NPASS Compound

Structure

NPC108744 OpenBabel07101718182D 33 36 0 0 1 0 0 0 0 0999 V2000 -1.1554 2.3801 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0685 -3.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9345 -3.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2588 -1.9659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2426 4.2426 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0532 1.6037 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4752 -1.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1213 2.1213 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3461 0.8966 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7944 2.5696 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.3801 1.1554 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8284 2.8284 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8660 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.0739 -2.4781 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6730 0.4483 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0685 -2.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0000 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.7321 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.0000 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5696 3.7944 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0 2.7321 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.6049 -0.0694 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4048 -3.2213 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.9319 -0.5176 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3198 -0.1910 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2588 0.9659 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.5015 3.2767 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7071 0.7071 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 11 1 0 0 0 0 2 21 1 0 0 0 0 3 21 1 0 0 0 0 4 22 1 0 0 0 0 5 32 1 0 0 0 0 6 13 2 0 0 0 0 6 14 1 0 0 0 0 7 12 2 0 0 0 0 7 23 1 0 0 0 0 8 15 1 0 0 0 0 8 22 1 0 0 0 0 9 12 1 0 0 0 0 9 26 2 0 0 0 0 10 21 1 0 0 0 0 10 23 1 0 0 0 0 11 16 2 0 0 0 0 11 17 1 0 0 0 0 12 24 1 0 0 0 0 13 16 1 0 0 0 0 13 27 1 0 0 0 0 14 17 2 0 0 0 0 14 32 1 0 0 0 0 15 24 1 1 0 0 0 15 33 1 0 0 0 0 16 20 1 0 0 0 0 17 25 1 0 0 0 0 18 19 1 0 0 0 0 18 22 1 6 0 0 0 18 23 1 0 0 0 0 19 21 1 0 0 0 0 19 28 1 6 0 0 0 20 29 2 0 0 0 0 20 33 1 0 0 0 0 22 24 1 6 0 0 0 23 30 1 1 0 0 0 24 31 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	480.16
Volume:	459.148
LogP:	3.36
LogD:	1.848
LogS:	-3.957
# Rotatable Bonds:	5
TPSA:	133.52
# H-Bond Aceptor:	8
# H-Bond Donor:	4
# Rings:	4
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.381
Synthetic Accessibility Score:	5.068
Fsp3:	0.583
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.02
MDCK Permeability:	1.4361155081132893e-05
Pgp-inhibitor:	0.003
Pgp-substrate:	0.383
Human Intestinal Absorption (HIA):	0.056
20% Bioavailability (F20%):	0.01
30% Bioavailability (F30%):	0.003

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.379
Plasma Protein Binding (PPB):	93.8078384399414%
Volume Distribution (VD):	1.11
Pgp-substrate:	4.465407371520996%

ADMET: Metabolism

CYP1A2-inhibitor:	0.186
CYP1A2-substrate:	0.386
CYP2C19-inhibitor:	0.619
CYP2C19-substrate:	0.504
CYP2C9-inhibitor:	0.763
CYP2C9-substrate:	0.757
CYP2D6-inhibitor:	0.483
CYP2D6-substrate:	0.151
CYP3A4-inhibitor:	0.731
CYP3A4-substrate:	0.272

ADMET: Excretion

Clearance (CL):	6.292
Half-life (T1/2):	0.207

ADMET: Toxicity

hERG Blockers:	0.043
Human Hepatotoxicity (H-HT):	0.235
Drug-inuced Liver Injury (DILI):	0.07
AMES Toxicity:	0.192
Rat Oral Acute Toxicity:	0.11
Maximum Recommended Daily Dose:	0.835
Skin Sensitization:	0.145
Carcinogencity:	0.647
Eye Corrosion:	0.006
Eye Irritation:	0.244
Respiratory Toxicity:	0.945

Download Data

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

Natural Product: NPC108744

Natural Product ID:	NPC108744
*Common Name:**	Melledonal C
IUPAC Name:	[(2R,2aS,4aR,7R,7aS,7bR)-3-formyl-2a,4a,7-trihydroxy-6,6,7b-trimethyl-2,5,7,7a-tetrahydro-1H-cyclobuta[e]inden-2-yl] 3-chloro-6-hydroxy-4-methoxy-2-methylbenzoate
Synonyms:	Melledonal C
Standard InCHIKey:	RCBZBPPFXBBNCD-IQEKTTGQSA-N
Standard InCHI:	InChI=1S/C24H29ClO8/c1-11-16(13(27)6-14(32-5)17(11)25)20(29)33-15-8-22(4)18-19(28)21(2,3)10-23(18,30)7-12(9-26)24(15,22)31/h6-7,9,15,18-19,27-28,30-31H,8,10H2,1-5H3/t15-,18-,19-,22-,23+,24+/m1/s1
SMILES:	Cc1c(c(cc(c1Cl)OC)O)C(=O)O[C@@H]1C[C@]2(C)[C@H]3[C@H](C(C)(C)C[C@]3(C=C(C=O)[C@]12O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1078144
PubChem CID:	189493
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001550] Sesquiterpenoids [CHEMONTID:0001777] Illudanes and illudins [CHEMONTID:0001776] Melleolides and analogues

*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
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]
NPO41429	Gloeophyllum abietinum + Heterobasidion annosum	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[8003259]
NPO41429	Gloeophyllum abietinum + Heterobasidion annosum	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[8216897]
NPO28689	Armillaria mellea	Species	Physalacriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28689	Armillaria mellea	Species	Physalacriaceae	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	4

Activity Type	# Activity
Cell Line	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT393	Cell Line	HCT-116	Homo sapiens	IC50	>	100000.0	nM	PMID[468898]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	100000.0	nM	PMID[468898]
NPT15	Cell Line	Jurkat	Homo sapiens	IC50	=	58750.0	nM	PMID[468898]
NPT404	Cell Line	CCRF-CEM	Homo sapiens	IC50	=	14750.0	nM	PMID[468898]

☑ 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 NPC108744 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	463
0.1-0.2	1916
0.2-0.3	4156
0.3-0.4	9932
0.4-0.5	10169
0.5-0.6	6133
0.6-0.7	9329
0.7-0.8	582
0.8-0.85	7
0.85-0.9	2
0.9-0.95	3
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.9778	High Similarity	NPC48822
0.9722	High Similarity	NPC247104
0.9667	High Similarity	NPC221185
0.9556	High Similarity	NPC470100
0.9389	High Similarity	NPC470103
0.9341	High Similarity	NPC470099
0.9333	High Similarity	NPC99937
0.8667	High Similarity	NPC165460
0.8611	High Similarity	NPC211592
0.8486	Intermediate Similarity	NPC477568
0.8325	Intermediate Similarity	NPC474499
0.8315	Intermediate Similarity	NPC472032
0.8182	Intermediate Similarity	NPC474857
0.8152	Intermediate Similarity	NPC470081
0.8142	Intermediate Similarity	NPC472405
0.8138	Intermediate Similarity	NPC470422
0.8112	Intermediate Similarity	NPC214901
0.8111	Intermediate Similarity	NPC470102
0.8098	Intermediate Similarity	NPC473696
0.8095	Intermediate Similarity	NPC264922
0.8065	Intermediate Similarity	NPC28669
0.8061	Intermediate Similarity	NPC220369
0.8043	Intermediate Similarity	NPC298401
0.804	Intermediate Similarity	NPC154720
0.803	Intermediate Similarity	NPC313541
0.803	Intermediate Similarity	NPC198163
0.8011	Intermediate Similarity	NPC58653
0.8011	Intermediate Similarity	NPC173352
0.8	Intermediate Similarity	NPC474096
0.7978	Intermediate Similarity	NPC472404
0.7968	Intermediate Similarity	NPC474061
0.7937	Intermediate Similarity	NPC277865
0.7908	Intermediate Similarity	NPC316091
0.7897	Intermediate Similarity	NPC191606
0.7895	Intermediate Similarity	NPC470560
0.7892	Intermediate Similarity	NPC472055
0.7876	Intermediate Similarity	NPC471801
0.7865	Intermediate Similarity	NPC45072
0.785	Intermediate Similarity	NPC193676
0.7842	Intermediate Similarity	NPC470562
0.7842	Intermediate Similarity	NPC107283
0.7838	Intermediate Similarity	NPC470339
0.7826	Intermediate Similarity	NPC472050
0.7817	Intermediate Similarity	NPC136411
0.7817	Intermediate Similarity	NPC313386
0.7807	Intermediate Similarity	NPC245122
0.7802	Intermediate Similarity	NPC215921
0.7802	Intermediate Similarity	NPC70016
0.7802	Intermediate Similarity	NPC200773
0.7802	Intermediate Similarity	NPC240768
0.7801	Intermediate Similarity	NPC188618
0.7778	Intermediate Similarity	NPC39409
0.776	Intermediate Similarity	NPC470340
0.7754	Intermediate Similarity	NPC117985
0.7749	Intermediate Similarity	NPC470565
0.7747	Intermediate Similarity	NPC179178
0.7744	Intermediate Similarity	NPC151292
0.7732	Intermediate Similarity	NPC28160
0.773	Intermediate Similarity	NPC280497
0.7727	Intermediate Similarity	NPC471812
0.7727	Intermediate Similarity	NPC471804
0.7727	Intermediate Similarity	NPC471803
0.772	Intermediate Similarity	NPC294149
0.7717	Intermediate Similarity	NPC155686
0.7708	Intermediate Similarity	NPC472620
0.7692	Intermediate Similarity	NPC237440
0.7692	Intermediate Similarity	NPC270160
0.7688	Intermediate Similarity	NPC246466
0.7688	Intermediate Similarity	NPC478225
0.7688	Intermediate Similarity	NPC473395
0.7672	Intermediate Similarity	NPC100849
0.765	Intermediate Similarity	NPC469619
0.765	Intermediate Similarity	NPC471807
0.765	Intermediate Similarity	NPC469670
0.765	Intermediate Similarity	NPC471806
0.765	Intermediate Similarity	NPC471810
0.7641	Intermediate Similarity	NPC471802
0.7632	Intermediate Similarity	NPC234053
0.7622	Intermediate Similarity	NPC478231
0.7609	Intermediate Similarity	NPC132990
0.7609	Intermediate Similarity	NPC46882
0.7604	Intermediate Similarity	NPC472619
0.7602	Intermediate Similarity	NPC306240
0.76	Intermediate Similarity	NPC471813
0.76	Intermediate Similarity	NPC121100
0.76	Intermediate Similarity	NPC471805
0.7596	Intermediate Similarity	NPC477566
0.7596	Intermediate Similarity	NPC477567
0.7594	Intermediate Similarity	NPC84935
0.7594	Intermediate Similarity	NPC472889
0.7594	Intermediate Similarity	NPC190020
0.7594	Intermediate Similarity	NPC77679
0.7592	Intermediate Similarity	NPC20237
0.7592	Intermediate Similarity	NPC125465
0.7582	Intermediate Similarity	NPC477569
0.7581	Intermediate Similarity	NPC99381
0.7581	Intermediate Similarity	NPC478221
0.7581	Intermediate Similarity	NPC69043
0.7581	Intermediate Similarity	NPC472890
0.7581	Intermediate Similarity	NPC478230
0.7581	Intermediate Similarity	NPC16082
0.7581	Intermediate Similarity	NPC68727
0.7581	Intermediate Similarity	NPC82592
0.7579	Intermediate Similarity	NPC470563
0.7579	Intermediate Similarity	NPC249181
0.7568	Intermediate Similarity	NPC167903
0.7568	Intermediate Similarity	NPC268992
0.7568	Intermediate Similarity	NPC51824
0.7568	Intermediate Similarity	NPC470338
0.7568	Intermediate Similarity	NPC113608
0.7568	Intermediate Similarity	NPC470337
0.7568	Intermediate Similarity	NPC180944
0.7566	Intermediate Similarity	NPC96031
0.7565	Intermediate Similarity	NPC313717
0.7565	Intermediate Similarity	NPC315306
0.7556	Intermediate Similarity	NPC51106
0.7552	Intermediate Similarity	NPC283041
0.7552	Intermediate Similarity	NPC473094
0.7541	Intermediate Similarity	NPC470359
0.754	Intermediate Similarity	NPC150227
0.7539	Intermediate Similarity	NPC68850
0.7539	Intermediate Similarity	NPC191930
0.7527	Intermediate Similarity	NPC281477
0.7527	Intermediate Similarity	NPC303950
0.7527	Intermediate Similarity	NPC260946
0.7527	Intermediate Similarity	NPC137301
0.7526	Intermediate Similarity	NPC470561
0.7514	Intermediate Similarity	NPC280404
0.7514	Intermediate Similarity	NPC210425
0.7514	Intermediate Similarity	NPC86373
0.7514	Intermediate Similarity	NPC277426
0.7513	Intermediate Similarity	NPC473096
0.7513	Intermediate Similarity	NPC470358
0.7513	Intermediate Similarity	NPC473095
0.75	Intermediate Similarity	NPC312630
0.75	Intermediate Similarity	NPC108278
0.75	Intermediate Similarity	NPC472621
0.75	Intermediate Similarity	NPC324220
0.75	Intermediate Similarity	NPC478050
0.7487	Intermediate Similarity	NPC199926
0.7487	Intermediate Similarity	NPC476822
0.7487	Intermediate Similarity	NPC170189
0.7487	Intermediate Similarity	NPC161151
0.7487	Intermediate Similarity	NPC208173
0.7487	Intermediate Similarity	NPC79998
0.7486	Intermediate Similarity	NPC53362
0.7486	Intermediate Similarity	NPC8817
0.7486	Intermediate Similarity	NPC166583
0.7473	Intermediate Similarity	NPC76041
0.7473	Intermediate Similarity	NPC184284
0.7473	Intermediate Similarity	NPC478224
0.7473	Intermediate Similarity	NPC115249
0.7461	Intermediate Similarity	NPC472622
0.7459	Intermediate Similarity	NPC469542
0.7459	Intermediate Similarity	NPC472006
0.7459	Intermediate Similarity	NPC225854
0.7448	Intermediate Similarity	NPC472049
0.7447	Intermediate Similarity	NPC4547
0.7447	Intermediate Similarity	NPC164427
0.7446	Intermediate Similarity	NPC73411
0.7446	Intermediate Similarity	NPC215711
0.7444	Intermediate Similarity	NPC1704
0.7444	Intermediate Similarity	NPC67650
0.7437	Intermediate Similarity	NPC182693
0.7437	Intermediate Similarity	NPC475148
0.7437	Intermediate Similarity	NPC475656
0.7435	Intermediate Similarity	NPC473022
0.7433	Intermediate Similarity	NPC472799
0.7433	Intermediate Similarity	NPC192189
0.7432	Intermediate Similarity	NPC473023
0.7432	Intermediate Similarity	NPC470357
0.7432	Intermediate Similarity	NPC107625
0.7426	Intermediate Similarity	NPC71385
0.7426	Intermediate Similarity	NPC230670
0.7421	Intermediate Similarity	NPC470810
0.7421	Intermediate Similarity	NPC313368
0.7421	Intermediate Similarity	NPC143050
0.7419	Intermediate Similarity	NPC221249
0.7409	Intermediate Similarity	NPC469394
0.7407	Intermediate Similarity	NPC478226
0.7405	Intermediate Similarity	NPC77325
0.7405	Intermediate Similarity	NPC4423
0.7403	Intermediate Similarity	NPC469579
0.7403	Intermediate Similarity	NPC474385
0.7398	Intermediate Similarity	NPC98776
0.7398	Intermediate Similarity	NPC472054
0.7394	Intermediate Similarity	NPC89625
0.7394	Intermediate Similarity	NPC317585
0.7394	Intermediate Similarity	NPC149618
0.7391	Intermediate Similarity	NPC137296
0.7391	Intermediate Similarity	NPC210320
0.7391	Intermediate Similarity	NPC472036
0.7389	Intermediate Similarity	NPC112708
0.7385	Intermediate Similarity	NPC241874
0.7382	Intermediate Similarity	NPC87431
0.7382	Intermediate Similarity	NPC92589
0.738	Intermediate Similarity	NPC256141
0.738	Intermediate Similarity	NPC271681
0.738	Intermediate Similarity	NPC273483
0.7377	Intermediate Similarity	NPC83272

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 NPC108744 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	388
0.1-0.2	1074
0.2-0.3	2339
0.3-0.4	2778
0.4-0.5	1747
0.5-0.6	616
0.6-0.7	202
0.7-0.8	6
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
0.7632	Intermediate Similarity	NPD2403	Approved
0.7377	Intermediate Similarity	NPD2534	Approved
0.7377	Intermediate Similarity	NPD2532	Approved
0.7377	Intermediate Similarity	NPD2533	Approved
0.7337	Intermediate Similarity	NPD6784	Approved
0.7337	Intermediate Similarity	NPD6785	Approved
0.7238	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7165	Intermediate Similarity	NPD6232	Discontinued
0.7143	Intermediate Similarity	NPD7473	Discontinued
0.7129	Intermediate Similarity	NPD8434	Phase 2
0.709	Intermediate Similarity	NPD4380	Phase 2
0.7068	Intermediate Similarity	NPD5760	Phase 2
0.7068	Intermediate Similarity	NPD7819	Suspended
0.7068	Intermediate Similarity	NPD5761	Phase 2
0.705	Intermediate Similarity	NPD6559	Discontinued
0.7047	Intermediate Similarity	NPD7075	Discontinued
0.7	Intermediate Similarity	NPD6599	Discontinued
0.6995	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD8438	Clinical (unspecified phase)
0.6935	Remote Similarity	NPD3818	Discontinued
0.6927	Remote Similarity	NPD6801	Discontinued
0.6908	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6904	Remote Similarity	NPD5710	Approved
0.6904	Remote Similarity	NPD5711	Approved
0.69	Remote Similarity	NPD5844	Phase 1
0.6891	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6891	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD4628	Phase 3
0.6882	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6881	Remote Similarity	NPD7685	Pre-registration
0.6872	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6853	Remote Similarity	NPD6959	Discontinued
0.6839	Remote Similarity	NPD37	Approved
0.6839	Remote Similarity	NPD1934	Approved
0.6837	Remote Similarity	NPD6234	Discontinued
0.6828	Remote Similarity	NPD2800	Approved
0.6825	Remote Similarity	NPD1578	Phase 2
0.6821	Remote Similarity	NPD3882	Suspended
0.6821	Remote Similarity	NPD4965	Approved
0.6821	Remote Similarity	NPD4966	Approved
0.6821	Remote Similarity	NPD4967	Phase 2
0.6806	Remote Similarity	NPD2370	Clinical (unspecified phase)
0.6789	Remote Similarity	NPD6273	Approved
0.6772	Remote Similarity	NPD6799	Approved
0.6769	Remote Similarity	NPD5402	Approved
0.6769	Remote Similarity	NPD3817	Phase 2
0.6768	Remote Similarity	NPD7199	Phase 2
0.6762	Remote Similarity	NPD4363	Phase 3
0.6762	Remote Similarity	NPD4360	Phase 2
0.6751	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.675	Remote Similarity	NPD6166	Phase 2
0.675	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.675	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6748	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6718	Remote Similarity	NPD2801	Approved
0.6718	Remote Similarity	NPD1465	Phase 2
0.6717	Remote Similarity	NPD5494	Approved
0.6716	Remote Similarity	NPD6764	Approved
0.6716	Remote Similarity	NPD6765	Approved
0.6715	Remote Similarity	NPD8150	Discontinued
0.6701	Remote Similarity	NPD3749	Approved
0.6701	Remote Similarity	NPD7411	Suspended
0.67	Remote Similarity	NPD7074	Phase 3
0.6685	Remote Similarity	NPD6651	Approved
0.6684	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6683	Remote Similarity	NPD7228	Approved
0.6683	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD920	Approved
0.6667	Remote Similarity	NPD2935	Discontinued
0.6667	Remote Similarity	NPD1551	Phase 2
0.6667	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6651	Remote Similarity	NPD4362	Clinical (unspecified phase)
0.6651	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6651	Remote Similarity	NPD4361	Phase 2
0.665	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.665	Remote Similarity	NPD8312	Approved
0.665	Remote Similarity	NPD8313	Approved
0.665	Remote Similarity	NPD7054	Approved
0.6649	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.663	Remote Similarity	NPD230	Phase 1
0.6618	Remote Similarity	NPD7472	Approved
0.6617	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6615	Remote Similarity	NPD958	Approved
0.6614	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6614	Remote Similarity	NPD3750	Approved
0.6613	Remote Similarity	NPD1510	Phase 2
0.66	Remote Similarity	NPD8127	Discontinued
0.6598	Remote Similarity	NPD3226	Approved
0.6596	Remote Similarity	NPD1549	Phase 2
0.6595	Remote Similarity	NPD1607	Approved
0.6591	Remote Similarity	NPD8151	Discontinued
0.659	Remote Similarity	NPD7435	Discontinued
0.6585	Remote Similarity	NPD6797	Phase 2
0.6584	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6583	Remote Similarity	NPD919	Approved
0.658	Remote Similarity	NPD5403	Approved
0.6576	Remote Similarity	NPD1240	Approved
0.6566	Remote Similarity	NPD7768	Phase 2
0.6562	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6553	Remote Similarity	NPD7251	Discontinued
0.6543	Remote Similarity	NPD5763	Approved
0.6543	Remote Similarity	NPD5762	Approved
0.6543	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6543	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6528	Remote Similarity	NPD6776	Approved
0.6528	Remote Similarity	NPD6778	Approved
0.6528	Remote Similarity	NPD6779	Approved
0.6528	Remote Similarity	NPD6780	Approved
0.6528	Remote Similarity	NPD6782	Approved
0.6528	Remote Similarity	NPD6781	Approved
0.6528	Remote Similarity	NPD6777	Approved
0.6522	Remote Similarity	NPD7808	Phase 3
0.651	Remote Similarity	NPD1511	Approved
0.6489	Remote Similarity	NPD6099	Approved
0.6489	Remote Similarity	NPD6100	Approved
0.6489	Remote Similarity	NPD2796	Approved
0.6477	Remote Similarity	NPD5401	Approved
0.6462	Remote Similarity	NPD957	Approved
0.6458	Remote Similarity	NPD7236	Approved
0.6458	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6455	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6455	Remote Similarity	NPD6004	Phase 3
0.6455	Remote Similarity	NPD6005	Phase 3
0.6455	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6455	Remote Similarity	NPD6002	Phase 3
0.6443	Remote Similarity	NPD1512	Approved
0.6439	Remote Similarity	NPD7799	Discontinued
0.6439	Remote Similarity	NPD3751	Discontinued
0.6438	Remote Similarity	NPD7497	Discontinued
0.6436	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6436	Remote Similarity	NPD1247	Approved
0.6429	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6425	Remote Similarity	NPD5953	Discontinued
0.6413	Remote Similarity	NPD7874	Approved
0.6413	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6406	Remote Similarity	NPD2354	Approved
0.6406	Remote Similarity	NPD3887	Approved
0.6404	Remote Similarity	NPD4665	Approved
0.6394	Remote Similarity	NPD7240	Approved
0.6387	Remote Similarity	NPD1243	Approved
0.6384	Remote Similarity	NPD7783	Phase 2
0.6384	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6378	Remote Similarity	NPD7239	Suspended
0.6376	Remote Similarity	NPD4914	Approved
0.6372	Remote Similarity	NPD7930	Approved
0.6368	Remote Similarity	NPD2346	Discontinued
0.6364	Remote Similarity	NPD7696	Phase 3
0.6364	Remote Similarity	NPD7697	Approved
0.6364	Remote Similarity	NPD7698	Approved
0.635	Remote Similarity	NPD2379	Clinical (unspecified phase)
0.6349	Remote Similarity	NPD3748	Approved
0.6349	Remote Similarity	NPD2799	Discontinued
0.6345	Remote Similarity	NPD7458	Discontinued
0.6345	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.634	Remote Similarity	NPD7390	Discontinued
0.6335	Remote Similarity	NPD7870	Phase 2
0.6335	Remote Similarity	NPD7871	Phase 2
0.6335	Remote Similarity	NPD4534	Discontinued
0.6335	Remote Similarity	NPD5958	Discontinued
0.6335	Remote Similarity	NPD8320	Phase 1
0.6335	Remote Similarity	NPD8319	Approved
0.633	Remote Similarity	NPD6653	Approved
0.6329	Remote Similarity	NPD7286	Phase 2
0.6327	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6324	Remote Similarity	NPD7229	Phase 3
0.6323	Remote Similarity	NPD7701	Phase 2
0.6321	Remote Similarity	NPD6190	Approved
0.6318	Remote Similarity	NPD6823	Phase 2
0.6316	Remote Similarity	NPD8404	Phase 2
0.6311	Remote Similarity	NPD7801	Approved
0.631	Remote Similarity	NPD4140	Approved
0.6308	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6304	Remote Similarity	NPD454	Approved
0.6302	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6296	Remote Similarity	NPD6535	Approved
0.6296	Remote Similarity	NPD6534	Approved
0.6293	Remote Similarity	NPD3926	Phase 2
0.629	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.629	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6277	Remote Similarity	NPD447	Suspended
0.6276	Remote Similarity	NPD1940	Clinical (unspecified phase)
0.6269	Remote Similarity	NPD5353	Approved
0.6269	Remote Similarity	NPD7003	Approved
0.6263	Remote Similarity	NPD7033	Discontinued
0.6263	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6261	Remote Similarity	NPD4111	Phase 1
0.6257	Remote Similarity	NPD6663	Approved
0.625	Remote Similarity	NPD5647	Approved
0.6244	Remote Similarity	NPD4386	Approved
0.6244	Remote Similarity	NPD4387	Approved
0.6244	Remote Similarity	NPD3787	Discontinued
0.6239	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6231	Remote Similarity	NPD7028	Phase 2
0.6231	Remote Similarity	NPD4972	Discontinued
0.6223	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.6223	Remote Similarity	NPD3620	Phase 2
0.6223	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6223	Remote Similarity	NPD943	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