NPASS Compound

Structure

CID104806 OpenBabel06191715452D 23 25 0 0 1 0 0 0 0 0999 V2000 -2.0908 -2.7247 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6594 -0.8912 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0981 2.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1248 -2.4659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -0.0000 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 2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 1.0000 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 0.0000 1.0000 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 1.7321 1.0000 0.0000 C 0 0 2 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 2.0981 2.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 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 2.5981 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5981 3.2321 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0981 2.3660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 5 2 0 0 0 0 5 17 1 0 0 0 0 6 9 1 0 0 0 0 6 10 1 0 0 0 0 7 11 1 0 0 0 0 7 15 1 0 0 0 0 8 12 1 0 0 0 0 8 14 1 0 0 0 0 9 18 1 0 0 0 0 10 19 1 0 0 0 0 11 17 1 0 0 0 0 12 20 1 0 0 0 0 13 17 1 0 0 0 0 13 20 1 0 0 0 0 14 18 1 1 0 0 0 14 19 1 0 0 0 0 15 18 1 1 0 0 0 15 20 1 0 0 0 0 16 19 1 0 0 0 0 16 21 2 0 0 0 0 16 22 1 0 0 0 0 17 2 1 1 0 0 0 18 3 1 1 0 0 0 19 4 1 6 0 0 0 20 23 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	320.24
Volume:	349.905
LogP:	3.347
LogD:	2.561
LogS:	-3.765
# Rotatable Bonds:	2
TPSA:	57.53
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.741
Synthetic Accessibility Score:	4.572
Fsp3:	0.85
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.599
MDCK Permeability:	1.1802442713815253e-05
Pgp-inhibitor:	0.016
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.076

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.122
Plasma Protein Binding (PPB):	87.4825668334961%
Volume Distribution (VD):	0.482
Pgp-substrate:	15.173713684082031%

ADMET: Metabolism

CYP1A2-inhibitor:	0.003
CYP1A2-substrate:	0.859
CYP2C19-inhibitor:	0.013
CYP2C19-substrate:	0.772
CYP2C9-inhibitor:	0.065
CYP2C9-substrate:	0.298
CYP2D6-inhibitor:	0.007
CYP2D6-substrate:	0.088
CYP3A4-inhibitor:	0.651
CYP3A4-substrate:	0.108

ADMET: Excretion

Clearance (CL):	1.848
Half-life (T1/2):	0.395

ADMET: Toxicity

hERG Blockers:	0.019
Human Hepatotoxicity (H-HT):	0.462
Drug-inuced Liver Injury (DILI):	0.01
AMES Toxicity:	0.005
Rat Oral Acute Toxicity:	0.134
Maximum Recommended Daily Dose:	0.266
Skin Sensitization:	0.272
Carcinogencity:	0.126
Eye Corrosion:	0.794
Eye Irritation:	0.362
Respiratory Toxicity:	0.96

Download Data

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

Natural Product: NPC104806

Natural Product ID:	NPC104806
*Common Name:**	Toonaciliatin M
IUPAC Name:	(1S,4aS,4bR,7S,8aR,10aR)-7-ethenyl-8a-hydroxy-1,4a,7-trimethyl-2,3,4,4b,5,6,8,9,10,10a-decahydrophenanthrene-1-carboxylic acid
Synonyms:	Toonaciliatin M
Standard InCHIKey:	PJBQQIKTIGUTST-PDURBABISA-N
Standard InCHI:	InChI=1S/C20H32O3/c1-5-17(2)11-7-15-18(3)9-6-10-19(4,16(21)22)14(18)8-12-20(15,23)13-17/h5,14-15,23H,1,6-13H2,2-4H3,(H,21,22)/t14-,15-,17+,18+,19+,20-/m1/s1
SMILES:	C=C[C@@]1(C)CC[C@H]2[C@@](C1)(O)CC[C@@H]1[C@]2(C)CCC[C@]1(C)C(=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL557698
PubChem CID:	42639333
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] 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
NPO13083	Toona ciliata	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19275174]
NPO6741	Metasequoia glyptostroboides	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21226514]
NPO6741	Metasequoia glyptostroboides	Species	Cupressaceae	Eukaryota	n.a.	stem	n.a.	PMID[21226514]
NPO6741	Metasequoia glyptostroboides	Species	Cupressaceae	Eukaryota	n.a.	leaf	n.a.	PMID[21226514]
NPO13083	Toona ciliata	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22537362]
NPO13083	Toona ciliata	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31503490]
NPO6741	Metasequoia glyptostroboides	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13083	Toona ciliata	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO6741	Metasequoia glyptostroboides	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13083	Toona ciliata	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13083	Toona ciliata	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO6741	Metasequoia glyptostroboides	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13083	Toona ciliata	Species	Meliaceae	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
MIC	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT329	Organism	Trichophyton rubrum	Trichophyton rubrum	MIC	=	12.5	ug.mL-1	PMID[537322]

☑ 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 NPC104806 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	182
0.1-0.2	1674
0.2-0.3	7269
0.3-0.4	16281
0.4-0.5	7128
0.5-0.6	5372
0.6-0.7	3671
0.7-0.8	1027
0.8-0.85	80
0.85-0.9	7
0.9-0.95	5
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9437	High Similarity	NPC162164
0.9167	High Similarity	NPC38426
0.9079	High Similarity	NPC20096
0.9079	High Similarity	NPC48673
0.8904	High Similarity	NPC255168
0.88	High Similarity	NPC472746
0.8649	High Similarity	NPC18819
0.8649	High Similarity	NPC46610
0.8625	High Similarity	NPC224345
0.8571	High Similarity	NPC19311
0.8571	High Similarity	NPC230047
0.8571	High Similarity	NPC231431
0.8553	High Similarity	NPC66105
0.8533	High Similarity	NPC201027
0.8514	High Similarity	NPC177826
0.8514	High Similarity	NPC36310
0.8462	Intermediate Similarity	NPC37038
0.8354	Intermediate Similarity	NPC473217
0.8354	Intermediate Similarity	NPC142244
0.8333	Intermediate Similarity	NPC41542
0.8312	Intermediate Similarity	NPC471899
0.8312	Intermediate Similarity	NPC471897
0.8312	Intermediate Similarity	NPC107039
0.8293	Intermediate Similarity	NPC72638
0.8293	Intermediate Similarity	NPC73038
0.8289	Intermediate Similarity	NPC192540
0.8289	Intermediate Similarity	NPC39362
0.8289	Intermediate Similarity	NPC279666
0.8267	Intermediate Similarity	NPC244708
0.8267	Intermediate Similarity	NPC330659
0.8267	Intermediate Similarity	NPC161187
0.8228	Intermediate Similarity	NPC469637
0.8219	Intermediate Similarity	NPC2648
0.8219	Intermediate Similarity	NPC290445
0.8219	Intermediate Similarity	NPC36616
0.8205	Intermediate Similarity	NPC280654
0.8205	Intermediate Similarity	NPC179028
0.8205	Intermediate Similarity	NPC110094
0.8205	Intermediate Similarity	NPC260385
0.8193	Intermediate Similarity	NPC102683
0.8193	Intermediate Similarity	NPC88716
0.8193	Intermediate Similarity	NPC18064
0.8193	Intermediate Similarity	NPC51700
0.8193	Intermediate Similarity	NPC98442
0.8193	Intermediate Similarity	NPC242468
0.8193	Intermediate Similarity	NPC130577
0.8193	Intermediate Similarity	NPC68160
0.8193	Intermediate Similarity	NPC293564
0.8193	Intermediate Similarity	NPC307426
0.8193	Intermediate Similarity	NPC142415
0.8193	Intermediate Similarity	NPC171203
0.8182	Intermediate Similarity	NPC198473
0.8182	Intermediate Similarity	NPC89294
0.8182	Intermediate Similarity	NPC246445
0.8182	Intermediate Similarity	NPC69143
0.8171	Intermediate Similarity	NPC264317
0.8171	Intermediate Similarity	NPC294438
0.8158	Intermediate Similarity	NPC103958
0.8158	Intermediate Similarity	NPC251970
0.8158	Intermediate Similarity	NPC183503
0.8158	Intermediate Similarity	NPC161923
0.8158	Intermediate Similarity	NPC283908
0.8158	Intermediate Similarity	NPC241854
0.8158	Intermediate Similarity	NPC476046
0.8148	Intermediate Similarity	NPC471037
0.8125	Intermediate Similarity	NPC471898
0.8125	Intermediate Similarity	NPC263272
0.8125	Intermediate Similarity	NPC267691
0.8125	Intermediate Similarity	NPC274050
0.8125	Intermediate Similarity	NPC162632
0.8108	Intermediate Similarity	NPC210323
0.8108	Intermediate Similarity	NPC196197
0.8101	Intermediate Similarity	NPC192744
0.8101	Intermediate Similarity	NPC199595
0.8101	Intermediate Similarity	NPC16394
0.8101	Intermediate Similarity	NPC263951
0.8095	Intermediate Similarity	NPC246708
0.8095	Intermediate Similarity	NPC470629
0.8095	Intermediate Similarity	NPC17733
0.8095	Intermediate Similarity	NPC182797
0.8095	Intermediate Similarity	NPC52169
0.8095	Intermediate Similarity	NPC473242
0.8095	Intermediate Similarity	NPC474512
0.8095	Intermediate Similarity	NPC181225
0.8095	Intermediate Similarity	NPC290690
0.8095	Intermediate Similarity	NPC40552
0.8077	Intermediate Similarity	NPC474433
0.8077	Intermediate Similarity	NPC68828
0.8077	Intermediate Similarity	NPC212661
0.8077	Intermediate Similarity	NPC471035
0.8072	Intermediate Similarity	NPC2783
0.8072	Intermediate Similarity	NPC12774
0.8072	Intermediate Similarity	NPC325594
0.8072	Intermediate Similarity	NPC187545
0.8052	Intermediate Similarity	NPC476844
0.8049	Intermediate Similarity	NPC156981
0.8049	Intermediate Similarity	NPC171789
0.8046	Intermediate Similarity	NPC60692
0.8025	Intermediate Similarity	NPC69101
0.8025	Intermediate Similarity	NPC251779
0.8025	Intermediate Similarity	NPC73882
0.8023	Intermediate Similarity	NPC301244
0.8	Intermediate Similarity	NPC225585
0.8	Intermediate Similarity	NPC274330
0.8	Intermediate Similarity	NPC290972
0.8	Intermediate Similarity	NPC263393
0.8	Intermediate Similarity	NPC143232
0.8	Intermediate Similarity	NPC127689
0.8	Intermediate Similarity	NPC477057
0.8	Intermediate Similarity	NPC25906
0.8	Intermediate Similarity	NPC64872
0.8	Intermediate Similarity	NPC474972
0.8	Intermediate Similarity	NPC91369
0.8	Intermediate Similarity	NPC293048
0.8	Intermediate Similarity	NPC61543
0.8	Intermediate Similarity	NPC163020
0.8	Intermediate Similarity	NPC121798
0.8	Intermediate Similarity	NPC59263
0.8	Intermediate Similarity	NPC234346
0.8	Intermediate Similarity	NPC198664
0.8	Intermediate Similarity	NPC104545
0.8	Intermediate Similarity	NPC470588
0.8	Intermediate Similarity	NPC30522
0.8	Intermediate Similarity	NPC270768
0.8	Intermediate Similarity	NPC161751
0.8	Intermediate Similarity	NPC130520
0.8	Intermediate Similarity	NPC95246
0.8	Intermediate Similarity	NPC476809
0.7976	Intermediate Similarity	NPC71507
0.7976	Intermediate Similarity	NPC269360
0.7976	Intermediate Similarity	NPC33768
0.7976	Intermediate Similarity	NPC476932
0.7976	Intermediate Similarity	NPC474684
0.7976	Intermediate Similarity	NPC264005
0.7976	Intermediate Similarity	NPC142361
0.7975	Intermediate Similarity	NPC321690
0.7975	Intermediate Similarity	NPC321514
0.7975	Intermediate Similarity	NPC476810
0.7955	Intermediate Similarity	NPC83693
0.7955	Intermediate Similarity	NPC290481
0.7952	Intermediate Similarity	NPC474537
0.7949	Intermediate Similarity	NPC20466
0.7945	Intermediate Similarity	NPC103734
0.7931	Intermediate Similarity	NPC158059
0.7931	Intermediate Similarity	NPC202728
0.7931	Intermediate Similarity	NPC275809
0.7931	Intermediate Similarity	NPC118519
0.7927	Intermediate Similarity	NPC477852
0.7927	Intermediate Similarity	NPC167103
0.7927	Intermediate Similarity	NPC70834
0.7922	Intermediate Similarity	NPC237591
0.7922	Intermediate Similarity	NPC3753
0.7907	Intermediate Similarity	NPC273621
0.7907	Intermediate Similarity	NPC227467
0.7907	Intermediate Similarity	NPC172361
0.7907	Intermediate Similarity	NPC120840
0.7907	Intermediate Similarity	NPC130278
0.7907	Intermediate Similarity	NPC113989
0.7907	Intermediate Similarity	NPC18872
0.7907	Intermediate Similarity	NPC7260
0.7907	Intermediate Similarity	NPC49320
0.7907	Intermediate Similarity	NPC111110
0.7907	Intermediate Similarity	NPC290614
0.7907	Intermediate Similarity	NPC291028
0.7907	Intermediate Similarity	NPC126369
0.7907	Intermediate Similarity	NPC210037
0.7907	Intermediate Similarity	NPC120968
0.7907	Intermediate Similarity	NPC477872
0.7907	Intermediate Similarity	NPC470589
0.7907	Intermediate Similarity	NPC86372
0.7907	Intermediate Similarity	NPC474728
0.7901	Intermediate Similarity	NPC221647
0.7901	Intermediate Similarity	NPC473420
0.7901	Intermediate Similarity	NPC147066
0.7901	Intermediate Similarity	NPC278459
0.7895	Intermediate Similarity	NPC72343
0.7895	Intermediate Similarity	NPC160817
0.7882	Intermediate Similarity	NPC471900
0.7882	Intermediate Similarity	NPC16377
0.7882	Intermediate Similarity	NPC48107
0.7882	Intermediate Similarity	NPC4309
0.7882	Intermediate Similarity	NPC474719
0.7882	Intermediate Similarity	NPC146937
0.7875	Intermediate Similarity	NPC215843
0.7857	Intermediate Similarity	NPC82979
0.7857	Intermediate Similarity	NPC324063
0.7848	Intermediate Similarity	NPC165711
0.7841	Intermediate Similarity	NPC6818
0.7841	Intermediate Similarity	NPC191412
0.7841	Intermediate Similarity	NPC80365
0.7841	Intermediate Similarity	NPC188102
0.7841	Intermediate Similarity	NPC114159
0.7838	Intermediate Similarity	NPC101307
0.7838	Intermediate Similarity	NPC117607
0.7838	Intermediate Similarity	NPC88454
0.7831	Intermediate Similarity	NPC96095
0.7821	Intermediate Similarity	NPC212733
0.7816	Intermediate Similarity	NPC52021
0.7816	Intermediate Similarity	NPC65120
0.7816	Intermediate Similarity	NPC228784

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 NPC104806 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	183
0.1-0.2	2185
0.2-0.3	4070
0.3-0.4	1823
0.4-0.5	482
0.5-0.6	203
0.6-0.7	174
0.7-0.8	30
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
0.8171	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7816	Intermediate Similarity	NPD7515	Phase 2
0.7733	Intermediate Similarity	NPD5361	Clinical (unspecified phase)
0.7733	Intermediate Similarity	NPD5360	Phase 3
0.7722	Intermediate Similarity	NPD6117	Approved
0.7703	Intermediate Similarity	NPD4224	Phase 2
0.7692	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.764	Intermediate Similarity	NPD7748	Approved
0.7625	Intermediate Similarity	NPD6116	Phase 1
0.7614	Intermediate Similarity	NPD8035	Phase 2
0.7614	Intermediate Similarity	NPD8034	Phase 2
0.7558	Intermediate Similarity	NPD3573	Approved
0.7531	Intermediate Similarity	NPD6115	Approved
0.7531	Intermediate Similarity	NPD6697	Approved
0.7531	Intermediate Similarity	NPD6118	Approved
0.7531	Intermediate Similarity	NPD6114	Approved
0.7436	Intermediate Similarity	NPD6081	Approved
0.7391	Intermediate Similarity	NPD7902	Approved
0.7386	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7294	Intermediate Similarity	NPD4788	Approved
0.7241	Intermediate Similarity	NPD3618	Phase 1
0.7241	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD6079	Approved
0.7215	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD4758	Discontinued
0.7209	Intermediate Similarity	NPD4786	Approved
0.7191	Intermediate Similarity	NPD5328	Approved
0.7179	Intermediate Similarity	NPD3699	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD3700	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD4223	Phase 3
0.7176	Intermediate Similarity	NPD4221	Approved
0.7176	Intermediate Similarity	NPD3667	Approved
0.7143	Intermediate Similarity	NPD6399	Phase 3
0.7126	Intermediate Similarity	NPD5329	Approved
0.7065	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7065	Intermediate Similarity	NPD7900	Approved
0.7045	Intermediate Similarity	NPD4623	Approved
0.7045	Intermediate Similarity	NPD6098	Approved
0.7045	Intermediate Similarity	NPD4519	Discontinued
0.7033	Intermediate Similarity	NPD5284	Approved
0.7033	Intermediate Similarity	NPD5281	Approved
0.7011	Intermediate Similarity	NPD4197	Approved
0.6957	Remote Similarity	NPD4202	Approved
0.6951	Remote Similarity	NPD3703	Phase 2
0.6951	Remote Similarity	NPD3702	Approved
0.6947	Remote Similarity	NPD7638	Approved
0.6941	Remote Similarity	NPD4695	Discontinued
0.6941	Remote Similarity	NPD7525	Registered
0.6915	Remote Similarity	NPD7614	Phase 1
0.6905	Remote Similarity	NPD5364	Discontinued
0.6905	Remote Similarity	NPD3617	Approved
0.69	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.69	Remote Similarity	NPD6899	Approved
0.69	Remote Similarity	NPD6881	Approved
0.6889	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD4245	Approved
0.6875	Remote Similarity	NPD4789	Approved
0.6875	Remote Similarity	NPD7639	Approved
0.6875	Remote Similarity	NPD4244	Approved
0.6875	Remote Similarity	NPD7640	Approved
0.6869	Remote Similarity	NPD7128	Approved
0.6869	Remote Similarity	NPD5739	Approved
0.6869	Remote Similarity	NPD6402	Approved
0.6869	Remote Similarity	NPD6675	Approved
0.6854	Remote Similarity	NPD7146	Approved
0.6854	Remote Similarity	NPD6409	Approved
0.6854	Remote Similarity	NPD7334	Approved
0.6854	Remote Similarity	NPD5330	Approved
0.6854	Remote Similarity	NPD4689	Approved
0.6854	Remote Similarity	NPD5205	Approved
0.6854	Remote Similarity	NPD4688	Approved
0.6854	Remote Similarity	NPD4690	Approved
0.6854	Remote Similarity	NPD4138	Approved
0.6854	Remote Similarity	NPD5690	Phase 2
0.6854	Remote Similarity	NPD4693	Phase 3
0.6854	Remote Similarity	NPD7521	Approved
0.6854	Remote Similarity	NPD6684	Approved
0.6842	Remote Similarity	NPD6084	Phase 2
0.6842	Remote Similarity	NPD6083	Phase 2
0.6824	Remote Similarity	NPD7645	Phase 2
0.6818	Remote Similarity	NPD3665	Phase 1
0.6818	Remote Similarity	NPD3666	Approved
0.6818	Remote Similarity	NPD3133	Approved
0.6813	Remote Similarity	NPD6673	Approved
0.6813	Remote Similarity	NPD6080	Approved
0.6813	Remote Similarity	NPD6904	Approved
0.6809	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.68	Remote Similarity	NPD5697	Approved
0.679	Remote Similarity	NPD5777	Approved
0.6765	Remote Similarity	NPD7290	Approved
0.6765	Remote Similarity	NPD6883	Approved
0.6765	Remote Similarity	NPD7102	Approved
0.675	Remote Similarity	NPD3698	Phase 2
0.6737	Remote Similarity	NPD5222	Approved
0.6737	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6737	Remote Similarity	NPD5221	Approved
0.6733	Remote Similarity	NPD6011	Approved
0.6733	Remote Similarity	NPD7320	Approved
0.6703	Remote Similarity	NPD5737	Approved
0.6703	Remote Similarity	NPD6903	Approved
0.6703	Remote Similarity	NPD5208	Approved
0.6703	Remote Similarity	NPD6672	Approved
0.6702	Remote Similarity	NPD6001	Approved
0.6701	Remote Similarity	NPD5286	Approved
0.6701	Remote Similarity	NPD4696	Approved
0.6701	Remote Similarity	NPD5285	Approved
0.6699	Remote Similarity	NPD6847	Approved
0.6699	Remote Similarity	NPD6649	Approved
0.6699	Remote Similarity	NPD6869	Approved
0.6699	Remote Similarity	NPD6650	Approved
0.6699	Remote Similarity	NPD6617	Approved
0.6699	Remote Similarity	NPD8130	Phase 1
0.6667	Remote Similarity	NPD6012	Approved
0.6667	Remote Similarity	NPD6013	Approved
0.6667	Remote Similarity	NPD6372	Approved
0.6667	Remote Similarity	NPD4139	Approved
0.6667	Remote Similarity	NPD4694	Approved
0.6667	Remote Similarity	NPD6373	Approved
0.6667	Remote Similarity	NPD4692	Approved
0.6667	Remote Similarity	NPD6411	Approved
0.6667	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5173	Approved
0.6667	Remote Similarity	NPD5280	Approved
0.6667	Remote Similarity	NPD6014	Approved
0.6667	Remote Similarity	NPD4755	Approved
0.6635	Remote Similarity	NPD8297	Approved
0.6635	Remote Similarity	NPD6882	Approved
0.6634	Remote Similarity	NPD5701	Approved
0.6633	Remote Similarity	NPD5223	Approved
0.6632	Remote Similarity	NPD5695	Phase 3
0.663	Remote Similarity	NPD4753	Phase 2
0.6629	Remote Similarity	NPD3668	Phase 3
0.6628	Remote Similarity	NPD4195	Approved
0.6627	Remote Similarity	NPD4784	Approved
0.6627	Remote Similarity	NPD4785	Approved
0.6598	Remote Similarity	NPD5696	Approved
0.6585	Remote Similarity	NPD4243	Approved
0.6566	Remote Similarity	NPD5224	Approved
0.6566	Remote Similarity	NPD5211	Phase 2
0.6566	Remote Similarity	NPD5225	Approved
0.6566	Remote Similarity	NPD4633	Approved
0.6566	Remote Similarity	NPD5226	Approved
0.6562	Remote Similarity	NPD4697	Phase 3
0.6559	Remote Similarity	NPD5207	Approved
0.6538	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6531	Remote Similarity	NPD4700	Approved
0.6512	Remote Similarity	NPD3671	Phase 1
0.65	Remote Similarity	NPD5174	Approved
0.65	Remote Similarity	NPD5175	Approved
0.6489	Remote Similarity	NPD5693	Phase 1
0.6489	Remote Similarity	NPD6050	Approved
0.6489	Remote Similarity	NPD5694	Approved
0.6458	Remote Similarity	NPD4629	Approved
0.6458	Remote Similarity	NPD5210	Approved
0.6452	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD6101	Approved
0.6438	Remote Similarity	NPD615	Clinical (unspecified phase)
0.6436	Remote Similarity	NPD5141	Approved
0.6415	Remote Similarity	NPD4632	Approved
0.6404	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.64	Remote Similarity	NPD7632	Discontinued
0.6392	Remote Similarity	NPD7732	Phase 3
0.6389	Remote Similarity	NPD7115	Discovery
0.6383	Remote Similarity	NPD5692	Phase 3
0.6374	Remote Similarity	NPD1694	Approved
0.6353	Remote Similarity	NPD6942	Approved
0.6353	Remote Similarity	NPD7339	Approved
0.6341	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6341	Remote Similarity	NPD4137	Phase 3
0.6337	Remote Similarity	NPD4754	Approved
0.633	Remote Similarity	NPD6335	Approved
0.6322	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6304	Remote Similarity	NPD5279	Phase 3
0.6296	Remote Similarity	NPD6868	Approved
0.6279	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6273	Remote Similarity	NPD7100	Approved
0.6273	Remote Similarity	NPD7101	Approved
0.6265	Remote Similarity	NPD4691	Approved
0.6265	Remote Similarity	NPD4747	Approved
0.6262	Remote Similarity	NPD8133	Approved
0.625	Remote Similarity	NPD7341	Phase 2
0.625	Remote Similarity	NPD5133	Approved
0.625	Remote Similarity	NPD4730	Approved
0.625	Remote Similarity	NPD4729	Approved
0.6239	Remote Similarity	NPD6009	Approved
0.6239	Remote Similarity	NPD6317	Approved
0.6235	Remote Similarity	NPD4058	Approved
0.622	Remote Similarity	NPD3621	Clinical (unspecified phase)
0.6216	Remote Similarity	NPD3194	Approved
0.6216	Remote Similarity	NPD4266	Approved
0.6216	Remote Similarity	NPD3195	Phase 2
0.6216	Remote Similarity	NPD3196	Approved
0.6214	Remote Similarity	NPD6008	Approved
0.6214	Remote Similarity	NPD4767	Approved
0.6214	Remote Similarity	NPD4768	Approved
0.6211	Remote Similarity	NPD4096	Approved
0.62	Remote Similarity	NPD6404	Discontinued
0.619	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.619	Remote Similarity	NPD8132	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