NPASS Compound

Structure

CID67377 OpenBabel06191715402D 22 25 0 0 0 0 0 0 0 0999 V2000 1.3048 -2.2764 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1774 -0.1656 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3028 0.7872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2895 -0.5333 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5421 2.3863 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5404 1.3723 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5271 0.0517 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7175 2.8779 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5295 1.4253 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0383 2.9001 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7987 2.4304 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6792 -0.0222 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6525 1.0045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8687 2.4084 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6920 0.9445 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8114 1.4694 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8419 -0.4861 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8560 1.4474 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0128 0.9667 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 -0.8385 -0.4743 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8335 -1.4433 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 22 1 0 0 0 0 2 3 2 0 0 0 0 2 4 1 0 0 0 0 3 6 1 0 0 0 0 4 7 2 0 0 0 0 5 8 2 0 0 0 0 5 9 1 0 0 0 0 6 13 2 0 0 0 0 7 13 1 0 0 0 0 8 14 1 0 0 0 0 9 15 2 0 0 0 0 10 11 2 0 0 0 0 10 14 1 0 0 0 0 11 16 1 0 0 0 0 12 15 1 0 0 0 0 12 17 2 0 0 0 0 13 16 1 0 0 0 0 14 18 2 0 0 0 0 15 18 1 0 0 0 0 16 19 2 0 0 0 0 17 20 1 0 0 0 0 17 22 1 0 0 0 0 18 19 1 0 0 0 0 19 20 1 0 0 0 0 20 21 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	286.1
Volume:	311.466
LogP:	4.491
LogD:	3.825
LogS:	-6.204
# Rotatable Bonds:	2
TPSA:	26.3
# H-Bond Aceptor:	2
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.683
Synthetic Accessibility Score:	2.227
Fsp3:	0.05
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:	-4.918
MDCK Permeability:	1.5495379557251e-05
Pgp-inhibitor:	0.977
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.002
20% Bioavailability (F20%):	0.218
30% Bioavailability (F30%):	0.918

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.076
Plasma Protein Binding (PPB):	99.60765838623047%
Volume Distribution (VD):	0.602
Pgp-substrate:	0.5847501754760742%

ADMET: Metabolism

CYP1A2-inhibitor:	0.984
CYP1A2-substrate:	0.784
CYP2C19-inhibitor:	0.892
CYP2C19-substrate:	0.066
CYP2C9-inhibitor:	0.757
CYP2C9-substrate:	0.905
CYP2D6-inhibitor:	0.413
CYP2D6-substrate:	0.869
CYP3A4-inhibitor:	0.666
CYP3A4-substrate:	0.193

ADMET: Excretion

Clearance (CL):	3.79
Half-life (T1/2):	0.061

ADMET: Toxicity

hERG Blockers:	0.468
Human Hepatotoxicity (H-HT):	0.844
Drug-inuced Liver Injury (DILI):	0.899
AMES Toxicity:	0.934
Rat Oral Acute Toxicity:	0.052
Maximum Recommended Daily Dose:	0.747
Skin Sensitization:	0.949
Carcinogencity:	0.908
Eye Corrosion:	0.004
Eye Irritation:	0.932
Respiratory Toxicity:	0.85

Download Data

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

Natural Product: NPC67377

Natural Product ID:	NPC67377
*Common Name:**	2-Methoxy-9-Phenylphenalen-1-One
IUPAC Name:	2-methoxy-9-phenylphenalen-1-one
Synonyms:
Standard InCHIKey:	NXRGWQRQXPUQSX-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C20H14O2/c1-22-17-12-15-9-5-8-14-10-11-16(13-6-3-2-4-7-13)19(18(14)15)20(17)21/h2-12H,1H3
SMILES:	COC1=Cc2cccc3c2c(C1=O)c(cc3)c1ccccc1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1164385
PubChem CID:	10085389
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000023] Naphthalenes [CHEMONTID:0002044] Phenylnaphthalenes

*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
NPO22441	Senna spectabilis	Species	Fabaceae	Eukaryota	flowers	n.a.	n.a.	PMID[30413343]
NPO23044	Aesculus hippocastanum	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[3783160]
NPO23044	Aesculus hippocastanum	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO10654	Lindera obtusiloba	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23044	Aesculus hippocastanum	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16782	Andrographis viscosula	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10654	Lindera obtusiloba	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10654	Lindera obtusiloba	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO23044	Aesculus hippocastanum	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO10654	Lindera obtusiloba	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO5869	Anthocercis albicans	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22441	Senna spectabilis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10984	Euclea crispa	Species	Ebenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11360	Tiliacora racemosa	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18427	Axinella agnata	Species	Axinellidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17900	Iotrochota birotulata	Species	Iotrochotidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3096	Verbascum laxum	Species	Scrophulariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10064	Diospyros canaliculata	Species	Ebenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19091	Bacterium from	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO23044	Aesculus hippocastanum	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16782	Andrographis viscosula	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16548	Chenopodium formosanum	Species	Chenopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10654	Lindera obtusiloba	Species	Lauraceae	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	2
IC50	4
Others	1

Activity Type	# Activity
Cell Line	1
Organism	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT83	Cell Line	MCF7	Homo sapiens	Inhibition	=	14.0	%	PMID[505667]
NPT634	Organism	Leishmania amazonensis	Leishmania amazonensis	IC50	=	9.04	ug.mL-1	PMID[505667]
NPT633	Organism	Leishmania donovani	Leishmania donovani	IC50	=	29.9	ug.mL-1	PMID[505667]
NPT580	Organism	Trypanosoma cruzi	Trypanosoma cruzi	IC50	=	48.35	ug.mL-1	PMID[505667]
NPT633	Organism	Leishmania donovani	Leishmania donovani	EC50	<	60.0	ug.mL-1	PMID[505668]
NPT1021	Organism	Leishmania infantum	Leishmania infantum	EC50	<	60.0	ug.mL-1	PMID[505668]
NPT633	Organism	Leishmania donovani	Leishmania donovani	IC50	=	35000.0	nM	PMID[505669]

☑ 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 NPC67377 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	315
0.1-0.2	1522
0.2-0.3	3475
0.3-0.4	11564
0.4-0.5	11484
0.5-0.6	11278
0.6-0.7	2755
0.7-0.8	271
0.8-0.85	26
0.85-0.9	4
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9429	High Similarity	NPC203732
0.9259	High Similarity	NPC186128
0.8919	High Similarity	NPC326664
0.8704	High Similarity	NPC134120
0.8595	High Similarity	NPC478165
0.8595	High Similarity	NPC478162
0.8534	High Similarity	NPC318173
0.8505	High Similarity	NPC112552
0.8482	Intermediate Similarity	NPC137315
0.8476	Intermediate Similarity	NPC12695
0.8468	Intermediate Similarity	NPC192577
0.8381	Intermediate Similarity	NPC472880
0.8364	Intermediate Similarity	NPC172483
0.8333	Intermediate Similarity	NPC143768
0.8319	Intermediate Similarity	NPC144547
0.8293	Intermediate Similarity	NPC428300
0.8264	Intermediate Similarity	NPC318067
0.8261	Intermediate Similarity	NPC241851
0.8246	Intermediate Similarity	NPC292834
0.8235	Intermediate Similarity	NPC232958
0.8235	Intermediate Similarity	NPC289432
0.8235	Intermediate Similarity	NPC988
0.8224	Intermediate Similarity	NPC103048
0.8205	Intermediate Similarity	NPC469843
0.8197	Intermediate Similarity	NPC164014
0.819	Intermediate Similarity	NPC470764
0.8182	Intermediate Similarity	NPC274443
0.8158	Intermediate Similarity	NPC291799
0.8148	Intermediate Similarity	NPC49994
0.8148	Intermediate Similarity	NPC145052
0.8136	Intermediate Similarity	NPC323440
0.8136	Intermediate Similarity	NPC80605
0.8136	Intermediate Similarity	NPC222968
0.8125	Intermediate Similarity	NPC100767
0.8113	Intermediate Similarity	NPC289883
0.8095	Intermediate Similarity	NPC476484
0.8091	Intermediate Similarity	NPC244427
0.8091	Intermediate Similarity	NPC222390
0.8087	Intermediate Similarity	NPC280789
0.8077	Intermediate Similarity	NPC186647
0.8053	Intermediate Similarity	NPC470391
0.8034	Intermediate Similarity	NPC474408
0.8034	Intermediate Similarity	NPC228936
0.8018	Intermediate Similarity	NPC247976
0.8017	Intermediate Similarity	NPC470253
0.8017	Intermediate Similarity	NPC13784
0.8	Intermediate Similarity	NPC265513
0.8	Intermediate Similarity	NPC472879
0.8	Intermediate Similarity	NPC476993
0.8	Intermediate Similarity	NPC277277
0.7983	Intermediate Similarity	NPC228318
0.7967	Intermediate Similarity	NPC328107
0.7966	Intermediate Similarity	NPC135730
0.7953	Intermediate Similarity	NPC27659
0.7949	Intermediate Similarity	NPC196673
0.7909	Intermediate Similarity	NPC476042
0.7905	Intermediate Similarity	NPC418308
0.789	Intermediate Similarity	NPC239185
0.7881	Intermediate Similarity	NPC474095
0.787	Intermediate Similarity	NPC260233
0.7857	Intermediate Similarity	NPC329556
0.7851	Intermediate Similarity	NPC476645
0.785	Intermediate Similarity	NPC155232
0.785	Intermediate Similarity	NPC153885
0.783	Intermediate Similarity	NPC303967
0.783	Intermediate Similarity	NPC173413
0.783	Intermediate Similarity	NPC67585
0.783	Intermediate Similarity	NPC110420
0.783	Intermediate Similarity	NPC19256
0.7818	Intermediate Similarity	NPC134882
0.7815	Intermediate Similarity	NPC62138
0.781	Intermediate Similarity	NPC267262
0.7798	Intermediate Similarity	NPC219573
0.7798	Intermediate Similarity	NPC185208
0.7797	Intermediate Similarity	NPC471721
0.7787	Intermediate Similarity	NPC238861
0.7787	Intermediate Similarity	NPC105709
0.7787	Intermediate Similarity	NPC77000
0.7778	Intermediate Similarity	NPC238219
0.7769	Intermediate Similarity	NPC470406
0.7757	Intermediate Similarity	NPC133461
0.7742	Intermediate Similarity	NPC65627
0.7739	Intermediate Similarity	NPC470007
0.7731	Intermediate Similarity	NPC215419
0.7727	Intermediate Similarity	NPC156021
0.7727	Intermediate Similarity	NPC265220
0.7719	Intermediate Similarity	NPC471186
0.7712	Intermediate Similarity	NPC93287
0.771	Intermediate Similarity	NPC474659
0.771	Intermediate Similarity	NPC23894
0.7692	Intermediate Similarity	NPC474057
0.7679	Intermediate Similarity	NPC109514
0.7672	Intermediate Similarity	NPC318327
0.7672	Intermediate Similarity	NPC470252
0.7667	Intermediate Similarity	NPC260886
0.7664	Intermediate Similarity	NPC472836
0.7658	Intermediate Similarity	NPC75724
0.7647	Intermediate Similarity	NPC196075
0.7642	Intermediate Similarity	NPC157778
0.7627	Intermediate Similarity	NPC212415
0.7627	Intermediate Similarity	NPC471189
0.7627	Intermediate Similarity	NPC66208
0.7619	Intermediate Similarity	NPC295664
0.7619	Intermediate Similarity	NPC307
0.7619	Intermediate Similarity	NPC160339
0.7615	Intermediate Similarity	NPC34243
0.7603	Intermediate Similarity	NPC158157
0.7597	Intermediate Similarity	NPC57552
0.7593	Intermediate Similarity	NPC103346
0.7593	Intermediate Similarity	NPC284475
0.7591	Intermediate Similarity	NPC478164
0.7589	Intermediate Similarity	NPC221825
0.7581	Intermediate Similarity	NPC472981
0.7561	Intermediate Similarity	NPC204784
0.7561	Intermediate Similarity	NPC202015
0.7557	Intermediate Similarity	NPC183103
0.7547	Intermediate Similarity	NPC69057
0.7547	Intermediate Similarity	NPC43945
0.7541	Intermediate Similarity	NPC61651
0.7541	Intermediate Similarity	NPC268930
0.754	Intermediate Similarity	NPC85511
0.754	Intermediate Similarity	NPC51079
0.7537	Intermediate Similarity	NPC264022
0.7523	Intermediate Similarity	NPC188844
0.7523	Intermediate Similarity	NPC59677
0.7523	Intermediate Similarity	NPC1682
0.7523	Intermediate Similarity	NPC323420
0.75	Intermediate Similarity	NPC83409
0.75	Intermediate Similarity	NPC185763
0.75	Intermediate Similarity	NPC477411
0.7482	Intermediate Similarity	NPC478160
0.7482	Intermediate Similarity	NPC478166
0.7479	Intermediate Similarity	NPC79496
0.7479	Intermediate Similarity	NPC218855
0.7478	Intermediate Similarity	NPC329282
0.746	Intermediate Similarity	NPC164947
0.7458	Intermediate Similarity	NPC273837
0.7447	Intermediate Similarity	NPC472839
0.7438	Intermediate Similarity	NPC93181
0.7436	Intermediate Similarity	NPC112903
0.7422	Intermediate Similarity	NPC236405
0.7417	Intermediate Similarity	NPC469547
0.7414	Intermediate Similarity	NPC105899
0.7411	Intermediate Similarity	NPC226041
0.7407	Intermediate Similarity	NPC325709
0.7405	Intermediate Similarity	NPC55949
0.7402	Intermediate Similarity	NPC135062
0.7402	Intermediate Similarity	NPC325740
0.7395	Intermediate Similarity	NPC210089
0.7387	Intermediate Similarity	NPC172925
0.7385	Intermediate Similarity	NPC96024
0.7385	Intermediate Similarity	NPC48248
0.7381	Intermediate Similarity	NPC269923
0.7381	Intermediate Similarity	NPC167323
0.7377	Intermediate Similarity	NPC226093
0.7376	Intermediate Similarity	NPC478163
0.7368	Intermediate Similarity	NPC225051
0.7364	Intermediate Similarity	NPC81135
0.7364	Intermediate Similarity	NPC177925
0.736	Intermediate Similarity	NPC476225
0.7355	Intermediate Similarity	NPC130591
0.7355	Intermediate Similarity	NPC234637
0.735	Intermediate Similarity	NPC37914
0.735	Intermediate Similarity	NPC94751
0.735	Intermediate Similarity	NPC142326
0.7348	Intermediate Similarity	NPC474517
0.7348	Intermediate Similarity	NPC72669
0.7344	Intermediate Similarity	NPC474766
0.7344	Intermediate Similarity	NPC142956
0.7343	Intermediate Similarity	NPC58310
0.7343	Intermediate Similarity	NPC295977
0.7333	Intermediate Similarity	NPC471188
0.7328	Intermediate Similarity	NPC34414
0.7328	Intermediate Similarity	NPC146647
0.7328	Intermediate Similarity	NPC249067
0.7328	Intermediate Similarity	NPC471832
0.7324	Intermediate Similarity	NPC472841
0.7315	Intermediate Similarity	NPC153308
0.7313	Intermediate Similarity	NPC1249
0.7308	Intermediate Similarity	NPC51448
0.7308	Intermediate Similarity	NPC115797
0.7299	Intermediate Similarity	NPC470407
0.7295	Intermediate Similarity	NPC217111
0.7295	Intermediate Similarity	NPC186933
0.7292	Intermediate Similarity	NPC472838
0.7292	Intermediate Similarity	NPC306011
0.7286	Intermediate Similarity	NPC245522
0.7286	Intermediate Similarity	NPC308006
0.7286	Intermediate Similarity	NPC114513
0.7279	Intermediate Similarity	NPC290601
0.7273	Intermediate Similarity	NPC471481
0.7273	Intermediate Similarity	NPC198305
0.7266	Intermediate Similarity	NPC69755
0.7265	Intermediate Similarity	NPC209632
0.7259	Intermediate Similarity	NPC309056
0.7259	Intermediate Similarity	NPC22644
0.7259	Intermediate Similarity	NPC283088
0.7248	Intermediate Similarity	NPC298115
0.7248	Intermediate Similarity	NPC113307
0.7241	Intermediate Similarity	NPC472691

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 NPC67377 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	325
0.1-0.2	992
0.2-0.3	1033
0.3-0.4	3016
0.4-0.5	2525
0.5-0.6	1052
0.6-0.7	182
0.7-0.8	25
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.789	Intermediate Similarity	NPD3495	Discontinued
0.7857	Intermediate Similarity	NPD1931	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD1930	Approved
0.7857	Intermediate Similarity	NPD1929	Approved
0.7787	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7787	Intermediate Similarity	NPD7163	Clinical (unspecified phase)
0.7731	Intermediate Similarity	NPD5951	Approved
0.7724	Intermediate Similarity	NPD4879	Approved
0.7692	Intermediate Similarity	NPD4141	Clinical (unspecified phase)
0.7627	Intermediate Similarity	NPD1609	Clinical (unspecified phase)
0.7611	Intermediate Similarity	NPD1932	Approved
0.7597	Intermediate Similarity	NPD7008	Discontinued
0.7593	Intermediate Similarity	NPD7609	Phase 3
0.7547	Intermediate Similarity	NPD650	Approved
0.7523	Intermediate Similarity	NPD7631	Approved
0.7477	Intermediate Similarity	NPD1989	Approved
0.744	Intermediate Similarity	NPD7457	Clinical (unspecified phase)
0.7434	Intermediate Similarity	NPD2066	Phase 3
0.7387	Intermediate Similarity	NPD688	Clinical (unspecified phase)
0.7373	Intermediate Similarity	NPD2329	Discontinued
0.7328	Intermediate Similarity	NPD1237	Approved
0.7273	Intermediate Similarity	NPD7094	Approved
0.7273	Intermediate Similarity	NPD6858	Approved
0.7258	Intermediate Similarity	NPD7610	Discontinued
0.72	Intermediate Similarity	NPD7009	Phase 2
0.7197	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7194	Intermediate Similarity	NPD7003	Approved
0.7188	Intermediate Similarity	NPD4878	Approved
0.7143	Intermediate Similarity	NPD942	Approved
0.7143	Intermediate Similarity	NPD1563	Approved
0.7143	Intermediate Similarity	NPD1651	Approved
0.7117	Intermediate Similarity	NPD1239	Approved
0.709	Intermediate Similarity	NPD7961	Discontinued
0.7077	Intermediate Similarity	NPD1876	Approved
0.7054	Intermediate Similarity	NPD1508	Approved
0.7054	Intermediate Similarity	NPD3972	Approved
0.6977	Remote Similarity	NPD1201	Approved
0.6977	Remote Similarity	NPD1281	Approved
0.6967	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD1566	Phase 3
0.6957	Remote Similarity	NPD1565	Approved
0.6957	Remote Similarity	NPD1564	Approved
0.6953	Remote Similarity	NPD5836	Discontinued
0.6942	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD1087	Approved
0.6906	Remote Similarity	NPD5404	Approved
0.6906	Remote Similarity	NPD5405	Approved
0.6906	Remote Similarity	NPD5406	Approved
0.6906	Remote Similarity	NPD5408	Approved
0.6894	Remote Similarity	NPD1470	Approved
0.6891	Remote Similarity	NPD164	Approved
0.6891	Remote Similarity	NPD5909	Discontinued
0.687	Remote Similarity	NPD1843	Approved
0.6857	Remote Similarity	NPD2346	Discontinued
0.6846	Remote Similarity	NPD6287	Discontinued
0.6842	Remote Similarity	NPD1202	Approved
0.6842	Remote Similarity	NPD5122	Clinical (unspecified phase)
0.6838	Remote Similarity	NPD1238	Approved
0.6838	Remote Similarity	NPD7713	Phase 3
0.6822	Remote Similarity	NPD2345	Approved
0.6818	Remote Similarity	NPD1283	Approved
0.6803	Remote Similarity	NPD2182	Approved
0.6783	Remote Similarity	NPD1693	Approved
0.6748	Remote Similarity	NPD2067	Discontinued
0.6746	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6738	Remote Similarity	NPD1471	Phase 3
0.6736	Remote Similarity	NPD7236	Approved
0.6729	Remote Similarity	NPD1507	Clinical (unspecified phase)
0.6726	Remote Similarity	NPD1089	Approved
0.6726	Remote Similarity	NPD1086	Approved
0.6726	Remote Similarity	NPD1090	Approved
0.6716	Remote Similarity	NPD2798	Approved
0.6695	Remote Similarity	NPD7798	Approved
0.6693	Remote Similarity	NPD3317	Approved
0.6691	Remote Similarity	NPD6966	Discovery
0.6689	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4869	Clinical (unspecified phase)
0.6642	Remote Similarity	NPD3764	Approved
0.6637	Remote Similarity	NPD800	Approved
0.6622	Remote Similarity	NPD7239	Suspended
0.662	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6615	Remote Similarity	NPD3025	Approved
0.6615	Remote Similarity	NPD3024	Approved
0.6609	Remote Similarity	NPD1088	Approved
0.6596	Remote Similarity	NPD3748	Approved
0.6596	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6591	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6585	Remote Similarity	NPD2342	Discontinued
0.6575	Remote Similarity	NPD7390	Discontinued
0.6565	Remote Similarity	NPD3019	Approved
0.6565	Remote Similarity	NPD2932	Approved
0.6547	Remote Similarity	NPD2979	Phase 3
0.6535	Remote Similarity	NPD1241	Discontinued
0.6531	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6529	Remote Similarity	NPD5700	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD2313	Discontinued
0.6518	Remote Similarity	NPD9257	Approved
0.6518	Remote Similarity	NPD9259	Approved
0.6515	Remote Similarity	NPD3026	Approved
0.6515	Remote Similarity	NPD3023	Approved
0.6512	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6503	Remote Similarity	NPD7702	Clinical (unspecified phase)
0.6486	Remote Similarity	NPD6273	Approved
0.6484	Remote Similarity	NPD2629	Approved
0.6481	Remote Similarity	NPD9490	Approved
0.648	Remote Similarity	NPD1317	Discontinued
0.6471	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD5616	Clinical (unspecified phase)
0.6467	Remote Similarity	NPD7458	Discontinued
0.6467	Remote Similarity	NPD3226	Approved
0.6463	Remote Similarity	NPD8165	Discontinued
0.6462	Remote Similarity	NPD6065	Approved
0.6435	Remote Similarity	NPD3672	Approved
0.6435	Remote Similarity	NPD3673	Approved
0.6434	Remote Similarity	NPD4198	Discontinued
0.6429	Remote Similarity	NPD4307	Phase 2
0.6423	Remote Similarity	NPD7084	Phase 3
0.6414	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6403	Remote Similarity	NPD5422	Clinical (unspecified phase)
0.6397	Remote Similarity	NPD1164	Approved
0.6396	Remote Similarity	NPD9491	Approved
0.6389	Remote Similarity	NPD225	Approved
0.6389	Remote Similarity	NPD227	Approved
0.637	Remote Similarity	NPD3750	Approved
0.637	Remote Similarity	NPD5159	Phase 2
0.637	Remote Similarity	NPD182	Clinical (unspecified phase)
0.637	Remote Similarity	NPD5157	Phase 1
0.637	Remote Similarity	NPD5158	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD3299	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD3135	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD1245	Approved
0.6364	Remote Similarity	NPD2799	Discontinued
0.6351	Remote Similarity	NPD3950	Discontinued
0.635	Remote Similarity	NPD2788	Approved
0.635	Remote Similarity	NPD4980	Approved
0.6343	Remote Similarity	NPD5618	Discontinued
0.6327	Remote Similarity	NPD3295	Clinical (unspecified phase)
0.6319	Remote Similarity	NPD2531	Phase 2
0.6319	Remote Similarity	NPD2438	Suspended
0.6316	Remote Similarity	NPD506	Clinical (unspecified phase)
0.6311	Remote Similarity	NPD2648	Phase 3
0.6311	Remote Similarity	NPD2193	Phase 2
0.6293	Remote Similarity	NPD9256	Approved
0.6293	Remote Similarity	NPD9258	Approved
0.6284	Remote Similarity	NPD3300	Phase 2
0.6276	Remote Similarity	NPD2344	Approved
0.626	Remote Similarity	NPD4576	Approved
0.626	Remote Similarity	NPD4574	Approved
0.6259	Remote Similarity	NPD7055	Discontinued
0.6259	Remote Similarity	NPD8166	Discontinued
0.625	Remote Similarity	NPD4308	Phase 3
0.6241	Remote Similarity	NPD5691	Approved
0.6241	Remote Similarity	NPD8032	Phase 2
0.6233	Remote Similarity	NPD2897	Discontinued
0.6231	Remote Similarity	NPD1246	Approved
0.6224	Remote Similarity	NPD6817	Clinical (unspecified phase)
0.6224	Remote Similarity	NPD1607	Approved
0.6222	Remote Similarity	NPD7436	Approved
0.6222	Remote Similarity	NPD7437	Approved
0.622	Remote Similarity	NPD3646	Clinical (unspecified phase)
0.6218	Remote Similarity	NPD7058	Phase 2
0.6218	Remote Similarity	NPD7057	Phase 3
0.6216	Remote Similarity	NPD226	Approved
0.6214	Remote Similarity	NPD6039	Approved
0.6207	Remote Similarity	NPD2796	Approved
0.6207	Remote Similarity	NPD2935	Discontinued
0.6204	Remote Similarity	NPD5667	Approved
0.6204	Remote Similarity	NPD1574	Approved
0.6202	Remote Similarity	NPD7635	Approved
0.6202	Remote Similarity	NPD1279	Clinical (unspecified phase)
0.62	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.62	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6198	Remote Similarity	NPD9495	Approved
0.6194	Remote Similarity	NPD4626	Approved
0.6179	Remote Similarity	NPD2196	Discontinued
0.6176	Remote Similarity	NPD3880	Clinical (unspecified phase)
0.6173	Remote Similarity	NPD7177	Discontinued
0.617	Remote Similarity	NPD6798	Discontinued
0.6164	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6164	Remote Similarity	NPD6959	Discontinued
0.6164	Remote Similarity	NPD2353	Approved
0.6159	Remote Similarity	NPD1593	Approved
0.6159	Remote Similarity	NPD3267	Approved
0.6159	Remote Similarity	NPD3266	Approved
0.6149	Remote Similarity	NPD4628	Phase 3
0.6148	Remote Similarity	NPD4136	Approved
0.6148	Remote Similarity	NPD4106	Approved
0.6148	Remote Similarity	NPD4135	Approved
0.6144	Remote Similarity	NPD6591	Clinical (unspecified phase)
0.6143	Remote Similarity	NPD6832	Phase 2
0.6135	Remote Similarity	NPD5844	Phase 1
0.6129	Remote Similarity	NPD6647	Phase 2
0.6127	Remote Similarity	NPD7715	Approved
0.6127	Remote Similarity	NPD6663	Approved
0.6127	Remote Similarity	NPD7714	Approved
0.6125	Remote Similarity	NPD6232	Discontinued
0.6119	Remote Similarity	NPD4105	Approved
0.6119	Remote Similarity	NPD4102	Approved
0.6118	Remote Similarity	NPD3873	Phase 3

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