NPASS Compound

Structure

NPC471396 OpenBabel07101718292D 40 46 0 0 1 0 0 0 0 0999 V2000 7.1777 -1.8679 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4457 1.1321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1205 -3.7828 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9486 -4.4551 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8096 -3.3995 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4316 -0.9079 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9871 -0.1604 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2388 2.2542 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2664 1.7539 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1339 2.0715 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9124 1.6220 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3117 -0.3679 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4457 -1.8679 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1575 1.1136 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6885 -2.1950 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3117 -1.3679 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.4457 0.1321 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.6885 -3.1950 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6395 -3.5040 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.2218 -2.5905 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6330 1.5704 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4232 1.2049 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5796 -1.3679 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9487 0.4882 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.5796 -0.3679 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.6286 -1.6770 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.0544 -0.1627 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.0408 -0.8679 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.2273 -2.6950 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0463 -0.9725 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.4506 -0.6898 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6286 -0.0589 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.2970 0.5887 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4681 -0.4644 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6395 -1.8860 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.8181 -1.4644 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1606 1.4779 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3157 -1.4527 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.6816 0.5983 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3 18 1 0 0 0 0 5 20 1 0 0 0 0 6 35 1 0 0 0 0 7 36 1 0 0 0 0 8 10 1 0 0 0 0 8 21 2 0 0 0 0 9 11 2 0 0 0 0 9 21 1 0 0 0 0 10 22 2 0 0 0 0 11 22 1 0 0 0 0 12 16 1 0 0 0 0 12 17 1 0 0 0 0 13 16 1 0 0 0 0 14 21 1 0 0 0 0 15 18 2 0 0 0 0 15 35 1 0 0 0 0 16 1 1 6 0 0 0 17 2 1 6 0 0 0 17 25 1 0 0 0 0 18 19 1 0 0 0 0 19 4 1 1 0 0 0 19 29 1 0 0 0 0 20 26 1 0 0 0 0 20 29 2 0 0 0 0 22 40 1 0 0 0 0 23 13 1 6 0 0 0 23 25 1 0 0 0 0 23 26 1 0 0 0 0 24 14 1 1 0 0 0 24 27 1 0 0 0 0 24 33 1 0 0 0 0 25 32 1 0 0 0 0 26 28 1 0 0 0 0 27 31 1 0 0 0 0 27 34 1 0 0 0 0 28 30 1 0 0 0 0 28 32 1 0 0 0 0 29 35 1 0 0 0 0 30 31 1 0 0 0 0 30 35 1 0 0 0 0 31 37 2 0 0 0 0 32 40 1 0 0 0 0 33 36 1 0 0 0 0 33 38 2 0 0 0 0 34 36 1 0 0 0 0 34 39 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	541.32
Volume:	579.087
LogP:	6.729
LogD:	5.002
LogS:	-3.553
# Rotatable Bonds:	0
TPSA:	71.69
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	8
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.35
Synthetic Accessibility Score:	6.838
Fsp3:	0.571
Lipinski Rule-of-5:	Rejected
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:	-4.839
MDCK Permeability:	2.1803141862619668e-05
Pgp-inhibitor:	0.985
Pgp-substrate:	0.993
Human Intestinal Absorption (HIA):	0.01
20% Bioavailability (F20%):	0.013
30% Bioavailability (F30%):	0.151

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.036
Plasma Protein Binding (PPB):	100.15753936767578%
Volume Distribution (VD):	0.886
Pgp-substrate:	1.7095677852630615%

ADMET: Metabolism

CYP1A2-inhibitor:	0.161
CYP1A2-substrate:	0.477
CYP2C19-inhibitor:	0.468
CYP2C19-substrate:	0.866
CYP2C9-inhibitor:	0.726
CYP2C9-substrate:	0.939
CYP2D6-inhibitor:	0.441
CYP2D6-substrate:	0.284
CYP3A4-inhibitor:	0.687
CYP3A4-substrate:	0.756

ADMET: Excretion

Clearance (CL):	6.846
Half-life (T1/2):	0.016

ADMET: Toxicity

hERG Blockers:	0.173
Human Hepatotoxicity (H-HT):	0.737
Drug-inuced Liver Injury (DILI):	0.95
AMES Toxicity:	0.023
Rat Oral Acute Toxicity:	0.87
Maximum Recommended Daily Dose:	0.956
Skin Sensitization:	0.121
Carcinogencity:	0.231
Eye Corrosion:	0.003
Eye Irritation:	0.011
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: NPC471396

Natural Product ID:	NPC471396
*Common Name:**	MAZDETZTAVRVEX-BKHPUCJFSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	MAZDETZTAVRVEX-BKHPUCJFSA-N
Standard InCHI:	InChI=1S/C35H43NO4/c1-16-12-17(2)25-23(13-16)26-20(5)29-19(4)18(3)15-35(29,6)30-28(26)32(25)40-22-10-8-21(9-11-22)14-24-27(31(30)37)34(39)36(7)33(24)38/h8-11,15-17,19,23-28,30,32H,12-14H2,1-7H3/t16-,17+,19-,23-,24-,25-,26-,27+,28+,30+,32-,35-/m0/s1
SMILES:	CC1CC(C2C(C1)C3C4C2OC5=CC=C(CC6C(C(=O)C4C7(C=C(C(C7=C3C)C)C)C)C(=O)N(C6=O)C)C=C5)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2431662
PubChem CID:	72701619
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0003909] Fatty Acyls [CHEMONTID:0000513] Eicosanoids [CHEMONTID:0000514] Prostaglandins and related compounds

*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
NPO32615	phoma sp. nrrl 46751	Species	Didymellaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24079882]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	1
MIC	2

Activity Type	# Activity
Cell Line	1
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT189	Cell Line	Vero	Chlorocebus aethiops	IC50	=	145300.0	nM	PMID[534517]
NPT88	Organism	Mycobacterium tuberculosis	Mycobacterium tuberculosis	MIC	>	100.0	ug.mL-1	PMID[534517]

☑ 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 NPC471396 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	306
0.1-0.2	1348
0.2-0.3	2871
0.3-0.4	9855
0.4-0.5	11032
0.5-0.6	15321
0.6-0.7	1928
0.7-0.8	32
0.8-0.85	0
0.85-0.9	3
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8571	High Similarity	NPC293164
0.8571	High Similarity	NPC471394
0.7952	Intermediate Similarity	NPC67080
0.7821	Intermediate Similarity	NPC106606
0.7751	Intermediate Similarity	NPC71205
0.7543	Intermediate Similarity	NPC211713
0.7543	Intermediate Similarity	NPC88378
0.7418	Intermediate Similarity	NPC471395
0.7378	Intermediate Similarity	NPC470273
0.7356	Intermediate Similarity	NPC469505
0.7273	Intermediate Similarity	NPC308709
0.7261	Intermediate Similarity	NPC283079
0.7219	Intermediate Similarity	NPC253591
0.7209	Intermediate Similarity	NPC25351
0.7178	Intermediate Similarity	NPC150712
0.7158	Intermediate Similarity	NPC206061
0.7151	Intermediate Similarity	NPC471863
0.7143	Intermediate Similarity	NPC469479
0.7135	Intermediate Similarity	NPC261659
0.7083	Intermediate Similarity	NPC56731
0.7081	Intermediate Similarity	NPC132308
0.7011	Intermediate Similarity	NPC476443
0.7011	Intermediate Similarity	NPC133817
0.7006	Intermediate Similarity	NPC75432
0.7006	Intermediate Similarity	NPC471003
0.6994	Remote Similarity	NPC196708
0.6989	Remote Similarity	NPC475780
0.6959	Remote Similarity	NPC93666
0.6941	Remote Similarity	NPC471292
0.6941	Remote Similarity	NPC324081
0.6923	Remote Similarity	NPC199044
0.6923	Remote Similarity	NPC238843
0.6909	Remote Similarity	NPC194359
0.6909	Remote Similarity	NPC21797
0.6909	Remote Similarity	NPC194847
0.6909	Remote Similarity	NPC28641
0.6904	Remote Similarity	NPC79130
0.6886	Remote Similarity	NPC56197
0.6882	Remote Similarity	NPC102760
0.6882	Remote Similarity	NPC185456
0.6871	Remote Similarity	NPC266425
0.6871	Remote Similarity	NPC471006
0.6864	Remote Similarity	NPC472564
0.6854	Remote Similarity	NPC254700
0.6848	Remote Similarity	NPC307682
0.6842	Remote Similarity	NPC470999
0.6834	Remote Similarity	NPC293347
0.6828	Remote Similarity	NPC115906
0.6824	Remote Similarity	NPC189908
0.6824	Remote Similarity	NPC251372
0.6811	Remote Similarity	NPC167340
0.6809	Remote Similarity	NPC214629
0.6807	Remote Similarity	NPC225745
0.6802	Remote Similarity	NPC476336
0.68	Remote Similarity	NPC246164
0.6796	Remote Similarity	NPC284842
0.6791	Remote Similarity	NPC229234
0.6786	Remote Similarity	NPC221134
0.6784	Remote Similarity	NPC247221
0.6778	Remote Similarity	NPC186617
0.6778	Remote Similarity	NPC471651
0.6776	Remote Similarity	NPC471860
0.6776	Remote Similarity	NPC471859
0.6768	Remote Similarity	NPC325568
0.6753	Remote Similarity	NPC33900
0.6734	Remote Similarity	NPC258128
0.6728	Remote Similarity	NPC59502
0.6726	Remote Similarity	NPC307883
0.6726	Remote Similarity	NPC234548
0.6726	Remote Similarity	NPC248287
0.6724	Remote Similarity	NPC471001
0.6724	Remote Similarity	NPC95526
0.6708	Remote Similarity	NPC269598
0.6707	Remote Similarity	NPC307401
0.6705	Remote Similarity	NPC224418
0.6705	Remote Similarity	NPC302987
0.6704	Remote Similarity	NPC472923
0.6703	Remote Similarity	NPC475421
0.6702	Remote Similarity	NPC473007
0.6701	Remote Similarity	NPC475747
0.6688	Remote Similarity	NPC321133
0.6688	Remote Similarity	NPC168050
0.6687	Remote Similarity	NPC180647
0.6686	Remote Similarity	NPC196846
0.6686	Remote Similarity	NPC146014
0.6684	Remote Similarity	NPC470112
0.6684	Remote Similarity	NPC470903
0.6684	Remote Similarity	NPC149285
0.6684	Remote Similarity	NPC99723
0.6684	Remote Similarity	NPC167763
0.6683	Remote Similarity	NPC476500
0.6667	Remote Similarity	NPC319320
0.6667	Remote Similarity	NPC223807
0.6667	Remote Similarity	NPC473748
0.6667	Remote Similarity	NPC287757
0.6667	Remote Similarity	NPC205392
0.6667	Remote Similarity	NPC235698
0.6667	Remote Similarity	NPC105942
0.6667	Remote Similarity	NPC98804
0.6649	Remote Similarity	NPC473008
0.6649	Remote Similarity	NPC470646
0.6649	Remote Similarity	NPC283207
0.6648	Remote Similarity	NPC272590
0.6648	Remote Similarity	NPC61967
0.6648	Remote Similarity	NPC62692
0.6648	Remote Similarity	NPC27541
0.6648	Remote Similarity	NPC126984
0.6648	Remote Similarity	NPC471000
0.6647	Remote Similarity	NPC233763
0.6647	Remote Similarity	NPC218092
0.6647	Remote Similarity	NPC252343
0.6647	Remote Similarity	NPC146872
0.6647	Remote Similarity	NPC162851
0.6647	Remote Similarity	NPC246474
0.6646	Remote Similarity	NPC475102
0.6646	Remote Similarity	NPC470278
0.6646	Remote Similarity	NPC470858
0.6633	Remote Similarity	NPC169605
0.663	Remote Similarity	NPC473502
0.663	Remote Similarity	NPC476751
0.6629	Remote Similarity	NPC323443
0.6629	Remote Similarity	NPC180756
0.6629	Remote Similarity	NPC234494
0.6629	Remote Similarity	NPC146388
0.6629	Remote Similarity	NPC470998
0.6627	Remote Similarity	NPC202260
0.6627	Remote Similarity	NPC233707
0.6627	Remote Similarity	NPC265335
0.6627	Remote Similarity	NPC470871
0.6616	Remote Similarity	NPC473005
0.6611	Remote Similarity	NPC84349
0.6611	Remote Similarity	NPC472823
0.6611	Remote Similarity	NPC474932
0.661	Remote Similarity	NPC471649
0.661	Remote Similarity	NPC470996
0.6609	Remote Similarity	NPC71821
0.6609	Remote Similarity	NPC471174
0.6607	Remote Similarity	NPC474610
0.6606	Remote Similarity	NPC279596
0.6606	Remote Similarity	NPC470977
0.6606	Remote Similarity	NPC196979
0.6606	Remote Similarity	NPC15083
0.6606	Remote Similarity	NPC470976
0.6606	Remote Similarity	NPC318862
0.6606	Remote Similarity	NPC239134
0.6605	Remote Similarity	NPC218323
0.6599	Remote Similarity	NPC67904
0.6593	Remote Similarity	NPC471858
0.6591	Remote Similarity	NPC472298
0.6591	Remote Similarity	NPC470997
0.659	Remote Similarity	NPC280717
0.659	Remote Similarity	NPC290038
0.659	Remote Similarity	NPC271607
0.6588	Remote Similarity	NPC76312
0.6587	Remote Similarity	NPC471864
0.6587	Remote Similarity	NPC109580
0.6587	Remote Similarity	NPC194970
0.6587	Remote Similarity	NPC37065
0.6585	Remote Similarity	NPC288290
0.6582	Remote Similarity	NPC293624
0.658	Remote Similarity	NPC473004
0.6578	Remote Similarity	NPC35680
0.6576	Remote Similarity	NPC310572
0.6575	Remote Similarity	NPC472574
0.6573	Remote Similarity	NPC27615
0.6573	Remote Similarity	NPC169742
0.6573	Remote Similarity	NPC44606
0.6571	Remote Similarity	NPC470082
0.6568	Remote Similarity	NPC236532
0.6567	Remote Similarity	NPC326895
0.6566	Remote Similarity	NPC169766
0.6566	Remote Similarity	NPC251549
0.6564	Remote Similarity	NPC30491
0.6564	Remote Similarity	NPC262936
0.6561	Remote Similarity	NPC293424
0.6559	Remote Similarity	NPC475641
0.6559	Remote Similarity	NPC475237
0.6557	Remote Similarity	NPC473693
0.6557	Remote Similarity	NPC471568
0.6557	Remote Similarity	NPC471850
0.6556	Remote Similarity	NPC476750
0.6556	Remote Similarity	NPC469847
0.6554	Remote Similarity	NPC140133
0.6554	Remote Similarity	NPC163002
0.655	Remote Similarity	NPC29599
0.655	Remote Similarity	NPC323601
0.655	Remote Similarity	NPC155552
0.655	Remote Similarity	NPC51181
0.6548	Remote Similarity	NPC42793
0.6548	Remote Similarity	NPC167944
0.6548	Remote Similarity	NPC477874
0.6548	Remote Similarity	NPC231884
0.6548	Remote Similarity	NPC173569
0.6545	Remote Similarity	NPC329731
0.6545	Remote Similarity	NPC4910
0.6545	Remote Similarity	NPC183348
0.6545	Remote Similarity	NPC282230
0.6543	Remote Similarity	NPC195972
0.6543	Remote Similarity	NPC137416
0.6541	Remote Similarity	NPC21216

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 NPC471396 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	199
0.1-0.2	717
0.2-0.3	1014
0.3-0.4	2326
0.4-0.5	2843
0.5-0.6	1626
0.6-0.7	410
0.7-0.8	15
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
0.7702	Intermediate Similarity	NPD7910	Clinical (unspecified phase)
0.7665	Intermediate Similarity	NPD7248	Discontinued
0.7371	Intermediate Similarity	NPD8051	Clinical (unspecified phase)
0.7342	Intermediate Similarity	NPD8032	Phase 2
0.7273	Intermediate Similarity	NPD5327	Phase 3
0.7151	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD3142	Approved
0.7081	Intermediate Similarity	NPD3140	Approved
0.7059	Intermediate Similarity	NPD5699	Approved
0.7052	Intermediate Similarity	NPD5714	Approved
0.7035	Intermediate Similarity	NPD5713	Approved
0.7011	Intermediate Similarity	NPD6668	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD7193	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD6353	Approved
0.6975	Remote Similarity	NPD4140	Approved
0.6971	Remote Similarity	NPD5616	Clinical (unspecified phase)
0.697	Remote Similarity	NPD4477	Approved
0.697	Remote Similarity	NPD4476	Approved
0.6966	Remote Similarity	NPD6457	Approved
0.6959	Remote Similarity	NPD7427	Discontinued
0.6957	Remote Similarity	NPD6812	Clinical (unspecified phase)
0.6952	Remote Similarity	NPD7693	Approved
0.6933	Remote Similarity	NPD4622	Approved
0.6933	Remote Similarity	NPD5735	Approved
0.6933	Remote Similarity	NPD4618	Approved
0.6919	Remote Similarity	NPD4210	Discontinued
0.6905	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD4110	Phase 3
0.6901	Remote Similarity	NPD6273	Approved
0.6899	Remote Similarity	NPD7258	Clinical (unspecified phase)
0.6899	Remote Similarity	NPD1876	Approved
0.6897	Remote Similarity	NPD7110	Phase 1
0.6897	Remote Similarity	NPD6677	Suspended
0.6897	Remote Similarity	NPD7109	Clinical (unspecified phase)
0.6893	Remote Similarity	NPD7831	Phase 2
0.6893	Remote Similarity	NPD7833	Phase 2
0.6893	Remote Similarity	NPD7832	Clinical (unspecified phase)
0.6886	Remote Similarity	NPD7037	Approved
0.6878	Remote Similarity	NPD5525	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD5978	Approved
0.6875	Remote Similarity	NPD5977	Approved
0.686	Remote Similarity	NPD6662	Clinical (unspecified phase)
0.686	Remote Similarity	NPD7131	Phase 3
0.6852	Remote Similarity	NPD7294	Phase 1
0.6848	Remote Similarity	NPD5688	Approved
0.6848	Remote Similarity	NPD5689	Approved
0.6842	Remote Similarity	NPD7020	Approved
0.6842	Remote Similarity	NPD7019	Approved
0.6839	Remote Similarity	NPD7028	Phase 2
0.6839	Remote Similarity	NPD6875	Approved
0.6839	Remote Similarity	NPD6876	Approved
0.6836	Remote Similarity	NPD4947	Clinical (unspecified phase)
0.6828	Remote Similarity	NPD2971	Approved
0.6828	Remote Similarity	NPD2968	Approved
0.6813	Remote Similarity	NPD7018	Phase 2
0.681	Remote Similarity	NPD6663	Approved
0.6788	Remote Similarity	NPD4579	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD2157	Approved
0.6768	Remote Similarity	NPD3109	Approved
0.6768	Remote Similarity	NPD3110	Approved
0.6761	Remote Similarity	NPD7577	Discontinued
0.6761	Remote Similarity	NPD6280	Approved
0.6761	Remote Similarity	NPD6279	Approved
0.676	Remote Similarity	NPD8245	Clinical (unspecified phase)
0.676	Remote Similarity	NPD6315	Phase 2
0.6758	Remote Similarity	NPD4481	Phase 3
0.675	Remote Similarity	NPD4098	Discontinued
0.6747	Remote Similarity	NPD743	Approved
0.6747	Remote Similarity	NPD7119	Phase 2
0.674	Remote Similarity	NPD7315	Approved
0.6728	Remote Similarity	NPD2614	Approved
0.6727	Remote Similarity	NPD6355	Discontinued
0.6726	Remote Similarity	NPD5865	Clinical (unspecified phase)
0.6725	Remote Similarity	NPD6667	Approved
0.6725	Remote Similarity	NPD6666	Approved
0.6724	Remote Similarity	NPD4124	Clinical (unspecified phase)
0.6722	Remote Similarity	NPD2042	Clinical (unspecified phase)
0.6722	Remote Similarity	NPD2041	Clinical (unspecified phase)
0.6706	Remote Similarity	NPD7466	Approved
0.6705	Remote Similarity	NPD1975	Clinical (unspecified phase)
0.6705	Remote Similarity	NPD6873	Phase 2
0.6703	Remote Similarity	NPD5441	Clinical (unspecified phase)
0.6701	Remote Similarity	NPD5564	Approved
0.6688	Remote Similarity	NPD2667	Approved
0.6688	Remote Similarity	NPD2668	Approved
0.6686	Remote Similarity	NPD2897	Discontinued
0.6686	Remote Similarity	NPD7596	Clinical (unspecified phase)
0.6685	Remote Similarity	NPD6620	Discovery
0.6685	Remote Similarity	NPD7177	Discontinued
0.6685	Remote Similarity	NPD8127	Discontinued
0.6685	Remote Similarity	NPD5967	Approved
0.6684	Remote Similarity	NPD7190	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5736	Approved
0.6667	Remote Similarity	NPD6844	Discontinued
0.6649	Remote Similarity	NPD7281	Phase 3
0.6649	Remote Similarity	NPD5312	Approved
0.6649	Remote Similarity	NPD5313	Approved
0.6649	Remote Similarity	NPD7280	Phase 3
0.6648	Remote Similarity	NPD6808	Phase 2
0.6647	Remote Similarity	NPD2976	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD3374	Clinical (unspecified phase)
0.6645	Remote Similarity	NPD3596	Phase 2
0.6626	Remote Similarity	NPD5752	Clinical (unspecified phase)
0.6624	Remote Similarity	NPD3445	Approved
0.6624	Remote Similarity	NPD6382	Discontinued
0.6624	Remote Similarity	NPD3024	Approved
0.6624	Remote Similarity	NPD3444	Approved
0.6624	Remote Similarity	NPD6830	Clinical (unspecified phase)
0.6624	Remote Similarity	NPD1651	Approved
0.6624	Remote Similarity	NPD3025	Approved
0.6624	Remote Similarity	NPD3443	Approved
0.6615	Remote Similarity	NPD2488	Approved
0.6615	Remote Similarity	NPD2490	Approved
0.6614	Remote Similarity	NPD6556	Clinical (unspecified phase)
0.661	Remote Similarity	NPD4424	Discontinued
0.6608	Remote Similarity	NPD5754	Discontinued
0.6607	Remote Similarity	NPD6029	Clinical (unspecified phase)
0.6607	Remote Similarity	NPD6028	Clinical (unspecified phase)
0.6606	Remote Similarity	NPD7265	Discontinued
0.6606	Remote Similarity	NPD7713	Phase 3
0.6605	Remote Similarity	NPD4624	Approved
0.6605	Remote Similarity	NPD7905	Discontinued
0.6596	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6591	Remote Similarity	NPD8158	Clinical (unspecified phase)
0.659	Remote Similarity	NPD7837	Clinical (unspecified phase)
0.6588	Remote Similarity	NPD3655	Clinical (unspecified phase)
0.6583	Remote Similarity	NPD7497	Discontinued
0.6582	Remote Similarity	NPD2932	Approved
0.6576	Remote Similarity	NPD3451	Clinical (unspecified phase)
0.6575	Remote Similarity	NPD7400	Phase 3
0.6571	Remote Similarity	NPD4727	Phase 1
0.6571	Remote Similarity	NPD3639	Approved
0.6571	Remote Similarity	NPD3641	Approved
0.6571	Remote Similarity	NPD3640	Phase 3
0.6571	Remote Similarity	NPD5586	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD1670	Discontinued
0.6568	Remote Similarity	NPD6032	Approved
0.6566	Remote Similarity	NPD2979	Phase 3
0.6562	Remote Similarity	NPD3972	Approved
0.6561	Remote Similarity	NPD8064	Clinical (unspecified phase)
0.6561	Remote Similarity	NPD6581	Approved
0.6561	Remote Similarity	NPD6580	Approved
0.6558	Remote Similarity	NPD1241	Discontinued
0.6557	Remote Similarity	NPD7608	Discontinued
0.6556	Remote Similarity	NPD5019	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD3688	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD3146	Approved
0.655	Remote Similarity	NPD2654	Approved
0.6548	Remote Similarity	NPD6895	Approved
0.6548	Remote Similarity	NPD6896	Approved
0.6541	Remote Similarity	NPD3026	Approved
0.6541	Remote Similarity	NPD3023	Approved
0.6538	Remote Similarity	NPD2904	Discontinued
0.6531	Remote Similarity	NPD2974	Approved
0.6531	Remote Similarity	NPD2975	Approved
0.6531	Remote Similarity	NPD2973	Approved
0.6529	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6529	Remote Similarity	NPD6004	Phase 3
0.6529	Remote Similarity	NPD5762	Approved
0.6529	Remote Similarity	NPD6005	Phase 3
0.6529	Remote Similarity	NPD6002	Phase 3
0.6529	Remote Similarity	NPD5763	Approved
0.6529	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6528	Remote Similarity	NPD3808	Clinical (unspecified phase)
0.6528	Remote Similarity	NPD6504	Approved
0.6528	Remote Similarity	NPD6505	Approved
0.6527	Remote Similarity	NPD3657	Discovery
0.6526	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD2969	Approved
0.6522	Remote Similarity	NPD2970	Approved
0.6515	Remote Similarity	NPD4580	Approved
0.651	Remote Similarity	NPD6040	Clinical (unspecified phase)
0.651	Remote Similarity	NPD7291	Discontinued
0.6506	Remote Similarity	NPD2245	Discovery
0.6503	Remote Similarity	NPD5647	Approved
0.6491	Remote Similarity	NPD1372	Clinical (unspecified phase)
0.6486	Remote Similarity	NPD2489	Approved
0.6486	Remote Similarity	NPD27	Approved
0.6485	Remote Similarity	NPD5746	Approved
0.6485	Remote Similarity	NPD5163	Phase 2
0.6484	Remote Similarity	NPD6862	Phase 2
0.6478	Remote Similarity	NPD2423	Clinical (unspecified phase)
0.6478	Remote Similarity	NPD3019	Approved
0.6474	Remote Similarity	NPD5084	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD2240	Approved
0.6471	Remote Similarity	NPD2239	Approved
0.6471	Remote Similarity	NPD2438	Suspended
0.6471	Remote Similarity	NPD3050	Clinical (unspecified phase)
0.6467	Remote Similarity	NPD3051	Approved
0.6461	Remote Similarity	NPD1337	Clinical (unspecified phase)
0.646	Remote Similarity	NPD2232	Approved
0.646	Remote Similarity	NPD2230	Approved
0.646	Remote Similarity	NPD2233	Approved
0.6453	Remote Similarity	NPD7179	Phase 2
0.6444	Remote Similarity	NPD5760	Phase 2
0.6444	Remote Similarity	NPD5761	Phase 2
0.6438	Remote Similarity	NPD7457	Clinical (unspecified phase)
0.6433	Remote Similarity	NPD7702	Clinical (unspecified phase)
0.6432	Remote Similarity	NPD4107	Approved
0.6429	Remote Similarity	NPD8005	Clinical (unspecified phase)

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