NPASS Compound

Structure

CID182907 OpenBabel06191715562D 25 29 0 0 0 0 0 0 0 0999 V2000 -1.4445 5.0665 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4396 3.3587 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8456 1.4365 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8374 0.4748 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0158 2.8997 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3572 1.9490 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3466 0.0014 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6938 0.9625 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0105 1.9331 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5113 1.4667 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5060 0.4929 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1979 1.4575 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1926 0.4837 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8135 3.3860 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8269 1.4583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6689 1.9444 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8392 0.4811 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6815 0.0035 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6508 2.9112 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.6912 -0.9653 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8065 4.3474 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4780 3.4035 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1257 1.7534 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1171 0.1778 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 22 1 0 0 0 0 2 23 1 0 0 0 0 3 4 2 0 0 0 0 3 9 1 0 0 0 0 4 20 1 0 0 0 0 5 9 2 0 0 0 0 5 14 1 0 0 0 0 6 10 2 0 0 0 0 6 12 1 0 0 0 0 7 11 2 0 0 0 0 7 13 1 0 0 0 0 8 24 1 0 0 0 0 8 25 1 0 0 0 0 9 15 1 0 0 0 0 10 11 1 0 0 0 0 10 16 1 0 0 0 0 11 18 1 0 0 0 0 12 13 2 0 0 0 0 12 24 1 0 0 0 0 13 25 1 0 0 0 0 14 19 2 0 0 0 0 14 22 1 0 0 0 0 15 16 2 0 0 0 0 15 17 1 0 0 0 0 16 19 1 0 0 0 0 17 18 1 0 0 0 0 17 20 2 0 0 0 0 18 21 2 0 0 0 0 19 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	335.08
Volume:	325.618
LogP:	3.552
LogD:	3.003
LogS:	-6.472
# Rotatable Bonds:	2
TPSA:	66.88
# H-Bond Aceptor:	6
# H-Bond Donor:	0
# Rings:	5
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.56
Synthetic Accessibility Score:	2.633
Fsp3:	0.158
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.958
MDCK Permeability:	3.320430914754979e-05
Pgp-inhibitor:	0.271
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.002
20% Bioavailability (F20%):	0.001
30% Bioavailability (F30%):	0.005

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.117
Plasma Protein Binding (PPB):	92.80331420898438%
Volume Distribution (VD):	0.718
Pgp-substrate:	3.201951503753662%

ADMET: Metabolism

CYP1A2-inhibitor:	0.885
CYP1A2-substrate:	0.878
CYP2C19-inhibitor:	0.886
CYP2C19-substrate:	0.35
CYP2C9-inhibitor:	0.683
CYP2C9-substrate:	0.905
CYP2D6-inhibitor:	0.184
CYP2D6-substrate:	0.87
CYP3A4-inhibitor:	0.816
CYP3A4-substrate:	0.217

ADMET: Excretion

Clearance (CL):	11.475
Half-life (T1/2):	0.234

ADMET: Toxicity

hERG Blockers:	0.048
Human Hepatotoxicity (H-HT):	0.308
Drug-inuced Liver Injury (DILI):	0.933
AMES Toxicity:	0.795
Rat Oral Acute Toxicity:	0.064
Maximum Recommended Daily Dose:	0.872
Skin Sensitization:	0.039
Carcinogencity:	0.944
Eye Corrosion:	0.003
Eye Irritation:	0.047
Respiratory Toxicity:	0.899

Download Data

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

Natural Product: NPC182907

Natural Product ID:	NPC182907
*Common Name:**	NFDVJYPMLVMXRR-UHFFFAOYSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	NFDVJYPMLVMXRR-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C19H13NO5/c1-22-14-5-9-3-4-20-17-15(9)16(19(14)23-2)10-6-12-13(25-8-24-12)7-11(10)18(17)21/h3-7H,8H2,1-2H3
SMILES:	COc1cc2ccnc3c2c(-c2cc4c(cc2C3=O)OCO4)c1OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1270949
PubChem CID:	3084224
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0000381] Aporphines

*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
NPO6333	Annona glabra	Species	Annonaceae	Eukaryota	n.a.	stem wood	n.a.	DOI[10.1021/np100247r]
NPO6333	Annona glabra	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10395501]
NPO6333	Annona glabra	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10425140]
NPO27883	Bursera simaruba	Species	Burseraceae	Eukaryota	Resin	n.a.	n.a.	PMID[1294696]
NPO28935	Ericameria laricifolia	Species	Asteraceae	Eukaryota	n.a.	Sonoran Desert	n.a.	PMID[15043404]
NPO6333	Annona glabra	Species	Annonaceae	Eukaryota	Fruits	n.a.	n.a.	PMID[15568797]
NPO29110	Litsea cubeba	Species	Lauraceae	Eukaryota	n.a.	aerial part	n.a.	PMID[18991207]
NPO27883	Bursera simaruba	Species	Burseraceae	Eukaryota	n.a.	bark	n.a.	PMID[19329133]
NPO6333	Annona glabra	Species	Annonaceae	Eukaryota	stem	Taipei Botanical Garden, Taipei, Taiwan, China	2006-MAR	PMID[20828184]
NPO29110	Litsea cubeba	Species	Lauraceae	Eukaryota	essential oil	Tibet	n.a.	PMID[20944522]
NPO6333	Annona glabra	Species	Annonaceae	Eukaryota	fruits	n.a.	n.a.	PMID[25499882]
NPO29110	Litsea cubeba	Species	Lauraceae	Eukaryota	Twigs	n.a.	n.a.	PMID[28541690]
NPO27903	Delphinium denudatum	Species	Ranunculaceae	Eukaryota	n.a.	root	n.a.	PMID[9170290]
NPO6333	Annona glabra	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9584397]
NPO6333	Annona glabra	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9599260]
NPO29110	Litsea cubeba	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO27724	Polygala senega	Species	Polygalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO6333	Annona glabra	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26851	Eupatorium rebaudianum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO27903	Delphinium denudatum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26851	Eupatorium rebaudianum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1079	Vachellia karroo	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18780	Diplacus aurantiacus	Species	Phrymaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27724	Polygala senega	Species	Polygalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6333	Annona glabra	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27903	Delphinium denudatum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29110	Litsea cubeba	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27724	Polygala senega	Species	Polygalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO27724	Polygala senega	Species	Polygalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO29110	Litsea cubeba	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO27724	Polygala senega	Species	Polygalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29411	Streptomyces nigrescens	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO29110	Litsea cubeba	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16079	Cephalaria leucantha	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26851	Eupatorium rebaudianum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26549	Polanisia trachysperma	Species	Cleomaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28959	Cissus quadrangularis	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29377	Callistemon speciosus	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27883	Bursera simaruba	Species	Burseraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1079	Vachellia karroo	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18780	Diplacus aurantiacus	Species	Phrymaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29218	Ramalina farinacea	Species	Ramalinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29144	Ormosia fordiana	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28935	Ericameria laricifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27903	Delphinium denudatum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28549	Mentha incana	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO862	Podocarpus elatus	Species	Podocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27256	Solanum boerhaavii	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6333	Annona glabra	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27562	Coleus wulfenioides	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29307	Loranthus longiflorus	Species	Loranthaceae	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
NPT66	Individual Protein	Acetylcholinesterase	Electrophorus electricus	IC50	>	150000.0	nM	PMID[476535]

☑ 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 NPC182907 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	558
0.1-0.2	2587
0.2-0.3	10072
0.3-0.4	7142
0.4-0.5	9124
0.5-0.6	10940
0.6-0.7	1927
0.7-0.8	267
0.8-0.85	56
0.85-0.9	4
0.9-0.95	9
0.95-1	11

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC189903
0.9952	High Similarity	NPC108342
0.9856	High Similarity	NPC22481
0.9764	High Similarity	NPC166722
0.9721	High Similarity	NPC124313
0.972	High Similarity	NPC84164
0.972	High Similarity	NPC207283
0.9713	High Similarity	NPC278525
0.9673	High Similarity	NPC210296
0.9619	High Similarity	NPC24019
0.95	High Similarity	NPC183537
0.9426	High Similarity	NPC210434
0.9412	High Similarity	NPC77878
0.9349	High Similarity	NPC90875
0.9346	High Similarity	NPC233334
0.914	High Similarity	NPC15406
0.9	High Similarity	NPC146976
0.8952	High Similarity	NPC236668
0.8726	High Similarity	NPC251160
0.8655	High Similarity	NPC253675
0.8632	High Similarity	NPC470020
0.8546	High Similarity	NPC119134
0.8485	Intermediate Similarity	NPC270515
0.8387	Intermediate Similarity	NPC235076
0.8372	Intermediate Similarity	NPC188420
0.8333	Intermediate Similarity	NPC322482
0.8294	Intermediate Similarity	NPC477019
0.8273	Intermediate Similarity	NPC23614
0.8273	Intermediate Similarity	NPC100079
0.8257	Intermediate Similarity	NPC149471
0.8257	Intermediate Similarity	NPC271215
0.8235	Intermediate Similarity	NPC46451
0.8228	Intermediate Similarity	NPC478045
0.8211	Intermediate Similarity	NPC53069
0.8211	Intermediate Similarity	NPC202768
0.8211	Intermediate Similarity	NPC296482
0.8208	Intermediate Similarity	NPC234197
0.8178	Intermediate Similarity	NPC470018
0.8148	Intermediate Similarity	NPC313189
0.8142	Intermediate Similarity	NPC74575
0.8128	Intermediate Similarity	NPC96405
0.8128	Intermediate Similarity	NPC171409
0.8125	Intermediate Similarity	NPC118121
0.8125	Intermediate Similarity	NPC122463
0.8108	Intermediate Similarity	NPC204446
0.8066	Intermediate Similarity	NPC132385
0.8065	Intermediate Similarity	NPC135549
0.8048	Intermediate Similarity	NPC195268
0.8048	Intermediate Similarity	NPC133140
0.8	Intermediate Similarity	NPC49547
0.7974	Intermediate Similarity	NPC470017
0.7973	Intermediate Similarity	NPC55470
0.7965	Intermediate Similarity	NPC216612
0.795	Intermediate Similarity	NPC137353
0.794	Intermediate Similarity	NPC470022
0.789	Intermediate Similarity	NPC16452
0.789	Intermediate Similarity	NPC36229
0.789	Intermediate Similarity	NPC476581
0.787	Intermediate Similarity	NPC246381
0.7824	Intermediate Similarity	NPC476582
0.7824	Intermediate Similarity	NPC4071
0.7824	Intermediate Similarity	NPC476578
0.7797	Intermediate Similarity	NPC174049
0.7759	Intermediate Similarity	NPC134637
0.7752	Intermediate Similarity	NPC31930
0.7741	Intermediate Similarity	NPC208522
0.7738	Intermediate Similarity	NPC193238
0.7719	Intermediate Similarity	NPC54066
0.7692	Intermediate Similarity	NPC471004
0.7679	Intermediate Similarity	NPC220337
0.7673	Intermediate Similarity	NPC318068
0.7658	Intermediate Similarity	NPC308943
0.7657	Intermediate Similarity	NPC72905
0.7644	Intermediate Similarity	NPC202605
0.7644	Intermediate Similarity	NPC112206
0.7635	Intermediate Similarity	NPC107123
0.7634	Intermediate Similarity	NPC290689
0.7632	Intermediate Similarity	NPC473822
0.7625	Intermediate Similarity	NPC142385
0.7615	Intermediate Similarity	NPC23080
0.7615	Intermediate Similarity	NPC193906
0.7611	Intermediate Similarity	NPC129897
0.7581	Intermediate Similarity	NPC191489
0.758	Intermediate Similarity	NPC5374
0.7573	Intermediate Similarity	NPC41501
0.7543	Intermediate Similarity	NPC94842
0.751	Intermediate Similarity	NPC302807
0.75	Intermediate Similarity	NPC222561
0.746	Intermediate Similarity	NPC315634
0.746	Intermediate Similarity	NPC100734
0.746	Intermediate Similarity	NPC88923
0.7455	Intermediate Similarity	NPC71124
0.7454	Intermediate Similarity	NPC312531
0.7453	Intermediate Similarity	NPC206201
0.7437	Intermediate Similarity	NPC255800
0.7437	Intermediate Similarity	NPC96584
0.7431	Intermediate Similarity	NPC254957
0.7426	Intermediate Similarity	NPC201508
0.7425	Intermediate Similarity	NPC477788
0.7419	Intermediate Similarity	NPC303374
0.7397	Intermediate Similarity	NPC148889
0.7397	Intermediate Similarity	NPC146724
0.7395	Intermediate Similarity	NPC204385
0.7393	Intermediate Similarity	NPC122436
0.739	Intermediate Similarity	NPC13603
0.7388	Intermediate Similarity	NPC1608
0.738	Intermediate Similarity	NPC232225
0.7371	Intermediate Similarity	NPC473833
0.7366	Intermediate Similarity	NPC207971
0.7355	Intermediate Similarity	NPC253482
0.7349	Intermediate Similarity	NPC85879
0.7349	Intermediate Similarity	NPC475301
0.7349	Intermediate Similarity	NPC249405
0.7349	Intermediate Similarity	NPC53255
0.7349	Intermediate Similarity	NPC326930
0.7344	Intermediate Similarity	NPC235685
0.7336	Intermediate Similarity	NPC475648
0.7333	Intermediate Similarity	NPC268077
0.7331	Intermediate Similarity	NPC473506
0.733	Intermediate Similarity	NPC224928
0.7327	Intermediate Similarity	NPC474009
0.7314	Intermediate Similarity	NPC101350
0.7312	Intermediate Similarity	NPC328928
0.7308	Intermediate Similarity	NPC280799
0.7302	Intermediate Similarity	NPC89549
0.73	Intermediate Similarity	NPC475600
0.73	Intermediate Similarity	NPC228377
0.73	Intermediate Similarity	NPC476110
0.73	Intermediate Similarity	NPC475631
0.73	Intermediate Similarity	NPC87152
0.73	Intermediate Similarity	NPC328186
0.73	Intermediate Similarity	NPC477787
0.73	Intermediate Similarity	NPC122968
0.7297	Intermediate Similarity	NPC127085
0.7294	Intermediate Similarity	NPC470042
0.7293	Intermediate Similarity	NPC208284
0.7284	Intermediate Similarity	NPC168922
0.728	Intermediate Similarity	NPC475303
0.728	Intermediate Similarity	NPC473689
0.728	Intermediate Similarity	NPC292416
0.728	Intermediate Similarity	NPC316841
0.728	Intermediate Similarity	NPC474688
0.728	Intermediate Similarity	NPC475596
0.7273	Intermediate Similarity	NPC298449
0.7273	Intermediate Similarity	NPC472061
0.7273	Intermediate Similarity	NPC4421
0.7269	Intermediate Similarity	NPC475644
0.7269	Intermediate Similarity	NPC471190
0.7269	Intermediate Similarity	NPC471977
0.7269	Intermediate Similarity	NPC470486
0.7265	Intermediate Similarity	NPC469439
0.7262	Intermediate Similarity	NPC284685
0.7261	Intermediate Similarity	NPC475406
0.7257	Intermediate Similarity	NPC38961
0.7254	Intermediate Similarity	NPC475844
0.7254	Intermediate Similarity	NPC217554
0.7253	Intermediate Similarity	NPC473089
0.7253	Intermediate Similarity	NPC6576
0.7253	Intermediate Similarity	NPC212768
0.7253	Intermediate Similarity	NPC75600
0.7253	Intermediate Similarity	NPC158020
0.7253	Intermediate Similarity	NPC473115
0.725	Intermediate Similarity	NPC244839
0.725	Intermediate Similarity	NPC319880
0.725	Intermediate Similarity	NPC320324
0.725	Intermediate Similarity	NPC30456
0.7237	Intermediate Similarity	NPC207873
0.7237	Intermediate Similarity	NPC100573
0.7236	Intermediate Similarity	NPC284141
0.7234	Intermediate Similarity	NPC477903
0.7231	Intermediate Similarity	NPC327904
0.7231	Intermediate Similarity	NPC38959
0.7225	Intermediate Similarity	NPC300156
0.7222	Intermediate Similarity	NPC179704
0.722	Intermediate Similarity	NPC329631
0.722	Intermediate Similarity	NPC237702
0.721	Intermediate Similarity	NPC246658
0.7208	Intermediate Similarity	NPC476999
0.7208	Intermediate Similarity	NPC260434
0.7203	Intermediate Similarity	NPC144452
0.719	Intermediate Similarity	NPC35208
0.719	Intermediate Similarity	NPC327769
0.719	Intermediate Similarity	NPC9482
0.7188	Intermediate Similarity	NPC280714
0.7183	Intermediate Similarity	NPC478083
0.7177	Intermediate Similarity	NPC475315
0.7177	Intermediate Similarity	NPC324619
0.7176	Intermediate Similarity	NPC471978
0.7174	Intermediate Similarity	NPC124086
0.7173	Intermediate Similarity	NPC250807
0.7173	Intermediate Similarity	NPC76565
0.7173	Intermediate Similarity	NPC57797
0.7172	Intermediate Similarity	NPC11408
0.7163	Intermediate Similarity	NPC287588
0.7162	Intermediate Similarity	NPC82548
0.7162	Intermediate Similarity	NPC90185
0.716	Intermediate Similarity	NPC471979
0.7155	Intermediate Similarity	NPC211920
0.7155	Intermediate Similarity	NPC324361
0.7155	Intermediate Similarity	NPC146824

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 NPC182907 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	326
0.1-0.2	677
0.2-0.3	942
0.3-0.4	1640
0.4-0.5	2632
0.5-0.6	2162
0.6-0.7	708
0.7-0.8	58
0.8-0.85	5
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8235	Intermediate Similarity	NPD3763	Approved
0.8211	Intermediate Similarity	NPD3816	Phase 1
0.8211	Intermediate Similarity	NPD3815	Phase 1
0.8048	Intermediate Similarity	NPD3924	Approved
0.8048	Intermediate Similarity	NPD3921	Approved
0.8048	Intermediate Similarity	NPD3922	Approved
0.8048	Intermediate Similarity	NPD3923	Approved
0.8033	Intermediate Similarity	NPD4926	Clinical (unspecified phase)
0.7722	Intermediate Similarity	NPD7885	Phase 2
0.7722	Intermediate Similarity	NPD7886	Phase 2
0.7714	Intermediate Similarity	NPD8091	Phase 3
0.7615	Intermediate Similarity	NPD6790	Phase 1
0.7611	Intermediate Similarity	NPD7571	Clinical (unspecified phase)
0.7581	Intermediate Similarity	NPD7708	Approved
0.7572	Intermediate Similarity	NPD8350	Clinical (unspecified phase)
0.7566	Intermediate Similarity	NPD7069	Discontinued
0.7542	Intermediate Similarity	NPD4885	Approved
0.7541	Intermediate Similarity	NPD6525	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD5801	Clinical (unspecified phase)
0.7524	Intermediate Similarity	NPD3920	Phase 2
0.751	Intermediate Similarity	NPD1483	Discontinued
0.749	Intermediate Similarity	NPD5805	Approved
0.746	Intermediate Similarity	NPD7803	Approved
0.7437	Intermediate Similarity	NPD6494	Phase 2
0.7414	Intermediate Similarity	NPD6242	Discontinued
0.741	Intermediate Similarity	NPD7862	Clinical (unspecified phase)
0.7398	Intermediate Similarity	NPD5482	Discontinued
0.7336	Intermediate Similarity	NPD5866	Approved
0.7328	Intermediate Similarity	NPD7395	Discontinued
0.7328	Intermediate Similarity	NPD6568	Discontinued
0.7306	Intermediate Similarity	NPD5483	Clinical (unspecified phase)
0.7281	Intermediate Similarity	NPD6257	Clinical (unspecified phase)
0.7262	Intermediate Similarity	NPD7956	Approved
0.7262	Intermediate Similarity	NPD7955	Approved
0.7261	Intermediate Similarity	NPD6963	Approved
0.7261	Intermediate Similarity	NPD6964	Approved
0.7243	Intermediate Similarity	NPD6727	Phase 2
0.722	Intermediate Similarity	NPD5040	Clinical (unspecified phase)
0.722	Intermediate Similarity	NPD6741	Clinical (unspecified phase)
0.721	Intermediate Similarity	NPD4989	Phase 2
0.7206	Intermediate Similarity	NPD5488	Discontinued
0.7189	Intermediate Similarity	NPD4889	Approved
0.7184	Intermediate Similarity	NPD7417	Discontinued
0.7179	Intermediate Similarity	NPD4429	Discontinued
0.7168	Intermediate Similarity	NPD6477	Clinical (unspecified phase)
0.7167	Intermediate Similarity	NPD4952	Phase 3
0.7154	Intermediate Similarity	NPD6716	Phase 1
0.7143	Intermediate Similarity	NPD2921	Clinical (unspecified phase)
0.7137	Intermediate Similarity	NPD6460	Clinical (unspecified phase)
0.7137	Intermediate Similarity	NPD3217	Phase 2
0.7137	Intermediate Similarity	NPD3326	Clinical (unspecified phase)
0.713	Intermediate Similarity	NPD7414	Clinical (unspecified phase)
0.7118	Intermediate Similarity	NPD5429	Discontinued
0.7098	Intermediate Similarity	NPD6530	Approved
0.7098	Intermediate Similarity	NPD6531	Approved
0.7095	Intermediate Similarity	NPD8052	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD4373	Phase 2
0.7071	Intermediate Similarity	NPD6247	Clinical (unspecified phase)
0.7069	Intermediate Similarity	NPD7927	Clinical (unspecified phase)
0.7054	Intermediate Similarity	NPD5450	Discontinued
0.7052	Intermediate Similarity	NPD7588	Discontinued
0.7046	Intermediate Similarity	NPD8479	Phase 2
0.7034	Intermediate Similarity	NPD3354	Phase 2
0.7031	Intermediate Similarity	NPD6228	Discontinued
0.7026	Intermediate Similarity	NPD5914	Approved
0.7026	Intermediate Similarity	NPD4997	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD5022	Discontinued
0.702	Intermediate Similarity	NPD7169	Suspended
0.702	Intermediate Similarity	NPD3006	Discontinued
0.7016	Intermediate Similarity	NPD6517	Phase 3
0.7013	Intermediate Similarity	NPD5658	Approved
0.7012	Intermediate Similarity	NPD3259	Approved
0.7009	Intermediate Similarity	NPD4418	Discontinued
0.6987	Remote Similarity	NPD5513	Phase 2
0.6987	Remote Similarity	NPD2285	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD1923	Clinical (unspecified phase)
0.6972	Remote Similarity	NPD3386	Phase 2
0.6971	Remote Similarity	NPD7426	Phase 1
0.6971	Remote Similarity	NPD3263	Phase 3
0.696	Remote Similarity	NPD6230	Discontinued
0.6958	Remote Similarity	NPD7278	Phase 2
0.6958	Remote Similarity	NPD7279	Phase 2
0.6957	Remote Similarity	NPD3946	Clinical (unspecified phase)
0.6947	Remote Similarity	NPD5459	Phase 2
0.694	Remote Similarity	NPD4859	Phase 1
0.6933	Remote Similarity	NPD5519	Discontinued
0.6932	Remote Similarity	NPD8468	Phase 2
0.693	Remote Similarity	NPD6219	Discontinued
0.6926	Remote Similarity	NPD7010	Phase 3
0.6926	Remote Similarity	NPD6962	Phase 2
0.6907	Remote Similarity	NPD3257	Approved
0.6891	Remote Similarity	NPD5632	Approved
0.6883	Remote Similarity	NPD5891	Approved
0.6878	Remote Similarity	NPD8149	Discontinued
0.6877	Remote Similarity	NPD4558	Phase 2
0.6875	Remote Similarity	NPD4923	Phase 1
0.6872	Remote Similarity	NPD7268	Clinical (unspecified phase)
0.6872	Remote Similarity	NPD7994	Phase 2
0.687	Remote Similarity	NPD7558	Phase 2
0.6867	Remote Similarity	NPD8016	Phase 3
0.6867	Remote Similarity	NPD7467	Discontinued
0.6867	Remote Similarity	NPD8017	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD7859	Phase 2
0.6857	Remote Similarity	NPD1505	Phase 2
0.6853	Remote Similarity	NPD5530	Phase 1
0.6847	Remote Similarity	NPD4375	Approved
0.6846	Remote Similarity	NPD6160	Clinical (unspecified phase)
0.6844	Remote Similarity	NPD6569	Phase 2
0.6844	Remote Similarity	NPD7710	Clinical (unspecified phase)
0.6833	Remote Similarity	NPD7180	Phase 3
0.6833	Remote Similarity	NPD5930	Phase 3
0.6833	Remote Similarity	NPD5850	Phase 3
0.6832	Remote Similarity	NPD7673	Phase 3
0.6831	Remote Similarity	NPD5640	Discontinued
0.683	Remote Similarity	NPD6281	Approved
0.6824	Remote Similarity	NPD6503	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD7222	Phase 2
0.6822	Remote Similarity	NPD7225	Discontinued
0.681	Remote Similarity	NPD4037	Approved
0.681	Remote Similarity	NPD4038	Approved
0.681	Remote Similarity	NPD4122	Approved
0.681	Remote Similarity	NPD31	Approved
0.681	Remote Similarity	NPD4039	Approved
0.681	Remote Similarity	NPD4036	Approved
0.681	Remote Similarity	NPD4033	Approved
0.681	Remote Similarity	NPD4034	Approved
0.681	Remote Similarity	NPD32	Approved
0.681	Remote Similarity	NPD4035	Approved
0.6806	Remote Similarity	NPD7924	Phase 2
0.6806	Remote Similarity	NPD7925	Phase 2
0.6806	Remote Similarity	NPD1078	Clinical (unspecified phase)
0.6804	Remote Similarity	NPD1620	Clinical (unspecified phase)
0.68	Remote Similarity	NPD2334	Discontinued
0.6798	Remote Similarity	NPD8100	Phase 3
0.6792	Remote Similarity	NPD3258	Approved
0.6792	Remote Similarity	NPD6974	Phase 3
0.6786	Remote Similarity	NPD7233	Approved
0.6786	Remote Similarity	NPD7234	Approved
0.6784	Remote Similarity	NPD5975	Clinical (unspecified phase)
0.6783	Remote Similarity	NPD4396	Clinical (unspecified phase)
0.6781	Remote Similarity	NPD5601	Phase 2
0.6776	Remote Similarity	NPD7555	Discontinued
0.6772	Remote Similarity	NPD8279	Clinical (unspecified phase)
0.6769	Remote Similarity	NPD5867	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD7538	Clinical (unspecified phase)
0.6763	Remote Similarity	NPD6745	Discontinued
0.676	Remote Similarity	NPD6825	Phase 1
0.6754	Remote Similarity	NPD5512	Phase 3
0.6754	Remote Similarity	NPD6550	Discontinued
0.6749	Remote Similarity	NPD7547	Clinical (unspecified phase)
0.6748	Remote Similarity	NPD7567	Approved
0.6747	Remote Similarity	NPD7853	Phase 2
0.6746	Remote Similarity	NPD4876	Phase 3
0.6746	Remote Similarity	NPD4875	Phase 3
0.674	Remote Similarity	NPD1038	Approved
0.674	Remote Similarity	NPD4551	Phase 2
0.674	Remote Similarity	NPD1304	Clinical (unspecified phase)
0.6736	Remote Similarity	NPD5612	Discontinued
0.6736	Remote Similarity	NPD2433	Clinical (unspecified phase)
0.6735	Remote Similarity	NPD4328	Approved
0.6735	Remote Similarity	NPD6553	Clinical (unspecified phase)
0.6735	Remote Similarity	NPD4845	Discontinued
0.6724	Remote Similarity	NPD6975	Discontinued
0.672	Remote Similarity	NPD4958	Clinical (unspecified phase)
0.672	Remote Similarity	NPD4846	Phase 2
0.6719	Remote Similarity	NPD8101	Phase 3
0.6713	Remote Similarity	NPD6872	Clinical (unspecified phase)
0.6709	Remote Similarity	NPD2060	Approved
0.6709	Remote Similarity	NPD7703	Clinical (unspecified phase)
0.6709	Remote Similarity	NPD6567	Clinical (unspecified phase)
0.6708	Remote Similarity	NPD6824	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD7807	Clinical (unspecified phase)
0.6706	Remote Similarity	NPD8358	Approved
0.6706	Remote Similarity	NPD6276	Discontinued
0.6706	Remote Similarity	NPD3328	Phase 2
0.6705	Remote Similarity	NPD5532	Phase 2
0.6705	Remote Similarity	NPD8463	Approved
0.6698	Remote Similarity	NPD2782	Approved
0.6698	Remote Similarity	NPD2780	Approved
0.6696	Remote Similarity	NPD4420	Approved
0.6695	Remote Similarity	NPD4667	Clinical (unspecified phase)
0.6694	Remote Similarity	NPD7858	Clinical (unspecified phase)
0.6694	Remote Similarity	NPD5070	Clinical (unspecified phase)
0.6693	Remote Similarity	NPD7729	Clinical (unspecified phase)
0.668	Remote Similarity	NPD5479	Discontinued
0.668	Remote Similarity	NPD8102	Discontinued
0.6679	Remote Similarity	NPD7690	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3394	Approved
0.6667	Remote Similarity	NPD3389	Approved
0.6667	Remote Similarity	NPD6298	Discontinued
0.6667	Remote Similarity	NPD3393	Approved
0.6667	Remote Similarity	NPD3947	Discontinued
0.6667	Remote Similarity	NPD4118	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4795	Phase 2
0.6667	Remote Similarity	NPD7689	Approved
0.6667	Remote Similarity	NPD6361	Phase 2
0.6667	Remote Similarity	NPD6138	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6987	Phase 1
0.6653	Remote Similarity	NPD3925	Approved
0.6653	Remote Similarity	NPD2739	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