NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	258.2
Volume:	295.096
LogP:	5.185
LogD:	4.271
LogS:	-6.006
# Rotatable Bonds:	0
TPSA:	9.23
# H-Bond Aceptor:	1
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	1

MedChem Properties

QED Drug-Likeness Score:	0.664
Synthetic Accessibility Score:	3.884
Fsp3:	0.667
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:	-5.006
MDCK Permeability:	1.1872861250594724e-05
Pgp-inhibitor:	0.929
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.029
20% Bioavailability (F20%):	0.907
30% Bioavailability (F30%):	0.427

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.365
Plasma Protein Binding (PPB):	97.02637481689453%
Volume Distribution (VD):	3.369
Pgp-substrate:	3.5024008750915527%

ADMET: Metabolism

CYP1A2-inhibitor:	0.216
CYP1A2-substrate:	0.798
CYP2C19-inhibitor:	0.451
CYP2C19-substrate:	0.934
CYP2C9-inhibitor:	0.244
CYP2C9-substrate:	0.403
CYP2D6-inhibitor:	0.112
CYP2D6-substrate:	0.71
CYP3A4-inhibitor:	0.069
CYP3A4-substrate:	0.698

ADMET: Excretion

Clearance (CL):	3.994
Half-life (T1/2):	0.063

ADMET: Toxicity

hERG Blockers:	0.016
Human Hepatotoxicity (H-HT):	0.073
Drug-inuced Liver Injury (DILI):	0.036
AMES Toxicity:	0.014
Rat Oral Acute Toxicity:	0.155
Maximum Recommended Daily Dose:	0.939
Skin Sensitization:	0.689
Carcinogencity:	0.041
Eye Corrosion:	0.005
Eye Irritation:	0.929
Respiratory Toxicity:	0.878

Download Data

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

Natural Product: NPC245927

Natural Product ID:	NPC245927
*Common Name:**	4,6,6,7,8,8-Hexamethyl-1,3,4,7-Tetrahydrocyclopenta[G]Isochromene
IUPAC Name:	4,6,6,7,8,8-hexamethyl-1,3,4,7-tetrahydrocyclopenta[g]isochromene
Synonyms:
Standard InCHIKey:	ONKNPOPIGWHAQC-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C18H26O/c1-11-9-19-10-13-7-15-16(8-14(11)13)18(5,6)12(2)17(15,3)4/h7-8,11-12H,9-10H2,1-6H3
SMILES:	CC1COCc2cc3c(cc12)C(C)(C)C(C)C3(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1883305
PubChem CID:	91497
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000123] Benzopyrans [CHEMONTID:0003411] 2-benzopyrans

*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
NPO20902	Atractylodes macrocephala	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17432574]
NPO16087	Atractylodes lancea	Species	Asteraceae	Eukaryota	n.a.	rhizome	n.a.	PMID[18787781]
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]
NPO16087	Atractylodes lancea	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9544564]
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]
NPO20902	Atractylodes macrocephala	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]
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]
NPO20902	Atractylodes macrocephala	Species	Asteraceae	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]
NPO20902	Atractylodes macrocephala	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16087	Atractylodes lancea	Species	Asteraceae	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
Potency	2

Activity Type	# Activity
Individual Protein	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT108	Individual Protein	Estrogen receptor alpha	Homo sapiens	Potency	n.a.	11220.2	nM	PMID[545686]
NPT610	Others	Molecular identity unknown		Potency	n.a.	70794.6	nM	PMID[545686]

☑ 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 NPC245927 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	404
0.1-0.2	1606
0.2-0.3	3281
0.3-0.4	12141
0.4-0.5	14403
0.5-0.6	9163
0.6-0.7	1580
0.7-0.8	112
0.8-0.85	5
0.85-0.9	1
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8505	High Similarity	NPC169616
0.8235	Intermediate Similarity	NPC289117
0.8142	Intermediate Similarity	NPC146673
0.8142	Intermediate Similarity	NPC233923
0.8053	Intermediate Similarity	NPC238582
0.7925	Intermediate Similarity	NPC471133
0.7905	Intermediate Similarity	NPC19856
0.79	Intermediate Similarity	NPC314690
0.783	Intermediate Similarity	NPC56168
0.783	Intermediate Similarity	NPC315794
0.78	Intermediate Similarity	NPC79917
0.7789	Intermediate Similarity	NPC106313
0.7788	Intermediate Similarity	NPC33900
0.7768	Intermediate Similarity	NPC474095
0.7757	Intermediate Similarity	NPC243601
0.7719	Intermediate Similarity	NPC45794
0.7652	Intermediate Similarity	NPC254233
0.7632	Intermediate Similarity	NPC472862
0.7624	Intermediate Similarity	NPC220596
0.7615	Intermediate Similarity	NPC472979
0.7615	Intermediate Similarity	NPC27252
0.7615	Intermediate Similarity	NPC472980
0.7611	Intermediate Similarity	NPC221275
0.7549	Intermediate Similarity	NPC128645
0.7545	Intermediate Similarity	NPC64642
0.7545	Intermediate Similarity	NPC472982
0.7545	Intermediate Similarity	NPC149455
0.7521	Intermediate Similarity	NPC77000
0.7521	Intermediate Similarity	NPC238861
0.75	Intermediate Similarity	NPC165212
0.75	Intermediate Similarity	NPC470723
0.7478	Intermediate Similarity	NPC312105
0.7477	Intermediate Similarity	NPC60373
0.7477	Intermediate Similarity	NPC273837
0.7477	Intermediate Similarity	NPC154905
0.7475	Intermediate Similarity	NPC93843
0.7438	Intermediate Similarity	NPC124030
0.7391	Intermediate Similarity	NPC469719
0.7391	Intermediate Similarity	NPC135730
0.7345	Intermediate Similarity	NPC471188
0.7339	Intermediate Similarity	NPC82712
0.7328	Intermediate Similarity	NPC105141
0.7328	Intermediate Similarity	NPC242764
0.7295	Intermediate Similarity	NPC100402
0.7295	Intermediate Similarity	NPC9180
0.7273	Intermediate Similarity	NPC51079
0.7273	Intermediate Similarity	NPC307139
0.7264	Intermediate Similarity	NPC226041
0.7264	Intermediate Similarity	NPC324602
0.7255	Intermediate Similarity	NPC1793
0.7255	Intermediate Similarity	NPC220893
0.7255	Intermediate Similarity	NPC199567
0.7227	Intermediate Similarity	NPC988
0.7227	Intermediate Similarity	NPC289432
0.7222	Intermediate Similarity	NPC469481
0.72	Intermediate Similarity	NPC58616
0.72	Intermediate Similarity	NPC474354
0.7193	Intermediate Similarity	NPC322753
0.719	Intermediate Similarity	NPC152946
0.7179	Intermediate Similarity	NPC247858
0.7179	Intermediate Similarity	NPC137496
0.7179	Intermediate Similarity	NPC474387
0.7179	Intermediate Similarity	NPC154511
0.7179	Intermediate Similarity	NPC474358
0.7179	Intermediate Similarity	NPC257540
0.7177	Intermediate Similarity	NPC186889
0.7172	Intermediate Similarity	NPC172984
0.717	Intermediate Similarity	NPC21959
0.7167	Intermediate Similarity	NPC316896
0.7167	Intermediate Similarity	NPC144547
0.7165	Intermediate Similarity	NPC85595
0.7157	Intermediate Similarity	NPC304760
0.7155	Intermediate Similarity	NPC228936
0.7143	Intermediate Similarity	NPC112903
0.713	Intermediate Similarity	NPC221825
0.7129	Intermediate Similarity	NPC474211
0.7129	Intermediate Similarity	NPC243166
0.712	Intermediate Similarity	NPC223912
0.7119	Intermediate Similarity	NPC25648
0.7117	Intermediate Similarity	NPC117115
0.7117	Intermediate Similarity	NPC471186
0.7105	Intermediate Similarity	NPC475002
0.7105	Intermediate Similarity	NPC210089
0.7105	Intermediate Similarity	NPC95126
0.7105	Intermediate Similarity	NPC132720
0.7105	Intermediate Similarity	NPC133308
0.71	Intermediate Similarity	NPC95429
0.71	Intermediate Similarity	NPC168855
0.7097	Intermediate Similarity	NPC5486
0.7094	Intermediate Similarity	NPC192948
0.7094	Intermediate Similarity	NPC35797
0.7094	Intermediate Similarity	NPC283169
0.7091	Intermediate Similarity	NPC24327
0.7091	Intermediate Similarity	NPC12870
0.7087	Intermediate Similarity	NPC78575
0.7083	Intermediate Similarity	NPC135467
0.7083	Intermediate Similarity	NPC232958
0.7083	Intermediate Similarity	NPC260832
0.708	Intermediate Similarity	NPC64586
0.7064	Intermediate Similarity	NPC316797
0.7059	Intermediate Similarity	NPC89377
0.7059	Intermediate Similarity	NPC164649
0.7059	Intermediate Similarity	NPC48342
0.7054	Intermediate Similarity	NPC83409
0.7054	Intermediate Similarity	NPC142326
0.7054	Intermediate Similarity	NPC185763
0.7054	Intermediate Similarity	NPC94751
0.7043	Intermediate Similarity	NPC260323
0.7043	Intermediate Similarity	NPC176279
0.7034	Intermediate Similarity	NPC477137
0.7034	Intermediate Similarity	NPC92
0.7034	Intermediate Similarity	NPC212891
0.7034	Intermediate Similarity	NPC469663
0.7034	Intermediate Similarity	NPC308311
0.7034	Intermediate Similarity	NPC38893
0.7025	Intermediate Similarity	NPC50872
0.7016	Intermediate Similarity	NPC4286
0.7016	Intermediate Similarity	NPC76119
0.7008	Intermediate Similarity	NPC196193
0.7008	Intermediate Similarity	NPC99795
0.7008	Intermediate Similarity	NPC470278
0.7008	Intermediate Similarity	NPC72915
0.6991	Remote Similarity	NPC151477
0.6991	Remote Similarity	NPC21929
0.6983	Remote Similarity	NPC13784
0.6983	Remote Similarity	NPC250323
0.6983	Remote Similarity	NPC128368
0.6975	Remote Similarity	NPC477136
0.6975	Remote Similarity	NPC172219
0.6975	Remote Similarity	NPC304510
0.6967	Remote Similarity	NPC474115
0.6967	Remote Similarity	NPC168707
0.6967	Remote Similarity	NPC475839
0.6967	Remote Similarity	NPC48623
0.696	Remote Similarity	NPC253681
0.6957	Remote Similarity	NPC167504
0.6952	Remote Similarity	NPC475023
0.6952	Remote Similarity	NPC475059
0.6952	Remote Similarity	NPC119631
0.6949	Remote Similarity	NPC226093
0.6942	Remote Similarity	NPC68339
0.6937	Remote Similarity	NPC234305
0.6935	Remote Similarity	NPC75432
0.6931	Remote Similarity	NPC304538
0.6929	Remote Similarity	NPC131684
0.6929	Remote Similarity	NPC288290
0.6923	Remote Similarity	NPC123175
0.6923	Remote Similarity	NPC196075
0.6923	Remote Similarity	NPC176730
0.6923	Remote Similarity	NPC173443
0.6923	Remote Similarity	NPC307651
0.6917	Remote Similarity	NPC154030
0.6917	Remote Similarity	NPC471671
0.6911	Remote Similarity	NPC297057
0.6911	Remote Similarity	NPC472703
0.6911	Remote Similarity	NPC182333
0.6911	Remote Similarity	NPC273336
0.6909	Remote Similarity	NPC211885
0.6907	Remote Similarity	NPC3190
0.6907	Remote Similarity	NPC249018
0.6905	Remote Similarity	NPC471077
0.6903	Remote Similarity	NPC326801
0.6903	Remote Similarity	NPC30416
0.6903	Remote Similarity	NPC21594
0.6899	Remote Similarity	NPC59239
0.6899	Remote Similarity	NPC321086
0.6897	Remote Similarity	NPC270699
0.6897	Remote Similarity	NPC111108
0.6897	Remote Similarity	NPC79496
0.6897	Remote Similarity	NPC82899
0.6891	Remote Similarity	NPC219112
0.6887	Remote Similarity	NPC475057
0.6885	Remote Similarity	NPC328504
0.6885	Remote Similarity	NPC212559
0.6885	Remote Similarity	NPC45663
0.6881	Remote Similarity	NPC470161
0.6875	Remote Similarity	NPC472221
0.6875	Remote Similarity	NPC249425
0.6875	Remote Similarity	NPC472222
0.687	Remote Similarity	NPC196246
0.687	Remote Similarity	NPC214067
0.6869	Remote Similarity	NPC328178
0.6864	Remote Similarity	NPC195922
0.6864	Remote Similarity	NPC473869
0.6864	Remote Similarity	NPC268160
0.6864	Remote Similarity	NPC274839
0.686	Remote Similarity	NPC469644
0.6857	Remote Similarity	NPC240108
0.6857	Remote Similarity	NPC213156
0.6855	Remote Similarity	NPC472704
0.6855	Remote Similarity	NPC77691
0.6852	Remote Similarity	NPC222146
0.6846	Remote Similarity	NPC203486
0.6842	Remote Similarity	NPC54269
0.6838	Remote Similarity	NPC228425
0.6838	Remote Similarity	NPC228452
0.6837	Remote Similarity	NPC224544
0.6833	Remote Similarity	NPC228318
0.6829	Remote Similarity	NPC77569
0.6829	Remote Similarity	NPC142198

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 NPC245927 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	342
0.1-0.2	994
0.2-0.3	1319
0.3-0.4	3248
0.4-0.5	2084
0.5-0.6	942
0.6-0.7	208
0.7-0.8	13
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
0.7807	Intermediate Similarity	NPD7741	Discontinued
0.7788	Intermediate Similarity	NPD4230	Clinical (unspecified phase)
0.757	Intermediate Similarity	NPD5700	Clinical (unspecified phase)
0.7521	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7417	Intermediate Similarity	NPD5327	Phase 3
0.7373	Intermediate Similarity	NPD5125	Phase 3
0.7373	Intermediate Similarity	NPD5126	Approved
0.7339	Intermediate Similarity	NPD3046	Approved
0.7339	Intermediate Similarity	NPD3048	Approved
0.7339	Intermediate Similarity	NPD3047	Approved
0.7203	Intermediate Similarity	NPD2106	Clinical (unspecified phase)
0.7167	Intermediate Similarity	NPD3897	Approved
0.7167	Intermediate Similarity	NPD3898	Approved
0.7167	Intermediate Similarity	NPD3896	Approved
0.7167	Intermediate Similarity	NPD3895	Approved
0.7097	Intermediate Similarity	NPD4624	Approved
0.7094	Intermediate Similarity	NPD4198	Discontinued
0.7064	Intermediate Similarity	NPD2553	Approved
0.7064	Intermediate Similarity	NPD2549	Approved
0.7064	Intermediate Similarity	NPD2558	Approved
0.7064	Intermediate Similarity	NPD2550	Approved
0.7064	Intermediate Similarity	NPD2555	Approved
0.7064	Intermediate Similarity	NPD2552	Approved
0.7059	Intermediate Similarity	NPD3091	Approved
0.7025	Intermediate Similarity	NPD7457	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD4188	Approved
0.7	Intermediate Similarity	NPD4189	Approved
0.7	Intermediate Similarity	NPD5691	Approved
0.6992	Remote Similarity	NPD6025	Phase 1
0.6957	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6942	Remote Similarity	NPD3095	Discontinued
0.6929	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD6353	Approved
0.6903	Remote Similarity	NPD3526	Approved
0.6903	Remote Similarity	NPD3524	Approved
0.6899	Remote Similarity	NPD4140	Approved
0.6846	Remote Similarity	NPD5735	Approved
0.6829	Remote Similarity	NPD3092	Approved
0.6803	Remote Similarity	NPD4059	Approved
0.6783	Remote Similarity	NPD2182	Approved
0.6772	Remote Similarity	NPD5736	Approved
0.6769	Remote Similarity	NPD3620	Phase 2
0.6769	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6754	Remote Similarity	NPD2559	Approved
0.6754	Remote Similarity	NPD2551	Approved
0.6752	Remote Similarity	NPD4573	Approved
0.6752	Remote Similarity	NPD4572	Approved
0.6752	Remote Similarity	NPD4571	Approved
0.6723	Remote Similarity	NPD4766	Approved
0.6723	Remote Similarity	NPD5951	Approved
0.6721	Remote Similarity	NPD3024	Approved
0.6721	Remote Similarity	NPD1651	Approved
0.6721	Remote Similarity	NPD3025	Approved
0.6718	Remote Similarity	NPD3657	Discovery
0.6697	Remote Similarity	NPD1809	Phase 2
0.6697	Remote Similarity	NPD1989	Approved
0.6695	Remote Similarity	NPD7094	Approved
0.6695	Remote Similarity	NPD7635	Approved
0.6695	Remote Similarity	NPD6858	Approved
0.6694	Remote Similarity	NPD3381	Discontinued
0.6693	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6692	Remote Similarity	NPD8032	Phase 2
0.6667	Remote Similarity	NPD845	Approved
0.6667	Remote Similarity	NPD7008	Discontinued
0.6667	Remote Similarity	NPD4626	Approved
0.6667	Remote Similarity	NPD2932	Approved
0.6667	Remote Similarity	NPD3019	Approved
0.6667	Remote Similarity	NPD6696	Suspended
0.6667	Remote Similarity	NPD2201	Approved
0.6667	Remote Similarity	NPD7157	Approved
0.6639	Remote Similarity	NPD4869	Clinical (unspecified phase)
0.6638	Remote Similarity	NPD4717	Approved
0.6638	Remote Similarity	NPD4718	Approved
0.6638	Remote Similarity	NPD4720	Approved
0.6615	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6615	Remote Similarity	NPD7294	Phase 1
0.6614	Remote Similarity	NPD3094	Phase 2
0.6613	Remote Similarity	NPD3026	Approved
0.6613	Remote Similarity	NPD3023	Approved
0.6612	Remote Similarity	NPD7340	Approved
0.6609	Remote Similarity	NPD811	Approved
0.6609	Remote Similarity	NPD812	Approved
0.6609	Remote Similarity	NPD810	Approved
0.6606	Remote Similarity	NPD6048	Clinical (unspecified phase)
0.6606	Remote Similarity	NPD6049	Phase 2
0.6606	Remote Similarity	NPD1432	Clinical (unspecified phase)
0.6585	Remote Similarity	NPD3444	Approved
0.6585	Remote Similarity	NPD3445	Approved
0.6585	Remote Similarity	NPD3443	Approved
0.6583	Remote Similarity	NPD2629	Approved
0.6581	Remote Similarity	NPD5237	Approved
0.6581	Remote Similarity	NPD5240	Approved
0.6581	Remote Similarity	NPD5239	Approved
0.6581	Remote Similarity	NPD5236	Approved
0.6581	Remote Similarity	NPD5235	Approved
0.6566	Remote Similarity	NPD9294	Approved
0.6565	Remote Similarity	NPD6663	Approved
0.656	Remote Similarity	NPD5618	Discontinued
0.656	Remote Similarity	NPD1281	Approved
0.6557	Remote Similarity	NPD7644	Approved
0.6557	Remote Similarity	NPD2484	Approved
0.6557	Remote Similarity	NPD2485	Approved
0.6552	Remote Similarity	NPD2342	Discontinued
0.6541	Remote Similarity	NPD4097	Suspended
0.6541	Remote Similarity	NPD2157	Approved
0.6535	Remote Similarity	NPD1876	Approved
0.6518	Remote Similarity	NPD3020	Approved
0.6515	Remote Similarity	NPD2979	Phase 3
0.6504	Remote Similarity	NPD2227	Clinical (unspecified phase)
0.65	Remote Similarity	NPD2991	Approved
0.65	Remote Similarity	NPD1398	Phase 1
0.65	Remote Similarity	NPD2988	Approved
0.65	Remote Similarity	NPD5283	Phase 1
0.65	Remote Similarity	NPD6010	Discontinued
0.6496	Remote Similarity	NPD2684	Approved
0.6493	Remote Similarity	NPD5886	Approved
0.6493	Remote Similarity	NPD41	Approved
0.6491	Remote Similarity	NPD3681	Approved
0.6491	Remote Similarity	NPD3683	Approved
0.6489	Remote Similarity	NPD6812	Clinical (unspecified phase)
0.6486	Remote Similarity	NPD288	Approved
0.6475	Remote Similarity	NPD7325	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD1137	Approved
0.6471	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD5763	Approved
0.6471	Remote Similarity	NPD1139	Approved
0.6471	Remote Similarity	NPD5762	Approved
0.6462	Remote Similarity	NPD7055	Discontinued
0.6457	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD5585	Approved
0.6435	Remote Similarity	NPD164	Approved
0.6434	Remote Similarity	NPD6085	Phase 2
0.6434	Remote Similarity	NPD5740	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD1611	Approved
0.6429	Remote Similarity	NPD5926	Approved
0.6429	Remote Similarity	NPD6287	Discontinued
0.6422	Remote Similarity	NPD1088	Approved
0.6417	Remote Similarity	NPD2496	Approved
0.6417	Remote Similarity	NPD1138	Approved
0.6417	Remote Similarity	NPD2497	Approved
0.6415	Remote Similarity	NPD1087	Approved
0.6412	Remote Similarity	NPD4625	Phase 3
0.6406	Remote Similarity	NPD1283	Approved
0.64	Remote Similarity	NPD7725	Approved
0.64	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.6396	Remote Similarity	NPD844	Approved
0.6393	Remote Similarity	NPD3317	Approved
0.6393	Remote Similarity	NPD6387	Discontinued
0.6391	Remote Similarity	NPD3110	Approved
0.6391	Remote Similarity	NPD3109	Approved
0.6389	Remote Similarity	NPD3672	Approved
0.6389	Remote Similarity	NPD3673	Approved
0.6385	Remote Similarity	NPD2861	Phase 2
0.6372	Remote Similarity	NPD1238	Approved
0.6357	Remote Similarity	NPD7236	Approved
0.6356	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6355	Remote Similarity	NPD1101	Approved
0.6333	Remote Similarity	NPD6124	Clinical (unspecified phase)
0.6328	Remote Similarity	NPD4749	Approved
0.6325	Remote Similarity	NPD3134	Approved
0.632	Remote Similarity	NPD1710	Approved
0.6316	Remote Similarity	NPD1616	Discontinued
0.6311	Remote Similarity	NPD9250	Approved
0.6306	Remote Similarity	NPD1693	Approved
0.6303	Remote Similarity	NPD551	Approved
0.6303	Remote Similarity	NPD4750	Phase 3
0.6303	Remote Similarity	NPD550	Approved
0.6303	Remote Similarity	NPD5451	Approved
0.6299	Remote Similarity	NPD3705	Approved
0.6293	Remote Similarity	NPD179	Clinical (unspecified phase)
0.6283	Remote Similarity	NPD4263	Approved
0.6283	Remote Similarity	NPD4813	Approved
0.6281	Remote Similarity	NPD7843	Approved
0.6279	Remote Similarity	NPD8651	Approved
0.6277	Remote Similarity	NPD2438	Suspended
0.6277	Remote Similarity	NPD2531	Phase 2
0.627	Remote Similarity	NPD4593	Approved
0.627	Remote Similarity	NPD4594	Approved
0.6269	Remote Similarity	NPD4060	Phase 1
0.6261	Remote Similarity	NPD4818	Approved
0.6261	Remote Similarity	NPD4817	Approved
0.626	Remote Similarity	NPD6671	Approved
0.626	Remote Similarity	NPD2557	Approved
0.625	Remote Similarity	NPD7250	Approved
0.625	Remote Similarity	NPD7239	Suspended
0.625	Remote Similarity	NPD3972	Approved
0.625	Remote Similarity	NPD2859	Approved
0.625	Remote Similarity	NPD2860	Approved
0.625	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.625	Remote Similarity	NPD7249	Approved
0.6241	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.624	Remote Similarity	NPD4479	Discontinued
0.6239	Remote Similarity	NPD1086	Approved
0.6239	Remote Similarity	NPD1090	Approved
0.6239	Remote Similarity	NPD1089	Approved
0.6232	Remote Similarity	NPD2174	Clinical (unspecified phase)
0.623	Remote Similarity	NPD498	Approved
0.623	Remote Similarity	NPD592	Approved
0.623	Remote Similarity	NPD594	Approved
0.623	Remote Similarity	NPD7159	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