NPASS Compound

Structure

CID171759 OpenBabel06191715542D 26 28 0 0 1 0 0 0 0 0999 V2000 -3.7187 -6.2744 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0464 -5.3088 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9481 1.5382 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2611 -2.4847 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9624 -1.1770 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7187 -5.3088 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5636 0.6683 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4722 -0.8878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8825 -4.8261 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5291 0.6683 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.3476 -1.5231 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0928 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9616 -0.0865 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.7451 -1.5231 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1765 -1.0279 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.1311 -0.0865 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.0464 -1.4468 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.8825 -3.8606 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3795 -0.8878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9163 -1.0279 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.5880 0.8288 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.8317 -2.4847 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.7187 -3.3778 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3208 -1.1027 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.0464 -3.3778 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 6 1 0 0 0 0 2 9 1 0 0 0 0 4 11 2 0 0 0 0 6 9 2 0 0 0 0 7 10 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 3 1 6 0 0 0 10 16 1 0 0 0 0 11 19 1 0 0 0 0 12 16 1 0 0 0 0 12 21 1 6 0 0 0 13 7 1 1 0 0 0 13 15 1 0 0 0 0 13 25 1 0 0 0 0 14 20 1 0 0 0 0 14 22 2 0 0 0 0 15 11 1 1 0 0 0 15 17 1 0 0 0 0 16 20 1 1 0 0 0 17 20 1 6 0 0 0 17 26 1 0 0 0 0 18 23 2 0 0 0 0 18 26 1 0 0 0 0 19 24 2 0 0 0 0 19 25 1 0 0 0 0 20 5 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	362.17
Volume:	368.366
LogP:	1.202
LogD:	1.74
LogS:	-2.911
# Rotatable Bonds:	3
TPSA:	89.9
# H-Bond Aceptor:	6
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.597
Synthetic Accessibility Score:	4.828
Fsp3:	0.65
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	2
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.772
MDCK Permeability:	2.861193752323743e-05
Pgp-inhibitor:	0.94
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.133
20% Bioavailability (F20%):	0.933
30% Bioavailability (F30%):	0.978

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.896
Plasma Protein Binding (PPB):	69.15081024169922%
Volume Distribution (VD):	0.6
Pgp-substrate:	25.646390914916992%

ADMET: Metabolism

CYP1A2-inhibitor:	0.089
CYP1A2-substrate:	0.164
CYP2C19-inhibitor:	0.323
CYP2C19-substrate:	0.596
CYP2C9-inhibitor:	0.727
CYP2C9-substrate:	0.092
CYP2D6-inhibitor:	0.015
CYP2D6-substrate:	0.097
CYP3A4-inhibitor:	0.832
CYP3A4-substrate:	0.36

ADMET: Excretion

Clearance (CL):	9.95
Half-life (T1/2):	0.919

ADMET: Toxicity

hERG Blockers:	0.037
Human Hepatotoxicity (H-HT):	0.488
Drug-inuced Liver Injury (DILI):	0.567
AMES Toxicity:	0.013
Rat Oral Acute Toxicity:	0.734
Maximum Recommended Daily Dose:	0.047
Skin Sensitization:	0.643
Carcinogencity:	0.428
Eye Corrosion:	0.821
Eye Irritation:	0.5
Respiratory Toxicity:	0.963

Download Data

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

Natural Product: NPC171759

Natural Product ID:	NPC171759
*Common Name:**	Arnifolin
IUPAC Name:	[(3aR,5R,5aS,6S,8aR,9S,9aR)-6-hydroxy-5,8a-dimethyl-1-methylidene-2,8-dioxo-3a,4,5,5a,6,7,9,9a-octahydroazuleno[6,5-b]furan-9-yl] (E)-2-methylbut-2-enoate
Synonyms:	Arnifolin
Standard InCHIKey:	OUCLBKPZGHAPKI-PFNWYZTJSA-N
Standard InCHI:	InChI=1S/C20H26O6/c1-6-9(2)18(23)26-17-15-11(4)19(24)25-13(15)7-10(3)16-12(21)8-14(22)20(16,17)5/h6,10,12-13,15-17,21H,4,7-8H2,1-3,5H3/b9-6+/t10-,12+,13-,15-,16-,17+,20-/m1/s1
SMILES:	C/C=C(C)/C(=O)O[C@H]1[C@@H]2C(=C)C(=O)O[C@@H]2C[C@@H](C)[C@@H]2[C@H](CC(=O)[C@@]12C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL452753
PubChem CID:	44559333
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones [CHEMONTID:0001543] Sesquiterpene lactones

*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
NPO5484	Arnica angustifolia	Species	Asteraceae	Eukaryota	n.a.	flower	n.a.	PMID[16644542]
NPO5484	Arnica angustifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23501116]
NPO8104	Trocholejeunea sandvicensis	Species	Lejeuneaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5919	Phoebe cinnamomifolia	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8104	Trocholejeunea sandvicensis	Species	Lejeuneaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5919	Phoebe cinnamomifolia	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3832	Abuta pahni	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5148	Geranium saxatile	Species	Geraniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7558	Primula sieboldi	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6083	Richardsonia scabra	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO2305	Naregamia alata	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5320	Fleischmannia multinervis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7061	Tabernaemontana laeta	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8104	Trocholejeunea sandvicensis	Species	Lejeuneaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5484	Arnica angustifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7218	Salvia montbretii	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8271	Aplophyllum tuberculatum	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO1006	Ipomoea asarifolia	Species	Convolvulaceae	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	5

Activity Type	# Activity
Individual Protein	2
NON-MOLECULAR	2
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	62000.0	nM	PMID[453877]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	4000.0	nM	PMID[453877]
NPT840	Individual Protein	Transcriptional activator Myb	Gallus gallus	IC50	=	21379.62	nM	PMID[453878]
NPT27	Others	Unspecified		IC50	>	30000.0	nM	PMID[453878]
NPT840	Individual Protein	Transcriptional activator Myb	Gallus gallus	IC50	=	21360.0	nM	PMID[453878]

☑ 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 NPC171759 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	258
0.1-0.2	1592
0.2-0.3	5731
0.3-0.4	10561
0.4-0.5	12592
0.5-0.6	6938
0.6-0.7	4037
0.7-0.8	819
0.8-0.85	97
0.85-0.9	51
0.9-0.95	17
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.957	High Similarity	NPC142529
0.957	High Similarity	NPC126156
0.957	High Similarity	NPC91771
0.9468	High Similarity	NPC170143
0.9468	High Similarity	NPC108475
0.9468	High Similarity	NPC213947
0.9362	High Similarity	NPC24956
0.9362	High Similarity	NPC18019
0.9247	High Similarity	NPC200237
0.914	High Similarity	NPC191339
0.914	High Similarity	NPC286341
0.9043	High Similarity	NPC473234
0.9043	High Similarity	NPC60386
0.9043	High Similarity	NPC473263
0.9043	High Similarity	NPC473273
0.9043	High Similarity	NPC308656
0.9043	High Similarity	NPC153590
0.9032	High Similarity	NPC54065
0.9032	High Similarity	NPC297474
0.8947	High Similarity	NPC473331
0.8936	High Similarity	NPC171360
0.8936	High Similarity	NPC133888
0.8936	High Similarity	NPC293001
0.8936	High Similarity	NPC63193
0.8936	High Similarity	NPC57304
0.8936	High Similarity	NPC475925
0.8936	High Similarity	NPC35959
0.8936	High Similarity	NPC29821
0.8925	High Similarity	NPC12872
0.8925	High Similarity	NPC168679
0.8925	High Similarity	NPC155935
0.89	High Similarity	NPC203659
0.8866	High Similarity	NPC311904
0.883	High Similarity	NPC19087
0.883	High Similarity	NPC35809
0.88	High Similarity	NPC110989
0.8788	High Similarity	NPC477950
0.8776	High Similarity	NPC141191
0.8737	High Similarity	NPC184063
0.8723	High Similarity	NPC38392
0.87	High Similarity	NPC225353
0.8673	High Similarity	NPC477949
0.8673	High Similarity	NPC169205
0.866	High Similarity	NPC48803
0.866	High Similarity	NPC193645
0.866	High Similarity	NPC163228
0.866	High Similarity	NPC275960
0.866	High Similarity	NPC90121
0.8627	High Similarity	NPC54737
0.8617	High Similarity	NPC217983
0.8617	High Similarity	NPC207114
0.8602	High Similarity	NPC238593
0.8602	High Similarity	NPC56593
0.8602	High Similarity	NPC64153
0.8571	High Similarity	NPC185553
0.8529	High Similarity	NPC100487
0.8526	High Similarity	NPC215556
0.8511	High Similarity	NPC201658
0.8511	High Similarity	NPC24728
0.8511	High Similarity	NPC118601
0.8485	Intermediate Similarity	NPC161493
0.8485	Intermediate Similarity	NPC471150
0.8469	Intermediate Similarity	NPC67584
0.8469	Intermediate Similarity	NPC52044
0.8469	Intermediate Similarity	NPC476053
0.8469	Intermediate Similarity	NPC213698
0.8454	Intermediate Similarity	NPC135776
0.8438	Intermediate Similarity	NPC216284
0.8431	Intermediate Similarity	NPC475945
0.8431	Intermediate Similarity	NPC475871
0.8421	Intermediate Similarity	NPC79549
0.8421	Intermediate Similarity	NPC178875
0.8421	Intermediate Similarity	NPC471149
0.8416	Intermediate Similarity	NPC150923
0.8404	Intermediate Similarity	NPC187661
0.8404	Intermediate Similarity	NPC236692
0.8404	Intermediate Similarity	NPC304558
0.8404	Intermediate Similarity	NPC309757
0.8384	Intermediate Similarity	NPC213078
0.8381	Intermediate Similarity	NPC139838
0.8381	Intermediate Similarity	NPC59489
0.8367	Intermediate Similarity	NPC477131
0.8367	Intermediate Similarity	NPC127019
0.8351	Intermediate Similarity	NPC74103
0.8351	Intermediate Similarity	NPC150978
0.8351	Intermediate Similarity	NPC70595
0.8351	Intermediate Similarity	NPC123177
0.8351	Intermediate Similarity	NPC221282
0.8351	Intermediate Similarity	NPC284185
0.8333	Intermediate Similarity	NPC474747
0.8333	Intermediate Similarity	NPC283409
0.8317	Intermediate Similarity	NPC280963
0.83	Intermediate Similarity	NPC474313
0.8283	Intermediate Similarity	NPC304886
0.8283	Intermediate Similarity	NPC170120
0.8283	Intermediate Similarity	NPC472873
0.828	Intermediate Similarity	NPC54468
0.8269	Intermediate Similarity	NPC243998
0.8247	Intermediate Similarity	NPC106510
0.8247	Intermediate Similarity	NPC253144
0.8247	Intermediate Similarity	NPC71533
0.8235	Intermediate Similarity	NPC474742
0.8235	Intermediate Similarity	NPC475099
0.82	Intermediate Similarity	NPC476009
0.8191	Intermediate Similarity	NPC224386
0.8191	Intermediate Similarity	NPC194859
0.819	Intermediate Similarity	NPC26617
0.8182	Intermediate Similarity	NPC198853
0.8182	Intermediate Similarity	NPC262133
0.8182	Intermediate Similarity	NPC470013
0.8182	Intermediate Similarity	NPC167219
0.8182	Intermediate Similarity	NPC470010
0.8182	Intermediate Similarity	NPC323008
0.8173	Intermediate Similarity	NPC474741
0.8173	Intermediate Similarity	NPC309190
0.8172	Intermediate Similarity	NPC246076
0.8165	Intermediate Similarity	NPC471380
0.8163	Intermediate Similarity	NPC131209
0.8163	Intermediate Similarity	NPC155215
0.8163	Intermediate Similarity	NPC133698
0.8144	Intermediate Similarity	NPC295312
0.8144	Intermediate Similarity	NPC117405
0.8144	Intermediate Similarity	NPC32922
0.8144	Intermediate Similarity	NPC52198
0.8137	Intermediate Similarity	NPC186861
0.8137	Intermediate Similarity	NPC471381
0.8131	Intermediate Similarity	NPC257240
0.8131	Intermediate Similarity	NPC477103
0.8105	Intermediate Similarity	NPC284534
0.8105	Intermediate Similarity	NPC300082
0.8105	Intermediate Similarity	NPC204105
0.81	Intermediate Similarity	NPC475900
0.81	Intermediate Similarity	NPC469873
0.81	Intermediate Similarity	NPC37408
0.8095	Intermediate Similarity	NPC223450
0.8085	Intermediate Similarity	NPC128246
0.8085	Intermediate Similarity	NPC111409
0.8081	Intermediate Similarity	NPC258216
0.8077	Intermediate Similarity	NPC474775
0.8073	Intermediate Similarity	NPC209058
0.8061	Intermediate Similarity	NPC37607
0.8061	Intermediate Similarity	NPC129419
0.8061	Intermediate Similarity	NPC301969
0.8058	Intermediate Similarity	NPC201718
0.8056	Intermediate Similarity	NPC474750
0.8039	Intermediate Similarity	NPC54843
0.8039	Intermediate Similarity	NPC221615
0.8037	Intermediate Similarity	NPC477102
0.8021	Intermediate Similarity	NPC470242
0.8018	Intermediate Similarity	NPC475305
0.8	Intermediate Similarity	NPC90453
0.8	Intermediate Similarity	NPC144625
0.7982	Intermediate Similarity	NPC123855
0.7982	Intermediate Similarity	NPC76550
0.7981	Intermediate Similarity	NPC86077
0.798	Intermediate Similarity	NPC261607
0.798	Intermediate Similarity	NPC111114
0.798	Intermediate Similarity	NPC300312
0.798	Intermediate Similarity	NPC290651
0.7961	Intermediate Similarity	NPC288876
0.7959	Intermediate Similarity	NPC268298
0.7959	Intermediate Similarity	NPC472872
0.7957	Intermediate Similarity	NPC73052
0.7957	Intermediate Similarity	NPC51507
0.7957	Intermediate Similarity	NPC6823
0.7957	Intermediate Similarity	NPC290508
0.7957	Intermediate Similarity	NPC293418
0.7946	Intermediate Similarity	NPC161060
0.7946	Intermediate Similarity	NPC475401
0.7946	Intermediate Similarity	NPC475372
0.7938	Intermediate Similarity	NPC270270
0.7928	Intermediate Similarity	NPC255450
0.7928	Intermediate Similarity	NPC170692
0.7925	Intermediate Similarity	NPC44004
0.7925	Intermediate Similarity	NPC179891
0.7925	Intermediate Similarity	NPC291643
0.7921	Intermediate Similarity	NPC471142
0.7909	Intermediate Similarity	NPC46269
0.7909	Intermediate Similarity	NPC106395
0.7905	Intermediate Similarity	NPC475873
0.7905	Intermediate Similarity	NPC472755
0.79	Intermediate Similarity	NPC81419
0.79	Intermediate Similarity	NPC179746
0.79	Intermediate Similarity	NPC475912
0.79	Intermediate Similarity	NPC475788
0.7895	Intermediate Similarity	NPC245665
0.789	Intermediate Similarity	NPC287311
0.7885	Intermediate Similarity	NPC472753
0.7885	Intermediate Similarity	NPC116139
0.7881	Intermediate Similarity	NPC13071
0.7879	Intermediate Similarity	NPC62815
0.7876	Intermediate Similarity	NPC477092
0.7876	Intermediate Similarity	NPC312536
0.7872	Intermediate Similarity	NPC126248
0.787	Intermediate Similarity	NPC474243
0.7864	Intermediate Similarity	NPC222011
0.7857	Intermediate Similarity	NPC473656
0.7857	Intermediate Similarity	NPC91248
0.7857	Intermediate Similarity	NPC202672
0.7857	Intermediate Similarity	NPC36754

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 NPC171759 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	276
0.1-0.2	2316
0.2-0.3	3811
0.3-0.4	1860
0.4-0.5	518
0.5-0.6	251
0.6-0.7	103
0.7-0.8	13
0.8-0.85	1
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.866	High Similarity	NPD1698	Clinical (unspecified phase)
0.819	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.8131	Intermediate Similarity	NPD6371	Approved
0.8061	Intermediate Similarity	NPD5785	Approved
0.76	Intermediate Similarity	NPD1695	Approved
0.7551	Intermediate Similarity	NPD5363	Approved
0.75	Intermediate Similarity	NPD6053	Discontinued
0.7475	Intermediate Similarity	NPD5786	Approved
0.7308	Intermediate Similarity	NPD5282	Discontinued
0.73	Intermediate Similarity	NPD4249	Approved
0.7245	Intermediate Similarity	NPD4269	Approved
0.7245	Intermediate Similarity	NPD6435	Approved
0.7245	Intermediate Similarity	NPD4270	Approved
0.7228	Intermediate Similarity	NPD4251	Approved
0.7228	Intermediate Similarity	NPD4250	Approved
0.7143	Intermediate Similarity	NPD5369	Approved
0.7117	Intermediate Similarity	NPD6008	Approved
0.7041	Intermediate Similarity	NPD4252	Approved
0.7041	Intermediate Similarity	NPD5368	Approved
0.7037	Intermediate Similarity	NPD7638	Approved
0.7037	Intermediate Similarity	NPD4225	Approved
0.703	Intermediate Similarity	NPD6082	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD46	Approved
0.7019	Intermediate Similarity	NPD6698	Approved
0.7	Intermediate Similarity	NPD5362	Discontinued
0.6972	Remote Similarity	NPD7639	Approved
0.6972	Remote Similarity	NPD7640	Approved
0.6967	Remote Similarity	NPD7492	Approved
0.6952	Remote Similarity	NPD7983	Approved
0.6917	Remote Similarity	NPD6319	Approved
0.6917	Remote Similarity	NPD6054	Approved
0.6911	Remote Similarity	NPD6616	Approved
0.6903	Remote Similarity	NPD5697	Approved
0.6887	Remote Similarity	NPD5778	Approved
0.6887	Remote Similarity	NPD5779	Approved
0.688	Remote Similarity	NPD7319	Approved
0.6869	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.686	Remote Similarity	NPD6016	Approved
0.686	Remote Similarity	NPD6015	Approved
0.6855	Remote Similarity	NPD7078	Approved
0.6842	Remote Similarity	NPD7320	Approved
0.6842	Remote Similarity	NPD6686	Approved
0.6842	Remote Similarity	NPD6881	Approved
0.6842	Remote Similarity	NPD6899	Approved
0.6814	Remote Similarity	NPD5739	Approved
0.6814	Remote Similarity	NPD6402	Approved
0.6814	Remote Similarity	NPD6675	Approved
0.6814	Remote Similarity	NPD7128	Approved
0.681	Remote Similarity	NPD6650	Approved
0.681	Remote Similarity	NPD6649	Approved
0.6807	Remote Similarity	NPD7115	Discovery
0.6803	Remote Similarity	NPD5988	Approved
0.6803	Remote Similarity	NPD6370	Approved
0.68	Remote Similarity	NPD7736	Approved
0.6783	Remote Similarity	NPD6373	Approved
0.6783	Remote Similarity	NPD6012	Approved
0.6783	Remote Similarity	NPD6372	Approved
0.6783	Remote Similarity	NPD6013	Approved
0.6783	Remote Similarity	NPD6014	Approved
0.6777	Remote Similarity	NPD6059	Approved
0.6774	Remote Similarity	NPD7507	Approved
0.6754	Remote Similarity	NPD5701	Approved
0.6733	Remote Similarity	NPD5209	Approved
0.6724	Remote Similarity	NPD6883	Approved
0.6724	Remote Similarity	NPD7102	Approved
0.6724	Remote Similarity	NPD7290	Approved
0.672	Remote Similarity	NPD8293	Discontinued
0.67	Remote Similarity	NPD4819	Approved
0.67	Remote Similarity	NPD4822	Approved
0.67	Remote Similarity	NPD4820	Approved
0.67	Remote Similarity	NPD4821	Approved
0.6699	Remote Similarity	NPD1694	Approved
0.6698	Remote Similarity	NPD7838	Discovery
0.6696	Remote Similarity	NPD6011	Approved
0.6695	Remote Similarity	NPD4632	Approved
0.6667	Remote Similarity	NPD4271	Approved
0.6667	Remote Similarity	NPD8130	Phase 1
0.6667	Remote Similarity	NPD6847	Approved
0.6667	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4268	Approved
0.6667	Remote Similarity	NPD7154	Phase 3
0.6667	Remote Similarity	NPD6617	Approved
0.6667	Remote Similarity	NPD6869	Approved
0.6636	Remote Similarity	NPD6084	Phase 2
0.6636	Remote Similarity	NPD7637	Suspended
0.6636	Remote Similarity	NPD6411	Approved
0.6636	Remote Similarity	NPD6083	Phase 2
0.661	Remote Similarity	NPD8297	Approved
0.661	Remote Similarity	NPD6882	Approved
0.6609	Remote Similarity	NPD6412	Phase 2
0.6606	Remote Similarity	NPD5695	Phase 3
0.6581	Remote Similarity	NPD4634	Approved
0.6577	Remote Similarity	NPD5696	Approved
0.6574	Remote Similarity	NPD6399	Phase 3
0.6569	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6549	Remote Similarity	NPD5211	Phase 2
0.6529	Remote Similarity	NPD6009	Approved
0.6518	Remote Similarity	NPD5285	Approved
0.6518	Remote Similarity	NPD4696	Approved
0.6518	Remote Similarity	NPD5286	Approved
0.6509	Remote Similarity	NPD6903	Approved
0.6505	Remote Similarity	NPD5331	Approved
0.6505	Remote Similarity	NPD5332	Approved
0.6486	Remote Similarity	NPD4755	Approved
0.6476	Remote Similarity	NPD7146	Approved
0.6476	Remote Similarity	NPD5330	Approved
0.6476	Remote Similarity	NPD6684	Approved
0.6476	Remote Similarity	NPD7521	Approved
0.6476	Remote Similarity	NPD7334	Approved
0.6476	Remote Similarity	NPD6409	Approved
0.6471	Remote Similarity	NPD4790	Discontinued
0.6452	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD5983	Phase 2
0.6449	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6449	Remote Similarity	NPD6101	Approved
0.6446	Remote Similarity	NPD6274	Approved
0.6442	Remote Similarity	NPD3133	Approved
0.6442	Remote Similarity	NPD3665	Phase 1
0.6442	Remote Similarity	NPD3666	Approved
0.6435	Remote Similarity	NPD5141	Approved
0.6404	Remote Similarity	NPD7632	Discontinued
0.6404	Remote Similarity	NPD5224	Approved
0.6404	Remote Similarity	NPD5225	Approved
0.6404	Remote Similarity	NPD4633	Approved
0.6404	Remote Similarity	NPD5226	Approved
0.6396	Remote Similarity	NPD7839	Suspended
0.6387	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6385	Remote Similarity	NPD7260	Phase 2
0.6372	Remote Similarity	NPD4700	Approved
0.6355	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6349	Remote Similarity	NPD7604	Phase 2
0.6348	Remote Similarity	NPD5175	Approved
0.6348	Remote Similarity	NPD5174	Approved
0.6336	Remote Similarity	NPD6845	Suspended
0.633	Remote Similarity	NPD5284	Approved
0.633	Remote Similarity	NPD5281	Approved
0.633	Remote Similarity	NPD5693	Phase 1
0.632	Remote Similarity	NPD8516	Approved
0.632	Remote Similarity	NPD8513	Phase 3
0.632	Remote Similarity	NPD8515	Approved
0.632	Remote Similarity	NPD8517	Approved
0.6316	Remote Similarity	NPD5223	Approved
0.6306	Remote Similarity	NPD5210	Approved
0.6306	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6306	Remote Similarity	NPD4629	Approved
0.6296	Remote Similarity	NPD4753	Phase 2
0.629	Remote Similarity	NPD7100	Approved
0.629	Remote Similarity	NPD7101	Approved
0.6283	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6279	Remote Similarity	NPD6033	Approved
0.626	Remote Similarity	NPD6317	Approved
0.625	Remote Similarity	NPD6336	Discontinued
0.625	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6239	Remote Similarity	NPD5207	Approved
0.6218	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.621	Remote Similarity	NPD6335	Approved
0.621	Remote Similarity	NPD6313	Approved
0.621	Remote Similarity	NPD6314	Approved
0.621	Remote Similarity	NPD7328	Approved
0.621	Remote Similarity	NPD7327	Approved
0.619	Remote Similarity	NPD8033	Approved
0.6183	Remote Similarity	NPD5956	Approved
0.6182	Remote Similarity	NPD6079	Approved
0.6176	Remote Similarity	NPD4802	Phase 2
0.6176	Remote Similarity	NPD4238	Approved
0.6174	Remote Similarity	NPD5344	Discontinued
0.6168	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6168	Remote Similarity	NPD3618	Phase 1
0.6167	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.616	Remote Similarity	NPD7516	Approved
0.6154	Remote Similarity	NPD4056	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD4057	Clinical (unspecified phase)
0.6147	Remote Similarity	NPD5370	Suspended
0.6147	Remote Similarity	NPD5328	Approved
0.6134	Remote Similarity	NPD5128	Approved
0.6134	Remote Similarity	NPD4730	Approved
0.6134	Remote Similarity	NPD4729	Approved
0.6126	Remote Similarity	NPD4202	Approved
0.6111	Remote Similarity	NPD8377	Approved
0.6111	Remote Similarity	NPD8294	Approved
0.6106	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6106	Remote Similarity	NPD5222	Approved
0.6106	Remote Similarity	NPD5221	Approved
0.6106	Remote Similarity	NPD4697	Phase 3
0.6103	Remote Similarity	NPD6333	Approved
0.6103	Remote Similarity	NPD6334	Approved
0.6102	Remote Similarity	NPD4767	Approved
0.6102	Remote Similarity	NPD4768	Approved
0.6095	Remote Similarity	NPD3667	Approved
0.6094	Remote Similarity	NPD7642	Approved
0.6094	Remote Similarity	NPD8328	Phase 3
0.6077	Remote Similarity	NPD8074	Phase 3
0.6071	Remote Similarity	NPD6001	Approved
0.6068	Remote Similarity	NPD4754	Approved
0.6063	Remote Similarity	NPD6909	Approved
0.6063	Remote Similarity	NPD8378	Approved
0.6063	Remote Similarity	NPD8267	Approved
0.6063	Remote Similarity	NPD8380	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