NPASS Compound

Structure

CID256555 OpenBabel06191716062D 21 23 0 0 0 0 0 0 0 0999 V2000 1.7321 -4.0000 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 -3.4641 -1.0000 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 -4.3301 -1.5000 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 -1.7321 0.0000 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 -2.5981 -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 -1.7321 -1.0000 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 -0.0000 -3.0000 0.0000 C 0 0 0 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 0.8660 -2.5000 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 -5.1962 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -4.0000 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 1.7321 -3.0000 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 20 1 0 0 0 0 2 4 1 0 0 0 0 2 9 2 0 0 0 0 3 5 2 0 0 0 0 3 9 1 0 0 0 0 4 10 2 0 0 0 0 5 10 1 0 0 0 0 6 12 2 0 0 0 0 6 13 1 0 0 0 0 7 11 2 0 0 0 0 7 16 1 0 0 0 0 8 14 2 0 0 0 0 8 15 1 0 0 0 0 9 11 1 0 0 0 0 10 17 1 0 0 0 0 11 12 1 0 0 0 0 12 14 1 0 0 0 0 13 15 2 0 0 0 0 13 18 1 0 0 0 0 14 21 1 0 0 0 0 15 20 1 0 0 0 0 16 19 2 0 0 0 0 16 21 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	284.07
Volume:	282.482
LogP:	2.578
LogD:	2.603
LogS:	-3.668
# Rotatable Bonds:	2
TPSA:	79.9
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.707
Synthetic Accessibility Score:	2.105
Fsp3:	0.062
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.735
MDCK Permeability:	1.4678390471090097e-05
Pgp-inhibitor:	0.003
Pgp-substrate:	0.994
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.979
30% Bioavailability (F30%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.039
Plasma Protein Binding (PPB):	96.92070770263672%
Volume Distribution (VD):	0.52
Pgp-substrate:	3.810863971710205%

ADMET: Metabolism

CYP1A2-inhibitor:	0.958
CYP1A2-substrate:	0.934
CYP2C19-inhibitor:	0.664
CYP2C19-substrate:	0.058
CYP2C9-inhibitor:	0.373
CYP2C9-substrate:	0.914
CYP2D6-inhibitor:	0.716
CYP2D6-substrate:	0.902
CYP3A4-inhibitor:	0.822
CYP3A4-substrate:	0.259

ADMET: Excretion

Clearance (CL):	11.942
Half-life (T1/2):	0.829

ADMET: Toxicity

hERG Blockers:	0.169
Human Hepatotoxicity (H-HT):	0.15
Drug-inuced Liver Injury (DILI):	0.891
AMES Toxicity:	0.074
Rat Oral Acute Toxicity:	0.1
Maximum Recommended Daily Dose:	0.624
Skin Sensitization:	0.841
Carcinogencity:	0.362
Eye Corrosion:	0.011
Eye Irritation:	0.949
Respiratory Toxicity:	0.195

Download Data

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

Natural Product: NPC256555

Natural Product ID:	NPC256555
*Common Name:**	Melanettin
IUPAC Name:	6-hydroxy-4-(4-hydroxyphenyl)-7-methoxychromen-2-one
Synonyms:
Standard InCHIKey:	HUGUGFBIYQBLCS-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C16H12O5/c1-20-15-8-14-12(6-13(15)18)11(7-16(19)21-14)9-2-4-10(17)5-3-9/h2-8,17-18H,1H3
SMILES:	COc1cc2c(cc1O)c(cc(=O)o2)c1ccc(cc1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2397755
PubChem CID:	442808
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0001614] Neoflavonoids [CHEMONTID:0001389] Neoflavones

*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
NPO26331	Plumbago auriculata	Species	Plumbaginaceae	Eukaryota	n.a.	flower	n.a.	PMID[22260638]
NPO20876	Arnica longifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23501116]
NPO18117	Dalbergia odorifera	Species	Fabaceae	Eukaryota	heartwood	n.a.	n.a.	PMID[23743282]
NPO18117	Dalbergia odorifera	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9525107]
NPO18117	Dalbergia odorifera	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23821	Rubus rigidus	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22848	Kaempferia galanga	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7149	Dalbergia melanoxylon	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22420	Lignum dalbergiae odoriferae rosewood	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TCMID]
NPO18117	Dalbergia odorifera	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23821	Rubus rigidus	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22848	Kaempferia galanga	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7149	Dalbergia melanoxylon	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO18117	Dalbergia odorifera	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO22848	Kaempferia galanga	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO22848	Kaempferia galanga	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO18117	Dalbergia odorifera	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO20888	Paraderris canarensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20876	Arnica longifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22848	Kaempferia galanga	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17889	Clerodendrum indicum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6173	Senegalia caesia	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26331	Plumbago auriculata	Species	Plumbaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23821	Rubus rigidus	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23269	Spodoptera exigua	Species	0ctuidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7149	Dalbergia melanoxylon	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18117	Dalbergia odorifera	Species	Fabaceae	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	1

Activity Type	# Activity
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	53200.0	nM	PMID[515662]

☑ 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 NPC256555 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	470
0.1-0.2	2122
0.2-0.3	5011
0.3-0.4	10788
0.4-0.5	6494
0.5-0.6	3929
0.6-0.7	5216
0.7-0.8	4995
0.8-0.85	2037
0.85-0.9	1185
0.9-0.95	436
0.95-1	14

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC34245
1.0	High Similarity	NPC91492
1.0	High Similarity	NPC110067
1.0	High Similarity	NPC7439
0.963	High Similarity	NPC38874
0.963	High Similarity	NPC474886
0.9504	High Similarity	NPC139839
0.9485	High Similarity	NPC52086
0.9485	High Similarity	NPC95162
0.9485	High Similarity	NPC20511
0.9485	High Similarity	NPC139548
0.9485	High Similarity	NPC148835
0.9485	High Similarity	NPC76336
0.9481	High Similarity	NPC234865
0.9437	High Similarity	NPC30688
0.9437	High Similarity	NPC176903
0.9433	High Similarity	NPC231149
0.9416	High Similarity	NPC13067
0.9412	High Similarity	NPC286843
0.9412	High Similarity	NPC82271
0.9412	High Similarity	NPC126682
0.9371	High Similarity	NPC21184
0.9371	High Similarity	NPC205727
0.9371	High Similarity	NPC294522
0.9371	High Similarity	NPC120426
0.9333	High Similarity	NPC277021
0.9296	High Similarity	NPC476347
0.9286	High Similarity	NPC236419
0.9265	High Similarity	NPC106215
0.9265	High Similarity	NPC92830
0.9241	High Similarity	NPC264875
0.9241	High Similarity	NPC120774
0.9241	High Similarity	NPC163598
0.9231	High Similarity	NPC476348
0.9231	High Similarity	NPC187398
0.9231	High Similarity	NPC48366
0.922	High Similarity	NPC185127
0.9191	High Similarity	NPC26673
0.9161	High Similarity	NPC275125
0.9161	High Similarity	NPC97937
0.9161	High Similarity	NPC15577
0.9161	High Similarity	NPC178129
0.9161	High Similarity	NPC170239
0.9149	High Similarity	NPC230157
0.9149	High Similarity	NPC6568
0.9137	High Similarity	NPC164148
0.9137	High Similarity	NPC43500
0.9124	High Similarity	NPC474600
0.9124	High Similarity	NPC111635
0.9118	High Similarity	NPC202762
0.9118	High Similarity	NPC137949
0.9118	High Similarity	NPC86655
0.9065	High Similarity	NPC102904
0.9065	High Similarity	NPC176051
0.9065	High Similarity	NPC103976
0.9065	High Similarity	NPC276490
0.9065	High Similarity	NPC107551
0.9065	High Similarity	NPC474282
0.9065	High Similarity	NPC326797
0.9051	High Similarity	NPC229442
0.9051	High Similarity	NPC168059
0.9051	High Similarity	NPC474810
0.9048	High Similarity	NPC150442
0.9044	High Similarity	NPC73738
0.9034	High Similarity	NPC113790
0.9021	High Similarity	NPC125617
0.9007	High Similarity	NPC300611
0.9	High Similarity	NPC25966
0.9	High Similarity	NPC245207
0.9	High Similarity	NPC319647
0.9	High Similarity	NPC127218
0.8993	High Similarity	NPC472334
0.8993	High Similarity	NPC472336
0.8986	High Similarity	NPC8712
0.898	High Similarity	NPC53587
0.898	High Similarity	NPC176186
0.898	High Similarity	NPC169404
0.8978	High Similarity	NPC245120
0.8978	High Similarity	NPC319969
0.8978	High Similarity	NPC127624
0.8971	High Similarity	NPC299221
0.8971	High Similarity	NPC234488
0.8971	High Similarity	NPC311680
0.8971	High Similarity	NPC51840
0.8971	High Similarity	NPC214860
0.8971	High Similarity	NPC91291
0.8971	High Similarity	NPC244799
0.8971	High Similarity	NPC240722
0.8958	High Similarity	NPC268515
0.8958	High Similarity	NPC287275
0.8958	High Similarity	NPC205361
0.8958	High Similarity	NPC40222
0.8951	High Similarity	NPC471763
0.8944	High Similarity	NPC469564
0.8944	High Similarity	NPC472335
0.8944	High Similarity	NPC472332
0.8929	High Similarity	NPC105493
0.8929	High Similarity	NPC476171
0.8921	High Similarity	NPC112246
0.8921	High Similarity	NPC472337
0.8921	High Similarity	NPC470356
0.8921	High Similarity	NPC195022
0.8921	High Similarity	NPC252095
0.8921	High Similarity	NPC474206
0.8921	High Similarity	NPC112939
0.8921	High Similarity	NPC94750
0.8921	High Similarity	NPC121812
0.8913	High Similarity	NPC241341
0.8913	High Similarity	NPC36437
0.8913	High Similarity	NPC233018
0.8912	High Similarity	NPC213197
0.8905	High Similarity	NPC142530
0.8905	High Similarity	NPC147317
0.8897	High Similarity	NPC27239
0.8897	High Similarity	NPC10225
0.8897	High Similarity	NPC123127
0.8897	High Similarity	NPC58164
0.8897	High Similarity	NPC45824
0.8881	High Similarity	NPC138212
0.8873	High Similarity	NPC471389
0.8865	High Similarity	NPC270256
0.8859	High Similarity	NPC7178
0.8859	High Similarity	NPC62903
0.8857	High Similarity	NPC162659
0.8857	High Similarity	NPC227503
0.8857	High Similarity	NPC248727
0.8857	High Similarity	NPC474639
0.8857	High Similarity	NPC173660
0.8857	High Similarity	NPC16435
0.8857	High Similarity	NPC265433
0.8857	High Similarity	NPC230734
0.8857	High Similarity	NPC167517
0.8857	High Similarity	NPC306441
0.8857	High Similarity	NPC270456
0.8849	High Similarity	NPC317380
0.8849	High Similarity	NPC473054
0.8849	High Similarity	NPC309953
0.8841	High Similarity	NPC6451
0.8841	High Similarity	NPC137669
0.8841	High Similarity	NPC474635
0.8828	High Similarity	NPC475896
0.8824	High Similarity	NPC266691
0.8824	High Similarity	NPC46274
0.8824	High Similarity	NPC226331
0.8811	High Similarity	NPC107161
0.8803	High Similarity	NPC160283
0.8803	High Similarity	NPC259519
0.8803	High Similarity	NPC254759
0.88	High Similarity	NPC155015
0.88	High Similarity	NPC142479
0.8794	High Similarity	NPC126206
0.8794	High Similarity	NPC211549
0.8786	High Similarity	NPC234333
0.8786	High Similarity	NPC201357
0.8786	High Similarity	NPC224941
0.8786	High Similarity	NPC472521
0.8786	High Similarity	NPC311430
0.8786	High Similarity	NPC47398
0.8786	High Similarity	NPC134968
0.8786	High Similarity	NPC281521
0.8786	High Similarity	NPC255147
0.8786	High Similarity	NPC61946
0.8786	High Similarity	NPC260898
0.8786	High Similarity	NPC151224
0.8777	High Similarity	NPC472522
0.8777	High Similarity	NPC11060
0.8777	High Similarity	NPC36661
0.8777	High Similarity	NPC475840
0.8776	High Similarity	NPC206264
0.8776	High Similarity	NPC212670
0.8776	High Similarity	NPC313334
0.8768	High Similarity	NPC474356
0.8768	High Similarity	NPC232275
0.8768	High Similarity	NPC12275
0.8768	High Similarity	NPC45715
0.8766	High Similarity	NPC234004
0.8759	High Similarity	NPC292256
0.875	High Similarity	NPC324112
0.875	High Similarity	NPC236791
0.875	High Similarity	NPC74817
0.875	High Similarity	NPC250432
0.875	High Similarity	NPC246620
0.875	High Similarity	NPC5447
0.875	High Similarity	NPC82679
0.875	High Similarity	NPC216836
0.875	High Similarity	NPC124452
0.875	High Similarity	NPC293054
0.875	High Similarity	NPC169474
0.875	High Similarity	NPC210355
0.875	High Similarity	NPC282000
0.875	High Similarity	NPC159968
0.8741	High Similarity	NPC168259
0.8741	High Similarity	NPC247291
0.8741	High Similarity	NPC472520
0.8741	High Similarity	NPC83375
0.8741	High Similarity	NPC279851
0.8741	High Similarity	NPC224876
0.8733	High Similarity	NPC268484
0.8732	High Similarity	NPC260741
0.8732	High Similarity	NPC70682

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 NPC256555 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	440
0.1-0.2	1036
0.2-0.3	1963
0.3-0.4	2604
0.4-0.5	1695
0.5-0.6	920
0.6-0.7	330
0.7-0.8	106
0.8-0.85	39
0.85-0.9	11
0.9-0.95	6
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8824	High Similarity	NPD1529	Clinical (unspecified phase)
0.8776	High Similarity	NPD1653	Approved
0.875	High Similarity	NPD1530	Clinical (unspecified phase)
0.8705	High Similarity	NPD1613	Approved
0.8705	High Similarity	NPD1612	Clinical (unspecified phase)
0.8609	High Similarity	NPD2801	Approved
0.8489	Intermediate Similarity	NPD3027	Phase 3
0.8444	Intermediate Similarity	NPD422	Phase 1
0.8421	Intermediate Similarity	NPD1934	Approved
0.8258	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8255	Intermediate Similarity	NPD1511	Approved
0.8194	Intermediate Similarity	NPD3817	Phase 2
0.8146	Intermediate Similarity	NPD1512	Approved
0.8129	Intermediate Similarity	NPD1465	Phase 2
0.8129	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8086	Intermediate Similarity	NPD5844	Phase 1
0.8026	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.8015	Intermediate Similarity	NPD1548	Phase 1
0.8	Intermediate Similarity	NPD7549	Discontinued
0.8	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7987	Intermediate Similarity	NPD1652	Phase 2
0.7933	Intermediate Similarity	NPD3750	Approved
0.7914	Intermediate Similarity	NPD1610	Phase 2
0.7914	Intermediate Similarity	NPD3818	Discontinued
0.7911	Intermediate Similarity	NPD3882	Suspended
0.7902	Intermediate Similarity	NPD4908	Phase 1
0.7901	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7901	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7901	Intermediate Similarity	NPD6166	Phase 2
0.7877	Intermediate Similarity	NPD5124	Phase 1
0.7877	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7866	Intermediate Similarity	NPD7054	Approved
0.7818	Intermediate Similarity	NPD7472	Approved
0.7818	Intermediate Similarity	NPD7074	Phase 3
0.7812	Intermediate Similarity	NPD6234	Discontinued
0.7808	Intermediate Similarity	NPD4060	Phase 1
0.7801	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7793	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7793	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD6232	Discontinued
0.7746	Intermediate Similarity	NPD3225	Approved
0.7736	Intermediate Similarity	NPD5402	Approved
0.7733	Intermediate Similarity	NPD7266	Discontinued
0.7727	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7716	Intermediate Similarity	NPD7199	Phase 2
0.7714	Intermediate Similarity	NPD3496	Discontinued
0.7708	Intermediate Similarity	NPD2861	Phase 2
0.7708	Intermediate Similarity	NPD3018	Phase 2
0.7692	Intermediate Similarity	NPD2797	Approved
0.7667	Intermediate Similarity	NPD2935	Discontinued
0.7665	Intermediate Similarity	NPD6797	Phase 2
0.7665	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7662	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.764	Intermediate Similarity	NPD7075	Discontinued
0.7636	Intermediate Similarity	NPD7473	Discontinued
0.7635	Intermediate Similarity	NPD230	Phase 1
0.7635	Intermediate Similarity	NPD447	Suspended
0.763	Intermediate Similarity	NPD228	Approved
0.7622	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD7251	Discontinued
0.761	Intermediate Similarity	NPD37	Approved
0.7603	Intermediate Similarity	NPD4625	Phase 3
0.76	Intermediate Similarity	NPD3748	Approved
0.7582	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7578	Intermediate Similarity	NPD4965	Approved
0.7578	Intermediate Similarity	NPD4966	Approved
0.7578	Intermediate Similarity	NPD4967	Phase 2
0.7574	Intermediate Similarity	NPD7808	Phase 3
0.7566	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7562	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7552	Intermediate Similarity	NPD4749	Approved
0.7552	Intermediate Similarity	NPD2983	Phase 2
0.7552	Intermediate Similarity	NPD2982	Phase 2
0.7551	Intermediate Similarity	NPD3268	Approved
0.7548	Intermediate Similarity	NPD6799	Approved
0.7546	Intermediate Similarity	NPD5494	Approved
0.7534	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD6190	Approved
0.7531	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7517	Intermediate Similarity	NPD4340	Discontinued
0.7516	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6233	Phase 2
0.75	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6801	Discontinued
0.7485	Intermediate Similarity	NPD919	Approved
0.7485	Intermediate Similarity	NPD7228	Approved
0.7484	Intermediate Similarity	NPD4380	Phase 2
0.7483	Intermediate Similarity	NPD1510	Phase 2
0.7483	Intermediate Similarity	NPD2981	Phase 2
0.7483	Intermediate Similarity	NPD7095	Approved
0.7453	Intermediate Similarity	NPD7819	Suspended
0.7451	Intermediate Similarity	NPD1549	Phase 2
0.745	Intermediate Similarity	NPD1558	Phase 1
0.7445	Intermediate Similarity	NPD5535	Approved
0.7434	Intermediate Similarity	NPD1551	Phase 2
0.7432	Intermediate Similarity	NPD1296	Phase 2
0.7432	Intermediate Similarity	NPD6798	Discontinued
0.7413	Intermediate Similarity	NPD1611	Approved
0.741	Intermediate Similarity	NPD6671	Approved
0.7405	Intermediate Similarity	NPD5403	Approved
0.7391	Intermediate Similarity	NPD5283	Phase 1
0.7389	Intermediate Similarity	NPD5401	Approved
0.7375	Intermediate Similarity	NPD6599	Discontinued
0.7368	Intermediate Similarity	NPD4308	Phase 3
0.7362	Intermediate Similarity	NPD7768	Phase 2
0.7355	Intermediate Similarity	NPD4628	Phase 3
0.7333	Intermediate Similarity	NPD1240	Approved
0.7329	Intermediate Similarity	NPD3266	Approved
0.7329	Intermediate Similarity	NPD3267	Approved
0.7329	Intermediate Similarity	NPD7411	Suspended
0.7325	Intermediate Similarity	NPD4357	Discontinued
0.732	Intermediate Similarity	NPD2796	Approved
0.7315	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD6559	Discontinued
0.7305	Intermediate Similarity	NPD5536	Phase 2
0.7292	Intermediate Similarity	NPD1535	Discovery
0.729	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7289	Intermediate Similarity	NPD1247	Approved
0.7285	Intermediate Similarity	NPD1933	Approved
0.7285	Intermediate Similarity	NPD6355	Discontinued
0.7278	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD4626	Approved
0.7255	Intermediate Similarity	NPD7033	Discontinued
0.7241	Intermediate Similarity	NPD1608	Approved
0.7241	Intermediate Similarity	NPD1481	Phase 2
0.7241	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7237	Intermediate Similarity	NPD1607	Approved
0.7235	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7233	Intermediate Similarity	NPD7314	Clinical (unspecified phase)
0.7229	Intermediate Similarity	NPD5677	Discontinued
0.7222	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD943	Approved
0.7216	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD3749	Approved
0.7211	Intermediate Similarity	NPD1203	Approved
0.7208	Intermediate Similarity	NPD6100	Approved
0.7208	Intermediate Similarity	NPD6099	Approved
0.7186	Intermediate Similarity	NPD8127	Discontinued
0.7179	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD6674	Discontinued
0.7172	Intermediate Similarity	NPD1091	Approved
0.717	Intermediate Similarity	NPD7447	Phase 1
0.7161	Intermediate Similarity	NPD3540	Phase 1
0.7161	Intermediate Similarity	NPD5763	Approved
0.7161	Intermediate Similarity	NPD5762	Approved
0.716	Intermediate Similarity	NPD4678	Approved
0.716	Intermediate Similarity	NPD4675	Approved
0.7143	Intermediate Similarity	NPD3686	Approved
0.7143	Intermediate Similarity	NPD3687	Approved
0.7134	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD4110	Phase 3
0.7132	Intermediate Similarity	NPD968	Approved
0.7107	Intermediate Similarity	NPD7213	Phase 3
0.7107	Intermediate Similarity	NPD7212	Phase 2
0.7105	Intermediate Similarity	NPD4307	Phase 2
0.7101	Intermediate Similarity	NPD3022	Approved
0.7101	Intermediate Similarity	NPD3021	Approved
0.7099	Intermediate Similarity	NPD3226	Approved
0.7097	Intermediate Similarity	NPD6032	Approved
0.7097	Intermediate Similarity	NPD3539	Phase 1
0.7091	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD4288	Approved
0.7089	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD2313	Discontinued
0.7083	Intermediate Similarity	NPD5691	Approved
0.7081	Intermediate Similarity	NPD920	Approved
0.7076	Intermediate Similarity	NPD3751	Discontinued
0.707	Intermediate Similarity	NPD1243	Approved
0.7063	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD2533	Approved
0.7063	Intermediate Similarity	NPD2532	Approved
0.7063	Intermediate Similarity	NPD2534	Approved
0.7059	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD9697	Approved
0.7055	Intermediate Similarity	NPD3705	Approved
0.7041	Intermediate Similarity	NPD7229	Phase 3
0.7034	Intermediate Similarity	NPD17	Approved
0.7034	Intermediate Similarity	NPD1778	Approved
0.7029	Intermediate Similarity	NPD2684	Approved
0.7027	Intermediate Similarity	NPD8651	Approved
0.7011	Intermediate Similarity	NPD7685	Pre-registration
0.7011	Intermediate Similarity	NPD7240	Approved
0.7007	Intermediate Similarity	NPD9269	Phase 2
0.7007	Intermediate Similarity	NPD9717	Approved
0.7006	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD2424	Discontinued
0.7006	Intermediate Similarity	NPD6971	Discontinued
0.7	Intermediate Similarity	NPD3926	Phase 2
0.7	Intermediate Similarity	NPD9494	Approved
0.7	Intermediate Similarity	NPD5242	Approved
0.6994	Remote Similarity	NPD4005	Discontinued
0.6994	Remote Similarity	NPD8158	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD3620	Phase 2
0.6993	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD4140	Approved
0.6989	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD8054	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