NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	246.12
Volume:	269.264
LogP:	4.538
LogD:	3.954
LogS:	-5.134
# Rotatable Bonds:	0
TPSA:	28.68
# H-Bond Aceptor:	2
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.486
Synthetic Accessibility Score:	2.49
Fsp3:	0.118
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.949
MDCK Permeability:	1.3145389857527334e-05
Pgp-inhibitor:	0.245
Pgp-substrate:	0.627
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.85
30% Bioavailability (F30%):	0.992

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.738
Plasma Protein Binding (PPB):	97.26129913330078%
Volume Distribution (VD):	1.192
Pgp-substrate:	1.346392273902893%

ADMET: Metabolism

CYP1A2-inhibitor:	0.981
CYP1A2-substrate:	0.938
CYP2C19-inhibitor:	0.774
CYP2C19-substrate:	0.416
CYP2C9-inhibitor:	0.581
CYP2C9-substrate:	0.791
CYP2D6-inhibitor:	0.875
CYP2D6-substrate:	0.873
CYP3A4-inhibitor:	0.768
CYP3A4-substrate:	0.226

ADMET: Excretion

Clearance (CL):	4.897
Half-life (T1/2):	0.179

ADMET: Toxicity

hERG Blockers:	0.156
Human Hepatotoxicity (H-HT):	0.851
Drug-inuced Liver Injury (DILI):	0.929
AMES Toxicity:	0.958
Rat Oral Acute Toxicity:	0.618
Maximum Recommended Daily Dose:	0.886
Skin Sensitization:	0.925
Carcinogencity:	0.688
Eye Corrosion:	0.01
Eye Irritation:	0.971
Respiratory Toxicity:	0.949

Download Data

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

Natural Product: NPC44773

Natural Product ID:	NPC44773
*Common Name:**	Olivacine
IUPAC Name:	1,5-dimethyl-6H-pyrido[4,3-b]carbazole
Synonyms:
Standard InCHIKey:	ZIXGXMMUKPLXBB-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C17H14N2/c1-10-12-7-8-18-11(2)14(12)9-15-13-5-3-4-6-16(13)19-17(10)15/h3-9,19H,1-2H3
SMILES:	Cc1nccc2c1cc1c3ccccc3[nH]c1c2C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL306472
PubChem CID:	5281407
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000211] Indoles and derivatives [CHEMONTID:0000210] Carbazoles

*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
NPO12133	Corchorus olitorius	Species	Malvaceae	Eukaryota	n.a.	leaf	n.a.	PMID[9658577]
NPO12133	Corchorus olitorius	Species	Malvaceae	Eukaryota	n.a.	leaf	n.a.	Database[Article]
NPO12133	Corchorus olitorius	Species	Malvaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO12133	Corchorus olitorius	Species	Malvaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO12133	Corchorus olitorius	Species	Malvaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO22383	Aspidosperma nigricans	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14143	Aspidosperma campus-belus	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18827	Aspidosperma olivaceum	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12133	Corchorus olitorius	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12985	Corchorus capsularis	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5413	Adonis mongolica	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18827	Aspidosperma olivaceum	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12133	Corchorus olitorius	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12985	Corchorus capsularis	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5413	Adonis mongolica	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22383	Aspidosperma nigricans	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14143	Aspidosperma campus-belus	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5413	Adonis mongolica	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12985	Corchorus capsularis	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18827	Aspidosperma olivaceum	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	7
Others	10

Activity Type	# Activity
Cell Line	6
Organism	8
Others	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1396	Cell Line	NCI-H69	Homo sapiens	IC50	=	1700.0	nM	PMID[507880]
NPT2943	Cell Line	NCI-H417	Homo sapiens	IC50	=	3400.0	nM	PMID[507880]
NPT397	Cell Line	NCI-H460	Homo sapiens	IC50	=	1600.0	nM	PMID[507880]
NPT2466	Cell Line	NCI-H358	Homo sapiens	IC50	=	2300.0	nM	PMID[507880]
NPT137	Cell Line	L1210	Mus musculus	ID50	=	2.03	uM	PMID[507881]
NPT137	Cell Line	L1210	Mus musculus	ILS	=	35.0	%	PMID[507881]
NPT32	Organism	Mus musculus	Mus musculus	LD0	=	250.0	mg kg-1	PMID[507881]
NPT605	Organism	Homo sapiens	Homo sapiens	TGI	=	3600.0	nM	PMID[507882]
NPT605	Organism	Homo sapiens	Homo sapiens	TGI	=	3700.0	nM	PMID[507882]
NPT2	Others	Unspecified		Ratio	=	1.0	n.a.	PMID[507882]
NPT605	Organism	Homo sapiens	Homo sapiens	TGI correlation coefficient	<	0.5	n.a.	PMID[507882]
NPT474	Organism	Plasmodium berghei	Plasmodium berghei	Inhibition	=	90.0	%	PMID[507883]
NPT474	Organism	Plasmodium berghei	Plasmodium berghei	Inhibition	=	48.0	%	PMID[507883]
NPT485	Organism	Plasmodium falciparum (isolate K1 / Thailand)	Plasmodium falciparum K1	IC50	=	400.0	nM	PMID[507883]
NPT757	Organism	Plasmodium falciparum 3D7	Plasmodium falciparum 3D7	IC50	=	1200.0	nM	PMID[507883]
NPT27	Others	Unspecified		IC50	>	140000.0	nM	PMID[507883]
NPT2	Others	Unspecified		Ratio IC50	>	290.0	n.a.	PMID[507883]

☑ 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 NPC44773 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	1261
0.1-0.2	11881
0.2-0.3	19075
0.3-0.4	5423
0.4-0.5	1849
0.5-0.6	1693
0.6-0.7	1089
0.7-0.8	339
0.8-0.85	54
0.85-0.9	29
0.9-0.95	2
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC215584
0.9276	High Similarity	NPC56765
0.9221	High Similarity	NPC90723
0.9026	High Similarity	NPC206819
0.9026	High Similarity	NPC318065
0.8961	High Similarity	NPC286427
0.8903	High Similarity	NPC41257
0.8889	High Similarity	NPC325903
0.8844	High Similarity	NPC169433
0.8808	High Similarity	NPC288838
0.8784	High Similarity	NPC312092
0.8758	High Similarity	NPC53947
0.8758	High Similarity	NPC33421
0.875	High Similarity	NPC201380
0.875	High Similarity	NPC179787
0.8693	High Similarity	NPC321911
0.8684	High Similarity	NPC63545
0.8649	High Similarity	NPC84911
0.8627	High Similarity	NPC469811
0.86	High Similarity	NPC469779
0.86	High Similarity	NPC469767
0.86	High Similarity	NPC469780
0.86	High Similarity	NPC469761
0.86	High Similarity	NPC469784
0.86	High Similarity	NPC469783
0.86	High Similarity	NPC469768
0.8581	High Similarity	NPC96102
0.8581	High Similarity	NPC470233
0.8581	High Similarity	NPC29886
0.8581	High Similarity	NPC261195
0.8543	High Similarity	NPC469766
0.8533	High Similarity	NPC110126
0.8533	High Similarity	NPC73767
0.8523	High Similarity	NPC251722
0.8523	High Similarity	NPC105127
0.8523	High Similarity	NPC314102
0.8519	High Similarity	NPC194411
0.85	High Similarity	NPC317105
0.8481	Intermediate Similarity	NPC216643
0.8435	Intermediate Similarity	NPC179365
0.8378	Intermediate Similarity	NPC473930
0.8367	Intermediate Similarity	NPC282398
0.8366	Intermediate Similarity	NPC190296
0.8365	Intermediate Similarity	NPC236711
0.8364	Intermediate Similarity	NPC275305
0.8364	Intermediate Similarity	NPC37423
0.8355	Intermediate Similarity	NPC279081
0.8323	Intermediate Similarity	NPC176199
0.8323	Intermediate Similarity	NPC215795
0.8313	Intermediate Similarity	NPC135141
0.8313	Intermediate Similarity	NPC92796
0.8311	Intermediate Similarity	NPC82295
0.8311	Intermediate Similarity	NPC475450
0.8302	Intermediate Similarity	NPC51054
0.8299	Intermediate Similarity	NPC473587
0.8267	Intermediate Similarity	NPC198988
0.8263	Intermediate Similarity	NPC68354
0.8261	Intermediate Similarity	NPC122141
0.8258	Intermediate Similarity	NPC314372
0.8243	Intermediate Similarity	NPC475428
0.8235	Intermediate Similarity	NPC230002
0.8231	Intermediate Similarity	NPC473762
0.8212	Intermediate Similarity	NPC325252
0.821	Intermediate Similarity	NPC470203
0.8205	Intermediate Similarity	NPC143872
0.8204	Intermediate Similarity	NPC280852
0.8165	Intermediate Similarity	NPC105818
0.8165	Intermediate Similarity	NPC24678
0.8153	Intermediate Similarity	NPC21605
0.8153	Intermediate Similarity	NPC477134
0.8153	Intermediate Similarity	NPC471957
0.8148	Intermediate Similarity	NPC470204
0.8141	Intermediate Similarity	NPC159856
0.8121	Intermediate Similarity	NPC22079
0.8117	Intermediate Similarity	NPC115611
0.8117	Intermediate Similarity	NPC59084
0.8117	Intermediate Similarity	NPC2949
0.8103	Intermediate Similarity	NPC95783
0.8095	Intermediate Similarity	NPC250361
0.8065	Intermediate Similarity	NPC473868
0.8065	Intermediate Similarity	NPC63157
0.8063	Intermediate Similarity	NPC259644
0.8063	Intermediate Similarity	NPC469763
0.8063	Intermediate Similarity	NPC469760
0.8063	Intermediate Similarity	NPC469786
0.8063	Intermediate Similarity	NPC73952
0.8063	Intermediate Similarity	NPC25008
0.8063	Intermediate Similarity	NPC469765
0.8052	Intermediate Similarity	NPC88097
0.805	Intermediate Similarity	NPC40070
0.8012	Intermediate Similarity	NPC70922
0.8012	Intermediate Similarity	NPC80597
0.8012	Intermediate Similarity	NPC211572
0.8012	Intermediate Similarity	NPC212376
0.8012	Intermediate Similarity	NPC75540
0.8	Intermediate Similarity	NPC284635
0.8	Intermediate Similarity	NPC274229
0.8	Intermediate Similarity	NPC470823
0.7959	Intermediate Similarity	NPC122718
0.795	Intermediate Similarity	NPC141926
0.795	Intermediate Similarity	NPC200214
0.7927	Intermediate Similarity	NPC229173
0.7925	Intermediate Similarity	NPC470111
0.7922	Intermediate Similarity	NPC150259
0.7917	Intermediate Similarity	NPC82331
0.7917	Intermediate Similarity	NPC201634
0.7911	Intermediate Similarity	NPC86288
0.791	Intermediate Similarity	NPC316359
0.791	Intermediate Similarity	NPC315617
0.791	Intermediate Similarity	NPC316018
0.791	Intermediate Similarity	NPC314058
0.7904	Intermediate Similarity	NPC201700
0.7904	Intermediate Similarity	NPC63751
0.7901	Intermediate Similarity	NPC34844
0.7891	Intermediate Similarity	NPC46358
0.7888	Intermediate Similarity	NPC216713
0.7882	Intermediate Similarity	NPC474958
0.787	Intermediate Similarity	NPC477611
0.7861	Intermediate Similarity	NPC208284
0.7857	Intermediate Similarity	NPC97343
0.7853	Intermediate Similarity	NPC184476
0.7853	Intermediate Similarity	NPC469785
0.7836	Intermediate Similarity	NPC151939
0.7836	Intermediate Similarity	NPC59269
0.7831	Intermediate Similarity	NPC472587
0.7823	Intermediate Similarity	NPC41174
0.7805	Intermediate Similarity	NPC469762
0.7799	Intermediate Similarity	NPC470440
0.7771	Intermediate Similarity	NPC282231
0.7771	Intermediate Similarity	NPC225018
0.7758	Intermediate Similarity	NPC221786
0.7758	Intermediate Similarity	NPC474880
0.7758	Intermediate Similarity	NPC475990
0.7746	Intermediate Similarity	NPC314919
0.7746	Intermediate Similarity	NPC300688
0.7742	Intermediate Similarity	NPC218268
0.7738	Intermediate Similarity	NPC474561
0.7738	Intermediate Similarity	NPC49954
0.7725	Intermediate Similarity	NPC194640
0.7725	Intermediate Similarity	NPC311276
0.7719	Intermediate Similarity	NPC471579
0.7711	Intermediate Similarity	NPC279918
0.7697	Intermediate Similarity	NPC231536
0.7692	Intermediate Similarity	NPC125746
0.7688	Intermediate Similarity	NPC204141
0.7687	Intermediate Similarity	NPC215519
0.7683	Intermediate Similarity	NPC476219
0.7683	Intermediate Similarity	NPC38736
0.7661	Intermediate Similarity	NPC313791
0.7657	Intermediate Similarity	NPC19679
0.7654	Intermediate Similarity	NPC124005
0.7651	Intermediate Similarity	NPC6436
0.7647	Intermediate Similarity	NPC474897
0.7647	Intermediate Similarity	NPC280548
0.764	Intermediate Similarity	NPC316069
0.7637	Intermediate Similarity	NPC229332
0.7633	Intermediate Similarity	NPC160105
0.7622	Intermediate Similarity	NPC138842
0.7619	Intermediate Similarity	NPC162799
0.7619	Intermediate Similarity	NPC478182
0.7619	Intermediate Similarity	NPC40779
0.7619	Intermediate Similarity	NPC478184
0.7616	Intermediate Similarity	NPC293216
0.7605	Intermediate Similarity	NPC131718
0.76	Intermediate Similarity	NPC27740
0.76	Intermediate Similarity	NPC307191
0.76	Intermediate Similarity	NPC191415
0.7586	Intermediate Similarity	NPC213468
0.7576	Intermediate Similarity	NPC476297
0.7574	Intermediate Similarity	NPC17751
0.7574	Intermediate Similarity	NPC280864
0.7571	Intermediate Similarity	NPC308931
0.7571	Intermediate Similarity	NPC99939
0.7571	Intermediate Similarity	NPC15102
0.7562	Intermediate Similarity	NPC20144
0.7551	Intermediate Similarity	NPC143603
0.7551	Intermediate Similarity	NPC91958
0.7551	Intermediate Similarity	NPC54102
0.7551	Intermediate Similarity	NPC162689
0.7545	Intermediate Similarity	NPC230869
0.7545	Intermediate Similarity	NPC477591
0.7545	Intermediate Similarity	NPC293487
0.7529	Intermediate Similarity	NPC284775
0.7529	Intermediate Similarity	NPC49217
0.7529	Intermediate Similarity	NPC54988
0.7515	Intermediate Similarity	NPC149265
0.7514	Intermediate Similarity	NPC324149
0.7514	Intermediate Similarity	NPC297034
0.7514	Intermediate Similarity	NPC284678
0.75	Intermediate Similarity	NPC470498
0.7485	Intermediate Similarity	NPC193740
0.7485	Intermediate Similarity	NPC167635
0.7484	Intermediate Similarity	NPC104483
0.7473	Intermediate Similarity	NPC326422
0.7469	Intermediate Similarity	NPC285731
0.7458	Intermediate Similarity	NPC48938
0.7458	Intermediate Similarity	NPC102755
0.7457	Intermediate Similarity	NPC314603
0.7456	Intermediate Similarity	NPC16667
0.7439	Intermediate Similarity	NPC187951

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 NPC44773 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	515
0.1-0.2	769
0.2-0.3	1094
0.3-0.4	2311
0.4-0.5	2059
0.5-0.6	1557
0.6-0.7	666
0.7-0.8	153
0.8-0.85	17
0.85-0.9	8
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9221	High Similarity	NPD3323	Discontinued
0.8926	High Similarity	NPD5254	Discontinued
0.891	High Similarity	NPD1853	Clinical (unspecified phase)
0.8816	High Similarity	NPD3100	Discontinued
0.8812	High Similarity	NPD3610	Approved
0.8812	High Similarity	NPD3609	Approved
0.8667	High Similarity	NPD1722	Approved
0.8645	High Similarity	NPD2837	Discontinued
0.8636	High Similarity	NPD2172	Phase 1
0.8627	High Similarity	NPD4547	Phase 3
0.8598	High Similarity	NPD4181	Approved
0.8581	High Similarity	NPD198	Clinical (unspecified phase)
0.8571	High Similarity	NPD4374	Clinical (unspecified phase)
0.8533	High Similarity	NPD786	Approved
0.8529	High Similarity	NPD5145	Clinical (unspecified phase)
0.8457	Intermediate Similarity	NPD4779	Clinical (unspecified phase)
0.8364	Intermediate Similarity	NPD4128	Approved
0.8355	Intermediate Similarity	NPD3943	Clinical (unspecified phase)
0.8344	Intermediate Similarity	NPD2641	Approved
0.8344	Intermediate Similarity	NPD2640	Approved
0.8323	Intermediate Similarity	NPD1683	Approved
0.8323	Intermediate Similarity	NPD5315	Discontinued
0.8313	Intermediate Similarity	NPD4075	Phase 2
0.8312	Intermediate Similarity	NPD1918	Clinical (unspecified phase)
0.8294	Intermediate Similarity	NPD6610	Clinical (unspecified phase)
0.8263	Intermediate Similarity	NPD3506	Approved
0.8263	Intermediate Similarity	NPD3505	Approved
0.8221	Intermediate Similarity	NPD5744	Clinical (unspecified phase)
0.8214	Intermediate Similarity	NPD4079	Approved
0.8214	Intermediate Similarity	NPD4076	Approved
0.8198	Intermediate Similarity	NPD3486	Clinical (unspecified phase)
0.8158	Intermediate Similarity	NPD1262	Discovery
0.8155	Intermediate Similarity	NPD6203	Clinical (unspecified phase)
0.8148	Intermediate Similarity	NPD1403	Approved
0.8148	Intermediate Similarity	NPD1404	Approved
0.8129	Intermediate Similarity	NPD3607	Clinical (unspecified phase)
0.8129	Intermediate Similarity	NPD4637	Clinical (unspecified phase)
0.8121	Intermediate Similarity	NPD3475	Approved
0.8121	Intermediate Similarity	NPD3476	Approved
0.8092	Intermediate Similarity	NPD8431	Approved
0.8079	Intermediate Similarity	NPD3385	Approved
0.8079	Intermediate Similarity	NPD2960	Clinical (unspecified phase)
0.8075	Intermediate Similarity	NPD2748	Clinical (unspecified phase)
0.8072	Intermediate Similarity	NPD5436	Phase 1
0.8061	Intermediate Similarity	NPD2642	Approved
0.8061	Intermediate Similarity	NPD2639	Approved
0.8039	Intermediate Similarity	NPD45	Approved
0.8039	Intermediate Similarity	NPD6554	Approved
0.8013	Intermediate Similarity	NPD2006	Phase 2
0.8012	Intermediate Similarity	NPD977	Approved
0.8012	Intermediate Similarity	NPD976	Approved
0.8012	Intermediate Similarity	NPD1895	Discontinued
0.8012	Intermediate Similarity	NPD5021	Discontinued
0.8012	Intermediate Similarity	NPD975	Approved
0.8012	Intermediate Similarity	NPD2185	Clinical (unspecified phase)
0.8012	Intermediate Similarity	NPD5069	Clinical (unspecified phase)
0.7987	Intermediate Similarity	NPD2430	Phase 2
0.7976	Intermediate Similarity	NPD4112	Clinical (unspecified phase)
0.7963	Intermediate Similarity	NPD2580	Discontinued
0.7953	Intermediate Similarity	NPD6277	Clinical (unspecified phase)
0.7937	Intermediate Similarity	NPD4463	Approved
0.7937	Intermediate Similarity	NPD4462	Approved
0.7929	Intermediate Similarity	NPD5065	Approved
0.7886	Intermediate Similarity	NPD3961	Discontinued
0.7882	Intermediate Similarity	NPD6375	Clinical (unspecified phase)
0.7861	Intermediate Similarity	NPD5106	Approved
0.7861	Intermediate Similarity	NPD5105	Approved
0.7857	Intermediate Similarity	NPD1254	Approved
0.7857	Intermediate Similarity	NPD1255	Approved
0.7857	Intermediate Similarity	NPD1253	Approved
0.7857	Intermediate Similarity	NPD1256	Approved
0.7843	Intermediate Similarity	NPD4028	Approved
0.7843	Intermediate Similarity	NPD4030	Approved
0.7843	Intermediate Similarity	NPD3944	Approved
0.7843	Intermediate Similarity	NPD3942	Approved
0.7843	Intermediate Similarity	NPD4029	Approved
0.7833	Intermediate Similarity	NPD6664	Approved
0.7829	Intermediate Similarity	NPD4426	Clinical (unspecified phase)
0.78	Intermediate Similarity	NPD2118	Approved
0.78	Intermediate Similarity	NPD2119	Approved
0.78	Intermediate Similarity	NPD991	Phase 2
0.78	Intermediate Similarity	NPD992	Clinical (unspecified phase)
0.7798	Intermediate Similarity	NPD4640	Approved
0.7798	Intermediate Similarity	NPD4638	Approved
0.7798	Intermediate Similarity	NPD4639	Approved
0.7784	Intermediate Similarity	NPD2310	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD4298	Clinical (unspecified phase)
0.7746	Intermediate Similarity	NPD6595	Phase 3
0.7733	Intermediate Similarity	NPD2144	Approved
0.7719	Intermediate Similarity	NPD3799	Suspended
0.7706	Intermediate Similarity	NPD5934	Clinical (unspecified phase)
0.7701	Intermediate Similarity	NPD1708	Approved
0.7701	Intermediate Similarity	NPD1707	Approved
0.7697	Intermediate Similarity	NPD947	Approved
0.7697	Intermediate Similarity	NPD1192	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD2390	Clinical (unspecified phase)
0.7679	Intermediate Similarity	NPD2719	Clinical (unspecified phase)
0.7679	Intermediate Similarity	NPD2720	Phase 1
0.7636	Intermediate Similarity	NPD2150	Discontinued
0.763	Intermediate Similarity	NPD7111	Discontinued
0.7619	Intermediate Similarity	NPD3583	Phase 2
0.76	Intermediate Similarity	NPD3038	Discontinued
0.7584	Intermediate Similarity	NPD5590	Clinical (unspecified phase)
0.7582	Intermediate Similarity	NPD6278	Clinical (unspecified phase)
0.7582	Intermediate Similarity	NPD3654	Approved
0.7564	Intermediate Similarity	NPD4880	Discontinued
0.7562	Intermediate Similarity	NPD2007	Clinical (unspecified phase)
0.756	Intermediate Similarity	NPD2385	Clinical (unspecified phase)
0.7544	Intermediate Similarity	NPD4184	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD715	Phase 3
0.75	Intermediate Similarity	NPD9583	Approved
0.75	Intermediate Similarity	NPD4649	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD5806	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6281	Approved
0.7486	Intermediate Similarity	NPD7394	Phase 2
0.7485	Intermediate Similarity	NPD2865	Clinical (unspecified phase)
0.747	Intermediate Similarity	NPD2165	Phase 1
0.7458	Intermediate Similarity	NPD1332	Clinical (unspecified phase)
0.7442	Intermediate Similarity	NPD1325	Approved
0.7442	Intermediate Similarity	NPD1326	Approved
0.743	Intermediate Similarity	NPD6217	Discontinued
0.743	Intermediate Similarity	NPD2793	Discontinued
0.7425	Intermediate Similarity	NPD3112	Approved
0.7425	Intermediate Similarity	NPD3115	Approved
0.7425	Intermediate Similarity	NPD3113	Approved
0.7425	Intermediate Similarity	NPD3114	Approved
0.7423	Intermediate Similarity	NPD1528	Clinical (unspecified phase)
0.7418	Intermediate Similarity	NPD3404	Approved
0.7416	Intermediate Similarity	NPD7564	Discontinued
0.741	Intermediate Similarity	NPD3339	Approved
0.7403	Intermediate Similarity	NPD6133	Discontinued
0.74	Intermediate Similarity	NPD268	Approved
0.74	Intermediate Similarity	NPD271	Approved
0.74	Intermediate Similarity	NPD270	Clinical (unspecified phase)
0.7399	Intermediate Similarity	NPD6828	Phase 2
0.7399	Intermediate Similarity	NPD6827	Clinical (unspecified phase)
0.7396	Intermediate Similarity	NPD6454	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD4326	Phase 2
0.7372	Intermediate Similarity	NPD1251	Discontinued
0.7368	Intermediate Similarity	NPD4550	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD9357	Approved
0.7363	Intermediate Similarity	NPD6180	Clinical (unspecified phase)
0.7363	Intermediate Similarity	NPD6630	Clinical (unspecified phase)
0.736	Intermediate Similarity	NPD3318	Approved
0.736	Intermediate Similarity	NPD5728	Clinical (unspecified phase)
0.736	Intermediate Similarity	NPD3319	Phase 1
0.736	Intermediate Similarity	NPD3320	Approved
0.7345	Intermediate Similarity	NPD702	Clinical (unspecified phase)
0.7337	Intermediate Similarity	NPD7619	Phase 3
0.7337	Intermediate Similarity	NPD7618	Phase 3
0.7337	Intermediate Similarity	NPD7024	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD4902	Discontinued
0.7318	Intermediate Similarity	NPD4957	Phase 2
0.7299	Intermediate Similarity	NPD1567	Clinical (unspecified phase)
0.7296	Intermediate Similarity	NPD7185	Discontinued
0.7292	Intermediate Similarity	NPD2125	Clinical (unspecified phase)
0.7277	Intermediate Similarity	NPD7445	Phase 1
0.7273	Intermediate Similarity	NPD749	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD768	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD2069	Approved
0.7267	Intermediate Similarity	NPD2074	Approved
0.7267	Intermediate Similarity	NPD2075	Approved
0.7267	Intermediate Similarity	NPD2068	Approved
0.7267	Intermediate Similarity	NPD2070	Approved
0.7267	Intermediate Similarity	NPD2073	Approved
0.7267	Intermediate Similarity	NPD2071	Approved
0.7267	Intermediate Similarity	NPD2072	Approved
0.7263	Intermediate Similarity	NPD5426	Phase 3
0.7253	Intermediate Similarity	NPD8110	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD9392	Approved
0.7248	Intermediate Similarity	NPD9396	Approved
0.7247	Intermediate Similarity	NPD5473	Discontinued
0.7238	Intermediate Similarity	NPD5820	Clinical (unspecified phase)
0.723	Intermediate Similarity	NPD269	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD1598	Discontinued
0.7225	Intermediate Similarity	NPD1248	Discontinued
0.7219	Intermediate Similarity	NPD473	Clinical (unspecified phase)
0.7216	Intermediate Similarity	NPD482	Approved
0.7212	Intermediate Similarity	NPD7469	Discontinued
0.7202	Intermediate Similarity	NPD2012	Clinical (unspecified phase)
0.7195	Intermediate Similarity	NPD3401	Clinical (unspecified phase)
0.7191	Intermediate Similarity	NPD3341	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD6838	Clinical (unspecified phase)
0.7182	Intermediate Similarity	NPD7424	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD8093	Discontinued
0.7176	Intermediate Similarity	NPD6497	Approved
0.7175	Intermediate Similarity	NPD3348	Phase 2
0.7174	Intermediate Similarity	NPD3419	Clinical (unspecified phase)
0.7169	Intermediate Similarity	NPD4703	Approved
0.7169	Intermediate Similarity	NPD4702	Approved
0.7151	Intermediate Similarity	NPD2479	Phase 3
0.7151	Intermediate Similarity	NPD2481	Approved
0.7143	Intermediate Similarity	NPD8094	Discontinued
0.7143	Intermediate Similarity	NPD8248	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD4922	Phase 2
0.7135	Intermediate Similarity	NPD5418	Discontinued
0.7135	Intermediate Similarity	NPD4615	Phase 2
0.7127	Intermediate Similarity	NPD6178	Phase 3
0.7121	Intermediate Similarity	NPD7423	Phase 2
0.7108	Intermediate Similarity	NPD6148	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