NPASS Compound

Structure

CID198853 OpenBabel06191715582D 22 24 0 0 1 0 0 0 0 0999 V2000 -1.4586 1.3465 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4546 -2.4237 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3272 -2.2213 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0096 -4.9901 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0341 0.5138 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3288 -0.4417 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7782 -2.6635 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0342 0.5288 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5410 -2.0169 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6581 -1.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5903 -4.1899 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7971 -2.4703 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.3364 -1.5827 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7110 -0.4175 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.7431 -0.6691 0.0000 C 0 0 1 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 -2.5111 -1.0174 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.5831 -4.3093 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7796 -0.0933 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2504 -1.9828 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1972 -3.2704 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 1 8 1 0 0 0 0 2 9 2 0 0 0 0 3 10 2 0 0 0 0 4 11 1 0 0 0 0 5 6 1 0 0 0 0 5 8 2 0 0 0 0 6 17 1 0 0 0 0 7 9 1 0 0 0 0 7 12 1 0 0 0 0 8 14 1 0 0 0 0 9 17 1 0 0 0 0 10 16 1 0 0 0 0 11 18 2 0 0 0 0 11 21 1 0 0 0 0 12 13 1 0 0 0 0 12 21 1 1 0 0 0 13 10 1 6 0 0 0 13 15 1 0 0 0 0 14 15 1 0 0 0 0 14 17 1 6 0 0 0 15 22 1 1 0 0 0 16 19 2 0 0 0 0 16 22 1 0 0 0 0 17 20 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	304.13
Volume:	307.688
LogP:	1.521
LogD:	1.413
LogS:	-3.046
# Rotatable Bonds:	2
TPSA:	72.83
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.453
Synthetic Accessibility Score:	4.795
Fsp3:	0.529
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:	-4.892
MDCK Permeability:	0.00010749335342552513
Pgp-inhibitor:	0.0
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.865
20% Bioavailability (F20%):	0.962
30% Bioavailability (F30%):	0.986

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.54
Plasma Protein Binding (PPB):	34.45560073852539%
Volume Distribution (VD):	0.857
Pgp-substrate:	57.452728271484375%

ADMET: Metabolism

CYP1A2-inhibitor:	0.097
CYP1A2-substrate:	0.072
CYP2C19-inhibitor:	0.024
CYP2C19-substrate:	0.262
CYP2C9-inhibitor:	0.016
CYP2C9-substrate:	0.041
CYP2D6-inhibitor:	0.031
CYP2D6-substrate:	0.107
CYP3A4-inhibitor:	0.118
CYP3A4-substrate:	0.243

ADMET: Excretion

Clearance (CL):	8.403
Half-life (T1/2):	0.131

ADMET: Toxicity

hERG Blockers:	0.016
Human Hepatotoxicity (H-HT):	0.742
Drug-inuced Liver Injury (DILI):	0.345
AMES Toxicity:	0.042
Rat Oral Acute Toxicity:	0.912
Maximum Recommended Daily Dose:	0.099
Skin Sensitization:	0.42
Carcinogencity:	0.205
Eye Corrosion:	0.497
Eye Irritation:	0.339
Respiratory Toxicity:	0.983

Download Data

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

Natural Product: NPC198853

Natural Product ID:	NPC198853
*Common Name:**	Rupicolin A-8-O-Acetate
IUPAC Name:	[(3aR,4S,6aS,9aR,9bS)-6a-hydroxy-9-methyl-3,6-dimethylidene-2-oxo-3a,4,5,7,9a,9b-hexahydroazuleno[4,5-b]furan-4-yl] acetate
Synonyms:
Standard InCHIKey:	YFKYWMBSLLLPGV-SOXILONMSA-N
Standard InCHI:	InChI=1S/C17H20O5/c1-8-5-6-17(20)9(2)7-12(21-11(4)18)13-10(3)16(19)22-15(13)14(8)17/h5,12-15,20H,2-3,6-7H2,1,4H3/t12-,13+,14+,15-,17+/m0/s1
SMILES:	CC1=CC[C@]2(C(=C)C[C@@H]([C@H]3C(=C)C(=O)O[C@@H]3[C@@H]12)OC(=O)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1172949
PubChem CID:	49799784
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 [CHEMONTID:0001770] Guaianolides and derivatives

*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
NPO25254	Vernonia colorata	Species	Asteraceae	Eukaryota	Leaves	n.a.	n.a.	PMID[15043416]
NPO25254	Vernonia colorata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19299148]
NPO28689	Armillaria mellea	Species	Physalacriaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19795841]
NPO28689	Armillaria mellea	Species	Physalacriaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[4040154]
NPO18720	Bertholletia excelsa	Species	Lecythidaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO18720	Bertholletia excelsa	Species	Lecythidaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO18720	Bertholletia excelsa	Species	Lecythidaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO25254	Vernonia colorata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18720	Bertholletia excelsa	Species	Lecythidaceae	Eukaryota	Seeds	n.a.		Database[Phenol-Explorer]
NPO25254	Vernonia colorata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28689	Armillaria mellea	Species	Physalacriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18720	Bertholletia excelsa	Species	Lecythidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20948	Gynoxys buxifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19402	Salvadora oleoides	Species	Salvadoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28689	Armillaria mellea	Species	Physalacriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19944	Trichilia roka	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20305	Stachytarpheta mutabilis	Species	Verbenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25254	Vernonia colorata	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
IC50	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	10.8	ug.mL-1	PMID[537010]

☑ 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 NPC198853 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	198
0.1-0.2	1204
0.2-0.3	4896
0.3-0.4	11183
0.4-0.5	12588
0.5-0.6	7425
0.6-0.7	3944
0.7-0.8	1013
0.8-0.85	204
0.85-0.9	22
0.9-0.95	7
0.95-1	13

Similarity Score	Similarity Level	Natural Product ID
0.9773	High Similarity	NPC262133
0.9773	High Similarity	NPC470010
0.9773	High Similarity	NPC323008
0.9773	High Similarity	NPC470013
0.977	High Similarity	NPC133698
0.9551	High Similarity	NPC477131
0.9545	High Similarity	NPC131209
0.9425	High Similarity	NPC91248
0.9231	High Similarity	NPC67584
0.9231	High Similarity	NPC304886
0.913	High Similarity	NPC213078
0.9101	High Similarity	NPC4986
0.9053	High Similarity	NPC86077
0.9032	High Similarity	NPC161493
0.9022	High Similarity	NPC52044
0.8989	High Similarity	NPC79549
0.8989	High Similarity	NPC207114
0.8989	High Similarity	NPC217983
0.8936	High Similarity	NPC221615
0.8913	High Similarity	NPC127019
0.8901	High Similarity	NPC475925
0.8901	High Similarity	NPC184063
0.8889	High Similarity	NPC215556
0.8817	High Similarity	NPC170120
0.8817	High Similarity	NPC213698
0.8804	High Similarity	NPC258216
0.8804	High Similarity	NPC135776
0.8791	High Similarity	NPC216284
0.8791	High Similarity	NPC37607
0.8791	High Similarity	NPC301969
0.8791	High Similarity	NPC19087
0.8776	High Similarity	NPC166115
0.8776	High Similarity	NPC223450
0.8776	High Similarity	NPC243998
0.8764	High Similarity	NPC187661
0.875	High Similarity	NPC150923
0.8696	High Similarity	NPC155215
0.8681	High Similarity	NPC38392
0.8652	High Similarity	NPC284534
0.8652	High Similarity	NPC300082
0.8652	High Similarity	NPC204105
0.8617	High Similarity	NPC476053
0.8617	High Similarity	NPC163228
0.8617	High Similarity	NPC472873
0.8587	High Similarity	NPC297474
0.8587	High Similarity	NPC54065
0.8571	High Similarity	NPC178875
0.8571	High Similarity	NPC124881
0.8556	High Similarity	NPC67493
0.8556	High Similarity	NPC64153
0.8539	High Similarity	NPC224386
0.8539	High Similarity	NPC194859
0.8526	High Similarity	NPC24956
0.8526	High Similarity	NPC18019
0.8523	High Similarity	NPC246076
0.8511	High Similarity	NPC474338
0.8506	High Similarity	NPC276356
0.85	High Similarity	NPC26617
0.8495	Intermediate Similarity	NPC63193
0.8495	Intermediate Similarity	NPC35959
0.8495	Intermediate Similarity	NPC57304
0.8495	Intermediate Similarity	NPC293001
0.8495	Intermediate Similarity	NPC29821
0.8495	Intermediate Similarity	NPC171360
0.8495	Intermediate Similarity	NPC133888
0.8478	Intermediate Similarity	NPC155935
0.8478	Intermediate Similarity	NPC472872
0.8478	Intermediate Similarity	NPC32922
0.8462	Intermediate Similarity	NPC118601
0.8462	Intermediate Similarity	NPC160138
0.8444	Intermediate Similarity	NPC235792
0.8438	Intermediate Similarity	NPC474313
0.8438	Intermediate Similarity	NPC181151
0.8427	Intermediate Similarity	NPC128246
0.8427	Intermediate Similarity	NPC245665
0.8427	Intermediate Similarity	NPC250315
0.8404	Intermediate Similarity	NPC125674
0.8404	Intermediate Similarity	NPC228451
0.8404	Intermediate Similarity	NPC475838
0.8404	Intermediate Similarity	NPC475912
0.8387	Intermediate Similarity	NPC475855
0.8387	Intermediate Similarity	NPC129419
0.8387	Intermediate Similarity	NPC179394
0.8387	Intermediate Similarity	NPC35809
0.8387	Intermediate Similarity	NPC144133
0.837	Intermediate Similarity	NPC224652
0.837	Intermediate Similarity	NPC202672
0.8352	Intermediate Similarity	NPC107787
0.8352	Intermediate Similarity	NPC304558
0.8333	Intermediate Similarity	NPC156485
0.8333	Intermediate Similarity	NPC115786
0.8316	Intermediate Similarity	NPC167219
0.8316	Intermediate Similarity	NPC474247
0.83	Intermediate Similarity	NPC100487
0.8298	Intermediate Similarity	NPC208886
0.8298	Intermediate Similarity	NPC12172
0.8298	Intermediate Similarity	NPC184463
0.828	Intermediate Similarity	NPC295312
0.828	Intermediate Similarity	NPC268298
0.828	Intermediate Similarity	NPC307411
0.8269	Intermediate Similarity	NPC35069
0.8269	Intermediate Similarity	NPC189338
0.8269	Intermediate Similarity	NPC258711
0.8269	Intermediate Similarity	NPC95290
0.8265	Intermediate Similarity	NPC70865
0.8265	Intermediate Similarity	NPC186861
0.8261	Intermediate Similarity	NPC24728
0.8252	Intermediate Similarity	NPC471884
0.8247	Intermediate Similarity	NPC213947
0.8247	Intermediate Similarity	NPC170143
0.8247	Intermediate Similarity	NPC471150
0.8247	Intermediate Similarity	NPC108475
0.8247	Intermediate Similarity	NPC169205
0.8242	Intermediate Similarity	NPC255307
0.8242	Intermediate Similarity	NPC78089
0.8242	Intermediate Similarity	NPC165162
0.8229	Intermediate Similarity	NPC220221
0.8229	Intermediate Similarity	NPC36954
0.8229	Intermediate Similarity	NPC224689
0.8229	Intermediate Similarity	NPC14961
0.8229	Intermediate Similarity	NPC270013
0.8222	Intermediate Similarity	NPC111409
0.8218	Intermediate Similarity	NPC54737
0.8211	Intermediate Similarity	NPC476300
0.8211	Intermediate Similarity	NPC212486
0.8211	Intermediate Similarity	NPC60386
0.8211	Intermediate Similarity	NPC473234
0.8211	Intermediate Similarity	NPC472874
0.8211	Intermediate Similarity	NPC473263
0.8211	Intermediate Similarity	NPC81419
0.8211	Intermediate Similarity	NPC473273
0.8211	Intermediate Similarity	NPC308656
0.8211	Intermediate Similarity	NPC179746
0.8202	Intermediate Similarity	NPC126248
0.8191	Intermediate Similarity	NPC51004
0.8182	Intermediate Similarity	NPC171759
0.8172	Intermediate Similarity	NPC471149
0.8163	Intermediate Similarity	NPC45125
0.8163	Intermediate Similarity	NPC187268
0.8163	Intermediate Similarity	NPC141191
0.8152	Intermediate Similarity	NPC50637
0.8152	Intermediate Similarity	NPC475461
0.8152	Intermediate Similarity	NPC56593
0.8152	Intermediate Similarity	NPC236692
0.8152	Intermediate Similarity	NPC305475
0.8152	Intermediate Similarity	NPC470242
0.8152	Intermediate Similarity	NPC309757
0.8152	Intermediate Similarity	NPC162071
0.8144	Intermediate Similarity	NPC142529
0.8144	Intermediate Similarity	NPC476315
0.8144	Intermediate Similarity	NPC279621
0.8144	Intermediate Similarity	NPC230800
0.8144	Intermediate Similarity	NPC91771
0.8144	Intermediate Similarity	NPC185553
0.8132	Intermediate Similarity	NPC191476
0.8132	Intermediate Similarity	NPC476804
0.8132	Intermediate Similarity	NPC165287
0.8132	Intermediate Similarity	NPC114979
0.8125	Intermediate Similarity	NPC474035
0.8125	Intermediate Similarity	NPC81386
0.8119	Intermediate Similarity	NPC203659
0.8113	Intermediate Similarity	NPC471380
0.8111	Intermediate Similarity	NPC89555
0.8105	Intermediate Similarity	NPC111114
0.8105	Intermediate Similarity	NPC300312
0.8105	Intermediate Similarity	NPC30515
0.8105	Intermediate Similarity	NPC261607
0.81	Intermediate Similarity	NPC474747
0.81	Intermediate Similarity	NPC225353
0.809	Intermediate Similarity	NPC74673
0.809	Intermediate Similarity	NPC258965
0.809	Intermediate Similarity	NPC156658
0.809	Intermediate Similarity	NPC69271
0.8085	Intermediate Similarity	NPC283409
0.8081	Intermediate Similarity	NPC471381
0.8077	Intermediate Similarity	NPC257240
0.8065	Intermediate Similarity	NPC237540
0.8065	Intermediate Similarity	NPC270270
0.8065	Intermediate Similarity	NPC190753
0.8061	Intermediate Similarity	NPC471462
0.8061	Intermediate Similarity	NPC477949
0.8061	Intermediate Similarity	NPC311904
0.8043	Intermediate Similarity	NPC215364
0.8041	Intermediate Similarity	NPC193645
0.8041	Intermediate Similarity	NPC48803
0.8041	Intermediate Similarity	NPC90121
0.8041	Intermediate Similarity	NPC275960
0.8039	Intermediate Similarity	NPC475217
0.8039	Intermediate Similarity	NPC179891
0.8022	Intermediate Similarity	NPC131669
0.8022	Intermediate Similarity	NPC473390
0.8022	Intermediate Similarity	NPC272814
0.8021	Intermediate Similarity	NPC153590
0.8021	Intermediate Similarity	NPC475788
0.802	Intermediate Similarity	NPC110989
0.802	Intermediate Similarity	NPC475871
0.802	Intermediate Similarity	NPC475945
0.8019	Intermediate Similarity	NPC209058
0.8	Intermediate Similarity	NPC474761
0.8	Intermediate Similarity	NPC25684

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 NPC198853 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	185
0.1-0.2	1808
0.2-0.3	3773
0.3-0.4	2338
0.4-0.5	649
0.5-0.6	321
0.6-0.7	59
0.7-0.8	14
0.8-0.85	1
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9101	High Similarity	NPD1695	Approved
0.85	High Similarity	NPD7899	Clinical (unspecified phase)
0.8077	Intermediate Similarity	NPD6371	Approved
0.8041	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7634	Intermediate Similarity	NPD5362	Discontinued
0.7579	Intermediate Similarity	NPD4249	Approved
0.75	Intermediate Similarity	NPD4250	Approved
0.75	Intermediate Similarity	NPD4251	Approved
0.7474	Intermediate Similarity	NPD1733	Clinical (unspecified phase)
0.7447	Intermediate Similarity	NPD7154	Phase 3
0.7431	Intermediate Similarity	NPD6053	Discontinued
0.74	Intermediate Similarity	NPD5282	Discontinued
0.7292	Intermediate Similarity	NPD6082	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD5785	Approved
0.7273	Intermediate Similarity	NPD6698	Approved
0.7273	Intermediate Similarity	NPD46	Approved
0.7128	Intermediate Similarity	NPD5790	Clinical (unspecified phase)
0.7128	Intermediate Similarity	NPD4820	Approved
0.7128	Intermediate Similarity	NPD4819	Approved
0.7128	Intermediate Similarity	NPD4821	Approved
0.7128	Intermediate Similarity	NPD4822	Approved
0.7113	Intermediate Similarity	NPD5363	Approved
0.7053	Intermediate Similarity	NPD5369	Approved
0.6979	Remote Similarity	NPD4270	Approved
0.6979	Remote Similarity	NPD4269	Approved
0.6979	Remote Similarity	NPD6435	Approved
0.6931	Remote Similarity	NPD7838	Discovery
0.6915	Remote Similarity	NPD4271	Approved
0.6915	Remote Similarity	NPD4268	Approved
0.6907	Remote Similarity	NPD5332	Approved
0.6907	Remote Similarity	NPD5331	Approved
0.6887	Remote Similarity	NPD7640	Approved
0.6887	Remote Similarity	NPD7639	Approved
0.6881	Remote Similarity	NPD6008	Approved
0.6875	Remote Similarity	NPD4790	Discontinued
0.6875	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6869	Remote Similarity	NPD5786	Approved
0.6863	Remote Similarity	NPD7983	Approved
0.6796	Remote Similarity	NPD6399	Phase 3
0.6796	Remote Similarity	NPD5779	Approved
0.6796	Remote Similarity	NPD5778	Approved
0.6792	Remote Similarity	NPD4225	Approved
0.6792	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD7638	Approved
0.6771	Remote Similarity	NPD4252	Approved
0.6771	Remote Similarity	NPD5368	Approved
0.6757	Remote Similarity	NPD6686	Approved
0.6737	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5695	Phase 3
0.6667	Remote Similarity	NPD5344	Discontinued
0.6636	Remote Similarity	NPD5696	Approved
0.6633	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.66	Remote Similarity	NPD1694	Approved
0.6581	Remote Similarity	NPD7115	Discovery
0.6574	Remote Similarity	NPD6648	Approved
0.6542	Remote Similarity	NPD6084	Phase 2
0.6542	Remote Similarity	NPD6083	Phase 2
0.6538	Remote Similarity	NPD7637	Suspended
0.6518	Remote Similarity	NPD5697	Approved
0.65	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.646	Remote Similarity	NPD7320	Approved
0.646	Remote Similarity	NPD6881	Approved
0.646	Remote Similarity	NPD6899	Approved
0.6435	Remote Similarity	NPD6649	Approved
0.6435	Remote Similarity	NPD6650	Approved
0.6429	Remote Similarity	NPD6675	Approved
0.6429	Remote Similarity	NPD6402	Approved
0.6429	Remote Similarity	NPD5739	Approved
0.6429	Remote Similarity	NPD7128	Approved
0.6423	Remote Similarity	NPD7507	Approved
0.6404	Remote Similarity	NPD6014	Approved
0.6404	Remote Similarity	NPD6012	Approved
0.6404	Remote Similarity	NPD6373	Approved
0.6404	Remote Similarity	NPD6013	Approved
0.6404	Remote Similarity	NPD6372	Approved
0.64	Remote Similarity	NPD6695	Phase 3
0.6381	Remote Similarity	NPD5693	Phase 1
0.6381	Remote Similarity	NPD5284	Approved
0.6381	Remote Similarity	NPD5281	Approved
0.6372	Remote Similarity	NPD5701	Approved
0.6364	Remote Similarity	NPD8513	Phase 3
0.6364	Remote Similarity	NPD8516	Approved
0.6364	Remote Similarity	NPD8517	Approved
0.6364	Remote Similarity	NPD8515	Approved
0.6355	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6348	Remote Similarity	NPD7102	Approved
0.6348	Remote Similarity	NPD7290	Approved
0.6348	Remote Similarity	NPD6883	Approved
0.6348	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6346	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6346	Remote Similarity	NPD6101	Approved
0.6341	Remote Similarity	NPD7492	Approved
0.6325	Remote Similarity	NPD4632	Approved
0.6316	Remote Similarity	NPD6011	Approved
0.6306	Remote Similarity	NPD7632	Discontinued
0.6306	Remote Similarity	NPD5211	Phase 2
0.63	Remote Similarity	NPD5209	Approved
0.6296	Remote Similarity	NPD7839	Suspended
0.6293	Remote Similarity	NPD6847	Approved
0.6293	Remote Similarity	NPD6869	Approved
0.6293	Remote Similarity	NPD6617	Approved
0.6293	Remote Similarity	NPD8130	Phase 1
0.629	Remote Similarity	NPD6616	Approved
0.6286	Remote Similarity	NPD5207	Approved
0.6281	Remote Similarity	NPD6054	Approved
0.6281	Remote Similarity	NPD6319	Approved
0.627	Remote Similarity	NPD7319	Approved
0.6261	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.625	Remote Similarity	NPD6903	Approved
0.624	Remote Similarity	NPD7078	Approved
0.6239	Remote Similarity	NPD8297	Approved
0.6239	Remote Similarity	NPD6882	Approved
0.623	Remote Similarity	NPD6015	Approved
0.623	Remote Similarity	NPD6016	Approved
0.6228	Remote Similarity	NPD6412	Phase 2
0.6226	Remote Similarity	NPD6411	Approved
0.6214	Remote Similarity	NPD6684	Approved
0.6214	Remote Similarity	NPD7334	Approved
0.6214	Remote Similarity	NPD5330	Approved
0.6214	Remote Similarity	NPD7146	Approved
0.6214	Remote Similarity	NPD6409	Approved
0.6214	Remote Similarity	NPD7521	Approved
0.6204	Remote Similarity	NPD5210	Approved
0.6204	Remote Similarity	NPD4629	Approved
0.6195	Remote Similarity	NPD5141	Approved
0.619	Remote Similarity	NPD4753	Phase 2
0.619	Remote Similarity	NPD7736	Approved
0.6179	Remote Similarity	NPD6370	Approved
0.6179	Remote Similarity	NPD5988	Approved
0.6167	Remote Similarity	NPD6009	Approved
0.6154	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD7524	Approved
0.6154	Remote Similarity	NPD7750	Discontinued
0.6148	Remote Similarity	NPD6059	Approved
0.6126	Remote Similarity	NPD4696	Approved
0.6126	Remote Similarity	NPD5286	Approved
0.6126	Remote Similarity	NPD5285	Approved
0.6116	Remote Similarity	NPD7328	Approved
0.6116	Remote Similarity	NPD7327	Approved
0.6111	Remote Similarity	NPD8074	Phase 3
0.6111	Remote Similarity	NPD6001	Approved
0.6111	Remote Similarity	NPD8293	Discontinued
0.61	Remote Similarity	NPD6930	Phase 2
0.61	Remote Similarity	NPD6931	Approved
0.6098	Remote Similarity	NPD5983	Phase 2
0.6098	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6098	Remote Similarity	NPD8033	Approved
0.6095	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6095	Remote Similarity	NPD5737	Approved
0.6095	Remote Similarity	NPD6672	Approved
0.6091	Remote Similarity	NPD4755	Approved
0.6091	Remote Similarity	NPD7902	Approved
0.6087	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6083	Remote Similarity	NPD6274	Approved
0.6075	Remote Similarity	NPD8034	Phase 2
0.6075	Remote Similarity	NPD8035	Phase 2
0.6066	Remote Similarity	NPD7516	Approved
0.605	Remote Similarity	NPD8133	Approved
0.6038	Remote Similarity	NPD6051	Approved
0.6038	Remote Similarity	NPD6904	Approved
0.6038	Remote Similarity	NPD6673	Approved
0.6038	Remote Similarity	NPD6080	Approved
0.6032	Remote Similarity	NPD8273	Phase 1
0.6019	Remote Similarity	NPD3133	Approved
0.6019	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6019	Remote Similarity	NPD4202	Approved
0.6019	Remote Similarity	NPD3666	Approved
0.6019	Remote Similarity	NPD4786	Approved
0.6019	Remote Similarity	NPD3665	Phase 1
0.6018	Remote Similarity	NPD5225	Approved
0.6018	Remote Similarity	NPD4633	Approved
0.6018	Remote Similarity	NPD5226	Approved
0.6018	Remote Similarity	NPD5224	Approved
0.6017	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6016	Remote Similarity	NPD8294	Approved
0.6016	Remote Similarity	NPD8377	Approved
0.6	Remote Similarity	NPD7604	Phase 2
0.6	Remote Similarity	NPD6929	Approved
0.5982	Remote Similarity	NPD4700	Approved
0.5981	Remote Similarity	NPD5692	Phase 3
0.598	Remote Similarity	NPD4221	Approved
0.598	Remote Similarity	NPD3667	Approved
0.598	Remote Similarity	NPD4223	Phase 3
0.5969	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.5968	Remote Similarity	NPD8335	Approved
0.5968	Remote Similarity	NPD7503	Approved
0.5968	Remote Similarity	NPD8379	Approved
0.5968	Remote Similarity	NPD8296	Approved
0.5968	Remote Similarity	NPD8378	Approved
0.5968	Remote Similarity	NPD8380	Approved
0.5965	Remote Similarity	NPD5175	Approved
0.5965	Remote Similarity	NPD5174	Approved
0.5963	Remote Similarity	NPD7748	Approved
0.596	Remote Similarity	NPD4756	Discovery
0.5948	Remote Similarity	NPD6685	Approved
0.5943	Remote Similarity	NPD5208	Approved
0.5941	Remote Similarity	NPD7332	Phase 2
0.5935	Remote Similarity	NPD7100	Approved
0.5935	Remote Similarity	NPD7101	Approved
0.5932	Remote Similarity	NPD4634	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