NPASS Compound

Structure

CID312872 OpenBabel06191716122D 22 24 0 0 0 0 0 0 0 0999 V2000 -1.7321 1.0000 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 6.9282 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 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 5.1962 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 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 4.3301 -1.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 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 21 1 0 0 0 0 2 22 1 0 0 0 0 3 4 2 0 0 0 0 3 5 1 0 0 0 0 4 6 1 0 0 0 0 5 15 2 0 0 0 0 6 17 2 0 0 0 0 7 10 1 0 0 0 0 7 14 1 0 0 0 0 8 12 2 0 0 0 0 8 14 1 0 0 0 0 9 11 2 0 0 0 0 9 15 1 0 0 0 0 10 16 1 0 0 0 0 11 16 1 0 0 0 0 12 18 1 0 0 0 0 13 14 2 0 0 0 0 13 19 1 0 0 0 0 15 17 1 0 0 0 0 16 20 2 0 0 0 0 17 20 1 0 0 0 0 18 19 2 0 0 0 0 18 21 1 0 0 0 0 19 22 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	293.14
Volume:	318.996
LogP:	3.791
LogD:	3.625
LogS:	-4.401
# Rotatable Bonds:	5
TPSA:	31.35
# H-Bond Aceptor:	3
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.711
Synthetic Accessibility Score:	1.795
Fsp3:	0.211
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:	-4.916
MDCK Permeability:	1.569892447150778e-05
Pgp-inhibitor:	0.959
Pgp-substrate:	0.031
Human Intestinal Absorption (HIA):	0.002
20% Bioavailability (F20%):	0.695
30% Bioavailability (F30%):	0.718

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.493
Plasma Protein Binding (PPB):	97.21382904052734%
Volume Distribution (VD):	0.998
Pgp-substrate:	1.338606595993042%

ADMET: Metabolism

CYP1A2-inhibitor:	0.972
CYP1A2-substrate:	0.969
CYP2C19-inhibitor:	0.952
CYP2C19-substrate:	0.428
CYP2C9-inhibitor:	0.864
CYP2C9-substrate:	0.887
CYP2D6-inhibitor:	0.484
CYP2D6-substrate:	0.938
CYP3A4-inhibitor:	0.897
CYP3A4-substrate:	0.608

ADMET: Excretion

Clearance (CL):	6.764
Half-life (T1/2):	0.444

ADMET: Toxicity

hERG Blockers:	0.812
Human Hepatotoxicity (H-HT):	0.202
Drug-inuced Liver Injury (DILI):	0.353
AMES Toxicity:	0.546
Rat Oral Acute Toxicity:	0.057
Maximum Recommended Daily Dose:	0.692
Skin Sensitization:	0.713
Carcinogencity:	0.64
Eye Corrosion:	0.004
Eye Irritation:	0.28
Respiratory Toxicity:	0.483

Download Data

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

Natural Product: NPC312872

Natural Product ID:	NPC312872
*Common Name:**	2-(3,4-Dimethoxyphenylethyl)-Quinoleine
IUPAC Name:	2-[2-(3,4-dimethoxyphenyl)ethyl]quinoline
Synonyms:
Standard InCHIKey:	OXJATSFPAYFXMW-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C19H19NO2/c1-21-18-12-8-14(13-19(18)22-2)7-10-16-11-9-15-5-3-4-6-17(15)20-16/h3-6,8-9,11-13H,7,10H2,1-2H3
SMILES:	COc1ccc(CCc2ccc3ccccc3n2)cc1OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL458340
PubChem CID:	11483233
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001253] Quinolines 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
NPO17983	Nigrosabulum globosum	Species	Bionectriaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11374942]
NPO13657	Peperomia pellucida	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16499324]
NPO13657	Peperomia pellucida	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19680	Haminoea orteai	Species	Haminoeidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16032	Xanthoparmelia quintaria	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17983	Nigrosabulum globosum	Species	Bionectriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13657	Peperomia pellucida	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18972	Astropecten indicus	Species	Astropectinidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18402	Tecoma peroba	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17868	Eucryphia glutinosa	Species	Cunoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO83	Saccharina angustata	Species	Laminariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18897	Cephalosporium gregatum	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14518	Ateleia herbert-smithii	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16708	Pinus abies	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16452	Iochroma coccineum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19489	Tylosema esculentum	Species	Fabaceae	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
Others	2

Activity Type	# Activity
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1208	Organism	Leishmania braziliensis	Leishmania braziliensis	IC90	=	100.0	ug.mL-1	PMID[496141]
NPT580	Organism	Trypanosoma cruzi	Trypanosoma cruzi	IC90	=	100.0	ug.mL-1	PMID[496141]

☑ 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 NPC312872 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	580
0.1-0.2	3553
0.2-0.3	13617
0.3-0.4	3110
0.4-0.5	12607
0.5-0.6	7053
0.6-0.7	1784
0.7-0.8	360
0.8-0.85	24
0.85-0.9	6
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9455	High Similarity	NPC204385
0.9448	High Similarity	NPC206201
0.9051	High Similarity	NPC26850
0.8861	High Similarity	NPC26872
0.8736	High Similarity	NPC133140
0.8736	High Similarity	NPC195268
0.8598	High Similarity	NPC118511
0.8547	High Similarity	NPC476582
0.8547	High Similarity	NPC476578
0.8547	High Similarity	NPC4071
0.85	High Similarity	NPC234197
0.8415	Intermediate Similarity	NPC16452
0.8415	Intermediate Similarity	NPC476581
0.8415	Intermediate Similarity	NPC36229
0.8313	Intermediate Similarity	NPC177404
0.8297	Intermediate Similarity	NPC477019
0.8251	Intermediate Similarity	NPC31930
0.8226	Intermediate Similarity	NPC313189
0.8207	Intermediate Similarity	NPC135887
0.8207	Intermediate Similarity	NPC199277
0.815	Intermediate Similarity	NPC283152
0.8108	Intermediate Similarity	NPC66815
0.8105	Intermediate Similarity	NPC112206
0.8105	Intermediate Similarity	NPC296482
0.8105	Intermediate Similarity	NPC202605
0.8105	Intermediate Similarity	NPC53069
0.8105	Intermediate Similarity	NPC202768
0.809	Intermediate Similarity	NPC66083
0.8065	Intermediate Similarity	NPC223427
0.8032	Intermediate Similarity	NPC135549
0.8023	Intermediate Similarity	NPC62069
0.8011	Intermediate Similarity	NPC114335
0.8011	Intermediate Similarity	NPC280964
0.8011	Intermediate Similarity	NPC141915
0.801	Intermediate Similarity	NPC251160
0.8	Intermediate Similarity	NPC188420
0.8	Intermediate Similarity	NPC290689
0.8	Intermediate Similarity	NPC472168
0.7989	Intermediate Similarity	NPC288943
0.7978	Intermediate Similarity	NPC42591
0.7969	Intermediate Similarity	NPC149471
0.7969	Intermediate Similarity	NPC271215
0.7969	Intermediate Similarity	NPC266931
0.7923	Intermediate Similarity	NPC131017
0.7919	Intermediate Similarity	NPC280272
0.7917	Intermediate Similarity	NPC96405
0.7917	Intermediate Similarity	NPC171409
0.7892	Intermediate Similarity	NPC72211
0.7876	Intermediate Similarity	NPC236668
0.7872	Intermediate Similarity	NPC162484
0.7865	Intermediate Similarity	NPC176127
0.7845	Intermediate Similarity	NPC242928
0.7838	Intermediate Similarity	NPC70956
0.7838	Intermediate Similarity	NPC243834
0.7835	Intermediate Similarity	NPC235076
0.7835	Intermediate Similarity	NPC146976
0.7821	Intermediate Similarity	NPC84478
0.7816	Intermediate Similarity	NPC258773
0.7809	Intermediate Similarity	NPC474798
0.7807	Intermediate Similarity	NPC11017
0.7807	Intermediate Similarity	NPC329747
0.7806	Intermediate Similarity	NPC100079
0.7806	Intermediate Similarity	NPC23614
0.7789	Intermediate Similarity	NPC304183
0.7784	Intermediate Similarity	NPC70259
0.7772	Intermediate Similarity	NPC279401
0.7772	Intermediate Similarity	NPC79293
0.7753	Intermediate Similarity	NPC168486
0.7753	Intermediate Similarity	NPC222592
0.7737	Intermediate Similarity	NPC285558
0.773	Intermediate Similarity	NPC43787
0.773	Intermediate Similarity	NPC205934
0.7727	Intermediate Similarity	NPC174049
0.772	Intermediate Similarity	NPC219664
0.7716	Intermediate Similarity	NPC204446
0.7713	Intermediate Similarity	NPC329793
0.7711	Intermediate Similarity	NPC200888
0.7708	Intermediate Similarity	NPC470931
0.7692	Intermediate Similarity	NPC162530
0.7677	Intermediate Similarity	NPC46451
0.7672	Intermediate Similarity	NPC267423
0.766	Intermediate Similarity	NPC287437
0.7656	Intermediate Similarity	NPC193777
0.7654	Intermediate Similarity	NPC478032
0.765	Intermediate Similarity	NPC122463
0.7644	Intermediate Similarity	NPC264166
0.7644	Intermediate Similarity	NPC274291
0.7644	Intermediate Similarity	NPC47059
0.7644	Intermediate Similarity	NPC165349
0.7644	Intermediate Similarity	NPC329708
0.7644	Intermediate Similarity	NPC118832
0.7641	Intermediate Similarity	NPC203168
0.7632	Intermediate Similarity	NPC475085
0.7632	Intermediate Similarity	NPC475112
0.7632	Intermediate Similarity	NPC291535
0.7629	Intermediate Similarity	NPC199667
0.7629	Intermediate Similarity	NPC470020
0.7626	Intermediate Similarity	NPC473822
0.7622	Intermediate Similarity	NPC60553
0.7609	Intermediate Similarity	NPC76748
0.7604	Intermediate Similarity	NPC472111
0.7592	Intermediate Similarity	NPC475774
0.7586	Intermediate Similarity	NPC24954
0.7581	Intermediate Similarity	NPC307963
0.7579	Intermediate Similarity	NPC476044
0.7577	Intermediate Similarity	NPC201697
0.7577	Intermediate Similarity	NPC469589
0.7577	Intermediate Similarity	NPC473181
0.7576	Intermediate Similarity	NPC473513
0.7568	Intermediate Similarity	NPC92111
0.7568	Intermediate Similarity	NPC469390
0.7566	Intermediate Similarity	NPC128823
0.7562	Intermediate Similarity	NPC118121
0.7562	Intermediate Similarity	NPC210434
0.7554	Intermediate Similarity	NPC296527
0.7552	Intermediate Similarity	NPC470930
0.7552	Intermediate Similarity	NPC137929
0.7552	Intermediate Similarity	NPC164374
0.7551	Intermediate Similarity	NPC316981
0.7542	Intermediate Similarity	NPC285941
0.7541	Intermediate Similarity	NPC61350
0.7538	Intermediate Similarity	NPC471304
0.7538	Intermediate Similarity	NPC173080
0.7526	Intermediate Similarity	NPC176538
0.7526	Intermediate Similarity	NPC475910
0.7513	Intermediate Similarity	NPC476106
0.7513	Intermediate Similarity	NPC323345
0.7513	Intermediate Similarity	NPC470164
0.75	Intermediate Similarity	NPC295228
0.75	Intermediate Similarity	NPC208284
0.75	Intermediate Similarity	NPC44161
0.75	Intermediate Similarity	NPC148409
0.7487	Intermediate Similarity	NPC475190
0.7487	Intermediate Similarity	NPC232727
0.7487	Intermediate Similarity	NPC470586
0.7474	Intermediate Similarity	NPC474595
0.7462	Intermediate Similarity	NPC48353
0.746	Intermediate Similarity	NPC267928
0.746	Intermediate Similarity	NPC474188
0.7449	Intermediate Similarity	NPC123976
0.7449	Intermediate Similarity	NPC167860
0.7448	Intermediate Similarity	NPC295898
0.7436	Intermediate Similarity	NPC82548
0.7435	Intermediate Similarity	NPC315957
0.7427	Intermediate Similarity	NPC24019
0.7424	Intermediate Similarity	NPC469592
0.7424	Intermediate Similarity	NPC471080
0.7414	Intermediate Similarity	NPC285635
0.7409	Intermediate Similarity	NPC245816
0.7409	Intermediate Similarity	NPC469440
0.7409	Intermediate Similarity	NPC476138
0.7407	Intermediate Similarity	NPC251090
0.7404	Intermediate Similarity	NPC473182
0.7398	Intermediate Similarity	NPC174758
0.7379	Intermediate Similarity	NPC476997
0.7374	Intermediate Similarity	NPC264176
0.7374	Intermediate Similarity	NPC472098
0.7374	Intermediate Similarity	NPC473180
0.7374	Intermediate Similarity	NPC94157
0.7368	Intermediate Similarity	NPC253675
0.7343	Intermediate Similarity	NPC476996
0.7343	Intermediate Similarity	NPC476998
0.7337	Intermediate Similarity	NPC478074
0.7333	Intermediate Similarity	NPC300156
0.7333	Intermediate Similarity	NPC45190
0.733	Intermediate Similarity	NPC127085
0.7327	Intermediate Similarity	NPC473179
0.7322	Intermediate Similarity	NPC190461
0.7322	Intermediate Similarity	NPC118776
0.731	Intermediate Similarity	NPC209769
0.7308	Intermediate Similarity	NPC201508
0.7308	Intermediate Similarity	NPC476999
0.7308	Intermediate Similarity	NPC88363
0.7302	Intermediate Similarity	NPC230403
0.7299	Intermediate Similarity	NPC473183
0.7297	Intermediate Similarity	NPC94943
0.7296	Intermediate Similarity	NPC193238
0.7296	Intermediate Similarity	NPC4687
0.7296	Intermediate Similarity	NPC249583
0.7295	Intermediate Similarity	NPC476994
0.7293	Intermediate Similarity	NPC56618
0.7293	Intermediate Similarity	NPC84347
0.7286	Intermediate Similarity	NPC473184
0.7277	Intermediate Similarity	NPC96321
0.7277	Intermediate Similarity	NPC469594
0.7277	Intermediate Similarity	NPC473041
0.7277	Intermediate Similarity	NPC224928
0.7268	Intermediate Similarity	NPC287588
0.7263	Intermediate Similarity	NPC473764
0.7263	Intermediate Similarity	NPC477888
0.7263	Intermediate Similarity	NPC314940
0.726	Intermediate Similarity	NPC278525
0.7258	Intermediate Similarity	NPC276674
0.7258	Intermediate Similarity	NPC314573
0.7258	Intermediate Similarity	NPC33902
0.7254	Intermediate Similarity	NPC19872
0.7249	Intermediate Similarity	NPC99666
0.7243	Intermediate Similarity	NPC190007
0.7241	Intermediate Similarity	NPC213530
0.7241	Intermediate Similarity	NPC193267

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 NPC312872 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	357
0.1-0.2	759
0.2-0.3	871
0.3-0.4	1094
0.4-0.5	2668
0.5-0.6	2436
0.6-0.7	815
0.7-0.8	141
0.8-0.85	4
0.85-0.9	4
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9325	High Similarity	NPD3920	Phase 2
0.8736	High Similarity	NPD3922	Approved
0.8736	High Similarity	NPD3923	Approved
0.8736	High Similarity	NPD3924	Approved
0.8736	High Similarity	NPD3921	Approved
0.8655	High Similarity	NPD5083	Clinical (unspecified phase)
0.8478	Intermediate Similarity	NPD5658	Approved
0.84	Intermediate Similarity	NPD6257	Clinical (unspecified phase)
0.8222	Intermediate Similarity	NPD6590	Discontinued
0.8177	Intermediate Similarity	NPD6550	Discontinued
0.814	Intermediate Similarity	NPD1923	Clinical (unspecified phase)
0.8105	Intermediate Similarity	NPD3816	Phase 1
0.8105	Intermediate Similarity	NPD3815	Phase 1
0.8077	Intermediate Similarity	NPD5512	Phase 3
0.8033	Intermediate Similarity	NPD6988	Phase 1
0.8022	Intermediate Similarity	NPD4418	Discontinued
0.8022	Intermediate Similarity	NPD6491	Clinical (unspecified phase)
0.8022	Intermediate Similarity	NPD6861	Clinical (unspecified phase)
0.7978	Intermediate Similarity	NPD4889	Approved
0.7937	Intermediate Similarity	NPD7222	Phase 2
0.7937	Intermediate Similarity	NPD5429	Discontinued
0.791	Intermediate Similarity	NPD7414	Clinical (unspecified phase)
0.791	Intermediate Similarity	NPD4204	Approved
0.791	Intermediate Similarity	NPD4203	Approved
0.7907	Intermediate Similarity	NPD6872	Clinical (unspecified phase)
0.7903	Intermediate Similarity	NPD6219	Discontinued
0.7861	Intermediate Similarity	NPD4724	Clinical (unspecified phase)
0.7849	Intermediate Similarity	NPD4118	Clinical (unspecified phase)
0.7819	Intermediate Similarity	NPD5669	Clinical (unspecified phase)
0.7817	Intermediate Similarity	NPD5930	Phase 3
0.7817	Intermediate Similarity	NPD5070	Clinical (unspecified phase)
0.7814	Intermediate Similarity	NPD6569	Phase 2
0.7784	Intermediate Similarity	NPD7571	Clinical (unspecified phase)
0.7749	Intermediate Similarity	NPD7453	Approved
0.7749	Intermediate Similarity	NPD7452	Approved
0.7709	Intermediate Similarity	NPD3386	Phase 2
0.7705	Intermediate Similarity	NPD2410	Phase 2
0.7696	Intermediate Similarity	NPD5530	Phase 1
0.768	Intermediate Similarity	NPD4502	Phase 2
0.7677	Intermediate Similarity	NPD3763	Approved
0.7667	Intermediate Similarity	NPD5522	Clinical (unspecified phase)
0.7662	Intermediate Similarity	NPD7719	Discontinued
0.7647	Intermediate Similarity	NPD6769	Clinical (unspecified phase)
0.7644	Intermediate Similarity	NPD31	Approved
0.7644	Intermediate Similarity	NPD4034	Approved
0.7644	Intermediate Similarity	NPD4033	Approved
0.7644	Intermediate Similarity	NPD4036	Approved
0.7644	Intermediate Similarity	NPD4035	Approved
0.7644	Intermediate Similarity	NPD32	Approved
0.7644	Intermediate Similarity	NPD4122	Approved
0.7644	Intermediate Similarity	NPD4037	Approved
0.7644	Intermediate Similarity	NPD4039	Approved
0.7644	Intermediate Similarity	NPD4038	Approved
0.764	Intermediate Similarity	NPD6159	Phase 2
0.7637	Intermediate Similarity	NPD2917	Approved
0.7634	Intermediate Similarity	NPD3324	Clinical (unspecified phase)
0.7627	Intermediate Similarity	NPD5602	Clinical (unspecified phase)
0.7614	Intermediate Similarity	NPD4083	Discontinued
0.761	Intermediate Similarity	NPD4885	Approved
0.7586	Intermediate Similarity	NPD2782	Approved
0.7586	Intermediate Similarity	NPD2780	Approved
0.7582	Intermediate Similarity	NPD6344	Clinical (unspecified phase)
0.7581	Intermediate Similarity	NPD1304	Clinical (unspecified phase)
0.7581	Intermediate Similarity	NPD1038	Approved
0.7574	Intermediate Similarity	NPD6476	Clinical (unspecified phase)
0.7574	Intermediate Similarity	NPD6158	Phase 2
0.7574	Intermediate Similarity	NPD2883	Discontinued
0.7573	Intermediate Similarity	NPD6494	Phase 2
0.7571	Intermediate Similarity	NPD677	Clinical (unspecified phase)
0.7563	Intermediate Similarity	NPD5902	Approved
0.7563	Intermediate Similarity	NPD5903	Approved
0.7562	Intermediate Similarity	NPD1954	Phase 1
0.7551	Intermediate Similarity	NPD7069	Discontinued
0.754	Intermediate Similarity	NPD6251	Discontinued
0.7514	Intermediate Similarity	NPD9705	Discontinued
0.7514	Intermediate Similarity	NPD112	Approved
0.7513	Intermediate Similarity	NPD4305	Clinical (unspecified phase)
0.7513	Intermediate Similarity	NPD6150	Discontinued
0.75	Intermediate Similarity	NPD2781	Approved
0.75	Intermediate Similarity	NPD6991	Approved
0.75	Intermediate Similarity	NPD3478	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD3477	Phase 2
0.7485	Intermediate Similarity	NPD1305	Clinical (unspecified phase)
0.7474	Intermediate Similarity	NPD3541	Clinical (unspecified phase)
0.7474	Intermediate Similarity	NPD3825	Phase 3
0.7471	Intermediate Similarity	NPD2882	Phase 1
0.7461	Intermediate Similarity	NPD4795	Phase 2
0.7452	Intermediate Similarity	NPD6964	Approved
0.7452	Intermediate Similarity	NPD6963	Approved
0.745	Intermediate Similarity	NPD7395	Discontinued
0.7437	Intermediate Similarity	NPD5612	Discontinued
0.7435	Intermediate Similarity	NPD1740	Approved
0.7435	Intermediate Similarity	NPD1739	Approved
0.7423	Intermediate Similarity	NPD3842	Clinical (unspecified phase)
0.7423	Intermediate Similarity	NPD3003	Approved
0.7416	Intermediate Similarity	NPD5680	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD2749	Discontinued
0.74	Intermediate Similarity	NPD3440	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD4996	Approved
0.7391	Intermediate Similarity	NPD4995	Approved
0.7387	Intermediate Similarity	NPD6140	Clinical (unspecified phase)
0.738	Intermediate Similarity	NPD2334	Discontinued
0.7374	Intermediate Similarity	NPD4927	Discontinued
0.7358	Intermediate Similarity	NPD6477	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD6208	Discontinued
0.7354	Intermediate Similarity	NPD3396	Approved
0.7354	Intermediate Similarity	NPD3810	Clinical (unspecified phase)
0.7354	Intermediate Similarity	NPD3395	Approved
0.7351	Intermediate Similarity	NPD4375	Approved
0.7347	Intermediate Similarity	NPD7671	Approved
0.7347	Intermediate Similarity	NPD7672	Approved
0.7346	Intermediate Similarity	NPD7729	Clinical (unspecified phase)
0.7343	Intermediate Similarity	NPD1900	Clinical (unspecified phase)
0.7343	Intermediate Similarity	NPD4925	Approved
0.7333	Intermediate Similarity	NPD8403	Phase 1
0.7323	Intermediate Similarity	NPD6220	Phase 3
0.7282	Intermediate Similarity	NPD3397	Phase 2
0.7277	Intermediate Similarity	NPD4429	Discontinued
0.7259	Intermediate Similarity	NPD5863	Clinical (unspecified phase)
0.7259	Intermediate Similarity	NPD5529	Phase 1
0.7259	Intermediate Similarity	NPD5528	Clinical (unspecified phase)
0.7256	Intermediate Similarity	NPD6230	Discontinued
0.7253	Intermediate Similarity	NPD4072	Approved
0.7253	Intermediate Similarity	NPD4071	Approved
0.7253	Intermediate Similarity	NPD5670	Approved
0.7249	Intermediate Similarity	NPD4372	Phase 1
0.7243	Intermediate Similarity	NPD4875	Phase 3
0.7243	Intermediate Similarity	NPD4876	Phase 3
0.7236	Intermediate Similarity	NPD5067	Phase 2
0.7236	Intermediate Similarity	NPD5416	Discontinued
0.7236	Intermediate Similarity	NPD6567	Clinical (unspecified phase)
0.7236	Intermediate Similarity	NPD5066	Phase 2
0.723	Intermediate Similarity	NPD5905	Phase 1
0.722	Intermediate Similarity	NPD6824	Clinical (unspecified phase)
0.7217	Intermediate Similarity	NPD5805	Approved
0.7216	Intermediate Similarity	NPD2358	Clinical (unspecified phase)
0.7213	Intermediate Similarity	NPD1503	Clinical (unspecified phase)
0.7213	Intermediate Similarity	NPD1620	Clinical (unspecified phase)
0.7211	Intermediate Similarity	NPD4551	Phase 2
0.7206	Intermediate Similarity	NPD7678	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD2177	Approved
0.7202	Intermediate Similarity	NPD2175	Phase 3
0.7202	Intermediate Similarity	NPD2176	Approved
0.7202	Intermediate Similarity	NPD4548	Discontinued
0.7202	Intermediate Similarity	NPD1768	Approved
0.7194	Intermediate Similarity	NPD3946	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD4899	Clinical (unspecified phase)
0.7178	Intermediate Similarity	NPD6147	Clinical (unspecified phase)
0.7166	Intermediate Similarity	NPD5256	Discontinued
0.7158	Intermediate Similarity	NPD3503	Approved
0.7158	Intermediate Similarity	NPD3504	Approved
0.7157	Intermediate Similarity	NPD7194	Discontinued
0.7151	Intermediate Similarity	NPD5917	Clinical (unspecified phase)
0.715	Intermediate Similarity	NPD7468	Clinical (unspecified phase)
0.715	Intermediate Similarity	NPD4131	Phase 3
0.7143	Intermediate Similarity	NPD5966	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7823	Clinical (unspecified phase)
0.7136	Intermediate Similarity	NPD1856	Discontinued
0.7129	Intermediate Similarity	NPD3257	Approved
0.7129	Intermediate Similarity	NPD5417	Clinical (unspecified phase)
0.7129	Intermediate Similarity	NPD7538	Clinical (unspecified phase)
0.7122	Intermediate Similarity	NPD6242	Discontinued
0.7121	Intermediate Similarity	NPD6290	Phase 2
0.712	Intermediate Similarity	NPD6046	Clinical (unspecified phase)
0.712	Intermediate Similarity	NPD6361	Phase 2
0.7118	Intermediate Similarity	NPD3301	Approved
0.7114	Intermediate Similarity	NPD5866	Approved
0.7113	Intermediate Similarity	NPD5999	Phase 2
0.7108	Intermediate Similarity	NPD3354	Phase 2
0.7105	Intermediate Similarity	NPD5641	Discontinued
0.7104	Intermediate Similarity	NPD4354	Approved
0.7102	Intermediate Similarity	NPD2581	Approved
0.7102	Intermediate Similarity	NPD2582	Approved
0.7102	Intermediate Similarity	NPD4671	Clinical (unspecified phase)
0.7102	Intermediate Similarity	NPD4670	Clinical (unspecified phase)
0.7102	Intermediate Similarity	NPD4669	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD5022	Discontinued
0.7088	Intermediate Similarity	NPD6607	Clinical (unspecified phase)
0.7085	Intermediate Similarity	NPD2189	Approved
0.7085	Intermediate Similarity	NPD2739	Clinical (unspecified phase)
0.7085	Intermediate Similarity	NPD2187	Approved
0.7083	Intermediate Similarity	NPD6517	Phase 3
0.7083	Intermediate Similarity	NPD5051	Phase 1
0.7081	Intermediate Similarity	NPD2599	Approved
0.7081	Intermediate Similarity	NPD6553	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD2601	Approved
0.7081	Intermediate Similarity	NPD2600	Approved
0.7079	Intermediate Similarity	NPD1684	Approved
0.7079	Intermediate Similarity	NPD1685	Approved
0.7077	Intermediate Similarity	NPD4396	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD3258	Approved
0.707	Intermediate Similarity	NPD7025	Clinical (unspecified phase)
0.7065	Intermediate Similarity	NPD5751	Clinical (unspecified phase)
0.7065	Intermediate Similarity	NPD5936	Approved
0.7065	Intermediate Similarity	NPD7703	Clinical (unspecified phase)
0.7065	Intermediate Similarity	NPD5939	Approved
0.7062	Intermediate Similarity	NPD6060	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD3525	Discontinued
0.7056	Intermediate Similarity	NPD6324	Phase 1
0.7053	Intermediate Similarity	NPD2285	Clinical (unspecified phase)

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