NPASS Compound

Structure

NPC594 OpenBabel07101719522D 51 50 0 0 1 0 0 0 0 0999 V2000 -25.9808 -21.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -25.9808 -20.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.6603 -8.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.6603 -7.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.5263 -8.5000 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 -9.5263 -9.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 -5.5000 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 -6.9282 -5.0000 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 -6.9282 -4.0000 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 -6.0622 -3.5000 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 -6.0622 -2.5000 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 -5.1962 -2.0000 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 -5.1962 -1.0000 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 -4.3301 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -15.5885 -11.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -16.4545 -11.5000 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 -22.5167 -17.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -21.6506 -17.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -23.3827 -17.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -16.4545 -12.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -20.7846 -17.0000 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 -24.2487 -17.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -17.3205 -13.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -19.9186 -17.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -25.1147 -17.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -17.3205 -14.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -19.0526 -17.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -25.1147 -18.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -17.3205 -15.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -18.1865 -16.5000 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 -25.9808 -19.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -17.3205 -16.0000 0.0000 C 0 0 2 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 -26.8468 -18.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -16.4545 -16.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 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 2 3 0 0 0 0 2 45 1 0 0 0 0 3 4 1 0 0 0 0 3 5 1 0 0 0 0 4 6 1 0 0 0 0 5 7 1 0 0 0 0 6 8 1 0 0 0 0 7 9 2 0 0 0 0 8 10 1 0 0 0 0 9 11 1 0 0 0 0 10 12 1 0 0 0 0 11 13 1 0 0 0 0 12 14 1 0 0 0 0 13 15 1 0 0 0 0 14 16 1 0 0 0 0 15 17 1 0 0 0 0 16 18 1 0 0 0 0 17 19 1 0 0 0 0 18 20 1 0 0 0 0 19 21 2 0 0 0 0 20 22 1 0 0 0 0 21 23 1 0 0 0 0 22 24 1 0 0 0 0 23 25 1 0 0 0 0 24 26 1 0 0 0 0 25 30 1 0 0 0 0 26 32 1 0 0 0 0 27 28 1 0 0 0 0 27 29 1 0 0 0 0 28 31 1 0 0 0 0 29 33 1 0 0 0 0 30 34 2 0 0 0 0 31 35 1 0 0 0 0 32 36 2 0 0 0 0 33 37 1 0 0 0 0 34 38 1 0 0 0 0 35 39 1 0 0 0 0 36 40 1 0 0 0 0 37 41 2 0 0 0 0 38 42 3 0 0 0 0 39 43 3 0 0 0 0 40 44 3 0 0 0 0 41 45 1 0 0 0 0 42 46 1 0 0 0 0 43 46 1 0 0 0 0 44 47 1 0 0 0 0 45 48 1 1 0 0 0 46 49 1 1 0 0 0 47 50 2 0 0 0 0 47 51 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	696.51
Volume:	819.718
LogP:	9.911
LogD:	4.357
LogS:	-1.671
# Rotatable Bonds:	30
TPSA:	77.76
# H-Bond Aceptor:	4
# H-Bond Donor:	3
# Rings:	0
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.04
Synthetic Accessibility Score:	4.673
Fsp3:	0.596
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	2
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.25
MDCK Permeability:	1.884961238829419e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.922
20% Bioavailability (F20%):	1.0
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0
Plasma Protein Binding (PPB):	108.51757049560547%
Volume Distribution (VD):	1.514
Pgp-substrate:	0.20068934559822083%

ADMET: Metabolism

CYP1A2-inhibitor:	0.192
CYP1A2-substrate:	0.108
CYP2C19-inhibitor:	0.58
CYP2C19-substrate:	0.062
CYP2C9-inhibitor:	0.23
CYP2C9-substrate:	1.0
CYP2D6-inhibitor:	0.532
CYP2D6-substrate:	0.133
CYP3A4-inhibitor:	0.574
CYP3A4-substrate:	0.01

ADMET: Excretion

Clearance (CL):	2.386
Half-life (T1/2):	0.438

ADMET: Toxicity

hERG Blockers:	0.001
Human Hepatotoxicity (H-HT):	0.835
Drug-inuced Liver Injury (DILI):	0.964
AMES Toxicity:	0.129
Rat Oral Acute Toxicity:	0.523
Maximum Recommended Daily Dose:	1.0
Skin Sensitization:	0.992
Carcinogencity:	0.17
Eye Corrosion:	0.739
Eye Irritation:	0.932
Respiratory Toxicity:	0.996

Download Data

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

Natural Product: NPC594

Natural Product ID:	NPC594
*Common Name:**	Petroformynic Acid B
IUPAC Name:	(4Z,20Z,26Z,30E,34S,43E,45S)-34,45-dihydroxyheptatetraconta-4,20,26,30,43-pentaen-2,32,35,46-tetraynoic acid
Synonyms:
Standard InCHIKey:	BZLCFINUEDERAD-JCPHLTBWSA-N
Standard InCHI:	InChI=1S/C47H68O4/c1-2-45(48)41-37-33-29-27-28-31-35-39-43-46(49)42-38-34-30-25-23-21-19-17-15-13-11-9-7-5-3-4-6-8-10-12-14-16-18-20-22-24-26-32-36-40-44-47(50)51/h1,7,9,19,21,30,32,34,36-37,41,45-46,48-49H,3-6,8,10-18,20,22-29,31,33,35H2,(H,50,51)/b9-7-,21-19-,34-30+,36-32-,41-37+/t45-,46-/m1/s1
SMILES:	C#C[C@H](/C=C/CCCCCCC#C[C@@H](C#C/C=C/CC/C=CCCCC/C=CCCCCCCCCCCCCCC/C=CC#CC(=O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL249074
PubChem CID:	24179503
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0003909] Fatty Acyls [CHEMONTID:0000262] Fatty acids and conjugates [CHEMONTID:0002950] Very long-chain fatty acids

*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
NPO32455	pertrosia sp.	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[17985844]

☑ 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

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT168	Cell Line	P388	Mus musculus	IC50	=	0.4	ug.mL-1	PMID[519912]

☑ 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 NPC594 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	160
0.1-0.2	4529
0.2-0.3	20203
0.3-0.4	11455
0.4-0.5	4797
0.5-0.6	1157
0.6-0.7	255
0.7-0.8	75
0.8-0.85	32
0.85-0.9	24
0.9-0.95	2
0.95-1	8

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC48968
0.9811	High Similarity	NPC311648
0.9811	High Similarity	NPC470964
0.9623	High Similarity	NPC470963
0.9623	High Similarity	NPC146551
0.9623	High Similarity	NPC474513
0.9623	High Similarity	NPC152668
0.9138	High Similarity	NPC470965
0.9074	High Similarity	NPC48058
0.8966	High Similarity	NPC475984
0.8868	High Similarity	NPC256656
0.8868	High Similarity	NPC55383
0.8868	High Similarity	NPC294278
0.8868	High Similarity	NPC76198
0.8868	High Similarity	NPC475477
0.8868	High Similarity	NPC329608
0.8868	High Similarity	NPC471959
0.8868	High Similarity	NPC477723
0.8868	High Similarity	NPC224148
0.8868	High Similarity	NPC9273
0.8868	High Similarity	NPC170776
0.8868	High Similarity	NPC197272
0.8868	High Similarity	NPC165447
0.8868	High Similarity	NPC89824
0.8793	High Similarity	NPC471278
0.8679	High Similarity	NPC471281
0.8679	High Similarity	NPC199286
0.8679	High Similarity	NPC477727
0.8491	Intermediate Similarity	NPC471276
0.8491	Intermediate Similarity	NPC471280
0.8491	Intermediate Similarity	NPC125122
0.8491	Intermediate Similarity	NPC471275
0.8393	Intermediate Similarity	NPC473532
0.8333	Intermediate Similarity	NPC325929
0.8333	Intermediate Similarity	NPC474642
0.8333	Intermediate Similarity	NPC473913
0.8333	Intermediate Similarity	NPC249670
0.8333	Intermediate Similarity	NPC66460
0.8333	Intermediate Similarity	NPC271282
0.8305	Intermediate Similarity	NPC473652
0.8276	Intermediate Similarity	NPC212730
0.8276	Intermediate Similarity	NPC470970
0.8276	Intermediate Similarity	NPC265551
0.8276	Intermediate Similarity	NPC471279
0.8276	Intermediate Similarity	NPC471277
0.8246	Intermediate Similarity	NPC473896
0.8246	Intermediate Similarity	NPC471239
0.8246	Intermediate Similarity	NPC475353
0.8246	Intermediate Similarity	NPC473910
0.8246	Intermediate Similarity	NPC473735
0.8246	Intermediate Similarity	NPC473721
0.8246	Intermediate Similarity	NPC473725
0.8197	Intermediate Similarity	NPC29697
0.8148	Intermediate Similarity	NPC248884
0.8148	Intermediate Similarity	NPC85079
0.8148	Intermediate Similarity	NPC31194
0.8113	Intermediate Similarity	NPC124183
0.8113	Intermediate Similarity	NPC35141
0.8103	Intermediate Similarity	NPC161838
0.8103	Intermediate Similarity	NPC471960
0.8103	Intermediate Similarity	NPC470967
0.8103	Intermediate Similarity	NPC475384
0.8103	Intermediate Similarity	NPC477661
0.8103	Intermediate Similarity	NPC470969
0.8103	Intermediate Similarity	NPC470966
0.8103	Intermediate Similarity	NPC473847
0.8103	Intermediate Similarity	NPC470968
0.8033	Intermediate Similarity	NPC168407
0.8	Intermediate Similarity	NPC72699
0.7966	Intermediate Similarity	NPC44542
0.7931	Intermediate Similarity	NPC477726
0.7931	Intermediate Similarity	NPC477725
0.7857	Intermediate Similarity	NPC151782
0.7818	Intermediate Similarity	NPC153538
0.7778	Intermediate Similarity	NPC19834
0.7778	Intermediate Similarity	NPC55063
0.7736	Intermediate Similarity	NPC101616
0.7667	Intermediate Similarity	NPC472445
0.7667	Intermediate Similarity	NPC193975
0.7627	Intermediate Similarity	NPC474644
0.7593	Intermediate Similarity	NPC269074
0.7586	Intermediate Similarity	NPC187361
0.7586	Intermediate Similarity	NPC26102
0.7586	Intermediate Similarity	NPC477724
0.7544	Intermediate Similarity	NPC93639
0.75	Intermediate Similarity	NPC474643
0.75	Intermediate Similarity	NPC470320
0.75	Intermediate Similarity	NPC226592
0.75	Intermediate Similarity	NPC473865
0.746	Intermediate Similarity	NPC477829
0.7458	Intermediate Similarity	NPC49059
0.7458	Intermediate Similarity	NPC256209
0.7424	Intermediate Similarity	NPC473752
0.7419	Intermediate Similarity	NPC474267
0.7419	Intermediate Similarity	NPC329424
0.7419	Intermediate Similarity	NPC222852
0.7414	Intermediate Similarity	NPC142092
0.7358	Intermediate Similarity	NPC149668
0.7302	Intermediate Similarity	NPC327112
0.7288	Intermediate Similarity	NPC61177
0.7241	Intermediate Similarity	NPC129263
0.7241	Intermediate Similarity	NPC71053
0.7241	Intermediate Similarity	NPC59408
0.7167	Intermediate Similarity	NPC269615
0.7167	Intermediate Similarity	NPC110732
0.7164	Intermediate Similarity	NPC99619
0.7164	Intermediate Similarity	NPC26500
0.7143	Intermediate Similarity	NPC180575
0.7143	Intermediate Similarity	NPC157096
0.7143	Intermediate Similarity	NPC322186
0.7121	Intermediate Similarity	NPC245947
0.7121	Intermediate Similarity	NPC255863
0.7121	Intermediate Similarity	NPC136164
0.7069	Intermediate Similarity	NPC291437
0.7069	Intermediate Similarity	NPC328784
0.7049	Intermediate Similarity	NPC474913
0.7037	Intermediate Similarity	NPC304151
0.7031	Intermediate Similarity	NPC299730
0.7031	Intermediate Similarity	NPC328311
0.7018	Intermediate Similarity	NPC471958
0.7	Intermediate Similarity	NPC34577
0.6984	Remote Similarity	NPC469373
0.6981	Remote Similarity	NPC329762
0.6981	Remote Similarity	NPC103236
0.6981	Remote Similarity	NPC27444
0.697	Remote Similarity	NPC476658
0.6957	Remote Similarity	NPC470436
0.6949	Remote Similarity	NPC474495
0.6949	Remote Similarity	NPC473672
0.6935	Remote Similarity	NPC324224
0.6935	Remote Similarity	NPC472808
0.6923	Remote Similarity	NPC321838
0.6923	Remote Similarity	NPC26810
0.6897	Remote Similarity	NPC302310
0.6875	Remote Similarity	NPC322002
0.6875	Remote Similarity	NPC318306
0.6875	Remote Similarity	NPC329249
0.6866	Remote Similarity	NPC326268
0.6866	Remote Similarity	NPC318420
0.6833	Remote Similarity	NPC106531
0.6825	Remote Similarity	NPC323436
0.6825	Remote Similarity	NPC129150
0.6786	Remote Similarity	NPC108195
0.6769	Remote Similarity	NPC243532
0.6765	Remote Similarity	NPC328653
0.6765	Remote Similarity	NPC476656
0.6765	Remote Similarity	NPC146811
0.6765	Remote Similarity	NPC476659
0.6721	Remote Similarity	NPC284224
0.6719	Remote Similarity	NPC223679
0.6714	Remote Similarity	NPC236208
0.6714	Remote Similarity	NPC143396
0.6667	Remote Similarity	NPC49863
0.6667	Remote Similarity	NPC470435
0.6667	Remote Similarity	NPC329890
0.6667	Remote Similarity	NPC55376
0.6667	Remote Similarity	NPC473829
0.6667	Remote Similarity	NPC475443
0.6667	Remote Similarity	NPC113293
0.6667	Remote Similarity	NPC478097
0.6667	Remote Similarity	NPC225272
0.6667	Remote Similarity	NPC201939
0.662	Remote Similarity	NPC4299
0.662	Remote Similarity	NPC476037
0.6618	Remote Similarity	NPC476654
0.6618	Remote Similarity	NPC323477
0.6618	Remote Similarity	NPC476657
0.6618	Remote Similarity	NPC476655
0.6618	Remote Similarity	NPC317881
0.6618	Remote Similarity	NPC323045
0.6613	Remote Similarity	NPC137538
0.6575	Remote Similarity	NPC227396
0.6571	Remote Similarity	NPC324981
0.6571	Remote Similarity	NPC141481
0.6571	Remote Similarity	NPC473559
0.6571	Remote Similarity	NPC48218
0.6562	Remote Similarity	NPC294938
0.6557	Remote Similarity	NPC236872
0.6557	Remote Similarity	NPC473705
0.6552	Remote Similarity	NPC308331
0.6515	Remote Similarity	NPC321919
0.6515	Remote Similarity	NPC81896
0.6508	Remote Similarity	NPC54766
0.6508	Remote Similarity	NPC52264
0.6508	Remote Similarity	NPC317899
0.6508	Remote Similarity	NPC45626
0.65	Remote Similarity	NPC473768
0.65	Remote Similarity	NPC59051
0.6486	Remote Similarity	NPC260396
0.6486	Remote Similarity	NPC285840
0.6486	Remote Similarity	NPC327041
0.6481	Remote Similarity	NPC15934
0.6479	Remote Similarity	NPC101622
0.6479	Remote Similarity	NPC473772
0.6462	Remote Similarity	NPC254095
0.6452	Remote Similarity	NPC217188
0.6452	Remote Similarity	NPC474496
0.6438	Remote Similarity	NPC329914
0.6438	Remote Similarity	NPC477085
0.6438	Remote Similarity	NPC325627

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 NPC594 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	119
0.1-0.2	4120
0.2-0.3	3834
0.3-0.4	891
0.4-0.5	112
0.5-0.6	70
0.6-0.7	3
0.7-0.8	1
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
0.7302	Intermediate Similarity	NPD4246	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD3197	Phase 1
0.6456	Remote Similarity	NPD5332	Approved
0.6456	Remote Similarity	NPD5331	Approved
0.6379	Remote Similarity	NPD39	Approved
0.6333	Remote Similarity	NPD4220	Pre-registration
0.6234	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6234	Remote Similarity	NPD4268	Approved
0.6234	Remote Similarity	NPD4271	Approved
0.6102	Remote Similarity	NPD4265	Approved
0.6094	Remote Similarity	NPD3194	Approved
0.6094	Remote Similarity	NPD3196	Approved
0.6094	Remote Similarity	NPD4266	Approved
0.6094	Remote Similarity	NPD3195	Phase 2
0.6087	Remote Similarity	NPD3210	Clinical (unspecified phase)
0.6076	Remote Similarity	NPD4821	Approved
0.6076	Remote Similarity	NPD4820	Approved
0.6076	Remote Similarity	NPD4252	Approved
0.6076	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6076	Remote Similarity	NPD4822	Approved
0.6076	Remote Similarity	NPD4819	Approved
0.6034	Remote Similarity	NPD5326	Phase 3
0.6	Remote Similarity	NPD4790	Discontinued
0.597	Remote Similarity	NPD6109	Phase 1
0.5942	Remote Similarity	NPD4192	Approved
0.5942	Remote Similarity	NPD4191	Approved
0.5942	Remote Similarity	NPD4194	Approved
0.5942	Remote Similarity	NPD4193	Approved
0.5938	Remote Similarity	NPD3172	Approved
0.5932	Remote Similarity	NPD6096	Approved
0.5932	Remote Similarity	NPD6097	Approved
0.5926	Remote Similarity	NPD4270	Approved
0.5926	Remote Similarity	NPD4269	Approved
0.5904	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.5902	Remote Similarity	NPD5343	Approved
0.5873	Remote Similarity	NPD6927	Phase 3
0.5873	Remote Similarity	NPD29	Approved
0.5873	Remote Similarity	NPD28	Approved
0.5854	Remote Similarity	NPD7154	Phase 3
0.5854	Remote Similarity	NPD5362	Discontinued
0.5833	Remote Similarity	NPD4222	Approved
0.5806	Remote Similarity	NPD3173	Approved
0.5775	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.5758	Remote Similarity	NPD4627	Clinical (unspecified phase)
0.5733	Remote Similarity	NPD3212	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD5363	Approved
0.5694	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.5672	Remote Similarity	NPD4219	Approved
0.5647	Remote Similarity	NPD5786	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