NPASS Compound

Structure

NPC471444 OpenBabel07101718202D 40 41 0 0 1 0 0 0 0 0999 V2000 4.3301 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -0.0000 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 4.3301 1.5000 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 3.4641 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 4.5000 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 6.0000 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 0.0000 6.0000 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 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 3.0000 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 -2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 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 -2.5981 -0.5000 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 -3.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 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 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 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 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 4 1 0 0 0 0 2 25 1 0 0 0 0 3 25 1 0 0 0 0 4 5 1 0 0 0 0 5 6 1 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 2 0 0 0 0 12 13 1 0 0 0 0 13 14 1 0 0 0 0 14 15 2 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 31 1 0 0 0 0 20 23 1 0 0 0 0 20 25 2 0 0 0 0 21 22 2 0 0 0 0 21 27 1 0 0 0 0 22 28 1 0 0 0 0 24 26 2 0 0 0 0 24 29 1 0 0 0 0 26 30 1 0 0 0 0 26 34 1 0 0 0 0 27 32 2 0 0 0 0 27 35 1 0 0 0 0 28 33 2 0 0 0 0 28 36 1 0 0 0 0 29 32 1 0 0 0 0 29 37 2 0 0 0 0 30 23 1 1 0 0 0 30 40 1 0 0 0 0 31 38 2 0 0 0 0 31 40 1 0 0 0 0 32 33 1 0 0 0 0 33 34 1 0 0 0 0 34 39 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	550.33
Volume:	605.884
LogP:	7.627
LogD:	4.776
LogS:	-1.755
# Rotatable Bonds:	18
TPSA:	107.22
# H-Bond Aceptor:	6
# H-Bond Donor:	4
# Rings:	2
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.039
Synthetic Accessibility Score:	3.47
Fsp3:	0.441
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
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:	-5.075
MDCK Permeability:	2.438078990962822e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.034
Human Intestinal Absorption (HIA):	0.061
20% Bioavailability (F20%):	1.0
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.003
Plasma Protein Binding (PPB):	102.34107208251953%
Volume Distribution (VD):	2.382
Pgp-substrate:	0.5392780303955078%

ADMET: Metabolism

CYP1A2-inhibitor:	0.758
CYP1A2-substrate:	0.297
CYP2C19-inhibitor:	0.844
CYP2C19-substrate:	0.061
CYP2C9-inhibitor:	0.398
CYP2C9-substrate:	0.989
CYP2D6-inhibitor:	0.864
CYP2D6-substrate:	0.925
CYP3A4-inhibitor:	0.116
CYP3A4-substrate:	0.063

ADMET: Excretion

Clearance (CL):	2.047
Half-life (T1/2):	0.945

ADMET: Toxicity

hERG Blockers:	0.018
Human Hepatotoxicity (H-HT):	0.26
Drug-inuced Liver Injury (DILI):	0.034
AMES Toxicity:	0.729
Rat Oral Acute Toxicity:	0.076
Maximum Recommended Daily Dose:	0.869
Skin Sensitization:	0.98
Carcinogencity:	0.206
Eye Corrosion:	0.042
Eye Irritation:	0.92
Respiratory Toxicity:	0.673

Download Data

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

Natural Product: NPC471444

Natural Product ID:	NPC471444
*Common Name:**	[(1R)-1-(5,8-Dihydroxy-1,4-Dioxonaphthalen-2-Yl)-4-Methylpent-3-Enyl] (6Z,9Z)-Octadeca-6,9-Dienoate
IUPAC Name:	[(1R)-1-(5,8-dihydroxy-1,4-dioxonaphthalen-2-yl)-4-methylpent-3-enyl] (6Z,9Z)-octadeca-6,9-dienoate
Synonyms:
Standard InCHIKey:	LRCJVQJYXQCXDX-PNURKKAPSA-N
Standard InCHI:	InChI=1S/C34H46O6/c1-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-31(38)40-30(23-20-25(2)3)26-24-29(37)32-27(35)21-22-28(36)33(32)34(26)39/h11-12,14-15,20-22,24,30,35-36H,4-10,13,16-19,23H2,1-3H3/b12-11-,15-14-/t30-/m1/s1
SMILES:	CCCCCCCCC=CCC=CCCCCC(=O)OC(CC=C(C)C)C1=CC(=O)C2=C(C=CC(=C2C1=O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL247861
PubChem CID:	44438574
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0003909] Fatty Acyls [CHEMONTID:0000504] Lineolic acids and derivatives

*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
NPO11776	Lithospermum erythrorhizon	Species	Boraginaceae	Eukaryota	n.a.	root	n.a.	DOI[10.1007/s11418-007-0221-0]
NPO11776	Lithospermum erythrorhizon	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17157006]
NPO11776	Lithospermum erythrorhizon	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19217780]
NPO11776	Lithospermum erythrorhizon	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[3373224]
NPO11776	Lithospermum erythrorhizon	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11776	Lithospermum erythrorhizon	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11776	Lithospermum erythrorhizon	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO11776	Lithospermum erythrorhizon	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO11776	Lithospermum erythrorhizon	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

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

NP Quantity Composition/Concentration

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

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

Biological Activity

Activity Type	# Activity
Others	2

Activity Type	# Activity
Individual Protein	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1214	Individual Protein	Acyl coenzyme A:cholesterol acyltransferase 1	Homo sapiens	Inhibition	=	5.0	%	PMID[532266]
NPT2584	Individual Protein	Acyl coenzyme A:cholesterol acyltransferase 2	Homo sapiens	Inhibition	=	4.0	%	PMID[532266]

☑ 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 NPC471444 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	295
0.1-0.2	1220
0.2-0.3	2874
0.3-0.4	6577
0.4-0.5	11405
0.5-0.6	5229
0.6-0.7	8552
0.7-0.8	6043
0.8-0.85	425
0.85-0.9	45
0.9-0.95	10
0.95-1	22

Similarity Score	Similarity Level	Natural Product ID
0.9851	High Similarity	NPC476477
0.9851	High Similarity	NPC306835
0.9851	High Similarity	NPC299405
0.9851	High Similarity	NPC256463
0.9851	High Similarity	NPC471602
0.9851	High Similarity	NPC29771
0.9851	High Similarity	NPC216312
0.9851	High Similarity	NPC111422
0.9778	High Similarity	NPC241349
0.9778	High Similarity	NPC42262
0.9778	High Similarity	NPC147542
0.9778	High Similarity	NPC327916
0.9778	High Similarity	NPC220496
0.9778	High Similarity	NPC32749
0.9778	High Similarity	NPC37992
0.9706	High Similarity	NPC257003
0.9635	High Similarity	NPC474300
0.9565	High Similarity	NPC476473
0.9496	High Similarity	NPC89664
0.9496	High Similarity	NPC274085
0.9416	High Similarity	NPC295339
0.9343	High Similarity	NPC61590
0.922	High Similarity	NPC103910
0.9185	High Similarity	NPC110609
0.9185	High Similarity	NPC246693
0.9185	High Similarity	NPC242358
0.9149	High Similarity	NPC21873
0.8881	High Similarity	NPC306765
0.8849	High Similarity	NPC281513
0.8849	High Similarity	NPC22222
0.8819	High Similarity	NPC477409
0.8714	High Similarity	NPC27407
0.8592	High Similarity	NPC305060
0.8582	High Similarity	NPC142027
0.8581	High Similarity	NPC94781
0.8571	High Similarity	NPC147250
0.8561	High Similarity	NPC7012
0.8542	High Similarity	NPC315578
0.8523	High Similarity	NPC280753
0.8523	High Similarity	NPC44378
0.8523	High Similarity	NPC120171
0.8519	High Similarity	NPC477153
0.8514	High Similarity	NPC119767
0.8503	High Similarity	NPC475923
0.8503	High Similarity	NPC474630
0.8503	High Similarity	NPC474309
0.85	High Similarity	NPC477406
0.8497	Intermediate Similarity	NPC29552
0.8483	Intermediate Similarity	NPC124365
0.8472	Intermediate Similarity	NPC477408
0.8472	Intermediate Similarity	NPC103337
0.8472	Intermediate Similarity	NPC114620
0.8472	Intermediate Similarity	NPC26924
0.8467	Intermediate Similarity	NPC1991
0.8467	Intermediate Similarity	NPC3224
0.8467	Intermediate Similarity	NPC231774
0.8462	Intermediate Similarity	NPC71256
0.8446	Intermediate Similarity	NPC120536
0.844	Intermediate Similarity	NPC43627
0.8435	Intermediate Similarity	NPC151607
0.8435	Intermediate Similarity	NPC42540
0.8429	Intermediate Similarity	NPC205992
0.8429	Intermediate Similarity	NPC470831
0.8429	Intermediate Similarity	NPC214702
0.8421	Intermediate Similarity	NPC218870
0.8421	Intermediate Similarity	NPC470408
0.8421	Intermediate Similarity	NPC182921
0.8421	Intermediate Similarity	NPC474824
0.8417	Intermediate Similarity	NPC278928
0.8408	Intermediate Similarity	NPC474301
0.8406	Intermediate Similarity	NPC471530
0.8403	Intermediate Similarity	NPC197666
0.8403	Intermediate Similarity	NPC478200
0.8403	Intermediate Similarity	NPC191835
0.8403	Intermediate Similarity	NPC221104
0.8403	Intermediate Similarity	NPC33144
0.8403	Intermediate Similarity	NPC126739
0.8394	Intermediate Similarity	NPC240744
0.8394	Intermediate Similarity	NPC167055
0.8392	Intermediate Similarity	NPC272268
0.8392	Intermediate Similarity	NPC141934
0.8392	Intermediate Similarity	NPC291454
0.838	Intermediate Similarity	NPC474097
0.8369	Intermediate Similarity	NPC309430
0.8367	Intermediate Similarity	NPC159721
0.8367	Intermediate Similarity	NPC471731
0.8367	Intermediate Similarity	NPC478202
0.8366	Intermediate Similarity	NPC66029
0.8358	Intermediate Similarity	NPC285829
0.8358	Intermediate Similarity	NPC206778
0.8357	Intermediate Similarity	NPC163169
0.8357	Intermediate Similarity	NPC123
0.8357	Intermediate Similarity	NPC475741
0.8356	Intermediate Similarity	NPC130485
0.8356	Intermediate Similarity	NPC313123
0.8356	Intermediate Similarity	NPC472603
0.8356	Intermediate Similarity	NPC478201
0.8356	Intermediate Similarity	NPC470842
0.8356	Intermediate Similarity	NPC478217
0.8356	Intermediate Similarity	NPC149533
0.8356	Intermediate Similarity	NPC283292
0.8356	Intermediate Similarity	NPC472035
0.8355	Intermediate Similarity	NPC281272
0.8345	Intermediate Similarity	NPC237225
0.8345	Intermediate Similarity	NPC165257
0.8345	Intermediate Similarity	NPC1268
0.8344	Intermediate Similarity	NPC315520
0.8333	Intermediate Similarity	NPC295202
0.8333	Intermediate Similarity	NPC49647
0.8333	Intermediate Similarity	NPC136342
0.8333	Intermediate Similarity	NPC245923
0.8333	Intermediate Similarity	NPC96915
0.8333	Intermediate Similarity	NPC70380
0.8333	Intermediate Similarity	NPC470479
0.8333	Intermediate Similarity	NPC227741
0.8322	Intermediate Similarity	NPC300540
0.8322	Intermediate Similarity	NPC161632
0.8321	Intermediate Similarity	NPC234890
0.8321	Intermediate Similarity	NPC74507
0.8321	Intermediate Similarity	NPC310540
0.8312	Intermediate Similarity	NPC474861
0.8312	Intermediate Similarity	NPC472050
0.8312	Intermediate Similarity	NPC478027
0.8311	Intermediate Similarity	NPC478203
0.8311	Intermediate Similarity	NPC126882
0.8311	Intermediate Similarity	NPC210966
0.831	Intermediate Similarity	NPC472591
0.8309	Intermediate Similarity	NPC307174
0.8301	Intermediate Similarity	NPC474621
0.8301	Intermediate Similarity	NPC477691
0.8301	Intermediate Similarity	NPC474622
0.8299	Intermediate Similarity	NPC329493
0.8299	Intermediate Similarity	NPC471733
0.8291	Intermediate Similarity	NPC71390
0.8289	Intermediate Similarity	NPC39819
0.8288	Intermediate Similarity	NPC472601
0.8288	Intermediate Similarity	NPC156872
0.8288	Intermediate Similarity	NPC472600
0.8284	Intermediate Similarity	NPC232178
0.8276	Intermediate Similarity	NPC94248
0.8276	Intermediate Similarity	NPC173980
0.8276	Intermediate Similarity	NPC472602
0.8276	Intermediate Similarity	NPC9121
0.8276	Intermediate Similarity	NPC177307
0.8276	Intermediate Similarity	NPC212693
0.8273	Intermediate Similarity	NPC45537
0.8264	Intermediate Similarity	NPC474813
0.8261	Intermediate Similarity	NPC287473
0.8261	Intermediate Similarity	NPC131799
0.8261	Intermediate Similarity	NPC103540
0.8258	Intermediate Similarity	NPC67197
0.8255	Intermediate Similarity	NPC83272
0.8255	Intermediate Similarity	NPC257558
0.8252	Intermediate Similarity	NPC288089
0.8243	Intermediate Similarity	NPC472006
0.8243	Intermediate Similarity	NPC469885
0.8239	Intermediate Similarity	NPC88864
0.8239	Intermediate Similarity	NPC477407
0.8239	Intermediate Similarity	NPC70622
0.8239	Intermediate Similarity	NPC58685
0.8239	Intermediate Similarity	NPC470160
0.8235	Intermediate Similarity	NPC180388
0.8235	Intermediate Similarity	NPC474534
0.8235	Intermediate Similarity	NPC115249
0.8235	Intermediate Similarity	NPC477690
0.8235	Intermediate Similarity	NPC474533
0.8231	Intermediate Similarity	NPC158634
0.8231	Intermediate Similarity	NPC472605
0.8231	Intermediate Similarity	NPC187843
0.8231	Intermediate Similarity	NPC472604
0.8231	Intermediate Similarity	NPC53649
0.8227	Intermediate Similarity	NPC31539
0.8227	Intermediate Similarity	NPC198305
0.8224	Intermediate Similarity	NPC205766
0.8224	Intermediate Similarity	NPC31132
0.8224	Intermediate Similarity	NPC56204
0.8214	Intermediate Similarity	NPC282923
0.8212	Intermediate Similarity	NPC2569
0.8212	Intermediate Similarity	NPC228012
0.8212	Intermediate Similarity	NPC172329
0.8207	Intermediate Similarity	NPC301915
0.8207	Intermediate Similarity	NPC261292
0.8207	Intermediate Similarity	NPC119542
0.8207	Intermediate Similarity	NPC474849
0.8207	Intermediate Similarity	NPC178467
0.8207	Intermediate Similarity	NPC65837
0.8207	Intermediate Similarity	NPC474771
0.8207	Intermediate Similarity	NPC149372
0.8207	Intermediate Similarity	NPC194579
0.8201	Intermediate Similarity	NPC474944
0.8201	Intermediate Similarity	NPC51037
0.82	Intermediate Similarity	NPC470570
0.82	Intermediate Similarity	NPC472033
0.82	Intermediate Similarity	NPC107625
0.82	Intermediate Similarity	NPC473023
0.8194	Intermediate Similarity	NPC254832
0.8194	Intermediate Similarity	NPC267539
0.8194	Intermediate Similarity	NPC176102
0.8194	Intermediate Similarity	NPC229638
0.8194	Intermediate Similarity	NPC283088

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 NPC471444 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	263
0.1-0.2	853
0.2-0.3	1531
0.3-0.4	2485
0.4-0.5	2182
0.5-0.6	1192
0.6-0.7	518
0.7-0.8	122
0.8-0.85	4
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8261	Intermediate Similarity	NPD1470	Approved
0.8158	Intermediate Similarity	NPD3226	Approved
0.8082	Intermediate Similarity	NPD2935	Discontinued
0.806	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.8027	Intermediate Similarity	NPD2346	Discontinued
0.7971	Intermediate Similarity	NPD1201	Approved
0.7949	Intermediate Similarity	NPD7819	Suspended
0.7895	Intermediate Similarity	NPD2532	Approved
0.7895	Intermediate Similarity	NPD2533	Approved
0.7895	Intermediate Similarity	NPD2534	Approved
0.787	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD8150	Discontinued
0.7778	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7748	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7733	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7724	Intermediate Similarity	NPD3764	Approved
0.7718	Intermediate Similarity	NPD5406	Approved
0.7718	Intermediate Similarity	NPD5404	Approved
0.7718	Intermediate Similarity	NPD5408	Approved
0.7718	Intermediate Similarity	NPD5405	Approved
0.7683	Intermediate Similarity	NPD7473	Discontinued
0.7679	Intermediate Similarity	NPD8312	Approved
0.7679	Intermediate Similarity	NPD8313	Approved
0.7664	Intermediate Similarity	NPD9493	Approved
0.7651	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7651	Intermediate Similarity	NPD2799	Discontinued
0.7632	Intermediate Similarity	NPD8166	Discontinued
0.7607	Intermediate Similarity	NPD6232	Discontinued
0.7603	Intermediate Similarity	NPD2313	Discontinued
0.7562	Intermediate Similarity	NPD5402	Approved
0.7554	Intermediate Similarity	NPD9545	Approved
0.7516	Intermediate Similarity	NPD3750	Approved
0.7516	Intermediate Similarity	NPD7768	Phase 2
0.7516	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD1551	Phase 2
0.7469	Intermediate Similarity	NPD7075	Discontinued
0.7451	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD3300	Phase 2
0.7403	Intermediate Similarity	NPD4628	Phase 3
0.7391	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD5844	Phase 1
0.7358	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD6832	Phase 2
0.7346	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7341	Intermediate Similarity	NPD8434	Phase 2
0.7333	Intermediate Similarity	NPD6959	Discontinued
0.7333	Intermediate Similarity	NPD447	Suspended
0.7333	Intermediate Similarity	NPD230	Phase 1
0.7333	Intermediate Similarity	NPD2182	Approved
0.7329	Intermediate Similarity	NPD2798	Approved
0.7325	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7325	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7315	Intermediate Similarity	NPD6663	Approved
0.7312	Intermediate Similarity	NPD4380	Phase 2
0.7303	Intermediate Similarity	NPD1510	Phase 2
0.7292	Intermediate Similarity	NPD9717	Approved
0.7289	Intermediate Similarity	NPD5710	Approved
0.7289	Intermediate Similarity	NPD5711	Approved
0.7285	Intermediate Similarity	NPD1607	Approved
0.7284	Intermediate Similarity	NPD2801	Approved
0.7279	Intermediate Similarity	NPD5736	Approved
0.7273	Intermediate Similarity	NPD1549	Phase 2
0.7267	Intermediate Similarity	NPD1240	Approved
0.7267	Intermediate Similarity	NPD7411	Suspended
0.7263	Intermediate Similarity	NPD7699	Phase 2
0.7263	Intermediate Similarity	NPD7700	Phase 2
0.7261	Intermediate Similarity	NPD7390	Discontinued
0.726	Intermediate Similarity	NPD1203	Approved
0.726	Intermediate Similarity	NPD1164	Approved
0.7253	Intermediate Similarity	NPD7435	Discontinued
0.7248	Intermediate Similarity	NPD411	Approved
0.7226	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD6844	Discontinued
0.7222	Intermediate Similarity	NPD1934	Approved
0.7219	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD2344	Approved
0.7208	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7206	Intermediate Similarity	NPD74	Approved
0.7206	Intermediate Similarity	NPD9266	Approved
0.7205	Intermediate Similarity	NPD6599	Discontinued
0.7203	Intermediate Similarity	NPD4626	Approved
0.7202	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7191	Intermediate Similarity	NPD6535	Approved
0.7191	Intermediate Similarity	NPD6534	Approved
0.719	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD3748	Approved
0.7179	Intermediate Similarity	NPD7003	Approved
0.717	Intermediate Similarity	NPD6273	Approved
0.7169	Intermediate Similarity	NPD5494	Approved
0.7158	Intermediate Similarity	NPD7698	Approved
0.7158	Intermediate Similarity	NPD7696	Phase 3
0.7158	Intermediate Similarity	NPD7697	Approved
0.7153	Intermediate Similarity	NPD3496	Discontinued
0.7152	Intermediate Similarity	NPD6799	Approved
0.7152	Intermediate Similarity	NPD943	Approved
0.7152	Intermediate Similarity	NPD3749	Approved
0.7151	Intermediate Similarity	NPD6559	Discontinued
0.7143	Intermediate Similarity	NPD2796	Approved
0.7135	Intermediate Similarity	NPD6213	Phase 3
0.7135	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD6212	Phase 3
0.7134	Intermediate Similarity	NPD6190	Approved
0.7133	Intermediate Similarity	NPD5691	Approved
0.7132	Intermediate Similarity	NPD9264	Approved
0.7132	Intermediate Similarity	NPD9263	Approved
0.7132	Intermediate Similarity	NPD9267	Approved
0.7125	Intermediate Similarity	NPD5403	Approved
0.712	Intermediate Similarity	NPD8319	Approved
0.712	Intermediate Similarity	NPD8320	Phase 1
0.712	Intermediate Similarity	NPD7871	Phase 2
0.712	Intermediate Similarity	NPD7870	Phase 2
0.7118	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD6801	Discontinued
0.7115	Intermediate Similarity	NPD2800	Approved
0.7112	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7112	Intermediate Similarity	NPD7874	Approved
0.7103	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD3882	Suspended
0.7088	Intermediate Similarity	NPD6780	Approved
0.7088	Intermediate Similarity	NPD6776	Approved
0.7088	Intermediate Similarity	NPD6781	Approved
0.7088	Intermediate Similarity	NPD6778	Approved
0.7088	Intermediate Similarity	NPD6777	Approved
0.7088	Intermediate Similarity	NPD6782	Approved
0.7088	Intermediate Similarity	NPD6779	Approved
0.7086	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD2932	Approved
0.708	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD1283	Approved
0.7067	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD1608	Approved
0.7048	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD2979	Phase 3
0.7037	Intermediate Similarity	NPD164	Approved
0.7037	Intermediate Similarity	NPD7458	Discontinued
0.703	Intermediate Similarity	NPD3817	Phase 2
0.7025	Intermediate Similarity	NPD2309	Approved
0.702	Intermediate Similarity	NPD7985	Registered
0.7019	Intermediate Similarity	NPD920	Approved
0.7018	Intermediate Similarity	NPD3818	Discontinued
0.7018	Intermediate Similarity	NPD7177	Discontinued
0.7011	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD6823	Phase 2
0.7005	Intermediate Similarity	NPD7701	Phase 2
0.7	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD5401	Approved
0.7	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD7635	Approved
0.6994	Remote Similarity	NPD5953	Discontinued
0.6987	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6987	Remote Similarity	NPD6005	Phase 3
0.6987	Remote Similarity	NPD1471	Phase 3
0.6987	Remote Similarity	NPD6002	Phase 3
0.6987	Remote Similarity	NPD5762	Approved
0.6987	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6987	Remote Similarity	NPD6004	Phase 3
0.6987	Remote Similarity	NPD5763	Approved
0.6981	Remote Similarity	NPD7236	Approved
0.698	Remote Similarity	NPD1019	Discontinued
0.6977	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD7286	Phase 2
0.6974	Remote Similarity	NPD520	Approved
0.6968	Remote Similarity	NPD4308	Phase 3
0.6968	Remote Similarity	NPD7033	Discontinued
0.6966	Remote Similarity	NPD1778	Approved
0.6966	Remote Similarity	NPD3019	Approved
0.6959	Remote Similarity	NPD6696	Suspended
0.6954	Remote Similarity	NPD7008	Discontinued
0.6948	Remote Similarity	NPD6651	Approved
0.6937	Remote Similarity	NPD1511	Approved
0.6936	Remote Similarity	NPD7074	Phase 3
0.6928	Remote Similarity	NPD4060	Phase 1
0.6923	Remote Similarity	NPD8127	Discontinued
0.6923	Remote Similarity	NPD6100	Approved
0.6923	Remote Similarity	NPD6099	Approved
0.6919	Remote Similarity	NPD3751	Discontinued
0.6913	Remote Similarity	NPD2797	Approved
0.6909	Remote Similarity	NPD37	Approved
0.6908	Remote Similarity	NPD3268	Approved
0.6908	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD6234	Discontinued
0.6901	Remote Similarity	NPD9281	Approved
0.6901	Remote Similarity	NPD6166	Phase 2
0.6901	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD5951	Approved
0.6897	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6895	Remote Similarity	NPD7801	Approved
0.6894	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6886	Remote Similarity	NPD4965	Approved
0.6886	Remote Similarity	NPD4967	Phase 2
0.6886	Remote Similarity	NPD4966	Approved
0.6884	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6883	Remote Similarity	NPD6355	Discontinued

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