NPASS Compound

Structure

CID297531 OpenBabel06191716102D 33 35 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 -0.5878 -4.2731 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 1.8171 3.1910 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 -2.0878 -3.4071 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 -1.5878 -2.5411 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 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 2.6831 5.6910 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 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 -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 1.8171 0.1910 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 2.6831 -0.3090 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 -0.5878 -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 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 -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 18 1 0 0 0 0 2 18 1 0 0 0 0 3 19 1 0 0 0 0 4 19 1 0 0 0 0 5 20 1 0 0 0 0 6 7 1 0 0 0 0 6 8 1 0 0 0 0 7 18 2 0 0 0 0 8 20 1 0 0 0 0 9 12 1 0 0 0 0 9 19 2 0 0 0 0 10 13 1 0 0 0 0 10 20 2 0 0 0 0 11 14 2 0 0 0 0 11 21 1 0 0 0 0 12 23 1 0 0 0 0 13 24 1 0 0 0 0 14 26 1 0 0 0 0 15 21 1 0 0 0 0 15 28 2 0 0 0 0 16 22 2 0 0 0 0 16 25 1 0 0 0 0 17 22 1 0 0 0 0 17 27 2 0 0 0 0 21 29 2 0 0 0 0 22 30 1 0 0 0 0 23 25 2 0 0 0 0 23 27 1 0 0 0 0 24 26 2 0 0 0 0 24 29 1 0 0 0 0 25 28 1 0 0 0 0 26 31 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:	7.986
LogD:	5.106
LogS:	-2.398
# Rotatable Bonds:	8
TPSA:	73.83
# H-Bond Aceptor:	4
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.307
Synthetic Accessibility Score:	3.235
Fsp3:	0.31
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.022
MDCK Permeability:	1.912598600029014e-05
Pgp-inhibitor:	0.731
Pgp-substrate:	0.544
Human Intestinal Absorption (HIA):	0.015
20% Bioavailability (F20%):	0.996
30% Bioavailability (F30%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.005
Plasma Protein Binding (PPB):	97.63915252685547%
Volume Distribution (VD):	3.198
Pgp-substrate:	2.8777246475219727%

ADMET: Metabolism

CYP1A2-inhibitor:	0.928
CYP1A2-substrate:	0.179
CYP2C19-inhibitor:	0.945
CYP2C19-substrate:	0.059
CYP2C9-inhibitor:	0.702
CYP2C9-substrate:	0.974
CYP2D6-inhibitor:	0.914
CYP2D6-substrate:	0.846
CYP3A4-inhibitor:	0.358
CYP3A4-substrate:	0.087

ADMET: Excretion

Clearance (CL):	9.348
Half-life (T1/2):	0.19

ADMET: Toxicity

hERG Blockers:	0.098
Human Hepatotoxicity (H-HT):	0.953
Drug-inuced Liver Injury (DILI):	0.271
AMES Toxicity:	0.011
Rat Oral Acute Toxicity:	0.054
Maximum Recommended Daily Dose:	0.889
Skin Sensitization:	0.903
Carcinogencity:	0.041
Eye Corrosion:	0.003
Eye Irritation:	0.346
Respiratory Toxicity:	0.871

Download Data

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

Natural Product: NPC297531

Natural Product ID:	NPC297531
*Common Name:**	Mulberrofuran D
IUPAC Name:	5-[7-[(2E)-3,7-dimethylocta-2,6-dienyl]-6-hydroxy-1-benzofuran-2-yl]-4-(3-methylbut-2-enyl)benzene-1,3-diol
Synonyms:	Mulberrofuran D
Standard InCHIKey:	WCJPAQJEARHLGS-KEBDBYFISA-N
Standard InCHI:	InChI=1S/C29H34O4/c1-18(2)7-6-8-20(5)10-13-24-26(31)14-11-21-15-28(33-29(21)24)25-16-22(30)17-27(32)23(25)12-9-19(3)4/h7,9-11,14-17,30-32H,6,8,12-13H2,1-5H3/b20-10+
SMILES:	C/C(=CCc1c(O)ccc2c1oc(c2)c1cc(O)cc(c1CC=C(C)C)O)/CCC=C(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL517247
PubChem CID:	5467256
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	=	83000.0	nM	PMID[514002]
NPT211	Individual Protein	Hypoxia-inducible factor 1 alpha	Homo sapiens	IC50	=	4050.0	nM	PMID[514003]
NPT178	Individual Protein	Protein-tyrosine phosphatase 1B	Homo sapiens	Km	=	2080000.0	nM	PMID[514004]
NPT178	Individual Protein	Protein-tyrosine phosphatase 1B	Homo sapiens	IC50	=	4300.0	nM	PMID[514004]
NPT178	Individual Protein	Protein-tyrosine phosphatase 1B	Homo sapiens	Vmax	=	5.78	microM/min	PMID[514004]
NPT1120	Individual Protein	Pancreatic triacylglycerol lipase	Sus scrofa	IC50	=	90.0	nM	PMID[514005]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	CC50	=	74000.0	nM	PMID[514002]
NPT27	Others	Unspecified		CC50	=	81000.0	nM	PMID[514002]
NPT27	Others	Unspecified		Ratio	=	1.0	n.a.	PMID[514002]
NPT20904	CELL-LINE	Hep 3B2	Homo sapiens	IC50	=	2170.0	nM	PMID[514003]
NPT21802	PROTEIN FAMILY	Hypoxia inducible factors; HIF-1-alpha, HIF-2-alpha	Homo sapiens	IC50	=	8760.0	nM	PMID[514003]

☑ 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 NPC297531 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	426
0.1-0.2	1706
0.2-0.3	3956
0.3-0.4	10634
0.4-0.5	7726
0.5-0.6	3655
0.6-0.7	5510
0.7-0.8	5021
0.8-0.85	2578
0.85-0.9	1345
0.9-0.95	113
0.95-1	27

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC213936
0.9932	High Similarity	NPC235333
0.9865	High Similarity	NPC148938
0.9864	High Similarity	NPC142308
0.9796	High Similarity	NPC23668
0.9796	High Similarity	NPC193976
0.9733	High Similarity	NPC164110
0.9733	High Similarity	NPC246647
0.9733	High Similarity	NPC96342
0.9733	High Similarity	NPC268360
0.9733	High Similarity	NPC212967
0.973	High Similarity	NPC207624
0.9728	High Similarity	NPC78335
0.9728	High Similarity	NPC230713
0.9667	High Similarity	NPC180924
0.9662	High Similarity	NPC106372
0.9662	High Similarity	NPC115324
0.9662	High Similarity	NPC170169
0.9662	High Similarity	NPC58668
0.966	High Similarity	NPC178202
0.96	High Similarity	NPC99199
0.9533	High Similarity	NPC472462
0.9527	High Similarity	NPC226644
0.9527	High Similarity	NPC37226
0.947	High Similarity	NPC198490
0.9463	High Similarity	NPC167576
0.9459	High Similarity	NPC135325
0.9456	High Similarity	NPC210826
0.9423	High Similarity	NPC53640
0.9404	High Similarity	NPC213608
0.9404	High Similarity	NPC183874
0.9404	High Similarity	NPC1477
0.9392	High Similarity	NPC12148
0.9392	High Similarity	NPC17816
0.9392	High Similarity	NPC130581
0.9388	High Similarity	NPC155144
0.9338	High Similarity	NPC5871
0.9333	High Similarity	NPC13282
0.9324	High Similarity	NPC51641
0.9324	High Similarity	NPC300267
0.932	High Similarity	NPC225884
0.9281	High Similarity	NPC160015
0.9281	High Similarity	NPC247677
0.9276	High Similarity	NPC72370
0.9267	High Similarity	NPC221868
0.9267	High Similarity	NPC39929
0.9267	High Similarity	NPC65775
0.9267	High Similarity	NPC37208
0.9267	High Similarity	NPC296030
0.9267	High Similarity	NPC10027
0.9257	High Similarity	NPC98926
0.9257	High Similarity	NPC230943
0.9221	High Similarity	NPC260902
0.9221	High Similarity	NPC296957
0.9221	High Similarity	NPC65504
0.9205	High Similarity	NPC227122
0.92	High Similarity	NPC272194
0.9189	High Similarity	NPC302181
0.9161	High Similarity	NPC40583
0.9161	High Similarity	NPC476350
0.9161	High Similarity	NPC244750
0.9161	High Similarity	NPC476349
0.9156	High Similarity	NPC137100
0.9145	High Similarity	NPC258249
0.9139	High Similarity	NPC223988
0.9122	High Similarity	NPC53192
0.9119	High Similarity	NPC253730
0.9119	High Similarity	NPC286230
0.9114	High Similarity	NPC39306
0.9103	High Similarity	NPC304839
0.9103	High Similarity	NPC220582
0.9103	High Similarity	NPC260296
0.9103	High Similarity	NPC115432
0.9085	High Similarity	NPC253872
0.9085	High Similarity	NPC263676
0.9085	High Similarity	NPC67654
0.9073	High Similarity	NPC37135
0.9073	High Similarity	NPC186397
0.9057	High Similarity	NPC277480
0.9054	High Similarity	NPC49108
0.9051	High Similarity	NPC159508
0.9051	High Similarity	NPC133065
0.9045	High Similarity	NPC30655
0.9045	High Similarity	NPC45124
0.9045	High Similarity	NPC74854
0.9026	High Similarity	NPC178964
0.9026	High Similarity	NPC122365
0.9026	High Similarity	NPC210942
0.9026	High Similarity	NPC95842
0.9026	High Similarity	NPC280530
0.9026	High Similarity	NPC169990
0.902	High Similarity	NPC116604
0.902	High Similarity	NPC156244
0.9013	High Similarity	NPC266499
0.9013	High Similarity	NPC158338
0.9013	High Similarity	NPC65589
0.9013	High Similarity	NPC288036
0.9013	High Similarity	NPC97029
0.9013	High Similarity	NPC317492
0.9013	High Similarity	NPC97028
0.9013	High Similarity	NPC100985
0.9	High Similarity	NPC247973
0.9	High Similarity	NPC50394
0.8994	High Similarity	NPC169471
0.8994	High Similarity	NPC37183
0.8994	High Similarity	NPC474591
0.8993	High Similarity	NPC226942
0.8993	High Similarity	NPC470636
0.8993	High Similarity	NPC96791
0.8987	High Similarity	NPC3448
0.8987	High Similarity	NPC84515
0.8987	High Similarity	NPC193998
0.8987	High Similarity	NPC312056
0.8987	High Similarity	NPC477239
0.8961	High Similarity	NPC40356
0.8961	High Similarity	NPC154683
0.8957	High Similarity	NPC227906
0.8947	High Similarity	NPC7025
0.8947	High Similarity	NPC145467
0.8947	High Similarity	NPC168085
0.8947	High Similarity	NPC256672
0.8947	High Similarity	NPC27221
0.8947	High Similarity	NPC39195
0.8933	High Similarity	NPC262935
0.8933	High Similarity	NPC251182
0.8933	High Similarity	NPC172182
0.8931	High Similarity	NPC155640
0.8924	High Similarity	NPC304387
0.8924	High Similarity	NPC188486
0.8919	High Similarity	NPC472366
0.8917	High Similarity	NPC472877
0.8912	High Similarity	NPC62735
0.891	High Similarity	NPC45131
0.8903	High Similarity	NPC329844
0.8896	High Similarity	NPC72958
0.8896	High Similarity	NPC478148
0.8896	High Similarity	NPC474417
0.8896	High Similarity	NPC149526
0.8896	High Similarity	NPC232645
0.8889	High Similarity	NPC269420
0.8889	High Similarity	NPC131866
0.8882	High Similarity	NPC150215
0.8882	High Similarity	NPC123202
0.8882	High Similarity	NPC308200
0.8882	High Similarity	NPC77903
0.8882	High Similarity	NPC7943
0.8882	High Similarity	NPC17101
0.8882	High Similarity	NPC22005
0.8875	High Similarity	NPC136641
0.8874	High Similarity	NPC311741
0.8874	High Similarity	NPC234629
0.8874	High Similarity	NPC29577
0.8868	High Similarity	NPC219861
0.8868	High Similarity	NPC272722
0.8867	High Similarity	NPC144499
0.8867	High Similarity	NPC84266
0.8867	High Similarity	NPC310340
0.8861	High Similarity	NPC470810
0.8859	High Similarity	NPC172986
0.8859	High Similarity	NPC261227
0.8859	High Similarity	NPC69769
0.8859	High Similarity	NPC275734
0.8859	High Similarity	NPC28337
0.8859	High Similarity	NPC270883
0.8854	High Similarity	NPC196448
0.8854	High Similarity	NPC236796
0.8854	High Similarity	NPC273843
0.8846	High Similarity	NPC66508
0.8846	High Similarity	NPC55662
0.8846	High Similarity	NPC166054
0.8846	High Similarity	NPC254351
0.8846	High Similarity	NPC226656
0.8839	High Similarity	NPC130015
0.8839	High Similarity	NPC217447
0.8839	High Similarity	NPC38361
0.8839	High Similarity	NPC125300
0.8839	High Similarity	NPC41326
0.8839	High Similarity	NPC474843
0.8839	High Similarity	NPC87708
0.8831	High Similarity	NPC295036
0.8831	High Similarity	NPC470107
0.8831	High Similarity	NPC202595
0.8831	High Similarity	NPC476185
0.8831	High Similarity	NPC321896
0.8831	High Similarity	NPC472406
0.8831	High Similarity	NPC119929
0.8831	High Similarity	NPC472421
0.8831	High Similarity	NPC101957
0.8831	High Similarity	NPC120105
0.8824	High Similarity	NPC105415
0.8824	High Similarity	NPC216624
0.8816	High Similarity	NPC290133
0.8816	High Similarity	NPC187282
0.8816	High Similarity	NPC24136
0.8816	High Similarity	NPC299011
0.8816	High Similarity	NPC477955
0.8816	High Similarity	NPC237208
0.8812	High Similarity	NPC38591
0.8812	High Similarity	NPC109180
0.8812	High Similarity	NPC472581

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 NPC297531 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	385
0.1-0.2	977
0.2-0.3	1484
0.3-0.4	2658
0.4-0.5	1929
0.5-0.6	1103
0.6-0.7	414
0.7-0.8	137
0.8-0.85	51
0.85-0.9	12
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8854	High Similarity	NPD3749	Approved
0.8782	High Similarity	NPD7819	Suspended
0.875	High Similarity	NPD4378	Clinical (unspecified phase)
0.8658	High Similarity	NPD2344	Approved
0.8627	High Similarity	NPD7410	Clinical (unspecified phase)
0.8571	High Similarity	NPD6959	Discontinued
0.8544	High Similarity	NPD2393	Clinical (unspecified phase)
0.8543	High Similarity	NPD2800	Approved
0.8506	High Similarity	NPD2533	Approved
0.8506	High Similarity	NPD2532	Approved
0.8506	High Similarity	NPD2534	Approved
0.8491	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8476	Intermediate Similarity	NPD7473	Discontinued
0.8438	Intermediate Similarity	NPD3882	Suspended
0.8431	Intermediate Similarity	NPD2309	Approved
0.8421	Intermediate Similarity	NPD1243	Approved
0.8405	Intermediate Similarity	NPD6232	Discontinued
0.8397	Intermediate Similarity	NPD920	Approved
0.8378	Intermediate Similarity	NPD1240	Approved
0.8355	Intermediate Similarity	NPD1549	Phase 2
0.8333	Intermediate Similarity	NPD6559	Discontinued
0.8323	Intermediate Similarity	NPD7768	Phase 2
0.8323	Intermediate Similarity	NPD1511	Approved
0.8313	Intermediate Similarity	NPD2801	Approved
0.8302	Intermediate Similarity	NPD7411	Suspended
0.8289	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8289	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8282	Intermediate Similarity	NPD5494	Approved
0.8278	Intermediate Similarity	NPD1510	Phase 2
0.8272	Intermediate Similarity	NPD7075	Discontinued
0.8269	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.8267	Intermediate Similarity	NPD1607	Approved
0.825	Intermediate Similarity	NPD1934	Approved
0.8247	Intermediate Similarity	NPD3750	Approved
0.8242	Intermediate Similarity	NPD3926	Phase 2
0.8239	Intermediate Similarity	NPD4380	Phase 2
0.8235	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8224	Intermediate Similarity	NPD2796	Approved
0.8217	Intermediate Similarity	NPD1512	Approved
0.8199	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8193	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8176	Intermediate Similarity	NPD3226	Approved
0.8158	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.8141	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.8121	Intermediate Similarity	NPD1247	Approved
0.8105	Intermediate Similarity	NPD2935	Discontinued
0.8095	Intermediate Similarity	NPD3818	Discontinued
0.8089	Intermediate Similarity	NPD7390	Discontinued
0.8052	Intermediate Similarity	NPD2346	Discontinued
0.8047	Intermediate Similarity	NPD5844	Phase 1
0.8039	Intermediate Similarity	NPD2799	Discontinued
0.8	Intermediate Similarity	NPD919	Approved
0.7976	Intermediate Similarity	NPD6166	Phase 2
0.7976	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7976	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7975	Intermediate Similarity	NPD6799	Approved
0.7964	Intermediate Similarity	NPD7229	Phase 3
0.7949	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7939	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7935	Intermediate Similarity	NPD1471	Phase 3
0.7922	Intermediate Similarity	NPD3748	Approved
0.7914	Intermediate Similarity	NPD6801	Discontinued
0.7901	Intermediate Similarity	NPD6599	Discontinued
0.7879	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7871	Intermediate Similarity	NPD6100	Approved
0.7871	Intermediate Similarity	NPD6099	Approved
0.7866	Intermediate Similarity	NPD1465	Phase 2
0.7857	Intermediate Similarity	NPD5711	Approved
0.7857	Intermediate Similarity	NPD5710	Approved
0.7836	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7836	Intermediate Similarity	NPD7286	Phase 2
0.7821	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7818	Intermediate Similarity	NPD2296	Approved
0.7818	Intermediate Similarity	NPD3817	Phase 2
0.7797	Intermediate Similarity	NPD4287	Approved
0.7792	Intermediate Similarity	NPD6651	Approved
0.7791	Intermediate Similarity	NPD7074	Phase 3
0.7778	Intermediate Similarity	NPD943	Approved
0.7763	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7763	Intermediate Similarity	NPD2313	Discontinued
0.7759	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7756	Intermediate Similarity	NPD1551	Phase 2
0.7746	Intermediate Similarity	NPD5953	Discontinued
0.7733	Intermediate Similarity	NPD7054	Approved
0.7697	Intermediate Similarity	NPD4625	Phase 3
0.7688	Intermediate Similarity	NPD7472	Approved
0.7674	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7673	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD3764	Approved
0.7643	Intermediate Similarity	NPD5405	Approved
0.7643	Intermediate Similarity	NPD5404	Approved
0.7643	Intermediate Similarity	NPD5406	Approved
0.7643	Intermediate Similarity	NPD5408	Approved
0.7605	Intermediate Similarity	NPD5402	Approved
0.76	Intermediate Similarity	NPD7251	Discontinued
0.758	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7562	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7557	Intermediate Similarity	NPD7808	Phase 3
0.755	Intermediate Similarity	NPD1203	Approved
0.755	Intermediate Similarity	NPD1470	Approved
0.7545	Intermediate Similarity	NPD5761	Phase 2
0.7545	Intermediate Similarity	NPD5760	Phase 2
0.7543	Intermediate Similarity	NPD6797	Phase 2
0.7532	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD8313	Approved
0.7514	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD8312	Approved
0.75	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7486	Intermediate Similarity	NPD8434	Phase 2
0.7485	Intermediate Similarity	NPD6280	Approved
0.7485	Intermediate Similarity	NPD6279	Approved
0.7458	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7453	Intermediate Similarity	NPD4628	Phase 3
0.7443	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7403	Intermediate Similarity	NPD6832	Phase 2
0.7403	Intermediate Similarity	NPD4908	Phase 1
0.7401	Intermediate Similarity	NPD3658	Clinical (unspecified phase)
0.74	Intermediate Similarity	NPD1201	Approved
0.7394	Intermediate Similarity	NPD5403	Approved
0.7389	Intermediate Similarity	NPD447	Suspended
0.7386	Intermediate Similarity	NPD1729	Discontinued
0.7386	Intermediate Similarity	NPD2798	Approved
0.7384	Intermediate Similarity	NPD7199	Phase 2
0.7378	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7371	Intermediate Similarity	NPD3751	Discontinued
0.7351	Intermediate Similarity	NPD9717	Approved
0.7351	Intermediate Similarity	NPD1608	Approved
0.7346	Intermediate Similarity	NPD7003	Approved
0.7341	Intermediate Similarity	NPD6808	Phase 2
0.7308	Intermediate Similarity	NPD3268	Approved
0.7299	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD4361	Phase 2
0.7294	Intermediate Similarity	NPD4288	Approved
0.7292	Intermediate Similarity	NPD8151	Discontinued
0.7284	Intermediate Similarity	NPD2654	Approved
0.7278	Intermediate Similarity	NPD230	Phase 1
0.7278	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD37	Approved
0.7273	Intermediate Similarity	NPD7177	Discontinued
0.7273	Intermediate Similarity	NPD5401	Approved
0.7267	Intermediate Similarity	NPD6234	Discontinued
0.7251	Intermediate Similarity	NPD4966	Approved
0.7251	Intermediate Similarity	NPD4965	Approved
0.7251	Intermediate Similarity	NPD4967	Phase 2
0.7243	Intermediate Similarity	NPD4360	Phase 2
0.7243	Intermediate Similarity	NPD4363	Phase 3
0.7241	Intermediate Similarity	NPD3787	Discontinued
0.7219	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD2797	Approved
0.7208	Intermediate Similarity	NPD1164	Approved
0.72	Intermediate Similarity	NPD1651	Approved
0.7197	Intermediate Similarity	NPD411	Approved
0.7179	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7173	Intermediate Similarity	NPD7871	Phase 2
0.7173	Intermediate Similarity	NPD7870	Phase 2
0.7171	Intermediate Similarity	NPD1610	Phase 2
0.7171	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7171	Intermediate Similarity	NPD422	Phase 1
0.7169	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7166	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7159	Intermediate Similarity	NPD2403	Approved
0.7152	Intermediate Similarity	NPD17	Approved
0.7143	Intermediate Similarity	NPD6777	Approved
0.7143	Intermediate Similarity	NPD1876	Approved
0.7143	Intermediate Similarity	NPD7033	Discontinued
0.7143	Intermediate Similarity	NPD6776	Approved
0.7143	Intermediate Similarity	NPD6782	Approved
0.7143	Intermediate Similarity	NPD6780	Approved
0.7143	Intermediate Similarity	NPD6779	Approved
0.7143	Intermediate Similarity	NPD4308	Phase 3
0.7143	Intermediate Similarity	NPD6778	Approved
0.7143	Intermediate Similarity	NPD6781	Approved
0.7143	Intermediate Similarity	NPD6696	Suspended
0.7143	Intermediate Similarity	NPD1283	Approved
0.7143	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7128	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7128	Intermediate Similarity	NPD7783	Phase 2
0.7126	Intermediate Similarity	NPD6273	Approved
0.7124	Intermediate Similarity	NPD3972	Approved
0.712	Intermediate Similarity	NPD7697	Approved
0.712	Intermediate Similarity	NPD7698	Approved
0.712	Intermediate Similarity	NPD7696	Phase 3
0.712	Intermediate Similarity	NPD7435	Discontinued
0.7115	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD4060	Phase 1
0.7104	Intermediate Similarity	NPD8150	Discontinued
0.7101	Intermediate Similarity	NPD7458	Discontinued
0.7093	Intermediate Similarity	NPD5616	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7079	Intermediate Similarity	NPD7228	Approved
0.7078	Intermediate Similarity	NPD4749	Approved
0.7076	Intermediate Similarity	NPD6844	Discontinued
0.7062	Intermediate Similarity	NPD4575	Clinical (unspecified phase)
0.7043	Intermediate Similarity	NPD3269	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