NPASS Compound

Structure

CID23086 OpenBabel06191715352D 22 24 0 0 1 0 0 0 0 0999 V2000 -2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5254 0.6088 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9568 -1.2247 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6516 -0.6741 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9909 -0.9659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1056 0.2169 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5075 0.4701 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.6639 -0.5176 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3985 0.9240 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 15 1 0 0 0 0 4 5 1 0 0 0 0 4 6 1 0 0 0 0 5 17 2 0 0 0 0 6 18 1 0 0 0 0 7 10 1 0 0 0 0 7 15 1 0 0 0 0 8 11 1 0 0 0 0 8 16 1 0 0 0 0 9 12 2 0 0 0 0 9 16 1 0 0 0 0 10 20 1 0 0 0 0 11 19 1 0 0 0 0 12 22 1 0 0 0 0 13 17 1 0 0 0 0 13 21 1 0 0 0 0 14 16 2 0 0 0 0 14 22 1 0 0 0 0 15 19 1 6 0 0 0 17 20 1 0 0 0 0 18 19 1 6 0 0 0 18 20 1 0 0 0 0 19 2 1 6 0 0 0 20 3 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	302.22
Volume:	338.478
LogP:	4.244
LogD:	4.084
LogS:	-4.731
# Rotatable Bonds:	4
TPSA:	33.37
# H-Bond Aceptor:	2
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.795
Synthetic Accessibility Score:	4.309
Fsp3:	0.7
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:	-4.504
MDCK Permeability:	2.0223806131980382e-05
Pgp-inhibitor:	0.01
Pgp-substrate:	0.004
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.462
30% Bioavailability (F30%):	0.185

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.058
Plasma Protein Binding (PPB):	97.91858673095703%
Volume Distribution (VD):	2.11
Pgp-substrate:	2.830051898956299%

ADMET: Metabolism

CYP1A2-inhibitor:	0.3
CYP1A2-substrate:	0.377
CYP2C19-inhibitor:	0.431
CYP2C19-substrate:	0.753
CYP2C9-inhibitor:	0.434
CYP2C9-substrate:	0.115
CYP2D6-inhibitor:	0.726
CYP2D6-substrate:	0.741
CYP3A4-inhibitor:	0.745
CYP3A4-substrate:	0.293

ADMET: Excretion

Clearance (CL):	9.808
Half-life (T1/2):	0.638

ADMET: Toxicity

hERG Blockers:	0.071
Human Hepatotoxicity (H-HT):	0.141
Drug-inuced Liver Injury (DILI):	0.029
AMES Toxicity:	0.007
Rat Oral Acute Toxicity:	0.819
Maximum Recommended Daily Dose:	0.52
Skin Sensitization:	0.287
Carcinogencity:	0.413
Eye Corrosion:	0.163
Eye Irritation:	0.932
Respiratory Toxicity:	0.974

Download Data

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

Natural Product: NPC23086

Natural Product ID:	NPC23086
*Common Name:**	Hardwickiol
IUPAC Name:	[(4aR,5S,6R,8aR)-5-[2-(furan-3-yl)ethyl]-5,6,8a-trimethyl-3,4,4a,6,7,8-hexahydronaphthalen-1-yl]methanol
Synonyms:	Hardwickiol
Standard InCHIKey:	YQRXYOHAFOQXMN-XCLNPWKQSA-N
Standard InCHI:	InChI=1S/C20H30O2/c1-15-7-10-20(3)17(13-21)5-4-6-18(20)19(15,2)11-8-16-9-12-22-14-16/h5,9,12,14-15,18,21H,4,6-8,10-11,13H2,1-3H3/t15-,18-,19+,20+/m1/s1
SMILES:	C[C@@H]1CC[C@@]2(C)C(=CCC[C@@H]2[C@@]1(C)CCc1ccoc1)CO
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL519662
PubChem CID:	44576133
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0001757] Colensane and clerodane diterpenoids

*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
NPO3487	Croton sonderianus	Species	Euphorbiaceae	Eukaryota	Roots	n.a.	n.a.	PMID[1812213]
NPO24912	Petasites kablikianus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23791	Menispermum canadense	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24912	Petasites kablikianus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23791	Menispermum canadense	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23791	Menispermum canadense	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO25077	Calvatia craniformis	Species	Lycoperdaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3487	Croton sonderianus	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24270	Alstonia congensis	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25380	Mycena galericulata	Species	Tricholomataceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23791	Menispermum canadense	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24912	Petasites kablikianus	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
Others	14

Activity Type	# Activity
Organism	14

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1815	Organism	Helminthosporium	Helminthosporium	IZ	=	1.0	mm	PMID[527445]
NPT1815	Organism	Helminthosporium	Helminthosporium	IZ	=	3.0	mm	PMID[527445]
NPT330	Organism	Trichophyton mentagrophytes	Trichophyton mentagrophytes	IZ	=	3.0	mm	PMID[527445]
NPT330	Organism	Trichophyton mentagrophytes	Trichophyton mentagrophytes	IZ	=	7.0	mm	PMID[527445]
NPT20	Organism	Candida albicans	Candida albicans	IZ	=	7.0	mm	PMID[527445]
NPT20	Organism	Candida albicans	Candida albicans	IZ	=	3.0	mm	PMID[527445]
NPT312	Organism	Saccharomyces cerevisiae	Saccharomyces cerevisiae	IZ	=	3.0	mm	PMID[527445]
NPT602	Organism	Mycobacterium smegmatis	Mycobacterium smegmatis	IZ	=	7.0	mm	PMID[527445]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	IZ	=	3.0	mm	PMID[527445]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	IZ	=	3.0	mm	PMID[527445]

☑ 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 NPC23086 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	252
0.1-0.2	1352
0.2-0.3	2837
0.3-0.4	6986
0.4-0.5	12620
0.5-0.6	11037
0.6-0.7	6872
0.7-0.8	604
0.8-0.85	72
0.85-0.9	42
0.9-0.95	20
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9669	High Similarity	NPC207294
0.9669	High Similarity	NPC112706
0.9496	High Similarity	NPC477967
0.9435	High Similarity	NPC61788
0.9426	High Similarity	NPC83178
0.9344	High Similarity	NPC46536
0.9344	High Similarity	NPC138139
0.9286	High Similarity	NPC218838
0.9268	High Similarity	NPC290955
0.9194	High Similarity	NPC477123
0.9194	High Similarity	NPC477966
0.9127	High Similarity	NPC89133
0.9098	High Similarity	NPC16922
0.9098	High Similarity	NPC272899
0.9068	High Similarity	NPC150895
0.904	High Similarity	NPC477039
0.904	High Similarity	NPC477040
0.9008	High Similarity	NPC90953
0.9	High Similarity	NPC243704
0.8992	High Similarity	NPC476947
0.8992	High Similarity	NPC158525
0.896	High Similarity	NPC246392
0.8952	High Similarity	NPC179354
0.8952	High Similarity	NPC303010
0.8898	High Similarity	NPC476925
0.8889	High Similarity	NPC476917
0.8889	High Similarity	NPC327527
0.8889	High Similarity	NPC26532
0.8889	High Similarity	NPC279877
0.8889	High Similarity	NPC329707
0.888	High Similarity	NPC74612
0.8871	High Similarity	NPC477965
0.8871	High Similarity	NPC243269
0.8871	High Similarity	NPC477038
0.8871	High Similarity	NPC130275
0.8862	High Similarity	NPC317217
0.8779	High Similarity	NPC46896
0.876	High Similarity	NPC212918
0.8731	High Similarity	NPC205765
0.8692	High Similarity	NPC471006
0.8682	High Similarity	NPC298190
0.8672	High Similarity	NPC223063
0.8672	High Similarity	NPC120836
0.8672	High Similarity	NPC59502
0.8657	High Similarity	NPC67003
0.8651	High Similarity	NPC300098
0.8615	High Similarity	NPC471995
0.8615	High Similarity	NPC473982
0.8607	High Similarity	NPC208906
0.8607	High Similarity	NPC144745
0.8603	High Similarity	NPC476946
0.8582	High Similarity	NPC202260
0.8571	High Similarity	NPC118853
0.856	High Similarity	NPC36255
0.8559	High Similarity	NPC177331
0.854	High Similarity	NPC476944
0.8537	High Similarity	NPC87466
0.8529	High Similarity	NPC52412
0.8519	High Similarity	NPC90296
0.8519	High Similarity	NPC148374
0.8507	High Similarity	NPC472376
0.8504	High Similarity	NPC471074
0.8504	High Similarity	NPC473885
0.8504	High Similarity	NPC290193
0.8496	Intermediate Similarity	NPC146872
0.8489	Intermediate Similarity	NPC250228
0.848	Intermediate Similarity	NPC97566
0.8478	Intermediate Similarity	NPC185456
0.8467	Intermediate Similarity	NPC243577
0.8433	Intermediate Similarity	NPC310830
0.8425	Intermediate Similarity	NPC83115
0.8421	Intermediate Similarity	NPC92941
0.8417	Intermediate Similarity	NPC346
0.8409	Intermediate Similarity	NPC470740
0.8394	Intermediate Similarity	NPC263337
0.8394	Intermediate Similarity	NPC121158
0.8385	Intermediate Similarity	NPC208389
0.837	Intermediate Similarity	NPC471996
0.8369	Intermediate Similarity	NPC470998
0.8359	Intermediate Similarity	NPC230979
0.8357	Intermediate Similarity	NPC471174
0.8357	Intermediate Similarity	NPC302987
0.8346	Intermediate Similarity	NPC471998
0.8345	Intermediate Similarity	NPC5676
0.8333	Intermediate Similarity	NPC267632
0.8298	Intermediate Similarity	NPC476941
0.8298	Intermediate Similarity	NPC476942
0.8296	Intermediate Similarity	NPC470742
0.8296	Intermediate Similarity	NPC307401
0.8273	Intermediate Similarity	NPC251865
0.8268	Intermediate Similarity	NPC473379
0.8268	Intermediate Similarity	NPC471549
0.8248	Intermediate Similarity	NPC56197
0.8239	Intermediate Similarity	NPC234494
0.8235	Intermediate Similarity	NPC236532
0.8235	Intermediate Similarity	NPC476943
0.8235	Intermediate Similarity	NPC220094
0.8227	Intermediate Similarity	NPC476937
0.8227	Intermediate Similarity	NPC476938
0.8227	Intermediate Similarity	NPC216755
0.8217	Intermediate Similarity	NPC474829
0.8197	Intermediate Similarity	NPC1811
0.8197	Intermediate Similarity	NPC26157
0.8195	Intermediate Similarity	NPC471817
0.8194	Intermediate Similarity	NPC33938
0.8189	Intermediate Similarity	NPC79557
0.8182	Intermediate Similarity	NPC196846
0.8182	Intermediate Similarity	NPC470997
0.8169	Intermediate Similarity	NPC471007
0.8168	Intermediate Similarity	NPC474279
0.8168	Intermediate Similarity	NPC474438
0.8162	Intermediate Similarity	NPC42400
0.8162	Intermediate Similarity	NPC186626
0.8162	Intermediate Similarity	NPC170604
0.8162	Intermediate Similarity	NPC4764
0.8162	Intermediate Similarity	NPC215109
0.8145	Intermediate Similarity	NPC28054
0.814	Intermediate Similarity	NPC178382
0.814	Intermediate Similarity	NPC188377
0.814	Intermediate Similarity	NPC65735
0.8129	Intermediate Similarity	NPC473152
0.8125	Intermediate Similarity	NPC263870
0.8116	Intermediate Similarity	NPC201370
0.8116	Intermediate Similarity	NPC473983
0.8115	Intermediate Similarity	NPC277525
0.8112	Intermediate Similarity	NPC195325
0.8112	Intermediate Similarity	NPC125182
0.8112	Intermediate Similarity	NPC69647
0.8112	Intermediate Similarity	NPC472654
0.8106	Intermediate Similarity	NPC198904
0.8099	Intermediate Similarity	NPC255414
0.8092	Intermediate Similarity	NPC474830
0.8092	Intermediate Similarity	NPC95567
0.8092	Intermediate Similarity	NPC476016
0.8092	Intermediate Similarity	NPC319140
0.8082	Intermediate Similarity	NPC35000
0.8077	Intermediate Similarity	NPC71274
0.8077	Intermediate Similarity	NPC75557
0.8069	Intermediate Similarity	NPC470996
0.8069	Intermediate Similarity	NPC469503
0.8031	Intermediate Similarity	NPC137710
0.8015	Intermediate Similarity	NPC474260
0.8015	Intermediate Similarity	NPC329694
0.8015	Intermediate Similarity	NPC81912
0.8015	Intermediate Similarity	NPC329922
0.8014	Intermediate Similarity	NPC30222
0.8014	Intermediate Similarity	NPC199044
0.8014	Intermediate Similarity	NPC57998
0.8014	Intermediate Similarity	NPC142113
0.8014	Intermediate Similarity	NPC238843
0.8014	Intermediate Similarity	NPC178932
0.8	Intermediate Similarity	NPC272590
0.8	Intermediate Similarity	NPC20578
0.8	Intermediate Similarity	NPC205523
0.8	Intermediate Similarity	NPC62103
0.8	Intermediate Similarity	NPC293253
0.7985	Intermediate Similarity	NPC477645
0.7967	Intermediate Similarity	NPC105249
0.7959	Intermediate Similarity	NPC155939
0.7959	Intermediate Similarity	NPC141538
0.7959	Intermediate Similarity	NPC92979
0.7959	Intermediate Similarity	NPC469336
0.7959	Intermediate Similarity	NPC281258
0.7959	Intermediate Similarity	NPC296807
0.7958	Intermediate Similarity	NPC247221
0.7945	Intermediate Similarity	NPC476940
0.7945	Intermediate Similarity	NPC121615
0.7945	Intermediate Similarity	NPC75906
0.7945	Intermediate Similarity	NPC44577
0.7945	Intermediate Similarity	NPC476939
0.7945	Intermediate Similarity	NPC246164
0.7945	Intermediate Similarity	NPC472672
0.7945	Intermediate Similarity	NPC294511
0.7943	Intermediate Similarity	NPC223415
0.7943	Intermediate Similarity	NPC470741
0.7941	Intermediate Similarity	NPC106247
0.7939	Intermediate Similarity	NPC471559
0.7937	Intermediate Similarity	NPC45536
0.7931	Intermediate Similarity	NPC212257
0.7931	Intermediate Similarity	NPC228842
0.7926	Intermediate Similarity	NPC473344
0.7926	Intermediate Similarity	NPC471544
0.7923	Intermediate Similarity	NPC476351
0.7917	Intermediate Similarity	NPC93666
0.7902	Intermediate Similarity	NPC470999
0.7902	Intermediate Similarity	NPC471292
0.7899	Intermediate Similarity	NPC473268
0.7891	Intermediate Similarity	NPC237259
0.7891	Intermediate Similarity	NPC34421
0.7891	Intermediate Similarity	NPC302054
0.7891	Intermediate Similarity	NPC253201
0.7891	Intermediate Similarity	NPC98206
0.7891	Intermediate Similarity	NPC282445
0.7891	Intermediate Similarity	NPC473969
0.7887	Intermediate Similarity	NPC137295
0.7887	Intermediate Similarity	NPC158871
0.7883	Intermediate Similarity	NPC265793
0.7874	Intermediate Similarity	NPC312525
0.7874	Intermediate Similarity	NPC217180
0.7869	Intermediate Similarity	NPC471521

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 NPC23086 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	261
0.1-0.2	975
0.2-0.3	1656
0.3-0.4	2728
0.4-0.5	2191
0.5-0.6	1094
0.6-0.7	238
0.7-0.8	7
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
0.7959	Intermediate Similarity	NPD5760	Phase 2
0.7959	Intermediate Similarity	NPD5761	Phase 2
0.7786	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7603	Intermediate Similarity	NPD6273	Approved
0.75	Intermediate Similarity	NPD4628	Phase 3
0.7292	Intermediate Similarity	NPD2344	Approved
0.7287	Intermediate Similarity	NPD1241	Discontinued
0.726	Intermediate Similarity	NPD7003	Approved
0.7259	Intermediate Similarity	NPD3972	Approved
0.7164	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD2799	Discontinued
0.7153	Intermediate Similarity	NPD1876	Approved
0.7117	Intermediate Similarity	NPD6764	Approved
0.7117	Intermediate Similarity	NPD6765	Approved
0.7108	Intermediate Similarity	NPD8434	Phase 2
0.7105	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD2797	Approved
0.7097	Intermediate Similarity	NPD5616	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD2309	Approved
0.7055	Intermediate Similarity	NPD1471	Phase 3
0.705	Intermediate Similarity	NPD2798	Approved
0.7027	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD4140	Approved
0.6959	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6946	Remote Similarity	NPD6784	Approved
0.6946	Remote Similarity	NPD6785	Approved
0.6939	Remote Similarity	NPD2346	Discontinued
0.6934	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD8032	Phase 2
0.6918	Remote Similarity	NPD4308	Phase 3
0.6906	Remote Similarity	NPD1283	Approved
0.6884	Remote Similarity	NPD1608	Approved
0.6884	Remote Similarity	NPD9717	Approved
0.6883	Remote Similarity	NPD7458	Discontinued
0.6871	Remote Similarity	NPD1551	Phase 2
0.6853	Remote Similarity	NPD2313	Discontinued
0.6853	Remote Similarity	NPD3268	Approved
0.6842	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6838	Remote Similarity	NPD5585	Approved
0.6831	Remote Similarity	NPD6832	Phase 2
0.6828	Remote Similarity	NPD6355	Discontinued
0.6824	Remote Similarity	NPD6005	Phase 3
0.6824	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD6004	Phase 3
0.6824	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD6002	Phase 3
0.68	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.68	Remote Similarity	NPD3750	Approved
0.68	Remote Similarity	NPD4110	Phase 3
0.6794	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6791	Remote Similarity	NPD7157	Approved
0.6788	Remote Similarity	NPD2932	Approved
0.6788	Remote Similarity	NPD1778	Approved
0.6769	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6761	Remote Similarity	NPD9494	Approved
0.6757	Remote Similarity	NPD6099	Approved
0.6757	Remote Similarity	NPD2935	Discontinued
0.6757	Remote Similarity	NPD4476	Approved
0.6757	Remote Similarity	NPD6100	Approved
0.6757	Remote Similarity	NPD4477	Approved
0.6738	Remote Similarity	NPD1049	Clinical (unspecified phase)
0.6738	Remote Similarity	NPD1203	Approved
0.6736	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6736	Remote Similarity	NPD3764	Approved
0.6733	Remote Similarity	NPD2800	Approved
0.6716	Remote Similarity	NPD5951	Approved
0.6715	Remote Similarity	NPD1651	Approved
0.6714	Remote Similarity	NPD5327	Phase 3
0.6712	Remote Similarity	NPD5735	Approved
0.6711	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD6559	Discontinued
0.6691	Remote Similarity	NPD1281	Approved
0.669	Remote Similarity	NPD5647	Approved
0.669	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6689	Remote Similarity	NPD8166	Discontinued
0.6667	Remote Similarity	NPD4626	Approved
0.6667	Remote Similarity	NPD3226	Approved
0.6667	Remote Similarity	NPD3019	Approved
0.6667	Remote Similarity	NPD7008	Discontinued
0.6667	Remote Similarity	NPD8127	Discontinued
0.6667	Remote Similarity	NPD17	Approved
0.6646	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD4575	Clinical (unspecified phase)
0.6645	Remote Similarity	NPD3869	Phase 3
0.6645	Remote Similarity	NPD3873	Phase 3
0.6645	Remote Similarity	NPD920	Approved
0.6644	Remote Similarity	NPD2796	Approved
0.6644	Remote Similarity	NPD4307	Phase 2
0.6644	Remote Similarity	NPD2979	Phase 3
0.6644	Remote Similarity	NPD3142	Approved
0.6644	Remote Similarity	NPD3140	Approved
0.6642	Remote Similarity	NPD9545	Approved
0.6642	Remote Similarity	NPD1894	Discontinued
0.6641	Remote Similarity	NPD2684	Approved
0.6624	Remote Similarity	NPD6599	Discontinued
0.6624	Remote Similarity	NPD7028	Phase 2
0.6623	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6623	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6621	Remote Similarity	NPD411	Approved
0.6619	Remote Similarity	NPD3496	Discontinued
0.6619	Remote Similarity	NPD7457	Clinical (unspecified phase)
0.6617	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6604	Remote Similarity	NPD7819	Suspended
0.6596	Remote Similarity	NPD4359	Approved
0.6594	Remote Similarity	NPD5691	Approved
0.6577	Remote Similarity	NPD3748	Approved
0.6575	Remote Similarity	NPD6663	Approved
0.6573	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6569	Remote Similarity	NPD9092	Discovery
0.6562	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD2296	Approved
0.6561	Remote Similarity	NPD2649	Approved
0.6561	Remote Similarity	NPD2651	Approved
0.6556	Remote Similarity	NPD1549	Phase 2
0.6556	Remote Similarity	NPD4534	Discontinued
0.6554	Remote Similarity	NPD6653	Approved
0.6554	Remote Similarity	NPD6353	Approved
0.6554	Remote Similarity	NPD1607	Approved
0.6549	Remote Similarity	NPD6696	Suspended
0.6547	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.6541	Remote Similarity	NPD7577	Discontinued
0.6541	Remote Similarity	NPD6279	Approved
0.6541	Remote Similarity	NPD6280	Approved
0.6531	Remote Similarity	NPD4060	Phase 1
0.6531	Remote Similarity	NPD1240	Approved
0.6528	Remote Similarity	NPD5736	Approved
0.6522	Remote Similarity	NPD7768	Phase 2
0.6516	Remote Similarity	NPD2533	Approved
0.6516	Remote Similarity	NPD2534	Approved
0.6516	Remote Similarity	NPD2532	Approved
0.6516	Remote Similarity	NPD4662	Approved
0.6516	Remote Similarity	NPD4661	Approved
0.6515	Remote Similarity	NPD2182	Approved
0.6513	Remote Similarity	NPD1243	Approved
0.6507	Remote Similarity	NPD6798	Discontinued
0.6503	Remote Similarity	NPD3267	Approved
0.6503	Remote Similarity	NPD6362	Approved
0.6503	Remote Similarity	NPD3266	Approved
0.6496	Remote Similarity	NPD9493	Approved
0.6494	Remote Similarity	NPD7236	Approved
0.6494	Remote Similarity	NPD7440	Discontinued
0.649	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.649	Remote Similarity	NPD5763	Approved
0.649	Remote Similarity	NPD5762	Approved
0.649	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6489	Remote Similarity	NPD3134	Approved
0.6486	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6486	Remote Similarity	NPD447	Suspended
0.6483	Remote Similarity	NPD2614	Approved
0.6481	Remote Similarity	NPD3749	Approved
0.6478	Remote Similarity	NPD7411	Suspended
0.6475	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD2629	Approved
0.6467	Remote Similarity	NPD1510	Phase 2
0.6467	Remote Similarity	NPD7033	Discontinued
0.6458	Remote Similarity	NPD1019	Discontinued
0.6458	Remote Similarity	NPD4624	Approved
0.6447	Remote Similarity	NPD5958	Discontinued
0.6447	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6447	Remote Similarity	NPD2424	Discontinued
0.6444	Remote Similarity	NPD7843	Approved
0.6438	Remote Similarity	NPD7095	Approved
0.6434	Remote Similarity	NPD8651	Approved
0.6429	Remote Similarity	NPD5844	Phase 1
0.6424	Remote Similarity	NPD2531	Phase 2
0.6424	Remote Similarity	NPD2438	Suspended
0.6423	Remote Similarity	NPD6671	Approved
0.642	Remote Similarity	NPD3882	Suspended
0.6419	Remote Similarity	NPD3620	Phase 2
0.6419	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6418	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6415	Remote Similarity	NPD4380	Phase 2
0.641	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6409	Remote Similarity	NPD3057	Approved
0.6408	Remote Similarity	NPD1481	Phase 2
0.6398	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6398	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6395	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.638	Remote Similarity	NPD7075	Discontinued
0.6377	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6376	Remote Similarity	NPD4618	Approved
0.6376	Remote Similarity	NPD4622	Approved
0.6369	Remote Similarity	NPD7177	Discontinued
0.6364	Remote Similarity	NPD968	Approved
0.6364	Remote Similarity	NPD4749	Approved
0.6351	Remote Similarity	NPD6233	Phase 2
0.6351	Remote Similarity	NPD4062	Phase 3
0.6351	Remote Similarity	NPD4870	Approved
0.6346	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6346	Remote Similarity	NPD6799	Approved
0.6341	Remote Similarity	NPD919	Approved
0.6338	Remote Similarity	NPD1535	Discovery
0.6338	Remote Similarity	NPD1201	Approved
0.6336	Remote Similarity	NPD1237	Approved
0.6335	Remote Similarity	NPD6801	Discontinued
0.6335	Remote Similarity	NPD6844	Discontinued
0.6333	Remote Similarity	NPD6651	Approved
0.6329	Remote Similarity	NPD7427	Discontinued

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