NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	264.16
Volume:	291.833
LogP:	3.574
LogD:	3.345
LogS:	-3.173
# Rotatable Bonds:	0
TPSA:	19.03
# H-Bond Aceptor:	2
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.713
Synthetic Accessibility Score:	4.749
Fsp3:	0.333
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:	-4.932
MDCK Permeability:	2.4246512111858465e-05
Pgp-inhibitor:	0.952
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.906
30% Bioavailability (F30%):	0.022

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.992
Plasma Protein Binding (PPB):	87.6463851928711%
Volume Distribution (VD):	2.36
Pgp-substrate:	10.527813911437988%

ADMET: Metabolism

CYP1A2-inhibitor:	0.912
CYP1A2-substrate:	0.544
CYP2C19-inhibitor:	0.785
CYP2C19-substrate:	0.188
CYP2C9-inhibitor:	0.557
CYP2C9-substrate:	0.483
CYP2D6-inhibitor:	0.95
CYP2D6-substrate:	0.89
CYP3A4-inhibitor:	0.054
CYP3A4-substrate:	0.273

ADMET: Excretion

Clearance (CL):	14.037
Half-life (T1/2):	0.164

ADMET: Toxicity

hERG Blockers:	0.427
Human Hepatotoxicity (H-HT):	0.104
Drug-inuced Liver Injury (DILI):	0.719
AMES Toxicity:	0.413
Rat Oral Acute Toxicity:	0.387
Maximum Recommended Daily Dose:	0.944
Skin Sensitization:	0.508
Carcinogencity:	0.803
Eye Corrosion:	0.004
Eye Irritation:	0.011
Respiratory Toxicity:	0.98

Download Data

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

Natural Product: NPC90723

Natural Product ID:	NPC90723
*Common Name:**	Pericalline
IUPAC Name:	n.a.
Synonyms:	Pericalline
Standard InCHIKey:	YBWKMVPRGFJPHD-LELDJUSMSA-N
Standard InCHI:	InChI=1S/C18H20N2/c1-3-13-10-20-7-5-16(13)12(2)17-9-18-14(4-6-19-18)8-15(17)11-20/h3-4,6,8-9,16,19H,2,5,7,10-11H2,1H3/b13-3-/t16-/m0/s1
SMILES:	C/C=C1/CN2CC[C@H]1C(=C)c1c(C2)cc2c(c1)[nH]cc2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL486306
PubChem CID:	6436240
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0004007] Benzazocines

*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
NPO5881	Catharanthus roseus	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12628396]
NPO5881	Catharanthus roseus	Species	Apocynaceae	Eukaryota	Hairy roots	n.a.	n.a.	PMID[19271765]
NPO5881	Catharanthus roseus	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26285573]
NPO5881	Catharanthus roseus	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[6619887]
NPO5881	Catharanthus roseus	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[6631435]
NPO5881	Catharanthus roseus	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7264679]
NPO5881	Catharanthus roseus	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7264682]
NPO5881	Catharanthus roseus	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7320741]
NPO30717	Metaplexis japonica	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12320	Adonis amurensis	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26820	Aspidosperma dasycarpon	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5881	Catharanthus roseus	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26820	Aspidosperma dasycarpon	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5881	Catharanthus roseus	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12320	Adonis amurensis	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4657	Cynanchum rostellatum	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12320	Adonis amurensis	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO5881	Catharanthus roseus	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO26820	Aspidosperma dasycarpon	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO30717	Metaplexis japonica	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO12320	Adonis amurensis	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4657	Cynanchum rostellatum	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5881	Catharanthus roseus	Species	Apocynaceae	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
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT459	Individual Protein	Human immunodeficiency virus type 1 reverse transcriptase	Human immunodeficiency virus 1	IC50	>	200.0	ug.mL-1	PMID[559502]

☑ 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 NPC90723 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	1002
0.1-0.2	9981
0.2-0.3	20893
0.3-0.4	5413
0.4-0.5	2112
0.5-0.6	1797
0.6-0.7	1062
0.7-0.8	333
0.8-0.85	77
0.85-0.9	20
0.9-0.95	6
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9408	High Similarity	NPC56765
0.9221	High Similarity	NPC44773
0.9221	High Similarity	NPC215584
0.9156	High Similarity	NPC318065
0.9156	High Similarity	NPC206819
0.8968	High Similarity	NPC286427
0.891	High Similarity	NPC41257
0.8792	High Similarity	NPC73767
0.8766	High Similarity	NPC33421
0.8733	High Similarity	NPC59084
0.8733	High Similarity	NPC469779
0.8733	High Similarity	NPC469761
0.8733	High Similarity	NPC469768
0.8733	High Similarity	NPC469783
0.8733	High Similarity	NPC469767
0.8733	High Similarity	NPC469780
0.8733	High Similarity	NPC469784
0.8675	High Similarity	NPC469766
0.8667	High Similarity	NPC110126
0.8658	High Similarity	NPC84911
0.8642	High Similarity	NPC194411
0.8591	High Similarity	NPC96102
0.8591	High Similarity	NPC29886
0.8591	High Similarity	NPC261195
0.8533	High Similarity	NPC105127
0.8526	High Similarity	NPC53947
0.8485	Intermediate Similarity	NPC37423
0.8485	Intermediate Similarity	NPC275305
0.8471	Intermediate Similarity	NPC470233
0.8462	Intermediate Similarity	NPC321911
0.8443	Intermediate Similarity	NPC176199
0.8443	Intermediate Similarity	NPC215795
0.8397	Intermediate Similarity	NPC179787
0.8397	Intermediate Similarity	NPC469811
0.8397	Intermediate Similarity	NPC201380
0.8387	Intermediate Similarity	NPC314372
0.8383	Intermediate Similarity	NPC68354
0.8377	Intermediate Similarity	NPC190296
0.8366	Intermediate Similarity	NPC279081
0.8355	Intermediate Similarity	NPC169433
0.8333	Intermediate Similarity	NPC63545
0.8333	Intermediate Similarity	NPC288838
0.8322	Intermediate Similarity	NPC82295
0.8313	Intermediate Similarity	NPC51054
0.8312	Intermediate Similarity	NPC63157
0.8312	Intermediate Similarity	NPC473868
0.8302	Intermediate Similarity	NPC325903
0.8291	Intermediate Similarity	NPC105818
0.8291	Intermediate Similarity	NPC24678
0.8289	Intermediate Similarity	NPC251722
0.8289	Intermediate Similarity	NPC314102
0.828	Intermediate Similarity	NPC21605
0.8278	Intermediate Similarity	NPC198988
0.8255	Intermediate Similarity	NPC282398
0.8247	Intermediate Similarity	NPC2949
0.8247	Intermediate Similarity	NPC230002
0.8224	Intermediate Similarity	NPC325252
0.8218	Intermediate Similarity	NPC95783
0.8217	Intermediate Similarity	NPC143872
0.8187	Intermediate Similarity	NPC469765
0.8187	Intermediate Similarity	NPC469786
0.8187	Intermediate Similarity	NPC469763
0.8187	Intermediate Similarity	NPC25008
0.8187	Intermediate Similarity	NPC259644
0.8187	Intermediate Similarity	NPC469760
0.8187	Intermediate Similarity	NPC200214
0.8187	Intermediate Similarity	NPC73952
0.8182	Intermediate Similarity	NPC312092
0.8165	Intermediate Similarity	NPC471957
0.8153	Intermediate Similarity	NPC159856
0.8148	Intermediate Similarity	NPC216643
0.8137	Intermediate Similarity	NPC70922
0.8137	Intermediate Similarity	NPC75540
0.8137	Intermediate Similarity	NPC80597
0.8137	Intermediate Similarity	NPC212376
0.8137	Intermediate Similarity	NPC211572
0.811	Intermediate Similarity	NPC470203
0.8079	Intermediate Similarity	NPC475450
0.8079	Intermediate Similarity	NPC179365
0.8065	Intermediate Similarity	NPC88097
0.8052	Intermediate Similarity	NPC150259
0.805	Intermediate Similarity	NPC477134
0.8049	Intermediate Similarity	NPC470204
0.8037	Intermediate Similarity	NPC236711
0.8025	Intermediate Similarity	NPC34844
0.8024	Intermediate Similarity	NPC201700
0.8013	Intermediate Similarity	NPC22079
0.8013	Intermediate Similarity	NPC475428
0.8012	Intermediate Similarity	NPC470823
0.7988	Intermediate Similarity	NPC135141
0.7988	Intermediate Similarity	NPC92796
0.7975	Intermediate Similarity	NPC469785
0.7964	Intermediate Similarity	NPC49954
0.7964	Intermediate Similarity	NPC474561
0.7963	Intermediate Similarity	NPC141926
0.7952	Intermediate Similarity	NPC317105
0.7947	Intermediate Similarity	NPC473587
0.7939	Intermediate Similarity	NPC122141
0.7927	Intermediate Similarity	NPC469762
0.7901	Intermediate Similarity	NPC216713
0.7898	Intermediate Similarity	NPC115611
0.7895	Intermediate Similarity	NPC280852
0.7895	Intermediate Similarity	NPC474958
0.7881	Intermediate Similarity	NPC473762
0.7871	Intermediate Similarity	NPC218268
0.7866	Intermediate Similarity	NPC184476
0.7857	Intermediate Similarity	NPC160105
0.7849	Intermediate Similarity	NPC151939
0.7845	Intermediate Similarity	NPC229332
0.7844	Intermediate Similarity	NPC472587
0.7844	Intermediate Similarity	NPC311276
0.7844	Intermediate Similarity	NPC194640
0.784	Intermediate Similarity	NPC40070
0.7826	Intermediate Similarity	NPC470111
0.7824	Intermediate Similarity	NPC82331
0.7824	Intermediate Similarity	NPC201634
0.7812	Intermediate Similarity	NPC204141
0.7812	Intermediate Similarity	NPC470440
0.7792	Intermediate Similarity	NPC473930
0.7785	Intermediate Similarity	NPC46358
0.7784	Intermediate Similarity	NPC282231
0.7778	Intermediate Similarity	NPC313791
0.7771	Intermediate Similarity	NPC474880
0.7771	Intermediate Similarity	NPC221786
0.7771	Intermediate Similarity	NPC475990
0.7759	Intermediate Similarity	NPC300688
0.7748	Intermediate Similarity	NPC250361
0.7738	Intermediate Similarity	NPC40779
0.7725	Intermediate Similarity	NPC279918
0.7718	Intermediate Similarity	NPC41174
0.7707	Intermediate Similarity	NPC125746
0.7706	Intermediate Similarity	NPC63751
0.7701	Intermediate Similarity	NPC213468
0.7697	Intermediate Similarity	NPC38736
0.7692	Intermediate Similarity	NPC274229
0.7674	Intermediate Similarity	NPC314603
0.7674	Intermediate Similarity	NPC477611
0.767	Intermediate Similarity	NPC19679
0.7669	Intermediate Similarity	NPC124005
0.7665	Intermediate Similarity	NPC6436
0.7661	Intermediate Similarity	NPC280548
0.7654	Intermediate Similarity	NPC316069
0.7651	Intermediate Similarity	NPC476464
0.7647	Intermediate Similarity	NPC49217
0.764	Intermediate Similarity	NPC474707
0.7633	Intermediate Similarity	NPC149265
0.763	Intermediate Similarity	NPC293216
0.7624	Intermediate Similarity	NPC316359
0.7624	Intermediate Similarity	NPC315617
0.7619	Intermediate Similarity	NPC131718
0.7619	Intermediate Similarity	NPC229173
0.7616	Intermediate Similarity	NPC27740
0.761	Intermediate Similarity	NPC104483
0.7598	Intermediate Similarity	NPC317030
0.7598	Intermediate Similarity	NPC204565
0.759	Intermediate Similarity	NPC476297
0.759	Intermediate Similarity	NPC476219
0.7588	Intermediate Similarity	NPC17751
0.7588	Intermediate Similarity	NPC280864
0.7584	Intermediate Similarity	NPC215519
0.7578	Intermediate Similarity	NPC20144
0.7561	Intermediate Similarity	NPC2272
0.756	Intermediate Similarity	NPC230869
0.7558	Intermediate Similarity	NPC97343
0.7557	Intermediate Similarity	NPC314919
0.7556	Intermediate Similarity	NPC173028
0.7556	Intermediate Similarity	NPC65215
0.7544	Intermediate Similarity	NPC54988
0.7543	Intermediate Similarity	NPC248454
0.7529	Intermediate Similarity	NPC271797
0.7529	Intermediate Similarity	NPC21174
0.7529	Intermediate Similarity	NPC162799
0.7528	Intermediate Similarity	NPC228835
0.7527	Intermediate Similarity	NPC314058
0.7527	Intermediate Similarity	NPC316018
0.7514	Intermediate Similarity	NPC233936
0.7514	Intermediate Similarity	NPC307191
0.7514	Intermediate Similarity	NPC470498
0.75	Intermediate Similarity	NPC193740
0.75	Intermediate Similarity	NPC11126
0.75	Intermediate Similarity	NPC32002
0.75	Intermediate Similarity	NPC167635
0.75	Intermediate Similarity	NPC316811
0.75	Intermediate Similarity	NPC315348
0.75	Intermediate Similarity	NPC129721
0.75	Intermediate Similarity	NPC122718
0.7471	Intermediate Similarity	NPC225018
0.7471	Intermediate Similarity	NPC16667
0.7458	Intermediate Similarity	NPC16659
0.7455	Intermediate Similarity	NPC187951
0.7455	Intermediate Similarity	NPC37548
0.7451	Intermediate Similarity	NPC166424
0.7451	Intermediate Similarity	NPC245244
0.7451	Intermediate Similarity	NPC146373
0.745	Intermediate Similarity	NPC143603
0.745	Intermediate Similarity	NPC91958
0.7444	Intermediate Similarity	NPC94752
0.7443	Intermediate Similarity	NPC14113
0.7443	Intermediate Similarity	NPC145885
0.7443	Intermediate Similarity	NPC59269

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 NPC90723 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	431
0.1-0.2	713
0.2-0.3	1112
0.3-0.4	2157
0.4-0.5	2210
0.5-0.6	1678
0.6-0.7	664
0.7-0.8	147
0.8-0.85	27
0.85-0.9	10
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9226	High Similarity	NPD3323	Discontinued
0.9073	High Similarity	NPD3100	Discontinued
0.8938	High Similarity	NPD3610	Approved
0.8938	High Similarity	NPD3609	Approved
0.8926	High Similarity	NPD1722	Approved
0.8808	High Similarity	NPD5254	Discontinued
0.8766	High Similarity	NPD2172	Phase 1
0.872	High Similarity	NPD4181	Approved
0.8696	High Similarity	NPD2640	Approved
0.8696	High Similarity	NPD2641	Approved
0.8667	High Similarity	NPD786	Approved
0.8591	High Similarity	NPD198	Clinical (unspecified phase)
0.858	High Similarity	NPD4779	Clinical (unspecified phase)
0.8434	Intermediate Similarity	NPD4075	Phase 2
0.8418	Intermediate Similarity	NPD2837	Discontinued
0.8397	Intermediate Similarity	NPD4547	Phase 3
0.8385	Intermediate Similarity	NPD1403	Approved
0.8385	Intermediate Similarity	NPD1404	Approved
0.8383	Intermediate Similarity	NPD3506	Approved
0.8383	Intermediate Similarity	NPD3505	Approved
0.8373	Intermediate Similarity	NPD4128	Approved
0.8344	Intermediate Similarity	NPD4374	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD1853	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD4079	Approved
0.8333	Intermediate Similarity	NPD1683	Approved
0.8333	Intermediate Similarity	NPD4076	Approved
0.8333	Intermediate Similarity	NPD5315	Discontinued
0.8324	Intermediate Similarity	NPD5145	Clinical (unspecified phase)
0.8314	Intermediate Similarity	NPD3486	Clinical (unspecified phase)
0.8293	Intermediate Similarity	NPD2642	Approved
0.8293	Intermediate Similarity	NPD2639	Approved
0.8255	Intermediate Similarity	NPD3475	Approved
0.8255	Intermediate Similarity	NPD3476	Approved
0.8247	Intermediate Similarity	NPD3943	Clinical (unspecified phase)
0.8246	Intermediate Similarity	NPD3607	Clinical (unspecified phase)
0.8242	Intermediate Similarity	NPD2185	Clinical (unspecified phase)
0.8232	Intermediate Similarity	NPD5744	Clinical (unspecified phase)
0.8199	Intermediate Similarity	NPD2580	Discontinued
0.8092	Intermediate Similarity	NPD4029	Approved
0.8092	Intermediate Similarity	NPD4030	Approved
0.8092	Intermediate Similarity	NPD4028	Approved
0.8054	Intermediate Similarity	NPD2118	Approved
0.8054	Intermediate Similarity	NPD2119	Approved
0.8025	Intermediate Similarity	NPD977	Approved
0.8025	Intermediate Similarity	NPD976	Approved
0.8025	Intermediate Similarity	NPD975	Approved
0.8025	Intermediate Similarity	NPD4637	Clinical (unspecified phase)
0.8024	Intermediate Similarity	NPD5069	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD3961	Discontinued
0.7989	Intermediate Similarity	NPD6610	Clinical (unspecified phase)
0.7989	Intermediate Similarity	NPD2960	Clinical (unspecified phase)
0.7988	Intermediate Similarity	NPD4112	Clinical (unspecified phase)
0.7965	Intermediate Similarity	NPD6277	Clinical (unspecified phase)
0.7953	Intermediate Similarity	NPD2144	Approved
0.7953	Intermediate Similarity	NPD6203	Clinical (unspecified phase)
0.7944	Intermediate Similarity	NPD6664	Approved
0.7919	Intermediate Similarity	NPD3038	Discontinued
0.7895	Intermediate Similarity	NPD6375	Clinical (unspecified phase)
0.7874	Intermediate Similarity	NPD5106	Approved
0.7874	Intermediate Similarity	NPD5105	Approved
0.787	Intermediate Similarity	NPD5436	Phase 1
0.7862	Intermediate Similarity	NPD1918	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD3385	Approved
0.7857	Intermediate Similarity	NPD3944	Approved
0.7857	Intermediate Similarity	NPD3942	Approved
0.7841	Intermediate Similarity	NPD4426	Clinical (unspecified phase)
0.784	Intermediate Similarity	NPD4463	Approved
0.784	Intermediate Similarity	NPD4462	Approved
0.7836	Intermediate Similarity	NPD5065	Approved
0.7829	Intermediate Similarity	NPD3654	Approved
0.7821	Intermediate Similarity	NPD1262	Discovery
0.7815	Intermediate Similarity	NPD992	Clinical (unspecified phase)
0.7815	Intermediate Similarity	NPD991	Phase 2
0.7811	Intermediate Similarity	NPD4640	Approved
0.7811	Intermediate Similarity	NPD4638	Approved
0.7811	Intermediate Similarity	NPD4639	Approved
0.7811	Intermediate Similarity	NPD5021	Discontinued
0.7799	Intermediate Similarity	NPD2007	Clinical (unspecified phase)
0.7799	Intermediate Similarity	NPD2006	Phase 2
0.7797	Intermediate Similarity	NPD8431	Approved
0.7778	Intermediate Similarity	NPD2430	Phase 2
0.7765	Intermediate Similarity	NPD4184	Clinical (unspecified phase)
0.7758	Intermediate Similarity	NPD2150	Discontinued
0.7714	Intermediate Similarity	NPD1707	Approved
0.7714	Intermediate Similarity	NPD1708	Approved
0.7711	Intermediate Similarity	NPD2865	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD2165	Phase 1
0.7651	Intermediate Similarity	NPD2748	Clinical (unspecified phase)
0.7651	Intermediate Similarity	NPD3114	Approved
0.7651	Intermediate Similarity	NPD3115	Approved
0.7651	Intermediate Similarity	NPD3113	Approved
0.7651	Intermediate Similarity	NPD3112	Approved
0.7633	Intermediate Similarity	NPD3583	Phase 2
0.7614	Intermediate Similarity	NPD1895	Discontinued
0.7602	Intermediate Similarity	NPD2390	Clinical (unspecified phase)
0.7598	Intermediate Similarity	NPD2310	Clinical (unspecified phase)
0.7595	Intermediate Similarity	NPD6554	Approved
0.7595	Intermediate Similarity	NPD45	Approved
0.7571	Intermediate Similarity	NPD5728	Clinical (unspecified phase)
0.7543	Intermediate Similarity	NPD7111	Discontinued
0.7532	Intermediate Similarity	NPD1256	Approved
0.7532	Intermediate Similarity	NPD1253	Approved
0.7532	Intermediate Similarity	NPD1254	Approved
0.7532	Intermediate Similarity	NPD1255	Approved
0.7514	Intermediate Similarity	NPD5934	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD2070	Approved
0.75	Intermediate Similarity	NPD2075	Approved
0.75	Intermediate Similarity	NPD2072	Approved
0.75	Intermediate Similarity	NPD2071	Approved
0.75	Intermediate Similarity	NPD2069	Approved
0.75	Intermediate Similarity	NPD2073	Approved
0.75	Intermediate Similarity	NPD2074	Approved
0.75	Intermediate Similarity	NPD1192	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD2068	Approved
0.75	Intermediate Similarity	NPD5590	Clinical (unspecified phase)
0.7472	Intermediate Similarity	NPD1332	Clinical (unspecified phase)
0.7471	Intermediate Similarity	NPD2385	Clinical (unspecified phase)
0.7458	Intermediate Similarity	NPD6595	Phase 3
0.7457	Intermediate Similarity	NPD1326	Approved
0.7457	Intermediate Similarity	NPD1325	Approved
0.7444	Intermediate Similarity	NPD6217	Discontinued
0.7429	Intermediate Similarity	NPD3799	Suspended
0.7425	Intermediate Similarity	NPD3339	Approved
0.7418	Intermediate Similarity	NPD6281	Approved
0.7417	Intermediate Similarity	NPD271	Approved
0.7417	Intermediate Similarity	NPD270	Clinical (unspecified phase)
0.7417	Intermediate Similarity	NPD268	Approved
0.7403	Intermediate Similarity	NPD9583	Approved
0.7391	Intermediate Similarity	NPD768	Clinical (unspecified phase)
0.7377	Intermediate Similarity	NPD6630	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD4880	Discontinued
0.7351	Intermediate Similarity	NPD7024	Clinical (unspecified phase)
0.7337	Intermediate Similarity	NPD473	Clinical (unspecified phase)
0.7337	Intermediate Similarity	NPD3404	Approved
0.7325	Intermediate Similarity	NPD715	Phase 3
0.7318	Intermediate Similarity	NPD4649	Clinical (unspecified phase)
0.7314	Intermediate Similarity	NPD6827	Clinical (unspecified phase)
0.7314	Intermediate Similarity	NPD6828	Phase 2
0.7312	Intermediate Similarity	NPD6278	Clinical (unspecified phase)
0.7306	Intermediate Similarity	NPD2125	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD40	Phase 2
0.7303	Intermediate Similarity	NPD5730	Phase 2
0.7289	Intermediate Similarity	NPD4703	Approved
0.7289	Intermediate Similarity	NPD4702	Approved
0.7288	Intermediate Similarity	NPD749	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD6180	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD2720	Phase 1
0.7283	Intermediate Similarity	NPD2719	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD3318	Approved
0.7278	Intermediate Similarity	NPD3319	Phase 1
0.7278	Intermediate Similarity	NPD803	Phase 1
0.7278	Intermediate Similarity	NPD3320	Approved
0.7273	Intermediate Similarity	NPD9357	Approved
0.7268	Intermediate Similarity	NPD8110	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD9392	Approved
0.7267	Intermediate Similarity	NPD9396	Approved
0.7261	Intermediate Similarity	NPD947	Approved
0.7258	Intermediate Similarity	NPD7619	Phase 3
0.7258	Intermediate Similarity	NPD7618	Phase 3
0.7248	Intermediate Similarity	NPD269	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD1248	Discontinued
0.7238	Intermediate Similarity	NPD7564	Discontinued
0.7238	Intermediate Similarity	NPD4957	Phase 2
0.7232	Intermediate Similarity	NPD482	Approved
0.7222	Intermediate Similarity	NPD7185	Discontinued
0.7219	Intermediate Similarity	NPD2012	Clinical (unspecified phase)
0.7216	Intermediate Similarity	NPD3117	Approved
0.7216	Intermediate Similarity	NPD3116	Approved
0.7207	Intermediate Similarity	NPD1327	Discontinued
0.7198	Intermediate Similarity	NPD4298	Clinical (unspecified phase)
0.7184	Intermediate Similarity	NPD4550	Clinical (unspecified phase)
0.7182	Intermediate Similarity	NPD2092	Phase 2
0.7182	Intermediate Similarity	NPD2094	Phase 2
0.7182	Intermediate Similarity	NPD2095	Phase 2
0.717	Intermediate Similarity	NPD1251	Discontinued
0.7167	Intermediate Similarity	NPD5473	Discontinued
0.7158	Intermediate Similarity	NPD5820	Clinical (unspecified phase)
0.7158	Intermediate Similarity	NPD2793	Discontinued
0.7151	Intermediate Similarity	NPD4615	Phase 2
0.7143	Intermediate Similarity	NPD2096	Phase 2
0.7143	Intermediate Similarity	NPD2091	Phase 2
0.7134	Intermediate Similarity	NPD1598	Discontinued
0.7127	Intermediate Similarity	NPD5806	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD1994	Approved
0.7125	Intermediate Similarity	NPD1993	Approved
0.7125	Intermediate Similarity	NPD1995	Approved
0.712	Intermediate Similarity	NPD7394	Phase 2
0.7113	Intermediate Similarity	NPD6838	Clinical (unspecified phase)
0.7112	Intermediate Similarity	NPD3485	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD3341	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD6661	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD1027	Approved
0.7101	Intermediate Similarity	NPD1029	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD1030	Approved
0.7098	Intermediate Similarity	NPD5426	Phase 3
0.7095	Intermediate Similarity	NPD3348	Phase 2
0.7095	Intermediate Similarity	NPD5100	Phase 3
0.7086	Intermediate Similarity	NPD1313	Approved
0.7083	Intermediate Similarity	NPD3015	Discontinued
0.7083	Intermediate Similarity	NPD1661	Suspended

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