NPASS Compound

Structure

NPC247104 OpenBabel07101719522D 31 34 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 2.7321 0.0000 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 3.4752 -1.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0739 -2.4781 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 -2.1213 2.1213 0.0000 C 0 0 0 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 1.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8660 -1.5000 0.0000 C 0 0 1 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 -1.6730 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 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 -1.9319 -0.5176 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 12 1 0 0 0 0 2 22 1 0 0 0 0 3 22 1 0 0 0 0 4 23 1 0 0 0 0 5 30 1 0 0 0 0 6 14 2 0 0 0 0 7 16 2 0 0 0 0 7 17 1 0 0 0 0 8 13 1 0 0 0 0 8 22 1 0 0 0 0 9 15 1 0 0 0 0 9 22 1 0 0 0 0 10 18 1 0 0 0 0 10 23 1 0 0 0 0 11 14 1 0 0 0 0 11 26 2 0 0 0 0 12 19 2 0 0 0 0 12 20 1 0 0 0 0 13 6 1 6 0 0 0 13 15 1 0 0 0 0 14 24 1 0 0 0 0 15 23 1 6 0 0 0 16 19 1 0 0 0 0 16 27 1 0 0 0 0 17 20 2 0 0 0 0 17 30 1 0 0 0 0 18 24 1 1 0 0 0 18 31 1 0 0 0 0 19 21 1 0 0 0 0 20 25 1 0 0 0 0 21 28 2 0 0 0 0 21 31 1 0 0 0 0 23 24 1 6 0 0 0 24 29 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	448.17
Volume:	441.568
LogP:	5.514
LogD:	4.223
LogS:	-5.166
# Rotatable Bonds:	5
TPSA:	93.06
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.529
Synthetic Accessibility Score:	4.74
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:	-4.72
MDCK Permeability:	2.2800080841989256e-05
Pgp-inhibitor:	0.013
Pgp-substrate:	0.006
Human Intestinal Absorption (HIA):	0.015
20% Bioavailability (F20%):	0.008
30% Bioavailability (F30%):	0.003

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.269
Plasma Protein Binding (PPB):	97.17681884765625%
Volume Distribution (VD):	1.848
Pgp-substrate:	2.843337059020996%

ADMET: Metabolism

CYP1A2-inhibitor:	0.396
CYP1A2-substrate:	0.672
CYP2C19-inhibitor:	0.907
CYP2C19-substrate:	0.658
CYP2C9-inhibitor:	0.897
CYP2C9-substrate:	0.818
CYP2D6-inhibitor:	0.781
CYP2D6-substrate:	0.277
CYP3A4-inhibitor:	0.846
CYP3A4-substrate:	0.602

ADMET: Excretion

Clearance (CL):	7.51
Half-life (T1/2):	0.184

ADMET: Toxicity

hERG Blockers:	0.183
Human Hepatotoxicity (H-HT):	0.449
Drug-inuced Liver Injury (DILI):	0.165
AMES Toxicity:	0.212
Rat Oral Acute Toxicity:	0.075
Maximum Recommended Daily Dose:	0.949
Skin Sensitization:	0.75
Carcinogencity:	0.836
Eye Corrosion:	0.043
Eye Irritation:	0.25
Respiratory Toxicity:	0.938

Download Data

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

Natural Product: NPC247104

Natural Product ID:	NPC247104
*Common Name:**	Armillaridin
IUPAC Name:	[(2R,2aS,4aS,7aS,7bR)-3-formyl-2a-hydroxy-6,6,7b-trimethyl-1,2,4a,5,7,7a-hexahydrocyclobuta[e]inden-2-yl] 3-chloro-6-hydroxy-4-methoxy-2-methylbenzoate
Synonyms:	Armillaridin
Standard InCHIKey:	QETHRCCHQRWBIJ-OXKPQTCESA-N
Standard InCHI:	InChI=1S/C24H29ClO6/c1-12-19(16(27)7-17(30-5)20(12)25)21(28)31-18-10-23(4)15-9-22(2,3)8-13(15)6-14(11-26)24(18,23)29/h6-7,11,13,15,18,27,29H,8-10H2,1-5H3/t13-,15+,18-,23-,24+/m1/s1
SMILES:	Cc1c(c(cc(c1Cl)OC)O)C(=O)O[C@@H]1C[C@]2(C)[C@H]3CC(C)(C)C[C@H]3C=C(C=O)[C@]12O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1762764
PubChem CID:	51351607
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
NPO32955	armillaria	Genus	Physalacriaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21376582]

☑ 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
EC50	5
IC50	4

Activity Type	# Activity
Cell Line	8
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	7800.0	nM	PMID[515142]
NPT15	Cell Line	Jurkat	Homo sapiens	IC50	=	3000.0	nM	PMID[515142]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	9200.0	nM	PMID[515142]
NPT111	Cell Line	K562	Homo sapiens	IC50	=	8900.0	nM	PMID[515142]
NPT165	Cell Line	HeLa	Homo sapiens	EC50	=	9200.0	nM	PMID[515143]
NPT111	Cell Line	K562	Homo sapiens	EC50	=	8900.0	nM	PMID[515143]
NPT2103	Cell Line	MONO-MAC-6	Homo sapiens	EC50	=	5600.0	nM	PMID[515143]
NPT1970	Cell Line	THP-1	Homo sapiens	EC50	=	4500.0	nM	PMID[515143]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	EC50	=	12300.0	nM	PMID[515143]

☑ 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 NPC247104 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	450
0.1-0.2	1890
0.2-0.3	4084
0.3-0.4	9822
0.4-0.5	10141
0.5-0.6	5712
0.6-0.7	9648
0.7-0.8	923
0.8-0.85	17
0.85-0.9	2
0.9-0.95	4
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9943	High Similarity	NPC221185
0.9722	High Similarity	NPC108744
0.9716	High Similarity	NPC470100
0.95	High Similarity	NPC48822
0.9494	High Similarity	NPC470099
0.9489	High Similarity	NPC99937
0.9326	High Similarity	NPC470103
0.8914	High Similarity	NPC165460
0.8722	High Similarity	NPC477568
0.8548	High Similarity	NPC474499
0.8547	High Similarity	NPC472032
0.8539	High Similarity	NPC211592
0.8371	Intermediate Similarity	NPC472405
0.8361	Intermediate Similarity	NPC470422
0.8325	Intermediate Similarity	NPC214901
0.8306	Intermediate Similarity	NPC474857
0.8278	Intermediate Similarity	NPC470081
0.8272	Intermediate Similarity	NPC220369
0.8268	Intermediate Similarity	NPC298401
0.8247	Intermediate Similarity	NPC154720
0.8239	Intermediate Similarity	NPC470102
0.8232	Intermediate Similarity	NPC173352
0.8232	Intermediate Similarity	NPC58653
0.8222	Intermediate Similarity	NPC473696
0.8222	Intermediate Similarity	NPC474096
0.8216	Intermediate Similarity	NPC264922
0.8202	Intermediate Similarity	NPC472404
0.8187	Intermediate Similarity	NPC28669
0.8152	Intermediate Similarity	NPC277865
0.8144	Intermediate Similarity	NPC198163
0.8087	Intermediate Similarity	NPC474061
0.8085	Intermediate Similarity	NPC471801
0.8075	Intermediate Similarity	NPC45072
0.8054	Intermediate Similarity	NPC107283
0.8054	Intermediate Similarity	NPC470562
0.8051	Intermediate Similarity	NPC313541
0.8045	Intermediate Similarity	NPC472050
0.8022	Intermediate Similarity	NPC245122
0.8021	Intermediate Similarity	NPC316091
0.8021	Intermediate Similarity	NPC313386
0.8011	Intermediate Similarity	NPC470560
0.7979	Intermediate Similarity	NPC39409
0.7959	Intermediate Similarity	NPC193676
0.7957	Intermediate Similarity	NPC470565
0.7956	Intermediate Similarity	NPC470339
0.7944	Intermediate Similarity	NPC280497
0.7927	Intermediate Similarity	NPC471804
0.7927	Intermediate Similarity	NPC471812
0.7927	Intermediate Similarity	NPC471803
0.7917	Intermediate Similarity	NPC191606
0.7914	Intermediate Similarity	NPC188618
0.7912	Intermediate Similarity	NPC472055
0.7877	Intermediate Similarity	NPC470340
0.7869	Intermediate Similarity	NPC117985
0.7865	Intermediate Similarity	NPC179178
0.7853	Intermediate Similarity	NPC151292
0.7846	Intermediate Similarity	NPC471807
0.7846	Intermediate Similarity	NPC471806
0.7846	Intermediate Similarity	NPC471810
0.7842	Intermediate Similarity	NPC471802
0.7842	Intermediate Similarity	NPC28160
0.7838	Intermediate Similarity	NPC234053
0.7835	Intermediate Similarity	NPC136411
0.7821	Intermediate Similarity	NPC200773
0.7821	Intermediate Similarity	NPC70016
0.7821	Intermediate Similarity	NPC240768
0.7821	Intermediate Similarity	NPC215921
0.7819	Intermediate Similarity	NPC472620
0.7809	Intermediate Similarity	NPC477567
0.7809	Intermediate Similarity	NPC237440
0.7809	Intermediate Similarity	NPC270160
0.7809	Intermediate Similarity	NPC477566
0.7802	Intermediate Similarity	NPC246466
0.7802	Intermediate Similarity	NPC478225
0.7801	Intermediate Similarity	NPC306240
0.7797	Intermediate Similarity	NPC477569
0.7796	Intermediate Similarity	NPC125465
0.7795	Intermediate Similarity	NPC121100
0.7795	Intermediate Similarity	NPC471813
0.7795	Intermediate Similarity	NPC471805
0.7784	Intermediate Similarity	NPC470563
0.7784	Intermediate Similarity	NPC100849
0.7747	Intermediate Similarity	NPC150227
0.7742	Intermediate Similarity	NPC68850
0.774	Intermediate Similarity	NPC260946
0.7737	Intermediate Similarity	NPC294149
0.7735	Intermediate Similarity	NPC478231
0.7735	Intermediate Similarity	NPC155686
0.773	Intermediate Similarity	NPC470561
0.7722	Intermediate Similarity	NPC46882
0.7722	Intermediate Similarity	NPC132990
0.7713	Intermediate Similarity	NPC472619
0.7705	Intermediate Similarity	NPC190020
0.7705	Intermediate Similarity	NPC84935
0.7705	Intermediate Similarity	NPC77679
0.7696	Intermediate Similarity	NPC108278
0.7692	Intermediate Similarity	NPC472890
0.7692	Intermediate Similarity	NPC82592
0.7692	Intermediate Similarity	NPC79998
0.7692	Intermediate Similarity	NPC16082
0.7692	Intermediate Similarity	NPC478221
0.7692	Intermediate Similarity	NPC199926
0.7688	Intermediate Similarity	NPC249181
0.7688	Intermediate Similarity	NPC476822
0.768	Intermediate Similarity	NPC76041
0.768	Intermediate Similarity	NPC51824
0.768	Intermediate Similarity	NPC470337
0.768	Intermediate Similarity	NPC167903
0.768	Intermediate Similarity	NPC115249
0.768	Intermediate Similarity	NPC113608
0.768	Intermediate Similarity	NPC470338
0.768	Intermediate Similarity	NPC184284
0.768	Intermediate Similarity	NPC268992
0.768	Intermediate Similarity	NPC180944
0.7676	Intermediate Similarity	NPC96031
0.7672	Intermediate Similarity	NPC315306
0.7672	Intermediate Similarity	NPC313717
0.767	Intermediate Similarity	NPC51106
0.767	Intermediate Similarity	NPC472006
0.7667	Intermediate Similarity	NPC469670
0.7667	Intermediate Similarity	NPC469619
0.7657	Intermediate Similarity	NPC1704
0.7657	Intermediate Similarity	NPC67650
0.765	Intermediate Similarity	NPC4547
0.7647	Intermediate Similarity	NPC191930
0.764	Intermediate Similarity	NPC107625
0.7637	Intermediate Similarity	NPC192189
0.7637	Intermediate Similarity	NPC137301
0.7637	Intermediate Similarity	NPC472799
0.7637	Intermediate Similarity	NPC281477
0.7637	Intermediate Similarity	NPC303950
0.7634	Intermediate Similarity	NPC473022
0.7627	Intermediate Similarity	NPC277426
0.7627	Intermediate Similarity	NPC86373
0.7627	Intermediate Similarity	NPC280404
0.7627	Intermediate Similarity	NPC210425
0.7624	Intermediate Similarity	NPC221249
0.7622	Intermediate Similarity	NPC313368
0.7622	Intermediate Similarity	NPC470810
0.7609	Intermediate Similarity	NPC472889
0.7609	Intermediate Similarity	NPC473395
0.7606	Intermediate Similarity	NPC472621
0.7606	Intermediate Similarity	NPC20237
0.7604	Intermediate Similarity	NPC478050
0.7598	Intermediate Similarity	NPC53362
0.7598	Intermediate Similarity	NPC8817
0.7598	Intermediate Similarity	NPC166583
0.7598	Intermediate Similarity	NPC137296
0.7596	Intermediate Similarity	NPC478230
0.7596	Intermediate Similarity	NPC208173
0.7596	Intermediate Similarity	NPC68727
0.7596	Intermediate Similarity	NPC99381
0.7596	Intermediate Similarity	NPC69043
0.7596	Intermediate Similarity	NPC170189
0.7584	Intermediate Similarity	NPC75694
0.7582	Intermediate Similarity	NPC271681
0.7571	Intermediate Similarity	NPC469542
0.7569	Intermediate Similarity	NPC472891
0.7569	Intermediate Similarity	NPC150928
0.7569	Intermediate Similarity	NPC119929
0.7569	Intermediate Similarity	NPC225854
0.7569	Intermediate Similarity	NPC96501
0.7566	Intermediate Similarity	NPC283041
0.7566	Intermediate Similarity	NPC473094
0.7566	Intermediate Similarity	NPC472622
0.7557	Intermediate Similarity	NPC90411
0.7556	Intermediate Similarity	NPC73411
0.7556	Intermediate Similarity	NPC172329
0.7556	Intermediate Similarity	NPC470359
0.7556	Intermediate Similarity	NPC215711
0.7556	Intermediate Similarity	NPC2569
0.7554	Intermediate Similarity	NPC313922
0.7554	Intermediate Similarity	NPC164427
0.7553	Intermediate Similarity	NPC314653
0.7553	Intermediate Similarity	NPC316262
0.7551	Intermediate Similarity	NPC471811
0.7551	Intermediate Similarity	NPC471809
0.7542	Intermediate Similarity	NPC472033
0.7542	Intermediate Similarity	NPC470357
0.7542	Intermediate Similarity	NPC473023
0.7538	Intermediate Similarity	NPC475148
0.7538	Intermediate Similarity	NPC182693
0.7538	Intermediate Similarity	NPC475656
0.7527	Intermediate Similarity	NPC143050
0.7527	Intermediate Similarity	NPC470358
0.7526	Intermediate Similarity	NPC473096
0.7526	Intermediate Similarity	NPC473095
0.7514	Intermediate Similarity	NPC474385
0.7514	Intermediate Similarity	NPC77325
0.7514	Intermediate Similarity	NPC322112
0.7514	Intermediate Similarity	NPC272196
0.7514	Intermediate Similarity	NPC469579
0.7514	Intermediate Similarity	NPC478226
0.7514	Intermediate Similarity	NPC4423
0.7513	Intermediate Similarity	NPC324220
0.7513	Intermediate Similarity	NPC312630
0.75	Intermediate Similarity	NPC471808
0.75	Intermediate Similarity	NPC149618
0.75	Intermediate Similarity	NPC89625
0.75	Intermediate Similarity	NPC195675

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 NPC247104 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	382
0.1-0.2	1039
0.2-0.3	2261
0.3-0.4	2748
0.4-0.5	1828
0.5-0.6	656
0.6-0.7	229
0.7-0.8	7
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
0.7838	Intermediate Similarity	NPD2403	Approved
0.7584	Intermediate Similarity	NPD2532	Approved
0.7584	Intermediate Similarity	NPD2533	Approved
0.7584	Intermediate Similarity	NPD2534	Approved
0.7443	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7263	Intermediate Similarity	NPD6232	Discontinued
0.7259	Intermediate Similarity	NPD6784	Approved
0.7259	Intermediate Similarity	NPD6785	Approved
0.724	Intermediate Similarity	NPD7473	Discontinued
0.7189	Intermediate Similarity	NPD6599	Discontinued
0.7166	Intermediate Similarity	NPD7819	Suspended
0.7143	Intermediate Similarity	NPD7075	Discontinued
0.7136	Intermediate Similarity	NPD8434	Phase 2
0.7128	Intermediate Similarity	NPD8438	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD4380	Phase 2
0.709	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD5710	Approved
0.7083	Intermediate Similarity	NPD5711	Approved
0.7074	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7074	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7072	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7056	Intermediate Similarity	NPD6559	Discontinued
0.7021	Intermediate Similarity	NPD1934	Approved
0.7017	Intermediate Similarity	NPD2800	Approved
0.7011	Intermediate Similarity	NPD1578	Phase 2
0.7	Intermediate Similarity	NPD3882	Suspended
0.699	Remote Similarity	NPD5844	Phase 1
0.6989	Remote Similarity	NPD2370	Clinical (unspecified phase)
0.6978	Remote Similarity	NPD4628	Phase 3
0.6957	Remote Similarity	NPD6799	Approved
0.6943	Remote Similarity	NPD6959	Discontinued
0.6939	Remote Similarity	NPD3818	Discontinued
0.6931	Remote Similarity	NPD6801	Discontinued
0.6927	Remote Similarity	NPD6234	Discontinued
0.6912	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6895	Remote Similarity	NPD2801	Approved
0.6895	Remote Similarity	NPD5761	Phase 2
0.6895	Remote Similarity	NPD5760	Phase 2
0.6891	Remote Similarity	NPD5494	Approved
0.6875	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD3749	Approved
0.6859	Remote Similarity	NPD3817	Phase 2
0.6851	Remote Similarity	NPD1551	Phase 2
0.6851	Remote Similarity	NPD2935	Discontinued
0.6845	Remote Similarity	NPD920	Approved
0.6845	Remote Similarity	NPD4363	Phase 3
0.6845	Remote Similarity	NPD4360	Phase 2
0.6842	Remote Similarity	NPD37	Approved
0.6839	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6828	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6823	Remote Similarity	NPD4965	Approved
0.6823	Remote Similarity	NPD4966	Approved
0.6823	Remote Similarity	NPD4967	Phase 2
0.6816	Remote Similarity	NPD230	Phase 1
0.6806	Remote Similarity	NPD1465	Phase 2
0.6796	Remote Similarity	NPD1510	Phase 2
0.6793	Remote Similarity	NPD3750	Approved
0.6789	Remote Similarity	NPD7411	Suspended
0.6789	Remote Similarity	NPD958	Approved
0.6778	Remote Similarity	NPD6651	Approved
0.6778	Remote Similarity	NPD1607	Approved
0.6776	Remote Similarity	NPD1549	Phase 2
0.6771	Remote Similarity	NPD5402	Approved
0.6771	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6769	Remote Similarity	NPD7199	Phase 2
0.676	Remote Similarity	NPD1240	Approved
0.6753	Remote Similarity	NPD919	Approved
0.6751	Remote Similarity	NPD6166	Phase 2
0.6751	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6751	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6749	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6738	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6736	Remote Similarity	NPD7768	Phase 2
0.6732	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6731	Remote Similarity	NPD4361	Phase 2
0.6731	Remote Similarity	NPD4362	Clinical (unspecified phase)
0.6721	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6721	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6716	Remote Similarity	NPD8150	Discontinued
0.6703	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6702	Remote Similarity	NPD6273	Approved
0.6701	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.67	Remote Similarity	NPD7074	Phase 3
0.6684	Remote Similarity	NPD1511	Approved
0.6684	Remote Similarity	NPD3226	Approved
0.6683	Remote Similarity	NPD7228	Approved
0.6683	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2796	Approved
0.6667	Remote Similarity	NPD6099	Approved
0.6667	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6100	Approved
0.665	Remote Similarity	NPD8312	Approved
0.665	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.665	Remote Similarity	NPD8313	Approved
0.665	Remote Similarity	NPD7054	Approved
0.6649	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6649	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6634	Remote Similarity	NPD7685	Pre-registration
0.6634	Remote Similarity	NPD6765	Approved
0.6634	Remote Similarity	NPD6764	Approved
0.6632	Remote Similarity	NPD957	Approved
0.6631	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6617	Remote Similarity	NPD7472	Approved
0.6614	Remote Similarity	NPD1512	Approved
0.6612	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6599	Remote Similarity	NPD8127	Discontinued
0.6599	Remote Similarity	NPD1247	Approved
0.659	Remote Similarity	NPD8151	Discontinued
0.6589	Remote Similarity	NPD7435	Discontinued
0.6584	Remote Similarity	NPD6797	Phase 2
0.6579	Remote Similarity	NPD5403	Approved
0.6578	Remote Similarity	NPD2354	Approved
0.6578	Remote Similarity	NPD3887	Approved
0.6559	Remote Similarity	NPD1243	Approved
0.6552	Remote Similarity	NPD7251	Discontinued
0.6541	Remote Similarity	NPD2346	Discontinued
0.6526	Remote Similarity	NPD6776	Approved
0.6526	Remote Similarity	NPD6779	Approved
0.6526	Remote Similarity	NPD6780	Approved
0.6526	Remote Similarity	NPD6778	Approved
0.6526	Remote Similarity	NPD6782	Approved
0.6526	Remote Similarity	NPD6781	Approved
0.6526	Remote Similarity	NPD6777	Approved
0.6522	Remote Similarity	NPD3748	Approved
0.6522	Remote Similarity	NPD2799	Discontinued
0.652	Remote Similarity	NPD7808	Phase 3
0.6517	Remote Similarity	NPD3751	Discontinued
0.6517	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6513	Remote Similarity	NPD2379	Clinical (unspecified phase)
0.651	Remote Similarity	NPD7458	Discontinued
0.6505	Remote Similarity	NPD4534	Discontinued
0.6505	Remote Similarity	NPD5958	Discontinued
0.6502	Remote Similarity	NPD5953	Discontinued
0.6485	Remote Similarity	NPD7286	Phase 2
0.6482	Remote Similarity	NPD7229	Phase 3
0.648	Remote Similarity	NPD454	Approved
0.6474	Remote Similarity	NPD5401	Approved
0.6473	Remote Similarity	NPD4665	Approved
0.6471	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6464	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD5762	Approved
0.6452	Remote Similarity	NPD5763	Approved
0.6448	Remote Similarity	NPD447	Suspended
0.644	Remote Similarity	NPD1940	Clinical (unspecified phase)
0.6436	Remote Similarity	NPD7003	Approved
0.6435	Remote Similarity	NPD7497	Discontinued
0.6432	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD5353	Approved
0.6425	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6421	Remote Similarity	NPD7390	Discontinued
0.6409	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6409	Remote Similarity	NPD7874	Approved
0.6406	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6393	Remote Similarity	NPD943	Approved
0.6392	Remote Similarity	NPD4972	Discontinued
0.639	Remote Similarity	NPD7240	Approved
0.6387	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.638	Remote Similarity	NPD7783	Phase 2
0.638	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6374	Remote Similarity	NPD3764	Approved
0.6374	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6372	Remote Similarity	NPD4914	Approved
0.6368	Remote Similarity	NPD3926	Phase 2
0.6368	Remote Similarity	NPD7236	Approved
0.6364	Remote Similarity	NPD2353	Approved
0.6364	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6359	Remote Similarity	NPD1184	Approved
0.6359	Remote Similarity	NPD7698	Approved
0.6359	Remote Similarity	NPD6355	Discontinued
0.6359	Remote Similarity	NPD7697	Approved
0.6359	Remote Similarity	NPD7696	Phase 3
0.6344	Remote Similarity	NPD7033	Discontinued
0.633	Remote Similarity	NPD7871	Phase 2
0.633	Remote Similarity	NPD7870	Phase 2
0.633	Remote Similarity	NPD8319	Approved
0.633	Remote Similarity	NPD8320	Phase 1
0.6329	Remote Similarity	NPD1852	Discontinued
0.6327	Remote Similarity	NPD4111	Phase 1
0.6318	Remote Similarity	NPD3787	Discontinued
0.6318	Remote Similarity	NPD7701	Phase 2
0.6316	Remote Similarity	NPD6190	Approved
0.6313	Remote Similarity	NPD6823	Phase 2
0.6311	Remote Similarity	NPD8404	Phase 2
0.631	Remote Similarity	NPD5405	Approved
0.631	Remote Similarity	NPD5404	Approved
0.631	Remote Similarity	NPD5408	Approved
0.631	Remote Similarity	NPD5406	Approved
0.6306	Remote Similarity	NPD7801	Approved
0.6304	Remote Similarity	NPD4060	Phase 1
0.6298	Remote Similarity	NPD9494	Approved
0.6295	Remote Similarity	NPD7930	Approved
0.6291	Remote Similarity	NPD6535	Approved
0.6291	Remote Similarity	NPD6534	Approved
0.629	Remote Similarity	NPD4978	Clinical (unspecified phase)
0.6287	Remote Similarity	NPD5242	Approved
0.6284	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6283	Remote Similarity	NPD5058	Phase 3
0.628	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6277	Remote Similarity	NPD2344	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