NPASS Compound

Structure

NPC118987 OpenBabel07101718332D 32 35 0 0 1 0 0 0 0 0999 V2000 -6.7910 -2.5305 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.6329 -1.0722 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6209 -2.4003 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3900 0.4877 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2651 1.8445 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9166 -0.6238 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5931 -5.7682 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5811 -1.0722 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4231 -1.5583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9490 -0.1000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2541 1.4387 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1070 -3.2423 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0823 1.5709 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5931 -2.4003 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2210 1.3371 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1070 0.3861 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8568 1.3193 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7910 -1.5583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9490 -1.0722 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5811 -0.1000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.8586 0.5505 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.2651 -1.0722 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.5931 -4.0842 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6118 0.7556 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1070 -1.5583 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.4231 0.3861 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.2651 -0.1000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9076 0.3484 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.5654 -4.0842 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5827 0.7047 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1070 -4.9262 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 18 2 0 0 0 0 2 18 1 0 0 0 0 4 26 1 0 0 0 0 7 31 1 0 0 0 0 8 9 1 0 0 0 0 8 20 1 0 0 0 0 9 22 1 0 0 0 0 10 16 1 0 0 0 0 10 19 1 0 0 0 0 11 15 1 0 0 0 0 12 14 1 0 0 0 0 12 23 1 0 0 0 0 13 17 1 0 0 0 0 13 24 1 0 0 0 0 14 25 1 0 0 0 0 15 26 1 0 0 0 0 16 27 1 0 0 0 0 17 28 1 0 0 0 0 18 19 1 0 0 0 0 19 25 1 6 0 0 0 20 21 1 0 0 0 0 20 26 1 1 0 0 0 21 11 1 6 0 0 0 21 28 1 0 0 0 0 22 25 1 6 0 0 0 22 27 1 0 0 0 0 23 29 2 0 0 0 0 23 31 1 0 0 0 0 24 30 2 0 0 0 0 24 32 1 0 0 0 0 25 3 1 6 0 0 0 26 27 1 6 0 0 0 27 5 1 6 0 0 0 28 6 1 1 0 0 0 28 32 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	444.32
Volume:	485.87
LogP:	5.829
LogD:	4.893
LogS:	-5.682
# Rotatable Bonds:	6
TPSA:	52.6
# H-Bond Aceptor:	4
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.36
Synthetic Accessibility Score:	4.718
Fsp3:	0.857
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.782
MDCK Permeability:	3.582072531571612e-05
Pgp-inhibitor:	0.996
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.002
20% Bioavailability (F20%):	0.01
30% Bioavailability (F30%):	0.689

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.039
Plasma Protein Binding (PPB):	87.6511459350586%
Volume Distribution (VD):	0.58
Pgp-substrate:	7.87965202331543%

ADMET: Metabolism

CYP1A2-inhibitor:	0.079
CYP1A2-substrate:	0.305
CYP2C19-inhibitor:	0.136
CYP2C19-substrate:	0.933
CYP2C9-inhibitor:	0.292
CYP2C9-substrate:	0.187
CYP2D6-inhibitor:	0.025
CYP2D6-substrate:	0.357
CYP3A4-inhibitor:	0.892
CYP3A4-substrate:	0.691

ADMET: Excretion

Clearance (CL):	8.397
Half-life (T1/2):	0.201

ADMET: Toxicity

hERG Blockers:	0.689
Human Hepatotoxicity (H-HT):	0.397
Drug-inuced Liver Injury (DILI):	0.49
AMES Toxicity:	0.003
Rat Oral Acute Toxicity:	0.078
Maximum Recommended Daily Dose:	0.32
Skin Sensitization:	0.962
Carcinogencity:	0.165
Eye Corrosion:	0.6
Eye Irritation:	0.047
Respiratory Toxicity:	0.946

Download Data

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

Natural Product: NPC118987

Natural Product ID:	NPC118987
*Common Name:**	Methyl Eichlerialactone
IUPAC Name:	methyl 3-[(3S,3aR,5aR,6S,7S,9aR,9bR)-6,9a,9b-trimethyl-3-[(2S)-2-methyl-5-oxooxolan-2-yl]-7-prop-1-en-2-yl-1,2,3,3a,4,5,5a,7,8,9-decahydrocyclopenta[a]naphthalen-6-yl]propanoate
Synonyms:
Standard InCHIKey:	JZVZOANCEJLALY-CSIKZEOISA-N
Standard InCHI:	InChI=1S/C28H44O4/c1-18(2)19-10-16-27(5)22(25(19,3)14-12-23(29)31-7)9-8-20-21(11-15-26(20,27)4)28(6)17-13-24(30)32-28/h19-22H,1,8-17H2,2-7H3/t19-,20+,21-,22+,25-,26+,27+,28-/m0/s1
SMILES:	C=C(C)[C@@H]1CC[C@]2(C)[C@H](CC[C@@H]3[C@H](CC[C@@]23C)[C@]2(C)CCC(=O)O2)[C@@]1(C)CCC(=O)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3109459
PubChem CID:	76335695
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones [CHEMONTID:0001538] Diterpene 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
NPO32464	dysoxylum binecteriferum	Species	Meliaceae	Eukaryota	stem bark	n.a.	n.a.	PMID[24547740]

☑ 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	4

Activity Type	# Activity
Cell Line	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT65	Cell Line	HepG2	Homo sapiens	IC50	>	50000.0	nM	PMID[483264]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	50000.0	nM	PMID[483264]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	50000.0	nM	PMID[483264]
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	31800.0	nM	PMID[483264]

☑ 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 NPC118987 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	186
0.1-0.2	1725
0.2-0.3	9805
0.3-0.4	13619
0.4-0.5	5884
0.5-0.6	6983
0.6-0.7	3843
0.7-0.8	609
0.8-0.85	29
0.85-0.9	11
0.9-0.95	0
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9865	High Similarity	NPC170038
0.9474	High Similarity	NPC232625
0.8875	High Similarity	NPC100391
0.8765	High Similarity	NPC470223
0.8675	High Similarity	NPC229407
0.8675	High Similarity	NPC250687
0.8675	High Similarity	NPC254572
0.8675	High Similarity	NPC48824
0.8667	High Similarity	NPC279241
0.8625	High Similarity	NPC476458
0.8625	High Similarity	NPC258153
0.859	High Similarity	NPC63020
0.8571	High Similarity	NPC269267
0.8554	High Similarity	NPC167877
0.8493	Intermediate Similarity	NPC469868
0.8481	Intermediate Similarity	NPC471475
0.8462	Intermediate Similarity	NPC238227
0.8462	Intermediate Similarity	NPC66105
0.8452	Intermediate Similarity	NPC28227
0.8395	Intermediate Similarity	NPC240302
0.8372	Intermediate Similarity	NPC471747
0.8354	Intermediate Similarity	NPC321690
0.8333	Intermediate Similarity	NPC476601
0.8333	Intermediate Similarity	NPC246445
0.8333	Intermediate Similarity	NPC92489
0.8313	Intermediate Similarity	NPC98270
0.8293	Intermediate Similarity	NPC170862
0.8293	Intermediate Similarity	NPC471037
0.8289	Intermediate Similarity	NPC197701
0.8235	Intermediate Similarity	NPC255176
0.8214	Intermediate Similarity	NPC471042
0.8202	Intermediate Similarity	NPC322063
0.8193	Intermediate Similarity	NPC475509
0.8182	Intermediate Similarity	NPC472223
0.8182	Intermediate Similarity	NPC472224
0.8118	Intermediate Similarity	NPC474174
0.8118	Intermediate Similarity	NPC251808
0.8118	Intermediate Similarity	NPC128644
0.8101	Intermediate Similarity	NPC20466
0.809	Intermediate Similarity	NPC280877
0.8068	Intermediate Similarity	NPC475700
0.8068	Intermediate Similarity	NPC470224
0.8049	Intermediate Similarity	NPC475951
0.8025	Intermediate Similarity	NPC192744
0.8023	Intermediate Similarity	NPC4309
0.8	Intermediate Similarity	NPC475932
0.8	Intermediate Similarity	NPC264127
0.8	Intermediate Similarity	NPC475007
0.8	Intermediate Similarity	NPC472505
0.8	Intermediate Similarity	NPC68828
0.8	Intermediate Similarity	NPC80590
0.8	Intermediate Similarity	NPC307164
0.7955	Intermediate Similarity	NPC160506
0.7955	Intermediate Similarity	NPC150383
0.7952	Intermediate Similarity	NPC133391
0.7952	Intermediate Similarity	NPC327969
0.7952	Intermediate Similarity	NPC321289
0.7949	Intermediate Similarity	NPC330659
0.7949	Intermediate Similarity	NPC244708
0.7949	Intermediate Similarity	NPC161187
0.7931	Intermediate Similarity	NPC474570
0.7931	Intermediate Similarity	NPC305039
0.7931	Intermediate Similarity	NPC473039
0.7931	Intermediate Similarity	NPC11611
0.7927	Intermediate Similarity	NPC476265
0.7927	Intermediate Similarity	NPC274522
0.7912	Intermediate Similarity	NPC475894
0.7912	Intermediate Similarity	NPC253586
0.7907	Intermediate Similarity	NPC265580
0.7907	Intermediate Similarity	NPC134197
0.7907	Intermediate Similarity	NPC33768
0.7901	Intermediate Similarity	NPC321514
0.7895	Intermediate Similarity	NPC290445
0.7895	Intermediate Similarity	NPC36616
0.7882	Intermediate Similarity	NPC269638
0.7882	Intermediate Similarity	NPC474971
0.7882	Intermediate Similarity	NPC201655
0.7857	Intermediate Similarity	NPC477373
0.7857	Intermediate Similarity	NPC167103
0.7857	Intermediate Similarity	NPC245866
0.7841	Intermediate Similarity	NPC471896
0.7831	Intermediate Similarity	NPC209318
0.7831	Intermediate Similarity	NPC327002
0.7831	Intermediate Similarity	NPC223330
0.7831	Intermediate Similarity	NPC147066
0.7826	Intermediate Similarity	NPC473155
0.7826	Intermediate Similarity	NPC271387
0.7826	Intermediate Similarity	NPC252295
0.7826	Intermediate Similarity	NPC153792
0.7816	Intermediate Similarity	NPC183374
0.7816	Intermediate Similarity	NPC472220
0.7816	Intermediate Similarity	NPC97884
0.7816	Intermediate Similarity	NPC472870
0.7816	Intermediate Similarity	NPC211162
0.7816	Intermediate Similarity	NPC474719
0.7805	Intermediate Similarity	NPC477371
0.7805	Intermediate Similarity	NPC158846
0.7791	Intermediate Similarity	NPC470050
0.7791	Intermediate Similarity	NPC12774
0.7791	Intermediate Similarity	NPC195640
0.7791	Intermediate Similarity	NPC2783
0.7791	Intermediate Similarity	NPC70661
0.7791	Intermediate Similarity	NPC470051
0.7778	Intermediate Similarity	NPC471035
0.7778	Intermediate Similarity	NPC100257
0.7778	Intermediate Similarity	NPC224410
0.7778	Intermediate Similarity	NPC212661
0.7765	Intermediate Similarity	NPC320801
0.7765	Intermediate Similarity	NPC263974
0.7753	Intermediate Similarity	NPC154101
0.7753	Intermediate Similarity	NPC471901
0.7742	Intermediate Similarity	NPC476303
0.7742	Intermediate Similarity	NPC470906
0.7742	Intermediate Similarity	NPC108371
0.7738	Intermediate Similarity	NPC100297
0.7738	Intermediate Similarity	NPC13494
0.7738	Intermediate Similarity	NPC226988
0.7733	Intermediate Similarity	NPC474768
0.7727	Intermediate Similarity	NPC288699
0.7727	Intermediate Similarity	NPC215029
0.7727	Intermediate Similarity	NPC474889
0.7727	Intermediate Similarity	NPC471043
0.7727	Intermediate Similarity	NPC476733
0.7727	Intermediate Similarity	NPC474679
0.7727	Intermediate Similarity	NPC116146
0.7727	Intermediate Similarity	NPC24772
0.7717	Intermediate Similarity	NPC469810
0.7711	Intermediate Similarity	NPC206735
0.7711	Intermediate Similarity	NPC304194
0.7701	Intermediate Similarity	NPC269360
0.7701	Intermediate Similarity	NPC96496
0.7701	Intermediate Similarity	NPC175293
0.7701	Intermediate Similarity	NPC264005
0.7701	Intermediate Similarity	NPC136948
0.7692	Intermediate Similarity	NPC469599
0.7692	Intermediate Similarity	NPC91369
0.7692	Intermediate Similarity	NPC279974
0.7683	Intermediate Similarity	NPC35574
0.7674	Intermediate Similarity	NPC329738
0.7674	Intermediate Similarity	NPC264317
0.7674	Intermediate Similarity	NPC283733
0.7674	Intermediate Similarity	NPC323765
0.7674	Intermediate Similarity	NPC294438
0.7667	Intermediate Similarity	NPC472225
0.7667	Intermediate Similarity	NPC475061
0.7667	Intermediate Similarity	NPC287118
0.7667	Intermediate Similarity	NPC471902
0.7667	Intermediate Similarity	NPC472226
0.7667	Intermediate Similarity	NPC294263
0.7667	Intermediate Similarity	NPC473690
0.7654	Intermediate Similarity	NPC41017
0.7654	Intermediate Similarity	NPC476985
0.7654	Intermediate Similarity	NPC474316
0.7654	Intermediate Similarity	NPC475744
0.7647	Intermediate Similarity	NPC472740
0.7647	Intermediate Similarity	NPC271784
0.7647	Intermediate Similarity	NPC469561
0.764	Intermediate Similarity	NPC475965
0.764	Intermediate Similarity	NPC148414
0.764	Intermediate Similarity	NPC111585
0.764	Intermediate Similarity	NPC472866
0.764	Intermediate Similarity	NPC474842
0.764	Intermediate Similarity	NPC175628
0.7632	Intermediate Similarity	NPC84562
0.7625	Intermediate Similarity	NPC46610
0.7625	Intermediate Similarity	NPC474524
0.7625	Intermediate Similarity	NPC166797
0.7625	Intermediate Similarity	NPC475517
0.7625	Intermediate Similarity	NPC18819
0.7619	Intermediate Similarity	NPC477372
0.7619	Intermediate Similarity	NPC58631
0.7619	Intermediate Similarity	NPC472230
0.7619	Intermediate Similarity	NPC38350
0.7619	Intermediate Similarity	NPC201912
0.7619	Intermediate Similarity	NPC474955
0.7619	Intermediate Similarity	NPC472229
0.7614	Intermediate Similarity	NPC56413
0.7614	Intermediate Similarity	NPC183546
0.7614	Intermediate Similarity	NPC117122
0.7614	Intermediate Similarity	NPC16377
0.7614	Intermediate Similarity	NPC474845
0.7614	Intermediate Similarity	NPC294480
0.7614	Intermediate Similarity	NPC226863
0.7604	Intermediate Similarity	NPC472227
0.7604	Intermediate Similarity	NPC471293
0.7604	Intermediate Similarity	NPC472228
0.7595	Intermediate Similarity	NPC72343
0.7595	Intermediate Similarity	NPC469940
0.759	Intermediate Similarity	NPC215843
0.759	Intermediate Similarity	NPC192999
0.759	Intermediate Similarity	NPC47808
0.759	Intermediate Similarity	NPC305835
0.759	Intermediate Similarity	NPC263951
0.759	Intermediate Similarity	NPC201459
0.759	Intermediate Similarity	NPC153987
0.759	Intermediate Similarity	NPC476438
0.759	Intermediate Similarity	NPC327674
0.759	Intermediate Similarity	NPC44083
0.7586	Intermediate Similarity	NPC155011
0.7586	Intermediate Similarity	NPC212843

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 NPC118987 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	165
0.1-0.2	2164
0.2-0.3	4368
0.3-0.4	1601
0.4-0.5	438
0.5-0.6	186
0.6-0.7	189
0.7-0.8	37
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8295	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.8023	Intermediate Similarity	NPD6672	Approved
0.8023	Intermediate Similarity	NPD5737	Approved
0.8	Intermediate Similarity	NPD6098	Approved
0.7955	Intermediate Similarity	NPD8035	Phase 2
0.7955	Intermediate Similarity	NPD8034	Phase 2
0.7931	Intermediate Similarity	NPD6673	Approved
0.7931	Intermediate Similarity	NPD6080	Approved
0.7931	Intermediate Similarity	NPD6904	Approved
0.7865	Intermediate Similarity	NPD6399	Phase 3
0.7841	Intermediate Similarity	NPD5207	Approved
0.7816	Intermediate Similarity	NPD6903	Approved
0.7791	Intermediate Similarity	NPD6409	Approved
0.7791	Intermediate Similarity	NPD7521	Approved
0.7791	Intermediate Similarity	NPD7334	Approved
0.7791	Intermediate Similarity	NPD7146	Approved
0.7791	Intermediate Similarity	NPD6684	Approved
0.7791	Intermediate Similarity	NPD5330	Approved
0.7778	Intermediate Similarity	NPD6001	Approved
0.7674	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7614	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7614	Intermediate Similarity	NPD5208	Approved
0.7556	Intermediate Similarity	NPD5693	Phase 1
0.7556	Intermediate Similarity	NPD6050	Approved
0.7527	Intermediate Similarity	NPD6084	Phase 2
0.7527	Intermediate Similarity	NPD6083	Phase 2
0.75	Intermediate Similarity	NPD6052	Approved
0.7447	Intermediate Similarity	NPD5696	Approved
0.7444	Intermediate Similarity	NPD5692	Phase 3
0.7442	Intermediate Similarity	NPD4788	Approved
0.7375	Intermediate Similarity	NPD5777	Approved
0.7363	Intermediate Similarity	NPD5694	Approved
0.7347	Intermediate Similarity	NPD6008	Approved
0.7326	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD3702	Approved
0.7312	Intermediate Similarity	NPD5695	Phase 3
0.7174	Intermediate Similarity	NPD5284	Approved
0.7174	Intermediate Similarity	NPD5281	Approved
0.716	Intermediate Similarity	NPD6081	Approved
0.7159	Intermediate Similarity	NPD4786	Approved
0.7143	Intermediate Similarity	NPD6051	Approved
0.7126	Intermediate Similarity	NPD4223	Phase 3
0.7126	Intermediate Similarity	NPD4221	Approved
0.7079	Intermediate Similarity	NPD5329	Approved
0.703	Intermediate Similarity	NPD7320	Approved
0.7024	Intermediate Similarity	NPD6117	Approved
0.7021	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD7900	Approved
0.7	Intermediate Similarity	NPD6402	Approved
0.7	Intermediate Similarity	NPD5739	Approved
0.7	Intermediate Similarity	NPD6675	Approved
0.7	Intermediate Similarity	NPD7128	Approved
0.6988	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD3668	Phase 3
0.6966	Remote Similarity	NPD4197	Approved
0.6962	Remote Similarity	NPD4224	Phase 2
0.6961	Remote Similarity	NPD6372	Approved
0.6961	Remote Similarity	NPD6373	Approved
0.6957	Remote Similarity	NPD4753	Phase 2
0.6947	Remote Similarity	NPD5654	Approved
0.6941	Remote Similarity	NPD6116	Phase 1
0.6932	Remote Similarity	NPD3667	Approved
0.6931	Remote Similarity	NPD6614	Approved
0.6923	Remote Similarity	NPD3573	Approved
0.6863	Remote Similarity	NPD6899	Approved
0.6863	Remote Similarity	NPD6881	Approved
0.686	Remote Similarity	NPD6115	Approved
0.686	Remote Similarity	NPD6118	Approved
0.686	Remote Similarity	NPD6697	Approved
0.686	Remote Similarity	NPD6114	Approved
0.6842	Remote Similarity	NPD7748	Approved
0.6835	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD4747	Approved
0.6827	Remote Similarity	NPD6649	Approved
0.6827	Remote Similarity	NPD6650	Approved
0.6813	Remote Similarity	NPD4690	Approved
0.6813	Remote Similarity	NPD4688	Approved
0.6813	Remote Similarity	NPD3618	Phase 1
0.6813	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD4693	Phase 3
0.6813	Remote Similarity	NPD4689	Approved
0.6813	Remote Similarity	NPD4138	Approved
0.6813	Remote Similarity	NPD5205	Approved
0.6804	Remote Similarity	NPD7902	Approved
0.6804	Remote Similarity	NPD5959	Approved
0.679	Remote Similarity	NPD5360	Phase 3
0.679	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.6778	Remote Similarity	NPD3665	Phase 1
0.6778	Remote Similarity	NPD3666	Approved
0.6778	Remote Similarity	NPD3133	Approved
0.6774	Remote Similarity	NPD5328	Approved
0.6771	Remote Similarity	NPD4629	Approved
0.6771	Remote Similarity	NPD5210	Approved
0.6765	Remote Similarity	NPD5701	Approved
0.6765	Remote Similarity	NPD5697	Approved
0.6735	Remote Similarity	NPD7638	Approved
0.6731	Remote Similarity	NPD6883	Approved
0.6731	Remote Similarity	NPD7102	Approved
0.6731	Remote Similarity	NPD7290	Approved
0.6707	Remote Similarity	NPD4137	Phase 3
0.6703	Remote Similarity	NPD1694	Approved
0.6699	Remote Similarity	NPD6011	Approved
0.6667	Remote Similarity	NPD7639	Approved
0.6667	Remote Similarity	NPD3617	Approved
0.6667	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6869	Approved
0.6667	Remote Similarity	NPD6847	Approved
0.6667	Remote Similarity	NPD7640	Approved
0.6667	Remote Similarity	NPD8130	Phase 1
0.6667	Remote Similarity	NPD6617	Approved
0.6635	Remote Similarity	NPD6013	Approved
0.6635	Remote Similarity	NPD6014	Approved
0.6635	Remote Similarity	NPD6012	Approved
0.6632	Remote Similarity	NPD7515	Phase 2
0.6632	Remote Similarity	NPD6079	Approved
0.663	Remote Similarity	NPD5280	Approved
0.663	Remote Similarity	NPD5690	Phase 2
0.663	Remote Similarity	NPD4694	Approved
0.6629	Remote Similarity	NPD4139	Approved
0.6629	Remote Similarity	NPD4692	Approved
0.6627	Remote Similarity	NPD4691	Approved
0.6627	Remote Similarity	NPD4789	Approved
0.6604	Remote Similarity	NPD6882	Approved
0.6604	Remote Similarity	NPD8297	Approved
0.6588	Remote Similarity	NPD5733	Approved
0.6585	Remote Similarity	NPD3621	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD4202	Approved
0.6548	Remote Similarity	NPD4243	Approved
0.6548	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6548	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6531	Remote Similarity	NPD5349	Clinical (unspecified phase)
0.6531	Remote Similarity	NPD4697	Phase 3
0.6517	Remote Similarity	NPD7525	Registered
0.6514	Remote Similarity	NPD7115	Discovery
0.6484	Remote Similarity	NPD5362	Discontinued
0.6477	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6465	Remote Similarity	NPD4755	Approved
0.6458	Remote Similarity	NPD7637	Suspended
0.6452	Remote Similarity	NPD5279	Phase 3
0.6444	Remote Similarity	NPD5369	Approved
0.6429	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD4244	Approved
0.6429	Remote Similarity	NPD4245	Approved
0.6421	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6404	Remote Similarity	NPD4195	Approved
0.6395	Remote Similarity	NPD4687	Approved
0.6395	Remote Similarity	NPD4058	Approved
0.6395	Remote Similarity	NPD4785	Approved
0.6395	Remote Similarity	NPD4784	Approved
0.6395	Remote Similarity	NPD6926	Approved
0.6395	Remote Similarity	NPD6924	Approved
0.6389	Remote Similarity	NPD8133	Approved
0.6364	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD5221	Approved
0.6364	Remote Similarity	NPD5222	Approved
0.6364	Remote Similarity	NPD7732	Phase 3
0.6353	Remote Similarity	NPD4758	Discontinued
0.6353	Remote Similarity	NPD5276	Approved
0.6337	Remote Similarity	NPD5285	Approved
0.6337	Remote Similarity	NPD5286	Approved
0.6337	Remote Similarity	NPD4700	Approved
0.6337	Remote Similarity	NPD4696	Approved
0.6333	Remote Similarity	NPD4695	Discontinued
0.6327	Remote Similarity	NPD5707	Approved
0.6322	Remote Similarity	NPD6942	Approved
0.6322	Remote Similarity	NPD7339	Approved
0.6322	Remote Similarity	NPD8039	Approved
0.631	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.631	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.631	Remote Similarity	NPD3698	Phase 2
0.6306	Remote Similarity	NPD6335	Approved
0.6304	Remote Similarity	NPD6695	Phase 3
0.63	Remote Similarity	NPD5173	Approved
0.6292	Remote Similarity	NPD5364	Discontinued
0.6289	Remote Similarity	NPD6411	Approved
0.6286	Remote Similarity	NPD6412	Phase 2
0.6277	Remote Similarity	NPD4519	Discontinued
0.6277	Remote Similarity	NPD4623	Approved
0.6275	Remote Similarity	NPD5223	Approved
0.6273	Remote Similarity	NPD6274	Approved
0.6273	Remote Similarity	NPD6868	Approved
0.6261	Remote Similarity	NPD7492	Approved
0.625	Remote Similarity	NPD1695	Approved
0.625	Remote Similarity	NPD7101	Approved
0.625	Remote Similarity	NPD7100	Approved
0.625	Remote Similarity	NPD6933	Approved
0.6239	Remote Similarity	NPD4632	Approved
0.6238	Remote Similarity	NPD4225	Approved
0.6237	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6216	Remote Similarity	NPD6317	Approved
0.6214	Remote Similarity	NPD5224	Approved
0.6214	Remote Similarity	NPD5211	Phase 2
0.6214	Remote Similarity	NPD5226	Approved
0.6214	Remote Similarity	NPD5225	Approved
0.6214	Remote Similarity	NPD5091	Approved
0.6214	Remote Similarity	NPD4633	Approved
0.6214	Remote Similarity	NPD7632	Discontinued
0.6207	Remote Similarity	NPD6616	Approved
0.6196	Remote Similarity	NPD6435	Approved
0.6195	Remote Similarity	NPD6059	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