NPASS Compound

Structure

NPC47883 OpenBabel07101718202D 34 38 0 0 0 0 0 0 0 0999 V2000 -5.4041 -3.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5380 -1.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2701 -4.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6720 -0.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2701 -2.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6720 -2.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6581 -2.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0739 -2.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3958 -0.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5823 0.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4041 -2.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5380 -2.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2079 -2.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4013 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6581 -1.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5768 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.1361 -3.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9836 -0.1045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.1361 -2.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8060 -2.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8060 -1.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9945 0.1045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0739 -1.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2079 -0.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1646 1.6180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2079 -3.9781 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.0021 -4.4781 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.9781 -0.2091 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.0021 -2.4781 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.9400 -2.9781 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.1591 1.5135 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.7579 2.5316 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.9400 -0.9781 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 3 2 0 0 0 0 1 11 1 0 0 0 0 2 4 2 0 0 0 0 2 12 1 0 0 0 0 3 17 1 0 0 0 0 4 21 1 0 0 0 0 5 11 2 0 0 0 0 5 19 1 0 0 0 0 6 12 2 0 0 0 0 6 20 1 0 0 0 0 7 13 2 0 0 0 0 7 15 1 0 0 0 0 8 13 1 0 0 0 0 8 23 2 0 0 0 0 9 14 1 0 0 0 0 9 18 2 0 0 0 0 10 16 2 0 0 0 0 10 22 1 0 0 0 0 11 12 1 0 0 0 0 13 26 1 0 0 0 0 14 15 1 0 0 0 0 14 22 2 0 0 0 0 15 24 2 0 0 0 0 16 18 1 0 0 0 0 16 25 1 0 0 0 0 17 19 2 0 0 0 0 17 27 1 0 0 0 0 18 28 1 0 0 0 0 19 29 1 0 0 0 0 20 21 2 0 0 0 0 20 30 1 0 0 0 0 21 33 1 0 0 0 0 22 34 1 0 0 0 0 23 24 1 0 0 0 0 23 33 1 0 0 0 0 24 34 1 0 0 0 0 25 31 2 0 0 0 0 25 32 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	460.08
Volume:	443.012
LogP:	5.027
LogD:	2.398
LogS:	-4.028
# Rotatable Bonds:	4
TPSA:	160.82
# H-Bond Aceptor:	9
# H-Bond Donor:	6
# Rings:	5
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.196
Synthetic Accessibility Score:	2.768
Fsp3:	0.0
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	2
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.842
MDCK Permeability:	6.410985861293739e-06
Pgp-inhibitor:	0.012
Pgp-substrate:	0.009
Human Intestinal Absorption (HIA):	0.312
20% Bioavailability (F20%):	0.948
30% Bioavailability (F30%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.013
Plasma Protein Binding (PPB):	95.67718505859375%
Volume Distribution (VD):	0.468
Pgp-substrate:	4.1287150382995605%

ADMET: Metabolism

CYP1A2-inhibitor:	0.77
CYP1A2-substrate:	0.07
CYP2C19-inhibitor:	0.043
CYP2C19-substrate:	0.033
CYP2C9-inhibitor:	0.562
CYP2C9-substrate:	0.116
CYP2D6-inhibitor:	0.034
CYP2D6-substrate:	0.134
CYP3A4-inhibitor:	0.081
CYP3A4-substrate:	0.033

ADMET: Excretion

Clearance (CL):	9.907
Half-life (T1/2):	0.908

ADMET: Toxicity

hERG Blockers:	0.049
Human Hepatotoxicity (H-HT):	0.348
Drug-inuced Liver Injury (DILI):	0.99
AMES Toxicity:	0.562
Rat Oral Acute Toxicity:	0.351
Maximum Recommended Daily Dose:	0.908
Skin Sensitization:	0.945
Carcinogencity:	0.598
Eye Corrosion:	0.003
Eye Irritation:	0.873
Respiratory Toxicity:	0.331

Download Data

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

Natural Product: NPC47883

Natural Product ID:	NPC47883
*Common Name:**	2,8-Dihydroxy-6-(3,3',4'-Trihydroxy-Biphenyl-4-Yloxy)-Dibenzofuran-3-Carboxylic Acid
IUPAC Name:	6-[4-(3,4-dihydroxyphenyl)-2-hydroxyphenoxy]-2,8-dihydroxydibenzofuran-3-carboxylic acid
Synonyms:
Standard InCHIKey:	VRTKLDOVWDISRQ-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C25H16O9/c26-13-7-15-14-9-18(28)16(25(31)32)10-22(14)34-24(15)23(8-13)33-21-4-2-12(6-20(21)30)11-1-3-17(27)19(29)5-11/h1-10,26-30H,(H,31,32)
SMILES:	Oc1cc(Oc2ccc(cc2O)c2ccc(c(c2)O)O)c2c(c1)c1cc(O)c(cc1o2)C(=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL251261
PubChem CID:	24178900
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000301] Benzofurans [CHEMONTID:0000015] Dibenzofurans

*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
NPO21285	Cladophora socialis	Species	Cladophoraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17949055]
NPO21285	Cladophora socialis	Species	Cladophoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	1

Activity Type	# Activity
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT178	Individual Protein	Protein-tyrosine phosphatase 1B	Homo sapiens	IC50	=	3710.0	nM	PMID[558960]

☑ 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 NPC47883 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	577
0.1-0.2	2327
0.2-0.3	5437
0.3-0.4	11148
0.4-0.5	5913
0.5-0.6	4198
0.6-0.7	5694
0.7-0.8	5107
0.8-0.85	1694
0.85-0.9	557
0.9-0.95	39
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
0.9765	High Similarity	NPC248315
0.9706	High Similarity	NPC226725
0.9647	High Similarity	NPC154527
0.9643	High Similarity	NPC98546
0.9643	High Similarity	NPC297807
0.9464	High Similarity	NPC216842
0.9464	High Similarity	NPC82217
0.9464	High Similarity	NPC476640
0.9458	High Similarity	NPC470704
0.9408	High Similarity	NPC287243
0.9405	High Similarity	NPC54098
0.9405	High Similarity	NPC230619
0.9353	High Similarity	NPC8127
0.9353	High Similarity	NPC49667
0.9349	High Similarity	NPC149846
0.9345	High Similarity	NPC476641
0.9306	High Similarity	NPC71260
0.9235	High Similarity	NPC65885
0.9205	High Similarity	NPC295436
0.9176	High Similarity	NPC174700
0.9128	High Similarity	NPC471841
0.9123	High Similarity	NPC473834
0.9107	High Similarity	NPC29411
0.9107	High Similarity	NPC36320
0.9107	High Similarity	NPC45449
0.908	High Similarity	NPC475996
0.9059	High Similarity	NPC280493
0.9059	High Similarity	NPC202470
0.9048	High Similarity	NPC263092
0.9048	High Similarity	NPC1755
0.9048	High Similarity	NPC1706
0.9048	High Similarity	NPC39305
0.9048	High Similarity	NPC59295
0.9017	High Similarity	NPC24258
0.9012	High Similarity	NPC117450
0.8988	High Similarity	NPC312056
0.8988	High Similarity	NPC84515
0.8988	High Similarity	NPC272722
0.8988	High Similarity	NPC238995
0.8976	High Similarity	NPC185526
0.8953	High Similarity	NPC247964
0.8953	High Similarity	NPC476370
0.8947	High Similarity	NPC476279
0.8929	High Similarity	NPC231758
0.8929	High Similarity	NPC188486
0.892	High Similarity	NPC471842
0.8916	High Similarity	NPC472461
0.8916	High Similarity	NPC137100
0.8902	High Similarity	NPC476374
0.8902	High Similarity	NPC261471
0.8895	High Similarity	NPC72696
0.8895	High Similarity	NPC218533
0.8895	High Similarity	NPC78830
0.8889	High Similarity	NPC86477
0.8889	High Similarity	NPC50394
0.8857	High Similarity	NPC475783
0.8844	High Similarity	NPC158226
0.8837	High Similarity	NPC247136
0.883	High Similarity	NPC272560
0.8824	High Similarity	NPC133065
0.8824	High Similarity	NPC89131
0.8817	High Similarity	NPC196179
0.8817	High Similarity	NPC34089
0.881	High Similarity	NPC196879
0.881	High Similarity	NPC16935
0.881	High Similarity	NPC195832
0.881	High Similarity	NPC154304
0.881	High Similarity	NPC190487
0.88	High Similarity	NPC164384
0.8793	High Similarity	NPC37606
0.8793	High Similarity	NPC310794
0.8779	High Similarity	NPC247973
0.8772	High Similarity	NPC39306
0.8772	High Similarity	NPC259757
0.8771	High Similarity	NPC269625
0.8771	High Similarity	NPC174486
0.8757	High Similarity	NPC300680
0.8757	High Similarity	NPC130955
0.8757	High Similarity	NPC188967
0.875	High Similarity	NPC77179
0.875	High Similarity	NPC23553
0.8743	High Similarity	NPC99591
0.8743	High Similarity	NPC227906
0.8736	High Similarity	NPC28589
0.8736	High Similarity	NPC248593
0.8735	High Similarity	NPC125300
0.8728	High Similarity	NPC163130
0.8728	High Similarity	NPC165979
0.8728	High Similarity	NPC49487
0.8728	High Similarity	NPC99613
0.8721	High Similarity	NPC277480
0.8713	High Similarity	NPC272064
0.8708	High Similarity	NPC240508
0.8701	High Similarity	NPC476273
0.8698	High Similarity	NPC115798
0.8698	High Similarity	NPC191459
0.8698	High Similarity	NPC18772
0.8698	High Similarity	NPC152166
0.8698	High Similarity	NPC25495
0.8698	High Similarity	NPC300943
0.8698	High Similarity	NPC261004
0.8698	High Similarity	NPC4481
0.8698	High Similarity	NPC19687
0.8698	High Similarity	NPC253634
0.8698	High Similarity	NPC176300
0.8698	High Similarity	NPC9609
0.8698	High Similarity	NPC22472
0.8698	High Similarity	NPC18607
0.8698	High Similarity	NPC204854
0.8698	High Similarity	NPC288669
0.8698	High Similarity	NPC193842
0.8698	High Similarity	NPC143828
0.8698	High Similarity	NPC105242
0.8698	High Similarity	NPC130894
0.8698	High Similarity	NPC7846
0.8693	High Similarity	NPC296018
0.8693	High Similarity	NPC154741
0.869	High Similarity	NPC45131
0.8686	High Similarity	NPC233956
0.8678	High Similarity	NPC28042
0.8678	High Similarity	NPC476365
0.8671	High Similarity	NPC234331
0.8671	High Similarity	NPC76482
0.8667	High Similarity	NPC47905
0.8667	High Similarity	NPC73929
0.8667	High Similarity	NPC139683
0.8663	High Similarity	NPC169471
0.8663	High Similarity	NPC291110
0.8663	High Similarity	NPC37183
0.8663	High Similarity	NPC280893
0.8659	High Similarity	NPC476170
0.8652	High Similarity	NPC97523
0.8644	High Similarity	NPC221820
0.8644	High Similarity	NPC476773
0.8644	High Similarity	NPC246877
0.8639	High Similarity	NPC472438
0.8639	High Similarity	NPC78302
0.8639	High Similarity	NPC75215
0.8639	High Similarity	NPC29841
0.8639	High Similarity	NPC110070
0.8639	High Similarity	NPC235215
0.8639	High Similarity	NPC224137
0.8639	High Similarity	NPC305663
0.8639	High Similarity	NPC7973
0.8639	High Similarity	NPC112954
0.8639	High Similarity	NPC176665
0.8639	High Similarity	NPC227192
0.8639	High Similarity	NPC163524
0.8639	High Similarity	NPC189179
0.8639	High Similarity	NPC203891
0.8639	High Similarity	NPC93376
0.8639	High Similarity	NPC287979
0.8639	High Similarity	NPC101830
0.8636	High Similarity	NPC289244
0.8636	High Similarity	NPC245975
0.8631	High Similarity	NPC292385
0.8631	High Similarity	NPC80489
0.8631	High Similarity	NPC125709
0.8629	High Similarity	NPC47386
0.8629	High Similarity	NPC262580
0.8629	High Similarity	NPC212038
0.8629	High Similarity	NPC81332
0.8629	High Similarity	NPC271848
0.8629	High Similarity	NPC289396
0.8626	High Similarity	NPC60848
0.8623	High Similarity	NPC27208
0.8621	High Similarity	NPC41494
0.8621	High Similarity	NPC186100
0.8621	High Similarity	NPC216403
0.8614	High Similarity	NPC260582
0.8613	High Similarity	NPC29160
0.8611	High Similarity	NPC304322
0.8605	High Similarity	NPC67959
0.8603	High Similarity	NPC246153
0.8603	High Similarity	NPC228209
0.8603	High Similarity	NPC36138
0.8596	High Similarity	NPC112418
0.8588	High Similarity	NPC156955
0.8588	High Similarity	NPC472877
0.8588	High Similarity	NPC107244
0.8588	High Similarity	NPC268533
0.8588	High Similarity	NPC36354
0.8588	High Similarity	NPC216307
0.8588	High Similarity	NPC287458
0.858	High Similarity	NPC474520
0.858	High Similarity	NPC100916
0.858	High Similarity	NPC55619
0.858	High Similarity	NPC247017
0.858	High Similarity	NPC98661
0.858	High Similarity	NPC245546
0.858	High Similarity	NPC30550
0.858	High Similarity	NPC265511
0.858	High Similarity	NPC200388
0.858	High Similarity	NPC178854
0.858	High Similarity	NPC268161
0.858	High Similarity	NPC266960
0.858	High Similarity	NPC292107
0.858	High Similarity	NPC49824
0.858	High Similarity	NPC43243
0.8571	High Similarity	NPC279209

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 NPC47883 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	477
0.1-0.2	1085
0.2-0.3	2070
0.3-0.4	2707
0.4-0.5	1624
0.5-0.6	794
0.6-0.7	250
0.7-0.8	113
0.8-0.85	21
0.85-0.9	9
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.858	High Similarity	NPD3882	Suspended
0.8547	High Similarity	NPD6232	Discontinued
0.8531	High Similarity	NPD4338	Clinical (unspecified phase)
0.8506	High Similarity	NPD7473	Discontinued
0.8471	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8462	Intermediate Similarity	NPD2801	Approved
0.8448	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8448	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8448	Intermediate Similarity	NPD6166	Phase 2
0.8421	Intermediate Similarity	NPD3749	Approved
0.8418	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8412	Intermediate Similarity	NPD3817	Phase 2
0.8352	Intermediate Similarity	NPD3818	Discontinued
0.8305	Intermediate Similarity	NPD5844	Phase 1
0.8286	Intermediate Similarity	NPD3926	Phase 2
0.8263	Intermediate Similarity	NPD1512	Approved
0.8246	Intermediate Similarity	NPD1465	Phase 2
0.8198	Intermediate Similarity	NPD5402	Approved
0.8187	Intermediate Similarity	NPD1934	Approved
0.8152	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.8144	Intermediate Similarity	NPD1511	Approved
0.8114	Intermediate Similarity	NPD5494	Approved
0.8103	Intermediate Similarity	NPD7075	Discontinued
0.807	Intermediate Similarity	NPD6599	Discontinued
0.8068	Intermediate Similarity	NPD1247	Approved
0.8066	Intermediate Similarity	NPD6559	Discontinued
0.8057	Intermediate Similarity	NPD919	Approved
0.8035	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8011	Intermediate Similarity	NPD6797	Phase 2
0.7968	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7967	Intermediate Similarity	NPD7251	Discontinued
0.7966	Intermediate Similarity	NPD6959	Discontinued
0.7956	Intermediate Similarity	NPD7074	Phase 3
0.7933	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7931	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7929	Intermediate Similarity	NPD6799	Approved
0.7923	Intermediate Similarity	NPD7808	Phase 3
0.7901	Intermediate Similarity	NPD7054	Approved
0.7874	Intermediate Similarity	NPD6801	Discontinued
0.7857	Intermediate Similarity	NPD7472	Approved
0.7841	Intermediate Similarity	NPD7768	Phase 2
0.7816	Intermediate Similarity	NPD7411	Suspended
0.7797	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7796	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7791	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7791	Intermediate Similarity	NPD5403	Approved
0.7778	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7759	Intermediate Similarity	NPD4380	Phase 2
0.7727	Intermediate Similarity	NPD7819	Suspended
0.7701	Intermediate Similarity	NPD3226	Approved
0.7679	Intermediate Similarity	NPD2344	Approved
0.7674	Intermediate Similarity	NPD5401	Approved
0.766	Intermediate Similarity	NPD8434	Phase 2
0.765	Intermediate Similarity	NPD3751	Discontinued
0.7647	Intermediate Similarity	NPD3750	Approved
0.7609	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7602	Intermediate Similarity	NPD6190	Approved
0.7594	Intermediate Similarity	NPD8312	Approved
0.7594	Intermediate Similarity	NPD8313	Approved
0.7584	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7572	Intermediate Similarity	NPD2533	Approved
0.7572	Intermediate Similarity	NPD2534	Approved
0.7572	Intermediate Similarity	NPD2532	Approved
0.7569	Intermediate Similarity	NPD7199	Phase 2
0.7563	Intermediate Similarity	NPD7435	Discontinued
0.7556	Intermediate Similarity	NPD6234	Discontinued
0.753	Intermediate Similarity	NPD943	Approved
0.7529	Intermediate Similarity	NPD1549	Phase 2
0.7527	Intermediate Similarity	NPD3787	Discontinued
0.7514	Intermediate Similarity	NPD7390	Discontinued
0.75	Intermediate Similarity	NPD2309	Approved
0.7487	Intermediate Similarity	NPD4287	Approved
0.7486	Intermediate Similarity	NPD920	Approved
0.7485	Intermediate Similarity	NPD1243	Approved
0.7471	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7471	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7471	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7456	Intermediate Similarity	NPD1510	Phase 2
0.744	Intermediate Similarity	NPD1607	Approved
0.7414	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7412	Intermediate Similarity	NPD2935	Discontinued
0.7412	Intermediate Similarity	NPD5406	Approved
0.7412	Intermediate Similarity	NPD1551	Phase 2
0.7412	Intermediate Similarity	NPD5405	Approved
0.7412	Intermediate Similarity	NPD5408	Approved
0.7412	Intermediate Similarity	NPD5404	Approved
0.7411	Intermediate Similarity	NPD6782	Approved
0.7411	Intermediate Similarity	NPD6778	Approved
0.7411	Intermediate Similarity	NPD6776	Approved
0.7411	Intermediate Similarity	NPD6777	Approved
0.7411	Intermediate Similarity	NPD6780	Approved
0.7411	Intermediate Similarity	NPD6779	Approved
0.7411	Intermediate Similarity	NPD6781	Approved
0.7381	Intermediate Similarity	NPD447	Suspended
0.7376	Intermediate Similarity	NPD8151	Discontinued
0.7374	Intermediate Similarity	NPD37	Approved
0.7371	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7366	Intermediate Similarity	NPD7228	Approved
0.7356	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD3748	Approved
0.7348	Intermediate Similarity	NPD4965	Approved
0.7348	Intermediate Similarity	NPD4967	Phase 2
0.7348	Intermediate Similarity	NPD4966	Approved
0.7341	Intermediate Similarity	NPD4628	Phase 3
0.734	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.734	Intermediate Similarity	NPD7874	Approved
0.7326	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD1240	Approved
0.731	Intermediate Similarity	NPD2796	Approved
0.7292	Intermediate Similarity	NPD8150	Discontinued
0.7283	Intermediate Similarity	NPD2800	Approved
0.7283	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD230	Phase 1
0.7273	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD2346	Discontinued
0.7264	Intermediate Similarity	NPD7870	Phase 2
0.7264	Intermediate Similarity	NPD7871	Phase 2
0.7259	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7251	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7247	Intermediate Similarity	NPD1653	Approved
0.7214	Intermediate Similarity	NPD7698	Approved
0.7214	Intermediate Similarity	NPD7696	Phase 3
0.7214	Intermediate Similarity	NPD7697	Approved
0.7186	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7168	Intermediate Similarity	NPD1471	Phase 3
0.7158	Intermediate Similarity	NPD5953	Discontinued
0.7157	Intermediate Similarity	NPD6534	Approved
0.7157	Intermediate Similarity	NPD6535	Approved
0.7157	Intermediate Similarity	NPD7701	Phase 2
0.7151	Intermediate Similarity	NPD2799	Discontinued
0.7143	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7136	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7136	Intermediate Similarity	NPD7783	Phase 2
0.7126	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.712	Intermediate Similarity	NPD7685	Pre-registration
0.7111	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD2313	Discontinued
0.7101	Intermediate Similarity	NPD3764	Approved
0.709	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7069	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD6233	Phase 2
0.7059	Intermediate Similarity	NPD5710	Approved
0.7059	Intermediate Similarity	NPD5711	Approved
0.7059	Intermediate Similarity	NPD7229	Phase 3
0.7053	Intermediate Similarity	NPD7801	Approved
0.705	Intermediate Similarity	NPD7700	Phase 2
0.705	Intermediate Similarity	NPD7699	Phase 2
0.7049	Intermediate Similarity	NPD8455	Phase 2
0.7045	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD1613	Approved
0.7017	Intermediate Similarity	NPD7458	Discontinued
0.7011	Intermediate Similarity	NPD6099	Approved
0.7011	Intermediate Similarity	NPD6100	Approved
0.7011	Intermediate Similarity	NPD2296	Approved
0.701	Intermediate Similarity	NPD8320	Phase 1
0.701	Intermediate Similarity	NPD8319	Approved
0.7006	Intermediate Similarity	NPD1203	Approved
0.7005	Intermediate Similarity	NPD8127	Discontinued
0.7	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6798	Discontinued
0.7	Intermediate Similarity	NPD7177	Discontinued
0.6995	Remote Similarity	NPD7907	Approved
0.6989	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.698	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD1933	Approved
0.6963	Remote Similarity	NPD7286	Phase 2
0.6949	Remote Similarity	NPD7003	Approved
0.6943	Remote Similarity	NPD7240	Approved
0.6931	Remote Similarity	NPD5242	Approved
0.6928	Remote Similarity	NPD9269	Phase 2
0.6912	Remote Similarity	NPD6823	Phase 2
0.6907	Remote Similarity	NPD7549	Discontinued
0.6901	Remote Similarity	NPD4665	Approved
0.6901	Remote Similarity	NPD4111	Phase 1
0.6895	Remote Similarity	NPD2403	Approved
0.6879	Remote Similarity	NPD6355	Discontinued
0.6878	Remote Similarity	NPD6808	Phase 2
0.6857	Remote Similarity	NPD4308	Phase 3
0.6852	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD7095	Approved
0.6842	Remote Similarity	NPD3027	Phase 3
0.6828	Remote Similarity	NPD4288	Approved
0.6823	Remote Similarity	NPD2163	Approved
0.6821	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6816	Remote Similarity	NPD2354	Approved
0.6806	Remote Similarity	NPD7784	Clinical (unspecified phase)
0.6805	Remote Similarity	NPD1470	Approved
0.6802	Remote Similarity	NPD411	Approved
0.6802	Remote Similarity	NPD3268	Approved
0.6796	Remote Similarity	NPD7680	Approved
0.6784	Remote Similarity	NPD4908	Phase 1
0.6784	Remote Similarity	NPD6832	Phase 2
0.678	Remote Similarity	NPD2493	Approved
0.678	Remote Similarity	NPD2494	Approved
0.678	Remote Similarity	NPD3450	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