NPASS Compound

Structure

NPC470243 OpenBabel07101718232D 22 24 0 0 1 0 0 0 0 0999 V2000 -2.9312 1.5294 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2596 -2.4705 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6975 -4.3185 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9511 -1.1703 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0694 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4467 -0.8827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5547 0.6645 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5147 0.6645 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.3456 -1.5144 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.6975 -3.3585 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1132 -0.0861 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9561 -0.0861 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.7237 -1.5144 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1698 -1.0220 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.0347 -1.4385 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.3773 -0.8827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8996 -1.0220 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.5288 -2.8785 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.8098 -2.4705 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3132 -1.0964 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.0347 -2.3985 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 10 1 0 0 0 0 4 17 1 0 0 0 0 5 6 1 0 0 0 0 5 11 1 0 0 0 0 6 13 1 0 0 0 0 7 8 1 0 0 0 0 8 1 1 6 0 0 0 8 11 1 0 0 0 0 9 2 1 6 0 0 0 9 14 1 0 0 0 0 9 16 1 0 0 0 0 10 18 2 0 0 0 0 10 21 1 0 0 0 0 11 17 1 1 0 0 0 12 7 1 6 0 0 0 12 14 1 0 0 0 0 12 22 1 0 0 0 0 13 17 1 0 0 0 0 13 19 2 0 0 0 0 14 15 1 0 0 0 0 15 17 1 0 0 0 0 15 21 1 0 0 0 0 16 20 2 0 0 0 0 16 22 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	308.16
Volume:	312.961
LogP:	1.65
LogD:	1.753
LogS:	-2.904
# Rotatable Bonds:	2
TPSA:	69.67
# H-Bond Aceptor:	5
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.694
Synthetic Accessibility Score:	4.462
Fsp3:	0.824
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-4.719
MDCK Permeability:	5.657151632476598e-05
Pgp-inhibitor:	0.997
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.014
20% Bioavailability (F20%):	0.108
30% Bioavailability (F30%):	0.981

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.96
Plasma Protein Binding (PPB):	39.419193267822266%
Volume Distribution (VD):	0.799
Pgp-substrate:	56.518089294433594%

ADMET: Metabolism

CYP1A2-inhibitor:	0.094
CYP1A2-substrate:	0.091
CYP2C19-inhibitor:	0.019
CYP2C19-substrate:	0.823
CYP2C9-inhibitor:	0.008
CYP2C9-substrate:	0.079
CYP2D6-inhibitor:	0.01
CYP2D6-substrate:	0.171
CYP3A4-inhibitor:	0.38
CYP3A4-substrate:	0.394

ADMET: Excretion

Clearance (CL):	7.933
Half-life (T1/2):	0.892

ADMET: Toxicity

hERG Blockers:	0.032
Human Hepatotoxicity (H-HT):	0.558
Drug-inuced Liver Injury (DILI):	0.824
AMES Toxicity:	0.02
Rat Oral Acute Toxicity:	0.174
Maximum Recommended Daily Dose:	0.049
Skin Sensitization:	0.769
Carcinogencity:	0.232
Eye Corrosion:	0.338
Eye Irritation:	0.39
Respiratory Toxicity:	0.74

Download Data

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

Natural Product: NPC470243

Natural Product ID:	NPC470243
*Common Name:**	Dihydroergolide
IUPAC Name:	[(1R,3aS,5R,5aS,8aR,9S,9aR)-1,5,8a-trimethyl-2,8-dioxo-3a,4,5,5a,6,7,9,9a-octahydro-1H-azuleno[6,5-b]furan-9-yl] acetate
Synonyms:	Dihydroergolide
Standard InCHIKey:	SLDGZDXXRTZQAQ-WUYYVTOLSA-N
Standard InCHI:	InChI=1S/C17H24O5/c1-8-7-12-14(9(2)16(20)22-12)15(21-10(3)18)17(4)11(8)5-6-13(17)19/h8-9,11-12,14-15H,5-7H2,1-4H3/t8-,9-,11+,12+,14-,15+,17+/m1/s1
SMILES:	CC(=O)O[C@H]1[C@H]2[C@@H](OC(=O)[C@@H]2C)C[C@H]([C@H]2[C@@]1(C)C(=O)CC2)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1912045
PubChem CID:	57403344
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
NPO22238	Inula falconeri	Species	Asteraceae	Eukaryota	aerial parts	Tibet, China	n.a.	PMID[21924800]
NPO22238	Inula falconeri	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
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	8340.0	nM	PMID[455991]

☑ 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 NPC470243 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	562
0.1-0.2	5459
0.2-0.3	15089
0.3-0.4	10028
0.4-0.5	7550
0.5-0.6	3441
0.6-0.7	486
0.7-0.8	77
0.8-0.85	2
0.85-0.9	0
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9286	High Similarity	NPC179922
0.9091	High Similarity	NPC157518
0.825	Intermediate Similarity	NPC238593
0.8108	Intermediate Similarity	NPC215030
0.7875	Intermediate Similarity	NPC54468
0.7867	Intermediate Similarity	NPC477867
0.7805	Intermediate Similarity	NPC70422
0.7805	Intermediate Similarity	NPC70555
0.7805	Intermediate Similarity	NPC104961
0.7765	Intermediate Similarity	NPC191339
0.7765	Intermediate Similarity	NPC286341
0.7746	Intermediate Similarity	NPC215987
0.7746	Intermediate Similarity	NPC306805
0.7738	Intermediate Similarity	NPC168679
0.7738	Intermediate Similarity	NPC12872
0.7733	Intermediate Similarity	NPC474755
0.7722	Intermediate Similarity	NPC51507
0.7722	Intermediate Similarity	NPC1882
0.7671	Intermediate Similarity	NPC119838
0.75	Intermediate Similarity	NPC73052
0.75	Intermediate Similarity	NPC290508
0.75	Intermediate Similarity	NPC6823
0.75	Intermediate Similarity	NPC293418
0.75	Intermediate Similarity	NPC476330
0.7442	Intermediate Similarity	NPC253144
0.7439	Intermediate Similarity	NPC157328
0.7416	Intermediate Similarity	NPC126156
0.7416	Intermediate Similarity	NPC91771
0.7416	Intermediate Similarity	NPC142529
0.7412	Intermediate Similarity	NPC53158
0.7375	Intermediate Similarity	NPC474754
0.7361	Intermediate Similarity	NPC314103
0.7356	Intermediate Similarity	NPC284185
0.7356	Intermediate Similarity	NPC70595
0.7356	Intermediate Similarity	NPC74103
0.7356	Intermediate Similarity	NPC123177
0.7356	Intermediate Similarity	NPC150978
0.7342	Intermediate Similarity	NPC471151
0.7333	Intermediate Similarity	NPC5714
0.7326	Intermediate Similarity	NPC117405
0.7326	Intermediate Similarity	NPC200580
0.7326	Intermediate Similarity	NPC52198
0.7317	Intermediate Similarity	NPC212340
0.7317	Intermediate Similarity	NPC13494
0.7294	Intermediate Similarity	NPC201658
0.7273	Intermediate Similarity	NPC473273
0.7273	Intermediate Similarity	NPC308656
0.7273	Intermediate Similarity	NPC153590
0.7273	Intermediate Similarity	NPC473263
0.7273	Intermediate Similarity	NPC473234
0.7273	Intermediate Similarity	NPC60386
0.7273	Intermediate Similarity	NPC248567
0.7262	Intermediate Similarity	NPC473350
0.726	Intermediate Similarity	NPC295256
0.726	Intermediate Similarity	NPC469926
0.7215	Intermediate Similarity	NPC471046
0.72	Intermediate Similarity	NPC319007
0.7191	Intermediate Similarity	NPC289004
0.7183	Intermediate Similarity	NPC472021
0.7176	Intermediate Similarity	NPC236692
0.7176	Intermediate Similarity	NPC304558
0.7176	Intermediate Similarity	NPC309757
0.7162	Intermediate Similarity	NPC315525
0.7162	Intermediate Similarity	NPC135043
0.7143	Intermediate Similarity	NPC25802
0.7143	Intermediate Similarity	NPC51135
0.7143	Intermediate Similarity	NPC82492
0.7143	Intermediate Similarity	NPC101138
0.7125	Intermediate Similarity	NPC477918
0.7125	Intermediate Similarity	NPC169389
0.7125	Intermediate Similarity	NPC208223
0.7097	Intermediate Similarity	NPC171759
0.7093	Intermediate Similarity	NPC24728
0.7089	Intermediate Similarity	NPC471491
0.7083	Intermediate Similarity	NPC469922
0.7079	Intermediate Similarity	NPC472238
0.7079	Intermediate Similarity	NPC472237
0.7079	Intermediate Similarity	NPC200237
0.7073	Intermediate Similarity	NPC134227
0.7067	Intermediate Similarity	NPC469925
0.7059	Intermediate Similarity	NPC319589
0.7051	Intermediate Similarity	NPC109510
0.7042	Intermediate Similarity	NPC472019
0.7042	Intermediate Similarity	NPC226602
0.7042	Intermediate Similarity	NPC472020
0.7033	Intermediate Similarity	NPC185553
0.7033	Intermediate Similarity	NPC193785
0.7024	Intermediate Similarity	NPC476721
0.7024	Intermediate Similarity	NPC472847
0.7011	Intermediate Similarity	NPC470009
0.7011	Intermediate Similarity	NPC471149
0.7	Intermediate Similarity	NPC470424
0.7	Intermediate Similarity	NPC473331
0.6988	Remote Similarity	NPC39411
0.6988	Remote Similarity	NPC255580
0.6977	Remote Similarity	NPC476717
0.6977	Remote Similarity	NPC477441
0.697	Remote Similarity	NPC305182
0.6962	Remote Similarity	NPC469641
0.6962	Remote Similarity	NPC469643
0.6957	Remote Similarity	NPC108475
0.6957	Remote Similarity	NPC213947
0.6957	Remote Similarity	NPC170143
0.6957	Remote Similarity	NPC169205
0.6947	Remote Similarity	NPC469350
0.6941	Remote Similarity	NPC65133
0.6941	Remote Similarity	NPC477434
0.6932	Remote Similarity	NPC283409
0.6923	Remote Similarity	NPC90121
0.6923	Remote Similarity	NPC197701
0.6923	Remote Similarity	NPC193645
0.6923	Remote Similarity	NPC275960
0.6923	Remote Similarity	NPC48803
0.6915	Remote Similarity	NPC162024
0.6915	Remote Similarity	NPC477950
0.6914	Remote Similarity	NPC143250
0.6905	Remote Similarity	NPC246076
0.6897	Remote Similarity	NPC118601
0.6889	Remote Similarity	NPC228700
0.6889	Remote Similarity	NPC476189
0.6882	Remote Similarity	NPC141191
0.6882	Remote Similarity	NPC54843
0.6882	Remote Similarity	NPC274695
0.6875	Remote Similarity	NPC132064
0.6875	Remote Similarity	NPC477934
0.6867	Remote Similarity	NPC125366
0.6866	Remote Similarity	NPC314084
0.6854	Remote Similarity	NPC54065
0.6854	Remote Similarity	NPC297474
0.6854	Remote Similarity	NPC19087
0.6849	Remote Similarity	NPC306750
0.6849	Remote Similarity	NPC253204
0.6835	Remote Similarity	NPC475232
0.6835	Remote Similarity	NPC473775
0.6835	Remote Similarity	NPC475260
0.6835	Remote Similarity	NPC473699
0.6835	Remote Similarity	NPC474100
0.6835	Remote Similarity	NPC51249
0.6824	Remote Similarity	NPC128246
0.6824	Remote Similarity	NPC111409
0.6824	Remote Similarity	NPC215294
0.6818	Remote Similarity	NPC178875
0.6813	Remote Similarity	NPC206878
0.6804	Remote Similarity	NPC228311
0.6804	Remote Similarity	NPC291643
0.6804	Remote Similarity	NPC168890
0.6804	Remote Similarity	NPC469441
0.6804	Remote Similarity	NPC41674
0.679	Remote Similarity	NPC477933
0.679	Remote Similarity	NPC477932
0.6786	Remote Similarity	NPC475951
0.6782	Remote Similarity	NPC243746
0.6782	Remote Similarity	NPC92139
0.6782	Remote Similarity	NPC475491
0.6782	Remote Similarity	NPC469626
0.6778	Remote Similarity	NPC133888
0.6778	Remote Similarity	NPC57304
0.6778	Remote Similarity	NPC35959
0.6778	Remote Similarity	NPC29821
0.6778	Remote Similarity	NPC216137
0.6778	Remote Similarity	NPC184063
0.6778	Remote Similarity	NPC293001
0.6778	Remote Similarity	NPC171360
0.6778	Remote Similarity	NPC63193
0.6774	Remote Similarity	NPC311904
0.6757	Remote Similarity	NPC474552
0.675	Remote Similarity	NPC320537
0.675	Remote Similarity	NPC143979
0.675	Remote Similarity	NPC125164
0.675	Remote Similarity	NPC55508
0.6747	Remote Similarity	NPC469620
0.6744	Remote Similarity	NPC319909
0.6742	Remote Similarity	NPC477443
0.6742	Remote Similarity	NPC61688
0.6742	Remote Similarity	NPC67653
0.6742	Remote Similarity	NPC471459
0.6742	Remote Similarity	NPC155935
0.6742	Remote Similarity	NPC38392
0.6742	Remote Similarity	NPC477440
0.6739	Remote Similarity	NPC470191
0.6739	Remote Similarity	NPC287354
0.6739	Remote Similarity	NPC62407
0.6739	Remote Similarity	NPC163228
0.6737	Remote Similarity	NPC304624
0.6737	Remote Similarity	NPC474053
0.6735	Remote Similarity	NPC290247
0.6735	Remote Similarity	NPC469788
0.6735	Remote Similarity	NPC176756
0.6735	Remote Similarity	NPC469787
0.6712	Remote Similarity	NPC478126
0.6712	Remote Similarity	NPC469921
0.6712	Remote Similarity	NPC66145
0.6709	Remote Similarity	NPC96322
0.6707	Remote Similarity	NPC307865
0.6707	Remote Similarity	NPC474003
0.6707	Remote Similarity	NPC214030
0.6707	Remote Similarity	NPC83108
0.6706	Remote Similarity	NPC148740
0.6706	Remote Similarity	NPC102156
0.6705	Remote Similarity	NPC475773

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 NPC470243 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	761
0.1-0.2	4521
0.2-0.3	2663
0.3-0.4	706
0.4-0.5	351
0.5-0.6	139
0.6-0.7	7
0.7-0.8	2
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
0.7671	Intermediate Similarity	NPD229	Approved
0.726	Intermediate Similarity	NPD9496	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD5777	Approved
0.6923	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD4238	Approved
0.6829	Remote Similarity	NPD4802	Phase 2
0.6575	Remote Similarity	NPD3198	Approved
0.6512	Remote Similarity	NPD6435	Approved
0.6463	Remote Similarity	NPD3702	Approved
0.6392	Remote Similarity	NPD1700	Approved
0.6364	Remote Similarity	NPD4056	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD4057	Clinical (unspecified phase)
0.6338	Remote Similarity	NPD3729	Clinical (unspecified phase)
0.631	Remote Similarity	NPD6116	Phase 1
0.6279	Remote Similarity	NPD5368	Approved
0.6222	Remote Similarity	NPD5786	Approved
0.6207	Remote Similarity	NPD5369	Approved
0.619	Remote Similarity	NPD6117	Approved
0.6154	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.6145	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6098	Remote Similarity	NPD6081	Approved
0.6076	Remote Similarity	NPD4224	Phase 2
0.6071	Remote Similarity	NPD3703	Phase 2
0.6049	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6049	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6049	Remote Similarity	NPD3698	Phase 2
0.6047	Remote Similarity	NPD6114	Approved
0.6047	Remote Similarity	NPD6115	Approved
0.6047	Remote Similarity	NPD6697	Approved
0.6047	Remote Similarity	NPD6118	Approved
0.6026	Remote Similarity	NPD7909	Approved
0.6022	Remote Similarity	NPD1695	Approved
0.6	Remote Similarity	NPD6399	Phase 3
0.598	Remote Similarity	NPD6008	Approved
0.5976	Remote Similarity	NPD4245	Approved
0.5976	Remote Similarity	NPD4244	Approved
0.597	Remote Similarity	NPD2699	Approved
0.5957	Remote Similarity	NPD5785	Approved
0.5955	Remote Similarity	NPD4269	Approved
0.5955	Remote Similarity	NPD4270	Approved
0.5942	Remote Similarity	NPD2266	Phase 2
0.5942	Remote Similarity	NPD6125	Clinical (unspecified phase)
0.5938	Remote Similarity	NPD5282	Discontinued
0.5914	Remote Similarity	NPD6903	Approved
0.5909	Remote Similarity	NPD387	Clinical (unspecified phase)
0.5904	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.5904	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.5895	Remote Similarity	NPD6411	Approved
0.5895	Remote Similarity	NPD8034	Phase 2
0.5895	Remote Similarity	NPD8035	Phase 2
0.589	Remote Similarity	NPD615	Clinical (unspecified phase)
0.587	Remote Similarity	NPD7334	Approved
0.587	Remote Similarity	NPD6684	Approved
0.587	Remote Similarity	NPD5330	Approved
0.587	Remote Similarity	NPD7146	Approved
0.587	Remote Similarity	NPD6409	Approved
0.587	Remote Similarity	NPD7521	Approved
0.5862	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.5797	Remote Similarity	NPD344	Approved
0.5797	Remote Similarity	NPD343	Approved
0.5797	Remote Similarity	NPD345	Approved
0.5783	Remote Similarity	NPD4789	Approved
0.5778	Remote Similarity	NPD7345	Approved
0.5769	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.5761	Remote Similarity	NPD1694	Approved
0.5761	Remote Similarity	NPD5363	Approved
0.5745	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.5745	Remote Similarity	NPD6672	Approved
0.5745	Remote Similarity	NPD5737	Approved
0.573	Remote Similarity	NPD4252	Approved
0.5728	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD7320	Approved
0.5714	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.5694	Remote Similarity	NPD9638	Phase 2
0.5684	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.5684	Remote Similarity	NPD6101	Approved
0.5676	Remote Similarity	NPD3728	Approved
0.5676	Remote Similarity	NPD3730	Approved
0.5673	Remote Similarity	NPD7128	Approved
0.5673	Remote Similarity	NPD6402	Approved
0.5673	Remote Similarity	NPD6675	Approved
0.5673	Remote Similarity	NPD5739	Approved
0.5667	Remote Similarity	NPD1780	Approved
0.5667	Remote Similarity	NPD1779	Approved
0.5663	Remote Similarity	NPD3726	Approved
0.5663	Remote Similarity	NPD3725	Approved
0.566	Remote Similarity	NPD6372	Approved
0.566	Remote Similarity	NPD6373	Approved
0.5652	Remote Similarity	NPD634	Phase 3
0.5625	Remote Similarity	NPD5207	Approved
0.5619	Remote Similarity	NPD5697	Approved
0.5619	Remote Similarity	NPD5701	Approved
0.5607	Remote Similarity	NPD6371	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