NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	216.15
Volume:	243.208
LogP:	4.256
LogD:	4.534
LogS:	-4.811
# Rotatable Bonds:	0
TPSA:	13.14
# H-Bond Aceptor:	1
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	1

MedChem Properties

QED Drug-Likeness Score:	0.596
Synthetic Accessibility Score:	4.082
Fsp3:	0.6
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:	-4.683
MDCK Permeability:	2.154674439225346e-05
Pgp-inhibitor:	0.162
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.82
30% Bioavailability (F30%):	0.04

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.405
Plasma Protein Binding (PPB):	95.31685638427734%
Volume Distribution (VD):	2.421
Pgp-substrate:	3.8025736808776855%

ADMET: Metabolism

CYP1A2-inhibitor:	0.533
CYP1A2-substrate:	0.653
CYP2C19-inhibitor:	0.481
CYP2C19-substrate:	0.41
CYP2C9-inhibitor:	0.363
CYP2C9-substrate:	0.529
CYP2D6-inhibitor:	0.353
CYP2D6-substrate:	0.91
CYP3A4-inhibitor:	0.481
CYP3A4-substrate:	0.256

ADMET: Excretion

Clearance (CL):	9.076
Half-life (T1/2):	0.219

ADMET: Toxicity

hERG Blockers:	0.022
Human Hepatotoxicity (H-HT):	0.224
Drug-inuced Liver Injury (DILI):	0.585
AMES Toxicity:	0.02
Rat Oral Acute Toxicity:	0.326
Maximum Recommended Daily Dose:	0.821
Skin Sensitization:	0.077
Carcinogencity:	0.388
Eye Corrosion:	0.005
Eye Irritation:	0.242
Respiratory Toxicity:	0.805

Download Data

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

Natural Product: NPC178382

Natural Product ID:	NPC178382
*Common Name:**	Atractylon
IUPAC Name:	(4aS,8aR)-3,8a-dimethyl-5-methylidene-4,4a,6,7,8,9-hexahydrobenzo[f][1]benzofuran
Synonyms:	Atractylon
Standard InCHIKey:	TYPSVDGIQAOBAD-DZGCQCFKSA-N
Standard InCHI:	InChI=1S/C15H20O/c1-10-5-4-6-15(3)8-14-12(7-13(10)15)11(2)9-16-14/h9,13H,1,4-8H2,2-3H3/t13-,15+/m0/s1
SMILES:	C=C1CCC[C@]2(C)Cc3c(C[C@@H]12)c(C)co3
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL486189
PubChem CID:	3080635
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001550] Sesquiterpenoids [CHEMONTID:0003655] Eremophilane, 8,9-secoeremophilane and furoeremophilane sesquiterpenoids

*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
NPO8063	Clerodendrum calamitosum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11473423]
NPO20902	Atractylodes macrocephala	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17432574]
NPO4682	Lindera aggregata	Species	Lauraceae	Eukaryota	n.a.	leaf	n.a.	PMID[17999353]
NPO16087	Atractylodes lancea	Species	Asteraceae	Eukaryota	n.a.	rhizome	n.a.	PMID[18787781]
NPO4682	Lindera aggregata	Species	Lauraceae	Eukaryota	Roots; Tubers	n.a.	n.a.	PMID[19639966]
NPO15890	Cimicifuga foetida	Species	Ranunculaceae	Eukaryota	Roots	n.a.	n.a.	PMID[20121210]
NPO16087	Atractylodes lancea	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21302967]
NPO16087	Atractylodes lancea	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27228227]
NPO15373	Actaea dahurica	Species	Ranunculaceae	Eukaryota	Roots	n.a.	n.a.	PMID[28558206]
NPO15373	Actaea dahurica	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32031796]
NPO40789	Atractylodes rhizomes	Species	Asteraceae	Eukaryota	Rhizomes	n.a.	n.a.	PMID[6418860]
NPO16087	Atractylodes lancea	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9544564]
NPO19048	Pinellia ternata	Species	Araceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12584	Atractylodes chinensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO16087	Atractylodes lancea	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO20902	Atractylodes macrocephala	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO4682	Lindera aggregata	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19048	Pinellia ternata	Species	Araceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12584	Atractylodes chinensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16087	Atractylodes lancea	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2727	Actaea simplex	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO389	Actaea heracleifolia	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15890	Cimicifuga foetida	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20902	Atractylodes macrocephala	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15373	Actaea dahurica	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19048	Pinellia ternata	Species	Araceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO20902	Atractylodes macrocephala	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO16087	Atractylodes lancea	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO12584	Atractylodes chinensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO13346	Lindera strichnifolia	Species	Tineidae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO19048	Pinellia ternata	Species	Araceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO389	Actaea heracleifolia	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO12584	Atractylodes chinensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO15373	Actaea dahurica	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO2727	Actaea simplex	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO20902	Atractylodes macrocephala	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO15890	Cimicifuga foetida	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO4682	Lindera aggregata	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO16087	Atractylodes lancea	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO10355	Echinopsis macrogona	Species	Cactaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16087	Atractylodes lancea	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8063	Clerodendrum calamitosum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12584	Atractylodes chinensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO389	Actaea heracleifolia	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20902	Atractylodes macrocephala	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4682	Lindera aggregata	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15890	Cimicifuga foetida	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15373	Actaea dahurica	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19048	Pinellia ternata	Species	Araceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2727	Actaea simplex	Species	Ranunculaceae	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	2
LD50	1
Others	7

Activity Type	# Activity
Cell Line	6
Individual Protein	3
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1135	Cell Line	Hepatocyte	Rattus norvegicus	Activity	=	67.0	%	PMID[454266]
NPT1135	Cell Line	Hepatocyte	Rattus norvegicus	Activity	=	99.0	%	PMID[454266]
NPT1135	Cell Line	Hepatocyte	Rattus norvegicus	Activity	=	53.0	%	PMID[454266]
NPT1135	Cell Line	Hepatocyte	Rattus norvegicus	Activity	=	92.0	%	PMID[454266]
NPT1135	Cell Line	Hepatocyte	Rattus norvegicus	Activity	=	25.0	%	PMID[454266]
NPT1135	Cell Line	Hepatocyte	Rattus norvegicus	Activity	=	84.0	%	PMID[454266]
NPT2967	Individual Protein	Alanine aminotransferase	Rattus norvegicus	Activity	=	106.0	%	PMID[454266]
NPT570	Individual Protein	Arachidonate 5-lipoxygenase	Homo sapiens	IC50	=	25100.0	nM	PMID[454267]
NPT30	Individual Protein	Cyclooxygenase-1	Homo sapiens	IC50	>	200000.0	nM	PMID[454267]
NPT1077	Organism	Drosophila melanogaster	Drosophila melanogaster	LD50	=	1.43	ug	PMID[454268]

☑ 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 NPC178382 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	414
0.1-0.2	1595
0.2-0.3	3288
0.3-0.4	9421
0.4-0.5	10837
0.5-0.6	8559
0.6-0.7	7870
0.7-0.8	624
0.8-0.85	72
0.85-0.9	11
0.9-0.95	5
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9426	High Similarity	NPC59502
0.9407	High Similarity	NPC97566
0.931	High Similarity	NPC79202
0.931	High Similarity	NPC59035
0.8992	High Similarity	NPC307401
0.8976	High Similarity	NPC293253
0.8908	High Similarity	NPC212918
0.888	High Similarity	NPC329707
0.8855	High Similarity	NPC202260
0.8837	High Similarity	NPC324117
0.879	High Similarity	NPC471074
0.879	High Similarity	NPC473885
0.8661	High Similarity	NPC198904
0.8657	High Similarity	NPC263337
0.8636	High Similarity	NPC177262
0.8593	High Similarity	NPC205071
0.8593	High Similarity	NPC64568
0.8571	High Similarity	NPC233707
0.855	High Similarity	NPC209858
0.8548	High Similarity	NPC36255
0.8487	Intermediate Similarity	NPC22678
0.848	Intermediate Similarity	NPC272899
0.8467	Intermediate Similarity	NPC56731
0.843	Intermediate Similarity	NPC150895
0.8413	Intermediate Similarity	NPC130275
0.8413	Intermediate Similarity	NPC83115
0.8406	Intermediate Similarity	NPC97904
0.8406	Intermediate Similarity	NPC62799
0.8385	Intermediate Similarity	NPC61788
0.837	Intermediate Similarity	NPC18904
0.8346	Intermediate Similarity	NPC230979
0.8346	Intermediate Similarity	NPC303010
0.8345	Intermediate Similarity	NPC71821
0.8333	Intermediate Similarity	NPC114513
0.8333	Intermediate Similarity	NPC16922
0.8333	Intermediate Similarity	NPC245522
0.8333	Intermediate Similarity	NPC290038
0.8321	Intermediate Similarity	NPC473982
0.8286	Intermediate Similarity	NPC93666
0.8286	Intermediate Similarity	NPC19747
0.8273	Intermediate Similarity	NPC478166
0.8273	Intermediate Similarity	NPC233763
0.8271	Intermediate Similarity	NPC476947
0.8261	Intermediate Similarity	NPC84479
0.8261	Intermediate Similarity	NPC158871
0.8258	Intermediate Similarity	NPC218838
0.8235	Intermediate Similarity	NPC473681
0.8235	Intermediate Similarity	NPC61157
0.8235	Intermediate Similarity	NPC218204
0.8227	Intermediate Similarity	NPC211625
0.8226	Intermediate Similarity	NPC87466
0.8226	Intermediate Similarity	NPC243704
0.8222	Intermediate Similarity	NPC471996
0.8217	Intermediate Similarity	NPC246392
0.8217	Intermediate Similarity	NPC290955
0.8209	Intermediate Similarity	NPC214572
0.8209	Intermediate Similarity	NPC46896
0.8203	Intermediate Similarity	NPC290193
0.8203	Intermediate Similarity	NPC179354
0.8182	Intermediate Similarity	NPC471995
0.8182	Intermediate Similarity	NPC279596
0.8169	Intermediate Similarity	NPC228842
0.8169	Intermediate Similarity	NPC212257
0.8154	Intermediate Similarity	NPC477040
0.8154	Intermediate Similarity	NPC279877
0.8154	Intermediate Similarity	NPC26532
0.8154	Intermediate Similarity	NPC327527
0.8154	Intermediate Similarity	NPC476917
0.8148	Intermediate Similarity	NPC310043
0.8148	Intermediate Similarity	NPC4764
0.8145	Intermediate Similarity	NPC227660
0.814	Intermediate Similarity	NPC138139
0.814	Intermediate Similarity	NPC23086
0.814	Intermediate Similarity	NPC74612
0.814	Intermediate Similarity	NPC46536
0.813	Intermediate Similarity	NPC205523
0.8125	Intermediate Similarity	NPC118853
0.8106	Intermediate Similarity	NPC298190
0.8102	Intermediate Similarity	NPC56197
0.8102	Intermediate Similarity	NPC148374
0.8099	Intermediate Similarity	NPC95526
0.8092	Intermediate Similarity	NPC120836
0.8092	Intermediate Similarity	NPC208389
0.8092	Intermediate Similarity	NPC223063
0.8085	Intermediate Similarity	NPC281398
0.8062	Intermediate Similarity	NPC300098
0.8056	Intermediate Similarity	NPC121615
0.8056	Intermediate Similarity	NPC294511
0.8056	Intermediate Similarity	NPC475777
0.8042	Intermediate Similarity	NPC472298
0.803	Intermediate Similarity	NPC476925
0.8016	Intermediate Similarity	NPC137710
0.8015	Intermediate Similarity	NPC112706
0.8015	Intermediate Similarity	NPC477123
0.8015	Intermediate Similarity	NPC215109
0.8015	Intermediate Similarity	NPC477966
0.8015	Intermediate Similarity	NPC170604
0.8015	Intermediate Similarity	NPC207294
0.8	Intermediate Similarity	NPC114880
0.8	Intermediate Similarity	NPC217180
0.8	Intermediate Similarity	NPC158525
0.8	Intermediate Similarity	NPC312525
0.8	Intermediate Similarity	NPC470858
0.7986	Intermediate Similarity	NPC472787
0.7986	Intermediate Similarity	NPC52412
0.7985	Intermediate Similarity	NPC471006
0.7971	Intermediate Similarity	NPC67003
0.7958	Intermediate Similarity	NPC224418
0.7956	Intermediate Similarity	NPC472376
0.7953	Intermediate Similarity	NPC246214
0.7951	Intermediate Similarity	NPC277525
0.7945	Intermediate Similarity	NPC25351
0.7945	Intermediate Similarity	NPC75310
0.7939	Intermediate Similarity	NPC83178
0.7939	Intermediate Similarity	NPC474737
0.7937	Intermediate Similarity	NPC206007
0.7929	Intermediate Similarity	NPC243577
0.791	Intermediate Similarity	NPC239134
0.791	Intermediate Similarity	NPC164295
0.7899	Intermediate Similarity	NPC474722
0.7891	Intermediate Similarity	NPC41880
0.7891	Intermediate Similarity	NPC104736
0.7879	Intermediate Similarity	NPC477039
0.7877	Intermediate Similarity	NPC44606
0.7872	Intermediate Similarity	NPC117674
0.7872	Intermediate Similarity	NPC238843
0.7872	Intermediate Similarity	NPC199044
0.7868	Intermediate Similarity	NPC265793
0.7862	Intermediate Similarity	NPC144010
0.7857	Intermediate Similarity	NPC62103
0.7857	Intermediate Similarity	NPC121158
0.7857	Intermediate Similarity	NPC20578
0.7852	Intermediate Similarity	NPC470740
0.7847	Intermediate Similarity	NPC192069
0.7846	Intermediate Similarity	NPC11799
0.7846	Intermediate Similarity	NPC188377
0.7846	Intermediate Similarity	NPC65735
0.7846	Intermediate Similarity	NPC141252
0.7842	Intermediate Similarity	NPC473983
0.7842	Intermediate Similarity	NPC201370
0.7838	Intermediate Similarity	NPC195954
0.7838	Intermediate Similarity	NPC304692
0.7838	Intermediate Similarity	NPC88007
0.7838	Intermediate Similarity	NPC7059
0.7838	Intermediate Similarity	NPC194499
0.7836	Intermediate Similarity	NPC89133
0.7836	Intermediate Similarity	NPC477645
0.7829	Intermediate Similarity	NPC477967
0.7829	Intermediate Similarity	NPC317217
0.7826	Intermediate Similarity	NPC476943
0.7826	Intermediate Similarity	NPC236532
0.7823	Intermediate Similarity	NPC472785
0.7823	Intermediate Similarity	NPC179170
0.7823	Intermediate Similarity	NPC88958
0.782	Intermediate Similarity	NPC50583
0.7817	Intermediate Similarity	NPC93241
0.7817	Intermediate Similarity	NPC185456
0.7817	Intermediate Similarity	NPC27798
0.781	Intermediate Similarity	NPC146872
0.7808	Intermediate Similarity	NPC246164
0.7808	Intermediate Similarity	NPC145830
0.7808	Intermediate Similarity	NPC115869
0.7801	Intermediate Similarity	NPC476946
0.7801	Intermediate Similarity	NPC103134
0.7794	Intermediate Similarity	NPC471998
0.7785	Intermediate Similarity	NPC474611
0.7785	Intermediate Similarity	NPC84349
0.7785	Intermediate Similarity	NPC472823
0.777	Intermediate Similarity	NPC265181
0.7762	Intermediate Similarity	NPC470999
0.7762	Intermediate Similarity	NPC471292
0.7761	Intermediate Similarity	NPC45947
0.7755	Intermediate Similarity	NPC282793
0.7755	Intermediate Similarity	NPC10429
0.7754	Intermediate Similarity	NPC470742
0.7754	Intermediate Similarity	NPC64157
0.7754	Intermediate Similarity	NPC278832
0.7754	Intermediate Similarity	NPC42400
0.7746	Intermediate Similarity	NPC251865
0.7733	Intermediate Similarity	NPC287559
0.7733	Intermediate Similarity	NPC8389
0.7727	Intermediate Similarity	NPC83301
0.7718	Intermediate Similarity	NPC81405
0.7714	Intermediate Similarity	NPC90296
0.771	Intermediate Similarity	NPC477038
0.771	Intermediate Similarity	NPC477965
0.7708	Intermediate Similarity	NPC302987
0.7708	Intermediate Similarity	NPC216755
0.7708	Intermediate Similarity	NPC471174
0.7703	Intermediate Similarity	NPC472786
0.7703	Intermediate Similarity	NPC469966
0.7698	Intermediate Similarity	NPC130976
0.7692	Intermediate Similarity	NPC5676
0.7692	Intermediate Similarity	NPC41182
0.7686	Intermediate Similarity	NPC42471
0.7682	Intermediate Similarity	NPC68848
0.7682	Intermediate Similarity	NPC471003
0.7682	Intermediate Similarity	NPC18986
0.7682	Intermediate Similarity	NPC79571
0.7681	Intermediate Similarity	NPC217914

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 NPC178382 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	392
0.1-0.2	984
0.2-0.3	1541
0.3-0.4	2795
0.4-0.5	2076
0.5-0.6	1062
0.6-0.7	288
0.7-0.8	12
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
0.7899	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.777	Intermediate Similarity	NPD1471	Phase 3
0.7634	Intermediate Similarity	NPD3972	Approved
0.754	Intermediate Similarity	NPD1241	Discontinued
0.7538	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7533	Intermediate Similarity	NPD5616	Clinical (unspecified phase)
0.7519	Intermediate Similarity	NPD1876	Approved
0.7518	Intermediate Similarity	NPD8032	Phase 2
0.7466	Intermediate Similarity	NPD6273	Approved
0.7462	Intermediate Similarity	NPD1651	Approved
0.7424	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7293	Intermediate Similarity	NPD1281	Approved
0.7273	Intermediate Similarity	NPD2344	Approved
0.7254	Intermediate Similarity	NPD2799	Discontinued
0.7237	Intermediate Similarity	NPD5761	Phase 2
0.7237	Intermediate Similarity	NPD5760	Phase 2
0.7197	Intermediate Similarity	NPD5585	Approved
0.7185	Intermediate Similarity	NPD5327	Phase 3
0.7153	Intermediate Similarity	NPD2346	Discontinued
0.7153	Intermediate Similarity	NPD2798	Approved
0.7143	Intermediate Similarity	NPD17	Approved
0.7143	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7132	Intermediate Similarity	NPD1283	Approved
0.7123	Intermediate Similarity	NPD4628	Phase 3
0.7123	Intermediate Similarity	NPD7003	Approved
0.7099	Intermediate Similarity	NPD6764	Approved
0.7099	Intermediate Similarity	NPD6765	Approved
0.7092	Intermediate Similarity	NPD2979	Phase 3
0.7083	Intermediate Similarity	NPD2796	Approved
0.7075	Intermediate Similarity	NPD2309	Approved
0.7068	Intermediate Similarity	NPD5691	Approved
0.7067	Intermediate Similarity	NPD920	Approved
0.7055	Intermediate Similarity	NPD1243	Approved
0.705	Intermediate Similarity	NPD6832	Phase 2
0.7047	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.6988	Remote Similarity	NPD8434	Phase 2
0.6985	Remote Similarity	NPD1608	Approved
0.6972	Remote Similarity	NPD4140	Approved
0.6966	Remote Similarity	NPD6099	Approved
0.6966	Remote Similarity	NPD6100	Approved
0.6957	Remote Similarity	NPD3266	Approved
0.6957	Remote Similarity	NPD3267	Approved
0.6957	Remote Similarity	NPD2797	Approved
0.695	Remote Similarity	NPD2313	Discontinued
0.6948	Remote Similarity	NPD6279	Approved
0.6948	Remote Similarity	NPD6280	Approved
0.6939	Remote Similarity	NPD2800	Approved
0.6939	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6934	Remote Similarity	NPD4359	Approved
0.6928	Remote Similarity	NPD6785	Approved
0.6928	Remote Similarity	NPD6784	Approved
0.6923	Remote Similarity	NPD6355	Discontinued
0.6899	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD3748	Approved
0.6892	Remote Similarity	NPD4110	Phase 3
0.6892	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD1778	Approved
0.6863	Remote Similarity	NPD7458	Discontinued
0.6863	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6853	Remote Similarity	NPD4307	Phase 2
0.6853	Remote Similarity	NPD3140	Approved
0.6853	Remote Similarity	NPD3142	Approved
0.6849	Remote Similarity	NPD2531	Phase 2
0.6849	Remote Similarity	NPD2438	Suspended
0.6849	Remote Similarity	NPD4477	Approved
0.6849	Remote Similarity	NPD4476	Approved
0.6846	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD3873	Phase 3
0.6842	Remote Similarity	NPD3869	Phase 3
0.6838	Remote Similarity	NPD7457	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD1049	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD919	Approved
0.6831	Remote Similarity	NPD3268	Approved
0.6831	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD2533	Approved
0.6821	Remote Similarity	NPD2534	Approved
0.6821	Remote Similarity	NPD2532	Approved
0.6818	Remote Similarity	NPD6599	Discontinued
0.6815	Remote Similarity	NPD4947	Clinical (unspecified phase)
0.6815	Remote Similarity	NPD3024	Approved
0.6815	Remote Similarity	NPD3025	Approved
0.6806	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6795	Remote Similarity	NPD7819	Suspended
0.6792	Remote Similarity	NPD5494	Approved
0.6779	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD4626	Approved
0.6765	Remote Similarity	NPD3019	Approved
0.6765	Remote Similarity	NPD2932	Approved
0.6761	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.675	Remote Similarity	NPD1247	Approved
0.6741	Remote Similarity	NPD1894	Discontinued
0.6735	Remote Similarity	NPD2935	Discontinued
0.6735	Remote Similarity	NPD1551	Phase 2
0.6715	Remote Similarity	NPD3026	Approved
0.6715	Remote Similarity	NPD3023	Approved
0.6711	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6711	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.671	Remote Similarity	NPD7028	Phase 2
0.669	Remote Similarity	NPD4618	Approved
0.669	Remote Similarity	NPD4622	Approved
0.669	Remote Similarity	NPD5735	Approved
0.6689	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6689	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD6559	Discontinued
0.6667	Remote Similarity	NPD4870	Approved
0.6667	Remote Similarity	NPD3750	Approved
0.6667	Remote Similarity	NPD1611	Approved
0.6667	Remote Similarity	NPD4308	Phase 3
0.6667	Remote Similarity	NPD1019	Discontinued
0.6667	Remote Similarity	NPD7644	Approved
0.6646	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD8127	Discontinued
0.6646	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6645	Remote Similarity	NPD2649	Approved
0.6645	Remote Similarity	NPD3226	Approved
0.6645	Remote Similarity	NPD2651	Approved
0.6644	Remote Similarity	NPD6651	Approved
0.6644	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6644	Remote Similarity	NPD6353	Approved
0.6644	Remote Similarity	NPD1549	Phase 2
0.6644	Remote Similarity	NPD1607	Approved
0.6642	Remote Similarity	NPD7157	Approved
0.6623	Remote Similarity	NPD3887	Approved
0.6621	Remote Similarity	NPD1240	Approved
0.6621	Remote Similarity	NPD4060	Phase 1
0.662	Remote Similarity	NPD9494	Approved
0.6619	Remote Similarity	NPD9717	Approved
0.6605	Remote Similarity	NPD6808	Phase 2
0.6599	Remote Similarity	NPD5689	Approved
0.6599	Remote Similarity	NPD5688	Approved
0.6597	Remote Similarity	NPD6798	Discontinued
0.6596	Remote Similarity	NPD1203	Approved
0.6594	Remote Similarity	NPD3496	Discontinued
0.6589	Remote Similarity	NPD3134	Approved
0.6584	Remote Similarity	NPD710	Clinical (unspecified phase)
0.6582	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6579	Remote Similarity	NPD7236	Approved
0.6577	Remote Similarity	NPD6002	Phase 3
0.6577	Remote Similarity	NPD6004	Phase 3
0.6577	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6577	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6577	Remote Similarity	NPD6005	Phase 3
0.6569	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6569	Remote Similarity	NPD3444	Approved
0.6569	Remote Similarity	NPD3443	Approved
0.6569	Remote Similarity	NPD3445	Approved
0.6564	Remote Similarity	NPD3926	Phase 2
0.6556	Remote Similarity	NPD8166	Discontinued
0.6554	Remote Similarity	NPD1510	Phase 2
0.6552	Remote Similarity	NPD6663	Approved
0.6549	Remote Similarity	NPD4624	Approved
0.6547	Remote Similarity	NPD6287	Discontinued
0.6547	Remote Similarity	NPD1201	Approved
0.6544	Remote Similarity	NPD5536	Phase 2
0.6543	Remote Similarity	NPD6959	Discontinued
0.6541	Remote Similarity	NPD5535	Approved
0.6541	Remote Similarity	NPD2296	Approved
0.6536	Remote Similarity	NPD6799	Approved
0.6533	Remote Similarity	NPD2897	Discontinued
0.6533	Remote Similarity	NPD4534	Discontinued
0.6528	Remote Similarity	NPD7095	Approved
0.6525	Remote Similarity	NPD6696	Suspended
0.6513	Remote Similarity	NPD3295	Clinical (unspecified phase)
0.6508	Remote Similarity	NPD1238	Approved
0.6503	Remote Similarity	NPD5736	Approved
0.65	Remote Similarity	NPD3882	Suspended
0.6494	Remote Similarity	NPD4662	Approved
0.6494	Remote Similarity	NPD4661	Approved
0.6494	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6493	Remote Similarity	NPD5283	Phase 1
0.6493	Remote Similarity	NPD1398	Phase 1
0.6489	Remote Similarity	NPD2182	Approved
0.6489	Remote Similarity	NPD2684	Approved
0.6483	Remote Similarity	NPD6812	Clinical (unspecified phase)
0.6483	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6483	Remote Similarity	NPD7985	Registered
0.6483	Remote Similarity	NPD3764	Approved
0.6483	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6483	Remote Similarity	NPD411	Approved
0.6478	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD7340	Approved
0.6467	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6467	Remote Similarity	NPD5763	Approved
0.6467	Remote Similarity	NPD5762	Approved
0.6467	Remote Similarity	NPD2353	Approved
0.6463	Remote Similarity	NPD1933	Approved
0.646	Remote Similarity	NPD3749	Approved
0.6458	Remote Similarity	NPD2614	Approved
0.6456	Remote Similarity	NPD6873	Phase 2
0.6456	Remote Similarity	NPD7411	Suspended
0.6452	Remote Similarity	NPD5049	Phase 3
0.6434	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6424	Remote Similarity	NPD4575	Clinical (unspecified phase)
0.6424	Remote Similarity	NPD2424	Discontinued
0.6424	Remote Similarity	NPD5958	Discontinued
0.6415	Remote Similarity	NPD1934	Approved
0.6415	Remote Similarity	NPD7577	Discontinued
0.6414	Remote Similarity	NPD7008	Discontinued
0.6412	Remote Similarity	NPD1358	Approved

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