NPASS Compound

Structure

NPC472462 OpenBabel07101719242D 23 26 0 0 0 0 0 0 0 0999 V2000 -1.3660 0.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8660 -0.5000 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 -0.8660 -1.5000 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 5.6369 -1.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6369 -0.1340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 -1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1369 -1.0000 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 0.8660 -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 5.1369 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6369 -1.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6369 -0.1340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1369 -1.0000 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 -0.5000 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 7.1369 -2.7321 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.1369 0.7321 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 -0.1910 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 19 1 0 0 0 0 2 19 1 0 0 0 0 3 4 2 0 0 0 0 3 11 1 0 0 0 0 4 19 1 0 0 0 0 5 11 1 0 0 0 0 5 12 2 0 0 0 0 6 13 2 0 0 0 0 6 14 1 0 0 0 0 7 13 1 0 0 0 0 7 15 2 0 0 0 0 8 12 1 0 0 0 0 8 16 2 0 0 0 0 9 14 2 0 0 0 0 9 15 1 0 0 0 0 10 17 2 0 0 0 0 10 18 1 0 0 0 0 11 18 2 0 0 0 0 12 17 1 0 0 0 0 13 16 1 0 0 0 0 14 20 1 0 0 0 0 15 21 1 0 0 0 0 16 22 1 0 0 0 0 17 22 1 0 0 0 0 18 23 1 0 0 0 0 19 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	308.1
Volume:	317.024
LogP:	4.968
LogD:	3.76
LogS:	-3.584
# Rotatable Bonds:	1
TPSA:	62.83
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.684
Synthetic Accessibility Score:	2.902
Fsp3:	0.158
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.881
MDCK Permeability:	1.3839318853570148e-05
Pgp-inhibitor:	0.168
Pgp-substrate:	0.925
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.374
30% Bioavailability (F30%):	0.855

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.02
Plasma Protein Binding (PPB):	99.93140411376953%
Volume Distribution (VD):	0.945
Pgp-substrate:	1.1291298866271973%

ADMET: Metabolism

CYP1A2-inhibitor:	0.986
CYP1A2-substrate:	0.535
CYP2C19-inhibitor:	0.876
CYP2C19-substrate:	0.061
CYP2C9-inhibitor:	0.698
CYP2C9-substrate:	0.934
CYP2D6-inhibitor:	0.958
CYP2D6-substrate:	0.886
CYP3A4-inhibitor:	0.937
CYP3A4-substrate:	0.155

ADMET: Excretion

Clearance (CL):	8.001
Half-life (T1/2):	0.47

ADMET: Toxicity

hERG Blockers:	0.274
Human Hepatotoxicity (H-HT):	0.399
Drug-inuced Liver Injury (DILI):	0.579
AMES Toxicity:	0.018
Rat Oral Acute Toxicity:	0.061
Maximum Recommended Daily Dose:	0.925
Skin Sensitization:	0.913
Carcinogencity:	0.473
Eye Corrosion:	0.003
Eye Irritation:	0.592
Respiratory Toxicity:	0.874

Download Data

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

Natural Product: NPC472462

Natural Product ID:	NPC472462
*Common Name:**	KIUJXFHVPMFXEJ-UHFFFAOYSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	KIUJXFHVPMFXEJ-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C19H16O4/c1-19(2)4-3-11-5-12-8-16(22-17(12)10-18(11)23-19)13-6-14(20)9-15(21)7-13/h3-10,20-21H,1-2H3
SMILES:	CC1(C=CC2=C(O1)C=C3C(=C2)C=C(O3)C4=CC(=CC(=C4)O)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3422851
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0003405] 2-arylbenzofuran flavonoids

*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
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20815207]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	root	n.a.	PMID[21319773]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	leaf	n.a.	PMID[21319773]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	bark	n.a.	PMID[21319773]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	leaf	n.a.	PMID[22207282]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	root	n.a.	PMID[23806866]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	Konya, Turkey	2007-APR	PMID[24901948]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	root bark	University of Veterinary and Pharmaceutical Sciences Brno (UVPS Brno), Brno, Czech Republic	2011-APR	PMID[24901948]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	leaves	Chungbuk, Korea	n.a.	PMID[25935644]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	root	n.a.	PMID[25981820]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	latex	n.a.	PMID[27294120]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	Root barks	n.a.	n.a.	PMID[3097265]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO28265	Morus alba	Species	Moraceae	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
Others	1

Activity Type	# Activity
Individual Protein	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1120	Individual Protein	Pancreatic triacylglycerol lipase	Sus scrofa	Inhibition	=	67.9	%	PMID[448525]
NPT1120	Individual Protein	Pancreatic triacylglycerol lipase	Sus scrofa	IC50	=	29200.0	nM	PMID[448525]

☑ 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 NPC472462 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	427
0.1-0.2	1845
0.2-0.3	4217
0.3-0.4	11077
0.4-0.5	6972
0.5-0.6	3873
0.6-0.7	5547
0.7-0.8	4756
0.8-0.85	2022
0.85-0.9	1720
0.9-0.95	213
0.95-1	28

Similarity Score	Similarity Level	Natural Product ID
0.9799	High Similarity	NPC268360
0.9795	High Similarity	NPC230713
0.9795	High Similarity	NPC78335
0.973	High Similarity	NPC72370
0.9728	High Similarity	NPC170169
0.9726	High Similarity	NPC178202
0.9726	High Similarity	NPC221868
0.9726	High Similarity	NPC37208
0.9664	High Similarity	NPC99199
0.9658	High Similarity	NPC272194
0.9597	High Similarity	NPC235333
0.9592	High Similarity	NPC37226
0.9592	High Similarity	NPC226644
0.9536	High Similarity	NPC65504
0.9533	High Similarity	NPC148938
0.9533	High Similarity	NPC297531
0.9533	High Similarity	NPC198490
0.9533	High Similarity	NPC213936
0.9527	High Similarity	NPC167576
0.9521	High Similarity	NPC210826
0.9467	High Similarity	NPC213608
0.9467	High Similarity	NPC183874
0.9467	High Similarity	NPC1477
0.9463	High Similarity	NPC23668
0.9463	High Similarity	NPC193976
0.9456	High Similarity	NPC12148
0.9456	High Similarity	NPC130581
0.9456	High Similarity	NPC17816
0.9452	High Similarity	NPC155144
0.9408	High Similarity	NPC96342
0.9408	High Similarity	NPC246647
0.9408	High Similarity	NPC164110
0.9408	High Similarity	NPC212967
0.94	High Similarity	NPC142308
0.94	High Similarity	NPC5871
0.94	High Similarity	NPC207624
0.9392	High Similarity	NPC135325
0.9388	High Similarity	NPC51641
0.9388	High Similarity	NPC300267
0.9384	High Similarity	NPC225884
0.9351	High Similarity	NPC45124
0.9351	High Similarity	NPC30655
0.9351	High Similarity	NPC74854
0.9342	High Similarity	NPC180924
0.9333	High Similarity	NPC115324
0.9333	High Similarity	NPC58668
0.9333	High Similarity	NPC106372
0.9329	High Similarity	NPC296030
0.9329	High Similarity	NPC39929
0.9329	High Similarity	NPC65775
0.9329	High Similarity	NPC317492
0.9329	High Similarity	NPC10027
0.932	High Similarity	NPC98926
0.932	High Similarity	NPC234629
0.932	High Similarity	NPC311741
0.929	High Similarity	NPC219861
0.929	High Similarity	NPC193998
0.9286	High Similarity	NPC304839
0.9286	High Similarity	NPC220582
0.9281	High Similarity	NPC260902
0.9281	High Similarity	NPC296957
0.9267	High Similarity	NPC101957
0.9267	High Similarity	NPC120105
0.9262	High Similarity	NPC186397
0.9262	High Similarity	NPC168085
0.9262	High Similarity	NPC37135
0.9252	High Similarity	NPC17262
0.9252	High Similarity	NPC302181
0.9247	High Similarity	NPC147688
0.9247	High Similarity	NPC64908
0.9247	High Similarity	NPC156590
0.9247	High Similarity	NPC205006
0.9247	High Similarity	NPC118840
0.9231	High Similarity	NPC159508
0.9221	High Similarity	NPC40583
0.9221	High Similarity	NPC244750
0.9216	High Similarity	NPC247677
0.9216	High Similarity	NPC160015
0.9216	High Similarity	NPC137100
0.9211	High Similarity	NPC122365
0.92	High Similarity	NPC223988
0.92	High Similarity	NPC266499
0.9189	High Similarity	NPC230943
0.9184	High Similarity	NPC144499
0.9184	High Similarity	NPC53192
0.9184	High Similarity	NPC226636
0.9184	High Similarity	NPC11561
0.9178	High Similarity	NPC270883
0.9178	High Similarity	NPC172986
0.9178	High Similarity	NPC261227
0.9178	High Similarity	NPC475680
0.9178	High Similarity	NPC305355
0.9178	High Similarity	NPC235239
0.9172	High Similarity	NPC204088
0.9172	High Similarity	NPC259007
0.9172	High Similarity	NPC329215
0.9161	High Similarity	NPC260296
0.9161	High Similarity	NPC115432
0.9145	High Similarity	NPC130015
0.9145	High Similarity	NPC327269
0.9145	High Similarity	NPC38361
0.9145	High Similarity	NPC31627
0.9145	High Similarity	NPC476238
0.9145	High Similarity	NPC263676
0.9145	High Similarity	NPC253872
0.9139	High Similarity	NPC472633
0.9133	High Similarity	NPC266572
0.9128	High Similarity	NPC124729
0.9122	High Similarity	NPC212932
0.9122	High Similarity	NPC38219
0.9122	High Similarity	NPC18585
0.9122	High Similarity	NPC166138
0.9122	High Similarity	NPC190637
0.9122	High Similarity	NPC106985
0.9122	High Similarity	NPC24821
0.9122	High Similarity	NPC9117
0.9122	High Similarity	NPC219915
0.9122	High Similarity	NPC293053
0.9116	High Similarity	NPC103362
0.9116	High Similarity	NPC110969
0.9114	High Similarity	NPC53640
0.9114	High Similarity	NPC323137
0.9114	High Similarity	NPC277480
0.911	High Similarity	NPC96565
0.911	High Similarity	NPC301217
0.911	High Similarity	NPC220062
0.911	High Similarity	NPC303633
0.911	High Similarity	NPC216978
0.911	High Similarity	NPC55018
0.9108	High Similarity	NPC155640
0.9108	High Similarity	NPC472581
0.9097	High Similarity	NPC476349
0.9097	High Similarity	NPC476350
0.9085	High Similarity	NPC95842
0.9085	High Similarity	NPC178964
0.9085	High Similarity	NPC280530
0.9079	High Similarity	NPC116604
0.9079	High Similarity	NPC258249
0.9079	High Similarity	NPC471675
0.9079	High Similarity	NPC154345
0.9073	High Similarity	NPC269420
0.9068	High Similarity	NPC310794
0.9067	High Similarity	NPC24673
0.9067	High Similarity	NPC201731
0.9067	High Similarity	NPC79469
0.9067	High Similarity	NPC104406
0.9067	High Similarity	NPC97716
0.9067	High Similarity	NPC14001
0.9067	High Similarity	NPC237635
0.9067	High Similarity	NPC166757
0.906	High Similarity	NPC216538
0.906	High Similarity	NPC326500
0.906	High Similarity	NPC273538
0.906	High Similarity	NPC278175
0.906	High Similarity	NPC257236
0.9057	High Similarity	NPC253730
0.9057	High Similarity	NPC50394
0.9057	High Similarity	NPC286230
0.9054	High Similarity	NPC293852
0.9054	High Similarity	NPC59739
0.9054	High Similarity	NPC473042
0.9054	High Similarity	NPC299080
0.9054	High Similarity	NPC200694
0.9054	High Similarity	NPC78803
0.9054	High Similarity	NPC217083
0.9054	High Similarity	NPC62840
0.9054	High Similarity	NPC214236
0.9051	High Similarity	NPC169471
0.9051	High Similarity	NPC136641
0.9051	High Similarity	NPC38914
0.9051	High Similarity	NPC37183
0.9048	High Similarity	NPC69769
0.9048	High Similarity	NPC159275
0.9048	High Similarity	NPC241100
0.9048	High Similarity	NPC150522
0.9041	High Similarity	NPC201395
0.9038	High Similarity	NPC328102
0.9032	High Similarity	NPC476981
0.9032	High Similarity	NPC196448
0.9026	High Similarity	NPC233776
0.9026	High Similarity	NPC472280
0.902	High Similarity	NPC285623
0.902	High Similarity	NPC142527
0.902	High Similarity	NPC45934
0.902	High Similarity	NPC67654
0.902	High Similarity	NPC473996
0.9013	High Similarity	NPC321896
0.9013	High Similarity	NPC88804
0.9013	High Similarity	NPC135303
0.9013	High Similarity	NPC476185
0.9013	High Similarity	NPC37348
0.9013	High Similarity	NPC148423
0.9013	High Similarity	NPC13282
0.9013	High Similarity	NPC3825
0.9013	High Similarity	NPC29777
0.9013	High Similarity	NPC471115
0.9013	High Similarity	NPC61258
0.9013	High Similarity	NPC227122
0.9013	High Similarity	NPC472421
0.9007	High Similarity	NPC244407

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 NPC472462 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	398
0.1-0.2	984
0.2-0.3	1508
0.3-0.4	2693
0.4-0.5	1885
0.5-0.6	1122
0.6-0.7	377
0.7-0.8	114
0.8-0.85	52
0.85-0.9	17
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.906	High Similarity	NPD4378	Clinical (unspecified phase)
0.906	High Similarity	NPD7410	Clinical (unspecified phase)
0.879	High Similarity	NPD3749	Approved
0.8718	High Similarity	NPD2393	Clinical (unspecified phase)
0.8618	High Similarity	NPD1511	Approved
0.86	High Similarity	NPD1243	Approved
0.8599	High Similarity	NPD2801	Approved
0.8591	High Similarity	NPD2344	Approved
0.8581	High Similarity	NPD1510	Phase 2
0.8571	High Similarity	NPD920	Approved
0.8533	High Similarity	NPD1549	Phase 2
0.8526	High Similarity	NPD4380	Phase 2
0.8523	High Similarity	NPD2796	Approved
0.8506	High Similarity	NPD1512	Approved
0.8494	Intermediate Similarity	NPD6559	Discontinued
0.8491	Intermediate Similarity	NPD3882	Suspended
0.8481	Intermediate Similarity	NPD7819	Suspended
0.8477	Intermediate Similarity	NPD2800	Approved
0.8471	Intermediate Similarity	NPD7411	Suspended
0.8467	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8467	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8442	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.8435	Intermediate Similarity	NPD1240	Approved
0.8428	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8418	Intermediate Similarity	NPD1934	Approved
0.8395	Intermediate Similarity	NPD6959	Discontinued
0.8366	Intermediate Similarity	NPD2309	Approved
0.8364	Intermediate Similarity	NPD3818	Discontinued
0.8333	Intermediate Similarity	NPD5494	Approved
0.8323	Intermediate Similarity	NPD7075	Discontinued
0.8322	Intermediate Similarity	NPD1607	Approved
0.8312	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.8282	Intermediate Similarity	NPD1247	Approved
0.8261	Intermediate Similarity	NPD7768	Phase 2
0.825	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8242	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8232	Intermediate Similarity	NPD6232	Discontinued
0.821	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8205	Intermediate Similarity	NPD2533	Approved
0.8205	Intermediate Similarity	NPD2532	Approved
0.8205	Intermediate Similarity	NPD2534	Approved
0.8193	Intermediate Similarity	NPD7473	Discontinued
0.8187	Intermediate Similarity	NPD6801	Discontinued
0.8182	Intermediate Similarity	NPD3750	Approved
0.8182	Intermediate Similarity	NPD3926	Phase 2
0.816	Intermediate Similarity	NPD919	Approved
0.8158	Intermediate Similarity	NPD2935	Discontinued
0.8133	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8133	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8133	Intermediate Similarity	NPD6166	Phase 2
0.8117	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8086	Intermediate Similarity	NPD3817	Phase 2
0.8054	Intermediate Similarity	NPD2313	Discontinued
0.8052	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8037	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8025	Intermediate Similarity	NPD6799	Approved
0.8	Intermediate Similarity	NPD3226	Approved
0.7988	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7974	Intermediate Similarity	NPD2799	Discontinued
0.7974	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7911	Intermediate Similarity	NPD7390	Discontinued
0.7907	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7882	Intermediate Similarity	NPD7054	Approved
0.7882	Intermediate Similarity	NPD5844	Phase 1
0.7871	Intermediate Similarity	NPD2346	Discontinued
0.7866	Intermediate Similarity	NPD5402	Approved
0.7857	Intermediate Similarity	NPD3748	Approved
0.784	Intermediate Similarity	NPD6599	Discontinued
0.7836	Intermediate Similarity	NPD7074	Phase 3
0.7836	Intermediate Similarity	NPD7472	Approved
0.7829	Intermediate Similarity	NPD943	Approved
0.7806	Intermediate Similarity	NPD6100	Approved
0.7806	Intermediate Similarity	NPD1551	Phase 2
0.7806	Intermediate Similarity	NPD6099	Approved
0.7791	Intermediate Similarity	NPD5953	Discontinued
0.7791	Intermediate Similarity	NPD6797	Phase 2
0.7778	Intermediate Similarity	NPD7286	Phase 2
0.7758	Intermediate Similarity	NPD2296	Approved
0.7756	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7746	Intermediate Similarity	NPD7251	Discontinued
0.774	Intermediate Similarity	NPD4287	Approved
0.7727	Intermediate Similarity	NPD6651	Approved
0.7722	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7722	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7701	Intermediate Similarity	NPD7808	Phase 3
0.7701	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD1465	Phase 2
0.7697	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD7229	Phase 3
0.7654	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7654	Intermediate Similarity	NPD5403	Approved
0.7643	Intermediate Similarity	NPD1471	Phase 3
0.7632	Intermediate Similarity	NPD4625	Phase 3
0.76	Intermediate Similarity	NPD1203	Approved
0.7588	Intermediate Similarity	NPD5711	Approved
0.7588	Intermediate Similarity	NPD5710	Approved
0.7586	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7582	Intermediate Similarity	NPD3764	Approved
0.7582	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.755	Intermediate Similarity	NPD2798	Approved
0.7531	Intermediate Similarity	NPD5401	Approved
0.7516	Intermediate Similarity	NPD7033	Discontinued
0.7516	Intermediate Similarity	NPD4308	Phase 3
0.7514	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD5761	Phase 2
0.7485	Intermediate Similarity	NPD5760	Phase 2
0.7468	Intermediate Similarity	NPD5405	Approved
0.7468	Intermediate Similarity	NPD3268	Approved
0.7468	Intermediate Similarity	NPD5406	Approved
0.7468	Intermediate Similarity	NPD5404	Approved
0.7468	Intermediate Similarity	NPD5408	Approved
0.7451	Intermediate Similarity	NPD4908	Phase 1
0.7436	Intermediate Similarity	NPD447	Suspended
0.7432	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7432	Intermediate Similarity	NPD4361	Phase 2
0.743	Intermediate Similarity	NPD8434	Phase 2
0.7429	Intermediate Similarity	NPD1729	Discontinued
0.7425	Intermediate Similarity	NPD6279	Approved
0.7425	Intermediate Similarity	NPD6280	Approved
0.7423	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.74	Intermediate Similarity	NPD9717	Approved
0.7391	Intermediate Similarity	NPD4628	Phase 3
0.7377	Intermediate Similarity	NPD4360	Phase 2
0.7377	Intermediate Similarity	NPD4363	Phase 3
0.7368	Intermediate Similarity	NPD1470	Approved
0.7368	Intermediate Similarity	NPD2797	Approved
0.7363	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7362	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7349	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD6832	Phase 2
0.7333	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD422	Phase 1
0.7329	Intermediate Similarity	NPD2654	Approved
0.7325	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7325	Intermediate Similarity	NPD230	Phase 1
0.7314	Intermediate Similarity	NPD3751	Discontinued
0.7297	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD1548	Phase 1
0.7296	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7285	Intermediate Similarity	NPD1608	Approved
0.7283	Intermediate Similarity	NPD6808	Phase 2
0.7273	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7263	Intermediate Similarity	NPD8312	Approved
0.7263	Intermediate Similarity	NPD8313	Approved
0.7262	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7261	Intermediate Similarity	NPD4307	Phase 2
0.7253	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD411	Approved
0.7237	Intermediate Similarity	NPD4749	Approved
0.7235	Intermediate Similarity	NPD4288	Approved
0.7225	Intermediate Similarity	NPD7199	Phase 2
0.7219	Intermediate Similarity	NPD1610	Phase 2
0.7219	Intermediate Similarity	NPD1201	Approved
0.7219	Intermediate Similarity	NPD6844	Discontinued
0.7215	Intermediate Similarity	NPD5124	Phase 1
0.7215	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD2403	Approved
0.719	Intermediate Similarity	NPD3225	Approved
0.7184	Intermediate Similarity	NPD3787	Discontinued
0.7178	Intermediate Similarity	NPD7003	Approved
0.7152	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD1613	Approved
0.7151	Intermediate Similarity	NPD6971	Discontinued
0.7151	Intermediate Similarity	NPD3658	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD3266	Approved
0.7143	Intermediate Similarity	NPD3267	Approved
0.7143	Intermediate Similarity	NPD1164	Approved
0.7135	Intermediate Similarity	NPD7584	Approved
0.7119	Intermediate Similarity	NPD7177	Discontinued
0.7118	Intermediate Similarity	NPD37	Approved
0.711	Intermediate Similarity	NPD6234	Discontinued
0.7101	Intermediate Similarity	NPD6585	Discontinued
0.7095	Intermediate Similarity	NPD1252	Clinical (unspecified phase)
0.7093	Intermediate Similarity	NPD4966	Approved
0.7093	Intermediate Similarity	NPD4967	Phase 2
0.7093	Intermediate Similarity	NPD4965	Approved
0.709	Intermediate Similarity	NPD6779	Approved
0.709	Intermediate Similarity	NPD6781	Approved
0.709	Intermediate Similarity	NPD6782	Approved
0.709	Intermediate Similarity	NPD6776	Approved
0.709	Intermediate Similarity	NPD6780	Approved
0.709	Intermediate Similarity	NPD6778	Approved
0.709	Intermediate Similarity	NPD6777	Approved
0.7088	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD17	Approved
0.7062	Intermediate Similarity	NPD3446	Phase 1
0.7062	Intermediate Similarity	NPD8151	Discontinued
0.7059	Intermediate Similarity	NPD3972	Approved
0.7055	Intermediate Similarity	NPD2424	Discontinued
0.7051	Intermediate Similarity	NPD2861	Phase 2
0.7041	Intermediate Similarity	NPD7458	Discontinued
0.7031	Intermediate Similarity	NPD7870	Phase 2
0.7031	Intermediate Similarity	NPD7871	Phase 2
0.7025	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD1296	Phase 2
0.7006	Intermediate Similarity	NPD4575	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD7422	Clinical (unspecified phase)

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