NPASS Compound

Structure

CID170169 OpenBabel06191715542D 29 31 0 0 0 0 0 0 0 0999 V2000 1.8171 6.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 6.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 3.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4152 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 4.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 4.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 3.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 1.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 -1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 1.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0878 -1.6750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0878 0.0570 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.6180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5878 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 5.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 2.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5878 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0878 -1.6750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0878 0.0570 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5878 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5878 -2.5411 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5878 0.9230 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 16 1 0 0 0 0 2 16 1 0 0 0 0 3 17 1 0 0 0 0 4 28 1 0 0 0 0 5 6 1 0 0 0 0 5 7 1 0 0 0 0 6 16 2 0 0 0 0 7 17 1 0 0 0 0 8 10 1 0 0 0 0 8 17 2 0 0 0 0 9 11 2 0 0 0 0 9 18 1 0 0 0 0 10 22 1 0 0 0 0 11 23 1 0 0 0 0 12 19 2 0 0 0 0 12 20 1 0 0 0 0 13 19 1 0 0 0 0 13 21 2 0 0 0 0 14 18 1 0 0 0 0 14 24 2 0 0 0 0 15 20 2 0 0 0 0 15 21 1 0 0 0 0 18 25 2 0 0 0 0 19 24 1 0 0 0 0 20 26 1 0 0 0 0 21 27 1 0 0 0 0 22 23 2 0 0 0 0 22 25 1 0 0 0 0 23 28 1 0 0 0 0 24 29 1 0 0 0 0 25 29 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	392.2
Volume:	426.719
LogP:	6.608
LogD:	4.759
LogS:	-3.557
# Rotatable Bonds:	7
TPSA:	62.83
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.436
Synthetic Accessibility Score:	2.855
Fsp3:	0.28
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:	-4.925
MDCK Permeability:	1.6429588868049905e-05
Pgp-inhibitor:	0.938
Pgp-substrate:	0.479
Human Intestinal Absorption (HIA):	0.014
20% Bioavailability (F20%):	0.984
30% Bioavailability (F30%):	0.979

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.012
Plasma Protein Binding (PPB):	98.28345489501953%
Volume Distribution (VD):	1.59
Pgp-substrate:	1.1937512159347534%

ADMET: Metabolism

CYP1A2-inhibitor:	0.977
CYP1A2-substrate:	0.47
CYP2C19-inhibitor:	0.969
CYP2C19-substrate:	0.065
CYP2C9-inhibitor:	0.817
CYP2C9-substrate:	0.969
CYP2D6-inhibitor:	0.965
CYP2D6-substrate:	0.902
CYP3A4-inhibitor:	0.859
CYP3A4-substrate:	0.108

ADMET: Excretion

Clearance (CL):	9.043
Half-life (T1/2):	0.424

ADMET: Toxicity

hERG Blockers:	0.145
Human Hepatotoxicity (H-HT):	0.881
Drug-inuced Liver Injury (DILI):	0.379
AMES Toxicity:	0.008
Rat Oral Acute Toxicity:	0.014
Maximum Recommended Daily Dose:	0.928
Skin Sensitization:	0.9
Carcinogencity:	0.037
Eye Corrosion:	0.003
Eye Irritation:	0.175
Respiratory Toxicity:	0.793

Download Data

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

Natural Product: NPC170169

Natural Product ID:	NPC170169
*Common Name:**	Mulberrofuran B
IUPAC Name:	5-[7-[(2E)-3,7-dimethylocta-2,6-dienyl]-6-methoxy-1-benzofuran-2-yl]benzene-1,3-diol
Synonyms:
Standard InCHIKey:	OZLRLDMVAJOIKX-CAOOACKPSA-N
Standard InCHI:	InChI=1S/C25H28O4/c1-16(2)6-5-7-17(3)8-10-22-23(28-4)11-9-18-14-24(29-25(18)22)19-12-20(26)15-21(27)13-19/h6,8-9,11-15,26-27H,5,7,10H2,1-4H3/b17-8+
SMILES:	CC(=CCC/C(=C/Cc1c(ccc2cc(c3cc(cc(c3)O)O)oc12)OC)/C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL461067
PubChem CID:	6440635
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
NPO9402	Morus mongolica	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11429996]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20815207]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	bark	n.a.	PMID[21319773]
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.	leaf	n.a.	PMID[22207282]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	root	n.a.	PMID[23806866]
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	n.a.	Konya, Turkey	2007-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]
NPO9402	Morus mongolica	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
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]
NPO9402	Morus mongolica	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9402	Morus mongolica	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[TCM_Taiwan]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO9402	Morus mongolica	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
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
Others	4

Activity Type	# Activity
Cell Line	1
NON-MOLECULAR	1
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT924	Cell Line	HSC-2	Homo sapiens	CC50	=	59000.0	nM	PMID[514200]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	CC50	=	59000.0	nM	PMID[514200]
NPT27	Others	Unspecified		CC50	=	71000.0	nM	PMID[514200]
NPT27	Others	Unspecified		Ratio	=	1.2	n.a.	PMID[514200]

☑ 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 NPC170169 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	394
0.1-0.2	1621
0.2-0.3	4021
0.3-0.4	10466
0.4-0.5	7826
0.5-0.6	3676
0.6-0.7	5412
0.7-0.8	5041
0.8-0.85	2136
0.85-0.9	1832
0.9-0.95	231
0.95-1	41

Similarity Score	Similarity Level	Natural Product ID
0.9931	High Similarity	NPC230713
0.9931	High Similarity	NPC78335
0.9861	High Similarity	NPC226644
0.9861	High Similarity	NPC178202
0.9861	High Similarity	NPC37226
0.9796	High Similarity	NPC148938
0.9796	High Similarity	NPC198490
0.9728	High Similarity	NPC472462
0.9728	High Similarity	NPC183874
0.9728	High Similarity	NPC235333
0.9722	High Similarity	NPC130581
0.9722	High Similarity	NPC17816
0.9722	High Similarity	NPC12148
0.9664	High Similarity	NPC212967
0.9664	High Similarity	NPC246647
0.9664	High Similarity	NPC96342
0.9664	High Similarity	NPC164110
0.9662	High Similarity	NPC213936
0.9662	High Similarity	NPC297531
0.966	High Similarity	NPC207624
0.9658	High Similarity	NPC167576
0.9655	High Similarity	NPC135325
0.9653	High Similarity	NPC300267
0.9653	High Similarity	NPC51641
0.9653	High Similarity	NPC210826
0.9597	High Similarity	NPC180924
0.9595	High Similarity	NPC213608
0.9595	High Similarity	NPC1477
0.9592	High Similarity	NPC193976
0.9592	High Similarity	NPC23668
0.9592	High Similarity	NPC115324
0.9592	High Similarity	NPC58668
0.9592	High Similarity	NPC106372
0.9589	High Similarity	NPC39929
0.9589	High Similarity	NPC296030
0.9583	High Similarity	NPC98926
0.9583	High Similarity	NPC155144
0.9533	High Similarity	NPC268360
0.9527	High Similarity	NPC5871
0.9527	High Similarity	NPC142308
0.9514	High Similarity	NPC302181
0.9514	High Similarity	NPC225884
0.9467	High Similarity	NPC247677
0.9467	High Similarity	NPC160015
0.9463	High Similarity	NPC72370
0.9456	High Similarity	NPC37208
0.9456	High Similarity	NPC221868
0.9448	High Similarity	NPC230943
0.9444	High Similarity	NPC53192
0.9408	High Similarity	NPC304839
0.9408	High Similarity	NPC220582
0.9404	High Similarity	NPC260902
0.9404	High Similarity	NPC65504
0.9404	High Similarity	NPC296957
0.94	High Similarity	NPC99199
0.9396	High Similarity	NPC253872
0.9396	High Similarity	NPC263676
0.9388	High Similarity	NPC272194
0.9346	High Similarity	NPC45124
0.9346	High Similarity	NPC30655
0.9346	High Similarity	NPC74854
0.9342	High Similarity	NPC476350
0.9342	High Similarity	NPC40583
0.9342	High Similarity	NPC476349
0.9333	High Similarity	NPC122365
0.9329	High Similarity	NPC116604
0.9324	High Similarity	NPC266499
0.9324	High Similarity	NPC317492
0.9286	High Similarity	NPC193998
0.9281	High Similarity	NPC115432
0.9281	High Similarity	NPC260296
0.9267	High Similarity	NPC67654
0.9262	High Similarity	NPC13282
0.9257	High Similarity	NPC186397
0.9257	High Similarity	NPC168085
0.9257	High Similarity	NPC37135
0.9231	High Similarity	NPC53640
0.9231	High Similarity	NPC277480
0.9221	High Similarity	NPC304387
0.9216	High Similarity	NPC244750
0.9211	High Similarity	NPC45131
0.9211	High Similarity	NPC137100
0.92	High Similarity	NPC156244
0.9195	High Similarity	NPC223988
0.9184	High Similarity	NPC311741
0.9184	High Similarity	NPC234629
0.9172	High Similarity	NPC50394
0.9172	High Similarity	NPC247973
0.9167	High Similarity	NPC37183
0.9161	High Similarity	NPC84515
0.9161	High Similarity	NPC219861
0.9161	High Similarity	NPC272722
0.9161	High Similarity	NPC312056
0.9139	High Similarity	NPC130015
0.9139	High Similarity	NPC38361
0.9133	High Similarity	NPC472421
0.9128	High Similarity	NPC39195
0.9122	High Similarity	NPC187282
0.9122	High Similarity	NPC24136
0.9122	High Similarity	NPC290133
0.9116	High Similarity	NPC17262
0.9116	High Similarity	NPC166138
0.9116	High Similarity	NPC18585
0.9116	High Similarity	NPC106985
0.911	High Similarity	NPC110969
0.9103	High Similarity	NPC477956
0.9103	High Similarity	NPC155640
0.9103	High Similarity	NPC472581
0.9103	High Similarity	NPC159508
0.9097	High Similarity	NPC188486
0.9097	High Similarity	NPC472419
0.9091	High Similarity	NPC472877
0.9091	High Similarity	NPC196879
0.9091	High Similarity	NPC16935
0.9073	High Similarity	NPC474772
0.9073	High Similarity	NPC472423
0.9073	High Similarity	NPC474744
0.9073	High Similarity	NPC318424
0.9067	High Similarity	NPC65775
0.9067	High Similarity	NPC10027
0.906	High Similarity	NPC198427
0.906	High Similarity	NPC308200
0.9057	High Similarity	NPC131866
0.9054	High Similarity	NPC273538
0.9054	High Similarity	NPC216538
0.9051	High Similarity	NPC253730
0.9051	High Similarity	NPC286230
0.9048	High Similarity	NPC144499
0.9048	High Similarity	NPC226942
0.9048	High Similarity	NPC96791
0.9048	High Similarity	NPC11561
0.9048	High Similarity	NPC470636
0.9048	High Similarity	NPC226636
0.9045	High Similarity	NPC38914
0.9045	High Similarity	NPC36320
0.9045	High Similarity	NPC169471
0.9041	High Similarity	NPC69769
0.9041	High Similarity	NPC172986
0.9041	High Similarity	NPC241100
0.9041	High Similarity	NPC270883
0.9041	High Similarity	NPC159275
0.9041	High Similarity	NPC261227
0.9041	High Similarity	NPC28337
0.9034	High Similarity	NPC124269
0.9034	High Similarity	NPC21350
0.9028	High Similarity	NPC477243
0.9028	High Similarity	NPC249606
0.9028	High Similarity	NPC1486
0.9028	High Similarity	NPC472364
0.9028	High Similarity	NPC274109
0.9028	High Similarity	NPC473391
0.9028	High Similarity	NPC477244
0.9028	High Similarity	NPC66349
0.9028	High Similarity	NPC150399
0.9028	High Similarity	NPC98115
0.9028	High Similarity	NPC168105
0.9028	High Similarity	NPC12165
0.9028	High Similarity	NPC41461
0.9028	High Similarity	NPC477242
0.9028	High Similarity	NPC25287
0.9028	High Similarity	NPC186838
0.9026	High Similarity	NPC269495
0.9026	High Similarity	NPC196448
0.902	High Similarity	NPC233776
0.9013	High Similarity	NPC473996
0.9013	High Similarity	NPC31627
0.9013	High Similarity	NPC476238
0.9013	High Similarity	NPC125300
0.9013	High Similarity	NPC327269
0.9007	High Similarity	NPC101957
0.9007	High Similarity	NPC37348
0.9007	High Similarity	NPC120105
0.9007	High Similarity	NPC148423
0.9007	High Similarity	NPC227122
0.9007	High Similarity	NPC135303
0.9007	High Similarity	NPC321896
0.9007	High Similarity	NPC476185
0.9007	High Similarity	NPC472406
0.9007	High Similarity	NPC472633
0.9	High Similarity	NPC145467
0.9	High Similarity	NPC266572
0.8994	High Similarity	NPC211309
0.8993	High Similarity	NPC124729
0.8993	High Similarity	NPC130176
0.8993	High Similarity	NPC196114
0.8993	High Similarity	NPC99454
0.8993	High Similarity	NPC477955
0.8993	High Similarity	NPC472629
0.8993	High Similarity	NPC178343
0.8993	High Similarity	NPC299011
0.8993	High Similarity	NPC306488
0.8993	High Similarity	NPC5820
0.8987	High Similarity	NPC323137
0.8986	High Similarity	NPC190637
0.8986	High Similarity	NPC257097
0.8986	High Similarity	NPC143896
0.8986	High Similarity	NPC310130
0.8986	High Similarity	NPC24821
0.8986	High Similarity	NPC149026
0.8986	High Similarity	NPC91560

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 NPC170169 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	360
0.1-0.2	962
0.2-0.3	1506
0.3-0.4	2648
0.4-0.5	1873
0.5-0.6	1181
0.6-0.7	425
0.7-0.8	129
0.8-0.85	47
0.85-0.9	19
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9054	High Similarity	NPD4378	Clinical (unspecified phase)
0.8831	High Similarity	NPD2393	Clinical (unspecified phase)
0.88	High Similarity	NPD7410	Clinical (unspecified phase)
0.8718	High Similarity	NPD3882	Suspended
0.8707	High Similarity	NPD2344	Approved
0.8684	High Similarity	NPD920	Approved
0.8681	High Similarity	NPD1240	Approved
0.8662	High Similarity	NPD3749	Approved
0.8649	High Similarity	NPD1549	Phase 2
0.8598	High Similarity	NPD6559	Discontinued
0.8591	High Similarity	NPD2800	Approved
0.8591	High Similarity	NPD1243	Approved
0.859	High Similarity	NPD2801	Approved
0.859	High Similarity	NPD7819	Suspended
0.8581	High Similarity	NPD1550	Clinical (unspecified phase)
0.8581	High Similarity	NPD7411	Suspended
0.8581	High Similarity	NPD1552	Clinical (unspecified phase)
0.8571	High Similarity	NPD1510	Phase 2
0.8562	High Similarity	NPD1607	Approved
0.8553	High Similarity	NPD642	Clinical (unspecified phase)
0.8535	High Similarity	NPD8443	Clinical (unspecified phase)
0.8526	High Similarity	NPD1934	Approved
0.8516	High Similarity	NPD4380	Phase 2
0.8514	High Similarity	NPD2796	Approved
0.85	High Similarity	NPD6959	Discontinued
0.8487	Intermediate Similarity	NPD1511	Approved
0.8477	Intermediate Similarity	NPD2309	Approved
0.8438	Intermediate Similarity	NPD5494	Approved
0.8431	Intermediate Similarity	NPD2532	Approved
0.8431	Intermediate Similarity	NPD2533	Approved
0.8431	Intermediate Similarity	NPD2534	Approved
0.8428	Intermediate Similarity	NPD7075	Discontinued
0.8421	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.8395	Intermediate Similarity	NPD3926	Phase 2
0.8389	Intermediate Similarity	NPD2935	Discontinued
0.8385	Intermediate Similarity	NPD1247	Approved
0.8377	Intermediate Similarity	NPD1512	Approved
0.8365	Intermediate Similarity	NPD7768	Phase 2
0.8354	Intermediate Similarity	NPD3818	Discontinued
0.8354	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8344	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD6232	Discontinued
0.8293	Intermediate Similarity	NPD7473	Discontinued
0.8261	Intermediate Similarity	NPD919	Approved
0.8247	Intermediate Similarity	NPD6799	Approved
0.8232	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8232	Intermediate Similarity	NPD6166	Phase 2
0.8232	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8224	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8199	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8176	Intermediate Similarity	NPD6801	Discontinued
0.8158	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8137	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8079	Intermediate Similarity	NPD2799	Discontinued
0.8075	Intermediate Similarity	NPD3817	Phase 2
0.8052	Intermediate Similarity	NPD3750	Approved
0.805	Intermediate Similarity	NPD6599	Discontinued
0.8026	Intermediate Similarity	NPD1551	Phase 2
0.7988	Intermediate Similarity	NPD5953	Discontinued
0.7987	Intermediate Similarity	NPD3226	Approved
0.7976	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7976	Intermediate Similarity	NPD5844	Phase 1
0.7976	Intermediate Similarity	NPD7286	Phase 2
0.7974	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7961	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7947	Intermediate Similarity	NPD6651	Approved
0.7933	Intermediate Similarity	NPD943	Approved
0.7929	Intermediate Similarity	NPD7074	Phase 3
0.7919	Intermediate Similarity	NPD2313	Discontinued
0.7919	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7898	Intermediate Similarity	NPD7390	Discontinued
0.7895	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.787	Intermediate Similarity	NPD7054	Approved
0.7857	Intermediate Similarity	NPD2346	Discontinued
0.7853	Intermediate Similarity	NPD2296	Approved
0.7853	Intermediate Similarity	NPD5402	Approved
0.7824	Intermediate Similarity	NPD7472	Approved
0.7821	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7784	Intermediate Similarity	NPD5711	Approved
0.7784	Intermediate Similarity	NPD7229	Phase 3
0.7784	Intermediate Similarity	NPD5710	Approved
0.7778	Intermediate Similarity	NPD6797	Phase 2
0.775	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7742	Intermediate Similarity	NPD1471	Phase 3
0.7733	Intermediate Similarity	NPD7251	Discontinued
0.7727	Intermediate Similarity	NPD3748	Approved
0.7706	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7703	Intermediate Similarity	NPD1203	Approved
0.7688	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7688	Intermediate Similarity	NPD7808	Phase 3
0.7683	Intermediate Similarity	NPD1465	Phase 2
0.7682	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7677	Intermediate Similarity	NPD6100	Approved
0.7677	Intermediate Similarity	NPD6099	Approved
0.7674	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.764	Intermediate Similarity	NPD5403	Approved
0.7627	Intermediate Similarity	NPD4287	Approved
0.7622	Intermediate Similarity	NPD6279	Approved
0.7622	Intermediate Similarity	NPD6280	Approved
0.7616	Intermediate Similarity	NPD1729	Discontinued
0.7595	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7595	Intermediate Similarity	NPD4628	Phase 3
0.755	Intermediate Similarity	NPD4908	Phase 1
0.755	Intermediate Similarity	NPD6832	Phase 2
0.7532	Intermediate Similarity	NPD230	Phase 1
0.7532	Intermediate Similarity	NPD2654	Approved
0.7532	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD447	Suspended
0.7516	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD5401	Approved
0.75	Intermediate Similarity	NPD9717	Approved
0.75	Intermediate Similarity	NPD4625	Phase 3
0.7471	Intermediate Similarity	NPD6808	Phase 2
0.747	Intermediate Similarity	NPD5760	Phase 2
0.747	Intermediate Similarity	NPD5761	Phase 2
0.7453	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7452	Intermediate Similarity	NPD5408	Approved
0.7452	Intermediate Similarity	NPD5406	Approved
0.7452	Intermediate Similarity	NPD5404	Approved
0.7452	Intermediate Similarity	NPD5405	Approved
0.7451	Intermediate Similarity	NPD3764	Approved
0.7439	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7432	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7418	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7418	Intermediate Similarity	NPD4361	Phase 2
0.7417	Intermediate Similarity	NPD2798	Approved
0.7416	Intermediate Similarity	NPD8434	Phase 2
0.7389	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD7033	Discontinued
0.7383	Intermediate Similarity	NPD1608	Approved
0.7363	Intermediate Similarity	NPD4363	Phase 3
0.7363	Intermediate Similarity	NPD4360	Phase 2
0.7351	Intermediate Similarity	NPD1470	Approved
0.7351	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7349	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7348	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7345	Intermediate Similarity	NPD8313	Approved
0.7345	Intermediate Similarity	NPD8312	Approved
0.7338	Intermediate Similarity	NPD3268	Approved
0.7338	Intermediate Similarity	NPD411	Approved
0.7333	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.733	Intermediate Similarity	NPD3658	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7315	Intermediate Similarity	NPD422	Phase 1
0.7315	Intermediate Similarity	NPD1610	Phase 2
0.731	Intermediate Similarity	NPD7199	Phase 2
0.7299	Intermediate Similarity	NPD3751	Discontinued
0.7283	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD2403	Approved
0.7279	Intermediate Similarity	NPD1548	Phase 1
0.7278	Intermediate Similarity	NPD4308	Phase 3
0.7267	Intermediate Similarity	NPD7003	Approved
0.7267	Intermediate Similarity	NPD3972	Approved
0.7255	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD1613	Approved
0.7237	Intermediate Similarity	NPD1164	Approved
0.7237	Intermediate Similarity	NPD2797	Approved
0.7235	Intermediate Similarity	NPD6971	Discontinued
0.7225	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD6844	Discontinued
0.7202	Intermediate Similarity	NPD37	Approved
0.72	Intermediate Similarity	NPD1201	Approved
0.72	Intermediate Similarity	NPD7177	Discontinued
0.7193	Intermediate Similarity	NPD6234	Discontinued
0.7184	Intermediate Similarity	NPD4575	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD17	Approved
0.7176	Intermediate Similarity	NPD4967	Phase 2
0.7176	Intermediate Similarity	NPD4965	Approved
0.7176	Intermediate Similarity	NPD4966	Approved
0.7168	Intermediate Similarity	NPD3787	Discontinued
0.7162	Intermediate Similarity	NPD9545	Approved
0.7161	Intermediate Similarity	NPD3027	Phase 3
0.7143	Intermediate Similarity	NPD2424	Discontinued
0.7143	Intermediate Similarity	NPD2861	Phase 2
0.7143	Intermediate Similarity	NPD9493	Approved
0.7135	Intermediate Similarity	NPD8151	Discontinued
0.7126	Intermediate Similarity	NPD7458	Discontinued
0.7118	Intermediate Similarity	NPD4288	Approved
0.7114	Intermediate Similarity	NPD1651	Approved
0.7105	Intermediate Similarity	NPD4749	Approved
0.7091	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD1933	Approved
0.7089	Intermediate Similarity	NPD5124	Phase 1
0.7081	Intermediate Similarity	NPD6002	Phase 3
0.7081	Intermediate Similarity	NPD6005	Phase 3
0.7081	Intermediate Similarity	NPD6004	Phase 3
0.7081	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7079	Intermediate Similarity	NPD1252	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD1019	Discontinued
0.7074	Intermediate Similarity	NPD6777	Approved
0.7074	Intermediate Similarity	NPD6782	Approved
0.7074	Intermediate Similarity	NPD6776	Approved
0.7074	Intermediate Similarity	NPD6779	Approved
0.7074	Intermediate Similarity	NPD6778	Approved
0.7074	Intermediate Similarity	NPD6781	Approved
0.7074	Intermediate Similarity	NPD6780	Approved
0.7072	Intermediate Similarity	NPD8055	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