NPASS Compound

Structure

CID117032 OpenBabel06191715472D 23 27 0 0 0 0 0 0 0 0999 V2000 1.7208 -1.9642 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0417 0.9696 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6808 -2.9095 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0415 -0.0010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8409 -3.3947 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2018 1.4548 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6806 -1.9395 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2014 -0.4859 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0008 -2.9099 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8403 1.4555 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0002 0.9706 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3612 0.9699 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6807 0.9703 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8404 -1.4548 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3610 -0.0007 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0005 -1.9400 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6805 -0.0003 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8399 -0.4852 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8402 -0.4848 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5209 -0.4855 0.0000 N 0 3 0 0 0 0 0 0 0 0 0 0 0.8397 -1.4552 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.7213 0.0243 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 21 1 0 0 0 0 2 4 1 0 0 0 0 2 6 2 0 0 0 0 3 5 2 0 0 0 0 3 7 1 0 0 0 0 4 8 2 0 0 0 0 5 9 1 0 0 0 0 6 12 1 0 0 0 0 7 14 2 0 0 0 0 8 15 1 0 0 0 0 9 16 2 0 0 0 0 10 11 1 0 0 0 0 10 13 1 0 0 0 0 11 22 1 0 0 0 0 12 13 2 0 0 0 0 12 15 1 0 0 0 0 13 17 1 0 0 0 0 14 16 1 0 0 0 0 14 19 1 0 0 0 0 15 20 2 0 0 0 0 16 21 1 0 0 0 0 17 18 2 0 0 0 0 17 20 1 0 0 0 0 18 21 1 0 0 0 0 18 22 1 0 0 0 0 19 22 1 0 0 0 0 19 23 2 0 0 0 0 M CHG 1 20 1 M END $$$$

Physi-Chem Properties

Molecular Weight:	301.12
Volume:	312.45
LogP:	3.283
LogD:	3.264
LogS:	-5.39
# Rotatable Bonds:	0
TPSA:	35.91
# H-Bond Aceptor:	4
# H-Bond Donor:	0
# Rings:	5
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.741
Synthetic Accessibility Score:	2.832
Fsp3:	0.158
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.56
MDCK Permeability:	3.1143346859607846e-05
Pgp-inhibitor:	0.052
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.111

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.66
Plasma Protein Binding (PPB):	94.02674102783203%
Volume Distribution (VD):	0.989
Pgp-substrate:	3.572718381881714%

ADMET: Metabolism

CYP1A2-inhibitor:	0.94
CYP1A2-substrate:	0.928
CYP2C19-inhibitor:	0.697
CYP2C19-substrate:	0.891
CYP2C9-inhibitor:	0.492
CYP2C9-substrate:	0.604
CYP2D6-inhibitor:	0.905
CYP2D6-substrate:	0.798
CYP3A4-inhibitor:	0.345
CYP3A4-substrate:	0.911

ADMET: Excretion

Clearance (CL):	1.227
Half-life (T1/2):	0.107

ADMET: Toxicity

hERG Blockers:	0.066
Human Hepatotoxicity (H-HT):	0.977
Drug-inuced Liver Injury (DILI):	0.962
AMES Toxicity:	0.246
Rat Oral Acute Toxicity:	0.678
Maximum Recommended Daily Dose:	0.322
Skin Sensitization:	0.158
Carcinogencity:	0.814
Eye Corrosion:	0.003
Eye Irritation:	0.013
Respiratory Toxicity:	0.931

Download Data

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

Natural Product: NPC117032

Natural Product ID:	NPC117032
*Common Name:**	Dehydroevodiamine
IUPAC Name:	n.a.
Synonyms:	Dehydroevidiamine; Dehydroevodiamine; Dehydroevodiamine HCl
Standard InCHIKey:	VXHNSVKJHXSKKM-UHFFFAOYSA-O
Standard InCHI:	InChI=1S/C19H15N3O/c1-21-16-9-5-3-7-14(16)19(23)22-11-10-13-12-6-2-4-8-15(12)20-17(13)18(21)22/h2-9H,10-11H2,1H3/p+1
SMILES:	O=c1c2ccccc2n(c2=C3C(=c4c(=[NH+]3)cccc4)CCn12)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL81923
PubChem CID:	156372
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000211] Indoles and derivatives [CHEMONTID:0001213] Pyridoindoles [CHEMONTID:0001914] Beta carbolines

*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
NPO19935	Evodia rutaecarpa	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7463094]
NPO19935	Evodia rutaecarpa	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8201313]
NPO19935	Evodia rutaecarpa	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8699182]
NPO30823	Evodia rutaecarpa	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[HerDing]
NPO19935	Evodia rutaecarpa	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO30823	Evodia rutaecarpa	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO19935	Evodia rutaecarpa	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO19935	Evodia rutaecarpa	Species	Rutaceae	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
EC50	4
IC50	5
Kd	1
Ki	2
Others	11

Activity Type	# Activity
Cell Line	9
Individual Protein	4
Others	3
Protein Family	1
Tissue	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1603	Individual Protein	Cytochrome P450 1A1	Homo sapiens	IC50	=	18050.0	nM	PMID[506258]
NPT208	Individual Protein	Cytochrome P450 1A2	Homo sapiens	IC50	=	5630.0	nM	PMID[506258]
NPT1604	Individual Protein	Cytochrome P450 1B1	Homo sapiens	IC50	=	330.0	nM	PMID[506258]
NPT113	Cell Line	RAW264.7	Mus musculus	Inhibition	=	80.6	%	PMID[506262]
NPT113	Cell Line	RAW264.7	Mus musculus	Inhibition	=	74.2	%	PMID[506262]
NPT113	Cell Line	RAW264.7	Mus musculus	Inhibition	=	44.0	%	PMID[506262]
NPT113	Cell Line	RAW264.7	Mus musculus	Inhibition	=	86.1	%	PMID[506262]
NPT113	Cell Line	RAW264.7	Mus musculus	Inhibition	=	78.1	%	PMID[506262]
NPT113	Cell Line	RAW264.7	Mus musculus	Inhibition	=	23.2	%	PMID[506262]
NPT113	Cell Line	RAW264.7	Mus musculus	Activity	=	84.3	%	PMID[506262]
NPT113	Cell Line	RAW264.7	Mus musculus	Activity	=	77.0	%	PMID[506262]
NPT113	Cell Line	RAW264.7	Mus musculus	Activity	=	24.2	%	PMID[506262]
NPT27	Others	Unspecified		IC50	=	3.0	nM	PMID[506258]
NPT27	Others	Unspecified		IC50	=	0.06	nM	PMID[506258]
NPT177	Tissue	Aorta	Rattus norvegicus	EC50	=	1640.0	nM	PMID[506259]
NPT177	Tissue	Aorta	Rattus norvegicus	Emax	=	100.0	%	PMID[506259]
NPT177	Tissue	Aorta	Rattus norvegicus	EC50	=	7780.0	nM	PMID[506259]
NPT177	Tissue	Aorta	Rattus norvegicus	EC50	=	1600.0	nM	PMID[506259]
NPT177	Tissue	Aorta	Rattus norvegicus	EC50	=	5830.0	nM	PMID[506259]
NPT2	Others	Unspecified		Kd	=	128.82	nM	PMID[506259]
NPT968	Protein Family	Adrenergic receptor alpha-1	Rattus norvegicus	Ki	=	2400.0	nM	PMID[506259]
NPT92	Individual Protein	Serotonin 1a (5-HT1a) receptor	Homo sapiens	Ki	=	36000.0	nM	PMID[506260]

☑ 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 NPC117032 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	504
0.1-0.2	6028
0.2-0.3	14176
0.3-0.4	14917
0.4-0.5	4117
0.5-0.6	2444
0.6-0.7	461
0.7-0.8	45
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.8333	Intermediate Similarity	NPC136002
0.8163	Intermediate Similarity	NPC300299
0.8133	Intermediate Similarity	NPC471574
0.8133	Intermediate Similarity	NPC2823
0.8107	Intermediate Similarity	NPC17273
0.8107	Intermediate Similarity	NPC141612
0.8107	Intermediate Similarity	NPC135601
0.7881	Intermediate Similarity	NPC83214
0.7838	Intermediate Similarity	NPC207428
0.7688	Intermediate Similarity	NPC295021
0.7674	Intermediate Similarity	NPC21429
0.7647	Intermediate Similarity	NPC469560
0.7639	Intermediate Similarity	NPC257490
0.7616	Intermediate Similarity	NPC316104
0.7616	Intermediate Similarity	NPC162417
0.7597	Intermediate Similarity	NPC207554
0.756	Intermediate Similarity	NPC355
0.7548	Intermediate Similarity	NPC471164
0.75	Intermediate Similarity	NPC291962
0.75	Intermediate Similarity	NPC177684
0.7485	Intermediate Similarity	NPC84317
0.7448	Intermediate Similarity	NPC179605
0.7448	Intermediate Similarity	NPC112373
0.7448	Intermediate Similarity	NPC258531
0.7448	Intermediate Similarity	NPC161956
0.7448	Intermediate Similarity	NPC279385
0.7429	Intermediate Similarity	NPC133003
0.7397	Intermediate Similarity	NPC103292
0.7347	Intermediate Similarity	NPC268534
0.7322	Intermediate Similarity	NPC106118
0.7321	Intermediate Similarity	NPC471130
0.7305	Intermediate Similarity	NPC88970
0.7289	Intermediate Similarity	NPC154478
0.7205	Intermediate Similarity	NPC324445
0.7203	Intermediate Similarity	NPC296163
0.7193	Intermediate Similarity	NPC471943
0.7179	Intermediate Similarity	NPC471123
0.7178	Intermediate Similarity	NPC473329
0.7168	Intermediate Similarity	NPC469529
0.7143	Intermediate Similarity	NPC471155
0.7143	Intermediate Similarity	NPC40364
0.7134	Intermediate Similarity	NPC122553
0.7123	Intermediate Similarity	NPC313449
0.7123	Intermediate Similarity	NPC192209
0.7105	Intermediate Similarity	NPC270241
0.709	Intermediate Similarity	NPC225400
0.7083	Intermediate Similarity	NPC187036
0.7072	Intermediate Similarity	NPC324091
0.7069	Intermediate Similarity	NPC470548
0.7065	Intermediate Similarity	NPC472539
0.7065	Intermediate Similarity	NPC470787
0.7065	Intermediate Similarity	NPC472540
0.7059	Intermediate Similarity	NPC113056
0.7059	Intermediate Similarity	NPC138293
0.7059	Intermediate Similarity	NPC209389
0.7053	Intermediate Similarity	NPC470786
0.7053	Intermediate Similarity	NPC472538
0.7044	Intermediate Similarity	NPC130251
0.7027	Intermediate Similarity	NPC472541
0.7027	Intermediate Similarity	NPC472542
0.7027	Intermediate Similarity	NPC471199
0.7024	Intermediate Similarity	NPC222029
0.7022	Intermediate Similarity	NPC470205
0.7012	Intermediate Similarity	NPC300596
0.7012	Intermediate Similarity	NPC237649
0.7011	Intermediate Similarity	NPC177261
0.7	Intermediate Similarity	NPC39818
0.6982	Remote Similarity	NPC276085
0.6971	Remote Similarity	NPC248862
0.6954	Remote Similarity	NPC254698
0.6928	Remote Similarity	NPC66936
0.6923	Remote Similarity	NPC473666
0.6913	Remote Similarity	NPC226143
0.691	Remote Similarity	NPC88110
0.6909	Remote Similarity	NPC109787
0.6895	Remote Similarity	NPC295548
0.6893	Remote Similarity	NPC14849
0.6871	Remote Similarity	NPC288232
0.6852	Remote Similarity	NPC238499
0.6842	Remote Similarity	NPC68650
0.6836	Remote Similarity	NPC471743
0.6815	Remote Similarity	NPC53044
0.6811	Remote Similarity	NPC272458
0.6796	Remote Similarity	NPC477003
0.6795	Remote Similarity	NPC472245
0.6793	Remote Similarity	NPC471196
0.6793	Remote Similarity	NPC471195
0.679	Remote Similarity	NPC301760
0.6788	Remote Similarity	NPC243850
0.6782	Remote Similarity	NPC114637
0.678	Remote Similarity	NPC328611
0.6763	Remote Similarity	NPC189116
0.676	Remote Similarity	NPC182057
0.676	Remote Similarity	NPC147298
0.676	Remote Similarity	NPC131450
0.6744	Remote Similarity	NPC27904
0.6742	Remote Similarity	NPC475607
0.6736	Remote Similarity	NPC471191
0.6735	Remote Similarity	NPC314141
0.6731	Remote Similarity	NPC150863
0.6725	Remote Similarity	NPC477887
0.6723	Remote Similarity	NPC161861
0.6723	Remote Similarity	NPC242269
0.6723	Remote Similarity	NPC252572
0.6713	Remote Similarity	NPC473498
0.6707	Remote Similarity	NPC469537
0.6705	Remote Similarity	NPC194881
0.6704	Remote Similarity	NPC474081
0.6701	Remote Similarity	NPC6865
0.6701	Remote Similarity	NPC153980
0.67	Remote Similarity	NPC248601
0.6688	Remote Similarity	NPC192533
0.6688	Remote Similarity	NPC9856
0.6687	Remote Similarity	NPC470440
0.6685	Remote Similarity	NPC475594
0.6667	Remote Similarity	NPC476341
0.6667	Remote Similarity	NPC476460
0.6667	Remote Similarity	NPC285192
0.6667	Remote Similarity	NPC307396
0.6667	Remote Similarity	NPC474041
0.665	Remote Similarity	NPC471197
0.665	Remote Similarity	NPC72956
0.6649	Remote Similarity	NPC198401
0.6648	Remote Similarity	NPC63047
0.6648	Remote Similarity	NPC117027
0.6648	Remote Similarity	NPC151635
0.6648	Remote Similarity	NPC475248
0.6632	Remote Similarity	NPC317701
0.663	Remote Similarity	NPC73994
0.6628	Remote Similarity	NPC104345
0.6625	Remote Similarity	NPC184437
0.6621	Remote Similarity	NPC302790
0.6617	Remote Similarity	NPC471198
0.6615	Remote Similarity	NPC471944
0.6611	Remote Similarity	NPC284775
0.6611	Remote Similarity	NPC28848
0.6611	Remote Similarity	NPC14325
0.6609	Remote Similarity	NPC476231
0.6604	Remote Similarity	NPC476687
0.6604	Remote Similarity	NPC476685
0.6604	Remote Similarity	NPC476689
0.6603	Remote Similarity	NPC252794
0.6591	Remote Similarity	NPC279527
0.6591	Remote Similarity	NPC214960
0.6587	Remote Similarity	NPC467188
0.6582	Remote Similarity	NPC194562
0.6582	Remote Similarity	NPC314431
0.6582	Remote Similarity	NPC280807
0.6582	Remote Similarity	NPC187231
0.6578	Remote Similarity	NPC276430
0.6578	Remote Similarity	NPC92803
0.6575	Remote Similarity	NPC475094
0.6575	Remote Similarity	NPC475761
0.6573	Remote Similarity	NPC318183
0.6571	Remote Similarity	NPC21174
0.6571	Remote Similarity	NPC478182
0.6571	Remote Similarity	NPC271797
0.6571	Remote Similarity	NPC478184
0.6561	Remote Similarity	NPC476950
0.6559	Remote Similarity	NPC18890
0.6552	Remote Similarity	NPC172170
0.655	Remote Similarity	NPC281094
0.6549	Remote Similarity	NPC291610
0.6548	Remote Similarity	NPC478186
0.6543	Remote Similarity	NPC325599
0.6533	Remote Similarity	NPC471193
0.6533	Remote Similarity	NPC471194
0.6526	Remote Similarity	NPC79356
0.6526	Remote Similarity	NPC102592
0.6517	Remote Similarity	NPC471192
0.6517	Remote Similarity	NPC472118
0.651	Remote Similarity	NPC57051
0.6506	Remote Similarity	NPC277157
0.6503	Remote Similarity	NPC191415
0.6497	Remote Similarity	NPC322433
0.6491	Remote Similarity	NPC70406
0.6486	Remote Similarity	NPC308931
0.6486	Remote Similarity	NPC99939
0.6485	Remote Similarity	NPC22082
0.6485	Remote Similarity	NPC186284
0.6477	Remote Similarity	NPC265100
0.6471	Remote Similarity	NPC144691
0.6467	Remote Similarity	NPC470822
0.6463	Remote Similarity	NPC65408
0.6461	Remote Similarity	NPC70949
0.6456	Remote Similarity	NPC476817
0.6455	Remote Similarity	NPC216550
0.6453	Remote Similarity	NPC251391
0.6448	Remote Similarity	NPC91179
0.6441	Remote Similarity	NPC115232
0.6441	Remote Similarity	NPC42372
0.6438	Remote Similarity	NPC316746
0.6433	Remote Similarity	NPC154602
0.6433	Remote Similarity	NPC243756
0.6432	Remote Similarity	NPC467063
0.6432	Remote Similarity	NPC285923
0.6432	Remote Similarity	NPC471742
0.6429	Remote Similarity	NPC83774
0.6424	Remote Similarity	NPC472243
0.6421	Remote Similarity	NPC304203

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 NPC117032 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	250
0.1-0.2	633
0.2-0.3	1087
0.3-0.4	1592
0.4-0.5	2889
0.5-0.6	2219
0.6-0.7	433
0.7-0.8	46
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
1.0	High Similarity	NPD3248	Phase 1
0.8082	Intermediate Similarity	NPD1919	Approved
0.8082	Intermediate Similarity	NPD1920	Approved
0.7806	Intermediate Similarity	NPD6017	Discontinued
0.7785	Intermediate Similarity	NPD6740	Clinical (unspecified phase)
0.7667	Intermediate Similarity	NPD2950	Approved
0.7667	Intermediate Similarity	NPD2949	Approved
0.7595	Intermediate Similarity	NPD4402	Clinical (unspecified phase)
0.7547	Intermediate Similarity	NPD4942	Approved
0.7532	Intermediate Similarity	NPD1524	Phase 1
0.7517	Intermediate Similarity	NPD4549	Discontinued
0.75	Intermediate Similarity	NPD2840	Approved
0.7436	Intermediate Similarity	NPD3434	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD6655	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD5918	Discontinued
0.7389	Intermediate Similarity	NPD6768	Approved
0.7375	Intermediate Similarity	NPD6466	Approved
0.7375	Intermediate Similarity	NPD6467	Approved
0.7342	Intermediate Similarity	NPD4464	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD4939	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD7072	Phase 2
0.7273	Intermediate Similarity	NPD5923	Phase 1
0.7273	Intermediate Similarity	NPD2351	Discontinued
0.7267	Intermediate Similarity	NPD7662	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD797	Clinical (unspecified phase)
0.7262	Intermediate Similarity	NPD2288	Clinical (unspecified phase)
0.726	Intermediate Similarity	NPD1306	Clinical (unspecified phase)
0.7257	Intermediate Similarity	NPD1966	Approved
0.7248	Intermediate Similarity	NPD1640	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD4077	Clinical (unspecified phase)
0.723	Intermediate Similarity	NPD4775	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD5042	Phase 1
0.7209	Intermediate Similarity	NPD7443	Clinical (unspecified phase)
0.7203	Intermediate Similarity	NPD5179	Approved
0.7203	Intermediate Similarity	NPD5180	Approved
0.7203	Intermediate Similarity	NPD5181	Approved
0.7186	Intermediate Similarity	NPD4393	Approved
0.7186	Intermediate Similarity	NPD33	Approved
0.7178	Intermediate Similarity	NPD5748	Phase 2
0.7175	Intermediate Similarity	NPD7564	Discontinued
0.7171	Intermediate Similarity	NPD1781	Discontinued
0.7143	Intermediate Similarity	NPD3079	Approved
0.7143	Intermediate Similarity	NPD3076	Approved
0.7143	Intermediate Similarity	NPD3077	Approved
0.7143	Intermediate Similarity	NPD3078	Approved
0.7134	Intermediate Similarity	NPD6342	Discontinued
0.7134	Intermediate Similarity	NPD6358	Phase 2
0.7123	Intermediate Similarity	NPD7481	Approved
0.7123	Intermediate Similarity	NPD7480	Approved
0.7104	Intermediate Similarity	NPD7406	Phase 2
0.7095	Intermediate Similarity	NPD5820	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD7254	Discontinued
0.7078	Intermediate Similarity	NPD1619	Phase 3
0.7078	Intermediate Similarity	NPD486	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD4300	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD6566	Discontinued
0.7056	Intermediate Similarity	NPD4988	Discontinued
0.7047	Intermediate Similarity	NPD1123	Approved
0.7047	Intermediate Similarity	NPD1124	Approved
0.7045	Intermediate Similarity	NPD2590	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD6575	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD5131	Approved
0.7011	Intermediate Similarity	NPD3868	Phase 1
0.7006	Intermediate Similarity	NPD6318	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD5400	Approved
0.6995	Remote Similarity	NPD4863	Approved
0.6987	Remote Similarity	NPD1527	Phase 2
0.6973	Remote Similarity	NPD7027	Phase 3
0.6966	Remote Similarity	NPD1175	Approved
0.6964	Remote Similarity	NPD951	Approved
0.695	Remote Similarity	NPD1065	Approved
0.695	Remote Similarity	NPD1064	Approved
0.6946	Remote Similarity	NPD7612	Clinical (unspecified phase)
0.6946	Remote Similarity	NPD2790	Discontinued
0.694	Remote Similarity	NPD1658	Discontinued
0.6933	Remote Similarity	NPD5933	Phase 3
0.6933	Remote Similarity	NPD5931	Phase 3
0.6933	Remote Similarity	NPD5932	Phase 3
0.6933	Remote Similarity	NPD1079	Discontinued
0.6932	Remote Similarity	NPD4091	Approved
0.6923	Remote Similarity	NPD7175	Phase 1
0.6914	Remote Similarity	NPD6301	Phase 2
0.691	Remote Similarity	NPD5473	Discontinued
0.691	Remote Similarity	NPD3989	Phase 3
0.691	Remote Similarity	NPD7014	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD979	Approved
0.6906	Remote Similarity	NPD4426	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD2918	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD2919	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD7795	Phase 2
0.6894	Remote Similarity	NPD2010	Phase 3
0.6893	Remote Similarity	NPD4092	Approved
0.689	Remote Similarity	NPD5839	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD1541	Approved
0.6872	Remote Similarity	NPD3990	Phase 3
0.6868	Remote Similarity	NPD3246	Discontinued
0.6862	Remote Similarity	NPD8050	Clinical (unspecified phase)
0.6859	Remote Similarity	NPD7207	Approved
0.6859	Remote Similarity	NPD7208	Approved
0.6859	Remote Similarity	NPD7209	Approved
0.6855	Remote Similarity	NPD5227	Clinical (unspecified phase)
0.6854	Remote Similarity	NPD7428	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD7088	Discontinued
0.6848	Remote Similarity	NPD5592	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD7441	Clinical (unspecified phase)
0.6846	Remote Similarity	NPD1668	Clinical (unspecified phase)
0.6845	Remote Similarity	NPD7572	Phase 2
0.6839	Remote Similarity	NPD2443	Approved
0.6839	Remote Similarity	NPD2442	Approved
0.6813	Remote Similarity	NPD5809	Phase 3
0.6811	Remote Similarity	NPD4922	Phase 2
0.6811	Remote Similarity	NPD7570	Approved
0.6811	Remote Similarity	NPD7569	Approved
0.6805	Remote Similarity	NPD4045	Phase 2
0.6805	Remote Similarity	NPD4042	Phase 2
0.6798	Remote Similarity	NPD3992	Approved
0.6798	Remote Similarity	NPD3994	Approved
0.6798	Remote Similarity	NPD3993	Approved
0.6798	Remote Similarity	NPD3991	Approved
0.6798	Remote Similarity	NPD7065	Clinical (unspecified phase)
0.6798	Remote Similarity	NPD3995	Approved
0.6798	Remote Similarity	NPD3996	Approved
0.679	Remote Similarity	NPD3625	Discontinued
0.6786	Remote Similarity	NPD5965	Clinical (unspecified phase)
0.6782	Remote Similarity	NPD4643	Clinical (unspecified phase)
0.678	Remote Similarity	NPD3522	Approved
0.6778	Remote Similarity	NPD2287	Clinical (unspecified phase)
0.6776	Remote Similarity	NPD4515	Suspended
0.6765	Remote Similarity	NPD7091	Discontinued
0.6765	Remote Similarity	NPD6855	Clinical (unspecified phase)
0.676	Remote Similarity	NPD3997	Approved
0.676	Remote Similarity	NPD3999	Approved
0.676	Remote Similarity	NPD3998	Approved
0.6757	Remote Similarity	NPD6180	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD1323	Discontinued
0.6755	Remote Similarity	NPD5446	Phase 2
0.6753	Remote Similarity	NPD4985	Clinical (unspecified phase)
0.675	Remote Similarity	NPD7192	Discontinued
0.675	Remote Similarity	NPD272	Approved
0.6744	Remote Similarity	NPD6454	Clinical (unspecified phase)
0.6742	Remote Similarity	NPD4385	Clinical (unspecified phase)
0.674	Remote Similarity	NPD3318	Approved
0.674	Remote Similarity	NPD3319	Phase 1
0.674	Remote Similarity	NPD3320	Approved
0.6738	Remote Similarity	NPD5853	Phase 3
0.6738	Remote Similarity	NPD5855	Phase 3
0.673	Remote Similarity	NPD7200	Approved
0.6722	Remote Similarity	NPD3927	Phase 2
0.672	Remote Similarity	NPD7786	Discontinued
0.672	Remote Similarity	NPD7995	Phase 2
0.6707	Remote Similarity	NPD5423	Phase 2
0.6702	Remote Similarity	NPD4848	Phase 1
0.6689	Remote Similarity	NPD1217	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD2791	Discontinued
0.6687	Remote Similarity	NPD175	Clinical (unspecified phase)
0.6685	Remote Similarity	NPD2770	Discontinued
0.6685	Remote Similarity	NPD4883	Approved
0.6684	Remote Similarity	NPD5854	Approved
0.6684	Remote Similarity	NPD7308	Discontinued
0.6667	Remote Similarity	NPD1952	Discontinued
0.6667	Remote Similarity	NPD1874	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7724	Phase 2
0.6667	Remote Similarity	NPD6395	Phase 2
0.6667	Remote Similarity	NPD6396	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD441	Approved
0.6649	Remote Similarity	NPD5489	Phase 1
0.6649	Remote Similarity	NPD5491	Phase 3
0.6649	Remote Similarity	NPD7024	Clinical (unspecified phase)
0.6649	Remote Similarity	NPD1284	Clinical (unspecified phase)
0.6648	Remote Similarity	NPD7401	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD6513	Approved
0.6646	Remote Similarity	NPD3482	Approved
0.6646	Remote Similarity	NPD6512	Approved
0.6645	Remote Similarity	NPD8128	Discontinued
0.6633	Remote Similarity	NPD2408	Discontinued
0.6632	Remote Similarity	NPD5856	Discontinued
0.663	Remote Similarity	NPD2479	Phase 3
0.663	Remote Similarity	NPD4330	Approved
0.663	Remote Similarity	NPD2481	Approved
0.663	Remote Similarity	NPD1291	Clinical (unspecified phase)
0.663	Remote Similarity	NPD4940	Approved
0.663	Remote Similarity	NPD4329	Approved
0.6626	Remote Similarity	NPD6606	Clinical (unspecified phase)
0.6616	Remote Similarity	NPD7656	Approved
0.6616	Remote Similarity	NPD7657	Approved
0.6615	Remote Similarity	NPD7817	Phase 1
0.6615	Remote Similarity	NPD3890	Phase 2
0.6615	Remote Similarity	NPD3891	Phase 2
0.6614	Remote Similarity	NPD1851	Clinical (unspecified phase)
0.6613	Remote Similarity	NPD1905	Clinical (unspecified phase)
0.6612	Remote Similarity	NPD8241	Phase 2
0.6611	Remote Similarity	NPD3792	Approved
0.6611	Remote Similarity	NPD5840	Discontinued
0.6606	Remote Similarity	NPD2129	Approved
0.6606	Remote Similarity	NPD2820	Phase 3
0.6606	Remote Similarity	NPD5527	Clinical (unspecified phase)
0.6606	Remote Similarity	NPD5526	Phase 2
0.66	Remote Similarity	NPD2464	Approved
0.66	Remote Similarity	NPD2467	Approved
0.66	Remote Similarity	NPD2463	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