NPASS Compound

Structure

CID24956 OpenBabel06191715352D 26 28 0 0 1 0 0 0 0 0999 V2000 -7.4187 -2.2629 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6040 -1.4222 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0533 1.5932 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2704 -2.5734 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0324 -1.2190 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6010 -2.8385 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6195 0.6922 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6320 -0.9195 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6936 -2.4182 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6195 0.6922 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.3600 -1.5775 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2389 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9960 -0.0896 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.8789 -1.5775 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.2185 -1.0646 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.2430 -0.0896 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.1195 -1.4985 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.8759 -2.9938 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3930 -0.9195 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0204 -1.0646 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.7518 0.8584 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1195 -2.4985 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.9655 -3.9898 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3680 -1.1420 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 -3.9685 -2.5734 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 6 0 0 0 14 26 1 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 22 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:	364.19
Volume:	371.002
LogP:	1.616
LogD:	1.686
LogS:	-2.593
# Rotatable Bonds:	3
TPSA:	93.06
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.573
Synthetic Accessibility Score:	4.892
Fsp3:	0.7
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:	-4.909
MDCK Permeability:	3.819495395873673e-05
Pgp-inhibitor:	0.014
Pgp-substrate:	0.005
Human Intestinal Absorption (HIA):	0.038
20% Bioavailability (F20%):	0.215
30% Bioavailability (F30%):	0.967

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.298
Plasma Protein Binding (PPB):	60.360050201416016%
Volume Distribution (VD):	0.98
Pgp-substrate:	27.910804748535156%

ADMET: Metabolism

CYP1A2-inhibitor:	0.18
CYP1A2-substrate:	0.124
CYP2C19-inhibitor:	0.087
CYP2C19-substrate:	0.501
CYP2C9-inhibitor:	0.493
CYP2C9-substrate:	0.091
CYP2D6-inhibitor:	0.012
CYP2D6-substrate:	0.087
CYP3A4-inhibitor:	0.474
CYP3A4-substrate:	0.269

ADMET: Excretion

Clearance (CL):	9.395
Half-life (T1/2):	0.892

ADMET: Toxicity

hERG Blockers:	0.079
Human Hepatotoxicity (H-HT):	0.607
Drug-inuced Liver Injury (DILI):	0.304
AMES Toxicity:	0.016
Rat Oral Acute Toxicity:	0.724
Maximum Recommended Daily Dose:	0.34
Skin Sensitization:	0.67
Carcinogencity:	0.118
Eye Corrosion:	0.073
Eye Irritation:	0.147
Respiratory Toxicity:	0.939

Download Data

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

Natural Product: NPC24956

Natural Product ID:	NPC24956
*Common Name:**	Deacetyl-4-O-Tigloylchamissonolide
IUPAC Name:	[(3aR,5R,5aS,6S,8R,8aR,9S,9aS)-6,9-dihydroxy-5,8a-dimethyl-1-methylidene-2-oxo-4,5,5a,6,7,8,9,9a-octahydro-3aH-azuleno[6,7-b]furan-8-yl] (E)-2-methylbut-2-enoate
Synonyms:
Standard InCHIKey:	WUMRXBPDXGXSJC-JYJHRMTHSA-N
Standard InCHI:	InChI=1S/C20H28O6/c1-6-9(2)18(23)26-14-8-12(21)16-10(3)7-13-15(11(4)19(24)25-13)17(22)20(14,16)5/h6,10,12-17,21-22H,4,7-8H2,1-3,5H3/b9-6+/t10-,12+,13-,14-,15-,16-,17+,20-/m1/s1
SMILES:	C/C=C(/C(=O)O[C@@H]1C[C@@H]([C@@H]2[C@]1(C)[C@@H](O)[C@H]1[C@@H](C[C@H]2C)OC(=O)C1=C)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL453279
PubChem CID:	44559337
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]
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]
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]

☑ 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	=	116000.0	nM	PMID[526253]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	10400.0	nM	PMID[526253]
NPT840	Individual Protein	Transcriptional activator Myb	Gallus gallus	IC50	=	29853.83	nM	PMID[526254]
NPT27	Others	Unspecified		IC50	>	30000.0	nM	PMID[526254]
NPT840	Individual Protein	Transcriptional activator Myb	Gallus gallus	IC50	=	29870.0	nM	PMID[526254]

☑ 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 NPC24956 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	245
0.1-0.2	1505
0.2-0.3	5601
0.3-0.4	13647
0.4-0.5	9735
0.5-0.6	7330
0.6-0.7	3648
0.7-0.8	836
0.8-0.85	71
0.85-0.9	47
0.9-0.95	19
0.95-1	13

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC18019
0.9551	High Similarity	NPC171360
0.9551	High Similarity	NPC293001
0.9551	High Similarity	NPC133888
0.9551	High Similarity	NPC63193
0.9551	High Similarity	NPC57304
0.9551	High Similarity	NPC35959
0.9551	High Similarity	NPC29821
0.9438	High Similarity	NPC297474
0.9438	High Similarity	NPC35809
0.9438	High Similarity	NPC54065
0.9362	High Similarity	NPC171759
0.9333	High Similarity	NPC475925
0.9326	High Similarity	NPC155935
0.9101	High Similarity	NPC24728
0.9043	High Similarity	NPC213947
0.9043	High Similarity	NPC170143
0.9043	High Similarity	NPC161493
0.9043	High Similarity	NPC108475
0.9032	High Similarity	NPC213698
0.9011	High Similarity	NPC216284
0.9	High Similarity	NPC217983
0.9	High Similarity	NPC471149
0.9	High Similarity	NPC207114
0.8989	High Similarity	NPC56593
0.8989	High Similarity	NPC64153
0.8936	High Similarity	NPC142529
0.8936	High Similarity	NPC126156
0.8936	High Similarity	NPC91771
0.8936	High Similarity	NPC213078
0.8925	High Similarity	NPC127019
0.8901	High Similarity	NPC215556
0.8901	High Similarity	NPC283409
0.883	High Similarity	NPC52044
0.883	High Similarity	NPC170120
0.883	High Similarity	NPC67584
0.883	High Similarity	NPC472873
0.8804	High Similarity	NPC19087
0.8791	High Similarity	NPC79549
0.8788	High Similarity	NPC54737
0.8778	High Similarity	NPC187661
0.8763	High Similarity	NPC150923
0.8723	High Similarity	NPC477131
0.871	High Similarity	NPC184063
0.871	High Similarity	NPC155215
0.8696	High Similarity	NPC38392
0.8646	High Similarity	NPC311904
0.8646	High Similarity	NPC471150
0.8632	High Similarity	NPC476053
0.8632	High Similarity	NPC304886
0.8617	High Similarity	NPC473263
0.8617	High Similarity	NPC200237
0.8617	High Similarity	NPC473234
0.8617	High Similarity	NPC473273
0.8617	High Similarity	NPC60386
0.8617	High Similarity	NPC308656
0.8617	High Similarity	NPC258216
0.8557	High Similarity	NPC221615
0.8556	High Similarity	NPC224386
0.8556	High Similarity	NPC194859
0.8539	High Similarity	NPC246076
0.8529	High Similarity	NPC59489
0.8529	High Similarity	NPC139838
0.8526	High Similarity	NPC470013
0.8526	High Similarity	NPC473331
0.8526	High Similarity	NPC262133
0.8526	High Similarity	NPC323008
0.8526	High Similarity	NPC470010
0.8526	High Similarity	NPC198853
0.8511	High Similarity	NPC133698
0.8511	High Similarity	NPC191339
0.8511	High Similarity	NPC131209
0.8511	High Similarity	NPC286341
0.8495	Intermediate Similarity	NPC472872
0.8462	Intermediate Similarity	NPC300082
0.8462	Intermediate Similarity	NPC204105
0.8462	Intermediate Similarity	NPC284534
0.8454	Intermediate Similarity	NPC477949
0.8444	Intermediate Similarity	NPC111409
0.8444	Intermediate Similarity	NPC128246
0.8438	Intermediate Similarity	NPC163228
0.8421	Intermediate Similarity	NPC153590
0.8404	Intermediate Similarity	NPC37607
0.8404	Intermediate Similarity	NPC301969
0.8384	Intermediate Similarity	NPC477950
0.837	Intermediate Similarity	NPC304558
0.8317	Intermediate Similarity	NPC203659
0.83	Intermediate Similarity	NPC86077
0.8298	Intermediate Similarity	NPC12872
0.8298	Intermediate Similarity	NPC168679
0.8283	Intermediate Similarity	NPC471381
0.8283	Intermediate Similarity	NPC186861
0.828	Intermediate Similarity	NPC201658
0.828	Intermediate Similarity	NPC118601
0.8265	Intermediate Similarity	NPC474313
0.8247	Intermediate Similarity	NPC37408
0.8242	Intermediate Similarity	NPC245665
0.8235	Intermediate Similarity	NPC243998
0.8229	Intermediate Similarity	NPC135776
0.8222	Intermediate Similarity	NPC126248
0.8218	Intermediate Similarity	NPC110989
0.8208	Intermediate Similarity	NPC273242
0.8191	Intermediate Similarity	NPC178875
0.8191	Intermediate Similarity	NPC91248
0.8182	Intermediate Similarity	NPC45125
0.8182	Intermediate Similarity	NPC141191
0.8172	Intermediate Similarity	NPC236692
0.8172	Intermediate Similarity	NPC309757
0.8172	Intermediate Similarity	NPC67493
0.8155	Intermediate Similarity	NPC26617
0.8131	Intermediate Similarity	NPC471380
0.8131	Intermediate Similarity	NPC121816
0.8125	Intermediate Similarity	NPC221282
0.8119	Intermediate Similarity	NPC225353
0.8105	Intermediate Similarity	NPC295312
0.81	Intermediate Similarity	NPC70865
0.81	Intermediate Similarity	NPC47024
0.8081	Intermediate Similarity	NPC181151
0.8081	Intermediate Similarity	NPC169205
0.8073	Intermediate Similarity	NPC161060
0.8065	Intermediate Similarity	NPC235792
0.8061	Intermediate Similarity	NPC193645
0.8061	Intermediate Similarity	NPC90121
0.8061	Intermediate Similarity	NPC48803
0.8061	Intermediate Similarity	NPC275960
0.8061	Intermediate Similarity	NPC469873
0.8058	Intermediate Similarity	NPC166115
0.8058	Intermediate Similarity	NPC223450
0.8056	Intermediate Similarity	NPC170692
0.8056	Intermediate Similarity	NPC255450
0.8043	Intermediate Similarity	NPC54468
0.8041	Intermediate Similarity	NPC475838
0.8041	Intermediate Similarity	NPC228451
0.8041	Intermediate Similarity	NPC472874
0.8041	Intermediate Similarity	NPC125674
0.8039	Intermediate Similarity	NPC124881
0.8039	Intermediate Similarity	NPC474775
0.8021	Intermediate Similarity	NPC469368
0.8021	Intermediate Similarity	NPC475855
0.8021	Intermediate Similarity	NPC129419
0.8019	Intermediate Similarity	NPC474750
0.8	Intermediate Similarity	NPC249171
0.8	Intermediate Similarity	NPC49833
0.8	Intermediate Similarity	NPC224652
0.7982	Intermediate Similarity	NPC36754
0.798	Intermediate Similarity	NPC185553
0.7979	Intermediate Similarity	NPC470242
0.7979	Intermediate Similarity	NPC107787
0.7979	Intermediate Similarity	NPC305475
0.7979	Intermediate Similarity	NPC475461
0.7979	Intermediate Similarity	NPC238593
0.7963	Intermediate Similarity	NPC471382
0.7961	Intermediate Similarity	NPC100487
0.7959	Intermediate Similarity	NPC474338
0.7959	Intermediate Similarity	NPC167219
0.7959	Intermediate Similarity	NPC90453
0.7959	Intermediate Similarity	NPC474247
0.7957	Intermediate Similarity	NPC156485
0.7938	Intermediate Similarity	NPC290651
0.7935	Intermediate Similarity	NPC89555
0.7925	Intermediate Similarity	NPC257240
0.7921	Intermediate Similarity	NPC280963
0.7917	Intermediate Similarity	NPC212664
0.7917	Intermediate Similarity	NPC4986
0.7917	Intermediate Similarity	NPC268298
0.7917	Intermediate Similarity	NPC32922
0.7912	Intermediate Similarity	NPC258965
0.7912	Intermediate Similarity	NPC156658
0.7909	Intermediate Similarity	NPC475372
0.79	Intermediate Similarity	NPC304445
0.79	Intermediate Similarity	NPC236580
0.7895	Intermediate Similarity	NPC270270
0.7895	Intermediate Similarity	NPC160138
0.7885	Intermediate Similarity	NPC44004
0.7879	Intermediate Similarity	NPC224689
0.7872	Intermediate Similarity	NPC78089
0.7872	Intermediate Similarity	NPC255307
0.7872	Intermediate Similarity	NPC165162
0.787	Intermediate Similarity	NPC209058
0.7864	Intermediate Similarity	NPC475945
0.7864	Intermediate Similarity	NPC221421
0.7864	Intermediate Similarity	NPC473148
0.7864	Intermediate Similarity	NPC475871
0.7857	Intermediate Similarity	NPC179746
0.7857	Intermediate Similarity	NPC475912
0.7857	Intermediate Similarity	NPC475788
0.7857	Intermediate Similarity	NPC81419
0.7838	Intermediate Similarity	NPC312536
0.7835	Intermediate Similarity	NPC179394
0.7835	Intermediate Similarity	NPC144133
0.783	Intermediate Similarity	NPC477102
0.7826	Intermediate Similarity	NPC47635
0.7822	Intermediate Similarity	NPC187268
0.7818	Intermediate Similarity	NPC473656
0.7812	Intermediate Similarity	NPC202672
0.78	Intermediate Similarity	NPC279621
0.78	Intermediate Similarity	NPC230800
0.78	Intermediate Similarity	NPC284518
0.7798	Intermediate Similarity	NPC123117
0.7789	Intermediate Similarity	NPC150755

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 NPC24956 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	254
0.1-0.2	2203
0.2-0.3	3841
0.3-0.4	2026
0.4-0.5	460
0.5-0.6	252
0.6-0.7	101
0.7-0.8	12
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8155	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.8061	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7925	Intermediate Similarity	NPD6371	Approved
0.7917	Intermediate Similarity	NPD1695	Approved
0.7835	Intermediate Similarity	NPD5785	Approved
0.7789	Intermediate Similarity	NPD4249	Approved
0.7708	Intermediate Similarity	NPD4250	Approved
0.7708	Intermediate Similarity	NPD4251	Approved
0.7615	Intermediate Similarity	NPD6053	Discontinued
0.734	Intermediate Similarity	NPD5790	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD5363	Approved
0.732	Intermediate Similarity	NPD6082	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD7638	Approved
0.73	Intermediate Similarity	NPD46	Approved
0.73	Intermediate Similarity	NPD6698	Approved
0.7292	Intermediate Similarity	NPD5362	Discontinued
0.7238	Intermediate Similarity	NPD7640	Approved
0.7238	Intermediate Similarity	NPD7639	Approved
0.7188	Intermediate Similarity	NPD6435	Approved
0.7158	Intermediate Similarity	NPD4821	Approved
0.7158	Intermediate Similarity	NPD4819	Approved
0.7158	Intermediate Similarity	NPD4820	Approved
0.7158	Intermediate Similarity	NPD4822	Approved
0.7128	Intermediate Similarity	NPD4271	Approved
0.7128	Intermediate Similarity	NPD4268	Approved
0.7113	Intermediate Similarity	NPD7154	Phase 3
0.7091	Intermediate Similarity	NPD6686	Approved
0.7087	Intermediate Similarity	NPD5282	Discontinued
0.701	Intermediate Similarity	NPD4269	Approved
0.701	Intermediate Similarity	NPD4270	Approved
0.6981	Remote Similarity	NPD4225	Approved
0.6979	Remote Similarity	NPD5368	Approved
0.6961	Remote Similarity	NPD7838	Discovery
0.6909	Remote Similarity	NPD6008	Approved
0.6907	Remote Similarity	NPD5369	Approved
0.69	Remote Similarity	NPD5786	Approved
0.6837	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6804	Remote Similarity	NPD4252	Approved
0.68	Remote Similarity	NPD1694	Approved
0.68	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6771	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD5332	Approved
0.6768	Remote Similarity	NPD5331	Approved
0.6735	Remote Similarity	NPD4790	Discontinued
0.6729	Remote Similarity	NPD6084	Phase 2
0.6729	Remote Similarity	NPD6083	Phase 2
0.6721	Remote Similarity	NPD7507	Approved
0.6698	Remote Similarity	NPD5695	Phase 3
0.6696	Remote Similarity	NPD6412	Phase 2
0.6696	Remote Similarity	NPD5697	Approved
0.6667	Remote Similarity	NPD5696	Approved
0.6667	Remote Similarity	NPD6399	Phase 3
0.6637	Remote Similarity	NPD6881	Approved
0.6637	Remote Similarity	NPD7320	Approved
0.6637	Remote Similarity	NPD6899	Approved
0.6636	Remote Similarity	NPD7632	Discontinued
0.661	Remote Similarity	NPD7115	Discovery
0.6609	Remote Similarity	NPD6650	Approved
0.6609	Remote Similarity	NPD6649	Approved
0.6607	Remote Similarity	NPD5739	Approved
0.6607	Remote Similarity	NPD6402	Approved
0.6607	Remote Similarity	NPD6675	Approved
0.6607	Remote Similarity	NPD7128	Approved
0.6602	Remote Similarity	NPD6903	Approved
0.6579	Remote Similarity	NPD6013	Approved
0.6579	Remote Similarity	NPD6372	Approved
0.6579	Remote Similarity	NPD6014	Approved
0.6579	Remote Similarity	NPD6012	Approved
0.6579	Remote Similarity	NPD6373	Approved
0.6571	Remote Similarity	NPD7983	Approved
0.6571	Remote Similarity	NPD7637	Suspended
0.6569	Remote Similarity	NPD6409	Approved
0.6569	Remote Similarity	NPD7146	Approved
0.6569	Remote Similarity	NPD5330	Approved
0.6569	Remote Similarity	NPD6684	Approved
0.6569	Remote Similarity	NPD7521	Approved
0.6569	Remote Similarity	NPD7334	Approved
0.656	Remote Similarity	NPD7319	Approved
0.6549	Remote Similarity	NPD5701	Approved
0.6535	Remote Similarity	NPD3666	Approved
0.6535	Remote Similarity	NPD3665	Phase 1
0.6535	Remote Similarity	NPD3133	Approved
0.6529	Remote Similarity	NPD8033	Approved
0.6522	Remote Similarity	NPD7102	Approved
0.6522	Remote Similarity	NPD6883	Approved
0.6522	Remote Similarity	NPD7290	Approved
0.6514	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6509	Remote Similarity	NPD5779	Approved
0.6509	Remote Similarity	NPD5778	Approved
0.6504	Remote Similarity	NPD7492	Approved
0.65	Remote Similarity	NPD5209	Approved
0.6496	Remote Similarity	NPD4632	Approved
0.6491	Remote Similarity	NPD6011	Approved
0.6466	Remote Similarity	NPD8130	Phase 1
0.6466	Remote Similarity	NPD6847	Approved
0.6466	Remote Similarity	NPD6869	Approved
0.6466	Remote Similarity	NPD6617	Approved
0.6466	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD6616	Approved
0.6446	Remote Similarity	NPD6054	Approved
0.6446	Remote Similarity	NPD6319	Approved
0.6442	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6435	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6417	Remote Similarity	NPD7328	Approved
0.6417	Remote Similarity	NPD7327	Approved
0.6415	Remote Similarity	NPD5284	Approved
0.6415	Remote Similarity	NPD5693	Phase 1
0.6415	Remote Similarity	NPD5281	Approved
0.641	Remote Similarity	NPD6882	Approved
0.641	Remote Similarity	NPD8297	Approved
0.64	Remote Similarity	NPD7078	Approved
0.6396	Remote Similarity	NPD5344	Discontinued
0.6393	Remote Similarity	NPD6016	Approved
0.6393	Remote Similarity	NPD6015	Approved
0.6389	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6389	Remote Similarity	NPD4629	Approved
0.6389	Remote Similarity	NPD5210	Approved
0.6381	Remote Similarity	NPD4753	Phase 2
0.6379	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD7516	Approved
0.6349	Remote Similarity	NPD7736	Approved
0.6341	Remote Similarity	NPD6370	Approved
0.6341	Remote Similarity	NPD5988	Approved
0.6339	Remote Similarity	NPD5211	Phase 2
0.6333	Remote Similarity	NPD6009	Approved
0.6321	Remote Similarity	NPD5207	Approved
0.6311	Remote Similarity	NPD8294	Approved
0.6311	Remote Similarity	NPD8377	Approved
0.6311	Remote Similarity	NPD6059	Approved
0.6306	Remote Similarity	NPD5286	Approved
0.6306	Remote Similarity	NPD4696	Approved
0.6306	Remote Similarity	NPD5285	Approved
0.6273	Remote Similarity	NPD4755	Approved
0.627	Remote Similarity	NPD8293	Discontinued
0.6262	Remote Similarity	NPD6411	Approved
0.6262	Remote Similarity	NPD8035	Phase 2
0.6262	Remote Similarity	NPD8034	Phase 2
0.626	Remote Similarity	NPD7503	Approved
0.626	Remote Similarity	NPD8380	Approved
0.626	Remote Similarity	NPD8378	Approved
0.626	Remote Similarity	NPD8296	Approved
0.626	Remote Similarity	NPD5983	Phase 2
0.626	Remote Similarity	NPD8335	Approved
0.626	Remote Similarity	NPD8379	Approved
0.626	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.625	Remote Similarity	NPD3618	Phase 1
0.625	Remote Similarity	NPD6274	Approved
0.625	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6228	Remote Similarity	NPD5141	Approved
0.6218	Remote Similarity	NPD8133	Approved
0.6214	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6214	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6204	Remote Similarity	NPD4202	Approved
0.6202	Remote Similarity	NPD7260	Phase 2
0.6195	Remote Similarity	NPD5226	Approved
0.6195	Remote Similarity	NPD5225	Approved
0.6195	Remote Similarity	NPD5224	Approved
0.6195	Remote Similarity	NPD4633	Approved
0.6186	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6176	Remote Similarity	NPD3667	Approved
0.6161	Remote Similarity	NPD4700	Approved
0.6161	Remote Similarity	NPD6648	Approved
0.616	Remote Similarity	NPD7604	Phase 2
0.6154	Remote Similarity	NPD6845	Suspended
0.6147	Remote Similarity	NPD6001	Approved
0.614	Remote Similarity	NPD5175	Approved
0.614	Remote Similarity	NPD5174	Approved
0.6132	Remote Similarity	NPD5737	Approved
0.6132	Remote Similarity	NPD6672	Approved
0.6126	Remote Similarity	NPD7902	Approved
0.6121	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6121	Remote Similarity	NPD6685	Approved
0.6117	Remote Similarity	NPD6695	Phase 3
0.6117	Remote Similarity	NPD4788	Approved
0.6106	Remote Similarity	NPD5223	Approved
0.6102	Remote Similarity	NPD4634	Approved
0.6098	Remote Similarity	NPD7101	Approved
0.6098	Remote Similarity	NPD7100	Approved
0.6095	Remote Similarity	NPD5279	Phase 3
0.6075	Remote Similarity	NPD6101	Approved
0.6075	Remote Similarity	NPD6080	Approved
0.6075	Remote Similarity	NPD6904	Approved
0.6075	Remote Similarity	NPD6051	Approved
0.6075	Remote Similarity	NPD6673	Approved
0.6075	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6068	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6066	Remote Similarity	NPD6317	Approved
0.6063	Remote Similarity	NPD6336	Discontinued
0.6058	Remote Similarity	NPD4786	Approved
0.6036	Remote Similarity	NPD7839	Suspended
0.6032	Remote Similarity	NPD6067	Discontinued
0.6019	Remote Similarity	NPD4223	Phase 3
0.6019	Remote Similarity	NPD4221	Approved
0.6019	Remote Similarity	NPD5692	Phase 3
0.6016	Remote Similarity	NPD6313	Approved
0.6016	Remote Similarity	NPD6335	Approved
0.6016	Remote Similarity	NPD6314	Approved
0.6	Remote Similarity	NPD8516	Approved
0.6	Remote Similarity	NPD8515	Approved
0.6	Remote Similarity	NPD8517	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