NPASS Compound

Structure

CID142308 OpenBabel06191715502D 33 35 0 0 0 0 0 0 0 0999 V2000 2.4122 -9.4693 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9122 -10.3353 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4122 -6.0052 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0878 -5.1391 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4122 -7.7372 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0878 -5.1391 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9122 -8.6032 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9122 -6.8712 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9122 -5.1391 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5878 -4.2731 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0878 -3.4071 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 2.6831 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5878 -2.5411 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 -2.0878 0.0570 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 1.8171 0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4122 -9.4693 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4122 -6.0052 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5878 -4.2731 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 2.6831 -0.3090 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 -2.0878 -1.6750 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 0.9511 -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 3.5491 0.1910 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 -3.5878 -2.5411 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 20 1 0 0 0 0 4 21 1 0 0 0 0 5 7 1 0 0 0 0 5 8 1 0 0 0 0 6 9 1 0 0 0 0 6 10 1 0 0 0 0 7 19 2 0 0 0 0 8 20 1 0 0 0 0 9 20 2 0 0 0 0 10 21 1 0 0 0 0 11 14 1 0 0 0 0 11 21 2 0 0 0 0 12 13 2 0 0 0 0 12 22 1 0 0 0 0 13 23 1 0 0 0 0 14 25 1 0 0 0 0 15 22 1 0 0 0 0 15 29 2 0 0 0 0 16 24 2 0 0 0 0 16 26 1 0 0 0 0 17 24 1 0 0 0 0 17 27 2 0 0 0 0 18 23 2 0 0 0 0 18 28 1 0 0 0 0 22 28 2 0 0 0 0 23 30 1 0 0 0 0 24 31 1 0 0 0 0 25 26 2 0 0 0 0 25 27 1 0 0 0 0 26 29 1 0 0 0 0 27 32 1 0 0 0 0 28 33 1 0 0 0 0 29 33 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	446.25
Volume:	493.267
LogP:	6.883
LogD:	4.691
LogS:	-2.65
# Rotatable Bonds:	9
TPSA:	73.83
# H-Bond Aceptor:	4
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.29
Synthetic Accessibility Score:	3.13
Fsp3:	0.31
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:	-4.936
MDCK Permeability:	1.8539820302976295e-05
Pgp-inhibitor:	0.594
Pgp-substrate:	0.707
Human Intestinal Absorption (HIA):	0.023
20% Bioavailability (F20%):	1.0
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.014
Plasma Protein Binding (PPB):	101.0121841430664%
Volume Distribution (VD):	2.906
Pgp-substrate:	0.316888689994812%

ADMET: Metabolism

CYP1A2-inhibitor:	0.959
CYP1A2-substrate:	0.452
CYP2C19-inhibitor:	0.94
CYP2C19-substrate:	0.062
CYP2C9-inhibitor:	0.614
CYP2C9-substrate:	0.984
CYP2D6-inhibitor:	0.983
CYP2D6-substrate:	0.943
CYP3A4-inhibitor:	0.673
CYP3A4-substrate:	0.119

ADMET: Excretion

Clearance (CL):	8.907
Half-life (T1/2):	0.757

ADMET: Toxicity

hERG Blockers:	0.408
Human Hepatotoxicity (H-HT):	0.801
Drug-inuced Liver Injury (DILI):	0.071
AMES Toxicity:	0.008
Rat Oral Acute Toxicity:	0.046
Maximum Recommended Daily Dose:	0.891
Skin Sensitization:	0.95
Carcinogencity:	0.036
Eye Corrosion:	0.003
Eye Irritation:	0.666
Respiratory Toxicity:	0.076

Download Data

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

Natural Product: NPC142308

Natural Product ID:	NPC142308
*Common Name:**	Mulberrofuran W
IUPAC Name:	5-(6-hydroxy-1-benzofuran-2-yl)-4-[(2Z,6Z)-3,7,11-trimethyldodeca-2,6,10-trienyl]benzene-1,3-diol
Synonyms:	Mulberrofuran W
Standard InCHIKey:	YUFBSQFJPYHMTK-QUYCRGELSA-N
Standard InCHI:	InChI=1S/C29H34O4/c1-19(2)7-5-8-20(3)9-6-10-21(4)11-14-25-26(16-24(31)17-27(25)32)29-15-22-12-13-23(30)18-28(22)33-29/h7,9,11-13,15-18,30-32H,5-6,8,10,14H2,1-4H3/b20-9-,21-11-
SMILES:	CC(=CCC/C(=CCC/C(=CCc1c(cc(cc1O)O)c1cc2ccc(cc2o1)O)/C)/C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL562810
PubChem CID:	45273151
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]
NPO2578	Morus sp.	Species	Sulidae	Eukaryota	n.a.	n.a.	n.a.	PMID[19072214]
NPO9402	Morus mongolica	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9402	Morus mongolica	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2578	Morus sp.	Species	Sulidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9402	Morus mongolica	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO9402	Morus mongolica	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	5
Others	6

Activity Type	# Activity
Cell Line	1
CELL-LINE	1
Individual Protein	5
NON-MOLECULAR	1
Others	2
PROTEIN FAMILY	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT924	Cell Line	HSC-2	Homo sapiens	CC50	=	70000.0	nM	PMID[489140]
NPT211	Individual Protein	Hypoxia-inducible factor 1 alpha	Homo sapiens	IC50	=	3620.0	nM	PMID[489141]
NPT178	Individual Protein	Protein-tyrosine phosphatase 1B	Homo sapiens	IC50	=	2700.0	nM	PMID[489142]
NPT178	Individual Protein	Protein-tyrosine phosphatase 1B	Homo sapiens	Km	=	3170000.0	nM	PMID[489142]
NPT178	Individual Protein	Protein-tyrosine phosphatase 1B	Homo sapiens	Vmax	=	5.49	microM/min	PMID[489142]
NPT1120	Individual Protein	Pancreatic triacylglycerol lipase	Sus scrofa	IC50	=	700.0	nM	PMID[489143]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	CC50	=	70000.0	nM	PMID[489140]
NPT27	Others	Unspecified		CC50	=	90000.0	nM	PMID[489140]
NPT27	Others	Unspecified		Ratio	=	1.3	n.a.	PMID[489140]
NPT20904	CELL-LINE	Hep 3B2	Homo sapiens	IC50	=	3050.0	nM	PMID[489141]
NPT21802	PROTEIN FAMILY	Hypoxia inducible factors; HIF-1-alpha, HIF-2-alpha	Homo sapiens	IC50	=	6070.0	nM	PMID[489141]

☑ 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 NPC142308 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	421
0.1-0.2	1654
0.2-0.3	4012
0.3-0.4	10570
0.4-0.5	7720
0.5-0.6	3636
0.6-0.7	5496
0.7-0.8	5230
0.8-0.85	2625
0.85-0.9	1226
0.9-0.95	83
0.95-1	24

Similarity Score	Similarity Level	Natural Product ID
0.9931	High Similarity	NPC23668
0.9931	High Similarity	NPC193976
0.9864	High Similarity	NPC297531
0.9864	High Similarity	NPC213936
0.9863	High Similarity	NPC207624
0.9796	High Similarity	NPC235333
0.9795	High Similarity	NPC106372
0.9795	High Similarity	NPC115324
0.9795	High Similarity	NPC58668
0.973	High Similarity	NPC99199
0.973	High Similarity	NPC148938
0.96	High Similarity	NPC212967
0.96	High Similarity	NPC164110
0.96	High Similarity	NPC96342
0.96	High Similarity	NPC268360
0.96	High Similarity	NPC246647
0.9592	High Similarity	NPC230713
0.9592	High Similarity	NPC167576
0.9592	High Similarity	NPC78335
0.9533	High Similarity	NPC180924
0.9527	High Similarity	NPC170169
0.9524	High Similarity	NPC178202
0.9521	High Similarity	NPC17816
0.9517	High Similarity	NPC155144
0.94	High Similarity	NPC72370
0.94	High Similarity	NPC472462
0.9392	High Similarity	NPC226644
0.9392	High Similarity	NPC37226
0.9384	High Similarity	NPC230943
0.9384	High Similarity	NPC98926
0.9338	High Similarity	NPC198490
0.9324	High Similarity	NPC135325
0.932	High Similarity	NPC210826
0.9315	High Similarity	NPC302181
0.9295	High Similarity	NPC53640
0.9276	High Similarity	NPC137100
0.9272	High Similarity	NPC1477
0.9272	High Similarity	NPC183874
0.9272	High Similarity	NPC213608
0.9257	High Similarity	NPC12148
0.9257	High Similarity	NPC130581
0.9247	High Similarity	NPC53192
0.9231	High Similarity	NPC39306
0.9205	High Similarity	NPC67654
0.9205	High Similarity	NPC5871
0.92	High Similarity	NPC13282
0.9189	High Similarity	NPC51641
0.9189	High Similarity	NPC300267
0.9184	High Similarity	NPC225884
0.9178	High Similarity	NPC49108
0.9167	High Similarity	NPC133065
0.915	High Similarity	NPC247677
0.915	High Similarity	NPC160015
0.9139	High Similarity	NPC156244
0.9133	High Similarity	NPC10027
0.9133	High Similarity	NPC39929
0.9133	High Similarity	NPC37208
0.9133	High Similarity	NPC221868
0.9133	High Similarity	NPC296030
0.9133	High Similarity	NPC65775
0.9108	High Similarity	NPC474591
0.9103	High Similarity	NPC312056
0.9103	High Similarity	NPC84515
0.9103	High Similarity	NPC477239
0.9103	High Similarity	NPC3448
0.9091	High Similarity	NPC65504
0.9091	High Similarity	NPC296957
0.9091	High Similarity	NPC260902
0.9073	High Similarity	NPC227122
0.9067	High Similarity	NPC272194
0.9045	High Similarity	NPC159508
0.9038	High Similarity	NPC188486
0.9032	High Similarity	NPC476349
0.9032	High Similarity	NPC244750
0.9032	High Similarity	NPC476350
0.9032	High Similarity	NPC40583
0.9032	High Similarity	NPC472877
0.9026	High Similarity	NPC45131
0.9013	High Similarity	NPC258249
0.9007	High Similarity	NPC223988
0.9	High Similarity	NPC77903
0.9	High Similarity	NPC17101
0.8994	High Similarity	NPC253730
0.8994	High Similarity	NPC286230
0.8993	High Similarity	NPC29577
0.8987	High Similarity	NPC169471
0.8986	High Similarity	NPC310340
0.8981	High Similarity	NPC272722
0.898	High Similarity	NPC275734
0.8974	High Similarity	NPC260296
0.8974	High Similarity	NPC304839
0.8974	High Similarity	NPC220582
0.8974	High Similarity	NPC115432
0.8954	High Similarity	NPC125300
0.8954	High Similarity	NPC253872
0.8954	High Similarity	NPC474843
0.8954	High Similarity	NPC263676
0.8954	High Similarity	NPC41326
0.8947	High Similarity	NPC295036
0.8947	High Similarity	NPC470107
0.894	High Similarity	NPC186397
0.894	High Similarity	NPC37135
0.894	High Similarity	NPC216624
0.8933	High Similarity	NPC237208
0.8933	High Similarity	NPC299011
0.8931	High Similarity	NPC277480
0.8917	High Similarity	NPC45124
0.8917	High Similarity	NPC74854
0.8917	High Similarity	NPC96031
0.8917	High Similarity	NPC30655
0.891	High Similarity	NPC196879
0.891	High Similarity	NPC16935
0.8903	High Similarity	NPC472461
0.8896	High Similarity	NPC178964
0.8896	High Similarity	NPC210942
0.8896	High Similarity	NPC95842
0.8896	High Similarity	NPC169990
0.8896	High Similarity	NPC122365
0.8896	High Similarity	NPC280530
0.8889	High Similarity	NPC116604
0.8882	High Similarity	NPC158338
0.8882	High Similarity	NPC288036
0.8882	High Similarity	NPC97028
0.8882	High Similarity	NPC6923
0.8882	High Similarity	NPC266499
0.8882	High Similarity	NPC317492
0.8882	High Similarity	NPC65589
0.8882	High Similarity	NPC97029
0.8882	High Similarity	NPC100985
0.8875	High Similarity	NPC50394
0.8875	High Similarity	NPC247973
0.8874	High Similarity	NPC259632
0.8874	High Similarity	NPC150215
0.8868	High Similarity	NPC45449
0.8868	High Similarity	NPC291110
0.8868	High Similarity	NPC36320
0.8868	High Similarity	NPC37183
0.8867	High Similarity	NPC134621
0.8867	High Similarity	NPC184649
0.8867	High Similarity	NPC303185
0.8867	High Similarity	NPC311144
0.8861	High Similarity	NPC193998
0.8859	High Similarity	NPC159855
0.8859	High Similarity	NPC96791
0.8859	High Similarity	NPC470636
0.8859	High Similarity	NPC226942
0.8859	High Similarity	NPC169479
0.8844	High Similarity	NPC112757
0.8844	High Similarity	NPC472368
0.8844	High Similarity	NPC124269
0.8836	High Similarity	NPC476333
0.8836	High Similarity	NPC472367
0.8836	High Similarity	NPC473391
0.8836	High Similarity	NPC472364
0.8834	High Similarity	NPC227906
0.8831	High Similarity	NPC40356
0.8831	High Similarity	NPC154683
0.8824	High Similarity	NPC307780
0.8824	High Similarity	NPC309979
0.8824	High Similarity	NPC60413
0.882	High Similarity	NPC247136
0.8816	High Similarity	NPC106328
0.8816	High Similarity	NPC172329
0.8816	High Similarity	NPC145467
0.8816	High Similarity	NPC39195
0.8816	High Similarity	NPC2569
0.8816	High Similarity	NPC27221
0.8816	High Similarity	NPC168085
0.8816	High Similarity	NPC256672
0.8816	High Similarity	NPC35150
0.8816	High Similarity	NPC7025
0.8808	High Similarity	NPC196114
0.8808	High Similarity	NPC99454
0.8808	High Similarity	NPC130176
0.8805	High Similarity	NPC263092
0.8805	High Similarity	NPC155640
0.8805	High Similarity	NPC1755
0.8805	High Similarity	NPC1706
0.8805	High Similarity	NPC59295
0.8805	High Similarity	NPC39305
0.88	High Similarity	NPC113770
0.88	High Similarity	NPC251182
0.88	High Similarity	NPC95123
0.88	High Similarity	NPC66404
0.88	High Similarity	NPC172182
0.88	High Similarity	NPC262935
0.8797	High Similarity	NPC304387
0.8792	High Similarity	NPC250755
0.8792	High Similarity	NPC96692
0.8792	High Similarity	NPC103752
0.8792	High Similarity	NPC18714
0.8792	High Similarity	NPC105648
0.8784	High Similarity	NPC472366
0.8782	High Similarity	NPC13879
0.8782	High Similarity	NPC472907
0.8776	High Similarity	NPC188879
0.8776	High Similarity	NPC228661
0.8776	High Similarity	NPC62735
0.8774	High Similarity	NPC89474
0.8774	High Similarity	NPC303950

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 NPC142308 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	380
0.1-0.2	965
0.2-0.3	1471
0.3-0.4	2675
0.4-0.5	1896
0.5-0.6	1126
0.6-0.7	447
0.7-0.8	126
0.8-0.85	49
0.85-0.9	15
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8968	High Similarity	NPD3749	Approved
0.8776	High Similarity	NPD2344	Approved
0.8654	High Similarity	NPD7819	Suspended
0.8618	High Similarity	NPD4378	Clinical (unspecified phase)
0.8544	High Similarity	NPD3882	Suspended
0.8543	High Similarity	NPD2309	Approved
0.8497	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8493	Intermediate Similarity	NPD1240	Approved
0.8467	Intermediate Similarity	NPD1549	Phase 2
0.8447	Intermediate Similarity	NPD6959	Discontinued
0.8431	Intermediate Similarity	NPD1511	Approved
0.8418	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8418	Intermediate Similarity	NPD2801	Approved
0.8411	Intermediate Similarity	NPD2800	Approved
0.84	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.84	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8389	Intermediate Similarity	NPD1510	Phase 2
0.8378	Intermediate Similarity	NPD1607	Approved
0.8377	Intermediate Similarity	NPD2532	Approved
0.8377	Intermediate Similarity	NPD2533	Approved
0.8377	Intermediate Similarity	NPD2534	Approved
0.8365	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8355	Intermediate Similarity	NPD3750	Approved
0.8354	Intermediate Similarity	NPD7473	Discontinued
0.8354	Intermediate Similarity	NPD1934	Approved
0.8344	Intermediate Similarity	NPD3926	Phase 2
0.8344	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD2796	Approved
0.8323	Intermediate Similarity	NPD1512	Approved
0.8289	Intermediate Similarity	NPD1243	Approved
0.8282	Intermediate Similarity	NPD6232	Discontinued
0.8269	Intermediate Similarity	NPD920	Approved
0.8214	Intermediate Similarity	NPD6559	Discontinued
0.8199	Intermediate Similarity	NPD7768	Phase 2
0.8193	Intermediate Similarity	NPD3818	Discontinued
0.8176	Intermediate Similarity	NPD7411	Suspended
0.816	Intermediate Similarity	NPD5494	Approved
0.8148	Intermediate Similarity	NPD7075	Discontinued
0.8141	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.8113	Intermediate Similarity	NPD4380	Phase 2
0.8077	Intermediate Similarity	NPD6799	Approved
0.8075	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8072	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8072	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8072	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8072	Intermediate Similarity	NPD6166	Phase 2
0.805	Intermediate Similarity	NPD3226	Approved
0.8037	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8026	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.8026	Intermediate Similarity	NPD3748	Approved
0.8013	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD6599	Discontinued
0.8	Intermediate Similarity	NPD1247	Approved
0.7975	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7974	Intermediate Similarity	NPD2935	Discontinued
0.7974	Intermediate Similarity	NPD6100	Approved
0.7974	Intermediate Similarity	NPD6099	Approved
0.7963	Intermediate Similarity	NPD1465	Phase 2
0.7962	Intermediate Similarity	NPD7390	Discontinued
0.7929	Intermediate Similarity	NPD5844	Phase 1
0.7922	Intermediate Similarity	NPD1471	Phase 3
0.7922	Intermediate Similarity	NPD2346	Discontinued
0.7914	Intermediate Similarity	NPD3817	Phase 2
0.7914	Intermediate Similarity	NPD2296	Approved
0.7908	Intermediate Similarity	NPD2799	Discontinued
0.7886	Intermediate Similarity	NPD4287	Approved
0.7882	Intermediate Similarity	NPD7074	Phase 3
0.7881	Intermediate Similarity	NPD943	Approved
0.7879	Intermediate Similarity	NPD919	Approved
0.7867	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD1551	Phase 2
0.7844	Intermediate Similarity	NPD7229	Phase 3
0.7824	Intermediate Similarity	NPD7054	Approved
0.7821	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7791	Intermediate Similarity	NPD6801	Discontinued
0.7778	Intermediate Similarity	NPD7472	Approved
0.7748	Intermediate Similarity	NPD3764	Approved
0.7738	Intermediate Similarity	NPD5711	Approved
0.7738	Intermediate Similarity	NPD5710	Approved
0.7719	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7719	Intermediate Similarity	NPD7286	Phase 2
0.7697	Intermediate Similarity	NPD5402	Approved
0.7692	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7688	Intermediate Similarity	NPD7251	Discontinued
0.7677	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7662	Intermediate Similarity	NPD6651	Approved
0.7658	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7658	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7651	Intermediate Similarity	NPD1203	Approved
0.7644	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7644	Intermediate Similarity	NPD7808	Phase 3
0.7632	Intermediate Similarity	NPD2313	Discontinued
0.763	Intermediate Similarity	NPD6797	Phase 2
0.763	Intermediate Similarity	NPD5953	Discontinued
0.7593	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7576	Intermediate Similarity	NPD6280	Approved
0.7576	Intermediate Similarity	NPD6279	Approved
0.7566	Intermediate Similarity	NPD4625	Phase 3
0.7558	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7547	Intermediate Similarity	NPD4628	Phase 3
0.7543	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7533	Intermediate Similarity	NPD1470	Approved
0.753	Intermediate Similarity	NPD5761	Phase 2
0.753	Intermediate Similarity	NPD5760	Phase 2
0.7529	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD5406	Approved
0.7516	Intermediate Similarity	NPD5408	Approved
0.7516	Intermediate Similarity	NPD5404	Approved
0.7516	Intermediate Similarity	NPD5405	Approved
0.75	Intermediate Similarity	NPD6832	Phase 2
0.75	Intermediate Similarity	NPD4908	Phase 1
0.7486	Intermediate Similarity	NPD3658	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD5403	Approved
0.7484	Intermediate Similarity	NPD447	Suspended
0.7483	Intermediate Similarity	NPD2798	Approved
0.7472	Intermediate Similarity	NPD8434	Phase 2
0.7471	Intermediate Similarity	NPD7199	Phase 2
0.7469	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7457	Intermediate Similarity	NPD3751	Discontinued
0.745	Intermediate Similarity	NPD9717	Approved
0.745	Intermediate Similarity	NPD1608	Approved
0.7427	Intermediate Similarity	NPD6808	Phase 2
0.7405	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7403	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7403	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7403	Intermediate Similarity	NPD3268	Approved
0.7401	Intermediate Similarity	NPD8313	Approved
0.7401	Intermediate Similarity	NPD8312	Approved
0.7394	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7384	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7383	Intermediate Similarity	NPD1201	Approved
0.7381	Intermediate Similarity	NPD4288	Approved
0.7375	Intermediate Similarity	NPD2654	Approved
0.7372	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7372	Intermediate Similarity	NPD230	Phase 1
0.7362	Intermediate Similarity	NPD5401	Approved
0.7326	Intermediate Similarity	NPD3787	Discontinued
0.7303	Intermediate Similarity	NPD2797	Approved
0.7301	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD411	Approved
0.7273	Intermediate Similarity	NPD1729	Discontinued
0.7273	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD1610	Phase 2
0.7267	Intermediate Similarity	NPD422	Phase 1
0.7262	Intermediate Similarity	NPD37	Approved
0.7251	Intermediate Similarity	NPD6234	Discontinued
0.7248	Intermediate Similarity	NPD17	Approved
0.7241	Intermediate Similarity	NPD2403	Approved
0.7237	Intermediate Similarity	NPD1876	Approved
0.7235	Intermediate Similarity	NPD4967	Phase 2
0.7235	Intermediate Similarity	NPD4965	Approved
0.7235	Intermediate Similarity	NPD4966	Approved
0.7233	Intermediate Similarity	NPD7033	Discontinued
0.7233	Intermediate Similarity	NPD4308	Phase 3
0.7222	Intermediate Similarity	NPD7003	Approved
0.7219	Intermediate Similarity	NPD3972	Approved
0.7211	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7189	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7189	Intermediate Similarity	NPD4361	Phase 2
0.7188	Intermediate Similarity	NPD8151	Discontinued
0.7171	Intermediate Similarity	NPD4749	Approved
0.716	Intermediate Similarity	NPD6844	Discontinued
0.7159	Intermediate Similarity	NPD7177	Discontinued
0.7143	Intermediate Similarity	NPD4575	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD4360	Phase 2
0.7135	Intermediate Similarity	NPD4363	Phase 3
0.7127	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.712	Intermediate Similarity	NPD3269	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD1548	Phase 1
0.7108	Intermediate Similarity	NPD6273	Approved
0.7101	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD2861	Phase 2
0.7093	Intermediate Similarity	NPD6971	Discontinued
0.7089	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD1613	Approved
0.7078	Intermediate Similarity	NPD3267	Approved
0.7078	Intermediate Similarity	NPD1164	Approved
0.7078	Intermediate Similarity	NPD3266	Approved
0.7076	Intermediate Similarity	NPD5616	Clinical (unspecified phase)
0.7068	Intermediate Similarity	NPD7870	Phase 2
0.7068	Intermediate Similarity	NPD7871	Phase 2
0.7067	Intermediate Similarity	NPD1651	Approved
0.7062	Intermediate Similarity	NPD7228	Approved
0.7059	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD6355	Discontinued
0.7039	Intermediate Similarity	NPD1252	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD6780	Approved
0.7037	Intermediate Similarity	NPD6777	Approved
0.7037	Intermediate Similarity	NPD6779	Approved
0.7037	Intermediate Similarity	NPD6781	Approved
0.7037	Intermediate Similarity	NPD6778	Approved
0.7037	Intermediate Similarity	NPD6782	Approved
0.7037	Intermediate Similarity	NPD6776	Approved
0.7026	Intermediate Similarity	NPD7783	Phase 2
0.7026	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7016	Intermediate Similarity	NPD7697	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