NPASS Compound

Structure

NPC170038 OpenBabel07101718322D 33 36 0 0 1 0 0 0 0 0999 V2000 -5.1110 -6.6152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7962 -2.5325 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.6388 -1.0730 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6245 -2.4021 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3934 0.4881 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2684 1.8459 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9173 -0.6242 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5975 -5.7726 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5831 -1.0730 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4257 -1.5595 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9536 -0.1001 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2558 1.4398 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1110 -3.2448 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0824 1.5721 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5975 -2.4021 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2234 1.3381 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1110 0.3864 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8574 1.3203 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7962 -1.5595 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9536 -1.0730 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5831 -0.1001 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.8601 0.5510 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.2684 -1.0730 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.5975 -4.0874 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6123 0.7561 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1110 -1.5595 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.4257 0.3864 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.2684 -0.1001 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9083 0.3487 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.5704 -4.0874 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5840 0.7052 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1110 -4.9300 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 19 2 0 0 0 0 3 19 1 0 0 0 0 5 27 1 0 0 0 0 8 32 1 0 0 0 0 9 10 1 0 0 0 0 9 21 1 0 0 0 0 10 23 1 0 0 0 0 11 17 1 0 0 0 0 11 20 1 0 0 0 0 12 16 1 0 0 0 0 13 15 1 0 0 0 0 13 24 1 0 0 0 0 14 18 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 29 1 0 0 0 0 19 20 1 0 0 0 0 20 26 1 6 0 0 0 21 22 1 0 0 0 0 21 27 1 1 0 0 0 22 12 1 6 0 0 0 22 29 1 0 0 0 0 23 26 1 6 0 0 0 23 28 1 0 0 0 0 24 30 2 0 0 0 0 24 32 1 0 0 0 0 25 31 2 0 0 0 0 25 33 1 0 0 0 0 26 4 1 6 0 0 0 27 28 1 6 0 0 0 28 6 1 6 0 0 0 29 7 1 1 0 0 0 29 33 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	458.34
Volume:	503.166
LogP:	6.094
LogD:	5.095
LogS:	-5.85
# Rotatable Bonds:	7
TPSA:	52.6
# H-Bond Aceptor:	4
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.322
Synthetic Accessibility Score:	4.699
Fsp3:	0.862
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.759
MDCK Permeability:	3.845732499030419e-05
Pgp-inhibitor:	0.996
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.002
20% Bioavailability (F20%):	0.022
30% Bioavailability (F30%):	0.565

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.022
Plasma Protein Binding (PPB):	91.57756805419922%
Volume Distribution (VD):	0.614
Pgp-substrate:	3.486633777618408%

ADMET: Metabolism

CYP1A2-inhibitor:	0.139
CYP1A2-substrate:	0.233
CYP2C19-inhibitor:	0.207
CYP2C19-substrate:	0.921
CYP2C9-inhibitor:	0.37
CYP2C9-substrate:	0.134
CYP2D6-inhibitor:	0.068
CYP2D6-substrate:	0.258
CYP3A4-inhibitor:	0.894
CYP3A4-substrate:	0.723

ADMET: Excretion

Clearance (CL):	8.081
Half-life (T1/2):	0.171

ADMET: Toxicity

hERG Blockers:	0.856
Human Hepatotoxicity (H-HT):	0.31
Drug-inuced Liver Injury (DILI):	0.401
AMES Toxicity:	0.003
Rat Oral Acute Toxicity:	0.065
Maximum Recommended Daily Dose:	0.228
Skin Sensitization:	0.962
Carcinogencity:	0.169
Eye Corrosion:	0.74
Eye Irritation:	0.13
Respiratory Toxicity:	0.953

Download Data

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

Natural Product: NPC170038

Natural Product ID:	NPC170038
*Common Name:**	Ethyl Eichlerialactone
IUPAC Name:	ethyl 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:	LRUQUTTZMVYITE-FENQSEDKSA-N
Standard InCHI:	InChI=1S/C29H46O4/c1-8-32-24(30)13-15-26(4)20(19(2)3)11-17-28(6)23(26)10-9-21-22(12-16-27(21,28)5)29(7)18-14-25(31)33-29/h20-23H,2,8-18H2,1,3-7H3/t20-,21+,22-,23+,26-,27+,28+,29-/m0/s1
SMILES:	CCOC(=O)CC[C@@]1(C)[C@@H](CC[C@@]2([C@@H]1CC[C@H]1[C@@]2(C)CC[C@@H]1[C@]1(C)CCC(=O)O1)C)C(=C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3109458
PubChem CID:	76332083
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	=	38400.0	nM	PMID[524104]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	50000.0	nM	PMID[524104]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	50000.0	nM	PMID[524104]
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	>	100000.0	nM	PMID[524104]

☑ 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 NPC170038 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	180
0.1-0.2	1679
0.2-0.3	9266
0.3-0.4	13899
0.4-0.5	5744
0.5-0.6	6940
0.6-0.7	4219
0.7-0.8	717
0.8-0.85	37
0.85-0.9	13
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9865	High Similarity	NPC118987
0.9351	High Similarity	NPC232625
0.9	High Similarity	NPC100391
0.8889	High Similarity	NPC470223
0.8795	High Similarity	NPC229407
0.8795	High Similarity	NPC48824
0.8795	High Similarity	NPC250687
0.8795	High Similarity	NPC254572
0.869	High Similarity	NPC269267
0.8675	High Similarity	NPC167877
0.8608	High Similarity	NPC471475
0.8571	High Similarity	NPC28227
0.8553	High Similarity	NPC279241
0.8519	High Similarity	NPC476458
0.8519	High Similarity	NPC258153
0.8488	Intermediate Similarity	NPC471747
0.8481	Intermediate Similarity	NPC63020
0.8462	Intermediate Similarity	NPC92489
0.8462	Intermediate Similarity	NPC476601
0.8434	Intermediate Similarity	NPC98270
0.8415	Intermediate Similarity	NPC170862
0.8415	Intermediate Similarity	NPC471037
0.8378	Intermediate Similarity	NPC469868
0.8354	Intermediate Similarity	NPC66105
0.8354	Intermediate Similarity	NPC238227
0.8353	Intermediate Similarity	NPC255176
0.8333	Intermediate Similarity	NPC471042
0.8315	Intermediate Similarity	NPC322063
0.8313	Intermediate Similarity	NPC475509
0.8293	Intermediate Similarity	NPC240302
0.825	Intermediate Similarity	NPC321690
0.8235	Intermediate Similarity	NPC474174
0.8235	Intermediate Similarity	NPC251808
0.8228	Intermediate Similarity	NPC246445
0.8202	Intermediate Similarity	NPC280877
0.8182	Intermediate Similarity	NPC470224
0.8182	Intermediate Similarity	NPC475700
0.8182	Intermediate Similarity	NPC197701
0.8171	Intermediate Similarity	NPC475951
0.814	Intermediate Similarity	NPC4309
0.8118	Intermediate Similarity	NPC472505
0.8118	Intermediate Similarity	NPC264127
0.8118	Intermediate Similarity	NPC80590
0.8118	Intermediate Similarity	NPC475007
0.8111	Intermediate Similarity	NPC307164
0.809	Intermediate Similarity	NPC472223
0.809	Intermediate Similarity	NPC472224
0.8068	Intermediate Similarity	NPC160506
0.8068	Intermediate Similarity	NPC150383
0.8049	Intermediate Similarity	NPC274522
0.8049	Intermediate Similarity	NPC476265
0.8046	Intermediate Similarity	NPC474570
0.8046	Intermediate Similarity	NPC11611
0.8023	Intermediate Similarity	NPC128644
0.8023	Intermediate Similarity	NPC33768
0.8023	Intermediate Similarity	NPC134197
0.8023	Intermediate Similarity	NPC265580
0.8022	Intermediate Similarity	NPC253586
0.8022	Intermediate Similarity	NPC475894
0.8	Intermediate Similarity	NPC474971
0.8	Intermediate Similarity	NPC201655
0.8	Intermediate Similarity	NPC20466
0.7976	Intermediate Similarity	NPC245866
0.7955	Intermediate Similarity	NPC471896
0.7952	Intermediate Similarity	NPC223330
0.7952	Intermediate Similarity	NPC209318
0.7952	Intermediate Similarity	NPC327002
0.7935	Intermediate Similarity	NPC252295
0.7935	Intermediate Similarity	NPC153792
0.7935	Intermediate Similarity	NPC271387
0.7935	Intermediate Similarity	NPC473155
0.7931	Intermediate Similarity	NPC474719
0.7931	Intermediate Similarity	NPC183374
0.7931	Intermediate Similarity	NPC97884
0.7931	Intermediate Similarity	NPC472220
0.7931	Intermediate Similarity	NPC211162
0.7927	Intermediate Similarity	NPC192744
0.7907	Intermediate Similarity	NPC2783
0.7907	Intermediate Similarity	NPC70661
0.7907	Intermediate Similarity	NPC470050
0.7907	Intermediate Similarity	NPC195640
0.7907	Intermediate Similarity	NPC12774
0.7907	Intermediate Similarity	NPC470051
0.7901	Intermediate Similarity	NPC68828
0.7901	Intermediate Similarity	NPC475932
0.7882	Intermediate Similarity	NPC263974
0.7865	Intermediate Similarity	NPC471901
0.7865	Intermediate Similarity	NPC154101
0.7857	Intermediate Similarity	NPC13494
0.7857	Intermediate Similarity	NPC327969
0.7857	Intermediate Similarity	NPC321289
0.7857	Intermediate Similarity	NPC226988
0.7857	Intermediate Similarity	NPC133391
0.7849	Intermediate Similarity	NPC470906
0.7849	Intermediate Similarity	NPC108371
0.7849	Intermediate Similarity	NPC476303
0.7848	Intermediate Similarity	NPC244708
0.7848	Intermediate Similarity	NPC330659
0.7848	Intermediate Similarity	NPC161187
0.7841	Intermediate Similarity	NPC116146
0.7841	Intermediate Similarity	NPC473039
0.7841	Intermediate Similarity	NPC474679
0.7841	Intermediate Similarity	NPC24772
0.7841	Intermediate Similarity	NPC288699
0.7841	Intermediate Similarity	NPC215029
0.7841	Intermediate Similarity	NPC471043
0.7841	Intermediate Similarity	NPC474889
0.7841	Intermediate Similarity	NPC305039
0.7841	Intermediate Similarity	NPC476733
0.7831	Intermediate Similarity	NPC206735
0.7831	Intermediate Similarity	NPC304194
0.7826	Intermediate Similarity	NPC469810
0.7821	Intermediate Similarity	NPC91369
0.7816	Intermediate Similarity	NPC269360
0.7816	Intermediate Similarity	NPC175293
0.7816	Intermediate Similarity	NPC96496
0.7816	Intermediate Similarity	NPC264005
0.7805	Intermediate Similarity	NPC35574
0.7805	Intermediate Similarity	NPC321514
0.7802	Intermediate Similarity	NPC469599
0.7802	Intermediate Similarity	NPC279974
0.7792	Intermediate Similarity	NPC36616
0.7792	Intermediate Similarity	NPC290445
0.7791	Intermediate Similarity	NPC323765
0.7791	Intermediate Similarity	NPC329738
0.7791	Intermediate Similarity	NPC269638
0.7791	Intermediate Similarity	NPC264317
0.7791	Intermediate Similarity	NPC283733
0.7791	Intermediate Similarity	NPC294438
0.7778	Intermediate Similarity	NPC473690
0.7778	Intermediate Similarity	NPC476985
0.7778	Intermediate Similarity	NPC294263
0.7778	Intermediate Similarity	NPC474316
0.7778	Intermediate Similarity	NPC471902
0.7778	Intermediate Similarity	NPC475061
0.7778	Intermediate Similarity	NPC287118
0.7778	Intermediate Similarity	NPC41017
0.7778	Intermediate Similarity	NPC475744
0.7765	Intermediate Similarity	NPC167103
0.7765	Intermediate Similarity	NPC477373
0.7753	Intermediate Similarity	NPC474842
0.7753	Intermediate Similarity	NPC148414
0.7753	Intermediate Similarity	NPC475965
0.7753	Intermediate Similarity	NPC175628
0.7753	Intermediate Similarity	NPC111585
0.775	Intermediate Similarity	NPC475517
0.775	Intermediate Similarity	NPC474524
0.7738	Intermediate Similarity	NPC58631
0.7738	Intermediate Similarity	NPC147066
0.7738	Intermediate Similarity	NPC474955
0.7727	Intermediate Similarity	NPC16377
0.7727	Intermediate Similarity	NPC294480
0.7727	Intermediate Similarity	NPC226863
0.7727	Intermediate Similarity	NPC56413
0.7727	Intermediate Similarity	NPC474845
0.7727	Intermediate Similarity	NPC472870
0.7727	Intermediate Similarity	NPC183546
0.7722	Intermediate Similarity	NPC469940
0.7722	Intermediate Similarity	NPC72343
0.7711	Intermediate Similarity	NPC327674
0.7711	Intermediate Similarity	NPC476438
0.7711	Intermediate Similarity	NPC477371
0.7711	Intermediate Similarity	NPC47808
0.7711	Intermediate Similarity	NPC153987
0.7711	Intermediate Similarity	NPC192999
0.7711	Intermediate Similarity	NPC44083
0.7711	Intermediate Similarity	NPC201459
0.7711	Intermediate Similarity	NPC158846
0.7711	Intermediate Similarity	NPC305835
0.7708	Intermediate Similarity	NPC472227
0.7708	Intermediate Similarity	NPC471293
0.7708	Intermediate Similarity	NPC472228
0.7703	Intermediate Similarity	NPC306750
0.7701	Intermediate Similarity	NPC155011
0.7701	Intermediate Similarity	NPC9231
0.7701	Intermediate Similarity	NPC212843
0.7692	Intermediate Similarity	NPC5714
0.7692	Intermediate Similarity	NPC100257
0.7692	Intermediate Similarity	NPC56525
0.7692	Intermediate Similarity	NPC224410
0.7692	Intermediate Similarity	NPC41649
0.7692	Intermediate Similarity	NPC159410
0.7692	Intermediate Similarity	NPC303863
0.7692	Intermediate Similarity	NPC124207
0.7683	Intermediate Similarity	NPC212661
0.7683	Intermediate Similarity	NPC471035
0.7674	Intermediate Similarity	NPC97505
0.7674	Intermediate Similarity	NPC165064
0.7674	Intermediate Similarity	NPC194937
0.7674	Intermediate Similarity	NPC109512
0.7674	Intermediate Similarity	NPC470011
0.7674	Intermediate Similarity	NPC139566
0.7674	Intermediate Similarity	NPC320801
0.7674	Intermediate Similarity	NPC469407
0.7674	Intermediate Similarity	NPC476038
0.7667	Intermediate Similarity	NPC470230
0.7667	Intermediate Similarity	NPC475416
0.7667	Intermediate Similarity	NPC218301
0.7667	Intermediate Similarity	NPC26888
0.7667	Intermediate Similarity	NPC470113

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 NPC170038 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	2099
0.2-0.3	4340
0.3-0.4	1670
0.4-0.5	454
0.5-0.6	184
0.6-0.7	191
0.7-0.8	43
0.8-0.85	4
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8202	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.814	Intermediate Similarity	NPD6672	Approved
0.814	Intermediate Similarity	NPD5737	Approved
0.8068	Intermediate Similarity	NPD8034	Phase 2
0.8068	Intermediate Similarity	NPD8035	Phase 2
0.7978	Intermediate Similarity	NPD6399	Phase 3
0.7931	Intermediate Similarity	NPD6903	Approved
0.7907	Intermediate Similarity	NPD5330	Approved
0.7907	Intermediate Similarity	NPD7521	Approved
0.7907	Intermediate Similarity	NPD7334	Approved
0.7907	Intermediate Similarity	NPD6409	Approved
0.7907	Intermediate Similarity	NPD7146	Approved
0.7907	Intermediate Similarity	NPD6684	Approved
0.7907	Intermediate Similarity	NPD6098	Approved
0.7841	Intermediate Similarity	NPD6673	Approved
0.7841	Intermediate Similarity	NPD6080	Approved
0.7841	Intermediate Similarity	NPD6904	Approved
0.7791	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7753	Intermediate Similarity	NPD5207	Approved
0.7727	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD6001	Approved
0.7634	Intermediate Similarity	NPD6083	Phase 2
0.7634	Intermediate Similarity	NPD6084	Phase 2
0.7558	Intermediate Similarity	NPD4788	Approved
0.7553	Intermediate Similarity	NPD5696	Approved
0.7528	Intermediate Similarity	NPD5208	Approved
0.75	Intermediate Similarity	NPD5777	Approved
0.7473	Intermediate Similarity	NPD5693	Phase 1
0.7473	Intermediate Similarity	NPD6050	Approved
0.7449	Intermediate Similarity	NPD6008	Approved
0.7442	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7439	Intermediate Similarity	NPD3702	Approved
0.7423	Intermediate Similarity	NPD6052	Approved
0.7419	Intermediate Similarity	NPD5695	Phase 3
0.7363	Intermediate Similarity	NPD5692	Phase 3
0.7283	Intermediate Similarity	NPD5694	Approved
0.7273	Intermediate Similarity	NPD4786	Approved
0.7253	Intermediate Similarity	NPD6051	Approved
0.7143	Intermediate Similarity	NPD6117	Approved
0.7129	Intermediate Similarity	NPD7320	Approved
0.7128	Intermediate Similarity	NPD7900	Approved
0.7128	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.71	Intermediate Similarity	NPD5739	Approved
0.71	Intermediate Similarity	NPD7128	Approved
0.71	Intermediate Similarity	NPD6675	Approved
0.71	Intermediate Similarity	NPD6402	Approved
0.7097	Intermediate Similarity	NPD5281	Approved
0.7097	Intermediate Similarity	NPD5284	Approved
0.7079	Intermediate Similarity	NPD3668	Phase 3
0.7073	Intermediate Similarity	NPD6081	Approved
0.7065	Intermediate Similarity	NPD4753	Phase 2
0.7059	Intermediate Similarity	NPD6116	Phase 1
0.7059	Intermediate Similarity	NPD6373	Approved
0.7059	Intermediate Similarity	NPD6372	Approved
0.7045	Intermediate Similarity	NPD4223	Phase 3
0.7045	Intermediate Similarity	NPD3667	Approved
0.7045	Intermediate Similarity	NPD4221	Approved
0.7	Intermediate Similarity	NPD5329	Approved
0.6977	Remote Similarity	NPD6114	Approved
0.6977	Remote Similarity	NPD6115	Approved
0.6977	Remote Similarity	NPD6697	Approved
0.6977	Remote Similarity	NPD6118	Approved
0.6962	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.6961	Remote Similarity	NPD6881	Approved
0.6961	Remote Similarity	NPD6899	Approved
0.6947	Remote Similarity	NPD7748	Approved
0.6923	Remote Similarity	NPD3618	Phase 1
0.6923	Remote Similarity	NPD6649	Approved
0.6923	Remote Similarity	NPD6650	Approved
0.6907	Remote Similarity	NPD7902	Approved
0.6889	Remote Similarity	NPD3133	Approved
0.6889	Remote Similarity	NPD3666	Approved
0.6889	Remote Similarity	NPD4197	Approved
0.6889	Remote Similarity	NPD3665	Phase 1
0.6882	Remote Similarity	NPD5328	Approved
0.6875	Remote Similarity	NPD5210	Approved
0.6875	Remote Similarity	NPD4224	Phase 2
0.6875	Remote Similarity	NPD4629	Approved
0.6875	Remote Similarity	NPD5654	Approved
0.6863	Remote Similarity	NPD5701	Approved
0.6863	Remote Similarity	NPD5697	Approved
0.6863	Remote Similarity	NPD6614	Approved
0.6848	Remote Similarity	NPD3573	Approved
0.6837	Remote Similarity	NPD7638	Approved
0.6827	Remote Similarity	NPD7290	Approved
0.6827	Remote Similarity	NPD6883	Approved
0.6827	Remote Similarity	NPD7102	Approved
0.6813	Remote Similarity	NPD1694	Approved
0.6796	Remote Similarity	NPD6011	Approved
0.6768	Remote Similarity	NPD7640	Approved
0.6768	Remote Similarity	NPD7639	Approved
0.6762	Remote Similarity	NPD6869	Approved
0.6762	Remote Similarity	NPD6847	Approved
0.6762	Remote Similarity	NPD8130	Phase 1
0.6762	Remote Similarity	NPD6617	Approved
0.6762	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6747	Remote Similarity	NPD4789	Approved
0.6747	Remote Similarity	NPD4747	Approved
0.6739	Remote Similarity	NPD4693	Phase 3
0.6739	Remote Similarity	NPD4689	Approved
0.6739	Remote Similarity	NPD4688	Approved
0.6739	Remote Similarity	NPD4138	Approved
0.6739	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD4690	Approved
0.6739	Remote Similarity	NPD5205	Approved
0.6737	Remote Similarity	NPD6079	Approved
0.6737	Remote Similarity	NPD7515	Phase 2
0.6735	Remote Similarity	NPD5959	Approved
0.6731	Remote Similarity	NPD6012	Approved
0.6731	Remote Similarity	NPD6014	Approved
0.6731	Remote Similarity	NPD6013	Approved
0.6707	Remote Similarity	NPD5360	Phase 3
0.6707	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.6698	Remote Similarity	NPD6882	Approved
0.6698	Remote Similarity	NPD8297	Approved
0.6667	Remote Similarity	NPD4202	Approved
0.6667	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6633	Remote Similarity	NPD4697	Phase 3
0.6633	Remote Similarity	NPD5349	Clinical (unspecified phase)
0.6629	Remote Similarity	NPD7525	Registered
0.6627	Remote Similarity	NPD4137	Phase 3
0.6606	Remote Similarity	NPD7115	Discovery
0.6593	Remote Similarity	NPD5362	Discontinued
0.6591	Remote Similarity	NPD3617	Approved
0.6591	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6566	Remote Similarity	NPD4755	Approved
0.6562	Remote Similarity	NPD7637	Suspended
0.6559	Remote Similarity	NPD5690	Phase 2
0.6559	Remote Similarity	NPD5280	Approved
0.6559	Remote Similarity	NPD5279	Phase 3
0.6559	Remote Similarity	NPD4694	Approved
0.6556	Remote Similarity	NPD4139	Approved
0.6556	Remote Similarity	NPD4692	Approved
0.6556	Remote Similarity	NPD5369	Approved
0.6548	Remote Similarity	NPD4245	Approved
0.6548	Remote Similarity	NPD4244	Approved
0.6548	Remote Similarity	NPD4691	Approved
0.6518	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6512	Remote Similarity	NPD6926	Approved
0.6512	Remote Similarity	NPD6924	Approved
0.6512	Remote Similarity	NPD5733	Approved
0.6506	Remote Similarity	NPD3621	Clinical (unspecified phase)
0.6481	Remote Similarity	NPD8133	Approved
0.6471	Remote Similarity	NPD4243	Approved
0.6465	Remote Similarity	NPD5221	Approved
0.6465	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6465	Remote Similarity	NPD5222	Approved
0.6437	Remote Similarity	NPD6942	Approved
0.6437	Remote Similarity	NPD7339	Approved
0.6437	Remote Similarity	NPD8039	Approved
0.6436	Remote Similarity	NPD5286	Approved
0.6436	Remote Similarity	NPD4700	Approved
0.6436	Remote Similarity	NPD4696	Approved
0.6436	Remote Similarity	NPD5285	Approved
0.6429	Remote Similarity	NPD3698	Phase 2
0.6429	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6413	Remote Similarity	NPD6695	Phase 3
0.64	Remote Similarity	NPD5173	Approved
0.6396	Remote Similarity	NPD6335	Approved
0.6392	Remote Similarity	NPD6411	Approved
0.6381	Remote Similarity	NPD6412	Phase 2
0.6373	Remote Similarity	NPD5223	Approved
0.6364	Remote Similarity	NPD6933	Approved
0.6364	Remote Similarity	NPD6868	Approved
0.6364	Remote Similarity	NPD6274	Approved
0.6354	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6354	Remote Similarity	NPD1695	Approved
0.6348	Remote Similarity	NPD7492	Approved
0.6344	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6339	Remote Similarity	NPD7101	Approved
0.6339	Remote Similarity	NPD7100	Approved
0.6337	Remote Similarity	NPD4225	Approved
0.6333	Remote Similarity	NPD4195	Approved
0.633	Remote Similarity	NPD4632	Approved
0.6322	Remote Similarity	NPD4687	Approved
0.6322	Remote Similarity	NPD4784	Approved
0.6322	Remote Similarity	NPD4785	Approved
0.6322	Remote Similarity	NPD4058	Approved
0.6311	Remote Similarity	NPD7632	Discontinued
0.6311	Remote Similarity	NPD5225	Approved
0.6311	Remote Similarity	NPD5224	Approved
0.6311	Remote Similarity	NPD5211	Phase 2
0.6311	Remote Similarity	NPD5226	Approved
0.6311	Remote Similarity	NPD4633	Approved
0.6306	Remote Similarity	NPD6317	Approved
0.6304	Remote Similarity	NPD6435	Approved
0.63	Remote Similarity	NPD7732	Phase 3
0.6293	Remote Similarity	NPD6616	Approved
0.6283	Remote Similarity	NPD6054	Approved
0.6283	Remote Similarity	NPD6059	Approved
0.6279	Remote Similarity	NPD5276	Approved
0.6279	Remote Similarity	NPD4758	Discontinued
0.6277	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6264	Remote Similarity	NPD4695	Discontinued
0.6263	Remote Similarity	NPD5707	Approved
0.625	Remote Similarity	NPD1145	Discontinued
0.625	Remote Similarity	NPD6313	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