NPASS Compound

Structure

NPC473910 OpenBabel07101718202D 49 48 0 0 1 0 0 0 0 0999 V2000 -19.0526 12.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6603 -6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -19.0526 11.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 -6.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -19.0526 10.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -18.1865 9.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -17.3205 10.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -16.4545 9.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -15.5885 10.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -14.7224 9.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -13.8564 10.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.9904 9.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.1244 10.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.2583 9.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.3923 10.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.5263 9.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.6603 10.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 9.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 10.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 9.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 10.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 9.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 8.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 8.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 7.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 6.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -6.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 -7.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7321 5.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 6.9282 -8.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 4.0000 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 3 3 0 0 0 0 2 4 3 0 0 0 0 3 5 1 0 0 0 0 4 44 1 0 0 0 0 5 6 2 0 0 0 0 6 7 1 0 0 0 0 7 8 1 0 0 0 0 8 9 1 0 0 0 0 9 10 1 0 0 0 0 10 11 1 0 0 0 0 11 12 1 0 0 0 0 12 13 1 0 0 0 0 13 14 1 0 0 0 0 14 15 1 0 0 0 0 15 16 1 0 0 0 0 16 17 1 0 0 0 0 17 18 1 0 0 0 0 18 19 1 0 0 0 0 19 20 1 0 0 0 0 20 21 1 0 0 0 0 21 22 2 0 0 0 0 22 23 1 0 0 0 0 23 27 1 0 0 0 0 24 25 1 0 0 0 0 24 26 1 0 0 0 0 25 28 1 0 0 0 0 26 29 1 0 0 0 0 27 30 1 0 0 0 0 28 31 1 0 0 0 0 29 34 1 0 0 0 0 30 35 1 0 0 0 0 31 36 1 0 0 0 0 32 33 1 0 0 0 0 32 37 1 0 0 0 0 33 38 1 0 0 0 0 34 39 2 0 0 0 0 35 40 2 0 0 0 0 36 41 3 0 0 0 0 37 42 1 0 0 0 0 38 43 3 0 0 0 0 39 44 1 0 0 0 0 40 45 1 0 0 0 0 41 46 1 0 0 0 0 42 45 1 0 0 0 0 43 46 1 0 0 0 0 44 47 1 6 0 0 0 45 48 1 0 0 0 0 46 49 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	670.53
Volume:	798.905
LogP:	10.061
LogD:	4.956
LogS:	-2.168
# Rotatable Bonds:	31
TPSA:	60.69
# H-Bond Aceptor:	3
# H-Bond Donor:	3
# Rings:	0
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.039
Synthetic Accessibility Score:	4.696
Fsp3:	0.652
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.297
MDCK Permeability:	4.4803787204728e-06
Pgp-inhibitor:	0.0
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.988
20% Bioavailability (F20%):	1.0
30% Bioavailability (F30%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0
Plasma Protein Binding (PPB):	103.80854034423828%
Volume Distribution (VD):	0.426
Pgp-substrate:	0.31305694580078125%

ADMET: Metabolism

CYP1A2-inhibitor:	0.161
CYP1A2-substrate:	0.114
CYP2C19-inhibitor:	0.712
CYP2C19-substrate:	0.063
CYP2C9-inhibitor:	0.184
CYP2C9-substrate:	0.999
CYP2D6-inhibitor:	0.106
CYP2D6-substrate:	0.013
CYP3A4-inhibitor:	0.535
CYP3A4-substrate:	0.04

ADMET: Excretion

Clearance (CL):	2.989
Half-life (T1/2):	0.123

ADMET: Toxicity

hERG Blockers:	0.0
Human Hepatotoxicity (H-HT):	0.179
Drug-inuced Liver Injury (DILI):	0.394
AMES Toxicity:	0.09
Rat Oral Acute Toxicity:	0.963
Maximum Recommended Daily Dose:	1.0
Skin Sensitization:	0.993
Carcinogencity:	0.032
Eye Corrosion:	0.013
Eye Irritation:	0.946
Respiratory Toxicity:	0.983

Download Data

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

Natural Product: NPC473910

Natural Product ID:	NPC473910
*Common Name:**	Petrocortyne E
IUPAC Name:	(3R,4E,14R,22E,27Z,43Z)-hexatetraconta-4,22,27,43-tetraen-1,12,15,45-tetrayne-3,14,21-triol
Synonyms:	Petrocortyne E
Standard InCHIKey:	YDDFBFYVVQPBKW-IHCRENFYSA-N
Standard InCHI:	InChI=1S/C46H70O3/c1-3-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22-23-27-30-35-40-45(48)42-37-32-33-38-43-46(49)41-36-31-28-25-24-26-29-34-39-44(47)4-2/h1-2,5-6,21-22,34-35,39-40,44-49H,7-20,23-33,37,42H2/b6-5-,22-21-,39-34+,40-35+/t44-,45?,46+/m0/s1
SMILES:	C#CC=CCCCCCCCCCCCCCCC=CCCCC=CC(CCCCC#CC(C#CCCCCCCC=CC(C#C)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL455028
PubChem CID:	10604495
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0003909] Fatty Acyls [CHEMONTID:0001334] Fatty alcohols

*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
NPO30927	Petrosia	Genus	Petrosiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[10514299]
NPO30927	Petrosia	Genus	Petrosiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[21534590]
NPO30927	Petrosia	Genus	Petrosiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[9784165]

☑ 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
Others	2

Activity Type	# Activity
Cell Line	1
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT111	Cell Line	K562	Homo sapiens	LC50	=	7000.0	nM	PMID[458506]
NPT545	Individual Protein	Phospholipase A2 group 1B	Homo sapiens	Inhibition	=	48.0	%	PMID[458506]

☑ 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 NPC473910 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	159
0.1-0.2	4432
0.2-0.3	19944
0.3-0.4	12089
0.4-0.5	4535
0.5-0.6	1165
0.6-0.7	222
0.7-0.8	52
0.8-0.85	21
0.85-0.9	28
0.9-0.95	31
0.95-1	19

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC473735
1.0	High Similarity	NPC473725
1.0	High Similarity	NPC473896
1.0	High Similarity	NPC473721
1.0	High Similarity	NPC475353
0.9808	High Similarity	NPC473847
0.9808	High Similarity	NPC161838
0.9808	High Similarity	NPC471960
0.9808	High Similarity	NPC475384
0.9808	High Similarity	NPC470969
0.9808	High Similarity	NPC470967
0.9808	High Similarity	NPC470966
0.9808	High Similarity	NPC470968
0.9808	High Similarity	NPC477661
0.9804	High Similarity	NPC473532
0.9623	High Similarity	NPC470970
0.9615	High Similarity	NPC477725
0.9615	High Similarity	NPC477726
0.9231	High Similarity	NPC187361
0.9231	High Similarity	NPC26102
0.9231	High Similarity	NPC477724
0.9216	High Similarity	NPC76198
0.9216	High Similarity	NPC170776
0.9216	High Similarity	NPC165447
0.9216	High Similarity	NPC329608
0.9216	High Similarity	NPC224148
0.9216	High Similarity	NPC475477
0.9216	High Similarity	NPC294278
0.9216	High Similarity	NPC256656
0.9216	High Similarity	NPC471959
0.9216	High Similarity	NPC197272
0.9216	High Similarity	NPC9273
0.9216	High Similarity	NPC477723
0.9216	High Similarity	NPC89824
0.9057	High Similarity	NPC256209
0.9057	High Similarity	NPC49059
0.902	High Similarity	NPC199286
0.902	High Similarity	NPC471281
0.902	High Similarity	NPC477727
0.8846	High Similarity	NPC55383
0.8846	High Similarity	NPC151782
0.8846	High Similarity	NPC129263
0.8824	High Similarity	NPC471275
0.8824	High Similarity	NPC471280
0.8824	High Similarity	NPC125122
0.8824	High Similarity	NPC471276
0.8793	High Similarity	NPC470965
0.8704	High Similarity	NPC48058
0.8704	High Similarity	NPC110732
0.8654	High Similarity	NPC473913
0.8654	High Similarity	NPC249670
0.8654	High Similarity	NPC72699
0.8654	High Similarity	NPC474642
0.8621	High Similarity	NPC475984
0.8519	High Similarity	NPC34577
0.8462	Intermediate Similarity	NPC248884
0.8462	Intermediate Similarity	NPC31194
0.8462	Intermediate Similarity	NPC85079
0.8462	Intermediate Similarity	NPC153538
0.8431	Intermediate Similarity	NPC35141
0.8431	Intermediate Similarity	NPC124183
0.8393	Intermediate Similarity	NPC470964
0.8393	Intermediate Similarity	NPC311648
0.8246	Intermediate Similarity	NPC594
0.8246	Intermediate Similarity	NPC48968
0.8214	Intermediate Similarity	NPC152668
0.8214	Intermediate Similarity	NPC470963
0.8214	Intermediate Similarity	NPC146551
0.8214	Intermediate Similarity	NPC474513
0.8148	Intermediate Similarity	NPC474495
0.8148	Intermediate Similarity	NPC71053
0.8148	Intermediate Similarity	NPC473672
0.8148	Intermediate Similarity	NPC59408
0.8148	Intermediate Similarity	NPC93639
0.8077	Intermediate Similarity	NPC19834
0.8077	Intermediate Similarity	NPC55063
0.8039	Intermediate Similarity	NPC101616
0.7966	Intermediate Similarity	NPC473652
0.7963	Intermediate Similarity	NPC328784
0.7963	Intermediate Similarity	NPC291437
0.7937	Intermediate Similarity	NPC473752
0.7895	Intermediate Similarity	NPC471239
0.7895	Intermediate Similarity	NPC474644
0.7885	Intermediate Similarity	NPC269074
0.7869	Intermediate Similarity	NPC29697
0.7857	Intermediate Similarity	NPC474496
0.7778	Intermediate Similarity	NPC302310
0.7759	Intermediate Similarity	NPC473865
0.7759	Intermediate Similarity	NPC474643
0.7736	Intermediate Similarity	NPC157096
0.7705	Intermediate Similarity	NPC66460
0.7705	Intermediate Similarity	NPC168407
0.7705	Intermediate Similarity	NPC271282
0.7705	Intermediate Similarity	NPC325929
0.7692	Intermediate Similarity	NPC108195
0.7679	Intermediate Similarity	NPC142092
0.7647	Intermediate Similarity	NPC149668
0.7627	Intermediate Similarity	NPC193975
0.7547	Intermediate Similarity	NPC76976
0.7541	Intermediate Similarity	NPC471278
0.746	Intermediate Similarity	NPC470320
0.746	Intermediate Similarity	NPC226592
0.7419	Intermediate Similarity	NPC477829
0.7407	Intermediate Similarity	NPC180575
0.7377	Intermediate Similarity	NPC122239
0.7308	Intermediate Similarity	NPC46248
0.7308	Intermediate Similarity	NPC249801
0.7308	Intermediate Similarity	NPC304151
0.7288	Intermediate Similarity	NPC317899
0.7258	Intermediate Similarity	NPC327112
0.7255	Intermediate Similarity	NPC329762
0.7255	Intermediate Similarity	NPC27444
0.7255	Intermediate Similarity	NPC103236
0.7222	Intermediate Similarity	NPC276825
0.7222	Intermediate Similarity	NPC140501
0.7213	Intermediate Similarity	NPC226848
0.717	Intermediate Similarity	NPC252978
0.7097	Intermediate Similarity	NPC475931
0.7077	Intermediate Similarity	NPC136164
0.7077	Intermediate Similarity	NPC245947
0.7077	Intermediate Similarity	NPC308844
0.7077	Intermediate Similarity	NPC255863
0.7049	Intermediate Similarity	NPC44542
0.7049	Intermediate Similarity	NPC212730
0.7049	Intermediate Similarity	NPC474577
0.7049	Intermediate Similarity	NPC265551
0.7049	Intermediate Similarity	NPC472445
0.7018	Intermediate Similarity	NPC473768
0.7018	Intermediate Similarity	NPC474460
0.7	Intermediate Similarity	NPC227135
0.6949	Remote Similarity	NPC284224
0.6949	Remote Similarity	NPC61177
0.6949	Remote Similarity	NPC217188
0.6935	Remote Similarity	NPC181872
0.6912	Remote Similarity	NPC291196
0.6912	Remote Similarity	NPC103712
0.6866	Remote Similarity	NPC26500
0.6866	Remote Similarity	NPC99619
0.6852	Remote Similarity	NPC116934
0.6842	Remote Similarity	NPC475153
0.6825	Remote Similarity	NPC222852
0.6825	Remote Similarity	NPC474267
0.678	Remote Similarity	NPC473705
0.678	Remote Similarity	NPC35756
0.6774	Remote Similarity	NPC471277
0.6774	Remote Similarity	NPC471279
0.6769	Remote Similarity	NPC55068
0.6731	Remote Similarity	NPC471282
0.6731	Remote Similarity	NPC15934
0.6731	Remote Similarity	NPC306850
0.6721	Remote Similarity	NPC329686
0.6721	Remote Similarity	NPC281590
0.6719	Remote Similarity	NPC243532
0.6719	Remote Similarity	NPC328311
0.6667	Remote Similarity	NPC213538
0.6667	Remote Similarity	NPC206906
0.6667	Remote Similarity	NPC256766
0.6667	Remote Similarity	NPC469373
0.6667	Remote Similarity	NPC470436
0.6667	Remote Similarity	NPC155025
0.6667	Remote Similarity	NPC216416
0.6667	Remote Similarity	NPC471958
0.6667	Remote Similarity	NPC300593
0.6618	Remote Similarity	NPC73603
0.6618	Remote Similarity	NPC259299
0.6615	Remote Similarity	NPC321838
0.6615	Remote Similarity	NPC113293
0.6615	Remote Similarity	NPC201939
0.6613	Remote Similarity	NPC324224
0.6613	Remote Similarity	NPC48891
0.6613	Remote Similarity	NPC472808
0.661	Remote Similarity	NPC200772
0.661	Remote Similarity	NPC29234
0.6607	Remote Similarity	NPC160628
0.6567	Remote Similarity	NPC318420
0.6567	Remote Similarity	NPC323045
0.6567	Remote Similarity	NPC317881
0.6567	Remote Similarity	NPC19569
0.6567	Remote Similarity	NPC326268
0.6562	Remote Similarity	NPC322002
0.6557	Remote Similarity	NPC137538
0.6538	Remote Similarity	NPC34873
0.6538	Remote Similarity	NPC40434
0.6528	Remote Similarity	NPC477422
0.6528	Remote Similarity	NPC288086
0.6522	Remote Similarity	NPC224532
0.6522	Remote Similarity	NPC305698
0.6515	Remote Similarity	NPC473508
0.6508	Remote Similarity	NPC52012
0.6481	Remote Similarity	NPC269823
0.6471	Remote Similarity	NPC328653
0.6471	Remote Similarity	NPC267027
0.6471	Remote Similarity	NPC213767
0.6462	Remote Similarity	NPC99487
0.6462	Remote Similarity	NPC471081
0.6462	Remote Similarity	NPC158368
0.6462	Remote Similarity	NPC154908
0.6462	Remote Similarity	NPC252851
0.6462	Remote Similarity	NPC226872
0.6462	Remote Similarity	NPC299730

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 NPC473910 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	156
0.1-0.2	4059
0.2-0.3	3748
0.3-0.4	980
0.4-0.5	142
0.5-0.6	57
0.6-0.7	6
0.7-0.8	2
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
0.7258	Intermediate Similarity	NPD4246	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD4265	Approved
0.6769	Remote Similarity	NPD3210	Clinical (unspecified phase)
0.6438	Remote Similarity	NPD8264	Approved
0.6418	Remote Similarity	NPD3197	Phase 1
0.6377	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD368	Approved
0.6203	Remote Similarity	NPD5331	Approved
0.6203	Remote Similarity	NPD5332	Approved
0.619	Remote Similarity	NPD342	Phase 1
0.6111	Remote Similarity	NPD3212	Clinical (unspecified phase)
0.6032	Remote Similarity	NPD3196	Approved
0.6032	Remote Similarity	NPD4266	Approved
0.6032	Remote Similarity	NPD3195	Phase 2
0.6032	Remote Similarity	NPD3194	Approved
0.5974	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.5974	Remote Similarity	NPD4271	Approved
0.5974	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.5974	Remote Similarity	NPD4268	Approved
0.5949	Remote Similarity	NPD6898	Phase 1
0.5946	Remote Similarity	NPD4732	Discontinued
0.5909	Remote Similarity	NPD585	Clinical (unspecified phase)
0.5873	Remote Similarity	NPD3172	Approved
0.5846	Remote Similarity	NPD4219	Approved
0.5823	Remote Similarity	NPD4820	Approved
0.5823	Remote Similarity	NPD4821	Approved
0.5823	Remote Similarity	NPD7332	Phase 2
0.5823	Remote Similarity	NPD4819	Approved
0.5823	Remote Similarity	NPD4252	Approved
0.5823	Remote Similarity	NPD7514	Phase 3
0.5823	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.5823	Remote Similarity	NPD4822	Approved
0.5769	Remote Similarity	NPD7145	Approved
0.5763	Remote Similarity	NPD39	Approved
0.575	Remote Similarity	NPD6902	Approved
0.575	Remote Similarity	NPD4790	Discontinued
0.5738	Remote Similarity	NPD3173	Approved
0.5714	Remote Similarity	NPD7750	Discontinued
0.5714	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.5696	Remote Similarity	NPD6683	Phase 2
0.5679	Remote Similarity	NPD4269	Approved
0.5679	Remote Similarity	NPD4270	Approved
0.5676	Remote Similarity	NPD7144	Approved
0.5676	Remote Similarity	NPD7143	Approved
0.5672	Remote Similarity	NPD6109	Phase 1
0.5663	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.5641	Remote Similarity	NPD5776	Phase 2
0.5641	Remote Similarity	NPD6925	Approved
0.561	Remote Similarity	NPD7154	Phase 3
0.561	Remote Similarity	NPD5362	Discontinued
0.56	Remote Similarity	NPD7150	Approved
0.56	Remote Similarity	NPD7152	Approved
0.56	Remote Similarity	NPD7151	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