate Similarity	NPD4675	Approved
0.7283	Intermediate Similarity	NPD7549	Discontinued
0.7282	Intermediate Similarity	NPD4040	Phase 1
0.7273	Intermediate Similarity	NPD1753	Discontinued
0.7267	Intermediate Similarity	NPD2669	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD3636	Approved
0.725	Intermediate Similarity	NPD3635	Approved
0.725	Intermediate Similarity	NPD3637	Approved
0.7247	Intermediate Similarity	NPD5677	Discontinued
0.7207	Intermediate Similarity	NPD7802	Discontinued
0.7202	Intermediate Similarity	NPD3060	Approved
0.7186	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD3057	Approved
0.7179	Intermediate Similarity	NPD3448	Approved
0.7179	Intermediate Similarity	NPD2491	Approved
0.7179	Intermediate Similarity	NPD5006	Approved
0.7179	Intermediate Similarity	NPD5005	Approved
0.7178	Intermediate Similarity	NPD4475	Approved
0.7178	Intermediate Similarity	NPD4474	Approved
0.7174	Intermediate Similarity	NPD6297	Approved
0.716	Intermediate Similarity	NPD4625	Phase 3
0.716	Intermediate Similarity	NPD3027	Phase 3
0.7159	Intermediate Similarity	NPD4585	Approved
0.7159	Intermediate Similarity	NPD2978	Approved
0.7159	Intermediate Similarity	NPD2977	Approved
0.7158	Intermediate Similarity	NPD42	Phase 2
0.7158	Intermediate Similarity	NPD6042	Phase 2
0.7151	Intermediate Similarity	NPD6090	Discontinued
0.7143	Intermediate Similarity	NPD5090	Approved
0.7143	Intermediate Similarity	NPD6072	Discontinued
0.7143	Intermediate Similarity	NPD5089	Approved
0.7135	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD3124	Discontinued
0.7134	Intermediate Similarity	NPD2238	Phase 2
0.7117	Intermediate Similarity	NPD3145	Approved
0.7117	Intermediate Similarity	NPD3144	Approved
0.7108	Intermediate Similarity	NPD2200	Suspended
0.7108	Intermediate Similarity	NPD6111	Discontinued
0.7108	Intermediate Similarity	NPD7718	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7093	Intermediate Similarity	NPD4160	Clinical (unspecified phase)
0.7092	Intermediate Similarity	NPD3533	Approved
0.7092	Intermediate Similarity	NPD2972	Approved
0.7087	Intermediate Similarity	NPD7907	Approved
0.7077	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7076	Intermediate Similarity	NPD6667	Approved
0.7076	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.7076	Intermediate Similarity	NPD6666	Approved
0.7062	Intermediate Similarity	NPD4420	Approved
0.7059	Intermediate Similarity	NPD5917	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD5754	Discontinued
0.7056	Intermediate Similarity	NPD4666	Phase 3
0.7041	Intermediate Similarity	NPD4256	Phase 2
0.7041	Intermediate Similarity	NPD4257	Approved
0.7037	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7035	Intermediate Similarity	NPD7598	Phase 2
0.703	Intermediate Similarity	NPD1613	Approved
0.703	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7029	Intermediate Similarity	NPD6523	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD7479	Phase 2
0.7026	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD6853	Approved
0.7021	Intermediate Similarity	NPD6851	Approved
0.7018	Intermediate Similarity	NPD5160	Discontinued
0.7017	Intermediate Similarity	NPD6107	Approved
0.7012	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD5976	Discontinued
0.7006	Intermediate Similarity	NPD6896	Approved
0.7006	Intermediate Similarity	NPD6895	Approved
0.7	Intermediate Similarity	NPD4236	Phase 3
0.7	Intermediate Similarity	NPD5709	Phase 3
0.7	Intermediate Similarity	NPD4237	Approved
0.6995	Remote Similarity	NPD6723	Discontinued
0.6994	Remote Similarity	NPD4123	Phase 3
0.699	Remote Similarity	NPD4111	Phase 1
0.699	Remote Similarity	NPD4665	Approved
0.6978	Remote Similarity	NPD4166	Phase 2
0.6973	Remote Similarity	NPD4873	Discontinued
0.6959	Remote Similarity	NPD7466	Approved
0.6959	Remote Similarity	NPD6748	Discontinued
0.6954	Remote Similarity	NPD5261	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD3647	Clinical (unspecified phase)
0.6946	Remote Similarity	NPD4579	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD5604	Discontinued
0.6943	Remote Similarity	NPD2226	Clinical (unspecified phase)
0.6941	Remote Similarity	NPD7037	Approved
0.6927	Remote Similarity	NPD6656	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD5978	Approved
0.6927	Remote Similarity	NPD5977	Approved
0.6919	Remote Similarity	NPD3692	Discontinued
0.6915	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD3055	Approved
0.6914	Remote Similarity	NPD2122	Discontinued
0.6914	Remote Similarity	NPD1914	Approved
0.6914	Remote Similarity	NPD4727	Phase 1

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