NPASS Compound

Structure

NPC174049 OpenBabel07101718332D 23 26 0 0 0 0 0 0 0 0999 V2000 -1.8122 0.4081 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5527 1.7735 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.7321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0470 -0.8443 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1810 -0.3443 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6251 -2.3624 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0373 -3.1714 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1810 -2.3443 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0470 -1.8443 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3150 -0.8443 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2184 -1.4488 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3150 -1.8443 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7761 -1.3443 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3639 -0.5353 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3639 -2.1533 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4581 -0.6718 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8109 0.0608 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9572 -3.0669 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 4.9131 -2.3443 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4469 -0.5228 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.1762 0.9916 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5000 0.8660 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 23 1 0 0 0 0 4 5 2 0 0 0 0 4 9 1 0 0 0 0 5 10 1 0 0 0 0 6 7 2 0 0 0 0 6 11 1 0 0 0 0 7 19 1 0 0 0 0 8 9 2 0 0 0 0 8 12 1 0 0 0 0 9 20 1 0 0 0 0 10 12 2 0 0 0 0 10 14 1 0 0 0 0 11 13 2 0 0 0 0 11 16 1 0 0 0 0 12 15 1 0 0 0 0 13 14 1 0 0 0 0 13 15 1 0 0 0 0 14 17 2 0 0 0 0 15 19 2 0 0 0 0 16 18 2 0 0 0 0 16 21 1 0 0 0 0 17 18 1 0 0 0 0 17 22 1 0 0 0 0 18 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	309.1
Volume:	310.724
LogP:	2.844
LogD:	2.823
LogS:	-4.227
# Rotatable Bonds:	3
TPSA:	60.81
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.626
Synthetic Accessibility Score:	2.598
Fsp3:	0.167
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:	-4.705
MDCK Permeability:	1.8920047295978293e-05
Pgp-inhibitor:	0.006
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.011
20% Bioavailability (F20%):	0.001
30% Bioavailability (F30%):	0.001

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.017
Plasma Protein Binding (PPB):	89.21800994873047%
Volume Distribution (VD):	0.643
Pgp-substrate:	8.725679397583008%

ADMET: Metabolism

CYP1A2-inhibitor:	0.65
CYP1A2-substrate:	0.966
CYP2C19-inhibitor:	0.607
CYP2C19-substrate:	0.577
CYP2C9-inhibitor:	0.216
CYP2C9-substrate:	0.906
CYP2D6-inhibitor:	0.138
CYP2D6-substrate:	0.906
CYP3A4-inhibitor:	0.582
CYP3A4-substrate:	0.324

ADMET: Excretion

Clearance (CL):	4.016
Half-life (T1/2):	0.358

ADMET: Toxicity

hERG Blockers:	0.218
Human Hepatotoxicity (H-HT):	0.179
Drug-inuced Liver Injury (DILI):	0.942
AMES Toxicity:	0.662
Rat Oral Acute Toxicity:	0.431
Maximum Recommended Daily Dose:	0.084
Skin Sensitization:	0.124
Carcinogencity:	0.108
Eye Corrosion:	0.006
Eye Irritation:	0.586
Respiratory Toxicity:	0.854

Download Data

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

Natural Product: NPC174049

Natural Product ID:	NPC174049
*Common Name:**	Imerubrine
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	NEVBZBLAKXUEPJ-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C18H15NO4/c1-21-16-11-6-7-19-15-12-8-9(20)4-5-10(12)14(13(11)15)17(22-2)18(16)23-3/h4-8,20H,1-3H3
SMILES:	COc1c2c3c(c4c2ccc(c4)O)nccc3c(c1OC)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL155844
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0002566] Isoquinolines 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
NPO1525	Pericampylus glaucus	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18396905]
NPO1525	Pericampylus glaucus	Species	Menispermaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[18396905]
NPO1525	Pericampylus glaucus	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1525	Pericampylus glaucus	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1525	Pericampylus glaucus	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
EC50	1
IC50	3
Others	4

Activity Type	# Activity
Cell Line	2
Organism	3
Others	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT168	Cell Line	P388	Mus musculus	IC50	=	1.2	ug.mL-1	PMID[485651]
NPT1452	Cell Line	C8166	Homo sapiens	CC50	=	493000.0	nM	PMID[485652]
NPT2	Others	Unspecified		Ratio CC50/IC50	>	4.17	n.a.	PMID[485652]
NPT963	Organism	Hepatitis B virus	Hepatitis B virus	IC50	=	930000.0	nM	PMID[485652]
NPT27	Others	Unspecified		CC50	>	3880000.0	nM	PMID[485652]
NPT963	Organism	Hepatitis B virus	Hepatitis B virus	IC50	>	3880000.0	nM	PMID[485652]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	EC50	=	10900.0	nM	PMID[485652]
NPT2	Others	Unspecified		Ratio CC50/EC50	=	45.74	n.a.	PMID[485652]

☑ 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 NPC174049 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	639
0.1-0.2	2893
0.2-0.3	12808
0.3-0.4	4785
0.4-0.5	9926
0.5-0.6	9259
0.6-0.7	2058
0.7-0.8	245
0.8-0.85	63
0.85-0.9	14
0.9-0.95	6
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9029	High Similarity	NPC122463
0.902	High Similarity	NPC473822
0.8731	High Similarity	NPC224928
0.8683	High Similarity	NPC112206
0.8683	High Similarity	NPC202605
0.8645	High Similarity	NPC201508
0.8622	High Similarity	NPC195268
0.8622	High Similarity	NPC133140
0.8565	High Similarity	NPC255800
0.8565	High Similarity	NPC96584
0.8522	High Similarity	NPC36229
0.8522	High Similarity	NPC16452
0.8522	High Similarity	NPC476581
0.8458	Intermediate Similarity	NPC4071
0.8458	Intermediate Similarity	NPC476582
0.8458	Intermediate Similarity	NPC476578
0.8416	Intermediate Similarity	NPC217554
0.8404	Intermediate Similarity	NPC118121
0.8389	Intermediate Similarity	NPC204446
0.8386	Intermediate Similarity	NPC284141
0.8374	Intermediate Similarity	NPC31930
0.8341	Intermediate Similarity	NPC15406
0.8326	Intermediate Similarity	NPC11408
0.8325	Intermediate Similarity	NPC234197
0.8325	Intermediate Similarity	NPC296482
0.8325	Intermediate Similarity	NPC477019
0.8325	Intermediate Similarity	NPC202768
0.8325	Intermediate Similarity	NPC53069
0.8319	Intermediate Similarity	NPC134637
0.8295	Intermediate Similarity	NPC476997
0.8276	Intermediate Similarity	NPC287437
0.8261	Intermediate Similarity	NPC313189
0.8257	Intermediate Similarity	NPC476996
0.8257	Intermediate Similarity	NPC476998
0.8246	Intermediate Similarity	NPC235076
0.8238	Intermediate Similarity	NPC171409
0.8238	Intermediate Similarity	NPC251160
0.8238	Intermediate Similarity	NPC96405
0.823	Intermediate Similarity	NPC188420
0.8211	Intermediate Similarity	NPC476994
0.8202	Intermediate Similarity	NPC183537
0.8182	Intermediate Similarity	NPC233334
0.8173	Intermediate Similarity	NPC135549
0.8164	Intermediate Similarity	NPC164374
0.8164	Intermediate Similarity	NPC137929
0.8131	Intermediate Similarity	NPC100079
0.8131	Intermediate Similarity	NPC23614
0.8125	Intermediate Similarity	NPC323345
0.8125	Intermediate Similarity	NPC470164
0.8122	Intermediate Similarity	NPC77878
0.8113	Intermediate Similarity	NPC271215
0.8113	Intermediate Similarity	NPC149471
0.8108	Intermediate Similarity	NPC90875
0.8093	Intermediate Similarity	NPC46451
0.8091	Intermediate Similarity	NPC469792
0.8069	Intermediate Similarity	NPC114335
0.8069	Intermediate Similarity	NPC141915
0.8069	Intermediate Similarity	NPC280964
0.8057	Intermediate Similarity	NPC290689
0.803	Intermediate Similarity	NPC329541
0.8028	Intermediate Similarity	NPC266931
0.8009	Intermediate Similarity	NPC210296
0.7982	Intermediate Similarity	NPC124313
0.7974	Intermediate Similarity	NPC207283
0.7974	Intermediate Similarity	NPC84164
0.7964	Intermediate Similarity	NPC246381
0.7956	Intermediate Similarity	NPC476995
0.7955	Intermediate Similarity	NPC200888
0.7931	Intermediate Similarity	NPC469390
0.7928	Intermediate Similarity	NPC24019
0.7926	Intermediate Similarity	NPC148409
0.791	Intermediate Similarity	NPC61350
0.786	Intermediate Similarity	NPC236668
0.7857	Intermediate Similarity	NPC469440
0.7851	Intermediate Similarity	NPC119134
0.7832	Intermediate Similarity	NPC108342
0.7832	Intermediate Similarity	NPC295228
0.7824	Intermediate Similarity	NPC146976
0.7818	Intermediate Similarity	NPC210434
0.7812	Intermediate Similarity	NPC476999
0.7798	Intermediate Similarity	NPC173080
0.7797	Intermediate Similarity	NPC182907
0.7797	Intermediate Similarity	NPC189903
0.7783	Intermediate Similarity	NPC304183
0.7763	Intermediate Similarity	NPC166722
0.7727	Intermediate Similarity	NPC312872
0.7696	Intermediate Similarity	NPC474594
0.7692	Intermediate Similarity	NPC473053
0.7665	Intermediate Similarity	NPC22481
0.7653	Intermediate Similarity	NPC210256
0.765	Intermediate Similarity	NPC316981
0.7647	Intermediate Similarity	NPC54066
0.7642	Intermediate Similarity	NPC66815
0.7639	Intermediate Similarity	NPC470020
0.7635	Intermediate Similarity	NPC62069
0.7611	Intermediate Similarity	NPC278525
0.7604	Intermediate Similarity	NPC208284
0.7585	Intermediate Similarity	NPC302807
0.7581	Intermediate Similarity	NPC474595
0.7578	Intermediate Similarity	NPC280272
0.757	Intermediate Similarity	NPC274291
0.757	Intermediate Similarity	NPC47059
0.757	Intermediate Similarity	NPC264166
0.757	Intermediate Similarity	NPC118832
0.757	Intermediate Similarity	NPC329708
0.757	Intermediate Similarity	NPC165349
0.7558	Intermediate Similarity	NPC11464
0.7537	Intermediate Similarity	NPC206201
0.7536	Intermediate Similarity	NPC127085
0.7534	Intermediate Similarity	NPC162530
0.7523	Intermediate Similarity	NPC193267
0.7523	Intermediate Similarity	NPC213530
0.7512	Intermediate Similarity	NPC289786
0.7511	Intermediate Similarity	NPC473513
0.7489	Intermediate Similarity	NPC107123
0.7478	Intermediate Similarity	NPC253675
0.7478	Intermediate Similarity	NPC214980
0.7477	Intermediate Similarity	NPC135887
0.7477	Intermediate Similarity	NPC199277
0.7476	Intermediate Similarity	NPC204385
0.7469	Intermediate Similarity	NPC129897
0.7455	Intermediate Similarity	NPC310118
0.7445	Intermediate Similarity	NPC110151
0.7442	Intermediate Similarity	NPC475774
0.7441	Intermediate Similarity	NPC251090
0.744	Intermediate Similarity	NPC180253
0.744	Intermediate Similarity	NPC219170
0.7419	Intermediate Similarity	NPC193777
0.7418	Intermediate Similarity	NPC132385
0.7407	Intermediate Similarity	NPC285558
0.7361	Intermediate Similarity	NPC223427
0.7356	Intermediate Similarity	NPC66083
0.7353	Intermediate Similarity	NPC270515
0.7346	Intermediate Similarity	NPC279401
0.7346	Intermediate Similarity	NPC307963
0.7346	Intermediate Similarity	NPC79293
0.7343	Intermediate Similarity	NPC276060
0.7339	Intermediate Similarity	NPC193238
0.7339	Intermediate Similarity	NPC473183
0.733	Intermediate Similarity	NPC203168
0.7324	Intermediate Similarity	NPC70956
0.7324	Intermediate Similarity	NPC243834
0.7321	Intermediate Similarity	NPC22928
0.7321	Intermediate Similarity	NPC320088
0.7318	Intermediate Similarity	NPC219664
0.7309	Intermediate Similarity	NPC8022
0.7309	Intermediate Similarity	NPC170114
0.7309	Intermediate Similarity	NPC470799
0.7306	Intermediate Similarity	NPC470931
0.7302	Intermediate Similarity	NPC176538
0.7299	Intermediate Similarity	NPC99666
0.7294	Intermediate Similarity	NPC472111
0.7265	Intermediate Similarity	NPC470549
0.7257	Intermediate Similarity	NPC469439
0.7253	Intermediate Similarity	NPC473184
0.7252	Intermediate Similarity	NPC48353
0.7246	Intermediate Similarity	NPC192939
0.7246	Intermediate Similarity	NPC215747
0.7243	Intermediate Similarity	NPC318068
0.724	Intermediate Similarity	NPC167860
0.724	Intermediate Similarity	NPC123976
0.7238	Intermediate Similarity	NPC296527
0.723	Intermediate Similarity	NPC85381
0.7227	Intermediate Similarity	NPC82548
0.7227	Intermediate Similarity	NPC208522
0.7225	Intermediate Similarity	NPC276674
0.7225	Intermediate Similarity	NPC33902
0.722	Intermediate Similarity	NPC283152
0.7217	Intermediate Similarity	NPC318805
0.7217	Intermediate Similarity	NPC41122
0.721	Intermediate Similarity	NPC473182
0.7204	Intermediate Similarity	NPC76748
0.7198	Intermediate Similarity	NPC260118
0.7198	Intermediate Similarity	NPC190461
0.7189	Intermediate Similarity	NPC232727
0.7179	Intermediate Similarity	NPC277351
0.7177	Intermediate Similarity	NPC28425
0.7177	Intermediate Similarity	NPC42591
0.7174	Intermediate Similarity	NPC470018
0.7171	Intermediate Similarity	NPC288943
0.717	Intermediate Similarity	NPC92111
0.7169	Intermediate Similarity	NPC475070
0.7162	Intermediate Similarity	NPC322482
0.7156	Intermediate Similarity	NPC475112
0.7156	Intermediate Similarity	NPC475085
0.7156	Intermediate Similarity	NPC291535
0.715	Intermediate Similarity	NPC177404
0.715	Intermediate Similarity	NPC131017
0.715	Intermediate Similarity	NPC29472
0.715	Intermediate Similarity	NPC265383
0.7149	Intermediate Similarity	NPC18348
0.7143	Intermediate Similarity	NPC74575
0.7143	Intermediate Similarity	NPC473185
0.7129	Intermediate Similarity	NPC119579
0.7123	Intermediate Similarity	NPC3715
0.7117	Intermediate Similarity	NPC174672
0.7117	Intermediate Similarity	NPC185782
0.7117	Intermediate Similarity	NPC174758
0.7117	Intermediate Similarity	NPC469589
0.7114	Intermediate Similarity	NPC473057

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 NPC174049 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	344
0.1-0.2	669
0.2-0.3	918
0.3-0.4	1617
0.4-0.5	2653
0.5-0.6	2228
0.6-0.7	638
0.7-0.8	77
0.8-0.85	4
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8622	High Similarity	NPD3922	Approved
0.8622	High Similarity	NPD3923	Approved
0.8622	High Similarity	NPD3924	Approved
0.8622	High Similarity	NPD3921	Approved
0.8325	Intermediate Similarity	NPD3816	Phase 1
0.8325	Intermediate Similarity	NPD3815	Phase 1
0.8227	Intermediate Similarity	NPD6494	Phase 2
0.8093	Intermediate Similarity	NPD3763	Approved
0.8061	Intermediate Similarity	NPD3920	Phase 2
0.7897	Intermediate Similarity	NPD7069	Discontinued
0.7889	Intermediate Similarity	NPD7414	Clinical (unspecified phase)
0.7889	Intermediate Similarity	NPD3386	Phase 2
0.7871	Intermediate Similarity	NPD6257	Clinical (unspecified phase)
0.7854	Intermediate Similarity	NPD6361	Phase 2
0.7822	Intermediate Similarity	NPD4375	Approved
0.7789	Intermediate Similarity	NPD1620	Clinical (unspecified phase)
0.7696	Intermediate Similarity	NPD7571	Clinical (unspecified phase)
0.7581	Intermediate Similarity	NPD7222	Phase 2
0.757	Intermediate Similarity	NPD4039	Approved
0.757	Intermediate Similarity	NPD4038	Approved
0.757	Intermediate Similarity	NPD4033	Approved
0.757	Intermediate Similarity	NPD4122	Approved
0.757	Intermediate Similarity	NPD4036	Approved
0.757	Intermediate Similarity	NPD32	Approved
0.757	Intermediate Similarity	NPD4035	Approved
0.757	Intermediate Similarity	NPD4037	Approved
0.757	Intermediate Similarity	NPD31	Approved
0.757	Intermediate Similarity	NPD4034	Approved
0.7545	Intermediate Similarity	NPD5612	Discontinued
0.7522	Intermediate Similarity	NPD6553	Clinical (unspecified phase)
0.7512	Intermediate Similarity	NPD4551	Phase 2
0.7511	Intermediate Similarity	NPD7558	Phase 2
0.7477	Intermediate Similarity	NPD6477	Clinical (unspecified phase)
0.7475	Intermediate Similarity	NPD5751	Clinical (unspecified phase)
0.7465	Intermediate Similarity	NPD5658	Approved
0.7465	Intermediate Similarity	NPD6219	Discontinued
0.7464	Intermediate Similarity	NPD6569	Phase 2
0.7463	Intermediate Similarity	NPD1923	Clinical (unspecified phase)
0.7454	Intermediate Similarity	NPD5530	Phase 1
0.7443	Intermediate Similarity	NPD4502	Phase 2
0.7437	Intermediate Similarity	NPD6872	Clinical (unspecified phase)
0.7427	Intermediate Similarity	NPD7169	Suspended
0.7427	Intermediate Similarity	NPD4889	Approved
0.7419	Intermediate Similarity	NPD7452	Approved
0.7419	Intermediate Similarity	NPD7453	Approved
0.7403	Intermediate Similarity	NPD6963	Approved
0.7403	Intermediate Similarity	NPD6964	Approved
0.7395	Intermediate Similarity	NPD6525	Clinical (unspecified phase)
0.7395	Intermediate Similarity	NPD6975	Discontinued
0.7364	Intermediate Similarity	NPD6503	Clinical (unspecified phase)
0.7362	Intermediate Similarity	NPD1483	Discontinued
0.7362	Intermediate Similarity	NPD4875	Phase 3
0.7362	Intermediate Similarity	NPD4876	Phase 3
0.7346	Intermediate Similarity	NPD1038	Approved
0.7345	Intermediate Similarity	NPD1856	Discontinued
0.7336	Intermediate Similarity	NPD7555	Discontinued
0.73	Intermediate Similarity	NPD6230	Discontinued
0.7294	Intermediate Similarity	NPD4305	Clinical (unspecified phase)
0.7285	Intermediate Similarity	NPD5939	Approved
0.7285	Intermediate Similarity	NPD5936	Approved
0.7269	Intermediate Similarity	NPD1954	Phase 1
0.7257	Intermediate Similarity	NPD5930	Phase 3
0.7257	Intermediate Similarity	NPD6856	Discontinued
0.7251	Intermediate Similarity	NPD2334	Discontinued
0.723	Intermediate Similarity	NPD4418	Discontinued
0.7227	Intermediate Similarity	NPD2739	Clinical (unspecified phase)
0.7227	Intermediate Similarity	NPD4350	Approved
0.7227	Intermediate Similarity	NPD4349	Approved
0.7213	Intermediate Similarity	NPD8091	Phase 3
0.7207	Intermediate Similarity	NPD4131	Phase 3
0.719	Intermediate Similarity	NPD7859	Phase 2
0.7188	Intermediate Similarity	NPD5903	Approved
0.7188	Intermediate Similarity	NPD5902	Approved
0.7183	Intermediate Similarity	NPD1304	Clinical (unspecified phase)
0.7178	Intermediate Similarity	NPD2781	Approved
0.7177	Intermediate Similarity	NPD6344	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD6656	Clinical (unspecified phase)
0.7164	Intermediate Similarity	NPD2782	Approved
0.7164	Intermediate Similarity	NPD2780	Approved
0.7163	Intermediate Similarity	NPD7948	Phase 1
0.7155	Intermediate Similarity	NPD7567	Approved
0.7143	Intermediate Similarity	NPD4396	Clinical (unspecified phase)
0.7129	Intermediate Similarity	NPD5083	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD4437	Phase 3
0.7115	Intermediate Similarity	NPD4204	Approved
0.7115	Intermediate Similarity	NPD4203	Approved
0.7105	Intermediate Similarity	NPD5070	Clinical (unspecified phase)
0.7103	Intermediate Similarity	NPD5575	Clinical (unspecified phase)
0.71	Intermediate Similarity	NPD7675	Phase 3
0.71	Intermediate Similarity	NPD7676	Clinical (unspecified phase)
0.71	Intermediate Similarity	NPD7674	Phase 3
0.7093	Intermediate Similarity	NPD3354	Phase 2
0.7093	Intermediate Similarity	NPD6568	Discontinued
0.7091	Intermediate Similarity	NPD4795	Phase 2
0.7072	Intermediate Similarity	NPD7672	Approved
0.7072	Intermediate Similarity	NPD7671	Approved
0.707	Intermediate Similarity	NPD3395	Approved
0.707	Intermediate Similarity	NPD3396	Approved
0.7061	Intermediate Similarity	NPD6500	Approved
0.7061	Intermediate Similarity	NPD6501	Approved
0.7059	Intermediate Similarity	NPD4724	Clinical (unspecified phase)
0.7056	Intermediate Similarity	NPD7862	Clinical (unspecified phase)
0.7046	Intermediate Similarity	NPD5805	Approved
0.7045	Intermediate Similarity	NPD7956	Approved
0.7045	Intermediate Similarity	NPD7955	Approved
0.7039	Intermediate Similarity	NPD5602	Clinical (unspecified phase)
0.7035	Intermediate Similarity	NPD6140	Clinical (unspecified phase)
0.7029	Intermediate Similarity	NPD7417	Discontinued
0.7027	Intermediate Similarity	NPD5429	Discontinued
0.7018	Intermediate Similarity	NPD4118	Clinical (unspecified phase)
0.7017	Intermediate Similarity	NPD7729	Clinical (unspecified phase)
0.7016	Intermediate Similarity	NPD7708	Approved
0.7014	Intermediate Similarity	NPD3397	Phase 2
0.7012	Intermediate Similarity	NPD7673	Phase 3
0.7012	Intermediate Similarity	NPD6773	Clinical (unspecified phase)
0.7009	Intermediate Similarity	NPD5801	Clinical (unspecified phase)
0.7009	Intermediate Similarity	NPD8052	Clinical (unspecified phase)
0.7005	Intermediate Similarity	NPD5100	Phase 3
0.7005	Intermediate Similarity	NPD2952	Discontinued
0.6996	Remote Similarity	NPD5863	Clinical (unspecified phase)
0.6995	Remote Similarity	NPD4021	Phase 2
0.6991	Remote Similarity	NPD5944	Phase 1
0.6991	Remote Similarity	NPD6491	Clinical (unspecified phase)
0.6991	Remote Similarity	NPD5945	Phase 1
0.6987	Remote Similarity	NPD7886	Phase 2
0.6987	Remote Similarity	NPD7885	Phase 2
0.6986	Remote Similarity	NPD1739	Approved
0.6986	Remote Similarity	NPD1740	Approved
0.6978	Remote Similarity	NPD5067	Phase 2
0.6978	Remote Similarity	NPD6220	Phase 3
0.6978	Remote Similarity	NPD5066	Phase 2
0.6971	Remote Similarity	NPD6159	Phase 2
0.6962	Remote Similarity	NPD2757	Phase 2
0.6959	Remote Similarity	NPD3477	Phase 2
0.6959	Remote Similarity	NPD3478	Clinical (unspecified phase)
0.6953	Remote Similarity	NPD7426	Phase 1
0.6951	Remote Similarity	NPD6290	Phase 2
0.6951	Remote Similarity	NPD1392	Approved
0.6943	Remote Similarity	NPD7395	Discontinued
0.6942	Remote Similarity	NPD1078	Clinical (unspecified phase)
0.6942	Remote Similarity	NPD4083	Discontinued
0.6941	Remote Similarity	NPD2177	Approved
0.6941	Remote Similarity	NPD3825	Phase 3
0.6941	Remote Similarity	NPD2175	Phase 3
0.6941	Remote Similarity	NPD2176	Approved
0.6927	Remote Similarity	NPD1229	Phase 2
0.6926	Remote Similarity	NPD8350	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD8442	Discontinued
0.6923	Remote Similarity	NPD7123	Suspended
0.692	Remote Similarity	NPD4080	Discontinued
0.6919	Remote Similarity	NPD5522	Clinical (unspecified phase)
0.6912	Remote Similarity	NPD6590	Discontinued
0.691	Remote Similarity	NPD7719	Discontinued
0.6906	Remote Similarity	NPD5601	Phase 2
0.6906	Remote Similarity	NPD3003	Approved
0.6905	Remote Similarity	NPD7803	Approved
0.69	Remote Similarity	NPD7823	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD7710	Clinical (unspecified phase)
0.6892	Remote Similarity	NPD6991	Approved
0.6883	Remote Similarity	NPD4926	Clinical (unspecified phase)
0.6883	Remote Similarity	NPD3590	Clinical (unspecified phase)
0.6881	Remote Similarity	NPD5512	Phase 3
0.688	Remote Similarity	NPD7050	Clinical (unspecified phase)
0.688	Remote Similarity	NPD7051	Phase 3
0.6878	Remote Similarity	NPD7134	Clinical (unspecified phase)
0.6878	Remote Similarity	NPD4885	Approved
0.6864	Remote Similarity	NPD4052	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD3837	Clinical (unspecified phase)
0.686	Remote Similarity	NPD5833	Phase 1
0.6856	Remote Similarity	NPD7112	Discontinued
0.6854	Remote Similarity	NPD8054	Approved
0.6854	Remote Similarity	NPD8053	Approved
0.6853	Remote Similarity	NPD5147	Discontinued
0.6849	Remote Similarity	NPD1622	Discontinued
0.6846	Remote Similarity	NPD5905	Phase 1
0.6844	Remote Similarity	NPD5488	Discontinued
0.6835	Remote Similarity	NPD3810	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD6861	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD6243	Phase 3
0.6829	Remote Similarity	NPD925	Approved
0.6829	Remote Similarity	NPD6244	Phase 3
0.6829	Remote Similarity	NPD926	Approved
0.6827	Remote Similarity	NPD677	Clinical (unspecified phase)
0.6826	Remote Similarity	NPD5164	Discontinued
0.6824	Remote Similarity	NPD6736	Discontinued
0.682	Remote Similarity	NPD4372	Phase 1
0.6818	Remote Similarity	NPD6790	Phase 1
0.6818	Remote Similarity	NPD2727	Phase 2
0.6816	Remote Similarity	NPD6276	Discontinued
0.6816	Remote Similarity	NPD4044	Discontinued
0.681	Remote Similarity	NPD6242	Discontinued
0.6806	Remote Similarity	NPD6281	Approved
0.6804	Remote Similarity	NPD6550	Discontinued
0.6797	Remote Similarity	NPD8109	Clinical (unspecified phase)
0.6795	Remote Similarity	NPD6306	Phase 2
0.6794	Remote Similarity	NPD9690	Approved
0.679	Remote Similarity	NPD6473	Phase 1
0.6787	Remote Similarity	NPD5999	Phase 2
0.6784	Remote Similarity	NPD6262	Clinical (unspecified phase)
0.6783	Remote Similarity	NPD6147	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