NPASS Compound

Structure

NPC166979 OpenBabel07101719242D 26 30 0 0 1 0 0 0 0 0999 V2000 -0.0000 4.8387 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1904 5.3226 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8381 1.4516 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1636 -1.0478 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8381 0.4839 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2012 -0.9466 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 2.9032 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4776 0.1354 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6762 1.9355 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0393 1.4305 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3157 2.5124 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.9355 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5573 -0.1637 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6762 2.9032 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8381 1.4516 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8381 3.3871 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6788 1.0820 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.9597 1.7295 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.3524 3.8710 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8381 0.4839 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 N 0 0 3 0 0 0 0 0 0 0 0 0 -4.1904 3.3871 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8381 4.3548 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3524 4.8387 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5169 1.5658 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3533 2.6136 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 23 1 0 0 0 0 2 24 1 0 0 0 0 3 5 1 0 0 0 0 3 12 1 0 0 0 0 4 6 1 0 0 0 0 4 13 1 0 0 0 0 5 21 1 0 0 0 0 6 21 1 0 0 0 0 7 12 2 0 0 0 0 7 16 1 0 0 0 0 8 13 2 0 0 0 0 9 14 1 0 0 0 0 9 15 2 0 0 0 0 10 20 1 0 0 0 0 11 25 1 0 0 0 0 11 26 1 0 0 0 0 12 15 1 0 0 0 0 13 20 1 0 0 0 0 14 16 2 0 0 0 0 14 19 1 0 0 0 0 15 20 1 0 0 0 0 16 23 1 0 0 0 0 17 8 1 6 0 0 0 17 18 1 0 0 0 0 17 25 1 0 0 0 0 18 10 1 6 0 0 0 18 26 1 0 0 0 0 19 22 2 0 0 0 0 19 24 1 0 0 0 0 20 21 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	357.16
Volume:	353.459
LogP:	2.604
LogD:	2.602
LogS:	-3.493
# Rotatable Bonds:	3
TPSA:	57.23
# H-Bond Aceptor:	6
# H-Bond Donor:	0
# Rings:	5
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.596
Synthetic Accessibility Score:	4.653
Fsp3:	0.55
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:	-4.735
MDCK Permeability:	1.9919316400773823e-05
Pgp-inhibitor:	0.029
Pgp-substrate:	0.597
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.036
30% Bioavailability (F30%):	0.016

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.988
Plasma Protein Binding (PPB):	47.609039306640625%
Volume Distribution (VD):	2.046
Pgp-substrate:	43.00745391845703%

ADMET: Metabolism

CYP1A2-inhibitor:	0.057
CYP1A2-substrate:	0.87
CYP2C19-inhibitor:	0.34
CYP2C19-substrate:	0.929
CYP2C9-inhibitor:	0.518
CYP2C9-substrate:	0.399
CYP2D6-inhibitor:	0.045
CYP2D6-substrate:	0.589
CYP3A4-inhibitor:	0.605
CYP3A4-substrate:	0.918

ADMET: Excretion

Clearance (CL):	12.208
Half-life (T1/2):	0.251

ADMET: Toxicity

hERG Blockers:	0.051
Human Hepatotoxicity (H-HT):	0.289
Drug-inuced Liver Injury (DILI):	0.216
AMES Toxicity:	0.678
Rat Oral Acute Toxicity:	0.327
Maximum Recommended Daily Dose:	0.916
Skin Sensitization:	0.038
Carcinogencity:	0.861
Eye Corrosion:	0.003
Eye Irritation:	0.013
Respiratory Toxicity:	0.897

Download Data

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

Natural Product: NPC166979

Natural Product ID:	NPC166979
*Common Name:**	WVGKKVOLNYNBFM-NSHGMRRFSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	WVGKKVOLNYNBFM-NSHGMRRFSA-N
Standard InCHI:	InChI=1S/C20H23NO5/c1-23-16-7-12-3-5-21-6-4-13-8-17-18(26-11-25-17)10-20(13,21)15(12)9-14(16)19(22)24-2/h7-9,17-18H,3-6,10-11H2,1-2H3/t17-,18+,20-/m0/s1
SMILES:	COC(=O)c1cc2c(cc1OC)CCN1[C@@]32C[C@H]2OCO[C@H]2C=C3CC1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL462800
PubChem CID:	16059819
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0001782] Erythrina alkaloids [CHEMONTID:0002780] Erythrinanes

*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
NPO19604	Hyperbaena valida	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17067175]
NPO19604	Hyperbaena valida	Species	Menispermaceae	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

Activity Type	# Activity
Protein Complex	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT417	Protein Complex	Neuronal acetylcholine receptor; alpha3/beta4	Rattus norvegicus	IC50	=	77000.0	nM	PMID[470563]

☑ 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 NPC166979 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	308
0.1-0.2	1481
0.2-0.3	4266
0.3-0.4	12065
0.4-0.5	6169
0.5-0.6	13832
0.6-0.7	4306
0.7-0.8	245
0.8-0.85	24
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8571	High Similarity	NPC226708
0.8541	High Similarity	NPC124302
0.8541	High Similarity	NPC14622
0.8541	High Similarity	NPC70290
0.8541	High Similarity	NPC73020
0.8541	High Similarity	NPC46744
0.8541	High Similarity	NPC215098
0.8457	Intermediate Similarity	NPC119818
0.8457	Intermediate Similarity	NPC2173
0.8457	Intermediate Similarity	NPC202771
0.8457	Intermediate Similarity	NPC328700
0.8449	Intermediate Similarity	NPC72788
0.8449	Intermediate Similarity	NPC314100
0.8449	Intermediate Similarity	NPC226652
0.8449	Intermediate Similarity	NPC120671
0.8436	Intermediate Similarity	NPC27887
0.8325	Intermediate Similarity	NPC80472
0.8235	Intermediate Similarity	NPC125924
0.8222	Intermediate Similarity	NPC283999
0.8207	Intermediate Similarity	NPC169387
0.8207	Intermediate Similarity	NPC477259
0.8202	Intermediate Similarity	NPC474708
0.8182	Intermediate Similarity	NPC469815
0.8182	Intermediate Similarity	NPC469816
0.8146	Intermediate Similarity	NPC475845
0.8138	Intermediate Similarity	NPC33256
0.8138	Intermediate Similarity	NPC477258
0.8098	Intermediate Similarity	NPC475981
0.8098	Intermediate Similarity	NPC474746
0.809	Intermediate Similarity	NPC474324
0.809	Intermediate Similarity	NPC57812
0.8075	Intermediate Similarity	NPC63152
0.8022	Intermediate Similarity	NPC35680
0.8011	Intermediate Similarity	NPC230098
0.7968	Intermediate Similarity	NPC141440
0.7967	Intermediate Similarity	NPC308267
0.7935	Intermediate Similarity	NPC474745
0.7917	Intermediate Similarity	NPC207239
0.7906	Intermediate Similarity	NPC24228
0.7903	Intermediate Similarity	NPC116007
0.7903	Intermediate Similarity	NPC83511
0.7887	Intermediate Similarity	NPC286135
0.788	Intermediate Similarity	NPC474325
0.7877	Intermediate Similarity	NPC231198
0.7869	Intermediate Similarity	NPC304675
0.7861	Intermediate Similarity	NPC223125
0.7857	Intermediate Similarity	NPC303581
0.7857	Intermediate Similarity	NPC67978
0.7845	Intermediate Similarity	NPC86469
0.7828	Intermediate Similarity	NPC46990
0.7826	Intermediate Similarity	NPC222524
0.7826	Intermediate Similarity	NPC237044
0.7802	Intermediate Similarity	NPC75958
0.7784	Intermediate Similarity	NPC78733
0.7771	Intermediate Similarity	NPC223124
0.7771	Intermediate Similarity	NPC148898
0.7754	Intermediate Similarity	NPC102760
0.7749	Intermediate Similarity	NPC94499
0.774	Intermediate Similarity	NPC476443
0.774	Intermediate Similarity	NPC133817
0.7725	Intermediate Similarity	NPC162694
0.7684	Intermediate Similarity	NPC208890
0.7654	Intermediate Similarity	NPC477080
0.7647	Intermediate Similarity	NPC149285
0.7634	Intermediate Similarity	NPC474470
0.7626	Intermediate Similarity	NPC268077
0.7624	Intermediate Similarity	NPC320104
0.7598	Intermediate Similarity	NPC478048
0.7596	Intermediate Similarity	NPC181653
0.7596	Intermediate Similarity	NPC210918
0.7596	Intermediate Similarity	NPC190332
0.7594	Intermediate Similarity	NPC121400
0.7576	Intermediate Similarity	NPC207971
0.7568	Intermediate Similarity	NPC65403
0.7561	Intermediate Similarity	NPC328856
0.7561	Intermediate Similarity	NPC478046
0.7561	Intermediate Similarity	NPC180210
0.7561	Intermediate Similarity	NPC478047
0.7561	Intermediate Similarity	NPC321226
0.7561	Intermediate Similarity	NPC314914
0.7556	Intermediate Similarity	NPC106786
0.7553	Intermediate Similarity	NPC244554
0.7542	Intermediate Similarity	NPC31311
0.7542	Intermediate Similarity	NPC234392
0.7527	Intermediate Similarity	NPC476569
0.7527	Intermediate Similarity	NPC59567
0.7524	Intermediate Similarity	NPC284236
0.7524	Intermediate Similarity	NPC316368
0.7514	Intermediate Similarity	NPC97072
0.7514	Intermediate Similarity	NPC160298
0.7514	Intermediate Similarity	NPC266753
0.7514	Intermediate Similarity	NPC215829
0.7514	Intermediate Similarity	NPC306902
0.7514	Intermediate Similarity	NPC232924
0.7514	Intermediate Similarity	NPC477559
0.75	Intermediate Similarity	NPC294790
0.75	Intermediate Similarity	NPC100566
0.75	Intermediate Similarity	NPC118633
0.75	Intermediate Similarity	NPC148693
0.7486	Intermediate Similarity	NPC16805
0.7486	Intermediate Similarity	NPC138487
0.7486	Intermediate Similarity	NPC41178
0.7486	Intermediate Similarity	NPC180306
0.7486	Intermediate Similarity	NPC302527
0.7486	Intermediate Similarity	NPC216459
0.7486	Intermediate Similarity	NPC167546
0.7473	Intermediate Similarity	NPC153631
0.7473	Intermediate Similarity	NPC149090
0.7473	Intermediate Similarity	NPC19520
0.7472	Intermediate Similarity	NPC233029
0.7472	Intermediate Similarity	NPC210148
0.746	Intermediate Similarity	NPC99723
0.7459	Intermediate Similarity	NPC241055
0.7459	Intermediate Similarity	NPC82533
0.7459	Intermediate Similarity	NPC290759
0.7459	Intermediate Similarity	NPC266176
0.7459	Intermediate Similarity	NPC158148
0.7452	Intermediate Similarity	NPC170101
0.7446	Intermediate Similarity	NPC24264
0.7446	Intermediate Similarity	NPC476432
0.7446	Intermediate Similarity	NPC476002
0.7444	Intermediate Similarity	NPC146288
0.7443	Intermediate Similarity	NPC475959
0.7419	Intermediate Similarity	NPC311991
0.7411	Intermediate Similarity	NPC71124
0.7411	Intermediate Similarity	NPC23080
0.7411	Intermediate Similarity	NPC193906
0.7409	Intermediate Similarity	NPC237579
0.7405	Intermediate Similarity	NPC247389
0.7405	Intermediate Similarity	NPC284842
0.7396	Intermediate Similarity	NPC18306
0.7391	Intermediate Similarity	NPC225774
0.7391	Intermediate Similarity	NPC306669
0.7389	Intermediate Similarity	NPC76079
0.7385	Intermediate Similarity	NPC302001
0.738	Intermediate Similarity	NPC225597
0.738	Intermediate Similarity	NPC477640
0.738	Intermediate Similarity	NPC470739
0.7371	Intermediate Similarity	NPC130926
0.7366	Intermediate Similarity	NPC475686
0.7366	Intermediate Similarity	NPC58766
0.7363	Intermediate Similarity	NPC118804
0.736	Intermediate Similarity	NPC475713
0.736	Intermediate Similarity	NPC474432
0.7354	Intermediate Similarity	NPC241704
0.7351	Intermediate Similarity	NPC219341
0.7337	Intermediate Similarity	NPC78944
0.7337	Intermediate Similarity	NPC474427
0.7333	Intermediate Similarity	NPC319549
0.7326	Intermediate Similarity	NPC474475
0.7318	Intermediate Similarity	NPC119669
0.7316	Intermediate Similarity	NPC477560
0.7316	Intermediate Similarity	NPC15919
0.7312	Intermediate Similarity	NPC298979
0.731	Intermediate Similarity	NPC470646
0.7306	Intermediate Similarity	NPC9867
0.7306	Intermediate Similarity	NPC214629
0.7302	Intermediate Similarity	NPC187678
0.73	Intermediate Similarity	NPC311781
0.7297	Intermediate Similarity	NPC168409
0.7297	Intermediate Similarity	NPC247972
0.7296	Intermediate Similarity	NPC254957
0.7295	Intermediate Similarity	NPC55470
0.7293	Intermediate Similarity	NPC93593
0.7286	Intermediate Similarity	NPC5374
0.7277	Intermediate Similarity	NPC32154
0.7258	Intermediate Similarity	NPC86144
0.7258	Intermediate Similarity	NPC304659
0.7249	Intermediate Similarity	NPC4669
0.7247	Intermediate Similarity	NPC59907
0.7247	Intermediate Similarity	NPC37144
0.724	Intermediate Similarity	NPC179704
0.7234	Intermediate Similarity	NPC6152
0.7228	Intermediate Similarity	NPC26353
0.7228	Intermediate Similarity	NPC205167
0.7225	Intermediate Similarity	NPC327005
0.7225	Intermediate Similarity	NPC309692
0.7222	Intermediate Similarity	NPC162653
0.7222	Intermediate Similarity	NPC476579
0.7211	Intermediate Similarity	NPC229166
0.7211	Intermediate Similarity	NPC199465
0.7211	Intermediate Similarity	NPC128560
0.7209	Intermediate Similarity	NPC7018
0.7207	Intermediate Similarity	NPC470088
0.7204	Intermediate Similarity	NPC15212
0.7204	Intermediate Similarity	NPC276944
0.7204	Intermediate Similarity	NPC232514
0.7204	Intermediate Similarity	NPC238530
0.7202	Intermediate Similarity	NPC275132
0.7202	Intermediate Similarity	NPC248642
0.7202	Intermediate Similarity	NPC116284
0.7196	Intermediate Similarity	NPC227683
0.7194	Intermediate Similarity	NPC82763
0.7188	Intermediate Similarity	NPC258695
0.7188	Intermediate Similarity	NPC126284
0.7188	Intermediate Similarity	NPC470879
0.7179	Intermediate Similarity	NPC214116
0.7179	Intermediate Similarity	NPC471650
0.7174	Intermediate Similarity	NPC115123
0.7174	Intermediate Similarity	NPC239113

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 NPC166979 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	201
0.1-0.2	679
0.2-0.3	1108
0.3-0.4	2249
0.4-0.5	2640
0.5-0.6	1787
0.6-0.7	469
0.7-0.8	14
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8541	High Similarity	NPD4420	Approved
0.8457	Intermediate Similarity	NPD5005	Approved
0.8457	Intermediate Similarity	NPD5006	Approved
0.7622	Intermediate Similarity	NPD5313	Approved
0.7622	Intermediate Similarity	NPD5312	Approved
0.7426	Intermediate Similarity	NPD4859	Phase 1
0.7424	Intermediate Similarity	NPD4107	Approved
0.7333	Intermediate Similarity	NPD7296	Approved
0.7303	Intermediate Similarity	NPD3640	Phase 3
0.7303	Intermediate Similarity	NPD3639	Approved
0.7303	Intermediate Similarity	NPD3641	Approved
0.73	Intermediate Similarity	NPD4482	Phase 3
0.724	Intermediate Similarity	NPD7281	Phase 3
0.724	Intermediate Similarity	NPD7280	Phase 3
0.7235	Intermediate Similarity	NPD6625	Approved
0.7213	Intermediate Similarity	NPD5616	Clinical (unspecified phase)
0.7213	Intermediate Similarity	NPD5978	Approved
0.7213	Intermediate Similarity	NPD5977	Approved
0.7204	Intermediate Similarity	NPD6107	Approved
0.7183	Intermediate Similarity	NPD5619	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD4481	Phase 3
0.7166	Intermediate Similarity	NPD5710	Approved
0.7166	Intermediate Similarity	NPD5711	Approved
0.7158	Intermediate Similarity	NPD3050	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD3446	Phase 1
0.7135	Intermediate Similarity	NPD8005	Clinical (unspecified phase)
0.7119	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD8285	Discontinued
0.711	Intermediate Similarity	NPD2569	Approved
0.711	Intermediate Similarity	NPD2567	Approved
0.7107	Intermediate Similarity	NPD5525	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD4584	Approved
0.709	Intermediate Similarity	NPD2898	Approved
0.7089	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7079	Intermediate Similarity	NPD5457	Discontinued
0.7068	Intermediate Similarity	NPD6020	Phase 2
0.7062	Intermediate Similarity	NPD2968	Approved
0.7062	Intermediate Similarity	NPD3534	Clinical (unspecified phase)
0.7062	Intermediate Similarity	NPD2971	Approved
0.7049	Intermediate Similarity	NPD5890	Approved
0.7049	Intermediate Similarity	NPD5889	Approved
0.7045	Intermediate Similarity	NPD4664	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD5242	Approved
0.7031	Intermediate Similarity	NPD5441	Clinical (unspecified phase)
0.7026	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.702	Intermediate Similarity	NPD3808	Clinical (unspecified phase)
0.7017	Intermediate Similarity	NPD1670	Discontinued
0.7016	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7015	Intermediate Similarity	NPD7238	Clinical (unspecified phase)
0.7015	Intermediate Similarity	NPD5564	Approved
0.701	Intermediate Similarity	NPD3057	Approved
0.701	Intermediate Similarity	NPD7190	Clinical (unspecified phase)
0.701	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7005	Intermediate Similarity	NPD7701	Phase 2
0.7005	Intermediate Similarity	NPD7291	Discontinued
0.699	Remote Similarity	NPD7607	Clinical (unspecified phase)
0.6984	Remote Similarity	NPD6747	Phase 1
0.6967	Remote Similarity	NPD7930	Approved
0.6957	Remote Similarity	NPD6873	Phase 2
0.693	Remote Similarity	NPD7907	Approved
0.6927	Remote Similarity	NPD3533	Approved
0.6927	Remote Similarity	NPD3448	Approved
0.6927	Remote Similarity	NPD2972	Approved
0.6927	Remote Similarity	NPD2491	Approved
0.6927	Remote Similarity	NPD956	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD7317	Phase 3
0.6919	Remote Similarity	NPD7248	Discontinued
0.6919	Remote Similarity	NPD7693	Approved
0.6912	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.691	Remote Similarity	NPD2654	Approved
0.6908	Remote Similarity	NPD7999	Approved
0.6902	Remote Similarity	NPD6585	Discontinued
0.6902	Remote Similarity	NPD1337	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD5980	Discovery
0.6898	Remote Similarity	NPD6997	Phase 2
0.6898	Remote Similarity	NPD4947	Clinical (unspecified phase)
0.6893	Remote Similarity	NPD7497	Discontinued
0.6888	Remote Similarity	NPD6146	Clinical (unspecified phase)
0.6865	Remote Similarity	NPD6386	Approved
0.6865	Remote Similarity	NPD6385	Approved
0.6863	Remote Similarity	NPD6874	Approved
0.6862	Remote Similarity	NPD1309	Phase 2
0.6862	Remote Similarity	NPD1307	Phase 2
0.6853	Remote Similarity	NPD6618	Phase 2
0.685	Remote Similarity	NPD2488	Approved
0.685	Remote Similarity	NPD2490	Approved
0.6849	Remote Similarity	NPD8469	Approved
0.6847	Remote Similarity	NPD2974	Approved
0.6847	Remote Similarity	NPD2975	Approved
0.6847	Remote Similarity	NPD2973	Approved
0.6845	Remote Similarity	NPD7318	Phase 3
0.6839	Remote Similarity	NPD7177	Discontinued
0.6837	Remote Similarity	NPD4111	Phase 1
0.6837	Remote Similarity	NPD4665	Approved
0.6831	Remote Similarity	NPD4727	Phase 1
0.6831	Remote Similarity	NPD7427	Discontinued
0.683	Remote Similarity	NPD7048	Phase 3
0.6828	Remote Similarity	NPD6844	Discontinued
0.6825	Remote Similarity	NPD7400	Phase 3
0.6821	Remote Similarity	NPD6297	Approved
0.6806	Remote Similarity	NPD4166	Phase 2
0.68	Remote Similarity	NPD7235	Clinical (unspecified phase)
0.6798	Remote Similarity	NPD7667	Clinical (unspecified phase)
0.6796	Remote Similarity	NPD160	Clinical (unspecified phase)
0.6794	Remote Similarity	NPD7584	Approved
0.6792	Remote Similarity	NPD7827	Phase 1
0.6784	Remote Similarity	NPD3863	Clinical (unspecified phase)
0.6782	Remote Similarity	NPD6213	Phase 3
0.6782	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.6782	Remote Similarity	NPD6212	Phase 3
0.6779	Remote Similarity	NPD8320	Phase 1
0.6779	Remote Similarity	NPD8319	Approved
0.6774	Remote Similarity	NPD4773	Phase 2
0.6774	Remote Similarity	NPD4772	Phase 2
0.6768	Remote Similarity	NPD6853	Approved
0.6768	Remote Similarity	NPD6851	Approved
0.6768	Remote Similarity	NPD6021	Clinical (unspecified phase)
0.6755	Remote Similarity	NPD5353	Approved
0.6748	Remote Similarity	NPD6779	Approved
0.6748	Remote Similarity	NPD6777	Approved
0.6748	Remote Similarity	NPD4580	Approved
0.6748	Remote Similarity	NPD6776	Approved
0.6748	Remote Similarity	NPD6780	Approved
0.6748	Remote Similarity	NPD6778	Approved
0.6748	Remote Similarity	NPD6782	Approved
0.6748	Remote Similarity	NPD6781	Approved
0.6745	Remote Similarity	NPD7783	Phase 2
0.6745	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6745	Remote Similarity	NPD5676	Approved
0.6736	Remote Similarity	NPD2248	Approved
0.6736	Remote Similarity	NPD2246	Approved
0.6732	Remote Similarity	NPD4668	Phase 2
0.6728	Remote Similarity	NPD5433	Clinical (unspecified phase)
0.6723	Remote Similarity	NPD743	Approved
0.672	Remote Similarity	NPD4581	Clinical (unspecified phase)
0.6719	Remote Similarity	NPD6071	Discontinued
0.6717	Remote Similarity	NPD4078	Clinical (unspecified phase)
0.6715	Remote Similarity	NPD3452	Approved
0.6715	Remote Similarity	NPD3450	Approved
0.6715	Remote Similarity	NPD2494	Approved
0.6715	Remote Similarity	NPD2493	Approved
0.6714	Remote Similarity	NPD6973	Clinical (unspecified phase)
0.6703	Remote Similarity	NPD6783	Clinical (unspecified phase)
0.6701	Remote Similarity	NPD7039	Approved
0.6701	Remote Similarity	NPD7038	Approved
0.6701	Remote Similarity	NPD6559	Discontinued
0.6699	Remote Similarity	NPD7565	Approved
0.6699	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6699	Remote Similarity	NPD3297	Approved
0.6698	Remote Similarity	NPD7874	Approved
0.6698	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6685	Remote Similarity	NPD5754	Discontinued
0.6684	Remote Similarity	NPD2970	Approved
0.6684	Remote Similarity	NPD8051	Clinical (unspecified phase)
0.6684	Remote Similarity	NPD2969	Approved
0.6683	Remote Similarity	NPD6823	Phase 2
0.6667	Remote Similarity	NPD2492	Phase 1
0.6667	Remote Similarity	NPD7837	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2563	Approved
0.6667	Remote Similarity	NPD6591	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2560	Approved
0.6667	Remote Similarity	NPD2651	Approved
0.6667	Remote Similarity	NPD6040	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2649	Approved
0.6667	Remote Similarity	NPD1945	Phase 1
0.6652	Remote Similarity	NPD8491	Approved
0.6651	Remote Similarity	NPD7435	Discontinued
0.6651	Remote Similarity	NPD8151	Discontinued
0.6651	Remote Similarity	NPD7696	Phase 3
0.6651	Remote Similarity	NPD7698	Approved
0.6651	Remote Similarity	NPD7697	Approved
0.665	Remote Similarity	NPD3823	Discontinued
0.6649	Remote Similarity	NPD2489	Approved
0.6649	Remote Similarity	NPD27	Approved
0.6648	Remote Similarity	NPD4477	Approved
0.6648	Remote Similarity	NPD3142	Approved
0.6648	Remote Similarity	NPD3140	Approved
0.6648	Remote Similarity	NPD4476	Approved
0.6648	Remote Similarity	NPD2935	Discontinued
0.6635	Remote Similarity	NPD7583	Approved
0.6634	Remote Similarity	NPD4361	Phase 2
0.6634	Remote Similarity	NPD4362	Clinical (unspecified phase)
0.6633	Remote Similarity	NPD8156	Discontinued
0.6632	Remote Similarity	NPD6808	Phase 2
0.6632	Remote Similarity	NPD7315	Approved
0.6632	Remote Similarity	NPD3051	Approved
0.663	Remote Similarity	NPD2534	Approved
0.663	Remote Similarity	NPD2533	Approved
0.663	Remote Similarity	NPD2532	Approved
0.6622	Remote Similarity	NPD8058	Clinical (unspecified phase)
0.6622	Remote Similarity	NPD8059	Phase 3
0.6621	Remote Similarity	NPD8366	Approved
0.662	Remote Similarity	NPD7047	Phase 3
0.6619	Remote Similarity	NPD4582	Approved
0.6619	Remote Similarity	NPD7870	Phase 2
0.6619	Remote Similarity	NPD7871	Phase 2
0.6619	Remote Similarity	NPD3298	Approved
0.6619	Remote Similarity	NPD4583	Approved
0.6618	Remote Similarity	NPD6181	Discontinued
0.6615	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