NPASS Compound

Structure

CID1580 OpenBabel06191715322D 35 38 0 0 1 0 0 0 0 0999 V2000 5.0629 -1.9487 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2191 4.3846 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6876 0.9744 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3753 0.9744 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2191 2.4359 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8438 1.4615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2191 1.4615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2191 3.4103 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3753 -1.9487 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5315 2.4359 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5315 2.4359 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8438 1.4615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2191 -1.4615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5315 1.4615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3753 1.9487 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 0.9744 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3753 3.8974 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2191 2.4359 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5315 3.4103 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5315 -1.4615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6876 0.9744 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3753 2.9231 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5315 -0.4872 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6876 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3753 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8438 -0.4872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3753 4.8718 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0629 2.9231 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6876 3.8974 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6876 -1.9487 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5315 1.4615 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8438 -1.4615 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3753 3.8974 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2191 -0.4872 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 13 1 0 0 0 0 2 33 1 0 0 0 0 3 6 2 0 0 0 0 3 14 1 0 0 0 0 4 7 2 0 0 0 0 4 14 1 0 0 0 0 5 8 2 0 0 0 0 5 15 1 0 0 0 0 6 16 1 0 0 0 0 7 18 1 0 0 0 0 8 17 1 0 0 0 0 9 13 2 0 0 0 0 9 20 1 0 0 0 0 10 14 2 0 0 0 0 10 22 1 0 0 0 0 11 15 2 0 0 0 0 11 19 1 0 0 0 0 12 16 2 0 0 0 0 12 21 1 0 0 0 0 13 34 1 0 0 0 0 16 35 1 0 0 0 0 17 19 2 0 0 0 0 17 27 1 0 0 0 0 18 22 2 0 0 0 0 18 28 1 0 0 0 0 19 29 1 0 0 0 0 20 23 1 0 0 0 0 20 30 2 0 0 0 0 21 24 2 0 0 0 0 21 31 1 0 0 0 0 22 33 1 0 0 0 0 23 24 1 6 0 0 0 23 25 1 0 0 0 0 24 26 1 0 0 0 0 25 15 1 1 0 0 0 25 34 1 0 0 0 0 26 32 2 0 0 0 0 26 35 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	478.13
Volume:	471.501
LogP:	2.916
LogD:	2.001
LogS:	-3.776
# Rotatable Bonds:	5
TPSA:	146.66
# H-Bond Aceptor:	9
# H-Bond Donor:	4
# Rings:	4
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.405
Synthetic Accessibility Score:	3.962
Fsp3:	0.154
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	2
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.437
MDCK Permeability:	1.5535259080934338e-05
Pgp-inhibitor:	0.018
Pgp-substrate:	0.565
Human Intestinal Absorption (HIA):	0.154
20% Bioavailability (F20%):	0.888
30% Bioavailability (F30%):	0.967

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.009
Plasma Protein Binding (PPB):	98.75829315185547%
Volume Distribution (VD):	0.371
Pgp-substrate:	1.6433162689208984%

ADMET: Metabolism

CYP1A2-inhibitor:	0.452
CYP1A2-substrate:	0.9
CYP2C19-inhibitor:	0.252
CYP2C19-substrate:	0.066
CYP2C9-inhibitor:	0.794
CYP2C9-substrate:	0.931
CYP2D6-inhibitor:	0.528
CYP2D6-substrate:	0.507
CYP3A4-inhibitor:	0.726
CYP3A4-substrate:	0.286

ADMET: Excretion

Clearance (CL):	4.761
Half-life (T1/2):	0.864

ADMET: Toxicity

hERG Blockers:	0.04
Human Hepatotoxicity (H-HT):	0.306
Drug-inuced Liver Injury (DILI):	0.947
AMES Toxicity:	0.431
Rat Oral Acute Toxicity:	0.284
Maximum Recommended Daily Dose:	0.92
Skin Sensitization:	0.947
Carcinogencity:	0.352
Eye Corrosion:	0.003
Eye Irritation:	0.319
Respiratory Toxicity:	0.129

Download Data

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

Natural Product: NPC1580

Natural Product ID:	NPC1580
*Common Name:**	Methyldavallialactone
IUPAC Name:	3-[(2S,3R)-2-(3,4-dihydroxyphenyl)-6-methyl-4-oxo-2,3-dihydropyran-3-yl]-4-hydroxy-6-[(E)-2-(4-hydroxy-3-methoxyphenyl)ethenyl]pyran-2-one
Synonyms:	Methyldavallialactone
Standard InCHIKey:	LDTVSIZNVSZWDV-DSJLGJJVSA-N
Standard InCHI:	InChI=1S/C26H22O9/c1-13-9-20(30)23(25(34-13)15-5-8-17(27)19(29)11-15)24-21(31)12-16(35-26(24)32)6-3-14-4-7-18(28)22(10-14)33-2/h3-12,23,25,27-29,31H,1-2H3/b6-3+/t23-,25-/m1/s1
SMILES:	CC1=CC(=O)[C@H](c2c(cc(/C=C/c3ccc(c(c3)OC)O)oc2=O)O)[C@@H](c2ccc(c(c2)O)O)O1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL204677
PubChem CID:	54726724
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000134] Phenols [CHEMONTID:0000190] Methoxyphenols

*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
NPO33057	Inonotus xeranticus	Species	Hymenochaetaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16488146]
NPO33057	Inonotus xeranticus	Species	Hymenochaetaceae	Eukaryota	n.a.	chonan-si, Korea	2005-APR	PMID[16499338]
NPO25991	Commiphora mukul	Species	Burseraceae	Eukaryota	n.a.	latex	n.a.	PMID[21800858]
NPO17752	Mentha X piperita	Strain	Lamiaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO17752	Mentha X piperita	Strain	Lamiaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO17752	Mentha X piperita	Strain	Lamiaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO17752	Mentha X piperita	Strain	Lamiaceae	Eukaryota	Shoot	n.a.	n.a.	Database[FooDB]
NPO17752	Mentha X piperita	Strain	Lamiaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO9049	Tanacetum parthenium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25991	Commiphora mukul	Species	Burseraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17752	Mentha X piperita	Strain	Lamiaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO17752	Mentha X piperita	Strain	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9049	Tanacetum parthenium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25991	Commiphora mukul	Species	Burseraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9049	Tanacetum parthenium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17752	Mentha X piperita	Strain	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5654	Pleocarphus revolutus	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO25991	Commiphora mukul	Species	Burseraceae	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
IC50	3

Activity Type	# Activity
Others	3

Target ID	Target Type	Target Name	Activity Type	Activity Relation	Value	Unit	Reference
NPT1	Others	Radical scavenging activity	IC50	=	5400.0	nM	PMID[464484]
NPT1	Others	Radical scavenging activity	IC50	=	1500.0	nM	PMID[464484]
NPT1	Others	Radical scavenging activity	IC50	=	18700.0	nM	PMID[464484]

☑ 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 NPC1580 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	383
0.1-0.2	1531
0.2-0.3	3712
0.3-0.4	8430
0.4-0.5	9901
0.5-0.6	3993
0.6-0.7	5152
0.7-0.8	6434
0.8-0.85	2632
0.85-0.9	510
0.9-0.95	16
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9643	High Similarity	NPC285550
0.9574	High Similarity	NPC183824
0.9195	High Similarity	NPC477299
0.911	High Similarity	NPC283081
0.911	High Similarity	NPC143892
0.911	High Similarity	NPC221383
0.911	High Similarity	NPC299090
0.9091	High Similarity	NPC9218
0.8973	High Similarity	NPC223185
0.8973	High Similarity	NPC258671
0.8973	High Similarity	NPC53884
0.8933	High Similarity	NPC95498
0.8933	High Similarity	NPC246566
0.8926	High Similarity	NPC32197
0.8904	High Similarity	NPC304956
0.8889	High Similarity	NPC289690
0.8889	High Similarity	NPC288452
0.8867	High Similarity	NPC300329
0.8857	High Similarity	NPC469480
0.8828	High Similarity	NPC100675
0.8811	High Similarity	NPC90431
0.8808	High Similarity	NPC476434
0.8803	High Similarity	NPC106406
0.88	High Similarity	NPC259576
0.88	High Similarity	NPC221091
0.8792	High Similarity	NPC98009
0.8786	High Similarity	NPC142985
0.8776	High Similarity	NPC470130
0.8759	High Similarity	NPC474784
0.8758	High Similarity	NPC131532
0.8742	High Similarity	NPC243891
0.8741	High Similarity	NPC113295
0.8741	High Similarity	NPC470990
0.8733	High Similarity	NPC125570
0.8684	High Similarity	NPC267091
0.8671	High Similarity	NPC68779
0.8671	High Similarity	NPC135127
0.8671	High Similarity	NPC176814
0.8671	High Similarity	NPC300776
0.8671	High Similarity	NPC5310
0.8671	High Similarity	NPC4982
0.8667	High Similarity	NPC472969
0.8654	High Similarity	NPC44507
0.8652	High Similarity	NPC244246
0.8652	High Similarity	NPC123196
0.8652	High Similarity	NPC215941
0.8652	High Similarity	NPC137427
0.8652	High Similarity	NPC319282
0.8652	High Similarity	NPC275724
0.8652	High Similarity	NPC195292
0.8652	High Similarity	NPC311419
0.8652	High Similarity	NPC65935
0.8649	High Similarity	NPC239608
0.8649	High Similarity	NPC46161
0.8649	High Similarity	NPC160378
0.8645	High Similarity	NPC40920
0.8645	High Similarity	NPC223335
0.8639	High Similarity	NPC253481
0.8639	High Similarity	NPC253722
0.8639	High Similarity	NPC31751
0.8639	High Similarity	NPC67467
0.863	High Similarity	NPC191280
0.863	High Similarity	NPC156709
0.863	High Similarity	NPC179505
0.863	High Similarity	NPC322021
0.8627	High Similarity	NPC473236
0.8621	High Similarity	NPC281780
0.8609	High Similarity	NPC478242
0.8609	High Similarity	NPC476394
0.8609	High Similarity	NPC98809
0.859	High Similarity	NPC469654
0.8581	High Similarity	NPC273657
0.8581	High Similarity	NPC478055
0.8581	High Similarity	NPC106920
0.8581	High Similarity	NPC470811
0.8581	High Similarity	NPC477696
0.8581	High Similarity	NPC477697
0.8571	High Similarity	NPC470991
0.8552	High Similarity	NPC471988
0.8542	High Similarity	NPC37065
0.8542	High Similarity	NPC67247
0.8533	High Similarity	NPC98356
0.8523	High Similarity	NPC473090
0.8523	High Similarity	NPC469615
0.8521	High Similarity	NPC285361
0.8519	High Similarity	NPC247964
0.8516	High Similarity	NPC476642
0.8506	High Similarity	NPC245615
0.8506	High Similarity	NPC299706
0.8506	High Similarity	NPC44730
0.8506	High Similarity	NPC115466
0.8506	High Similarity	NPC61604
0.8506	High Similarity	NPC295646
0.8503	High Similarity	NPC147379
0.85	High Similarity	NPC84076
0.85	High Similarity	NPC207575
0.85	High Similarity	NPC90128
0.85	High Similarity	NPC13481
0.85	High Similarity	NPC303680
0.8493	Intermediate Similarity	NPC279676
0.8493	Intermediate Similarity	NPC308976
0.8493	Intermediate Similarity	NPC67349
0.8493	Intermediate Similarity	NPC126206
0.8491	Intermediate Similarity	NPC134047
0.8491	Intermediate Similarity	NPC89131
0.8491	Intermediate Similarity	NPC272750
0.8491	Intermediate Similarity	NPC223006
0.8491	Intermediate Similarity	NPC173729
0.8483	Intermediate Similarity	NPC311742
0.8483	Intermediate Similarity	NPC477301
0.8477	Intermediate Similarity	NPC229264
0.8472	Intermediate Similarity	NPC155209
0.8472	Intermediate Similarity	NPC168799
0.8472	Intermediate Similarity	NPC475468
0.8472	Intermediate Similarity	NPC327410
0.8471	Intermediate Similarity	NPC76211
0.8467	Intermediate Similarity	NPC469683
0.8462	Intermediate Similarity	NPC473275
0.8462	Intermediate Similarity	NPC470896
0.8462	Intermediate Similarity	NPC471405
0.8462	Intermediate Similarity	NPC318799
0.8452	Intermediate Similarity	NPC136757
0.8452	Intermediate Similarity	NPC25127
0.8452	Intermediate Similarity	NPC469888
0.8452	Intermediate Similarity	NPC287504
0.8451	Intermediate Similarity	NPC241354
0.8451	Intermediate Similarity	NPC64111
0.8451	Intermediate Similarity	NPC304622
0.8446	Intermediate Similarity	NPC326065
0.8446	Intermediate Similarity	NPC477279
0.8446	Intermediate Similarity	NPC29599
0.8442	Intermediate Similarity	NPC270268
0.8442	Intermediate Similarity	NPC477699
0.8442	Intermediate Similarity	NPC75695
0.8442	Intermediate Similarity	NPC93498
0.8442	Intermediate Similarity	NPC163883
0.844	Intermediate Similarity	NPC20287
0.844	Intermediate Similarity	NPC123722
0.844	Intermediate Similarity	NPC5018
0.844	Intermediate Similarity	NPC12022
0.844	Intermediate Similarity	NPC123228
0.844	Intermediate Similarity	NPC20404
0.844	Intermediate Similarity	NPC293641
0.844	Intermediate Similarity	NPC151167
0.844	Intermediate Similarity	NPC276466
0.8438	Intermediate Similarity	NPC471788
0.8435	Intermediate Similarity	NPC284409
0.8429	Intermediate Similarity	NPC53305
0.8429	Intermediate Similarity	NPC257589
0.8429	Intermediate Similarity	NPC280767
0.8428	Intermediate Similarity	NPC144557
0.8425	Intermediate Similarity	NPC471664
0.8425	Intermediate Similarity	NPC120852
0.8425	Intermediate Similarity	NPC471665
0.8421	Intermediate Similarity	NPC116229
0.8421	Intermediate Similarity	NPC192568
0.8421	Intermediate Similarity	NPC471076
0.8418	Intermediate Similarity	NPC53889
0.8418	Intermediate Similarity	NPC130955
0.8414	Intermediate Similarity	NPC471110
0.8411	Intermediate Similarity	NPC30890
0.8411	Intermediate Similarity	NPC213482
0.8408	Intermediate Similarity	NPC108456
0.8408	Intermediate Similarity	NPC268602
0.8408	Intermediate Similarity	NPC286919
0.8408	Intermediate Similarity	NPC475663
0.8403	Intermediate Similarity	NPC61
0.8403	Intermediate Similarity	NPC18074
0.8403	Intermediate Similarity	NPC5419
0.8403	Intermediate Similarity	NPC25581
0.84	Intermediate Similarity	NPC27159
0.8397	Intermediate Similarity	NPC10205
0.8397	Intermediate Similarity	NPC38699
0.8389	Intermediate Similarity	NPC477278
0.8389	Intermediate Similarity	NPC140502
0.8389	Intermediate Similarity	NPC52664
0.8389	Intermediate Similarity	NPC477277
0.8387	Intermediate Similarity	NPC65591
0.8387	Intermediate Similarity	NPC146277
0.8387	Intermediate Similarity	NPC327225
0.8387	Intermediate Similarity	NPC199773
0.8387	Intermediate Similarity	NPC178574
0.8387	Intermediate Similarity	NPC19380
0.838	Intermediate Similarity	NPC278308
0.838	Intermediate Similarity	NPC167463
0.838	Intermediate Similarity	NPC226661
0.838	Intermediate Similarity	NPC46192
0.8378	Intermediate Similarity	NPC106055
0.8378	Intermediate Similarity	NPC110699
0.8377	Intermediate Similarity	NPC32079
0.8369	Intermediate Similarity	NPC127937
0.8369	Intermediate Similarity	NPC92207
0.8369	Intermediate Similarity	NPC118584
0.8369	Intermediate Similarity	NPC213552
0.8369	Intermediate Similarity	NPC179777
0.8369	Intermediate Similarity	NPC120225
0.8366	Intermediate Similarity	NPC474903
0.8365	Intermediate Similarity	NPC112418
0.8365	Intermediate Similarity	NPC216916
0.8365	Intermediate Similarity	NPC26326

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 NPC1580 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	333
0.1-0.2	912
0.2-0.3	1802
0.3-0.4	2566
0.4-0.5	1913
0.5-0.6	1007
0.6-0.7	440
0.7-0.8	134
0.8-0.85	34
0.85-0.9	9
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8269	Intermediate Similarity	NPD1934	Approved
0.8228	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8217	Intermediate Similarity	NPD2801	Approved
0.8165	Intermediate Similarity	NPD3817	Phase 2
0.8125	Intermediate Similarity	NPD6234	Discontinued
0.811	Intermediate Similarity	NPD3818	Discontinued
0.8105	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.8101	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8098	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8098	Intermediate Similarity	NPD6166	Phase 2
0.8098	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8092	Intermediate Similarity	NPD6190	Approved
0.8084	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8061	Intermediate Similarity	NPD7054	Approved
0.8049	Intermediate Similarity	NPD7473	Discontinued
0.8028	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.8012	Intermediate Similarity	NPD7074	Phase 3
0.8012	Intermediate Similarity	NPD7472	Approved
0.7975	Intermediate Similarity	NPD6232	Discontinued
0.7947	Intermediate Similarity	NPD7266	Discontinued
0.7945	Intermediate Similarity	NPD3027	Phase 3
0.7941	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7937	Intermediate Similarity	NPD5402	Approved
0.7925	Intermediate Similarity	NPD37	Approved
0.7917	Intermediate Similarity	NPD7685	Pre-registration
0.7911	Intermediate Similarity	NPD4380	Phase 2
0.7907	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7892	Intermediate Similarity	NPD7228	Approved
0.7888	Intermediate Similarity	NPD3882	Suspended
0.7888	Intermediate Similarity	NPD4965	Approved
0.7888	Intermediate Similarity	NPD4966	Approved
0.7888	Intermediate Similarity	NPD4967	Phase 2
0.7871	Intermediate Similarity	NPD1511	Approved
0.7857	Intermediate Similarity	NPD6797	Phase 2
0.7811	Intermediate Similarity	NPD7251	Discontinued
0.7792	Intermediate Similarity	NPD4628	Phase 3
0.7792	Intermediate Similarity	NPD8166	Discontinued
0.7771	Intermediate Similarity	NPD1512	Approved
0.7765	Intermediate Similarity	NPD7808	Phase 3
0.7751	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.773	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.773	Intermediate Similarity	NPD7075	Discontinued
0.7722	Intermediate Similarity	NPD5403	Approved
0.7697	Intermediate Similarity	NPD8127	Discontinued
0.7677	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7677	Intermediate Similarity	NPD4110	Phase 3
0.7654	Intermediate Similarity	NPD1465	Phase 2
0.7651	Intermediate Similarity	NPD6798	Discontinued
0.7647	Intermediate Similarity	NPD2935	Discontinued
0.7636	Intermediate Similarity	NPD5494	Approved
0.7616	Intermediate Similarity	NPD230	Phase 1
0.7616	Intermediate Similarity	NPD6355	Discontinued
0.761	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD6233	Phase 2
0.7595	Intermediate Similarity	NPD5401	Approved
0.7593	Intermediate Similarity	NPD6801	Discontinued
0.7568	Intermediate Similarity	NPD9494	Approved
0.7562	Intermediate Similarity	NPD1653	Approved
0.755	Intermediate Similarity	NPD1613	Approved
0.755	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7546	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7535	Intermediate Similarity	NPD5536	Phase 2
0.7529	Intermediate Similarity	NPD5844	Phase 1
0.7516	Intermediate Similarity	NPD7097	Phase 1
0.7516	Intermediate Similarity	NPD3226	Approved
0.75	Intermediate Similarity	NPD447	Suspended
0.75	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD7199	Phase 2
0.7484	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD7033	Discontinued
0.7468	Intermediate Similarity	NPD1510	Phase 2
0.7468	Intermediate Similarity	NPD2799	Discontinued
0.7466	Intermediate Similarity	NPD1608	Approved
0.7452	Intermediate Similarity	NPD3750	Approved
0.7439	Intermediate Similarity	NPD7819	Suspended
0.7436	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7434	Intermediate Similarity	NPD4060	Phase 1
0.7432	Intermediate Similarity	NPD2797	Approved
0.7427	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7423	Intermediate Similarity	NPD6386	Approved
0.7423	Intermediate Similarity	NPD6385	Approved
0.7423	Intermediate Similarity	NPD7411	Suspended
0.7421	Intermediate Similarity	NPD6799	Approved
0.7417	Intermediate Similarity	NPD3268	Approved
0.7417	Intermediate Similarity	NPD2313	Discontinued
0.7414	Intermediate Similarity	NPD8313	Approved
0.7414	Intermediate Similarity	NPD8312	Approved
0.74	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7399	Intermediate Similarity	NPD6559	Discontinued
0.7399	Intermediate Similarity	NPD7240	Approved
0.7396	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7383	Intermediate Similarity	NPD5647	Approved
0.7376	Intermediate Similarity	NPD5283	Phase 1
0.7375	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7372	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7372	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD4062	Phase 3
0.7357	Intermediate Similarity	NPD228	Approved
0.7351	Intermediate Similarity	NPD7095	Approved
0.7342	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7325	Intermediate Similarity	NPD1549	Phase 2
0.7318	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD2438	Suspended
0.7308	Intermediate Similarity	NPD2796	Approved
0.7303	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD3764	Approved
0.7301	Intermediate Similarity	NPD3455	Phase 2
0.7288	Intermediate Similarity	NPD8434	Phase 2
0.7273	Intermediate Similarity	NPD4340	Discontinued
0.7267	Intermediate Similarity	NPD3751	Discontinued
0.7267	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD2798	Approved
0.7267	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7261	Intermediate Similarity	NPD2346	Discontinued
0.726	Intermediate Similarity	NPD17	Approved
0.7256	Intermediate Similarity	NPD7028	Phase 2
0.7256	Intermediate Similarity	NPD6599	Discontinued
0.7248	Intermediate Similarity	NPD3225	Approved
0.7248	Intermediate Similarity	NPD1283	Approved
0.7246	Intermediate Similarity	NPD7768	Phase 2
0.7229	Intermediate Similarity	NPD8455	Phase 2
0.7222	Intermediate Similarity	NPD6273	Approved
0.7219	Intermediate Similarity	NPD2861	Phase 2
0.7208	Intermediate Similarity	NPD2979	Phase 3
0.7208	Intermediate Similarity	NPD943	Approved
0.7208	Intermediate Similarity	NPD3620	Phase 2
0.7208	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD1240	Approved
0.72	Intermediate Similarity	NPD7039	Approved
0.72	Intermediate Similarity	NPD7038	Approved
0.7197	Intermediate Similarity	NPD6032	Approved
0.7195	Intermediate Similarity	NPD7458	Discontinued
0.7176	Intermediate Similarity	NPD6959	Discontinued
0.7175	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7162	Intermediate Similarity	NPD1535	Discovery
0.7161	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7161	Intermediate Similarity	NPD1933	Approved
0.7161	Intermediate Similarity	NPD5124	Phase 1
0.716	Intermediate Similarity	NPD919	Approved
0.716	Intermediate Similarity	NPD2533	Approved
0.716	Intermediate Similarity	NPD2532	Approved
0.716	Intermediate Similarity	NPD2534	Approved
0.7151	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD3787	Discontinued
0.7134	Intermediate Similarity	NPD3748	Approved
0.7125	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7123	Intermediate Similarity	NPD9545	Approved
0.7123	Intermediate Similarity	NPD1894	Discontinued
0.7115	Intermediate Similarity	NPD1607	Approved
0.7115	Intermediate Similarity	NPD6653	Approved
0.7114	Intermediate Similarity	NPD1481	Phase 2
0.7108	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD5958	Discontinued
0.7107	Intermediate Similarity	NPD4534	Discontinued
0.7095	Intermediate Similarity	NPD3847	Discontinued
0.7095	Intermediate Similarity	NPD8150	Discontinued
0.7093	Intermediate Similarity	NPD3926	Phase 2
0.7093	Intermediate Similarity	NPD5242	Approved
0.7092	Intermediate Similarity	NPD3021	Approved
0.7092	Intermediate Similarity	NPD3022	Approved
0.7089	Intermediate Similarity	NPD1551	Phase 2
0.7086	Intermediate Similarity	NPD3266	Approved
0.7086	Intermediate Similarity	NPD3267	Approved
0.7083	Intermediate Similarity	NPD5353	Approved
0.7081	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD5585	Approved
0.7059	Intermediate Similarity	NPD6832	Phase 2
0.7059	Intermediate Similarity	NPD4908	Phase 1
0.7047	Intermediate Similarity	NPD3705	Approved
0.7047	Intermediate Similarity	NPD1281	Approved
0.7044	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD2344	Approved
0.703	Intermediate Similarity	NPD3687	Approved
0.703	Intermediate Similarity	NPD3686	Approved
0.7021	Intermediate Similarity	NPD7680	Approved
0.7019	Intermediate Similarity	NPD7003	Approved
0.7	Intermediate Similarity	NPD3749	Approved
0.6994	Remote Similarity	NPD4357	Discontinued
0.6988	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6987	Remote Similarity	NPD1558	Phase 1
0.6987	Remote Similarity	NPD825	Approved
0.6987	Remote Similarity	NPD826	Approved
0.698	Remote Similarity	NPD3496	Discontinued
0.6977	Remote Similarity	NPD1247	Approved
0.6974	Remote Similarity	NPD1203	Approved
0.6968	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD7549	Discontinued
0.6964	Remote Similarity	NPD6844	Discontinued
0.6959	Remote Similarity	NPD1651	Approved
0.6957	Remote Similarity	NPD1652	Phase 2
0.6957	Remote Similarity	NPD6674	Discontinued
0.6954	Remote Similarity	NPD2982	Phase 2
0.6954	Remote Similarity	NPD2983	Phase 2
0.6951	Remote Similarity	NPD3688	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD3146	Approved
0.695	Remote Similarity	NPD1358	Approved
0.6949	Remote Similarity	NPD5953	Discontinued
0.6944	Remote Similarity	NPD5535	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