NPASS Compound

Structure

CID8337 OpenBabel06191715332D 25 28 0 0 1 0 0 0 0 0999 V2000 -4.6916 1.5037 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6042 0.9268 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8025 -1.3893 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9249 -2.7784 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9943 0.8014 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9945 1.7279 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4070 0.4626 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8026 1.3895 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3323 -1.3903 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8022 -0.4634 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7285 -0.4631 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6048 0.9261 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6046 -0.0004 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3329 -0.4640 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3331 0.4624 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5299 -1.8530 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0002 0.9264 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 -1.7279 -1.3894 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5309 -0.0004 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.7967 1.2644 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.5294 -2.7793 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8019 1.3898 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8023 -0.4630 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9255 -1.8521 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 21 1 0 0 0 0 2 23 1 0 0 0 0 3 24 1 0 0 0 0 4 25 1 0 0 0 0 5 6 1 0 0 0 0 6 21 1 0 0 0 0 7 12 1 0 0 0 0 8 12 2 0 0 0 0 8 17 1 0 0 0 0 9 14 2 0 0 0 0 9 16 1 0 0 0 0 10 13 2 0 0 0 0 10 18 1 0 0 0 0 11 19 2 0 0 0 0 11 20 1 0 0 0 0 12 13 1 0 0 0 0 13 20 1 0 0 0 0 14 15 1 0 0 0 0 14 20 1 0 0 0 0 15 7 1 1 0 0 0 15 21 1 0 0 0 0 16 19 1 0 0 0 0 16 22 2 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 25 1 0 0 0 0 20 5 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	341.16
Volume:	350.589
LogP:	1.422
LogD:	1.425
LogS:	-2.101
# Rotatable Bonds:	3
TPSA:	48.0
# H-Bond Aceptor:	5
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.844
Synthetic Accessibility Score:	4.346
Fsp3:	0.45
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.662
MDCK Permeability:	2.0549639884848148e-05
Pgp-inhibitor:	0.019
Pgp-substrate:	0.121
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	0.977
30% Bioavailability (F30%):	0.933

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.994
Plasma Protein Binding (PPB):	58.864967346191406%
Volume Distribution (VD):	1.902
Pgp-substrate:	30.334747314453125%

ADMET: Metabolism

CYP1A2-inhibitor:	0.048
CYP1A2-substrate:	0.945
CYP2C19-inhibitor:	0.161
CYP2C19-substrate:	0.948
CYP2C9-inhibitor:	0.04
CYP2C9-substrate:	0.331
CYP2D6-inhibitor:	0.082
CYP2D6-substrate:	0.808
CYP3A4-inhibitor:	0.098
CYP3A4-substrate:	0.938

ADMET: Excretion

Clearance (CL):	9.718
Half-life (T1/2):	0.649

ADMET: Toxicity

hERG Blockers:	0.113
Human Hepatotoxicity (H-HT):	0.611
Drug-inuced Liver Injury (DILI):	0.067
AMES Toxicity:	0.018
Rat Oral Acute Toxicity:	0.522
Maximum Recommended Daily Dose:	0.901
Skin Sensitization:	0.269
Carcinogencity:	0.895
Eye Corrosion:	0.003
Eye Irritation:	0.008
Respiratory Toxicity:	0.985

Download Data

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

Natural Product: NPC8337

Natural Product ID:	NPC8337
*Common Name:**	DBPGJIUVRZHFCM-YWZLYKJASA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	DBPGJIUVRZHFCM-YWZLYKJASA-N
Standard InCHI:	InChI=1S/C20H23NO4/c1-21-6-5-20-11-19(25-4)16(22)9-14(20)15(21)7-12-8-17(23-2)18(24-3)10-13(12)20/h8-11,15H,5-7H2,1-4H3/t15-,20-/m0/s1
SMILES:	CN1CC[C@]23C=C(C(=O)C=C3[C@@H]1Cc1cc(c(cc21)OC)OC)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL224744
PubChem CID:	10405046
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000025] Phenanthrenes 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
NPO18509	Fissistigma oldhamii	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10978218]
NPO4041	Guatteria multivenia	Species	Annonaceae	Eukaryota	Roots	n.a.	n.a.	PMID[12088427]
NPO18509	Fissistigma oldhamii	Species	Annonaceae	Eukaryota	stem	n.a.	n.a.	PMID[17081761]
NPO3079	Cassytha filiformis	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18217715]
NPO12425	Combretum griffithii	Species	Combretaceae	Eukaryota	n.a.	stem	n.a.	PMID[21919533]
NPO1168	Euphorbia sikkimensis	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23327832]
NPO12425	Combretum griffithii	Species	Combretaceae	Eukaryota	Stems	n.a.	n.a.	PMID[23795891]
NPO1168	Euphorbia sikkimensis	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26756779]
NPO3079	Cassytha filiformis	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[Article]
NPO3079	Cassytha filiformis	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9266	Stephania delavayi	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3371	Podocarpus nubigenus	Species	Podocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9266	Stephania delavayi	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3079	Cassytha filiformis	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3371	Podocarpus nubigenus	Species	Podocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9266	Stephania delavayi	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO3371	Podocarpus nubigenus	Species	Podocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO2292	Teclea verdoorniana	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4563	Clinopodium acinos	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12425	Combretum griffithii	Species	Combretaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4041	Guatteria multivenia	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7993	Euclea pseudebenus	Species	Ebenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13101	Passiflora hybrid	Species	Passifloraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12769	Hosta sieboldii	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1798	Duguetia obovata	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9266	Stephania delavayi	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4973	Cirsium rivulare	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3079	Cassytha filiformis	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1168	Euphorbia sikkimensis	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6236	Polymastia boletiformis	Species	Polymastiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3371	Podocarpus nubigenus	Species	Podocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18509	Fissistigma oldhamii	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10358	Bupleurum gerardi	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10562	Aglaia archboldiana	Species	Meliaceae	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	3
Others	3

Activity Type	# Activity
Cell Line	1
Others	4
Tissue	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1076	Cell Line	B-cells		IC50	=	3970.0	nM	PMID[510674]
NPT27	Others	Unspecified		CC50	=	58900.0	nM	PMID[510674]
NPT2	Others	Unspecified		IC50	=	39300.0	nM	PMID[510674]
NPT2	Others	Unspecified		Ratio CC50/IC50	=	1.0	n.a.	PMID[510674]
NPT2	Others	Unspecified		Ratio CC50/IC50	=	15.0	n.a.	PMID[510674]
NPT177	Tissue	Aorta	Rattus norvegicus	IC50	=	28900.0	nM	PMID[510675]

☑ 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 NPC8337 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	285
0.1-0.2	1602
0.2-0.3	5430
0.3-0.4	12181
0.4-0.5	5507
0.5-0.6	14279
0.6-0.7	2791
0.7-0.8	567
0.8-0.85	47
0.85-0.9	2
0.9-0.95	2
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC85747
0.953	High Similarity	NPC226428
0.9342	High Similarity	NPC3375
0.9342	High Similarity	NPC255607
0.906	High Similarity	NPC476579
0.8896	High Similarity	NPC475780
0.875	High Similarity	NPC476580
0.8598	High Similarity	NPC298339
0.859	High Similarity	NPC118804
0.859	High Similarity	NPC106786
0.8581	High Similarity	NPC57512
0.8544	High Similarity	NPC476569
0.8544	High Similarity	NPC59567
0.8523	High Similarity	NPC136860
0.8523	High Similarity	NPC128019
0.8523	High Similarity	NPC476567
0.8514	High Similarity	NPC188163
0.8514	High Similarity	NPC474915
0.8514	High Similarity	NPC328750
0.8514	High Similarity	NPC213206
0.8462	Intermediate Similarity	NPC323443
0.8462	Intermediate Similarity	NPC180756
0.8446	Intermediate Similarity	NPC314682
0.8333	Intermediate Similarity	NPC214629
0.8323	Intermediate Similarity	NPC81733
0.8323	Intermediate Similarity	NPC326316
0.8301	Intermediate Similarity	NPC476144
0.8301	Intermediate Similarity	NPC51957
0.8301	Intermediate Similarity	NPC106295
0.8301	Intermediate Similarity	NPC16107
0.8301	Intermediate Similarity	NPC210437
0.828	Intermediate Similarity	NPC325871
0.828	Intermediate Similarity	NPC99659
0.8261	Intermediate Similarity	NPC2770
0.8261	Intermediate Similarity	NPC39103
0.8247	Intermediate Similarity	NPC7467
0.8221	Intermediate Similarity	NPC470324
0.8205	Intermediate Similarity	NPC218575
0.8204	Intermediate Similarity	NPC149285
0.8176	Intermediate Similarity	NPC476572
0.817	Intermediate Similarity	NPC185838
0.8163	Intermediate Similarity	NPC325568
0.8148	Intermediate Similarity	NPC306669
0.8141	Intermediate Similarity	NPC97221
0.8141	Intermediate Similarity	NPC192768
0.8141	Intermediate Similarity	NPC151895
0.8141	Intermediate Similarity	NPC220858
0.8141	Intermediate Similarity	NPC88249
0.8141	Intermediate Similarity	NPC223125
0.8129	Intermediate Similarity	NPC428
0.8129	Intermediate Similarity	NPC24233
0.8129	Intermediate Similarity	NPC135538
0.8129	Intermediate Similarity	NPC476571
0.8129	Intermediate Similarity	NPC130941
0.8129	Intermediate Similarity	NPC147390
0.8129	Intermediate Similarity	NPC246587
0.8129	Intermediate Similarity	NPC475959
0.8098	Intermediate Similarity	NPC124657
0.8089	Intermediate Similarity	NPC476568
0.8082	Intermediate Similarity	NPC160193
0.8077	Intermediate Similarity	NPC219162
0.8077	Intermediate Similarity	NPC92541
0.8065	Intermediate Similarity	NPC191376
0.8065	Intermediate Similarity	NPC179825
0.8065	Intermediate Similarity	NPC321505
0.8054	Intermediate Similarity	NPC11147
0.8052	Intermediate Similarity	NPC130926
0.8049	Intermediate Similarity	NPC471604
0.8047	Intermediate Similarity	NPC115906
0.8038	Intermediate Similarity	NPC210148
0.8038	Intermediate Similarity	NPC470924
0.8038	Intermediate Similarity	NPC223124
0.8038	Intermediate Similarity	NPC233029
0.8026	Intermediate Similarity	NPC470925
0.8	Intermediate Similarity	NPC170503
0.8	Intermediate Similarity	NPC203784
0.8	Intermediate Similarity	NPC126519
0.7975	Intermediate Similarity	NPC324144
0.7964	Intermediate Similarity	NPC4669
0.7963	Intermediate Similarity	NPC166014
0.7963	Intermediate Similarity	NPC266753
0.7963	Intermediate Similarity	NPC160298
0.7963	Intermediate Similarity	NPC27410
0.7963	Intermediate Similarity	NPC232924
0.7963	Intermediate Similarity	NPC306902
0.7963	Intermediate Similarity	NPC477559
0.7955	Intermediate Similarity	NPC279665
0.7949	Intermediate Similarity	NPC144863
0.7949	Intermediate Similarity	NPC90844
0.7949	Intermediate Similarity	NPC476151
0.7949	Intermediate Similarity	NPC253883
0.7949	Intermediate Similarity	NPC95075
0.7947	Intermediate Similarity	NPC253429
0.7937	Intermediate Similarity	NPC184026
0.7937	Intermediate Similarity	NPC278799
0.7937	Intermediate Similarity	NPC2413
0.7937	Intermediate Similarity	NPC193949
0.7937	Intermediate Similarity	NPC127674
0.7937	Intermediate Similarity	NPC216459
0.7937	Intermediate Similarity	NPC204828
0.7937	Intermediate Similarity	NPC187022
0.7937	Intermediate Similarity	NPC189266
0.7937	Intermediate Similarity	NPC276588
0.7937	Intermediate Similarity	NPC207757
0.7937	Intermediate Similarity	NPC54379
0.7937	Intermediate Similarity	NPC5238
0.7937	Intermediate Similarity	NPC469817
0.7937	Intermediate Similarity	NPC249797
0.7937	Intermediate Similarity	NPC41178
0.7937	Intermediate Similarity	NPC39701
0.7937	Intermediate Similarity	NPC172765
0.7937	Intermediate Similarity	NPC78733
0.7937	Intermediate Similarity	NPC295691
0.7937	Intermediate Similarity	NPC110416
0.7937	Intermediate Similarity	NPC138487
0.7937	Intermediate Similarity	NPC80129
0.7929	Intermediate Similarity	NPC21885
0.7927	Intermediate Similarity	NPC16805
0.7927	Intermediate Similarity	NPC167546
0.7927	Intermediate Similarity	NPC78222
0.7927	Intermediate Similarity	NPC196447
0.7927	Intermediate Similarity	NPC136508
0.7927	Intermediate Similarity	NPC477563
0.7927	Intermediate Similarity	NPC212794
0.7927	Intermediate Similarity	NPC306843
0.7927	Intermediate Similarity	NPC13504
0.7927	Intermediate Similarity	NPC96603
0.7927	Intermediate Similarity	NPC302527
0.7927	Intermediate Similarity	NPC253043
0.7892	Intermediate Similarity	NPC241055
0.7888	Intermediate Similarity	NPC25084
0.7888	Intermediate Similarity	NPC147091
0.7888	Intermediate Similarity	NPC190931
0.7888	Intermediate Similarity	NPC146288
0.7888	Intermediate Similarity	NPC247639
0.7881	Intermediate Similarity	NPC42793
0.7881	Intermediate Similarity	NPC167944
0.7881	Intermediate Similarity	NPC231884
0.7879	Intermediate Similarity	NPC476432
0.7879	Intermediate Similarity	NPC24264
0.787	Intermediate Similarity	NPC241704
0.7852	Intermediate Similarity	NPC118419
0.7848	Intermediate Similarity	NPC207824
0.7848	Intermediate Similarity	NPC477565
0.7848	Intermediate Similarity	NPC103379
0.7848	Intermediate Similarity	NPC60538
0.7831	Intermediate Similarity	NPC210918
0.7831	Intermediate Similarity	NPC306555
0.7831	Intermediate Similarity	NPC12053
0.7831	Intermediate Similarity	NPC247389
0.7831	Intermediate Similarity	NPC81218
0.7831	Intermediate Similarity	NPC474931
0.7831	Intermediate Similarity	NPC145832
0.7831	Intermediate Similarity	NPC158376
0.7831	Intermediate Similarity	NPC117188
0.7831	Intermediate Similarity	NPC205421
0.7829	Intermediate Similarity	NPC196231
0.7826	Intermediate Similarity	NPC244112
0.7818	Intermediate Similarity	NPC231198
0.7818	Intermediate Similarity	NPC225774
0.7812	Intermediate Similarity	NPC37272
0.7799	Intermediate Similarity	NPC274026
0.7791	Intermediate Similarity	NPC216816
0.7791	Intermediate Similarity	NPC477080
0.7791	Intermediate Similarity	NPC111485
0.7778	Intermediate Similarity	NPC234392
0.7778	Intermediate Similarity	NPC32154
0.7778	Intermediate Similarity	NPC31311
0.7778	Intermediate Similarity	NPC186063
0.7771	Intermediate Similarity	NPC219341
0.775	Intermediate Similarity	NPC277669
0.775	Intermediate Similarity	NPC76213
0.7744	Intermediate Similarity	NPC205167
0.7735	Intermediate Similarity	NPC244191
0.7725	Intermediate Similarity	NPC474324
0.7725	Intermediate Similarity	NPC298979
0.7725	Intermediate Similarity	NPC57812
0.7725	Intermediate Similarity	NPC204947
0.7711	Intermediate Similarity	NPC168409
0.7703	Intermediate Similarity	NPC172403
0.7702	Intermediate Similarity	NPC133011
0.7702	Intermediate Similarity	NPC148898
0.7702	Intermediate Similarity	NPC26601
0.7702	Intermediate Similarity	NPC82285
0.7697	Intermediate Similarity	NPC174783
0.7692	Intermediate Similarity	NPC149090
0.7692	Intermediate Similarity	NPC19520
0.7692	Intermediate Similarity	NPC239775
0.7682	Intermediate Similarity	NPC160692
0.7679	Intermediate Similarity	NPC475845
0.7674	Intermediate Similarity	NPC220961
0.7665	Intermediate Similarity	NPC35627
0.7665	Intermediate Similarity	NPC86144
0.7665	Intermediate Similarity	NPC304659
0.7665	Intermediate Similarity	NPC476573
0.7665	Intermediate Similarity	NPC81247
0.7662	Intermediate Similarity	NPC231572
0.7661	Intermediate Similarity	NPC222524
0.7661	Intermediate Similarity	NPC35680
0.7654	Intermediate Similarity	NPC14005

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 NPC8337 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	188
0.1-0.2	774
0.2-0.3	961
0.3-0.4	2295
0.4-0.5	2592
0.5-0.6	1681
0.6-0.7	523
0.7-0.8	124
0.8-0.85	11
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8598	High Similarity	NPD3534	Clinical (unspecified phase)
0.8514	High Similarity	NPD4664	Clinical (unspecified phase)
0.8301	Intermediate Similarity	NPD4584	Approved
0.8221	Intermediate Similarity	NPD2898	Approved
0.8221	Intermediate Similarity	NPD4481	Phase 3
0.8194	Intermediate Similarity	NPD3641	Approved
0.8194	Intermediate Similarity	NPD3640	Phase 3
0.8194	Intermediate Similarity	NPD3639	Approved
0.8163	Intermediate Similarity	NPD3110	Approved
0.8163	Intermediate Similarity	NPD3109	Approved
0.8082	Intermediate Similarity	NPD2669	Clinical (unspecified phase)
0.8047	Intermediate Similarity	NPD2971	Approved
0.8047	Intermediate Similarity	NPD2968	Approved
0.7987	Intermediate Similarity	NPD5241	Discontinued
0.7939	Intermediate Similarity	NPD2969	Approved
0.7939	Intermediate Similarity	NPD2970	Approved
0.7937	Intermediate Similarity	NPD7298	Approved
0.7905	Intermediate Similarity	NPD5718	Phase 2
0.7892	Intermediate Similarity	NPD27	Approved
0.7892	Intermediate Similarity	NPD2489	Approved
0.7888	Intermediate Similarity	NPD4585	Approved
0.7881	Intermediate Similarity	NPD6895	Approved
0.7881	Intermediate Similarity	NPD6896	Approved
0.7879	Intermediate Similarity	NPD3051	Approved
0.7862	Intermediate Similarity	NPD4017	Approved
0.7829	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7829	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD2490	Approved
0.7771	Intermediate Similarity	NPD2488	Approved
0.773	Intermediate Similarity	NPD5977	Approved
0.773	Intermediate Similarity	NPD5978	Approved
0.7722	Intermediate Similarity	NPD4107	Approved
0.7673	Intermediate Similarity	NPD3647	Clinical (unspecified phase)
0.7654	Intermediate Similarity	NPD5089	Approved
0.7654	Intermediate Similarity	NPD5090	Approved
0.7654	Intermediate Similarity	NPD2975	Approved
0.7654	Intermediate Similarity	NPD4773	Phase 2
0.7654	Intermediate Similarity	NPD2973	Approved
0.7654	Intermediate Similarity	NPD2974	Approved
0.7654	Intermediate Similarity	NPD4772	Phase 2
0.7651	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7625	Intermediate Similarity	NPD4727	Phase 1
0.7625	Intermediate Similarity	NPD6030	Approved
0.7625	Intermediate Similarity	NPD6031	Approved
0.7605	Intermediate Similarity	NPD6107	Approved
0.7582	Intermediate Similarity	NPD4482	Phase 3
0.7546	Intermediate Similarity	NPD7109	Clinical (unspecified phase)
0.7546	Intermediate Similarity	NPD7110	Phase 1
0.7546	Intermediate Similarity	NPD6873	Phase 2
0.7545	Intermediate Similarity	NPD7201	Clinical (unspecified phase)
0.7541	Intermediate Similarity	NPD3057	Approved
0.7532	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.7529	Intermediate Similarity	NPD7313	Approved
0.7529	Intermediate Similarity	NPD7311	Approved
0.7529	Intermediate Similarity	NPD7310	Approved
0.7529	Intermediate Similarity	NPD7312	Approved
0.7527	Intermediate Similarity	NPD4580	Approved
0.7486	Intermediate Similarity	NPD2494	Approved
0.7486	Intermediate Similarity	NPD3452	Approved
0.7486	Intermediate Similarity	NPD3450	Approved
0.7486	Intermediate Similarity	NPD2493	Approved
0.7486	Intermediate Similarity	NPD7309	Approved
0.7484	Intermediate Similarity	NPD7124	Phase 2
0.7468	Intermediate Similarity	NPD2492	Phase 1
0.7458	Intermediate Similarity	NPD7906	Approved
0.7456	Intermediate Similarity	NPD4166	Phase 2
0.7456	Intermediate Similarity	NPD4010	Discontinued
0.7446	Intermediate Similarity	NPD3533	Approved
0.7446	Intermediate Similarity	NPD2972	Approved
0.7438	Intermediate Similarity	NPD3124	Discontinued
0.7427	Intermediate Similarity	NPD5602	Clinical (unspecified phase)
0.7425	Intermediate Similarity	NPD7833	Phase 2
0.7425	Intermediate Similarity	NPD7832	Clinical (unspecified phase)
0.7425	Intermediate Similarity	NPD7831	Phase 2
0.7407	Intermediate Similarity	NPD6662	Clinical (unspecified phase)
0.7384	Intermediate Similarity	NPD8099	Discontinued
0.7384	Intermediate Similarity	NPD8251	Approved
0.7384	Intermediate Similarity	NPD8252	Approved
0.7378	Intermediate Similarity	NPD6875	Approved
0.7378	Intermediate Similarity	NPD6876	Approved
0.7375	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.7366	Intermediate Similarity	NPD4582	Approved
0.7366	Intermediate Similarity	NPD4583	Approved
0.736	Intermediate Similarity	NPD7291	Discontinued
0.7358	Intermediate Similarity	NPD5754	Discontinued
0.7351	Intermediate Similarity	NPD3448	Approved
0.7351	Intermediate Similarity	NPD3637	Approved
0.7351	Intermediate Similarity	NPD3635	Approved
0.7351	Intermediate Similarity	NPD2491	Approved
0.7351	Intermediate Similarity	NPD3636	Approved
0.7349	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.7341	Intermediate Similarity	NPD5313	Approved
0.7341	Intermediate Similarity	NPD8156	Discontinued
0.7341	Intermediate Similarity	NPD5312	Approved
0.733	Intermediate Similarity	NPD4578	Approved
0.733	Intermediate Similarity	NPD4577	Approved
0.7329	Intermediate Similarity	NPD2421	Approved
0.7329	Intermediate Similarity	NPD2420	Approved
0.7312	Intermediate Similarity	NPD4002	Approved
0.7312	Intermediate Similarity	NPD4004	Approved
0.731	Intermediate Similarity	NPD6687	Approved
0.731	Intermediate Similarity	NPD6688	Approved
0.7303	Intermediate Similarity	NPD3594	Approved
0.7303	Intermediate Similarity	NPD2605	Approved
0.7303	Intermediate Similarity	NPD2606	Approved
0.7303	Intermediate Similarity	NPD4663	Approved
0.7303	Intermediate Similarity	NPD3595	Approved
0.7294	Intermediate Similarity	NPD7802	Discontinued
0.7285	Intermediate Similarity	NPD7905	Discontinued
0.7284	Intermediate Similarity	NPD1754	Clinical (unspecified phase)
0.7262	Intermediate Similarity	NPD6788	Approved
0.7261	Intermediate Similarity	NPD1753	Discontinued
0.7257	Intermediate Similarity	NPD6297	Approved
0.7255	Intermediate Similarity	NPD5156	Approved
0.7255	Intermediate Similarity	NPD5155	Approved
0.7251	Intermediate Similarity	NPD6071	Discontinued
0.725	Intermediate Similarity	NPD6658	Clinical (unspecified phase)
0.7247	Intermediate Similarity	NPD5087	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD4579	Clinical (unspecified phase)
0.7229	Intermediate Similarity	NPD6386	Approved
0.7229	Intermediate Similarity	NPD6385	Approved
0.7225	Intermediate Similarity	NPD5676	Approved
0.7202	Intermediate Similarity	NPD2560	Approved
0.7202	Intermediate Similarity	NPD2563	Approved
0.7197	Intermediate Similarity	NPD6111	Discontinued
0.7191	Intermediate Similarity	NPD6618	Phase 2
0.7181	Intermediate Similarity	NPD4040	Phase 1
0.7161	Intermediate Similarity	NPD554	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD2422	Clinical (unspecified phase)
0.7158	Intermediate Similarity	NPD4859	Phase 1
0.7143	Intermediate Similarity	NPD42	Phase 2
0.7143	Intermediate Similarity	NPD6042	Phase 2
0.7135	Intermediate Similarity	NPD5917	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD2653	Approved
0.7128	Intermediate Similarity	NPD5980	Discovery
0.7117	Intermediate Similarity	NPD5297	Approved
0.7108	Intermediate Similarity	NPD4005	Discontinued
0.7099	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD6812	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD8054	Approved
0.7095	Intermediate Similarity	NPD8053	Approved
0.7095	Intermediate Similarity	NPD6851	Approved
0.7095	Intermediate Similarity	NPD6853	Approved
0.7081	Intermediate Similarity	NPD3060	Approved
0.7081	Intermediate Similarity	NPD4162	Approved
0.7081	Intermediate Similarity	NPD4236	Phase 3
0.7081	Intermediate Similarity	NPD4237	Approved
0.7081	Intermediate Similarity	NPD5177	Phase 3
0.7075	Intermediate Similarity	NPD5536	Phase 2
0.7071	Intermediate Similarity	NPD7907	Approved
0.7066	Intermediate Similarity	NPD1337	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD2668	Approved
0.7047	Intermediate Similarity	NPD2667	Approved
0.7045	Intermediate Similarity	NPD5095	Phase 3
0.7045	Intermediate Similarity	NPD5096	Phase 3
0.7039	Intermediate Similarity	NPD7258	Clinical (unspecified phase)
0.7034	Intermediate Similarity	NPD5283	Phase 1
0.7006	Intermediate Similarity	NPD7261	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD4098	Discontinued
0.699	Remote Similarity	NPD7047	Phase 3
0.6989	Remote Similarity	NPD5564	Approved
0.6987	Remote Similarity	NPD7294	Phase 1
0.6982	Remote Similarity	NPD7945	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD5709	Phase 3
0.6974	Remote Similarity	NPD1669	Approved
0.6952	Remote Similarity	NPD4420	Approved
0.6951	Remote Similarity	NPD3845	Phase 1
0.6949	Remote Similarity	NPD3933	Discontinued
0.6946	Remote Similarity	NPD4210	Discontinued
0.6943	Remote Similarity	NPD4475	Approved
0.6943	Remote Similarity	NPD4474	Approved
0.6936	Remote Similarity	NPD4666	Phase 3
0.6935	Remote Similarity	NPD7667	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD6331	Phase 2
0.6908	Remote Similarity	NPD2233	Approved
0.6908	Remote Similarity	NPD2230	Approved
0.6908	Remote Similarity	NPD2232	Approved
0.6905	Remote Similarity	NPD3866	Clinical (unspecified phase)
0.6902	Remote Similarity	NPD5525	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD5616	Clinical (unspecified phase)
0.6899	Remote Similarity	NPD3140	Approved
0.6899	Remote Similarity	NPD3142	Approved
0.6889	Remote Similarity	NPD3936	Clinical (unspecified phase)
0.6884	Remote Similarity	NPD4111	Phase 1
0.6884	Remote Similarity	NPD4665	Approved
0.6879	Remote Similarity	NPD5111	Phase 2
0.6879	Remote Similarity	NPD5110	Phase 2
0.6879	Remote Similarity	NPD5109	Approved
0.6878	Remote Similarity	NPD5457	Discontinued
0.6867	Remote Similarity	NPD1424	Approved
0.6855	Remote Similarity	NPD3657	Discovery
0.6852	Remote Similarity	NPD4726	Approved
0.6852	Remote Similarity	NPD4725	Approved
0.6852	Remote Similarity	NPD4721	Approved
0.6842	Remote Similarity	NPD5772	Approved
0.6842	Remote Similarity	NPD2978	Approved
0.6842	Remote Similarity	NPD2977	Approved
0.6842	Remote Similarity	NPD5773	Approved
0.6839	Remote Similarity	NPD5677	Discontinued
0.6835	Remote Similarity	NPD3532	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